CN108727408B - A kind of pyrido-oxifurazan energetic compound and preparation method thereof - Google Patents
A kind of pyrido-oxifurazan energetic compound and preparation method thereof Download PDFInfo
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 7
- 238000006243 chemical reaction Methods 0.000 claims abstract description 24
- URQUBZWTCDKZBI-UHFFFAOYSA-N 2,6-dichloro-3,5-dinitropyridin-4-amine Chemical compound NC1=C([N+]([O-])=O)C(Cl)=NC(Cl)=C1[N+]([O-])=O URQUBZWTCDKZBI-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 12
- 239000000203 mixture Substances 0.000 claims abstract description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000012074 organic phase Substances 0.000 claims abstract description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 33
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 20
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 claims description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
- 239000011259 mixed solution Substances 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 230000035484 reaction time Effects 0.000 claims description 3
- 150000003536 tetrazoles Chemical class 0.000 abstract description 14
- 238000005474 detonation Methods 0.000 abstract description 6
- GZBKVUGZEAJYHH-UHFFFAOYSA-N 2-nitropyridin-3-amine Chemical compound NC1=CC=CN=C1[N+]([O-])=O GZBKVUGZEAJYHH-UHFFFAOYSA-N 0.000 abstract description 5
- 239000000706 filtrate Substances 0.000 abstract description 5
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 239000000463 material Substances 0.000 abstract description 4
- PMYJGTWUVVVOFO-UHFFFAOYSA-N 4-phenyl-3-furoxancarbonitrile Chemical compound N#CC1=[N+]([O-])ON=C1C1=CC=CC=C1 PMYJGTWUVVVOFO-UHFFFAOYSA-N 0.000 abstract description 3
- 239000000047 product Substances 0.000 abstract description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 abstract 1
- CSXNUSFEISIXCN-UHFFFAOYSA-N [1,2,5]oxadiazolo[3,4-b]pyridine Chemical compound C1=CC=NC2=NON=C21 CSXNUSFEISIXCN-UHFFFAOYSA-N 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- 238000003912 environmental pollution Methods 0.000 abstract 1
- 238000000605 extraction Methods 0.000 abstract 1
- 238000012805 post-processing Methods 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- 238000013341 scale-up Methods 0.000 abstract 1
- JKFAIQOWCVVSKC-UHFFFAOYSA-N furazan Chemical compound C=1C=NON=1 JKFAIQOWCVVSKC-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- UWUYVPVCKDCBBP-UHFFFAOYSA-N 5-nitro-2h-1,2,5-oxadiazol-4-amine Chemical compound NC1=CNON1[N+]([O-])=O UWUYVPVCKDCBBP-UHFFFAOYSA-N 0.000 description 7
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 6
- 239000002360 explosive Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- -1 tetrazolo [1,5-a ] pyridine-3-oxide Chemical compound 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- ILVXOBCQQYKLDS-UHFFFAOYSA-N pyridine N-oxide Chemical compound [O-][N+]1=CC=CC=C1 ILVXOBCQQYKLDS-UHFFFAOYSA-N 0.000 description 2
- 238000000197 pyrolysis Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- IBTGEEMBZJBBSH-UHFFFAOYSA-N 2,6-dimethoxypyridine Chemical compound COC1=CC=CC(OC)=N1 IBTGEEMBZJBBSH-UHFFFAOYSA-N 0.000 description 1
- BLBDTBCGPHPIJK-UHFFFAOYSA-N 4-Amino-2-chloropyridine Chemical compound NC1=CC=NC(Cl)=C1 BLBDTBCGPHPIJK-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N DMSO-d6 Substances [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 238000004774 atomic orbital Methods 0.000 description 1
- 238000004364 calculation method Methods 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000004776 molecular orbital Methods 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
- C07D498/14—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
本发明公开了一种吡啶并氧化呋咱含能化合物及其制备方法。该方法是在一定温度下实现对4‑氨基‑2,6‑二氯‑3,5‑二硝基吡啶的叠氮化及脱氮闭环反应，反应结束后将混合物减压旋蒸，加水溶解，经萃取后有机相用无水硫酸钠干燥，过滤，滤液减压旋蒸即可。本发明合成的含能化合物结构新颖，反应条件温和，不需要特别装置、工艺和操作过程简单、生产安全可靠、产物后处理便捷、环境污染小，满足工业放大生产的基本要求；该化合物兼具四唑、氧化呋咱和氨基硝基吡啶的结构，在含能材料领域有潜在的应用，理论计算爆速达到8754 m/s。
The invention discloses a pyridofurazan energetic compound and a preparation method thereof. The method is to realize the azide and denitrification ring-closure reaction of 4-amino-2,6-dichloro-3,5-dinitropyridine at a certain temperature, and after the reaction is completed, the mixture is decompressed and rotary-evaporated, and dissolved in water. After extraction, the organic phase was dried with anhydrous sodium sulfate, filtered, and the filtrate was evaporated under reduced pressure. The energy-containing compound synthesized by the invention has novel structure, mild reaction conditions, no need for special devices, simple process and operation process, safe and reliable production, convenient product post-processing, low environmental pollution, and meets the basic requirements of industrial scale-up production; the compound has both The structures of tetrazole, furoxan and aminonitropyridine have potential applications in the field of energetic materials, and the theoretical detonation velocity reaches 8754 m/s.
