吡唑含能离子盐的合成研究进展
收稿日期: 2020-09-08
修回日期: 2020-09-28
网络出版日期: 2020-11-04
基金资助
中国科学院绿色过程制造创新研究院自主部署联合基金(IAGM2020C06)
Progress in the Synthesis of Energetic Salts Based on Pyrazole
Received date: 2020-09-08
Revised date: 2020-09-28
Online published: 2020-11-04
Supported by
Innovation Academy for Green Manufacture, Chinese Academy of Sciences(IAGM2020C06)
吡唑环上有三个可修饰的碳位点和一个可修饰的NH位点, 通过对这四个位点的修饰(主要是引入硝基、硝胺基、氨基、羟基以及形成稠环等), 可设计出种类丰富的吡唑含能化合物. 同时, 相对于2,4,6-三硝基甲苯(TNT)、黑索金(RDX)、奥克托今(HMX)等常规含能化合物, 吡唑含能化合物具有氮含量高、生成焓高及感度低等优势. 近年来, 国内外基于吡唑骨架设计并合成了大量吡唑含能离子盐, 其中很多种化合物表现出高能及钝感等特性. 按单环吡唑含能离子盐、联环吡唑含能离子盐及稠环吡唑含能离子盐, 分类综述了近年来所报道的吡唑含能离子盐的合成及性能, 并对该类化合物的应用前景进行了展望.
李光磊 , 黄海丰 , 杨军 , 段红珍 . 吡唑含能离子盐的合成研究进展[J]. 有机化学, 2021 , 41(4) : 1466 -1488 . DOI: 10.6023/cjoc202009019
The pyrazole ring has three modifiable carbon sites and one modifiable NH site. Based on the pyrazole ring, a variety of pyrazole energetic compounds can be designed by the introduction of nitro, nitramino, amino and hydroxyl group and the formation of fused rings. At the same time, compared with conventional energetic compounds such as 2,4,6-trinitro- benzene (TNT), hexahydro-1,3,5-trinitro-triazine (RDX) and 1,3,5,7-tetranitro-1,3,5,7-tetrazocane (HMX), energetic pyrazoles have the advantages of high nitrogen content, high enthalpy of formation and low sensitivities. In recent years, a large number of energetic salts based on pyrazole have been designed and synthesized around the world, including monocyclic energetic salts, bicyclic energetic salts and fused energetic salts based on pyrazole. Many of them exhibit the characteristics of high energy and low sensitivity. The synthesis and properties of recently reported energetic salts based on pyrazole are reviewed, and their applications in the field of energetic materials are prospected.
Key words: energetic material; energetic salt; pyrazole; nitramino
| [1] | Yang, G.-C.; Li, X.-D. Chin. J. Energ. Mater. 2018, 26,1000. (in Chinese) |
| [1] | ( 杨光成, 李小东, 含能材料, 2018, 26,1000.) |
| [2] | Lu, M. Chin. J. Energ. Mater. 2018, 26,373. (in Chinese) |
| [2] | ( 陆明, 含能材料, 2018, 26,373.) |
| [3] | Huo, H.; Zhang, J.; Dong, J.; Zhai, L.; Guoy, T.; Wang, Z.; Bi, F.; Wang, B. RSC Adv. 2020, 10,11816. |
| [4] | Fischer, N.; Fischer, D.; Klap?tke, T.M.; Piercey, D.G.; Stierstorfer, J. J. Mater. Chem. 2012, 22,20418. |
