312
Views
0
CrossRef citations to date
0
Altmetric
Articles

Identification of transformation products during Doxylamine chloramination for NDMA mitigation

ORCID Icon, ORCID Icon, ORCID Icon & ORCID Icon
Pages 1024-1039 | Received 16 Dec 2021, Accepted 01 Oct 2022, Published online: 26 Oct 2022

References

  • Sacher F. Strategies for minimizing nitrosamine formation during disinfection. Scitech Book News. 2008;32.
  • Wagner ED, Hsu KM, Lagunas A, et al. Comparative genotoxicity of nitrosamine drinking water disinfection byproducts in Salmonella and mammalian cells. Mutat Res Genet Toxicol Environ Mutagen. 2012;741(1-2):109–115. doi:10.1016/j.mrgentox.2011.11.006.
  • Scanlan RA. Volatile nitrosamines in foods-an update. Dev Food Sci. 1995;37:685–704.
  • Cadwallader A, Rice-Boayue J, VanBriesen JM. Impact of nitrogen removal in wastewater treatment on NDMA formation at downstream drinking-water treatment plants. J Environ Eng. 2021;147:12. doi:10.1061/(ASCE)EE.1943-7870.0001927.
  • Charrois JWA. Detection, occurence and risk assessment of N-nitrosamines in drinking water. University of Alberta, Edmonton Alberta; 2006.
  • Mitch WA, Gerecke AC, Sedlak DL. A N-nitrosodimethylamine (NDMA) precursor analysis for chlorination of water and wastewater. Water Res. 2003a;37(15):3733–3741. doi:10.1016/S0043-1354(03)00289-6.
  • Choi J, Valentine RL. Formation of N-nitrosodimethylamine (NDMA) from reaction of monochloramine: a new disinfection by-product. Water Res. 2002;36:817–824. doi:10.1016/S0043-1354(01)00303-7.
  • Li S, Shu Y, Tang X, et al. Reaction patterns of NDMA precursors during the sequential chlorination process of short-term free chlorination and monochloramination. Sep Purif Technol. 2018;204:196–204. doi:10.1016/j.seppur.2018.04.055.
  • Mitch WA, Sedlak DL. Formation of N-nitrosodimethylamine (NDMA) from dimethylamine during chlorination. Environ Sci Technol. 2002;36(4):588–595. doi:10.1021/es010684q.
  • Zhang S, Zhou Y, Liu YD, et al. Reinvestigation of NDMA formation mechanisms from tertiary amines during chloramination: a DFT study. Environ Sci: Water Res Technol. 2020a;6(8):2078–2088. doi:10.1039/D0EW00098A.
  • Zhang X, Kim D, Freedman DL, et al. Impact of biological wastewater treatment on the reactivity of N-Nitrosodimethylamine precursors. Water Res. 2020b;186:116315, doi:10.1016/j.watres.2020.116315.
  • USEPA. (2014). Technical fact sheet –N-Nitroso-dimethylamine (NDMA). Available from: https://www.epa.gov/fedfac/technical-fact-sheet-n-nitroso-dimethylamine-ndma.
  • Hattori M. (2006). Overview on drinking water quality management in Japan [2020 June 1]. Available from: https://www.niph.go.jp/soshiki/suido/pdf/h19JPUS/abstract/r01.pdf.
  • National Water Quality Management Strategy Australian Drinking Water Guidelines 6. 2011.
  • USEPA. (2017). Technical fact sheet –N-Nitroso-dimethylamine (NDMA).
  • Guidelines for Canadian Drinking Water Quality: Guideline Technical Document N-Nitrosodimethylamine (NDMA). (2011).
  • Knight N, Watson K, Farre MJ, et al. N-nitrosodimethylamine and trihalomethane formation and minimisation in southeast Queensland drinking water. Environ Monit Assess. 2012;184(7):4207–4222. doi:10.1007/s10661-011-2256-7.
  • Krasner SW MW, McCurry DL, Hanigan D, et al. Formation, precursors, control, and occurrence of nitrosamines in drinking water: a review. Water Res. 2013;47(13):4433–4450. doi:10.1016/j.watres.2013.04.050.
  • Nawrocki J, Andrzejewski P. Nitrosamines and water. J Hazard Mater. 2011;189(1-2):1–18. doi:10.1016/j.jhazmat.2011.02.005.
  • Shen R, Andrews SA. Demonstration of 20 pharmaceuticals and personal care products (PPCPs) as nitrosamine precursors during chloramine disinfection. Water Res. 2011a;45(2):944–952. doi:10.1016/j.watres.2010.09.036.
  • Zhao Y-Y, Boyd JM, Woodbeck M, et al. Formation of N-nitrosamines from eleven disinfection treatments of seven different surface waters. Environ Sci Technol. 2008;42(13):4857–4862. doi:10.1021/es7031423.
