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CATALYSIS FOR RENEWABLE CHEMICALS
Pramod Kumbhar
Ex. Vice President-R&D
Praj Matrix
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Outline
• Renewable chemicals : Basics
• Biomass valorization strategies
• Bio-catalysis
• Chemo-catalysis
• Conclusions
• Praj and Praj Matrix
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Definitions
A renewable resource is a natural resource with the ability to reproduce
through biological or natural processes and replenished with the passage
of time.
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• No!!
• Mid to let 1800’s
• Methanol, acetic acid and acetone : Pyrolysis of pine wood
• Ethanol, butanol and acetone : Fermentation of sugar and starches
Renewable chemicals : Is it new?
• Rayon, the first synthetic fabric, and celluloid, the earliest form of film
stock : partially derived from bio-based sources.
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Renewable chemicals : Is it new?
• In 1897 Eduard Buchner began to study the ability of yeast
extracts to ferment sugar despite the absence of living yeast cells.
In a series of experiments at the University of Berlin, he found
that the sugar was fermented even when there were no living
yeast cells in the mixture. He named the enzyme that brought
about the fermentation of sucrose "zymase".In 1907 he received
the Nobel Prize in Chemistry "for his biochemical research and
his discovery of cell-free fermentation".
As recently as the late 1940s, the world depended on bio-based processes
to produce many chemicals
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Motherhood statement!!
Why will chemical industry embrace it??
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Renewable vs. Petroleum raw material prices
Competitive feed stock : key for profitability!
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Non Renewable Renewable
Witnessing Shift in Feed stocks
From hydrocarbons to carbohydrates
19th century 20th century
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Fundamental challenge for catalysis
Opportunity
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Three degrees of Complexities
1st gen Corn
Sugar cane
Cassava
2nd Gen Agriculture biomass
Vegetable oil products
Bio-catalytic Enzymes
Yeast
Bacteria
Chemo-catalytic
Thermochemical
Renewable Drop in replacement
New Molecules
Existing molecules with
Different economics
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Biomass Valorization Strategies
11
• Highly selective
• Low temperature (< 70 °C)
• Aqueous phase
• Primarily batch processes
• Low productivity
• Selective chemistry
• Moderate temperatures
(< 350 °C)
• Various reaction medias
• Batch and continuous
processes
• Non-selective chemistry
• High temperatures (350-600°C)
• Compactification of biomass
• Total decomposition
• Very high T
(>800 °C)
Bio-catalysis Chemo-Catalysis Pyrolysis Gasification
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Possible renewable chemicals
*Source DOE Report
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Top 12 sugar based building blocks
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Bio-catalysis
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Desired molecule
Design of a bio-catalyst :
Traditional Approach
Desired biochemical
• Genes selected rationally
• Trial and error approach
• Amplifying one gene at a time
• Lower productivity
The Ability to Cut and Paste Genes in Microbes Allows Us to Work
Like Never Before!
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Desired molecule
Design of a bio-catalyst :
Computational approach
• Strain Engineering
Rapid : Simultaneous testing of pathway diversity
Efficacious : Most productive gene combination selected by the organism!
Combinatorial pathway engineering accelerates the strain development!
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Desired molecule
Design of a bio-catalyst :
Computational approach
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Bio Succinic Acid
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Succinic acid : Market data
Total volume : 30000 MTA
Application : Polyester, polyols, coatings
Petrochemical route : Based on Maleic anhydride
Interested companies in Bio succinc acid : BASF/Purac, Bioamber, DSM,
Myriant/PTGC/Mitsubishi
Petrochemical route too expensive
Biochemical route attractive!!
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E.Coli : Mixed acid fermentation
Need to block the undesired pathways!
Myriant did it with strain engineering!!
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Scale-up of Myriants succinic acid
technology
2007 2010 2012 2014
(strain Engineering)
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Bio Adipic Acid
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Adipic acid : Market data
Conventional process
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Verdezyne Bio-catalytic process
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Bio 1,4-Butanediol (BDO)
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Bio 1,4-BDO : Opportunity
• It is a non natural compound
• Not synthesized by any organism
• No complete biosynthetic pathway to harness BDO production
Need a deNovo approach to make in bio-catalytically !!
