5,5'-(2-三氟甲基)-咪唑-4,5-二(1H-四唑)及其含能离子盐的合成与表征
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摘要
以二氨基马来腈为原料,经过与三氟乙酸酐缩合、环化,与叠氮化纳再次缩合,合成得到了新型含能化合物5,5'-(2-三氟甲基)-咪唑-4,5-二(1H-四唑),收率61.3%;基于该化合物的酸性,设计合成了2种含能离子盐5,5'-(2-三氟甲基)-咪唑-4,5-二(1H-四唑)的羟胺盐和胍盐。利用红外光谱、核磁共振和元素分析对中间体及产物结构进行了表征。探讨了生成5,5'-(2-三氟甲基)-咪唑-4,5-二(1H-四唑)过程中影响四唑环化反应的关键因素,确定的最佳反应条件为:反应介质为水,n(2-三氟甲基-4,5-二氰基咪唑)∶n(Na N3)=1∶2.4,反应温度98℃,反应时间4 h。收率最高达86.3%。通过DSC-TG研究了5,5'-(2-三氟甲基)-咪唑-4,5-二(1H-四唑)的热分解性能,热分解曲线表明化合物直到223.65℃才开始分解,整个分解过程经历了两个主要的放热分解阶段和热失重阶段,最大放热峰温度为285.78℃,说明该化合物结构比较稳定。
Using diaminomaleonitrile as starting material,a novel energetic compound 5,5'-(2-(trifluoromethyl)-1H-imidazole-4,5-diyl) bis(1H-tetrazole) was synthesized by condensation cyclization reaction with trifluoroacetic anhydride and the second condensation cyclization reaction withNaN_3 in the yield of 61. 3%; based on acidity of the compound,two energetic ionic salts of hydroxylamine and guanidine of 5,5'-(2-(trifluoromethyl)-1H-imidazole-4,5-diyl) bis(1H-tetrazole) were designed and synthesized. The structures of products and intermediates were characterized by IR,NMR and elemental analysis. Key factors affecting the cyclization reaction for tetrazole in the formation process of5,5'-(2-(trifluoromethyl)-1H-imidazole-4,5-diyl) bis(1H-tetrazole) were discussed,the optimum reaction conditions were determined as:H2O as reaction medium,n(2-(trifluoromethyl)-1H-imidazole-4,5-dicarbonitrile) ∶ n(NaN_3) = 1∶ 2. 4,reaction temperature 98 ℃,reaction time 4 h,yield up to 86. 3%. The thermal decomposition of 5,5'-(2-(trifluoromethyl)-1H-imidazole-4,5-diyl) bis(1H-tetrazole) was studied by DSC-TG,which shown the compound decomposition starts at 223. 65 ℃,and the whole decomposition process undergos two main exothermic decomposition stages and weight loss stages,the maximum exothermic peak temperature is 285. 78 ℃,the structure of the compound is relatively stable.
Using diaminomaleonitrile as starting material,a novel energetic compound 5,5'-(2-(trifluoromethyl)-1H-imidazole-4,5-diyl) bis(1H-tetrazole) was synthesized by condensation cyclization reaction with trifluoroacetic anhydride and the second condensation cyclization reaction withNaN_3 in the yield of 61. 3%; based on acidity of the compound,two energetic ionic salts of hydroxylamine and guanidine of 5,5'-(2-(trifluoromethyl)-1H-imidazole-4,5-diyl) bis(1H-tetrazole) were designed and synthesized. The structures of products and intermediates were characterized by IR,NMR and elemental analysis. Key factors affecting the cyclization reaction for tetrazole in the formation process of5,5'-(2-(trifluoromethyl)-1H-imidazole-4,5-diyl) bis(1H-tetrazole) were discussed,the optimum reaction conditions were determined as:H2O as reaction medium,n(2-(trifluoromethyl)-1H-imidazole-4,5-dicarbonitrile) ∶ n(NaN_3) = 1∶ 2. 4,reaction temperature 98 ℃,reaction time 4 h,yield up to 86. 3%. The thermal decomposition of 5,5'-(2-(trifluoromethyl)-1H-imidazole-4,5-diyl) bis(1H-tetrazole) was studied by DSC-TG,which shown the compound decomposition starts at 223. 65 ℃,and the whole decomposition process undergos two main exothermic decomposition stages and weight loss stages,the maximum exothermic peak temperature is 285. 78 ℃,the structure of the compound is relatively stable.
引文
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