  • Mitch WA, Sharp JO, Trussell RR, et al. N-Nitrosodimethylamine (NDMA) as a drinking water contaminant: a review. Environ Eng Sci. 2003;20(5):389–404. doi:10.1089/109287503768335896.
  • Pehlivanoglu-Mantas E, Sedlak DL. The fate of wastewater-derived NDMA precursors in the aquatic environment. Water Res. 2006a;40(6):1287–1293. doi:10.1016/j.watres.2006.01.012.
  • Pehlivanoglu-Mantas E, Sedlak DL. Wastewater-derived dissolved organic nitrogen: analytical methods, characterization, and effects—a review. Crit Rev Environ Sci Technol. 2006b;36(3):261–285.
  • Sgroi M, Vagliasindi FGA, Snyder SA, et al. N-Nitrosodimethylamine (NDMA) and its precursors in water and wastewater: A review on formation and removal. Chemosphere. 2018;191:685–703. doi:10.1016/j.chemosphere.2017.10.089.
  • Allinson M, Kadokami K, Shiraishi F, et al. Wastewater recycling in Antarctica: performance assessment of an advanced water treatment plant in removing trace organic chemicals. J Environ Manag. 2018;224:122–129. doi:10.1016/j.jenvman.2018.07.020.
  • Armbruster D, Happel O, Scheurer M, et al. Emerging nitrogenous disinfection byproducts: transformation of the antidiabetic drug metformin during chlorine disinfection of water. Water Res. 2015;79:104–118. doi:10.1016/j.watres.2015.04.020.
  • Batt AL, Kincaid TM, Kostich MS, et al. Evaluating the extent of pharmaceuticals in surface waters of the United States using a national-scale rivers and streams assessment survey. Environ Toxicol Chem. 2016;35(4):874–881. doi:10.1002/etc.3161.
  • Farre MJ, Radjenovic J, Gernjak W. Assessment of degradation byproducts and NDMA formation potential during UV and UV/H2O2Treatment of doxylamine in the presence of monochloramine. Environ Sci Technol. 2012;46(23):12904–12912. doi:10.1021/es302883n.
  • Jeon D, Kim J, Shin J, et al. Transformation of ranitidine during water chlorination and ozonation: Moiety-specific reaction kinetics and elimination efficiency of NDMA formation potential. J Hazard Mater. 2016;318:802–809. doi:10.1016/j.jhazmat.2016.06.039.
  • Qi W, Fang Yee L, Jiangyong H. Relationship between organic precursors and N-nitrosodimethylamine (NDMA) formation in tropical water sources. J Water Health. 2014;12(4):736–746. doi:10.2166/wh.2014.117.
  • Roux JL, Gallard H, Croue JP, et al. NDMA formation by chloramination of ranitidine: kinetics and mechanism. Environ Sci Technol. 2012;46(20):11095–11103. doi:10.1021/es3023094.
  • Shen R, Andrews SA. NDMA formation kinetics from three pharmaceuticals in four water matrices. Water Res. 2011b;45(17):5687–5694. doi:10.1016/j.watres.2011.08.034.
  • Shen R, Andrews SA. Formation of NDMA from ranitidine and sumatriptan: the role of pH. Water Res. 2013;47(2):802–810. doi:10.1016/j.watres.2012.11.004.
  • Wang J, Wang S. Removal of pharmaceuticals and personal care products (PPCPs) from wastewater: A review. J Environ Manag. 2016;182:620–640. doi:10.1016/j.jenvman.2016.07.049.
  • Woods GC, Sadmani AH, Andrews SA, et al. Rejection of pharmaceutically-based N-nitrosodimethylamine precursors using nanofiltration. Water Res. 2016;93:179–186. doi:10.1016/j.watres.2016.02.002.
  • Patel M, Kumar R, Kishor K, et al. Pharmaceuticals of emerging concern in aquatic systems: chemistry, occurrence, effects, and removal methods. Chem Rev. 2019;119(6):3510–3673. doi:10.1021/acs.chemrev.8b00299.
  • Vallerand A, Sanoski C, Deglin JH. (2014). Davis's drug guide for nurses. Available from: http://ebookcentral.proquest.com/lib/itup/detail.action?docID = 1716114
  • Farre MJ, Reungoat J, Argaud FX, et al. Fate of N-nitrosodimethylamine,: trihalomethane and haloacetic acid precursors in tertiary treatment including biofiltration. Water Res. 2011;45(17):5695–5704. doi:10.1016/j.watres.2011.08.033.
  • Wang X, Yang H, Zhou B, et al. Effect of oxidation on amine-based pharmaceutical degradation and N-Nitrosodimethylamine formation. Water Res. 2015;87:403–411. doi:10.1016/j.watres.2015.07.045.
  • Liu YD, Selbes M, Zeng C, et al. Formation mechanism of NDMA from ranitidine, trimethylamine, and other tertiary amines during chloramination: a computational study. Environ Sci Technol. 2014;48(15):8653–8663. doi:10.1021/es500997e.