| [5] | Huang, X.-C.; Guo, T.; Liu, M.; Wang, Z.-J.; Qiu, S.-J.; Ge, Z.-X. Chin. J. Energ. Mater. 2015, 23,291. (in Chinese) |
| [5] | ( 黄晓川, 郭涛, 刘敏, 王子俊, 邱少君, 葛忠学, 含能材料, 2015, 23,291.) |
| [6] | Trache, D.; Klap?tke, T.M.; Maiz, L.; Abd-Elghany, M..; DeLuca, L.T. Green Chem. 2017, 19,4711. |
| [7] | Oommen, C.; Jain, S.R. J. Hazard. Mater. 1999, 67,253. |
| [8] | Jos, J.; Mathew, S. Crit. Rev. Solid State Mater. Sci. 2017, 42,470. |
| [9] | Venkatachalam, S.; Santhosh, G.; Ninan, K.N. Propellants, Explos.,Pyrotech. 2004, 29,178. |
| [10] | Schoyer, H.F. R.; Welland-Veltmans, W.H. M.; Louwers, J.; Korting, P. A., O.G.; Heijden, A. E., D.M.; Keizers, H.L. J.; Berg, R.P. J. Propul. Power 2002, 18,131. |
| [11] | Freudenmann, D.; Ciezki, H.K. Propellants, Explos.,Pyrotech. 2019, 44,1084. |
| [12] | Drake, G.; Hawkins, T.; Brand, A.; Hall, L.; Mckay, M. Propellants, Explos.,Pyrotech. 2003, 28,174. |
| [13] | Singh, R.P.; Verma, R.D.; Shreeve, J.M. Angew. Chem., Int. Ed. 2006, 45,3584. |
| [14] | Gao, H.; Shreeve, J.M. Chem. Rev. 2011, 111,7377. |
| [15] | Gao, H.; Zhang, Q.; Shreeve, J.M. J. Mater. Chem. A 2020, 8,4193. |
| [16] | He, P.; Zhang, J.G.; Yin, X.; Wu, J.T.; Wu, L.; Zhou, Z.N.; Zhang, T.L. Chem.-Eur. J. 2016, 22,7670. |
| [17] | Zhang, Y.; Gao, H.; Joo, Y.H.; Shreeve, J.M. Angew Chem., Int. Ed. 2011, 50,9554. |
| [18] | Zhou, Y.-F.; Wang, T.; Wang, Q.-X.; Gao, H.-X. Chin. J. Energ. Mater. 2018, 26,967. (in Chinese) |
| [18] | ( 周奕霏, 汪涛, 王秋晓, 高海翔, 含能材料, 2018, 26,967.) |
| [19] | Wang, R.; Xu, H.; Guo, Y.; Sa, R.; Shreeve, J.M. J. Am. Chem. Soc. 2010, 132,11904. |
| [20] | Dippold, A.A.; Klap?tke, T.M. J. Am. Chem. Soc. 2013, 135,9931. |
| [21] | Chen, S.; Liu, Y.; Feng, Y.; Yang, X.; Zhang, Q. Chem. Commun. 2020, 56,1493. |
| [22] | Yang, F.; Zhang, P.; Zhou, X.; Lin, Q.; Wang, P.; Lu, M. Cryst. Growth Des. 2020, 20,3737. |
| [23] | Zhao, G.; Kumar, D.; Yin, P.; He, C.; Imler, G.H.; Parrish, D.A.; Shreeve, J.M. Org. Lett. 2019, 21,1073. |
| [24] | Zhao, T.-X.; Li, L.; Dong, Z.; Zhang, Y.; Zhang, G.-Q.; Huang, M.; Li, H.-B. Chin. J. Org. Chem. 2014, 34,304. (in Chinese) |
| [24] | ( 赵廷兴, 李磊, 董战, 张勇, 张光全, 黄明, 李鸿波, 有机化学, 2014, 34,304.) |
