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Covalent Binding of Aromatic Amines to Natural Organic Matter: Study of Reaction Mechanisms and Development of Remediation Schemes
Citation:
WEBER, E. J., D. COLON, L. Matheson, AND M. Elovitz. Covalent Binding of Aromatic Amines to Natural Organic Matter: Study of Reaction Mechanisms and Development of Remediation Schemes. Presented at Biosystems Symposium on Bioremediation of Hazardous Wastes: Research, Development & Field Evaluations, San Francisco, CA, June 28 - 30, 1994.
Impact/Purpose:
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Description:
Aromatic amines comprise an important class of environmental contaminants. Concern over their environmental fate arises from the toxic effects that certain aromatic amines exhibit toward microbial populations and reports that they can be toxic or carcinogenic to animals. Aromatic amines can enter the environment from the degradation of textile dyes, munitions, and numerous herbicides. Because of their importance as synthetic building blocks for many industrial processes or improper treatment of industrial waste streams. The high probably of contamination of soils, sediments, and ground-water aquifers with aromatic amines necessitates the development of innovative, cost-effective in situ remediation techniques for their treatment. Numerous studies have demonstrated that aromatic amines become covalently bound to the organic fraction of soils and sediments through oxidative coupling or nucleophilic addition reactions (1-4). It is generally accepted that once bound, the bound residue is less bioavailable and less mobile than the parent compound. Thus, procedures for enhancing the irreversible binding of aromatic amines to soil constituents could potentially serve as remediation technologies. Model studies suggest that oxidative enzymes derived from soil microorganisms play a significant role in catalyzing the formation of bound residues (5,6). Stimulation of these naturally occurring enzymes could provide an effective in situ method for the treatment of soils, sediments, and ground-water aquifers contaminated with aromatic amines (7). For example, Berry and Boyd (8) were able to enhance the covalent binding of the potent carcinogen 3,3’-dichlorobenzidine (DCB) in a soil by the addition of highly reactive substrates (i.e., ferulic acid and hydrogen peroxide). They concluded that by providing the indigenous peroxidose enzymes with highly reactive substrates, the overall level of oxidative coupling in the soil was increased, which lead to enhanced incorporation of DCB. To gain a more in-depth understanding of the enzyme-mediated binding of organic amines to soils and sediments, we have studied the effects of enzyme-mediated binding of organic amines to soils and sediments, we have studied the effects of enzyme amendments to sediments treated with aromatic amines such as aniline, reduction products of TNT and atrazine, and metabolic reaction products of atrazine.