NDMA formation from amine-based pharmaceuticals - Impact from prechlorination and water matrix

Water Research

Volumn 47, Issue 7, 2013, Pages 2446-2457

  Shen, Ruqiao ^a   Andrews, Susan A ^a  

^a UNIVERSITY OF TORONTO   (Canada)

Author keywords

NDMA; NOM; Prechlorination; Ranitidine; Sumatriptan

Indexed keywords

AMINATION; BIOLOGICAL MATERIALS; POTABLE WATER; REACTION KINETICS;

CHLORAMINATION; DIMETHYLAMINES; N-NITROSODIMETHYLAMINE; NATURAL ORGANIC MATTERS; PRE-OXIDATION; PRECHLORINATION; RANITIDINE; SINGLE PRECURSORS; SUMATRIPTAN; WATER MATRICES;

AMINES;

CHLORINE; DIMETHYLNITROSAMINE; NATURAL ORGANIC MATTER; SUMATRIPTAN;

CHLORINATION; DRINKING WATER; DRUG; INHIBITION; ORGANIC MATTER; OXIDATION; POLLUTANT REMOVAL;

ARTICLE; CHEMICAL REACTION KINETICS; CHLORINATION; PRIORITY JOURNAL;

EID: 84875615961     PISSN: 00431354     EISSN: 18792448     Source Type: Journal    
DOI: 10.1016/j.watres.2013.02.017     Document Type: Article

References (56)

