CN108299326B - 1,5-二硝胺基四唑-3,4-二氨基呋咱盐化合物 - Google Patents
1,5-二硝胺基四唑-3,4-二氨基呋咱盐化合物 Download PDFInfo
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- 239000000463 material Substances 0.000 abstract description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 239000007787 solid Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 229910052757 nitrogen Inorganic materials 0.000 description 9
- ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- ZWWCURLKEXEFQT-UHFFFAOYSA-N dinitrogen pentaoxide Chemical compound [O-][N+](=O)O[N+]([O-])=O ZWWCURLKEXEFQT-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- -1 nitro, trinitro- ethylamino, azo group Chemical group 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- JHJVSUCUNFXIHN-UHFFFAOYSA-N 1,2,5-oxadiazole-3,4-diamine Chemical compound NC1=NON=C1N JHJVSUCUNFXIHN-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 238000005474 detonation Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- BSPUVYFGURDFHE-UHFFFAOYSA-N Nitramine Natural products CC1C(O)CCC2CCCNC12 BSPUVYFGURDFHE-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000004880 explosion Methods 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- POCJOGNVFHPZNS-UHFFFAOYSA-N isonitramine Natural products OC1CCCCC11CNCCC1 POCJOGNVFHPZNS-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 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 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 238000004566 IR spectroscopy Methods 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 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
- 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
- 239000005457 ice water Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 125000003831 tetrazolyl group Chemical group 0.000 description 2
- 238000010792 warming Methods 0.000 description 2
- 229910014288 N-N Inorganic materials 0.000 description 1
- 229910014320 N—N Inorganic materials 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001412 amines Chemical class 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
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000003749 cleanliness Effects 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 238000003810 ethyl acetate extraction Methods 0.000 description 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- 238000006386 neutralization 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
- 239000000376 reactant 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
- C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D257/04—Five-membered rings
- C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
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- C06B25/34—Compositions containing a nitrated organic compound the compound being a nitrated acyclic, alicyclic or heterocyclic amine
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/08—1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles
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Abstract
