The Diels-Alder reaction between alkali conjugated and elaidinized safflower oil fatty acids and maleic anhydride was studied under various experimental conditions. The principal product which was obtained in 51-55% yields was a mixture of the adduct of maleic anhydride and maleic acid in 40:60 proportions. The isolation and properties of this mixed adducts from the reaction mixture and their conversion to trimethyl, tributyl and triallyl esters are described. The trimethyl ester was also obtained in good yield from the methyl esters of the fatty acids and dimethyl maleate.
The Diels-Alder adducts from alkali conjugated and elaidinized safflower fatty acids with acrylic, methacrylic, crotonic and cinnamic acids and their esters as dienophiles were obtained in 40-64% yields. Low yields of t6-18% were obtained when 10-undecenoic acid and its ester were used. Most of the adducts could be estimated quantitatively in the reaction products by column chromatography or gas liquid chromatography (GLC). For the estimation of the adducts from crotonic and 10-undecenoic acids a combination of column chromatography and GLC techniques was employed. Partitioning between hexane and 90% methanol, partial esterification with alkali washing, and splitting and fractional distillation under reduced pressure were methods used to obtain the adducts in 90-95% purity.
Methyl esters of alkali‐isomerized safflower oil fatty acids after elaidinization with sulfur were treated with styrene in the presence of hydroquinone, with or without solvents. A combination of column chromatography and gas liquid chromatography techniques was employed for the estimation of the methyl esters of unreacted fatty acids, Diels‐Alder adduct and polymers in the reaction products. Maximum yield of the Diels‐Alder adduct (26.6%) was obtained when the elaidinized methyl esters of the fatty acids were treated with 1.5 moles of styrene per mole of linoleic acid in safflower oil fatty acids at 200–210 C for 6 hr. The methyl ester of the adduct was isolated in about 90% purity from the reaction product by vacuum distillation followed by solvent fractionation. The butyl ester of the adduct and the epoxy derivative of the methyl ester adduct were prepared and characterized.
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