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Mechanism of the dehydration of d-fructose to 5-hydroxymethylfurfural in dimethyl sulfoxide at 150°C: an NMR study
Open accessAbstract
The anomeric composition of D-fructose in dimethyl sulfoxide changes when the solution is heated from room temperature to 150 °C, with a small increase in the α-furanose form at the expense of the β-pyranose tautomer. Additionally, a small amount of α-pyranose form was also observed at 150 °C. A mechanism is proposed for the dehydration of D-fructose to 5-hydroxymethylfurfural in DMSO at 150 °C, where the solvent acts as the catalyst. A key intermediate in the reaction was identified as (4R,5R)-4-hydroxy-5-hydroxymethyl-4,5-dihydrofuran-2-carbaldehyde by using 1H and 13C NMR spectra of the sample during the reaction.
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Cites
Chemical Routes for the Transformation of Biomass into Chemicals
Corma, A., Iborra, S., & Velty, A. (2007) · Chemical Reviews · doi:10.1021/cr050989d · Cited by 5,970
Cited by
Hydroxymethylfurfural, A Versatile Platform Chemical Made from Renewable Resources
van Putten, R.-J., van der Waal, J. C., de Jong, E., Rasrendra, C. B., Heeres, H. J., & de Vries, J. G. (2013) · Chemical Reviews · doi:10.1021/cr300182k · Cited by 2,886
Organic Solvent Effects in Biomass Conversion Reactions
Shuai, L., & Luterbacher, J. (2016) · ChemSusChem · doi:10.1002/cssc.201501148 · Cited by 445
Gandini, A. (2010) · Polym. Chem. · doi:10.1039/b9py00233b · Cited by 295
Wang, C., Zhang, X., Liu, Q., Zhang, Q., Chen, L., & Ma, L. (2020) · Fuel Processing Technology · doi:10.1016/j.fuproc.2020.106485 · Cited by 157
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
- Amarasekara, A. S., Williams, L. D., & Ebede, C. C.
- Venue
- Carbohydrate Research
- Publisher
- Elsevier BV
- Published
- 2008-12
- Volume
- 343
- Issue
- 18
- Pages
- 3021-3024
- ISSN
- 0008-6215 (ISSN-L)
- OpenAlex
- W1975914784
- Cited by
- 355
- References
- 1
- FWCI
- 7.89
- Type
- journal article
- Language
- en
- Open access
- green
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- Amarasekara, A. S., Williams, L. D., & Ebede, C. C. (2008). Mechanism of the dehydration of d-fructose to 5-hydroxymethylfurfural in dimethyl sulfoxide at 150°C: an NMR study. Carbohydrate Research. https://doi.org/10.1016/j.carres.2008.09.008
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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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