Skip to main content
U.S. Department of Energy
Office of Scientific and Technical Information

Synthesis of biomass-derived feedstocks for the polymers and fuels industries from 5-(hydroxymethyl)furfural (HMF) and acetone

Journal Article · · Green Chemistry
DOI:https://doi.org/10.1039/c9gc01859j· OSTI ID:1799487

We show that 5-(hydroxymethyl) furfural (HMF) and acetone can be selectively converted into a range of biomass-derived high molecular weight chemicals in high yield (>90%). HMF was condensed with acetone and purified to produce HMF-Acetone-HMF dimer (HAH). We then selectively synthesized various compounds from HAH by the sequential catalytic reaction pathway of hydrogenation, ring-opening, and hydrodeoxygenation. These synthesized HMF-derived chemicals were characterized by 1D and 2D NMR spectra and high resolution mass spectrometry (HRMS). The HMF-derived molecules described in this paper can be feedstocks for the polymer, pigment, and petroleum industries.

Research Organization:
Univ. of Tennessee, Knoxville, TN (United States); Univ. of Wisconsin, Madison, WI (United States)
Sponsoring Organization:
USDOE Office of Energy Efficiency and Renewable Energy (EERE)
Grant/Contract Number:
EE0008353; SC0018409
OSTI ID:
1799487
Alternate ID(s):
OSTI ID: 1557333
Journal Information:
Green Chemistry, Journal Name: Green Chemistry Journal Issue: 20 Vol. 21; ISSN GRCHFJ; ISSN 1463-9262
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English

References (36)

Pd/NbOPO 4 Multifunctional Catalyst for the Direct Production of Liquid Alkanes from Aldol Adducts of Furans journal July 2014
Selective Conversion of Cellulose to Hydroxymethylfurfural in Polar Aprotic Solvents journal July 2014
Liquid Alkanes with Targeted Molecular Weights from Biomass-Derived Carbohydrates journal May 2008
Biomass into Chemicals: Aerobic Oxidation of 5-Hydroxymethyl-2-furfural into 2,5-Furandicarboxylic Acid with Gold Nanoparticle Catalysts journal December 2009
Diesel and Alkane Fuels From Biomass by Organocatalysis and Metal-Acid Tandem Catalysis journal August 2013
Catalytic Upgrading of 5-Hydroxymethylfurfural to Drop-in Biofuels by Solid Base and Bifunctional Metal-Acid Catalysts journal November 2015
Liquid phase aldol condensation reactions with MgO–ZrO2 and shape-selective nitrogen-substituted NaY journal January 2011
Comparison of HMF hydrodeoxygenation over different metal catalysts in a continuous flow reactor journal November 2015
Single-reactor process for sequential aldol-condensation and hydrogenation of biomass-derived compounds in water journal June 2006
Heterogeneous catalyst-assisted thermochemical conversion of food waste biomass into 5-hydroxymethylfurfural journal February 2015
Polar aprotic solvent-water mixture as the medium for catalytic production of hydroxymethylfurfural (HMF) from bread waste journal December 2017
Biodegradable and non-retrogradable eco-films based on starch–glycerol with citric acid as crosslinking agent journal March 2016
An overview of aqueous-phase catalytic processes for production of hydrogen and alkanes in a biorefinery journal January 2006
Etherification of 5-hydroxymethyl-2-furfural (HMF) with ethanol to biodiesel components using mesoporous solid acidic catalysts journal October 2011
Synthesis of diesel range alkanes with 2-methylfuran and mesityl oxide from lignocellulose journal October 2014
NaOH catalyzed condensation reactions between levulinic acid and biomass derived furan-aldehydes in water journal March 2015
Esterification by solid acid catalysts—a comparison journal December 2004
Carbon–carbon bond formation for biomass-derived furfurals and ketones by aldol condensation in a biphasic system journal December 2008
Synthesis and thermal cure of high molecular weight polybenzoxazine precursors and the properties of the thermosets journal December 2005
Synthesis of 1,6-Hexanediol from Cellulose Derived Tetrahydrofuran-Dimethanol with Pt-WO x /TiO 2 Catalysts journal January 2018
Formation and Growth of Humins via Aldol Addition and Condensation during Acid-Catalyzed Conversion of 5-Hydroxymethylfurfural journal October 2011
Synthesis of Diesel or Jet Fuel Range Cycloalkanes with 2-Methylfuran and Cyclopentanone from Lignocellulose journal July 2014
Production of dimethylfuran for liquid fuels from biomass-derived carbohydrates journal June 2007
Synthesis of renewable high-density fuel with isophorone journal July 2017
Production and upgrading of 5-hydroxymethylfurfural using heterogeneous catalysts and biomass-derived solvents journal January 2013
Targeted chemical upgrading of lignocellulosic biomass to platform molecules journal January 2014
Lignosulfonate-based acidic resin for the synthesis of renewable diesel and jet fuel range alkanes with 2-methylfuran and furfural journal January 2015
CO 2 -Catalysed aldol condensation of 5-hydroxymethylfurfural and acetone to a jet fuel precursor journal January 2016
Propylene carbonate and γ-valerolactone as green solvents enhance Sn( iv )-catalysed hydroxymethylfurfural (HMF) production from bread waste journal January 2018
Solvent system for effective near-term production of hydroxymethylfurfural (HMF) with potential for long-term process improvement journal January 2019
Sustainable bio-based furan epoxy resin with flame retardancy journal January 2019
Calculation of Flame Ionization Detector Relative Response Factors Using the Effective Carbon Number Concept journal August 1985
Toward biomass-derived renewable plastics: Production of 2,5-furandicarboxylic acid from fructose journal January 2018
Production of Liquid Alkanes by Aqueous-Phase Processing of Biomass-Derived Carbohydrates journal June 2005
Electrically conducting polymers: a review of the electropolymerization reaction, of the effects of chemical structure on polymer film properties, and of applications towards technology journal January 1986
Regioselective Polymerization of Sorbitol and Divinyl Sebacate Using Lipase Catalyst journal July 2000