Photochemical Degradation of 2,4,6-Trichlorophenol in the Presence of a Nonionic Surfactant: pH Control on Reaction Kinetics
Publication: Journal of Environmental Engineering
Volume 133, Issue 6
Abstract
The photochemical degradation of 2,4,6-trichlorophenol (2,4,6-TCP) has been studied in the presence of a nonionic surfactant. A faster decay of 2,4,6-TCP could be achieved by the addition of surfactant depending on the pH levels. By examining the TCP decay at different solution pH and surfactant concentrations, the variations in photodecay rates were dominated by the existence of surfactant micelles. In water or when surfactant dosage was below the critical micellar concentration, the photodecay of 2,4,6-TCP was found to be faster at high pH levels, mainly due to the higher absorption of TCP and additional hydrogen source (from surfactant monomer). On the contrary, in the presence of micelles, faster decay of 2,4,6-TCP was obtained at lower pH levels. This was possibly due to the domination of both photochemical homolysis and electron transfer processes in acidic condition, but the latter was inhibited at alkaline condition. In addition, the cage effect of surfactant micelles may possibly hinder the -catalyzed photohydrolysis in the solution, so the TCP decay in micellar solution was reduced at high pH levels.
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Acknowledgments
The work described in this paper was fully supported by a grant from the Research Grants Council of the Hong Kong Special Administrative Region, China (Project No. UNSPECIFIEDPolyU 5038/02E).
References
Allard, A.-S., Remberger, M., Viktor, T., and Neilson, A. H. (1988). “Environmental fate of chloroguaiacols and chlorocatechols.” Water Sci. Technol., 20(2), 131–141.
Cheah, E. P. S., Reible, D. D., Valsaraj, K. T., Constant, W. D., Walsh, B. W., and Thibodeaux, L. J. (1998). “Simulation of soil washing with surfactants.” J. Hazard. Mater., 59, 107–122.
Chu, W., and Jafvert, C. T. (1994). “Photodechlorination of polychlorobenzene congeners in surfactant micelle solutions.” Environ. Sci. Technol., 28(13), 2415–2422.
Chu, W., Jafvert, C. T., Diehl, C. A., Marley, K., and Larson, R. A. (1998). “Phototransformation of polychlorobiphenyls in Brij 58 micellar solutions.” Environ. Sci. Technol., 32(13), 1989–1993.
Chu, W., and Kwan, C. Y. (2003). “Reactor design and kinetics study of -dichlorobiphenyl photodecay in surfactant solution by using a photosensitizer and hydrogen source.” Water Res., 37(10), 2442–2448.
Conrad, D. J., and Huck, P. M. (1996). “Chlorination by-products from ferulic acid (a lignin model compound) and biologically treated thermomechanical chemithermomechanical pulp mill effluents.” Water Res., 30(11), 2776–2784.
Frendler, J. H., and Fendler, E. J. (1975). Catalysis in micellar and macromolecular systems, Academic, New York, 86–103.
Galve, R., Nichkova, M., Camps, F., Sanchez-Baeza, F., and Marco, M. P. (2001). “Development and evaluation of an immunoassay for biological monitoring chlorophenols in urine as potential indicators of occupational exposure.” Anal. Chem., 74(2), 468–478.
Gehlen, M. H., Ferreira, M., and Neumann, M. G. (1995). “Interaction of methyl orange with cationic micelles and its effect on dye photochemistry.” J. Photochem. Photobiol., A, 87(1), 55–60.
Huang, G. L., Xiao, H., Chi, J., Shiu, W. Y., and Mackay, D. (2000). “Effects of pH on the aqueous solubility of selected chlorinated phenols.” J. Chem. Eng. Data, 45, 411–414
Jafvert, C. T., Health, J. K., and Van Hoof, P. L. (1994). “Solubilization of nonpolar compounds by nonionic surfactant micelles.” Water Res., 28(5), 1009–1017.
Jafvert, C. T., Van Hoof, P. L., and Chu, W. (1995). “The phase distribution of polychlorobiphenyl congeners in surfactant-amended sediment slurries.” Water Res., 29(10), 2387–2397.
