Experimental and theoretical insight into hydroxyl and sulfate radicals-mediated degradation of carbamazepine
Tài liệu tham khảo
Ali, 2018, Carbamazepine degradation by UV and UV-assisted AOPs: kinetics, mechanism and toxicity investigations, Process Saf. Environ., 117, 307, 10.1016/j.psep.2018.05.004
Anipsitakis, 2004, Radical generation by the interaction of transition metals with common oxidants, Environ. Sci. Technol., 38, 3705, 10.1021/es035121o
Baeza, 2011, Transformation kinetics of biochemically active compounds in low-pressure UV Photolysis and UV/H2O2 advanced oxidation processes, Water Res., 45, 4531, 10.1016/j.watres.2011.05.039
Becke, 1988, Density-functional exchange-energy approximation with correct asymptotic behavior, Phys. Rev. A, 38, 3098, 10.1103/PhysRevA.38.3098
Beitz, 1998, Investigations of reactions of selected azaarenes with radicals in water. 1. Hydroxyl and sulfate radicals, J. Phys. Chem., 102, 6760, 10.1021/jp980654i
Beltran, 1995, Oxidation of polynuclear aromatic hydrocarbons in water. 2. UV radiation and ozonation in the presence of UV radiation, Ind. Eng. Chem. Res., 34, 1607, 10.1021/ie00044a013
Benitez, 2004, Modeling of photooxidation of acetamide herbicides in natural waters by UV radiation and the combinations UV/H2O2 and UV/O3, 987
Benotti, 2009, Pharmaceuticals and endocrine disrupting compounds in U.S. drinking water, Environ. Sci. Technol., 43, 597, 10.1021/es801845a
Bolton, 2002, Fundamental photochemical approach to the concepts of fluence (UV dose) and electrical energy efficiency in photochemical degradation reactions, Res. Chem. Intermed., 28, 857, 10.1163/15685670260469474
Buxton, 1988, Critical review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals (⋅OH/O⋅−) in aqueous solution, J. Phys. Chem. Ref. Data, 17, 513, 10.1063/1.555805
Calais, 1993, Density-functional theory of atoms and molecules, Int. J. Quantum Chem., 47
Campillo, 2004, A study of peculiar tautomerism of pyrido 2,3-c 1,2,6 thiadiazine 2,2-dioxide system, J. Mol. Struc. Theochem., 678, 83, 10.1016/j.theochem.2004.03.014
Clara, 2004, Carbamazepine as a possible anthropogenic marker in the aquatic environment: investigations on the behaviour of Carbamazepine in wastewater treatment and during groundwater infiltration, Water Res., 38, 947, 10.1016/j.watres.2003.10.058
Criquet, 2010, Enhancement of carboxylic acid degradation with sulfate radical generated by persulfate activation, Water Sci. Technol., 61, 1221, 10.2166/wst.2010.008
Cvetnic, 2019, Key structural features promoting radical driven degradation of emerging contaminants in water, Environ. Int., 124, 38, 10.1016/j.envint.2018.12.043
Daisuke, 2011, Linear free energy relationships between aqueous phase hydroxyl radical reaction rate constants and free energy of activation, Environ. Sci. Technol., 45, 3479, 10.1021/es1020313
De la Cruz, 2012, Degradation of 32 emergent contaminants by UV and neutral photo-fenton in domestic wastewater effluent previously treated by activated sludge, Water Res., 46, 1947, 10.1016/j.watres.2012.01.014
Deng, 2013, Degradation of the antiepileptic drug carbamazepine upon different UV-based advanced oxidation processes in water, Chem. Eng. J., 222, 150, 10.1016/j.cej.2013.02.045
Devi, 2016, In-situ chemical oxidation: principle and applications of peroxide and persulfate treatments in wastewater systems, Sci. Total Environ., 571, 643, 10.1016/j.scitotenv.2016.07.032
Ding, 2019, Theoretical investigation on atmospheric oxidation of fluorene initiated by OH radical, Sci. Total Environ., 669, 920, 10.1016/j.scitotenv.2019.02.400
