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 »
- Authors:
- Publication Date:
- Research Org.:
- National Renewable Energy Laboratory (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:
- 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},
journal = {Biotechnology for Biofuels},
number = 1,
volume = 12,
place = {Netherlands},
year = {Sat Oct 26 00:00:00 EDT 2019},
month = {Sat Oct 26 00:00:00 EDT 2019}
}
https://doi.org/10.1186/s13068-019-1595-4
Web of Science
Works referenced in this record:
On the Effect of Tetraborate Ions in the Generation of Colored Products in Thermally Processed Glycine−Carbohydrate Solutions
journal, March 2007
- Rizzi, George P.
- Journal of Agricultural and Food Chemistry, Vol. 55, Issue 5
One-pot Formation of Furfural from Xylose via Isomerization and Successive Dehydration Reactions over Heterogeneous Acid and Base Catalysts
journal, August 2010
- Takagaki, Atsushi; Ohara, Mika; Nishimura, Shun
- Chemistry Letters, Vol. 39, Issue 8
Integrating enzymatic and acid catalysis to convert glucose into 5-hydroxymethylfurfural
journal, January 2010
- Huang, Renliang; Qi, Wei; Su, Rongxin
- Chem. Commun., Vol. 46, Issue 7, p. 1115-1117
Xylose Isomerization to Xylulose and its Dehydration to Furfural in Aqueous Media
journal, October 2011
- Choudhary, Vinit; Pinar, Ana B.; Sandler, Stanley I.
- ACS Catalysis, Vol. 1, Issue 12
Production of 5-hydroxymethylfurfural and furfural by dehydration of biomass-derived mono- and poly-saccharides
journal, January 2007
- Chheda, Juben N.; Román-Leshkov, Yuriy; Dumesic, James A.
- Green Chem., Vol. 9, Issue 4, p. 342-350
Conversion of Xylose to Furfural Using Lewis and Brønsted Acid Catalysts in Aqueous Media
journal, August 2012
- Choudhary, Vinit; Sandler, Stanley I.; Vlachos, Dionisios G.
- ACS Catalysis, Vol. 2, Issue 9
The role of biomass in America's energy future: framing the analysis
journal, March 2009
- Lynd, Lee R.; Larson, Eric; Greene, Nathanael
- Biofuels, Bioproducts and Biorefining, Vol. 3, Issue 2
Ethanol Can Contribute to Energy and Environmental Goals
journal, January 2006
- Farrell, A. E.
- Science, Vol. 311, Issue 5760
Condition screening and process investigation of aldose transformation in borate-containing acidic phosphate buffer system under microwave irradiation
journal, January 2014
- Yan, Yani; Wu, Qingbin; Guo, Xiao
- RSC Adv., Vol. 4, Issue 74
Effect of Borate on the Alkali-catalyzed Isomerization of Sugars 1
journal, September 1960
- Mendicino, Joseph F.
- Journal of the American Chemical Society, Vol. 82, Issue 18
Production of Furfural from Process-Relevant Biomass-Derived Pentoses in a Biphasic Reaction System
journal, June 2017
- Mittal, Ashutosh; Black, Stuart K.; Vinzant, Todd B.
- ACS Sustainable Chemistry & Engineering, Vol. 5, Issue 7
Phase Modifiers Promote Efficient Production of Hydroxymethylfurfural from Fructose
journal, June 2006
- Roman-Leshkov, Yuriy; Chheda, Juben N.; Dumesic, James A.
- Science, Vol. 312, Issue 5782, p. 1933-1937
Kinetics of Glucose Isomerization to Fructose by Immobilized Glucose Isomerase (Sweetzyme IT)
journal, April 2009
- Dehkordi, Asghar Molaei; Tehrany, Mehrdad Shoai; Safari, Iman
- Industrial & Engineering Chemistry Research, Vol. 48, Issue 7
Use of Sweetzyme in Industrial Continuous Isomerization Various Process Alternatives and Corresponding Product Types
journal, January 1976
- Oestergaard, J.; Knudsen, S. L.
- Starch - Stärke, Vol. 28, Issue 10
Conversion of fructose to 5-hydroxymethylfurfural using ionic liquids prepared from renewable materials
journal, January 2008
- Hu, Suqin; Zhang, Zhaofu; Zhou, Yinxi
- Green Chemistry, Vol. 10, Issue 12
The structure and (local) stability constants of borate esters of mono- and di-saccharides as studied by 11B and 13C NMR spectroscopy
journal, February 1994
- van den Berg, Ron; Peters, Joop A.; van Bekkum, Herman
- Carbohydrate Research, Vol. 253
Efficient conversion of glucose into 5-hydroxymethylfurfural catalyzed by a common Lewis acid SnCl4 in an ionic liquid
journal, January 2009
- Hu, Suqin; Zhang, Zhaofu; Song, Jinliang
- Green Chemistry, Vol. 11, Issue 11
A highly efficient dilute alkali deacetylation and mechanical (disc) refining process for the conversion of renewable biomass to lower cost sugars
journal, January 2014
- Chen, Xiaowen; Shekiro, Joseph; Pschorn, Thomas
- Biotechnology for Biofuels, Vol. 7, Issue 1
Effect of mechanical disruption on the effectiveness of three reactors used for dilute acid pretreatment of corn stover Part 1: chemical and physical substrate analysis
journal, January 2014
- Wang, Wei; Chen, Xiaowen; Donohoe, Bryon S.
- Biotechnology for Biofuels, Vol. 7, Issue 1
Kinetics of furfural production by dehydration of xylose in a biphasic reactor with microwave heating
journal, January 2010
- Weingarten, Ronen; Cho, Joungmo; Conner, Jr., Wm. Curtis
- Green Chemistry, Vol. 12, Issue 8
Dehydration of xylose into furfural over micro-mesoporous sulfonic acid catalysts
journal, January 2005
- Dias, A.; Pillinger, M.; Valente, A.
- Journal of Catalysis, Vol. 229, Issue 2
Kinetic studies of the enzymatic isomerization of xylose
journal, March 1985
- Roman, Graciela N.; Jansen, Norman B.; Hsiao, Humg-Yu
- Enzyme and Microbial Technology, Vol. 7, Issue 3