Chain dechlorination of organic chlorinated compounds in alcohol solutions by 60Co .GAMMA.-Rays. II. Chlorinated benzenes in alkaline 2-propanol solutions.:Chlorinated Benzenes in Alkaline 2-Propanol Solutions

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Chlorinated benzenes dissolved in deoxygenated alkaline 2-propanol were dechlorinated by irradiating with 60Co γ-rays to produce the lower chlorinated benzenes and chloride ion. The yield of dechlorination was found to depend on the number of chlorine atoms on the benzene ring, the G(Cl-)-values being, for instance, 6, 500, 480 and 2.0 for 0.07 M penta-chlorobenzene, 1, 2, 4-trichlorobenzene, and monochlorobenzene, respectively, in 0.2 M KOH-2-propanol solution. In contrast, the values of G(Cl-) differed little between the isomers of trichlorobenzene. The large difference in G(Cl-) according to the number of chlorine atoms can be explained by considering the redox potential of the chlorinated benzenes and the ketyl radical ion. Trichlorobenzene is dechlorinated to dichlorobenzene and then to monochlorobenzene while producing potassium chloride and acetone, and consuming hydroxide ion. In the experiment, some chlorinated benzene derivatives were observed to be generated in the course of this process--probably dichlorophenyl-2-propanol and monochlorophenyl-2-pro-panol, judging from observation by gaschromatograph-mass spectrometer and from the path-way of formation. The observation also indicated the presence of dichloropheny1-2-propanol in predominant amounts in 1, 3, 5-trichlorobenzene solution, but only in a small fraction in 1, 2, 3-trichlorobenzene.
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