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 language | Undefined/Unknown |
|---|---|
| Pages (from-to) | 1901–1907 |
| Number of pages | 7 |
| Journal | Catalysis Science and Technology |
| Volume | 2 |
| Issue number | 9 |
| DOIs | |
| Publication status | Published - 2012 |
| MoE publication type | A1 Journal article-refereed |