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- W2085190872 abstract "Summary Beta ‐propiolactone has been employed as the dienophile component in the Diels‐Alder reaction with alpha ‐ and beta ‐eleostearates, yielding acrylic acid adducts. Catalytic amounts of potassium carbonate were used to induce polymerization of beta ‐propiolac‐tone to a polyester and to assist in its pyrolysis to acrylic acid. The ethyl and n ‐butyl esters of the mixed fatty acids of alpha ‐and of beta ‐tung oil, containing about 75% eleostearates, were reacted with the theoretical amount of beta ‐propiolactone at 200°C. for a period of 1.5 hrs. Spectral analyses indicated nearly quantitative conversion of the reactants to the expected Diels‐Alder products. The acrylic acid adducts were esterified in their reaction mixtures with the appropriate alcohols to produce the corresponding di‐esters. These esters were purified by means of high vacuum distillation. Fractional crystallization of the free acids obtained by saponification of the di‐butyl esters of the alpha ‐eleostearic acid adducts yielded two isomeric dicarboxylic acids, melting at 113°C. and 85°C. These isomers differ only in the position of the carboxyl group on the cyclohexene nucleus of the adduct. The di‐ethyl and di‐butyl esters of both the alpha ‐and beta ‐eleostearic acid adducts and their hydrogenated derivatives have been intercompared as primary plasticizers for vinyl type resins. The hydrogenated di‐esters of the beta ‐eleostearic acid adducts were found to be the most effective." @default.
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- W2085190872 date "1955-10-01" @default.
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- W2085190872 title "The reaction of beta-propiolactone with alpha-and beta-eleostearates and plasticizer properties of derived esters" @default.
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- W2085190872 doi "https://doi.org/10.1007/bf02639668" @default.
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