Reactions of chlorine with inorganic and organic compounds during water treatment—Kinetics and mechanisms: A critical review

Water Research - Tập 42 Số 1-2 - Trang 13-51 - 2008
Marie Deborde1, Urs von Gunten1,2
1Department of Water Resources and Drinking Water, Eawag: Swiss Federal Institute of Aquatic Science and Technology, Ueberlandstrasse 133, CH-8600 Dübendorf, Switzerland
2Institute of Biogeochemistry and Pollutant Dynamics, ETH Zürich, CH-8092 Zürich, Switzerland

Tóm tắt

Từ khóa


Tài liệu tham khảo

Abia, 1998, Oxidation of aliphatic amines by aqueous chlorine, Tetrahedron, 54, 521, 10.1016/S0040-4020(97)10312-X

Acero, 2005, Kinetics of reactions between chlorine and the cyanobacterial toxins microcystins, Water Res., 39, 1628, 10.1016/j.watres.2005.01.022

Acero, 2005, Kinetics and mechanisms of formation of bromophenols during drinking water chlorination: assessment of taste and odor development, Water Res., 39, 2979, 10.1016/j.watres.2005.04.055

Antelo, 1985, A kinetic study of the chlorination of tertiary alcoholamines in alkaline media, Int. J. Chem. Kinet., 17, 1231, 10.1002/kin.550171109

Antelo, 1992, Kinetics of the N-chlorination of 2-aminobutyric, 3-aminobutyric, 3-aminoisobutyric and 4-aminobutyric acids in aqueous solution, Int. J. Kinet., 24, 1093, 10.1002/kin.550241207

Antelo, 1995, Kinetic study of the formation of N-chloramines, Int J. Chem. Kinet., 27, 637, 10.1002/kin.550270703

Armesto, 1993, α-amino acids chlorination in aqueous media, Tetrahedron, 49, 275, 10.1016/S0040-4020(01)80525-1

Armesto, 1994, Chlorination of dipeptides by hypochlorous acid in aqueous solution, Gazz. Chim. Ital., 124, 519

Armesto, 1994, N reactivity vs O reactivity in aqueous chlorination, Int. J. Chem. Kinet., 26, 1135, 10.1002/kin.550261108

Armesto, 1994, Concerted grob fragmentation in N-halo-α-amino acid decomposition, J. Org. Chem., 59, 4659, 10.1021/jo00095a048

Armesto, 2000, First steps in the oxidation of sulfur-containing amino acids by hypohalogenation: very fast generation of intermediate sulfenyl halides and halosulfonium cations, Tetrahedron, 56, 1103, 10.1016/S0040-4020(99)01066-2

Armesto, 2001, Intracellular oxidation of dipeptides: very fast halogenation of the amino-terminal residue, J. Chem. Perkin Trans., 2, 608, 10.1039/b007208g

Arotsky, 1962, Halogen cations, Q. Rev. Chem. Soc., 16, 282, 10.1039/qr9621600282

Banker, 2001, Uracil moiety is required for toxicity of the cyanobacterial hepatotoxin cylindrospermopsin, J. Toxicol. Environ. Heallth, Part A, 62, 281, 10.1080/009841001459432

Bedner, 2006, Transformation of acetaminophen by chlorination produces the toxicants 1,4-benzoquinone and N-acetyl-p-benzoquinone imine, Environ. Sci. Technol., 40, 516, 10.1021/es0509073

Bichsel, 2000, Formation of iodo-trihalomethanes during disinfection and oxidation of iodide-containing waters, Environ. Sci. Technol., 34, 2784, 10.1021/es9914590

Blackburn, 1995, Concentrations of alkylphenols in rivers and estuaries in England and Wales, Water Res., 29, 1623, 10.1016/0043-1354(94)00340-D

Bois, 1997, Dynamic modelling of bacteria in a pilot drinking-water distribution system, Water Res., 31, 3146, 10.1016/S0043-1354(97)00178-4

