Diphenylamine

Diphenylamine

[dahy-fen-l-uh-meen, -am-in, -feen-]

Diphenylamine is the organic compound with the formula (C6H5)2NH. It is a colourless solid, but samples are often yellow due to oxidized impurities.

Preparation and reactivity

Diphenylamine is manufactured by the thermal deamination of aniline over oxide catalysts:
2 C6H5NH2 → (C6H5)2NH + NH3
It is a weak base, with a KB of 10-14. With strong acids, it forms the water soluble salt.

Applications

Diphenylaniline itself has few applications but its derivatives are more useful. Ring-alkylated derivatives of diphenylamine are used as "antiozinates" in the manufacture of rubber products, reflecting the antioxidant nature of aniline derivatives. The compound undergoes various cyclisaton reactions. With sulfur, it gives phenothiazine, a precursor to certain pharmaceuticals.
(C6H5)2NH + 2 S → S(C6H4)2NH + H2S
With iodine, it cyclises to carbazole:
(C6H5)2NH + I2 → (C6H4)2NH + 2 HI
Arylation with iodobenzene gives triphenylamine.

Safety

Diphenylamine, like other arylamines, is toxic. Exposure is highly regulated in most countries. See MSDS.

References

External links

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