skip to main content
DOE Patents title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Method for selectively preparing evoglucosenone (LGO) and other anhydrosugars from biomass in polar aprotic solvents

Abstract

A method to produce 5-hydroxymethylfurfural (HMF) is described in which a reactant including cellulose, lignocellulose, or a combination thereof, in a reaction mixture of a polar, aprotic solvent and an acid is reacted for a time, at a temperature, and at a hydrogen ion concentration wherein at least a portion of the cellulose or lignocellulose present in the reactant is converted to HMF. The reaction mixture is initially substantially devoid of water. As the reaction proceeds, dehydration of intermediates causes the water concentration in the reaction mixture to rise to no more than about 2.0 wt % water.

Inventors:
; ; ;
Issue Date:
Research Org.:
Wisconsin Alumni Research Foundation, Madison, WI (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1344773
Patent Number(s):
9,376,451
Application Number:
14/588,178
Assignee:
Wisconsin Alumni Research Foundation (Madison, WI)
DOE Contract Number:  
FC02-07EF64494
Resource Type:
Patent
Resource Relation:
Patent File Date: 2014 Dec 31
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 59 BASIC BIOLOGICAL SCIENCES

Citation Formats

Huber, George W., Cao, Fei, Dumesic, James A., and Schwartz, Thomas J. Method for selectively preparing evoglucosenone (LGO) and other anhydrosugars from biomass in polar aprotic solvents. United States: N. p., 2016. Web.
Huber, George W., Cao, Fei, Dumesic, James A., & Schwartz, Thomas J. Method for selectively preparing evoglucosenone (LGO) and other anhydrosugars from biomass in polar aprotic solvents. United States.
Huber, George W., Cao, Fei, Dumesic, James A., and Schwartz, Thomas J. Tue . "Method for selectively preparing evoglucosenone (LGO) and other anhydrosugars from biomass in polar aprotic solvents". United States. https://www.osti.gov/servlets/purl/1344773.
@article{osti_1344773,
title = {Method for selectively preparing evoglucosenone (LGO) and other anhydrosugars from biomass in polar aprotic solvents},
author = {Huber, George W. and Cao, Fei and Dumesic, James A. and Schwartz, Thomas J.},
abstractNote = {A method to produce 5-hydroxymethylfurfural (HMF) is described in which a reactant including cellulose, lignocellulose, or a combination thereof, in a reaction mixture of a polar, aprotic solvent and an acid is reacted for a time, at a temperature, and at a hydrogen ion concentration wherein at least a portion of the cellulose or lignocellulose present in the reactant is converted to HMF. The reaction mixture is initially substantially devoid of water. As the reaction proceeds, dehydration of intermediates causes the water concentration in the reaction mixture to rise to no more than about 2.0 wt % water.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2016},
month = {6}
}

Patent:

Save / Share:

Works referenced in this record:

Pre-treatment of biomass with phosphoric acid prior to fast pyrolysis
journal, August 2003

  • Dobele, G.; Dizhbite, T.; Rossinskaja, G.
  • Journal of Analytical and Applied Pyrolysis, Vol. 68-69, p. 197-211
  • DOI: 10.1016/S0165-2370(03)00063-9

Efficient levoglucosenone production by catalytic pyrolysis of cellulose mixed with ionic liquid
journal, January 2011

  • Kudo, Shinji; Zhou, Zhenwei; Norinaga, Koyo
  • Green Chemistry, Vol. 13, Issue 11
  • DOI: 10.1039/C1GC15975E

Sulfonate Ionic Liquid as a Stable and Active Catalyst for Levoglucosenone Production from Saccharides via Catalytic Pyrolysis
journal, September 2013


Influence of pyrolysis temperature and time on the cellulose fast pyrolysis products: Analytical Py-GC/MS study
journal, November 2011

  • Lu, Qiang; Yang, Xiao-chu; Dong, Chang-qing
  • Journal of Analytical and Applied Pyrolysis, Vol. 92, Issue 2, p. 430-438
  • DOI: 10.1016/j.jaap.2011.08.006

Microwave pyrolysis of cellulosic materials for the production of anhydrosugars
journal, December 2001

  • Miura, Masakatsu; Kaga, Harumi; Yoshida, Takashi
  • Journal of Wood Science, Vol. 47, Issue 6
  • DOI: 10.1007/BF00767906

Design, Synthesis, and Biological Evaluation of Levoglucosenone-Derived Ras Activation Inhibitors
journal, April 2009

  • Müller, Christian; Gomez-Zurita Frau, Maria Antonia; Ballinari, Dario
  • ChemMedChem, Vol. 4, Issue 4
  • DOI: 10.1002/cmdc.200800416

Total Synthesis of (+)-Chloriolide
journal, April 2014

  • Ostermeier, Michael; Schobert, Rainer
  • The Journal of Organic Chemistry, Vol. 79, Issue 9
  • DOI: 10.1021/jo500527g

An efficient microwave-assisted green transformation of cellulose into levoglucosenone. Advantages of the use of an experimental design approach
journal, January 2007

  • Sarotti, Ariel M.; Spanevello, Rolando A.; Suárez, Alejandra G.
  • Green Chemistry, Vol. 9, Issue 10
  • DOI: 10.1039/B703690F

Recent Applications of Levoglucosenone as Chiral Synthon
journal, July 2012

  • M. Sarotti, Ariel; M. Zanardi, Maria; A. Spanevello, Rolando
  • Current Organic Synthesis, Vol. 9, Issue 4
  • DOI: 10.2174/157017912802651401

Some reactions of levoglucosenone
journal, June 1979

  • Shafizadeh, Fred; Furneaux, Richard H.; Stevenson, Thomas T.
  • Carbohydrate Research, Vol. 71, Issue 1, p. 169-191
  • DOI: 10.1016/S0008-6215(00)86069-3

Dihydrolevoglucosenone (Cyrene) as a bio-based alternative for dipolar aprotic solvents
journal, January 2014

  • Sherwood, James; De bruyn, Mario; Constantinou, Andri
  • Chem. Commun., Vol. 50, Issue 68
  • DOI: 10.1039/C4CC04133J

Preparation of levoglucosenone through sulfuric acid promoted pyrolysis of bagasse at low temperature
journal, January 2012


Fast pyrolysis of cellulose with solid acid catalysts for levoglucosenone
journal, May 2014

  • Wei, Xinlai; Wang, Zhi; Wu, Yang
  • Journal of Analytical and Applied Pyrolysis, Vol. 107, p. 150-154
  • DOI: 10.1016/j.jaap.2014.02.015

Feasibility of broadening the feedstock choice for levoglucosenone production by acid pre-treatment of wood and catalytic pyrolysis of the obtained lignocellulose
journal, September 2013

  • Zandersons, Janis; Zhurinsh, Aivars; Dobele, Galina
  • Journal of Analytical and Applied Pyrolysis, Vol. 103, p. 222-226
  • DOI: 10.1016/j.jaap.2013.01.014