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WO 2014/138594 Al 12 September 2014 (12.09.2014) P O P C T

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WO 2014/138594 Al 12 September 2014 (12.09.2014) P O P C T (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization International Bureau (10) International Publication Number (43) International Publication Date WO 2014/138594 Al 12 September 2014 (12.09.2014) P O P C T (51) International Patent Classification: ue, Unit 1, Somerville, Massachusetts 02143 (US). PA- C12P 7/52 (2006.01) POULIS, Andrew; 186 Turnpike Street, Canton, Mas sachusetts 02021 (US). KORYABKINA, Natalya A.; (21) International Application Number: 6214 Avalon Drive, Wilmington, Massachusetts 01887 PCT/US20 14/02 1796 (US). (22) International Filing Date: (74) Agents: MORRELL, Dennis G. et al; 271 Salem Street, 7 March 2014 (07.03.2014) Unit L, Woburn, Massachusetts 01801 (US). (25) Filing Language: English (81) Designated States (unless otherwise indicated, for every (26) Publication Language: English kind of national protection available): AE, AG, AL, AM, AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, (30) Priority Data: BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, 61/774,684 8 March 2013 (08.03.2013) US DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, 61/774,773 8 March 2013 (08.03.2013) US HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, 61/774,73 1 8 March 2013 (08.03.2013) us KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, 61/774,735 8 March 2013 (08.03.2013) us MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, 61/774,740 8 March 2013 (08.03.2013) us OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, 61/774,744 8 March 2013 (08.03.2013) us SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, 61/774,746 8 March 2013 (08.03.2013) us TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, 61/774,750 8 March 2013 (08.03.2013) us ZW. 61/774,752 8 March 2013 (08.03.2013) us 61/774,754 8 March 2013 (08.03.2013) us (84) Designated States (unless otherwise indicated, for every 61/774,775 8 March 2013 (08.03.2013) us kind of regional protection available): ARIPO (BW, GH, 61/774,780 8 March 2013 (08.03.2013) us GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, 61/774,761 8 March 2013 (08.03.2013) us UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, 61/774,723 8 March 2013 (08.03.2013) us TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, 61/793,336 15 March 2013 (15.03.2013) us EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, (71) Applicant: XYLECO, INC. [US/US]; 271 Salem Street, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, GW, Unit L, Woburn, Massachusetts 01801 (US). KM, ML, MR, NE, SN, TD, TG). (72) Inventors: MEDOFF, Marshall; 90 Addington Road, Published: Brookline, Massachusetts 02445 (US). MASTERMAN, Thomas Craig; 6 Marshall Street, Rockport, Massachu — with international search report (Art. 21(3)) setts 01966 (US). FINN, Michael W.; 215 Highland Aven (54) Title: PROCESSING AND TRANSFORMING BIOMASS FIG. 2 (57) Abstract: Biomass (e.g., plant biomass, animal biomass, and municipal waste biomass) is processed to produce useful interme diates and products, such as energy, fuels, foods or materials. The saccharified biomass is fermented in two steps to form two separ - ate products. The second product can be a carboxylic acid which is reacted with an alcohol to form an ester. The alcohol used for the esterification may be obtained from the biomass. The ester is hydrogenated to alcohols with catalysts. PROCESSING AND TRANSFORMING BIOMASS CROSS REFERENCE TO RELATED APPLICATIONS [0001] This application incorporates by reference the full disclosure of the following co pending provisional applications: the co-pending provisionals filed March 8, 2013: USSN 61/774,684; USSN 61/774,773; USSN 61/774,731; USSN 61/774,735; USSN 61/774,740; USSN 61/774,744; USSN 61/774,746; USSN 61/774,750; USSN 61/774,752; USSN 61/774,754; USSN 61/774,775; USSN 61/774,780; USSN 61/774,761; USSN 61/774,723; and USSN 61/793,336, filed March 15, 2013. BACKGROUND OF THE INVENTION [0002] As demand for petroleum increases, so too does interest in renewable feedstocks for manufacturing biofuels and biochemicals. The use of lignocellulosic biomass as a feedstock for such manufacturing processes has been studied since the 1970s. Lignocellulosic biomass is attractive because it is abundant, renewable, domestically produced, and does not compete with food industry uses. [0003] Many potential lignocellulosic feedstocks are available today, including agricultural residues, woody biomass, municipal waste, oilseeds/cakes and sea weeds, to name a few. At present these materials are either used as animal feed, biocompost materials, burned in a co-generation facility or are landfilled. [0004] Lignocellulosic