Kinetics and mechanisms of pH-dependent degradation of halonitromethanes by UV photolysis
Abstract
Halonitromethanes (HNMs) are one of the most toxic groups of disinfection by-products. The pH-dependent degradation kinetics and pathways of four HNMs, namely bromonitromethane (BNM), dichloronitromethane (DCNM), dibromonitromethane (DBNM) and trichloronitromethane (TCNM), by ultraviolet (UV) photolysis at 254 nm were studied at pH 3-9. The UV photolysis in a dilute aqueous solution followed first-order kinetics. The photolysis rates of all four HNMs were low at pH 3-5, while that of TCNM was low at all pHs tested. Nevertheless, the photolysis rates of BNM, DCNM and DBNM increased with increasing pH, showing sharp increases as the pH neared their pK(a) values. The increases were correlated with their pH-dependent molar absorptivities, which were determined by the sizes of their deprotonated fractions. Homolysis was likely to be the major photolysis pathway for all four HNMs to produce halides, nitrite and nitrate at acidic pHs when the HNMs were not deprotonated. At high pHs, however, the conjugation systems of the deprotonated mono- and di-HNMs made heterolysis possibly the dominant pathway for the formation of carbon dioxide, nitrite and halides as major products for di-HNMs, and the formation of nitrite, halides and other unknown organics for mono-HNMs. The UV energy required for a 50% degradation of deprotonated HNMs in the real water sample was similar to that needed in UV disinfection processes, suggesting the effectiveness of UV photolysis in controlling HNMs that form conjugation systems at neutral to alkaline pHs.
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HNMs underwent homolysis or heterolysis to produce halides, nitrite, nitrate, and/or carbon dioxide under UV254 radiation.
“HNMs underwent homolysis or heterolysis to produce halides, nitrite, nitrate, and/or carbon dioxide under UV254 radiation (Fang et al., 2013).”
From Regulation, formation, exposure, and treatment of disinfection by-products (DBPs) in swimming pool waters: A critical review (2018) · cites this paper as Fang et al., 2013
Neutral to alkaline pHs typical for swimming pool waters contribute to HNM degradation due to their high UV molar absorptivity at these pHs.
“Neutral to alkaline pHs which are typical for SPWs, contribute to HNM degradation due to their high UV molar absorptivity at these pHs.”
From Regulation, formation, exposure, and treatment of disinfection by-products (DBPs) in swimming pool waters: A critical review (2018) · cites this paper as Fang et al., 2013
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- Authors
- Fang, J.-Y., Ling, L., & Shang, C.
- Affiliations
- Hong Kong University of Science and Technology (HK)
- Corresponding author
- Shang, Chii
- ORCID
- Venue
- Water Research
- Publisher
- Elsevier BV
- Published
- 2013-03
- Volume
- 47
- Issue
- 3
- Pages
- 1257-1266
- ISSN
- 0043-1354 (ISSN-L)
- OpenAlex
- W2072396093
- Cited by
- 88
- References
- 33
- Citations by year
- 2026: 2 · 2025: 3 · 2024: 9 · 2023: 7 · 2022: 8 · 2021: 7 · 2020: 9 · 2019: 7 · 2018: 9 · 2017: 8 · 2016: 9 · 2015: 6 · 2014: 2 · 2013: 2
- FWCI
- 2.22
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Water Research (publishedVersion)
- PubMed (publishedVersion)
- Rare & Special e-Zone (The Hong Kong University of Science and Technology) (submittedVersion)
- Funders
- Research Grants Council of Hong Kong
- Topics
- Physical Sciences › Environmental Science › Health, Toxicology and Mutagenesis › Water Treatment and Disinfection
- Physical Sciences › Environmental Science › Water Science and Technology › Advanced oxidation water treatment
- Physical Sciences › Energy › Renewable Energy, Sustainability and the Environment › Advanced Photocatalysis Techniques
- Keywords
- halonitromethanes, disinfection by-products, UV photolysis, pH-dependent degradation, bromonitromethane, chloropicrin, photolysis kinetics, homolysis, heterolysis, deprotonation, nitrite production, ultraviolet disinfection, water treatment
- MeSH terms
- Bromides, Ethane, Hydrocarbons, Chlorinated, Hydrogen-Ion Concentration, Kinetics, Methane, Nitro Compounds, Photolysis, Ultraviolet Rays, Halogenation
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