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

van Putten, R-J., van der Waal, J. C., Harmse, M., van de Bovenkamp, H. H., de Jong, E. & Heeres, H. J., 21-Jul-2016, In : Chemsuschem. 9, 14, p. 1827-1834 8 p.

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  • A Comparative Study on the Reactivity of Various Ketohexoses

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DOI

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.

Original languageEnglish
Pages (from-to)1827-1834
Number of pages8
JournalChemsuschem
Volume9
Issue number14
Publication statusPublished - 21-Jul-2016

    Keywords

  • biomass, carbohydrates, oxygen heterocycles, isotopic labelling, reaction mechanisms, D-FRUCTOSE, LEVULINIC ACID, D-PSICOSE, D-GLUCOSE, CONVERSION, MONOSACCHARIDES, DEHYDRATION, CELLULOSE, WATER

ID: 36607811