全部 标题 作者
关键词 摘要

OALib Journal期刊
ISSN: 2333-9721
费用:99美元

查看量下载量

相关文章

更多...
含能材料  2015 

硝基咪唑类含能化合物的合成研究进展

DOI: 10.11943/j.issn.1006-9941.2015.04.013

Keywords: 多硝基咪唑 含能化合物 合成 炸药

Full-Text   Cite this paper   Add to My Lib

Abstract:

综述了10种硝基咪唑类含能化合物的合成及性能,包括1, 4-二硝基咪唑(1, 4-DNI),2, 4-二硝基咪唑(2, 4-DNI),4, 5-二硝基咪唑(4, 5-DNI),2, 4, 5-三硝基咪唑(2, 4, 5-TNI),1-甲基-2, 4-二硝基咪唑(2, 4-MDNI),1-甲基-4, 5-二硝基咪唑(4, 5-MDNI),1-甲基-2, 4, 5-三硝基咪唑(MTNI),1-苦基-2, 4-三硝基咪唑(2, 4-PDNI),1-乙酸乙酯-2, 4, 5-三硝基咪唑(CTNII),1-苦基-2, 4, 5-三硝基咪唑(PTNI)。对高能钝感炸药1, 4-DNI、2, 4-DNI及MTNI的合成与性能进行了详细介绍并对路线中存在的问题进行了简要评述。同时提出了一条理论上可行的合成MTNI的新路线,即碘代-硝化法:以N-甲基咪唑为原料经碘化得到1-甲基-2, 4, 5-三碘基咪唑(MTII),然后再用超酸硝化得到目标物

