Halogenation of bisphenol-A, triclosan, and phenols in chlorinated waters containing iodide

Environmental Science and Technology

Volumn 47, Issue 13, 2013, Pages 6764-6772

  Vikesland, Peter J ^a   Fiss, E Matthew ^a   Wigginton, Krista R ^a   McNeill, Kristopher ^b   Arnold, William A ^b  

^a Virginia Polytechnic Institute and State University   (United States)

^b UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 ,4-DICHLOROPHENOL; CHLORINATED WATERS; DAUGHTER PRODUCTS; MEDIATED REACTIONS; PHENOLIC COMPOUNDS; SECOND-ORDER RATE CONSTANTS; TOXIC BY-PRODUCTS; TRANSFORMATION KINETICS;

BYPRODUCTS; CHLORINATION; CHLORINE; IODINE; OXIDANTS; PHENOLS; RATE CONSTANTS;

CHLORINE COMPOUNDS;

2,4 DICHLOROPHENOL; 4 BROMOPHENOL; 4 CHLOROPHENOL; 4 IODOPHENOL; 4,4' ISOPROPYLIDENEDIPHENOL; CHLORINE; IODIDE; IODINE; OXIDIZING AGENT; PHENOL; PHENOL DERIVATIVE; TRICLOSAN; UNCLASSIFIED DRUG; WATER;

ANTIBIOTICS; CONCENTRATION (COMPOSITION); DISINFECTION; HALOGENATED HYDROCARBON; IODINE; OXIDANT; OXIDATION; PH; PHENOL; TOXICITY;

ARTICLE; BATCH REACTOR; CHLORINATION; COLORIMETRY; HALOGENATION; MASS FRAGMENTOGRAPHY; PH; SUBSTITUTION REACTION; WATER QUALITY;

BENZHYDRYL COMPOUNDS; CHLORINE; CHLOROPHENOLS; HALOGENATION; IODIDES; MODELS, CHEMICAL; PHENOLS; TRICLOSAN; WATER POLLUTANTS, CHEMICAL;

EID: 84880123299     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es304927j     Document Type: Article

References (60)