Description
Technical Field
The invention belongs to the technical field of explosive synthesis processes, and particularly relates to a synthesis method of an energetic compound 4-amino-5-nitro- [1,2,5] oxadiazole [3,4-e ] tetrazole [1,5-a ] pyridine-3-oxide.
Background
In the field of energetic materials, an energetic derivative taking a furazan oxide group as an explosive group has the following characteristics: 1) furazan oxide groups can provide relatively higher energy densities; 2) the effective oxygen content is high, and the furoxan derivative as an energetic additive can improve the oxygen balance of a system; 3) the furoxan group can endow the derivative with ring tension and high standard formation enthalpy. If one nitro group is replaced by one furazan oxide group, the density can be improved by 0.06-0.08 g/cm3The detonation velocity can be improved by 300 m/s. Furthermore, the introduction of heterocyclic systems may greatly favor combinations of their atomic orbitals over carbocyclic systems due to intramolecular perturbations, since heteroatoms play an important role in the lowest molecular orbital level. But additionallyThe stabilization effect brought by the charge density can often improve the heat resistance of the explosive and reduce the mechanical sensitivity of the explosive. The introduction of ortho amino and nitro groups on the pyridine ring to form intramolecular and intermolecular hydrogen bonds can improve the safety performance and crystal density of energetic compounds; the introduction of nitrogen-rich compounds increases the energy of the energy-containing compounds. However, researchers at home and abroad have only reported on compounds having tetrazole, furazan oxide and amino nitropyridine structures.
J Energ Mater,2005,23(2):99-106 reported that a synthetic route of an energetic compound having tetrazole, furazan oxide groups is shown as follows. The route takes 2, 6-dimethoxy pyridine as a raw material, and 7-nitrotetrazolyl [1,5-f ] furazano [4,5-b ] pyridine-1-oxide (NFP) is synthesized by nitration, hydrazine substitution, azidation and pyrolysis denitrification, and the decomposition point is about 160 ℃. The method has long synthetic route and low utilization rate of substituent groups of pyridine rings.
Chin J Chem,2013,31:1299-1304 reports a synthetic route of an energy-containing compound with a furazan oxide ring and an amino nitropyridine structure as shown in the following formula. The method takes 2-chloro-4-aminopyridine as a raw material, takes ethanol/water as a solvent, completes an azidation reaction at room temperature, and performs pyrolysis denitrification and ring closure under an acidic condition to obtain the 7-amino-6-nitro- [1,2,5] oxadiazol [3,4-b ] pyridine-1-oxide. The theoretical calculation detonation velocity of the compound is only 7.51km/s, and the detonation performance of the pyridine ring series energetic compound cannot be fully exerted.
Disclosure of Invention
The invention aims to provide a pyridofuroxan energetic compound 4-amino-5-nitro- [1,2,5] oxadiazole [3,4-e ] tetrazole [1,5-a ] pyridine-3-oxide and a preparation method thereof.
In order to solve the technical problems, the invention adopts a technical scheme that:
a pyridofuroxan energetic compound (named 4-amino-5-nitro- [1,2,5] oxadiazole [3,4-e ] tetrazole [1,5-a ] pyridine-3-oxide) has the following structure:
the preparation method of the compound comprises the following steps:
dissolving 4-amino-2, 6-dichloro-3, 5-dinitropyridine in an organic solvent, adding sodium azide at room temperature, and stirring for reaction for more than 30 min;
and secondly, adding a small amount of concentrated hydrochloric acid into the reaction mixed solution, heating to react for a period of time, evaporating the solvent from the mixed solution under reduced pressure after the reaction is finished, adding water to dissolve the solvent, extracting with ethyl acetate, drying the organic phase, and distilling under reduced pressure to obtain the target compound.
