Citation: Yong-Tao Gao, Lin-Man Zhao, Fu-Qing Pang, Xiu-Juan Qi, Jing-Lun Huang, Fu-Xue Chen. Synthesis and properties of energetic salts based on 3-nitro-5-nitroimino-1,2,4-oxadiazole[J]. Chinese Chemical Letters, ;2016, 27(03): 433-436. doi: 10.1016/j.cclet.2015.12.008 shu

Synthesis and properties of energetic salts based on 3-nitro-5-nitroimino-1,2,4-oxadiazole

a.
a. School of Chemical Engineering and the Environment, Beijing Institute of Technology, Beijing 100081, China;
b.
b. Research Center of Energetic Material Genome Science, Institute of Chemical Materials, China Academy of Engineering Physics, Mianyang 621050, China

Corresponding author: Fu-Xue Chen,
Received Date: 23 September 2015
Available Online: 20 November 2015
Fund Project:

A series of 3-nitro-5-nitroimino-1,2,4-oxadiazole-based energetic salts were synthesized from 3-nitro-5-nitroimino-1,2,4-oxadiazole anion and nitrogen-rich cations. They were fully characterized by IR, elemental analysis and NMR spectroscopy. The structure of triaminoguanidinium salt (1-e) was confirmed by single crystal X-ray diffraction. All salts showed good thermal stability with decomposed temperature ranging from 155℃ to 258℃, and positive heats of formation from 226.0 kJ/mol to 554.1 kJ/mol. Thus, the theoretic detonation pressure was predicted from 28.70 GPa to 37.60 GPa and velocities from 8526 m/s to 9354 m/s. Among them, guanidinium salt (1-c) exhibited both high decomposition temperature (258℃) and detonation velocity (9319 m/s).
- Energetic salts,
- Explosives,
- Ionic salts,
- Nitrogen-rich cations,
- Nitroamines,
- 1,2,4-Oxadiazole
1. [1]
  [1] D.M. Badgujar, M.B. Talawar, S.N. Asthana, P.P. Mahulikar, Advances in science and technology of modern energetic materials:an overview, J. Hazard. Mater. 151(2008) 289-305.
2. [2]
  [2] Q.H. Zhang, J.M. Shreeve, Energetic ionic liquids as explosives and propellant fuels:a new journey of ionic liquid chemistry, Chem. Rev. 114(2014) 110527-110574.
3. [3]
  [3] M.B. Talawar, R. Sivabalan, T. Mukundan, et al., Environmentally compatible next generation green energetic materials (GEMs), J. Hazard. Mater. 161(2009) 589-607.
4. [4]
  [4] P.F. Pagoria, G.S. Lee, A.R. Mitchell, R.D. Schmidt, A review of energetic materials synthesis, Thermochim. Acta 384(2002) 187-204.
5. [5]
  [5] J.P. Agrawal, Recent trends in high-energy materials, Prog. Energy Combust. Sci. 24(1998) 1-30.
6. [6]
  [6] H.X. Gao, J.M. Shreeve, The many faces of FOX-7:a precursor to high-performance energetic materials, Angew. Chem. (Ⅰ)nt. Ed. 54(2015) 6335-6338.
7. [7]
  [7] X. Yin, J.T. Wu, X. Jin, et al., Nitrogen-rich salts of 1-aminotetrazol-5-one:oxygencontaining insensitive energetic materials with high thermal stability, RSC Adv. 5(2015) 60005-60014.
8. [8]
  [8] (a) L. Liu, Y.Q. Zhang, Z.M. Li, S.J. Zhang, Nitrogen-rich energetic 4-R-5-nitro-1,2,3-triazolate salts (R=-CH₃,-NH₂,-N₃,-NO₂ and-NHNO₂) as high performance energetic materials, J. Mater. Chem. A 3(2015) 14768-14778;
9. [9]
  (b) C.L. He, J.H. Zhang, D.A. Parrish, J.M. Shreeve, 5-Chloro-3,5-dinitropyrazole:a precursor for promising insensitive energetic compounds, J. Mater. Chem. A 1(2013) 2863-2868;
10. [10]
  (c) Y.C. Li, Q. Cai, S.H. Li, et al., 1,1'-Azobis-1,2,3-triazole:a high-nitrogen compound with stable N8 structure and photochromism, J. Am. Chem. Soc. 132(2010) 12172-12173.