1. Onodera, S.; Ogawa, M.; Suzuki, S. Chemical changes of organic compounds in chlorinated water. XIII. Gas chromatographic-mass spectrometric studies of the reactions of Irgasan dp 300 [5-chloro-2-(2,4-dichlorophenoxy)phenol] with chlorine in dilute aqueous solutions J. Chromatogr. 1987, 392, 267-275
2. Haderlein, S. B.; Schwarzenbach, R. P. Adsorption of substituted nitrobenzenes and nitrophenols to mineral surfaces Environ. Sci. Technol. 1993, 27 (2) 316-326
3. Gallard, H.; Von Gunten, U. Chlorination of phenols: Kinetics and formation of chloroform Environ. Sci. Technol. 2002, 36 (5) 884-890
4. Bichsel, Y.; von Gunten, U. Formation of iodo-trihalomethanes during disinfection and oxidation of iodide containing waters Environ. Sci. Technol. 2000, 34 (13) 2784-2791
5. Deborde, M.; von Gunten, U. Reactions of chlorine with inorganic and organic compounds during water treatment-Kinetics and mechanisms: A critical review Water Res. 2008, 42 (1-2) 13-51
6. Rule, K. L.; Ebbett, V. R.; Vikesland, P. J. Formation of chloroform and chlorinated organics by free-chlorine-mediated oxidation of triclosan Environ. Sci. Technol. 2005, 39, 3176-3185
7. Gallard, H.; Leclercq, A.; Croue, J. P. Chlorination of bisphenol a: Kinetics and by-products formation Chemosphere 2004, 56 (5) 465-473
8. Yamamoto, T.; Yasuhara, A. Chlorination of bisphenol a in aqueous media: Formation of chlorinated bisphenol a congeners and degradation to chlorinated phenolic compounds Chemosphere 2002, 46 (8) 1215-1223
9. Canosa, P.; Morales, S.; Rodriguez, I.; Rubi, E.; Cela, R.; Gomez, M. Aquatic degradation of triclosan and formation of toxic chlorophenols in presence of low concentrations of free chlorine Anal. Bioanal. Chem. 2005, 383 (7-8) 1119-1126
10. Fiss, E. M.; Rule, K. L.; Vikesland, P. J. Formation of chloroform and other chlorinated byproducts by chlorination of triclosan-containing antibacterial products Environ. Sci. Technol. 2007, 41 (7) 2387-2394
11. 2) as active chlorinating agents in reaction of dimethenamid with aqueous free chlorine Environ. Sci. Technol. 2010, 44 (9) 3357-3362
12. Moran, J. E.; Oktay, S. D.; Santschi, P. H. Sources of iodine and iodine 129 in rivers. Water Resour. Res. 2002, 38, (8).
13. Bichsel, Y.; von Gunten, U. Oxidation of iodide and hypoiodous acid in the disinfection of natural waters Environ. Sci. Technol. 1999, 33 (22) 4040-4045
14. Hua, G. H.; Reckhow, D. A.; Kim, J. Effect of bromide and iodide ions on the formation and speciation of disinfection byproducts during chlorination Environ. Sci. Technol. 2006, 40 (9) 3050-3056
15. Nagy, J. C.; Kumar, K.; Margerum, D. W. Non-metal redox kinetics-Oxidation of iodide by hypochlorous acid and by nitrogen trichloride measured by the pulsed-accelerated-flow method Inorg. Chem. 1988, 27 (16) 2773-2780
16. Lengyel, I.; Li, J.; Kustin, K.; Epstein, I. R. Rate constants for reactions between iodine- and chlorine-containing species: A detailed mechanism of the chlorine dioxide/chlorite-iodide reaction J. Am. Chem. Soc. 1996, 118 (15) 3708-3719
17. Nagy, K.; Kortvelyesi, T.; Nagypal, I. Iodine hydrolysis equilibrium J. Solution Chem. 2003, 32 (5) 385-393
18. Kazantseva, N. N.; Ernepesova, A.; Khodjamamedov, A.; Geldyev, O. A.; Krumgalz, B. S. Spectrophotometric analysis of iodide oxidation by chlorine in highly mineralized solutions Anal. Chim. Acta 2002, 456 (1) 105-119
19. Gottardi, W. Iodine and disinfection: Theoretical study on mode of action, efficiency, stability, and analytical aspects in the aqueous system Arch. Pharm. 1999, 332 (5) 151-157
20. Schmitz, G. Inorganic reactions of iodine(+1) in acidic solutions Int. J. Chem. Kinetics 2004, 36 (9) 480-493
21. Lengyel, I.; Epstein, I. R.; Kustin, K. Kinetics of iodine hydrolysis Inorg. Chem. 1993, 32 (25) 5880-5882
