Issue 22, 2019

Solvent basicity controlled deformylation for the formation of furfural from glucose and fructose

Abstract

The conversion of glucose and fructose to furfural can improve the productivity of furfural synthesis from biomass. We report that sulfolane, a weakly basic polar aprotic solvent, promoted the formation of furfural from hexoses with a maximum yield of 50% obtained from fructose. Addition of Sn/SBA-15 that acted as a Lewis acid catalyst enabled the conversion of glucose to furfural with 36% yield. Analysis of products obtained from isotopically labelled glucose showed that furfural is produced by elimination of the C6 carbon atom as a formaldehyde molecule. DFT calculations revealed that this elimination reaction is plausible in the presence of weakly basic solvents that are unable to abstract the proton from the C–H bond in the last step of the reaction, which would otherwise lead to formation of 5-HMF. The furfural yield was correlated with the basicity of solvents, calculated as proton affinity (Epa), confirming the hypothesis that the basicity of solvent determines the selectivity for the formation of furfural or 5-HMF. Hence furfural formation from hexoses can be achieved by acid catalysed reaction of hexoses in the presence of low basicity polar aprotic solvents.

Graphical abstract: Solvent basicity controlled deformylation for the formation of furfural from glucose and fructose

Supplementary files

Article information

Article type
Paper
Submitted
26 7 2019
Accepted
18 10 2019
First published
18 10 2019

Green Chem., 2019,21, 6146-6153

Solvent basicity controlled deformylation for the formation of furfural from glucose and fructose

M. Asakawa, A. Shrotri, H. Kobayashi and A. Fukuoka, Green Chem., 2019, 21, 6146 DOI: 10.1039/C9GC02600B

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements