|本期目录/Table of Contents|

[1]李亚南,胡建建,常佩,等.1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑-氨基脲盐的合成、晶体结构及性能[J].火炸药学报,2019,42(4):341-345.[doi:10.14077/j.issn.1007-7812.2019.04.004]
 LI Ya-nan,HU Jian-jian,CHANG Pei,et al.Synthesis, Crystal Structure and Properties of 1,4-Dinitramino-3,6-dinitropyrazolo[4,3-c]pyrazole’s Aminourea Salt[J].,2019,42(4):341-345.[doi:10.14077/j.issn.1007-7812.2019.04.004]
点击复制

1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑-氨基脲盐的合成、晶体结构及性能()
     
分享到:

《火炸药学报》[ISSN:1007-7812/CN:61-1310/TJ]

卷:
42卷
期数:
2019年第4期
页码:
341-345
栏目:
出版日期:
2019-08-31

文章信息/Info

Title:
Synthesis, Crystal Structure and Properties of 1,4-Dinitramino-3,6-dinitropyrazolo[4,3-c]pyrazole’s Aminourea Salt
作者:
李亚南 胡建建 常佩 陈涛 张红武 王彬
西安近代化学研究所, 陕西 西安 710065
Author(s):
LI Ya-nan HU Jian-jian CHANG Pei CHEN Tao ZHANG Hong-wu WANG Bin
Xi’an Modern Chemistry Research Institute, Xi’an 710065, China
关键词:
有机化学含能材料14-二硝胺基-36-二硝基吡唑[43-c]并吡唑-氨基脲盐高能量密度材料晶体结构
Keywords:
organic chemistryenergetic material14-dinitramino-36-dinitropyrazolo[43-c]pyrazole’s aminourea salthigh energy density materialcrystal structure
分类号:
TJ55;O62
DOI:
10.14077/j.issn.1007-7812.2019.04.004
文献标志码:
-
摘要:
以1,4-二氨基-3,6-二硝基吡唑[4,3-c]并吡唑(DADNP)为原料,经硝化、中和、复分解等反应合成了1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑-氨基脲盐(DAUDNANP),采用红外光谱、1H NMR、13C NMR及元素分析等方法表征了目标物结构;获得了1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑(DNANP·C2H5OH)和DAUDNANP的单晶并进行了晶体结构解析;利用DSC方法对DAUDNANP的热稳定性进行了研究;采用Gaussian 09程序中的CBS-4M方法和Kamlet-Jacobs方程预估了DAUDNANP的爆轰性能。结果表明,化合物DNANP·C2H5OH晶体为三斜晶系,空间群为P-1,晶体学参数为:a=0.974 6(3) nm,b=0.995 2(3) nm,c=1.088 3(3) nm,α=112.344(4)°,β=109.918(5)°,γ=94.820(5)°,V=0.889 9(4) nm3Z=2,μ=0.140 mm-1F(0 0 0)=424;化合物DAUDNANP晶体为三斜晶系,空间群为P-1,晶体学参数为:a=0.486 13(11) nm,b=0.915 3(2) nm,c=1.018 6(2) nm,α=94.446(3)°,β=103.120(3)°,γ=97.230(3)°,V=0.43524(17) nm3Z=1,μ=0.164 mm-1F(0 0 0)=240;DAUDNANP的两个热分解峰温度分别为158.1和176.4℃,晶体密度为1.79 g/cm3,爆速为8 516 m/s,爆压为32.6 GPa,生成热为409.7 kJ/mol,爆热为5 750 kJ/kg。DAUDNANP是一种性能较好的新型高能量密度材料。
Abstract:
1,4-Dinitramino-3,6-dinitropyrazolo[4,3-c]pyrazole’s aminourea salt (DAUDADNP) was synthesized by the reactions of nitrification, neutralization, and metathesis using 1,4-diamino-3,6-dinitropyrazolo[4,3-c]pyrazole (DADNP) as starting material. The structure of target compound was characterized by means of IR spectra, NMR (1H and 13C) and elemental analysis. The single crystals of 1,4-dinitramino-3,6-dinitropyrazolo[4,3-c]pyrazole (DNANP·C2H5OH) and DAUDADNP were obtained, and their crystal structures were analyzed.The thermal stability of DAUDADNP was tested by DSC method. The detonation properties of DAUDADNP were estimated by CBS-4M methed and Kamlet-Jacobs equation in Gaussian 09 program. The results show that the crystal of DNANP·C2H5OH belongs to the triclinic system, space group P-1, cell parameters:a=0.974 6(3) nm, b=0.995 2(3) nm, c=1.088 3(3) nm,α=112.344(4)°,β=109.918(5)°,γ=94.820(5)°,V=0.889 9(4) nm3,Z=2,μ=0.140 mm-1,F(0 0 0)=424. The crystal of DAUDNANP belongs to the triclinic system,space group P-1, cell parameters:a=0.486 13(11) nm, b=0.915 3(2) nm, c=1.018 6(2) nm, α=94.446(3)°, β=103.120(3)°, γ=97.230(3)°, V=0.435 24(17) nm3, Z=1, μ=0.164 mm-1, F(0 0 0)=240. The two thermal decomposition peak temperatures of DAUDADNP were 158.1℃ and 176.4℃, respectively. The formation heat of DAUDADNP was 409.7 kJ/mol and the crystal density was 1.79 g/cm3, the detonation velocity was 8 516 m/s, the detonation pressure was 32.6 GPa, and the heat of detonation was 5 750 kJ/kg, showing that DAUDNANP is a new high energy density material with preferable properties.

