CN115677706A - Synthesis method of 2,2' -bis (2, 4, 6-trinitro) bis-triazolobenzoquinone - Google Patents
Synthesis method of 2,2' -bis (2, 4, 6-trinitro) bis-triazolobenzoquinone Download PDFInfo
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- CN115677706A CN115677706A CN202211272659.3A CN202211272659A CN115677706A CN 115677706 A CN115677706 A CN 115677706A CN 202211272659 A CN202211272659 A CN 202211272659A CN 115677706 A CN115677706 A CN 115677706A
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- triazolobenzoquinone
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- trinitrochlorobenzene
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- 238000001308 synthesis method Methods 0.000 title abstract description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims abstract description 54
- 238000006243 chemical reaction Methods 0.000 claims abstract description 35
- HJRJRUMKQCMYDL-UHFFFAOYSA-N 1-chloro-2,4,6-trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(Cl)C([N+]([O-])=O)=C1 HJRJRUMKQCMYDL-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000007787 solid Substances 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims abstract description 15
- 239000002904 solvent Substances 0.000 claims abstract description 15
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000003756 stirring Methods 0.000 claims abstract description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000002156 mixing Methods 0.000 claims abstract description 9
- 230000035484 reaction time Effects 0.000 claims abstract description 5
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims abstract description 4
- 238000005406 washing Methods 0.000 claims abstract description 4
- 238000001035 drying Methods 0.000 claims abstract description 3
- 238000001914 filtration Methods 0.000 claims abstract description 3
- 239000000203 mixture Substances 0.000 claims description 6
- 230000002194 synthesizing effect Effects 0.000 claims 5
- 239000002994 raw material Substances 0.000 abstract description 6
- 230000001988 toxicity Effects 0.000 abstract description 5
- 231100000419 toxicity Toxicity 0.000 abstract description 5
- 239000006227 byproduct Substances 0.000 abstract description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 239000000126 substance Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 238000005979 thermal decomposition reaction Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 4
- YSIBQULRFXITSW-OWOJBTEDSA-N 1,3,5-trinitro-2-[(e)-2-(2,4,6-trinitrophenyl)ethenyl]benzene Chemical compound [O-][N+](=O)C1=CC([N+](=O)[O-])=CC([N+]([O-])=O)=C1\C=C\C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O YSIBQULRFXITSW-OWOJBTEDSA-N 0.000 description 3
- XPARNGAWWCCOIM-UHFFFAOYSA-N 2-fluoro-1,3,5-trinitrobenzene Chemical compound [O-][N+](=O)C1=CC([N+]([O-])=O)=C(F)C([N+]([O-])=O)=C1 XPARNGAWWCCOIM-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- -1 picryl Chemical group 0.000 description 3
- QNZDCKBBTJYQDT-UHFFFAOYSA-N 3,5-dinitropyridin-2-amine Chemical compound NC1=NC=C([N+]([O-])=O)C=C1[N+]([O-])=O QNZDCKBBTJYQDT-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Chemical group 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000004880 explosion Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 239000003779 heat-resistant material Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical group C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a synthesis method of 2,2' -bis (2, 4, 6-trinitro) bis-triazolobenzoquinone, which comprises the following steps: mixing the bis-triazolobenzoquinone, a solvent, triethylamine and 2,4, 6-trinitrochlorobenzene, stirring and reacting for 3-12 h at 10-30 ℃, filtering precipitated solid, washing and drying the obtained solid to obtain the 2,2 '-bis (2, 4, 6-trinitro) bis-triazolobenzoquinone, wherein the solvent is N, N' -dimethylformamide, acetonitrile or N-methylpyrrolidone. The method has the advantages of easily obtained reaction raw materials, short reaction time, no obvious toxicity of by-products in the synthetic route, weak corrosivity, low requirement on equipment and easy industrialization.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a synthesis method of 2,2' -bis (2, 4, 6-trinitro) bis-triazolobenzoquinone.
