TECHNICAL PAPERS
May 1, 1999

Kinetic and Mechanistic Study of Ozonation of Three Dichlorophenols in Aqueous Solutions

Publication: Journal of Environmental Engineering
Volume 125, Issue 5

Abstract

This research investigates the kinetic parameters associated with the ozonation of 2,3-, 2,4-, and 2,5-dichlorophenols (DCPs) in aqueous solutions at 25°C. The overall ozonation kinetics of each DCP was found to be first order with respect to each reactant concentration (i.e., DCP and ozone). Among the three isomers studied, the ozonation of 2,5-DCP was the fastest with the overall rate constant varying from 68,500 to 7,750,000 M−1 s−1 within a pH range of 2.1 to 5.0. The overall rate constant increased with pH because of the increase in the degree of dissociation of the DCP molecules to dichlorophenoxide ions. The electrophilic addition of ozone at the ortho and para positions of the molecular and ionic forms of the DCPs was postulated to be the likely mechanism for the degradation of the DCPs to chlorobenzenediols, monochlorophenols, chlorocyclohexadienediones, ethylacetate, heptanone, carboxylic acids, and other by-products that were detected using gas chromatograph/mass spectrometry analysis.

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References

1.
Ahlborg, U. G., and Thunberg, T. M. ( 1980). “Chlorinated phenols: Occurrence, toxicity, metabolism and environmental impact.” CRC Critical Rev. in Tox., 7(1), 1–35.
2.
Bailey, P. S. ( 1973). “Reactivity of ozone with various organic functional groups important to water purification.” Proc., 1st Int. Symp. on Ozone for Water and Wastewater Treatment, Washington, D.C., 101–117.
3.
Benoit-Guyod, J. L., Bruckner, C., and Benoit-Guyod, M. ( 1994). “Degradation of chlorophenols by ozone and light.” Fresenius Envir. Bull., 3, 331–338.
4.
Chelkowska, K., Grasso, D., Faboan, I., and Gordon, G. ( 1992). “Numerical simulations of aqueous ozone decomposition.” Ozone Sci. and Engrg., 14, 33–49.
5.
Decoret C., Royer, J., Legube, B., and Dore, M. ( 1984). “Experimental and theoretical studies of the mechanism of the initial attack of ozone on some aromatics in aqueous medium.” Envir. Technol. Letters, 5, 207–218.
6.
Duguet, J. P., Dussert, B., Mallevialle, J., and Fiessinger, F. ( 1987). “Polymerization effects of ozone: Applications to the removal of phenolic compounds from industrial wastewaters.” Water Sci. and Technol., 19, 919–930.
7.
Gilbert, E. ( 1976). “Ozonolysis of chlorophenols and maleic acid in aqueous solution.” Proc., 2nd Int. Symp. on Ozone Technol., International Ozone Institute, Montreal, 253–261.
8.
Gilbert, E. ( 1978). “Reactions of ozone with organic compounds in dilute aqueous solution: Identification of their oxidation products.” Ozone/chlorine dioxide oxidation products of organic materials, R. G. Rice and J. A. Cotruvo, eds., International Ozone Association, Cleveland, 227–242.
9.
Hoigne, J., and Bader, H. ( 1976). “The role of hydroxyl radical reactions in ozonation processes in aqueous solutions.” Water Res., 10, 377–386.
10.
Hoigne, J., and Bader, H. ( 1983). “Rate constants of reactions of ozone with organic and inorganic compounds in water—II. Dissociating organic compounds.” Water Res., 17, 175–194.
11.
Hong, A., Zappi, M. E., Kuo, C. H., and Hill, D. (1996). “Modeling kinetics of illuminated and dark advanced oxidation.”J. Envir. Engrg., ASCE, 1, 58–62.
12.
Hu, S. T., and Yu, Y. H. ( 1994). “Preozonation of chlorophenolic wastewater for subsequent biological treatment.” Ozone Sci. and Engrg., 16, 13–28.
13.
Kuo, C. H., and Huang, C. H. ( 1995). “Aqueous phase ozonation of chlorophenols.” J. Haz. Mat., 41, 31–45.
14.
Kuo, C. H., Zhong, L., Wang, J., and Zappi, M. ( 1997). “Vapor and liquid phase ozonation of benzene.” Ozone Sci. and Engrg., 19(2), 109–127.
15.
Langlais, B., Reckhow, D. A., and Brink, D. R. ( 1991). Ozone in water treatment . Lewis, Boca Raton, Fla.
16.
Li, K. Y., Weeks, J. L., and Kuo, C. H. ( 1979). “A kinetic study of ozone-phenol reaction in aqueous solutions.” AIChE J., 25, 583–591.
17.
McMurry, J. ( 1992). Organic chemistry, 3rd Ed., Brooks/Vole Publishing Co.
18.
Verschueren, K. ( 1983). Handbook of environmental data on organic chemicals . Van Nostrand Reinhold, New York.
19.
Wang, Y. T., Pai, P. C., and Latxhaw, J. L. ( 1989). “Effects of preozonation of the methanogenic toxicity of 2,5-dichlorophenol.” J. Water Pollution Control Fed., 61(3), 320–326.
20.
Zappi, M., Hong, A., and Cerar, R. ( 1993). “Treatment of groundwater contaminated with high levels of explosives using traditional and non-traditional advanced oxidation processes.” Proc., 1993 Superfund Conf., Washington, D.C.
21.
Zheng, Y., Hill, D. O., and Kuo, C. H. ( 1993). “Rates of ozonation of cresol isomers in aqueous solutions.” Ozone Sci. and Engrg., 15, 267–278.
22.
Zheng, Y., and Kuo, C. K. ( 1996). “Kinetics and mechanism of the reaction between ozone and o-cresol in aqueous solutions.” Chem. Engrg. Comm., 145, 33–51.

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Published In

Go to Journal of Environmental Engineering
Journal of Environmental Engineering
Volume 125Issue 5May 1999
Pages: 441 - 450

History

Received: Aug 20, 1997
Published online: May 1, 1999
Published in print: May 1999

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Member, ASCE,
Dept. of Chemical Engrg., Mississippi State Univ., Mississippi State, MS 39762.
Dept. of Chemical Engrg., Mississippi State Univ., Mississippi State, MS; corresponding author. E-mail: [email protected]
Dept. of Chemical Engrg., Mississippi State Univ., Mississippi State, MS.
Envir. Lab., U.S. Army Engrs. Waterways Experiment Station, 3909 Halls Ferry Rd., Vicksburg, MS 39180.

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