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Design and Synthesis of Energetic Materials towards Versatile Applications by N-trinitromethyl and N-nitromethyl Functionalization of Nitroimidazoles.
ChemPlusChem ( IF 3.0 ) Pub Date : 2018-08-01 , DOI: 10.1002/cplu.201800305
Xin Yin 1, 2 , Jie Li 1 , Guojie Zhang 1 , Zhenqi Zhang 1 , Qing Ma 1 , Jun Wang 1 , Shumin Wang 2
Affiliation  

Modifying the properties of energetic materials is important not only for gaining insight into the relationship between structures and properties but also for multiple applications. A new family of energetic compounds, polynitroimidazoles featuring trinitromethyl, nitromethyl and methyl acetate moieties at the nitrogen position of heterocyclic rings were synthesized. The high-energy oxidizers 2-nitro and 4-nitro-1-(trinitromethyl)-1H-imidazoles were obtained by nitration of 1-acetonylpolynitroimidazoles in fuming HNO3 and concentrated H2 SO4 . 4,5-Dinitro-1-(nitromethyl)-1H-imidazole and 4,5-dinitro-1-(acetate methyl)-1H-imidazole were afforded by using 68 % HNO3 and concentrated H2 SO4 through controllable synthesis. All the intermediates and the target compounds were confirmed by X-ray diffraction. It is noteworthy that one of the N-trinitromethyl nitroimidazole derivatives showed high density (ρ: 1.88 g cm-3 ), attractive positive oxygen balance (Ω: +18.3 %) and good detonation performance (D: 9003 m s-1 ) exceeding those of ADN, while N-nitromethyl derivative behaved higher thermal stability and lower sensitivity in contrast to those of NG. N-acetate methyl derivative gave an interesting melt-castable property (Tm.p .: 86 o C, Td : 224 o C), acceptable detonation performance as well as low sensitivity towards impact and friction (IS>40 J, FS>360 N), making it a competitive replacement for DNAN. These chemical and physical properties indicate that these novel materials show promising energetic performance towards future applications.

中文翻译:

硝基咪唑的N-三硝基甲基和N-硝基甲基官能化的应用领域的能量材料的设计和合成。

修改高能材料的特性不仅对于深入了解结构与特性之间的关系很重要,而且对于多种应用而言也很重要。合成了新的高能化合物家族,即在杂环的氮位置具有三硝基甲基,硝基甲基和乙酸甲酯部分的聚硝基咪唑。通过在发烟的HNO3和浓H2 SO4中硝化1-乙酰基多硝基咪唑制得高能氧化剂2-硝基和4-硝基-1-(三硝基甲基)-1H-咪唑。通过使用68%的HNO 3和可控的合成浓缩的H 2 SO 4,得到4,5-二硝基-1-(硝基甲基)-1H-咪唑和4,5-二硝基-1-(乙酸甲基)-1H-咪唑。通过X射线衍射确认所有的中间体和目标化合物。值得注意的是,一种N-三硝基甲基硝基咪唑衍生物显示出高密度(ρ:1.88 g cm-3),有吸引力的正氧平衡(Ω:+18.3%)和良好的爆炸性能(D:9003 m s-1)。与NG相比,N-硝基甲基衍生物具有更高的热稳定性和更低的灵敏度,而ADN则具有更高的热稳定性和更低的灵敏度。N-乙酸甲酯衍生物具有有趣的熔体可铸性(Tm.p.:86 o C,Td:224 o C),可接受的爆震性能以及对冲击和摩擦的低敏感性(IS> 40 J,FS> 360 N),使其成为DNAN的竞争替代品。这些化学和物理性质表明,这些新颖的材料在未来的应用中显示出令人鼓舞的能量性能。优于ADN的正负氧平衡(Ω:+18.3%)和良好的爆炸性能(D:9003 m s-1),而N-硝基甲基衍生物与NG相比表现出更高的热稳定性和更低的灵敏度。N-乙酸甲酯衍生物具有有趣的熔体可铸性(Tm.p.:86 o C,Td:224 o C),可接受的爆震性能以及对冲击和摩擦的低敏感性(IS> 40 J,FS> 360 N),使其成为DNAN的竞争替代品。这些化学和物理性质表明,这些新颖的材料在未来的应用中显示出令人鼓舞的能量性能。优于ADN的正负氧平衡(Ω:+18.3%)和良好的爆炸性能(D:9003 m s-1),而N-硝基甲基衍生物与NG相比表现出更高的热稳定性和更低的灵敏度。N-乙酸甲酯衍生物具有有趣的熔体可铸性(Tm.p.:86 o C,Td:224 o C),可接受的爆震性能以及对冲击和摩擦的低敏感性(IS> 40 J,FS> 360 N),使其成为DNAN的竞争替代品。这些化学和物理性质表明,这些新颖的材料在未来的应用中显示出令人鼓舞的能量性能。N-乙酸甲酯衍生物具有有趣的熔体可铸性(Tm.p.:86 o C,Td:224 o C),可接受的爆震性能以及对冲击和摩擦的低敏感性(IS> 40 J,FS> 360 N),使其成为DNAN的竞争替代品。这些化学和物理性质表明,这些新颖的材料在未来的应用中显示出令人鼓舞的能量性能。N-乙酸甲酯衍生物具有有趣的熔体可铸性(Tm.p.:86 o C,Td:224 o C),可接受的爆震性能以及对冲击和摩擦的低敏感性(IS> 40 J,FS> 360 N),使其成为DNAN的竞争替代品。这些化学和物理性质表明,这些新颖的材料在未来的应用中显示出令人鼓舞的能量性能。
更新日期:2018-08-22
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