Chlorination in dilute aqueous systems; 2,4,6-trichlorophenol

Chlorination of wastewaters can cause extensive transformations of organic contaminants. In the case of phenol, the reaction path is only partially understood. In an effort to elucidate this reaction, 2,4,6-trichlorophenol in dilute aqueous solution was treated with excess hypochlorous acid at pH 3.5-6. The major products were 2,6-dichloroquinone and 2,4,4,6-tetrachloro-2,5-cyclohexadienone. Additional polychlorinated species are formed in minor amounts by the addition of chlorine and/or hypochlorous acid to the aromatic ring.