11. [11]
  [9] (a) P.M. Jadhav, S. Radhakrishnan, V.D. Ghule, R.K. Pandey, Energetic salts from nitroformate ion, J. Mol. Model. 21(2015) 1-5;
12. [12]
  (b) H. Wei, C.L. He, J.H. Zhang, J.M. Shreeve, Combination of 1, 2,4-oxadiazole and 1,2,5-oxadiazole moieties for the generation of high performance energetic materials, Angew. Chem. (Ⅰ)nt. Ed. 54(2015) 9367-9371;
13. [13]
  (c) M.A. Kettner, T.M. Klapçtke, T.G. Witkowski, F. von Hundling, Synthesis, characterisation and crystal structures of two bi-oxadiazole derivatives featuring the trifluoromethyl group, Chem. Eur. J. 21(2015) 4238-4241.
14. [14]
  [10] (a) Z.D. Fu, R. Su, Y.Wang, et al., Synthesis and characterization of energetic 3-nitro-1,2,4-oxadiazoles, Chem. Eur. J. 18(2012) 1886-1889;
15. [15]
  (b) Z.D. Fu, C. He, F.X. Chen, Synthesis and characteristics of a novel, high-nitrogen, heat-resistant, insensitive material (NOG2Tz), J. Mater. Chem. 22(2012) 60-63;
16. [16]
  (c) Z.D. Fu, Y. Wang, L. Yang, et al., Synthesis and characteristics of novel, high nitrogen 1,2,4-oxadiazoles, RSC Adv. 4(2014) 11859-11861;
17. [17]
  (d) A.B. Sheremetev, The chemistry of furazans fused to six-and seven-membered heterocycles with one heteroatom, Russ. Chem. Rev. 68(1999) 137-148.
18. [18]
  [11] (a) Z.D. Fu, Y. Wang, F.X. Chen, Comparison of thermal performance of new energetic materials NONHT and NONsHT, Acta Armamentarii 34(2012) 235-239;
19. [19]
  (b) Y. Wang, Z.D. Fu, F.X. Chen, Effect of new energetic materials NOG2TZ to HMX thermal decomposition behavior, Chin. J. Energy Mater. 22(2014) 22-25;
20. [20]
  (c) Z.D. Fu, Y. Wang, F.X. Chen, The thermal decomposition behavior of new energetic materials NOG, Chin. J. Energy Mater. 20(2012) 583-586.
21. [21]
  [12] Y. K. Wu, G. Y. Chen, Z. M. Zhou, H. S. Dong, A method of prediction compound crystal density, CN 101957300 A (2009).
22. [22]
  [13] H.X. Gao, J.M. Shreeve, Azole-based energetic salts, Chem. Rev. 111(2011) 7377-7436.
23. [23]
  [14] M.J. Frisch, Gaussian 09, Gaussian, (Ⅰ)nc, Wallingford, CT, 2009.
24. [24]
  [15] R.G. Parr, W. Yang, Density Functional Theory of Atoms and Molecules, Oxford University Press, New York, NY, 1989.
25. [25]
  [16] H.D. Jenkins, D. Tudeal, L. Glasser, Lattice potential energy estimation for complex ionic salts from density measurements, (Ⅰ)norg. Chem. 41(2002) 2364-2367.
