Methods and systems for generating polyols
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 glycol 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.
- Inventors:
- Issue Date:
- Research Org.:
- Virent, Inc., Madison, WI (United States)
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1531839
- Patent Number(s):
- 8198486
- Application Number:
- 13/170,757
- Assignee:
- Virent, Inc. (Madison, WI)
- Patent Classifications (CPCs):
-
B - PERFORMING OPERATIONS B01 - PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL B01J - CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY
C - CHEMISTRY C01 - INORGANIC CHEMISTRY C01B - NON-METALLIC ELEMENTS
- DOE Contract Number:
- FG36-05GO15046
- Resource Type:
- Patent
- Resource Relation:
- Patent File Date: 2011-06-28
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 09 BIOMASS FUELS; 08 HYDROGEN; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Citation Formats
Cortright, Randy D. Methods and systems for generating polyols. United States: N. p., 2012.
Web.
Cortright, Randy D. Methods and systems for generating polyols. United States.
Cortright, Randy D. Tue .
"Methods and systems for generating polyols". United States. https://www.osti.gov/servlets/purl/1531839.
@article{osti_1531839,
title = {Methods and systems for generating polyols},
author = {Cortright, Randy D.},
abstractNote = {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 glycol 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.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2012},
month = {6}
}
Works referenced in this record:
Method for the catalytic conversion of organic materials into a product gas
patent, April 1997
- Elliott, Douglas C.; Sealock, Jr., L. John; Baker, Eddie G.
- US Patent Document 5,616,154
Steam reformer with internal hydrogen purification
patent, January 1999
- Edlund, David J.
- US Patent Document 5,861,137
Conversion of hydrocarbons and alcohols for fuel cells
journal, January 2001
- Rostrup-Nielsen, Jens R.
- Physical Chemistry Chemical Physics, Vol. 3, Issue 3
Method of producing hydrogen from biomass
patent, July 1997
- Yokoyama, Shinya; Ogi, Tomoko; Minowa, Tomoaki
- US Patent Document 5,651,953
Converting sugars to sugar alcohols by aqueous phase catalytic hydrogenation
patent, May 2003
- Elliott, Douglas C.; Werpy, Todd; Wang, Yong
- US Patent Document 6,570,043
Low-temperature hydrogen production from oxygenated hydrocarbons
patent-application, September 2005
- Cortright, Randy D.; Dumesic, James A.
- US Patent Application 11/124717; 20050207971
Systems and methods for hydrogen production
patent-application, January 2006
- Jiang, Yi; Wright, Harold A.; Jack, Doug S.
- US Patent Application 10/889740; 20060013759
Catalyst system for converting oxygenated hydrocarbons to aromatics
patent, April 2002
- Wu, An-hsiang; Drake, Charles A.
- US Patent Document 6,372,680
Manufacture of 1,2-propylene glycol
patent, April 1994
- Gehrer, Eugen; Harder, Wolfgang
- US Patent Document 5,306,847
Internal combustion engine with SCR and integrated ammonia production
patent, May 2004
- Mulligan, D. Neal
- US Patent Document 6,739,125
Production of hydrogen from carbon monoxide and water
patent, September 1980
- Novotny, Miroslav; Anderson, Lowell R.
- US Patent Document 4,223,001
Hydrogen Production from Wet Cellulose by Low Temperature Gasification Using a Reduced Nickel Catalyst
journal, October 1995
- Minowa, Tomoaki; Ogi, Tomoko; Yokoyama, Shin-ya
- Chemistry Letters, Vol. 24, Issue 10
Low-pressure hydrogenolysis of glycerol to propylene glycol
journal, March 2005
- Dasari, Mohanprasad A.; Kiatsimkul, Pim-Pahn; Sutterlin, Willam R.
- Applied Catalysis A: General, Vol. 281, Issue 1-2, p. 225-231
Low-temperature hydrogen production from oxygenated hydrocarbons
patent, November 2005
- Cortright, Randy D.; Dumesic, James A.
- US Patent Document 6,964,758
Low-temperature hydrogen production from oxygenated hydrocarbons
patent, November 2005
- Cortright, Randy D.; Dumesic, James A.