Wherein, in the first step, the mol ratio of the 4-amino-2, 6-dichloro-3, 5-dinitropyridine to the sodium azide is 1:2-1: 4.
In the first step, the organic solvent comprises acetonitrile, ethyl acetate, tetrahydrofuran, acetone, methanol, ethanol and a mixture thereof, preferably any one or a combination of acetonitrile, tetrahydrofuran and acetone.
In the second step, the mass of the concentrated hydrochloric acid is 1/20-1/30 of 4-amino-2, 6-dichloro-3, 5-dinitropyridine, the reaction temperature of the mixed solution is 30-50 ℃, and the reaction time is 1-3 hours.
Compared with the prior art, the invention has the following remarkable advantages: the invention synthesizes the fully-substituted pyridofuroxan energetic compound for the first time: the 4-amino-5-nitro- [1,2,5] oxadiazole [3,4-e ] tetrazole [1,5-a ] pyridine-3-oxide has the advantages of simple synthesis reaction steps, mild conditions, no need of special devices, safe and reliable production, simple product post-treatment, small environmental hazard and capability of meeting the basic requirements of industrial amplification production; the compound has the structure of tetrazole, furazan oxide and amino nitropyridine, the detonation velocity is 8754m/s theoretically calculated, and the compound can be possibly used in the field of high-energy insensitive energetic materials.
The present invention is described in further detail below with reference to the attached drawing figures.
Drawings
FIG. 1 of pyridofuroxan energetic compounds of the invention1H NMR spectrum.
Detailed Description
The following detailed description of the preferred embodiments of the present invention is provided to enable those skilled in the art to more readily understand the advantages and features of the present invention, and to clearly and unequivocally define the scope of the present invention.
The 4-amino-5-nitro- [1,2,5] of the invention]Oxadiazole [3,4-e ] s]Tetrazole [1,5-a ]]Pyridine-3-oxides having the formula C5H2N8O4The structural formula is as follows:
the synthetic route of the 4-amino-5-nitro- [1,2,5] oxadiazole [3,4-e ] tetrazole [1,5-a ] pyridine-3-oxide is as follows:
the invention relates to a preparation method of 4-amino-5-nitro- [1,2,5] oxadiazole [3,4-e ] tetrazole [1,5-a ] pyridine-3-oxide, which comprises the following steps:
dissolving 4-amino-2, 6-dichloro-3, 5-dinitropyridine in a proper solvent, adding sodium azide at room temperature, and stirring for reaction for 1 h;
and secondly, adding a small amount of concentrated hydrochloric acid into the reaction mixed solution, heating to react for a period of time, evaporating the solvent from the mixed solution under reduced pressure after the reaction is finished, adding water to dissolve the solvent, extracting the mixture by ethyl acetate, drying an organic phase, and distilling under reduced pressure to obtain the 4-amino-5-nitro- [1,2,5] oxadiazole [3,4-e ] tetrazole [1,5-a ] pyridine-3-oxide.
Wherein, in the first step, the mol ratio of the 4-amino-2, 6-dichloro-3, 5-dinitropyridine to the sodium azide is 1:2-1:4, and the solvent for dissolving the 4-amino-2, 6-dichloro-3, 5-dinitropyridine comprises acetonitrile, ethyl acetate, tetrahydrofuran, acetone, methanol, ethanol and a mixture thereof. Wherein, the reaction solvent preferably comprises acetonitrile, tetrahydrofuran and acetone.
In the second step, the mass of the concentrated hydrochloric acid is 1/20-1/30 of 4-amino-2, 6-dichloro-3, 5-dinitropyridine, the reaction temperature of the mixed solution is 30-50 ℃, and the reaction time is 1-3 hours.
