Article ID Journal Published Year Pages File Type
65683 Journal of Molecular Catalysis A: Chemical 2013 5 Pages PDF
Abstract

•Glycosidic bond hydrolysis couples with fructose dehydration to promote reaction.•1,2-Glycosidic bond was more difficult cleavage than 1,4-glycosidic bond.•Amino group plays a great role in the rate-determining step of glucose isomerization.•COOH well catalyzes sucrose hydrolysis and fructose dehydration.•Tyrosine displays the best activity in sucrose conversion to 5-HMF.

In this study, the synthesis of 5-hydroxymethylfurfural (5-HMF) from sucrose was carried out in ionic liquids 1-ethyl-3-methylimidazolium bromide ([Emim]Br) catalyzed by amino acids, and tyrosine displays the best activity. Under the optimal reaction conditions, 76.0% yield of 5-HMF from sucrose was obtained at 160 °C for 4 h. The uniquely effective activity of tyrosine for sucrose conversion into 5-HMF in [Emim]Br is mainly attributed to its two types of active sites, free base NH2 and dissociated H+ sites. The former one plays a crucial role in the isomerization of glucose to fructose, and the latter one is active in the hydrolysis of sucrose into monosaccharides and dehydration of generated fructose to 5-HMF. Furthermore, the presence of acidic phenol group in tyrosine also has the synergic catalytic effect on sucrose conversion. In addition, with the use of tyrosine catalyst, other carbohydrates to form 5-HMF were also tested, and the effects of solvent, reaction temperature and reaction time on sucrose conversion into 5-HMF were investigated in detail. A possible mechanism for this catalytic process has been proposed.

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Physical Sciences and Engineering Chemical Engineering Catalysis
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