Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2011-08-02
2011-08-02
Witherspoon, Sikarl (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C568S840000, C568S852000, C568S860000
Reexamination Certificate
active
07989664
ABSTRACT:
Disclosed are methods for generating propylene glycol, ethylene glycol and other polyols, diols, ketones, aldehydes, carboxylic acids and alcohols from biomass using hydrogen produced from the biomass. The methods involve reacting a portion of an aqueous stream of a biomass feedstock solution over a catalyst under aqueous phase reforming conditions to produce hydrogen, and then reacting the hydrogen and the aqueous feedstock solution over a catalyst to produce propylene glycol, ethylene glycal and the other polyols, diols, ketones, aldehydes, carboxylic acids and alcohols. The disclosed methods can be run at lower temperatures and pressures, and allows for the production of oxygenated hydrocarbons without the need for hydrogen from an external source.
REFERENCES:
patent: 2965679 (1960-12-01), Conradin et al.
patent: 4223001 (1980-09-01), Novotny et al.
patent: 4401823 (1983-08-01), Arena
patent: 4476331 (1984-10-01), Dubeck et al.
patent: 4496780 (1985-01-01), Arena
patent: 4554260 (1985-11-01), Pieters et al.
patent: 4642394 (1987-02-01), Che
patent: 5019135 (1991-05-01), Sealock, Jr. et al.
patent: 5026927 (1991-06-01), Andrews et al.
patent: 5139002 (1992-08-01), Lynch et al.
patent: 5214219 (1993-05-01), Casale et al.
patent: 5306847 (1994-04-01), Gehrer et al.
patent: 5326912 (1994-07-01), Gubitosa et al.
patent: 5354914 (1994-10-01), Gubitosa et al.
patent: 5496786 (1996-03-01), Gubitosa et al.
patent: 5543379 (1996-08-01), Gubitosa et al.
patent: 5578647 (1996-11-01), Li et al.
patent: 5600028 (1997-02-01), Gubitosa et al.
patent: 5616154 (1997-04-01), Elliott et al.
patent: 5616817 (1997-04-01), Schuster et al.
patent: 5651953 (1997-07-01), Yokoyama et al.
patent: 5660602 (1997-08-01), Collier, Jr. et al.
patent: 5666923 (1997-09-01), Collier, Jr. et al.
patent: 5787864 (1998-08-01), Collier, Jr. et al.
patent: 5861137 (1999-01-01), Edlund
patent: 6059995 (2000-05-01), Topsoe et al.
patent: 6152975 (2000-11-01), Elliott et al.
patent: 6171992 (2001-01-01), Autenrieth et al.
patent: 6207132 (2001-03-01), Lin et al.
patent: RE37329 (2001-08-01), Gubitosa et al.
patent: 6280701 (2001-08-01), Autenrieth et al.
patent: 6291725 (2001-09-01), Chopade et al.
patent: 6361757 (2002-03-01), Shikada et al.
patent: 6372680 (2002-04-01), Wu et al.
patent: 6387554 (2002-05-01), Verykios
patent: 6397790 (2002-06-01), Collier, Jr.
patent: 6413449 (2002-07-01), Wieland et al.
patent: 6429167 (2002-08-01), Maeno et al.
patent: 6440895 (2002-08-01), Tonkovich et al.
patent: 6479428 (2002-11-01), Tonkovich et al.
patent: 6479713 (2002-11-01), Werpy et al.
patent: 6508209 (2003-01-01), Collier, Jr.
patent: 6570043 (2003-05-01), Elliott et al.
patent: 6607707 (2003-08-01), Reichman et al.
patent: 6670300 (2003-12-01), Werpy et al.
patent: 6677385 (2004-01-01), Werpy et al.
patent: 6699457 (2004-03-01), Cortright et al.
patent: 6739125 (2004-05-01), Mulligan
patent: 6749828 (2004-06-01), Fukunaga
patent: 6762149 (2004-07-01), Tonkovich et al.
patent: 6765101 (2004-07-01), Bhasin et al.
patent: 6841085 (2005-01-01), Werpy et al.
patent: 6953873 (2005-10-01), Cortright et al.
patent: 6964757 (2005-11-01), Cortright et al.
patent: 6964758 (2005-11-01), Cortright et al.
patent: 6969506 (2005-11-01), Tonkovich et al.
patent: 6982328 (2006-01-01), Werpy et al.
patent: 7038094 (2006-05-01), Werpy et al.
patent: 7186668 (2007-03-01), Werpy et al.
patent: 7199250 (2007-04-01), Werpy et al.
patent: 7767867 (2010-08-01), Cortright et al.
patent: 2003/0099593 (2003-05-01), Cortright et al.
patent: 2004/0175806 (2004-09-01), Werpy et al.
patent: 2005/0064560 (2005-03-01), Werpy et al.
patent: 2005/0065337 (2005-03-01), Werpy et al.
patent: 2005/0203195 (2005-09-01), Wang et al.
patent: 2005/0207971 (2005-09-01), Cortright et al.
patent: 2005/0244312 (2005-11-01), Suppes et al.
patent: 2005/0244329 (2005-11-01), Casanave et al.
