1-甲基-3,4,5-三硝基吡唑合成工艺研究进展
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摘要
1-甲基-3,4,5-三硝基吡唑(MTNP)是一种高能钝感的低熔点单质炸药,其爆轰性能与RDX相当,感度接近B炸药,是一种潜在可替代TNT作为熔铸炸药载体的含能材料。总结了近年来国内外有关MTNP的合成研究报道,分析了各种合成工艺的优劣,并对其合成工艺进行了展望。
1-methyl-3,4,5-trinitropyrazole(MTNP)is a kind of high-energy insensitive explosive with low melting point,and its detonation properties are similar to RDX and the sensitivity is close to B explosives. All these characteristics indicate that MTNP could be a potential energetic material as cast explosive carrier which will replace TNT. This paper summarizes the research reports on the synthesis of MTNP at domestic and foreign in recent years,analyzing the advantages and disadvantages of various synthetic processes and put forward a positive outlook to its synthesis.
1-methyl-3,4,5-trinitropyrazole(MTNP)is a kind of high-energy insensitive explosive with low melting point,and its detonation properties are similar to RDX and the sensitivity is close to B explosives. All these characteristics indicate that MTNP could be a potential energetic material as cast explosive carrier which will replace TNT. This paper summarizes the research reports on the synthesis of MTNP at domestic and foreign in recent years,analyzing the advantages and disadvantages of various synthetic processes and put forward a positive outlook to its synthesis.
引文
[1]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):475-484.
[2]安守忠.含氮有机化合物概论[M].北京:科学出版社,1983.
[3]徐松林,阳世清,岳守体.偶氮四唑类高氮含能化合物的合成及表征[J].火炸药学报,2005,28(3):52-54.
[4]郭俊玲,曹端林,王建龙,等.硝基吡唑类化合物的合成研究进展[J].含能材料,2014,22(6):872-879.
[5]李翠屏,孙天旭,陈新志,等.3-硝基吡唑的合成[J].染料与染色,2004,41(3):168-169.
[6]Li Y F,Fan X W,Wang Z Y,et al.A density functional study of substituted pyrazole derivatives[J].Journal of Molecular Structure Theochem,2009,896(1-3):96-102.
[7]李洪丽,熊彬,姜俊,等.3-硝基吡唑及其盐类的合成与表征[J].火炸药学报,2007,31(2):102-108.
[8]Ravi P,Gore G M,Sikder A K,et al.Thermal decomposition kinetics of 1-methyl-3,4,5-trinitropyrazole[J].Thermochimica Acta,2012,528(2):53-57.
[9]HervéG.Dinitropyrazole Derivatives,Their Preparation and Energetic Compositions Comprising Them[P].U.S.Patent:200901016931,2009-7-23.
[10]Herve G,Roussel C,Graindorge H.Selective preparation of3,4,5-trinitro-1H-pyrazole:a stable all-carbon-nitrated arene[J].Angewandte Chemie,2010,49(18):3177.
[11]Ravi P,Chaganti K R,Ananta S,et al.Nitrodeiodination of Polyiodopyrazoles[J].Propellants Explos.Pyrotech,2012,37(2):167-171.
[12]Ravi P,Surya P.Facile and environmentally friendly synthesis of nitropyrazoles using montmorillonite K-10 impregnated with bismuth nitrate[J].Catalysis Communications,2012(19):37-41.
[13]Ravi P,Surya P.Faujasite catalyzed nitrodeiodination of iodopyrazoles[J].Catalysis Communications,2013(42):35-39.
[14]Dalinger I L,Vatsadze I A,Shkineva T K,et al.The specific reactivity of 3,4,5-trinitro-1H-pyrazole[J].Mendeleev Commun,2010,20(5):253-254.
[15]Dalinger I L,Vatsadze I A,Shkineva T K,et al.Synthesis and Comparison of the Reactivity of 3,4,5-1H-Trinitropyrazole and Its N-Methyl Derivative[J].Journal of Heterocyclic Chemistry,2013,50(4):911-924.
[16]李雅津,曹端林,李永祥,等.1-甲基-3,4,5-三硝基吡唑的合成与表征[J].火炸药学报,2013,36(3):28-30.
[17]李雅津.1-甲基-3,4,5-三硝基吡唑的合成工艺研究[D].中北大学,2014.
