Ethenolysis of methyl oleate in room-temperature ionic liquids.

ChemSusChem (2008-07-09)
Cyril Thurier, Cédric Fischmeister, Christian Bruneau, Hélène Olivier-Bourbigou, Pierre H Dixneuf
ABSTRACT

Unsaturated vegetable oils are an attractive renewable feedstock, and the selective cleavage of unsaturated fatty esters is an important transformation in this respect. The efficient and selective cross-metathesis of methyl oleate with ethylene was achieved under mild conditions with ruthenium-alkylidene catalysts in toluene and room-temperature ionic liquids (RTILs) to give two important chemical intermediates, 1-decene and methyl 9-decenoate, without double-bond migration. As recovery of the catalyst is an important target with respect to industrial applications, catalyst recycling studies were also carried out in RTILs with the first-generation Hoveyda catalyst.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Methyl oleate, 99%
Supelco
Methyl oleate, analytical standard
Sigma-Aldrich
Methyl oleate, technical grade, 70%
Sigma-Aldrich
Methyl elaidate, ≥99% (capillary GC)
Supelco
cis-9-Octadecenoic acid methyl ester, certified reference material, 10 mg/mL in heptane
Supelco
Methyl elaidate, analytical standard