Judd, M. C., Stuthridge, T. R., McFarlane, P. N., Anderson, S. M., and Bergman, I. (1996). “Bleached kraft pulp mill sourced organic chemicals in sediments from a New Zealand River. Part II: Tarawera River.” Chemosphere, 33(11), 2209–2220.
Kishino, T., and Kobayshi, K. (1996). “Studies on the mechanism of toxicity of chlorophenols found in fish through quantitative structure-activity relationships.” Chemosphere, 30(2), 393–399.
Kukkonen, J. V. K., Eadie, B. J., Oikari, A., Holmbom, B., and Lansing, M. B. (1996). “Chlorophenolic and isotopic tracers of pulp mill effluent in sedimenting particles collected from southern Lake Saimaa, Finland.” Sci. Total Environ., 188(1), 15–27.
Larson, R. A., Jafvert, C. T., Bosca, F., Marley, K. A., and Miller, P. L. (2000). “Effects of surfactants on reduction and photolysis of nitroaromatic compounds.” Environ. Sci. Technol., 34(3), 505–508.
Lyytikäinen, M., Sormunen, A., Peräniemi, S., and Kukkonen, J. V. K. (2001). “Environmental fate and bioavailability of wood preservatives in freshwater sediments near an old sawmill site.” Chemosphere, 44(3), 341–350.
Mata-Sandoval, J. C., Karns, J., and Torrents, A. (2002). “Influence of Rhamnolipids and Triton X-100 on the desorption of pesticides from soils.” Environ. Sci. Technol., 36(21), 4669–4675.
Owens, J. W., Swanson, S. M., and Birkholz, D. A. (1994). “Environmental monitoring of bleached kraft pulp mill chlorophenolic compounds in a northern Canadian river system.” Chemosphere, 29(1), 89–109.
Palm, H., and Lammi, R. (1995). “Fate of pulp mill organochlorines in the Gulf of Bothnia sediments.” Environ. Sci. Technol., 29(7), 1722–1727.
Peuravuori, J., Passo, N., and Pihlaja, K. (2002). “Sorption behaviour of some chlorophenols in lake humic matter.” Talanta, 56(3), 523–538.
Shi, Z., Sigman, M. E., Ghosh, M. M., and Dabestani, R. (1997). “Photolysis of 2-chlorophenol dissolved in surfactant solutions.” Environ. Sci. Technol., 31(12), 3581–3587.
Sithole, B. B., and Williams, D. T. (1986). “Halogenated phenols in water at 40 Canadian potable water-treatment facilities.” J. Assoc. Off. Anal. Chem., 69(5), 807.
Skurlatov, Y. I., Ernestova, L. S., Vichutinskaya, E. V., Samsonv, D. P., Semenova, I. V., Rod’ko, I. Ya., Shvidky, V. O., Pervunina, R. I., and Kemp, T. J. (1997). “Photochemical transformation of polychlorinated phenols.” J. Photochem. Photobiol., A, 107, 207–213.
U.S. Environmental Protection Agency (USEPA). (1996). “Pump-and-treat ground-water remediation—A guide for decision makers and practitioners.” USEPA/625/R-95/005, 59.
World Health Organization (WHO). (1989). “Environmental health criteria 93. Chlorophenols other than pentachlorophenol.” Geneva, Switzerland.
Yoshida, K., Shigeoka, T., and Yamamuchi, F. (1987). “Evaluation of aquatic environmental fate of 2,4,6-trichlorophenol with a mathematical model.” Chemosphere, 16(10–12), 2531–2544.
You, C. N., and Liu, J. C. (1996). “Desorptive behavior of chlorophenols in contaminated soils.” Water Sci. Technol., 33(6), 263–270.
Information & Authors
Information
Published In
Journal of Environmental Engineering
Volume 133 • Issue 6 • June 2007
Pages: 641 - 645
Copyright
© 2007 ASCE.
History
Received: Mar 17, 2004
Accepted: May 25, 2006
Published online: Jun 1, 2007
Published in print: Jun 2007
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