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Oxidation of steroid estrogens by peroxymonosulfate (PMS) and effect of bromide and chloride ions: Kinetics, products, and modeling.
Water Res. 2018 07 01; 138:56-66.WR

Abstract

Recently, in situ chemical oxidation (ISCO) using peroxymonosulfate (PMS) for environmental decontamination has received increasing interest. In this study, oxidation kinetics and products of four steroid estrogens (i.e., estrone, 17β-estradiol, estriol, and 17α-ethinylestradiol) by PMS under various conditions were investigated. PMS could fairly degrade steroid estrogens over the pH range of 7-10, and the degradation rate increased with the increase of solution pH. This pH-dependence was well described by parallel reactions between individual acid-base species of steroid estrogens (E and E-) and PMS (HSO5- and SO52-), where specific second-order rate constants for E- with HSO5- and SO52- were in the range of 2.11-5.58 M-1s-1 and 0.77-1.25 M-1s-1, respectively. Identification of oxidation products by liquid chromatography/electrospray ionization quadrupole time-of-flight mass spectrometer showed that PMS readily oxidized the phenolic group of steroid estrogens, leading to the generation of hydroxylated and ring-opening products. The presence of bromide and chloride ions (Br- and Cl-) at environmentally relevant levels could greatly accelerate the degradation of steroid estrogens by PMS with the formation of halogenated aromatic products. This effect was quantitatively estimated by a kinetic model, where the formation of free bromine and chorine and their rapid electrophilic substitution with steroid estrogens were taken into consideration. Eco-toxicity of transformation products of 17α-ethinylestradiol by PMS treatment in the absence and presence of bromide and chloride was estimated by quantitative structure-activity relationship analysis using ECOSAR. These findings advance the understanding of ISCO using PMS.

Authors+Show Affiliations

State Key Laboratory of Urban Water Resource and Environment, School of Environment, Harbin Institute of Technology, Harbin 150090, China.State Key Laboratory of Urban Water Resource and Environment, School of Environment, Harbin Institute of Technology, Harbin 150090, China. Electronic address: jiangjinhit@126.com.State Key Laboratory of Urban Water Resource and Environment, School of Environment, 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 Environment, 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 Environment, Harbin Institute of Technology, Harbin 150090, China.College of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin 150040, China.

Pub Type(s)

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

Language

eng

PubMed ID

29573629

Citation

Zhou, Yang, et al. "Oxidation of Steroid Estrogens By Peroxymonosulfate (PMS) and Effect of Bromide and Chloride Ions: Kinetics, Products, and Modeling." Water Research, vol. 138, 2018, pp. 56-66.
Zhou Y, Jiang J, Gao Y, et al. Oxidation of steroid estrogens by peroxymonosulfate (PMS) and effect of bromide and chloride ions: Kinetics, products, and modeling. Water Res. 2018;138:56-66.
Zhou, Y., Jiang, J., Gao, Y., Pang, S. Y., Ma, J., Duan, J., Guo, Q., Li, J., & Yang, Y. (2018). Oxidation of steroid estrogens by peroxymonosulfate (PMS) and effect of bromide and chloride ions: Kinetics, products, and modeling. Water Research, 138, 56-66. https://doi.org/10.1016/j.watres.2018.03.045
Zhou Y, et al. Oxidation of Steroid Estrogens By Peroxymonosulfate (PMS) and Effect of Bromide and Chloride Ions: Kinetics, Products, and Modeling. Water Res. 2018 07 1;138:56-66. PubMed PMID: 29573629.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Oxidation of steroid estrogens by peroxymonosulfate (PMS) and effect of bromide and chloride ions: Kinetics, products, and modeling. AU - Zhou,Yang, AU - Jiang,Jin, AU - Gao,Yuan, AU - Pang,Su-Yan, AU - Ma,Jun, AU - Duan,Jiebin, AU - Guo,Qin, AU - Li,Juan, AU - Yang,Yue, Y1 - 2018/03/16/ PY - 2017/12/23/received PY - 2018/03/13/revised PY - 2018/03/16/accepted PY - 2018/3/25/pubmed PY - 2018/9/8/medline PY - 2018/3/25/entrez KW - Bromide ion KW - Chloride ion KW - In situ chemical oxidation KW - Peroxymonosulfate KW - Steroid estrogens SP - 56 EP - 66 JF - Water research JO - Water Res. VL - 138 N2 - Recently, in situ chemical oxidation (ISCO) using peroxymonosulfate (PMS) for environmental decontamination has received increasing interest. In this study, oxidation kinetics and products of four steroid estrogens (i.e., estrone, 17β-estradiol, estriol, and 17α-ethinylestradiol) by PMS under various conditions were investigated. PMS could fairly degrade steroid estrogens over the pH range of 7-10, and the degradation rate increased with the increase of solution pH. This pH-dependence was well described by parallel reactions between individual acid-base species of steroid estrogens (E and E-) and PMS (HSO5- and SO52-), where specific second-order rate constants for E- with HSO5- and SO52- were in the range of 2.11-5.58 M-1s-1 and 0.77-1.25 M-1s-1, respectively. Identification of oxidation products by liquid chromatography/electrospray ionization quadrupole time-of-flight mass spectrometer showed that PMS readily oxidized the phenolic group of steroid estrogens, leading to the generation of hydroxylated and ring-opening products. The presence of bromide and chloride ions (Br- and Cl-) at environmentally relevant levels could greatly accelerate the degradation of steroid estrogens by PMS with the formation of halogenated aromatic products. This effect was quantitatively estimated by a kinetic model, where the formation of free bromine and chorine and their rapid electrophilic substitution with steroid estrogens were taken into consideration. Eco-toxicity of transformation products of 17α-ethinylestradiol by PMS treatment in the absence and presence of bromide and chloride was estimated by quantitative structure-activity relationship analysis using ECOSAR. These findings advance the understanding of ISCO using PMS. SN - 1879-2448 UR - https://www.unboundmedicine.com/medline/citation/29573629/Oxidation_of_steroid_estrogens_by_peroxymonosulfate__PMS__and_effect_of_bromide_and_chloride_ions:_Kinetics_products_and_modeling_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0043-1354(18)30241-0 DB - PRIME DP - Unbound Medicine ER -