1. Abia L., Armesto X.L., Canle L.M., Garcia M.V., Santaballa J.A. Oxidation of aliphatic amines by aqueous chlorine. Tetradedron 1998, 54:521-530.
2. Andrzejewski P., Kasprzyk-Hordern B., Nawrocki J. N-nitrosodimethylamine (NDMA) formation during ozonation of dimethylamine-containing waters. Water Research 2008, 42:863-870.
3. Ballard B.D., Mackay A.A. Estimating the removal of anthropogenic organic chemicals from raw drinking water by coagulation flocculation. Journal of Environmental Engineering 2005, 131:108-118.
4. Carey F.A. Organic Chemistry 2008, McGraw-Hill, New York, Chapter 12. Reactions of Arenes: Electrophilic Aromatic Substitution. pp. 496-498. seventh ed.
5. Charrois J.W.A., Hrudey S.E. Breakpoint chlorination and free-chlorine contact time: implications for drinking water N-nitrosodimethylamine concentrations. Water Research 2007, 41:674-682.
6. Chen Z., Valentine R.L. Formation of N-Nitrosodimethylamine (NDMA) from humic substances in natural water. Environmental Science and Technology 2007, 41:6059-6065.
7. Chen Z., Valentine R.L. The influence of the pre-oxidation of natural organic matter on the formation of N-Nitrosodimethylamine (NDMA). Environmental Science and Technology 2008, 42:5062-5067.
8. Chen Z., Yang L., Zhai X., Zhao S., Li A., Shen J. N-nitrosamine formation during chlorination/chloramination of bromide-containing water. Water Science and Technology: Water Supply 2010, 10:462-471.
9. Choi J.H., Valentine R.L. N-Nitrosodimethylamine formation by free-chlorine-enhanced nitrosation of dimethylamine. Environmental Science and Technology 2003, 37:4871-4876.
10. Comerton A.M., Andrews R.C., Bagley D.M. Impact of blending reuse and lake water on treated water quality. Journal of Environmental Engineering and Science 2006, 5:359-363.
11. De Ridder D.J., Verliefde A.R.D., Heijman S.G.J., Verberk Q.J.C., Rietveld L.C., van der Aa L.T.J., Amy G.L., van Dijk J.C. Influence of natural organic matter on equilibrium adsorption of neutral and charged pharmaceuticals onto activated carbon. Water Science and Technology 2011, 63:416-423.
12. Deborde M., von Gunten U. Reactions of chlorine with inorganic and organic compounds during water treatment - kinetics and mechanisms: a critical review. Water Research 2008, 42:13-51.
13. Diemert, S.A., 2012. The Impact of Coagulation on Endocrine Disrupting Compounds, Pharmaceutically Active Compounds and Natural Organic Matter. Master's thesis, University of Toronto, Ontario.
14. Ding Y., Teppen B.J., Boyd S.A., Li H. Measurement of associations of pharmaceuticals with dissolved humic substances using solid phase extraction. Chemosphere 2012, http://dx.doi.org/10.1016/j.chemosphere.2012.11.039.
15. Dotson A., Westerhoff P., Krasner S.W. Nitrosamine formation from natural organic matter isolates and sunlight photolysis of nitrosamines. Proceedings of AWWA Annual Conference and Exposition. Toronto, ON, Canada, June 24-28, 2007 2007.
16. EPA Integrated Risk Information System (IRIS), 1993. N-Nitrosodimethylamine; CASRN 62-75-9. http://www.epa.gov/iris/subst/0045.htm.
17. Gerecke A.C., Sedlak D.L. Precursors of N-Nitrosodimethylamine in natural waters. Environmental Science and Technology 2003, 37:1331-1336.
18. Gilow H.M., Burton D.E. Bromination and chlorination of pyrrole and some reactive 1-substituted pyrroles. Journal of Organic Chemistry 1981, 46:2221-2225.
19. Harvey, M, 2009. The Impacts of UV Direct Photolysis and UV/H2O2 Advanced Oxidation Processes on the Formation of Nitrosamines and Organic Chloramines from Subsequent Chlor(am)ination. Master's thesis, University of Toronto, Ontario.
20. Health Canada Guideline Technical Document on N-nitrosodimethylamine (NDMA) in Drinking Water for Public Comment 2010, http://www.hc-sc.gc.ca/ewh-semt/consult/_2010/ndma/draft-ebauche-eng.php#a3.
21. Huber S.A., Balz A., Abert M., Pronk W. Characterisation of aquatic humic and non-humic matter with size-exclusion chromatography - organic carbon detection - organic nitrogen detection (LC-OCD-OND). Water Research 2011, 45:879-885.
22. Kemper J.M., Walse S.S., Mitch W.A. Quaternary amines as nitrosamine precursors: a role for consumer products?. Environmental Science and Technology 2010, 44:1224-1231.
23. Kohut K.D., Andrews S.A. Polyelectrolyte age and N-nitrosodimethylamine formation in drinking water treatment. Water Quality Research Journal of Canada 2003, 38(4):719-735.
24. Krasner S.W. The formation and control of emerging disinfection by-products of health concern. Philosophical Transactions of the Royal Society A Mathematical and Physical Sciences 2009, 367:4077-4095.
25. Le Roux J., Gallard H., Croue J. Chloramination of nitrogenous contaminants (pharmaceuticals and pesticides): NDMA and halogenated DBPs formation. Water Research 2011, 45:3164-3174.
26. Le Roux J., Gallard H., Croue J. Formation of NDMA and halogenated DBPs by chloramination of tertiary amines: the influence of bromide ion. Environmental Science and Technology 2012, 46:1581-1589.
27. Le Roux J., Gallard H., Croue J., Papot S., Deborde M. NDMA formation by chloramination of ranitidine: kinetics and mechanism. Environmental Science and Technology 2012, 46:11095-11103.
28. Lee C., Schimidt C., Yoon J., Von Gunten U. Oxidation of N-Nitrosodimethylamine (NDMA) precursors with ozone and chlorine dioxide: kinetics and effect on NDMA formation potential. Environmental Science and Technology 2007, 41:2056-2063.
29. Lee C., Lee Y., Schmidt C., Yoon J., Von Gunten U. Oxidation of suspected N-nitrosodimethylamine (NDMA) precursors by ferrate (VI): kinetics and effect on the NDMA formation potential of natural waters. Water Research 2008, 42:433-441.
