Summary
Methyl oleate, oleic acid, and ethyl linoleate were chlorinated with elemental chlorine at temperatures near −20°C. Approximately quantitative yields of the addition products were obtained, with little or no concurrent substitution. The products prepared in this manner had not previously been reported in the pure state. Two new compounds, ethyl tetrachlorostearate and tetrachlorostearic acid, were prepared.
Methyl dichlorostearate was found to distil with no apparent decomposition at 190–200°C. under pressures below 1 mm. Removal of the chlorine atoms required more drastic conditions that removal of bromine atoms from the same positions and was accompanied by complicating side reactions.
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Journal Paper No. 755 of the Purdue University Agricultural Experiment Station, Lafayette, Ind.
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Lyness, W.I., Quackenbush, F.W. Addition of chlorine to unsaturated fatty acids and esters. J Am Oil Chem Soc 32, 520–521 (1955). https://doi.org/10.1007/BF02639662
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DOI: https://doi.org/10.1007/BF02639662