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Cairns Convention Centre

Cnr Wharf & Sheridan Streets

Cairns Queensland Australia

Meeting Room 5 (Mezzanine Level)

5

Physical and Electrochemical Properties and Applications of Ionic Liquids

Pre-Congress Workshop Programme

Sunday 31 May 2009, Cairns Convention Centre

Time Speaker Title

12:45 – 12:50 Mike Horne/Pat Howlett, Welcome & Introduction

12:50 – 1:20 Frank Endres, TU Clausthal, Germany

The interface Au(111)/ionic liquid: what can in situ STM/AFM tell us on the

interactions?

1:20 – 1:40 Alexander Wulf, University of Rostock, Germany

The importance of hydrogen bonding in aprotic and protic ionic liquids for the

understanding of physicochemical properties

1:40 – 2:00 Avise Perosa, Università Ca’ Foscari, Italy

Not merely solvents: task-specific ionic liquids made by green syntheses.

2:00 – 2:20 Vera Lockett, University of South Australia, Australia

Differential Capacitance of the Double Layer at Electrodes Immersed in Ionic

Liquids

2:20 – 2:50 Urs Welz-Biermann, Dalian Institute of Chemical Physics (DICP), China

Ionic Liquids - an efficient tool for future clean(er) energy related processes

and applications

2:50 – 3:10 Break

3:10 – 3:40 Yashushi Katayama, Keio University, Japan

Anode Reaction of Tin for Rechargeable Lithium Batteries Using an Ionic

Liquid Electrolyte with Some Glymes

3:40 – 4:00 Junhua Huang, Energy Technology, CSIRO, Australia

Application of Ionic Liquids for CO2 Capture

4:00 – 4:20 Andrea Balducci, University of Münster, Germany

Toward Greener Batteries: Fluorine-free binder in combination with ionic

liquid based electrolytes

4:20 – 4:40

6

7

The interface Au(111)/ionic liquid: what can in situ STM/AFM tell us on the

interactions?

Endres, F.

TU Clausthal, Robert-Koch Str. 42, 38678 Clausthal-Zellerfeld

In this lecture selected in situ STM/AFM results of the interface Au(111)/ionic liquid ([Py1,4]

Tf2N and [EMIm] Tf2N) are presented. Both local probe methods show that the gold surface is

subject to a strong interaction with the ionic liquid. The in situ STM shows in both cases that

the gold surface is worm-like structured at the open circuit potential. In the case of [Py1,4] Tf2N

more than -1 Volt is required to transform the wormlike surface to a flat one, whereas for

[EMIm]Tf2N only -0,3 V are required. In situ AFM/force measurements support this

observation: [Py1,4]Tf2N is more strongly adsorbed than [EMIm]Tf2N. Such a strong

interaction is rather unusual but might be considered for all reactions at the interface between

solids and ionic liquids.

8

The importance of hydrogen bonding in aprotic and protic ionic

liquids for the understanding of physicochemical properties

Koichi Fumino, Alexander Wulf and Ralf Ludwig

Institute of Chemistry, Physical Chemistry, University of Rostock,

Dr. Lorenz-Weg 1, D-18051 Rostock, Germany

Email: ralf.ludwig@uni-rostock.de

Cohesion energies determine the phase behaviour of materials. The understanding of

interaction energies is in particular interesting for ionic liquids. Continuous effort is made for

designing task-specific ionic liquids with desired physicochemical properties for potential

applications such as novel synthesis, electrolyte devices, photochemical cells, separations and

catalysis.1-3

This requires detailed insight into the nature of this new class of materials.

Here we show experimentally that, in accord with theoretical work, the intermolecular cation-

anion interactions in aprotic and protic ionic liquids can be detected by far FTIR spectroscopy

in the THz region.4 It can be also shown that these interactions are described by characteristic

ratios between Coulomb forces and hydrogen bonds.5 Protic Ionic Liquids (PILs) are a subset

of ionic liquids formed by an equimolar combination of a Brønsted acid and a Brønsted base.6

The possibility of proton transfer between acid and base leads to proton-donor and proton

acceptor sites building up a hydrogen-bonded network in PILs. Thus PILs have a number of

unique properties compared to other ILs such as water to normal molecular liquids. Going from

aprotic ILs with weakly interacting anions to PILs the ratio between Coulomb forces and

hydrogen bonds can be varied towards increasing hydrogen bond contributions. This is

reflected in important macroscopic properties of ionic liquids such as enthalpies of vaporization

and viscosities. This opens a new path for tuning the desired properties of this new class of

material.

