Degradation of sulfamethoxazole using ozone and chlorine dioxide - Compound-specific stable isotope analysis, transformation product analysis and mechanistic aspects

Abellán, 2008, Detection and identification of degradation products of sulfamethoxazole by means of LC/MS and -MS(n) after ozone treatment, Water Sci. Technol., 58, 1803, 10.2166/wst.2008.539

Aguilar, 2014, Kinetics and mechanism for the oxidation of anilines by ClO2: a combined experimental and computational study, J. Phys. Org. Chem., 27, 440, 10.1002/poc.3281

Birkigt, 2015, Carbon stable isotope fractionation of sulfamethoxazole during biodegradation by microbacterium sp. strain BR1 and upon direct photolysis, Environ. Sci. Technol., 49, 6029, 10.1021/acs.est.5b00367

Boreen, 2004, Photochemical fate of sulfa drugs in the aquatic environment: sulfa drugs containing five-membered heterocyclic groups, Environ. Sci. Technol., 38, 3933, 10.1021/es0353053

Bu, 2013, Pharmaceuticals and personal care products in the aquatic environment in China: a review, J. Hazard. Mater., 262, 189, 10.1016/j.jhazmat.2013.08.040

Carballa, 2004, Behavior of pharmaceuticals, cosmetics and hormones in a sewage treatment plant, Water Res., 38, 2918, 10.1016/j.watres.2004.03.029

Dodd, 2006, Oxidation of antibacterial molecules by aqueous ozone: moiety-specific reaction kinetics and application to ozone-based wastewater treatment, Environ. Sci. Technol., 40, 1969, 10.1021/es051369x

Elsner, 2005, A new concept linking observable stable isotope fractionation to transformation pathways of organic pollutants, Environ. Sci. Technol., 39, 6896, 10.1021/es0504587

Elsner, 2012, Current challenges in compound-specific stable isotope analysis of environmental organic contaminants, Anal. Bioanal. Chem., 403, 2471, 10.1007/s00216-011-5683-y

Federherr, 2016, A novel high-temperature combustion interface for compound-specific stable isotope analysis of carbon and nitrogen via high-performance liquid chromatography/isotope ratio mass spectrometry, Rapid Commun. Mass Spectrom., 30, 944, 10.1002/rcm.7524

Flyunt, 2001, OH radical-induced oxidation of methanesulfinic acid. The reactions of the methanesulfonyl radical in the absence and presence of dioxygen, J. Chem. Soc. Perkin Trans., 2, 787, 10.1039/b009631h

Gates, 1998

Gao, 2014, Oxidation of sulfamethoxazole (SMX) by chlorine, ozone and permanganate—a comparative study, J. Hazard. Mater., 274, 258, 10.1016/j.jhazmat.2014.04.024

Gómez-Ramos, 2011, Chemical and toxicological evolution of the antibiotic sulfamethoxazole under ozone treatment in water solution, J. Hazard. Mater., 192, 18

Guo, 2015, Sulfamethoxazole degradation by ultrasound/ozone oxidation process in water: kinetics, mechanisms, and pathways, Ultrason. Sonochem., 22, 182, 10.1016/j.ultsonch.2014.07.008

Hartenbach, 2008, Carbon, hydrogen, and nitrogen isotope fractionation during light-induced transformations of atrazine, Environ. Sci. Technol., 42, 7751, 10.1021/es800356h

Hoigné, 1994, Kinetics of reactions of chlorine dioxide (OClO) in water-I. Rate constants for inorganic and organic compounds, Water Res., 28, 45, 10.1016/0043-1354(94)90118-X

Huber, 2005, Oxidation of pharmaceuticals during water treatment with chlorine dioxide, Water Res., 39, 3607, 10.1016/j.watres.2005.05.040

Hull, 1967, Oxidations of amines. III. Duality of mechanism in the reaction of amines with chlorine dioxide, J. Am. Chem. Soc., 89, 1163, 10.1021/ja00981a023