biomass comprises crystalline cellulose fibrils embedded in a hemicellulose matrix, surrounded by lignin. This produces a compact matrix that is difficult to access by enzymes and other chemical, biochemical and/or biological processes. Cellulosic biomass materials (i.e., biomass material from which the lignin has been removed) is more accessible to enzymes and other conversion processes, but even so, naturally- occurring cellulosic materials often have low yields (relative to theoretical yields) when contacted with hydrolyzing enzymes. Lignocellulosic biomass is even more recalcitrant to enzyme attack. Furthermore, each type of lignocellulosic biomass has its own specific composition of cellulose, hemicellulose and lignin. SUMMARY [0005] Generally, this invention relates to systems, methods and processes for converting a biomass feedstock, e.g., cellulosic, starchy or lignocellulosic materials, to useful primary products, for example, alcohols, acids, esters, and sugars. The invention also relates to equipment, methods and systems to convert these primary products to useful secondary products, for example, converting esters by hydrogenolysis to alcohols (e.g., n-butanol, sec- butanol, iso-butanol, t-butanol, ethanol, and mixtures of any of these). [0006] In one aspect the invention relates to methods of making products. The method includes producing one or more acids (e.g., acetic acid, n-butyric acid, iso-butyric acid) from biomass, e. g., saccharified biomass, sugars e. g., sugar in a saccharified biomass, the sugar fraction of a saccharified biomass, and converting the one or more acids into one or more esters. The method further includes hydrogenating the one or more esters utilizing a catalyst and hydrogen to produce one or more products, such as alcohols. Optionally, the one or more acids are produced by fermentation of the saccharified biomass sugars. Optionally, the saccharified biomass sugars are produced by saccharification of a cellulosic or lignocellulosic biomass material with one or more enzymes and/or one or more acids, such as by first using an acid and then using the one or more enzymes. The method can also further include recalcitrance reducing the cellulosic or lignocellulosic material e. g., by electron beam irradiation, e.g., delivering a dose of irradiation is between 10 and 200 Mrad to the material. Optionally, the catalyst can include a metal such as Pt, Pd, Re, Os, Ru, Rb, Ni, Co, Mo, W, n, Cr, Cu oxides of these and combinations of these. During the hydrogenation, a hydrogen pressure between about 5 and 120 atm. while utilizing the catalyst to produce one or more alcohols. Optionally, the method includes isolating at least one of the carboxylic acids (e.g., butyric acid) prior to converting the one or more acids into one or more esters (e.g., ethyl butyrate). Optionally, the method can be used to produce esters including ethyl butyrate, butyl butyrate, hexyl butyrate, and octyl butyrate. The alcohol portion of the ester maybe derived from biomass processing or by petrochemical processing. The carboxylic acid and alcohol can be reacted by known chemical processes to obtain the ester. [0007] Another aspect of the invention features a method for making a product including converting the product of the fermentation of a saccharified treated lignocellulosic material to an ester, and producing an alcohol by passing the ester over a first catalyst e. g., a catalyst in the presence of hydrogen. The method can further include passing the ester over a second catalyst e. g., a catalyst. The first and the second catalysts can be different kinds of catalysts, for example they can have different compositions (e.g., including supports such as silica and AI2O 3) . Alternatively, the first and second catalyst can be the same kind of catalysts. [0008] In some implementations the method includes applying a first pressure of hydrogen while passing the ester over the first catalyst and applying a second pressure of hydrogen while passing the ester over the second catalyst, wherein the first pressure is higher than the second pressure by at least 0.5 atm. Optionally, the method can further include heating the first catalyst to a first temperature while passing the ester over the first catalyst and heating the second catalyst to a second temperature while passing the ester over the second catalyst, wherein the first temperature is higher than the second temperature by at least 10 0 C. Alternatively, the temperature of the second reactor can be higher than the first and the pressure can be increased between the two reactors. Optionally, the first and second catalysts can include metals in their compositions that include Pt, Pd, Re, Os, Ru, Rb, Ni, Co, Mo, W, n, Cr, Cu, oxides of these and combinations of these.
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