The elaidinization of methyl oleate with mercaptans

Methyl oleate is transformed into methyl elaidate by mercaptans. The equilibrium mixture, containing 77% elaidate, can be obtained from either isomer. A concomitant, although much slower reaction, is the addition of the sulfhydry group to the double bond of either ester. The effects of numerous reaction conditions on the extent and rate of the isomerization are given. The reaction is presented as an incipient addition of the mercaptan to the double bond, as a reversible thiyl radical attack on one of the unsaturated carbon atoms.