Formation, precursors, control, and occurrence of nitrosamines in drinking water: a review.

This review summarizes major findings over the last decade related to nitrosamines in drinking water, with a particular focus on N-nitrosodimethylamine (NDMA), because it is among the most widely detected nitrosamines in drinking waters. The reaction of inorganic dichloramine with amine precursors is likely the dominant mechanism responsible for NDMA formation in drinking waters. Even when occurrence surveys found NDMA formation in chlorinated drinking waters, it is unclear whether chloramination resulted from ammonia in the source waters. NDMA formation has been associated with the use of quaternary amine-based coagulants and anion exchange resins, and wastewater-impaired source waters. Specific NDMA precursors in wastewater-impacted source waters may include tertiary amine-containing pharmaceuticals or other quaternary amine-containing constituents of personal care products. Options for nitrosamine control include physical removal of precursors by activated carbon or precursor deactivation by application of oxidants, particularly ozone or chlorine, upstream of chloramination. Although NDMA has been the most prevalent nitrosamine detected in worldwide occurrence surveys, it may account for only ≈ 5% of all nitrosamines in chloraminated drinking waters. Other significant contributors to total nitrosamines are poorly characterized. However, high levels of certain low molecular weight nitrosamines have been detected in certain Chinese waters suspected to be impaired by industrial effluents. The review concludes by identifying research needs that should be addressed over the next decade.

[1]  Wontae Lee,et al.  Dissolved organic nitrogen as a precursor for chloroform, dichloroacetonitrile, N-nitrosodimethylamine, and trichloronitromethane. , 2007, Environmental science & technology.

[2]  S. Hrudey,et al.  Solid-phase extraction and high-performance liquid chromatography mass spectrometry analysis of nitrosamines in treated drinking water and wastewater , 2011 .

[3]  J. Croué,et al.  Chloramination of nitrogenous contaminants (pharmaceuticals and pesticides): NDMA and halogenated DBPs formation. , 2011, Water research.

[4]  S. Andrews,et al.  Polyelectrolyte Age and N-Nitrosodimethylamine Formation in Drinking Water Treatment , 2003 .

[5]  S. Walse,et al.  Nitrosamine carcinogens also swim in chlorinated pools. , 2008, Environmental science & technology.

[6]  Susan A Andrews,et al.  Demonstration of 20 pharmaceuticals and personal care products (PPCPs) as nitrosamine precursors during chloramine disinfection. , 2011, Water research.

[7]  Jianying Hu,et al.  Occurrence and source of nitrosamines and secondary amines in groundwater and its adjacent Jialu River basin, China. , 2012, Environmental science & technology.

[8]  J. Nawrocki,et al.  Nitrosamines and water. , 2011, Journal of hazardous materials.

[9]  A. Royce,et al.  Effectiveness of UV Advanced Oxidation for Destruction of Micro-Pollutants , 2008 .

[10]  Ching-Hua Huang,et al.  Oxidation of dithiocarbamates to yield N-nitrosamines by water disinfection oxidants. , 2013, Water research.

[11]  William A Arnold,et al.  Kinetics and mechanisms of N-nitrosodimethylamine formation upon ozonation of N,N-dimethylsulfamide-containing waters: bromide catalysis. , 2010, Environmental science & technology.

[12]  E. Michael Thurman,et al.  Response to Comment on “Pharmaceuticals, Hormones, and Other Organic Wastewater Contaminants in U.S. Streams, 1999−2000: A National Reconnaissance” , 2002 .

[13]  Carsten K Schmidt,et al.  N,N-dimethylsulfamide as precursor for N-nitrosodimethylamine (NDMA) formation upon ozonation and its fate during drinking water treatment. , 2008, Environmental science & technology.

[14]  David L Sedlak,et al.  Characterization and fate of N-nitrosodimethylamine precursors in municipal wastewater treatment plants. , 2004, Environmental science & technology.

[15]  Brett J. Vanderford,et al.  A QSAR-like analysis of the adsorption of endocrine disrupting compounds, pharmaceuticals, and personal care products on modified activated carbons. , 2009, Water research.

[16]  B. Kasprzyk-Hordern,et al.  N-nitrosodimethylamine (NDMA) formation during ozonation of dimethylamine-containing waters. , 2008, Water research.

[17]  P. Westerhoff,et al.  Case studies on nitrosamine formation and control at full-scale drinking water treatment plants , 2012 .

