2005 OBP Biennial Peer Review Chemicals and Materials Valerie Sarisky-Reed Melissa Klembara Mark Decot November 14,2006

Introduction Major Elements in the Chemicals and Materials Platform Chemicals and materials are co-produced with ethanol or other liquid transportation fuels The liquid transportation fuels drive the economy of scale while the chemicals and materials can improve overall plant economics Products can cross a broad array of pathways including the corn wet mill, corn dry mill, lignocellulosic and oils pathways

Baseline for Chemicals and Materials from Renewables Super Commodities Multi Billion Pounds Commodities Hundreds of Million Pounds Specialties Millions of Pounds Nutra Pharma Ethylene, Propylene, BTX Acetic Acid Acrylic Acid, 1,4-BDO, THF 1,3-PDO, PLA, EG, PG, PO Isosorbide, Amines PHA’s, Acrylamides Sterols, Tocopherols Vitamin E Pharmaceuticals $ Hundreds of Dollars $ $ Tens of Dollars All prices have been escalating because of increased oil and natural gas costs

Reference Baseline Systems Figure 1: Internal Rate of Return of the Scenarios ($1.20/gallon ethanol selling price)

Major Technical Hurdles In order to be economically viable several key technical/economic barriers need to be addressed

Technical Approach The current program is focused on three basic technical approaches Direct fermentation to products Direct fermentation of glucose to produce PHA’s Direct chemical/catalytic conversion to products Production of propylene glycol from glycerol; production of polyurethanes from vegetable oils Combination of fermentation followed by chemical/catalytic conversion Production of acrylic acid and other derivatives from 3- HP

Specific Economic Targets Develop technologies that enable aerobic fermentations for the production of chemical building blocks identified in the “Top Ten” report for less than $0.35/pound from $0.10/pound sugars. Develop technologies that enable anaerobic fermentations for the production of chemical building blocks identified in the “Top Ten” report for less than $0.25/pound from $0.10/pound sugars. Develop selective aqueous phase catalytic and bio-catalytic transformations of carbohydrates for the production of building blocks at less than $0.25/pound. Develop chemical or biological transformations for the conversion of platform building blocks to secondary products, including hydrogenation, oxidation, dehydration, hydrogenolysis, and dehydroxylation at a transformation cost of between $0.03 and $0.07/pound. Develop separation technologies for recovering products from dilute (less than 25% product) aqueous solutions for less than $0.05/pound

Example of Economics Butane 1,4-Butanediol Maleic Anhydride 1,4-BDO Current Petrochemical Route Potential Biochemical Route Glucose Succinic Acid 1,4-BDO Oxidation HydrogenationPurification Hydrogenation Purification Fermentation $0.08/lb$ /lb$ /lb $0.08/lb$ /lb$ /lb

TitleOrganizationFY04FY05FY06 Development of Yeast for the Fermentation of Agricultural Feedstocks to Chemicals NatureWorks, LLC $399,434$55,0000 (project completed) Fungal GenomicsPNLNA$1,200,000$1,500,000 Advanced Catalysis Development for Polyolsl Production PNL/ADM/UOP$350,000$900,000$800,000 Pyrolysis Oil Upgrading ProjectPNL/UOP/NREL$675,000$360,000TBD New Sustainable Chemicstry for Adhesives, Elastomers, and Foams Rohm & Haas Company $750,000$450,000$1,000,000 Separative BioreactorANL/ADM$450,000$250,000 Development of Improved Chemicals and Plastics from Oilseeds Dow Chemical Company $2,418,698$1,000,000$437,000 Platform Chemicals for an Oilseed Biorefinery Cargill$873,000$406,000TBD Biomass Biorefinery for the Production of Polymers and Fuels Matabolix, Inc$1,600,000$800,000$1,800,000 TOTAL C&M Projects (does not include 04 earmarks)$7,516,132$5,221,000$5,786,698 % of Total FY Budget for Products27%32%36% Project Overview

Earmarked Projects TitleRecipientFY04 Biobased Products by the New Uses Information and Entrepreneur Development Center, Belvidere, IL City of Belviedere, Illinois $981,000 Development of Sustainable Biobased Products and Bioenergy at Purdue University in Cooperaiton with the Midwest Consortium for Sustainable Biobased Products and Bioenergy* Purdue University$1,963,000 Reactive distillation for esterification of bio-based organic acids* NCGA$1,000,000 Maine Forest Bioproducts R&D*Maine Technology Institute $981,000 TOTAL Chemical and Material related Earmarks$4,925,000 C&M earmarks as % of Total Products Funding for FY0418% C&M projects (including earmarks) as % of Total Products Funding for FY0445% Earmarked projects related to Chemicals and Materials R&D (*participated in the Aug 05 Interim Stage Gate Review) (All are included in poster session)

