Hydrogenation of triple bonds to double bonds in conjugated methyl octadecadiynoate and methyl santalbate

Abstract

A study was made of the noncatalytic hydrogenation of acetylenic bonds in fatty esters tocis double bonds using various metals in different solvent systems. The best results were obtained with 15% propanol in water using iron. The yields ofcis double bonds for the nonconjugated diynoate and monoynoate ranged from 90% to 99% and for the conjugated diynoate the yields ranged from 56% to 77%. In the reduction of methyl santalbate to a conjugated diene, the yields were ca. 85%.