One-pot conversion of carbohydrates into 5-ethoxymethylfurfural and ethyl d-glucopyranoside in ethanol catalyzed by a silica supported sulfonic acid catalyst

Abstract

In this study, prepared silica supported sulfonic acid was used as a heterogeneous catalyst for the production of 5-ethoxymethylfurfural (EMF) from fructose based carbohydrates and the synthesis of ethyl D-glucopyranoside from glucose based carbohydrates in ethanol. EMF was obtained in a high yield of 83.8% from 5-hydroxymethylfurfural (HMF) after 10 h, and a 63.1% yield was obtained from fructose at 100 °C for 24 h. Temperature experiments demonstrated that a higher reaction temperature (in the case of 120 °C) resulted in side reactions such as polymerization of HMF and alcoholysis of HMF into ethyl levulinates. When di- and poly-saccharides (sucrose and inulin) were used, the fructose moieties in sucrose and inulin were also successfully converted into EMF. However, the silica supported sulfonic acid catalyst was inert for the production of EMF from aldose based carbohydrates such as glucose and cellobiose. Ethyl D-glucopyranoside was formed in a high yield of 91.7% from glucose. More importantly, the catalyst could be reused several times without losing its catalytic activity with an average EMF yield of around 60% from a one-pot reaction of fructose. This work provides a good outlook for the conversion of carbohydrates into fine chemicals and biofuel additive.