green chemistry by design - renewable bioproducts...
TRANSCRIPT
Green Chemistry by Design
Renewables – the Future of the Chemical Industry?
Ray W. Miller, GT BChE ‘72Chief Business Officer
RBI ConferenceGeorgia TechMarch 10, 2015
Agenda
• Global drivers for industrial biotechnology• Market analysis and opportunities for renewables• The case for partnering• Examples of successful partnering:
- Bio-PDO™/Sorona®- Other Platform Bio-based Molecules- PEF for bottles
• Verdezyne’s Diacid Platform• Concluding remarks
2
World Crude Oil Prices
Source: Chemtech Group
Price Volatility of Oil has Dramatically Increased
Last 5 Years Show an Upward Cost Trend
If current consumption trends continue:50% of the oil the world needs in 2030
is not yet found or developed
Recent supply/demand imbalance is not sustainable.
The Real Cost of Oil Is Actually Higher
This does not include the costsfrom defending world oil supplies.
Global Warming Consequence: Rising Sea Levels
Some models predict a rise of 6 feet by 2100
Key Questions: How do we?
Sustain a planet approaching 9 billion people?
Engineer and implement solutions that are affordable?
Enter Industrial Biotechnology
Major Drivers for Industrial Biotechnology
• Growing cost and environmental advantage vs. petrochemical routes
- Renewable feed stocks provide a hedge against rising and volatile oil prices
- Lower fossil carbon footprints provide regulatory advantages
• Need to satisfy a growing consumer preference for “sustainable” products
• Biological tools are rapidly evolving • Growing recognition that many existing petro-based products
can be made using bio-based processes
Market Force Analysis
Supply DriversPolicy
RegulationR&D Investment
Applications
OpportunitiesCost ReductionMarket GrowthSupply Control
ConstraintsDevelopment TimeCost to implement
Starting Scale
Demand DriversLCA
Cost StabilityAvailabilityPreferences
PartnershipsTo CreateBio-basedProducts
Applications
New FeedstockTechnologiesAnd Sources
Enabling Technologies:FermentationBiocatalystsThermal Conversions
Chemicals From RenewableResources*
~$200B by 2014
Market Opportunity for Renewables
*Milken study: $720B opportunityin the next decade or 20% of theChemicals markets
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PetroleumOnline.com
Value created by chemicals is up to 20X higher per ton of carbon vs. fuels
Bio-Refineries for Chemicals
Source: CBiRC
Oil refiners have shown the way.
Rings Diols
Dienes
Multifunctionals
Glucose
AcidsR
AlcoholsR
R
Olefins
Source: CBiRC
Bio-based Platform Chemical Opportunities
Diacids
Reasons for Partnering
• Secure feedstock supplies• Access scale up capabilities• Prove technology readiness• Finance commercial facilities• Provide channels to markets
R&D in this area is the focus for most new entrants
Secret to Success: Connecting the Value Chain
Technology Developers
Integrated Biological and Chemical Companies
Chemical Companies
End Users
Biomass PrimaryIntermediates
SecondaryIntermediates
BioproductsSugars Uses
Biomass Processing Refining Catalysis Intermediates Applications Uses
Biomass Processors Partnerships are Key!(no single player has it all)
Source: CBiRC
+ DMT / TPA
Application Partnerships:
• Fibers for:
– Floor Coverings
– Apparel
– Auto Interior
• Resins for:
– Molding Applications
– Packaging
• PDO Direct uses
Catalyst
1,3-propanediol (PDO)
Sorona® polymer
DuPont™ Sorona® was Commercialized thru Partnerships
nC C
OOCH2CH2CH2O
O
DuPont Tate & Lyle JV for Bio-PDO™ Production
The dawn of industrial biotech at Loudon, TN
Co-located at a corn wet mill
Butanediol (BDO)
Acrylic Acid
Source: Chemtech Group
Partnerships Enable Bio-based Value Chains
FDCA: PTA “Equivalent” from Renewable Sources
Avantium converts C5/C6 to HMF to 2,5 furandicarboxcylic acid (FDCA)FDCA can be polymerized with bio-sourced EG to Polyethylenefuran (PEF)
Coca-Cola® / Advantium Polyethylenefuran (PEF):A promising alternative to PET bottles
Building a Bio-based Chemical Intermediates Platform
Adipic acid
Sebacic acid
Dodecanedioic acid
Plasticizers
Thermoplastic polyurethane
PolyamideN6,6N6,10 N6,12others
Polyester polyols
Biodegradable plastic
Fibers
Parts
Resins
Home• carpets• upholstery• furniture Automotive/Transportation
• seats and dashboards• tire cord• lubricants• belts and hosesFoams
Elastic parts
Films
Adhesives
Resins
Spray coatings
Thermo-set articles
Ag Covering
Packaging
Industrial• commercial carpet• paints• coatings• adhesives
Personal• packaging• cosmetics• flavorings
Recreation• footwear• apparel• camping gear
End Use Markets For Major Dicarboxylic Acids
Paints/Coatings
Current Feedstocks Used for Dicarboxylic acids
Adipic Acid3,000 KTA3% CAGR
Sebacic Acid70 KTA
10% CAGR
Crude Oil
Castor Bean oil
Benzene
Butadiene
Alkanes
RicinoleicAcid
Dodecanedioic Acid
40 KTA8% CAGR
About Verdezyne
• Privately-held industrial biotech company• Formed in 2008 to develop renewable
fuels and chemicals• Current product portfolio includes
materials used in the nylon and thermoplastic polyurethane markets
• Headquartered in Carlsbad, California• 70 full-time employees• Venture backed by strategic and financial
investors
Feedstock Strategy Proprietary Technology Chemical Intermediates End-Products
• Non-food plant oils• Soap stocks and
distillates• Other oil co-products (i.e.
