Mechanism and Malleability of Glucose Dehydration to HMF: Entry Points and Water-Induced Diversions

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Abstract

The stoichiometric dehydration of glucose to 5-hydroxymethylfurfural (HMF) converts an abundant substrate to a versatile chemical. HMF formation can be optimized by using suitable solvents including ionic liquids and DMSO, and by cosolvents such as water. A prerequisite for efficient glucose influx into pathways to HMF is the isomerization of glucose to a ketose, typically the Lewis acid catalyzed conversion to fructose. Here, influx of glucose into pathways to HMF is compared through kinetic observations under reaction conditions and through isotope distributions in the product. Diversions from the path to HMF in the presence of water are described for the popular CrCl3/DMSO system. Addition of water to this system favors the formation of a useful byproduct instead of a mixture of inert compounds.
Original languageEnglish
JournalCatalysis Science and Technology
Pages (from-to)1724-1730
ISSN2044-4753
DOIs
Publication statusPublished - 2020

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