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有机化学
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有机化学 ›› 2011, Vol. 31 ›› Issue (9): 1484-1489. 上一篇    下一篇

研究简报

4,4,6,6-四叠氮基偶氮-1,3,5-三嗪(TAAT)的合成、表征与热分解研究

李玉川1，张雪娇1，付耿2，庞思平1，赵长禄*,2   

  1. (1北京理工大学材料学院 北京 100081)
    (2北京理工大学机械与车辆学院 北京 100081)
  • 收稿日期:2011-09-19 修回日期:2011-03-08 发布日期:2011-04-12
  • 通讯作者: 李玉川 E-mail:yuchuanyh@yahoo.com.cn

Synthesis, Characterization and Thermal Decomposition Mechanism of 4,4,6,6-Tetra(azido)azo-1,3,5-triazine (TAAT)

Li Yuchuan1 Zhang Xuejiao1 Fu Geng2 Pang Siping1 Zhao Changlu*,2   

  1. (1 School of Material Science and Engineering, Beijing Institute of Technology, Beijing 100081)
    (2 School of Mechanical Engineering, Beijing Institute of Technology, Beijing 100081)
  • Received:2011-09-19 Revised:2011-03-08 Published:2011-04-12
  • Contact: LI Yu-Chuan E-mail:yuchuanyh@yahoo.com.cn

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以4,4,6,6-四叠氮基联氨-1,3,5-三嗪(TAHT)为原料, 经三氯异氰尿酸(TCI)、二氯异氰尿酸(DCI)、二氯异氰尿酸钠(SDCI)、二溴异氰尿酸钠(SDBI)、N-氯代丁二酰亚胺(NCS)、N-溴代丁二酰亚胺(NBS)、氯气(Cl2)、液溴(Br2)、次氯酸钠(NaClO)等氧化联氨键形成偶氮键合成了4,4,6,6-四叠氮基偶氮-1,3,5-三嗪(TAAT), 产率72%～93%. 通过FT-IR, 13C NMR, MS, 元素分析等手段对其进行了表征|考察了不同氧化剂对氧化联氨键形成偶氮键反应的影响, 验证了TAHT氧化合成TAAT的机理. 通过DSC、程序升温FT-IR等测试结果, 提出了TAAT的热分解机理.

关键词: 叠氮化合物, 三嗪, 合成, 氧化反应, 热分解, 机理

4,4,6,6-Tetra(azido)azo-1,3,5-triazine (TAAT) was synthesized from 4,4,6,6-tetra(azido)hy-drazo-1,3,5-triazine (TAHT) by the oxidative reaction with trichloroisocyanuric acid (TCI), dichloro- isocyanuric acid (DCI), sodium dichloroisocyanurate (SDCI), sodium dibromoisocyanurate (SDBI), N-chlorosuccinide (NCS), N-bromosuccinide (NBS), Cl2, Br2 and sodium hypochlorite (NaClO) with the yields of 72%～93%. Its structure was characterized by FT-IR, 13C NMR, MS techniques and elemental analysis. The effects of different oxidants on oxidation reaction of hydrazo group were investigated, the oxidation mechanism of TAHT was proved and a thermal decomposition mechanism of TAAT was presented based on the results of DSC and FTIR with a dynamic heating process from 50 ℃ to 600 ℃.

Key words: diazoimido compound, triazine, synthesis, oxidation reaction, thermal decomposition, mechanism