Mild electrocatalytic hydrogenation of lactic acid to lactaldehyde and propylene glycol

Tulika S. Dalavoy, James E. Jackson, Greg M. Swain, Dennis J. Miller, Jie Li, Jacek Lipkowski

    Research output: Contribution to journalArticle

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    Abstract

    Reduction of fermentation-derived lactic acid (LA) offers a renewables-based pathway to propylene glycol (PG), a large-scale commodity chemical, currently manufactured by the oxidation of petroleum-derived propene. Complementing our previously described catalytic hydrogenation of LA to PG, we now report electrocatalytic hydrogenation (ECH) of LA in an aqueous electrolyte using constant current electrolysis. A reticulated vitreous carbon (RVC) electrode serves to agglomerate, support, and supply current to a 5% Ru/C powder catalyst, the same catalyst used in the classical hydrogenations. The ECH conditions are mild (ambient pressure, 70 °C vs 1500 psi H2, 150 °C) relative to the chemical hydrogenation. More surprisingly, the major electrohydrogenation product is lactaldehyde (LAL), with small quantities of PG also formed. Variable current studies in the range of 10-100 mA show an increase in product yields and a shift in selectivity toward PG with increasing current. Experiments carried out with different acids as electrolytes reveal a distinct effect of the anion on the yields of the two products. In situ ATR-FTIR studies of the ECH of LA point to a chelating bidentate carboxylate adsorption mode for lactate on the Ru surface and offer insight into the effects of electrolyte anions on surface adsorption and reactivity.

    Original languageEnglish (US)
    Pages (from-to)15-28
    Number of pages14
    JournalJournal of Catalysis
    Volume246
    Issue number1
    DOIs
    StatePublished - Feb 15 2007

    Profile

    hydrogenation
    Hydrogenation
    Deoxyribonucleoproteins
    Propylene
    lactic acid
    propylene
    glycols
    Lactic acid
    Glycols
    electrolytes
    products
    Electrolytes
    anions
    catalysts
    adsorption
    Negative ions
    Adsorption
    Catalysts
    Edema Disease of Swine
    Afferent Loop Syndrome

    Keywords

    • ATR
    • Electrocatalytic hydrogenation
    • Electrosynthesis
    • FTIR
    • Green chemistry
    • Lactaldehyde
    • Lactic acid
    • Organic electrochemistry
    • Propylene glycol
    • Reticulated vitreous carbon
    • SEIRAS

    ASJC Scopus subject areas

    • Catalysis
    • Process Chemistry and Technology

    Cite this

    Mild electrocatalytic hydrogenation of lactic acid to lactaldehyde and propylene glycol. / Dalavoy, Tulika S.; Jackson, James E.; Swain, Greg M.; Miller, Dennis J.; Li, Jie; Lipkowski, Jacek.

    In: Journal of Catalysis, Vol. 246, No. 1, 15.02.2007, p. 15-28.

    Research output: Contribution to journalArticle

    Dalavoy, Tulika S.; Jackson, James E.; Swain, Greg M.; Miller, Dennis J.; Li, Jie; Lipkowski, Jacek / Mild electrocatalytic hydrogenation of lactic acid to lactaldehyde and propylene glycol.

    In: Journal of Catalysis, Vol. 246, No. 1, 15.02.2007, p. 15-28.

    Research output: Contribution to journalArticle

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