Bousher, 1986, Rate of hypobromite formation in chlorinated seawater, Water Res., 20, 865, 10.1016/0043-1354(86)90174-0

Boyce, 1983, Reaction pathways of trihalomethane formation from the halogenation of dihydroxyaromatic model compounds for humic acid, Environ. Sci. Technol., 17, 202, 10.1021/es00110a005

Bruchet, 2004, Role of oxidants and disinfectants on the removal masking and generation of tastes and odours, Water Sci. Technol., 49, 297, 10.2166/wst.2004.0589

Burlingame, 1992, Cucumber flavour in Philadelphia's drinking water, J. Am. Water Works Assoc., 84, 92, 10.1002/j.1551-8833.1992.tb07416.x

Burttschell, 1959, Chlorine derivatives of phenol causing taste and odor, J. Am. Water Works Assoc., 51, 205, 10.1002/j.1551-8833.1959.tb15722.x

Cancho, 2000, Determination, synthesis and survey of iodinated trihalomethanes in water treatment processes, Water Res., 34, 3380, 10.1016/S0043-1354(00)00079-8

Canle, 1994

Carlson, 1978, Organochemical implications of water chlorination, vol. 1, 65

Carlson, 1978, Aqueous chlorination products of polynuclear aromatic hydrocarbons, vol. 2, 59

Chamberlain, 2006, Oxidation of sulfonamides, macrolides, and carbadox with free chlorine and monochloramine, Water Res., 40, 2517, 10.1016/j.watres.2006.04.039

Cherney, 2006, Monitoring the speciation of aqueous free chlorine from pH 1 to 12 with Raman spectroscopy to determine the identity of potent low-pH oxidant, Appl. Spectrosc., 60, 764, 10.1366/000370206777887062

Choppin, 1937, The oxidation of aqueous sulfide solutions by hypochlorites, J. Am. Chem. Soc., 59, 2203, 10.1021/ja01290a033

Conyers, 1997, Chloramines V: products and implications of the chlorination of lysine in municipal wastewaters, Environ. Sci. Technol., 31, 1680, 10.1021/es960534t

Cullen, 1989, Arsenic speciation in the environment, Chem. Rev., 89, 713, 10.1021/cr00094a002

Davies, 2000, Hypochlorite-induces oxidation of thiols: formation of thiyl radicals and the role of sulfenyl chlorides as intermediates, Free Rad. Res., 33, 719, 10.1080/10715760000301241

De Laat, 1981. Contribution à l’étude du mécanisme de formation des trihalométhanes: incidence de l’azote ammoniacal et des traitements de préoxydation. Ph.D. Thesis, Laboratoire de Chimie de l’Eau et de l’Environnement, Poitiers.

De Laat, 1982, Chloration de composés organiques: demande en chlore et réactivité vis à vis de la formation des trihalométhanes, Water Res., 16, 1437, 10.1016/0043-1354(82)90242-1

Deborde, 2004, Aqueous chlorination kinetics of some endocrine disruptors, Environ. Sci. Technol., 38, 5577, 10.1021/es040006e

Deborde, 2005, Kinetics of aqueous ozone-induces oxidation of some endocrine disruptors, Environ. Sci. Technol., 39, 6086, 10.1021/es0501619

Diurk, 2006, Degradation of chlorpyrifos in aqueous chlorine solutions: pathways, kinetics and modelling, Environ. Sci. Technol., 40, 546, 10.1021/es0516615

Dodd, 2004, Transformation of the antibacterial agent sulfamethoxazole in reactions with chlorine: kinetics, mechanisms, and pathways, Environ. Sci. Technol., 38, 5607, 10.1021/es035225z

Dodd, 2007, Aqueous chlorination of the antibacterial agent trimethoprim: reaction kinetics and pathways, Water Res., 41, 647, 10.1016/j.watres.2006.10.029

Dodd, 2005, Interactions of fluoroquinolone antibacterial agents with aqueous chlorine: reaction kinetics, mechanisms, and transformation pathways, Environ. Sci. Technol., 39, 7065, 10.1021/es050054e

Dodd, 2006, Kinetics and mechanistic aspects of As(III) oxidation by aqueous chlorine, chloramines and ozone: relevance to drinking water treatment, Environ. Sci. Technol., 40, 3285, 10.1021/es0524999

Doré, M., 1989. Chimie des oxydants et traitement des eaux, Edition Technique et Documentation. Lavoisier, Paris.

