Chemical Changes of Organic Compounds in Chlorinated Water. XIX. Production of Alkylpolychlorinated Phenoxyphenols (Predioxins) by Aqueous Chlorination of Alkylphenols

Aqueous alkylphenol solutions were treated with chlorine at 20°C under various experimental conditions. Changes in the compositions of the chlorination products in water were determined by gas chromatographic (GC) and GC-mass spectrometric (GC-MS) analyses of diethyl ether extracts. Alkylphenols were shown to produce a variety of chlorinated compounds, including alkylpolychlorinated phenoxyphenols (predioxins), having one to five chlorine atoms, as by-products in chlorine-treated water. Production of some of these predioxins is dependent on the number of equivalents of chlorine per mol of compound and on the reaction pH. These results suggest that chlorine treatment of water contaminated with alkylphenols leads to the production of predioxins, which are precursors of the highly toxic chlorinated dibenzo-p-dioxins.