Nitramines (N-nitroamines) are nitro derivatives of amines containing one or more -NO 2 nitro groups as substituents on the amino group of the general formula R 1 R 2 NNO 2 formally derivatives of nitrous acid amide O 2 NNH 2 [1] .
There are primary nitramines (R 1 = H), secondary nitramines (R 1 , R 1 = Alk, Ar), dinitramines (R 1 = NO 2 ) and N-nitramides of the general formula RN (NO 2 ) X, where R = H, Alk, Ar; X = COOR 1 , COR 1 , SO 2 R 1 , etc.
Reactivity
Primary nitramines are weak acids that form salts with strong bases:
- RNH-NO 2 + NaOH
RN = N (O) 2 - Na + + H 2 O
The negative charge in the salts of primary nitramines due to the resonance is delocalized on the nitrogen and oxygen atoms of the nitro group; therefore, the alkylation of such salts with alkyl halides, dialkyl sulfates and diazoalkanes forms as N-derivatives - secondary nitramines):
- RN = N (O) 2 - + R 1 Hal
and O-derivatives:
- RN = N (O) 2 - + R 1 Hal
the ratio of N- and O-alkylation products depends on the reaction conditions and the nature of the reagents.
Application
Many compounds of the class N-nitramines are explosives (BB) and are widely used in military and industrial applications. This class includes:
- tetryl
- hexogen
- octogen
- ethylene-N, N-dinitramine (edna)
- nitroguanidine
- nitride urea
- N-diethanol-N-nitramindinitrate (DIN)
Some N-nitramines (for example, Octogen) have a high thermal stability and are used as components of rocket fuels and industrial explosives for deep-seated work.
The production of compounds of this class is massive in many countries. The main raw materials for their production are aliphatic and aromatic amines, sulfuric , nitric and acetic acids . They have a greater oxygen balance and greater performance than nitro compounds . Sensitivity to external influences is quite high, so N-nitramines are often used in a phlegmatized form.