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ALSO IN THIS ISSUE: Breath analysis in medical diagnostics • Government grantsfor small business: worth the effort? • Tribute to Sir John Cornforth

chemistryin AustraliaApril 2014

WWI centenary series:blood on the battlefield

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Key DatesCall for Abstracts Opens 2 December 2013

Registration Opens 2 December 2013

Abstract Submission Deadline 9 May 2014

Notification of Acceptance of Abstract June 2014

Early Bird Registration Closes 1 August 2014

Accommodation Booking Deadline 30 September 2014

Congress Dates 7-12 December 2014

Contact UsRACI2014 Congress Secretariat ICMS AustralasiaGPO Box 3270, Sydney NSW 2001Ph: +61 2 9254 5000 • Fax: +61 2 9251 [email protected]

Call forAbstracts isnow open!ABSTRACT SUBMISSION DEADLINE 9 MAY 2014

The RACI2014 Scientific Program Committee invitesauthors to submit abstracts for presentation within any ofthe RACI2014 symposia. Submissions are sought for oraland poster presentations at the RACI National Congressto be held from 7-12 December 2014 in Adelaide.

A stimulating scientific program is being planned withplenary lectures, abstracts and thematic poster sessions.

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For the full biographies of confirmed speakers to theRACI 2014 National Congress please visit the Congresswebsite at www.racicongress.com

Scientific Program Themes• Synthetic Chemistry • Fundamental Interactions inChemistry • Advanced Materials • Chemical Health andSafety • Chemistry in Health • Chemical Analysis andSensing • Community Engagement

views & reviews4 Editorial6 Your say28 Careers30 Books33 Education34 Conservation36 Cholesterol38 Environment39 Grapevine40 Bioindustry41 Letter from Melbourne

April 2014

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cover story

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news & research7 News8 Research42 Cryptic chemistry42 Events

members26 Obituary

16 Breath-taking: how to catch a chemical signature Breath analysis is a powerful and adaptable tool for medical diagnosis and therapeutic monitoring.

20 Corrections for AASAAS is generally free of interferences common to other methods, but three minor types do occur.

22 Marionette moneyGovernment grants for business are readily available, but are they worth the trouble?

Fighting fitResearchers are turning to everything from common plastics tonanotechnology to try and save lives on the battlefield.

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EDITOR Sally WoollettPh (03) 5623 [email protected]

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editorial

Chemistry in Australia4 | April 2014

The streets in my new neighbourhood have related names. Ineedn’t mention more than Tobruk and Kokoda for you to guessthe theme. Other namesakes include Normanby Island(southernmost of the D’Entrecasteaux Islands, north-east ofPapua and involved in the Pacific War), Field Marshal BernardMontgomery and the naval ship USS Rutland.

Nearby but slightly removed from this group is Nobel St.Perhaps its placement signifies the dearth of laureates duringthe world wars. Recipient of one of the few Nobel Prizesawarded during World War I was Adelaide-born Lawrence Bragg,who at the tender age of 25 shared the 1915 Nobel Prize forPhysics with his father, William, ‘for their services in theanalysis of crystal structure by means of X-rays’. He was awardedthe Military Cross during the war, for his work in sound-ranging:detecting the position of enemy artillery by recording andanalysing the boom of their weapon fire.

This year is the centenary of World War I, the ‘chemists’ war’.In coming issues, our feature contributors will explore theinvolvement of chemistry and other sciences, and scientists(professionally or in military action), in World War I and in warmore generally.

A June 1927 edition of the Adelaide Mail’s Prominent Mensection showed me that William Bragg and John Monash werevery similar in age. At that time, the former was Director andFullerian Professor of Chemistry at the Royal Institution ofBritain, while Monash was Chairman of the State ElectricityCommission of Victoria, tackling an ‘intricate combination ofadministrative, financial and engineering questions … entirelyto his taste’.* Look out for more about Monash – civil engineer

and exceptional wartime military commander, described by theMail as ‘a great Australian of the war period and since’ – in afuture edition.

In her guest editorial last month (p. 4) ChemistryInternational editor Fabienne Meyers congratulated theOrganisation for the Prohibition of Chemical Weapons (OPCW)on their Nobel Peace Prize, received in 2013 ‘for its extensiveefforts to eliminate chemical weapons’. Disarmament was animportant message in Alfred Nobel’s will. Next month we willmeet the OPCW Temporary Working Group on Education andOutreach and learn about Australia’s OPCW involvement.

Future issues will feature Australia’s first defence scientist,Cecil Napier Hake, and his role in the establishment of thegovernment’s first cordite factory, managed by Arthur Leighton;and some wartime science in the sky.

Medical personnel in World War I could only dream of usingmaterials such as polyurethane (first made by Otto Bayer andcolleagues in 1937) and synthetic amino acids in field hospitalsto reduce blood loss. Polymers and nanotechnology for thispurpose are now realities in modern warfare, as you’ll read inthis month’s cover story, p. 12. Also in this issue, we paytribute to Sir John Cornforth, who was born during the GreatWar and died in December last year.

War and peace

Sally Woollett ([email protected])

* Searle G. John Monash: a biography. Melbourne University Press, 1982, p. 437.

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your say

6 | April 2014Chemistry in Australia

Picric acid disposalThe article on picric acid by Dr Roger Read (February issue, p. 20)recalled an article on the same subject I had in my files by MarkCameron, CIH, entitled ‘Picric Acid Hazards’ and dated 18 June2002. I can’t recall where I obtained the article (probably viaGoogle). Dr Read acknowledges an article by Cameron from 2007and provides a link. It may well be the same document.

As the former owner of a hazardous waste disposal firm, weregularly encountered picric acid in many forms, including bottlesthat had dried out. Many years ago, we were able to have theformer Department of Labour and Industry (DLI) explosivesdepartment collect all our stored picric acid for disposal at the oldQueen Street, Altona, explosives and firing range. The DLI werealso disposing of some old detonators, detonator cord, ’sweating’gelignite and the like. My 20 or so bottles of picric acid, whichwere all fully wetted naturally, were systematically wrapped in theold detonator cord, along with the other materials, and eventuallythe whole lot was blown up. However, the explosion did not setoff the picric acid; in fact, the explosion resulted in a large craterwith a distinct yellow tinge about it.

Both articles mention that there has been no known incidentinvolving picric acid in a laboratory and that the metal andcalcium salts are far more sensitive to heat and shock and presenta far greater danger. Some years ago, a colleague of mine used toimport picric acid from Spain in 40-kilogram steel tubs, and as itwas transported with 30% of its weight with water, according tothe international transport requirement, he had to dry the picricbefore he could use it. He did his research and came to the sameconclusion that wet picric does not present an explosion hazardand dried the picric acid in stainless steel trays over a gas ring.

The only time we would not collect a bottle of dry picric acidfor disposal was if the bottle had a metal lid. The mention of thedangers of having dried crystals in the thread of a screw cap orbetween the surfaces in a glass-stoppered bottle is also a littleapocryphal. LoveToKnow 1911 Online Encyclopedia states: ‘Whenignited, picric acid burns quietly with a smoky flame, and it is verydifficult to detonate by percussion; its salts, however, are morereadily detonated.’ Both articles suggest disposal of surplus or oldpicric acid as hazardous waste, which is where we would come in.The reductive disposal methods mentioned by Dr Read (details ofwhich are to found in Lunn and Sansone’s Destruction of hazardouschemicals in the laboratory or Amour’s Hazardous laboratorychemicals disposal guide) are not used in the chemical disposalindustry as it is not a good idea to simply treat something to formsomething else that remains toxic but no longer explosive. Thebest way is to dissolve the picric acid in waste solvent, followedby incineration. Blowing the stuff up doesn’ t seem to workanyway.

The explosion risk presented by picric acid use (wet or dry) inthe laboratory is an overrated one. Metal picrates certainly are adetonation hazard. Picric acid was not treated as a particularlydangerous chemical for disposal and there are far worse materialspresenting more danger to the hazardous chemical disposal firm.These include hydrofluoric acid, isocyanates, chloropicrin (made

with picric acid), organic peroxides that form in certain solvents,and, probably the worst of all, white phosphorus. There are manyothers, but these particular items always elicited a groan when wewere asked to collect and dispose of them. I won’t mentionmercaptans either!

Michael Pola MRACI CChem

Praise from the fringesI work on the fringes of science at an engineering consultancy,where I do mostly policy and infrastructure approvals. Rarely do Ihave the opportunity to exercise my chemistry skills, so it’s niceto at least read on academic and featured chemistry topics in themagazine. Having said that, I do enjoy reading articles andcolumns that come a little closer to home for me. In particular,the columns on environmental science and contaminated landtopics from Paul Moritz. Anything in that vein would be great. Ialso really like to read articles and columns from Ian Maxwell. Heis a thought-provoking columnist, but I’m sure that his ideas arenot to everyone’s liking. I want to voice my support of hiscolumns and possibly offset other members who might grumble.

Lastly, thank you very much for your work on the magazine.The format and variety of content have improved over the lastcouple of years, making it a much easier read.

Steven Cox MRACI CChem

A little more on Charles CoulsonOn reading Peter Karuso’s article (March issue, p. 16), I note morethan a passing reference to Charles Coulson. I was anundergraduate in chemistry at Leeds at the time of Coulson’suntimely death in 1974. In our quantum mechanics lectures byP.B. Ayscough the previous academic year, we had been referred toCoulson’s book Valence (2nd edition, OUP 1961).

At the time of Coulson’s death, there was a good deal ofcomment on his contributions to the study of religion. His worksin this area include ‘Science, Technology and the Christian’ (1953)and ‘Science and Christian Belief’ (1955). He was a ‘man of affairs’in religion as well as in the physical sciences, having, for example,served on the World Council of Churches. His own affiliation waswith the Methodist church, but his thinking was much tooexpansive to be restricted or even strongly influenced bydenominational boundaries.

The old controversy between ‘science and religion’ has largelybeen relegated to the past, but it was an issue in Coulson’s day. Irecall at the time of Coulson’s death having a social conversationwith a retired professor of mathematics at Leeds, who had himselfcontributed significantly to quantum mechanics. I do not knowwhether he knew Coulson personally, although he probably did. Hesaid that men like Coulson who so effectively united science andreligion were a valuable influence in times of ‘materialism’. Articlesabout Coulson in history of science journals have developed thispoint.

Clifford Jones FRACI CChem

news

7|April 2014 Chemistry in Australia

New research by the University ofTasmania has examined the toxic effectsof seabirds ingesting marine plasticpollution and population decline.

UTAS’s Institute for Marine andAntarctic Studies (IMAS) Research FellowDr Jennifer Lavers conducted the studyover four years in collaboration withresearchers at the Lord Howe IslandMuseum and Royal Society for theProtection of Birds.

The study sampled the breast feathersand stomach contents from flesh-footedshearwater fledglings in eastern Australiaand the results have been publishedonline in Environmental Pollution(bit.ly/1gLhM1Z).

The number of birds ingesting plasticincreased over the four-year study, withmore than 60% of fledglings exceedinginternational targets for plastic ingestionby seabirds, and 16% of fledglings failingthose targets after a single feeding. Birdswith high levels of ingested plasticexhibited reduced body condition andincreased contaminant load.

Lavers said this is the first paperanywhere in the world to link high levelsof trace metals to the ingestion of marineplastic pollution.

‘What we have been missing from theequation is the ability to look beyond thevisual – beyond the plastic bits – andinto the animal’s tissues to see whatdamage the plastic has caused by

introducing toxins (such as trace metalslike mercury and arsenic) into the birds,’she said.

Lavers said while the researchreported an increase from 79% to 90% infrequency of plastic consumption, it alsorecorded the highest total amount (mass)of plastic ingested by any marine speciesworldwide.

‘We are providing quantitative data onthe demographic impact of ingestedplastic (i.e. reduced seabird bodycondition and likely reduced juvenilesurvival), which is crucial information forwildlife managers to be able to account

for mortality and morbidity in theirmanagement plans,’ she said.

‘It seems obvious that ingestingplastic would be bad for wildlife, butuntil now, no one has been able to showwhat role plastic plays in drivingpopulation trends.

‘Our results indicate marine plasticpollution is a serious threat to the flesh-footed shearwater, a worrying result inlight of increasing demand for plasticproducts and the more than 20 millionnew pieces of plastic that enter theworld’s oceans every day.’UNIVERSITY OF TASMANIA

Trace metals linked to ingestion of plastic by seabirds

Researchers at RMIT University havedeveloped a concept hydrogen batterybased simply on storing protons producedby splitting water. The concept advancesthe potential for hydrogen to replacelithium in battery-powered devices.

The proton flow battery concepteliminates the need for the production,storage and recovery of hydrogen gas,which currently limit the efficiency ofconventional hydrogen-based electricalenergy storage systems.

Lead researcher Associate ProfessorJohn Andrews, from RMIT’s School of

Aerospace, Mechanical and ManufacturingEngineering, said the novel conceptcombined the best aspects of hydrogenfuel cells and battery-based electricalpower.

The concept integrates a metalhydride storage electrode into areversible proton exchange membranefuel cell. During charging, protonsproduced from splitting water are directlycombined with electrons and metalparticles in one electrode of a fuel cell,forming a solid-state metal hydride asthe energy storage. To resupply

electricity, this process is reversed.Published in the International Journal

of Hydrogen Energy (bit.ly/1jJWKVd), theresearch found that, in principle, theenergy efficiency of the proton flowbattery could be as high as that of alithium ion battery, while storing moreenergy per unit mass and volume.

The published paper is the first toarticulate and name the proton flowbattery concept, and the first to includean experimental preliminary proof ofconcept.RMIT UNIVERSITY

Concept proton flow battery to advance hydrogen power

Dr Lavers with a shearwater

research


Masterpieces of cubism: nanoscaleLiH clusters Well-defined molecular hydride complexes of the alkali metalsare still very rare, despite great potential importance forchemical synthesis, catalysis and hydrogen storage applications,and their parent metal hydrides are too insoluble and stable formany applications. Theoretical studies suggest that nanosizedmetal hydride clusters have significantly different and highlybeneficial properties, compared with their bulk phases, thoughthe generation of the nanoclusters remains a syntheticchallenge. Now, Andreas Stasch from Monash University reportson the bottom-up synthesis and characterisation of a family ofligand-stabilised LiH compounds with metal–hydride cores inthe nanometre region (Stasch A. Angew. Chem. Int. Ed. 2014,53, 1338–41). Mixtures of butyllithium, 3,5-di-t-butyl -pyrazolate (pz–) and a silane afford stable, hydrocarbon-solubleand hydride-rich cluster compounds that have been structurallycharacterised using synchrotron radiation (e.g. [(pz)12Li37H25],pictured). The pyrazolate ligands occupy all corner and someedge positions in the structures and stabilise and solubilise aLiH core with numerous LiH cubes of approximately 1 nmdiameter. These examples represent the largest molecular Liaggregates and some of the largest well-defined metal-hydrideclusters of all elements known to date. The clusters arestabilised by a simple pyrazolate ligand and one aim is toextend this strategy to other light metal hydrides and mixedmetal systems.