• Market size : 1 MM MTA
• Produced synthetically from petroleum source
• Used in PBT, polyesters and for making THF
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Strain Engineering for BDO by
Genomatica
Nature Biology. Vol. 7, 445, 22nd May 2011
BDO biosynthetic pathways introduced into E. coli. Enzymes for each numbered step are as follows: (1)
2-oxoglutarate decarboxylase; (2) succinyl-CoA synthetase; (3) CoA-dependent succinate semialdehyde
dehydrogenase; (4) 4-hydroxybutyrate dehydrogenase; (5) 4-hydroxybutyryl- CoA transferase; (6) 4-
hydroxybutyryl-CoA reductase; (7) alcohol dehydrogenase. Steps 2 and 7 occur naturally in E. coli
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1,4-BDO : Genomatica
Catalyst : genetically
engineered E-coli
Higher Titre, rate and yield
The power of strain engineering!!
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Direct gaseous fermentation to Isobutene
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Isobutene : Applications
Diesel
Isooctane
Jet fuel
Tires
Lubricants,
Plastics
pET
Organic glass
Isobutene
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What is the difficulty?
• Microorganisms naturally do not produce light olefins
• Classical bio-process are based on improving existing metabolic pathways
• De novo design of metabolic pathways is necessary to bio-produce light
olefins
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Global Bioernergies, France
• Successfully created an artificial metabolic pathway to Isobutene
Isobutene
Glucose Clostridium
pathway
HMG-CoA synthase
Di-P-mevalonate
decarboxylase Patent EP2304040
Patent WO2011032934
Hydroxyisovalerate
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e.g. high purity
Isobutene
Low quality
Glucose
Genetically engineered
micro-organism
Reduced costs and improved environmental impact due to:
- No product toxicity, no feedback-inhibition no back-
flux,
- No distillation or liquid from liquid extraction
Proof of Concept
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0.0
100.0
200.0
300.0
400.0
500.0
600.0
0 20 40 60 80 100 120 140 160 180 200
Co
st o
f ra
w s
ug
ar
($/t
on)
PROFIT AREA –
No profit area
Bio-isobutene price = fossile high-purity isobutene price
Price of oil ($/barrel)
No profit area
1998 1997
1996 1995
2010 2011
2009 2008
2007
2006
2005
2005
2004 2003
2002
2001
2010
2009 2008
2007
2006
2004
2003
2002
2001 2000
1994
1993 1992
1991
2011
1999
1999
1998 1997
1996
2000
1995
1994
1993
1992
1991
Sugar cane
Sugar beet
The profitability question
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Edward Buchner : Nobel lecture “Cell free fermentation” 11th Dec. 1907
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Chemo-Catalysis
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Challenges with respect to carbohydrate
chemistry for Chemo-Catalysis
ACTIVATION OF
ALKANES,
OLEFINS etc.
MULTIPLE
FUNCTIONALITIES
COMPETING REACTIONS
– BY PRODUCTS
DOWN STREAM
PROCESS
GAS and LIQUID
PHASE
NONVOLATILE
CONDENSED/LIQUID
PHASE
SURFACE CHEMISTRY
ADSORPTION
/DESORPTION SMALL
MOLECULES
LARGE COMPLEX
MOLECULES
MESOPOROUS
CATALYSTS
ACTIVE SITE &
REACTION SPHERE
CHEMISTRY
NON AQUEOUS
CHEMISTRY
WATER INTEGRAL
PART HYDROTHERMAL
STABILITY
SINGLE
FUNCTIONALITIES
CATALYST POROSITY
LIMITED SOLUBLITY
IN NON-AQUEOUS
SOLVENTS
Conventional Catalysis
Carbohydrate Catalysis
Challenges Possible
remed ies
END PRODUCT
SELECTION
REDESIGN
CATALYSTS
Oxygenated
compounds
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Levulinic acid: A Green platform chemical
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Levulinic acid Ketals by Segetis
ROUGH ESTIMATES SHOW A REPLACEMENT POTENTIAL OF
50 MTPA @ 1USD/KG
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Conversion of Glucose to Levulinic acid
HUMINS
Polymerization
Etherification
Ref.: Rackeman D. W. , Doherty W.O.S, Biofpr. 5:198-214(2011)
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Technology wrap - up
TECHNOLOGIES BASED ON MINERAL ACIDS DUAL SOLVENT FOR ENHANCED SOLUBILITY
Ref.: Rackeman D. W. , Doherty W.O.S, Biofpr. 5:198-214(2011)
TECHNOLOGIES BASED ON SOLID CATALYSTS
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Biofine process for Levulinic acid
Highly capital intensive!
