Method to convert biomass to 5-(hydroxymethyl)-furfural (HMF) and furfural using lactones, furans, and pyrans as solvents
Abstract
Described is a process to produce hydroxymethyl furfural (HMF) from biomass-derived sugars. The process includes the steps of reacting a C5 and/or C6 sugar-containing reactant derived from biomass in a monophasic or biphasic reaction solution comprising water and a co-solvent. The co-solvent can be beta-, gamma-, and/or delta-lactones derived from biomass, tetrahydrofuran (THF) derived from biomass, and/or methyltetrahydrofuran (MTHF) derived from biomass. The reaction takes place in the presence of an acid catalyst and a dehydration catalyst for a time and under conditions such that at least a portion of glucose or fructose present in the reactant is converted to HMF.
- Inventors:
- Issue Date:
- Research Org.:
- Wisconsin Alumni Research Foundation, Madison, WI (USA).
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1137200
- Patent Number(s):
- 8772515
- Application Number:
- 13/649,891
- Assignee:
- Wisconsin Alumni Research Foundation (Madison, WI)
- Patent Classifications (CPCs):
-
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
- DOE Contract Number:
- FG02-84ER13183
- Resource Type:
- Patent
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 60 APPLIED LIFE SCIENCES
Citation Formats
Dumesic, James A., Ribeiro Gallo, Jean Marcel, and Alonso, David. Method to convert biomass to 5-(hydroxymethyl)-furfural (HMF) and furfural using lactones, furans, and pyrans as solvents. United States: N. p., 2014.
Web.
Dumesic, James A., Ribeiro Gallo, Jean Marcel, & Alonso, David. Method to convert biomass to 5-(hydroxymethyl)-furfural (HMF) and furfural using lactones, furans, and pyrans as solvents. United States.
Dumesic, James A., Ribeiro Gallo, Jean Marcel, and Alonso, David. Tue .
"Method to convert biomass to 5-(hydroxymethyl)-furfural (HMF) and furfural using lactones, furans, and pyrans as solvents". United States. https://www.osti.gov/servlets/purl/1137200.
@article{osti_1137200,
title = {Method to convert biomass to 5-(hydroxymethyl)-furfural (HMF) and furfural using lactones, furans, and pyrans as solvents},
author = {Dumesic, James A. and Ribeiro Gallo, Jean Marcel and Alonso, David},
abstractNote = {Described is a process to produce hydroxymethyl furfural (HMF) from biomass-derived sugars. The process includes the steps of reacting a C5 and/or C6 sugar-containing reactant derived from biomass in a monophasic or biphasic reaction solution comprising water and a co-solvent. The co-solvent can be beta-, gamma-, and/or delta-lactones derived from biomass, tetrahydrofuran (THF) derived from biomass, and/or methyltetrahydrofuran (MTHF) derived from biomass. The reaction takes place in the presence of an acid catalyst and a dehydration catalyst for a time and under conditions such that at least a portion of glucose or fructose present in the reactant is converted to HMF.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {Tue Jul 08 00:00:00 EDT 2014},
month = {Tue Jul 08 00:00:00 EDT 2014}
}
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.
Works referenced in this record:
Catalytic process for producing furan derivatives in a biphasic reactor
patent, August 2009
- Dumesic, James A.; Rom{acute over (α)}n-Leshkov, Yuriy; Chheda, Juben Nemchand
- US Patent Document 7,572,925
Production of liquid alkanes in the jet fuel range (C8-C15) from biomass-derived carbohydrates
patent, February 2011
- Dumesic, James A.; Roman-Leshkov, Yuriy
- US Patent Document 7,880,049
Method to produce, recover and convert furan derivatives from aqueous solutions using alkylphenol extraction
patent, March 2013
- Dumesic, James A.; Alonso, David Martin; Bond, Jesse Quentin
- US Patent Document 8,389,749
Biomass Refining by Selective Chemical Reactions
patent-application, March 2011
- Robinson, J. Michael
- US Patent Application 12/566427; 20110071306
Isomerization of Sugars
patent-application, August 2011
- Moliner-Marin, Manuel; Roman-Leshkov, Yuriy; Davis, Mark E.
- US Patent Application 13/007389; 20110207923
Mechanism of the dehydration of d-fructose to 5-hydroxymethylfurfural in dimethyl sulfoxide at 150°C: an NMR study
journal, December 2008
- Amarasekara, Ananda S.; Williams, LaToya D.; Ebede, Chidinma C.
- Carbohydrate Research, Vol. 343, Issue 18, p. 3021-3024
Mechanism of formation of 5-(hydroxymethyl)-2-furaldehyde from d-fructose and sucrose
journal, May 1990
- Antal, Michael Jerry; Mok, William S. L.; Richards, Geoffrey N.
- Carbohydrate Research, Vol. 199, Issue 1, p. 91-109
Simple Chemical Transformation of Lignocellulosic Biomass into Furans for Fuels and Chemicals
journal, February 2009
- Binder, Joseph B.; Raines, Ronald T.