[18]  W. Mitch,et al.  Degradation of tertiary alkylamines during chlorination/chloramination: implications for formation of aldehydes, nitriles, halonitroalkanes, and nitrosamines. , 2008, Environmental science & technology.

[19]  D. Dixon,et al.  Detection of polyelectrolytes at trace levels in water by fluorescent tagging , 2004 .

[20]  U. von Gunten,et al.  Trade-offs in disinfection byproduct formation associated with precursor preoxidation for control of N-nitrosodimethylamine formation. , 2012, Environmental science & technology.

[21]  W. Mitch,et al.  Enhanced nitrogenous disinfection byproduct formation near the breakpoint: implications for nitrification control. , 2007, Environmental science & technology.

[22]  Stuart W. Krasner,et al.  Formation and control of emerging C‐ and N‐DBPs in drinking water , 2012 .

[23]  Ning Dai,et al.  Measurement of nitrosamine and nitramine formation from NOx reactions with amines during amine-based carbon dioxide capture for postcombustion carbon sequestration. , 2012, Environmental science & technology.

[24]  P. Westerhoff,et al.  Nitrogen enriched dissolved organic matter (DOM) isolates and their affinity to form emerging disinfection by-products. , 2009, Water science and technology : a journal of the International Association on Water Pollution Research.

[25]  Alicia C. Diehl,et al.  DBP formation during chloramination , 2000 .

[26]  David L. Sedlak,et al.  Measurement of dissolved organic nitrogen forms in wastewater effluents: concentrations, size distribution and NDMA formation potential. , 2008, Water research.

[27]  S. Canonica,et al.  Enhanced N-nitrosamine formation in pool water by UV irradiation of chlorinated secondary amines in the presence of monochloramine. , 2013, Water research.

[28]  S. Kunikane,et al.  Identification of antiyellowing agents as precursors of N-nitrosodimethylamine production on ozonation from sewage treatment plant influent. , 2009, Environmental science & technology.

[29]  S. Walse,et al.  Quaternary amines as nitrosamine precursors: a role for consumer products? , 2010, Environmental science & technology.

[30]  T. Young,et al.  NDMA formation during chlorination and chloramination of aqueous diuron solutions. , 2008, Environmental science & technology.

[31]  J. Croué,et al.  NDMA formation mechanism by chloramination of tertiary amines , 2012 .

[32]  S. Andrews,et al.  NDMA formation kinetics from three pharmaceuticals in four water matrices. , 2011, Water research.

[33]  S. Andra,et al.  Tobacco-specific nitrosamines in water: an unexplored environmental health risk. , 2011, Environment international.

[34]  Cordelia J. Hwang,et al.  Contribution of wastewater to DBP formation , 2005 .

[35]  J. Croué,et al.  Formation of NDMA and halogenated DBPs by chloramination of tertiary amines: the influence of bromide ion. , 2012, Environmental science & technology.

[36]  John Gregory,et al.  Organic polyelectrolytes in water treatment. , 2007, Water research.

[37]  Michael J. McGuire,et al.  AWWARF Trihalomethane Survey , 1988 .

[38]  Wolfgang Gernjak,et al.  Fate of N-nitrosodimethylamine, trihalomethane and haloacetic acid precursors in tertiary treatment including biofiltration. , 2011, Water research.

[39]  T. Karanfil,et al.  MIEX® treatment of an effluent‐impacted stream , 2013 .

[40]  David L Sedlak,et al.  Formation of N-nitrosodimethylamine (NDMA) from dimethylamine during chlorination. , 2002, Environmental science & technology.

[41]  R. Flowers,et al.  Anion exchange resins as a source of nitrosamines and nitrosamine precursors. , 2013, Environmental science & technology.

[42]  E. Thurman,et al.  Pharmaceuticals, hormones, and other organic wastewater contaminants in U.S. streams, 1999-2000: a national reconnaissance. , 2002 .

[43]  David L Sedlak,et al.  A N-Nitrosodimethylamine (NDMA) precursor analysis for chlorination of water and wastewater. , 2003, Water research.

[44]  R. Trussell,et al.  NDMA Formation in Water and Wastewater , 2001 .

[45]  J. A. Incavo,et al.  Simplified method for the determination of N-nitrosamines in rubber vulcanizates , 2006 .