patent: 2005/0271579 (2005-12-01), Rogers
patent: 2006/0013759 (2006-01-01), Jiang et al.
patent: 2007/0123739 (2007-05-01), Crabtree et al.
patent: 2007/0135301 (2007-06-01), Holcomb, Jr.
patent: 2007/0149830 (2007-06-01), Tuck et al.
patent: 2007/0173643 (2007-07-01), Werpy et al.
patent: 2007/0173651 (2007-07-01), Holladay et al.
patent: 2007/0173652 (2007-07-01), Holladay et al.
patent: 2007/0293665 (2007-12-01), Holcomb
patent: W003/045851 (2003-06-01), None
patent: WO 2007/027832 (2007-03-01), None
patent: WO 2007/053705 (2007-05-01), None
patent: WO 2007/075476 (2007-07-01), None
patent: WO 2007/099161 (2007-09-01), None
Badger, P.C., “Ethanol From Cellulose: A General Review,” Ethanol From Cellulose: A General Review (2002).
Bardin, B.B., et al, “Acidity of Keggin-Type Heteropolycompounds Evaluated by Catalytic Probe Reactions, Sorption Microcalorimetry, and Density Functional Quantum Chemical Calculations,” J. Phys. Chem. B 102:10817-10825 (1998).
Brown, N.F., et al., “Carbon-Halogen Bond Scission and Rearrangement of Beta-Halohydrins on the Rh(111) Surface,” J. Phys. Chem. 98:12737-12745 (1994).
Chen, N.Y., et al., “Liquid Fuel From Carbohydrates,” Chemtech Aug. 1986 p. 506-509.
Chiu C-W., et al., “Distrbution of Methanol and Catalysts between Biodiesel and Glycerin Phases,” AlChE Jounal 51:1274-1278 (2005).
Chiu, C-W., et al., “Removal of Residual Catalyst from Simulated Biodiesel's Crude Glycerol for Glycerol Hydrogenolysis to Propylene Glycol,” Ind. Eng. Chem. Res 45:791-795 (2006).
Cortright, R.D., “Hydrogen from catalytic reforming of biomass-derived hydrocarbons in liquid water,” Nature 418:964-967 (2002).
Crabtree, S.P., et. al., “Novel Catalysis for Glycol Manufacture”.
Dasari M.A., et al.,“Low pressure hydrogenolysis of gycerol to propylene gycol,” Applied catalysis A: General 281:225-231 (2005).
Elliott, D.C., et al., “Chemical Processing in High-Pressure Aqueous Environments. 7. Process Development for Catalytic Gasification of Wet Biomass Feedstocks,” Ind. Eng. Chem. Res. 43:1999-2004 (2004).
Fraser, J., “Roadmap for Cellulosic Ethanol Production,” U.S. Department of Energy, Jun. 2006.
Fukuoka, A., et al., “Catalytic Conversion of Cellulose into Sugar Alcohols,” Angew. Chem. Int. Ed. 45:5161-5163 (2006).
Greer, D., “Creating Cellulosic Ethanol: Spinning Straw into Fuel,” May 2005 eNews Bulletin.
Huber, G.W., et al., “Raney Ni-Sn Catalyst for H2 Production from Biomass-Derived Hydrocarbons,” Science 300:2075-2077 (2003).
Kawai M., et al., “Production of Hydrogen and Hydocarbon From Cellulose and Water,” Chemistry Letters 1981 pp. 1185-1188.
Minowa, T., et al., “Hydrogen production from Wet Cellulose by Low Temperature Gasification Using a reduced Nickel Catalyst,” Chemistry Letters 1995 pp. 937-938.
Minowa, T., et al., “Hydrogen production from Cellulose in Hot Compressed Water using Reduced Nickel Catalyst: Product Distribution at Different Reaction Temperatures,” J. of Chem. Eng. of Japan 31:488-491 (1998).
Miyazawa, T., et al., “Glycerol conversion in the aqueous solution under hydrogen over Ru/C + an ion-exchange resin and its reaction mechanism,” J. of Catalysis 240:213-221 (2006).
Nelson, D.A., et al., “Application of Direct Thermal Liquefaction for the Conversion of Cellulosic Biomass,” Ind. Eng. Chem. Prod. Res. Dev. 23:471-475 (1984).
Oregon Cellulose-Ethanol Study, Appendix B Overview of Cellulose-Ethanol Production Technology.
Rostrup-Nielsen,J.R., “Conversion of hydrocarbons and alcohols for fuel cells,” Phys. Chem. Chem. Phys. 3:283-288 (2001).
Davda, R.R., et al., “Aqueous-phase reforming of ethylene glycol on silica-supported metal catalysts,” Applied Catalysis B: Environmental 43:13-26 (2003).
Shabaker, J.W., et al., Aqueous-phase reforming of oxygenated hydrocarbons over Sn-modified Ni catalysts, J. of Catalysis 222:180-191 (2004).
Wang, D., et al., “Catalytic steam reforming of biomass-derived oxygenates: acetic acid and hydroxyacetaldehyde,”
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Virent Energy Systems, Inc.
Witherspoon Sikarl
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