CN108218877A - 1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑氨基脲盐化合物 - Google Patents
1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑氨基脲盐化合物 Download PDFInfo
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- -1 pyrazoles semicarbazides salt compound Chemical class 0.000 title claims abstract description 23
- 239000000463 material Substances 0.000 abstract description 3
- 150000003217 pyrazoles Chemical class 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 9
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 125000003368 amide group Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 238000005474 detonation Methods 0.000 description 5
- 238000004880 explosion Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 125000003831 tetrazolyl group Chemical group 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000002360 explosive Substances 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000005649 metathesis reaction Methods 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- POCJOGNVFHPZNS-ZJUUUORDSA-N (6S,7R)-2-azaspiro[5.5]undecan-7-ol Chemical compound O[C@@H]1CCCC[C@]11CNCCC1 POCJOGNVFHPZNS-ZJUUUORDSA-N 0.000 description 1
- 229910014288 N-N Inorganic materials 0.000 description 1
- BSPUVYFGURDFHE-UHFFFAOYSA-N Nitramine Natural products CC1C(O)CCC2CCCNC12 BSPUVYFGURDFHE-UHFFFAOYSA-N 0.000 description 1
- 229910014320 N—N Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- POCJOGNVFHPZNS-UHFFFAOYSA-N isonitramine Natural products OC1CCCCC11CNCCC1 POCJOGNVFHPZNS-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000005691 oxidative coupling reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004449 solid propellant Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C06—EXPLOSIVES; MATCHES
- C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
- C06B25/00—Compositions containing a nitrated organic compound
- C06B25/34—Compositions containing a nitrated organic compound the compound being a nitrated acyclic, alicyclic or heterocyclic amine
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Abstract
本发明公开了一种1,4‑二硝胺基‑3,6‑二硝基吡唑[4,3‑c]并吡唑氨基脲盐化合物,其结构式如(I)所示:
Description
技术领域
本发明涉及一种含能材料,具体涉及一种1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑氨基脲盐化合物。
背景技术
目前,氮杂芳环含能化合物的设计、合成及性能研究受到含能材料工作者的普遍关注,这类化合物分子中含有大量的C-N、C=N、N-N、N=N键,具有较高的正生成热,是其能量的主要来源,高氮、低碳氢含量使该类化合物更容易达到氧平衡,而较高的氮含量使其分解产物主要为氮气,清洁无污染,且产气量较大,未来在混合炸药、固体推进剂和气体发生剂等领域具有广阔的应用前景。5-氨基四唑是一种重要的氮杂环含能化合物前体,利用其结构中氨基的反应活性,可进一步形成硝基、硝胺基、三硝基乙氨基、偶氮基等含能基团,从而设计、合成出多种性能较好的四唑含能衍生物。利用该化合物分子中氨基的氧化偶联反应可制备出5,5′-偶氮双四唑,该化合物进一步与氮、氢含量高的有机胺发生复分解反应,可设计合成出一系列的5,5′-偶氮双四唑有机铵盐含能化合物。
Haixiang Gao等《Azole-Based Energetic Salts》,Chem.Rev.,2011,111,7377–7436一文公开了一种5,5′-偶氮双四唑氨基脲盐的结构及性能,其结构如(II)所示:
该化合物的密度为1.61g/cm3,其计算生成热为483kJ/mol,爆速为8125m/s,爆压为23.4GPa。但是该化合物密度较小、能量较低。
发明内容
本发明所要解决的技术问题是克服背景技术的不足和缺陷,提供一种密度较大、能量较高的1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑氨基脲盐化合物。
本发明的1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑氨基脲盐化合物的合成路线如下:
以1,4-二氨基-3,6-二硝基吡唑[4,3-c]并吡唑为原料,首先与硝硫混酸反应生成1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑,然后与碳酸氢钠(NaHCO3)、氨基脲盐酸盐(AU-HCl)发生复分解反应生成1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑氨基脲盐。
