Mechanism study of sugar and sugar alcohol hydrogenolysis using 1,3-diol model compounds

Keyi Wang, Martin C. Hawley, Todd D. Furney

Research output: Contribution to journalArticle

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Abstract

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-C cleavage in sugar and sugar alcohol hydrogenolysis, and has not provided any definitive evidence to elucidate either the C-C or C-O cleavage mechanism. In this work, we present a mechanism study carried out using 1,3-diol model compounds. Our experimental results indicate that cleavage of the C-C and C-O bonds in hydrogenolysis is through retro-aldolization and dehydration of a β-hydroxyl carbonyl, respectively. The structure of this β-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-C and C-O cleavage are subsequently hydrogenated to yield alcohols or polyols. This mechanism of sugar and sugar alcohol hydrogenolysis provides us 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.

LanguageEnglish (US)
Pages3766-3770
Number of pages5
JournalIndustrial and Engineering Chemistry Research
Volume34
Issue number11
StatePublished - 1995

Profile

Sugar Alcohols
Hydrogenolysis
Sugars
alcohol
sugar
cleavage
Hydroxyl Radical
Molecules
Polyols
Dehydrogenation
Dehydration
Alcohols
dehydration

ASJC Scopus subject areas

  • Polymers and Plastics
  • Environmental Science(all)
  • Chemical Engineering (miscellaneous)

Cite this

Mechanism study of sugar and sugar alcohol hydrogenolysis using 1,3-diol model compounds. / Wang, Keyi; Hawley, Martin C.; Furney, Todd D.

In: Industrial and Engineering Chemistry Research, Vol. 34, No. 11, 1995, p. 3766-3770.

Research output: Contribution to journalArticle

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