where’s the puck going to be? - reluceo...
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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
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Major Opportunity for Underutilized
Non-Food Biomass
Renewable Chemicals
and Materials
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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
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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
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Principal Sources of Biomass
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• Plants
– Agricultural, Forestry, Algae
• Animals
– Livestock, marine organisms
• Microorganisms
– Fungi/yeast, bacteria, microalgae
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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
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• Chemistry
• Price
• Quantity
• Consolidation
• Seasonality
• Sizing
• Competing Uses
Evaluation of Biomass Sources
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C5, C6
C6
C5, C6
C6
Hemicellulose
20-35%
Representative Cellulosic Biomass Composition
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• 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
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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)
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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
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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
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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.
• There are over 100 bio-based industrial chemical compounds in production practice and at developmental stages
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Drop-in Example
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Plant-based PET bottles are recyclable,
but not degradable
Bio-Ethanol Ethylene Ethylene Glycol PET
http://www.germanbeerinstitute.com/history.html
Millennia of Brewing to Alcohols
http://www.minnpost.com
…from Booze to Fuel
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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
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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
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About 100 Years Later…
The Early 20th Century
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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
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McKinsey & Company
Boom of Petrochemical Industry
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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
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HOLDINGS LLC
2013
Levulinic Ketals Technology Platform
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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
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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)
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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
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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
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Thank You
Contact: Olga Selifonova – olga_selifonova@reluceo.com
P.O. Box 47855, Plymouth, MN 55447, USA; Tel: +1-612-701-2280
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