Oxanilide. nitration

On nitration, oxanilide yields expl tetra- and hexanitrates (see below)... 

N 21.96% crysts, mp 295-300°(dec) si sol in hot ale Sc benz very low expin temp. It was prepd by nitrating oxanilide. Its power Sc brisance are comparable with those values of TNT Pb block expansion test — 70% Picric Acid. It is reported to be chemically unstable or reactive with moisture (Refs 6, 7, 8 8t 9) Refs 1) Beil 12, 284, (207) Sc [l65]... 

This substance, m.p. 295-300°, results from the direct nitration of oxanilide.119 It is stable and about as powerful as TNT, and is reported to explode with the production of a temperature which is distinctly lower than that produced by many high explosives. 

The compound is prepared by the direct nitration of oxanilide (Mixter and Walther [40]). Domanski and Mieszkis [41] investigated the explosive properties of hexanitro-oxanilide and found the following values for the rate of detonation of the pressed product mixed with 2% of dinitrotoluene ... 

This compound is prepared by nitration of oxanilide. It is of interest as being relatively stable at high temperatures. The decomposition reaction above 304 °C is endothermic. 

Oxalic acid can also be used for the prepn of glycerol monoformin, CH2OH.CHOH.CH2OH+ (COOH) 2 - CH2(0.CH0).CH0H.CH 2OH+CO2 +H2 O, which on nitration gives an expl dinitrate (Ref 4 Vol 6, F173-R). The Soci te Anonyme d Explosifs et de Produits Chimiques in 1907 proposed the use of oxalic acid for the prepn of oxanilide, from vdiich the expl Hexanitro-oxanilide is obtained (Ref 5)... 

Another process starts from oxanilide, which is obtained from oxalic acid and aniline at 200°. Oxanilide is sulfonated by concentrated sulfuric acid on a water bath, cooled to 50°, and nitrated with mixed acid [equal parts of nitric acid (cf 1.44) and concentrated sulfuric acid] at that temperature. The oxalyl and sulfo groups are successively removed by dilution of the reaction mixture with water and boiling for several hours. 

In the United Kingdom, work on slow-burning mixtures has continued to follow the trend of employing high-gassing mixtures using such fuels as tetranitro oxanilide or tetranitrocarbazole with barium nitrate. 

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