- US Patent Document 6,964,757
Method of producing lower alcohols from glycerol
patent-application, November 2005
- Suppes, Galen J.; Sutterlin, William Rusty; Dasari, Mohanprasad
- US Patent Application 11/088603; 20050244312
Catalyst, method of making, and reactions using the catalyst
patent, July 2004
- Tonkovich, Anna Lee; Wang, Yong; Gao, Yufei
- US Patent Document 6,762,149
Reformed natural gas for powering an internal combustion engine
patent, January 2003
- Collier, Jr., R. Kirk
- US Patent Document 6,508,209
Special purpose blends of hydrogen and natural gas
patent, August 1992
- Lynch, Frank; Marmaro, Roger W.
- US Patent Document 5,139,002
Methods of producing compounds from plant material
patent, January 2006
- Werpy, Todd; Schmidt, Andrew J.; Frye, Jr., John G.
- US Patent Document 6,982,328
Hydrogen enriched natural gas as a clean motor fuel
patent, August 1997
- Collier, Robert; Hoekstra, Robert L.; Mulligan, David Neal
- US Patent Document 5,660,602
Low temperature methods for hydrogen production
patent-application, December 2005
- Rogers, Charles J.
- US Patent Application 11/143301; 20050271579
Production of Hydrogen and Hydrocarbon from Cellulose and Water
journal, August 1981
- Kawai, Maki; Kawai, Tomoji; Tamaru, Kenzi
- Chemistry Letters, Vol. 10, Issue 8
Method of hydrogenating glycerol
patent, May 1993
- Casale, Bruno; Gomez, Ana Maria
- US Patent Document 5,214,219
Catalyst for the production of polyols by hydrogenolysis of carbohydrates
patent-application, June 2007
- Holcomb, JR., Dale E.
- US Patent Application 11/296913; 20070135301
Long life hydrocarbon conversion catalyst and method of making
patent, November 2002
- Tonkovich, Anna Lee; Wang, Yong; Gao, Yufei
- US Patent Document 6,479,428
Hydrogenolysis of sugar feedstock
patent-application, May 2007
- Crabtree, Simon Peter; Tyers, Derek Vincent
- US Patent Application 10/576487; 20070123739
Hydrogen from catalytic reforming of biomass-derived hydrocarbons in liquid water
journal, August 2002
- Cortright, R. D.; Davda, R. R.; Dumesic, J. A.
- Nature, Vol. 418, Issue 6901
Process and preparation of hydrogen-rich gas
patent, May 2000
- Topsoe, Haldor F. A.; Dybkj. ae butted. r., Ib; Nielsen, Poul Erik Højlund
- US Patent Document 6,059,995
Textured catalysts, methods of making textured catalysts, and methods of catalyzing reactions conducted in hydrothermal conditions
patent, December 2003
- Werpy, Todd; Frye, Jr., John G.; Wang, Yong
- US Patent Document 6,670,300
Aqueous-phase reforming of oxygenated hydrocarbons over Sn-modified Ni catalysts
journal, February 2004
- Shabaker, J. W.; Huber, G. W.; Dumesic, J. A.
- Journal of Catalysis, Vol. 222, Issue 1, p. 180-191
Two stage hydrogenolysis of carbohydrate to glycols using sulfide modified ruthenium catalyst in second stage
patent, October 1984
- Dubeck, Michael; Knapp, Gordon G.
- US Patent Document 4,476,331
Preparation of 1,2-propanediol
patent, April 1997
- Schuster, Ludwig; Eggersdorfer, Manfred
- US Patent Document 5,616,817
Chemical Processing in High-Pressure Aqueous Environments. 7. Process Development for Catalytic Gasification of Wet Biomass Feedstocks
journal, April 2004
- Elliott, Douglas C.; Neuenschwander, Gary G.; Hart, Todd R.
- Industrial & Engineering Chemistry Research, Vol. 43, Issue 9, p. 1999-2004
Production of hydrogen from hydrocarbons and oxygenated hydrocarbons
patent, August 2003
- Reichman, Benjamin; Mays, William
- US Patent Document 6,607,707
Application of direct thermal liquefaction for the conversion of cellulosic biomass
journal, September 1984
- Nelson, David A.; Molton, Peter M.; Russell, Janet A.
- Industrial & Engineering Chemistry Product Research and Development, Vol. 23, Issue 3
Method for producing lower polyhydric alcohols and a new ruthenium-based catalyst used in this method
patent, February 1997
- Gubitosa, Giuseppe; Casale, Bruno
- US Patent Document 5,600,028
Two stage process for improving the catalyst life of zeolites in the synthesis of lower olefins from alcohols and their ether derivatives
patent, November 1985
- Pieters, Wim J. M.; Okumura, Yoshiharu
- US Patent Document 4,554,260
Hydrogenation catalyst, and a method for its preparation and use, in particular for hydrogenation and/or hydrogenolysis of carbohydrates and polyhydric alcohols
patent, July 1994
- Gubitosa, Guiseppe; Casale, Bruno
- US Patent Document 5,326,912
Method for the catalytic conversion of lignocellulosic materials
patent, May 1991
- Sealock, Jr., L. John; Elliott, Douglas C.
