Publication
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.Research output: Contribution to journal › Article › Academic › peer-review

Documents
- A Comparative Study on the Reactivity of Various Ketohexoses
Final publisher's version, 883 KB, PDF document
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 language | English |
---|---|
Pages (from-to) | 1827-1834 |
Number of pages | 8 |
Journal | Chemsuschem |
Volume | 9 |
Issue number | 14 |
Publication status | Published - 21-Jul-2016 |
- biomass, carbohydrates, oxygen heterocycles, isotopic labelling, reaction mechanisms, D-FRUCTOSE, LEVULINIC ACID, D-PSICOSE, D-GLUCOSE, CONVERSION, MONOSACCHARIDES, DEHYDRATION, CELLULOSE, WATER
Keywords
ID: 36607811