Project Overview Project Development of Yeast for the Fermentation of Agricultural Feedstocks to Chemicals (Lactic Acid and Ethanol) Project Team Nature Works, Abengoa Energy Major Technical Objective Develop a yeast strain capable of fermenting xylose to lactic acid and ethanol Lactic acid: 80 % yield, 1g/L*h productivity Major Economic Target Reduce the production cost of PLA by 30% Barriers Addressed Improve fermentation productivity Utilization of five carbon sugars Reduction in capital costs Organism development

Project Overview Pathways Addressed Corn wet mill, corn dry mill and lignocellulosic Project Budget 2005 $55, $0 Significant Comments from Interim Stage Gate Review (review held on August 9, 2005) Excellent strategic fit with program goals Reduced cost affords clear competitive advantage Success could be undermined by issues with hydrolysate (organism robustness to impurities) Path Forward Project is complete and not requesting additional funding

Project Overview Project Fungal genomics: to develop tools to enable application of fungal fermentation technology to produce Top Ten products in the biorefinery Project Team PNNL and an external Partners Review Board (Cargill, Tate &Lyle, GPC,,Genencor, Novozymes, Dyadic, ICPB, Diversa ) Major Technical Objective Demonstrate in model a system(s) that genome-based tools improve product yield and productivity (e.g. Organic acid: 80 % yield, 1g/L*h productivity) Major Economic Target Reduce the production cost of Top Ten products Barriers Addressed Improve fungal fermentation productivity Control Morphology Define and control Hyper-producivity Develop genome-based tools to shorten process development time Transfer genome-based tools to bioprocess improvement Organism development

Project Overview Pathways Addressed Corn wet mill, corn dry mill and lignocellulosic Project Budget 2005 $ 1,200, $ 1,500,000 Significant Comments from Interim Stage Gate Review (review held on August 9, 2005) Fungal systems could prove to be a valuable system. The linkages to the goals and objectives of the MYTP were clearly presented. Project has great potential for this relatively unexplored area. Path Forward The project milestones are being adjusted to meet budg et

Project Overview Project Advanced Catalyst Development for Converting Glycerol to Propylene Glycol Project Team ADM, UOP, PNNL Major Technical Objective Develop a highly selective catalyst for conversion of glycerol to PG Conversion 90%, Selectivity 90%, 1 Year catalyst lifetime Major Economic Target PG production at a cost of 80-90% of current technology from propylene Barriers Addressed Catalyst development in aqueous phase Improve catalyst selectivity and robustness Cost reduction for chemical conversion

Project Overview Pathways Addressed Oil biorefinery (creates value from glycerol produced with biodiesel) Project Budget 2005 $700, $800,000 Significant Comments from Interim Stage Gate Review (review held on August 9, 2005) Excellent strategic fit with program goals Ensures financials/metrics are on target Milestones well established Feedstock and scale up critical to making this a desirable commercial project Path Forward Project is moving forward on schedule to meet milestones

Project Overview Project Pyrolysis Oil Upgrading Project Team UOP, PNNL, NREL Major Technical Objective Development of enabling technology for pyrolysis-based methods to introduce biomass into a petroleum refinery Major Economic Target Product costs need to be competitive with petroleum feedstocks 4 year plant payback at $50/barrel crude oil Barriers Addressed Catalyst development Improve catalyst selectivity and robustness Cost reduction for chemical conversion

Project Overview Pathways Addressed Lignocellulosic biorefinery Project Budget 2005 $360, TBD Significant Comments from Interim Stage Gate Review (review held on August 9, 2005) Customers and markets identified UOP involvement critical step The alignment of project activities with MYTP objectives was clearly pointed out Industry partnerships will help clarify targets Path Forward Project is moving forward on schedule to meet milestones within budget

Project Overview Project New Sustainable Chemistry for Adhesives, Elastomers and Foams Project Team Rohm and Haas, Virginia Tech Major Technical Objective Develop new, commercially-viable biobased, non-isocyanate based chemistries to replace existing 2-part polyurethane adhesives for various uses Major Economic Target Broad application at $1.20-$2.00/pound Required costs and performance appear achievable for adhesives for initial target markets Barriers Addressed Catalyst development Improved “chemistry”/catalysts for polymers Cost reduction for chemical conversion

