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(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 2014/138600 Al 12 September 2014 (12.09.2014) P O P C T (51) International Patent Classification: 61/774,723 8 March 2013 (08.03.2013) US CUP 7/ 0 (2006.01) 61/793,336 15 March 2013 (15.03.2013) US (21) International Application Number: (71) Applicant: XYLECO, INC. [US/US]; 271 Salem Street, PCT/US2014/021815 Unit E, Woburn, Massachusetts 01801 (US). (22) International Filing Date: (72) Inventors: MEDOFF, Marshall; 90 Addington Road, 7 March 2014 (07.03.2014) Brookline, Massachusetts 02445 (US). MASTERMAN, Thomas Craig; 26 Linden Street, Brookline, Massachu Filing Language: English setts 02445 (US). MUKHERJEE, Maia Stapleton; 3 Re Publication Language: English gis Road, Arlington, Massachusetts 02474 (US). COOPER, Christopher; 96 New Street, Rehoboth, Mas (30) Priority Data: sachusetts 02769 (US). 61/774,684 8 March 2013 (08.03.2013) US 61/774,773 8 March 2013 (08.03.2013) US (74) Agent: MORRELL, Dennis G.; XYLECO, INC., 271 61/774,73 1 8 March 2013 (08.03.2013) u s Salem Street, Unit E, Woburn, Massachusetts 01801 (US). 61/774,735 8 March 2013 (08.03.2013) u s (81) Designated States (unless otherwise indicated, for every 61/774,740 8 March 2013 (08.03.2013) u s kind of national protection available): AE, AG, AL, AM, 61/774,744 8 March 2013 (08.03.2013) u s AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, 61/774,746 8 March 2013 (08.03.2013) u s BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DK, DM, 61/774,750 8 March 2013 (08.03.2013) u s DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, 61/774,752 8 March 2013 (08.03.2013) u s HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, 61/774,754 8 March 2013 (08.03.2013) u s KZ, LA, LC, LK, LR, LS, LT, LU, LY, MA, MD, ME, 61/774,775 8 March 2013 (08.03.2013) u s MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, 61/774,780 8 March 2013 (08.03.2013) u s OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, 61/774,761 8 March 2013 (08.03.2013) u s SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, [Continued on nextpage] (54) Title: UPGRADING PROCESS STREAMS FIG. 1A ELECTRODIALYSIS SYSTEM 40 DEMINERALIZED 10 PRODUCT E.G. FEED PROCESS SUGARS (REDUCED (DILUTE) SALT STREAM CONCENTRATIONS E.G. SUGARS PER PASS THROUGH AND SALTS DC ELECTRODYALYSIS VOLTAGE SYSTEM) 30 20 E.G.,ION • TRANSFER, BRINE MAKEUP 50 WATER BRINE BLOWDOWN (TYPICALLY (CONCENTRATE) REVERSE STREAM WITH SALT OSMOSIS OR TRANSFERRED o SOFTENED FROM FEED CITY WATER) 00 (57) Abstract: Biomass (e.g., plant biomass, animal biomass, and municipal waste biomass) is processed to produce useful interme - o diates and products, such as energy, fuels, foods or materials.. Systems, methods and equipment are described for upgrading process streams using electrodialysis or electrodialysis reversal. ] Many potential lignocellulosic feedstocks are available today, including o agricultural residues, woody biomass, municipal waste, oilseeds/cakes and seaweed, to name a few. w o 2014/138600 A i llll II II 11III I II I III 11II II II III II I II TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, ΓΓ, LT, LU, ZW. LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, (84) Designated States (unless otherwise indicated, for every GW, KM, ML, MR, NE, SN, TD, TG). kind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, SZ, TZ, Published: UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, TJ, — with international search report (Art. 21(3)) TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, UPGRADING PROCESS STREAMS CROSS REFERENCE TO RELATED APPLICATIONS [0001] This application claims priority from the following provisional applications: USSN 61/774,684, filed March 8, 2013; USSN 61/774,773, filed March 8, 2013; USSN 61/774,731, filed March 8, 2013; USSN 61/774,735, filed March 8, 2013; USSN 61/774,740, filed March 8, 2013; USSN 61/774,744, filed March 8, 2013; USSN 61/774,746, filed March 8, 2013; USSN 61/774,750, filed March 8, 2013; USSN 61/774,752, filed March 8, 2013; USSN 61/774,754, filed March 8, 2013; USSN 61/774,775, filed March 8, 2013; USSN 61/774,780, filed March 8, 2013; USSN 61/774,761, filed March 8, 2013; USSN 61/774,723, filed March 8, 2013; and USSN 61/793,336, filed March 15, 2013. The full disclosure of each of these provisional applications is incorporated by reference herein. BACKGROUND OF THE INVENTION [0002] Many potential lignocellulosic feedstocks are