An efficient catalytic dehydration of fructose and sucrose to 5-hydroxymethylfurfural with protic ionic liquids

Xinli Tong; Yang Ma; Yongdan Li

doi:10.1016/j.carres.2010.05.019

An efficient catalytic dehydration of fructose and sucrose to 5-hydroxymethylfurfural with protic ionic liquids

Carbohydr Res. 2010 Aug 16;345(12):1698-701. doi: 10.1016/j.carres.2010.05.019. Epub 2010 May 27.

Authors

Xinli Tong¹, Yang Ma, Yongdan Li

Affiliation

¹ Tianjin Key Laboratory of Applied Catalysis Science and Technology and State Key Laboratory of Chemical Engineering, School of Chemical Engineering, Tianjin University, Tianjin 300072, China.

PMID: 20598294
DOI: 10.1016/j.carres.2010.05.019

Abstract

The renewable furan-based platform chemical, 5-hydroxymethylfurfural (HMF), has been efficiently synthesized from d-fructose and sucrose in the presence of a catalytic amount of protic ionic liquids. The 1-methylimidazolium-based and N-methylmorpholinium-based ionic liquids are employed. As a result, 74.8% and 47.5% yields of HMF are obtained from d-fructose and sucrose, respectively, at 90 degrees C for 2h under nitrogen atmosphere when N-methylmorpholinium methyl sulfonate ([NMM](+)[CH(3)SO(3)](-)) is used as the catalyst in an N,N-dimethylformamide-lithium bromide (DMF-LiBr) system. The acidities of ionic liquids are determined by the Hammett method, and the correlation between acidity and catalytic activity is discussed. Moreover, the effects of reaction temperature and time are investigated, and a plausible reaction mechanism for the dehydration of d-fructose is proposed.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Dehydration
Fructose / chemistry*
Furaldehyde / analogs & derivatives*
Furaldehyde / chemical synthesis
Furaldehyde / chemistry
Ionic Liquids / chemistry*
Molecular Structure
Protons*
Sucrose / chemistry*
Temperature

Substances

Ionic Liquids
Protons
Fructose
Sucrose
5-hydroxymethylfurfural
Furaldehyde