Helical peptides as tunable molecularwires Helical domains in peptides and proteins provide a good mediumfor electron transfer over surprisingly long molecular distances.Such structures are ideal candidates for use as molecular wires,particularly when combined with an ability to be preciselyfunctionalised. However, more detailed understanding of exactlywhat defines and controls the mechanisms and efficiency ofelectron transfer in peptides is required before this promise canbe fully realised. With this in mind, researchers at the Universityof Adelaide and Flinders University have investigated two helicalpeptides, one linear, the other constrained by a covalent side-chain staple (Yu J., Horsley J.R., Moore K.E., Shapter J.G., AbellA.D. Chem. Commun. 2014, 50, 1652–4). Electrochemical studiesrevealed that the constrained peptide exhibits a significantformal potential shift to the positive (480mV), and a substantialdecrease in the electron transfer rate constant (25%), comparedto the linear analogue. High-level calculations confirmed thatthe additional reorganisation energy barrier is a direct result ofthe backbone rigidity imparted by the side-bridge constraint.These findings provide a new means to fine tune the rates ofelectron transfer in peptides, an important step towards theirimplementation into molecular electronic assemblies.

April 2014

Exploiting a,b-unsaturated N-acyliminium ions

Researchers at the University ofTasmania, University of Edinburgh,and University College London havepooled their complementary expertisein synthetic and computationalmacrocyclic lanthanide and actinidechemistry to prepare a series ofactinide complexes that display rarep-arene binding modes, which switchin response to metal oxidation statechanges and M–L covalency needs(Arnold P.L., Farnaby P.H., White R.C.,Kaltsoyannis N., Gardiner M.G., Love

J.B. Chem. Sci. 2014, 5, 756–65). Ofwide fundamental and appliedinterest, the binding modes of thismacrocyclic ligand with lanthanideand actinide complexes appear to beexclusive for the higher metaloxidation states. This is adiscrimination offering a cleardirection to pursue in future studiestargeting nuclear fuel wasteprocessing, as this structural featureshould carry through to physicaldifferences that can be exploited.

Switchable binding could aid nuclear fuelprocessing

A new strategy for the synthesis ofspiro and bridged heterocycles has beendeveloped by Dr Arife Yazici andProfessor Stephen Pyne from theUniversity of Wollongong (Org. Lett.2013, 15, 5878–81). This newprocedure involves novel sequential 1,4- and 1,2-addition reactions oflatent bis-nucleophiles to a,b-unsaturated N-acyliminium ions. Unlikethe more common simple

N-acyliminium ions, the chemistry oftheir a,b-unsaturated cousins has beenlittle explored. The new method allowsrapid access to molecular complexitythrough reactions that result information of two or three new chemicalbonds in a one-pot process, and thesynthesis of novel natural product-likescaffolds, including the ones shownbelow. This chemistry is currently beingexplored in new drug discovery

M1097_TOCApplikonStrAdv_76x275_20140221.indd 1 21/02/2014 14:21

research


Art imitates life

Compiled by Matthew Piggott MRACI CChem ([email protected]). This section showcases the very best research carried out primarily in Australia. RACI memberswhose recent work has been published in high impact journals (e.g. Nature, J. Am. Chem. Soc., Angew. Chem. Int. Ed.) are encouraged to contribute general summaries, of nomore than 200 words, and an image to Matthew.

The alkaloid incargranine B was isolated in 2010 by Zhang andcoworkers from Incarvillea mairei var. grandiflora, a floweringplant native to the mountains of central and southern China.Based on their analysis of the obtained spectroscopic data, theisolation chemists proposed an indolo[1.7]naphthyridinestructure for incargranine B. This exotic structure caught theattention of a team of synthetic chemists led by Dr AndrewLawrence at the Australian National University. By consideringthe likely biosynthetic origins of this new alkaloid the ANUteam were able to propose a different structure for incargranineB that still accounted perfectly for all the obtained

spectroscopic data. The ANU chemists were able to prove thisnewly proposed structure was correct via a short biomimetictotal synthesis (Brown P.D., Willis A.C., Sherburn M.S., LawrenceA.L. Angew. Chem. Int. Ed. 2013, 52, 13273–5). The synthesis,which was carried out by PhD student Mr Patrick Brown, reliedupon a key biomimetic domino Mannich/electrophilic aromaticsubstitution reaction sequence. This domino process formed twonew C–C bonds, two new C–N bonds and three new rings in justone chemical reaction. This work is a clear demonstration of thepower of biosynthetic considerations in aiding thedetermination/reassignment of natural product structures.

A multinational team led by Anna Chrostowska (University ofPau, France), Stanislaw Lesniak (University of Lodz, Poland) andCurt Wentrup (University of Queenland) have reported new freeradical rearrangement reactions induced by flash vacuumthermolysis of N-t-butylimines (Vu T.Y., Chrostowska A., JustynaK., Pasternak B., Lesniak S., Wentrup C. Chem. Eur. J. 2013, 19,14983–8). Efficient methyl group loss from the t-butyl groupsaffords iminoalkyl radicals, which can undergo 1,4-H shifts

followed by cyclisation to isoquinolines, or onto the N atom ofa pyridine ring to afford an imidazo[1,5-a]pyridine. Theiminoalkyl radicals can also cyclise to the little-known class ofaziridinyl radicals, which by ring opening and addition tobenzene rings give rise to indoles. Thus, a variety ofheterocycles can be generated quite selectively inunprecedented high-temperature and high-yield radicalreactions.

Radical rearrangements

Chemistry in Australia 11|April 2014

The March issue contains 28 papers authored byparticipants in the 6th Heron Island Conference onReactive Intermediates and Unusual Molecules,held in July 2013.

Shunichi Fukuzumi and coworkers (Osaka)report the reduction of O2 using cobaltphthalocyanine and other catalysts to generateH2O2, and its use as an energy carrier for a fuel cellto generate electricity.

M.P. Doyle and X. Xu (Maryland)review recent uses of metal carbenoidsderived from silylated enol-diazoacetates in the synthesis ofheterocyclic compounds, includingfurans, pyrroles, lactones, tropanes,oxazines, tetrahydropyridazines,pyranones and oxepins.

The importance of reactiveintermediates in total synthesis ofcomplex natural products should neverbe underestimated, and suchapplications are always represented atthe Heron Island conferences. Al Padwa(Emory) has used RhII-catalysedcarbenoid reactions of diazocompounds extensively in totalsyntheses, and reports here the use ofthis protocol with 2-(diazomethyl)indolyl derivatives as aroute to scandine, a member of themelodinum alkaloid family.

Both fluorine and benzynechemistries are experiencingrenaissances, and fluorine-containingcompounds are of widespreadimportance in medicine, materialsscience, electronics etc. TakashiIkawa (Osaka) reports a newpreparation of aryl fluorides usingbenzyne chemistry. This one-potreaction is completed in 90 minutes.

Three papers from Stephen Hashmi’s group (Heidelberg)describe N-heterocyclic carbene-PtII-isocyanide and gold catalysisin organic chemistry as well as gold catalysis of styrenepolymerisation. John P. Maier (Basel) reports spectroscopiccharacterisation of the methyltriacetylene cation, CH3–C≡C–C≡C–C≡C–H•+, and Michael Oelgemöller (Townsville) reviews the rathernew and important field of micro-flow photochemistry.

The 7th Heron Island Conference, organised by CraigWilliams and Curt Wentrup, will be held 9–15 July 2016,immediately following the IUPAC International Conference onPhysical Organic Chemistry in Sydney. The latter is organised byJason Harper (University of New South Wales) et al.

Aust J Chem

Curt Wentrup FAA, FRACI CChem ([email protected])http://researchers.uq.edu.au/researcher/3606

Blood loss is the major causeof death for soldiers, whetherthey have been hit by aroadside bomb or by a bullet.

And since the main priority for themilitary is to return wounded soldiersto active duty, many of the emergingmilitary medical techniques focus onthe need to reduce blood loss –especially from hard-to-treat internalinjuries. At the same time, any systemmust be portable enough to becarried around on the battlefield.

One ingenious idea uses aneveryday plastic, polyurethane (PU),which is used everywhere from shoesoles to mattresses. It takes the form ofa solid foam, but is supplied as twoliquids – a di-isocyanate and a diol ortriol – which when mixed together withwater form a foam. US-based ArsenalMedical has devised a specialformulation of PU so that the twoliquids can be injected into theabdominal cavity via the belly buttonof wounded soldiers: as the liquids mix

and solidify the resulting foam acts asan ‘internal tourniquet’ by puttingpressure on bleeding internal organs.

‘Intra-abdominal haemorrhage is aleading cause of death on thebattlefield,’ says Upma Sharma,director of materials science andengineering at Arsenal Medical. ‘Theonly current solution is to evacuate thewounded as quickly as possible.’

The abdominal cavity is so largeand complex that an exact wounddiagnosis is difficult, she says. It could


be anything from a gunshot wound tothe liver, to a punctured spleen. Themost effective treatment – performingsurgery on the spot – is just notpossible in the heat of combat. ‘Oursystem tries to extend life, by givingenough time to get the patient tosurgical care,’ she says. ‘It appliespressure at the wound site and slowsthe bleeding for long enough to buytime.’

The company has worked withDavid King, a trauma surgeon atMassachusetts General Hospital in

Boston, US, to develop the system. ‘Hesays that – if you could see some ofthese internal wounds – you could stopthe bleeding with your thumb,’ saysSharma. By applying pressure acrossthe whole abdominal cavity, the systemacts like a ‘thumb’ on every potentialwound site. The system is expected toform part of the combat medic’sbackpack armoury but will need to beperfected before it can becommercialised, which might take upto 10 years.

Filling a mould to make a PU shoe

sole is one thing, but doing the samewith the human abdominal cavity is amuch more precise operation. Sharmasays that a multitude of factors must betaken into account to make it work.

The first complication is that theabdominal cavity is filled with bloodfrom the wound. Sharma likens it to amoat around a castle, stopping theprogress of the foam. The PU mustforce its way through this, and find itsway to the wound site. This means thatthe reaction kinetics – whichdetermine how quickly the injected


Researchers are turning to everything fromcommon plastics to nanotechnology to tryand save lives on the battlefield.

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liquids become a foam – must beconsidered and carefully controlled.

The liquid components of the foamare hydrophobic, so will not mix withthe blood. Rather than ‘absorbing’ theblood within the body – which thecompany had originally planned to do– the hydrophobic liquid pushes theblood aside, before forming a foamaround the internal organs.

The expansion ratio of the materialis thus another importantconsideration: the volume of thestarting liquids has to be as small aspossible so that the system is portable,but there needs to be enough of theliquids so that the resulting foam fitsthe large expanse of the abdominalcavity. ‘This is not an off-the-shelfgrade of PU,’ says Sharma. ‘We havelooked at more than 1000 grades tofind one that meets all our needs.’

The system has been tested onpigs, in which their liver was severed –an injury that would cause death for90% of animals in the first hour. Butinjecting with this PU system helped100% of the animals to survive the firsthour, and 80% were still alive afterthree hours. The next step is to begindiscussions with the US Food and DrugAdministration (FDA) to investigate thepossibility of starting human trials inthe future.

An earlier aspiration, based on agovernment request, was to developsomething to deliver peptides or other‘therapeutic payloads’ to the injuredtissue. In that case, the foam wouldhave acted as the transportmechanism. But the early testing datashowed that the current idea could be

realised more quickly. ‘As soon as wegot the foam data back, we knew wehad something good,’ says Sharma.

Acid testThere are other ways of approachingthe problem of bleeding on thebattlefield. UK researchers at theLondon School of Hygiene andTropical Medicine, for example, haveconvinced the British Army to startusing a proven medication to treatblood-loss in its field hospitals. IanRoberts, professor of epidemiologyand public health, led a clinical studyinto the effectiveness of tranexamicacid – a ‘synthetic amino acid’ that iscommonly used in surgery to stemblood flow and reduce the need for ablood transfusion, and also used totreat women suffering with heavymenstrual periods.

Tranexamic acid works byinhibiting the enzyme plasmin, whichbreaks down blood clots. ‘That’susually a good thing, because it stopsclots forming where you don’t wantthem,’ says Roberts. ‘But it’s not goodwhen you’re bleeding to death.’ Sotranexamic acid promotes bloodclotting to stop the bleeding.

The clinical trial involved 20 000people, who were randomly assignedthe drug, or given a placebo.Receiving tranexamic acid within onehour helped to reduce the risk ofbleeding to death by 30%. This wasreduced to 20% if administered withinthe first three hours – but wasineffective if used any later. ‘It’s alwaysbetter to treat sooner rather than later,’says Roberts, adding, ‘The trialproduced a very strong result. I’ve

done clinical trials for 20 years, andnothing has gone from trial totreatment so quickly.’

Within two weeks of these resultsbeing published, the British Army hadintroduced tranexamic acid into fieldhospitals in Afghanistan – though theirUS colleagues were initially scepticaland refused to follow suit. ‘But therewas evidence that it was saving lives –those who received it were less likelyto die, and that convinced theAmericans to start using it,’ saysRoberts.

In a civilian spin-off, UK paramedicswill now start carrying – and using –tranexamic acid from April 2013.

Clot formationMeanwhile, US researchers, led byErin Lavik at Case Western ReserveUniversity in Ohio, have devised nano-sized polymer particles that bind toblood platelets, helping them to formclots more quickly. This has thepotential to slow down bleeding fromserious wounds – especially internalinjuries – and again keep injuredsoldiers alive while they are beingtransferred to surgery. A solution of thenanoparticles could be injected intothe patient on the battlefield.

The nanoparticle has three parts, allof which are in common medical use: apolymer core made from abiodegradable plastic (PLGA), whichis used for dissolvable sutures; aseries of ‘arms’ made frompolyethylene glycol (PEG); and, at theend of each arm, a tripeptide (RGD)comprising L-arginine, glycine and L-aspartic acid.

Any kind of blood loss – from apaper cut to a severed artery –activates the body’s repair mechanism.Platelets play an important factor inrepairing the wound by comingtogether and forming a clot. ‘We thinkthat the particle is speeding up theformation of initial clots,’ says Lavik.‘When they become active, plateletschange shape – and expose receptors,’says Lavik. ‘The peptide can now bindwith these receptors.’


Receivingtranexamic acidwithin one hourhelped to reducethe risk of bleedingto death by 30%.

The team has tested the strength ofthe ‘augmented’ platelets and foundthem to be equivalent to their ‘natural’counterparts. At the same time, theclots formed were as robust as anatural clot.

Lavik says that the nanoparticlestructure is very simple, although hepoints out that it has taken six years ofresearch to attain this simplicity. Oneimportant factor was getting the ‘armlength’ correct. ‘We spent a lot of timeon this,’ she says. ‘If they are too short,the peptide won’t stick to the

receptors. If they’re too long, the arms“fold over” and shield the peptidefrom the receptor: this reducesbinding, leading to slower clotting.’

Overall particle size is also of vitalimportance. Lavik explains: ‘If theparticle is too large, it could get stuckin the blood vessel, potentially leadingto a stroke or a heart attack.’ Lavikcomments that the lungs and brain aremost likely to be affected because thecritical blood vessels leading to themare smaller. ‘If you damage the liningof the blood vessel, it sends out signals

that will get platelets to form a clot,’ sheexplains.

The size of the particle is 200–300 nm in diameter, which is quite a lotsmaller than the 1–2 microns of aplatelet. Particles are cleared from thebody within 24 hours, she says.

So far, the experiments have beendone on rats, with larger animal testsjust beginning. However, the resultshave been very promising, Lavik says.Surviving the first hour of a lethal liverinjury increased from 47% (treatmentwith saline) to 80% (treatment with thenanoparticles). There was also someevidence that blood loss was slowed.

