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.

    Original languageEnglish (US)
    Pages (from-to)3766-3770
    Number of pages5
    JournalIndustrial and Engineering Chemistry Research
    Volume34
    Issue number11
    StatePublished - 1995

    Profile

    Hydrogenolysis
    Sugars
    Sugar Alcohols
    Carbohydrates
    Pharmacy Legislation
    sugar
    alcohol
    Blood Flow Velocity
    cleavage
    Hydroxyl Radical
    Molecules
    Anthralin
    Dehydration
    Alcohols
    Polyols
    Dehydrogenation
    Ephemeral Fever
    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

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

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

    Research output: Contribution to journalArticle

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