Aqueous Chlorination of Diclofenac: Kinetic Study and Transformation Products Identification
Abstract
Diclofenac reactivity and fate during water chlorination was investigated in this work. In the first step, chlorination kinetic of diclofenac (DCF) was studied in the pH range of 4-10 at 20 ± 2 °C and in the presence of an excess of total chlorine. A second-order reaction (first-order relative to DCF concentration and first-order relative to free chlorine concentration) was shown with rate constant about 3.89 ± 1.17 M(-1) s(-1) at pH 7. The elementary reactions (i.e. reactions of hypochlorous acid (HOCl) with neutral and ionized forms of DCF, and acid-catalysed reaction of HOCl with neutral and ionized forms of DCF) were proposed to explain the pH-dependence of the rate constants and intrinsic constant of each of them were calculated. In the second step, several degradation products formed during chlorination of DCF were identified. These compounds could come from an initial chlorine electrophilic attack on aromatic ring or amine function of DCF. Some of these chlorinated derivatives seem to accumulate in solution in the presence of an excess of chlorine.
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Common drugs including metformin, diclofenac, and tamoxifen entering freshwater sources are subject to direct chlorination causing drinking water contamination associated with largely unexplored implications for human health.
“For example, common drugs including metformin, diclofenac, and tamoxifen entering freshwater sources are subject to direct chlorination causing drinking water contamination associated with largely unexplored implications for human health (126–129).”
From Hypochlorous Acid: From Innate Immune Factor and Environmental Toxicant to Chemopreventive Agent Targeting Solar UV-Induced Skin Cancer (2022) · cites this paper as [126]
PPCPs introduced into the water supply are subject to HOCl-mediated chlorination and subsequent formation of CBPs.
“Additionally, PPCPs introduced into the water supply are subject to HOCl-mediated chlorination and subsequent formation of CBPs.”
From Hypochlorous Acid: From Innate Immune Factor and Environmental Toxicant to Chemopreventive Agent Targeting Solar UV-Induced Skin Cancer (2022) · cites this paper as [126]
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- Authors
- Soufan, M., Deborde, M., & Legube, B.
- Affiliations
- Centre National de la Recherche Scientifique (FR)
- Corresponding author
- Deborde, M.
- ORCID
- Deborde, M.
- Venue
- Water Research
- Publisher
- Elsevier BV
- Published
- 2012-06
- Volume
- 46
- Issue
- 10
- Pages
- 3377-3386
- ISSN
- 0043-1354 (ISSN-L)
- OpenAlex
- W2052824194
- Cited by
- 128
- References
- 34
- Citations by year
- 2026: 5 · 2025: 6 · 2024: 5 · 2023: 12 · 2022: 9 · 2021: 7 · 2020: 8 · 2019: 10 · 2018: 11 · 2017: 8 · 2016: 7 · 2015: 15 · 2014: 13 · 2013: 10 · 2012: 2
- FWCI
- 8.85
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Water Research (publishedVersion)
- PubMed (publishedVersion)
- HAL (submittedVersion)
- 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 › Environmental Science › Pollution › Pharmaceutical and Antibiotic Environmental Impacts
- Keywords
- diclofenac, aqueous chlorination, chlorination kinetics, degradation intermediates, hypochlorous acid, pH dependence, second-order reaction, free chlorine, drug degradation, water disinfection by-products
- MeSH terms
- Chlorine, Chromatography, Liquid, Diclofenac, Hydrogen-Ion Concentration, Kinetics, Models, Chemical, Oxidation-Reduction, Solutions, Spectrophotometry, Ultraviolet, Mass Spectrometry, Water Pollutants, Chemical, Halogenation
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