参考文献/References:

[1] Gao Hai-xiang, Shreeve J M. Azole-based energetic salts[J]. Chemical Reviews, 2011, 111(11):7377-7436.
[2] Zhang Qing-hua, Shreeve J M. Energetic ionic liquids as explosives and propellant fuels:a new journey of ionic liquid chemistry[J]. Chemical Reviews, 2014, 114(20):10527-10574.
[3] 李亚南, 张生勇, 舒远杰, 等. 1,1’-二硝氨基-5,5’-偶氮双四唑钾盐的合成、结构及性能[J]. 火炸药学报, 2017, 40(4):52-56. LI Ya-nan, ZHANG Sheng-yong, SHU Yuan-jie, et al. Synthesis, structure and properties of dipotassium 1,1’-dinitramino-5,5’-azobitetrazolate[J]. Chinese Journal of Explosives & Propellants(Huozhayao Xuebao), 2017, 40(4):52-56.
[4] Li Yu-chuan, Liu Wei, Pang Si-ping. Synthesis and characterization of 5-nitro-2-nitratomethyl-1,2,3,4-tetrazole:a high nitrogen energetic compound with good oxygen balance[J]. Molecules, 2012, 17(5):5040-5049.
[5] Fischer N, Izsák D, Klapötke T M, et al. The chemistry of 5-(tetrazol-1-yl)-2H-tetrazole:an extensive study of structural and energetic properties[J]. Chemistry-A European Journal, 2013, 19(27):8948-8957.
[6] Dippold A A, Klapötke T M, Oswald M. Asymmetrically substituted 5,5’-bistriazoles-nitrogen rich materials with various energetic functionalities[J]. Dalton Transactions, 2013, 42(31):11136-11145.
[7] Tang Yong-xing, Yang Hong-wei, Wu Bo, et al. Synthesis and characterization of a stable, catenated N11 energetic salt[J]. Angewandte Chemie International Edition, 2013, 52(18):4875-4877.
[8] 李亚南, 王伯周, 廉鹏, 等. 1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑化合物:ZL, 201418000726.6[P]. 2014. LI Ya-nan, WANG Bo-zhou, LIAN Peng, et al. 1,4-Dinitramino-3,6-dinitropyrazolo[4,3-c]pyrazole compound:ZL, 201418000726.6[P]. 2014.
[9] Yin Ping, Zhang Jia-heng, Mitchell L A, et al. 3,6-Dinitropyrazolo[4,3-c]pyrazole-based multipurpose energetic materials through versatile N-functionalization strategies[J]. Angewandte Chemie International Edition, 2016, 55, 12895-12897.
[10] Philip F P, Gregory S L, Alexander R M, et al. A review of energetic materials synthesis[J]. Thermochimi Acta, 2002, 384:187-204.
[11] 李亚南, 唐婷, 廉鹏, 等. 1,4-二氨基-3,6-二硝基吡唑[4,3-c]并吡唑(LLM-119)的合成、热性能及量子化学研究[J]. 有机化学, 2012, 32(3):580-588. LI Ya-nan, TANG Ting, LIAN Peng, et al. Synthesis, thermal performance and quantum chemistry study on 1,4-diamino-3,6-dinitropyrazolo[4,3-c]pyrazole(LLM-119)[J]. Chinese Journal of Organic Chemistry, 2012, 32(3):580-588.
[12] Frisch M J, Trucks G W, Schlegel H B, et al. Gaussian 09[CP/DK].Wallingford CT:Gaussian, Inc.,2009.
[13] Montgomery J A, Frisch M J, Ochterski J W, et al. A complete basis set model chemistry VⅡ. use of the minimum population localization method[J]. Journal of Chemistry Physical, 2000, 112:6532-6542.
[14] Kamlet M J, Jacobs S J. Chemistry of detonation I. A simple method for calculating detonation properties of CHNO explosives[J]. Journal of Chemistry Physical, 1968, 48(1):23-35.
[15] Li Ya-nan, Shu Yuan-jie, Wang Bo-zhou, et al. Synthesis, structure and properties of neutral energetic materials based on N-functionalization of 3,6-dinitropyrazolo[4,3-c]pyrazole[J]. RSC Advances, 2016, 6(25):84760-84768.

