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

doi:10.6023/cjoc201712022

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

Articles

十二氢十二硼酸双(二烷基-5-氨基四唑)盐的合成、表征及热性能

绳利丽^a, 单自兴^a,b, 郭晓燕^a, 杨荣杰^a

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 E-mail:yrj@bit.edu.cn
基金资助:
中国人民解放军装备发展部创新（No.71314093）资助项目.

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

Sheng Lili^a, Shan Zixing^a,b, Guo Xiaoyan^a, Yang Rongjie^a

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 E-mail:yrj@bit.edu.cn
Supported by:
Project supported by the Fund of PLA's Equipment Development Department.

We tried combining dodecahydrodecaborane anion (B₁₂H₁₂^2-) 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

Cite this article

Sheng Lili, Shan Zixing, Guo Xiaoyan, Yang Rongjie. Synthesis, Characterization and Thermal Behavior of Bis(dialkyl-5-aminotetrazolium) Dodecadodecaborates[J]. Chin. J. Org. Chem., 2018, 38(8): 2093-2100.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Balucani, N.; Zhang, F. T.; Kaiser, R. I. Chem. Rev. 2010, 110, 5107.
[2] Hansen, B. R. S.; Paskevicius, M.; Li, H. W.; Akiba, E.; Jensen, T. R. Coord. Chem. Rev. 2015, 323, 60.
[3] Tang, S. Q.; Ding, H. X. J. Propul. Technol. 1983, 4, 35(in Chinese). (唐松青, 丁宏勋, 推进技术, 1983, 4, 35.)
[4] Wang, W. Q.; Xue, Y. N.; Yang, J. M.; Li,Y. N.; Yu, Q. W.; Mei, S. N. Chin. J. Energy Mater. 2012, 20, 132.
[5] Shan, Z. X.; Sheng, L. L.; Yang, R. J. Chin. J. Explos. Propell. 2017, 40, 1(in Chinese). (单自兴, 绳利丽, 杨荣杰, 火炸药学报, 2017, 40, 1.)
[6] Gao, X.; Shreeve, J. M. Chem. Rev. 2011, 111, 7377.
[7] Li, Y. L.; Xue, M.; Wang, J. L.; Cao, D. L.; Ma, Z. L. Chin. J. Org. Chem. 2016, 36, 1528(in Chinese). (李云路, 薛梅, 王建龙, 曹端林, 马忠亮, 有机化学, 2016, 36, 1528.)
[8] Singh, R. P.; Verma, R. D.; Meshri, D. T.; Shreeve, J. M. Angew. Chem., Int. Ed. 2006, 45, 3584.
[9] Hiskey, M.; Chavez, D.; Son, S. F. Proc. 27th International Pyrotechnics Seminar, Colorado, USA, 2000, pp. 3~14.
[10] Klapötke, T. M. Struct. Bonding 2007, 125, 85.
[11] Miller, C. G.; Williams, G. K. US 0199937, 2009.
[12] Miller, C. G.; Williams, G. K. US 0099111, 2008.
[13] Zhang, S. H.; Han, L.; Wang, X. D. Chin. J. Luoyang Normal Univ. 2005, 5, 74(in Chinese). (张苏杭, 韩琳, 王新德, 洛阳师范学院报, 2005, 5, 74.)
[14] Veronika, E.; Klapötke, T. M.; Jörg, S. Z. Anorg. Allg. Chem. 2010, 633, 879.
[15] Herbst, R. M.; Garrison, J. A. J. Org. Chem. 1953, 18, 941.
[16] Denffer, M. V.; Klapötke, T. M.; Heeb, G. Propellants, Explos., Pyrotech. 2005, 30, 191.
[17] Rittenhouse, C. T.; Ariz, G. US 3663553, 1972.
[18] Sinditskii, V. P.; Fogelzang, A. E.; Levshenkov, A. I. Proceedings of the 21st International Pyrotechnics Seminar, Beijing, 1995, pp. 762~773.
[19] Denffer, M. V.; Klapötke, T. M.; Sabat, C. M. Z. Anorg. Allg. Chem. 2008, 634, 2575.
[20] Brill, T. B.; Ramanathan, H. Combust. Flame 2000, 122, 165.
[21] Jin, C.; Ye, C.; Piekarski, C.; Twamley, B.; Shreeve, J. M. Eur. J. Inorg. Chem. 2005, 18, 3760.
[22] Zhang, Q.; Shreeve, J. M. Chem. Rev. 2014, 114, 10527.
[23] Mccrary, P. D.; Barber, P. S.; Kelley, S. P.; Rogers, R. D. Inorg. Chem. 2014, 53, 4770.
[24] Zhang, W.; Qi, X.; Huang, S.; Li, J.; Tang, C.; Li, J. J. Mater. Chem. A 2016, 4, 8978.
[25] Xue, Y. N.; Wang, W. Q.; Li, J. Y.; Lu, J. Y.; Lü, J. Chin. Energy Mater. 2016, 24, 274(in Chinese). (薛云娜, 王为强, 李娇毅, 路居有, 吕剑, 含能材料, 2016, 24, 274.)
[26] Rao, M. H.; Muralidharan, K. Polyhedron 2016, 115, 105.
[27] Janiak, C.; Esser, L. Chem. Sci. 1993, 48, 394.
[28] Belletire, J. L.; Schneider, S.; Wight, B. A.; Strauss, S. L.; Shackelford, S. A. Synth. Commun. 2012, 42, 155.
[29] Thomas, M. K.; Karaghiosoff, K.; Mayer, P.; Penger, A.; Jan, M. W. Propellants, Explos., Pyrotech. 2006, 31, 188.
[30] Thomas, M, K.; Carles, M. S.; Magdalena, R. Z. Anorg. Allg. Chem. 2008, 634, 688.
[31] Herbst, R. M.; Percival, D. F. J. Org. Chem. 1954, 17, 439.
[32] Murphy, D. B.; Picard, J. P. J. Org. Chem. 1954, 17, 1807.
[33] Henry, R. A.; Finnegan, W. G. J. Am. Chem. Soc. 1954, 76, 923.