[18]郭俊玲,李永祥,王建龙,等.超酸硝化法合成1-甲基-3,4,5-三硝基吡唑[J].合成化学,2015,23(2):161-163.
[19]郭俊玲,李永祥,王建龙,等.1-甲基-3,4,5-三硝基吡唑的一步法合成及热性能[J].含能材料,2015,23(3):304-306.
[20]吴霏,李永祥,郝彩丽,等.N5O2/发烟硫酸体系一步法合成1-甲基-3,4,5-三硝基吡唑[J].含能材料,2016,24(6):618-620.
[21]陶文昌.1-甲基-3,4,5-三硝基吡唑(MTNP)的制备及性能[D].北京理工大学,2016.
[22]蒋涛.两种吡唑类含能化合物的合成及相关物的理论研究[D].西南科技大学,2016.
[2]安守忠.含氮有机化合物概论[M].北京:科学出版社,1983.
[3]徐松林,阳世清,岳守体.偶氮四唑类高氮含能化合物的合成及表征[J].火炸药学报,2005,28(3):52-54.
[4]郭俊玲,曹端林,王建龙,等.硝基吡唑类化合物的合成研究进展[J].含能材料,2014,22(6):872-879.
[5]李翠屏,孙天旭,陈新志,等.3-硝基吡唑的合成[J].染料与染色,2004,41(3):168-169.
[6]Li Y F,Fan X W,Wang Z Y,et al.A density functional study of substituted pyrazole derivatives[J].Journal of Molecular Structure Theochem,2009,896(1-3):96-102.
[7]李洪丽,熊彬,姜俊,等.3-硝基吡唑及其盐类的合成与表征[J].火炸药学报,2007,31(2):102-108.
[8]Ravi P,Gore G M,Sikder A K,et al.Thermal decomposition kinetics of 1-methyl-3,4,5-trinitropyrazole[J].Thermochimica Acta,2012,528(2):53-57.
[9]HervéG.Dinitropyrazole Derivatives,Their Preparation and Energetic Compositions Comprising Them[P].U.S.Patent:200901016931,2009-7-23.
[10]Herve G,Roussel C,Graindorge H.Selective preparation of3,4,5-trinitro-1H-pyrazole:a stable all-carbon-nitrated arene[J].Angewandte Chemie,2010,49(18):3177.
[11]Ravi P,Chaganti K R,Ananta S,et al.Nitrodeiodination of Polyiodopyrazoles[J].Propellants Explos.Pyrotech,2012,37(2):167-171.
[12]Ravi P,Surya P.Facile and environmentally friendly synthesis of nitropyrazoles using montmorillonite K-10 impregnated with bismuth nitrate[J].Catalysis Communications,2012(19):37-41.
[13]Ravi P,Surya P.Faujasite catalyzed nitrodeiodination of iodopyrazoles[J].Catalysis Communications,2013(42):35-39.
[14]Dalinger I L,Vatsadze I A,Shkineva T K,et al.The specific reactivity of 3,4,5-trinitro-1H-pyrazole[J].Mendeleev Commun,2010,20(5):253-254.
[15]Dalinger I L,Vatsadze I A,Shkineva T K,et al.Synthesis and Comparison of the Reactivity of 3,4,5-1H-Trinitropyrazole and Its N-Methyl Derivative[J].Journal of Heterocyclic Chemistry,2013,50(4):911-924.
[16]李雅津,曹端林,李永祥,等.1-甲基-3,4,5-三硝基吡唑的合成与表征[J].火炸药学报,2013,36(3):28-30.
[17]李雅津.1-甲基-3,4,5-三硝基吡唑的合成工艺研究[D].中北大学,2014.
[18]郭俊玲,李永祥,王建龙,等.超酸硝化法合成1-甲基-3,4,5-三硝基吡唑[J].合成化学,2015,23(2):161-163.
[19]郭俊玲,李永祥,王建龙,等.1-甲基-3,4,5-三硝基吡唑的一步法合成及热性能[J].含能材料,2015,23(3):304-306.
[20]吴霏,李永祥,郝彩丽,等.N5O2/发烟硫酸体系一步法合成1-甲基-3,4,5-三硝基吡唑[J].含能材料,2016,24(6):618-620.
[21]陶文昌.1-甲基-3,4,5-三硝基吡唑(MTNP)的制备及性能[D].北京理工大学,2016.
[22]蒋涛.两种吡唑类含能化合物的合成及相关物的理论研究[D].西南科技大学,2016.