Abstract
Reports on the separation of polymers obtained from autoxidized fats and esters of usual fatty acids have been published, but there are probably no papers on polymers obtained from autoxidized esters of highly unsaturated acids. Methyl esters of highly unsaturated acids (saponification value : 177.3, iodine value : 322.5) from cuttlefish oil were oxidized by blowing dried air at 35°C in the scattered sunlight to prepare the product with peroxide value (m eq./kg) of 2.73 ×103. This was extracted by a mixed solvent, n-hexane and diethyl ether, and separated into 15 fractions by increasing the mixing ratio of diethyl ether from 0 to 75%. The extracted fractions, 3 (I), 11 (II), and 13 (III) correspond to monomer, dimer, and trimer and for which the ultraviolet and infrared absorption spectra were determined. (I), (II), and (III) contained considerable conjugated dienes, and no conjugated triene or higher. These products had the absorption band arising from the-OOH group in which high-frequency shifts were slightly seen. In this case the scission products, such as aldehydes, may be produced. Trans-trans conjugated diene presents in (II) and (III). The absorption band of cis nonconjugated forms decreasases in (II) and (III).
