Robust and Selective Metathesis Catalysts for Oleochemical Applications

Abstract

The screening of known ruthenium alkylidene complexes in the ethenolysis of methyl oleate shows that the Grubbs-type Ru-catalysts bearing two phosphine donor ligands exhibit high selectivity for the formation of terminal olefins. Second-generation ruthenium catalysts promote almost the exclusive formation of self-metathesis products. Complexes with chelating alkylidene moieties (Hoveyda-type) generally exhibit poor selectivity for both ethenolysis and self-metathesis products. Complexes 2b and 2d promote self-metathesis of methyl oleate with catalyst loading of 2 ppm without significant isomerization up to 110 °C (using 2d) and up to 150 °C (using 2b).