Quaternary amines as nitrosamine precursors: A role for consumer products?

Environmental Science and Technology

Volumn 44, Issue 4, 2010, Pages 1224-1231

  Kemper, Jerome M ^a   Walse, Spencer S ^a   Mitch, William A ^a  

^a Yale University   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL AMINES; AMINE PRECURSOR; FABRIC SOFTENER; FORMATION PATHWAYS; FREE CHLORINE; HIGH LOADINGS; LOW-YIELD; PRE-TREATMENT; QUATERNARY AMINES; WASTEWATER EFFLUENTS;

CHLORINE; CONSUMER PRODUCTS; EFFLUENTS; EXPERIMENTS; OZONE; SOAPS (DETERGENTS); WASTEWATER; WASTEWATER RECLAMATION; WASTEWATER TREATMENT;

AMINES;

CHLORINE; NITROSAMINE; OZONE; RADICAL;

EFFLUENT; RADICAL; SEDIMENTATION; WASTEWATER; WATER TREATMENT;

ARTICLE; DEGRADATION; ELIMINATION REACTION; SEDIMENTATION; WASTE WATER MANAGEMENT;

AMINES; MOLECULAR STRUCTURE; NITROSAMINES; WATER POLLUTANTS, CHEMICAL; WATER PURIFICATION;

EID: 77249131338     PISSN: 0013936X     EISSN: 15205851     Source Type: Journal    
DOI: 10.1021/es902840h     Document Type: Article

References (34)