Example 1
1.26g (5mmol) of 4-amino-2, 6-dichloro-3, 5-dinitropyridine was dissolved in 15mL of acetonitrile, and 0.65g (10mmol) of sodium azide was added thereto at room temperature under stirring, followed by reaction with stirring for 30 min. 1 drop of concentrated hydrochloric acid is added into the reaction mixture, and the temperature is raised to 30 ℃ for reaction for 3 hours. After the reaction is finished, the mixed solution is decompressed and steamed, dissolved by adding water, extracted by ethyl acetate, dried and filtered by the organic phase, and the filtrate is decompressed and distilled to obtain yellow solid 4-amino-5-nitro- [1,2, 5-nitro- [1]Oxadiazole [3,4-e ] s]Tetrazole [1,5-a ]]Pyridine-3-oxide 0.89g, yield 75%. m.p.150-151 ℃ (dec.);1H NMR(DMSO-d6,400MHz):δ10.17(s,1H),9.50(s,1H)；13C NMR(DMSO-d6100MHz) delta 148.96,144.27,141.87,111.17,105.06; MS (ESI) M/z:239.0(M + H), see FIG. 1.
The compound has the structures of tetrazole, furazan oxide and amino nitropyridine, the detonation velocity is calculated up to 8754m/s theoretically, and the compound has potential application in the field of high-energy insensitive energetic materials.
Example 2
1.26g (5mmol) of 4-amino-2, 6-dichloro-3, 5-dinitropyridine is dissolved in 15mL of a mixed solvent of ethyl acetate and acetone, 0.98g (15mmol) of sodium azide is added under stirring at room temperature, and the mixture is stirred and reacted for 30 min. 1 drop of concentrated hydrochloric acid is added into the reaction mixture, and the temperature is raised to 35 ℃ for reaction for 2.5 h. After the reaction, the mixture was rotary-distilled under reduced pressure, dissolved in water, extracted with ethyl acetate, the organic phase was dried, filtered, and the filtrate was distilled under reduced pressure to give 0.71g of 4-amino-5-nitro- [1,2,5] oxadiazol [3,4-e ] tetrazolo [1,5-a ] pyridine-3-oxide as a yellow solid in 60% yield.
Example 3
1.26g (5mmol) of 4-amino-2, 6-dichloro-3, 5-dinitropyridine is dissolved in 15mL of ethanol, 0.98g (15mmol) of sodium azide is added under stirring at room temperature, and the mixture is stirred and reacted for 30 min. 1 drop of concentrated hydrochloric acid is added into the reaction mixture, and the temperature is raised to 50 ℃ for reaction for 1.5 h. After the reaction, the mixture was rotary-distilled under reduced pressure, dissolved in water, extracted with ethyl acetate, the organic phase was dried, filtered, and the filtrate was distilled under reduced pressure to give 0.62g of 4-amino-5-nitro- [1,2,5] oxadiazol [3,4-e ] tetrazolo [1,5-a ] pyridine-3-oxide as a yellow solid in 52% yield.
Example 4
1.26g (5mmol) of 4-amino-2, 6-dichloro-3, 5-dinitropyridine was dissolved in 15mL of acetone, and 1.30g (20mmol) of sodium azide was added thereto at room temperature with stirring, followed by reaction with stirring for 30 min. 1 drop of concentrated hydrochloric acid is added into the reaction mixture, and the temperature is raised to 30 ℃ for reaction for 2 hours. After the reaction, the mixture was rotary-distilled under reduced pressure, dissolved in water, extracted with ethyl acetate, the organic phase was dried, filtered, and the filtrate was distilled under reduced pressure to give 0.80g of 4-amino-5-nitro- [1,2,5] oxadiazol [3,4-e ] tetrazolo [1,5-a ] pyridine-3-oxide as a yellow solid in 67% yield.
The above description is only an embodiment of the present invention, and not intended to limit the scope of the present invention, and all modifications of equivalent structures and equivalent processes performed by the present specification and drawings, or directly or indirectly applied to other related technical fields, are included in the scope of the present invention.
Claims (7)
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| 7-氨基-6-硝基-［1，2，5］噁二唑并［3，4-b］吡啶-1-氧化物合成及性能;马丛明，等;《含能材料》;20141231;第22卷(第14期);第573页化合物3，合成路线、实验内容 * |
| Preparation, characterization, and properties of 7-nitrotetrazolo[1,5-f]furazano[4,5-b]pyridine 1-oxide;My Hang V. Huynh，等;《Journal of Energetic Materials》;20060902;第23卷(第2期);第100页化合物NFP，102页NFP合成路线 * |
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