Catalytic conversion of cellulose to liquid hydrocarbon fuels by progressive removal of oxygen to facilitate separation processes and achieve high selectivities
Abstract
Described is a method to make liquid chemicals. The method includes deconstructing cellulose to yield a product mixture comprising levulinic acid and formic acid, converting the levulinic acid to .gamma.-valerolactone, and converting the .gamma.-valerolactone to pentanoic acid. Alternatively, the .gamma.-valerolactone can be conveted to a mixture of n-butenes. The pentanoic acid can be decarboxylated yield 1-butene or ketonized to yield 5-nonanone. The 5-nonanone can be hydrodeoxygenated to yield nonane, or 5-nonanone can be reduced to yield 5-nonanol. The 5-nonanol can be dehydrated to yield nonene, which can be dimerized to yield a mixture of C.sub.9 and C.sub.18 olefins, which can be hydrogenated to yield a mixture of alkanes.
- Inventors:
-
- Verona, WI
- Madison, WI
- Issue Date:
- Research Org.:
- Wisconsin Alumni Research Foundation, Madison, WI, USA
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1113976
- Patent Number(s):
- 8624043
- Application Number:
- 13/369,388
- Assignee:
- Wisconsin Alumni Research Foundation (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:
- FG02-03ER15468
- Resource Type:
- Patent
- Resource Relation:
- Patent File Date: 2012 Feb 09
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 09 BIOMASS FUELS
Citation Formats
Dumesic, James A, Ruiz, Juan Carlos Serrano, and West, Ryan M. Catalytic conversion of cellulose to liquid hydrocarbon fuels by progressive removal of oxygen to facilitate separation processes and achieve high selectivities. United States: N. p., 2014.
Web.
Dumesic, James A, Ruiz, Juan Carlos Serrano, & West, Ryan M. Catalytic conversion of cellulose to liquid hydrocarbon fuels by progressive removal of oxygen to facilitate separation processes and achieve high selectivities. United States.
Dumesic, James A, Ruiz, Juan Carlos Serrano, and West, Ryan M. Tue .
"Catalytic conversion of cellulose to liquid hydrocarbon fuels by progressive removal of oxygen to facilitate separation processes and achieve high selectivities". United States. https://www.osti.gov/servlets/purl/1113976.
@article{osti_1113976,
title = {Catalytic conversion of cellulose to liquid hydrocarbon fuels by progressive removal of oxygen to facilitate separation processes and achieve high selectivities},
author = {Dumesic, James A and Ruiz, Juan Carlos Serrano and West, Ryan M},
abstractNote = {Described is a method to make liquid chemicals. The method includes deconstructing cellulose to yield a product mixture comprising levulinic acid and formic acid, converting the levulinic acid to .gamma.-valerolactone, and converting the .gamma.-valerolactone to pentanoic acid. Alternatively, the .gamma.-valerolactone can be conveted to a mixture of n-butenes. The pentanoic acid can be decarboxylated yield 1-butene or ketonized to yield 5-nonanone. The 5-nonanone can be hydrodeoxygenated to yield nonane, or 5-nonanone can be reduced to yield 5-nonanol. The 5-nonanol can be dehydrated to yield nonene, which can be dimerized to yield a mixture of C.sub.9 and C.sub.18 olefins, which can be hydrogenated to yield a mixture of alkanes.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2014},
month = {1}
}
Works referenced in this record:
Lignocellulose degradation to furfural and levulinic acid
patent, January 1990
- Fitzpatrick, Stephen W.
- US Patent Document 4,897,497
Hydrogenated 5-carbon compound and method of making
patent, March 1999
- Elliott, Douglas C.; Frye, Jr., John G.
- US Patent Document 5,883,266
Process for the hydrogenation of a lactone or of a carboxylic acid or an ester having a gamma-carbonyl group
patent-application, July 2006
- Van Den Brink, Peter John; Von Hebel, Klaas Lambertus; Lange, Jean-Paul
- US Patent Application 11/314404; 20060162239
Hydrogenation Process for the Conversion of a Carboxylic Acid or an Ester Having a Carbonyl Group
patent-application, September 2007
- Haan, Rene John; Lange, Jean-Paul; Petrus, Leonardus
- US Patent Application 11/680437; 20070208183
Chemical Routes for the Transformation of Biomass into Chemicals
journal, June 2007
- Corma, Avelino; Iborra, Sara; Velty, Alexandra
- Chemical Reviews, Vol. 107, Issue 6, p. 2411-2502
Kinetics of reactions of C8 olefins on HY zeolite
journal, December 1987
- Abbot, J.