相似文献/References:

[1]周彦水,李建康,黄新萍,等.3,4-双(4′-氨基呋咱基-3′)氧化呋咱的合成及性能[J].火炸药学报,2007,30(1):54.
[2]彭汝芳,金 波,马冬梅,等.2-(2-硝基苯基)吡咯烷[3′,4′∶1,2][60]富勒烯的合成[J].火炸药学报,2007,30(2):29.
[3]马海霞,宋纪蓉,胡荣祖,等.HMX,CL-20和DNTF自由基的光照检测[J].火炸药学报,2007,30(2):33.
[4]陈 斌,张志忠,姬月萍.偕二硝基类含能增塑剂的合成及应用[J].火炸药学报,2007,30(2):67.
[5]莫洪昌,甘孝贤.3-硝酸酯甲基-3-甲基氧杂环丁烷的合成及表征[J].火炸药学报,2006,29(6):58.
[6]郑晓东,马晓东,邱少君,等.一种新型叠氮含能固化剂的合成及性能[J].火炸药学报,2006,29(5):63.
[7]韩涛,甘孝贤,邢颖,等.3-叠氮甲基-3-乙基氧杂环丁烷及其均聚物的合成与性能[J].火炸药学报,2006,29(5):72.
[8]曹继平,李东林,王吉贵.不饱和聚酯包覆含DNT双基推进剂的研究[J].火炸药学报,2006,29(4):41.
[9]李东林,曹继平,王吉贵.不饱和聚酯包覆层的耐烧蚀性能[J].火炸药学报,2006,29(3):17.
[10]钱华,吕春绪,叶志文.绿色硝解合成六硝基六氮杂异伍兹烷[J].火炸药学报,2006,29(3):52.
[11]王小军,曹端林,李永祥,等.1-甲基-2,4,5-三硝基咪唑的合成新工艺[J].火炸药学报,2009,32(3):16.
 WANG Xiao jun,CAO Duan lin,LI Yong xiang,et al.New Technology for Synthesis of 1Methyl2,4,5trinitroimidazoles[J].,2009,32(4):16.
[12]何冬梅,程广斌,吕春绪.四嗪类高氮含能化合物的合成与表征[J].火炸药学报,2010,33(5):8.
 HE Dong-mei,CHENGGuang-bin,Lü Chun-xu.Synthesis and Characterization of High nitrogen Energetic Compounds Derived from Tetrazine[J].,2010,33(4):8.
[13]沈华平,卢艳华,曹一林,等.亚甲基-双-(3-硝氨基-4-甲基呋咱)的合成与性能[J].火炸药学报,2011,34(4):37.
 SHEN Hua-ping,LU Yan-hua,CAO Yi-lin,et al.Synthesis and Properties of Methylene-bis-(3-nitramino-4-methylfurazan[J].,2011,34(4):37.
[14]黄海丰,周智明.基于有机阴离子的含能离子盐研究进展[J].火炸药学报,2012,35(3):1.
 HUANG Hai-feng,ZHOU Zhi-ming.Progress of Study on Organic Anion Based Energetic Salts[J].,2012,35(4):1.
