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

Abstract

A process to produce furandicarboxylic acid (FDCA). The process includes the steps of reacting a C6 sugar-containing reactant in a reaction solution comprising a first organic solvent selected from the group consisting of beta-, gamma-, and delta-lactones, hydrofurans, hydropyrans, and combinations thereof, in the presence of an acid catalyst for a time and under conditions wherein at least a portion of the C6 sugar present in the reactant is converted to 5-(hydroxymethyl)furfural (HMF); oxidizing the HMF into FDCA with or without separating the HMF from the reaction solution; and extracting the FDCA by adding an aprotic organic solvent having a dipole moment of about 1.0 D or less to the reaction solution.

Inventors:
;
Issue Date:
Research Org.:
Wisconsin Alumni Research Foundation, Madison, WI (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1351100
Patent Number(s):
9617234
Application Number:
14/974,468
Assignee:
Wisconsin Alumni Research Foundation
Patent Classifications (CPCs):
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
DOE Contract Number:  
FC02-07ER64494
Resource Type:
Patent
Resource Relation:
Patent File Date: 2015 Dec 18
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Dumesic, James A., and Motagamwala, Ali Hussain. Method to produce furandicarboxylic acid (FDCA) from 5-hydroxymethylfurfural (HMF). United States: N. p., 2017. Web.
Dumesic, James A., & Motagamwala, Ali Hussain. Method to produce furandicarboxylic acid (FDCA) from 5-hydroxymethylfurfural (HMF). United States.
Dumesic, James A., and Motagamwala, Ali Hussain. Tue . "Method to produce furandicarboxylic acid (FDCA) from 5-hydroxymethylfurfural (HMF)". United States. https://www.osti.gov/servlets/purl/1351100.
@article{osti_1351100,
title = {Method to produce furandicarboxylic acid (FDCA) from 5-hydroxymethylfurfural (HMF)},
author = {Dumesic, James A. and Motagamwala, Ali Hussain},
abstractNote = {A process to produce furandicarboxylic acid (FDCA). The process includes the steps of reacting a C6 sugar-containing reactant in a reaction solution comprising a first organic solvent selected from the group consisting of beta-, gamma-, and delta-lactones, hydrofurans, hydropyrans, and combinations thereof, in the presence of an acid catalyst for a time and under conditions wherein at least a portion of the C6 sugar present in the reactant is converted to 5-(hydroxymethyl)furfural (HMF); oxidizing the HMF into FDCA with or without separating the HMF from the reaction solution; and extracting the FDCA by adding an aprotic organic solvent having a dipole moment of about 1.0 D or less to the reaction solution.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2017},
month = {4}
}

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Works referenced in this record:

Catalytic conversion of biomass to biofuels
journal, January 2010


Mechanism of the dehydration of d-fructose to 5-hydroxymethylfurfural in dimethyl sulfoxide at 150°C: an NMR study
journal, December 2008


Mechanism of formation of 5-(hydroxymethyl)-2-furaldehyde from d-fructose and sucrose
journal, May 1990


Simple Chemical Transformation of Lignocellulosic Biomass into Furans for Fuels and Chemicals
journal, February 2009


Production of 5-hydroxymethylfurfural and furfural by dehydration of biomass-derived mono- and poly-saccharides
journal, January 2007


Acid-Functionalized SBA-15-Type Silica Catalysts for Carbohydrate Dehydration
journal, May 2011


Oxidation of 5-hydroxymethylfurfural over supported Pt, Pd and Au catalysts
journal, February 2011


On the mechanism of selective oxidation of 5-hydroxymethylfurfural to 2,5-furandicarboxylic acid over supported Pt and Au catalysts
journal, January 2012


Direct conversion of cellulose and lignocellulosic biomass into chemicals and biofuel with metal chloride catalysts
journal, April 2012


Versatile dual hydrogenation–oxidation nanocatalysts for the aqueous transformation of biomass-derived platform molecules
journal, January 2012


The mechanism of glucose conversion to 5-hydroxymethylfurfural catalyzed by metal chlorides in ionic liquid: A theoretical study
journal, February 2011


Integrating enzymatic and acid catalysis to convert glucose into 5-hydroxymethylfurfural
journal, January 2010


Catalytic synthesis of α-methylene-γ-valerolactone: a biomass-derived acrylic monomer
journal, September 2004


Tin-containing zeolites are highly active catalysts for the isomerization of glucose in water
journal, March 2010


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


“One-Pot” Synthesis of 5-(Hydroxymethyl)furfural from Carbohydrates using Tin-Beta Zeolite
journal, April 2011


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
  • https://doi.org/10.1098/rspa.2012.0047

Glucose Reversion Reaction Kinetics
journal, May 2010


Phase Modifiers Promote Efficient Production of Hydroxymethylfurfural from Fructose
journal, June 2006


Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates
journal, June 2007


Solvent Effects on Fructose Dehydration to 5-Hydroxymethylfurfural in Biphasic Systems Saturated with Inorganic Salts
journal, January 2009


Transformations of biomass-derived platform molecules: from high added-value chemicals to fuels via aqueous-phase processing
journal, January 2011


Direct hydrothermal synthesis of mesoporous Sn-SBA-15 materials under weak acidic conditions
journal, March 2007


Enhanced production of hydroxymethylfurfural from fructose with solid acid catalysts by simple water removal methods
journal, August 2009


A one-pot reaction for biorefinery: combination of solid acid and base catalysts for direct production of 5-hydroxymethylfurfural from saccharides
journal, January 2009


Synthesis of (±)-4-alkanolides from pent-4-enoic acid
journal, March 2008


Production of levulinic acid and gamma-valerolactone (GVL) from cellulose using GVL as a solvent in biphasic systems
journal, January 2012


Coordinated development of leading biomass pretreatment technologies
journal, December 2005


Efficient Catalytic System for the Selective Production of 5-Hydroxymethylfurfural from Glucose and Fructose
journal, October 2008


Ionic Liquid-Mediated Formation of 5-Hydroxymethylfurfural—A Promising Biomass-Derived Building Block
journal, February 2011


Optimal design and operation of SMB bioreactor: production of high fructose syrup by isomerization of glucose
journal, October 2004


Metal Chlorides in Ionic Liquid Solvents Convert Sugars to 5-Hydroxymethylfurfural
journal, June 2007


Solid acid catalysis of tandem isomerization-lactonization of olefinic acids
journal, December 2007


Influence of Reaction Conditions on Diacid Formation During Au-Catalyzed Oxidation of Glycerol and Hydroxymethylfurfural
journal, February 2012