Aqueous chlorination of the antibacterial agent trimethoprim: Reaction kinetics and pathways

Water Research

Volumn 41, Issue 3, 2007, Pages 647-655

  Dodd, Michael C ^a   Huang, Ching Hua ^a  

^a Georgia Institute of Technology   (United States)

Author keywords

Antibiotic; Chlorination; Kinetics; Methoxybenzene; Pharmaceutical; Pyrimidine

Indexed keywords

CHLORINATION; PH EFFECTS; POTABLE WATER; REACTION KINETICS; SURFACE WATERS; WASTEWATER;

METHOXYBENZENE; PYRIMIDINE; REAGENT WATER SYSTEMS;

ANTIBIOTICS;

2,4 DIAMINO 5 METHYLPYRIMIDINE; 3,4,5 TRIMETHOXYTOLUENE; BENZYL DERIVATIVE; CHLORINE; DRINKING WATER; PYRIMIDINE DERIVATIVE; SURFACE WATER; TOLUENE DERIVATIVE; TRIMETHOPRIM; UNCLASSIFIED DRUG;

ANTIBIOTICS; CHLORINATION; PH EFFECTS; POTABLE WATER; REACTION KINETICS; SURFACE WATERS; WASTEWATER;

ANTIBIOTICS; CHLORINATION; PH; REACTION KINETICS; SPECIATION (CHEMISTRY); WASTE TREATMENT; WASTEWATER;

ARTICLE; CHEMICAL REACTION KINETICS; CHLORINATION; HALOGENATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PH; PRIORITY JOURNAL; WASTE WATER; WATER SUPPLY;

EID: 33846084123     PISSN: 00431354     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.watres.2006.10.029     Document Type: Article

References (30)