本发明公开了一种1,5‑二硝胺基四唑‑3,4‑二氨基呋咱盐化合物，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1,5-二硝胺基四唑-3,4-二氨基呋咱盐化合物。
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，可进一步形成硝胺基、硝基、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。将分子中的氨基转化成硝胺基可制备5-硝胺基四唑，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-硝胺基四唑有机铵盐含能化合物，具有优良的爆轰性能。
Haixiang Gao等《Azole-Based Energetic Salts》，Chem.Rev.,2011,111,7377–7436一文公开了一种5-硝胺基四唑-5-氨基四唑盐的结构及性能，其结构如(II)所示：
该化合物的密度为1.63g/cm3，其计算生成热为488kJ/mol，爆速为8276m/s，爆压为25.5GPa。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1,5-二硝胺基四唑-3,4-二氨基呋咱盐化合物。
本发明的1,5-二硝胺基四唑-3,4-二氨基呋咱盐化合物的合成路线如下：
以1-甲氧基甲酰基-1,5-二氨基四唑为原料，首先与五氧化二氮、氢氧化钾、盐酸水溶液反应生成1,5-二硝胺基四唑，然后与3,4-二氨基呋咱(DAF)发生中和反应生成1,5-二硝胺基四唑-3,4-二氨基呋咱盐。
本发明的1,5-二硝胺基四唑-3,4-二氨基呋咱盐化合物，其结构式如(I)所示：
本发明的1,5-二硝胺基四唑-3,4-二氨基呋咱盐的合成方法，包括以下步骤：
(1)1,5-二硝胺基四唑的合成
室温下，将1-甲氧基甲酰基-1,5-二氨基四唑加入乙腈中，冰水浴冷却至0～5℃，滴加五氧化二氮的乙腈溶液，在0～5℃反应1h，继续加入氢氧化钾水溶液，反应0.5h，蒸除溶剂得淡黄色固体，加入甲醇搅拌2h，过滤、干燥得白色固体；向上述白色固体中加入2mol/L的盐酸搅拌0.5h，乙酸乙酯萃取，无水硫酸镁干燥，蒸除溶剂、干燥得白色固体1,5-二硝胺基四唑；其中1-甲氧基甲酰基-1,5-二氨基四唑、五氧化二氮与氢氧化钾的摩尔比为1:2～4:4～8。
(2)1,5-二硝胺基四唑-3,4-二氨基呋咱盐的合成
室温下，将1,5-二硝胺基四唑、甲醇加入反应瓶中，搅拌10min后，加入3,4-二氨基呋咱，升温至35℃反应1.5h，冷却、蒸除溶剂，加入乙醚搅拌，过滤、干燥得米色固体1,5-二硝胺基四唑-3,4-二氨基呋咱盐；其中1,5-二硝胺基四唑与3,4-二氨基呋咱的摩尔比为1:2.0～2.2。
本发明的优点：
本发明的1,5-二硝胺基四唑-3,4-二氨基呋咱盐化合物密度较高，其密度为1.75g/cm3，对比文件的5-硝胺基四唑-5-氨基四唑盐的密度为1.63g/cm3；本发明的1,5-二硝胺基四唑-3,4-二氨基呋咱盐化合物能量较大，其计算爆速为9026m/s，爆压为33.0GPa，生成热为1148kJ/mol，对比文件的5-硝胺基四唑-5-氨基四唑盐的计算爆速为8276m/s，爆压为25.5GPa，生成热为488kJ/mol。
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)1,5-二硝胺基四唑的合成
室温下，将2.21g(14mmol)1-甲氧基甲酰基-1,5-二氨基四唑加入42.0mL乙腈中，冰水浴冷却至0～5℃，滴加42.0mL含4.54g(42mmol)五氧化二氮的乙腈溶液，在0～5℃反应1h，继续加入42.0mL含4.70g(84mmol)氢氧化钾水溶液，反应0.5h，蒸除溶剂得淡黄色固体，加入70.0mL甲醇搅拌2h，过滤、干燥得白色固体；向上述白色固体中加入44.0mL 2mol/L的盐酸搅拌0.5h，乙酸乙酯萃取(40.0mL×4)，无水硫酸镁干燥，蒸除溶剂、干燥得2.11g白色固体1,5-二硝胺基四唑，收率为79.3％。
结构鉴定：
红外光谱：IR(KBr,cm-1),υ：3205,3144,1596,1579,1508,1476,1453,1413,1332,1287,1245,1058,1037,987
核磁光谱：1H NMR(DMSO-d6,500MHz),δ：12.22(s,2H,2NH)
13C NMR(DMSO-d6,125MHz),δ：147.60
元素分析：分子式CH2N8O4
理论值：C 6.32,H 1.06,N 58.95
实测值：C 6.44,H 1.16,N 59.09。
上述结构鉴定数据证实得到物质确实是1,5-二硝胺基四唑。
(2)1,5-二硝胺基四唑-3,4-二氨基呋咱盐的合成
室温下，将0.095g(0.5mmol)1,5-二硝胺基四唑、2.0mL甲醇加入反应瓶中，搅拌10min后，加入0.105g(1.05mmol)3,4-二氨基呋咱，升温至35℃反应1.5h，冷却、蒸除溶剂，加入乙醚搅拌，过滤、干燥得0.15g米色固体1,5-二硝胺基四唑-3,4-二氨基呋咱盐，收率为76.9％。
结构鉴定：
红外光谱：IR(KBr,cm-1),υ：3437,3322,3261,3198,1646,1590,1508,1475,1352,974,861
核磁光谱：1H NMR(DMSO-d6,500MHz),δ：5.80(s,2AFH+)
13C NMR(DMSO-d6,125MHz),δ：148.26,150.18,154.07
元素分析：分子式C5H10N16O6
理论值：C 15.39,H 2.58,N 57.43
实测值：C 15.45,H 2.53,N 57.49。
上述结构鉴定数据证实得到物质确实是1,5-二硝胺基四唑-3,4-二氨基呋咱盐。
本发明1,5-二硝胺基四唑-3,4-二氨基呋咱盐的性能
(1)物化性能
外观：米色固体
溶解度：易溶于二甲基亚砜、N,N-二甲基甲酰胺、甲醇、水等；不溶于石油醚、正己烷、乙醚等
密度：1.75g/cm3 Gaussian 09程序B3LYP方法
(2)爆轰性能
本发明的1,5-二硝胺基四唑-3,4-二氨基呋咱盐的用途
本发明的1,5-二硝胺基四唑-3,4-二氨基呋咱盐具有密度高、能量大等优点，有望应用于混合炸药和高能推进剂等领域。
Claims (1)
1.一种1,5-二硝胺基四唑-3,4-二氨基呋咱盐化合物，其结构式如(I)所示：
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| "4，4’，5，5’-四硝基-2，2’-联咪唑及其含能离子盐的合成及热性能";李亚南，等;《含能材料》;20171231;第25卷(第4期);第298-303页 * |
| "基于1,5-二硝胺基四唑高能材料的合成及性能";李亚南，等;《火炸药学报》;20151231;第38卷(第6期);第16-20页 * |
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