Abstract
Aqueous acetonitrile solution-phase photoincorporations of six polychlorobenzenes (PCBzs) into some humic model monomers such as benzoic acid, benzaldehyde, vanillic acid, vanillin, syringic acid and syringaldehyde were investigated using UV light centered at 300 nm. All the PCBzs studied except hexachlorobenzene yielded photoproducts by the reaction of the poly-chlorophenyl radicals with the individual humic monomers. Chlorophenylation of humic model monomers occurred in the case of benzoic acid and benzaldehyde; substituted polychlorodiphenyl ethers were also formed when monomers containing a phenolic OH group were present. Furthermore, the irradiation of 1,2,4,5-tetrachlorobenzene in solution in the presence of vanillic acid produced monochloro- and dichloromethoxydibenzofuran carboxylic acids in addition to the other photoincorporated products.
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