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Title: Simultaneous upgrading of biomass-derived sugars to HMF/furfural via enzymatically isomerized ketose intermediates

Abstract

Abstract Background Recently, exploring fermentative or chemical pathways that convert biomass-derived sugars to fuels/chemicals has attracted a lot of interest from many researchers. We are investigating a hydrocarbon pathway from mixed sugars via 5-hydroxymethyl furfural (HMF) and furfural intermediates. To achieve this goal, we must first convert glucose and xylose to HMF and furfural in favorable yields. Current processes to produce HMF/furfural generally involve the use of acid catalysts in biphasic systems or solvents such as ionic liquids. However, the yield from transforming glucose to HMF is lower than the yield of furfural from xylose. Results In this study, we present an efficient chemical pathway simultaneously transforming glucose and xylose to HMF and furfural via ketose intermediates, i.e., fructose and xylulose, which were generated from glucose and xylose via enzymatic isomerization. In the enzymatic isomerization, by adding sodium borate to complex with the ketoses, xylose conversion reached equilibrium after 2 h with a conversion of 91% and glucose conversion reached 84% after 4 h. By enzymatically isomerizing the aldoses to ketoses, the following dehydration reactions to HMF and furfural could be performed at low process temperatures (i.e., 110–120 °C) minimizing the side reactions of the sugars and limiting the degradation of furfurals tomore » humins and carboxylic acids. At 120 °C, pH 0.5, and 15 min reaction time, mixed ketose sugars were converted to HMF and furfural in yields of 77% and 96%, respectively (based on starting aldose concentrations). Conclusion Taken together, our results demonstrate that this combined biological and chemical process could be an effective pathway to simultaneously convert biomass-derived glucose and xylose to HMF and furfural, for use as intermediates in the production of hydrocarbons.« less

Authors:
; ; ; ; ;
Publication Date:
Research Org.:
National Renewable Energy Lab. (NREL), Golden, CO (United States)
Sponsoring Org.:
USDOE Office of Energy Efficiency and Renewable Energy (EERE)
OSTI Identifier:
1618769
Alternate Identifier(s):
OSTI ID: 1574197
Report Number(s):
NREL/JA-2700-75135
Journal ID: ISSN 1754-6834; 253; PII: 1595
Grant/Contract Number:  
AC36-08GO28308
Resource Type:
Journal Article: Published Article
Journal Name:
Biotechnology for Biofuels
Additional Journal Information:
Journal Name: Biotechnology for Biofuels Journal Volume: 12 Journal Issue: 1; Journal ID: ISSN 1754-6834
Publisher:
Springer Science + Business Media
Country of Publication:
Netherlands
Language:
English
Subject:
09 BIOMASS FUELS; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; glucose; xylose; enzymatic isomerization; ketose; HMF; dehydration; furfural