[46]  Amy Borello Creative Engineering Through AWWA , 2012 .

[47]  Heng Liang,et al.  Reinvestigation of the nitrosamine-formation mechanism during ozonation. , 2009, Environmental science & technology.

[48]  P. Westerhoff,et al.  Dissolved organic nitrogen removal during water treatment by aluminum sulfate and cationic polymer coagulation. , 2006, Water research.

[49]  Boris Mizaikoff,et al.  Degradation of amine-based water treatment polymers during chloramination as N-nitrosodimethylamine (NDMA) precursors. , 2009, Environmental science & technology.

[50]  R. L. Valentine,et al.  Formation of N-nitrosodimethylamine (NDMA) from reaction of monochloramine: a new disinfection by-product. , 2002, Water research.

[51]  Boris Mizaikoff,et al.  PolyDADMAC and dimethylamine as precursors of N-nitrosodimethylamine during ozonation: reaction kinetics and mechanisms. , 2011, Environmental science & technology.

[52]  K. Hanaki,et al.  Removal of odorous compounds in wastewater by using activated carbon, ozonation and aerated biofilter , 1994 .

[53]  Mari Asami,et al.  A nationwide survey of NDMA in raw and drinking water in Japan. , 2009, The Science of the total environment.

[54]  David C. Stuckey,et al.  A REVIEW OF SOLUBLE MICROBIAL PRODUCTS (SMP) IN WASTEWATER TREATMENT SYSTEMS , 1999 .

[55]  R. L. Valentine,et al.  Formation of N-nitrosodimethylamine (NDMA) from humic substances in natural water. , 2007, Environmental science & technology.

[56]  Clifford C. Chan,et al.  NDMA formation from gaskets used in water storage tanks , 2014 .

[57]  P. Westerhoff,et al.  Predicting disinfection by-product formation potential in water. , 2010, Water research.

[58]  S. Hrudey,et al.  Breakpoint chlorination and free-chlorine contact time: implications for drinking water N-nitrosodimethylamine concentrations. , 2007, Water research.

[59]  K. Linge,et al.  Formation of Nitrogenous Disinfection By-Products (N-DBPs) in Raw and Treated Drinking Water , 2011 .

[60]  J. Hollender,et al.  Assessing the fate of nitrosamine precursors in wastewater treatment by physicochemical fractionation. , 2010, Environmental science & technology.

[61]  B. Spiegelhalder,et al.  Nitrosamines and rubber. , 1982, IARC scientific publications.

[62]  K. Linden,et al.  Experimental and model comparisons of low- and medium-pressure Hg lamps for the direct and H2O2 assisted UV photodegradation of N-nitrosodimethylamine in simulated drinking water. , 2003, Environmental science & technology.

[63]  M. R. Templeton,et al.  NDMA and seven other nitrosamines in selected UK drinking water supply systems , 2010 .

[64]  G. White The Handbook of Chlorination and Alternative Disinfectants , 1992 .

[65]  S. Rocks,et al.  A comparison of disinfection by-products found in chlorinated and chloraminated drinking waters in Scotland. , 2009, Water research.

[66]  J. Yu,et al.  Occurrence of nine nitrosamines and secondary amines in source water and drinking water: Potential of secondary amines as nitrosamine precursors. , 2011, Water research.

[67]  Katherine C. McKinstry,et al.  Application of an optimized total N-nitrosamine (TONO) assay to pools: placing N-nitrosodimethylamine (NDMA) determinations into perspective. , 2010, Environmental science & technology.

[68]  Elisabeth L. Hawley,et al.  Minimization of NDMA Formation during Chlorine Disinfection of Municipal Wastewater by Application of Pre-Formed Chloramines , 2005 .

[69]  U. von Gunten,et al.  Oxidative transformation of micropollutants during municipal wastewater treatment: comparison of kinetic aspects of selective (chlorine, chlorine dioxide, ferrate VI, and ozone) and non-selective oxidants (hydroxyl radical). , 2010, Water research.

[70]  William A. Mitch,et al.  Relative importance of N-nitrosodimethylamine compared to total N-nitrosamines in drinking waters. , 2013, Environmental science & technology.

[71]  B. Mariñas,et al.  Bromide ion effect on N-nitrosodimethylamine formation by monochloramine. , 2012, Environmental science & technology.

[72]  W. Mitch,et al.  Influence of the order of reagent addition on NDMA formation during chloramination. , 2005, Environmental science & technology.

