Catalytic conversion of cellulose to liquid hydrocarbon fuels by progressive removal of oxygen to facilitate separation processes and achieve high selectivities

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

Patent · 30 June 2015

OSTI ID:1187952

Dumesic, James A.; Ruiz, Juan Carlos Serrano; West, Ryan M.

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 converted 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.

View Patent

Research Organization:: Wisconsin Alumni Research Foundation, Madison, WI (United States)

Sponsoring Organization:: USDOE

DOE Contract Number:: FG02-03ER15468

Assignee:: Wisconsin Alumni Research Foundation (Madison, WI)

Patent Number(s):: 9,067,903

Application Number:: 14/093,907

OSTI ID:: 1187952

Country of Publication:: United States

Language:: English

References (22)

Furfural: Hemicellulose/xylosederived biochemical Mamman, Ajit Singh; Lee, Jong-Min; Kim, Yeong-Cheol Biofuels, Bioproducts and Biorefining, Vol. 2, Issue 5, p. 438-454 https://doi.org/10.1002/bbb.95	journal	September 2008
Liquid Alkanes with Targeted Molecular Weights from Biomass-Derived Carbohydrates West, Ryan M.; Liu, Zhen Y.; Peter, Maximilian ChemSusChem, Vol. 1, Issue 5 https://doi.org/10.1002/cssc.200800001	journal	May 2008
Kinetics of reactions of C8 olefins on HY zeolite Abbot, J. Journal of Catalysis, Vol. 108, Issue 2 https://doi.org/10.1016/0021-9517(87)90183-7	journal	December 1987
The Renewable Chemicals Industry Christensen, Claus Hviid; Rass-Hansen, Jeppe; Marsden, Charlotte C. ChemSusChem, Vol. 1, Issue 4 https://doi.org/10.1002/cssc.200700168	journal	April 2008
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 Koppatz, Stefan; Pfeifer, Christoph; Rauch, Reinhard Fuel Processing Technology, Vol. 90, Issue 7-8, p. 914-921 https://doi.org/10.1016/j.fuproc.2009.03.016	journal	July 2009
Combined dehydration/(transfer)-hydrogenation of C6-sugars (D-glucose and D-fructose) to γ-valerolactone using ruthenium catalysts Heeres, Hans; Handana, Ratna; Chunai, Dai Green Chemistry, Vol. 11, Issue 8 https://doi.org/10.1039/b904693c	journal	January 2009
Kinetic Study on the Acid-Catalyzed Hydrolysis of Cellulose to Levulinic Acid Girisuta, B.; Janssen, L. P. B. M.; Heeres, H. J. Industrial & Engineering Chemistry Research, Vol. 46, Issue 6 https://doi.org/10.1021/ie061186z	journal	March 2007
Hydrogen from catalytic reforming of biomass-derived hydrocarbons in liquid water Cortright, R. D.; Davda, R. R.; Dumesic, J. A. Nature, Vol. 418, Issue 6901 https://doi.org/10.1038/nature01009	journal	August 2002
Chemical Routes for the Transformation of Biomass into Chemicals Corma, Avelino; Iborra, Sara; Velty, Alexandra Chemical Reviews, Vol. 107, Issue 6, p. 2411-2502 https://doi.org/10.1021/cr050989d	journal	June 2007
Ketonization of Carboxylic Acids by Decarboxylation: Mechanism and Scope Renz, Michael European Journal of Organic Chemistry, Vol. 2005, Issue 6 https://doi.org/10.1002/ejoc.200400546	journal	March 2005
Synergies between Bio- and Oil Refineries for the Production of Fuels from Biomass Huber, George W.; Corma, Avelino Angewandte Chemie International Edition, Vol. 46, Issue 38, p. 7184-7201 https://doi.org/10.1002/anie.200604504	journal	September 2007
Synthesis of Transportation Fuels from Biomass: Chemistry, Catalysts, and Engineering Huber, George W.; Iborra, Sara; Corma, Avelino Chemical Reviews, Vol. 106, Issue 9, p. 4044-4098 https://doi.org/10.1021/cr068360d	journal	September 2006
