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Title: 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:
 [1];  [2];  [2]
  1. Verona, WI
  2. Madison, WI
Issue Date:
Research Org.:
Wisconsin Alumni Research Foundation, Madison, WI, USA
Sponsoring Org.:
USDOE
OSTI Identifier:
1113976
Patent Number(s):
8,624,043
Application Number:
13/369,388
Assignee:
Wisconsin Alumni Research Foundation (Madison, WI)
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}
}

Patent:

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Works referenced in this record:

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
  • DOI: 10.1021/cr050989d

Kinetics of reactions of C8 olefins on HY zeolite
journal, December 1987


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
  • DOI: 10.1002/anie.200604274

The Renewable Chemicals Industry
journal, April 2008

  • Christensen, Claus Hviid; Rass-Hansen, Jeppe; Marsden, Charlotte C.
  • ChemSusChem, Vol. 1, Issue 4
  • DOI: 10.1002/cssc.200700168

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
  • DOI: 10.1038/nature01009

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
  • DOI: 10.1021/ie0487843

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
  • DOI: 10.1016/j.jcat.2009.05.015

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
  • DOI: 10.1021/ie061186z

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
  • DOI: 10.1002/anie.200604504

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
  • DOI: 10.1021/cr068360d

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
  • DOI: 10.1016/j.fuproc.2009.03.016

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
  • DOI: 10.1021/ie801542g

Catalytic Conversion of Biomass to Monofunctional Hydrocarbons and Targeted Liquid-Fuel Classes
journal, October 2008


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
  • DOI: 10.1002/bbb.95

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
  • DOI: 10.1021/jo00053a008

Ketonization of Carboxylic Acids by Decarboxylation: Mechanism and Scope
journal, March 2005


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
  • DOI: 10.1016/j.biombioe.2003.09.005

Effect of the support composition on the vapor-phase hydrogenation of crotonaldehyde over Pt/CexZr1−xO2 catalysts
journal, July 2006


Liquid Alkanes with Targeted Molecular Weights from Biomass-Derived Carbohydrates
journal, May 2008