Method to convert biomass to 5-(hydroxymethyl)-furfural (HMF) and furfural using lactones, furans, and pyrans as solvents

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

Patent · Tue Jul 08 00:00:00 EDT 2014

OSTI ID:1137200

Dumesic, James A.; Ribeiro Gallo, Jean Marcel; Alonso, David

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.

View Patent

Research Organization:: Wisconsin Alumni Research Foundation, Madison, WI (USA).

Sponsoring Organization:: USDOE

DOE Contract Number:: FG02-84ER13183

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

Patent Number(s):: 8,772,515

Application Number:: 13/649,891

OSTI ID:: 1137200

Country of Publication:: United States

Language:: English

References (41)

Efficient Catalytic System for the Selective Production of 5-Hydroxymethylfurfural from Glucose and Fructose Yong, Gen; Zhang, Yugen; Ying, Jackie Y. Angewandte Chemie, Vol. 120, Issue 48, p. 9485-9488 https://doi.org/10.1002/ange.200803207	journal	October 2008
Integrating enzymatic and acid catalysis to convert glucose into 5-hydroxymethylfurfural Huang, Renliang; Qi, Wei; Su, Rongxin Chem. Commun., Vol. 46, Issue 7, p. 1115-1117 https://doi.org/10.1039/B921306F	journal	January 2010
Transformations of biomass-derived platform molecules: from high added-value chemicals to fuels via aqueous-phase processing Serrano-Ruiz, Juan Carlos; Luque, Rafael; Sepúlveda-Escribano, Antonio Chemical Society Reviews, Vol. 40, Issue 11, p. 5266-5281 https://doi.org/10.1039/C1CS15131B	journal	January 2011
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 Pagán-Torres, Yomaira J.; Wang, Tianfu; Gallo, Jean Marcel R. ACS Catalysis, Vol. 2, Issue 6, p. 930-934 https://doi.org/10.1021/cs300192z	journal	April 2012
Glucose Reversion Reaction Kinetics Pilath, Heidi M.; Nimlos, Mark R.; Mittal, Ashutosh Journal of Agricultural and Food Chemistry, Vol. 58, Issue 10, p. 6131-6140 https://doi.org/10.1021/jf903598w	journal	May 2010
“One-Pot” Synthesis of 5-(Hydroxymethyl)furfural from Carbohydrates using Tin-Beta Zeolite Nikolla, Eranda; Román-Leshkov, Yuriy; Moliner, Manuel ACS Catalysis, Vol. 1, Issue 4, p. 408-410 https://doi.org/10.1021/cs2000544	journal	April 2011
Tin-containing silicates: structure-activity relations 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 https://doi.org/10.1098/rspa.2012.0047	journal	February 2012
Tin-containing zeolites are highly active catalysts for the isomerization of glucose in water Moliner, M.; Roman-Leshkov, Y.; Davis, M. E. Proceedings of the National Academy of Sciences, Vol. 107, Issue 14, p. 6164-6168 https://doi.org/10.1073/pnas.1002358107	journal	March 2010
Direct conversion of cellulose and lignocellulosic biomass into chemicals and biofuel with metal chloride catalysts Dutta, Saikat; De, Sudipta; Alam, Md. Imteyaz Journal of Catalysis, Vol. 288, p. 8-15 https://doi.org/10.1016/j.jcat.2011.12.017	journal	April 2012
Direct hydrothermal synthesis of mesoporous Sn-SBA-15 materials under weak acidic conditions Shah, P.; Ramaswamy, A. V.; Lazar, K. Microporous and Mesoporous Materials, Vol. 100, Issue 1-3, p. 210-226 https://doi.org/10.1016/j.micromeso.2006.10.042	journal	March 2007
Solvent Effects on Fructose Dehydration to 5-Hydroxymethylfurfural in Biphasic Systems Saturated with Inorganic Salts Román-Leshkov, Yuriy; Dumesic, James A. Topics in Catalysis, Vol. 52, Issue 3, p. 297-303 https://doi.org/10.1007/s11244-008-9166-0	journal	January 2009
Dehydration of fructose and sucrose into 5-hydroxymethylfurfural in the presence of 1-H-3-methyl imidazolium chloride acting both as solvent and catalyst Moreau, Claude; Finiels, Annie; Vanoye, Laurent Journal of Molecular Catalysis A: Chemical, Vol. 253, Issue 1-2, p. 165-169 https://doi.org/10.1016/j.molcata.2006.03.046	journal	July 2006
Metal Chlorides in Ionic Liquid Solvents Convert Sugars to 5-Hydroxymethylfurfural Zhao, H.; Holladay, J. E.; Brown, H. Science, Vol. 316, Issue 5831, p. 1597-1600 https://doi.org/10.1126/science.1141199	journal	June 2007
