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3,5-二氯-2,4,6-三硝基苯胺及其衍生物的合成

侯可辉,刘祖亮*   

  1. (南京理工大学化工学院 南京 210094)
  • 收稿日期:2013-01-21 修回日期:2013-04-12 出版日期:2013-11-10 发布日期:2013-11-10
  • 通讯作者: 刘祖亮，教授; Tel:025-84318865; Fax:025-84315030; E-mail:liuzl@mail.njust.edu.cn; 研究方向：含能化合物的合成

Synthesis of 3,5-Dichloro-2,4,6-trinitrobenzenamine and Its Derivatives

HOU Kehui, LIU Zuliang*   

  1. (School of Chemical Engineering,Nanjing University of Science and Technology,Nanjing 21009,China)
  • Received:2013-01-21 Revised:2013-04-12 Published:2013-11-10 Online:2013-11-10

PDF

1590

被引次数

1

摘要： 分别以3,5-二氯苯胺为原料，经N保护、硝化、水解以及以1,3,5-三氯-2,4,6-三硝基苯(TCTNB)为原料，经叔丁胺化，再在三氟乙酸中脱叔丁基2种方法合成了3,5-二氯-2,4,6-三硝基苯胺。 与甲胺反应,合成了3,5-二甲氨基-2,4,6-三硝基苯胺，收率85%，再用混酸硝化合成了3,5-二甲硝胺基-2,4,6-三硝基苯胺的硝酸盐，收率70%。 采用核磁共振、质谱、红外和元素分析等进行了结构表征。 探讨了不同参数下TCTNB的氨化结果。 优化的条件为：n(TCTNB)∶n(叔丁胺)=1∶2，CuO为催化剂，KHCO3为碱。

关键词: 合成, 二氯三硝基苯胺, 二甲氨基三硝基苯胺, 二甲硝胺基三硝基苯胺硝酸盐, 含能材料

Abstract: Two synthetic methods have been developed for the synthesis of 3,5-dichloro-2,4,6-trinitrobenzenamine. In the first process, 3,5-dichlorobenzenamine was selected as precursor, followed by N-protection, nitration, and hydrolysis. In another process, 1,3,5-trichloro-2,4,6-tri-nitrobenzene(TCTNB) reacted with 2-amino-2-methylpropane and then trifluoroacetic acid to deprotect. The condensation between 3,5-dichloro-2,4,6-trinitrobenzenamine and methylamine gave 3,5-dimethylamino-2,4,6-trinitrobenzenamine in 85% yield which can be converted to the nitrate of 3,5-dimethylnitramino-2,4,6-trinitrobenzenamine in 70% yield. The structure of the product was confirmed by 1H NMR, MS, IR and elemental analysis. The results of selective of TCTNB under different conditions were discussed. The optimized conditions are：n(TCTNB)∶n(t-butylamine)=1∶2, CuO as catalyst, KHCO3 as base.

Key words: synthesis, dichloro-trinitrobenzenamine, dimethylamino-trinitrobenzenamine, dimethylnitramino-trinitrobenzenamine nitrate, enegetic material

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