Diphenylamine explosives stabilizer

In explosives, diphenylamine stabilizes cellulose nitrate by reacting with nitrogen oxides (see Explosives and propellants). The products formed include /V-nitrosodiphenylamine and mono andpolynitro derivatives. 

Although these are no longer used as explosives, they are formed from diphenylamine that is used as a stabilizer for nitrocellulose explosives. The metabolism of nitrodiphenylamines has been examined under anaerobic conditions, and phenazine and 4-aminoacridine that are cyclization products of the initially formed 2-aminodiphenylamine have been identified (Drzyzga et al. 1996). 

The presence of N02 and other nitrogen oxides and/or acids in explosives (especially in smokeless powders and dynamites)is very undesirable because they act as catalyzers and promote further, more rapid decomposition. Most of the stabilizers used in smokeless powder, such as diphenylamine, centralites, urethanes etc are really inhibitors because they react with N02 and other nitrogen oxides to form nitroso- and nitrocompounds. 

As a safety precaution against EXPLOSION (in case the purification has been insufficiently thorough) at least a quarter of the total volume of ether should remain in the distilling flask when the distillation is discontinued. To minimize peroxide formation, ethers should be stored in dark bottles and, if they are liquids, they should be left in contact with type 4A Linde molecular sieves, in a cold place, over sodium amalgam. The rate of formation of peroxides depends on storage conditions and is accelerated by heat, light, air and moisture. The formation of peroxides is inhibited in the presence of diphenylamine, di-tert-butylphenol, or other antioxidant as stabilizer. 

Trojan Explosive. A Nitrostarch based expl used by the USA during WWI and to a limited extent in WWII in demolition charges. It contained Nitrostarch 40, Na nitrate 37.7, Ba nitrate 20, oil 0.8, and stabilizer (diphenylamine or Ca carbonate) 1.5% grey solid pressed in Vi and 1-lb... 

Nitration of p-nitroaniline (15b), or reacting picric acid with phosphorus pentachloride, yields trinitrochlorobenzene, which on amination affords 2,4,6-trinitroaniline, the explosive picramide. Phosgenation of /V-ethylaniline (26) gives a substituted urea used as a stabilizer for explosives. Diphenylamine (8) is used as a stabilizer, for nitrocellulose explosives as well as for celluloid, and also as a solid rocket propellant. Ethylaniline 26 is employed in the manufacture of centralite, a stabilizer in smokeless powder. Other uses for 15b, the largest volume nitroaniline, include in the production of dyes, antioxidants and pharmaceuticals. 

VINYL ACETATE or VINYL ACETATE HQ or VINYL ACETATE MONOMER (108-05-4) C4HSO2 Forms explosive mixture with air [explosion limits in air (vol %) 2.6 to 13.4 fiashpoint 18°F/-7°C autoignition temp 756°F/402°C Fire Rating 3]. Polymerizes readily if not inhibited elevated temperatures and the influence of light, air, oxygen, water, or peroxides initiates violent reaction. Must be stabilized (hydroquinone or diphenylamine has been recommended) to prevent polymerization. Violent reaction with strong oxidizers, non-oxidizing mineral acids, 2-aminoethanol, butyl acrylate ... 

Diarylarnines are of the greatest industrial importance as stabilizers and antioxidants (qv) for polymers, stabilizers for explosives, polymerization inhibitors, and in dyes. Today, the use of these materials as antioxidants is essentially limited to derivatives of diphenylamine since AJ-phen5i-2-naphth5iamine is no longer used. 

Diphenylamine is used in the mannfacture of dyes, as a stabilizer for nitrocellulose explosives, and as an analytical reagent for colorimetric tests for nitrate and chlorate. 

Composition C-4 (RDX + polyisobutylene + motor oil + di-(2-ethylhexyl) sebacate) Gunpowder (nitrocellulose + nitroglycerine) with stabilizers such as diphenylamine and diethyldiphenylurea, burning rate modifiers and coolants such as potassium nitrate, potassium sulfate, barium nitrate, or dinitrotoluene HMX (High Melting Explosive)... 

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