1. [1]
  Peiyan Zhu , Yanyan Yang , Hui Li , Jinhua Wang , Shiqing Li . Rh(Ⅲ)‐Catalyzed sequential ring‐retentive/‐opening [4 + 2] annulations of 2H‐imidazoles towards full‐color emissive imidazo[5,1‐a]isoquinolinium salts and AIE‐active non‐symmetric 1,1′‐biisoquinolines. Chinese Chemical Letters, 2024, 35(10): 109533-. doi: 10.1016/j.cclet.2024.109533
2. [2]
  Liangfeng Yang , Liang Zeng , Yanping Zhu , Qiuan Wang , Jinheng Li . Copper-catalyzed photoredox 1,4-amidocyanation of 1,3-enynes with N-amidopyridin-1-ium salts and TMSCN: Facile access to α-amido allenyl nitriles. Chinese Chemical Letters, 2024, 35(11): 109685-. doi: 10.1016/j.cclet.2024.109685
3. [3]
  Yu Yao , Jinqiang Zhang , Yantao Wang , Kunsheng Hu , Yangyang Yang , Zhongshuai Zhu , Shuang Zhong , Huayang Zhang , Shaobin Wang , Xiaoguang Duan . Nitrogen-rich carbon for catalytic activation of peroxymonosulfate towards green synthesis. Chinese Chemical Letters, 2024, 35(11): 109633-. doi: 10.1016/j.cclet.2024.109633
4. [4]
  Ruilong Geng , Lingzi Peng , Chang Guo . Dynamic kinetic stereodivergent transformations of propargylic ammonium salts via dual nickel and copper catalysis. Chinese Chemical Letters, 2024, 35(8): 109433-. doi: 10.1016/j.cclet.2023.109433
5. [5]
  Rong-Nan Yi , Wei-Min He . Electron donor-acceptor complex enabled arylation of dithiocarbamate anions with thianthrenium salts under aqueous micellar conditions. Chinese Chemical Letters, 2024, 35(11): 110194-. doi: 10.1016/j.cclet.2024.110194
6. [6]
  Junxin Li , Chao Chen , Yuzhen Dong , Jian Lv , Jun-Mei Peng , Yuan-Ye Jiang , Daoshan Yang . Ligand-promoted reductive coupling between aryl iodides and cyclic sulfonium salts by nickel catalysis. Chinese Chemical Letters, 2024, 35(11): 109732-. doi: 10.1016/j.cclet.2024.109732
7. [7]
  Rong-Nan Yi , Wei-Min He . Visible light/copper catalysis enabled radial type ring-opening of sulfonium salts. Chinese Chemical Letters, 2025, 36(4): 110787-. doi: 10.1016/j.cclet.2024.110787
8. [8]
  Jiaojiao Liang , Youming Peng , Zhichao Xu , Yufei Wang , Menglong Liu , Xin Liu , Di Huang , Yuehua Wei , Zengxi Wei . Boron/phosphorus co-doped nitrogen-rich carbon nanofiber with flexible anode for robust sodium-ion battery. Chinese Chemical Letters, 2025, 36(1): 110452-. doi: 10.1016/j.cclet.2024.110452
9. [9]
  Xueru Zhao , Aopu Wang , Shimin Wang , Zhijie Song , Li Ma , Li Shao . Adsorption and visual detection of nitro explosives by pillar[n]arenes-based host–guest interactions. Chinese Chemical Letters, 2025, 36(4): 110205-. doi: 10.1016/j.cclet.2024.110205
10. [10]
  Chunhua Ma , Mengjiao Liu , Siyu Ouyang , Zhenwei Cui , Jingjing Bi , Yuqin Jiang , Zhiguo Zhang . Metal-free construction of diverse 1,2,4-triazolo[1,5-a]pyridines on water. Chinese Chemical Letters, 2025, 36(1): 109755-. doi: 10.1016/j.cclet.2024.109755
11. [11]
  Shiqi Xu , Zi Ye , Shuang Shang , Fengge Wang , Huan Zhang , Lianguo Chen , Hao Lin , Chen Chen , Fang Hua , Chong-Jing Zhang . Pairs of thiol-substituted 1,2,4-triazole-based isomeric covalent inhibitors with tunable reactivity and selectivity. Chinese Chemical Letters, 2024, 35(7): 109034-. doi: 10.1016/j.cclet.2023.109034
