Process Production of Conventional Liquid Fuels from Sugar

BioForming Process Production of Conventional Liquid Fuels from Sugar Dr. Randy D. Cortright CTO/Founder Virent Energy Systems www.virent.com ACS/EPA Green Chemistry Conference June 23, 2009

Virent s BioForming Concept Process Heat Lignin C 1 -C 4 Alkanes Aromatics, Alkanes Lignocellulosic Materials Soluble Sugars Starches Biomass Fractionation and Pretreament Hydrogenolysis Polysaccharides C 5 &C 6 Sugars Furans Phenolics Acids C 2 -C 6 Oxygenates H 2 H 2 Aqueous Phase Reforming Base Catalyzed Condensation ZSM-5 HDO Alkanes Gasoline Kerosene Jet Fuel Hydrogenation Sugar Alcohols Dehydration Alkene Oligomerization Alkene Saturation Alkanes Diesel http://www.virent.com/bioforming/virent_technology_whitepaper.pdf

BioForming Process to Liquid Fuels Carbon Number BioForming Process Glycerol Sorbitol Xylose Glucose Sucrose Polysaccharides Cellulose Hemi-Cellulose H H O O C C ] H H [ n H 2 O H H 2 C C * * H alkanes H x O C C * * H 2 O OH x H x O C H 2 C-C cleavage C * * * * OH x H 2 H 2 CO,H 2 H 2 O CO 2 WGS CO 2,H 2 3

Generation of Hydrocarbons from Sugar with In-situ Hydrogen Generation HO HO CH 2 OH O OH OH H 2 O H 2 CO 2 n-paraff ins iso-paraffins Aromatics +H 2 O Overall Theoretical Stoichiometry 3.58 C 6 H 12 O 6 -> C 14 H 30 + 7.5 CO 2 + 6.5 H 2 O Hydrocarbon contains 65 % of Sugar Carbon Hydrocarbon contains 94% of LHV of Sugar

Reaction Pathways to Liquid Fuels

Virent s Sucrose to Gasoline Process Process Heat C 1 -C 4 Alkanes C 4 -C 11 Aromatics, Alkanes Sucrose Pretreamen nt C 6 Sugars Aqueous Phase Reforming Oxygenated Intermediates ZSM-5 C 12+ Aromatic Byproduct Gasoline Kerosene Jet Fuel H 2 Hydrogenation Sugar Alcohols

Reaction of Oxygenates over ZSM-5 Isopropyl Alcohol Acetone Hydride Transfer H* Aldol Condensation/ Eneone Cracking Dehydration Acetic Acid H 2 O + Isobutene Propylene Reducing Equivalents 0.5 + 0.5 Olefin Aromatics and Pool Paraffins H* Acetic Acid Acetone Ketonization 0.5 + CO 2 H 2 O + Ethylene H* Hydride Transfer Acetaldehyde Ethanol Dehydration H* Hydride Transfer

Conversion of Sugars to Liquid Fuels A Sucrose + Xylose H 2 B Hydrogenation Ru/Carbon Aqueous Phase Reforming Pt+Re/ Carbon Tungstated Zirconia ZSM-5 %Carbon % LHV Feeds Sucrose + 100 87 Xylose Hydrogen - 12 Products CO 2 25 - H 2-3 C 1 -C 4 26 31 C 5 -C 9 43 53 C 10+ 5 6 http://www.virent.com/bioforming/virent_technology_whitep aper.pdf

Cane Sugar and Xylose to Bio-Gasoline

Bio-Gasoline Composition Same Components as Standard Unleaded Gasoline Unleaded Gasoline 115,000 BTUs/Gal Unleaded Gasoline Bioforming Green Gasoline Bioforming Green Gasoline 125,000 BTUs/Gal Ethanol 76,000 BTUs/Gal

Hydrocarbon Composition http://www.virent.com/bioforming/virent_technology_whitepa per.pdf

Bio-Gasoline PFD

Bio-Gasoline via the BioForming Process Catalytic Process: Fast process Low residence time. Feedstock Flexible: Products of cellulosic processing can be converted directly with BioForming s large process window. Can process a mixture of sugars including polysaccharides, C5 sugars, and C6 sugars. Water Positive: Bioforming makes water when taking the oxygen off of sugar streams. Low Energy Separation: Gasoline floats on water, requiring minimal distillation. Produces gasoline with >50% higher net energy yield per acre than the corn ethanol process. CO 2 Neutral: Low energy input and biomass based feedstocks offer near-zero CO 2 emissions.

Land Area 100 MGPY Bio-gasoline Illustration Wheat Straw Perennial Grasses Sugar Beets Corn & Stover Corn Sweet Sorghum Hardwoods Sugarcane & Residue Sugarcane HB Sorghum

Bio-Gasoline - Cash Cost *Internal transfer 5 cent / lb sugar price deduct 50 cent per gallon tax incentive

BioJet Fuel Jet Fuel Requires High Energy Density and Low Freeze Point Aromatic content required 23 Billion gallon domestic market Military market

Oligomerization of Olefins Jet Range (C 9 C 13 13 ) Diesel Range (C 14 C 25 14 25 ) Gasoline Range (C 5 C 8 ) Oligomerization pathway allows production of Jet as well as Diesel Components

Generation of Jet Fuel using the BioForming Process Non-Oxygenated Hydrocarbon Product Low Freezing Point High Energy Content http://www.virent.com/bioformi ng/virent_technology_whitepa per.pdf

2008 Progress- Liquid Fuels Gasoline Production Demonstrated - 1 liter/day integrated production from Sugar. - Product testing initiated- including engine testing. - Demonstrated economically viable yields to gasoline from C5 sugars, C6 sugars and sucrose. - Entering 2 nd year of Shell Collaboration Gasoline Process Demonstration in Progress - 10,000 gallons/year capacity - 35,000 sq ft facility expansion - Skid Fabrication started in November (Delivery Summer 2009) Jet Fuel - Demonstrated Jet Fuel Production - Developing Jet Fuel within a Separate Unannounced Collaboration

Virent s BioForming Technology Protected by an Extensive Intellectual Property Platform Lignocellulosic Materials Soluble Sugars Starches Biomass Fractionation and Pretreament Lignin Process Heat Hydrogenolysis Polysaccharides C 5 &C 6 Sugars Furans Phenolics Acids Hydrogenation C 2 -C 6 Oxygenates H 2 Aqueous Phase Reforming Sugar Alcohols C 1 -C 4 Alkanes H 2 Base Catalyzed Condensation Dehydration ZSM-5 HDO Alkene Oligomerization Aromatics, Alkanes Alkanes Alkene Saturation Gasoline Kerosene Jet Fuel Alkanes Diesel Fast and Robust - Inorganic Catalysts - Moderate Conditions - Industry Proven Scalability Energy Efficient - Exothermic - Low Energy Separation - Low Carbon Footprint Premium Drop-in Products - Tunable - Infrastructure Compatible Feedstock Flexible - Conventional Sugars - Non-Food Sugars

Contact Information Randy D. Cortright, PhD CTO and Founder Virent Energy Systems, Inc 3571 Anderson Street Madison, WI 53704 E-Mail: randy_cortright@virent.com Phone: 608-663-0228 Cell: 608-345-8702 Fax: 608-663-1630 www.virent.com