Project Overview Pathways Addressed Oils biorefinery and corn wet milling Project Budget 2005 $450, $1,000,000 Significant Comments from Interim Stage Gate Review (review held on August 9, 2005) Excellent project from the MYTP perspective. Technical barriers well identified and discussed thoroughly The competitive advantages of the adhesives and foams are not entirely (or perhaps even significantly) based on cost-question about widespread adoption of commodity materials like these bases. Path Forward Project is moving forward on schedule to meet milestones within budget

Project Overview Project Separative Bioreactor Project Team ADM, ANL Major Technical Objective Develoment of a membrane ED process for the direct capture of organic acids from fermentation broths Major Economic Target Reduce fermentation/recovery costs of organic acids by 20-30% Barriers Addressed Improve fermentation productivity Lower cost of recovery Eliminate waste streams associated with fermentation (cost reduction) Separation technology development

Project Overview Pathways Addressed Corn wet mill, corn dry mill and lignocellulosic Project Budget 2005 $250, $250,000 Significant Comments from Interim Stage Gate Review (review held on August 9, 2005) Excellent strategic fit with program goals Reduced cost affords clear competitive advantage Ability to integrate into current plants; incremental capital and manpower costs relative to benefit may not be realized with commodities versus value added (being addressed by ADM) Path Forward Working within current budget to meet commercial targets and project milestones

Project Overview Project Development of Improved Chemicals and Plastics from Oilseeds Project Team DOW, USDA, Castor Oil Inc. Major Technical Objective Develop new, commercially viable chemical processes and enabling catalyst technologies to convert seed oils to novel materials and polymers. Comparable properties to existing products. Major Economic Target Overall economics must be competitive with existing petrochemical based targets Barriers Addressed Improve catalyst performance Lower cost of recovery Product yield Catalyst development

Project Overview Pathways Addressed Oil biorefinery Project Budget 2005 $1,000, $437,000 Significant Comments from Interim Stage Gate Review (review held on August 9, 2005) An area of potential interest but little developed so it was worth the investment LCA work was of good value and was a strong outcome Technical and market knowledge Seems very internal to DOW with little technology transfer to the outside world except through IP protection. Path Forward Working within current budget to meet commercial targets and project milestones

Project Overview Project Development of Improved Chemicals and Plastics from Oilseeds Project Team Cargill Major Technical Objective Identify and optimize metathesis catalysts and associated processes as applied to unsaturated fatty acids and products derived there from Major Economic Target Overall economics must be competitive with existing petrochemical based targets Barriers Addressed Improve catalyst performance Lower cost of recovery Product yield Catalyst development

Project Overview Pathways Addressed Oil biorefinery Project Budget 2005 $406, TBD Significant Comments from Interim Stage Gate Review (review held on August 9, 2005) Internal knowledge, capabilities and commitment. Clear industrial focus and commercialization drive DOE’s work catalyzed some commercial products although not specifically in the product lines they anticipated Performance indicators were not clearly/quantitatively defined, but it is understood that these are internal Path Forward Working within current budget to meet commercial targets and project milestones

Project Overview Project Biomass Biorefinery for Production of Polymers and Fuels Project Team Metabolix, Inc. Major Technical Objective Identify and optimize fermentation organism for the production of PHA’s to achieve commercially viable polymers; 90% polymer recovery and 99% polymer purity Major Economic Target Overall economics must be competitive with existing petrochemical based targets Barriers Addressed Organism development Lower cost of recovery Product yield Feedstock utilization

Project Overview Pathways Addressed Corn wet mill, corn dry mill, lignocellulosic Project Budget 2005 $800, $1,800,000 Significant Comments from Interim Stage Gate Review (review held on August 9, 2005) Linking with ADM and British Petroleum is a good sign that the work has commercial potential Clear focus on what they can do with limited resources Nice staggering of commercial introductions based on demonstrated success Price points may not be attractive enough for large markets with large energy impacts. Path Forward Working within current budget to meet commercial targets and project milestones

Program Summary Program has several specific projects that are addressing the barriers identified in the multi-year technical plan Barriers are identified within each project and progress is monitored project by project to ensure progress towards overall program goals Project portfolio is well suited to support the biorefinery concept- several projects are poised for commercial success In the future: Product specific projects will be rolled up into the integrated biorefinery platform Core research directed at overcoming major barriers will continue Continuation of projects will be based on likelihood of success, commercial potential and availability of funding