Abstract
To compare the effects of various metals (periodic group VI) on the autoxidation of methyl oleate and the decomposition of methyl oleate hydroperoxide in methyl oleate, the substrates were kept with metal carbonyls [Mo (CO) 6, Cr (CO) 6 and W (CO) 6] at 80°C.The effects of the catalysts were investigated by observing the changes in peroxide value, iodine value, saponification value, refractive index, molecular weight, and trans isomer content. The identification of autoxidation products of methyl oleate and decomposition products of methyl oleate hydroperoxide were carried out by gas chromatography of trimethylsilyl ether derivatives.Mo (CO) 6 showed marked effect on the autoxidation of methyl oleate and the decomposition of methyl oleate hydroperoxide. The products were found as methyl cis-epoxyoctadecanoate and methyl hydroxyoctadecenoate, which were produced by intermolecular reaction among methyl oleate and methyl oleate hydroperoxide. Moreover, methyl hydroxyepoxyoctadecanoate was also produced by intramolecular reaction of methyl oleate hydroperoxide itself.Cr (CO) 6 showed more marked effect than Mo (CO) 6. The autoxidized products of methyl oleate were identified as methyl trans-epoxyoctadecanoate, methyl cis-epoxyoctadecanoate, methyl hydroxyoctadecenoate and methyl oxooctadecenoate, but methyl hydroxyepoxyoctadecanoate was not produced. Methyl oxooctadecenoate and methyl hydroxyoctadecenoate were produced by decomposition of methyl oleate hydroperoxide in the presence of Cr (CO) 6, but W (CO) 6 showed almost no effects.
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