Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 360, Issue 12, Pages 2358-2363Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201800058
Keywords
Isomerisation; Hydrogen Isotope Exchange; Ru/C; Isohexide; Isohexide Ether
Categories
Funding
- German Federal Ministry of Food and Agriculture [FKZ: 22024111, 22026615]
- Max Buchner Foundation [3415]
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In this article we show that the catalytic isomerization of isohexide sugar alcohols as well as their respective ethers can occur by a hydride-based mechanism rather than a dehydrogenation/re-hydrogenation. C-H bonds in-position to hydroxy and ether groups are activated using Ru/C as solid catalyst at temperatures as high as 160 degrees C and above. Hydrogen isotope exchange experiments proved that a full hydride exchange and isomerization is possible for isohexides but unexpectedly also for their methyl ethers. This is of great importance as it proves the co-existence of the both mechanisms for reactions that were so far assumed to occur solely by a dehydrogenation/re-hydrogenation. Hence, this co-existence should be taken into account for kinetic investigations of such reaction systems especially in the conversion of biomass-based chemicals under hydrogenation conditions.
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