- Journal of Catalysis, Vol. 108, Issue 2
Liquid-Phase Catalytic Processing of Biomass-Derived Oxygenated Hydrocarbons to Fuels and Chemicals
journal, September 2007
- Chheda, Juben N.; Huber, George W.; Dumesic, James A.
- Angewandte Chemie International Edition, Vol. 46, Issue 38, p. 7164-7183
The Renewable Chemicals Industry
journal, April 2008
- Christensen, Claus Hviid; Rass-Hansen, Jeppe; Marsden, Charlotte C.
- ChemSusChem, Vol. 1, Issue 4
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
Oligomerization of 1-Hexene and 1-Octene over Solid Acid Catalysts
journal, May 2005
- de Klerk, Arno
- Industrial & Engineering Chemistry Research, Vol. 44, Issue 11
Catalytic coupling of carboxylic acids by ketonization as a processing step in biomass conversion
journal, August 2009
- Gaertner, Christian A.; Serrano-Ruiz, Juan Carlos; Braden, Drew J.
- Journal of Catalysis, Vol. 266, Issue 1, p. 71-78
Kinetic Study on the Acid-Catalyzed Hydrolysis of Cellulose to Levulinic Acid
journal, March 2007
- Girisuta, B.; Janssen, L. P. B. M.; Heeres, H. J.
- Industrial & Engineering Chemistry Research, Vol. 46, Issue 6
Synergies between Bio- and Oil Refineries for the Production of Fuels from Biomass
journal, September 2007
- Huber, George W.; Corma, Avelino
- Angewandte Chemie International Edition, Vol. 46, Issue 38, p. 7184-7201
Synthesis of Transportation Fuels from Biomass: Chemistry, Catalysts, and Engineering
journal, September 2006
- Huber, George W.; Iborra, Sara; Corma, Avelino
- Chemical Reviews, Vol. 106, Issue 9, p. 4044-4098
H2 rich product gas by steam gasification of biomass with in situ CO2 absorption in a dual fluidized bed system of 8 MW fuel input
journal, July 2009
- Koppatz, Stefan; Pfeifer, Christoph; Rauch, Reinhard
- Fuel Processing Technology, Vol. 90, Issue 7-8, p. 914-921
Methods for Pretreatment of Lignocellulosic Biomass for Efficient Hydrolysis and Biofuel Production
journal, April 2009
- Kumar, Parveen; Barrett, Diane M.; Delwiche, Michael J.
- Industrial & Engineering Chemistry Research, Vol. 48, Issue 8, p. 3713-3729
Catalytic Conversion of Biomass to Monofunctional Hydrocarbons and Targeted Liquid-Fuel Classes
journal, October 2008
- Kunkes, E. L.; Simonetti, D. A.; West, R. M.
- Science, Vol. 322, Issue 5900
Furfural: Hemicellulose/xylosederived biochemical
journal, September 2008
- Mamman, Ajit Singh; Lee, Jong-Min; Kim, Yeong-Cheol
- Biofuels, Bioproducts and Biorefining, Vol. 2, Issue 5, p. 438-454
A highly catalytic and selective conversion of carboxylic acids to 1-alkenes of one less carbon atom
journal, January 1993
- Miller, Joseph A.; Nelson, Jeffrey A.; Byrne, Michael P.
- The Journal of Organic Chemistry, Vol. 58, Issue 1
Ketonization of Carboxylic Acids by Decarboxylation: Mechanism and Scope
journal, March 2005
- Renz, Michael
- European Journal of Organic Chemistry, Vol. 2005, Issue 6
The use of catalytic hydrogenation to intercept carbohydrates in a dilute acid hydrolysis of biomass to effect a clean separation from lignin
journal, May 2004
- Michael Robinson, J.; E. Burgess, Caroline; A. Bently, Melissa
- Biomass and Bioenergy, Vol. 26, Issue 5, p. 473-483
Effect of the support composition on the vapor-phase hydrogenation of crotonaldehyde over Pt/CexZr1−xO2 catalysts
journal, July 2006
- Serranoruiz, J.; Luettich, J.; Sepulvedaescribano, A.
- Journal of Catalysis, Vol. 241, Issue 1
Liquid Alkanes with Targeted Molecular Weights from Biomass-Derived Carbohydrates
journal, May 2008
- West, Ryan M.; Liu, Zhen Y.; Peter, Maximilian
- ChemSusChem, Vol. 1, Issue 5
Works referencing / citing this record:
Biofuel containing furanic compounds and alkoxy benzene compounds and the process for obtaining these compounds from sugar cane by hydrolysis of cellulose, sugars and lignin in ionic liquids
patent, February 2016
- Brito da Silva Correia, Pedro Manuel
- US Patent Document 9,260,674