Drozdz, 1988, Oxidation of amino-acids and peptides in reaction with myeloperoxidase, chloride and hydrogen peroxide, Biochim. Biophys. Acta., 957, 47, 10.1016/0167-4838(88)90155-0

Edmond, 1949, The mechanism of formation of dialkylchloramines from hypochlorous acid, J. Chem. Soc., 2942, 10.1039/jr9490002942

Ellis, 1954, Studies of N-halogeno-compounds, Part VI. The kinetics of chlorination of tertiary amines. J.Chem. Soc., 1750

Farkas, 1949, The reaction between hypochlorite and bromides, J. Am. Chem. Soc., 71, 1988, 10.1021/ja01174a025

Fogelman, 1989, Non-metal redox kinetics: hypochlorite and hypochlorous acid reactions with sulfite, Inorg. Chem., 28, 986, 10.1021/ic00305a002

Folkes, 1995, Kinetics and mechanisms of hypochlorous acid reactions, Arch. Biochem. Biophys., 323, 120, 10.1006/abbi.1995.0017

Fox, 1997, Chloramines VII: chlorination of alanylphenylalanine in model solutions and in a wastewater, Environ. Sci. Technol., 31, 1979, 10.1021/es9607953

Friend, A.G., 1954. Rates of N-chlorination of amino acids. Ph.D. Thesis, Harvard University.

Fu, 2002, Generation of intramolecular and intermolecular sufenamides, sulfinamides and sulfonamides by hypochlorous acid: a potential pathway for oxidative cross-linking of low-density lipoprotein by myeloperoxidase, Biochemistry, 41, 1293, 10.1021/bi015777z

Gallard, 2002, Chlorination of phenols: kinetics and formation of chloroform, Environ. Sci. Technol., 36, 884, 10.1021/es010076a

Gallard, 2003, Rate constants of reactions of bromine with phenols in aqueous solution, Water Res., 37, 2883, 10.1016/S0043-1354(03)00132-5

Gallard, 2004, Chlorination of bisphenol a: kinetics and byproducts formation, Chemosphere, 56, 465, 10.1016/j.chemosphere.2004.03.001

Gassman, 1972, Nucleophilic aromatic substitution of anilines via aryl nitrenium ions (anilenium ions), J. Am. Chem. Soc., 94, 3884, 10.1021/ja00766a037

Gerritsen, 1990, Non- metal kinetics: hypochlorite and hypochlorous acid reactions with cyanide, Inorg. Chem., 29, 2757, 10.1021/ic00340a010

Ghanbari, 1983, Reactions of chlorine and chlorine dioxide with free fatty acids, fatty acid esters, and triglycerides, vol. 4, 167

Ghurye, 2004, As III oxidation using chemical and solid-phase oxidants, J Am. Water Works Assoc., 96, 84, 10.1002/j.1551-8833.2004.tb10536.x

Gibson, 1986, Chlorination of fatty acids during water treatment disinfection: reactivity and product identification, Environ. Technol. Lett., 7, 365, 10.1080/09593338609384423

Gottschalk, 2000

Gould, 1984, The kinetics and primary products of uracil chlorination, Water Res., 18, 205, 10.1016/0043-1354(84)90070-8

Gould, 1984, The formation of stable organic chloramines during the aqueous chlorination of cytosine and 5-methylcytosine, Water Res., 18, 991, 10.1016/0043-1354(84)90250-1

