Conclusions
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1.
In the reaction of radical-chain chlorination of alkylaromatic compounds (cumene, ethylbenzene) by tert-butyl hypochlorite, with increasing pressure the content of theα-isomer, formed in a larger amount than theβ-isomer at atmospheric pressure, increases.
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2.
In the competitive chlorination of alkyl aromatic compounds by tert-butyl hypochlorite, the ratio of the monochlorosubstituted compounds formed is determined chiefly by the reaction of stripping of hydrogen atoms by the chlorine atoms present in theπ-complex with the aromatic ring.
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3.
The accelerating effect of pressure in the stripping of hydrogen atoms is greater, the higher the rate constant of the reaction.
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4.
When chlorination is conducted in the presence of trichloroethylene, the mechanism of the process is changed, which was noted according to the change in the ratio of the chlorination products at atmospheric pressure and according to the decrease in the influence of the pressure on the composition of monochloro-substituted compounds.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 2, pp. 293–298, February, 1975.
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Zhulin, V.M., Rubinshtein, B.I. & Botnikov, M.Y. Chlorination of certain monoalkylbenzenes with tert-butyl hypochlorite at high pressures. Russ Chem Bull 24, 230–234 (1975). https://doi.org/10.1007/BF00925760
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DOI: https://doi.org/10.1007/BF00925760