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AZOIMIDE

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Originally appearing in Volume V03, Page 83 of the 1911 Encyclopedia Britannica.
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AZOIMIDE , or HYDRAZO1c See also:

ACID, N3H, a See also:compound of See also:nitrogen and See also:hydrogen, first isolated in 1890 by Th. See also:Curtius (Berichte, 189o, 23, p. 3023). It is the hydrogen compound corresponding to P. Greiss' diazoimino See also:benzene, C6H5N3, which is prepared by the addition of See also:ammonia to diazobenzene perbromide. Curtius found that benzoyl glycollic acid gavcbenzoyl See also:hydrazine with hydrazine See also:hydrate: C6H2OCO•CH2000H+2N2H4•H2O = H20+C5H5CONH •NH2+ NH2•NH•CH2.COOH. (See also:Ethyl benzoate may be employed instead of benzoyl glycollic acid for this reaction.) This compound gave a nitroso compound with nitrous acid, which changed spontaneously into benzoylazoimide by loss of See also:water: CSHSCO-NH.See also:NH2+MONO =H20+C€H5CO-N(NO) •NH2. C/H5CO-N (NO) •NH2 =See also:H2O +CSHNCO-Na• The resulting benzoylazoimide is easily hydrolysed by boiling with alcoholic solutions of See also:caustic alkalis, a benzoate of the See also:alkali See also:metal and an alkali See also:salt of the new acid being obtained; the latter is precipitated in crystalline See also:condition on See also:standing. An improved method of preparation was found in the use of hippuric acid, which reacts with hydrazine hydrate to See also:form hippuryl hydrazine, C6H5CONH.CH2CONH•NH2, and this sub-stance is converted by nitrous acid into diazo-hippuramide, C6H5CONH•CH2•CO•NH•N2.OH, which is hydrolysed by the See also:action of caustic alkalis with the See also:production of salts of hydrazoic acid. To obtain the See also:free acid it is best to dissolve the diazohippuramide in dilute soda, warm the See also:solution to ensure the formation of the See also:sodium salt, and distil the resulting liquid with dilute sulphuric acid. The pure acid may be obtained by fractional See also:distillation as a colourless liquid of very unpleasant See also:shell, boiling at 3o° C., and extremely explosive. It is soluble in water, and the solution dissolves many metals (See also:zinc, See also:iron, &c.) with liberation of hydrogen and formation of salts (azoimides, azides or hydrazoates).

All the salts are explosive and readily interact with the alkyl iodides. In its properties it shows some See also:

analogy to the halogen acids, since it forms difficultly soluble See also:lead, See also:silver and mercurous salts. The metallic salts all crystallize in the anhydrous condition and decompose on See also:heating, leaving a See also:residue of the pure metal. The acid is a " weak " acid, being ionized only to a very slight extent in dilute aqueous solution. E. NoeIting and E. Grandmougin (Berichie, 1891, 24, p. 2546) obtained azoimide from dinitraniline, C6H3(NO2)2•NH2, by diazotization and See also:conversion of the diazo compound into the perbromide, (NO2)2C6H3•N2•Br3. This compound is then decomposed by ammonia, dinitrophenylhydrazoate being formed, which on See also:hydrolysis with alcoholic potash gives See also:potassium hydrazoate (azide) and dinitrophenol. The solution is then acidified and distilled, when azoimide passes over. Somewhat later, they found that it could be prepared from diazobenzene imide, provided a nitro See also:group were See also:present in the ortho or See also:para position to the diazo group. The para-nitro compound is dropped slowly into a See also:cold solution of one See also:part of caustic potash in ten parts of See also:absolute See also:alcohol; the solution becomes dark red in See also:colour and is then warmed for two days on the water See also:bath.

After the greater portion of the alcohol has distilled off, the solution is acidified with sulphuric acid and the azoimide distilled over. The yield obtained is only about 40% of that required by theory, on See also:

account of secondary reactions taking See also:place. Orthonitro-diazobenzene imide only yields 30%. W. See also:Wislicenus (Berichte, 1892, 25, p. 2084) has prepared the sodium salt by passing nitrous See also:oxide over sodamide at high temperatures. The acid can also be obtained by the action of nitrous acid on hydrazine sulphate; by the oxidation of hydrazine by hydrogen peroxide and sulphuric acid (A. W. See also:Browne, J. Amer. Chem. See also:Soc., 1905, 25, p.

251), or by ammonium metavanadate (A. W. Browne and F. F. Shetterly, Abst. J.C.S., 1907, ii. p. 863). Ammonium azoimide, N3•NH4, may be prepared by boiling diazohippuramide with alcoholic ammonia, until no more ammonia escapes, the following reaction taking place: CeH.CO•NHCH2CONH-N2-OH±2NH3 =N,-NH4+H20+ C6H5CO-NH•CH2•CO•NH2. The liquid is then allowed to stand for twelve See also:

hours, and the clear alcoholic solution is decanted from the precipitated hippuramide. To the alcoholic solution, four times its See also:volume of See also:ether is added, when the ammonium salt is precipitated. It is then filtered, washed with ether, and See also:air-dried. The salt is readily soluble in water, and is only feebly alkaline.

It is extremely explosive. Hydrazine azoimide, N5I15, is also known. Chloroazoimide, Cl•N3, the chloride corresponding to -azoimide,83 was obtained by F. Raschig (Ber., 1908, 41,p.

End of Article: AZOIMIDE

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