- US Patent Document 5,019,135
Tailored Fischer-Tropsch synthesis product distribution
patent-application, September 2005
- Wang, Yong; Cao, Chunshe; Li, Xiaohong Shari
- US Patent Application 10/911976; 20050203195
Hydrogenolysis of 5-carbon sugars, sugar alcohols, and methods of making propylene glycol
patent, May 2006
- Werpy, Todd; Frye, Jr., John G.; Zacher, Alan H.
- US Patent Document 7,038,094
Method for producing lower polyhydric alcohols by hydrogenolysis of higher polyhydric alcohols
patent, October 1994
- Gubitosa, Guiseppe; Casale, Bruno
- US Patent Document 5,354,914
Hydrogen enriched natural gas as a motor fuel with variable air fuel ratio and fuel mixture ratio control
patent, August 1998
- Collier, Robert; Hoekstra, Robert L.; Mulligan, David Neal
- US Patent Document 5,787,864
Ruthenium-based catalyst for producing lower polyhydric alcohols
patent, August 2001
- Gubitosa, Giuseppe; Casale, Bruno
- US Patent Document RE37,329
Octane enhanced natural gas for internal combustion engine
patent, June 2002
- Collier, Jr., R. Kirk
- US Patent Document 6,397,790
Low-temperature hydrogen production from oxygenated hydrocarbons
patent, March 2004
- Cortright, Randy D.; Dumesic, James A.
- US Patent Document 6,699,457
Hydrogenation catalyst, and a method for its preparation and use, in particular for hydrogenation and/or hydrogenolysis of carbohydrates and polyhydric alcohols
patent, August 1996
- Gubitosa, Giuseppe; Casale, Bruno
- US Patent Document 5,543,379
Process for the Production of Glycerol and Glycols from Sugar Alcohols
patent, December 1960
- Conrafin, Fritz; Graubunden, Tamins; Bertossa, Giuseppe
- US Patent Document 2,965,679
Hydrogenolysis of 5-carbon sugars, sugar alcohols, and other methods and compositions for reactions involving hydrogen
patent, November 2002
- Werpy, Todd; Frye, Jr., John G.; Zacher, Alan H.
- US Patent Document 6,479,713
Two-stage dehydration of sugars
patent-application, July 2007
- Holladay, Johnathan E.; Hu, Jianli; Wang, Yong
- US Patent Application 11/341930; 20070173651
Process for producing cyclic compounds
patent, April 2007
- Werpy, Todd; Frye, Jr., John G.; White, James F.
- US Patent Document 7,199,250
Catalyst and Method for Production of Polyols by Hydrogenolysis of Carbohydrates
patent-application, December 2007
- Holcomb, Dale E.
- US Patent Application 11/845155; 20070293665
Methods of producing compounds from plant materials
patent-application, March 2005
- Werpy, Todd A.; Schmidt, Andrew J.; Frye, JR., John G.
- US Patent Application 10/980928; 20050065337
Synthesis of lower alkylene oxides and lower alkylene glycols from lower alkanes and/or lower alkenes
patent, July 2004
- Bhasin, Madan M.; King, Stephen W.
- US Patent Document 6,765,101
Method for the treatment of a methanol reforming catalyst
patent, August 2001
- Autenrieth, Rainer; Krumberger, Otto
- US Patent Document 6,280,701
Process for Producing Cyclic Compounds
patent-application, July 2007
- Werpy, Todd A.; Frye, JR., John G.; White, James F.
- US Patent Application 11/688022; 20070173643
Catalytic Conversion of Cellulose into Sugar Alcohols
journal, August 2006
- Fukuoka, Atsushi; Dhepe, Paresh L.
- Angewandte Chemie International Edition, Vol. 45, Issue 31, p. 5161-5163
Methods of producing compounds from plant material
patent-application, September 2004
- Werpy, Todd A.; Schmidt, Andrew J.; Frye, JR., John G.
