AROMATIC NITRAMINES Tetryl

The key representative of aromatic nitramines is the trinitro derivative of phenyl-methylnitramine—tetryl. This is 2,4,6-trinitrophenyhnethylnitramineorpicrylmethyl-nitramine or N-2,4,6-tetranitro-N-methylaniline. 

Tetryl is a widely-used explosive. It is also known under the names of Pyronite, Tetrylit, Tetralite, Tetralita. In England it has been known for some time as Composition Exploding—CE. The incorrect name—tetranitromethylaniline—may sometimes be encountered in the literature. 

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Numerous aromatic nitramines have been synthesized but only A,2,4,6-tetranitro-A-methylaniline (tetryl) and l-(2-nitroxyethylnitramino)-2,4,6-trinitrobenzene (pentryl) have found practical use as explosives. Both tetryl and pentryl are more powerful than TNT. Tetryl is widely used in boosters and as a component of explosive formulations like tetrytol (tetryl/TNT), PTX-1 (tetryl/RDX/TNT) and Composition C-3 (tetryl/RDX/TNT/DNT/MNT/NC). 

Aromatic nitramines undergo a rearrangement in which the nitro group migrates to the benzene ring. Such a rearrangement is believed to occur in the synthesis of tetryl, which is made by the nitration and nitrolysis... 

Nitrations of aromatic amines often involve the intermediate formation of N-nitramines, although these are rarely seen under the strongly acidic conditions of mixed acid nitration (Section 4.5). N,2,4,6-Tetranitro-N-methylaniline (tetryl) is an important secondary high explosive usually synthesized from the nitration of N,N-dimethylaniline or 2,4-dinitro-N-methylaniline. ° The synthesis of tetryl is discussed in Section 5.14. 

The majority of aromatic-aliphatic nitramines undergo denitration on heating with phenol, especially in the presence of sulphuric acid. Tetryl, for example, undergoes the following reaction ... 

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