where’s the puck going to be? - reluceo...

Where’s the Puck Going to Be? Opportunities for Renewable Biochemistry

Agriculture and Rural

Executive Conference

Marshall, MN March 11, 2014

Bio-based Chemicals: What, Why, How…

Olga Selifonova

Reluceo Holdings LLC

All Sustainable Wealth of Civilization

is Derived from Agriculture and Forestry

2 2014 Reluceo Holdings LLC

FOOD

FEED

FUEL

FIBER


Major Opportunity for Underutilized

Non-Food Biomass

Renewable Chemicals

and Materials


Definitions

• Biomass - rapidly renewable organic matter

recently produced by modern living organisms – as opposed to accumulated “fossil” organic matter over

geological periods lasting many millions of years (e.g. diagenesis

processes leading to the formation of petroleum and coal)

• Bio-based Chemicals – biochemicals produced

from sugars or its derivatives, fats, vegetable oils

and other biomass components via biological or

chemical conversions

• Conversion Technologies – fermentation,

biocatalysis, thermochemical conversions

2014 Reluceo Holdings LLC 5

Aspirations for Industrial Bio-based Chemicals

• Planet and People friendly products – with exceptional performance

– devoid of toxins

– simple to make from renewable sources

– beautifully designed to re-enter the carbon cycle when

they are no longer needed

– at competitive price

• Enable participation of Ag producers in

higher value applications for underutilized

non-food biomass


Principal Sources of Biomass


• Plants

– Agricultural, Forestry, Algae

• Animals

– Livestock, marine organisms

• Microorganisms

– Fungi/yeast, bacteria, microalgae


C6 CO2

H2O

Sun light

Cellulose (C6)

Hemicellulose (C5, C6)

Lignin

Starch (C6) Sucrose (C6)

N, K, P …

Carbohydrates (C, H, O)

Feedstock complexity

• “Soft” Feedstocks – Starch, Glucose, Sucrose

– Vegetable Oils, Fats

– Existing efficient crop processing technologies

• Dry and wet corn milling

• Beet or cane sugar extraction

• Vegetable oil extraction from oilseed…

• “Hard” Feedstocks – Grassy/Woody Biomass

– Processing technologies for chemical separation are still

limited or under development


• Chemistry

• Price

• Quantity

• Consolidation

• Seasonality

• Sizing

• Competing Uses

Evaluation of Biomass Sources


C5, C6

C6

C5, C6

C6

Hemicellulose

20-35%

Representative Cellulosic Biomass Composition


• Carbohydrates (C6 and C5) are the most abundant form of organic carbon

– Lignin is the second most abundant form of organic carbon (a complex aromatic cross-linked polymer)

– Other classes of biomass derived organic compounds are proteins, fats, oils, DNA, isoprenoids, etc. (limited scalability for high volume industrial uses)

• Pentosanes (C5) of hemicellulose are the easiest

to separate under mildest industrial conditions – with a century of industrial practice

– furfural (for furfuryl alcohol)

– xylose (for xylitol)

• Cellulose (C6) is currently used in chiefly intact

form, with some chemical modifications – pulp and paper

– soluble cellulose fibers

– cellulose esters and ethers

– fundamentals of the current state of cellulosic sugar technology (chemical, enzymatic, pre-treatments) do not support cost-effective entry into commodity chemicals or biofuels


Proven Conversion and Separation

Technologies for Cellulosic Biomass

Bio-based Chemical Products

• Simple organic molecules

• Medium complexity compounds

(surfactants, “pre-polymers”, etc.)

• Large linear or branched/crosslinked

polymers/and co-polymers (plastics and

thermosets)


Age of Petroleum:

Fossil Carbon Use Peak


years

Bio-based Chemicals for Industrial Production

• “Drop-in” compounds: structures match exactly of those produced industrially using temporarily available fossil carbon sources (petroleum, gas, coal)

– Examples: ethanol, ethylene, polyethylene, ethylene glycol, vinyl acetate, polyvinyl alcohol, 1,3-propanediol, 1,2-propylene glycol, butanol, acetone, isobutanol, acrylic acid, propylene, isoprene, 1,4-butanediol





• “Naturogenic” compounds: biochemical metabolites and their derivatives with no practical or cost-effective routes available using fossil carbon sources

– Fermentation-based examples: lactic acid and esters, citric acid, itaconic acid, gluconic acid, lysine, glutamic acid

– Thermochemical process examples: sorbitol, xylitol, glycerol





• “Naturogenic” compounds: biochemical metabolites and their derivatives with no practical or cost-effective routes available using fossil carbon sources

– Fermentation-based examples: lactic acid and esters, citric acid, itaconic acid, gluconic acid, lysine, glutamic acid

– Thermochemical process examples: sorbitol, xylitol, glycerol.