12. [12]
  Zhenyu Hu , Zhenchun Yang , Shiqi Zeng , Kun Wang , Lina Li , Chun Hu , Yubao Zhao . Cationic surface polarization centers on ionic carbon nitride for efficient solar-driven H₂O₂ production and pollutant abatement. Chinese Chemical Letters, 2024, 35(10): 109526-. doi: 10.1016/j.cclet.2024.109526
13. [13]
  Jincheng Zhang , Mengjie Sun , Jiali Ren , Rui Zhang , Min Ma , Qingzhong Xue , Jian Tian . Oxygen vacancies-rich molybdenum tungsten oxide nanowires as a highly active nitrogen fixation electrocatalyst. Chinese Chemical Letters, 2025, 36(1): 110491-. doi: 10.1016/j.cclet.2024.110491
14. [14]
  You Zhou , Li-Sheng Wang , Shuang-Gui Lei , Bo-Cheng Tang , Zhi-Cheng Yu , Xing Li , Yan-Dong Wu , Kai-Lu Zheng , An-Xin Wu . I₂-DMSO mediated tetra-functionalization of enaminones for the construction of novel furo[2′,3′:4,5]pyrimido[1,2-b]indazole skeletons via in situ capture of ketenimine cations. Chinese Chemical Letters, 2025, 36(1): 109799-. doi: 10.1016/j.cclet.2024.109799
15. [15]
  Ze-Yuan Ma , Mei Xiao , Cheng-Kun Li , Adedamola Shoberu , Jian-Ping Zou . S-(1,3-Dioxoisoindolin-2-yl)O,O-diethyl phosphorothioate (SDDP): A practical electrophilic reagent for the phosphorothiolation of electron-rich compounds. Chinese Chemical Letters, 2024, 35(5): 109076-. doi: 10.1016/j.cclet.2023.109076
16. [16]
  Tianlong Zhang , Rongling Zhang , Hongsheng Tang , Yan Li , Hua Li . Online Monitoring and Mechanistic Analysis of 3,5-diamino-1,2,4-triazole (DAT) Synthesis via Raman Spectroscopy: A Recommendation for a Comprehensive Instrumental Analysis Experiment. University Chemistry, 2024, 39(6): 303-311. doi: 10.3866/PKU.DXHX202312006
17. [17]
  Yixia Zhang , Caili Xue , Yunpeng Zhang , Qi Zhang , Kai Zhang , Yulin Liu , Zhaohui Shan , Wu Qiu , Gang Chen , Na Li , Hulin Zhang , Jiang Zhao , Da-Peng Yang . Cocktail effect of ionic patch driven by triboelectric nanogenerator for diabetic wound healing. Chinese Chemical Letters, 2024, 35(8): 109196-. doi: 10.1016/j.cclet.2023.109196
18. [18]
  Pei Cao , Yilan Wang , Lejian Yu , Miao Wang , Liming Zhao , Xu Hou . Dynamic asymmetric mechanical responsive carbon nanotube fiber for ionic logic gate. Chinese Chemical Letters, 2024, 35(6): 109421-. doi: 10.1016/j.cclet.2023.109421
19. [19]
  Qiangwei Wang , Huijiao Liu , Mengjie Wang , Haojie Zhang , Jianda Xie , Xuanwei Hu , Shiming Zhou , Weitai Wu . Observation of high ionic conductivity of polyelectrolyte microgels in salt-free solutions. Chinese Chemical Letters, 2024, 35(4): 108743-. doi: 10.1016/j.cclet.2023.108743
20. [20]
  Hao-Cong Li , Ming Zhang , Qiyan Lv , Kai Sun , Xiao-Lan Chen , Lingbo Qu , Bing Yu . Homogeneous catalysis and heterogeneous separation: Ionic liquids as recyclable photocatalysts for hydroacylation of olefins. Chinese Chemical Letters, 2025, 36(2): 110579-. doi: 10.1016/j.cclet.2024.110579

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(637)
HTML views(34)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142