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The “Praj ELA” process
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C6 sugars
Ethyl levulinate (ELA)
Ethyl Formate
Ligneous char
Ethanol
Heterogeneous
catalyst
• Single step “green” process
• 50% of theoretical yield
achieved
• Process demonstrated on
Lab/semi pilot scale
• Scale-up to pilot in progress
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Gold : thought to be inactive as catalyst
because
• Glitters eternally: chemically inert
• Does not dissociatively adsorb H2 and O2
• Low Melting point : sintering temperature
1063 ℃ vs 1769℃ (Pt)
Catalysis by Gold
Gold : Neglected metal catalyst!
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Prof. Haruta
Tokyo Metropolitan University
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Conditions for Gold to be active
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Sugar acids using gold catalyst
Prof. Vorlop, 2012
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Renovia adipic acid process
• Pt and gold based catalysts
• Cash cost below cyclohexane process
US patent application : 20110306790
Pilot plant operating at 1lb/hr
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• Renewable Chemicals: The Future is Now
• Catalysis will be the key to the success
• Interdisciplinary (chemists, bio-chemists, microbiologists
and chemical engineers) team approach essential to make
it happen
• There is no such thing as “Green premium”
Summary
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Praj and Praj Matrix
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Praj Industries Limited - Background
Established in 1984
1st Company to avail VC funding in India
Listed on Indian Stock Exchanges
Business Lines
BioEthanol
Breweries
Water and Wastewater
Inputs and Chemicals
Energy Crops Services
Customized Engineering and Manufacturing
Over 450 references in 60 countries
Over 275,000 sq ft of world class
manufacturing facilities meeting global
standards.
Largest Resource Base for Bio Ethanol Industry
Diverse Global Feedstock Experience
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Praj Matrix – The Innovation Center
US$ 20+ Mn investment
80,000 sq ft of Labs, PP, and
Offices
14 Well Equipped Labs
125 technologists and growing
30 PhDs, 80 Masters
Pilot Plants
2 TPD Cellulosic Ethanol pilot plant
Two 750 kg/d Chemical pilot plants
500 sq ft Open Raceway Pond for
Algal Cultivation
IP - 11 granted patents
Bench and Pilot scale facilities to enable validation of
scientific assumptions and rapid commercialization
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Emerging Value Chain
Technology Engineering
Plant & Machinary
Customers Feed Stock
Agri- Processing Companies
• BIOFUEL • CHEMICAL • BIOCHEMICAL • FOOD • FEED • PHARMA
Technology Partners
Partnerships Across Value Chain
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The Biorefinery approach by Praj
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Mechanical and
Hydrothermal
pretreatment
C5 and C6 sugars
Enzymatic
hydrolysis
Ethanol,
i-Butanol,
Isopropanol
2,3-BDO
1.4-BDO
Propanediol
Fermentation/Bio
catalysis
Chemo-Catalysis
LA/ELA, Furfural,
HMF, polyols Ethylene, iso butylene,
Butadiene, MEK, Acrylic acid
Lignin and residues
Power and
phenolics
Lignocellulosic biomass
Asia’s first 2nd Generation ethanol plant in India
Will be converted to a biorefinery in phase II
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Thank You
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Praj Matrix – The Innovation Center
Nexant's analysis shows several clear trends:
The dominant chemicals in terms of announced capacities are methanol/DME, metathesis oils, and
ethylene.
In terms of chemical classification, bio-based alcohols, olefins and oils are the areas with the most
planned commercialization.
Fungible (i.e. drop-in) chemicals are the main focus of chemical development and represent roughly
75% of the projects examined by Nexant. If metathesis oils are not included, fungible chemicals
constitute over 90%.
There is roughly an even split between projects that use first- and second-generation feedstocks.
Some 58% of projects examined use corn, cane sugar, dextrose or plant oil as a feedstock. The
remaining 42% use cellulose, lignocellulosic biomass, or other exotic feedstocks.
But the strength of the technology alone will not determine the success or failure of these ventures. It is
unlikely that all of these projects will reach fruition.
As well as the perennial risks associated with new ventures and biotechnology, projects have to
contend with the overall economic climate. Feedstock price changes may also doom infant
technologies.
More than any other factor, this may alter whether or not bio-based routes to chemicals will be
competitive.
Although some bio-based feedstock prices have shown increased volatility - particularly corn and
sugarcane - the primary source of risk is in hydrocarbon prices.
Despite these risks, Nexant believes that nearly two-thirds of announced capacity - some 4m
tonnes/year of production by 2015 - is likely to reach completion, putting the growth at 1m tonnes/year.
Bio-based chemical producers have the potential to build extensive alternative supply chains for a
variety of chemicals. While risks in the sector remain high, newly commercializing players have the
potential to become strong competitors.
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Praj Matrix – The Innovation Center
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Emerging biobased chemcials