1. F. Endres, S. Z. El Abedin, Phys. Chem. Chem. Phys., 2006, 8, 2101-2116.

2. R. D. Rogers, K. R. Seddon, Science, 2003, 302, 792-793.

3. Ionic Liquids in Synthesis, 2nd Ed., Eds.: P. Wasserscheid, T. Welton, VCH-Wiley,

Weinheim, 2008.

4. K. Fumino, A. Wulf, R. Ludwig, Angew. Chem. Int. Ed., 2008, 47, 3830-3834.

5. K. Fumino, A. Wulf, R. Ludwig, Angew. Chem. Int. Ed. ,2008, 47, 8731-8734.

6. T. L. Greaves, C. J. Drummond, Chem. Rev., 2008, 108, 206-237.

9

Not merely solvents: task-specific ionic liquids made by green syntheses.

Alvise Perosa, Maurizio Selva, Massimo Fabris, Marco Noè, Vittorio Lucchini

Dipartimento di Scienze Ambientali, Università Ca’ Foscari

Dorsoduro 2137 – 30123 Venezia, Italy

alvise@unive.it

We describe a class of phosphonium and ammonium ionic liquids made by green synthesis (A)

and designed to be solvents (B), catalysts (C), and to aid in product separation (D).

Synthesis Amines and phosphines with dimethylcarbonate (DMC), yield pure methyl-

ammonium and methyl-phosphonium salts. The substituents on the nitrogen and phosphorous

determine whether the products are liquid, i.e. ionic liquids (ILs), and their solvent ability. The

quaternarization with DMC is a green alternative to methylation using methyl halides and

dimethylsulfate, and affords directly an IL that is set up for a simple and halide-free anion

metathesis step. The metathesis is carried out using the conjugated acid of the desired anion,

CH3OH and CO2 are the only by-products. These ILs are characterized in the neat state by

one- and two-dimensional NMR. With a view of using them as task-specific solvents, the neat

NMR spectra provide a degree of information on the cation-anion interactions. And, in

perspective, on reactant-IL interactions as well.

Applications in synthesis This class of ionic liquids has so far found applications in multiphase

catalysis,1,2

nanoparticle formation,3 and ionic liquid mediated carbon- carbon bond forming

reactions. We will describe the synthesis, characterisation, and application of these ILs. They

are very active basic catalysts for base-promoted C-C bond forming addition reactions such as

the Michael, Henry, nitroaldol, and Baylis-Hillman reactions. These do not require added

solvents, or catalysis by base or metals.

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10

Differential Capacitance of the Double Layer at Electrodes Immersed in

Ionic Liquids

Vera Lockett, Rossen Sedev, Mike Horne, Theo Rodopoulos

and John Ralston

Ian Wark Research Institute, University of South Australia, Mawson Lakes, SA

5095, Australia

CSIRO Minerals, Box 312, Clayton South, VIC 3168, Australia

Many electrochemical processes happen at the electrode/electrolyte interface under electric

polarisation and therefore knowledge of the double layer behaviour is very important. The

differential capacitance reflects the processes occurring at the interface when a potential is

applied. The potential dependence of the differential capacitance for different electrodes in

ionic liquids was studied with impedance spectroscopy. The influence of the ionic liquid,

electrode and temperature on the double layer structure was investigated1. Experimental results

published by different researchers are in apparent contradiction. Factors which can explain

these discrepancies are discussed. Our results are supported by spectroscopic measurements2, 3

and novel theoretical predictions about the double layer structure4.

(1) Lockett, V.; Sedev, R.; Ralston, J.; Rodopoulos, T.; Horne, M. J. Phys. Chem. C 2008,

112, 7486-7495.

(2) Aliaga, C.; Baldelli, S. J. Phys. Chem. B 2006, 110, 18481-18491.

(3) Mezger, M.; Schroder, H.; Reichert, H.; Schramm, S.; Okasinki, J. S.; Schroder, S.;

Honkimaki, V.; Deutsch, M.; Ocko, B. M.; Ralston, J.; Rohwerder, M.; Stratmann, M.;

Dosch, H. Science 2008, 322, 424-428.

(4) Kornyshev, A. A. J. Phys. Chem. 2007, 111, 5545-5557.

11

Ionic Liquids - an efficient tool for future clean(er) energy related processes

and applications

Commercial success stories and future challenges

- with a special outlook on China -

Prof. Dr. Urs Welz-Biermann

Director of China Ionic Liquid Laboratory (CHILL),

Dalian Institute of Chemical Physics (DICP), Dalian China

Ionic Liquids are making the transition up from laboratory curiosities to useful tools for a wide

range of applications. As solvents, catalysts and electrolytes for use in sustainable processes,

Ionic Liquids represent a bold opportunity to innovate. Their low vapor pressures make them

ideal replacements for highly volatile organic solvents, reducing the pollution caused by solvent

evaporation. And their intrinsically conductive nature makes them favored materials for use in

electrochemical technologies, such as super capacitors and dye-sensitized solar cells. To make

use of these materials scientists and engineers need to appreciate how structural differences

between Ionic Liquids lead and differences in physicochemical properties, which in turn lead to

differences in performances in a given process or application.

