The DOI matches its Crossref record; 28 of the 28 references it cites were found in a registry or an index.
Oxidative Transformation of Triclosan and Chlorophene by Manganese Oxides
Abstract
The antibacterial agents triclosan (5-chloro-2-(2,4-dichlorophenoxy)phenol) and chlorophene (4-chloro-2-(phenylmethyl)phenol) show similar susceptibility to rapid oxidation by manganese oxides (delta-MnO2 and MnOOH) yielding Mn(II) ions. Both the initial reaction rate and adsorption of triclosan to oxide surfaces increase as pH decreases. The reactions are first-order with respect to the antibacterial agent and MnO2. The apparent reaction orders to H+ were determined to be 0.46 +/- 0.03 and 0.50 +/- 0.03 for triclosan and chlorophene, respectively. Dissolved metal ions (Mn(II), Zn(II), and Ca(II)) and natural organic matter decrease the reaction rate by competitively adsorbing and reacting with MnO2. Product identification indicates that triclosan and chlorophene oxidation occurs at their phenol moieties and yields primarily coupling and p-(hydro)quinone products. A trace amount of 2,4-dichlorophenol is also produced in triclosan oxidation, suggesting bond-breaking of the ether linkage. The experimental results support the mechanism that after formation of a surface precursor complex of the antibacterial agent and the surface-bound Mn(IV), triclosan and chlorophene are oxidized to phenoxy radicals followed by radical coupling and further oxidation to form the end products. Compared to several structurally related substituted phenols (i.e., 2-methyl-4-chlorophenol, 2,4-dichlorophenol, 3-chlorophenol, and phenol), triclosan and chlorophene exhibit comparable or higher reactivities toward oxidation by manganese oxides. The higher reactivities are likely affected by factors including electronic and steric effects of substituents and compound hydrophobicity. Once released into the environment, partitioning of triclosan and chlorophene to soils and sediments is expected because of their relatively hydrophobic nature. Results of this study indicate that manganese oxides in soils will facilitate transformation of these antibacterial agents.
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Cites
Kolpin, D. W., Furlong, E. T., Meyer, M. T., Thurman, E. M., Zaugg, S. D., Barber, L. B., & Buxton, H. T. (2002) · Environmental Science & Technology · doi:10.1021/es011055j · Cited by 7,953
Triclosan targets lipid synthesis
McMurry, L. M., Oethinger, M., & Levy, S. B. (1998) · Nature · doi:10.1038/28970 · Cited by 1,019
Orvos, D. R., Versteeg, D. J., Inauen, J., Capdevielle, M., Rothenstein, A., & Cunningham, V. (2002) · Environmental Toxicology and Chemistry · doi:10.1002/etc.5620210703 · Cited by 629
Lindström, A., Buerge, I. J., Poiger, T., Bergqvist, P.-A., Müller, M. D., & Buser, H.-R. (2002) · Environmental Science & Technology · doi:10.1021/es0114254 · Cited by 537
Reductive Dissolution of Manganese(III/Iv) Oxides by Substituted Phenols
Stone, A. T. (1987) · Environmental Science & Technology · doi:10.1021/es50001a011 · Cited by 523
Molecular basis of triclosan activity
Levy, C. W., Roujeinikova, A., Sedelnikova, S., Baker, P. J., Stuitje, A. R., Slabas, A. R., Rice, D. W., & Rafferty, J. B. (1999) · Nature · doi:10.1038/18803 · Cited by 518
The surface chemistry of hydrous manganese dioxide
Murray, J. W. (1974) · Journal of Colloid and Interface Science · doi:10.1016/0021-9797(74)90045-9 · Cited by 505
Measurement of triclosan in wastewater treatment systems
McAvoy, D. C., Schatowitz, B., Jacob, M., Hauk, A., & Eckhoff, W. S. (2002) · Environmental Toxicology and Chemistry · doi:10.1002/etc.5620210701 · Cited by 448
Stone, A. T., & Morgan, J. J. (1984) · Environmental Science & Technology · doi:10.1021/es00126a010 · Cited by 437
Colloid-chemical properties of manganese dioxide
Morgan, J. J., & Stumm, W. (1964) · Journal of Colloid Science · doi:10.1016/0095-8522(64)90036-4 · Cited by 386
Cited by
A critical review of the reactivity of manganese oxides with organic contaminants
Remucal, C. K., & Ginder-Vogel, M. (2014) · Environmental Science: Processes & Impacts · doi:10.1039/c3em00703k · Cited by 375
Formation of chloroform and chlorinated organics by free-chlorine-mediated oxidation of triclosan
Rule, K. L., Ebbett, V. R., & Vikesland, P. J. (2005) · Environmental Science & Technology · doi:10.1021/es048943+ · Cited by 293
Metadata
- Authors
- Zhang, H., & Huang, C.-H.
- Venue
- Environmental Science & Technology
- Publisher
- American Chemical Society (ACS)
- Published
- 2003-04-26
- Volume
- 37
- Issue
- 11
- Pages
- 2421-2430
- ISSN
- 0013-936X (ISSN-L)
- 1520-5851
- OpenAlex
- W2000153282
- Cited by
- 386
- References
- 28
- FWCI
- 9.43
- Type
- journal article
- Language
- en
- Open access
- closed
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