- US Patent Application 10/379299; 20040175806
Transformation of Oxygenate Components of Biomass Pyrolysis Oil on a HZSM-5 Zeolite. I. Alcohols and Phenols
journal, May 2004
- Gayubo, Ana G.; Aguayo, Andrés T.; Atutxa, Alaitz
- Industrial & Engineering Chemistry Research, Vol. 43, Issue 11
Catalyst for manufacturing hydrogen or synthesis gas and manufacturing method of hydrogen or synthesis gas
patent, March 2002
- Shikada, Tsutomu; Ohno, Yotaro; Inoue, Norio
- US Patent Document 6,361,757
Catalysts and process for hydrogenolysis of sugar alcohols to polyols
patent, September 2001
- Chopade, Shubham P.; Miller, Dennis J.; Jackson, James
- US Patent Document 6,291,725
Aqueous-phase reforming of ethylene glycol on silica-supported metal catalysts
journal, June 2003
- Davda, R. R.; Shabaker, J. W.; Huber, G. W.
- Applied Catalysis B: Environmental, Vol. 43, Issue 1, p. 13-26
Transformation of Oxygenate Components of Biomass Pyrolysis Oil on a HZSM-5 Zeolite. II. Aldehydes, Ketones, and Acids
journal, May 2004
- Gayubo, Ana G.; Aguayo, Andrés T.; Atutxa, Alaitz
- Industrial & Engineering Chemistry Research, Vol. 43, Issue 11
Glycerol conversion in the aqueous solution under hydrogen over Ru/C + an ion-exchange resin and its reaction mechanism
journal, June 2006
- Miyazawa, Tomohisa; Kusunoki, Yohei; Kunimori, Kimio
- Journal of Catalysis, Vol. 240, Issue 2, p. 213-221
Hydrocracking of carbohydrates making glycerol, glycols and other polyols
patent, June 1991
- Andrews, Mark; Klaeren, Stephen A.
- US Patent Document 5,026,927
Catalyst for reducing lower polyhydric alcohols by hydrogenolysisal higher polyhydric alcohols and method for preparing catalyst
patent, March 1996
- Gubitosa, Giuseppe; Casale, Bruno
- US Patent Document 5,496,786
Methods and systems for generating polyols
patent, August 2010
- Cortright, Randy D.
- US Patent Document 7,767,867
Process
patent-application, June 2007
- Tuck, Michael William MArshall; Tilley, Simon Nicholas
- US Patent Application 11/668884; 20070149830
Hydrogenolysis of polyhydroxylated compounds
patent, August 1983
- Arena, Blaise J.
- US Patent Document 4,401,823
Carbon-Halogen Bond Scission and Rearrangement of .beta.-Halohydrins on the Rh(111) Surface
journal, December 1994
- Brown, Nicole F.; Barteau, Mark A.
- The Journal of Physical Chemistry, Vol. 98, Issue 48
Low-temperature hydrocarbon production from oxygenated hydrocarbons
patent, October 2005
- Cortright, Randy D.; Dumesic, James A.
- US Patent Document 6,953,873
Process for the production of hydrogen with very high purity from alcohols that comprise at least two carbon atoms
patent-application, November 2005
- Casanava, Dominique; Boudet, Nicolas
- US Patent Application 11/075965; 20050244329
Catalyst, method of making, and reactions using the catalyst
patent, August 2002
- Tonkovich, Anna Lee; Wang, Yong; Gao, Yufei
- US Patent Document 6,440,895
Distribution of methanol and catalysts between biodiesel and glycerin phases
journal, January 2005
- Chiu, Chuang-Wei; Goff, Michael J.; Suppes, Galen J.
- AIChE Journal, Vol. 51, Issue 4, p. 1274-1278
Methods and systems for generating polyols
patent, August 2011
- Cortright, Randy D.
- US Patent Document 7,989,664
Hydrogenolysis of 5-carbon sugars, sugar alcohols and compositions for reactions involving hydrogen
patent, January 2004
- Werpy, Todd; Frye, Jr., John G.; Zacher, Alan H.
- US Patent Document 6,677,385
Hydrogenolysis of 6-carbon sugars and other organic compounds
patent, January 2005
- Werpy, Todd; Frye, Jr., John G.; Zacher, Alan H.
- US Patent Document 6,841,085
Methods of producing compounds from plant material
patent-application, March 2005
- Werpy, Todd A.; Schmidt, Andrew J.; Frye, Jr., John G.
- US Patent Application 10/980927; 20050064560
Alumina-supported ruthenium catalyst
patent, August 2002
- Maeno, Hironobu; Matsumoto, Hiroto
- US Patent Document 6,429,167
Catalytic steam reforming of biomass-derived oxygenates: acetic acid and hydroxyacetaldehyde
journal, August 1996
- Wang, D.; Montané, D.; Chornet, E.
