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Decomposition of Benzidine, -Naphthylamine, and p-Toluidine in Soils¹

ABSTRACT

Decomposition of ¹⁴C-labeled benzidine, -naphthylamine, and p-toluidine in soil was studied in laboratory experiments by monitoring CO₂ production during a 308- to 365-d incubation period. The importance of microbial activity in decomposition of all three aromatic amines was shown by decreased ¹⁴CO² evolution in ⁶⁰Co treated soils. After 365 d of incubation, 8.4 to 12% of added benzidine (54.3 µmol kg^–1) was evolved as CO₂ while 17 to 31% of added -naphthylamine (69.8 µmol kg^–1) and 19 to 35% of added p-toluidine (93.3 µmol kg^–1) were evolved as CO₂ in 308 d. Decomposition of benzidine, -naphthylamine, and p-toluidine was greatest at a water potential of –0.033 MPa and decreased at both 0 and –0.5 MPa. Decomposition was enhanced by increasing the temperature from 12 to 30°C. The absolute amount of -naphthylamine and p-toluidine decomposed increased while the percentage of added amine degraded decreased as application rate was increased from 1 to 1000 mg kg^–1. For benzidine, both the amount and proportion decomposed increased with an increase in application rate. Decomposition of aromatic amines was not enhanced by the addition of decomposable substrates. Differences in decomposition of aromatic amines occurred among soils, but consistent relationships between decomposition of amines and soil properties were not observed. In batch equilibration studies, the Freundlich equation described aromatic amine sorption. Isotherms were nonlinear for benzidine and -naphthylamine and linear for p-toluidine. Desorption of sorbed amines followed the order: benzidine < p-toluidine < -naphthylamine and was inversely related to the extent of decomposition.

Key Words: aromatic amines • 4,4'-diaminobiphenyl • 1-aminonaphthalene • 4-methylaniline • sorption

¹ Contribution of the Purdue Univ. Agric. Exp. Stn., Journal Paper no. 10 000, Dep. of Agronomy, W. Lafayette, IN 47907.

² Former Graduate Assistant and Professors, respectively. The senior author is currently Assistant Professor, Dep. of Plant and Soil Sci., Univ. of Tennessee, Knoxville and the third author is Professor and Head, Dep. of Agronomy, Univ. of Nebraska, Lincoln, 68583.

Received for publication July 25, 1984.