As ever, animal models are only astarting point for assessing thepotential benefit to humans. ‘One bigdifference between humans and rats ishaemodynamics,’ says Lavik. ‘Rats aretougher, and humans bleed faster. Weneed larger animal testing to see whatthe proposition in humans would be.’ Ifthis is successful, the next step ishuman testing, which she thinks is still5–10 years away.

Serious injury and violent deathcontinue to be a reality for the modernsoldier. While injuries like shrapneland bullet wounds are similar to thoseseen in the past, the ability to treatthem has improved vastly, allowingcasualties to be stabilised long enoughto evacuate them to a field hospital.

Lou Reade is a freelance science writer based inKent, UK.

First published in Chemistry&Industry, April2013 (www.soci.org/chemistryandindustry).Reproduced with permission.


Attacking hypothermiaBlood loss may be the leading cause of death for injured soldiers, buthypothermia can be a complicating factor. The usual treatment on the battlefieldis basic: intravenous fluids and a blanket. This can take up to 16 hours to stabilisea patient’s core body temperature.

Now, design students at Stevens Institute of Technology in New Jersey, US,have developed a prototype that could cut this recovery time to just four hours.The ‘Heat Wave’ delivers warm, humid air into the lungs via an oxygen mask. Itworks on the principle that all blood circulates through the lungs – so this wouldbe an ideal way of raising body temperature because heat transfer is highlydependent on maximising surface area. ‘The surface area of the alveoli – the tinyair sacs in the lungs that take in oxygen – is the same as that of a tennis court,’explains Vikki Hazelwood, professor of biomedical engineering at StevensInstitute.

The prototype incorporates a tiny humidifier and an electric motor. To date, ithas been used to pump air through an insulated container – simulating the lungs– which is connected to a second container that simulates the cardiovascularsystem. ‘Controlling the temperature is important, because you don’t want toscorch the lungs,’ says Hazelwood. Heat was transferred between the containersthrough a water-filled tube, which simulates convection between the lungs andthe bloodstream. Heat and humidity were recorded using sensors wired to a laptopcomputer.

While the prototype shows proof-of-concept, more work is needs to be donebefore the researchers can present it to investors for commercialisation.

Online indexesThe latest Chemistry in Australia indexes are now online.Browse or search our archived back issues from 2003onwards.

To view the latest indexes, visit www.raci.org.au/resourcecentre/further-information/indexes.

iStockphoto/Onur Döngel


Breath-taking

BY ANTON AMANN AND

AGAPIOS AGAPIOU

How to catcha chemicalsignature

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Breath analysis is a young fieldof research with old roots.Hippocrates (460–370 BCE,Kos, Greece) first described

fetor oris and fetor hepaticus in histreatise on breath aroma and disease.Much later, in 1782–83, AntoineLavoisier detected carbon dioxide inthe exhaled breath of guinea pigs andinterpreted this as a product ofcombustion. In 1898, Johannes Müllerperformed the first quantitativeinvestigations of acetone in exhaledbreath. In 1971, Linus Pauling showedthat more than 30 different volatileorganic compounds (VOCs) arecontained in breath. Another influentialstudy published by Simenhoff et al. in1977 showed that dimethylamine andtrimethylamine appear in the ‘uremicbreath’ of patients suffering from end-stage renal disease.

Since then, several hundreds ofdifferent VOCs have been detected inexhaled breath, with concentrationpatterns that may be used for medicaldiagnosis and therapeutic monitoring.

A particularly fascinating novelfocus is real-time analysis of exhaledbreath, even in breath-to-breathresolution. This can be done duringexertion on a stationary bicycle(bit.ly/1eIICcH) or during sleep(bit.ly/NsqQPH). Breath is collectedthrough a mask (pictured, p. 18) and

analysed in real-time by protontransfer reaction-mass spectrometry(PTR-MS). In parallel, different medicalparameters (ECG, oxygen saturation,blood pressure, cardiac output andalveolar minute volume) aredetermined. The correlation of vitalparameters with breath analysis isespecially useful in emergencyapplications such as in intensive careunits or when entombed victims aredetected but their rescue will takehours.

Abnormalities in the concentrationsof endogenous VOCs provide clues formedical disease diagnosis. One of themost prominent volatiles in exhaledbreath is isoprene (2-methyl-1,3-butadiene), a branched-chainunsaturated hydrocarbon that is part ofthe cholesterol biosynthetic pathway.Isoprene is stored in the periphery ofthe human body and released duringexercise. Its output increases by afactor of approximately 10 duringexertion. This increase in output isshown in the diagram on page 19,which depicts an experiment withmeasurement of isoprene, carbondioxide and acetone for a healthyvolunteer on a stationary bicycle(bit.ly/1eIICcH).

When measuring the baselineconcentration of isoprene in exhaledbreath of patients, the samplingprocedure is crucial. In clinical studies,volunteers and patients are asked to sitquietly for about 10 minutes so thattheir baseline concentrations ofexhaled isoprene, mainly produced inthe liver (not the increased isopreneconcentration in the muscles), can bemeasured. Isoprene shows a lowerconcentration in exhaled breath ofpatients with lung cancer


Breath analysis is a powerful andadaptable tool for medical diagnosis andtherapeutic monitoring.

Breath tests approved by the FDA Breath carbon dioxide test for capnography

Breath carbon monoxide test for neonatal jaundice (CO is produced by heme catabolism)

Breath hydrogen and methane tests to detect disaccharidase absorption deficiency,gastrointestinal transit time, bacterial overgrowth, intestinal status

Breath nitric oxide test for monitoring of asthma therapy

Breath test for detection of heart transplant rejection13C-urea breath test for detection of H. pylori infection

Breath ethanol test for blood alcohol (law enforcement)

(bit.ly/M4yuyH) or breast cancer, incomparison with healthy volunteers.The decrease of isoprene in breath oflung cancer patients correlates withthe activation of the immune system, asmeasured by the concentration ofneopterin in blood (bit.ly/1cnN0rB).

Standard clinical analysis often usesinvasive test procedures, but breathanalysis and breath tests are a non-invasive medical diagnostic tool. Theyare an easily applicable, cost-effectivealternative for detection, assessmentand treatment response. Breath analysiscan be performed continuously, andeven during surgery (bit.ly/NstZPq) orat an intensive care unit.

A different approach in breathanalysis is administration of specificprecursor compounds (e.g. 13C-dextromethorphan or valproate) topatients and volunteers, withsubsequent observation of ametabolite (e.g. 13CO2 or 3-heptanone)in exhaled breath. This allows thephenotype of enzyme activity to bemeasured and enzyme deficiencies(bit.ly/1iFcFks) or bacterial infection(e.g. by Helicobacter pylori) to bedetermined. The 13C-urea breath testfor gastric infection by H. pylori is oneof only a few breath tests approved bythe US Food and Drug Administrationor the European Medicines Agency

(see table, page 17 (Solga S. et al. inVolatile biomarkers: Non-invasivediagnosis in physiology and medicine,eds Amann A., Smith D., 2013, Elsevier,pp. 19–24)); it is the only FDA-approved breath test using13C-labelled precursor compounds.

Exogenous compounds and theirvolatile metabolites in exhaled breathmay also be valuable in assessingdiseases. VOCs from exogenoussources (for example, fromenvironmental exposure to jet fuel,from smoking or from ingestion of foodand of drugs) may reflect the exposurehistory of a specific person(bit.ly/1h3htD9).

In recent years, breath analysis hasbeen expanded beyond the traditionalexpected applications, covering,among others, the areas of exposure,hygiene and safety.

For analysis of volatiles, a variety ofdifferent analytical instruments is used,including gas chromatography–massspectrometry (GC-MS) and PTR-MSwith quadrupole and time-of-flightanalysers, various types of ion mobilityspectrometry (IMS) such as aspirationIMS (A-IMS), field-asymmetric IMS(FAIMS) and IMS coupled to amulticapillary column (MCC-IMS),selected ion flow tube–massspectrometry (SIFT-MS), electronicnoses and different types of sensors.These state-of-the-art analyticalinstruments are combined withdifferent preconcentration methods(e.g. solid phase microextraction(SPME), solid phase extraction (SPE)with thermodesorption (TD), needletrap devices (NTD)), so as to overcomethe low concentrations of breathbiomarkers. In addition, laserspectroscopy is used for the detectionof small molecules such as ethane,propane, methane, H2 and pentane,and is considered another promisingtool for real-time analysis of exhaledbreath. Moreover, infraredspectrometry is also used for thedetermination of the isotopic ratio13CO2/

12CO2 in exhaled breath forspecific breath tests (e.g. 13C-uracil


Experimental set-up for real-time analysis of exhaled breath duringexertion on a stationary bicycle© Anton Amann

Volatile analysis fields Human mouth hygiene (e.g. halitosis)

Human odour signature (analysis of breath or of skin emanations)

Physiology and medicine (e.g. cancer, diabetes, asthma, oxidative stress, liver kidney dialysis,ventilated intensive care unit patients, uremia)

Headspace analysis of cells and bacterial cultures

Human daily activities (e.g. real-time analysis of exhaled breath during cycling, sleeping)

Safety and security applications (e.g. alcoholmeter, detection of victims trapped under the debris of collapsed buildings after earthquakes, explosions and other catastrophes)

Forensic applications (e.g. drug abuse)

Exposure to xenobiotic volatiles (e.g. industrial/working/manufacturing exposure, contaminated water exposure, swimming in chlorinated water, post-anaesthesia units)

Non-human applications (e.g. livestock, animal welfare monitoring)

breath test, 13C-dextromethorphanbreath test, 13C-pantoprazol breathtest).

Another focus of volatiles analysis isrelated to compounds produced bybacteria and fungi in the airways or inthe intestines. For example, hydrogenand methane are produced by gutbacteria consuming, for example,fructose or lactose that is not absorbedor metabolised owing tomalabsorption or enzyme deficiency(e.g. lactase). Particularly interestingare compounds not normally observedin exhaled breath. These includehydrogen cyanide and ethyl 2-methylbutyrate produced byPseudomonas aeruginosa or 3-phenylfuran produced byStreptococcus pneumoniae.

Another promising application isthe field detection and identification ofhuman-origin volatile biomarker(s), assigns of life, which are released fromhuman tissues (skin, lungs) andbiological fluids (sweat, urine) underthe ruins of collapsed buildings. Thisapplication is modelled along the useof dogs in urban search and rescueoperations. The sniffer dogs haveexcellent olfactory real-timecapabilities but have short workingtimes (20–30 minutes) and requiretime-consuming training. Theselimitations can be overcome bydeveloping novel chemical methodsmimicking canine sniffing, which couldcomplement the dogs’ work. Theidentification of the chemical signs ofhuman presence is a challenging

research field because of the low VOCconcentrations and the dynamicbackground.

Breath analysis is still in its infancy,and more attention is now being givento the overall validation of analyticalfindings. Data quality assurance has anenormous impact on the field and haslaid the ground for elucidation of thebiochemical background of volatilebiomarkers. Particularly important isthe validated identification of GC-MSpeaks by spectral library identificationand comparison of retention times.Such validated identification has beenrecently performed in analysis ofexhaled breath and in headspaceanalysis (the analysis of the gas spaceabove the sample) of cell and bacterialcultures (bit.ly/1lUKWkE).

In addition to the wealth andimportance of information provided byVOCs, the parallel study of biggerbiomolecules (e.g. adenosine,isoprostanes, leukotrienes, peptidesand cytokines) through the analysis ofexhaled breath condensate offers aneven more complete picture of expiredair analysis. This is a challengingresearch area with numerous

biomedical applications. Analysis ofexhaled breath condensate is a non-invasive method that has greatpotential for the classification andquantification of airway inflammationassociated with various pulmonarydiseases, as well as for longitudinalstudies and for assessing the responseto pharmacological therapy.

The combination of breath analysiswith information and communicationtechnology progress reveals apromising future that will soon beexpanded and established through thedevelopment of handheld breath-analysers (e.g. embedded chemicalbreath-analysers in smart mobilephones). The development of portablebreath-analysers will be a realtechnological revolution for themedical community and will open newhorizons for remote medical diagnosis.

Anton Amann is at the Breath Research Institute,Leopold-Franzens University of Innsbruck, Dornbirn,and University Clinic for Anesthesia, Innsbruck MedicalUniversity, Innsbruck, Austria. Agapios Agapiou is atthe School of Chemical Engineering, National TechnicalUniversity of Athens, Field Analytical Chemistry andTechnology Unit, Athens, Greece.


Standard clinicalanalysis often usesinvasive testprocedures, butbreath analysis andbreath tests are anon-invasive medicaldiagnostic tool.

Output of isoprene (nmol/min), acetone (arbitrary units) and CO2 (L/min) for a healthy volunteer duringrest phases and exertion of an effort of 75watts on a stationary bicycle. Isoprene output through exhaledbreath may increase up to a factor about 10 during exertion, and the concentration in breath increasesup to a factor of about five. (Image from King J. et al. J. Breath Res. 2009, 3(2), 027006, doi10.1088/1752-7155/3/2/027006, reproduced by permission of IOP Publishing)

After its development in thelate 1950s (by Australianchemist Sir Alan Walsh),AAS was initially thought to

be largely interference free, and to acertain extent this is correct. Forabsorption by a metal to occur, it isnecessary to select a resonance line(transition from the ground state) foreach hollow cathode lamp, the samplecell (e.g. flame) to convert moleculesto the atomic state, and for thespectrometer to be adjusted to theprecise wavelength. Typical resonancelines are less than 0.002 nanometreswide and very few resonance lines forother elements are close enough tooverlap. Hence, AAS is very specific tothe element chosen, but it is notentirely free of interference.

The first type of error involves alkalielements that ionise readily at lowtemperatures. For example, theelement potassium gives low

absorption when the flametemperature is high. If the temperatureof the flame for the standards isdifferent from that of the samples, thena lower percentage of the elementpresent is in the ground state at thehigher temperature and results willhave a bias. This is easily corrected byadding an excess of caesium to bothstandards and samples; its ionisationpotential is lower, releasing electrons,ensuring all potassium remains in theground state. This process is looselyknown as radiation buffering.

For AAS to work, the analyte mustbe in the atomic state in the samplecell. Some high-temperature stablecompounds do exist and these causelow analysis results when aninterfering element is present. Thisoccurs for calcium when samplescontain aluminium, which forms atemperature-stable ceramiccompound. It is impractical to


AAS is generallyfree of interferencescommon to othermethods, but threeminor types dooccur.

Corrections for AAS

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accurately matrix match standards andsamples, but the error can beeliminated by adding an excess ofstrontium to all solutions. Strontium ischemically similar to but more reactivethan calcium and will preferentiallybond with all the aluminium and leavethe calcium in the atomic state foraccurate results. An alternative way isto change from air acetylene to thehigh-temperature nitrous oxideacetylene flame, ensuring completedecomposition of compounds.

The third type of error that canaffect AAS involves trace analysis insamples with a high matrixcomponent. For flames, only about 5%of the sample is vaporised todecompose compounds and thesensitivity is typically limited to theppm range. A 1000-fold improvementin sensitivity is achieved with graphitefurnace methods for the sample cell.Here, all of a small sample (10mL) isinjected into a graphite tube and athree-stage heating program is used toprogressively remove water (150°C),the matrix (1500°C) and then atomisethe analyte (2500°C). A trace ofabsorbance during the heating cyclegives three peaks. During the first twostages, compounds are evolved andthese invariably have broadabsorption bands that absorb at theresonance line wavelength. If they arenot removed completely before theelement of interest is vaporised, thenthe results are in error.

