Hydrogenation of geraniol using ruthenium–BINAP catalysts

Heidi Bernas, Andreas Bernas, Päivi Mäki-Arvela, Reko Leino, Dmitry Murzin

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    Abstract

    The asymmetric hydrogenation of geraniol (3,7-dimethylocta-2,6-dien-1-ol) to citronellol was performed using ruthenium BINAP catalysts at 60 degrees C. The influence of solvent (methanol, ethanol, 1-propanol, and 2-propanol), catalyst type (Ru(OAc)(2)(BINAP), R-Ru(OAc)(2)(T-BINAP), and R-RuCl[(p-cymene)(BINAP)]Cl), and hydrogen pressure (5-40 bar) was studied. The reaction rate decreased in the order methanol > ethanol > 1-propanol > 2-propanol, but the selectivity and enantiomeric excess were independent of solvent. R-Ru(OAc)(2)(T-BINAP) afforded the highest enantiomeric excess of S-citronellol. The reaction rate and enantioselectivity increased with hydrogen pressure. A kinetic model was developed based on the proposed reaction mechanism with subsequent parameter estimation.
    Original languageUndefined/Unknown
    Pages (from-to)1901–1907
    Number of pages7
    JournalCatalysis Science and Technology
    Volume2
    Issue number9
    DOIs
    Publication statusPublished - 2012
    MoE publication typeA1 Journal article-refereed

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