Advanced Open‐Chain Nitramines as Energetic Materials: Heterocyclic‐Substituted 1,3‐Dichloro‐2‐nitrazapropane

Abstract

There are great demands to develop explosives with higher performance accompanied by reduced sensitivities towards external stimuli, higher thermal stability and improved environmental acceptability. This contribution presents modified nitramines, which were investigated by nucleophilic substitution reactions of potassium salts of 5‐amino‐3‐nitro‐1,2,4‐triazole, 3,5‐dinitro‐1,2,4‐triazole, 3,5‐dinitroimidazole, 2,4‐dinitroimidazole, 4‐amino‐3,5‐dinitropyrazole, 3,5‐dinitropyrazole, 3,4‐dinitropyrazole and 3,4,5‐trinitropyrazole on 1,3‐dichloro‐2‐nitrazapropane. The energetic compounds were comprehensively characterized and their detonation parameters were calculated by the EXPLO5 code. Heats of formation were calculated by the atomization method using CBS‐4M electronic enthalpies. The presented compounds show detonation performances comparable to pentaerythritol tetranitrate (PETN). In addition, they possess high thermal stabilities and low sensitivities, which make them interesting for further investigations and possible applications as insensitive, high‐energy dense materials.

Synthesis and characterization of a new family of energetic salts based on guanidinium cation containing furoxanyl functionality

“…As illustrated in Table 2, the electrostatic sensitivities of salts 3 (0.750 J), 6 (0.720 J), 8 (0.500 J) and 10 (0.450 J) were significantly lower than that of RDX (0.200 J). 16 The electrostatic sensitivity values of salts 5 and 9 were 0.280 J and 0.180 J, respectively, which were comparable to that of RDX (0.200 J). 16 In agreement with other reports describing sensitive azide 4 compounds, salt 7 (0.050 J) was sensitive towards electrostatic discharge.…”

“…Based on the classification standard of sensitivities, 19 salts 3 and 6 are classified as less sensitive due to their impact sensitivities of 40 and 38 J ,and friction sensitivity of 360 N. The impact sensitivities of salts 8 and 10 were 32 and 35 J, respectively, which were comparable to that of TATB (30 -34 J). 17 Salts 4 and 5 were less sensitive to impact and friction than RDX (7.4 J, 120 N) 16 due to their impact sensitivities of 25 and 15 J, and friction sensitivities of 280 and 120 N, respectively. Salts 7 and 9 exhibited high sensitivities towards impact and friction, because of the presence of azido and nitramine groups within their structures, respectively.…”

Trigger bond analysis of nitroaromatic energetic materials using wiberg bond indices

“…Explosophores such as nitro (NO 2 ) and azide (N 3 ) functional groups are generally needed to sensitize energetic materials. X‐NO 2 (X = N,C,O) bonds substituted on energetic materials have been proposed to form “trigger bonds,” activated (i.e., more readily cleaved) bonds that break to initiate an explosive reaction .…”

Energized nitro-substituted azoles through ether bridges

“…Compounds 4 and 11 possess low impact and friction sensitivities (IS: > 40 J; FS: > 360 N), whereas compound 5 has an impact sensitivity of 10 J and friction sensitivity of 240 N, which have similar trends as demonstrated by 2nitrazapropane bridged compounds [1,3-bis(3,5-dinitropyrazol-1-yl)-2-nitrazapropane at 8 J vs 1,3-bis(3,4-dinitropyrazol-1-yl)-2-nitrazapropane at > 40 J)]. 10,15 Conclusions A family of ether-bridged energetic compounds was synthesized by two methods: 1) condensation of paraformaldehyde with nitrogen-rich heterocyclic compounds, and 2) reaction of salts of azoles with bis(chloromethyl)ether. All of new salts were fully characterized.…”

“…Compounds 1 and 4-6 were examined by 15 N NMR spectroscopy ( Figure 1). Compounds 1 and 6 were measured in CD 3 CN, and 4 and 5 in d 6 -DMSO.…”