30. Lin S., Carlson R.M. Susceptibility of environmentally important heterocycles to chemical disinfection: reactions with aqueous chlorine, chlorine dioxide, and chloramine. Environmental Science and Technology 1984, 18:743-748.
31. Massachusetts Department of Environmental Protection (MassDEP) Current Regulatory Limit: n-Nitrosodimethylamine (NDMA) 2004, CASRN 62759. http://www.mass.gov/dep/water/drinking/standards/ndma.htm.
32. Mitch W.A., Krasner S.W., Lee C.F.T., Wong T.M. Tradeoffs in DBP formation during chloramination following pre-oxidation for nitrosamine control. Proceedings of the AWWA Water Quality Technology Conference, Savannah, GA, November 14-18, 2010 2010.
33. Mitch W.A., Schreiber I.M. Degradation of tertiary alkylamines during chlorination/chloramination: implications for formation of aldehydes, nitriles, halonitroalkanes, and nitrosamines. Environmental Science and Technology 2008, 42:4811-4817.
34. Mitch W.A., Sedlak D.L. Characterization and fate of N-nitrosodimethylamine precursors in municipal wastewater treatment plants. Environmental Science and Technology 2004, 38:1445-1454.
35. MOE, 2003. Ontario Regulation 268/03 Made under the Safe Drinking Water Act, 2002. http://www.e-laws.gov.on.ca/html/source/regs/english/2003/elaws_src_regs_r03268_e.htm.
36. Najm I., Trussell R.R. NDMA formation in water and wastewater. Journal of the American Water Works Association 2001, 93(2):92-99.
37. Office of Environmental Health Hazard Assessment (OEHHA) Public Health Goal for N-nitrosodimethylamine and Cadmium in Drinking Water 2006, http://www.oehha.org/water/phg/cadndma122206.html.
38. Oya M., Kosaka K., Asami M., Kunikane S. Formation of N-nitrosodimethylamine (NDMA) by ozonation of dyes and related compounds. Chemosphere 2008, 73:1724-1730.
39. Pisarenko A.N., Stanford B.D., Yan D., Gerrity D., Snyder S.A. Effects of ozone and ozone/peroxide on trace organic contaminants and NDMA in drinking water and water reuse applications. Water Research 2012, 46:316-326.
40. 2 in the presence of chloramines on NDMA formation potential of tramadol. Environmental Science and Technology 2012, 46:8356-8364.
41. Schmidt C.K., Brauch H.J. N, N-Dimethylsulfamide as precursor for N-Nitrosodimethylamine (NDMA) formation upon ozonation and its fate during drinking water treatment. Environmental Science and Technology 2008, 42:6340-6346.
42. Schmidt C.K., Sacher F., Brauch H.J. Strategies for minimizing formation of NDMA and other nitrosamines during disinfection of drinking water. Proceedings of the AWWA Water Quality Technology Conference, Denver, C.O., November 5-9, 2006 2006.
43. Schreiber I.M., Mitch W.A. Influence of the order of reagent addition on NDMA formation during chloramination. Environmental Science and Technology 2005, 39:3811-3818.
44. Schreiber I.M., Mitch W.A. Nitrosamine formation pathway revisited: the importance of chloramines speciation and dissolved oxygen. Environmental Science and Technology 2006, 40:6007-6014.
45. Schreiber I.M., Mitch W.A. Occurrence and fate of nitrosamines and nitrosamine precursor in wastewater-impacted surface waters using boron as a conservative tracer. Environmental Science and Technology 2006, 40:3203-3210.
46. Shah A.D., Krasner S.W., Lee C.F.T., von Gunten U., Mitch W.A. Trade-offs in disinfection byproduct formation associated with precursor preoxidation for control of N-Nitrosodimethylamine formation. Environmental Science and Technology 2012, 46:4809-4818.
47. Shen R., Andrews S.A. Demonstration of 20 pharmaceuticals and personal care products (PPCPs) as nitrosamine precursors during chloramine disinfection. Water Research 2011, 45:944-952.
48. Shen R., Andrews S.A. NDMA formation kinetics from three pharmaceuticals in four water matrices. Water Research 2011, 45:5687-5694.
49. Stackelberg P.E., Gibs J., Furlong E.T., Meyer M.T., Zaugg S.D., Lippincott R.L. Efficiency of conventional drinking-water-treatment processes in removal of pharmaceuticals and other organic compounds. Science of the Total Environment 2007, 377:255-272.
50. USEPA Contaminant Candidate List 3 (CCL3) 2009, http://water.epa.gov/scitech/drinkingwater/dws/ccl/ccl3.cfm.
51. Valentine R.L., Choi J., Chen Z., Barrett S.E., Hwang C., Guo Y.C., Wehner M., Fitzsimmons S., Andrews S.A., Werker A.G., Brubacher C., Kohut K. Factors Affecting the Formation of NDMA in Water and Occurrence 2005, Denver, CO, pp. 81-90.
52. Vieno N., Tuhkanen T., Kronberg L. Removal of pharmaceuticals in drinking water treatment: effect of chemical coagulation. Environmental Technology 2006, 27:183-192.
53. Westerhoff P., Yoon Y., Snyder S., Wert E. Fate of endocrine-disruptor, pharmaceutical, and personal care product chemicals during simulated drinking water treatment processes. Environmental Science and Technology 2005, 39:6649-6663.
54. Wilczak A., Assadi-Rad A., Lai H.H., Hoover L.L., Smith J.F., Berger R., Rodigari F., Beland J.W., Lazzelle L.J., Kincannon E.G., Baker H., Heaney C.T. Formation of NDMA in chloraminated water coagulated with DADMAC cationic polymer. Journal of the American Water Works Association 2003, 95(9):94-106.
55. Woodbeck, M., 2007. Evaluating the Potential Genotoxicity of Disinfected Source Waters. Master's thesis, University of Toronto, Ontario.
56. Xu X., Bartlett M.G., Stewart J.T. Determination of degradation products of sumatriptan succinate using LC-MS and LC-MS-MS. Journal of Pharmaceutical and Biomedical Analysis 2001, 26:367-377.