Mechanism of the dehydration of d-fructose to 5-hydroxymethylfurfural in dimethyl sulfoxide at 150°C: an NMR study Amarasekara, Ananda S.; Williams, LaToya D.; Ebede, Chidinma C. Carbohydrate Research, Vol. 343, Issue 18, p. 3021-3024 https://doi.org/10.1016/j.carres.2008.09.008	journal	December 2008
Direct conversion of carbohydrates to 5-hydroxymethylfurfural using Sn-Mont catalyst Wang, Jianjian; Ren, Jiawen; Liu, Xiaohui Green Chemistry, Vol. 14, Issue 9 https://doi.org/10.1039/C2GC35699F	journal	January 2012
Simple Chemical Transformation of Lignocellulosic Biomass into Furans for Fuels and Chemicals Binder, Joseph B.; Raines, Ronald T. Journal of the American Chemical Society, Vol. 131, Issue 5, p. 1979-1985 https://doi.org/10.1021/ja808537j	journal	February 2009
Oxidation of 5-hydroxymethylfurfural over supported Pt, Pd and Au catalysts Davis, Sara E.; Houk, Levi R.; Tamargo, Erin C. Catalysis Today, Vol. 160, Issue 1, p. 55-60 https://doi.org/10.1016/j.cattod.2010.06.004	journal	February 2011
Conversion of carbohydrates and lignocellulosic biomass into 5-hydroxymethylfurfural using AlCl₃·6H₂O catalyst in a biphasic solvent system Yang, Yu; Hu, Chang-wei; Abu-Omar, Mahdi M. Green Chem., Vol. 14, Issue 2, p. 509-513 https://doi.org/10.1039/C1GC15972K	journal	January 2012
5-Hydroxymethylfurfural (HMF). A Review Focussing on its Manufacture Kuster, B. F. M. Starch - Stärke, Vol. 42, Issue 8 https://doi.org/10.1002/star.19900420808	journal	January 1990
A one-pot reaction for biorefinery: combination of solid acid and base catalysts for direct production of 5-hydroxymethylfurfural from saccharides Takagaki, Atsushi; Ohara, Mika; Nishimura, Shun Chemical Communications, Vol. 0, Issue 41, p. 6276-6278 https://doi.org/10.1039/B914087E	journal	January 2009
Solid acid catalysis of tandem isomerization-lactonization of olefinic acids Zhou, Yibo; Woo, L. Keith; Angelici, Robert J. Applied Catalysis A: General, Vol. 333, Issue 2, p. 238-244 https://doi.org/10.1016/j.apcata.2007.09.013	journal	December 2007
Ionic Liquid-Mediated Formation of 5-Hydroxymethylfurfural—A Promising Biomass-Derived Building Block Zakrzewska, Małgorzata E.; Bogel-Łukasik, Ewa; Bogel-Łukasik, Rafał Chemical Reviews, Vol. 111, Issue 2, p. 397-417 https://doi.org/10.1021/cr100171a	journal	February 2011
Enhanced production of hydroxymethylfurfural from fructose with solid acid catalysts by simple water removal methods Shimizu, Ken-ichi; Uozumi, Rie; Satsuma, Atsushi Catalysis Communications, Vol. 10, Issue 14, p. 1849-1853 https://doi.org/10.1016/j.catcom.2009.06.012	journal	August 2009
Production of levulinic acid and gamma-valerolactone (GVL) from cellulose using GVL as a solvent in biphasic systems Wettstein, Stephanie G.; Alonso, David Martin; Chong, Yuxuan Energy & Environmental Science, Vol. 5, Issue 8, p. 8199-8203 https://doi.org/10.1039/C2EE22111J	journal	January 2012
Technology development for the production of biobased products from biorefinery carbohydrates—the US Department of Energy’s “Top 10” revisited Bozell, Joseph J.; Petersen, Gene R. Green Chemistry, Vol. 12, Issue 4, p. 539-554 https://doi.org/10.1039/B922014C	journal	January 2010
Optimal design and operation of SMB bioreactor: production of high fructose syrup by isomerization of glucose Zhang, Yan; Hidajat, Kus; Ray, Ajay K. Biochemical Engineering Journal, Vol. 21, Issue 2, p. 111-121 https://doi.org/10.1016/j.bej.2004.05.007	journal	October 2004
Coordinated development of leading biomass pretreatment technologies Wyman, Charles E.; Dale, Bruce E.; Elander, Richard T. Bioresource Technology, Vol. 96, Issue 18, p. 1959-1966 https://doi.org/10.1016/j.biortech.2005.01.010	journal	December 2005
