Rethinking electrochemical oxidation of bisphenol A in chloride medium: Formation of toxic chlorinated oligomers

Using boron-doped diamond (BDD) anodes to degrade bisphenol A (BPA) had been an active area of research interest within the past 20 years. A major concern about the process lie in the formation of toxic chlorinated aromatic by-products when chloride electrolytes were present in the reaction system. In this contribution, we highlighted the formation of complex poly-chlorinated oligomer by-products in electrochemical oxidation processes, which had often been overlooked in previous studies. Moreover, the distribution and complexity of the chlorinated oligomers were found to be strongly linked to the adopted initial chloride concentration. Formation of simple chlorinated by-products was ascribed to the electrophilic substitution reactions mediated by active chlorine species, while the oligomer by-products (including chlorinated dimers, trimers and tetramers) were generated through the coupling reactions between various chlorinated phenoxy radicals. The possible mechanisms describing the formation of these by-products were also proposed. The obtained results shed light on the possible risk of BDD technology in the treatment of phenolic wastewater containing chloride electrolytes.