| [25] | Fustero, S.; Sánchez-Roselló, M.; Barrio, P.; Simón-Fuentes, A. Chem. Rev. 2011, 111,6984. |
| [26] | Zheng, K.; Iqbal, S.; Hernandez, P.; Park, H.; LoGrasso, P.V.; Feng, Y. J. Med. Chem. 2014, 57,10013. |
| [27] | Urich, R.; Grimaldi, R.; Luksch, T.; Frearson, J.A.; Brenk, R.; Wyatt, P.G. J. Med. Chem. 2014, 57,75369. |
| [28] | Lahm, G.P.; Cordova, D.; Barry, J.D. Bioorg. Med. Chem. 2009, 17,4127. |
| [29] | Weston, C.E.; Richardson, R.D.; Haycock, P.R.; White, A.J. P.; Fuchter, M.J. J. Am. Chem. Soc. 2014, 136,11878. |
| [30] | Hervé, G.; Roussel, C.; Graindorge, H. Angew. Chem., Int. Ed. 2010, 49,3177. |
| [31] | Tang, Y.; Kumar, D.; Shreeve, J.M. J. Am. Chem. Soc. 2017, 139,13684. |
| [32] | Kumar, D.; He, C.; Mitchell, L.A.; Parrish, D.A.; Shreeve, J.M. J. Mater. Chem. A 2016, 4,9220. |
| [33] | Yin, P.; Zhang, J.; He, C.; Parrish, D.A.; Shreeve, J.M. J. Mater. Chem. A. 2014, 2,3200. |
| [34] | Huang, H.; Shi, Y.; Li, H.; Li, H.; Pang, A.; Yang, J. Org. Lett. 2020, 22,5866. |
| [35] | Drukenmüller, I.E.; Klap?tke, T.M.; Morgenstern, Y.; Rusan, M.; Stierstorfer, J.; Z. Anorg. Allg. Chem. 2014, 640,2139. |
| [36] | Jiang, T.; Zhang, X.-Y.; Jing, M.; Shu, Y.-J.; Wang, J. Chin. J. Energ. Mater. 2014, 222,654. (in Chinese) |
| [36] | ( 蒋涛, 张晓玉, 景梅, 舒远杰, 王军, 含能材料, 2014, 222,654.) |
| [37] | Zhao, X.X.; Qi, C.; Zhang, L.B. Molecules 2014, 19,896. |
| [38] | Politzer, P.; Lane, P.; Murray, J.S. Mol. Phys. 2013, 112,719. |
| [39] | Wu, J.-P.; Cao, D.-L.; Wang, J.-L.; Liu, Y.; Li, Y.-X. Chin. J. Energ. Mater. 2016, 24,1121. (in Chinese) |
| [39] | ( 吴军鹏, 曹端林, 王建龙, 刘洋, 李永祥, 含能材料, 2016, 24,1121.) |
| [40] | Wang, W.-J.; Li, H.; Pan, R.-M.; Zhu, W.-H. Chin. J. Org. Chem. 2019, 39,1362. (in Chinese) |
| [40] | ( 王万军, 李欢, 潘仁明, 朱卫华, 有机化学, 2019, 39,1362.) |
| [41] | Zhang, Y.Q.; Guo, Y.; Joo, Y.H. Chem.-Eur. J. 2010, 116,10778. |
| [42] | Zhang, Y.Q.; Parrish, D.A.; Shreeve, J.M. J. Mater. Chem. 2012, 22,12659. |
| [43] | Schmidt, R.D.; Lee, G.S.; Pagoria, P.F.; Mitchell, A.R. J. Heterocycl. Chem. 2001,38, 1227. |
| [44] | Zhang, Y.Q.; Parrish, D.A.; Shreeve, J.M. Chem.-Eur. J. 2012, 18,987. |
| [45] | Yin, P.; Parrish, D.A.; Shreeve, J.M. J. Am. Chem. Soc. 2015, 1137,4778. |
| [46] | Deng, M.-C.; Wang, Y.; Zhang, W.-Q.; Zhang, Q.-H. Chin. J. Energ. Mater. 2017, 25,646. (in Chinese) |