[15]赵晓锋,刘祖亮,姚其正,等.2,6-二氨基-3,5-二硝基吡嗪-1-氧化物的合成[J].火炸药学报,2012,35(3):15.
 ZHAO Xiao-feng,LIU Zu-liang,YAO Qi-zheng,et al.Synthesis of 2,6-Diamino-3,5-dinitropyrazine-1-oxide[J].,2012,35(4):15.
[16]高莉,杨红伟,汤永兴,等.偶氮及氧化偶氮呋咱化合物的合成与表征[J].火炸药学报,2013,36(1):47.
 GAO Li,YANG Hong-wei,TANG Yong-xing,et al.Synthesis and Characterization of Azofurazan and Azoxyfurazan[J].,2013,36(4):47.
[17]毕福强,樊学忠,许诚,等.1, 1′-二羟基-5, 5′-联四唑的合成及理论研究[J].火炸药学报,2013,36(4):22.
 BI Fu-qiang,FAN Xue-zhong,XU Cheng,et al.Synthesis and Theoretical Study of 1,1′-Dihydroxy-5,5′-bitetrazole[J].,2013,36(4):22.
[18]林智辉,高莉,李敏霞,等.几种呋咱类含能化合物的合成、热行为及理论爆轰性能预估[J].火炸药学报,2014,37(3):6.
[19]王小军,张晓鹏,宋磊,等.5,5′-联四唑-1,1′-二氧氨盐的合成、晶体结构及性能[J].火炸药学报,2015,38(4):35.[doi:10.14077/j.issn.1007-7812.2015.04.008]
 WANG Xiao-jun,ZHANG Xiao-peng,SONG Lei,et al.Synthesis, Crystal Structure and Properties of the Ammonia Salt of 5,5′-Bistetrazole -1,1′-diolate[J].,2015,38(4):35.[doi:10.14077/j.issn.1007-7812.2015.04.008]
[20]雷晴,卢艳华,何金选.二硝酰胺钾的合成、晶体结构及性能[J].火炸药学报,2017,40(2):57.[doi:10.14077/j.issn.1007-7812.2017.02.010]
 LEI Qing,LU Yan-hua,HE Jin-xuan.Synthesis, Crystal Structure and Properties of Potassium Dinitramide[J].,2017,40(4):57.[doi:10.14077/j.issn.1007-7812.2017.02.010]

备注/Memo

备注/Memo:
收稿日期:2018-09-02;改回日期:2018-10-10。
基金项目:国家自然科学基金(No.21805222;No.21875185)
作者简介:李亚南(1984-),男,博士,副研究员,从事含能材料合成、性能及中试工艺研究。E-mail:lyn2003080094@126.com
更新日期/Last Update: 1900-01-01