There are many reports on the detection and removal of emerging pollutants in the wastewater effluents, while the fate of their chlorinated derivatives generated during chlorination is not well understood. Here we investigated the photodegradation of chlorinated derivatives of bisphenol A (CDBPAs), mainly including 3-chlorobisphenol A, 3,3′-dichlorobisphenol A, 3,5-dichlorobisphenol A, 3,3′,5-trichlorobisphenol A, and 3,3′,5,5′-tetrachlorobisphenol A, under simulated sunlight. Distinct from BPA, CDBPAs underwent rapid direct photodegradation due to a pronounced bathochromic shift of UV absorption. The photodegradation of CDBPAs was significantly enhanced by effluent organic matter (EfOM) from the wastewater effluent. A series of quenching experiments and laser flash photolysis analysis verified the contribution of triplet states of EfOM (³EfOM∗) for the indirect photodegradation of CDBPAs with rate constant of ∼10⁹ M⁻¹ s⁻¹. Both direct and EfOM-induced indirect photodegradation of CDBPAs increased with a higher degree of chlorination. Furthermore, high-resolution mass spectrometry showed similar photoproducts for direct and indirect photodegradation of CDBPAs, mainly ascribed to the cleavage of C–Cl bond and hydroxylation with further cleavage of the benzene ring. The estrogenic activity of the photoproducts was diminished. These findings suggest that photodegradation is an important pathway for the removal and detoxication of CDBPAs from effluents and receiving natural waters under sunlight.

关于检测和去除废水中新出现的污染物的报道很多，但是人们对在氯化过程中产生的氯代衍生物的去向却知之甚少。在这里，我们研究了双酚A（CDBPA）的氯化衍生物的光降解作用，主要包括3-氯双酚A，3,3'-二氯双酚A，3,5-二氯双酚A，3,3'，5-三氯双酚A和3， 3'，5,5'-四氯双酚A，在模拟阳光下。与BPA不同，由于UV吸收的显着红移，CDBPA经历了直接的直接光降解。废水中的有机物（EfOM）显着增强了CDBPAs的光降解。一系列淬火实验和激光闪光光解分析证明了EfOM的三重态的贡献（³ EfOM *）用于CDBPA的间接光降解，速率常数约为^{10 9}  M ^-1  s ^-1。CDBPAs的直接和EfOM诱导的间接光降解都随着氯化程度的提高而增加。此外，高分辨率质谱法显示出用于CDBPAs直接和间接光降解的类似光产物，主要归因于C–Cl键的裂解和羟基化以及苯环的进一步裂解。光产物的雌激素活性降低。这些发现表明，光降解是从废水中和在日光下接受天然水去除CDBPA和使其脱毒的重要途径。