Title
Mechanism of the dehydration of d-fructose to 5-hydroxymethylfurfural in dimethyl sulfoxide at 150 °C: an NMR study
Document Type
Article
Publication Date
12-8-2008
Abstract
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. © 2008 Elsevier Ltd. All rights reserved.
Recommended Citation
Amarasekara, A., Williams, L., & Ebede, C. (2008). Mechanism of the dehydration of d-fructose to 5-hydroxymethylfurfural in dimethyl sulfoxide at 150 °C: an NMR study. Retrieved from https://digitalcommons.pvamu.edu/chemistry-physics-facpubs/100