For assurance of accurate traceanalysis in complex matrices, a traceof the background absorption is alsoneeded. Two methods have beendeveloped. One uses hydrogen ordeuterium lamps that give out white

(or continuous) radiation near theregion of the resonance line. Then asystem of rotation mirrors flicks the twobeams alternatively through thesample. As the band pass for thespectrometer is typically onenanometre, this is 1000 times theinherent line width of the resonanceline and if the percentage absorbanceis equal for both beams, then anypeaks are interference only and thesample contains no detectable analyte.The second background method doesnot use a second lamp. This neatarrangement was developed by USanalytical chemists S.B. Smith and G.M.Hieftje and uses a specially excitedhollow cathode lamp. At high powerlevels, all hollow cathode lamps givelower sensitivity and if the lampcurrent is high enough, then resonancelines are totally self-absorbed. (Thiswas first noted in a spectral analysis ofsodium in the sun; its doublet gave twoblack bands.) With this backgrounddetection method, the analyteabsorption is detected during the low-current part of the cycle and thematrix absorbance during the high-current phase, using the immediatelyadjacent light in this broadened beam.

In an earlier article, a low-costthree-way spectrometer produced byIEC (Thornbury, Victoria) for teachingwas described (see August 2005 issue,pp. 3–6). The initial design used atomicspectral lamps (e.g. Na and K) as thelight sources for teaching AAS. Allschools teaching science weresupplied with these some 50 years agowhen spectroscopy methods werestarting to be used in industry.However, many schools in those daysdid not have these available, and anattempt to produce a source for Nawas made using a low-cost Na gardenlamp. As sold, this lamp gave nilatomic absorbance for sodium (likeSmith–Hieftje background light).However, I tested their prototype tosee if lower power could solve thisproblem. By adding a variabletransformer and plotting the outputspectrum at various power settings, we

were able to go from total self-absorption at the sodium doublet at240 volts to a well-defined doublet at110 volts. This lower voltage gaveadequate sensitivity for teaching AASusing sodium. IEC simply added adouble choke to the circuit andmarketed this lamp for school use.

This proved beneficial for manyschools as their distilled water was oftenstill too high in Na for good AAS graphs– the lower sensitivity of this lampminimised the problem of the highblank. In the full power mode, it candemonstrate how backgroundcorrection is achieved. In addition, itproved possible to analyse all salinelevels without dilution by merely settingthe appropriate voltage for the Na lamp.Compared to hollow cathode lamps,which can analyse sodium in the subppm range, the original sodium spectrallamps covered 0–10ppm and themodified sodium garden lamp was bestin the 10–100ppm range. Other powerlevels would allow analysis at higherlevels. Most water quality saline testmethods use conductivity, but this is notspecific to sodium.

Hollow cathode lamps do age withuse and volatile elements such assodium become depleted. Whenargon is the filler gas, two nearby lines(583 and 588 nanometres) thenpredominate and can be mistakenlyset. It becomes frustrating when noabsorption can be obtained. In thesecircumstances, acceptable results areobtained by narrowing thespectrometer band pass to0.1 nanometre and carefully scanningthe region – the proper sodiumdoublet is at 589.0 and589.6 nanometres in the ratio of 2:1 andfor an aged lamp once these areidentified, the photomultiplier gain isincreased to give normal calibrationgraphs. The 588 Ar line which is non-absorbing for Na could be used forbackground correction if needed.

Ray Hodges FRACI CChem([email protected]) is now retired but stilldoes consulting in alternative fuels and atomicspectroscopy.


Atomic absorption spectroscopy(AAS) was first developed for metallicelemental analysis and foundimmediate application for miningindustries. In medicine, AAS givesbetter sensitivity for magnesium, akey electrolyte in blood for heartrhythm, than other methods.

The near-desperation of manysmall businesses for funding,particularly in the earlystages of their business cycle,

was very clear at a series of events Iattended last year. The events’ aim wasto help small businesses identifypotential sources of governmentfunding relevant to their businesscircumstances and provide adviceabout approaching the applicationprocess. This juxtaposes with the viewI encounter at many larger, moreestablished businesses, whose attitudeto government grants is more typicallya roll of the eyes and a dismissive sigh.

Many companies that have beenaround for a while tend to look atgovernment grants as ‘marionettemoney’ – money with strings.

Why the difference in opinion? Atleast part of this is just experience. Itcan be quite true that for some grants,the time, paperwork and cost, both forapplying for the grant and thencomplying with the resulting reportingrequirements, can approach or evenexceed the value of the grant itself.This is particularly true of some of thesmaller grant amounts – where ‘small’is a subjective term that will vary frombusiness to business.

Even for the Federal R&D TaxIncentive, which is one of the morestraightforward programs and is anentitlement based on eligible R&Dactivity rather than a discretionarygrant, some companies choose not totake up their entitlements ‘because it isjust too much trouble’.

By contrast, I am ever the optimist.Sure, there are programs that Iprobably wouldn’t bother with, butwith more than 700 business grants (!)available at the federal, state and localgovernment levels, totalling well over$50 billion of budgeted governmentfunds annually for businesses, there isbound to be a program to suit almostevery business.

Currently, I concentrate on just threeprograms: the R&D Tax Incentive (upto 45% cash rebate for eligible R&Dexpenses), the Export MarketDevelopment Grant (EMDG) (a 50%cash rebate for eligible internationalmarketing expenses, capped at$150 000) and CommercialisationAustralia grants (‘CA grants’, up to$2 million of funding on a 1:1 basis). Aslegislated programs, these are morepredictable from year to year, and arenot subject to ministerial discretion.

To learn more about the other 697


Government grantsfor business arereadily available,but are they worththe trouble?

Marionettemoney

BY DAVE SAMMUT

programs (or more), I recommend oneof the subscription services or‘specialist grant gurus’ that maintainand continuously update accuratedatabases, and (for a fee) can assistwith selecting grants most appropriateto your business.

In describing the advantages ofgrants as a means of supportingbusiness, Craig Hunter of governmentgrant specialists Grant Ready notes,‘Grants are a useful means ofgovernment being able to implementeconomic policy at arm’s length at astate and federal level, and can beused to stimulate specific industrysectors’.

As an industry-oriented consultant,I’m not going to discuss the academicresearch grants such as the ARCgrants. They sound great, but I’m noexpert on them. I’m interested in andimpressed by the industry-orientedprograms.

Starting with the R&D Tax Incentive,there is support for companies todevelop new products, processes andservices, either alone or in conjunctionwith R&D providers (academicinstitutions, registered ResearchService Providers, or more generalcontractors).

The Commercialisation Australiagrants are intended to pick up oncethe R&D is basically ‘complete’ (albeitthat it may continue as ongoingproduct development) and to coverwhat AusIndustry describes as ‘the

valley of death’ between commercialreadiness and first sales.

The Export Market DevelopmentGrant can assist companies as theyseek to expand from the domestic tointernational markets, excluding NewZealand, Iran and North Korea. (I amcurrently doing an environmentalproject in Iran using new Australianchemical technology, with the full inputof the Department of Foreign Affairsand Trade. It has been an extremelypositive experience, and the people ofIran are delightful.)

Once a company is established andhas at least $1.5 million of turnover, theEnterprise Connect programs canassist companies to expand and grow.Together, that seems a prettycomprehensive sequence.

There is not space to do justice toall of these programs, but having had avery positive experience withEnterprise Connect’s Researchers inBusiness (RiB) program during the lastcouple of years, I will use thisopportunity for an introduction.

The RiB program offers up to$50 000 of research salary costs on a1:1 basis over a 2–12-month period. Itsaim is ‘to help break down the culturaldivide between business and the


… with more than700 businessgrants available atthe federal, stateand localgovernment levels,totalling well over$50 billion ofbudgetedgovernment fundsannually forbusinesses, thereis bound to be aprogram to suitalmost everybusiness.

iStockphoto/Kreatiw

research sector by speeding up thedistribution of knowledge andexpertise and accelerating theadoption of new ideas andtechnologies’.

From one point of view, the programsuffers from many of the sameproblems that limit the desirability of‘free’ government money. First, themaximum payment is sufficiently trivialthat most medium-sized and largerorganisations would find it hard toargue that without this funding theselected project would not go ahead.

Second, the list of eligibility criteriaruns to several pages (quite literally:see RIB_CIG.pdf atwww.enterpriseconnect.gov.au).Indeed, as someone who has workedhis entire career in the private sector. Ican’t help but raise a sardonic smilethat one of the criteria to exclude aproject from eligibility is that it‘involves an activity that would bemore effectively undertaken by aprivate sector organisation’ … not that

I would ever be ungenerous to myesteemed colleagues in academia.

Third, there is the reporting – aminimum of three reports over the lifeof the project, plus participation inpublished case studies (which may notsuit all businesses).

Last, and by a long margin not least,any cooperation between academiaand business faces the enormouschallenge of intellectual property (seebox).

Notwithstanding these limitations, Ihad a very good experience with thisprogram in 2011. On a particularlyserendipitous day, I was sitting at mydesk mulling over the solution to aproblem in a new technology programI had been developing. Breaking myconcentration, I received anunsolicited call from a representativeof the CSIRO asking ‘Do you have anyresearch that needs doing?’ ‘As amatter of fact, yes.’ Mr Jim Grigoriouquickly found me a very well-suitedresearcher through CSIRO Minerals in

Perth (Dr Chu Yong Cheng, workingfor Dr Dave Robinson – see November2013 issue, p. 24). Jim took care ofmost of the paperwork – with the RiBprogram supporting direct applicationby the research institution – and withquick approval on the funding both byEnterprise Connect and the company,we were ready to start in a matter ofweeks. The process was so fast thatour team had to scramble to preparethe process intermediates that were toform the feedstock to the researchproject!

Cheng and his team worked to apretty aggressive timetable, reportingregularly, and ultimately delivering asuccessful result. And while the largerproject temporarily ‘fell over’ thefollowing year due to factors beyondanyone’s control, the combinedtechnology from the company andCSIRO stands ready to apply. I will takea great deal of pleasure in taking thattechnology to market at the firstchance I get over the next few years.

The Enterprise Connect websitelists well over 100 RiB projectssuccessfully completed, with nearly 30more currently underway. It’s great tosee that the program seems to beworking, and it is proof positive thatthese programs can achieve theirintended outcomes.

I applaud the efforts of the hard-working representatives of our variousgovernments, who work tirelessly (andsometimes thanklessly) to support andencourage Australia to continue to bethe clever country.

While plenty of businesses canmanage just fine using their ownresources and revenues, for the rest ofus there are excellent avenues ofsupport, both small and large. Eitherway, I would encourage every businessto at least be aware of the support thatis available.

Dave Sammut MRACI CChem is Principal at DCSTechnical Pty Ltd. As an associate to Access RnD TaxSolutions, DCS Technical provides consulting serviceson the R&D Tax Incentive, EMDG andCommercialisation Australia grants.


IP: a hurdle between government and businessSponsoring an honours project, for example, is basically just a gift to a uni. Fewhonours projects will turn up anything interesting, let alone insightful. PhDsmight provide some novelty, but the time frames aren’t appropriate for mostcommercial needs, and the costs are no better than hiring an internal junior. Sothe anticipated commercial outcomes of such projects are limited at best, andmore typically negligible.

Yet time and again, when basically offering such a gift to a university out ofgoodwill, I have been stumped by the uni then demanding ownership of mycompany’s intellectual property (IP). It’s a nonsensical approach that shows littleunderstanding of the commercial world. After all, when a company pays anemployee or a contractor, the company retains the IP. Why would the situationchange when the money flows to an institution? Quite simply, it should not, andtime and again my proposed cooperation has fallen at this hurdle.

However, my experience with the RiB program was different. I had a particularidea that I wanted to explore, with a great opportunity to cooperate in itsdevelopment. Most of the IP was already in place, but there was just one piece ofthe puzzle yet to fit. And CSIRO came to the table. We were able to agree that thecompany would own all of the IP resulting from the project, with CSIRO retainingthe right to use the fruits of its own work for its future work.

At the December RACI NSW Consultants Group meeting, I was pleased to hearthat several institutions have been coming around in recent years to a morerealistic approach to IP, and I find this very encouraging.

To the other institutions, still holding out with ‘sticky fingers,’ I say, ‘He whopays the piper calls the tune’.


REGISTER NOW 24th Anniversary World Congress on Biosensors – topics include:Bioelectronics Commercial biosensors, manufacturing and markets DNA chips, nucleic acid sensors and aptasensors Enzyme-based biosensors Immunosensors Lab-on-a-chip Microfluidics and immobilisation technology Nanobiosensors, nanomaterials & nanoanalytical systems Natural & synthetic receptors Organism- and whole cell-based biosensors Printed biosensors and microfabrication Proteomics, single-cell analysis and cancer-cell detection Signal transduction technology Theranostics & implantable sensors

Congress chairAnthony P F Turner, Linköping University, Sweden

Plenary speakersFrank Caruso, University of Melbourne, AustraliaAndrew de Mello, ETH Zürich, SwitzerlandJ. Justin Gooding, University of New South Wales, AustraliaWolfgang Knoll, Austrian Institute of Technology, AustriaTanya Monro, University of Adelaide, AustraliaJoseph Wang, University of California, San Diego, USA

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The national awards recogniseand promote the contributionsand achievements of ourmembers.

The awards cover a broadrange of areas and are aimed atthe full membershipdemographics.

They are open to all membersof the RACI. Some can beapplied for by the candidate;others have to be nominated bythird parties.

• Leighton Memorial Award• H.G. Smith Memorial Award• Rennie Memorial Award• Cornforth Award• Masson Memorial Award• C.S. Piper Award• Applied Research Award• Distinguished Contribution to

Economic Advancement(Weickhardt) Award

• Fensham Award for OutstandingContribution to ChemicalEducation

• Pearson Education/RACIChemistry Educator of the YearAward

• Centenary of Federation –Primary and Secondary TeachingAward

• Citations – Contributions toChemistry & Chemical Profession

• Distinguished Fellowship Award

RACI National Awards

Full details of the awards andthe requirement criteria can befound at www.raci.org.au.

Stockphoto/grandeduc

I was born on 7 September 1917 at Sydney in Australia. My fatherwas English-born and a graduate of Oxford; my mother, born HildaEipper, was descended from a German minister of religion whosettled in New South Wales in 1832. I was the second of fourchildren.

Part of my childhood was spent in Sydney and part in ruralNew South Wales, at Armidale. When I was about ten years old,the first signs of deafness (from otosclerosis) becamenoticeable. The total loss of hearing was a process that lastedmore than a decade, but it was sufficiently gradual for me toattend Sydney Boys’ High School and to profit from theteaching there. In particular, a good young teacher, LeonardBasser, influenced me in the direction of chemistry; and thisseemed to offer a career where deafness might not be aninsuperable handicap.

I entered Sydney University at the age of 16, and though bythat time unable to hear any lecture, I was attracted bylaboratory work in organic chemistry (which I had done in animprovised laboratory at home since the age of 14) and by theavailability of the original chemical literature. In 1937, Igraduated with first-class honours and a University medal. Aftera year of postgraduate research I won an 1851 Exhibitionscholarship to work at Oxford with Robert Robinson. Two suchscholarships were awarded each year, and the other was won byRita Harradence, also of Sydney and also an organic chemist.This began an association which continues to this day. We weremarried in 1941, and have three children and twograndchildren.

