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Issue 9, 2012
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Hydrogenation of geraniol using ruthenium–BINAP catalysts

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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 °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.

Graphical abstract: Hydrogenation of geraniol using ruthenium–BINAP catalysts

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Publication details

The article was received on 14 Mar 2012, accepted on 25 Apr 2012 and first published on 25 Apr 2012


Article type: Paper
DOI: 10.1039/C2CY20249B
Citation: Catal. Sci. Technol., 2012,2, 1901-1907
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    Hydrogenation of geraniol using ruthenium–BINAP catalysts

    H. Bernas, A. Bernas, P. Mäki-Arvela, R. Leino and D. Yu. Murzin, Catal. Sci. Technol., 2012, 2, 1901
    DOI: 10.1039/C2CY20249B

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