Abstract
The reaction of methyl linoleate and methyl acrylate in the presence of the conjugation catalyst such as nickel-on-carbon, palladium-on-carbon, chromium hexacarbonyl, methyl benzoate-chromium tricarbonyl, iron pentacarbonyl, anthraquinone, activated aluminium oxide and potassium tert.-butoxide was studied. Among the catalysts employed in this study, iron pentacarbonyl was found to be the most effective. The 1 : 1 Diels-Alder adduct from methyl linoleate and methyl acrylate was obtained in 76% yield by heating a mixture of methyl linoleate, methyl acrylate (1.5 moles per mole of methyl linoleate) and iron pentacarbonyl (5mol% of methyl linoleate) for 17hr at 230°C under nitrogen pressure of about 5kg/cm2. The yield of 1 : 1 adduct increased to 88% when about 5kg/cm2 of carbon monoxide was used instead of nitrogen. Besides the 1 : 1 adduct as the main product, 1 : 2 adduct, 1 : 3 adduct, and copolymer of methyl linoleate and methyl acrylate were also formed.