Background
The picryl energetic compounds mostly have a larger pi conjugated system, so that the whole molecule has more excellent heat resistance than a general structure, for example: 2,2', 4', 6' -hexanitrodiphenylethylene (hexanitrostilbene, HNS), the picryl and ethylene form a conjugated system, the thermal decomposition temperature is 332 ℃, and the conjugated system becomes one of the representative compounds of the early heat-resistant explosive; 5,5 '-biter-2, 2' -di (1, 3, 4-oxadiazole) (TKX-55) adopts two groups of oxadiazole rings to be coplanar, and is combined with the biter to form a conjugated system which is larger than PYX, and the thermal decomposition peak temperature is 370 ℃, and is increased by nearly 40 ℃ compared with the HNS decomposition temperature; 2, 6-di-bitter amino-3, 5-dinitropyridine (PYX) introduces a pyridine ring and is conjugated with a di-bitter group, so that the thermal decomposition peak temperature of the PYX is equivalent to that of TKX-55; 4, 8-bistoury-bis-furazano-pyrazine (TNBP) forms an ultra-large conjugated system due to the introduction of bis-furazan-pyrazine into a bistoury structure, and the thermal decomposition peak temperature is as high as 418 ℃, which is increased by about 50 ℃ compared with the thermal decomposition temperatures of TKX-55 and PYX. Therefore, the compound related to the invention relates to a large conjugated system of bis-triazolobenzoquinone in a bis-bitter-based conjugated system, so as to obtain the heat-resistant energetic material 2,2' -bis (2, 4, 6-trinitro) bis-triazolobenzoquinone, which has the following structural formula:
due to the introduction of a bis-triazolobenzoquinone structure, the compound has a similar ultra-large n conjugated system with TNBP, a better thermal stability effect is reflected, the thermal explosion temperature reaches 430 ℃, the compound is an energetic material with excellent heat resistance, the material can keep good physical and chemical stability under a high-temperature condition, and the compound becomes a compound with potential important application in the field of ultra-high temperature heat-resistant energetic materials.
In 1975, berlin Jane K. And Coburn Michael D. In the rules derivatives of benzole [1,2-d:4,5-d' ] bistriale and benzole [1,2d:
the route adopts bis-triazolobenzoquinone and 2,4, 6-trinitrofluorobenzene as reaction raw materials, and generates 2,2' -bis (2, 4, 6-trinitro) bis-triazolobenzoquinone by removing HF between molecules, wherein the reaction yield is 96%. From this reaction scheme, it can be seen that although the yield of this reaction scheme is high, there are two problems with this reaction: on one hand, a large amount of HF gas is generated in the reaction, and as HF is a gas with strong acidity and toxicity and the substance also has a corrosion effect on glassware, the synthetic route has greater limitation and is not easy to industrialize; on the other hand, the 2,4, 6-trinitrofluorobenzene adopted as the raw material in the reaction is rarely sold as an industrial product or is expensive.
Disclosure of Invention
Based on the above purpose, the invention provides a synthesis method of 2,2' -bis (2, 4, 6-trinitro) bistriazoloquinone, which solves the problems of expensive synthesis raw materials, and reaction toxicity and corrosivity existing in the existing method.
In order to achieve the purpose, the invention adopts the following technical scheme to realize the purpose:
the invention discloses a synthesis method of 2,2' -bis (2, 4, 6-trinitro) bis-triazolobenzoquinone, which comprises the following steps:
mixing bis-triazolobenzoquinone, a solvent, triethylamine and 2,4, 6-trinitrochlorobenzene, stirring and reacting for 3-12 h at 10-30 ℃, filtering precipitated solid, washing and drying the obtained solid to obtain 2,2' -bis (2, 4, 6-trinitro) bis-triazolobenzoquinone;
the mixing ratio of the bis-triazolobenzoquinone to the solvent is 1g: 10-20 mL; the molar ratio of the bis-triazolobenzoquinone to the triethylamine is 1: 2-5, wherein the molar ratio of the bis-triazolobenzoquinone to the 2,4, 6-trinitrochlorobenzene is 1:2 to 2.5; the solvent is N, N' -dimethylformamide, acetonitrile or N-methylpyrrolidone.
In the preferred method of the invention, the solid obtained is washed with water and acetone separately.
Preferably, the mixing process of the bis-triazolobenzoquinone, the solvent, the triethylamine and the 2,4, 6-trinitrochlorobenzene comprises the following steps: at 10-30 ℃, bis-triazolobenzoquinone is mixed with a solvent, triethylamine is added under the stirring state, the mixture is stirred until the bis-triazolobenzoquinone is completely dissolved, and then 2,4, 6-trinitrochlorobenzene is added. It should be noted that since the initial stage of the dropwise addition of 2,4, 6-trinitrochlorobenzene is exothermic, it is preferable to add 2,4, 6-trinitrochlorobenzene slowly to avoid too high a reaction temperature.
Preferably, the reaction temperature is 25 ℃, and the reaction time is 8-10 h.