References

[1]  郑保辉,罗观,舒远杰,等.熔铸炸药研究现状与发展趋势[J].化工进展,2013,32(6): 1341-1346.ZHENG Bao-hui, LUO Guan, SHU Yuan-jie, et al.Research status and prospect of melt-cast explosive[J].Chemical Industry and Engineering Progress, 2013,32(6): 1341-1346.
[2]  Pagoria P F, Lee G S, Mitchell A R, et al.The synthesis of amino and nitrosubstituted heterocycles as insensitive energetic materials[R], 2001, Report UCRL-ID-142918.
[3]  Maxime D C, Celine Botta, Monique Gasquet, et al.Lowering of 5-nitroimidazole′s matagenicity: Towards optimal antiparasitic pharmacophore[J].European Journal of Medicinal Chemistry, 2008,11(7): 113-118.
[4]  Viviane M, Michel M.Process for the preparation of 1-(3-chloro-2-hydroxyalkyl)-2methyl-5-nitro- imidazole (ornidazole):EP 399901[P], 1990.
[5]  Boiani M, González M.Imidazole and benzimidazole derivatives as chemotherapeutic agents[J].Mini Rev Med Chem, 2005,5(4): 409-424.
[6]  Damavarpu R, Jayasuriya K, Theodore V, et al.2,4-dinitroimidazole: a less sensitive explosive and propellant made by thermal rearrangement of molten 1,4-dinitroimidazole: USP 5387297[P],1995.
[7]  Cho J R, Kim K J, Cho S G, et al.Synthesis and characterization of 1-methyl-2,4,5-trinitroimidazole (MTNI)[J].J.Heterocyclic Chem, 2001,38: 141-147.
[8]  曹端林,刘慧君,李永祥.1,4-二硝基咪唑的合成及热分解[J].火炸药学报,2005,28(3): 60-62.CAO Duan-lin, LIU Hui-jun, LI Yong-xiang.Synthesis and thermal decomposition of 1,4-dinitromidazole[J].Chinese Journal of Explosives and Propellants, 2005,28(3): 60-62.
[9]  Suwinski J, Salwinska E.Nitroimidazoles, part IX some reactions of 1,4-DNI[J].Pol J Chem, 1987,61(7-12): 613-920.
[10]  杨利,高福磊,凡庆涛,等.咪唑类含能化合物的研究进展[J].含能材料,2009,17(3): 375-377.YANG Li, GAO Fu-lei, FAN Qing-tao, et al.Progress in imidazolium-based energetic compounds[J].Chinese Journal of Energetic Materials(Hanneng Cailiao),2009,17(3): 375-377.
[11]  Novikov S S, Khmel′nitskii L I, Novikova T S, et al.Dinitroimidazde and derivatives[J].Chem Heterocycl Compd( Engl Transl), 1979,6: 614.
[12]  杨国臣, 刘慧君, 曹端林.4,5-二硝基咪唑的制备[J].含能材料,2006,14(5): 349-351.YANG Guo-chen, LIU Hui-jun, CAO Duan-lin.Prepration of 4,5-nitroimidazole[J].Chinese Journal of Energetic Materials(Hanneng Cailiao), 2006,14(5): 349-351.
[13]  Vadimiroff T.Acidity and basicidity of nitro substituted imidazoles technical rept, ADA2939969[R].Springlield: NT IS, 1995.
[14]  Gao H X, Ye C F, Gupta O D, et a1.2,4,5-Ttinitroimidazole-based energetic salts[J].Chem Eur J, 2007,13(14): 3854-3860.
[15]  Jadhav H S, Talawar M B, Sivabalan R, et al.Synthesis, characterization and thermolysis studies on new derivatives of 2,4,5- trinitroimidazoles: Potential insensitive high energy materials.Journal of Hazardous Materials, 2006,143: 192-197.
[16]  Qi-Long Yan, Svatopiuk Zeman, Ahmed Elbeih.Recent advances in thermal analysis and stability evaluation of insensitive plastic bonded explosives[J].Thermochimica Acta.2012,3(3): 1-12.
[17]  Cho J R, Kim K J, Cho S G, et al.Synthesis and characterization of 1-methyl-2,4,5-trinitroimidazoles (MTNI)[J].Journal of Heterocyclic Chemistry, 2002,39(1): 141-147.
[18]  杨威, 姬月萍, 汪伟, 等.1-甲基-2,4-二硝基咪唑的合成及反应动力学[J].火炸药学报,2010,33(3): 63-67.YANG Wei, JI Yue-ping, WANG Wei, et al.Synthesis and kinetics of 1-methyl-2,4-dinitroimidazol[J].Chinese Journal of Explosives and Propellants, 2010,33(3): 63-67.
[19]  张晓玉, 池钰, 黄明, 等.1-甲基-2,4-基咪唑的晶体结构与热力学性质[J].含能材料,2012,20(6): 685-689.ZHANG Xiao-yu, CHI Yu, HUANG Ming, et al.Crystal structure and thermodynamic properties of 1-methyl-2,4-dinitroimidazole[J].Chinese Journal of Energetic Materials(Hanneng Cailiao), 2012,20(6): 685-689.
[20]  陈丽珍, 王小军, 耿天齐, 等.1-甲基-4,5-二硝基咪唑的晶体结构与热分解特性[J].中北大学学报(自然科学版),2012,33(2): 159-163.CHEN Li-zhen, WANG Xiao-jun, GENG Tian-qi, et al.Crystal structure and thermal decomposition of 1-methyl-4,5-dinitroimidazole[J].Journal of North University of China(Natural Science), 2012,33(2): 159-163.
