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Non-activated peroxymonosulfate oxidation of sulfonamide antibiotics in water: Kinetics, mechanisms, and implications for water treatment.
Water Res. 2018 12 15; 147:82-90.WR

Abstract

Despite that sulfate radical-based activated peroxymonosulfate (PMS) oxidation processes (e.g., UV/PMS, Co2+/PMS, etc.) have been widely applied for decontamination, the direct oxidation of organic contaminants by PMS per se is less known. This contribution reports that certain contaminants, such as sulfonamides (SAs), are amendable to direct oxidation by PMS without activation. Using sulfamethoxazole (SMX) as a representative, kinetics and density functional theory (DFT)-based computational methods were applied to elucidate the underlying mechanisms and pathways through which SMX was transformed by direct PMS oxidation. High resolution mass spectrometry (HR-MS) coupled with high performance liquid chromatography (HPLC) analyses using authentic standards were adopted to qualifying and quantifying SMX transformation products. Our results reveal that nonradical oxidation of SMX by PMS was initiated by formation of a transition state complex between PMS molecule and amino functional group of SMX. Such reaction was assisted by two water molecules, which significantly reduced energy barrier. Direct PMS oxidation of SMX led to the formation of N4-hydroxyl-sulfamethoxazole (N4-OH-SMX), 4-nitroso-sulfamethoxazole (4-NO-SMX), and 4-nitro-sulfamethoxazole (4-NO2-SMX), sequentially. Implications of PMS oxidation with SAs to water treatment were further evaluated by investigating the effects of PMS dosage, pH, and natural water matrices. While PMS has a potential to transform a suite of SAs with similar structures (SMX, sulfisoxazole, sulfamethizole, sulfapyridine, sulfadiazine, and sulfachloropyridazine), the formation of potential hazardous nitroso- and nitro-byproducts should be scrutinized before this technology can be safely used for water and wastewater treatment.

Authors+Show Affiliations

College of Resources and Environmental Sciences, Nanjing Agricultural University, Nanjing, 210095, China.College of Resources and Environmental Sciences, Nanjing Agricultural University, Nanjing, 210095, China. Electronic address: jhlu@njau.edu.cn.College of Resources and Environmental Sciences, Nanjing Agricultural University, Nanjing, 210095, China.College of Resources and Environmental Sciences, Nanjing Agricultural University, Nanjing, 210095, China.College of Resources and Environmental Sciences, Nanjing Agricultural University, Nanjing, 210095, China.College of Resources and Environmental Sciences, Nanjing Agricultural University, Nanjing, 210095, China.State Environmental Protection Key Lab of Environmental Risk Assessment and Control on Chemical Processes, School of Resources & Environmental Engineering, East China University of Science and Technology, Shanghai, 200237, China; Shanghai Institute of Pollution Control and Ecological Security, Shanghai, 200092, China. Electronic address: zhoulei@ecust.edu.cn.Univ Lyon, Université Claude Bernard Lyon 1, CNRS, IRCELYON, F-69626, Villeurbanne, France.Univ Lyon, Université Claude Bernard Lyon 1, CNRS, IRCELYON, F-69626, Villeurbanne, France.

Pub Type(s)

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

Language

eng

PubMed ID

30300784

Citation

Ji, Yuefei, et al. "Non-activated Peroxymonosulfate Oxidation of Sulfonamide Antibiotics in Water: Kinetics, Mechanisms, and Implications for Water Treatment." Water Research, vol. 147, 2018, pp. 82-90.
Ji Y, Lu J, Wang L, et al. Non-activated peroxymonosulfate oxidation of sulfonamide antibiotics in water: Kinetics, mechanisms, and implications for water treatment. Water Res. 2018;147:82-90.
Ji, Y., Lu, J., Wang, L., Jiang, M., Yang, Y., Yang, P., Zhou, L., Ferronato, C., & Chovelon, J. M. (2018). Non-activated peroxymonosulfate oxidation of sulfonamide antibiotics in water: Kinetics, mechanisms, and implications for water treatment. Water Research, 147, 82-90. https://doi.org/10.1016/j.watres.2018.09.037
Ji Y, et al. Non-activated Peroxymonosulfate Oxidation of Sulfonamide Antibiotics in Water: Kinetics, Mechanisms, and Implications for Water Treatment. Water Res. 2018 12 15;147:82-90. PubMed PMID: 30300784.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Non-activated peroxymonosulfate oxidation of sulfonamide antibiotics in water: Kinetics, mechanisms, and implications for water treatment. AU - Ji,Yuefei, AU - Lu,Junhe, AU - Wang,Lu, AU - Jiang,Mengdi, AU - Yang,Yan, AU - Yang,Peizeng, AU - Zhou,Lei, AU - Ferronato,Corinne, AU - Chovelon,Jean-Marc, Y1 - 2018/10/01/ PY - 2018/06/14/received PY - 2018/09/03/revised PY - 2018/09/20/accepted PY - 2018/10/10/pubmed PY - 2019/9/26/medline PY - 2018/10/10/entrez KW - 4-Nitro-sulfamethoxazole KW - Peroxymonosulfate KW - Sulfamethoxazole KW - Sulfonamide antibiotics KW - Transformation SP - 82 EP - 90 JF - Water research JO - Water Res. VL - 147 N2 - Despite that sulfate radical-based activated peroxymonosulfate (PMS) oxidation processes (e.g., UV/PMS, Co2+/PMS, etc.) have been widely applied for decontamination, the direct oxidation of organic contaminants by PMS per se is less known. This contribution reports that certain contaminants, such as sulfonamides (SAs), are amendable to direct oxidation by PMS without activation. Using sulfamethoxazole (SMX) as a representative, kinetics and density functional theory (DFT)-based computational methods were applied to elucidate the underlying mechanisms and pathways through which SMX was transformed by direct PMS oxidation. High resolution mass spectrometry (HR-MS) coupled with high performance liquid chromatography (HPLC) analyses using authentic standards were adopted to qualifying and quantifying SMX transformation products. Our results reveal that nonradical oxidation of SMX by PMS was initiated by formation of a transition state complex between PMS molecule and amino functional group of SMX. Such reaction was assisted by two water molecules, which significantly reduced energy barrier. Direct PMS oxidation of SMX led to the formation of N4-hydroxyl-sulfamethoxazole (N4-OH-SMX), 4-nitroso-sulfamethoxazole (4-NO-SMX), and 4-nitro-sulfamethoxazole (4-NO2-SMX), sequentially. Implications of PMS oxidation with SAs to water treatment were further evaluated by investigating the effects of PMS dosage, pH, and natural water matrices. While PMS has a potential to transform a suite of SAs with similar structures (SMX, sulfisoxazole, sulfamethizole, sulfapyridine, sulfadiazine, and sulfachloropyridazine), the formation of potential hazardous nitroso- and nitro-byproducts should be scrutinized before this technology can be safely used for water and wastewater treatment. SN - 1879-2448 UR - https://www.unboundmedicine.com/medline/citation/30300784/Non_activated_peroxymonosulfate_oxidation_of_sulfonamide_antibiotics_in_water:_Kinetics_mechanisms_and_implications_for_water_treatment_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0043-1354(18)30752-8 DB - PRIME DP - Unbound Medicine ER -