Hydrogenation of geraniol using ruthenium–BINAP catalysts

A1 Journal article (refereed)


Internal Authors/Editors


Publication Details

List of Authors: Heidi Bernas, Andreas Bernas, Päivi Mäki-Arvela, Reko Leino, Dmitry Yu. Murzin
Publisher: ROYAL SOC CHEMISTRY
Publication year: 2012
Journal: Catalysis Science and Technology
Journal acronym: CATAL SCI TECHNOL
Volume number: 2
Issue number: 9
Start page: 1901
End page: 1907
Number of pages: 7
ISSN: 2044-4753
eISSN: 2044-4761


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.

Last updated on 2019-06-12 at 03:31