Chinese Journal of Organic Chemistry >
Synthesis, Characterization and Thermal Behavior of Bis(dialkyl-5-aminotetrazolium) Dodecadodecaborates
Received date: 2017-12-15
Revised date: 2018-03-20
Online published: 2018-05-03
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.
Sheng Lili , Shan Zixing , Guo Xiaoyan , Yang Rongjie . Synthesis, Characterization and Thermal Behavior of Bis(dialkyl-5-aminotetrazolium) Dodecadodecaborates[J]. Chinese Journal of Organic Chemistry, 2018 , 38(8) : 2093 -2100 . DOI: 10.6023/cjoc201712022
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