CHINESE JOURNAL OF ENERGETIC MATERIALS
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1-羟基-1,2,3-三唑并[4,5-e]-5,7-二氧化-1,2,3,4-四嗪合成、晶体结构及性能
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1.西安近代化学研究所,陕西 西安710065;2.氟氮化工资源高效开发与利用国家重点实验室,陕西 西安710065

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国家自然科学基金(21503162)


Synthesis, Crystal Structure and Performance of 1-Hydroxy-1H-[1,2,3]triazolo[4,5-e][1,2,3,4]tetrazine 5,7-dioxide
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1.Xi′an Modern Chemistry Research Institute, Xi′an 710065, China;2.State Key Laboratory of Fluorine & Nitrogen Chemicals, Xi′an 710065, China

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    摘要:

    以3-氨基-4-(叔丁基-NNO-氧化偶氮基)呋咱(ABAoF)为原料,经重氮化开环、肟化、氧化、氨化和硝化环化五步反应得到目标化合物1-羟基-1,2,3-三唑并[4,5-e]-5,7-二氧化-1,2,3,4-四嗪(HTTDO),总收率24.1%,采用红外光谱、核磁共振、质谱及元素分析对中间体及产物的结构进行了表征;探讨了氨化及硝化环化的反应机理;培养了HTTDO·4.5H2O的单晶,X射线衍射分析表明,其为正斜方晶系,空间群为Pna2(1),晶体密度为1.659 g·cm-3;利用Gaussian 09程序和Kamlet-Jacobs方程计算HTTDO理论密度为1.88 g·cm-3,爆速为9393 m·s-1,爆压为41.9 GPa,爆热为8010 J·g-1;采用差示扫描量热(DSC)研究了HTTDO的热性能:其在热分解过程中,放热剧烈,峰温最高达194.5 ℃。

    Abstract:

    Using 3-amino-4-(tert-butyl-NNO-azoxy) furazan (ABAoF) as starting material, 1-hydroxy-1H[-1, 2, 3] triazolo [4, 5-e] [1, 2, 3, 4] tetrazine 5, 7-dioxide (HTTDO) was synthesized by 5-steps reactions including diazotization, oximation, oxidation, amination and nitration cyclization, with a total yield of 24.1%. HTTDO and the associate dintermediates were characterized by FT-IR, NMR, mass spectrometry and elementary analysis. Further, the reaction mechanisms of amination and nitration cyclization were clarified. In this work, the single crystal of HTTDO·4.5H2O was cultivated for the first time, and the crystal structure of which was determined by X-ray diffraction analysis, demonstrating that HTTDO·4.5H2O crystallized in the orthorhombic space group Pna2(1). The physico-chemistry and detonation properties of HTTDO were calculated by Gaussian 09 program and Kam let-Jacobs formula. The detonation velocity of HTTDO was 9393 m·s-1, and the detonation pressure was 41.9 GPa and the detonation heat was 8010 J·g-1. In addition, the thermal behaviors of HTTDO were studied by differential scanning calorimetry (DSC). During the exothermic thermal decomposition process of HTTDO, a sharp peak occurred at 194.5 ℃.

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罗义芬,毕福强,翟连杰,等.1-羟基-1,2,3-三唑并[4,5-e]-5,7-二氧化-1,2,3,4-四嗪合成、晶体结构及性能[J].含能材料, 2018, 26(11):919-924. DOI:10.11943/CJEM2018070.
LUO Yi-fen, BI Fu-qiang, ZHAI Lian-jie, et al. Synthesis, Crystal Structure and Performance of 1-Hydroxy-1H-[1,2,3]triazolo[4,5-e][1,2,3,4]tetrazine 5,7-dioxide[J]. Chinese Journal of Energetic Materials, 2018, 26(11):919-924. DOI:10.11943/CJEM2018070.

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  • 收稿日期: 2018-03-19
  • 最后修改日期: 2018-09-26
  • 录用日期: 2018-08-21
  • 在线发布日期: 2018-09-13
  • 出版日期: 2018-11-25