Citation Formats

Wang, Wei, Mittal, Ashutosh, Pilath, Heidi, Chen, Xiaowen, Tucker, Melvin P., and Johnson, David K. Simultaneous upgrading of biomass-derived sugars to HMF/furfural via enzymatically isomerized ketose intermediates. Netherlands: N. p., 2019. Web. doi:10.1186/s13068-019-1595-4.
Wang, Wei, Mittal, Ashutosh, Pilath, Heidi, Chen, Xiaowen, Tucker, Melvin P., & Johnson, David K. Simultaneous upgrading of biomass-derived sugars to HMF/furfural via enzymatically isomerized ketose intermediates. Netherlands. https://doi.org/10.1186/s13068-019-1595-4
Wang, Wei, Mittal, Ashutosh, Pilath, Heidi, Chen, Xiaowen, Tucker, Melvin P., and Johnson, David K. Sat . "Simultaneous upgrading of biomass-derived sugars to HMF/furfural via enzymatically isomerized ketose intermediates". Netherlands. https://doi.org/10.1186/s13068-019-1595-4.
@article{osti_1618769,
title = {Simultaneous upgrading of biomass-derived sugars to HMF/furfural via enzymatically isomerized ketose intermediates},
author = {Wang, Wei and Mittal, Ashutosh and Pilath, Heidi and Chen, Xiaowen and Tucker, Melvin P. and Johnson, David K.},
abstractNote = {Abstract Background Recently, exploring fermentative or chemical pathways that convert biomass-derived sugars to fuels/chemicals has attracted a lot of interest from many researchers. We are investigating a hydrocarbon pathway from mixed sugars via 5-hydroxymethyl furfural (HMF) and furfural intermediates. To achieve this goal, we must first convert glucose and xylose to HMF and furfural in favorable yields. Current processes to produce HMF/furfural generally involve the use of acid catalysts in biphasic systems or solvents such as ionic liquids. However, the yield from transforming glucose to HMF is lower than the yield of furfural from xylose. Results In this study, we present an efficient chemical pathway simultaneously transforming glucose and xylose to HMF and furfural via ketose intermediates, i.e., fructose and xylulose, which were generated from glucose and xylose via enzymatic isomerization. In the enzymatic isomerization, by adding sodium borate to complex with the ketoses, xylose conversion reached equilibrium after 2 h with a conversion of 91% and glucose conversion reached 84% after 4 h. By enzymatically isomerizing the aldoses to ketoses, the following dehydration reactions to HMF and furfural could be performed at low process temperatures (i.e., 110–120 °C) minimizing the side reactions of the sugars and limiting the degradation of furfurals to humins and carboxylic acids. At 120 °C, pH 0.5, and 15 min reaction time, mixed ketose sugars were converted to HMF and furfural in yields of 77% and 96%, respectively (based on starting aldose concentrations). Conclusion Taken together, our results demonstrate that this combined biological and chemical process could be an effective pathway to simultaneously convert biomass-derived glucose and xylose to HMF and furfural, for use as intermediates in the production of hydrocarbons.},
doi = {10.1186/s13068-019-1595-4},
url = {https://www.osti.gov/biblio/1618769}, journal = {Biotechnology for Biofuels},
issn = {1754-6834},
number = 1,
volume = 12,
place = {Netherlands},
year = {2019},
month = {10}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record at https://doi.org/10.1186/s13068-019-1595-4

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Cited by: 3 works
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Works referenced in this record:

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


Xylose Isomerization to Xylulose and its Dehydration to Furfural in Aqueous Media
journal, October 2011


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


Conversion of Xylose to Furfural Using Lewis and Brønsted Acid Catalysts in Aqueous Media
journal, August 2012


The role of biomass in America's energy future: framing the analysis
journal, March 2009


Ethanol Can Contribute to Energy and Environmental Goals
journal, January 2006


Worldwide production of high-fructose syrup and crystalline fructose
journal, November 1993


Effect of Borate on the Alkali-catalyzed Isomerization of Sugars 1
journal, September 1960


Production of Furfural from Process-Relevant Biomass-Derived Pentoses in a Biphasic Reaction System
journal, June 2017


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


Kinetics of Glucose Isomerization to Fructose by Immobilized Glucose Isomerase (Sweetzyme IT)
journal, April 2009


Conversion of fructose to 5-hydroxymethylfurfural using ionic liquids prepared from renewable materials
journal, January 2008


Efficient conversion of glucose into 5-hydroxymethylfurfural catalyzed by a common Lewis acid SnCl4 in an ionic liquid
journal, January 2009


Kinetics of furfural production by dehydration of xylose in a biphasic reactor with microwave heating
journal, January 2010


Dehydration of xylose into furfural over micro-mesoporous sulfonic acid catalysts
journal, January 2005


Production of Ethanol from d-Xylose by Using d-Xylose Isomerase and Yeasts
journal, January 1981


Kinetic studies of the enzymatic isomerization of xylose
journal, March 1985