Other energetic nitramines 283Nitramine-nitrates of general structure (133) are known as NENAs and are conveniently
prepared from the nitrative cleavage ofN-alkylaziridines^53 ,^54 with dinitrogen pentoxide or
from the direct nitration of the corresponding aminoalcohols.^55 These compounds find use
as energetic plastisizers in explosive and propellant formulations; Bu-NENA (R=n-Bu) is a
component of some LOVA (low vulnerability ammunition) propellants.^56
NO 2
C
NO 2
134F +HOCH 2 CNO 2NO 2
89NO 2
CNO 2
135CH 2 NHCH 2 CH 2 NHCH 2 CNO 2NO 2FCNO 2NO 2FC
NO 2
136CF 2 CH 2 CH 2 NNCH CH 2 CNO 2NO 2NO 2 NO 2 NO 2 NO 2NO 2FHNO 3 , H 2 SO 4CH 2 NH 2 CH 2 OHFigure 6.40A large number of energetic materials containing nitramino functionality in conjunction
with aliphaticC-nitro groups have been reported. Many of these contain dinitromethyl, trini-
tromethyl or fluorodinitromethyl functionality. The bis-nitramine (136) has been synthesized
from the mixed acid nitration of the diamine (135), the latter being the condensation product
of 2-fluoro-2,2-dinitroethylamine (134) with 2,2-dinitro-1,3-propanediol (89). Bis-nitramine
(136) has been suggested as a high-energy oxidizer in propellants.^57
NO 2
C 2 NCHNO 2NO 2
137HO (CH 2 )n CH 2 CO 2 HNO 2
C 2 NCHNO 2NO 2
138HO (CH 2 )n CH 2 OHFigure 6.41Some compounds of general structures (137) and (138) have hydroxy or carboxy termini,
making them potential monomers for the synthesis of energetic polymers (binders) and plas-
ticizers for both explosive and propellant formulations.^58
NO 2
CF
NO 2N CH 2 CNO 2NO 2FNO100 % HNO 3139
HNO 3 , H 2 SO 4NaNO 2 , H 2 SO 4 ,
-10 °CCH 2NO 2
CF
NO 2NCH 2 CNO 2NO 2F
141CH 2NO 2
CF
NO 2NCH 2 CNO 2 NO 2NO 2F140CH 2HFigure 6.42