Abstract
Since nitrosamine disinfection by products is highly carcinogenic, they have attracted considerable attention due to their increased presence in ambient waterways and potable water supplies. For the present study, the potential formation of nitrosamines from corresponding precursor secondary amines during ozonation was investigated. The results revealed that five nitrosamines were observed during the ozonation of their corresponding secondary amines. The molar yields initially increased and then decreased with longer contact times and higher ozone doses. These phenomena indicated that ozone not only promoted nitrosamine formation but also degraded the formed nitrosamines. High pH had a positive influence on nitrosamine formation at room temperature. Further, coexisting substances including nitrate, nitrite, humic acid, and tert-butanol inhibited the generation of nitrosamines due to hydroxyl radical (·OH) competition and scavengers, whereas in the presence of hydroxylamine, nitrosamine formation increased considerably without ozone due to its capacity for independent formation between secondary amines and hydroxylamine. Further, the generation of nitrosamines from secondary amines was primarily attributed to O3 and ·OH oxidation, which was produced through the decomposition of ozone. The transformation pathways were mainly comprised of the indirect routes between the O3/·OH intermediates. The findings of this study were helpful toward expanding the knowledge of nitrosamine formation during the corresponding precursor secondary amine ozonation process.
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References
Andrzejewskia, P., Kasprzyk-Hordern, B., & Nawrocki, J. (2008). N-nitrosodimethylamine (NDMA) formation during ozonation of dimethylamine-containing waters. Water Research, 42, 863–870.
Asami, M., Oya, M., & Kosaka, K. (2009). A nationwide survey of NDMA in raw and drinking water in Japan. Science of the Total Environment, 407(11), 3540–3545.
Chen, W. H., & Thomas, M. Y. (2008). NDMA formation during chlorination and chloramination of aqueous diuron solutions. Environmental Science & Technology, 42, 1072–1077.
Chen, W. H., & Thomas, M. Y. (2009). Influence of nitrogen source on NDMA formation during chlorination of diuron. Water Research, 43, 3047–3056.
Choi, J., & Valentine, R. L. (2002). Formation of N-nitrosamine (NDMA) from reaction of monochloramone: a new disinfection by-product. Water Research, 36, 817–824.
Dries, J., Bastiaens, L., Springael, D., Kuypers, S., Agathos, S. N., & Diels, L. (2005). Effect of humic acids on heavy metal removal by zero-valent iron in batch and continuous flow column systems. Water Research, 39(15), 3531–3540.
Krasner, S. W., Mitch, W. A., Mccurry, D. L., Hanigan, D., & Westerhoff, P. (2013). Formation, precursors, control, and occurrence of nitrosamines in drinking water: a review. Water Research, 47(13), 4433–4450.
Lim, S., Lee, W., Na, S. Y., Shin, J., & Lee, Y. H. (2016). N-nitrosodimethylamine (NDMA) formation during ozonation of N,N-dimethylhydrazine compounds: reaction kinetics, mechanisms, and implications for NDMA formation control. Water Research, 105, 119–128.
Lv, J., Li, Y. M., & Song, Y. (2013). Reinvestigation on the ozonation of N-nitrosodimethylamine: influencing factors and degradation mechanism. Water Resarch, 47, 4993–5002.
Lv, J., Wang, L., Song, Y., & Lia, Y. M. (2015). N-nitrosodimethylamine formation from ozonation of chlorpheniramine: influencing factors and transformation mechanism. Journal of Hazardous Materials, 299, 584–594.
Marti, E. J., Pisarenko, A. N., Peller, J. R., & Dickenson, E. J. R. (2015). N-nitrosodimethylamine (NDMA) formation from the ozonation of model compounds. Water Research, 72, 262–270.
Oya, M., Kosaka, K., Asami, M., & Kunikane, S. (2008). Formation of N-nitrosodimethylamine (NDMA) by ozonation of dyes and related compounds. Chemosphere, 73(11), 1724–1730.
Park, S. H., Wei, S., Mizaikoff, B., Taylor, A. E., Favero, C., & Huang, C. H. (2009). Degradation of amine-based water treatment polymers during chloramination as N-nitrosodimethylamine (NDMA) precursors. Environmental Science & Technology, 43(5), 1360–1366.