本发明的1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑氨基脲盐化合物,其结构式如(I)所示:
本发明的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方法,包括以下步骤:
(1)1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑的合成
室温下,将1,4-二氨基-3,6-二硝基吡唑[4,3-c]并吡唑、95%~98%(质量)浓硫酸加入反应瓶中,搅拌溶解后,冰盐浴冷却至-15℃~-10℃,缓慢滴加纯硝酸,控制体系温度不高于-10℃,加完后维持-15℃~-10℃反应2h,向体系中加入三氟乙酸,搅拌5min后,低温快速过滤、三氟乙酸洗涤、真空干燥得淡灰色固体1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑;其中纯硝酸的用量为每克1,4-二氨基-3,6-二硝基吡唑[4,3-c]并吡唑10.0~20.0mL,浓硫酸的用量为每克1,4-二氨基-3,6-二硝基吡唑[4,3-c]并吡唑50.0~100.0mL。
(2)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
室温下,依次将1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑、水和碳酸氢钠加入反应瓶中,搅拌15min后,待体系无气泡产生时,加入氨基脲盐酸盐,升温至50℃反应1h,反应液浓缩、冷却、过滤、干燥得黄色固体1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑氨基脲盐;其中1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑与氨基脲盐酸盐的摩尔比为1:2.0~2.2。
本发明的优点:
本发明的1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑氨基脲盐化合物密度较高,其密度为1.80g/cm3,对比文件的5,5′-偶氮双四唑氨基脲盐的密度为1.61g/cm3;本发明的1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑氨基脲盐化合物能量较高,其计算爆速为8559m/s,爆压为33.1GPa,对比文件的5,5′-偶氮双四唑氨基脲盐的计算爆速为8125m/s,爆压为23.4GPa。
具体实施方式
以下结合实施例对本发明作进一步详细说明。
实施例1
(1)1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑的合成
室温下,将0.456g(2mmol)1,4-二氨基-3,6-二硝基吡唑[4,3-c]并吡唑、50.0mL浓硫酸加入反应瓶中,搅拌溶解后,冰盐浴冷却至-15℃~-10℃,缓慢滴加10.0mL 100%纯硝酸,控制体系温度不高于-10℃,加完后维持-15℃~-10℃反应2h,向体系中加入50.0mL冷的三氟乙酸,搅拌5min后,低温快速过滤、三氟乙酸洗涤、真空干燥得0.59g淡灰色固体1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑,收率为92.8%。
结构鉴定:
红外光谱:IR(KBr,cm-1),υ:3216,1633,1556,1422,1376,1359,1297,1187,1112,1056,926
核磁光谱:1H NMR(DMSO-d6,500MHz),δ:10.87(s,2H,2NH)
13C NMR(DMSO-d6,125MHz),δ:128.60,133.44
元素分析:分子式C4H2N10O8
理论值:C 15.10,H 0.63,N 44.03
实测值:C 15.21,H 0.54,N 44.15。
上述结构鉴定数据证实得到物质确实是1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑。
(2)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
室温下,依次将0.159g(0.5mmol)1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑、6.0mL水和0.088g(1.05mmol)碳酸氢钠加入反应瓶中,搅拌15min后,待体系无气泡产生时,加入0.118g(1.05mmol)氨基脲盐酸盐,升温至50℃反应1h,反应液浓缩、冷却、过滤、干燥得0.15g黄色固体1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑氨基脲盐,收率为64.1%。
结构鉴定:
红外光谱:IR(KBr,cm-1),υ:3478,3379,3183,2923,1709,1611,1536,1419,1384,1322,1279,1202,1122,1023,903
核磁光谱:1H NMR(DMSO-d6,500MHz),δ:6.58(s,4H,2NH2),8.60(s,2H,2NH2),9.72(s,6H,2NH3 +)
13C NMR(DMSO-d6,125MHz),δ:128.48,133.19,158.28
元素分析:分子式C6H12N16O10
理论值:C 15.39,H 2.58,N 47.86
实测值:C 15.49,H 2.52,N 47.94。
上述结构鉴定数据证实得到物质确实是1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑氨基脲盐。
本发明1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑氨基脲盐的性能
(1)物化性能
外观:黄色固体
溶解度:易溶于二甲基亚砜、N,N-二甲基甲酰胺、水等;不溶于石油醚、正己烷、乙醚等
密度:1.80g/cm3 Gaussian 09程序B3LYP方法
(2)爆轰性能
爆速:密度为1.80g/cm3,计算爆速为8559m/s K-J方程
爆压:密度为1.80g/cm3,计算爆压为33.1GPa K-J方程
爆热:密度为1.80g/cm3,计算爆热为5750kJ/mol K-J方程
本发明的1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑氨基脲盐的用途
本发明的1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑氨基脲盐具有密度大、能量高等优点,有望应用于混合炸药和推进剂技术领域。
Claims (1)
1.一种1,4-二硝胺基-3,6-二硝基吡唑[4,3-c]并吡唑氨基脲盐化合物,其结构式如(I)所示:
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CN110606851A (zh) * | 2019-10-14 | 2019-12-24 | 中国工程物理研究院化工材料研究所 | 一种热稳定性优异的钝感高能含能化合物及其制备方法 |
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