Metathesis of methyl soyate with ruthenium catalysts

Three ruthenium catalysts were investigated for the metathesis reaction of methyl soyate. Dichlorotris (triphenylphosphine) ruthenium II and bis (tricyclohexyl phosphine) benzylidine ruthenium (IV) dichloride displayed no reactivity at 40 °C and atmospheric pressure. However, ruthenium [1,3-bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene] dichloro (phenylmethylene) tricyclohexylphosphine, Grubbs second generation catalyst, exhibited high activity at these mild conditions. After 2 h, 46% of the unsaturated methyl esters in a commercial methyl soyate were metathesized. This suggests a method to modify the structure of methyl soyate to improve diesel fuel performance properties.