Nitro derivatives of melamine

Melamine is now a very important chemical product since it is a starting substance for the manufacture of plastics. The presence in melamine of a triazine ring, as in cyclonite, and of three amino groups induced attempts to nitrate this substance in order to obtain an explosive nitramine. 

Whitmore and Cason [73] examined the mechanism of the direct nitration of melamine with nitric acid in the presence of acetic anhydride at 5°C and obtained an explosive product (I). By nitrating a triacetyl derivative of melamine with nitric acid in the presence of acetic anhydride at 20-25°C Cason prepared product (II). This substance hydrolyses, losing N20, which results in the formation of a stable compound (III) 

Atkinson and Whitmore [74] elucidated the structure of these compounds. They showed that compound (I) is N,N -dinitroammeline, compound (II) nitroammelide and compound (III) cyanuric acid. The authors also showed that fuming nitric acid at 20-25°C transforms triacetylmelamine into N-nitro-N, N -diacetyl melamine (IV) 

All these substances decompose without melting. Only dinitroammeline (I) has explicit explosive properties. 

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