Pyrolytic release of tightly complexed 4-chloroaniline from soils and soil humic acids

Worobey, Brian L.; Webster, G. R. B.

doi:10.1021/jf00109a036

Cited by 8 publications

(6 citation statements)

References 4 publications

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“…Numerous studies have concentrated on transport and transformation of aromatic amines in the environment. These investigations have frequently focused on the irreversible sorption of agrochemicals with aromatic amine groups in soils and sediments (18)(19)(20)(21)(22)(23)(24). Irreversible binding of aromatic amines to carbonyl moieties in the natural organic matter (NOM) (e.g., via 1,4-nucleophilic addition to quinone moieties) is thought to be the predominant factor governing their fate in the environment (18,21,25).…”

Section: Introductionmentioning

confidence: 99%

Sediment-Mediated Reduction of 2,4,6-Trinitrotoluene and Fate of the Resulting Aromatic (Poly)amines

Elovitz

Weber

1999

Environ. Sci. Technol.

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2,4,6-Trinitrotoluene is a major surface and subsurface contaminant found at numerous munitions production and storage facilities. The reductive transformation of 2,4,6-trinitrotoluene (TNT) to aromatic (poly)amines and the consequent fate of these products were studied in anaerobic and aerobic sediment−water systems. Reduction of TNT was rapid under both anaerobic and aerobic conditions. Nitro-reduction was regioselective, leading to the preferential formation of 4-amino-2,6-dinitrotoluene (4-ADNT) and 2,4-diamino-6-nitrotoluene (2,4-DANT). Subsequent sorption of 2,4-DANT was rapid under aerobic conditions and resulted in nearly complete, irreversible retention by the sediment phase. Under anaerobic conditions, the rapidly formed 2,4-DANT displayed little affinity for the sediment phase. Instead, 2,4-DANT was further transformed to products that remained in the aqueous phase. Sorption studies in nontransforming sediments indicated increased irreversible sorption with replacement of nitro groups with amino groups. Covalent binding of the DANTs was partially inhibited under anoxic conditions, but sorption of TNT and the ADNTs was unaffected by changes in redox conditions.

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Section: Introductionmentioning

confidence: 99%

Sediment-Mediated Reduction of 2,4,6-Trinitrotoluene and Fate of the Resulting Aromatic (Poly)amines

Elovitz

Weber

1999

Environ. Sci. Technol.

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“…BFs-Methanol Ex- Extractability of tightly complexed 4-chloroaniline from treated soil humic acids. (*) These values are described in the following paper (Worobey and Webster, 1982). yielded 82.7 and 77.2%, respectively, leaving 18 and 27.2% in the residues.…”

Section: Resultsmentioning

confidence: 85%

“…This technique, developed to release the chloroanilines, was based on the use of pyrolysis. Similar methodology was investigated in this laboratory to release tightly complexed humic acid-4chloroaniline, the results of which are reported in Worobey and Webster (1982). Khan and Hamilton (1980) succeeded in releasing tightly complexed prometryn from soil via pyrolysis; it thus appears that the chemical nature of the compound is of importance in effecting its release from soil.…”

mentioning

confidence: 95%

“…Extractability of tightly complexed 4-chloroaniline from treated soil humic acids. (*) These values are described in the following paper(Worobey and Webster, 1982).…”

mentioning

confidence: 99%

“…Analytical techniques for the determination of tightly complexed ("bound") pesticides and/or their degradation products are not yet readily available. Worobey and Webster (1982) recently reported a sensitive quantitative method for the determination of 4-chloroaniline tightly complexed to a soil humic acid. Several methods were investigated, and alkaline hydrolysis under reflux yielded the greatest amounts of intact 4-chloroaniline quantified by electron-capture gas-liquid chromatography (EC-GLC) Pesticide Research Laboratory, Department of Soil Science, University of Manitoba, Winnipeg, Manitoba, Canada R3T 2N2. Present address: Food Research Division, Bureau of Chemical Safety, Health and Welfare Canada, Ottawa, Ontario, Canada K1A 0L2.…”

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confidence: 99%

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Hydrolytic release of tightly complexed 4-chloroaniline from soil humic acids: an analytical method

Worobey¹,

Webster²

1982

J. Agric. Food Chem.

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Research was conducted to develop a method to release and quantitate "bound" or tightly complexed 4-chloroaniline (4-CA) from soil humic acids. An evaluation of several techniques to release tightly complexed [14C]-4-CA from soil humic acids resulted in the development of an analytical method using alkaline hydrolysis and quantitation of the released 4-CA as its heptafluorobutyryl derivative detected by electron-capture gas-liquid chromatography (EC-GLC). Soil humic acids were treated with [14C]-4-CA at 477 ppm. Two percent of the applied radioactivity was uncomplexed, 10% was extractable into benzene and acetone (loosely complexed), and 88% remained tightly complexed. The alkaline hydrolysis released 80% of the applied radioactivity (91% of tightly complexed residue), with 46% of the applied 4-CA reproducibly quantitated as its JV-(heptafluorobutyryl)-4-chloroaniline derivative. Other extraction methods such as acid hydrolysis, methylation, heptafluorobutyrylation, sonication, or pyrolysis were not as efficient in releasing tightly complexed 4-CA.Substituted chloroanilines are derived from several pesticides but especially phenylureas, phenylcarbamates, and anilide herbicides. It has been shown, for example, that herbicide-derived 4-chloroaniline (4-CA) and 3,4-dichloroaniline are bound abundantly and tenaciously to soil and particularly to soil humic acids (Hsu and Bartha, 1974a, 1976). A soil-bound residue has been defined as the chemically unidentified pesticide residue or its degradation product remaining in fulvic acid, humic acid, and humin soil fractions after exhaustive sequential extraction with

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Mixtures of diflubenzuron and p-chloroaniline changes the activities of enzymes biomarkers on tilapia fish (Oreochromis niloticus) in the presence and absence of soil

Dantzger

Jonsson

Aoyama

2018

Ecotoxicology and Environmental Safety

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Pyrolytic release of tightly complexed 4-chloroaniline from soils and soil humic acids

Cited by 8 publications

References 4 publications

Sediment-Mediated Reduction of 2,4,6-Trinitrotoluene and Fate of the Resulting Aromatic (Poly)amines

Sediment-Mediated Reduction of 2,4,6-Trinitrotoluene and Fate of the Resulting Aromatic (Poly)amines

Hydrolytic release of tightly complexed 4-chloroaniline from soil humic acids: an analytical method

Mixtures of diflubenzuron and p-chloroaniline changes the activities of enzymes biomarkers on tilapia fish (Oreochromis niloticus) in the presence and absence of soil

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