Identification of a toxic impurity in commercial diphenylamine.

Abstract

The impurity in commercial diphenylamine which induces polycystic kidney disease in rats has been identified as N,N,N'-triphenyl-p-phenylenediamine. The structure of the compound was confirmed by mass and proton magnetic resonance spectrometry and by comparison with a synthetic standard prepared by the Ullman coupling of iodobenzene and p-phenylenediamine or N,N-diphenyl-p-phenylenediamine. Laboratory studies with highly purified diphenylamine indicated that N,N,N'-triphenyl-p-phenylenediamine can be formed by heating diphenylamine.

• Authors: S Clegg, S Safe, J F Crocker
• Journal: Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes (J Environ Sci Health B) Vol. 16 Issue 2 Pg. 125-30 ( 1981) ISSN: 0360-1234 [Print] England
• PMID: 7252059 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Aniline Compounds
• Phenylenediamines
• N,N,N'-triphenyl-4-phenylenediamine
• Diphenylamine

Topics

• Aniline Compounds (analysis)
• Animals
• Diphenylamine (analysis)
• Drug Contamination
• Phenylenediamines (isolation & purification, toxicity)
• Rats