Influence of Reaction Conditions on Diacid Formation During Au-Catalyzed Oxidation of Glycerol and Hydroxymethylfurfural Zope, Bhushan N.; Davis, Sara E.; Davis, Robert J. Topics in Catalysis, Vol. 55, Issue 1-2, p. 24-32 https://doi.org/10.1007/s11244-012-9777-3	journal	February 2012
Dehydration of d-fructose to hydroxymethylfurfural in sub- and supercritical fluids Bicker, M.; Kaiser, D.; Ott, L. The Journal of Supercritical Fluids, Vol. 36, Issue 2, p. 118-126 https://doi.org/10.1016/j.supflu.2005.04.004	journal	December 2005
Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates Román-Leshkov, Yuriy; Barrett, Christopher J.; Liu, Zhen Y. Nature, Vol. 447, Issue 7147, p. 982-985 https://doi.org/10.1038/nature05923	journal	June 2007
Versatile dual hydrogenation–oxidation nanocatalysts for the aqueous transformation of biomass-derived platform molecules García-Suárez, Eduardo J.; Balu, Alina Mariana; Tristany, Mar Green Chemistry, Vol. 14, Issue 5, p. 1434-1439 https://doi.org/10.1039/C2GC35176E	journal	January 2012
Production and upgrading of 5-hydroxymethylfurfural using heterogeneous catalysts and biomass-derived solvents Gallo, Jean Marcel R.; Alonso, David Martin; Mellmer, Max A. Green Chem., Vol. 15, Issue 1 https://doi.org/10.1039/C2GC36536G	journal	January 2013
Synthesis of (±)-4-alkanolides from pent-4-enoic acid Ugurchieva, T. M.; Lozanova, A. V.; Zlokazov, M. V. Russian Chemical Bulletin, Vol. 57, Issue 3, p. 657-659 https://doi.org/10.1007/s11172-008-0103-y	journal	March 2008
Catalytic conversion of biomass to biofuels Alonso, David Martin; Bond, Jesse Q.; Dumesic, James A. Green Chemistry, Vol. 12, Issue 9, p. 1493-1513 https://doi.org/10.1039/C004654J	journal	January 2010
Acid-Functionalized SBA-15-Type Silica Catalysts for Carbohydrate Dehydration Crisci, Anthony J.; Tucker, Mark H.; Lee, Ming-Yung ACS Catalysis, Vol. 1, Issue 7, p. 719-728 https://doi.org/10.1021/cs2001237	journal	May 2011
On the mechanism of selective oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over supported Pt and Au catalysts Davis, Sara E.; Zope, Bhushan N.; Davis, Robert J. Green Chemistry, Vol. 14, Issue 1, p. 143-147 https://doi.org/10.1039/C1GC16074E	journal	January 2012
The selective hydrogenation of biomass-derived 5-hydroxymethylfurfural using heterogeneous catalysts Alamillo, Ricardo; Tucker, Mark; Chia, Mei Green Chemistry, Vol. 14, Issue 5, p. 1413-1419 https://doi.org/10.1039/C2GC35039D	journal	January 2012
Phase Modifiers Promote Efficient Production of Hydroxymethylfurfural from Fructose Roman-Leshkov, Yuriy; Chheda, Juben N.; Dumesic, James A. Science, Vol. 312, Issue 5782, p. 1933-1937 https://doi.org/10.1126/science.1126337	journal	June 2006
Mechanism of formation of 5-(hydroxymethyl)-2-furaldehyde from d-fructose and sucrose Antal, Michael Jerry; Mok, William S. L.; Richards, Geoffrey N. Carbohydrate Research, Vol. 199, Issue 1, p. 91-109 https://doi.org/10.1016/0008-6215(90)84096-D	journal	May 1990
Catalytic synthesis of α-methylene-γ-valerolactone: a biomass-derived acrylic monomer Manzer, Leo E. Applied Catalysis A: General, Vol. 272, Issue 1-2, p. 249-256 https://doi.org/10.1016/j.apcata.2004.05.048	journal	September 2004
The mechanism of glucose conversion to 5-hydroxymethylfurfural catalyzed by metal chlorides in ionic liquid: A theoretical study Guan, Jing; Cao, Quan; Guo, Xingcui Computational and Theoretical Chemistry, Vol. 963, Issue 2-3, p. 453-462 https://doi.org/10.1016/j.comptc.2010.11.012	journal	February 2011

Similar Records

Method to produce furandicarboxylic acid (FDCA) from 5-hydroxymethylfurfural (HMF)

Patent · Tue Apr 11 00:00:00 EDT 2017 · OSTI ID:1351100

Method to produce water-soluble sugars from biomass using solvents containing lactones

Patent · Tue Oct 01 00:00:00 EDT 2019 · OSTI ID:1576250

Related Subjects

60 APPLIED LIFE SCIENCES

Method to convert biomass to 5-(hydroxymethyl)-furfural (HMF) and furfural using lactones, furans, and pyrans as solvents

Citation Formats

References (41)

Similar Records

Related Subjects