War broke out as we journeyed to Oxford and after completingour work (on steroid synthesis) for doctorates we became part ofthe chemical effort on penicillin, which was the major chemicalproject in Robinson’s laboratory during the war. We madecontributions, and I helped to write The chemistry of penicillin(Princeton University Press, 1949), the record of a greatinternational effort. However, I had earlier discovered what wasto prove a key reaction for the synthesis of the sterols; and afterthe war I returned to this pursuit. The collaboration withRobinson continued after I joined (1946) the scientific staff ofthe Medical Research Council and worked at its NationalInstitute, first at Hampstead and then at Mill Hill. In the end(1951), we were able to complete, simultaneously withWoodward, the first total synthesis of the non-aromatic steroids.

At the National Institute for Medical Research, I came intocontact with biological scientists and formed collaborativeprojects with several of them. In particular, George Popják and Ishared an interest in cholesterol. At this time, Konrad Bloch wasbeginning his work on the biosynthesis of the sterols and Popjákand I began to concert experiments in which the disciplines of

chemistry and biochemistry could be applied to this subject. Wewere led to devise a complete carbon-by-carbon degradation ofthe 19-carbon ring structure of cholesterol and to identify, bymeans of radioactive tracers, the arrangement of the acetic acidmolecules from which the system is built. As knowledge of theintermediate stages became more complete, our experiments couldbe planned to give more and more information.

In 1962, Popják and I left the service of the MedicalResearch Council and became co-directors of the MilsteadLaboratory of Chemical Enzymology set up by Shell ResearchLtd. Lord Rothschild was influential in the decision to establishthis laboratory and I was his subordinate until he left Shell in1970. At Milstead, a project already conceived – the study ofthe stereochemistry of enzymic reactions by means ofasymmetry artificially introduced by isotopic substitution – wasdeveloped. It continued after 1968, when Popják left Milsteadto go to the University of California at Los Angeles, until 1975,when I left to take up my present position of Royal SocietyResearch Professor at the University of Sussex. In 1967, I hadformed a collaboration with Hermann Eggerer, then of München;and together we solved the problem of the ‘asymmetric methyl

26 April 2014

obituary

Sir John Cornforth (1917–2013), an autobiography

Nick Sinclair/Science Photo Library

We were led to devise acomplete carbon-by-carbondegradation of the 19-carbonring structure of cholesteroland to identify, by means ofradioactive tracers, thearrangement of the aceticacid molecules from whichthe system is built.

group’, and applied the solution in some of the many ways thathave proved possible.

My work has received ample recognition as it progressed: Iwas elected to the Royal Society in 1953; the Chemical Society

has awarded me its Corday Morgan medal (1953), Flintoff medal(1965), and Pedler (1968) and Robert Robinson (1971)lectureships; the American Chemical Society gave me its ErnestGuenther award (1968); and I received the Prix Roussel in1972. Popják and I were jointly awarded the BiochemicalSociety’s Ciba medal (1965); the Stouffer prize (1967); and theRoyal Society’s Davy Medal (1968).

Throughout my scientific career, my wife has been my mostconstant collaborator. Her experimental skill made majorcontributions to the work; she has eased for me beyond measurethe difficulties of communication that accompany deafness; herencouragement and fortitude have been my strongest supports.

Sir John died on 8 December 2013. His wife Rita passed away on 6 November 2012.

UNIVERSITY OF SYDNEY


‘Kappa’My first meeting with Kappa was in September 1978 when Iarrived in his labs at the University of Sussex. A year later,my study leave was over, but a close friendship continuedright up until the last few years.

I have memories of a tall and handsome man with agenerous and friendly smile, of a man with a wonderfulsense of humour, of a man of great humility, of a man ofextraordinary intellectual ability, and of a man whoaccepted my own family as part of his wide group of familyand friends.

I have memories of my son perched on Kappa’s shouldersso that the little boy had a better view of the Guy Fawkesprocession through Lewes in 1978. I have memories of mylittle daughter looking up in admiration at the elegantKappa on my property in the Blue Mountains: ‘Why wouldsuch a great man show such a keen interest in a little girl?’I wondered. Years later, I have memories of Kappadescribing his medal collection to another son: Nobel Prize,Davy Medal – more gold in a bunch of medals than I haveever cast eyes on – but at last he narrated: ‘And this is myfirst and most prized medal. It’s the University Medal fromthe University of Sydney.’

I have memories of playing scrabble, chess, ‘Take me’(chess in which the winner is he who loses all his piecesfirst), tennis. Kappa was determined to beat me in everyevent; of course, he succeeded, except in tennis – but thenI was half his age. ‘Why do you always hit balls straightback to me?’ he questioned (smilingly). We drank beers inthe Juggs Arms near Lewes. We wrote chemical,mathematical and sporting problems to each other ontablecloths, serviettes – whatever we could find.

Kappa loved to tell limericks, and jokes. Generally, jokeswere ... how should I put it ... rather intellectual.Somewhat off-putting was his intensive stare on completionof the joke – but then I realised he was lip-reading (yourlaughter)!

In the professional world, I learned from Kappa theimportance of being exact, and of questioning when indoubt. If Kappa didn’t totally understand something, hewould question you intently. This was never intimidating;the way of Kappa was a gentle, supportive and respectfulway.

Kappa’s greatness in chemistry and in science wasmatched by his greatness as a man. I was very privileged tohave known him as a friend.

Damon Ridley

Cornforth: a tribute Like so many Australian chemists of his generation, Sir JohnCornforth made his career in England. In 1975, Cornforthreceived the Nobel Prize in Chemistry, jointly with VladimirPrelog.

A centrally important fact about Cornforth is that, fromhis late teens, he was totally deaf. He therefore belongs tothat group of people who reached eminence and internationalstature while suffering from a serious disability. Others areBeethoven and John Oriel, a pioneering chemical engineer,who lost his eyesight through exposure to mustard gas butwent on to become a major influence in the formation of theInstitution of Chemical Engineers in the UK.

Cornforth was able to overcome the disability of hisdeafness through his marriage to another highly capableorganic chemist, Rita Harradence. She and John Cornforthwere approximate contemporaries as chemistry students atthe University of Sydney and obtained support to do theirPhDs in England. They travelled to England together for thatpurpose and were married in England in 1941.

To assert simply that Cornforth’s wife ‘helped him toovercome his disability’ would be but a shadow of the truth.Her being there would not have enabled him to overcome allthe problems due to his deafness. When I first heard ofCornforth a couple of years before his Nobel Prize, I was toldthat although Cornforth was obviously more than eligible fora university chair on any academic reckoning, his deafnesswould have made for difficulty in his occupancy of a chair inthe conventional sense because the incumbent would berequired to attend numerous meetings and hold conversationswith colleagues and outsiders. Rita’s support did not simplyconsist of her doing what John could not do for himself. Itwas at a much deeper level than that and was derived fromthe quality of their relationship. Happily, they each lived to avery good age, Rita predeceasing John by only one year.

Clifford Jones FRACI CChem

Establishing your research group as a young academic dependson many things, such as the availability of quality students,adequate lab space and a well-balanced teaching load. Arguablythe most important factor is the acquisition of funding for youractivities. Given that Australian Research Council (ARC) successrates are around 20% (for Discovery Projects), it is unlikely thata successful researcher can rely on ARC funding alone.Academics need a diversified funding strategy.

Whether this be internaluniversity funding initiatives,state government fundingschemes or strategiccollaborations with well-funded, more senioracademics, it is important forthe viability of your career tohave more than one source ofmoney. These varied sources offunding can provide a safetynet for your research, allowing you to continue to keep upproductivity in the event that any one route of funding driesup.

One way to diversify your research income, which also hasmany other benefits, is gaining funding from industry. Industry-linked research can be a source of substantial funds andprovides context and relevance for your research. Projects canbe in the form of ARC-linked funding (e.g. Linkage Projectscheme; matching funding from the ARC for industrially fundedprojects) or direct one-to-one industry projects.

But before we consider how to approach working withindustry, let’s look at why you might not want to. First, you liketo choose your own research direction. The idea ofsubcontracting out your time and skills to a third party (whowill tell you what to do) does not sound appealing. I wouldargue that your subdiscipline of chemistry, plus specific aspectsof your research infrastructure and academic network, have justas big a role to play in defining your research direction as yourdesire to chart your own trajectory. Working with industry isjust one additional driver for your research direction.

Second, you might be concerned that spending time doingindustrially linked research will produce outputs that are not

publishable, or are of lower perceived quality. While this may bea problem in some fields of science, it is rarely the case forchemistry. Publication is normally achievable with a slight delay(allowing for legal/technical review by your partner, orlodgement of provisional patents), and is often encouraged bypartners as it provides advertisement and credibility to thechemicals, materials and processes that they eventually want tosell.

The simplest and easiest way to begin working with industryis to become involved in existing industry projects. If you arelucky, there will be senior academics in your department whoalready work with industry, and are keen to encourage theiryounger colleagues to engage with industry. In this way, youcan experience industry-linked research with your ‘trainingwheels’ still on, and watch experienced academics handle themany complexities of the industry–academy relationship, suchas project management, accountability and responsibility,reporting and presenting skills, and most crucially, thedevelopment of trust between academic and industry partners.

However, for many younger researchers, this mentoringprocess may not be possible, and you have no prior industrycontacts. How do you start ‘from scratch’?

careers


Industry and research: cultivating a connection

Persuading industry to invest inresearch isn’t easy, but it makessense as part of a good fundingstrategy.

iStockphoto/fruttipics

Who can you help?If you don’t know which industry sector might be interested inyour research, then you have probably never written amanuscript introduction or grant application. We have all statedthe relevance and importance of our work, and connected it toindustry sector A, B or C. This is where you look when you wantto figure out which industry might be interested in workingwith you. Focus on your specific expertise, and where thisconnects with industrial processes or challenges.

How do you make contact?The best way to make contact is not by cold-calling companyreps. Start by doing some research that is relevant and willmake them interested in your work. You then need to makecontact with them in a neutral setting that encourages dialogueand interaction, i.e. at conferences that have industry andacademic attendees. This is where you pitch the quality andrelevance of your work in a forum that will allow you to speakto industry technical representatives. If your work sparksinterest, then you can start a relationship with the right peoplefrom the industry partner – the ones who will champion anypotential engagement from inside the industry partner.

What problems can you solve?Do not approach industry interactions as a way to get fundingfor your pet project. You are trying to solve their problems –not yours. Once you have made contact, the next step is to visitthe industry partner, or have them visit you. You can then givethem a full picture of your group’s capabilities and the kind ofscience you do. It is also when you do the most importantthing in the beginning of a new interaction: you listen to theirresearch problems. You can then link the two together: matchup industry problems with your group’s expertise. Use the visitto make explicit the potential for future interactions, and getagreement that you are a potential research provider to thecompany.

Do I get the money now?Don’t get ahead of yourself – there is still a long way to gobefore you get a funded research project. There are importantsteps to take before you can build enough trust for them toinvest financially. Also, at this stage, it is possible that youmay have won over the technical rep, but there will be acomplex path of internal company approvals (which will bedominated by business decision) that have to be followedbefore getting a funded project. It is important that you keepinteracting with the partner during the period immediately aftera successful visit to get sufficient momentum to pass throughall of these processes.

How do I keep their interest and build trust?The best way to allow the relationship to develop to the pointwhere they might fund you directly is to do some work probono. The interest you have built to this point will enable youto start a small research activity that extends from your initialpitch research, and uses materials and chemicals from yourpartner. Many chemical companies will be happy to providecommercially available material for a short investigation,sometimes with the requirement that you sign a non-disclosureagreement. You need to use this opportunity to impress themwith your ability to deliver accurate, timely results that have aconcrete impact. Once they see that you can deliver, you arethen in a position to propose a full project (based on thecreation of value for your industry partner), which will hopefullybe funded.

From that point onward, the industry interaction is yours touse or abuse. Working with industry requires more care andattention than the research you do for funded grants in termsof doing what you said you would do, but if you continue todeliver results that help them, you have a chance to grow theamount of funding, and the scale of the projects that youpursue for them. As you build the relationship, your industryinteractions will hopefully mature to the point where you canperform quite fundamental research, with aims and objectivesthat look to the future to address problems that will beimportant for your partner in five years rather than in sixmonths.

I have purposely focused on aspects of industry engagementthat should apply across many industry sectors. For sector-specific aspects, advice from your peers and mentors will beinvaluable, combined with some sound judgement and intuitionon your part. Good luck.

David Beattie MRACI CChem is Associate Research Professor and ARC FutureFellow at the Ian Wark Research Institute, University of South Australia.


Publication is normallyachievable with a slight delay… and is often encouragedby partners as it providesadvertisement and credibilityto the chemicals, materialsand processes that theyeventually want to sell.

books

REACH compliance: the great challenge forglobally actingenterprises Kamptmann S., Wiley, 2013, hardcover, 304 pp.,ISBN 9783527333165, $157.95

Susanne Kamptmann’s REACH compliance isaimed squarely at those assigned the

unenviable and thankless task of ensuring that their chemical-related business achieves its REACH obligations. The REACHregulation, Registration, Evaluation, Authorisation andRestriction of Chemicals commenced in 2006 with the intent ofensuring a high level of protection of human health and theenvironment and encouraging innovation and competitiveness.Chemical industry companies are responsible for demonstratingthe efficacy and safety of substances they place in the market.REACH applies within the European Economic Area (EEA), whichincludes all member states of the European Union (EU) plusNorway, Iceland and Liechtenstein. A new European Authority,the Helsinki-based European Chemicals Agency (ECHA) wascreated to administer REACH. How the Finns won oversight ofREACH is not articulated.

REACH as Kamptmann conveys is a lofty and ambitious pieceof legislation. It presently comprises 15 titles (e.g. Datasharing and avoidance of unnecessary testing) and 17 annexes(e.g. Standard information requirements for substancesmanufactured or imported in quantities of 10 tonnes or more)with each title split into several chapters and further intoarticles. To Kamptmann’s credit, she has managed to distil andexplore (albeit occasionally in a convoluted manner) the mostsalient parts of REACH over a mere 300 pages or so. Shearranges the text consistent with each part (letter) of REACH.Kamptmann describes the regulation’s fundamentals in intimatedetail, including at the end of each chapter a set of ‘self-help’questions and exercises, presumably aimed at the SMEs the textprimarily purports to assist. Recommended solutions areprovided in the book’s only appendix.

Beneficially, Kamptmann identifies potential and recognisedpitfalls that chemical and related companies should heed duringthe various stages of REACH. Most problems appear to arisefrom underestimating timelines and costs for registration, poorcommunication between supply chain participants andwrangling over cost sharing/recovery concerning substancedata. Kamptmann’s sample strategies and solutions that bothsatisfy REACH’s requirements and minimise business costs(optimise sales) often involve a fictional manufacturingbusiness in Switzerland with chemical sales in the EEA. Nodoubt she writes from professional experience as REACHmanager in a real company with a Swiss subsidiary.*

Briefly, REACH is about compiling and managing – in a verydeliberate and coordinated manner – a centrally governedrepository or library about the properties (including impacts onhuman health and the environment) of existing and newchemical substances used and produced particularly within theEEA. This dynamic library of ‘chemical intelligence’ in principleallows more informed, precise monitoring of chemical substancetraffic (volumes and movements), more opportunity for seamlesspeer-to-peer data sharing with less data duplication and moresystematic identification and elimination (or restricted use) of‘substances of very high concern’ (SVHC) – one of thelegislation’s key objectives.