| [46] | ( 邓沐聪, 王毅, 张文全, 张庆华, 含能材料, 2017, 25,646.) |
| [47] | Yin, P.; Mitchell, L.A.; Parrish, D.A. Chem.-Asian J. 2017, 112,378. |
| [48] | B?lter, M.F.; Klap?tke, T.M.; Kustermann, T.; Lenz, T.; Stierstorfer, J. Eur. J. Inorg. Chem. 2018, 37,4125. |
| [49] | Zhang, Y.Y.; Li, Y.N. Dalton Trans. 2019, 448,1524. |
| [50] | Zhang, Y.Y.; Li, Y.N.; Yu, T.; Liu, Y.Z.; Chen, S.P.; Ge, Z.X.; Sun, C.H.; Pang, S.P. ACS Omega 2019, 44,19011. |
| [51] | Lei, C.J.; Yang, H.W.; Cheng, G.B. Dalton Trans. 2020, 49,1660. |
| [52] | Hervé, G.; Roussel, C.; Graindorge, H. Angew. Chem., Int. Ed. 2010, 122,3177. |
| [53] | Dalinger, I.L.; Vatsadze, I.A.; Shkineva, T.K.; Popova, G.P.; Shevelev, S.A. Mendeleev Commun. 2010, 20,253. |
| [54] | Ravi, P.; Tewari, S.P. Catal. Commun. 2012, 19,37. |
| [55] | Ravi, P.; Gore, G.M.; Tewari, S.P.; Sikder, A, K. J. Heterocycl. Chem. 2013, 50,1322. |
| [56] | Zhao, X.X.; Zhang, J.C.; Li, S.H.; Yang, Q.P.; Liu, Y.C.; Pang, S.P. Org. Process Res. Dev. 2014, 18,886. |
| [57] | Ravi, P.; Gore, G.M.; Sikder, A.K.; Tewari, S.P. Synth. Commun. 2012, 42,3463. |
| [58] | B?lter, M.F.; Harter, A.; Klap?tke, T.M.; Stierstorfer, J. ChemPlusChem 2018, 83,804. |
| [59] | Janssen, J. W., A.M.; Habraken, C.L. J. Org. Chem. 1971, 36,3081. |
| [60] | Janssen, J. W., A.M.; Koeners, H.J.; Kruse, C.G.; Habraken, C.L. J. Org. Chem. 1973, 38,1777. |
| [61] | Makosza, M.; Winiarski, J. Acc. Chem. Res. 1987, 20,282. |
| [62] | Li, C.; Liang, L.X.; Wang, K.; Bian, C.M.; Zhang, J.; Zhou, Z.M. J. Mater. Chem. A 2014, 22,18097. |
| [63] | Li, C.; Zhang, M.; Chen, Q.S.; Li, Y.Y.; Gao, H.Q.; Fu, W.; Zhou, Z.M. Dalton Trans. 2016, 445,17956. |
| [64] | Kumar, D.; Imler, G.H.; Parrish, D.A.; Shreeve, J.M. Chem.-Eur. J. 2017, 23,7876. |
| [65] | Fu, W.; Zhao, B.J.; Zhang, M.; Li, C.; Gao, H.Q.; Zhang, J.; Zhou, Z.M. J. Mater. Chem. A 2017, 5,5044. |
| [66] | Tang, Y.X.; Ma, J.C.; Imler, G.H.; Parrish, D.A.; Shreeve, J.M. Dalton Trans. 2019, 48,14490. |
| [67] | Sheremetev, A.B.; Yudin, I.L.; Palysaeva, N.V.; Suponitsky, K. Y. J. Heterocycl. Chem. 2012, 49,394. |
| [68] | Tang, Y.X.; He, C.L.; Imler, G.H.; Parrish, D.A.; Shreeve, J.M. J. Mater. Chem. A 2018, 6,5136. |
| [69] | Xu, M.X.; Cheng, G.B.; Xiong, H.L.; Wang, B.H.; Ju, X.H.; Yang, H.W. New J. Chem. 2019, 43,11157. |