Despite all the recent advances, Ionic Liquids are still alien materials to most members

of the scientific community, especially to the many potential users in key application areas. But

more and more commercial applications have been disclosed, providing first evidence of their

general usefulness.

This presentation will address some important issues related to the future success of

Ionic Liquids based applications. It will also give a general overview of Ionic Liquids activities

in China, the most rapid developing country in this emerging technology:

• What beneficial properties do Ionic Liquids have for applications in the field of clean

energy and where are their limitations today?

• Tools to overcome the technology gap between university and industry

• Recent Ionic Liquids developments in China?

• What is special/unique about Ionic Liquids activities in China?

In January 2008 the new China Ionic Liquid Laboratory was established within the Fine Chemicals Department of

the Dalian Institute of Chemical Physics (DICP). The principal aim of this laboratory is to explore, develop and

understand the role of ionic liquids as media for a wide range of applications e.g. green chemistry, clean energy,

biotechnology, catalysis, organic and inorganic synthesis. First work will focus on the design, preparation,

chemistry and properties of new functionalized ionic liquids and their environmental impact.

12

Anode Reaction of Tin for Rechargeable Lithium Batteries Using an Ionic Liquid

Electrolyte with Some Glymes

Yasushi Katayama, Sodai Miyashita, and Takashi Miura

Department of Applied Chemistry, Faculty of Science and Technology, Keio University,

Hiyoshi 3-14-1, Kohoku-ku, Yokohama, Kanagawa 223-8522, Japan

katayama@applc.keio.ac.jp

There is a growing demand for safety of rechargeable lithium batteries, which are expected to

be applied for various power applications, such as hybrid and pure electric vehicles. Flammable

organic electrolytes used in existing lithium-ion batteries may cause explosion

and/orcombustion in case of accidents. Therefore, employing non- flammable electrolytes is

rechargeable lithium batteries. Ionic liquids have been investigated extensively as non-

flammable electrolytes for rechargeable lithium batteries. However, the ionic liquids which

meet such practical requirements as high electrochemical stability and high ionic conductivity

have not been developed yet. In the present study, the effect of some additives on the lithium

dope and undope reactions of a tin electrode has been investigated in an electrolyte based on a

hydrophobic ionic liquid, 1-butyl-1- methylpyrrolidinium bis(trifluoromethylsulfonyl)amide

(BMPTFSA).

Lithium dope and undope reactions for a Sn electrode were found to be possible in 1 M

LiTFSA/BMPTFSA regardless of addition of some glymes, CH3–O–(CH2–CH2– O)n–CH3 (n =

1 ~ 4), which are denoted as 1G ~ 4G. In addition, formation of passivation film on the Sn

electrode was not confirmed by X-ray photoelectron

spectroscopy. However, the charge transfer resistance

measured at a composition of LiSn in 1 M

LiTFSA/BMPTFSA was about ten times larger than

those in conventional organic electrolytes. On the

other hand, the charge

transfer resistances decreased dramatically with

addition of a small amount of glymes (0.2 M)to 1 M

LiTFSA/BMPTFSA, as shown in Fig. 1. Since the

donor properties of the glymes are considered to be

higher than that of TFSA–, lithium cations are

expected to be coordinated selectively with the

glymes. Thus, it is suggested that the coordination

environment of lithium cation strongly affects the

electrode kinetics in ionic liquids.

Acknowledgement

This work was financially supported by Li-EAD (Li-ion and Excellent Advanced Battery

Development) project of NEDO (New Energy and industrial technology Development

Organization).

13

Application of Ionic Liquids for CO2 Capture

Junhua Huang

Energy Technology, CSIRO, BOX 312, Clayton South, VIC 3169, Australia

Jewel.Huang@csiro.au

As the climate debate is hotting up, so is the (re)search for finding new methods and powerful

materials for the efficient and cost effective removal of CO2 from flue-gas streams of power

plants and other emission sources. Ideally, the absorbents would have high absorption

capacity, fast ab/desorption kinetics, balanced reaction enthalpy, high stability and

environmental friendliness.