REACH is also about legislative harmonisation, soKamptmann describes how it interacts with various EUdirectives and those directives it replaces. Presumably,legislative (and classification and labelling) harmonisation ishow competitiveness of the EEA’s chemical industry can beenhanced; greater competitiveness is another of REACH’s toutedobjectives. REACH’s evolution and track record are,unfortunately, only hinted at. How members of the EEA,especially their chemical industries, were convinced about themerits of and involved in the development of REACH would befascinating to know. So too would the plight of companiesendeavouring to comply with legislation now in its eighth year,in terms of various socio-economic and environmentalindicators. How many SVHC have been removed from themarketplace and substituted with a safer material? Somequantitative cost–benefit analysis would have also beenadvantageous for SME officers with REACH obligations.Admittedly these aspects were not the text’s primary concern,being as it is a ‘how to’ or guide book, but some furtherelaboration about the legislation’s operating history would haveassisted the text’s intended audience.

REACH defines the roles and responsibilities of all ‘actors’ inthe supply chain. Every EEA-located manufacturer or importerthat produces or introduces an amount of substance greaterthan one tonne per annum must register a suite of informationabout this substance by considering the substance’s whole-of-life uses, placements and impacts. Of course, there are a varietyof exclusions and exemptions from registration too, such as‘non-isolated intermediates’ consumed in house and ‘productand process oriented research and development’.

Registrants to be must initially create and submit aregistration ‘dossier’ (so much more chic than ‘file’ or ‘record’)when intending to register a new chemical substance or aninquiry dossier when searching the chemical ‘library’ toascertain if the agent is already (or in the process of being)registered.† Companies intending to register the samesubstance(s) are obliged to enter a ‘substance informationexchange forum’ (SIEF), with the aim of optimising datagathering (reducing duplication) and cost sharing. SIEF


*Tellingly, Kamptmann’s bio describes her employer as a generic ‘company’ with sites in Europe, Switzerland and Asia. A deliberate ploy to confound potentialcompetitors with REACH obligations?†A guiding principle of REACH is ‘one substance, one registration’.

members must also conduct deliberations with respect tocompetition law, a major friction point Kamptmann reveals.SIEF interactions is the part of REACH where costs can rapidlydwarf any fee that ECHA levels to register, evaluate, authoriseor generally uphold compliance.

It is in the data realm that REACH truly strains a company’sresources and patience. Data – its gathering, validation,storing, upkeep, control and trading – is the system’s prime andmost precious commodity. While REACH sets out basic data-sharing protocols and ECHA can intervene and exercise ‘remedialtools’ if necessary, how data access and sharing develops andproceeds is largely left to the individual players. This is where,as Kamptmann reveals, data holders can (and do) exhort ratheropen-ended fees from aspiring registrants for particularsubstance details (e.g. toxicology) and registration timelinescan blow out. One imagines that the competitiveness andinnovation of the EEA chemical industry is not best served byunreasonable data access and sharing demands. Kamptmann’sbest advice to avoid and minimise data disputes is to negotiateclear agreements (examples provided) between parties,particularly with respect to costs, timelines and responsibilities.

ECHA subjects dossiers to a battery of validation checks (the‘Evaluation’ process in REACH) including technical and financialcompleteness. ECHA issues substance registration numbers (andinvoices of course) to the businesses whose dossiers passmuster and ‘please explain’ notices to companies whose dossiersdon’t. This vetting process identifies SVHC, which arecandidates for banning unless a business can demonstrate thatthe substance has overwhelming socio-economic benefit or itsuse can be strictly controlled (the key criteria for substance‘Authorisation’). Another dossier is required for substancesidentified as SVHC. Each year, ECHA is obliged to audit no lessthan 5% of submitted registration dossiers in every tonnageband. At the end of 2013, ECHA had completed over 1100compliance checks of registration dossiers for substances in the‘greater than 100 tpa’ band. Of all evaluated dossiers in thisband, 69% were non-compliant (echa.europa.eu 28 January2013).

It’s a grand scheme, the success of which hinges on theinterplays between the various members of the (chemical)supply chain. REACH’s effective function relies heavily andintrinsically on the cooperation, trust and good will of multipleplayers, many of whom may be direct competitors. Kamptmannemphasises communication’s pivotal role in all effective,efficient REACH interactions by devoting an entire chapter tothis topic. There’s also a useful chapter dedicated to identifying

and applying the necessary processes in order to achieve REACHcompliance for a single enterprise.

Stylistically the text’s a very dry affair, clunky and oftencontaining sections where a point or procedure is mangled byoverwrought minutiae. One can avoid developing a throbbingheadache by judicious scanning; regulatory affairs officers withmore (vested) interest and REACH responsibilities will not beafforded this luxury. REACH is jargon laden and as aconsequence, this is reflected in Kamptmann’s book. This is notin itself an issue, but routinely an acronym would precede(often by several pages or in the case of ‘SIEF’, not at all) thecomplete term, which created quite a degree of frustration. Aconsidered glossary would have greatly assisted readability.

I found myself referring to the text in tandem with ECHA’sexcellent online content, especially in instances where I desiredfurther clarity. ECHA’s website hosts a wealth of extremelyuseful practical tools (e.g. IUCLID 5, REACH-IT) and information(e.g. fact sheets, guidance documents) to help businesses (andother REACH stakeholders) know and meet their REACHresponsibilities. It’s the primary interface between registrantsand ECHA in terms of dossier planning, preparation, submission,evaluation and reporting. Combined with Kamptmann’sinstructive text, ECHA’s website tools, information and advisoryservice grant potential REACH participants a better than evenchance of appreciating and fulfilling their considerable REACHobligations.

Damien Blackwell MRACI CChem


John Wiley & Sons books are now available to RACI members at a 25%discount. Log in to the members area of the RACI website, register onthe Wiley Landing Page, in the Members Benefits area, search andbuy. Your 25% discount will be applied to your purchase at the end ofthe process.

books

The elementsI recall the total fascination as a student absorbing the earlydevelopments of the periodic classification of the chemicalelements and the later experiments that gave rise to theparticulate structure of the atom. Little did I think that thesebeautiful constructs in logic would be reignited by a series ofrelatively new publications that are currently on the market.

The first of these is themagnificently illustrated Theelements by Theodore Gray,published in 2009 (ISBN139781579128142), which offersin colour a ‘mesmerisingphotographic display of the 118elements in the periodic table’(photos by Theodore Gray and NickMann), and is now available for$19.99 in paperback from someAustralia Post Offices near you. Thepublishers Black Dog and

Leventhal, New York, are to be commended on this visualexploration of the elements, which compares more than favourablywith the Periodic Table of Videos made by the University ofNottingham and driven excellently by Professor Martyn Poliakof.My grandson has remarked how this book helped him top hischemistry exams in high school.

A more recent book by Sam Keen has themost unlikely title The disappearing spoon, atleast for a book dedicated to the history ofthe elements and the characters behind theirdiscovery, and their logical placementthrough periodicity. This book was firstpublished in the US in 2010 by TransworldPublishers (Random House Group Company),and in the UK in 2011 as a Black Swanedition (ISBN 9780552777506). It probablyrates as one of the best written and, at times,totally enthralling books on science. Iparticularly like the description of theamateur scientist/tailor William Crookes, whobasically discovered selenium and thallium

and consequently was elected a member of the Royal Society. Henearly blew this prestige consequent to his protestations onspiritualism. The author winds this story into the theme of‘pathological science’ and neatly ties in the reactions in the 1980sto the discovery of high-temperature superconductors ‘as thephysics equivalent of finding the coelacanth’ for many; and shortlythereafter how this fervour led to a temporary suspension ofjudgement on the topic of ‘cold fusion’ that followed in 1989. Yetanother fascinating link is that drawn between Roentgen andCrookes in the former’s discovery of X-rays.

Finally, I draw attention to Professor Mario Markus’s Chemicalpoems – one on each element, published by Dos Madres Press,2013 (ISBN 9781933675985) in English. Markus has amultidisciplinary background and although retired as a physicist,he maintains a position at the Max Planck Institute for MolecularPhysiology in Dortmund, Germany. He appears to have venturedinto poetry as he had earlier in art when exploring human nature.According to his publisher: ‘Markus shows poets that chemistryprovides valuable lyrical material, which has rarely been used. Onthe other hand, the chemistry students can be made aware of thebeauty of poetry.’ The poems appear in sequence of atomic numberaccompanied by a facing page on the chemistry of the element. Inthe art world, Markus was one of the leaders of the ‘fractalist’movement and has produced some startling art works based onchaos theory. A quote from one of the poems seems appropriate. Ihave selected ‘Carbon’:

VirginalIt captures light,Is the hardest, the softestlubricant,Midwife of metals,hunter of poisons, ink or pencilof Portraits

Impure,It moves all life, propels machines.It’s the sinof breathing,of the loveof cars, It’s the dark essenceof things, plastics,perfumes.

Miraculous element,The former keeps the balance:it wipes out the guilt, if intact, and will not redeemif raped.

Speaking of poetry inevitably leads me to song, and I recall‘The Elements’, sung by Tom Lehrer, which was unique in its dayand continues to be available on CD and atwww.privatehand.com/flash/elements.html. However, we shouldnot forget the ‘New Periodic Table’ song available on YouTube byAsapScience, and sung in atomic number sequence to the tune ofOffenbach’s music for the Can-Can atwww.youtube.com/watch?v=1cqauZq4uYM.

Dr Alan J. Jones FRACI CChem


CHEMICAL POEMS: ONE ON EACH ELEMENT

MARIO MARKUS

The most popular model of how students learn is known as theconstructivist model of learning. There are variants of thismodel, but the main features are that learning occurs in thecontext of pre-existing experiences and ideas, that newconcepts are transformed to fit or build on those existing ideas,and that learning occurs in a social or cultural context.

Learners are not empty vessels into which new knowledgecan be injected. New concepts that are consistent with andextend pre-existing experiences and ideas are easily andeffectively assimilated. Learning is difficult when learners havepre-existing incorrect ideas or alternative conceptions, as theymust first unlearn the misconceptions in order to incorporatethe new information. Similarly, it is usually much harder andmore expensive to retrofit an existing house than to build fromscratch. It is also very hard to overcome bad habits. I havepreviously noted that we simplify ideas when teachingchemistry to younger students, but warned that over-simplification often results in misconceptions that will hinderfuture learning (July 2013, p. 35).

Most chemistry educators favour constructivism, becausethere are similarities with the process of discovery in science.First, the advancement of scientific knowledge builds on pastexperiences and knowledge: Isaac Newton famouslyacknowledged, ‘If I have seen further, it is by standing on theshoulders of giants’. Second, observations and data are notmeaningful until that information has been transformed toextend existing ideas: Nobel Laureate Lawrence Bragg wrote,‘The important thing in science is not so much to obtain newfacts as to discover new ways of thinking about them’.

It is harder for scientists and chemists to accept that thethird feature of constructivism, new ideas depend on social orcultural context, also mirrors the advancement of scientificknowledge. True, we recognise that student discussions aidsactive and effective learning, and that unguided discussionmight result in students negotiating conceptual understandingsthat are different from accepted scientific knowledge. However,we have an instinctive belief that scientific knowledge isassociated with universal truths, that matter has the sameproperties and chemical reactions will have similar outcomes,independent of context, and that true scientific understandingof those phenomena will be the same for all scientistseverywhere. If knowledge depends on social or cultural context,then scientists in different contexts may have differentunderstandings of the same things.

In the modern world, we have a sophisticated understandingof chemistry, from the quantum mechanical behaviour ofmolecules at the atomic and subatomic levels, to the propertiesof bulk materials. It is too easy to view chemistry, and sciencein general, as a fixed body of universally accepted knowledge.‘Accepted’ chemistry knowledge does depend on the social orcultural context. Consider the case of serial numbers imprintedin polymer surfaces: after these markings are erased by

abrasion, it is sometimes possible to visualise these erasedmarkings by chemical or heat treatment. Furthermore, it hasbeen observed that different solvents will recover erasedcharacters on different polymers. However, there is nouniversally agreed understanding in the published literature forhow or why solvents that successfully treat one polymer will notwork for another polymer; different communities of chemistsfavour different explanations.

Science as a Human Endeavour (SHE) is one of the strands inthe Australian Curriculum. Similarly, one of the learningoutcomes in the Draft Chemistry Academic Standards is thatgraduates will be able to recognise the creative endeavourinvolved in acquiring knowledge and to recognise the testableand contestable nature of chemistry. Science is practisedindividually and collectively by people. Human beings, whohave human virtues and fallibilities, are responsible forscientific advancements. New knowledge is constructed in theminds of learners and scientists. Just as discussions in workteams, workshops, conferences and the scientific literature helpscientists to extend and improve scientific understanding, theimportant role of teachers is to guide students to refine, alterand improve their scientific understanding when extending theirscientific boundaries.

education


Constructing knowledge

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uts (UK)

Kieran F. Lim ( ) FRACI CChem([email protected]) is an associate professor in the Schoolof Life and Environmental Sciences at Deakin University.

The SS Xantho steam engine presented the single biggestconservation problem I’ve had to solve. After 25 years ofconservation work, the engine was reassembled and is able tobe turned over after 112 years of immersion in seawater.

Beginning in 1982, with Neil North and visiting marinebiologist C.J. Beegle, we conducted the first integrated surveyof the physical, electrochemical and marine biologicalassessment of the historic iron shipwreck. As the workprogressed, we were to realise that the Xantho engine was theonly remaining example of the first mass-produced high-pressure marine steam engine.

The massive 5.5-tonne high-pressure marine steam enginewas built by John Penn of Greenwich, England, who had won aRoyal Navy contract to build a suite of horizontal trunk enginesfor gunboats in the Crimean War (1853–6). Penn’s genius was tosend out the work, making the component parts of iron andbronze at foundries in England, then coordinate the building ofthe engines in a very short time frame. The mass constructionalso saw the development of the world’s first standardised nutsand bolts – the Whitworth thread had been established.

The Xantho began its life as a Scottish ocean-going paddlesteamer that was refitted as a screw-driven vessel and sold toCharles Broadhurst, a colonial businessman who worked it invarious enterprises off the Western Australian coast until shewas wrecked off Port Gregory, Western Australia, in 1872. At

that time she was carrying a cargo of galena (PbS) fromAustralia’s first commercially viable Geraldine lead mine in thebed of the Murchison River. The bronze plate was cathodicallyprotected by the cast iron valve chest to which it was attached.Penn’s engineering works went on to produce the giant trunkengines for HMS Warrior, which kept the French at bay for morethan 30 years.

The Xantho engine had all the bronze and other fittingsstamped ‘56.30’ with the first numbers apparently denoting theyear of assembly and the 30 denoting the 30th engine producedin that year. Records show that our engine was assembled in1861.

The physical, electrochemical and marine biological survey ofthe wreck before excavation established the benchmark for theeffective management of the historic resources tied up in theiron steamship wrecks around the Australian coast. The wrecksite also records the first application of sacrificial anodes to thetask of in-situ preservation of iron wrecks and objects such ascannon and anchors (see box).