- Journal of the American Chemical Society, Vol. 131, Issue 5, p. 1979-1985
Acid-Functionalized SBA-15-Type Silica Catalysts for Carbohydrate Dehydration
journal, May 2011
- Crisci, Anthony J.; Tucker, Mark H.; Lee, Ming-Yung
- ACS Catalysis, Vol. 1, Issue 7, p. 719-728
Oxidation of 5-hydroxymethylfurfural over supported Pt, Pd and Au catalysts
journal, February 2011
- Davis, Sara E.; Houk, Levi R.; Tamargo, Erin C.
- Catalysis Today, Vol. 160, Issue 1, p. 55-60
On the mechanism of selective oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over supported Pt and Au catalysts
journal, January 2012
- Davis, Sara E.; Zope, Bhushan N.; Davis, Robert J.
- Green Chemistry, Vol. 14, Issue 1, p. 143-147
Direct conversion of cellulose and lignocellulosic biomass into chemicals and biofuel with metal chloride catalysts
journal, April 2012
- Dutta, Saikat; De, Sudipta; Alam, Md. Imteyaz
- Journal of Catalysis, Vol. 288, p. 8-15
Versatile dual hydrogenation–oxidation nanocatalysts for the aqueous transformation of biomass-derived platform molecules
journal, January 2012
- García-Suárez, Eduardo J.; Balu, Alina Mariana; Tristany, Mar
- Green Chemistry, Vol. 14, Issue 5, p. 1434-1439
The mechanism of glucose conversion to 5-hydroxymethylfurfural catalyzed by metal chlorides in ionic liquid: A theoretical study
journal, February 2011
- Guan, Jing; Cao, Quan; Guo, Xingcui
- Computational and Theoretical Chemistry, Vol. 963, Issue 2-3, p. 453-462
Integrating enzymatic and acid catalysis to convert glucose into 5-hydroxymethylfurfural
journal, January 2010
- Huang, Renliang; Qi, Wei; Su, Rongxin
- Chem. Commun., Vol. 46, Issue 7, p. 1115-1117
Catalytic synthesis of α-methylene-γ-valerolactone: a biomass-derived acrylic monomer
journal, September 2004
- Manzer, Leo E.
- Applied Catalysis A: General, Vol. 272, Issue 1-2, p. 249-256
Tin-containing zeolites are highly active catalysts for the isomerization of glucose in water
journal, March 2010
- Moliner, M.; Roman-Leshkov, Y.; Davis, M. E.
- Proceedings of the National Academy of Sciences, Vol. 107, Issue 14, p. 6164-6168
Dehydration of fructose and sucrose into 5-hydroxymethylfurfural in the presence of 1-H-3-methyl imidazolium chloride acting both as solvent and catalyst
journal, July 2006
- Moreau, Claude; Finiels, Annie; Vanoye, Laurent
- Journal of Molecular Catalysis A: Chemical, Vol. 253, Issue 1-2, p. 165-169
“One-Pot” Synthesis of 5-(Hydroxymethyl)furfural from Carbohydrates using Tin-Beta Zeolite
journal, April 2011
- Nikolla, Eranda; Román-Leshkov, Yuriy; Moliner, Manuel
- ACS Catalysis, Vol. 1, Issue 4, p. 408-410
Tin-containing silicates: structure-activity relations
journal, February 2012
- Osmundsen, C. M.; Holm, M. S.; Dahl, S.
- Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences, Vol. 468, Issue 2143, p. 2000-2016
Production of 5-Hydroxymethylfurfural from Glucose Using a Combination of Lewis and Brønsted Acid Catalysts in Water in a Biphasic Reactor with an Alkylphenol Solvent
journal, April 2012
- Pagán-Torres, Yomaira J.; Wang, Tianfu; Gallo, Jean Marcel R.
- ACS Catalysis, Vol. 2, Issue 6, p. 930-934
Glucose Reversion Reaction Kinetics
journal, May 2010
- Pilath, Heidi M.; Nimlos, Mark R.; Mittal, Ashutosh
- Journal of Agricultural and Food Chemistry, Vol. 58, Issue 10, p. 6131-6140
Phase Modifiers Promote Efficient Production of Hydroxymethylfurfural from Fructose
journal, June 2006
- Roman-Leshkov, Yuriy; Chheda, Juben N.; Dumesic, James A.
- Science, Vol. 312, Issue 5782, p. 1933-1937
Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates
journal, June 2007
- Román-Leshkov, Yuriy; Barrett, Christopher J.; Liu, Zhen Y.
- Nature, Vol. 447, Issue 7147, p. 982-985
Solvent Effects on Fructose Dehydration to 5-Hydroxymethylfurfural in Biphasic Systems Saturated with Inorganic Salts
journal, January 2009
- Román-Leshkov, Yuriy; Dumesic, James A.
