Dehydration of fructose to 5-hydroxymethylfurfural by rare earth metal trifluoromethanesulfonates in organic solvents

The catalytic dehydration of fructose to 5-hydroxymethylfurfural (HMF) was investigated by using various rare earth metal trifluoromethanesulfonates, that is, Yb(OTf)3, Sc(OTf)3, Ho(OTf)3, Sm(OTf)3, Nd(OTf)3 as catalysts in DMSO. It is found that the catalytic activity increases with decreasing ionic radius of rare earth metal cations. Among the examined catalysts, Sc(OTf)3 exhibits the highest catalytic activity. Fructose conversion of 100% and a HMF yield of 83.3% are obtained at 120 °C after 2 h by using Sc(OTf)3 as the catalyst. Moreover, the catalytic dehydration of fructose was also carried out in different solvents, for example, DMA, 1,4-dioxane, and a mixture of PEG-400 and water. The results show that among the solvents DMSO is the most efficient in promoting the dehydration of fructose to HMF, and no rehydration byproducts such as levulinic acid and formic acid are detected.

Graphical abstractThe catalytic activity of various rare earth metal trifluoromethanesulfonates in the dehydration of fructose to 5-hydroxymethylfurfural (HMF) increases with decreasing ionic radius of rare earth metal cations.Figure optionsDownload full-size imageDownload as PowerPoint slide