PKO, PFAD)
Robust yeast platform using industrial
fermentation methods Total $70B+ Market
• Nylon and polyesters• Fibers• Polyurethanes• Engineered plastics• Resins• Lubricants• Coatings• Adhesives• Corrosion inhibitors• Transparent
Thermoplastics
Total $1.5T+ Market
Using fatty acids from any source to produce
chemicals
• Organisms engineered for yield and selectivity
• Fermentation-based production
• Highest quality products
• Diacids used in fibers, polymers and coatings
• Other organic diacids• Diamines and diols from
diacids• Acrylic intermediates
Engineering Organisms & Processes for Cost-effective Renewable Chemicals
The Verdezyne Business Platform
Bio-Sebacic Acid
• Robust under industrial processing conditions
Uses inexpensive feedstocks Produces multiple products Fermentation at acidic pH Phage resistant
• Tolerant to saturating product concentrations
• Host genome sequence and advanced genetic toolbox allows rapid development for new products with no heterologous genes
Verdezyne Uses a Proprietary Yeast
A Superior Host for Production of Renewable Chemicals
FA-CoA
Acyl-CoAligase
CoA, ATPAMP, PPi
Fatty acids
Enoyl-CoAhydratase
H2O
O2
H2O2
3-L-hydroxyacyl-CoA dehydrogenase
NAD+
NADH, H+
β-ketoacylthiolase
CoA
Ac-CoA
Acyl-CoA oxidase
Ac-CoA
β-oxidation
Alkanesω-oxidation
Gen 2 strain is partially β-blocked and converts a mixture of alkanes or fatty acids with different carbon lengths to a single chain length dicarboxylic acid
Gen 3 strain in development
Dicarboxylic acidsω-oxidation
Parental strain utilizes alkanes or fatty acids as sole carbon source for growth via β-oxidation
Metabolic Engineering of a Production Strain
FAn-2-CoA
Gen 1 strain is β-blocked and converts alkanes or fatty acids to the corresponding dicarboxylic acids at high yield and selectivity
Plant Oils are Worldwide Commodities
9
1928
3
2
912
2
2 3
5
3
11
11
4
1
1
7
7
2
21
11
1
11
2
1
2
1
Coconut Cottonseed Palm Oil Peanut Olive Rapeseed Soybean SunflowerPhilippines China Colombia China EU Canada Argentina ArgentinaIndonesia India Ecuador India China Brazil EU
Pakistan Indonesia EU China RussiaMalaysia India EU TurkeyNigeria Japan India UkrainePapua New Guinea Mexico MexicoThailand US US
Production in Million MTA as of 2012
Verdezyne Uses Non-food Feedstocks
Crude Plant Oil
Degumming Degumming
Neutralization
Bleaching
Bleaching
Steam Refining-Deodorization
Deodorization
Refined Oil
Soapstock
Splitting
Free FattyAcids
Feedstocks for Verdezyne Process30
Worldwide major plant oil production (billions of pounds) in 2012 Oil Type Asia Europe Americas Other World Total Distillates PKOPalm 104.1 N/A 2.0 9.2 115.2 5.8 13.1Soybean 28.9 4.5 52.2 9.9 95.5 3.8Rapeseed/Canola 19.7 19.8 6.3 6.9 52.7 1.1Coconut 7.0 N/A 0.8 N/A 7.8 0.3Total 159.6 24.3 61.2 26.1 271.3 10.9 13.1
Est. By-products
Cost Advantaged Non-food Feedstock Strategy
• “Feedstock” is that raw material used by the organism to reproduce, for energy and to produce target chemicals
• Cost of feedstock can be from 50% to 80% of total cash cost to manufacture
• Fatty acid based production is advantaged over incumbent petrochemical production and sugars in both cost and volatility
By-products/co-products Verdezyne’s preferred feedstocks are the distillates and fatty acidsproduced in the plant oil refining and fractionation process
10x Scale Up 40x Scale Up 6x Scale Up
Proof of Concept Lab Validation Pilot Small Commercial
25,000 L
400 L
10 L1 L
• Functional pathway for production of target
• Measureable outputs
• Design fermentation process
• Commercially relevant yield (50% of maximum)
• Process optimization• Demo process at scale• Proof of concept• Produce market samples
• Data to construct commercial facility
• Establish offtake
July’11: Pilot Plant project launched
Sep’11: 400 liter pilot fermentor commissioned
Oct’11: Successful testing of first adipic acid fermentations
Jan’12: Polymer-grade adipic acid samples produced for customers
June’13: Polymer-grade dodecanedioic acid produced for customers
March’15: Running Demonstration at 25K L scale
4,000 L
9x Scale Up
Demonstration• Confirm process • Scale up samples• Reduce scale-up risk
Process Development With Rapid Scale-Up