| [70] | Benz, M.; Klap?tke, T.M.; Stierstorfer, J. Z. Anorg. Allg. Chem. 2020, 646,1. |
| [71] | Gospodinov, I.; Domasevitch, K.V.; Unger, C.C.; Klap?tke, T.M. Cryst. Growth Des. 2020, 20,755. |
| [72] | Ma, Q.; Zhang, G.J.; Li, J.; Zhang, Z.Q.; Lu, H.C.; Liao, L.Y.; Fan, G.J.; Nie, F. Chem. Eng. J. 2020, 379,1. |
| [73] | Tang, Y.; He, C.; Mitchell, L.A.; Parrish, D.A.; Shreeve, J.M. Angew. Chem., Int. Ed. 2016, 55,5565. |
| [74] | Zhang, M.; Fu, W.; Li, C.; Gao, H.Q.; Tang, L.W.; Zhou, Z.M. Eur. J. Inorg. Chem. 2017, 22,2883. |
| [75] | Schulze, M.C.; Scott, B.L.; Chavez, D.E. J. Mater. Chem. A 2015, 3,17963. |
| [76] | Klenov, M.S.; Guskov, A.A.; Anikin, O.V.; Churakov, A.M.; Strelenko, Y.A.; Fedyanin, I.V.; Lyssenko, K.A.; Tartakovsky, V.A. Angew. Chem., Int. Ed. 2016, 55,11472. |
| [77] | Chavez, E.E.; Parrish, D.A.; Mitchell, L.; Imler, G.H. Angew. Chem., Int. Ed. 2017, 56,3575. |
| [78] | Yin, P.; Zhang, J.; Imler, G.H.; Parrish, D.A.; Shreeve, J.M. Angew. Chem., Int. Ed. 2017, 56,8834. |
| [79] | Zhang, J.; Yin, P.; Mitchell, L.A.; Parrish, D.A.; Shreeve, J.M. J. Mater. Chem. A 2016, 4,7430. |
| [80] | Shevelev, S.A.; Dalinger, I.L.; Shkineva, T.K.; Gulevskaya, B. I., U. V. I.; Kanishichev, M.I. Russ. Chem. Bull. 1993. 42,1063. |
| [81] | Zhang, J.H.; Parrish, D.A.; Shreeve, J.M. Chem.-Asian J. 2014, 99,2953. |
| [82] | Yin, P.; He, C.L.; Shreeve, J.M. J. Mater. Chem. A 2016, 4,1514. |
| [83] | Yin, P.; Zhang, J.H.; Mitchell, L.A.; Parrish, D.A.; Shreeve, J.M. Angew. Chem., Int. Ed. 2016, 555,12895. |
| [84] | Li, Y.N.; Hu, J.J.; Chang, P.; Chen, T.; Zhang, H.W.; Wang, B. Chin. J. Expl. Propell. 2019, 42,341. (in Chinese) |
| [84] | ( 李亚南, 胡建建, 常佩, 陈涛, 张红武, 王彬, 火炸药学报, 2019, 42,341.) |
| [85] | Xia, H.L.; Zhang, W.Q.; Jin, Y.H. ACS Appl. Mater. Interfaces 2019, 111,45914. |
| [86] | Zhang, W.Q.; Xia, H.L.; Yu, R.J.; Zhang, J.H.; Wang, K.C.; Zhang, Q.H. Propellants, Explos.,Pyrotech. 2020, 45,546. |
| [87] | Luo, Y.-F.; Ge, Z.-X.; Wang, B.-Z.; Zhang, H.-H; Liu, X. Chin. J. Energ. Mater. 2007, 15,205. (in Chinese) |
| [87] | ( 罗义芬, 葛忠学, 王伯周, 张海昊, 刘愆, 含能材料, 2007, 15,205.) |
| [88] | Cameron, M.; Gowenlock, B.G.; Boyd, A.F. J. Chem. Soc.,Perkin Trans. 2 1996, 11,2271. |
/
| 〈 |
|
〉 |