1. Gerecke, A. C.; Sedlak, D. L. Precursors of N-nitrosodimethylamine in natural waters. Environ. Sci. Technol. 2003, 37, 1331-1336.
2. Sedlak, D. L.; Deeb, R. A.; Hawley, E. L.; Mitch, W. A.; Durbin, T. D.; Mowbray, S.; Carr, S. Sources and fate of nitrosodimethylamine and its precursors in municipal wastewater treatment plants. Water Environ. Res. 2005, 77, 32-39.
3. Walse, S. S.; Mitch, W. A. Nitrosamine carcinogens also swim in chlorinated pools. Environ. Sci. Technol. 2008, 42, 1032-1037.
4. Mitch, W. A.; Sharp, J. O.; Trussell, R. R.; Valentine, R. L.; Alvarez-Cohen, L.; Sedlak, D. L. N-nitrosodimethylamine (NDMA) as a drinking water contaminant: a review. Environ. Eng. Sci. 2003, 20 (5), 389-404.
5. Mitch, W. A.; Krasner, S. W.; Westerhoff, P.; Dotson, A. Occurrence and Formation of Nitrogenous Disinfection By-Products; Final report for AwwaRF Project 3014, Water Research Foundation: Denver, CO, 2009.
6. Wilczak, A.; Assadi-Rad, A.; Lai, H. H.; Hoover, L. L.; Smith, J. F.; Berger, R.; Rodigari, F.; Beland, J. W.; Lazzelle, L. J.; Kinicannon, E. G.; Baker, H.; Heaney, C. T. Formation of NDMA in chloraminated water coagulated with DADMAC cationic polymer. J. Am. Water Works Assoc. 2003, 95, 94-106.
7. Valentine, R. L.; Choi, Z.; Chen, Z.; Barrett, S. E.; Hwang, C.; Guo, Y. C.; Wehner, M.; Fitzsimmons, S.; Andrews, S. A.; Werker, A. G.; C. Brubacher, C.; Kohut, K. Factors Affecting the Formation of NDMA in Water and Occurrence; Final report for AwwaRF Project 2678, Water Research Foundation: Denver, CO, 2005.
8. Mitch, W. A.; Sedlak, D. L. Characterization and fate of N-nitrosodimethylamine precursors in municipal wastewater treatment plants. Environ. Sci. Technol. 2004, 38, 1445-1454.
9. Schreiber, I. M.; Mitch,W.A. Occurrenceandfate of nitrosamines and nitrosamine precursors in wastewater-impacted surface waters using boron as a conservative tracer. Environ. Sci. Technol. 2006, 40, 3203-3210.
10. Zuppi, C.; Messana, I.; Forni, F.; Rossi, C.; Pennacchietti, L.; Ferrari, F.; Giardina, B. H-1 NMR spectra of normal urines: Reference ranges of the major metabolites. Clin. Chim. Acta 1997, 265, 85-97.
11. Mills, G. A.; Walker, V.; Mughal, H. Quantitative determination of trimethylamine in urine by solid-phase microextraction and gas chromatography mass spectrometry. J. Chromatogr. B 1999, 723, 281-285.
12. Mitch, W. A.; Schreiber, I. M. Degradation of tertiary alkylamines during chlorination/chloramination: Implications for formation of aldehydes, nitriles, halonitroalkanes, and nitrosamines. Environ. Sci. Technol. 2008, 42, 4811-4817.
13. Spiegelhalder, B.; Preussmann, R. Contamination of toiletries and cosmetic products with volatile and nonvolatile N-nitroso carcinogens. J. Cancer Res. Clin. Oncol. 1984, 108, 160-163.
14. Schreiber, I. M.; Mitch, W. A. Nitrosamine formation pathway revisited: The importance of chloramine speciation and dissolved oxygen. Environ. Sci. Technol. 2006, 40, 6007-6014.
15. Park, S. H.; Wei, S.; Mizaikoff, B.; Taylor, A. E.; Favero, C.; Huang, C. H. Degradation of amine-based water treatment polymers during chloramination as N-nitrosodimethylamine (NDMA) precursors. Environ. Sci. Technol. 2009, 43, 1360-1366.
16. Kemper, J. M.; Westerhoff, P.; Dotson, A.; Mitch, W. A. Nitrosamine, dimethylnitramine, and chloropicrin formation during strong base anion-exchange treatment. Environ. Sci. Technol. 2009, 43, 466-472.
17. Schreiber, I. M.; Mitch, W. A. Influence of the order of reagent addition on NDMA formation during chloramination. Environ. Sci. Technol. 2005, 39, 3811-3818.
18. Lee, C.; Schmidt, C.; Yoon, J.; von Gunten, U. Oxidation of N-nitrosodimethylamine (NDMA) precursors with ozone and chlorine dioxide: Kinetics and effect on NDMA formation potential. Environ. Sci. Technol. 2007, 41, 2056-2063.
19. Standard Methods for the Examination of Water and Wastewater, 20th ed.; American Public Health Association, American Water Works Association, Environmental Federation Publishers: Washington, DC, 1998.
20. Mitch, W. A.; Gerecke, A. C.; Sedlak, D. L. A N-nitrosodimethylamine (NDMA) precursor analysis for chlorination of water and wastewater. Water Res. 2003, 37, 3733-3741.
21. Sacher, F.; Schmidt, C. K.; Lee, C.; von Gunten, U. Strategies for Minimizing Nitrosamine Formation during Disinfection; Final report for AwwaRF Project 2979, Water Research Foundation: Denver, CO, 2007.
22. Giroux, R. Shampoo. Chem. Eng. News 2002, 80, 42-42.
23. Clara, M.; Scharf, S.; Scheffknecht, C.; Gans, O. Occurrence of selected surfactants in untreated and treated sewage. Water Res. 2007, 41, 4339-4348.
24. Loretz, L.; Api, A. M.; Barraj, L.; Burdick, J.; Davis, D. A.; Dressler, W.; Gilberti, E.; Jarrett, G.; Mann, S.; Pan, Y. H. L.; Re, T.; Renskers, K.; Scrafford, C.; Vater, S. Exposure data for personal care products: Hairspray, spray perfume, liquid foundation, shampoo, body wash, and solid antiperspirant. Food Chem. Toxicol. 2006, 44, 2008-2018.
25. Nishiyama, N.; Toshima, Y.; Ikeda, Y. Biodegradation of alkyltrimethylammonium salts in activated sludge. Chemosphere 1995, 30, 593-603.
26. von Gunten, U. Ozonation of drinking water: Part I. Oxidation kinetics and product formation. Water Res. 2003, 37, 1443-1467.
27. NDRL Radiation Chemistry Data Center; http://allen.rad.nd.edu/browse- compil.html (accessed January 2, 2009).
28. Andrzejewski, P.; Kasprzyk-Hordern, B.; Nawrocki, J. N-nitrosodimethylamine (NDMA) formation during ozonation of dimethylamine containing waters. Water Res. 2008, 42, 863-870.
29. Heasley, V. L.; Fisher, A. M.; Herman, E. E.; Jacobsen, F. E.; Miller, E. W.; Ramirez, A. M.; Royer, N. R.; Whisenand, J. M.; Zoetewey, D. L.; Shellhamer, D. F. Investigations of the reactions of monochloramine and dichloramine with selected phenols: Examination of humic acid models and water contaminants. Environ. Sci. Technol. 2004, 38, 5022-5029.
30. Vikesland, P. J.; Valentine, R. L. Reaction pathways involved in the reduction of monochloramine by ferrous iron. Environ. Sci. Technol. 2000, 34, 83-90.
31. Farnia, G.; Tomat, R.; Vianello, E. Relative reactivities of aliphatic alcohols and amines towards aminyl radicals. J. Chem. Soc., Perkin Trans. 2 1975, 763-768.
32. 2̇ reactions with oxygen, amino acids, and melanins. J. Phys. Chem. A 2008, 112, 1234-1237.
33. Schreiber, I. M.; Mitch, W. A. Enhanced nitrogenous disinfection byproduct formation near the breakpoint: Implications for nitrification control. Environ. Sci. Technol. 2007, 41, 7039-7046.
34. Jafvert, C. T.; Valentine, R. L. Reaction scheme for the chlorination of ammoniacal water. Environ. Sci. Technol. 1992, 26, 577-586.