Irreversible Binding of Chlorophenols to Soil and Its Impact on Bioavailability
Publication: Journal of Environmental Engineering
Volume 123, Issue 5
Abstract
Experiments were conducted to quantify binding of phenol, 4-chlorophenol (4-CP), 2,4,6-trichlorophenol (TCP), and pentachlorophenol (PCP) to a sandy surface soil under aerobic and anoxic conditions, with and without autoclaving. Water and methylene chloride were used to extract the physisorbed contaminants. The chemically bound contaminant was characterized as biologically or abiotically coupled. A portion of the residual contamination on soil was attributed to the presence of a desorbable but mass transfer-rate limited component of the sorbate. Autoclaving the soil or eliminating O2 from the system had no observable effect on the total sorption of chlorophenols. However, the amount of bound material that was resistant to extraction was at least twice as high in nonautoclaved soils under oxic conditions as compared to soil in systems from which O2 or biochemical activity, or both had been eliminated. The initial aqueous concentration of the contaminant appeared to govern the amount of nonextractable material. A biodegradation study found that approximately 50% of the coupled contaminant was bioavailable.
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References
1.
Ball, W. P., and Roberts, P. V.(1991). “Long-term sorption of halogenated organic chemicals by aquifer material. Part 2. Intraparticle diffusion.”Envir. Sci. and Technol., 25(7), 1237–1249.
2.
Barr, D. P., and Aust, S. D. (1994). “Mechanisms white rot fungi use to degrade pollutants.”Envir. Sci. and Technol., 28(2), 78A–87A.
3.
Berry, D. F., and Boyd, S. A.(1984). “Oxidative coupling of phenols and anilines by peroxidases: structure-activity relationships.”J. Soil Sci. Soc. Am., 48, 565–569.
4.
Berry, D. F., and Boyd, S. A.(1985a). “Reaction rates of phenolic humus constituents and anilines during cross-coupling.”Soil Biol. Biochem., 17(5), 631–636.
5.
Berry, D. F., and Boyd, S. A.(1985b). “Decontamination of soil through enhanced formation of bound residues.”Envir. Sci. and Technol., 19(11), 1132–1133.
6.
Bhandari, A., Novak, J. T., and Berry, D. F.(1996). “Binding of 4-monochlorophenol to soil.”Envir. Sci. and Technol., 30(7), 2305–2311.
7.
Bollag, J.-M.(1992). “Decontaminating soil with enzymes.”Envir. Sci. and Technol., 26(10), 876–881.
8.
Bollag, J.-M., Liu, S.-Y., and Minard, R. D.(1980). “Cross-coupling of phenolic humus constituents and 2,4-dichlorophenol.”J. Soil Sci. Soc. Am., 44, 52–56.
9.
Burgos, W. D. (1995). “Reversible and irreversible adsorption of α-naphthol to soil,” PhD dissertation, Virginia Polytechnic Inst. and State Univ., Blacksburg, Va.
10.
Brezny, R., Joyce, T. W., Gonzalez, B., and Slimak, M.(1993). “Biotransformation and toxicity changes of chlorolignins in soil.”Envir. Sci. and Technol., 27(9), 1880–1884.
11.
Cookson, J. T. Jr. (1995). Bioremediation engineering: design and application. McGraw-Hill Book Co., Inc., New York, N.Y.
12.
Dec, J., and Bollag, J.-M.(1988). “Microbial release and degradation of catechol and chlorophenols bound to synthetic humic acid.”J. Soil Sci. Soc. Am., 52, 1366–1371.
13.
Dec., J., and Bollag, J.-M.(1990). “Detoxification of substituted phenols by oxidoreductive enzymes through polymerization reactions.”Archives Envir. Contamination and Toxicology, 19, 543–550.
14.
Dec, J., and Bollag, J.-M. (1994). “Dehalogenation of chlorinated phenols during oxidative coupling.”Envir. Sci. and Technol., 28(3), 484–490.
15.
Dec, J., and Bollag, J.-M.(1995). “Effect of various factors on dehalogenation of chlorinated phenols and anilines during oxidative coupling.”Envir. Sci. and Technol., 29(3), 657–663.
16.
Dec, J., Shuttleworth, K. L., and Bollag, J.-M.(1990). “Microbial release of 2,4-dichlorophenol bound to humic acid or incorporated during humification.”J. Envir. Quality, 19, 546–551.
17.
Grant, T. M., and King, C. J.(1990). “Mechanisms of irreversible adsorption of phenolic compounds by activated carbon.”Industrial Engrg. Chem. Res., 29(2), 264–271.
18.
Isaacson, P. J., and Frink, C. R.(1984). “Nonreversible sorption of phenolic compounds by sediment fractions: the role of sediment organic matter.”Envir. Sci. and Technol., 18(1), 43–48.
19.
