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Mechanistic insights on the conversion of sugars into 5-hydroxymethylfurfural
Abstract
A sustainable bio-economy requires the efficient utilization of all of the components of biomass. After glucose, mannose and galactose are the most abundant 6-carbon sugars in plant hemicellulose; lactose is a common dairy byproduct. Here, we demonstrate the conversion of these sugars into 5-hydroxymethylfurfural (HMF), a key intermediate for renewable fuels and chemicals. Chromium salts enable the efficient conversion of mannose into HMF but are less effective for galactose, lactose, and the related hexulose, tagatose. Isotopic labeling studies and the reactivity of psicose and sorbose indicate that the key aldose-to-ketose conversion occurs via a 1,2-hydride shift, which is followed by dehydration of the furanose tautomer. These data valorize mannose, galatactose, and lactose as sources of HMF, and inform the design of new catalysts for the conversion of aldoses to ketoses.
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Citations
Cites
Metal Chlorides in Ionic Liquid Solvents Convert Sugars to 5-Hydroxymethylfurfural
Zhao, H., Holladay, J. E., Brown, H., & Zhang, Z. C. (2007) · Science · doi:10.1126/science.1141199 · Cited by 1,997
Cited by
Activation of Carbonyl-Containing Molecules with Solid Lewis Acids in Aqueous Media
Román-Leshkov, Y., & Davis, M. E. (2011) · ACS Catalysis · doi:10.1021/cs200411d · Cited by 401
Visions of sustainability in bioeconomy research
Pfau, S., Hagens, J., Dankbaar, B., & Smits, A. (2014) · Sustainability · doi:10.3390/su6031222 · Cited by 398
“…II Benning et al. [24] The Plant Journal Resources II Bergmann et al. [25] Renewable and Sustainable Energy Reviews Resources I Binder et al. [26] Energy and Environmental Science Processing and Technology II Boehlje et al. [27] International Food and Agribusiness Management Review Economics…”
Potential of hydrothermal treatments in lignocellulose biorefineries
Gullón, P., Romaní, A., Vila, C., Garrote, G., & Parajó, J. C. (2012) · Biofuels, Bioproducts and Biorefining · doi:10.1002/bbb.339 · Cited by 140
Organocatalysis in biorefining for biomass conversion and upgrading
Liu, D. (. J. )., & Chen, E. Y.-X. (2014) · Green Chem. · doi:10.1039/c3gc41934g · Cited by 101
Metadata
- Authors
- Binder, J. B., Cefali, A. V., Blank, J. J., & Raines, R. T.
- Venue
- Energy & Environmental Science
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 2010
- Volume
- 3
- Issue
- 6
- Pages
- 765
- ISSN
- 1754-5692 (ISSN-L)
- 1754-5706
- OpenAlex
- W2165792953
- Cited by
- 191
- References
- 1
- FWCI
- 8.92
- Type
- journal article
- Language
- en
- Open access
- closed
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Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
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