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2-硝基-2-氮杂金刚烷-4,8-二醇二硝酸酯的合成与表征
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作者单位:

(南京理工大学化工学院, 江苏 南京 210094)

作者简介:

阮宏伟(1991-),男,硕士研究生,主要从事有机合成化学研究。e-mail: rhwnjust@163.com 通信联系人: 罗军(1975-),男,教授,主要从事有机合成化学研究。e-mail: luojun@njust.edu.cn

通讯作者:

罗军(1975-),男,教授,主要从事有机合成化学研究。e-mail: luojun@njust.edu.cn

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Synthesis and Characterization of 2-Nitro-2-azaadamantane-4,8-diyl Dinitrate
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(School of Chemical Engineering, Nanjing University of Science and Technology, Nanjing 210094, China)

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    摘要:

    以双环[3.3.1]壬烷-2, 6-二酮为原料, 经腙化、消除、环氧化、环合、乙酰化、硝化等步骤, 合成了一种新型硝基笼形化合物2-硝基-2-氮杂金刚烷-4, 8-二醇二硝酸酯, 总收率为27%。以硝硫混酸为硝化剂, 考察了硫酸与硝酸摩尔比、反应温度、反应时间对硝化反应的影响。确定的最佳反应条件为:摩尔比n(H2SO4):n(HNO3)=1:2, 反应温度60 ℃, 反应时间4 h, 此时, 硝化反应收率达81%。利用热重分析(TG)和差示扫描量热法(DSC)研究了目标化合物的热性能, 发现其从170.0 ℃开始分解, 热分解峰温为193.7 ℃。通过Kamlet-Jacobs公式预估了目标化合物的物化与爆轰性能, 其密度为1.71 g·cm-3, 爆速为5780 m·s-1, 爆压为11.0 GPa。

    Abstract:

    2-Nitro-2-azaadamantane-4, 8-diyl dinitrate, a new energetic cage compound, was synthesized with a total yield of 27% from bicyclo[3.3.1]nonane-2, 6-dione via hydrazonation, elimination, epoxidation, cyclization, acetylation and nitration.Nitric-sulfuric acid was applied as nitrating agent and nitration conditions such as molar ratio between H2SO4 and HNO3, reaction temperature and reaction time were investigated and the optimal reaction conditions was as follows:n(H2SO4):n(HNO3)=1:2 and 60 ℃ for 4 h with yield of nitration reaction as 81%.The thermal stability of target product was studied by thermogravimetry(TG) and differential scanning calorimetry(DSC).The detonation properties were predicted by Kamlet-Jacobs formula.Results show that the compound starts to decompose at 170.0 ℃ and the decomposition peak temperature is 193.7 ℃, and the density, detonation velocity, detonation pressure are 1.71 g·cm-3, 5780 m·s-1, 11.0 GPa, respectively.

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引用本文

阮宏伟,凌亦飞,王桂香,等.2-硝基-2-氮杂金刚烷-4,8-二醇二硝酸酯的合成与表征[J].含能材料, 2016, 24(6):544-549. DOI:10.11943/j. issn.1006-9941.2016.06.005.
RUAN Hong-wei, LING Yi-fei, WANG Gui-xiang, et al. Synthesis and Characterization of 2-Nitro-2-azaadamantane-4,8-diyl Dinitrate[J]. Chinese Journal of Energetic Materials, 2016, 24(6):544-549. DOI:10.11943/j. issn.1006-9941.2016.06.005.

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历史
  • 收稿日期: 2015-09-16
  • 最后修改日期: 2015-11-21
  • 录用日期: 2015-12-08
  • 在线发布日期: 2016-05-20
  • 出版日期: 2016-06-03