Drewes, 2002, Fate of pharmaceuticals during indirect potable reuse, Water Sci. Technol., 46, 73, 10.2166/wst.2002.0058
Ensano, 2017, Removal of pharmaceuticals from wastewater by intermittent electrocoagulation, Water, 9, 85, 10.3390/w9020085
Fekadu, 2019, Pharmaceuticals in freshwater aquatic environments: a comparison of the African and European challenge, Sci. Total Environ., 654, 324, 10.1016/j.scitotenv.2018.11.072
Frisch, 2009
Gao, 2019, Mechanistic study on the role of soluble microbial products in sulfate radical-mediated degradation of pharmaceuticals, Environ. Sci. Technol., 53, 342, 10.1021/acs.est.8b05129
Galano, 2011, Glutathione: mechanism and kinetics of its non-enzymatic defense action against free radicals, RSC Adv., 1, 1763, 10.1039/c1ra00474c
Gao, 2014, Mechanism, kinetics and toxicity assessment of OH-initiated transformation of triclosan in aquatic environments, Water Res., 49, 360, 10.1016/j.watres.2013.10.027
Gao, 2016, Bioaccumulation and ecotoxicity increase during indirect photochemical transformation of polycyclic musk tonalide: a modeling study, Water Res., 105, 47, 10.1016/j.watres.2016.08.055
Gao, 2019, New theoretical insight into indirect photochemical transformation of fragrance nitro-musks: mechanisms, eco-toxicity and health effects, Environ. Int., 129, 68, 10.1016/j.envint.2019.05.020
Ghanbari, 2017, Application of peroxymonosulfate and its activation methods for degradation of environmental organic pollutants: Review, Chem. Eng. J., 310, 41, 10.1016/j.cej.2016.10.064
Greenspan, 1948, Analysis of aliphatic per acids, Anal. Chem., 20, 1061, 10.1021/ac60023a020
Haag, 1992, Rate constants for reaction of hydroxyl radicals with several drinking water contaminants, Environ. Sci. Technol., 26, 1005, 10.1021/es00029a021
Halgren, 1996, Merck molecular force field. I. Basis, form, scope, parameterization, and performance of MMFF94, J. Comput. Chem., 17, 490, 10.1002/(SICI)1096-987X(199604)17:5/6<490::AID-JCC1>3.0.CO;2-P
Hatchard, 1956, A new sensitive chemical actinometer-II. Potassium ferrioxalate as a standard chemical actinometer, vol. 235, 518
Hosoi, 2015, Mechanistic aspects of asymmetric intramolecular Heck reaction involving dynamic kinetic resolution: flexible conformation of the cyclohexenylidene–benzene system, Tetrahedron, 71, 2317, 10.1016/j.tet.2015.01.020
Huber, 2005, Oxidation of pharmaceuticals during ozonation of municipal wastewater effluents: a pilot study, Environ. Sci. Technol., 39, 4290, 10.1021/es048396s
Ilho, 2009, Photodegradation characteristics of PPCPs in water with UV treatment, Environ. Int., 35, 0
Jones, 2002, Aquatic environmental assessment of the top 25 English prescription pharmaceuticals, Water Res., 36, 5013, 10.1016/S0043-1354(02)00227-0
Khan, 2014, Kinetic and mechanism investigation on the photochemical degradation of atrazine with activated H2O2, S2O82− and HSO5−, Chem. Eng. J., 252, 393, 10.1016/j.cej.2014.04.104
Khan, 2017, Degradation kinetics and mechanism of desethyl-atrazine and desisopropyl-atrazine in water with •OH and SO4•− based-AOPs, Chem. Eng. J., 325, 485, 10.1016/j.cej.2017.05.011
Kiassen, 1994, H2O2 determination by the I3- method and by KMnO4 titration, Anal. Chem., 66, 2921, 10.1021/ac00090a020
Kim, 2009, Photodegradation of pharmaceuticals and personal care products during UV and UV/H2O2 treatments, Chemosphere, 77, 518, 10.1016/j.chemosphere.2009.07.041
Kong, 2009, Aerobic granulation in sequencing batch reactors with different reactor height/diameter ratios, Enzym. Microb. Technol., 45, 379, 10.1016/j.enzmictec.2009.06.014