available today, including agricultural residues, woody biomass, municipal waste, oilseeds/cakes and seaweed, to name a few. At present, these materials are often under-utilized, being used, for example, as animal feed, biocompost materials, burned in a co-generation facility or even landfilled. [0003] Lignocellulosic biomass includes 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 (e.g., 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 [0004] Generally, the methods and equipment used for producing useful products from a biomass material are described herein. Generally, many methods include treating a recalcitrant biomass, e. g. treating with electron beams, and then biochemically and/or chemically processing the reduced recalcitrance material to a mixture of sugars, for example, glucose, xylose, arabinose, fructose, sugar alcohols, e. g. xylitol and other products. Salts (e.g., ions) generated during processing of the feedstock can be removed via the process of electrodialysis, e. g. common or standard electrodialysis (ED), electrodialysis reversal (EDR) and/or bipolar membrane electrodialysis (EDBM). The method of electrodialysis can help in removing the bulk salts from the sugar solution, or electrodialysis can be used to separate the organic acids from other compounds in a mixture. Prior to and/or after electrodialysis the biomass liquids can be also treated to remove other impurities and color. [0005] In one aspect the invention features methods for removing and/or separating salts, partially ionized acids or fully ionized acids, from saccharified biomass liquids, such as including sugars and/or fermented liquids utilizing an electrodialysis system. The methods can therefor provide a processed solution (e.g., purified solution, upgraded process steam, purified process stream). Optionally, the electrodialysis system utilizes standard electrodialysis or electrodialysis reversal. Also optionally, the saccharified biomass liquids includes a reduced recalcitrance cellulosic or lignocellulosic material that has been saccharified. For example, saccharification can be done by utilizing one or more enzymes and/or one or more acids, such as sulfuric acid. For example, saccharification can be done by using an enzyme, using an acid, using an acid and then an enzyme, using an enzyme and then an acid or using an enzyme and an acid concurrently. Optionally, the cellulosic or lignocellulosic material has had its recalcitrance reduced by treatment with ionizing radiation (e.g., with between about 10 and about 50 Mrad of radiation). For example, the ionizing radiation can be in the form of accelerated electrons. [0006] In another embodiment the saccharified product is fermented and then electrodialysis is applied with or without purification. In this embodiment fermentation broth can often include a product from converting one of the sugars to specific product and another sugar that remains unconverted during the fermentation. The fermentation broth can be subject to electrodialysis to remove salts that it been formed. Then the product can be isolated by using a bipolar electrodialysis operation. [0007] In some implementation, while utilizing the electrodialysis system, a voltage of between about 10 and 600V across ion selective membranes can be applied while flowing the saccharified biomass liquids and/or the fermentation product liquids past the membranes. Optionally, the voltage can be between 25 and 500 V. Additionally, the voltage can be 40 to 450 V. These voltages can be across multiple membranes. [0008] In some implementations, the saccharified biomass liquids can be further processed with a fermentation step to produce fermentation products, such as an alcohol, organic acids. Optionally, the saccharified biomass liquids are liquids wherein a fermentation product (e.g., an alcohol such as ethanol, propanol or butanol or an organic acid such as acetic acid, propionic acid, succinic acid, tartaric acid, butyric acid and lactic acid) has been removed therefrom by electrodialysis or other isolation means (e.g., by distillation). [0009] In some implementations, the ionic strength of the saccharified liquid prior to electrodialysis is between about 500 and about 50,000 ιη (microSiemens/cm), and wherein an ionic strength of the saccharified biomass liquids after utilizing the electrodialysis system (e.g., the processed solution, purified solution, upgraded process steam or purified process stream) is between 1 and 100 ιη.
