Mechanism study of sugar and sugar alcohol hydrogenolysis using 1,3-diol model compounds
- Michigan State Univ., East Lansing, MI (United States). Dept. of Chemical Engineering
Knowledge of the bond cleavage mechanism governing sugar and sugar alcohol hydrogenolysis is important to control of the selectivity of sugar and sugar alcohol hydrogenolysis. Previous work by others has resulted in the suggestion of a variety of mechanisms to explain the C{single_bond}C cleavage in sugar and sugar alcohol hydrogenolysis, and has not provided any definitive evidence to elucidate either the C{single_bond}C or C{single_bond}O cleavage mechanism. In this work, the authors present a mechanism study carried out using 1,3-diol model compounds. Experimental results indicate that cleavage of the C{single_bond}C and C{single_bond}O bonds in hydrogenolysis is through retro-aldolization and dehydration of a {beta}-hydroxyl carbonyl, respectively. The structure of this {beta}-hydroxyl carbonyl is already contained in an open-chain sugar molecule, and is generated from the sugar alcohol molecule by dehydrogenation. The intermediates from both C{single_bond}C and C{single_bond}O cleavage are subsequently hydrogenated to yield alcohols or polyols. This mechanism of sugar and sugar alcohol hydrogenolysis provides a good background to understand factors that control the selectivity in sugar and sugar alcohol hydrogenolysis. Based on this understanding, a rational approach to control of the selectivity of sugar and sugar alcohol hydrogenolysis may be developed.
- Sponsoring Organization:
- USDOE
- OSTI ID:
- 183114
- Journal Information:
- Industrial and Engineering Chemistry Research, Vol. 34, Issue 11; Other Information: PBD: Nov 1995
- Country of Publication:
- United States
- Language:
- English
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