22. Plewa, M. J.; Wagner, E. D.; Richardson, S. D.; Thruston, A. D.; Woo, Y. T.; McKague, A. B. Chemical and biological characterization of newly discovered iodoacid drinking water disinfection byproducts Environ. Sci. Technol. 2004, 38 (18) 4713-4722
23. Cancho, B.; Ventura, F.; Galceran, M.; Diaz, A.; Ricart, S. Determination, synthesis and survey of iodinated trihalomethanes in water treatment processes Water Res. 2000, 34 (13) 3380-3390
24. Hua, G. H.; Reckhow, D. A. Comparison of disinfection byproduct formation from chlorine and alternative disinfectants Water Res. 2007, 41 (8) 1667-1678
25. Lee, Y.; Von Gunten, U. Transformation of 17 alpha-ethinylestradiol during water chlorination: Effects of bromide on kinetics, products, and transformation pathways Environ. Sci. Technol. 2009, 43 (2) 480-487
26. Bichsel, Y. Ph.D. Dissertation, Behavior of iodine species in oxidative processes during drinking water treatment. Swiss Federal Institute of Technology Zurich, Zurich, 2000.
27. Truesdale, V. W.; Luther, G. W.; Greenwood, J. E. The kinetics of iodine disproportionation: A system of parallel second-order reactions sustained by a multi-species pre-equilibrium Phys. Chem. Chem. Phys. 2003, 5 (16) 3428-3435
28. Bichsel, Y.; von Gunten, U. Hypoiodous acid: Kinetics of the buffer-catalyzed disproportionation Water Res. 2000, 34 (12) 3197-3203
29. Criquet, J.; Allard, S.; Salhi, E.; Joll, C. A.; Heitz, A.; von Gunten, U. Iodate and iodo-trihalomethane formation during chlorination of iodide-containing waters: Role of bromide Environ. Sci. Technol. 2012, 46 (13) 7350-7357
30. Aiello, A. E.; Marshall, B.; Levy, S. B.; Della-Latta, P.; Lin, S. X.; Larson, E. Antibacterial cleaning products and drug resistance Emerg. Infect. Dis. 2005, 11 (10) 1565-1570
31. Singer, H.; Muller, S.; Tixier, C.; Pillonel, L. Triclosan: Occurence and fate of a widely used biocide in the aquatic environment: Field measurements in wastewater treatment plants, surface waters, and lake sediments Environ. Sci. Technol. 2002, 36 (23) 4998-5004
32. Federle, T. W.; Kaiser, S. K.; Nuck, B. A. Fate and effects of triclosan in activated sludge Environ. Toxicol. Chem. 2002, 21 (7) 1330-1337
33. Lindstrom, A.; Buerge, I. J.; Poiger, T.; Bergqvist, P.-A.; Muller, M. D.; Buser, H.-R. Occurrence and environmental behavior of the bactericide triclosan and its methyl derivative in surface waters and in wastewater Environ. Sci. Technol. 2002, 36 (11) 2322-2329
34. Buth, J. M.; Grandbois, M.; Vikesland, P. J.; McNeill, K.; Arnold, W. A. Aquatic photochemistry of chlorinated triclosan derivatives: Potential source of polychlorodibenzo-p-dioxins Environ. Toxicol. Chem. 2009, 28 (12) 2555-2563
35. Buth, J. M.; Ross, M. R.; McNeill, K.; Arnold, W. A. Removal and formation of chlorinated triclosan derivatives in wastewater treatment plants using chlorine and UV disinfection Chemosphere 2011, 84 (9) 1238-1243
36. Buth, J. M.; Steen, P. O.; Sueper, C.; Blumentritt, D.; Vikesland, P. J.; Arnold, W. A.; McNeill, K. Dioxin photoproducts of triclosan and its chlorinated derivatives in sediment cores Environ. Sci. Technol. 2010, 44 (12) 4545-4551
37. Venkatesan, A. K.; Pycke, B. F. G.; Barber, L. B.; Lee, K. E.; Halden, R. U. Occurrence of triclosan, triclocarban, and its lesser chlorinated congeners in Minnesota freshwater sediments collected near wastewater treatment plants J. Hazard. Mater. 2012, 229, 29-35
38. Ash, M.; Ash, I. Handbook of Plastic and Rubber Chemical Additives; Synapse Information Resources, Inc.: Hampshire, UK, 2004.
39. U.S. EPA. Bisphenol-a Action Plan. http://www.epa.gov/oppt/ existingchemicals/pubs/actionplans/bpa-action-plan.pdf (Accessed October 24, 2012).