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    Carbohydrate Research, 129 (1984) 149-157 Elsevier Science Publishers B.V.. Amsterdam-Printed in The Netherlands ANHYDROALDITOLS IN THE SUGAR ANALYSIS OF METHANOLY- SATES OF ALDITOLS AND OLIGOSACCHARIDE-ALDITOLS* GEKKITJ. GEKWIG,JCIHANNIS P. KAM~KLIW. AND JUHANNESF. G. VLIEGENTHAKI Department of Bio-Organic Chemistry, State University of Vtrecht, Croesestraat 79, NL-3522 A D Vtrecht (The Netherlands) (Received October 13th, 1983; accepted for publication, December 16th. 1983) ABSTRACT In the context of the methanolysis procedure for sugar analysis, several al- ditols were investigated for their capacity to form anhydro derivatives in M methanolic HCl (24 h, 85’). Xylitol, D-arabinitol, L-fucitol, D-glucitol, galactitol, 2- acetamido-2-deoxy-D-galactitol, and the alditols of N-acetylneuraminic acid were very prone to form anhydrides, whereas 2-amino-2-deoxy-D-galactitol, 2-amino-2- deoxy-D-glucitol, D-mannitol, and 2-acetamido-2-deoxy-D-glucitol formed little anhydride. Anhydride formation was observed for the relevant alditols when pre- sent in reduced oligosaccharides. This finding is of importance in the quantification of sugar residues based on methanolysis, N-(re)acetylation, trimethylsilylation, and subsequent capillary g.1.c. INTRODUCTION Various derivatives are employed for the determination of the sugar compo- sition of complex carbohydrates by g.1.c. Neutral and aminodeoxy sugars, obtained by acid hydrolysis, are usually analysed as alditol acetateslM3. Methyl glycosides of neutral monosaccharides, aminodeoxy sugars, uranic acids (methyl esters), and sialic acids (methyl esters) obtained by methanolysis can be determined after N- acetylation-trimethylsilylation4-6 or trifluoroacetylation’. Each monosaccharide gives rise to a characteristic group of methyl glycosides.
  • (12) Patent Application Publication (10) Pub. No.: US 2006/0165623 A1 Workman Et Al

    (12) Patent Application Publication (10) Pub. No.: US 2006/0165623 A1 Workman Et Al

    US 2006O165623A1 (19) United States (12) Patent Application Publication (10) Pub. No.: US 2006/0165623 A1 Workman et al. (43) Pub. Date: Jul. 27, 2006 (54) NATURAL IDEODORANT COMPOSITION (57) ABSTRACT (75) Inventors: Tanya Workman, Mansonville (CA); Svetlana Ratnikova, Toronto (CA) The present invention relates to a natural deodorant system and a natural system for topical and systemic delivery of Correspondence Address: active ingredients, both systems being primarily free of Louis C. Paul, Esq. preferably substantially free of more preferably essentially CTSW free of, and most preferably completely free of ethoxylates Suite 2400 or other petrochemical derivatives, and comprising: (a) at least one of (1) glycerine (preferably of plant origin), (2) a 420 Lexington Avenue polyol selected from the group consisting of galactitol, New York, NY 10170 (US) erythritol, inositol, ribitol, dithioerythritol, dithiothreitol, (3) a Sugar alcohol, selected from the group consisting of (73) Assignee: Terra Firma Natuals, Inc. mannitol, Sorbitol. Xylitol and maltitol, (4) a hydrogenated starch hydrosylates of at least one of berries, apples or (21) Appl. No.: 11/042,569 plums, and (5) mixtures thereof; (b) water or a lower monohydric alcohol, selected from the group of methanol, (22) Filed: Jan. 24, 2005 ethanol, propanol and isoproponal, or mixtures thereof, present at a combined concentration of at least 20%; (c) one Publication Classification or more carrageenans (preferably of plant origin) or algi nates, or mixtures thereof, present in combined concentra (51) Int. C. tions of less than about 2%; and (d) optionally, one or more A6 IK 8/73 (2006.01) thickeners or gums selected from the group consisting of tara, guar, Xanthan, Arabic, tragacanth, agar, locust bean (52) U.S.