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Catalytic Conversion of Fructose, Glucose, and Sucrose to 5-(Hydroxymethyl)furfural and Levulinic and Formic Acids in γ-Valerolactone As a Green Solvent

Qi, Long, Mui, Yiu Fung, Lo, See Wing, Lui, Matthew Y., Akien, Geoffrey R., Horváth, István T.·2014·ACS Catalysis

Abstract

The conversion of fructose, glucose, and sucrose to 5-(hydroxymethyl)furfural (HMF) and levulinic acid (LA)/formic acid (FA) was investigated in detail using sulfuric acid as the catalyst and γ-valerolactone (GVL) as a green solvent. The H 2 SO 4 /GVL/H 2 O system can be tuned to produce either HMF or LA/FA by changing the acid concentration and thus allowing selective switching between the products. Although the best yields of HMF were around 75%, the LA/FA yields ranged from 50% to 70%, depending on the structure of the carbohydrates and the reaction parameters, including temperature, acid, and carbohydrate concentrations. While the conversion of fructose is much faster than glucose, sucrose behaves like a 1:1 mixture of fructose and glucose, indicating facile hydrolysis of the glycosidic bond in sucrose. The mechanism of the conversion of glucose to HMF or LA/FA in GVL involves three intermediates: 1,6-anhydro-β- d -glucofuranose, 1,6-anhydro-β- d -glucopyranose, and levoglucosenone.

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Metadata

Authors
Qi, L., Mui, Y. F., Lo, S. W., Lui, M. Y., Akien, G. R., & Horváth, I. T.
Venue
ACS Catalysis
Published
2014-04-10
Volume
4
Issue
5
Pages
1470-1477
ISSN
2155-5435 (ISSN-L)
OpenAlex
W2330618456
Cited by
307
References
2
FWCI
17.88
Type
journal article
Language
en
Open access
closed

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