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Chlorination of bisphenol S: Kinetics, products, and effect of humic acid.
Water Res. 2018 03 15; 131:208-217.WR

Abstract

Bisphenol S (BPS), as a main alternative of bisphenol A for the production of industrial and consumer products, is now frequently detected in aquatic environments. In this work, it was found that free chlorine could effectively degrade BPS over a wide pH range from 5 to 10 with apparent second-order rate constants of 7.6-435.3 M-1s-1. A total of eleven products including chlorinated BPS (i.e., mono/di/tri/tetrachloro-BPS), 4-hydroxybenzenesulfonic acid (BSA), chlorinated BSA (mono/dichloro-BSA), 4-chlorophenol (4CP), and two polymeric products were detected by high performance liquid chromatography and electrospray ionization-tandem quadrupole time-of-flight mass spectrometry. Two parallel transformation pathways were tentatively proposed: (i) BPS was attacked by stepwise chlorine electrophilic substitution with the formation of chlorinated BPS. (ii) BPS was oxidized by chlorine via electron transfer leading to the formation of BSA, 4CP and polymeric products. Humic acid (HA) significantly suppressed the degradation rates of BPS even taking chlorine consumption into account, while negligibly affected the products species. The inhibitory effect of HA was reasonably explained by a two-channel kinetic model. It was proposed that HA negligibly influenced pathway i while appreciably inhibited the degradation of BPS through pathway ii, where HA reversed BPS phenoxyl radical (formed via pathway ii) back to parent BPS.

Authors+Show Affiliations

State Key Laboratory of Urban Water Resource and Environment, School of Municipal and Environmental Engineering, Harbin Institute of Technology, Harbin 150090, China.State Key Laboratory of Urban Water Resource and Environment, School of Municipal and Environmental Engineering, Harbin Institute of Technology, Harbin 150090, China. Electronic address: jiangjinhit@126.com.State Key Laboratory of Urban Water Resource and Environment, School of Municipal and Environmental Engineering, Harbin Institute of Technology, Harbin 150090, China.School of Municipal and Environmental Engineering, Jilin Jianzhu University, Changchun 130118, China. Electronic address: psyhit@126.com.State Key Laboratory of Urban Water Resource and Environment, School of Municipal and Environmental Engineering, Harbin Institute of Technology, Harbin 150090, China.School of Civil and Environmental Engineering, Shenzhen Polytechnic, Shenzhen 518055, China.College of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin 150040, China.State Key Laboratory of Urban Water Resource and Environment, School of Municipal and Environmental Engineering, Harbin Institute of Technology, Harbin 150090, China.State Key Laboratory of Urban Water Resource and Environment, School of Municipal and Environmental Engineering, Harbin Institute of Technology, Harbin 150090, China.College of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin 150040, China.College of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin 150040, China.State Key Laboratory of Urban Water Resource and Environment, School of Municipal and Environmental Engineering, Harbin Institute of Technology, Harbin 150090, China.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

29289922

Citation

Gao, Yuan, et al. "Chlorination of Bisphenol S: Kinetics, Products, and Effect of Humic Acid." Water Research, vol. 131, 2018, pp. 208-217.
Gao Y, Jiang J, Zhou Y, et al. Chlorination of bisphenol S: Kinetics, products, and effect of humic acid. Water Res. 2018;131:208-217.
Gao, Y., Jiang, J., Zhou, Y., Pang, S. Y., Ma, J., Jiang, C., Yang, Y., Huang, Z. S., Gu, J., Guo, Q., Duan, J. B., & Li, J. (2018). Chlorination of bisphenol S: Kinetics, products, and effect of humic acid. Water Research, 131, 208-217. https://doi.org/10.1016/j.watres.2017.12.049
Gao Y, et al. Chlorination of Bisphenol S: Kinetics, Products, and Effect of Humic Acid. Water Res. 2018 03 15;131:208-217. PubMed PMID: 29289922.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Chlorination of bisphenol S: Kinetics, products, and effect of humic acid. AU - Gao,Yuan, AU - Jiang,Jin, AU - Zhou,Yang, AU - Pang,Su-Yan, AU - Ma,Jun, AU - Jiang,Chengchun, AU - Yang,Yue, AU - Huang,Zhuang-Song, AU - Gu,Jia, AU - Guo,Qin, AU - Duan,Jie-Bin, AU - Li,Juan, Y1 - 2017/12/23/ PY - 2017/09/09/received PY - 2017/12/18/revised PY - 2017/12/19/accepted PY - 2018/1/1/pubmed PY - 2019/1/8/medline PY - 2018/1/1/entrez KW - Bisphenol S KW - Chlorine KW - Electron transfer KW - Electrophilic substitution KW - Humic acid SP - 208 EP - 217 JF - Water research JO - Water Res. VL - 131 N2 - Bisphenol S (BPS), as a main alternative of bisphenol A for the production of industrial and consumer products, is now frequently detected in aquatic environments. In this work, it was found that free chlorine could effectively degrade BPS over a wide pH range from 5 to 10 with apparent second-order rate constants of 7.6-435.3 M-1s-1. A total of eleven products including chlorinated BPS (i.e., mono/di/tri/tetrachloro-BPS), 4-hydroxybenzenesulfonic acid (BSA), chlorinated BSA (mono/dichloro-BSA), 4-chlorophenol (4CP), and two polymeric products were detected by high performance liquid chromatography and electrospray ionization-tandem quadrupole time-of-flight mass spectrometry. Two parallel transformation pathways were tentatively proposed: (i) BPS was attacked by stepwise chlorine electrophilic substitution with the formation of chlorinated BPS. (ii) BPS was oxidized by chlorine via electron transfer leading to the formation of BSA, 4CP and polymeric products. Humic acid (HA) significantly suppressed the degradation rates of BPS even taking chlorine consumption into account, while negligibly affected the products species. The inhibitory effect of HA was reasonably explained by a two-channel kinetic model. It was proposed that HA negligibly influenced pathway i while appreciably inhibited the degradation of BPS through pathway ii, where HA reversed BPS phenoxyl radical (formed via pathway ii) back to parent BPS. SN - 1879-2448 UR - https://www.unboundmedicine.com/medline/citation/29289922/Chlorination_of_bisphenol_S:_Kinetics_products_and_effect_of_humic_acid_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0043-1354(17)31044-8 DB - PRIME DP - Unbound Medicine ER -