Formation of novel disinfection by-products chlorinated benzoquinone, phenyl benzoquinones and polycyclic aromatic hydrocarbons during chlorination treatment on UV filter 2,4-dihydroxybenzophenone in swimming pool water

2,4-Dihydroxybenzophenone (BP-1) is an important component and metabolite of benzophenone-type (BPs) UV filters, it is widely used in commercial products and frequently detected in environmental media and organism samples. The transformation characteristics and genotoxicity changes of BP-1 during chlorination disinfection process were explored. Nineteen transformation products were separated and tentatively identified, eleven of which were not previously reported. Most importantly, nine novel by-products including one chlorobenzoquinone, four phenyl benzoquinones, and four polycyclic aromatic hydrocarbons were formed during BP-1 chlorination. Plausible transformation pathways for BP-1 during chlorination treatment were proposed, in which chlorination substitution, Baeyer-Villiger oxidation, hydrolysis, and C-C coupling reactions were involved. The C-C coupling reaction is firstly observed in chlorination disinfection system. Higher pH values and chlorine doses would be a benefit for BP-1 transformation. The genotoxicity of the reaction mixture increased significantly with increasing chlorine dose under acid and neutral conditions due to the formation of benzoquinones and polycyclic aromatic hydrocarbons. It was noted that BP-1 and its chlorinated products were found in swimming pool water samples. This work inferred that BP-1 and its analogs are transformed during the chlorination disinfection process and may cause potential ecological and health risks.