Schmidt, C. K., & Brauch, H. J. (2008). N,n-dimethylsulfamide as precursor for N-nitrosodimethylamine (NDMA) formation upon ozonation and its fate during drinking water treatment. Environmental Science & Technology, 42(17), 6340–6346.
Shen, R., & Andrews, S. A. (2010). Demonstration of 20 pharmaceuticals and personalcare products (PPCPs) as nitrosamine precursors during chloraminedisinfection. Water Research, 45, 944–952.
U.S. Environmental Protection Agency. (2009). Contaminant Candidate List3 (CCL3). https://www.epa.gov/ccl/contaminant-candidate-list-3-ccl-3. Accessed 31 Aug 2018.
U.S. Environmental Protection Agency. (2012). Integrated Risk Information System: N-nitrosodimethylamine (CASRN 62-75-9). https://cfpub.epa.gov/ncea/iris2/chemicalLanding.cfm?substance_nmbr=45. . Accessed 31 Aug 2018.
Von Gunten, U. (2003). Ozonation of drinking water: part I. Oxidation kinetics and product formation. Water Research, 37, 1443–1467.
Von Gunten, U., Salhi, E., Schmidt, C. K., & Arnold, W. A. (2010). Kinetics and mechanisms of N-nitrosodimethylamine formation upon ozonation of N, n-dimethylsulfamide containing waters: bromide catalysis. Environmental Science & Technology, 44(15), 5762–5768.
Wang, W. F., Ren, S. Y., Zhang, H. F., Yu, J. W., Hu, J. Y., & Yang, M. (2011). Occurrence of nine nitrosamines and secondary amines in source water and drinking water: potential of secondary amines as nitrosamine precursors. Water Research, 45, 4930–4938.
Wang, W. F., Yu, J. W., An,W., Yang, M. (2016). Occurrence and profiling of multiple nitrosamines in source water and drinking water of China. Science of the Total Environment, 551–552, 489–495.
William, H. G., & Kang, J. W. (1989). Advanced oxidation processes. Description of a kinetic model for the oxidation of hazardous materials in aqueous media with ozone and hydrogen peroxide in a semibatch reactor. Industrial & Engineering Chemistry Research, 28, 1573–1580.
Yang, L., Chen, Z., Shen, J., Xu, Z., Liang, H., Tian, J., Ben, Y., Zhai, X., Shi, W., & Li, G. (2009). Reinvestigation of the nitrosamine formation mechanism during ozonation. Environmental Science & Technology, 43, 5481–5487.
Yang, J. X., Li, J., Dong, W. Y., & Ma, J. (2016). Study on enhanced degradation of atrazine by ozonation in the presence of hydroxylamine. Journal of Hazardous Materials, 316, 110–121.
Yoon, S., & Tanaka, H. (2014). Formation of N-nitrosamines by chloramination or ozonation of amines listed in Pollutant Release and Transfer Registers (PRTRs). Chemosphere, 95, 88–95.
Zhang, S. Y., Yu, G., Chen, L. W., Wang, B., Huang, J., & Deng, S. B. (2014). Unveiling formation mechanisms of carcinogenic N-nitrosodimethylamine in ozonation of dimethylamine: a density functional theoretical investigation. Journal of Hazardous Materials, 279, 330–335.
Zhao, Y., Boyd, J. M.,Woodbeck, M., Andrews, R. C., Qin, F., Hrudey, S. E., Li, X. (2008). Formation of N-nitrosamines from eleven disinfection treatments of seven different surface waters. Environmental Science Technology 42(13), 4857–4862.
Acknowledgements
We thank Mr. Frank Boehm from Lakehead University in Canada, for reviewing the paper and correcting the English.
Funding
This work was supported by the National Special Funding Project for Water Pollution Control and Management of China (2014ZX07405001); the National Natural Science Foundation of China (No. 51208184); the special fund of Key Laboratory of Drinking Water Science and Technology, Research Center for Eco-Environmental Sciences, Chinese Academy of Sciences (Project No. 18K04KLDWST); and the Technology Department of the Henan Science and Technology Fund Project (No. 172102310590).
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Wang, W., Liang, F., Guo, Y. et al. Formation of Multiple Nitrosamines from the Ozonation of Corresponding Precursor Secondary Amines: Influencing Factors and Transformation Mechanisms. Water Air Soil Pollut 230, 41 (2019). https://doi.org/10.1007/s11270-019-4091-3
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DOI: https://doi.org/10.1007/s11270-019-4091-3