Free radical chemistry of disinfection byproducts. 2. Rate constants and degradation mechanisms of trichloronitromethane (chloropicrin)

Environmental Science and Technology

Volumn 41, Issue 3, 2007, Pages 863-869

  Cole, S Kirkham ^a   Cooper, William J ^b   Fox, Robert V ^c   Gardinali, Piero R ^d   Mezyk, Stephen P ^e   Mincher, Bruce J ^c   O'Shea, Kevin E ^d  

^a Old Dominion University   (United States)

^b University of California at Irvine   (United States)

^c IDAHO NATIONAL LABORATORY   (United States)

^d FLORIDA INTERNATIONAL UNIVERSITY   (United States)

^e CALIFORNIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KINETIC COMPUTER MODEL; TRANSIENT ABSORPTION SPECTROSCOPY;

DEGRADATION; DISINFECTION; MATHEMATICAL MODELS; OXIDATION; RADIOLYSIS; RATE CONSTANTS;

METHANE;

CHLOROPICRIN; FREE RADICAL;

DEGRADATION; DISINFECTION; MATHEMATICAL MODELS; METHANE; OXIDATION; RADIOLYSIS; RATE CONSTANTS;

CHLORIDE; COBALT ISOTOPE; COMPUTER SIMULATION; DEGRADATION; DISINFECTION; FREE RADICAL; GAMMA RAY RADIATION; HYDROXYL RADICAL; NITRATE; ORGANIC COMPOUND; PESTICIDE; REACTION KINETICS; REDOX CONDITIONS;

ABSORPTION SPECTROSCOPY; ARTICLE; CHEMICAL REACTION KINETICS; COMPUTER MODEL; DEGRADATION; DISINFECTION; GAMMA IRRADIATION; OXIDATION REDUCTION REACTION; RADIOLYSIS;

CHLORIDES; COBALT RADIOISOTOPES; DISINFECTION; DOSE-RESPONSE RELATIONSHIP, RADIATION; FREE RADICALS; GAMMA RAYS; HYDROCARBONS, CHLORINATED; IONS; KINETICS; MODELS, CHEMICAL; NITRATES; WASTE DISPOSAL, FLUID; WATER POLLUTANTS, CHEMICAL;

EID: 33846847928     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es061410b     Document Type: Article

References (75)

