The reaction between hydrocarbon and hydrogen chloride in silent electrical discharge. I. The reaction of ethylene with hydrogen chloride.

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Silent discharge was found to induce the reaction of ethylene and hydrogen chloride and to give mainly addition and telomerization products. Discharge on a mixture of ethylene and hydrogen chloride in an ozonizer under atmospheric pressure gave chloroethane, 1-chlorobutane, and 1,4-dichlorobutane as the main products. Besides these compounds, chloroethylene, 2-chlorobutane, 1,3-dichlorobutane, 2,3-dichlorobutane, 1,2-dichlorobutane, 1-chlorohexane, 1,2-dichloroethane, and gaseous products were also formed. The maximum yield of the liquid products was obtained when ethylene and hydrogen chloride were mixed in the ratio of approximately 1:1. The formation of telomers was favored by a low ratio of the hydrogen chloride to the ethylene concentration, and by a low temperature in the discharge reaction. On the other hand, gaseous products increased with the rise in the discharge temperature and with an increase in the ratio of ethylene to hydrogen chloride. Judging from the product distribution, the reaction may be explained in terms of radical reactions involving vinyl, ethyl, and chlorine radicals. Among the reactions between ethylene and HX, such as hydrogen cyanide, hydrogen sulfide, and hydrogen chloride, the highest conversion was obtained by using the hydrogen chloride as the reactant.
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