Jekel, 2015, Selection of organic process and source indicator substances for the anthropogenically influenced water cycle, Chemosphere, 125, 155, 10.1016/j.chemosphere.2014.12.025

Jia, 2000, General-acid-catalyzed reactions of hypochlorous acid and acetyl hypochlorite with chlorite ion, Inorg. Chem., 39, 2614, 10.1021/ic991486r

Jochmann, 2006, A new approach to determine method detection limits for compound-specific isotope analysis of volatile organic compounds, Rapid Commun. Mass Spectrom., 20, 3639, 10.1002/rcm.2784

Jochmann, 2012

Knopp, 2016, Elimination of micropollutants and transformation products from a wastewater treatment plant effluent through pilot scale ozonation followed by various activated carbon and biological filters, Water Res., 100, 580, 10.1016/j.watres.2016.04.069

Kümmerer, 2009, Antibiotics in the aquatic environment - a review - Part I, Chemosphere, 75, 417, 10.1016/j.chemosphere.2008.11.086

Kujawinski, 2012, When other separation techniques fail: compound-specific carbon isotope ratio analysis of sulfonamide containing pharmaceuticals by high-temperature-liquid chromatography-isotope ratio mass spectrometry, Anal. Chem., 84, 7656, 10.1021/ac300116w

Lee, 2010, Oxidative transformation of micropollutants during municipal wastewater treatment: comparison of kinetic aspects of selective (chlorine, chlorine dioxide, ferrateVI, and ozone) and non-selective oxidants (hydroxyl radical), Water Res., 44, 555, 10.1016/j.watres.2009.11.045

Maier, 2016, Exploring trends of C and N isotope fractionation to trace transformation reactions of diclofenac in natural and engineered systems, Environ. Sci. Technol., 50, 10933, 10.1021/acs.est.6b02104

Martín de Vidales, 2012, Removal of sulfamethoxazole from waters and wastewaters by conductive-diamond electrochemical oxidation, J. Chem. Technol. Biotechnol., 87, 1441, 10.1002/jctb.3766

Rav-Acha, 1987, Aqueous reactions of chlorine dioxide with hydrocarbons, Environ. Sci. Technol., 21, 1069, 10.1021/es00164a004

Rudy, 1973, Sulfamethoxazole, Anal. Profiles Drug Subst. Excipients, 2, 467

Sein, 2008, Oxidation of diclofenac with ozone in aqueous solution, Environ. Sci. Technol., 42, 6656, 10.1021/es8008612

Sherwood Lollar, 2007, An approach for assessing total instrumental uncertainty in compound-specific carbon isotope analysis: implications for environmental remediation studies, Anal. Chem., 79, 3469, 10.1021/ac062299v

Shimizu, 2013, Ubiquitous occurrence of sulfonamides in tropical Asian waters, Sci. Total Environ., 452–453, 108, 10.1016/j.scitotenv.2013.02.027

Tekle-Röttering, 2016, Ozonation of anilines: kinetics, stoichiometry, product identification and elucidation of pathways, Water Res., 98, 147, 10.1016/j.watres.2016.04.001

Veltwisch, 1980, Primary processes in the reaction of OH·-radicals with sulphoxides, J. Chem. Soc. Perkin Trans., 2, 146, 10.1039/P29800000146

Verlicchi, 2012, Occurrence of pharmaceutical compounds in urban wastewater: removal, mass load and environmental risk after a secondary treatment-a review, Sci. Total Environ., 429, 123, 10.1016/j.scitotenv.2012.04.028

von Sonntag, 2012

Wajon, 1982, Oxidation of phenol and hydroquinone by chlorine dioxide, Environ. Sci. Technol., 16, 396, 10.1021/es00101a006

Werner, 2001, Referencing strategies and techniques in stable isotope ratio analysis, Rapid Commun. Mass Spectrom., 15, 501, 10.1002/rcm.258

Yu, 2017, The degradation mechanism of sulfamethoxazole under ozonation: a DFT study, Environ. Sci. Process. Impacts, 379, 10.1039/C6EM00698A