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Bottles R O O OH OH OH R

Bottles R O O OH OH OH R OH R Xylose Oligomers HO O O OH OH O HO OH OH OH HO O OH O O O OH OH OH HO Cellulose Oligomers O O O OH HMF OH OH OH OH Glucose O OH Benzoic Acid OH OH Xylose OH O O Levulinic Acid OH OH R R R R O O O OH R HO OH R OH O O O OH O OH APR Reactant APR Products Figure 3. Virent uses catalysts to reduce the oxygen content of the feedstock. Once formed, the mono-oxygenated species are converted to non-oxygenated hydrocarbons in a continuous process using conventional catalytic condensation and hydrotreating techniques. Virent Energy Systems, Inc. Virent was founded in 2002 and is headquartered in Madison, WI, USA. The company produces the chemicals and fuels the world demands from a wide range of naturally occurring, renewable resources. Using patented catalytic chemistry, Virent converts soluble biomass-derived sugars into products molecularly-identical to those made with petroleum, including gasoline, diesel, jet fuel, and chemicals used for plastics and fibers. Virent’s technology has the potential to replace over 90% of the products derived from a barrel of crude oil. technology with modified conventional catalytic processing technologies. The APR technology was discovered at the University of Wisconsin in 2001 by Virent’s founder and Chief Technology Officer, Dr. Randy Cortright. The BioForming platform expands the utility of the APR process by combining APR with catalysts and reactor systems similar to those found in standard petroleum oil refineries and petrochemical complexes. The process converts aqueous carbohydrate solutions into a mix of hydrocarbons. The BioForming process has been demonstrated with conventional sugars as well as a wide variety of cellulosic biomass from non-food sources. Virent’s aqueous phase reforming methods utilize heterogeneous catalysts at moderate temperatures (450 to 575 K) and pressure (10 to 90 bar) in a number of series and parallel reactions to reduce the oxygen content of the feedstock. The reactions include: (1) reforming to generate hydrogen, (2) dehydrogenation of alcohols/hydrogenation of carbonyls; (3) deoxygenation reactions; (4) hydrogenolysis; and (5) cyclization. Once formed, Virent has found that these mono-oxygenated species (e.g. alcohols, ketones and aldehydes) can be converted to non-oxygenated hydrocarbons in a continuous process using conventional catalytic condensation and hydrotreating techniques. The production of Virent’s bio-paraxylene, branded BioFormPX involves the APR process followed by a modified acid condensation catalyst (ZSM-5) which produces a stream similar to a petroleum derived reformate, branded BioFormate. In the acid condensation step, the APR products are converted into a mixture of hydrocarbons, including paraffins, aromatics and olefins. The similarity between Virent’s BioFormate stream and a typical petroleum reformate stream is shown in Fig 4. The resultant BioFormate stream has been blended into the gasoline pool and can be subsequently processed into high value chemical intermediates, such as paraxylene using commercially proven and practiced technologies. Virent’s BioFormate stream has been blended by Royal Dutch Shell into a gasoline fuel used by the Scuderia Ferrari Formula 1 racing team. Virent has produced sufficient quantities of its BioFormate through operation of its 37,800 Liter (10,000 gallon) per year demonstration plant to generate volumes for further processing to paraxylene. Virent completed in house purification through the use of commercial crystallization techniques to produce a purified bio-paraxylene product. The use of crystallization technology is used to meet the industry required specification of 99.7+% purity. 16 bioplastics MAGAZINE [04/11] Vol. 6

Bottles Petroleum Reformate Stream Virent’s BioFormate Figure 4: Virent’s plant-based reformate bears striking resemblance to that found at a typical refinery Road to Commercialization Virent is currently in discussions with a number of major end users of PET fiber, bottle resin and film, to commercialize the BioForming platform for the production of BioFormPX. Manufacturers involved in the traditional petrochemical PET supply chain have also expressed interest in contributing to building out the biobased PET supply chain. The ability of Virent to use existing petrochemical assets and technologies accelerates the time to commercial deployment. Virent is targeting commercial production of its BioFormPX by 2015 or earlier and believes that the demand pull from the major end users of PET is crucial to the initial commercialization and success of bio-based PET. Virent’s BioForming platform for BioFormPX produces other bio-based aromatic intermediates, including benzene, toluene and other xylenes, as well as biofuels. These other aromatic intermediates can be used to produce biobased polystyrene, polycarbonate, and polyurethane. This diversified product slate allows for de-risking of commercial deployments as the profitability is not dependent on one molecule or market. Virent has produced material that would be suitable using today’s aromatics processing infrastructure from its 37,800 Liter per year demonstration plant. While that is sufficient volume to provide samples to prospective partners, the current demand for plant-based paraxylene is even more significant and is poised to grow at high rates in the future. Virent envisions the BioForming platform as being an industry wide solution enabling 100% bio-based PET while complementing petroleum based PET. The ability of Virent to use existing petrochemical assets and technologies accelerates the time to commercial deployment. The scale of this plant is yet to be finalized and will depend on a number of factors including feedstock source, logistics, and customer demand. Potential plant sizes range from 30,000 tonnes/yr to 225,000 tonnes/yr of BioFormPX production. The large scale plant could produce 30 Billion 0.295 Liter (10 oz) bio PET water bottles or 17 Billion 0.590 Liter (20 oz) bio PET soft drink bottles. The introduction of this first plant can have a large impact on the PET bottle industry and the implementation of future plants will increase the impact. Figure 5. Virent’s 10,000 gallon/yr BioFormate demonstration plant (top) and Virent’s BioFormPX (bottom) in its crystalline form during in house purification. bioplastics MAGAZINE [04/11] Vol. 6 17

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