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diphenylamine : ウィキペディア英語版
diphenylamine

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Diphenylamine is an organic compound with the formula (C6H5)2NH. The compound is a derivative of aniline, consisting of an amine bound to two phenyl groups. The compound is a colorless solid, but commercial samples are often yellow due to oxidized impurities.〔P. F. Vogt, J. J. Gerulis, "Amines, Aromatic" in Ullmann’s Encyclopedia of Industrial Chemistry 2005, Wiley-VCH, Weinheim. 〕 Diphenylamine dissolves well in many common organic solvents, and is moderately soluble in water. It is used mainly for its antioxidant properties.
==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 ''K''b of 10−14. With strong acids, it forms salts. For example, treatment with sulfuric acid gives the bisulfate ()+() as a white or yellowish powder with m.p. 123-125 °C.〔''The Merck Index, 10th Ed.'', (1983), p.485, Rahway: Merck & Co.〕
Diphenylamine undergoes various cyclisation reactions. With sulfur, it gives phenothiazine, a precursor to pharmaceuticals.〔T. Kahl, K.-W. Schröder, F. R. Lawrence, W. J. Marshall, Hartmut Höke, Rudolf Jäckh, "Aniline" in Ullmann's Encyclopedia of Industrial Chemistry, 2005, Wiley-VCH: Weinheim. 〕
: (C6H5)2NH + 2 S → S(C6H4)2NH + H2S
With iodine, it undergoes dehydrogenation to give carbazole, with release of hydrogen iodide:
: (C6H5)2NH + I2 → (C6H4)2NH + 2 HI
Arylation with iodobenzene gives triphenylamine.

抄文引用元・出典: フリー百科事典『 ウィキペディア(Wikipedia)
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