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

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

EUROPEAN JOURNAL OF LIPID SCIENCE AND TECHNOLOGY

WILEY-V C H VERLAG GMBH

Lugar: Weinheim; Año: 2016 vol. 118 p. 1722 - 1729

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 323K 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 (hCM) and selectivity (SCM) 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, hCM and SCM were 74 and 83%, respectively, at R3PN/MO¼5. Nevertheless, the HG complex was significantly deactivated when high R3PN/MO values were employed.