40. Kolpin, D. W.; Furlong, E. T.; Meyer, M. T.; Thurman, E. M.; Zaugg, S. D.; Barber, L. B.; Buxton, H. T. Pharmaceuticals, hormones, and other organic wastewater contaminants in U.S. Streams, 1999-2000: A national reconnaissance Environ. Sci. Technol. 2002, 36 (6) 1202-1211
41. Geens, T.; Aerts, D.; Berthot, C.; Bourguignon, J. P.; Goeyens, L.; Lecomte, P.; Maghuin-Rogister, G.; Pironnet, A. M.; Pussemier, L.; Scippo, M. L.; Van Loco, J.; Covaci, A. A review of dietary and non-dietary exposure to bisphenol-a Food Chem. Toxicol. 2012, 50 (10) 3725-3740
42. Kanetoshi, A.; Ogawa, H.; Katsura, E.; Kaneshima, H. Chlorination of Irgasan dp300 and formation of dioxins from its chlorinated derivatives J. Chromatogr. 1987, 389, 139-153
43. Buffle, M. O.; Schumacher, J.; Salhi, E.; Jekel, M.; von Gunten, U. Measurement of the initial phase of ozone decomposition in water and wastewater by means of a continuous quench-flow system: Application to disinfection and pharmaceutical oxidation Water Res. 2006, 40 (9) 1884-1894
44. Standard Methods for the Examination of Water and Wastewater, 18 th ed.; APHA/AWWA/WEF: Washington, DC, 1992.
45. Jones, D. B.; Saglam, A.; Song, H. C.; Karanfil, T. The impact of bromide/iodide concentration and ratio on iodinated trihalomethane formation and speciation Water Res. 2012, 46 (1) 11-20
46. Greyshock, A. E.; Vikesland, P. J. Triclosan reactivity in chloraminated waters Environ. Sci. Technol. 2006, 40, 2615-2622
47. Arnold, W. A.; Roberts, A. L. Pathways and kinetics of chlorinated ethylene and chlorinated acetylene reaction with Fe(0) particles Environ. Sci. Technol. 2000, 34 (9) 1794-1805
48. Guo, G. M.; Chen, X. D. Halogenating reaction activity of aromatic organic compounds during disinfection of drinking water J. Hazard. Mater. 2009, 163 (2-3) 1207-1212
49. Lee, Y.; Yoon, J.; Von Gunten, U. Kinetics of the oxidation of phenols and phenolic endocrine disruptors during water treatment with ferrate (Fe(VI)) Environ. Sci. Technol. 2005, 39 (22) 8978-8984
50. Acero, J. L.; Piriou, P.; von Gunten, U. Kinetics and mechanisms of formation of bromophenols during drinking water chlorination: Assessment of taste and odor development Water Res. 2005, 39 (13) 2979-2993
51. Gallard, H.; Pellizzari, F.; Croue, J. P.; Legube, B. Rate constants of reactions of bromine with phenols in aqueous solution Water Res. 2003, 37 (12) 2883-2892
52. Tee, O. S.; Paventi, M.; Bennett, J. M. Kinetics and mechanism of the bromination of phenols and phenoxide ions in aqueous solution-diffusion- controlled rates J. Am. Chem. Soc. 1989, 111 (6) 2233-2240
53. Schwarzenbach, R. P.; Gschwend, P. M.; Imboden, D. M. Environmental Organic Chemistry, 2 nd ed.; John Wiley & Sons: Hoboken, NJ, 2003.
54. Staples, C. A.; Dorn, P. B.; Klecka, G. M.; O'Block, S. T.; Branson, D. R.; Harris, L. R. Bisphenol a concentrations in receiving waters near us manufacturing and processing facilities Chemosphere 2000, 40 (5) 521-525
55. Rebenne, L. M.; Gonzalez, A. C.; Olson, T. M. Aqueous chlorination kinetics and mechanism of substituted dihydroxybenzenes Environ. Sci. Technol. 1996, 30 (7) 2235-2242
56. Deborde, M.; Rabouan, S.; Gallard, H.; Legube, B. Aqueous chlorination kinetics of some endocrine disruptors Environ. Sci. Technol. 2004, 38 (21) 5577-5583
57. 2O, and HOCl toward aromatic ethers Environ. Sci. Technol. 2012, 46 (4) 2141-2147
58. Cherney, D. P.; Duirk, S. E.; Tarr, J. C.; 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. 2006, 60 (7) 764-772
59. Carroll, F. A. Perspectives on Structure and Mechanism in Organic Chemistry; Brooks/Cole Publishing Company: Pacific Grove, CA, 1998.
60. Hu, J. Y.; Aizawa, T.; Ookubo, S. Products of aqueous chlorination of bisphenol a and their estrogenic activity Environ. Sci. Technol. 2002, 36 (9) 1980-1987