  • Pham HT, Wahman DG, Fairey JL. Updated reaction pathway for dichloramine decomposition: formation of reactive nitrogen species and N-nitrosodimethylamine. Environ Sci Technol. 2021;55(3):1740–1749. doi:10.1021/acs.est.0c06456.
  • Schreiber IM, Mitch WA. Nitrosamine formation pathway revisited:  The importance of chloramine speciation and dissolved oxygen. Environ Sci Technol. 2006;40(19):6007–6014.
  • Zhang A, Li Y, Song Y, et al. Characterization of pharmaceuticals and personal care products as N-nitrosodimethylamine precursors during disinfection processes using free chlorine and chlorine dioxide. J Hazard Mater. 2014;276:499–509. doi:10.1016/j.jhazmat.2014.05.069.
  • Schymanski EL, Singer HP, Slobodnik J, et al. Non-target screening with high-resolution mass spectrometry: critical review using a collaborative trial on water analysis. Anal Bioanal Chem. 2015;407(21):6237–6255. doi:10.1007/s00216-015-8681-7.
  • Topuz E, Aydin E, Pehlivanoglu-Mantas E. A practical LC-MS/MS method for the detection of NDMA at nanogram per liter concentrations in multiple water matrices. Water Air Soil Pollut. 2012;223(9):5793–5802. doi:10.1007/s11270-012-1315-1.
  • Gonzalez de Vega R, Cameron A, Clases D, et al. Simultaneous targeted and non-targeted analysis of per- and polyfluoroalkyl substances in environmental samples by liquid chromatography-ion mobility-quadrupole time of flight-mass spectrometry and mass defect analysis. J Chromatogr A. 2021;1653:Article 462423, doi:10.1016/j.chroma.2021.462423.
  • Kunzelmann M, Winter M, Aberg M, et al. Non-targeted analysis of unexpected food contaminants using LC-HRMS. Anal Bioanal Chem. 2018;410(22):5593–5602. doi:10.1007/s00216-018-1028-4.
  • Panagopoulos Abrahamsson D, Wang A, Jiang T, et al.. A comprehensive non-targeted analysis study of the prenatal exposome. Environ Sci Technol. 2021;55(15):10542–10557. doi:10.1021/acs.est.1c01010.
  • Sanchis J, Redondo-Hasselerharm PE, Villanueva CM, et al. Non targeted screening of nitrogen containing disinfection by-products in formation potential tests of river water and subsequent monitoring in tap water samples. Chemosphere. 2022;303(Pt 2):135087, doi:10.1016/j.chemosphere.2022.135087.
  • Sobus JR, Wambaugh JF, Isaacs KK, … Newton SR. Integrating tools for non-targeted analysis research and chemical safety evaluations at the US EPA. J Expo Sci Environ Epidemiol. 2018;28(5):411–426. doi:10.1038/s41370-017-0012-y.
  • Hanigan D, Ferrer I, Thurman EM, et al. LC/QTOF-MS fragmentation of N-nitrosodimethylamine precursors in drinking water supplies is predictable and aids their identification. J Hazard Mater. 2017;323(Pt A):18–25. doi:10.1016/j.jhazmat.2016.04.023.
  • Krauss M, Hollender J. Analysis of nitrosamines in wastewater: exploring the trace level quantification capabilities of a hybrid linear ion trap/orbitrap mass spectrometer. Anal Chem. 2008;80:834–842.
  • Chen Z, Fang J, Fan C, et al. Oxidative degradation of N-Nitrosopyrrolidine by the ozone/UV process: kinetics and pathways. Chemosphere. 2016;150:731–739. doi:10.1016/j.chemosphere.2015.12.046.
  • Hu H, Jiang C, Ma H, et al.. Removal characteristics of DON in pharmaceutical wastewater and its influence on the N-nitrosodimethylamine formation potential and acute toxicity of DOM. Water Res. 2017;109:114–121. doi:10.1016/j.watres.2016.10.010.
  • Gan W, Bond T, Yang X, et al. Role of chlorine dioxide inN-nitrosodimethylamine formation from oxidation of model amines. Environ Sci Technol. 2015;49(19):11429–11437. doi:10.1021/acs.est.5b01729.
  • Seid MG, Chung J, Choe J, et al. Role of ranitidine in N-nitrosodimethylamine formation during chloramination of competing micropollutants. Sci Total Environ. 2021;756:144156, doi:10.1016/j.scitotenv.2020.144156.
  • Hatt J W, Lamy C, Germain E, Tupper M, Judd S, Jeng NDMA formation in secondry wastewater effluent. Chemosphere. 2013; 91(1), 83–7. doi: 10.1016/j.chemosphere.2012.11.003

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.