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Formation of Chloroform and Chlorinated Organics by Free-Chlorine-Mediated Oxidation of Triclosan
Abstract
The widely used antimicrobial agent triclosan (5-chloro-2-(2,4-dichlorophenoxy)phenol) readily reacts with free chlorine under drinking water treatment conditions. Overall second-order kinetics were observed, first-order in free chlorine and first-order in triclosan. Over the pH range of 4-11.5, the kinetics were pH sensitive as a result of the pH dependent speciation of both triclosan and free chlorine. Using a Marquardt-Levenberg routine, it was determined that this pH effect indicates that the dominant reaction in this system is between the ionized phenolate form of triclosan and hypochlorous acid (HOCl). The overall second-order rate coefficient was determined to be kArO- = 5.40 (+/- 1.82) x 10(3) M(-1) s(-1). Three chlorophenoxyphenols and two chlorophenols were identified by gas chromatographic-mass spectroscopic analysis. The chlorophenoxyphenol compounds include two monochlorinated triclosan derivatives (5,6-dichloro-2-(2,4-dichlorophenoy)phenol and 4,5-dichloro-2-(2,4-dichlorophenoxy)phenol) and one dichlorinated derivative (4,5,6-trichloro-(2,4-dichlorophenoxy)phenol); these species form via bimolecular electrophilic substitution of triclosan. 2,4-Dichlorophenol was detected under all reaction conditions and forms via ether cleavage of triclosan. In experiments with excess free chlorine, 2,4,6-trichlorophenol was formed via electrophilic substitution of 2,4-dichlorophenol. Chloroform formation was observed when an excess of free chlorine was present. A Hammett-type linear free-energy relationship (LFER) using Brown-Okamoto parameters (sigma+) was established to correlate the reactivity of HOCI and the phenolate forms of triclosan and other chlorophenols (log kArO- = -(10.7 +/- 2.2)Sigmasigma(+)o,m,p + 4.43). This LFER was used to obtain estimates of rate coefficients describing the reactivity of the intermediates 5,6-dichloro-2-(2,4-dichlorophenoy)phenol (kArO- approximately equal to 6 x 10(2)), 4,5-dichloro-2-(2,4-dichlorophenoxy)phenol (kArO- approximately equal to 3 x 10(2)), and 4,5,6-trichloro-(2,4-dichlorophenoxy)phenol (kArO- approximately equal to 4 x 10(1)).
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“Triclosan as an antibacterial agent, widely used in hand soaps, toothpastes, deodorants, mouthwash, etc., is a chlorine-sensitive compound.Its formation of chloroform and other Cl-DBPs under chlorination or chloramination has been reported (Greyshock and Vikesland, 2006;Rule et al., 2005).”
From Regulation, formation, exposure, and treatment of disinfection by-products (DBPs) in swimming pool waters: A critical review (2018) · cites this paper as Rule et al., 2005
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Triclosan: environmental exposure, toxicity and mechanisms of action
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Metadata
- Authors
- Rule, K. L., Ebbett, V. R., & Vikesland, P. J.
- Affiliations
- Department of Civil and Environmental Engineering, 418 Durham Hall, Virginia Polytechnic and State University, Blacksburg, Virginia 24060-0361
- Virginia Tech (US)
- Corresponding author
- Vikesland, Peter J.
- ORCID
- Vikesland, Peter J.
- Venue
- Environmental Science & Technology
- Publisher
- American Chemical Society (ACS)
- Published
- 2005-04-02
- Volume
- 39
- Issue
- 9
- Pages
- 3176-3185
- ISSN
- 0013-936X (ISSN-L)
- 1520-5851
- OpenAlex
- W2051663204
- Cited by
- 293
- References
- 57
- Citations by year
- 2026: 3 · 2025: 6 · 2024: 3 · 2023: 7 · 2022: 6 · 2021: 11 · 2020: 12 · 2019: 18 · 2018: 17 · 2017: 17 · 2016: 28 · 2015: 18 · 2014: 15 · 2013: 26 · 2012: 20
- FWCI
- 11.20
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Environmental Science & Technology (publishedVersion)
- PubMed (publishedVersion)
- Funders
- National Science Foundation
- Water Research Foundation
- American Water Works Association Research Foundation
- 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
- Life Sciences › Immunology and Microbiology › Applied Microbiology and Biotechnology › Antimicrobial agents and applications
- Keywords
- triclosan, free chlorine, chlorophenols, chloroform formation, disinfection by-products, drinking water disinfection, hypochlorous acid, electrophilic substitution, ether cleavage, 2,4-dichlorophenol, 2,4,6-trichlorophenol, reaction kinetics, pH dependence, antimicrobial agents
- MeSH terms
- Anti-Infective Agents, Local, Chlorine, Chloroform, Disinfection, Hydrogen-Ion Concentration, Models, Theoretical, Organic Chemicals, Oxidation-Reduction, Solvents, Triclosan, Water Purification
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