I spent a lot of my time in the first seven years and less inthe following 14 years treating the engine but in the process wehave learned a lot and written about our successes and failuresto ensure that others with similar problems do not make thesame mistakes. Thus, the team working in US on the USSMonitor engine, condenser and turret are having success after


Afterlife of a Scottish steamship

conservation

SS Xantho water colour (Ian Warne) Maritime Archaeological Association of Western Australia


success thanks to our advice and engagement. We havedeveloped similar close relationships with the team working onthe US colonial submarine HL Hunley, which sank the USSHousatonic in 1864 and so became the first submarine to sinkan enemy warship.

Reconstruction of the engine room is presently under wayand the quite remarkable story can be found by searchingXantho on the WA Museum website at www.museum.wa.gov.au.Without the commitment of Geoff Kimpton, Michael McCarthyand my conservation colleagues Richard Garcia, Jon Carpenterand Alex Kilpa (who have done most of the hands-onconservation in more recent years), the present exhibitionwould not have been possible.

SS Xantho’s bronze makers’plate, found to be in excellentcondition

The mass construction alsosaw the development of theworld’s first standardisednuts and bolts – theWhitworth thread had beenestablished.

Ian D. MacLeod FRACI CChem is Executive Director, FremantleMuseums & Maritime Heritage, Western Australian MaritimeMuseum, Fremantle, Western Australia.

Corrosion and reconstructionBefore excavation of the Xantho, the conservation teamput anodes on the engine with the view to stoppingcorrosion in its tracks and ensuring that it would still bein a reasonable state even if recovery took years (which itdid) because of funding issues. Geoff Kimpton used athermal lance to cut the bearers of the engine free andlower the object onto a steel sled supported under theengine with air bags.

The whole assembly was dragged up and along thebeach and craned onto a truck. The 7.5-tonne object wasdriven 500 kilometres to the conservation laboratory inFremantle. Over the next 2.5 years, more than 2.5 tonnesof concretion and corrosion products were removed fromthe engine by hand. During the times when it was notbeing worked on, it was stored in a sodium hydroxidesolution to passivate the iron and keep chlorides comingout by hydrolysis of iron corrosion products.

After deconcretion was completed, we began DCelectrolysis of the engine and I monitored the solutionsand the voltage and the chloride levels. Imagine mychagrin and dismay when checks on a steam pump, whichwas opened to see what was inside it, showed that theflanges were virtually unchanged in chloride levels afterfour years of treatment. This meant that every flange andsealed joint was likely to be harbouring large amounts ofchloride, still more than 1.5 times the salinity of theseawater, so we decided to undo the whole engine andseparate every component.

This was very hard work but eventually we succeededthanks to Richard Garcia developing his now famous flamedeconcreting method – heating up the nuts and boltswith an oxy-acetylene flame caused the concretions toglow red hot and then pop off with steam pressure as ironcorrosion products changed phases and becamedehydrated. Very clever! This separation work took upanother seven years, and then the slow process oftreating hundreds of components and reconstructingdamaged bits of totally graphitised cast iron began.

cholesterol

Many of us may spend a large fraction of our time and moneymaking sure that we don’t die ‘before our time’ – a basic humanmotivation that has spawned a massive health and medicalindustry. One class of drugs, the statins, generates approximately$29billion per annum in global revenues for the pharmaceuticalindustry despite controversy about their use and effectiveness.

The hypothesis behind statin use seems simple: highcholesterol in blood is correlated to heart disease, a major causeof poor health and early death in many developed countries; iftaken regularly, statins lower the measured cholesterol in blood.Therefore, if your blood cholesterol is greater than a certainconcentration, then your general practitioner may advise you totake statins.

But does this hypothesis bear scrutiny? When I was younger,my cholesterol readings were just fine and then they suddenly‘went up’ around the time I turned 40. What had changed? Was itmy diet, an effect of ageing, or both? Examining my mildlyelevated cholesterol results, my general practitioner advised me tostart taking statins.

Being awful at pill-taking routines, I admit I was looking forreasons not to take the statins. Fortunately, having done a periodof industrial R&D into blood glucose, I had a head-start. Also,around that time I read Ben Goldacre’s book Bad science, whichconvinced me that my scepticism of the processes used by thepharmaceutical industry to get drugs approved and marketed waswarranted.

Statins are prescribed to patients with high levels of the ‘bad’LDL particles in their blood (see box) because over time, thesepatients may suffer from atherosclerosis (which is just one form ofarteriosclerosis). In this process, the LDL particles that are able toget behind the small layer of cells that lines the walls of bloodvessels get stuck and their molecular contents slowly oxidise. Ifthese are not removed by HDL particles, then this can trigger animmune response; first, the immune system sends specialisedwhite blood cells (macrophages and T-lymphocytes) to absorb theoxidised molecules, forming specialised ‘foam’ cells to absorb theoxidised lipid molecules. These foam cells can grow and thenrupture, depositing a greater amount of oxidised lipid moleculesinto the artery wall, causing lesions. This triggers more whiteblood cells, thus continuing the cycle. Eventually, the arterybecomes inflamed. The ‘cholesterol’ plaque causes the muscle cellsto enlarge and form a hard cover over the affected area. This hardcover narrows the arteries, reducing blood flow and increasingblood pressure. This process shifts to an unfavourable steady stateequilibrium if there are insufficient HDL particles (relative to thenumber of LDL particles) to remove cholesterol and other lipidsfrom the arterial walls (before the damage is done) and carry themback to the liver.

A key cause of elevated levels of the too-small LDL particles is‘trans fat’ – unsaturated long-chain hydrocarbons, typically with atleast one unsaturated bond (the trans-isomer) and a carboxylicacid group at one end. Trans fats occur during the processing of

vegetable oils (e.g. oleic acid) into polyunsaturated fats for foodproduction. This process occurs by high-pressure catalysedhydrogenation, which only partially hydrogenates the doublebonds. The primary benefit of this process is to turn cheap liquidoil into a higher melting point fat; unfortunately in the processthe residual cis-isomers around the double bonds are converted totrans-isomers. In nature, cis-isomers dominate and trans-isomerfats are less common; we pretty much evolved without high levelsof them, and especially without partially hydrogenatedunsaturated trans fats.

The liver reacts to ingested trans fats by altering the types ofLDL particles that it pumps out. Specifically in response to transfats, the LDL particles become about 10% smaller and they alsohave a different composition (by percentage composition and notmolecule type) from those expressed under a more natural diet.Often, there are also more LDL particles in response to a fixedcalorific intake when comparing unnatural and natural fats(possibly because of the smaller size of particles in the formercase) and this may tip a system into net lipid deposition inarterial walls. This change in LDL particle expression in responseto unnatural fats is not well understood, but is likely to beaffected by multiple mechanisms whose expression may vary fromperson to person. Unfortunately, the level of HDL particles thatclean up after the impact of excessive number of LDL particlesisn’t changed as much by the ingestion of trans fats. Over time,with excessive consumption of trans fats, the increased relativeconcentration of smaller LDL particles and the unfavourableimbalance between LDL and HDL particles can lead toatherosclerosis.

The problem is that trans fats are the cheapest fats availableand are therefore almost ubiquitous in processed and pre-preparedfoods. Avoiding them can be very difficult and costly. The use ofstatins may represent an easier or more effective (depending onyour disposition) alternative in the instance that their continuedingestion leads to high blood cholesterol.

However, statins also interfere with complex biochemicalpathways via mechanisms that are only partially understood. Thelikelihood of unwanted side effects is almost inevitable. The mostcommon side effects of statins are (surprise, surprise) raised liverenzymes and liver damage, and muscle problems.

High levels of triglycerides in the bloodstream have also beenlinked to atherosclerosis and, by extension, the risk of heartdisease and stroke. This risk is not well understood but isdemonstrated by a strong inverse relationship between triglyceridelevels and the good HDL particle concentrations. Although theycan be directly consumed, triglycerides are also synthesised in theliver and represent one of the key fats for storing excess ingestedfood energy. In order to keep triglyceride levels down, a diet hasto be low in refined carbohydrates (including sugars), yet anotherfood component that is hard to dodge in the modern diet.

More recently, trans fats have started being replaced with otherfats, such as the so-called inter-esterified fats. Natural


Blood cholesterol – a chemist’s perspective I

triglycerides contain a mixture of saturated, monounsaturated andpolyunsaturated fatty acid monomers on the glycerol backbone.Inter-esterification is carried out by catalytically rearrangingunsaturated bonds across the three fatty acids monomers. Thisdecreases the melting point of the triglycerides significantly andmakes them useful in the manufacture of processed foods.However, studies have shown that these unnatural inter-esterifiedfats usually do not reduce the as-measured blood cholesterol andit would be a fair assumption that there is no free lunch with anyunnatural fat.

Does everyone with elevated bad LDL particles in their bloodend up with atherosclerosis, and those with high HDL levelsnot? Not according to a major meta-study (a statistical analysisof many clinical trials) that claims that lowering measuredcholesterol concentrations does not reduce mortality and isunlikely to prevent coronary heart disease. (Br. Med. J. 1992,vol. 305(6844), pp. 15–19.) This meta-study also concludedthat claims of the opposite are based on preferential citation ofsupportive trials. Of course, there have been many studies, andmany meta-studies combining other studies, and there is muchcontroversy in the interpretation of all these results. It shouldbe noted that some of the highest profile supporting articles inthe area are based on biochemical (and largely non-kinetic)insight (e.g. Nature Medicine, vol. 8(11), pp. 1211–17) and notupon clinical trial results. The fundamental issue that remains,and the reason the use of statins is controversial in somequarters, is that statins act to reduce the as-measured value ofjust one marker, which correlates to the disease of interest insome people under certain conditions; and yet this approachstill has conflicting clinical value and negative side effects.

One issue with the dominance of statins to treat peopledeemed at risk of atherosclerosis is that other approaches totreating the disease are not being properly promoted. Forexample, it might be far more effective to measure the initiationof arterial lesions as a risk factor. We might all be well advised todo fasting and non-fasting cholesterol profiling to see if ourindividual peak risk factors after eating are worryingly high,independent of the baseline fasting value. Another issue is thatmany people are possibly suffering the side effects of statins quiteunnecessarily, especially if they have not been tested to have afamilial deficiency in their LDL lipoprotein receptor.

The evidence that some people can live quite happily withhigh levels of measured LDL cholesterol, or even high ratios ofLDL to HDL cholesterol, in their blood suggest that themechanisms for atherosclerosis are quite complex and possiblypeculiar to individual diets, lifestyles and genetic make-up. Thisresult might also be partially interpreted by the over-simplifiedand error-prone techniques for measuring blood ‘cholesterol’components, which I will discuss next month.


Ian A. Maxwell ([email protected]) is a serial (andsometimes parallel) entrepreneur, venture capitalist and AdjunctProfessor in Electrical and Computer Engineering at RMITUniversity, who started out his career as a physical polymerchemist.

The good, the bad and the proxyThe measurement for blood ‘cholesterol’ level is (sort of) ameasure of the concentration of the molecular cholesterolin various fractions of blood (more on this next month),and this is a proxy for a measure of the concentration (orparticle number) of small colloidal lipoprotein particles.From a colloid chemist’s perspective, these particles aremicelles or unilamellar vesicles, swollen with lipidmolecules and thermodynamically stabilised by the presenceof large protein molecules. Broadly speaking, there are fivecategories of lipid particles in human blood. I will focus onjust two, the larger and lower density lipoproteins (LDL)particles and the smaller and higher density lipoproteins(HDL) particles. They differ in their function in the body,their size and density, their active proteins and enzymes,and the relative percentages of the various constituent lipidmolecules.

Each LDL particle has a hydrophobic core regionconsisting of polyunsaturated fatty acids, many proteinmolecules, enzymes, hundreds to thousands of esterifiedcholesterol molecules, varying numbers of triglycerides andother fats. This hydrophobic core is surrounded by a morehydrophilic shell of phospholipid surfactant molecules andunesterified cholesterol acting as a co-surfactant, as well asa protein receptor. LDL particles are approximately22 nanometres in diameter. HDL particles have differentbinding proteins and more of their mass is made up ofphospholipid surfactant molecules and they are smaller(diameter 7–12 nanometres).

The principal role of LDL particles is to transporttriglycerides ‘forward’ as a source of fatty acids from theintestines or liver to the peripheral tissues. In contrast, theHDL particles remove excess cholesterol from peripheraltissues and deliver it to the liver for excretion in bile in theform of bile acids, and these get larger as they absorbcholesterol. While these functions are often consideredseparately, these processes are highly complex and inter-related, and they involve transfer of protein receptors,enzymes and lipid molecules.

An LDL lipoprotein receptor that is found in allnucleated cells, but mainly in the liver, acts to enable theremoval by liver cells of approximately 70% of all excessLDL particles from blood circulation. The LDL receptorsallow LDL particles to be bound and internalised in theliver, a process known as endocytosis. This receptor isdeficient in many patients with familial heart disease.Statins, which are HMG-CoA reductase molecules, effectivelyattenuate the generation of LDL particles in the liver andhence, in order to redress the imbalance, promote theremoval of excess LDL particles from the blood. Thispartially overcomes, in some people, the deficiency in LDLlipoprotein receptors.

environment


By the time this article is published in April 2014, it is likelythat the southern Australian heatwave of mid-January and earlyFebruary will be just a memory. The Bureau of Meteorologydescribed the heatwave in January as one of the mostsignificant on record. Using some local examples and personalobservations, I’ll discuss what the various responses to theheatwave might say about government and communitypreparedness for dealing with the effects of climate changealready with us. This is distinct from what we might do as anation to mitigate the long-term effects (typically a 30–100-year time frame) of a changing climate.

High on the minds of many Melbournians in January was theimpact of the high temperatures on the Australian Open tennis,the first week of which coincided with the most extremetemperatures. In 2013, it was the second week. That thechampionship was moved to this time of year as recently as1988 suggests that extreme January temperatures in Melbourneweren’t considered likely when that decision was made. Theexperience of the 1980s, and probably decades before that, wasthat February was the month when temperatures in Melbournewould be highest. This year and last, the radio airwaves wereoccupied with commentary about the implementation of thetennis organisers’ extreme heat policy, and the now-regularadvocacy of moving the Open to later in the year. What seemedto pass without comment was the nightly TV advertisement forthe Open’s wine sponsor. Its ‘Cool Harvest’ range of whites wasbeing picked ‘right now in the cool of the evening’. In fact, onmany nights when that advertisement went to air around 10 pm,the temperature in Melbourne was 28°C, about what you’dexpect on a warm summer’s day. This suggests to me that it isnot only the organisers of sporting events who need to thinkabout how they react to more frequent occurrences of hightemperatures.

Geoff Scollary is better placed than me to comment on theeffect of shorter, more intense ripening periods for grapes, butit does seem to me that some wine styles and products to whichwe have grown accustomed may not be so readily available in ahotter future. Viticulturists and vignerons are not the onlygroup of plant growers likely affected. Anecdotally, thestrawberry season in southern Victoria has not been good thisyear, and radio talkback gardening experts suggest that it is nolonger worthwhile trying to grow silver birch trees in Victoria.