This presentation is intended to evaluate the advantages and disadvantages of the application of

ionic liquids (ILs) to capture CO2 from flue gas streams in the process of Post Combustion

Capture (PCC), and to provide an overview of the recent development of ILs in this area.

In conventional ionic liquids, CO2 is absorbed by occupying the free space between the ions

through physical absorption mechanisms. As another promising strategy, task specific ionic

liquids (TSILs) have been studied which, by attaching functional groups to the ions, allow the

formation of chemical bonds to improve the overall absorption capacity during the CO2 capture

process (Fig. 1). Other strategies include using ILs as reaction media or as selective absorption

materials.

14

Toward Greener Batteries: Fluorine-free binder in combination with ionic

liquid based electrolytes

Simon Lux, Sang-Sik Jeong, Stefano Passerini, Martin Winter and Andrea

Balducci

Institute of Physical Chemistry, Westfälische Wilhelms University of Münster, Germany

andrea.balducci@uni-muenster.de

Lithium-ion batteries are today the only high-energy density portable power sources

commercially available. These devices have several advantages such high energy density and

good cycling stability, however, as organic carbonates are used as electrolyte, safety problem

and limitation on the operative temperature range are still present 1.

Ionic Liquids (ILs) are today considered as very attractive candidates for electrolytes in

electrochemical devices such as batteries, and different type of ILs have already been used in

combination with different anodic and cathodic materials in lithium batteries with promising

results 2.

The interest on the use of Na-CMC as electrode binder in strongly increased in the past

year. During the electrode preparation Na-CMC can be processed in aqueous solution and in

addition it is cheaper with respect the binder used today in the commercial systems 3.

For these reasons, the introduction of Na-CMC in system based on ILs could be an

important contribution for the realization of greener and cheaper batteries.

In this work are reported the electrochemical performance of different electrode materials

containing Na-CMC as binder in electrolytic solutions based on N-methyl-N-propyl

pyrrolidinium bis(fluorosulfonyl) imide, PYR13FSI, and N-butyl-N-methylpyrrolidinium

bis(trifluoromethansulfonyl) imide PYR14TFSI (Figure 1).

Fig.1. Electrochemical performance of silicon composite electrode containing Na-CMC as binder in

electrolytic solution based on 0.3M LiTFSI in PYR14TFSI + 5wt. % VC.

1. G-A Nazri, G.Pistoia, Lithium Batteries, 2004, Kluwer Academic/Plenum Publisher

2. M. Ishikawa et al., J. of Power Sources, 2006, 162(1), 658-662

3. N.S. Hochgatterer et al., Electrochemical Solid-State Letters, 2008, 11, 5, A80

15

Effect of moisture on the phase transformation of the electrodeposited nickel in 1-

ethyl-3-methylimidazolium chloride

Abhishek Lahiri and Ramana G Reddy

Department of Metallurgy and Materials Engineering, The University of Alabama, Tuscaloosa,

AL 35487

Email: lahiri.abhishek@gmail.com

Nickel has been electrodeposited from NiCl2-1-ethyl-3-methylimidazolium chloride in both

hexagonal closed pack (HCP) and face centered cubic (FCC) separately by controlling the

electrolysis temperature and moisture content in the sample.

Nickel is a transition metal having remarkable corrosion resistant property and therefore is

extensively used in alloys and electroplating1. The electrodeposition of metals from metal chloride is

a new approach for metal production2. Considerably less work has been performed on the

electrodeposition of nickel3, 4

. In this paper we show an interesting phenomenon during the

electrodepositing of nickel from nickel chloride. It was observed that during electrolysis the presence

of moisture in the sample resulted in the production of HCP nickel whereas in absence of moisture

FCC phase was produced. To evaluate the effect of moisture and electrolysis temperature, the

electrodeposited sample and the electrolyte were characterized using scanning electron microscopy

(SEM), energy dispersive X-ray (EDX), X-ray diffraction (XRD) and Fourier transform infrared

spectroscopy (FTIR) techniques. The electrodeposition of HCP and FCC structure of nickel at two

different electrolysis temperatures are evident from the XRD in Figure 1. The effect of moisture on

the formation of the two structures was identified by performing FTIR on the electrolyte which is

demonstrated in Figure 2.

Thus from figures 1 and 2, it can be confirmed that both temperature and moisture content results in

the formation of two different crystal structures and by controlling the two factors the crystal

structure can be altered.

1 M. Popczyk, A. Budniok and E. Lagiewka, Mater. Charact., 2007, 58, 371-375.

2 F. Endres, ChemPhysChem, 2002, 3, 144.

3 A. P. Abbott, K. El Ttaib, K. S. Ryder and E. L. Smith, Trans. Inst. Metal Finish.,

2008, 86, 234-240.

