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A Comparative Study on the Reactivity of Various Ketohexoses to Furanics in Methanol
Author(s) -
van Putten RobertJan,
van der Waal Jan C.,
Harmse Martin,
van de Bovenkamp Henk H.,
de Jong Ed,
Heeres Hero J.
Publication year - 2016
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201600252
Subject(s) - sorbose , chemistry , yield (engineering) , methanol , reactivity (psychology) , sulfuric acid , organic chemistry , fructose , ketose , ether , aldose , glycoside , medicine , materials science , alternative medicine , pathology , metallurgy
The acid‐catalysed dehydration of the four 2‐ketohexoses (fructose, sorbose, tagatose and psicose) to furanics was studied in methanol (65 g L −1 substrate concentration, 17 and 34 m m sulfuric acid, 100 °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 13 C NMR spectroscopy with labelled sorbose, which provided new insights into the reaction mechanism.