1. Rook, J. J. Formation of haloforms during chlorination of natural waters, water treatment and examination. Soc. Water 1974, 23 (PT.2), 234-243.
2. Fed. Regist. 1998, 90 (3), 69389.
3. Richardson, S. D. Water analysis: Emerging contaminants and current issues. Anal. Chem. 2003, 75, 2831-2857.
4. Richardson, S. D.; Thruston, A. D., Jr.; Caughran, T. V.; Chen, P. H.; Collette, T. W., Schenck, K. M.; Lykins, B. W., Jr.; RavAcha, C.; Glezer, V. Identification of new drinking water disinfection by-products from ozone, chlorine dioxide, chloramine, and chlorine. Water, Air, Soil Pollut. 2000, 123, 95-102.
5. Krasner, S. W.; Weinberg, H. S.; Richardson, S. D.; Pastor, S. J.; Chinn, R.; Sclimenti, M. J.; Onstad, G. D.; Thurston, A. D., Jr. Occurrence of a new generation of disinfection byproducts. Environ. Sci. Technol. 2007, in press.
6. Sayato, Y.; Nakmuro, K.; Matsui, S. Studies on mechanism of volatile chlorinated organic compound formation (III). Mechanism of formation of chloroform and chloropicrin by chlorination of humic acid. Suishitsu Odaku Kenkyu. Jpn. J. Water Pollut. Res. 1982, 5, 127-128.
7. Becke, C.; Maier, D.; Sonthheimer, H. Herkunft von trichlornitromethan im trinkwasser, (Origin of trichloronitromethane in drinking water). Vom Wasser 1984, 62, 125-135.
8. Merlet, N.; Thibaud, H.; Dore, M. Chloropicrin formation during oxidative treatments in the preparation of drinking water. Sci. Total Environ. 1985, 47, 223-228.
9. Duguet, J. P.; Tsutsumi, Y.; Bruchet, A.; Mallevialle, J. Chloropicrin in potable water: Conditions for formation and production during treatment. In Proceedings of the 5th Conferenceon Water Chlorination: Environmental Impact and Health Effects Williamsburg, Virginia, June 3-8; Jolley, R. L., Bull, R. J., Davis, W. P., Eds.; Lewis Publishers: Chelsea, MI, 1984; pp 1201-1213.
10. Thibaud, H.; Laat, D. J.; Merlet, N.; Doré, M. Chloropicrin formation in aqueous solution: effect of nitrites on precursors formation during the oxidation of organic compounds. Water Res. 1987, 21, 813-821.
11. Hoigné, J.; Bader, H. The formation of trichloronitromethane (chloropicrin) and chloroform in a combined ozonation/chlorination treatment of drinking water. Water Res. 1988, 22, 313-319.
12. Jacangelo, J. G.; Patania, N. L; Reagan, K. M.; Aieta, E. M.; Krasner, S. W.; McGuire, M. J. Impact of ozonation on the formation and control of disinfection byproducts in drinking water. J. Am. Water Works Assoc. 1989, 81(8), 74-83.
13. U.S. Environmental Protection Agency. The occurrence of disinfection by-products (DPBs) of health concern in drinking water: Results of a nationwide occurrence study 2002; EPA/600/R-02/068; U.S. EPA National Exposure Research Laboratory: Athens, GA, 2002.
14. Park, D.-S.; Grodnitzky, J. A.; Coats, J. R. QSAR evaluation of cyanohydrins' fumigation toxicity to house fly (Musca domestica) and lesser grain borer (Rhyzopertha dominica). J. Agric. Food Chem. 2002, 50, 5617-5620.
15. Selala, M. I.; Janssens, J. J.; Jorens, Ph. G.; Bossaert, L. L.; Beaucourt, L.; Schepens, P.J.C. An improperly labeled container of chloropicrin: A farmer's nightmare. Bull. Environ. Contam. Toxicol. 1989, 42, 202-208.
16. Plewa, M. J.; Wagner, E. D.; Jazwierska, P.; Richardson, S. D.; Chen, P. H.; McKague, A. B. Halonitromethane drinking water disinfection byproducts: chemical characterization and mammalian cell cytotoxicity and genotoxicity. Environ. Sci. Technol. 2004, 38, 62-68.
17. Sparks, S. E.; Quistad, G. B.; Li, W.; Casida, J. E. Chloropicrin dechlorination in relation to toxic action. J. Biochem. Mol. Toxicol. 2000, 14, 26-32.
18. Giller, S.; Le, Curieux, F.; Gauthier, L.; Erb, F.; Marzin, D. Genotoxicity assay of chloral hydrate and chloropicrin. Mutat. Res. 1995, 348, 147-152.
19. Schneider, M.; Quistad, G. B.; Casida, J. E. Glutathione activation of chloropicrin in the salmonella mutagenicity test. Mutat. Res. 1999, 439, 233-238.
20. Moureu, H.; Chovin, P.; Truffert, L. Sur la transformation photochimique de la chloropicrine en phosgene. Arch. Maladies Prof. Med. Trav. Secur. Soc. 1950, 11(5), 445-452.