Gray, 1978, Chloramine equilibria and kinetics of disproportionation in aqueous solution, 264

Guthrie, 1986, Chlorination of acetone: a complete kinetic analysis, Can. J. Chem., 64, 1250, 10.1139/v86-208

Guthrie, 1984, Halogenation of acetone. A method for determining pKaS of ketones in aqueous solution, with an examination of the thermodynamics and kinetics of alkaline halogenation and a discussion of the best value for the rate constant for a “diffusion-controlled reaction”. Energetic requirements for a diffusion-controlled reaction involving heavy-atom bond formation, J. Am. Chem. Soc., 106, 1351, 10.1021/ja00317a030

Haberfield, 1965, The chlorination of anilines. Proof of the existence of an N-chloro intermediate, J. Am. Chem. Soc., 87, 5502, 10.1021/ja00951a052

Hand, 1983, Kinetics and mechanisms of the decomposition of dichloramine in aqueous solution, Inorg. Chem., 22, 1449, 10.1021/ic00152a007

Hao, 1991, Kinetics of manganese (II) oxidation with chlorine, J. Environ. Eng., 117, 359, 10.1061/(ASCE)0733-9372(1991)117:3(359)

Hawkins, 2003, Hypochlorite-induced oxidation of amino acids, peptides and proteins, Amino Acids, 25, 259, 10.1007/s00726-003-0016-x

Hine, J., 1962. Physical organic chemistry, second ed. Mc Graw-Hill, New York.

Hirsch, 1999, Occurrence of antibiotics in the environment, Sci. Tot. Environ., 225, 109, 10.1016/S0048-9697(98)00337-4

Ho, 2006, Differences in the chlorine reactivity of four microcystin analogues, Water Res., 40, 1200, 10.1016/j.watres.2006.01.030

Hoff, 1981, Comparison of the biocidal efficiency of alternative disinfectants, J. Am. Water Works Assoc., 73, 40, 10.1002/j.1551-8833.1981.tb04636.x

Hoigné, 1998, Chemistry of aqueous ozone and transformation of pollutants by ozonation and advances oxidation processes

Hoyano, 1973, Chlorination studies. IV. The reaction of aqueous hypochlorous acid with pyrimidine and purine bases, Biochem. Biophys. Commun., 53, 1195, 10.1016/0006-291X(73)90591-3

Hu, 2002, Products of aqueous chlorination of bisphenol A and their estrogenic activity, Environ. Sci. Technol., 36, 1980, 10.1021/es011177b

Hu, 2002, Products of aqueous chlorination of 4-nonylphenol and their estrogenic activity, Environ. Toxicol. Chem., 21, 2034, 10.1002/etc.5620211005

Hu, 2003, Products of aqueous chlorination of 17β-estradiol and their activities, Environ. Sci. Technol., 37, 5665, 10.1021/es034324+

Hu, 2006, Transformation of pyrene in aqueous chlorination in the presence and absence of bromide ion: kinetics, products and their aryl hydrocarbon receptor-mediated activities, Environ. Sci. Technol., 40, 487, 10.1021/es0516108

Huber, 2003, Oxidation of pharmaceuticals during ozonation and advanced oxidation processes, Environ. Sci. Technol., 37, 1016, 10.1021/es025896h

Isaac, R.A., 1981. Transfer of active chlorine from NH2Cl to organic nitrogenous compounds. Ph.D. Thesis, Harvard University, Cambridge.