Kwon, 2015, Comparative evaluation of ibuprofen removal by UV/H2O2 and UV/S2O82− processes for wastewater treatment, Chem. Eng. J., 269, 379, 10.1016/j.cej.2015.01.125
Lam, 2005, Photodegradation of the pharmaceuticals atorvastatin, carbamazepine, levofloxacin, and sulfamethoxazole in natural waters, Aquat. Sci., 67, 177, 10.1007/s00027-004-0768-8
Lindsey, 2000, Inhibition of hydroxyl radical reaction with aromatics by dissolved natural organic matter, Environ. Sci. Technol., 34, 444, 10.1021/es990457c
Liu, 2013, Application potential of carbon nanotubes in water treatment: a review, J. Environ. Sci., 25, 1263, 10.1016/S1001-0742(12)60161-2
Liu, 2016, Kinetics and mechanism investigation on the destruction of oxytetracycline by UV-254nm activation of persulfate, J. Hazard Mater., 305, 229, 10.1016/j.jhazmat.2015.11.043
Luo, 2018, Kinetic and mechanistic aspects of hydroxyl radical‒mediated degradation of naproxen and reaction intermediates, Water Res., 137, 233, 10.1016/j.watres.2018.03.002
Luo, 2017, Mechanistic insight into reactivity of sulfate radical with aromatic contaminants through single-electron transfer pathway, Chem. Eng. J., 327, 1056, 10.1016/j.cej.2017.06.179
Luo, 2018, UV direct photolysis of sulfamethoxazole and ibuprofen: an experimental and modelling study, J. Hazard Mater., 343, 132, 10.1016/j.jhazmat.2017.09.019
Matta, 2011, Removal of carbamazepine from urban wastewater by sulfate radical oxidation, Environ. Chem. Lett., 9, 347, 10.1007/s10311-010-0285-z
Mercado, 2018, Reaction kinetics and mechanisms of organosilicon fungicide flusilazole with sulfate and hydroxyl radicals, Chemosphere, 190, 327, 10.1016/j.chemosphere.2017.09.134
Nakada, 2006, Pharmaceutical chemicals and endocrine disrupters in municipal wastewater in Tokyo and their removal during activated sludge treatment, Water Res., 40, 3297, 10.1016/j.watres.2006.06.039
Nassef, 2010, Acute effects of triclosan, diclofenac and carbamazepine on feeding performance of Japanese medaka fish (Oryzias latipes), Chemosphere, 80, 1095, 10.1016/j.chemosphere.2010.04.073
Neta, 1977, Rate constants and mechanism of reaction of sulfate radical anion with aromatic compounds, J. Am. Chem. Soc., 99, 163, 10.1021/ja00443a030
Norman, 1970, Electron spin resonance studies. Part XXV. Reactions of the sulphate radical anion with organic compounds, J. Chem. Soc. B Phys. Org., 1087, 10.1039/j29700001087
Obot, 2013, Anticorrosion potential of 2-Mesityl-1H-imidazo[4,5-f][1,10]phenanthroline on mild steel in sulfuric acid solution: experimental and theoretical study, Ind. Eng. Chem. Res., 50, 2098, 10.1021/ie102034c
Packer, 2003, Photochemical fate of pharmaceuticals in the environment: naproxen, diclofenac, clofibric acid, and ibuprofen, Aquat. Sci., 65, 342, 10.1007/s00027-003-0671-8
Parker, 1953, A new sensitive chemical actinometer. I. Some trials with potassium ferrioxalate, vol. 220, 104
Ramirez-Arizmendi, 2001, Hydrogen atom abstraction and addition reactions of charged phenyl radicals with aromatic substrates in the gas phase, Int. J. Mass Spectrom., 210, 511, 10.1016/S1387-3806(01)00452-3
Rao, 2014, Degradation of carbamazepine by Fe(II)-activated persulfate process, J. Hazard Mater., 268, 23, 10.1016/j.jhazmat.2014.01.010
Razmi, 2010, Non-enzymatic hydrogen peroxide sensor using an electrode modified with iron pentacyanonitrosylferrate nanoparticles, Microchimi. Acta, 171, 257, 10.1007/s00604-010-0426-x
