Trace determination and occurrence of eight chlorophenylacetonitriles: An emerging class of aromatic nitrogenous disinfection byproducts in drinking water

Zhang, Di; Bond, Tom; Krasner, Stuart W.; Chu, Wenhai; Pan, Yang; Xu, Bin; Yin, Daqiang

doi:10.1016/j.chemosphere.2018.12.127

Cited by 43 publications

(19 citation statements)

References 37 publications

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“…To ensure an adequate reaction between chlorine and organic matter, FP tests was performed over 24 h. , The samples were kept in the dark in a 25 °C thermostatic incubator for 24 h. At prescribed reaction times, sodium sulfite at 120% of molality of chlorine was added to quench the residual chlorine. Following this, a solid-phase extraction (SPE) preconcentration procedure was conducted according to the previous work . Finally, 1 mL of the extract was obtained for subsequent CPAN determination.…”

Section: Materials and Methodsmentioning

confidence: 99%

“…Following this, a solid-phase extraction (SPE) preconcentration procedure was conducted according to the previous work. 22 Finally, 1 mL of the extract was obtained for subsequent CPAN determination. FP tests for the water sample were performed within 72 h after the samples were initially collected.…”

Section: Chemicals and Reagentsmentioning

confidence: 99%

“…Numerous epidemiologic and metabolomic observations have identified associations between the long-term consumption of chlorinated drinking water and adverse health risks such as abnormal pregnancy outcomes, bladder cancer, and cardiac birth defects. − Many researchers have aimed to identify the DBP that may act as toxicity drivers in drinking water. − Since chloroform was first reported in chlorinated drinking water in the 1970s, more than 800 DBPs have been identified and confirmed. − Trihalomethanes (THMs) and haloacetic acids (HAAs), carbonaceous DBPs (C-DBPs), are currently regulated by the United States Environmental Potency Agency, but no evidence has shown that they are drivers of elevated bladder cancer risk. , Nitrogenous DBPs (N-DBPs) are reported to be more toxic than C-DBPs. , Recently, a number of aromatic DBPs have been identified in drinking waters. − Aromatic DBPs are of concern due to their high toxicity, often 3 to 4 orders of magnitude higher than regulated DBPs. , Furthermore, it has been reported that the metabolic rate of aromatic nitrogenous groups in heterotrophic organisms was significantly lower than that of non-nitrogenous aromatic groups, indicating they are slowly metabolized by humans. , In other words, aromatic N-DBPs in drinking water may be important components of the overall toxicity. Recently, chlorophenylacetonitriles (CPANs), an emerging class of aromatic N-DBPs, have been identified in drinking water. , Chronic cytotoxicity tests based on Chinese hamster ovarian (CHO) cells have shown that the CPANs are 2 to 3 orders of magnitude more cytotoxic than regulated THMs and HAAs. Furthermore, they are quite stable during drinking water distribution.…”

Section: Introductionmentioning

confidence: 99%

“…Recently, chlorophenylacetonitriles (CPANs), an emerging class of aromatic N-DBPs, have been identified in drinking water. 21,22 Chronic cytotoxicity tests based on Chinese hamster ovarian (CHO) cells have shown that the CPANs are 2 to 3 orders of magnitude more cytotoxic than regulated THMs and HAAs. Furthermore, they are quite stable during drinking water distribution.…”

Section: ■ Introductionmentioning

confidence: 99%

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Ozonation Treatment Increases Chlorophenylacetonitrile Formation in Downstream Chlorination or Chloramination

Zhang

Bond

et al. 2021

Environ. Sci. Technol.

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Chlorophenylacetonitriles (CPANs) are an emerging group of aromatic nitrogenous disinfection byproducts (DBPs). However, their dominant precursors and formation pathways remain unclear, which hinders the further development of effective control strategies. For the first time, CPAN precursors were screened by conducting formation potential (FP) tests on real water samples from six drinking water treatment plants (DWTPs). The average overall removal of CPAN precursors across all six DWTPs was only 10%. Moreover, ozonation increased CPAN precursors by 140% on average. Fluorescence spectroscopy showed a dramatic reduction in aromatic proteins, tyrosine-like proteins, and tryptophan-like proteins following ozonation. Low-apparent-molecular-weight (AMW) (<1 kDa) substances were correlated with the CPAN FP in these samples. We therefore hypothesized that protein fragments with low AMW, such as amino acids, are important CPAN precursors during downstream chlor(am)ination. Two aromatic free amino acids, tyrosine and tryptophan, were selected to investigate the formation of CPANs during chlor(am)ination. Both amino acids were found to act as CPAN precursors for the first time. CPAN formation pathways from these model precursors were proposed based on the frontier molecular orbital theory and intermediate products identified using high-resolution mass spectrometry. This study provides a powerful theoretical foundation for controlling CPAN formation in drinking water.