Isaac, 1985, HOBr–NH3–Org–N reactions, vol. 5, 985

Jafvert, 1992, Reaction scheme for the chlorination of ammoniacal water, Environ. Sci. Technol., 26, 577, 10.1021/es00027a022

Jobling, 1998, Widespread sexual disruption in wild fish, Environ, Sci. Technol., 32, 2498, 10.1021/es9710870

Johnson, 1991, Non-metal redox kinetics: a reexamination of the mechanism of the reaction between hypochlorite and nitrite ions, Inorg. Chem., 30, 4845, 10.1021/ic00025a031

Jolley, 1978, vol. 1

Jolley, 1978, vol. 2

Jolley, 1980, vol. 3

Jolley, 1983, vol. 4

Jolley, 1985, vol. 5

Jonsson, 1993, Redox chemistry of substituted benzenes. The one-electron reduction potentials of methoxy-substututed benzene radical cations, J. Phys. Chem., 97, 11278, 10.1021/j100145a027

Keefe, 1997, Chloramines VI: chlorination of glycylphenylalanine in model solutions and in wastewater, Environ. Sci. Technol., 31, 1973, 10.1021/es960794a

Knocke, 1987, Using alternative oxidants to removal dissolved manganese from waters laden with organics, J. Am. Water Works Assoc., 79, 75, 10.1002/j.1551-8833.1987.tb02818.x

Kolpin, 2002, Pharmaceuticals hormones and other organic wasterwater contaminants in US streams, 1999–2000: a national reconnaissance, Environ. Sci. Technol., 36, 1202, 10.1021/es011055j

Kopperman, 1976, Aqueous chlorination of α-terpineol, Tetrahedron, 32, 1621, 10.1016/0040-4020(76)85148-4

Krasner, 2006, Occurrence of a new generation of disinfection byproducts, Environ. Sci. Technol., 40, 7175, 10.1021/es060353j

Kumar, 1987, kinetics and mechanism of general-acid-assisted oxidation of bromide by hypochlorite and hypochlorous acid, Inorg. Chem., 26, 2706, 10.1021/ic00263a030

Kumar, 1986, Atom-transfer redox kinetics: general acid-assisted oxidation of iodide by chloramines and hypochlorite, Inorg. Chem., 25, 4344, 10.1021/ic00244a012

Lahoutifard, 2003, Kinetics and mechanism of nitrite oxidation by hypochlorous acid in the aqueous phase, Chemosphere, 50, 1349, 10.1016/S0045-6535(02)00765-8

Larson, 1979, Chloroform and chlorophenol production by decarboxylation of natural acids during aqueous chlorination, Environ. Sci. Technol., 13, 325, 10.1021/es60151a014

Larson, 1994

Larsson, 1999, Ethinyl oestradiol—an undesired fish contraceptive?, Aquat. Toxicol., 45, 91, 10.1016/S0166-445X(98)00112-X

Le Chevallier, 1988, Factors promoting survival of bacteria in chlorinated water supplies, Appl. Environ. Microbiol., 54, 649, 10.1128/AEM.54.3.649-654.1988

Le Cloirec, 1985, Evolution of amino acids in water treatment plants and the effect of chlorination on amino acids, vol. 5, 821

Lee, 1962, Kinetics of chlorination of phenol-chlorophenolic tastes and odors, Int. J. Air Water Pollut., 6, 419

Legube, B., 2003. Ozonation By-products. The Handbook of Environmental Chemistry, vol. 5 (Part G), pp. 95–116.

Legube, 1980, Reactions of ozone with aromatics in dilute aqueous solution : reactivity and biodegradability of oxidation products, Prog. Water Technol., 12, 553

Leupin, 2005, Arsenic removal from Bangladesh tube well water with filter columns containing zerovalent iron filings and sand, Environ. Sci. Technol., 39, 8032, 10.1021/es050205d

Lin, 1984, Susceptibility of environmentally important heterocycles to chemical disinfection: reactions with aqueous chlorine, chlorine dioxide, and chloramine, Environ. Sci. Technol., 18, 743, 10.1021/es00128a005

Liukkonen, 1983, Product distribution and relative rates of reaction of aqueous chlorine and chlorine dioxide with polynuclear aromatic hydrocarbons, vol. 4, 151

Lopez, 1994, Oxidation of sulfur-containing S-triazines during groundwater hypochlorination, Water Sci. Technol., 30, 53, 10.2166/wst.1994.0304

