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Soil-catalyzed Complexation of the Pollutant 2,6-Diethylaniline with Syringic Acid¹

ABSTRACT

The catalytic capability of a soil-water slurry has been demonstrated by the rapid and substantial formation of a hybrid dimer from the incubation of the slurry with 2,6-diethylaniline (2,6-DEA) and syringic acid. After a 1-d incubation, >60% of the added chemicals were incorporated into the hybrid dimer N-(2,6-diethylphenyl)-2,6-dimethoxy-p-benzoquinone imine. No further increase or decrease in the concentration of the hybrid dimer was observed during the 6-d incubation. Sterilization of the soil by -irradiation decreased the yield of the hybrid dimer by 22%, and autoclaving the soil completely destroyed its catalytic ability. The persistence of the hybrid dimer was determined by incubating its radiolabeled analogue with the soil-water slurry. The hybrid dimer was quite stable; after incubation for 45 d about 92% of the added radioactivity was recovered, of which 84% was found to be the unchanged hybrid dimer. Our results provide evidence that covalent binding of pollutants to humus constituents can occur readily and can provide a means for containing pollutants from the environment.

Key Words: oxidative coupling • soil decontamination • substituted anilines • herbicides

¹ Contribution from the Laboratory of Soil Microbiology, Dep. of Agronomy and Dep. of Chemistry. Pennsylvania State Univ., University Park, PA 16802. Journal Series no. 7387 of the Pennsylvania Agric. Exp. Stn. This work was partially supported by the Office of Research and Development, Environmental Protection Agency (Grant no. R-811518).

² Research Associate, Lecturer in Chemistry, and Professor of Soil Microbiology, respectively.

Received for publication May 16, 1986.

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