Soybean soapstock utilization: Fatty acid adducts with ethylene and 1-butene

The relation of certain reaction variables to yield was investigated in the preparation of ethylene and 1-butene Diels-Alder adducts with alkali conjugated linoleic and linolenic acid soaps derived from soybean oil soapstock. Adduct yields generally increased with pressure at the 295 C reaction temperature. Maximum yields obtained with fatty acids derived from soapstock were ca. 80% of theory with ethylene and 40% of theory with 1-butene. Purification of adduct methyl esters by vacuum fractional distillation gave adducts with >95% purity. Ethylene adduct amides showed promise as antiblock agents for plastic film.