[21]  曹端林, 王小军, 杨彩云, 等.1-甲基-4,5-二硝基咪唑合成工艺[J].含能材料,2009,17(6): 678-680.CAO Duan-lin, WANG Xiao-jun, YANG Cai-yun, et al.Synthesis of 1-methyl-4,5-dinitroimidazole[J].Chinese Journal of Energetic Materials(Hanneng Cailiao), 2009,17(6): 678-680.
[22]  宋磊, 王建龙, 李永祥, 等.1-甲基-4,5-二硝基咪唑的合成及表征[J].含能材料,2009.17(5): 531-533.SONG Lei, WANG Jian-long, LI Yong-xiang, et al.Synthesis and characterization of 1-methyl-4,5-dinitroimidazole[J].Chinese Journal of Energetic Materials(Hanneng Cailiao), 2009,17(5): 531-533.
[23]  曹端林, 王小军, 杨彩云, 等.1-甲基-4,5-二硝基咪唑合成工艺[J].含能材料,2009,17(6): 678-680.CAO Duan-lin, WANG Xiao-jun, YANG Cai-yun, et al.Synthesis of 1-methyl-4,5-dinitroimidazole[J].Chinese Journal of Energetic Materials(Hanneng Cailiao), 2009,17(6): 678-680.
[24]  汪伟, 杨威, 姬月萍, 等.1-甲基-2,4,5-三硝基咪唑的合成及表征[J].火炸药学报,2008,31(6): 32-38.WANG Wei, YANG Wei, JI Yue-ping, et al.Synthesis and characterization of 1-methyl-2,4,5-trinitroimidazol[J].Chinese Journal of Explosives and Propellants, 2008,31(6): 32-38.
[25]  殷明, 舒远杰, 熊鹰, 等.硝基咪唑化合物结构与性质的理论研究[J].化学学报,2008,66(19): 2117-2123.YIN Ming, SHU Yuan-jie, XIONG Ying, et al.Theoretical studies on structures and properties of nitroimidazole compounds.Acta Chimica Sinica, 2008,66(19): 2117-2123.
[26]  Gary K Lund,Ogden,Tom K.Highsmith,et al.Insensitive high performance explosive compositions: US 5529649[P], 1996-07-25.
[27]  Damavarapu, Paritosh R, Zhang M X, et al.Melt-cast explosive material: US 7304164[P], 2007-12-04.
[28]  Jadhav H S, Talawar M B, Sivabalan R, et al.Synthesis, characterization and thermolysis studies on new derivatives of 2,4,5-trinitroimidazoles: Potential insensitive high energy materials[J].Journal of Hazardous Materials, 2006,143: 192-197.
[29]  刁莹, 王建龙, 王文艳, 等.碘代法合成1-甲基-2,4,5-三硝基咪唑[J].火炸药学报,2012,35(2): 40-43.DIAO Ying, WANG Jian-long, WANG Wen-yan, et al.Synthesis of 1-methyl-2,4,5-trinitroimidazole by iodo method[J].Chinese Journal of Explosives and Propellants, 2012,35(2): 40-43.
[30]  王小军,曹端林,李永祥,等.1-甲2,4, 5-三硝基咪唑的合成新工艺[J].火炸药学报,2009,32(3): 16-18.WANG Xiao-jun, CAO Duan-lin, LI Yong-xiang, et al.New technology for synthesis of 1-methyl-2,4,5- trinitroimidazoles[J].Chinese Journal of Explosives and Propellants,2009,32(3): 16-18.
[31]  Duddu R, Zhang Mao-Xi, Damavarapu R, et al.Molten-state nitration of substituted imidazoles: new synthetic approaches to the novel melt-cast energetic material, 1-methyl-2,4,5-trinitroimidazole[J].Synthesis,2011,17: 2859-2864.
[32]  Ravi P, Tewari S P.Microwave-assisted synthesis of 1-methyl-2,4,5-trinitroimidazole[J].Propellants, Explosives, Pyrotechnics, 2012,37: 544-548.
[33]  王小军,王霞,鲁智艳,等.1-苦基-2,4-二硝基咪唑的合成及表征[J].火工品, 2012(5): 33-35.WANG Xiao-jun, WANG Xia, LU Zhi-yan, et al.Synthesis and characterization of 1-(2,4,6-trinitrophe nyl)-2,4-dinitroimidazole[J].Initiators & Pyrotechnics, 2012(5): 33-35.
[34]  Jadhav P M, Sarangapani R, Prasanth H, et al.Quantum-chemical studies on thermodynamic feasibility of 1-methyl-2,4,5-trinitroimidazole processes[J].J Mol Model,2013,19: 3027-3032.
[35]  Ravi P, Koti R C, Saikia A, et al.Nitrodeiodination of polyiodopyrazoles[J].Propellants Explosive Pyrotechnics, 2012,37: 167-171.
[36]  Ravi P, Tewari S P.Facil and environmentally friendly synthesis of nitropyrazoles using montmorillonite K-10 impregnated with bismuth nitrate[J].Catalysis Communications,2012,19: 37-41.
[37]  阳世清,徐松林,雷永鹏.氮杂环含能化合物的研究进展[J].含能材料,2006,14(6): 475-477.YANG Shi-qing, XU Song-lin, LEI Yong-peng.The research progress of nitrogen heterocyclic compounds[J].Chinese Journal of Energetic Materials(Hanneng Cailiao), 2006,14(6): 475-477.
[38]  曹端林,李雅津,杜耀,等.熔铸炸药载体的研究评述[J].含能材料,2013,21(2): 157-165.CAO Duan-lin, LI Ya-jin, DU Yao, et al.Review on carriers for melt-cast explosives[J].Chinese Journal of Energetic Materials(Hanneng Cailiao), 2013,21(2): 157-165.
[39]  Albert B, Viviane M, Michel M.Process for the preparation of 1-hydroxyalky1-5-nitroimidazoles: EP 325513[P], 1989.
[40]  Sharni G P, Fassakhov R K, OrLov P P.2,4(5)-Dinitroimidazole :US 458553[P],1975.