1. Adams C., Wang Y., Loftin K., and Meyer M. Removal of antibiotics from surface and distilled water in conventional water treatment processes. J. Environ. Eng. 128 (2002) 253-260
2. APHA. Standard Methods for the Examination of Water and Wastewater (1998), APHA, AWWA, WPCF, Washington, DC
3. Brain R.A., Johnson D.J., Richards S.M., Hanson M.L., Sanderson H., Lam M.W., Young C., Mabury S.A., Sibley P.K., and Solomon K.R. Microcosm evaluation of the effects of an eight pharmaceutical mixture to the aquatic macrophytes Lemna gibba and Myriophyllum sibiricum. Aquat. Toxicol. 70 (2004) 23-40
4. Cherney D.P., Duirk S.E., Tarr J.C., and Collette T.W. Monitoring the speciation of aqueous free chlorine from pH 1 to 12 with Raman spectroscopy to determine the identity of the potent low-pH oxidant. Appl. Spectrosc. 60 (2006) 764-772
5. Dodd M.C., and Huang C.-H. Transformation of the antibacterial agent sulfamethoxazole in reactions with chlorine: kinetics, mechanisms, and pathways. Environ. Sci. Technol. 38 (2004) 5607-5615
6. Dodd M.C., Buffle M.-O., and von Gunten U. Oxidation of antibacterial molecules by aqueous ozone: Moiety-specific reaction kinetics and application to ozone-based wastewater treatment. Environ. Sci. Technol. 40 (2006) 1969-1977
7. Eliopoulos G.M., and Moellering R.C.J. In: Lorian V. (Ed). Antibiotics in Laboratory Medicine (1996), Waverly and Wilkins, Baltimore, MD 331-396
8. Escher B.I., Bramaz N., Eggen R.I.L., and Richter M. In vitro assessment of modes of toxic action of pharmaceuticals in aquatic life. Environ. Sci. Technol. 39 (2005) 3090-3100
9. Gallard H., and von Gunten U. Chlorination of phenols: kinetics and formation of chloroform. Environ. Sci. Technol. 36 (2002) 884-890
10. Gerritsen C.M., and Margerum D.W. Non-metal redox kinetics: hypochlorite and hypochlorous acid reactions with cyanide. Inorg. Chem. 29 (1990) 2757-2762
11. Glassmeyer S.T., Furlong E.T., Kolpin D.W., Cahill J.D., Zaugg S.D., Werner S.L., Meyer M.T., and Kryak D.D. Transport of chemical and microbial compounds from known wastewater discharges: Potential for use as indicators of human fecal contamination. Environ. Sci. Technol. 39 (2005) 5157-5169
12. Göbel A., Thomsen A., McArdell C.S., Joss A., and Giger W. Occurrence and sorption behavior of sulfonamides, macrolides, and trimethoprim in activated sludge treatment. Environ. Sci. Technol. 39 (2005) 3981-3989
13. Hirsch R., Ternes T.A., Haberer K., and Kratz K.-L. Occurrence of antibiotics in the environment. Sci. Total Environ. 225 (1999) 109-118
14. Junker T., Alexy R., Knacker T., and Kummerer K. Biodegradability of C-14-labeled antibiotics in a modified laboratory scale sewage treatment plant at environmentally relevant concentrations. Environ. Sci. Technol. 40 (2006) 318-324
15. Kolpin D.W., Furlong E.T., Meyer M.T., Thurman E.M., Zaugg S.D., Barber L.B., and Buxton H.T. Pharmaceuticals, hormones, and other organic wastewater contaminants in US Streams, 1999-2000: a national reconnaissance. Environ. Sci. Technol. 36 (2002) 1202-1211
16. Lai W.G., Zahid N., and Uetrecht J.P. Metabolism of trimethoprim to a reactive iminoquinone methide by activated human neutrophils and hepatic microsomes. J. Pharmacol. Exp. Ther. 291 (1999) 292-299
17. Lindberg R.H., Wennberg P., Johansson M.I., Tysklind M., and Andersson B.A.V. Screening of human antibiotic substances and determination of weekly mass flows in five sewage treatment plants in Sweden. Environ. Sci. Technol. 39 (2005) 3421-3429
18. Morris J.C. Acid ionization constant of HOCl from 5 to 35°. J. Phys. Chem. 70 (1966) 3798-3805
19. Nicolle L.E. In: Lorian V. (Ed). Antibiotics in Laboratory Medicine (1996), Waverly and Wilkins, Baltimore, MD 793-812
20. Patton W., Pereira W., Duffield A.M., Bacon V., Halpern B., Hoyano Y., and Lederber J. Chlorination studies.1. Reaction of aqueous hypochlorous acid with cytosine. Biochem. Biophys. Res. Commun. 48 (1972) 880-884
21. Pinkston K.E., and Sedlak D.L. Transformation of aromatic ether- and amine-containing pharmaceuticals during chlorine disinfection. Environ. Sci. Technol. 38 (2004) 4019-4025
22. Qiang Z.M., and Adams C. Potentiometric determination of acid dissociation constants (pK(a)) for human and veterinary antibiotics. Water Res. 38 (2004) 2874-2890
23. Rebenne L.M., Gonzalez A.C., and Olson T.M. Aqueous chlorination kinetics and mechanism of substituted dihydroxybenzenes. Environ. Sci. Technol. 30 (1996) 2235-2242
24. Renew J.E., and Huang C.-H. Simultaneous determination of fluoroquinolone, sulfonamide, and trimethoprim antibiotics in wastewater using tandem solid phase extraction and liquid chromatography-electrospray mass spectrometry. J. Chromatogr. A 1042 (2004) 113-121
25. Reynolds G.L., Filaderli H.A., McIntyre A.E., Graham N.J.D., and Perry R. Isolation and identification of reaction products arising from the chlorination of cytosine in aqueous solution. Environ. Sci. Technol. 22 (1988) 1425-1429
26. Roth B., and Strelitz J.Z. The protonation of 2,4-diaminopyrimidines. I. Dissociation constants and substituent effects. J. Org. Chem. 34 (1969) 821-836
27. Rule K.L., Ebbett V.R., and Vikesland P.J. Formation of chloroform and chlorinated organics by free-chlorine-mediated oxidation of triclosan. Environ. Sci. Technol. 39 (2005) 3176-3185
28. Walsh C. Antibiotics: Actions, Origins, Resistance (2003), ASM Press, Washington, DC
29. Wang T.X., and Margerum D.W. Kinetics of reversible chlorine hydrolysis-temperature-dependence and general acid base-assisted mechanisms. Inorg. Chem. 33 (1994) 1050-1055
30. Westerhoff P., Yoon Y., Snyder S., and Wert E. Fate of endocrine-disruptor, pharmaceutical, and personal care product chemicals during simulated drinking water treatment processes. Environ. Sci. Technol. 39 (2005) 6649-6663