A Comparative Study on the Reactivity of Various Ketohexoses to Furanics in Methanol

作者:van Putten Robert Jan*; van der Waal Jan C; Harmse Martin; van de Bovenkamp Henk H; de Jong Ed; Heeres Hero J*
来源:Chemsuschem, 2016, 9(14): 1827-1834.
DOI:10.1002/cssc.201600252

摘要

The acid-catalysed dehydration of the four 2-ketohexoses (fructose, sorbose, tagatose and psicose) to furanics was studied in methanol (65 gL(-1) substrate concentration, 17 and 34 mm sulfuric acid, 100 degrees C) with Avantium high-throughput technology. Significant differences in the reactivities of the hexoses and yields of 5-hydroxymethylfurfural (HMF) and its methyl ether (MMF) were observed. Psicose and tagatose were the most reactive, and psicose also afforded the highest combined yield of MMF and HMF of approximately 55% at 96% sugar conversion. Hydroxyacetylfuran and its corresponding methyl ether were formed as byproducts, particularly for sorbose and tagatose, with a maximum combined yield of 8% for sorbose. The formation of hydroxyacetylfuran was studied through C-13 NMR spectroscopy with labelled sorbose, which provided new insights into the reaction mechanism.

  • 出版日期2016-7-21