After the tennis, our minds turned to the threat of bushfires.While residents were exhorted to prepare and implement theirbushfire plans, experts in forestry and the science of bushfireswere opining that more preparation was needed before thebushfire season started. High on the agenda was an emphasis

on more fuel reduction burning, notably in National Parks andState forests. However, with governments at all levels preachingfiscal restraint, budget cutbacks that don’t target front lineservices frequently mean that long-term management, such asfuel reduction burning, is pushed back to another time. Alsocomplicating matters in this instance is the debate aboutwhether fuel reduction burning has a positive environmentalimpact. Anecdotally, the Aboriginal communities of pre-European settlement managed the landscape by periodic ‘cool’burning. However, the reliance on oral tradition and culturalheritage to pass on this knowledge, and the lack ofdocumentary evidence in the Western tradition, means that thispre-existing knowledge is perhaps given less weight in thedebate about public land management. Close to home, I seethis first hand where the grass on creek-side walking and biketracks is almost waist high. A swathe of less than a metre hasbeen cut either side, mostly to ensure that snakes crossing thepath are visible to users before they (the snakes) reach thepaved surface. While Melbourne water users are billed an AnnualParks Charge, the funds raised aren’t applied to management ofmost creek-side reserves, which is the responsibility of localcouncils.

The effect of the heat was also seen on other essentialservices. Hospitals were advised to expect more admissions, andthe ambulance service reported a marked increase in calls torespond to cardiac arrests. This was happening during what wasregarded as the holiday period, when many workers were ontheir summer break. Normally, non-essential hospital serviceswould not be expected to be available at this time, as hospitalstaff also took leave. I have heard nothing to suggest thatthere was an impact on service delivery during the hot weather,but it may be a significant factor in future planning to dealwith extreme weather.

So, regardless of whether a price on carbon dioxideemissions or direct government payments to emitters will bemore effective at reducing emission, it seems pretty clear thatthere has been some change in the climate in the past 30 years,whether due to natural or anthropogenic effects. The immediateconcern is how we cope with the degree of change now evident.How well governments, communities, industries and privatecitizens adapt, now, may be an indicator of how we adapt tolonger term climate changes.

Returning the serve from the weather

Paul Moritz MRACI CChem ([email protected]) isa Principal with Douglas Partners, and an EPA-appointedEnvironmental Auditor in Victoria. Preparation of this article wasalmost delayed by a bushfire emergency.

Oak vessels have been used in winemaking for at least2000 years, although the focus on the introduction of oakcharacters in wine perhaps commenced in the US in the 1960sand was taken up with great gusto by the Australian industryfrom the 1970s onwards. Oak vessels may be used infermentation, for maturation of a wine and for extraction of oakflavours. Barrels include barriques (225–228 litres), puncheons(318 litres) and hogsheads (238 litres), while a port pipe is500 litres. Oak casks, or foudres, vary between about 2000 and12 000 litres. I prefer to use foudre, as ‘cask’ is also used todescribe a bag-in-box container. And there is the cuvetronconique of 6000–7000 litres. A foudre is positionedhorizontally, while a cuve tronconique (sawn-off cone) standsupright with a removal lid.

White wine fermentation is possible in barrels and a morerobust wine style is the outcome. It is not unusual in Australiafor a Chardonnay blend to include a component of barrel-fermented wine. The approach also works for Sauvignon Blanc,Viognier and Sémillon. The temperature is best maintainedbetween 15°C and 18°C, so the ferment may takes two weeks tocomplete. Maturation on yeast lees is most easily performedfollowing barrel fermentation.

With red wines, removing the skins and seeds through thebarrel bung hole presents a major challenge. However, a pressedred wine with the skins and seeds removed and with someresidual sugar can be allowed to complete its fermentation inbarrel. In a cuve tronconique, fermentation on skins can beachieved just as easily as in a stainless steel vessel. At the endof the fermentation, the lid can be put in place for up to threeweeks of post-fermentation maceration or immediatelytransferred to the press to separate the wine from skins andseeds.

Wines can be matured in oak for up to 12months or morepost-fermentation. Oak vessels are composed of staves and thegap between the staves allows air ingress that in turn gives riseto slow oxidation processes. On the other hand, loss of somearoma compounds from the wine to the exterior is possible,although attempts to quantify this have not been successful.Storage conditions including temperature and humidity arecritical, as evaporative losses can be significant. Barrels must bechecked continuously and topped up when required, as an air gap(ullage) can lead to the growth of spoilage yeasts and bacteria.

The maturation or elevation in oak vessels may involve theextraction of oak characters or simply the development orrounding of the palate structure. The extent of oak extractiondepends on the age of the barrel, decreasing each time thebarrel is used; this will be the subject of my next column. Olderbarrels and foudres can be used for wine development withoutimparting oak aroma characters.

Maturing wine on yeast lees is not new: the earliest accountthat I have seen is in the Book of Isaiah. Essentially, at the endof the fermentation, the wine is left in barrel on lees. This

works well with Chardonnay, although my favourite is MuscadetSevre-et-Maine made from Melon de Bourgogne in the westernLoire region of France. Stirring or bâtonnage is used during thesur lie period to distribute the yeast lees. Minimising air ingressduring stirring is a challenge.

My fascination with Riesling and Pinot Gris led me severalyears ago to explore the wines of Alsace. The image shown hereis of the foudres in the cellars at Domaines-Schlumberger where,after fermentation, the wines are taken off gross lees and thenreturned to the foudres on fine lees for eight or so months. Toensure that there are no oak characters in the wines, the foudresare over 100 years old. The wines show an amazing richness anddepth of palate structure. I still have some 2004 and 2008 winesthat may not last much longer once I finish this article.


Oak in winemaking

Cuve tronconique

Foudres

Segu

in M

orea

u

Domaines-Schlumberger

grapevine

Geoffrey R. Scollary FRACI CChem ([email protected])was the foundation professor of oenology at Charles SturtUniversity and foundation director of the National Wine andGrape Industry Centre. He continues his wine research at theUniversity of Melbourne and Charles Sturt University.

bioindustry

I didn’t bat an eyelid when my friend announced that her dogwas having cataract surgery. It’s not at all unusual these daysto know of someone who has spent tens of thousands of dollarson their dog. I don’t mean over the course of the dog’s life, butto address an acute or chronic condition such as kidney diseaseor orthopaedic challenges. Once our primary concern with thefamily dog or cat was viral, bacterial and parasitic infections;now we are requesting and buying treatments for the onset ofage-related chronic conditions.

Companion animals are more than pets – they are now moreoften regarded as an integral family member and thereforesubject to a high degree of attention and investment, bothemotional and physical. This combination of factors has createda very attractive opportunity for biotechnology. A growingmarket, faster drug development times, fewer regulatoryhurdles, existing animal data in early phase clinical studies anda roadmap for short and mid-term revenues make this sector anattractive play for biotech.

We are spending more on our pets than ever before. Theanimal health market is $22.8 billion in total, 41% of which isspent on companion animals.

The billion dollar worldwide animal therapeutics anddiagnostics market is undoubtedly helping to boost biotechindustry revenues by a robust average annual rate of 7.9%through 2016, to an estimated $11 billion, according to aJanuary 2012 report from market research firm IBISWorld.

This considerable market growth is due to the changing roleof the companion animal over the last decade. Pet owners todayare demanding better care and access to cutting-edgetechnologies and services for their animals. Pharmaceutical,food and biotech companies are hearing the call. It is onlysince relatively recently that we can access veterinaryspecialists – oncologists, ophthalmologists, orthopaedicsurgeons – once the domain of professional breeders and showanimals.

Another reason for growth in the companion animal marketmay have to do with improved nutrition. As a result of high-quality pet nutrition products, vaccinations and quality ofveterinary care, our animals are living longer, and they havedifferent health needs related to ageing over longer periods oftime.

Biotech companies are turning to the companion animalmarket early in product development – reversing the traditionalroute by which new drugs are approved first in humans and thenlater applied to animals.

Animal clinical trials can be faster and considerably lessexpensive than their human counterparts. Human trials can taketwo to three times the calendar time because of the oftenlengthy process of approval and patient recruitment. Drugs forhumans can take 10–15 years to commercialise compared tothree to six years for animals.

Animal products can produce reliable and quite considerablecash flow in the short to medium term via revenue or licensingdeals, and they can also provide valuable experience with issuessuch as manufacturing and market access, providing anexcellent growth and development opportunity for the mainhuman drug target. It also proves to shareholders that themanagement and development team can commercialise acandidate, successfully generating revenues that help fund thecompany’s core projects.

Nexvet is a Melbourne-based biotech that was establishedrecently to develop and commercialise monoclonal antibodydrugs to treat osetoarthritis, skin conditions and pain incompanion animals, including cats, dogs and horses. Biotechentrepreneurs Mark Heffernan and David Gearing, co-founders ofNexvet, have found initial investors to be enthusiastic inAustralia and overseas. The extraordinary performance of Zoetis,the animal health spin-off from Pfizer, at initial public offering(IPO) a few years ago, sets an impressive benchmark for theanimal biotech sector. Just over a year ago, Zoetis raisedUS$2.2 billion, the biggest US IPO since the Facebook float. Thebiotech investment landscape is certainly improving this yearand animal biotech is likely to receive a warm reception frominvestors. Watch this space.


Animal attraction

Michelle Gallaher ([email protected]) is CEO ofBioMelbourne Network, having had 20 years in research and listedbiotech companies. She is one of the most prolific social mediacommentators on science and biotech in the Asia–Pacific.

Pet owners today aredemanding better care andaccess to cutting-edgetechnologies and services fortheir animals.Pharmaceutical, food andbiotech companies arehearing the call.

iStockphoto/minemero

The chemist Michel Eugène Chevreul was born on 31 August1786 in Anger, France, and died in Paris on 9 April 1889 at 102,leaving behind a massive legacy in three fields of science. Thefirst was the outcome of his work on animal fats and the acids(fatty acids) that were components of the natural glycerides.Purifying the separated acids was a very difficult task, andChevreul was guided in his work by the use of melting points,which (in most cases, and fortunately for the ones he studied)were at a maximum for the pure substance, and depressed bythe presence of impurities. Second, he identified the source ofvariations in colour produced by a single hue as being due tocomparison with adjacent colours. In other words, colourperception was subjective. His industry partners benefitted fromthis knowledge, as did painters who used tiny dots of colour tobuild up an image, as ‘pointillists’ such as Georges Seurat did.His third contribution was a stand against the pseudo-scienceof spiritualism and psychic ‘research’. The initial work ingerontology has also been ascribed to Chevreul.

On his 100th birthday, Chevreul was interviewed byjournalist Nadar, in what some believe was the world’s firstmedia interview. Nadar’s son Paul took a series of photographsduring the interview, and the dialogue was recorded by ashorthand stenographer. One commentator said that theoutcome was ‘something between a strip cartoon and the firstfilmed interview, and was catchily entitled ‘The Art of Living toOne Hundred’. Gaspard-Félix Tournachon (‘Nadar’) (1820–1910)was an early balloonist who in 1853 had taken the first aerialphotographs. Confined to earth in later years, he became acelebrity photographer with a sideline in pornography.

The interview between Chevreul and Nadar was recreated inAustralia in 2010, for screening on ABC television. Two actorswere made up to play the roles of the two Frenchmen so thatthey appeared in the way that Nadar Jr’s photographs hadrecorded them. The pictures are dageurrotypes, with the imageformed in a silver salt emulsion on a copper plate. Chevreulmade the point in the interview that he was president of theAcademie Francaise in 1839 when Louis Jacques-MendéDageurre revealed his process.

The text of the interview was likewise available, and theactors spoke in French while English subtitles were shown inthe screen. The interview was recorded in such a way that itlooked like a scratchy flickering early movie that had survivedall those years. The first real movie appeared in 1891, sowithout a good knowledge of cinematographic history, it’s easyto believe that the Chevreul interview is the real thing. It’savailable on DVD and it makes fascinating viewing.

Describing the original interview, one author referred to ‘thespry, twinkling Chevreul, with his wild mop of white hair …talking and gesticulating’ and that’s exactly what I saw in theAustralian recreation. Asked about his philosophy of life,Chevreul said that ‘one should aim for infallibility without everclaiming to have achieved it’, a maxim that he had adoptedfrom the work of 17th century French philosopher NicolasMalebranche. His secret of longevity was an orderly life,although he also acknowledged heredity – his father died at age91 and his mother at 93 – as an important predeterminant.Others were:• to dine at fixed times, chewing his food well but always

leaving the table with a little appetite• no tobacco (he didn’t like the smell)• varied activities, so that, for example, each day he had time

for some science in the morning, philosophy in theafternoon, and in the evening some music or poetry

• no discussion over dinner, and especially no politics (‘itwould be like swallowing a pin-cushion’).Asked whether he thought that living so long was a good

thing, Chevreul shot back ‘Do you doubt it?’ and went on toobserve that although ‘virility loses the double effect ofphysical and intellectual properties’, his curiosity wasundiminished and he retained ‘the habit of being an observer atall times’.

He expressed admiration of the author Moliere (‘the man whobest knew human nature’) and of course for Pasteur, ‘one of thegreatest geniuses of the century’, who had warned that ‘thegreatest malfunction of the spirit is to believe things becausewe want them to be true’.

Chevreul also asked Nadar about his ‘aerial navigation’, andthe former balloonist, who had endured some hair-raising tripsdriven by unfavourable winds, said that there was as yet no wayknown to steer a balloon.

Chevreul’s was one of 72 names of French scientists,engineers and mathematicians engraved in the metalwork ofGustave Eiffel’s tower, which was completed in 1889, andopened (although the lifts were not yet working) just 10 daysbefore Chevreul’s death. The names were painted over early inthe 20th century but restored in the 1980s; I saw them on avisit a few years ago, but ran out of gawking time before Ispotted Chevreul. Since then, the names have been repainted intheir original gold so I’ll pay closer attention next time.

letter from melbourne


Ian D. Rae FRACI CChem ([email protected]) is a veterancolumnist, having begun his Letters in 1984. When he is notcompiling columns, he writes on the history of chemistry anddispenses advice on chemical hazards and pollution.

The good life


cryptic chemistry

Across1 Proton Rh factor. (8)5 Like turf? (5)10 Tanned but burnt. (9)11 Spooner’s bunk, yes? (5)12 Zit we folk burst. (9)15 14 in 10. (5)17 List essential human nutrients first. (4)18 A chipped rock. (5)20 Wild rage. (4)21 In your eye. (4)23 Mug. (5)24 Got up. (4)28 Hearings at alternate choices. (5)29 Hears ruin repaired. (9)31 Pipe holding a . . . (5)33 . . . mixture of KCN, AmOI and N2. (9)36 Master erbium. (5)37 Radical grading calamity. (8)

Down1 Armaments manufacturer, without

tungsten, blew no bomb. (5)2 Wart treatment eliminates tungsten

source. (3)3 After loss of tungsten, showman smashed

cab. (6)

4 Tungsten in on grant. (3)6 Kink heard uneven song. (6)7 Copy name. (3)8 Quality university of Swiss and French

frequency. (4)9 Neumeier gives sauce. (8)13 Note that human angiogenic factor is

coming up. (3)14 Picture in picture in batch. (5)16 One horse antibody isotype. (3)17 Last-minute holding of CO(NH2)2

celebrated. (8) 19 Tree 8165368. (5)22 Electron on time period. (3)25 Sash worn by half the Queensland

town? (3)26 C2H4 inside the next reactor. (6)27 Considering the sense. (6)29 Gas my host! (4)30 Council of academics coming up with

inclusion of yttrium. (5)32 Anomalous aerial observation of uranium

is returning. (3)34 Auto catecholamine releaser. (3)35 Is it C10H7CH2CO2H or C6H9NO5? (3)

Graham Mulroney FRACI CChem is Emeritus Professor of Industry Education at RMIT University.Solution available online.

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The solution to each of the Across clues is a Chemistry 1 Down 17 Down.Otherwise, the Across clues do not contain a definition.

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