Magara, 1994, Degradation of pesticides by chlorination during water purification, Water Sci. Technol., 30, 119, 10.2166/wst.1994.0323

Margerum, 1978, Chlorination and the formation of N-chloro-compounds in water treatment, 278

Masuda, 2001, Chlorination of guanosine nucleosides by hypochlorous acid and myeloperoxidase of activated human neutrophils, J. Biol. Chem., 276, 40486, 10.1074/jbc.M102700200

Mathews, 1947, Iron and manganese removal by free residual chlorination, J. Am. Water Works Assoc., 39, 680, 10.1002/j.1551-8833.1947.tb20577.x

Mauger, 1946, Acid catalysis in formation of chloramides from hypochlorous acid, J. Chem. Soc., 71, 10.1039/jr9460000071

Mitch, 2003, N-nitrosodimethylamine (NDMA) as a drinking water contaminant: a review, Environ. Eng. Sci., 20, 389, 10.1089/109287503768335896

Moriyama, 2004, Identification and behaviour of reaction products formed by chlorination of ethynylestradiol, Chemosphere, 55, 839, 10.1016/j.chemosphere.2003.11.045

Morris, 1966, The acid ionization constant of HOCl from 5 to 35°, J. Phys. Chem., 70, 3798, 10.1021/j100884a007

Morris, 1967, Kinetics of reactions between aqueous chlorine and nitrogen compounds, 23

Morris, 1978, The chemistry of aqueous chlorine in relation to water chlorination, vol. 1, 21

Morris, 1986, Aqueous chlorine in treatment of water supplies, 33

Morris, 1983, A critical review of kinetic and thermodynamic constants for aqueous chlorine-ammonia system, vol. 4, 49

Nagy, 1988, Non-metal kinetics: oxidation of iodide by hypochlorous acid and nitrogen trichloride measured by the pulsed-accelerated-flow method, Inorg. Chem., 27, 2773, 10.1021/ic00289a007

Neta, 1988, Rate constants for reactions of inorganic radicals in aqueous solution, J. Phys. Chem. Ref. Data, 17, 1027, 10.1063/1.555808

Nweke, 1989, Stable N-chloramines and other products of the chlorination of isoleucine in model solutions and in a wastewater, Environ. Sci. Technol., 23, 989, 10.1021/es00066a010

Oliveira, 2006, Mutagenic compounds generated from the chlorination of disperse azo-dyes and their presence in drinking water, Environ. Sci. Technol., 40, 6682, 10.1021/es061020p

Onstad, 2005, Evaluation of the stability and analysis of halogenated furanones in disinfected drinking waters, Anal. Chim. Acta, 534, 281, 10.1016/j.aca.2004.11.046

Oyler, 1983, Chlorine disinfection chemistry of aromatic compounds. Polynuclear aromatic hydrocarbons: rates, products and mechanisms, Environ. Sci. Technol., 17, 334, 10.1021/es00112a006

Ozekin, 1996, Modeling the decomposition of disinfecting residuals of chloramine, 115

Pattison, 2001, Absolute rate constants for the reaction of hypochlorous acid with protein side chains and peptide bonds, Chem. Res. Toxicol., 14, 1453, 10.1021/tx0155451

Patton, 1972, Chlorination studies. I. The reaction of aqueous hypochlorous acid with cytosine, Biochem. Biophys. Res. Commun., 48, 880, 10.1016/0006-291X(72)90690-0

Pereira, 1973, Chlorination studies II. The reaction of aqueous hypochlorous acid with α-amino acids and dipeptides, Biochim. Biophys. Acta, 313, 170, 10.1016/0304-4165(73)90198-0

Perrin, 1981

Pinkston, 2004, Transformation of aromatic ether- and amine-containing pharmaceuticals during chlorine disinfection, Environ. Sci. Technol., 38, 4019, 10.1021/es035368l