Roberto, 2002, Carbamazepine in water: persistence in the environment, ozonation treatment and preliminary assessment on algal toxicity, Water Res., 36, 2869, 10.1016/S0043-1354(01)00500-0
Shah, 2013, Efficient removal of endosulfan from aqueous solution by UV-C/peroxides: a comparative study, J. Hazard Mater., 263, 584, 10.1016/j.jhazmat.2013.10.019
Tomas, 2014, Ecological effects of pharmaceuticals in aquatic systems-impacts through behavioural alterations, Philos. Trans. R. Soc. Lond. B Biol. Sci., 369, 20130580, 10.1098/rstb.2013.0580
Vernouillet, 2010, Toxic effects and bioaccumulation of carbamazepine evaluated by biomarkers measured in organisms of different trophic levels, Chemosphere, 80, 1062, 10.1016/j.chemosphere.2010.05.010
Villamena, 2007, Rate constants of hydroperoxyl radical addition to cyclic nitrones: a DFT study, J. Phys. Chem., 111, 9995, 10.1021/jp073615s
Vogna, 2004, Kinetic and chemical assessment of the UV/H2O2 treatment of antiepileptic drug carbamazepine, Chemosphere, 54, 497, 10.1016/S0045-6535(03)00757-4
Wang, 2018, Degradation kinetic of dibutyl phthalate (DBP) by sulfate radical- and hydroxyl radical-based advanced oxidation process in UV/persulfate system, Separ. Purif. Technol., 195, 92, 10.1016/j.seppur.2017.11.072
Wei, 2019, Electrophilicity index as a critical indicator for the biodegradation of the pharmaceuticals in aerobic activated sludge processes, Water Res., 160, 10, 10.1016/j.watres.2019.05.057
Wols, 2012, Review of photochemical reaction constants of organic micropollutants required for UV advanced oxidation processes in water, Water Res., 46, 2815, 10.1016/j.watres.2012.03.036
Wu, 2017, Theoretical and shock tube study of the rate constants for hydrogen abstraction reactions of ethyl formate, J. Phys. Chem., 121, 6304, 10.1021/acs.jpca.7b06119
Wu, 2019, Modelling study on the effects of chloride on the degradation of bezafibrate and carbamazepine in sulfate radical-based advanced oxidation processes: conversion of reactive radicals, Chem. Eng. J., 358, 1332, 10.1016/j.cej.2018.10.125
Xiao, 2017, Mechanistic insight into degradation of endocrine disrupting chemical by hydroxyl radical: an experimental and theoretical approach, Environ. Pollut., 231, 1446, 10.1016/j.envpol.2017.09.006
Xiao, 2019, Inactivation of pathogenic microorganisms by sulfate radical: present and future, Chem. Eng. J., 371, 222, 10.1016/j.cej.2019.03.296
Xiao, 2015, Kinetic modeling and energy efficiency of UV/H2O2 treatment of iodinated trihalomethanes, Water Res., 75, 259, 10.1016/j.watres.2015.02.044
Yang, 1987, Mechanism of the reduction of ketones by trialkylsilane: hydride transfer, SET-hydrogen atom abstraction, or free radical addition, ChemInform, 18, 2267, 10.1002/chin.198701088
Yang, 2017, Comparison of the reactivity of ibuprofen with sulfate and hydroxyl radicals: an experimental and theoretical study, Sci. Total Environ., 590–591, 751, 10.1016/j.scitotenv.2017.03.039
Zhang, 2015, Degradation of pharmaceuticals and metabolite in synthetic human urine by UV, UV/H2O2, and UV/PDS, Environ. Sci. Technol., 49, 3056, 10.1021/es504799n
Zhang, 2016, Catalytic degradation of diethyl phthalate in aqueous solution by persulfate activated with nano-scaled magnetic CuFe2O4/MWCNTs, Chem. Eng. J., 301, 1, 10.1016/j.cej.2016.04.096
Zhang, 2008, Carbamazepine and diclofenac: removal in wastewater treatment plants and occurrence in water bodies, Chemosphere, 73, 1151, 10.1016/j.chemosphere.2008.07.086
Zhao, 2008, The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06 functionals and 12 other functionals, Theor. Chem. Acc., 119, 10.1007/s00214-007-0401-8
