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Activation of peroxymonosulfate by phenols: Important role of quinone intermediates and involvement of singlet oxygen.
Water Res. 2017 11 15; 125:209-218.WR

Abstract

In this study, the kinetics of reactions of peroxymonosulfate (PMS) with ten model phenols (including phenol, methylphenols, methoxyphenols, and dihydroxybenzenes) were examined. The oxidation kinetics of these phenols by PMS except for catechol and resorcinol showed autocatalysis in alkaline conditions (pH 8.5 and 10), due to the contribution of singlet oxygen (1O2) produced from PMS activation by quinone intermediates formed from their phenolic parents. The oxidation rates of ortho- and meta-substituted methylphenols and methoxyphenols by PMS were much higher than their para-substituted counterparts under similar conditions. This was attributed to the relatively low yields of quinone intermediates from para-substituted phenols. SMX could be efficiently degraded by PMS in the presence of phenols which showed great autocatalysis when they individually reacted with PMS, and the addition of methanol in excess had negligible influence suggesting that 1O2 rather than hydroxyl radical and sulfate radical played an important role. Transformation of SMX by 1O2 underwent three pathways including hydroxylation of aniline ring, oxidation of aromatic amine group to generate nitro-SMX, and oxidative coupling to generate azo-SMX and hydroxylated azo-SMX. These results obtained in this work improve the understanding of in situ chemical oxidation using PMS for remediation of subsurface, where phenolic and quinonoid moieties are ubiquitous.

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.Key Laboratory of Green Chemical Engineering and Technology of College of Heilongjiang Province, College of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin, 150040, 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.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.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.State Key Laboratory of Urban Water Resource and Environment, School of Municipal and Environmental Engineering, Harbin Institute of Technology, Harbin, 150090, China.Key Laboratory of Green Chemical Engineering and Technology of College of Heilongjiang Province, College of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin, 150040, China.Key Laboratory of Green Chemical Engineering and Technology of College of Heilongjiang Province, College of Chemical and Environmental Engineering, Harbin University of Science and Technology, Harbin, 150040, China.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

28863343

Citation

Zhou, Yang, et al. "Activation of Peroxymonosulfate By Phenols: Important Role of Quinone Intermediates and Involvement of Singlet Oxygen." Water Research, vol. 125, 2017, pp. 209-218.
Zhou Y, Jiang J, Gao Y, et al. Activation of peroxymonosulfate by phenols: Important role of quinone intermediates and involvement of singlet oxygen. Water Res. 2017;125:209-218.
Zhou, Y., Jiang, J., Gao, Y., Pang, S. Y., Yang, Y., Ma, J., Gu, J., Li, J., Wang, Z., Wang, L. H., Yuan, L. P., & Yang, Y. (2017). Activation of peroxymonosulfate by phenols: Important role of quinone intermediates and involvement of singlet oxygen. Water Research, 125, 209-218. https://doi.org/10.1016/j.watres.2017.08.049
Zhou Y, et al. Activation of Peroxymonosulfate By Phenols: Important Role of Quinone Intermediates and Involvement of Singlet Oxygen. Water Res. 2017 11 15;125:209-218. PubMed PMID: 28863343.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Activation of peroxymonosulfate by phenols: Important role of quinone intermediates and involvement of singlet oxygen. AU - Zhou,Yang, AU - Jiang,Jin, AU - Gao,Yuan, AU - Pang,Su-Yan, AU - Yang,Yi, AU - Ma,Jun, AU - Gu,Jia, AU - Li,Juan, AU - Wang,Zhen, AU - Wang,Li-Hong, AU - Yuan,Li-Peng, AU - Yang,Yue, Y1 - 2017/08/23/ PY - 2017/06/19/received PY - 2017/08/21/revised PY - 2017/08/22/accepted PY - 2017/9/2/pubmed PY - 2018/7/17/medline PY - 2017/9/2/entrez KW - Peroxymonosulfate KW - Phenols KW - Quinone intermediates KW - Singlet oxygen KW - Sulfamethoxazole SP - 209 EP - 218 JF - Water research JO - Water Res. VL - 125 N2 - In this study, the kinetics of reactions of peroxymonosulfate (PMS) with ten model phenols (including phenol, methylphenols, methoxyphenols, and dihydroxybenzenes) were examined. The oxidation kinetics of these phenols by PMS except for catechol and resorcinol showed autocatalysis in alkaline conditions (pH 8.5 and 10), due to the contribution of singlet oxygen (1O2) produced from PMS activation by quinone intermediates formed from their phenolic parents. The oxidation rates of ortho- and meta-substituted methylphenols and methoxyphenols by PMS were much higher than their para-substituted counterparts under similar conditions. This was attributed to the relatively low yields of quinone intermediates from para-substituted phenols. SMX could be efficiently degraded by PMS in the presence of phenols which showed great autocatalysis when they individually reacted with PMS, and the addition of methanol in excess had negligible influence suggesting that 1O2 rather than hydroxyl radical and sulfate radical played an important role. Transformation of SMX by 1O2 underwent three pathways including hydroxylation of aniline ring, oxidation of aromatic amine group to generate nitro-SMX, and oxidative coupling to generate azo-SMX and hydroxylated azo-SMX. These results obtained in this work improve the understanding of in situ chemical oxidation using PMS for remediation of subsurface, where phenolic and quinonoid moieties are ubiquitous. SN - 1879-2448 UR - https://www.unboundmedicine.com/medline/citation/28863343/Activation_of_peroxymonosulfate_by_phenols:_Important_role_of_quinone_intermediates_and_involvement_of_singlet_oxygen_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0043-1354(17)30711-X DB - PRIME DP - Unbound Medicine ER -