Catalytic valorization of oil-derived fatty esters via cross-metathesis with nitriles

Abstract

The cross-metathesis of methyl oleate with 3-pentenenitrile to obtain 2-undecene, methyl 9-undecenoate, methyl 11-cyano-9-undecenoate and 3-dodecenenitrile was studied at 323 K in a batch reactor using second-generation Hoveyda-Grubbs (HG) catalysts. Self-metathesis of methyl oleate was the main undesired secondary reaction. For a 3-pentenenitrile/methyl oleate reactant ratio (R3PN/MO) of one, the yield (η_(C-M)) and selectivity (S_(C-M)) to cross-metathesis products were 47% and 63%, respectively. The formation of cross-metathesis products increased with increasing 3-pentene initial concentrations, essentially because the reaction equilibrium was shifted to higher methyl oleate conversions. Thus, η_(C-M) and S_(C-M) were 74% and 83%, respectively, at R3PN/MO = 5. Nevertheless, the HG complex was significantly deactivated when high R3PN/MO values were employed.