CHINESE JOURNAL OF ENERGETIC MATERIALS
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3,5-二氨基氧化哒嗪含能衍生物合成及性能
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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 and Performance of 3,5-Diaminopyridazine-1-oxide Energetic Derivatives
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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3,5-二氯哒嗪为原料,经过取代、氧化、硝化、氨解四步反应分别合成3,5-二氨基-4,6-二硝基氧化哒嗪(DADNPO)和未见文献报道的3,5-二氨基-4-硝基氧化哒嗪(DANPO),并采用红外光谱、1H NMR、13C NMR及元素分析对中间体及产物结构进行了表征;探究了硝化反应条件对硝化产物及收率的影响,确定制备3,5-二甲氧基-4,6-二硝基氧化哒嗪较佳条件为:硝硫混酸作为硝化试剂,反应温度50~55 ℃,反应时间为15 h。利用Gaussian 09 程序和Kamlet-Jacobs方程计算DADNPO和DANPO的爆速分别为8.486 km·s-1和7.224 km·s-1,爆压分别为30.2 GPa和23.09 GPa。采用差示扫描量热(DSC)研究了这两种化合物的热性能,结果表明, DADNPO、DANPO放热分解峰温分别为244.4°C和325.2°C,DANPO的热稳定性更好。

    Abstract:

    Using 3,5-dichloropyridazine as starting material, 3,5-diamino-4,6-dinitropyridazine-1-oxide(DADNPO)and a new energetic compound 3,5-diamino-4-nitropyridazine-1-oxide(DANPO)were synthesized by substitution, oxidation, nitration and amination reactions. The structure of products and their intermediates were characterized by IR spectra, 1H NMR, 13C NMR and elemental analysis. The effects of nitrification conditions on the purity and yield of nitrification were studied. The results show that the best nitration reagent of synthesized 3,5-dimethoxy-4,6-dinitropyridazine-1-oxide is nitric acid and sulfuric acid, the reaction temperature is 50~55 ℃, and the reaction time is 15 h. The detonation properties of DADNPO and DANPO were calculated by Gaussian 09 program and Kamlet-Jacobs formula. The results show that the detonation velocities are 8.486 km·s-1and 7.224 km·s-1, and the detonation pressures are 30.2 GPa and 23.09 GPa, respectively. Meanwhile, the thermal behaviors of two compounds were studied with differential scanning calorimetry (DSC). The exothermic decomposition peak temperatures of DADNPO and DANPO are 244.4 ℃ and 325.2 ℃ respectively, indicating that DANPO has better thermal stability than DADNPO.

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罗义芬,毕福强,胡米,等.3,5-二氨基氧化哒嗪含能衍生物合成及性能[J].含能材料,2020,28(3):177-181. DOI:10.11943/CJEM2019100.
LUO Yi-fen, BI Fu-qiang, HU Mi, et al. Synthesis and Performance of 3,5-Diaminopyridazine-1-oxide Energetic Derivatives[J]. Chinese Journal of Energetic Materials, 2020, 28(3):177-181. DOI:10.11943/CJEM2019100.

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历史
  • 收稿日期: 2019-04-15
  • 最后修改日期: 2019-10-30
  • 录用日期: 2019-09-11
  • 在线发布日期: 2019-10-08
  • 出版日期: 2020-04-03