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Section: Materials and Methodsmentioning

confidence: 99%

Section: Chemicals and Reagentsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Ozonation Treatment Increases Chlorophenylacetonitrile Formation in Downstream Chlorination or Chloramination

Zhang

Bond

et al. 2021

Environ. Sci. Technol.

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“…It was found that the eight new DBPs were ubiquitously present in the two real drinking water samples at levels between 0.47 (5-bromo-2-chloro-3-pyridinol) to 5.21 ng/L (3,5,6-trichloro-2-pyridinol) in sample A and 0.18 (2,6-dibromo-3-pyridinol) to 3.44 ng/L (3,5,6-trichloro-2-pyridinol) in sample B. For the other two emerging groups of aromatic N-DBPs, halogenated phenylacetonitriles and dipeptides, they were also reported at nanogram/liter levels in real water samples. ,, …”

Section: Results and Discussionmentioning

confidence: 95%

A New Group of Heterocyclic Nitrogenous Disinfection Byproducts (DBPs) in Drinking Water: Role of Extraction pH in Unknown DBP Exploration

Tang

Zhong

Pan

et al. 2021

Environ. Sci. Technol.

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pH adjustment prior to extraction is an important step in water sample pretreatment processes for exploration of new/unknown disinfection byproducts (DBPs) in drinking water. To achieve a better extraction efficiency, the pH of a water sample is usually adjusted to a low level (e.g., < 0.5) to ensure that target DBPs are in their neutral forms. However, such a practice may elude some amphoteric DBPs (especially those nitrogenous DBPs with multiple functional groups), which can accept protons at a low pH and lose protons at a high pH. In this study, with careful extraction pH selection and optimization, we first report the detection and identification of a new group of heterocyclic nitrogenous DBPs, halogenated pyridinols, in simulated drinking water using ultra performance liquid chromatography/electrospray ionization-triple quadrupole mass spectrometry and time-of-flight mass spectrometry, including 5-chloro-3-pyridinol, 2-bromo-3-pyridinol, 2,6-dichloro-4-pyridinol, 2,6-dibromo-3-pyridinol, 3-bromo-2-chloro-5-pyridinol, 5-bromo-2-chloro-3-pyridinol, 3,5,6-trichloro-2-pyridinol, and 2,4,6-tribromo-3-pyridinol. On the basis of the speciation of dissociated chemical species and recovery tests at different extraction pH values, it was found that, only at a pH of 3.0, all the eight new DBPs could achieve recoveries of >50%. With subsequent instrumental parameter optimization, the method detection and quantitation limits of the eight new DBPs were determined to be 0.04–1.58 and 0.15–4.11 ng/L, respectively. The optimized method enabled an accurate detection of the eight new DBPs in two real drinking water samples. Further aided with in vivo developmental and acute toxicity assays using zebrafish embryos, the developmental and acute toxicity of the new DBPs were found to be slightly lower than those of halogenated benzoquinones but dozens of times higher than those of commonly known DBPs such as tribromomethane and iodoacetic acid.

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Formation, Analysis, and Removal of Halogenated Cyclic DBPs

Meng,

Zhou,

Xie

et al. 2024

The Handbook of Environmental Chemistry

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Trace determination and occurrence of eight chlorophenylacetonitriles: An emerging class of aromatic nitrogenous disinfection byproducts in drinking water

Cited by 43 publications

References 37 publications

Ozonation Treatment Increases Chlorophenylacetonitrile Formation in Downstream Chlorination or Chloramination

Ozonation Treatment Increases Chlorophenylacetonitrile Formation in Downstream Chlorination or Chloramination

A New Group of Heterocyclic Nitrogenous Disinfection Byproducts (DBPs) in Drinking Water: Role of Extraction pH in Unknown DBP Exploration

Formation, Analysis, and Removal of Halogenated Cyclic DBPs

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