Catalytic coupling of carboxylic acids by ketonization as a processing step in biomass conversion Gaertner, Christian A.; Serrano-Ruiz, Juan Carlos; Braden, Drew J. Journal of Catalysis, Vol. 266, Issue 1, p. 71-78 https://doi.org/10.1016/j.jcat.2009.05.015	journal	August 2009
Catalytic Conversion of Biomass to Monofunctional Hydrocarbons and Targeted Liquid-Fuel Classes Kunkes, E. L.; Simonetti, D. A.; West, R. M. Science, Vol. 322, Issue 5900 https://doi.org/10.1126/science.1159210	journal	October 2008
Liquid-Phase Catalytic Processing of Biomass-Derived Oxygenated Hydrocarbons to Fuels and Chemicals Chheda, Juben N.; Huber, George W.; Dumesic, James A. Angewandte Chemie International Edition, Vol. 46, Issue 38, p. 7164-7183 https://doi.org/10.1002/anie.200604274	journal	September 2007
Oligomerization of 1-Hexene and 1-Octene over Solid Acid Catalysts de Klerk, Arno Industrial & Engineering Chemistry Research, Vol. 44, Issue 11 https://doi.org/10.1021/ie0487843	journal	May 2005
Effect of the support composition on the vapor-phase hydrogenation of crotonaldehyde over Pt/CexZr1−xO2 catalysts Serranoruiz, J.; Luettich, J.; Sepulvedaescribano, A. Journal of Catalysis, Vol. 241, Issue 1 https://doi.org/10.1016/j.jcat.2006.04.006	journal	July 2006
The interconversion of formic acid and hydrogen/carbon dioxide using a binuclear ruthenium complex catalyst Gao, Yuan; Kuncheria, Joshi K.; Jenkins, Hilary A. Journal of the Chemical Society, Dalton Transactions, Issue 18 https://doi.org/10.1039/b004234j	journal	January 2000
Dissolution of cellulose with ionic liquids and its application: a mini-review Zhu, Shengdong; Wu, Yuanxin; Chen, Qiming Green Chemistry, Vol. 8, Issue 4, p. 325-327 https://doi.org/10.1039/b601395c	journal	January 2006
A highly catalytic and selective conversion of carboxylic acids to 1-alkenes of one less carbon atom Miller, Joseph A.; Nelson, Jeffrey A.; Byrne, Michael P. The Journal of Organic Chemistry, Vol. 58, Issue 1 https://doi.org/10.1021/jo00053a008	journal	January 1993
The use of catalytic hydrogenation to intercept carbohydrates in a dilute acid hydrolysis of biomass to effect a clean separation from lignin Michael Robinson, J.; E. Burgess, Caroline; A. Bently, Melissa Biomass and Bioenergy, Vol. 26, Issue 5, p. 473-483 https://doi.org/10.1016/j.biombioe.2003.09.005	journal	May 2004
Methods for Pretreatment of Lignocellulosic Biomass for Efficient Hydrolysis and Biofuel Production Kumar, Parveen; Barrett, Diane M.; Delwiche, Michael J. Industrial & Engineering Chemistry Research, Vol. 48, Issue 8, p. 3713-3729 https://doi.org/10.1021/ie801542g	journal	April 2009

Similar Records

Catalytic conversion of cellulose to liquid hydrocarbon fuels by progressive removal of oxygen to facilitate separation processes and achieve high selectivities

Patent · 2014 · OSTI ID:1113976

Catalytic conversion of cellulose to liquid hydrocarbon fuels by progressive removal of oxygen to facilitate separation processes and achieve high selectivities

Patent · 2012 · OSTI ID:1041034

Production of levulinic acid, furfural, and gamma valerolactone from C.sub.5 and C.sub.6 carbohydrates in mono- and biphasic systems using gamma-valerolactone as a solvent

Patent · 2013 · OSTI ID:1083032

Related Subjects

09 BIOMASS FUELS
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Catalytic conversion of cellulose to liquid hydrocarbon fuels by progressive removal of oxygen to facilitate separation processes and achieve high selectivities

Citation Formats

References (22)

Similar Records

Related Subjects