Plewa, 2004, Chemical and biological characterization of newly discovered iodoacid drinking water disinfection byproducts, Environ. Sci. Technol., 38, 4713, 10.1021/es049971v

Poncin, 1984, Kinetic studies on the chlorination of methylamine by sodium hypochlorite in dilute aqueous medium, Environ. Technol. Lett., 5, 263, 10.1080/09593338409384275

Pouvreau, 1984, Elimination spécifique du fer et du manganese, J. Franç. Hydrol., 15, 169, 10.1051/water/19841502169

Prütz, 1996, Hypochlorous acids interactions with thiols, nucleotides, DNA and other biological substrates, Arch. Biochem. Biophys., 332, 110, 10.1006/abbi.1996.0322

Prütz, 1998, Reactions of hypochlorous acid with biological substrates are activated catalytically by tertiary amines, Arch. Biochem. Biophys., 357, 265, 10.1006/abbi.1998.0822

Prütz, 1998, Interaction of hypochlorous acid with pyrimidine nucleotides, and secondary reactions of chlorinated pyrimidines with GSH, NADH and other substrates, Arch. Biochem. Biophys., 349, 183, 10.1006/abbi.1997.0440

Prütz, 1999, Consecutive halogen transfer between various functional groups induced by reaction of hypohalous acids: NADH oxidation by halogenated amide groups, Arch. Biochem. Biophys., 371, 107, 10.1006/abbi.1999.1377

Qiang, 2004, Determination of monochloramine formation rate constants with stopped-flow spectrometry, Environ. Sci. Technol., 38, 1435, 10.1021/es0347484

Rebenne, 1996, Aqueous chlorination kinetics and mechanism of substituted dihydrobenzenes, Environ. Sci. Technol., 30, 2235, 10.1021/es950607t

Reinhard, 1980, Kinetics of chlorination of p-xylene in aqueous solution, vol. 3, 209

Reynolds, 1988, Isolation and identification of reaction products arising from the chlorination of cytosine in aqueous solution, Environ. Sci. Technol., 22, 1425, 10.1021/es00177a006

Richardson, 2005, New disinfection by-product issues: emerging DBPs and alternative routes of exposure, Global NEST J., 7, 43

Richardson, 2003, Tribromopyrrole, brominated acids and other disinfection byproducts produced by disinfection of drinking water rich in bromide, Environ. Sci. Technol., 37, 3782, 10.1021/es030339w

Roberts, 1968

Rockwell, 1978, Aqueous chlorination of some phenolic acids, vol. 2, 67

Rodriguez, 2007, Kinetics of the oxidation of cylindrospermopsin and anatoxin-a with chlorine, monochloramine and permanganate, Water Res., 41, 2048, 10.1016/j.watres.2007.01.033

Rule, 2005, Formation of chloroform and chlorinated organics by free-chlorine-mediated oxidation of triclosan, Environ. Sci. Technol., 39, 3176, 10.1021/es048943+

Samples, W.R., 1959. A study on the chlorination of urea. Ph.D. Thesis, Harvard University.

Savige, 1966, Oxidation of disulphides with special reference to cystine, vol. 2, 367

Sawyer, 1978

Serjeant, 1979

Silverstein, 1974, The chloroperoxidase-catalysed oxidation of thiols and disulfides to sulfenyl chlorides, Biochemistry, 13, 5069, 10.1021/bi00722a001

Simmons, 2002, Development of a research strategy for integrated technology-based toxicological and chemical evaluation of complex mixtures of drinking water disinfection byproducts, Environ. Health Perspect., 110, 1013, 10.1289/ehp.02110s61013

Sorasuchart, 1999, Drug release from spray layered and coated drug-containing beads: effects of pH and comparison of different dissolution methods, Drug Dev. Ind. Pharm., 25, 1093, 10.1081/DDC-100102274