21. Wade, E. A.; Reak, K. E.; Parsons, B. F.; Clemes, T. P.; Singmaster, K. A. Photochemistry of chloropicrin in cryogenic matrices. Chem. Phys. Lett. 2002, 365, 473-479.
22. Wilhelm, S. N.; Shepler, K.; Lawrence, L. J.; Lee, H. Environment fate of chloropicrin in fumigants: environmental fate, exposure, and analysis. In Fumigants Environmental fates, Analysis, Exposure; Seiber, J. N., Woodrow, J. E., Yates, M. V., Knuteson, J. A., Wolfe, N. L., Yates, S. R., Eds.; ACS Symp. Ser. 652; American Chemical Society: Washington, DC, 1996; Chapter 8, pp 80-93.
23. Zhang, G.; Hua, I. Ultrasonic degradation of trichloroacetonitrile, chloropicrin and bromobenzene: design factors and matrix effects. Adv. Environ. Res. 2000, 4, 211-218.
24. Whitham, K.; Lyons, S.; Miller, R.; Nett, D.; Treas, P.; Zante, A.; Fessenden, R. W.; Thomas, M. D.; Wang, Y. Linear accelerator for radiation chemistry research at Notre Dame 1995. In IEEE Proceedings Particle Accelerator Conference and International Conference on High Energy Accelerators; Dallas, Texas, 1995; pp 131-133.
25. Button, G. V.; Greenstock, C. L.; Helman, W. P.; Ross, A. B. Critical review of rate constants for reactions of hydrated electrons, hydrogen atoms and hydroxyl radicals (OH/O-) in aqueous solutions. J. Phys. Chem. Ref. Data 1988, 17, 513-886.
26. Spinks, J. W. T.; Woods, R.J. An Introduction to Radiation Chemistry; John Wiley & Sons: New York, 1990.
27. Mezyk, S. P.; Cooper, W. J.; Madden, K. P.; Bartels, D. M. Free radical destruction of n-nitrosodimethylamine in water. Environ. Sci. Technol. 2004, 38, 3161-3167.
28. Asmus, K.-D. Pulse radiolysis methodology. Methods Enzymol. 1984, 105, 167-178.
29. Carver, M. B.; Hanley, D. V.; Chapin, K. R. MAKSIMA-CHEMIST, A program for mass action kinetic simulated manipulation and integration using stiff techniques; Chalk River Nuclear River Laboratories Report; Atomic Energy of Canada, Ltd.: 6413, 1979; pp 1-28.
30. Gear C. W. The automatic integration of ordinary differential equations. Comm. ACM 1971, 14(3), 176-179.
31. Schwarz, H. A. A determination of some rate constants for the radical processes in the radiation chemistry of water. J. Phys. Chem. 1962, 66, 255-262.
32. Mezyk, S. P.; Helgeson, T.; Cole, S. K.; Cooper, W. J.; Fox, R. F.; Gardinali, P. R.; Mincher, B. J. Free radical chemistry of disinfection by-products 1. Kinetics of hydrated electron and hydroxyl radical reactions with halomethanes in water. J. Phys. Chem. 2006, 110, 2176-2180.
33. Hart, E. J.; Anbar, M. The Hydrated Electron; Wiley-Interscience: New York, 1970.
34. Asmus, K.-D.; Henglein, A.; Ebert, M.; Keene, J. P. Pulsradiolytische Untersuchung schneller Reaktionen von hydratisierten Elektronen, freien Radikalen und Ionen mit Tetranitromethan in Waessriger Loesun. Ber. Bunsenges. Phys. Chem. 1964, 68, 657-663.
35. Rabani, J.; Mulac, W. A.; Matheson, M. S. The pulse radiolysis of aqueous tetranitromethane. I. Rate constants and the extinction coefficient of eaq-. II. Oxygenated solutions. J. Phys. Chem. 1965, 69, 53-70.
36. 2. Chem.-Biol. 1983, 47, 15-27.
37. Neta, P.; Huie, R. E.; Ross, A. B. Rate constants for reactions of peroxyl radicals in fluid solutions. J. Phys. Chem. Ref. Data 1990, 19, 413-513.
38. Von Sonntag, C.; Schuchmann, H.-P. Peroxyl radicals in aqueous solutions. In Peroxyl Radicals; Alfassi, Z. B., Ed.; John Wiley & Sons: New York, 1997; pp 173-234.
39. Bonifačić, M.; Schöneich, C.; Asmus, K.-D. Halogenated peroxyl radicals as multi-electron oxidants: Pulse radiolysis study on the reactions of trichloromethyl peroxyl radicals with iodide. J. Chem. Soc., Chem. Commun. 1991, 1117-1119.
40. Simic, M. G.; Hunter, E. P. L. Reaction mechanisms of peroxyl and C-centered radicals with sulfhydryls. Free Radical Biol. Med. 1986, 2, 227-230.
41. Khaikin, G. I.; Alfassi, Z. B.; Neta, P. Formation and reaction of halogenated phenylperoxyl radicals in aqueous alcohol solutions. J. Phys. Chem. 1995, 99, 11447-11451.
42. Mertens, R.; von Sonntag, C.; Lind, J.; Merenyi, G. A kinetic study of the hydrolysis of phosgene in aqueous solution by pulse radiolysis. Angew. Chem., Int. Ed. Engl. 1994, 33, 1259-1261.
43. Løgager, T.; Sehested, K. Formation and decay of peroxynitrous acid: A pulse radiolysis study. J. Phys. Chem. 1993, 97, 6664-6669.