- Topics in Catalysis, Vol. 52, Issue 3, p. 297-303
Direct hydrothermal synthesis of mesoporous Sn-SBA-15 materials under weak acidic conditions
journal, March 2007
- Shah, P.; Ramaswamy, A. V.; Lazar, K.
- Microporous and Mesoporous Materials, Vol. 100, Issue 1-3, p. 210-226
Enhanced production of hydroxymethylfurfural from fructose with solid acid catalysts by simple water removal methods
journal, August 2009
- Shimizu, Ken-ichi; Uozumi, Rie; Satsuma, Atsushi
- Catalysis Communications, Vol. 10, Issue 14, p. 1849-1853
A one-pot reaction for biorefinery: combination of solid acid and base catalysts for direct production of 5-hydroxymethylfurfural from saccharides
journal, January 2009
- Takagaki, Atsushi; Ohara, Mika; Nishimura, Shun
- Chemical Communications, Vol. 0, Issue 41, p. 6276-6278
Synthesis of (±)-4-alkanolides from pent-4-enoic acid
journal, March 2008
- Ugurchieva, T. M.; Lozanova, A. V.; Zlokazov, M. V.
- Russian Chemical Bulletin, Vol. 57, Issue 3, p. 657-659
Coordinated development of leading biomass pretreatment technologies
journal, December 2005
- Wyman, Charles E.; Dale, Bruce E.; Elander, Richard T.
- Bioresource Technology, Vol. 96, Issue 18, p. 1959-1966
Conversion of carbohydrates and lignocellulosic biomass into 5-hydroxymethylfurfural using AlCl3·6H2O catalyst in a biphasic solvent system
journal, January 2012
- Yang, Yu; Hu, Chang-wei; Abu-Omar, Mahdi M.
- Green Chem., Vol. 14, Issue 2, p. 509-513
Efficient Catalytic System for the Selective Production of 5-Hydroxymethylfurfural from Glucose and Fructose
journal, October 2008
- Yong, Gen; Zhang, Yugen; Ying, Jackie Y.
- Angewandte Chemie, Vol. 120, Issue 48, p. 9485-9488
Ionic Liquid-Mediated Formation of 5-Hydroxymethylfurfural—A Promising Biomass-Derived Building Block
journal, February 2011
- Zakrzewska, Małgorzata E.; Bogel-Łukasik, Ewa; Bogel-Łukasik, Rafał
- Chemical Reviews, Vol. 111, Issue 2, p. 397-417
Optimal design and operation of SMB bioreactor: production of high fructose syrup by isomerization of glucose
journal, October 2004
- Zhang, Yan; Hidajat, Kus; Ray, Ajay K.
- Biochemical Engineering Journal, Vol. 21, Issue 2, p. 111-121
Metal Chlorides in Ionic Liquid Solvents Convert Sugars to 5-Hydroxymethylfurfural
journal, June 2007
- Zhao, H.; Holladay, J. E.; Brown, H.
- Science, Vol. 316, Issue 5831, p. 1597-1600
Solid acid catalysis of tandem isomerization-lactonization of olefinic acids
journal, December 2007
- Zhou, Yibo; Woo, L. Keith; Angelici, Robert J.
- Applied Catalysis A: General, Vol. 333, Issue 2, p. 238-244
Influence of Reaction Conditions on Diacid Formation During Au-Catalyzed Oxidation of Glycerol and Hydroxymethylfurfural
journal, February 2012
- Zope, Bhushan N.; Davis, Sara E.; Davis, Robert J.
- Topics in Catalysis, Vol. 55, Issue 1-2, p. 24-32
Direct conversion of carbohydrates to 5-hydroxymethylfurfural using Sn-Mont catalyst
journal, January 2012
- Wang, Jianjian; Ren, Jiawen; Liu, Xiaohui
- Green Chemistry, Vol. 14, Issue 9
5-Hydroxymethylfurfural (HMF). A Review Focussing on its Manufacture
journal, January 1990
- Kuster, B. F. M.
- Starch - Stärke, Vol. 42, Issue 8
Production and upgrading of 5-hydroxymethylfurfural using heterogeneous catalysts and biomass-derived solvents
journal, January 2013
- Gallo, Jean Marcel R.; Alonso, David Martin; Mellmer, Max A.
- Green Chem., Vol. 15, Issue 1
Works referencing / citing this record:
Oxidation catalyst for furfural compounds and applying method thereof
patent, July 2017
- Huang, Ying-Ting; Wong, Jinn-Jong; Chen, Jau-Hong
- US Patent Document 9,707,547
Conversion of fructose-containing feedstocks to HMF-containing product
patent, April 2017
- Boussie, Thomas R.; Dias, Eric L.; Murphy, Vincent J.
- US Patent Document 9,611,241
Method to produce water-soluble sugars from biomass using solvents containing lactones
patent, June 2015
- Dumesic, James A.; Luterbacher, Jeremy S.
- US Patent Document 9,045,804