[73]  Chen-yan Hu,et al.  Measurement of dissolved organic nitrogen in a drinking water treatment plant: size fraction, fate, and relation to water quality parameters. , 2011, The Science of the total environment.

[74]  B. Bolto Reaction of chlorine with organic polyelectrolytes in water treatment: A review , 2005 .

[75]  W. Kimoto,et al.  Role of strong ion exchange resins in nitrosamine formation in water , 1980 .

[76]  Unexpected Role of Activated Carbon in Promoting Transformation of Secondary Amines to , 2010 .

[77]  Mary Drikas,et al.  Nitrosamines from pipeline materials in drinking water distribution systems , 2011 .

[78]  J. Novak,et al.  Chemical Sludge Dewatering on Sand Beds , 1975 .

[79]  Chao Chen,et al.  Adsorption of N-nitrosodimethylamine precursors by powdered and granular activated carbon. , 2012, Environmental science & technology.

[80]  Jeyong Yoon,et al.  Oxidation of suspected N-nitrosodimethylamine (NDMA) precursors by ferrate (VI): kinetics and effect on the NDMA formation potential of natural waters. , 2008, Water research.

[81]  Baiyang Chen,et al.  Impact of wastewater treatment processes on organic carbon, organic nitrogen, and DBP precursors in effuent organic matter. , 2009, Environmental science & technology.

[82]  David L. Sedlak,et al.  Precursors of N-Nitrosodimethylamine in Natural Waters , 2003 .

[83]  M. R. Templeton,et al.  Occurrence and control of nitrogenous disinfection by-products in drinking water--a review. , 2011, Water research.

[84]  Andrzej Wilczak,et al.  Formation of NDMA in Chloraminated Water Coagulated with DADMAC Cationic Polymer , 2003 .

[85]  R. L. Valentine,et al.  N-nitrosodimethylamine formation by free-chlorine-enhanced nitrosation of dimethylamine. , 2003, Environmental science & technology.

[86]  R. L. Valentine,et al.  The influence of the pre-oxidation of natural organic matter on the formation of N-nitrosodimethylamine (NDMA). , 2008, Environmental science & technology.

[87]  W. Mitch,et al.  Occurrence and fate of nitrosamines and nitrosamine precursors in wastewater-impacted surface waters using boron as a conservative tracer. , 2006, Environmental science & technology.

[88]  W. Mitch,et al.  Nitrosamine formation pathway revisited: the importance of chloramine speciation and dissolved oxygen. , 2006, Environmental science & technology.

[89]  Zaid K. Chowdhury,et al.  Nationwide assessment of nitrosamine occurrence and trends , 2012 .

[90]  S. Krasner The formation and control of emerging disinfection by-products of health concern , 2009, Philosophical Transactions of the Royal Society A: Mathematical, Physical and Engineering Sciences.

[91]  P. Westerhoff,et al.  Nitrosamine, dimethylnitramine, and chloropicrin formation during strong base anion-exchange treatment. , 2009, Environmental science & technology.

[92]  P. Westerhoff,et al.  Using formation potential tests to elucidate the reactivity of dbp precursors with chlorine versus with chloramines , 2007 .

[93]  W. Mitch,et al.  Halonitroalkanes, halonitriles, haloamides, and N-nitrosamines: a critical review of nitrogenous disinfection byproduct formation pathways. , 2012, Environmental science & technology.

[94]  Jeyong Yoon,et al.  Oxidation of N-nitrosodimethylamine (NDMA) precursors with ozone and chlorine dioxide: kinetics and effect on NDMA formation potential. , 2007, Environmental science & technology.

[95]  Baiyang Chen,et al.  Occurrence of disinfection byproducts in United States wastewater treatment plant effluents. , 2009, Environmental science & technology.

[96]  J. Ridd Nitrosation, diazotisation, and deamination , 1961 .

[97]  B. Hertzberg,et al.  N-nitrosamines formation from secondary amines by nitrogen fixation on the surface of activated carbon. , 2011, Environmental science & technology.

[98]  R. Rhodes Trussell,et al.  N-Nitrosodimethylamine (NDMA) as a Drinking Water Contaminant: A Review , 2003 .

[99]  John T. Novak,et al.  The Use of Polymers for Improving Chemical Sludge Dewatering on Sand Beds , 1977 .