44. Barker, G. C.; Fowles, P.; Stringer, B. Pulse radiolytic induced transient electrical conductance in liquid solutions. Trans. Faraday Soc. 1970, 66, 1509-1519.
45. 4 in aqueous solutions. J. Am. Chem. Soc. 1970, 92, 5821-5828.
46. -. Trans. Faraday Soc. 1969, 65, 2150-2158.
47. Adams, G. E.; Boag, J. W.; Michael, B. D. Reactions of the hydroxyl radical part 2. Determination of absolute rate constants. Trans. Faraday Soc. 1965, 61, 1417-1424.
48. Adams, G. E; Boag, J. W. Spectroscopic studies of reactions of the OH radical. Proc. Chem. Soc. 1964, 112.
49. - in aqueous solution. J. Phys. Chem. 1988, 92, 6278-6283.
50. Løgager, T.; Sehested, K. Formation and decay of peroxynitric acid: A pulse radiolysis study. J. Phys. Chem. 1993, 97, 10047-10052.
51. Merényi, G.; Lind, J;, Goldstein, S.; Czapski, G. Mechanism and thermochemistry of peroxynitrite decomposition in water. J. Phys. Chem. A 1999, 103, 5685-5691.
52. •-: A pulse radiolysis study. Free Radical Biol. Med. 1995, 19, 505-510.
53. Pryor, W. A.; Squadrito, G. L. The chemistry of peroxynitrite: A product from the reaction of nitric oxide with superoxide. Am. J. Physiol. (Lung Cell. MoI. Physiol.) 1995, 12, L699-722.
54. Kissner, R; Nauser, T.; Bugnon, P.; Lye, P. G.; Koppenol, W. H. Formation and properties of peroxynitrite as studied by laser flash photolysis, high-pressure stopped-flow technique, and pulse radiolysis. Chem. Res. Toxicol. 1997, 10, 1285-1292.
55. Goldstein, S.; Lind, J.; Merenyi, G. Chemistry of peroxynitrites as compared to peroxynitrates. Chem. Rev. 2005, 105, 2457-2470.
56. - in aqueous solution. J. Phys. Chem. 1990, 94, 2435-2441.
57. - atoms. Ber. Bunsenges. Phys. Chem. 1985, 89, 243-245.
58. Cambron, R. T.; Harris, J. M. Photothermal investigation of chlorine photodissociation and nongeminate recombination in liquids. J. Phys. Chem. 1995, 99, 695-706.
59. - in aqueous NaCl solutions. J. Photochem. 1980, 14, 303-310.
60. -. J. Phys. Chem. 2004, 108, 295-308.
61. •-. J. Chem. Soc., Faraday Trans. 1998, 94, 653-657.
62. Jayson, G. G.; Parsons, B. J.; Swallow, A. J. Some simple, highly reactive, inorganic chlorine derivatives in aqueous solution their formation using pulses of radiation and their role in the mechanism of the Fricke dosimeter. J. Chem. Soc., Faraday Trans. I 1973, 69, 1597-1607.
63. - reactions: The dependence of the rates of radical disproportionation and oxidation of Mn(II) complexes on field intensity. J. Phys. Chem. 1993, 97, 2793-2797.
64. -, with anions. J. Phys. Chem. 1990, 94, 8561-8567.
65. - radical anion in aqueous solution. J. Chem. Phys. 1988, 89, 3565-3572.
66. -. Inorg. Chem. 1987, 26, 1408-1410.
67. Gogolev, A. V.; Makarov, I. E.; Pikaev, A. K. Pulsed radiolysis of concentrated hydrochloric acid. High Energy Chem. 1984, 18, 390-395.
68. Navaratnam, S.; Parsons, B. J.; Swallow, A. J. Some reactions of the dichloride anion radical. Radiat. Phys. Chem. 1980, 15, 159-161.
69. - anion-radicals during pulse radiolysis of concentrated aqueous lithium chloride solutions. Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transi.) 1974, 23, 877-878.
70. - radicals. J. Phys. Chem. 1978, 82, 854-857.
71. Neta, P.; Fessenden, R. W.; Schuler, R. H. An electron spin resonance study of the rate constants for reactions of hydrogen atoms with organic compounds in aqueous solution. J. Phys. Chem. 1971, 75, 1654-1666.
72. Köester, R.; Asmus, K.-D. Die Reduktion von Tetrachlorkohlenstoff durch hydratisierte Elektronen, H-Atome und reduzierende Radikale. Z. Naturforsch. Teil B 1971, 26, 1104-1108.
73. Pimblott, S. Milosavljevic, B. H.; LaVerne, J. A. Radiolysis of aqueous solutions of 1,1- and 1,2-dichloroethane. J. Phys. Chem. 2005, 109, 10294-10301.
74. Asmus, K.-D.; Henglein, A.; Ebert, M.; Keene, J. P. Pulsradiolytische Untersuchung schneller Reaktionen von hydratisierten Elektronen, freien Radikalen und Ionen mit Tetranitromethan in wässriger Lösung. Ber. Bunsenges. Phys. Chem. 1964, 68, 657-663.
75. Hiller, K.-O.; Asmus, K.-D. Formation and reduction reactions of á-amino radicals derived from methionine and its derivatives in aqueous solutions. J. Phys. Chem. 1983, 87, 3682-3688.