4 S. P. Gou and I. W. Sun, Electrochim. Acta, 2008, 53, 2538-2544.

16

CONTINUOUS ENZYMATIC REACTORS IN IONIC

LIQUIDS/SUPERCRITICAL CARBON DIOXIDE BIPHASIC SYSTEMS

Pedro Lozano1, Teresa De Diego

1, Michel Vaultier

2 and José L. Iborra

1

1 Departamento de Bioquímica y Biología Molecular B e Inmunología. Facultad de Química.

Universidad de Murcia. P.O. Box 4021. E-30100 Murcia, Spain 2 Département de Chimie et Electrochimie Organique. UMR CNRS 6510. Université de

Rennes-1..Campus de Beaulieu. Avenue du Général Leclerc. F-35042- Rennes. France.

Green Chemistry is based on the use of safer solvents and reaction conditions, and encourages

the use of environmentally benign non-aqueous solvents and efficient catalysts for chemical

reactions and/or processes. Enzymes, as catalysts of living systems, clearly constitute powerful

green tools for chemical processes, since their activity and selectivity (stereo-, chemo- and

regioselectivity) for catalyzed reactions are far-ranging. However, the use of biocatalysts in

non-aqueous media is limited because the native structure of the enzyme can easily be

destroyed, resulting in deactivation.

In this context, ionic liquids (ILs) and supercritical fluids (SCFs) are the non-aqueous green

solvents which have received most attention worldwide for use in enzyme catalysis, because of

their excellent characteristics for enzymatic processes1. The unique solvent properties of ILs,

especially as regards their polar character (which depends on the nature of the involved ions)

have opened an alternative door for using as non-aqueous liquid environments in enzyme

catalysis. Thus, research on enzymatic catalysis in ILs was firstly focused on the potential of

these neoteric solvents as reaction media, then on understanding the exceptional behavior of

enzymes in some kinds of ILs, and finally on the development of integrated

biotransformation/separation systems made possible by the unique properties of ILs.

On the other hand, the classical advantages of supercritical carbon dioxide (scCO2) to extract,

dissolve and transport chemicals are tarnished in the case of enzymatic processes because of its

denaturative effect on enzyme 2. Additionally, both ILs and scCO2 neoteric solvents have

interesting two cross-points: they are not-miscible and can be easily separated from substrates

and products, and they can be reused. As the scCO2 can dissolve in the IL phase (up 0.7 mole

fraction), a new concept of biphasic bioreactors for Fine Chemicals syntheses may be

developed by using both enzyme and chemical catalysts “immobilized” into the IL phase, and

substrates transported by the scCO2 phase 3. Several types of continuous reactors based on

enzymatic or chemoenzymatic catalysis have been tested for the resolution of different racemic

mixtures (i.e. rac-1-phenylethanol, ketoprofen, etc), even including a separation step by using a

membrane module 4. For the case of the continuous chemoenzymatic dynamic kinetic

resolution (DKR) of rac-1-phenylethanol, the reactor was continuously operated by using

simultaneously immobilized lipase (Novozym 435) and acid zeolites catalysts in IL/scCO2 at

50 ºC and 100 bar, providing an excellent yield (up 98.0 %) for R-phenylethyl propionate

product and enantioselectivity (up 97.3 %), and without any activity loss for 14 days of

operation 5.

17

References

1. P. Lozano, T. de Diego, D. Carrié, M. Vaultier, J.L. Iborra, Continuous green biocatalytic

processes using ionic liquids and supercritical carbon dioxide, Chem. Commun. 2002, 692-

693.

2. P. Lozano, T. de Diego, S. Gmouh, M. Vaultier, J.L. Iborra, Criteria to design green

enzymatic processes in ionic liquid/supercritical carbon dioxide system, Biotechnol. Prog.

2004, 20, 661-669.

3. P. Lozano, T. De Diego, J.L. Iborra, Enzymatic catalysis in ionic liquids and supercritical carbon dioxide biphasic systems Chem. Today, 2007, 25, 76-79.

4. P. Lozano, T. De Diego, A. Manjón, M.A. Abad, M. Vaulltier, J.L. Iborra. 2008. 236th

ACS

National Meeting. Philadelphia.

5. P. Lozano et al.. Long term continuous green chemoenzymatic dynamic kinetic resolution of

rac-1-phenylethanol using ionic liquids and supercritical carbon dioxide. Green Chem., 2009,

11, 538 - 542

Acknowledgements.

Work partially supported by CICYT (Ref: CTQ2008-00877/PPQ) and SENECA Foundation

(Ref.: 08616/PI/08) grants

18