Isomerization of soybean oil, methyl oleate, and methyl linoleate with thionyl chloride was investigated under various conditions. The amounts of conjugated dienes formed are relatively small, and infrared spectroscopic study shows that conjugated dienes are mainly of the trans-trans form. In the isomerization of methyl oleate with 1% thionyl chloride at 180°-250°C, the double bond migrates from 6 to 12 position.
The thermal decomposition of thionyl chloride was examined by the IR spectral analysis and organoleptic test. Moreover, the effects of the possible thermal decomposition products of thionyl chloride, Cl
2, SO
2, and S
2Cl
2, upon the isomerization of soybean oil were studied. From the results, it can be inferred that, in the isomerization of soybean oil with thionyl chloride a greater fraction of the thionyl chloride will remain unchanged below 220°C. Moreover, it is considered that some of the decomposition products of thionyl chloride, if formed in small quantities, may play a role of catalyst.
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