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

NIERES, PABLO D.; ZELIN, JUAN; TRASARTI, ANDRÉS F.; APESTEGUÍA, CARLOS R.

EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY

WILEY-V C H VERLAG GMBH

Lugar: Weinheim; Año: 2016

1438-7697

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 (ηC-M) and selectivity (SC-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, ηC-M and SC-M were 74 and 83%, respectively, at R3PN/MO = 5. Nevertheless, the HG complex was significantly deactivated when high R3PN/MO values were employed.