Chemical changes of organic compounds in chlorinated water : VI. Gas chromatographic and mass spectrometric studies of the reactions of phenylphenols with hypochlorite in dilute aqueous solution

Abstract

Diethyl ether-extracted products obtained from phenylphenol solutions after treatment with hypochlorite under various conditions have been investigated for their nature and contents of chlorination products in water. The ether extracts were chromatographed on polar and non-polar gas—liquid chromatographic (GLC) columns and the peaks were assigned on the basis of plots of log t R against the number of expected chlorine atoms. They were subsequently identified from the mass spectra of the extracts. The GLC and mass spectral analyses of these products indicated that the reactions involve chlorination to chlorophenylphenols (A), oxidation of compounds A to chlorophenylquinones (B), oxidative degradation of compounds B to phenylcarboxylic acids and condensation of compounds A to the corresponding ethers and dioxins. The residual amounts of chlorinated compounds of phenylphenols in water were found to be dependent on the pH of the solution.