Pounds of annual production capacity 4,000 30,000 0.5 million
Current DDDA scale
Current AA scale
Flexible Feedstocks Tested for Adipic Acid
• Laboratory scale• Oleic Acid• Crude Palm Oil• C16:C18 FAME• Tall Oil• Corn Oil• Canola Soapstock• Soy Soapstock• Peanut Oil Distillates• Tallow • PFAD• PKO FAD • Trap Grease • Yellow Grease
• Pilot scale• CPO • Oleic Acid• Canola Soapstock• C16:18 FAME• PFAD
Yellow GreaseTrap Grease
PFAD PKO FAD
FAME Canola SS
• Demonstrated process scalability
• Producing kilogram quantities of purified bio-based adipic acid for market development
• Demonstrated synthesis of renewable Nylon 6,6 polymer and fibers
• Working on lower cost Gen 3 for scale up
Consistent Performance at 300L Scale
Adipic acid HMDABiolon™ Nylon 6,6
Bio-based Adipic Acid for Renewable Nylon 6,6
Dodecanedioic Acid• Generation 1 Technology (Gen 2
to be implemented later)• Aerobic fed batch process• Final Titer over 120 g/l of DDDA • Fermentation demonstrated at
4K l and 25K l scale• Downstream purification
proven at similar scale
Bio-DDDA Process Demonstration Timeline
Process Successfully Piloted (beyond 400 L at Verdezyne)• Completed at BEI/MBI in Q1-2014• Process demonstrated at 4,000 L scale• Over 1 metric ton of Bio-DDDA producedDemonstration campaign underway• In progress now at ICM/ChemDesign• Scheduled to be completed by Q2-2015• Process now demonstrated at 25k L scale• ~50MT DDDA available for seeding the markets
Property Minimum Maximum Measured1,12 Dodecanedioic Acid (wt %) 98.6 NA > 99.4Total Nitrogen (ppm) NA 34 < 21Ash (ppm) NA 2 < 2Monobasic Acids (wt %) NA 0.08 < 0.06Iron (ppm) NA 1 < 1.0Water (wt %) NA 0.4 < 0.04Other Dicarboxylic Acids (wt %) NA 1 < 0.1
BEI FacilityBio-DDDA
N6,12 madew/Bio-DDDA
Bio-DDDA Commercialization Timeline
BioNexusStatus in Malaysia
Sime Darby $30M investment
BioXcellselected as the site for 1st
commercial plant
Full financing for the commercial plant secured
Commercial plant scheduled to be commissioned
Sept – 2013 April – 2014 Nov - 2014 Q4 - 2016
Robust Partnership & Customer Pipeline
Feedstock End Markets
Supply Agreements Offtake / Licensing / Distribution Agreements
Metabolic Engineering
Chemical Production
Joint VenturesJoint Development Agreements
Key Collaborations/Agreements in Place with Industry Leading Partners
Partnerships with Plant Oil
Processors
JDA’s for Targets and
Downstream Separations
Design/EngineeringCaptive and
Supply Partnerships
Many Expressionsof Interest
Verdezyne Status and Path ForwardVerdezyne technology enables the conversion of plant oil
byproducts into high value intermediates
Engineering industrial yeast strains with robust performance at commercial scale
Feedstock flexibility allows the conversion of different sources into commercially important chemicals
High purity DDDA, adipic acid, and sebacic acid are being produced at credible scales from renewable non-food sources
Other organic acids being piloted now as extensions of technology platform
Kilogram quantity samples of products available for qualification testing Metric ton quantities of Bio-DDDA available starting in Q1-2015 Construction of commercial facility to commence Q2-2015
Providing Markets with Bio-based Solutions
Bio-Adipic acid
Bio-Sebacic acid
Bio-Dodecanedioic Acid
Thermoplastic Polyurethane
Plasticizers
PolyamideN6,6 N6,10 N6,12
Others
Biodegradable Plastic
Polyester Polyol
Resins
Paints/Coatings
Foams
Elastic Parts
Adhesives
Fibers
Resins
Parts
Films
Films
Ag Covering
Packaging
Spray Coatings
Thermo-Set Articles
Office• commercial carpet• paints• coatings• adhesives
Automotive/Transportation• Seats and dashboards• Tire cord• lubricants• belts and hoses
Home• carpets• upholstery• furniture
Recreation• footwear• apparel• camping gear
Personal• packaging• cosmetics• flavorings
Concluding Remarks
• White Biotechnology is accelerating!
• Renewably sourced chemicals are increasingly motivated by rising oil price, price volatility and lower environmental footprint
• Societal support is on the rise
• Partnerships help with lowering risk and executing more rapidly
• Connecting the value chain is the key to success.• Chemical Engineers will help make it happen!
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