• There are over 100 bio-based industrial chemical compounds in production practice and at developmental stages


Drop-in Example


Plant-based PET bottles are recyclable,

but not degradable

Bio-Ethanol Ethylene Ethylene Glycol PET

Renewable Bio-based Chemicals:

Not a New Idea


http://www.germanbeerinstitute.com/history.html

Millennia of Brewing to Alcohols

http://www.minnpost.com

…from Booze to Fuel


Albert Boehringer

(1861-1939)

1895 - The company pioneered

industrial scale production of

lactic acid for:

• dyeing

• leather

• textile

• food industry http://www.boehringer-ingelheim.com/news/image_gallery/history.html

In 1893, Boehringer discovered that

lactic acid can be produced by bacteria

“Biotech” of the 19th Century


NatureWorks LLC

2003 – world largest Lactic Acid

and PLA (polylactic acid polymer)

manufacturing

began in 1989 as a Cargill research project looking

for innovative uses of carbohydrates from plants as

feedstock for more sustainable plastics http://www.natureworksllc.com/About-NatureWorks-LLC


About 100 Years Later…

The Early 20th Century


1864-1943

Invented over 100 bio-based

products: plastics, paints, dyes, fuel

from agricultural feedstocks

(peanuts, soybeans, etc.)

Combining the auto industry with

agriculture

https://www.thehenryford.org/research/soybeancar.aspx

1941 - Henry Ford’s “Soybean Car” George Washington Carver

Mid-Late 20th Century

Availability of affordable

petroleum and globalization

suppressed development

of bio-based chemicals

and materials from

agricultural raw materials


McKinsey & Company

Boom of Petrochemical Industry


21th Century –

Time for Bio-Economy


Produced by the Staff at

Pacific Northwest National Laboratory (PNNL)

National Renewable Energy Laboratory (NREL)

Office of Biomass Program (EERE)

For the Office of the Biomass Program

T. Werpy and G. Petersen, Editors, 2004

The twelve sugar-based building blocks are 1,4-diacids

(succinic, fumaric and malic), 2,5-furan dicarboxylic acid, 3-

hydroxy propionic acid, aspartic acid, glucaric acid, glutamic

acid, itaconic acid, levulinic acid, 3-hydroxybutyrolactone,

glycerol, sorbitol, and xylitol/arabinitol.

HOOH

O

O

O

O

OH

O

HO

HO OH

O

HO OH

OH

O

O

OH

O

OHOOH

HO

O

O NH2

OH OH

OH

OHOH

OH

OH

OH

OH

OH OH

OH

O

NH2

HO

O

HOOH

O

O

HOOH

OH

OH

OH

OH

O

O

A version of graphic representation of

“Top 12 DOE platform chemicals from glucose”

http://www.osti.gov/scitech/biblio/926125

http://www.amazon.com/Top-Value-Added-Chemicals-

Biomass/dp/1249193028/ref=sr_1_fkmr1_1?ie=UTF8&qid=1393721710

&sr=8-1-

fkmr1&keywords=Top+Value+Added+Chemicals+from+Biomass+Volum

e+I%E2%80%94Results+of+Screening+for+Potential+Candidates+from

+Sugars+and+Synthesis+Gas

XLTerra

2002

2006

2009

2009

Our Green Chemistry Startups


HOLDINGS LLC

2013

Levulinic Ketals Technology Platform


2006

The first of the L-ketals discovered at Aromagen,

Ethyl Levulinate Glycerol Ketal has been

commercially introduced by Segetis.

As a key formulation ingredient, it can be found in

concentrated detergents and cleaning products

produced by Method and Seventh Generation.

O

O

HO

O

OR


C5 Chemical Platform

PXLK, Poly(Xylitan Levulinate Ketal), the

pinnacle of levulinic ketal platform chemistry,

is a colorless, ductile (not brittle), bioplastic

displaying:

• exceptional optical clarity

• high impact resistance

• thermostability

• high heat deflection (Tg 115oC)

• excellent tensile strength

PXLK is superior to PLA and PHAs

PXLK can compete with best petroleum-

based plastics.

XLTerra

PXLK

OO

O

O

O

O

n

Transparent Bioplastic

…from Biomass

High Performance Bioplastic from True

Biomass: Exceptional Value Proposition for

Conversion of Pentosanes (Hemicellulose)


Novel Degradable PVGA SAP

based on industrial, degradable and

renewable polymer poly(vinyl alcohol)

acetalized with glyoxylic acid

(an ubiquitous natural product

produced commercially)

The PVGA SAP has exceptional

potential for water management and

water retention systems in precision

agriculture and re-vegetation, as well

as environmentally-responsible

personal hygiene products

(including baby diapers)

OH OH OH

HO

CO2H

+

poly(vinyl alcohol)

glyoxylate

O O OH

CO2(Na, K)

Na, K PVGA*

n

*representative repeat unit

-H2O

Beyond Acrylics: Alternative

Superabsorbent Polymer (SAP)

C2 Chemical Platform

Based on Bio- Ethanol

Drought stress survival extended by 2 weeks in sand

No SAP +0.1% PVGA


Reluceo Holdings LLC has been formed and funded by Sergey

Selifonov and Olga Selifonova in December 2013 to continue building

our brand on intellectual and technology traditions for discovery and

pursuit of one-of-a-kind rule changing green chemistry processes and

renewable materials.

Formation of Reluceo Holdings LLC sets the scene for new projects,

opportunities and ventures.

HOLDINGS LLC


Thank You

Contact: Olga Selifonova – [email protected]

P.O. Box 47855, Plymouth, MN 55447, USA; Tel: +1-612-701-2280

mailto:[email protected]

where’s the puck going to be? - reluceo...

Documents