Stanbro, 1979, Kinetics and mechanism of the decomposition of N-chloroalanine in aqueous solution, Environ. Sci. Technol., 13, 446, 10.1021/es60152a002

Stumm, 1970

Swain, 1953, Quantitative correlation of relative rates. Comparison of hydroxide ion with other nucleophilic reagents toward alkyl halides, esters, epoxides and acyl halides, J. Am. Chem. Soc., 75, 141, 10.1021/ja01097a041

Tachikawa, 2002, Effects of isocyanuric acid on the monochlorodimedone chlorinating rates with free chlorine and ammonia chloramine in water, Water Res., 36, 2547, 10.1016/S0043-1354(01)00482-1

Ternes, 1998, Occurrence of drugs in German sewage treatment plants and rivers, Water Res., 32, 3245, 10.1016/S0043-1354(98)00099-2

Thomm, 1969, N-chlorination of secondary amides II. Effects of substituents on rates of N-chlorination, Can. J. Chem., 47, 3289, 10.1139/v69-548

Tratnyek, 1994, Kinetics of reactions of chlorine dioxide (OClO) in water-II. Quantitative structure–activity relationships for phenolic compounds, Water Res., 28, 57, 10.1016/0043-1354(94)90119-8

2000

Vikesland, 2001, Monochloramine decay in model and distribution system waters, Water Res., 35, 1766, 10.1016/S0043-1354(00)00406-1

von Gunten, 2003, Ozonation of drinking water: Part I. Oxidation kinetics and product formation, Water Res., 37, 1443, 10.1016/S0043-1354(02)00457-8

von Gunten, 2006, Removal of PPCP during drinking water treatment

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

Wang, 1994, Kinetics of reversible chlorine hydrolysis: temperature dependence and general-acid/base-assisted mechanisms, Inorg. Chem., 33, 1050, 10.1021/ic00084a014

Weber, E.J., Kenneke, J.F. SPARC (〈http://www.epa.gov/athens/research/projects/sparc〉) US EPA. National Exposure Research Laboratory, Athens, GA.

Weil, 1949, Kinetic studies on the chloramines. I. The rates of formation of monochloramine, N-chlormethylamine and N-chlordimethylamine, J. Am. Chem. Soc., 71, 1664, 10.1021/ja01173a033

White, 1986

Winterbourn, 1997, Characterization of the oxidation products of the reaction between reduced gluthatione and hypochlorous acid, Biochem. J., 326, 87, 10.1042/bj3260087

Wolfe, 1984, Inorganic chloramines as water disinfectants: a review, J. Am. Water Works Assoc., 76, 74, 10.1002/j.1551-8833.1984.tb05337.x

Wong, 1984, Chlorination-filtration for iron and manganese removal, J. Am. Water Works Assoc., 76, 76, 10.1002/j.1551-8833.1984.tb05265.x

Wu, 2003, Abiotic transformation of chlorpyrifos to chlorpyrifos oxon in chlorinated water, Environ. Toxicol. Chem., 22, 261, 10.1002/etc.5620220204

Yamamoto, 2002, Chlorination of bisphenol a in aqueous media: formation of chlorinated bisphenol A congeners and degradation to chlorinated phenolic compounds, Chemosphere, 46, 1215, 10.1016/S0045-6535(01)00198-9

Ying, 2002, Occurrence and fate of hormone steroids in the environment, Environ. Int., 28, 545, 10.1016/S0160-4120(02)00075-2

Yoon, 1993, Distribution of aqueous chlorine with nitrogenous compounds: chlorine transfer from organic chloramines to ammonia, Environ. Sci. Technol., 27, 403, 10.1021/es00039a022

Young, 1994, Byproducts of the aqueous chlorination of purines and pyrimidines, Environ. Sci. Technol., 28, 1755, 10.1021/es00058a029

Zimmermann, 1957, Equilibria and spectra of aqueous chlorine solutions, J. Am. Chem. Soc., 79, 2063, 10.1021/ja01566a011