The chlorination transformation characteristics of benzophenone-4 in the presence of iodide ions
Fan Yang , Dongbin Wei , Ming Xiao , Xuefeng Sun , Qiaorong Guo , Yi Liu , Yuguo Du
DOI:10.1016/j.jes.2017.04.023
Received January 16, 2017,Revised April 08, 2017, Accepted April 20, 2017, Available online May 03, 2017
Volume 29,2017,Pages 93-101
Benzophenone-type UV filters are a group of compounds widely used to protect human skin from damage of UV irradiation. Benzophenone-4 (BP-4) was targeted to explore its transformation behaviors during chlorination disinfection treatment in the presence of iodide ions. With the help of ultra performance liquid phase chromatograph and high-resolution quadrupole time-of-flight mass spectrometer, totally fifteen halogenated products were identified, and five out of them were iodinated products. The transformation mechanisms of BP-4 involved electrophilic substitution generating mono- or di-halogenated products, which would be oxidized into esters and further hydrolyzed into phenolic derivatives. The desulfonation and decarboxylation were observed in chlorination system either. Obeying the transformation pathways, five iodinated products formed. The pH conditions of chlorination system determined the reaction types of transformation and corresponding species of products. The more important was that, the acute toxicity had significant increase after chlorination treatment on BP-4, especially in the presence of iodide ions. When the chlorination treatment was performed on ambient water spiked with BP-4 and iodide ions, iodinated by-products could be detected.