Khan, S. U. (1982). “Studies on bound 14C-prometryn residues in soil and plants.”Chemosphere, 11, 771–795.
20.
Larson, R. A., and Hufnal, J. M. Jr.(1980). “Oxidative polymerization of dissolved phenols by soluble and insoluble inorganic species.”Limnology and Oceanography, 25(3), 505–512.
21.
Larson, R. A., and Weber, E. J. (1994). Reaction mechanisms in environmental organic chemistry. Lewis Publishers, Boca Raton, Fla.
22.
McBride, M. B.(1989). “Oxidation of dihydroxybenzenes in hydrated aqueous suspension of birnessite.”Clays and Clay Minerals, 37(4), 341–347.
23.
Mortland, M. M., and Halloran, L. J.(1986). “Polymerization of aromatic molecules on smectite.”J. Soil Sci. Soc. Am., 40, 367–370.
24.
Nakhla, G., Qubaih, J., Abu-Zaid, N., and Abdulappa, M.(1990). “Impact of nitrogen on the absorptive capacity of activated charcoal.”Envir. Technol., 11, 731–738.
25.
Paul, E. A., and Clark, F. E. (1989). Soil microbiology and biochemistry. Academic Press, Inc., San Diego, Calif.
26.
Robinson, K. G. (1990). “Influence of organic matter on the sorption and bioavailability of 2,4,6-trichloro-(14C)-phenol,” PhD dissertation, Virginia Polytechnic Inst. and State Univ., Blacksburg, Va.
27.
Sarkar, J. M., Malcolm, R. L., and Bollag, J.-M.(1988). “Enzymatic coupling of 2,4-dichlorophenol to stream fulvic acid in the presence of oxidoreductases.”J. Soil Sci. Soc. Am., 52, 688–694.
28.
Shindo, H., and Huang, P. M.(1984). “Catalytic effect of manganese (IV), iron(III), aluminum and silicon oxides on the formation of phenolic polymers.”J. Soil Sci. Soc. Am., 48, 927–934.
29.
Shuttleworth, K. L., and Bollag, J.-M.(1986). “Soluble and immobilized laccase as catalysts for transformation of substituted phenols.”Enzyme Microbiol. Technol., 8, 171–177.
30.
Sorial, G. A., Suidan, M. T., Vidic, R. D., and Maloney, S. W.(1993a). “Competitive adsorption of phenols on GAC: I. Adsorption equilibrium.”J. Envir. Engrg., ASCE, 119(6), 1026–1043.
31.
Sorial, G. A., Suidan, M. T., Vidic, R. D., and Maloney, S. W.(1993b). “Competitive adsorption of phenols on GAC: II. Adsorption dynamics under anoxic conditions.”J. Envir. Engrg., ASCE, 119(6), 1044–1058.
32.
Stevenson, F. J. (1982). Humus chemistry: genesis, composition, reactions. John Wiley & Sons, Inc., New York, N.Y.
33.
Stone, A. T.(1987). “Reductive dissolution of Mn(III/IV) oxides by substituted phenols.”Envir. Sci. and Technol., 21(10), 979–988.
34.
Sun, W.-Q., Payne, G. F., Moas, M. S. G. L., Chu, J. H., and Wallace, K. K.(1992). “Tyrosinase reaction/chitosan adsorption for removing phenols from wastewater.”Biotechnol. Progress, 8, 179–186.
35.
Ulrich, H.-J., and Stone, A. T.(1989). “Oxidation of chlorophenols adsorbed to manganese oxide surfaces.”Envir. Sci. and Technol., 23(4), 421–428.
36.
Verschueren, K. (1983). Handbook of environmental data on organic chemicals, 2nd ed., Van Nostrand Reinhold Co., New York, N.Y.
37.
Vidic, R. D., and Suidan, M. T.(1991). “Role of dissolved oxygen on the adsorptive capacity of activated carbon for synthetic and natural organic matter.”Envir. Sci. and Technol., 25(9), 1612–1618.
38.
Wang, T. S. C., Li, S. W., and Ferng, Y. L. (1978). Catalytic polymerization of phenolic compounds by clay minerals.”J. Soil Sci., 126(1), 15–21.
39.
Weber, W. J. Jr., and Huang, W.(1996). “A distributed reactivity model for sorption by soils and sediments. 4. Intraparticle heterogeneity and phase-distribution relationships under nonequilibrium conditions.”Envir. Sci. and Technol., 30(3), 881–888.
40.
Wu, S., and Gschwend, P. M.(1986). “Sorption kinetics of hydrophobic organic compounds to natural sediments and soils.”Envir. Sci. and Technol., 20(7), 717–725.
Information & Authors
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Published In
Journal of Environmental Engineering
Volume 123 • Issue 5 • May 1997
Pages: 506 - 513
Copyright
Copyright © 1997 American Society of Civil Engineers.
History
Published online: May 1, 1997
Published in print: May 1997
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