一种新型高氮含能化合物5-((5-硝基-2H-四唑-2-基)甲基)-1H-四唑-1-醇的合成与表征
Synthesis and Characterization of a Novel High Nitrogen Energetic Compound 5-((5-Nitro-2H-tetrazol-2-yl)methyl)-1H-tetrazol-1-ol
Received date: 2014-07-29
Revised date: 2014-09-01
Online published: 2014-09-16
以5-氨基四唑为起始原料, 经重氮化-硝化、烷基化、肟化、重氮化-氯化、叠氮化和环合等单元反应以19%的总产率合成了一种新型含能化合物5-[(5-硝基-2H-四唑-2-基)甲基]-1H-四唑-1-醇. 利用NMR, IR, MS及元素分析等进行了结构表征; 利用X射线单晶衍射法测试了该化合物的晶型结构, 该化合物属于单斜晶系, 空间群P2(1)/c, 晶胞参数: a=3.3619(11) Å, b=9.3910(19) Å, c=8.2060(16) Å, β=101.44 (3)°, Z=2, Dc=1.748 g·cm-3, μ=0.153 mm-1, F(000)=216; 利用差示扫描量热法(DSC)和热重(TG)分析研究了该化合物的热性能, 分解温度为202.25 ℃, 热重变化范围130～320 ℃, 总失重78.6%; 利用Kamlet-Jacobs公式估算了该化合物的爆轰性能, 理论爆速和爆压分别为8500 m·s-1和31.53 GPa.
居平文 , 凌亦飞 , 王桂香 , 罗军 . 一种新型高氮含能化合物5-((5-硝基-2H-四唑-2-基)甲基)-1H-四唑-1-醇的合成与表征[J]. 有机化学, 2015 , 35(1) : 236 -240 . DOI: 10.6023/cjoc201407044
Using 5-aminotetrazole as starting material, a novel high nitrogen energetic compound 5-((5-nitro-2H-tetrazol-2- yl)methyl)-1H-tetrazol-1-ol was synthesized with a total yield of 19% via diazotization-nitration, alkylation, oximation, diazotization-chlorination, azidation and cyclization. It was characterized by NMR, MS, IR and elemental analysis. The crystal structure of this compound was determined by X-ray single crystal diffraction analysis. The results indicated that it belonged to monoclinic system with space group P2(1), and the crystal parameters were a=3.3619(11) Å, b=9.3910(19) Å, c=8.2060(16) Å, β=101.44(3)°, Z=2, Dc=1.748 g·cm-3, μ=0.153 mm-1, F(000)=216. The thermal properties were studied by differential scanning calorimeter (DSC) and thermogravimetric (TG) analyzer analyses, which showed that the decomposition temperature of target compound was 202.25 ℃, and the mass loss due to overall reaction (130～320 ℃) was 78.6%. The detonation velocity and detonation pressure of this compound calculated by Kamlet-Jacobs formula are 8500 m·s-1 and 31.53 Gpa, respectively.
Key words： high-nitrogen energetic compound; tetrazole; synthesis; characterization
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