- Applied Catalysis A: General, Vol. 143, Issue 2, p. 245-270
Treatment process for a methanol reforming catalyst therefor
patent, January 2001
- Autenrieth, Rainer; Christen, Andreas; Zur Megede, Detlef
- US Patent Document 6,171,992
Process for the production of hydrogen and electrical energy from reforming of bio-ethanol with the use of fuel cells and with zero emission of pollutants
patent, May 2002
- Verykios, Xenophon
- US Patent Document 6,387,554
Low-Temperature Hydrogen Production from Oxygenated Hydrocarbons
patent-application, May 2003
- Cortright, Randy D.; Dumesic, James A.
- US Patent Application 09/998552; 20030099593
Method for aqueous phase reactions
patent, November 2000
- Elliott, Douglas C.; Hart, Todd R.
- US Patent Document 6,152,975
Process for producing high purity hydrogen
patent, March 2001
- Lin, Yu-Ming; Rei, Min-Hon
- US Patent Document 6,207,132
Methods of conducting simultaneous exothermic and endothermic reactions
patent, November 2005
- Tonkovich, Anna Lee; Roberts, Gary; Perry, Steven T.
- US Patent Document 6,969,506
Hydrogen enriched natural gas as a motor fuel with variable air fuel ratio and fuel mixture ratio control
patent, September 1997
- Collier, Robert; Hoekstra, Robert L.; Mulligan, David Neal
- US Patent Document 5,666,923
Method of producing off-gas having a selected ratio of carbon monoxide to hydrogen
patent, November 1996
- Li, Lixiong; Gloyna, Earnest F.
- US Patent Document 5,578,647
Acidity of Keggin-Type Heteropolycompounds Evaluated by Catalytic Probe Reactions, Sorption Microcalorimetry, and Density Functional Quantum Chemical Calculations
journal, December 1998
- Bardin, Billy B.; Bordawekar, Shailendra V.; Neurock, Matthew
- The Journal of Physical Chemistry B, Vol. 102, Issue 52, p. 10817-10825
Hydrogen Production from Cellulose in Hot Compressed Water Using Reduced Nickel Catalyst: Product Distribution at Different Reaction Temperatures.
journal, January 1998
- Minowa, Tomoaki; Fang, Zhen
- JOURNAL OF CHEMICAL ENGINEERING OF JAPAN, Vol. 31, Issue 3
Removal of Residual Catalyst from Simulated Biodiesel's Crude Glycerol for Glycerol Hydrogenolysis to Propylene Glycol
journal, January 2006
- Chiu, Chuang-Wei; Dasari, Mohanprasad A.; Sutterlin, Willam R.
- Industrial & Engineering Chemistry Research, Vol. 45, Issue 2
Gasification of Cellulose, Xylan, and Lignin Mixtures in Supercritical Water
journal, November 2001
- Yoshida, Takuya; Matsumura, Yukihiko
- Industrial & Engineering Chemistry Research, Vol. 40, Issue 23
Method of using catalyst for steam reforming of alcohols
patent, July 2002
- Wieland, Stefan; Baumann, Frank; Adam, Frank
- US Patent Document 6,413,449
Method of forming a dianhydrosugar alcohol
patent-application, July 2007
- Holladay, Johnathan E.; Hu, Jianli; Wang, Yong
- US Patent Application 11/341961; 20070173652
Raney Ni-Sn Catalyst for H2 Production from Biomass-Derived Hydrocarbons
journal, June 2003
- Huber, G. W.
- Science, Vol. 300, Issue 5628
Textured catalysts and methods of making textured catalysts
patent, March 2007
- Werpy, Todd; Frye, Jr., John G.; Wang, Yong
- US Patent Document 7,186,668
Works referencing / citing this record:
Production of aromatics from di- and polyoxygenates
patent, September 2016
- Beck, Taylor; Blank, Brian; Jones, Casey
- US Patent Document 9,440,892
Hydrotreating carbohydrates
patent, May 2014
- Sughrue, II, Edward L.; Yao, Jianhua
- US Patent Document 8,729,322
Sugar alcohol split injection conversion
patent, June 2016
- Yao, Jianhua; Sughrue, II, Edward L.; Brown, Ronald E.
- US Patent Document 9,358,520
Production of aromatics from di- and polyoxygenates
patent, August 2016
- Beck, Taylor; Blank, Brian; Jones, Casey
- US Patent Document 9,403,736