Chin. J. Org. Chem. ›› 2018, Vol. 38 ›› Issue (8): 2093-2100.DOI: 10.6023/cjoc201712022 Previous Articles     Next Articles



绳利丽a, 单自兴a,b, 郭晓燕a, 杨荣杰a   

  1. a 北京理工大学材料学院 北京 100081;
    b 武汉大学化学与分子科学学院 武汉 430072
  • 收稿日期:2017-12-15 修回日期:2018-03-20 发布日期:2018-05-03
  • 通讯作者: 杨荣杰
  • 基金资助:


Synthesis, Characterization and Thermal Behavior of Bis(dialkyl-5-aminotetrazolium) Dodecadodecaborates

Sheng Lilia, Shan Zixinga,b, Guo Xiaoyana, Yang Rongjiea   

  1. a School of Materials Science & Engineering, Beijing Institute of Technology, Beijing 100081;
    b Chemistry and Molecular Science College, Wuhan University, Wuhan 430072
  • Received:2017-12-15 Revised:2018-03-20 Published:2018-05-03
  • Contact: 10.6023/cjoc201712022
  • Supported by:

    Project supported by the Fund of PLA's Equipment Development Department.

We tried combining dodecahydrodecaborane anion (B12H122-) with aminotetrazole cation into a series of new borohydrino-tetrazolium salt as a kind of energetic materials. Firstly, by using 1-or 2-5-aminotetrazole (5-ATZ) as the raw material, dialkylated 5-aminotetrazolium iodide was synthesized via dialkylation reaction with methyl iodide and ethyl iodide. And then, the dialkylated 5-aminotetrazolium iodides was used to react with potassium dodecylhydrodecaborate in an aqueous solution by metathesis. Finally, eleven novel bis(dialkyl-5-aminotetrazolium) dodecahydrododecaborates were synthesized. All of them were in yield of above 70%, and their chemical properties were stable under the conditions of purification and drying. These compounds have been characterized by FT-IR, 1H NMR, 13C NMR, 11B NMR, mass spectrometry, and elemental analysis. In inspecting their thermal properties using differential scanning calorimetry (DSC) and thermogravimetric analysis (TG) technologies, the results showed that eleven kinds of bis(dialkyl-5-aminotetrazolium) dodecahydrododecaborates have higher thermal stability and the thermal decomposition temperatures of them are mostly above 200℃. In molecular structures, their thermal stability decrease with the increase of the 4-position alkyl when the 1-position alkyl maintains the same. The rapid thermal decomposition of the five compounds, 1,4-dimethyl, 1-methyl-4-ethyl, 1,3-dimethyl, 1-methyl-3-ethyl, and 1-ethyl-3-methyl, occurred before the melting, and the rapid thermal decomposition of the other 6 compounds occurred after the crystals melting. These high-energetic compounds are of great importance in developing new high-performance propellants.

Key words: dodecadodecaborate, tetrazolium, dialkyl-5-aminotetrazole, energetic material, synthesis, thermal property