[41]  Lancini G C,Maggi N,Sensi P.Synthesis of some derivatives of 2-nitroimidazole with potential antitriehomonas activity[J].Ed Sci, 1963,18(3): 390-39.
[42]  Grigoreva V N, Fassakhov R K, Gafarow A N, et al.Method of preparing 1,4-dinitroimidazole: SU, 1416488[P], 1983.
[43]  Grimmett M R, Hua S T, Chang K C, et al.1,4-dinitroimidazole and derivatives: Structure and thermal rearrangement [J].Aust, Chem, 1989,42(8): 1281-1289.
[44]  刘慧君,樊月琴,冯峰,等.1,4-DNI的绿色合成[J].山西大同大学学报,2011,27(2): 37-38.LIU Hui-jun, FAN Yue-qin, FENG Feng, et al.The green synthesis of 1,4-DNI[J].Journal of Shanxi Datong University (Natural Science), 2011,27(2): 37-38.
[45]  张俊娜,兰婷,李明华,等.1,4-二硝基咪唑的制备与晶体结构[J].应用化工,2012,41(9): 1664-1667.ZHANG Jun-na, LAN Ting, LI Ming-hua, et al.Preparation and crystal structure of 1,4-dinitroimidazole[J].Applied Chemical Industry,2012,41(9): 1664-1667.
[46]  刘慧君,曹端林,李永祥,等.2,4-DNI的研究进展[J].含能材料,2005,13(4): 269-271.LIU Hui-jun, CAO Duan-lin, LI Yong-xiang, et al.The progress of 2,4-DNI[J].Chinese Journal of Energetic Materials(Hanneng Cailiao), 2005,15(4): 269-272.
[47]  Bracuti A J.Crystal structure of 2,4-dinitroimidazole (24DNI)[J].Journal of Chemical Crystallography, 1995,25(10): 625-627.
[48]  WANG Jun, DONG Hai-shan, ZHANG Xiao-yu, et al.Synthesis, Thermal stability and sensitivity of 2,4-dinitroimidazole[J].Chinese Journal of Energetic Materials(Hanneng Cailiao), 2010,18(6): 728-729.
[49]  赵廷兴, 李磊, 董战, 等.硝基唑类含能化合物的合成研究进展[J].有机化学,2014,34: 304-315.ZHAO Ting-xing, LI Lei, DONG Zhan, et al.Research progress on the synthesis of energetic nitroazoles [J].Chinese Journal of Organic Chemistry, 2014,34: 304-315.
[50]  杨威, 姬月萍, 汪伟, 等.2,4-二硝基咪唑有机胺盐合成与性能[J].含能材料,2010,18(3): 270-272.YANG Wei, JI Yue-ping, WANG Wei, et al.Synthesis and properties of 2,4-dinitroimidazole(2,4-DNI)salts[J].Chinese Journal of Energetic Materials(Hanneng Cailiao), 2010,18(3): 270-272.
[51]  郑晓东,崔荣,李洪丽,等.2,4-DNI 铅盐的合成及性能[J].火炸药学报,2006,29(16): 23-26.ZHENG Xiao-dong, CUI Rong, LI Hong-li, et al.Synthesis and properties of 2,4-dinitroimidazole lead salt[J].Chinese Journal of Explosives and Propellants, 2006,29(16): 23-26.
[52]  崔荣, 郑晓东, 毛治华, 等.2,4-二硝基咪唑铜配合物[Cu(DNI)2(H2O)]·3H2O的制备和晶体结构[J].火炸药学报,2007,30(6): 27-30.CUI Rong, ZHENG Xiao-dong, MAO Zhi-hua, et al.Preparationand crystal structure of [Cu(DNI)2(H2O)]·3H2O[J].Chinese Journal of Explosives and Propellants, 2007,30(6): 27-30.
[53]  Lancini G C, Maggi N, Sensi P.Synthesis of some derivatives of 2-nitroimidazole with potential anti-triehomonas activity[J].Ed Sci, 1963,18(3): 390-396.
[54]  Sharnin G P, Fassakhov R K, Orlov P P, et al.Potential radiosensitizing agents[J].Chem Abstu, 1975,82: 156316.
[55]  Ravi P, Tewari S P.Microwave-assisted synthesis of 1-methyl-2,4,5-trinitroimidazole[J].Propellants, Explosives, Pyrotechnics, 2012,37: 544-548.
[56]  Bracutin A J.Crystal structure of 4,5-dinitroimidazole (4,5-DNI)[J].Journal of Chemical Crystallgraphy, 1998,28(5): 367-371.
[57]  Bracutin A J.Molecular structure of a new potential propellant oxidizer 4,5-DNI[J].Journal of Chemical Crystallography, 1998,28(5): 367-371.
[58]  李永祥, 王建龙, 曹端林, 等.4,5-二硝基咪唑有机铵盐的制备[J].火炸药学报,2011,34(3): 35-37.LI Yong-xiang, WANG Jian-long, CAO Duan-lin, et al.Synthesis of ammonium salt of 4,5-dinitroimida zole[J].Chinese Journal of Explosives and Propellants, 2011,34(3): 35-37.
[59]  Bhaumik K,Akamanchi K G.2,4-dinitroimidazole: Microwave assisted synthesis and use in synthesis of 2,3-dihydro-6-nitroimidazo oxazole analogues with antimycobacterial activity[J].Journal of Heterocyclic Chemistry, 2004, (1): 52-55.
[60]  刘慧君, 樊月琴, 冯峰, 等.微波辅助合成2,4-二硝基咪唑[J].含能材料,2012,18(1): 1-3.LIU Hui-jun, FAN Yue-qin, FENG Feng, et al.Synthesis of 2,4-dinitroimidazole by microwave heating[J].Chinese Journal of Energetic Materials(Hanneng Cailiao), 2012,18(1):1-3.

Full-Text

Contact Us

service@oalib.com

QQ:3279437679

WhatsApp +8615387084133