十二氢十二硼酸双(二烷基-5-氨基四唑)盐的合成、表征及热性能

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

PDF

Knowledge

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Penghui Li, Qingyang Xie, Fuxian Wan, Yuanhong Zhang, Lin Jiang. Synthesis and Fungicidal Activity of Novel Substituted Pyrimidine-5-carboxamides Bearing Cyclopropyl Moiety [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 650-656.
[2]	Fakai Zou, Nengzhong Wang, Hui Yao, Hui Wang, Mingguo Liu, Nianyu Huang. Regio- and Stereo-selective Synthesis of 1β-/3R-Aryl Thiosugar [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 593-604.
[3]	Luyao Li, Zhongwen He, Zhenguo Zhang, Zhenhua Jia, Teck-Peng Loh. Application of Triaryl Carbenium in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 421-437.
[4]	Qinggang Mei, Qinghan Li. Recent Progress of Visible Light-Induced the Synthesis of C(3) (Hetero)arylthio Indole Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(2): 398-408.
[5]	Weiqing Yang, Yanbing Ge, Yuanyuan Chen, Ping Liu, Haiyan Fu, Menglin Ma. Design and Synthesis of Fluorescent 1,8-Napthalimide Derivatives and Their Identification of Cysteine [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 180-194.
[6]	Qianfan Zhao, Yongzheng Chen, Shiming Zhang. Application and Mechanism Study of Carbon-Based Metal-Free Catalysts in Organic Synthesis [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 137-147.
[7]	Shan Chen, Zhilin Chen, Qiong Hu, Yanshuang Meng, Yue Huang, Pingfang Tao, Liru Lu, Guobao Huang. Recognition of Bis-thiourea Tweezers to Neutral Molecules in Non-Polar Solvent [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 277-281.
[8]	Huakun Wang, Xiaolong Ren, Yining Xuan. Study of the Halide Salt Catalyzed [3＋2] Cycloaddition of α,β-Epoxy Carboxylate with Isocyanate [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 251-258.
[9]	Yukun Jin, Baoyi Ren, Fushun Liang. Visible Light-Mediated Selective C—F Bond Cleavage of Trifluoromethyl Groups and Its Application in Synthesizing gem-Difluoro-Containing Compounds [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 85-110.
[10]	Cuiyun Ma, Hailan Luo, Fuhua Zhang, Dan Guo, Shuxing Chen, Fei Wang. Green Biosynthesis, Photophysical Properties and Application of 3-Pyrrolyl BODIPY [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 216-223.
[11]	Bozhen Wang, Jie Zhang, Chunhui Nian, Mingming Jin, Miaomiao Kong, Wulan Li, Wenfei He, Jianzhang Wu. Synthesis and Antitumor Activity of 3,4-Dichlorophenyl Amides [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 232-241.
[12]	Shihang Yu, Jiawei Liu, Biyu An, Qinghua Bian, Min Wang, Jiangchun Zhong. Asymmetric Synthesis of the Contact Sex Pheromone of Neoclytus acuminatus acuminatus (Fabricius) [J]. Chinese Journal of Organic Chemistry, 2024, 44(1): 301-308.
[13]	Ruixia Cao, Yuping Jia. Synthesis and Biological Activity of Novel Pyrrolo[2,3-d]pyrimidine Derivatives Containing Coumarin [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3304-3311.
[14]	Huanqing Li, Zhaohua Chen, Zujia Chen, Qiwen Qiu, Youcai Zhang, Sihong Chen, Zhaoyang Wang. Research Progress in Mercury Ion Fluorescence Probes Based on Organic Small Molecules [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3067-3077.
[15]	Ran Zhou, Chunmei Yuan, Tao Zhang, Piao Mao, Yi Liu, Kaini Meng, Hui Xin, Wei Xue. Design, Synthesis and Bioactivity of Chalcone Derivative Containing Quinazolinone [J]. Chinese Journal of Organic Chemistry, 2023, 43(9): 3196-3209.