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Title: Toward biomass-derived renewable plastics: Production of 2,5-furandicarboxylic acid from fructose

Abstract

We report a process for converting fructose, at a high concentration (15 weight %), to 2,5-furandicarboxylic acid (FDCA), a monomer used in the production of polyethylene furanoate, a renewable plastic. In our process, fructose is dehydrated to hydroxymethylfurfural (HMF) at high yields (70%) using a γ-valerolactone (GVL)/H 2O solvent system. HMF is subsequently oxidized to FDCA over a Pt/C catalyst with 93% yield. The advantage of our system is the higher solubility of FDCA in GVL/H 2O, which allows oxidation at high concentrations using a heterogeneous catalyst that eliminates the need for a homogeneous base. In addition, FDCA can be separated from the GVL/H 2O solvent system by crystallization to obtain >99% pure FDCA. Our process eliminates the use of corrosive acids, because FDCA is an effective catalyst for fructose dehydration, leading to improved economic and environmental impact of the process. Our techno-economic model indicates that the overall process is economically competitive with current terephthalic acid processes.

Authors:
ORCiD logo [1];  [1]; ORCiD logo [1]; ORCiD logo [2]; ORCiD logo [1]; ORCiD logo [1]
  1. Univ. of Wisconsin, Madison, WI (United States). Dept. of Chemical and Biological Engineering. Great Lakes Bioenergy Research Center
  2. Univ. of Wisconsin, Madison, WI (United States). Dept. of Chemical and Biological Engineering
Publication Date:
Research Org.:
Univ. of Wisconsin, Madison, WI (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Biological and Environmental Research (BER) (SC-23)
OSTI Identifier:
1499959
Grant/Contract Number:  
FC02-07ER64494
Resource Type:
Accepted Manuscript
Journal Name:
Science Advances
Additional Journal Information:
Journal Volume: 4; Journal Issue: 1; Journal ID: ISSN 2375-2548
Publisher:
AAAS
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Motagamwala, Ali Hussain, Won, Wangyun, Sener, Canan, Alonso, David Martin, Maravelias, Christos T., and Dumesic, James A. Toward biomass-derived renewable plastics: Production of 2,5-furandicarboxylic acid from fructose. United States: N. p., 2018. Web. doi:10.1126/sciadv.aap9722.
Motagamwala, Ali Hussain, Won, Wangyun, Sener, Canan, Alonso, David Martin, Maravelias, Christos T., & Dumesic, James A. Toward biomass-derived renewable plastics: Production of 2,5-furandicarboxylic acid from fructose. United States. doi:10.1126/sciadv.aap9722.
Motagamwala, Ali Hussain, Won, Wangyun, Sener, Canan, Alonso, David Martin, Maravelias, Christos T., and Dumesic, James A. Fri . "Toward biomass-derived renewable plastics: Production of 2,5-furandicarboxylic acid from fructose". United States. doi:10.1126/sciadv.aap9722. https://www.osti.gov/servlets/purl/1499959.
@article{osti_1499959,
title = {Toward biomass-derived renewable plastics: Production of 2,5-furandicarboxylic acid from fructose},
author = {Motagamwala, Ali Hussain and Won, Wangyun and Sener, Canan and Alonso, David Martin and Maravelias, Christos T. and Dumesic, James A.},
abstractNote = {We report a process for converting fructose, at a high concentration (15 weight %), to 2,5-furandicarboxylic acid (FDCA), a monomer used in the production of polyethylene furanoate, a renewable plastic. In our process, fructose is dehydrated to hydroxymethylfurfural (HMF) at high yields (70%) using a γ-valerolactone (GVL)/H2O solvent system. HMF is subsequently oxidized to FDCA over a Pt/C catalyst with 93% yield. The advantage of our system is the higher solubility of FDCA in GVL/H2O, which allows oxidation at high concentrations using a heterogeneous catalyst that eliminates the need for a homogeneous base. In addition, FDCA can be separated from the GVL/H2O solvent system by crystallization to obtain >99% pure FDCA. Our process eliminates the use of corrosive acids, because FDCA is an effective catalyst for fructose dehydration, leading to improved economic and environmental impact of the process. Our techno-economic model indicates that the overall process is economically competitive with current terephthalic acid processes.},
doi = {10.1126/sciadv.aap9722},
journal = {Science Advances},
number = 1,
volume = 4,
place = {United States},
year = {2018},
month = {1}
}

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Works referenced in this record:

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
  • DOI: 10.1039/C1GC16074E