Preferably, the mixing ratio of the bis-triazolobenzoquinone to the mixture is 1g: 18-20 mL, wherein the molar ratio of the bis-triazolobenzoquinone to the triethylamine is 1:2.5, the molar ratio of the bis-triazolobenzoquinone to the 2,4, 6-trinitrochlorobenzene is 1:2.2.
in a preferred embodiment of the present invention, the solvent is N, N' -dimethylformamide.
Compared with the prior art, the invention has the beneficial effects that:
(1) The method has the advantages that the reaction raw materials are easy to obtain: the 2,4, 6-trinitrochlorobenzene adopted by the invention is an important intermediate raw material for preparing a plurality of heat-resistant materials, and is easier to obtain compared with 2,4, 6-trinitrofluorobenzene.
(2) The method has short reaction time: compared with the reaction time of the prior art (16 h at room temperature), the method can achieve the yield which is equivalent to that of the prior art after reacting for about 8 h.
(3) The method of the invention has low reaction toxicity: the method can realize the reaction process under mild conditions, and the byproduct HCl in the synthetic route has no obvious toxicity, is easy to volatilize, has weak corrosivity, has low requirement on equipment and is easy to industrialize.
Detailed Description
The following embodiments of the present invention are given, it should be noted that the present invention is not limited to the following embodiments, and all equivalent changes based on the technical solutions of the present invention are within the protection scope of the present invention.
Example 1
Bis-triazolobenzoquinone (0.152g, 0.8mmol) and N, N' -dimethylformamide (3 mL) were charged into a reaction vessel at a temperature of 25 ℃, triethylamine (0.202g, 2.0 mmol) was added thereto under stirring until the bis-triazolobenzoquinone was completely dissolved, 2,4, 6-trinitrochlorobenzene (0.436 g, 1.76mmol) was slowly added thereto, and the mixture was stirred at room temperature for reaction for 8 hours. After the reaction is finished, the precipitated solid is filtered, water and acetone are used for washing the solid respectively, and the product is dried to obtain 0.483g, the yield is 98.6 percent, and the purity is 98.5 percent.
The structure of the obtained product is identified, and the result is as follows:
infrared spectrum: IR (KBr, cm) -1 )ν:3440,3094,1709,1619,1552,1508,1486,1458,1416,1346,1185,1167,1121,1072,1016,972,925,824,785,750,718,673,483,422cm -1 .
Nuclear magnetic spectrum: 1 H NMR(DMSO-d 6 ,500MHz),δ:9.40ppm；
13 C NMR(DMSO-d 6 ,125MHz),δ:165.98,147.35,146.97,144.04,127.05,122.91
elemental analysis: structural formula C 18 H 4 N 12 O 14
Theoretical value: c35.31, H0.66, N27.45;
measured value: c35.60, H0.68, N27.30;
the above structural identification data confirmed that the resulting product was 2,2' -bis (2, 4, 6-trinitro) bistriazoloquinone.
Example 2
Bis-triazolobenzoquinone (0.152g, 0.8mmol) and N, N' -dimethylformamide (3 mL) were charged into a reaction flask at a temperature of 20 ℃ and triethylamine (0.283g, 2.8mmol) was added under stirring and sufficiently stirred until bis-triazolobenzoquinone was completely dissolved, and then 2,4, 6-trinitrochlorobenzene (0.495g, 2.0mmol) was slowly added and, after completion of the addition, the reaction was stirred at 20 ℃ for 12 hours. After the reaction was completed, the precipitated solid was filtered, and the solid was washed with water and acetone, respectively, and dried to obtain 0.477g of a product, 97.3% in yield, and 98.0% in purity.
The product structure identification result of this example is the same as that of example 1, and the obtained substance is 2,2' -bis (2, 4, 6-trinitro) bistriazoloquinone.
Example 3
Bis-triazolobenzoquinone (0.152g, 0.8mmol) and N, N' -dimethylformamide (1.6 mL) were charged into a reaction flask at a temperature of 15 ℃ and triethylamine (0.202g, 2.0mmol) was added under stirring and sufficiently stirred until bis-triazolobenzoquinone was completely dissolved, and 2,4, 6-trinitrochlorobenzene (0.396g, 1.6mmol) was slowly added and, after completion of the addition, the reaction was stirred at 15 ℃ for 10 hours. After the reaction, the precipitated solid was filtered, and the solid was washed with water and acetone, respectively, and dried to obtain 0.466g of a product, 95.1% in yield and 97.6% in purity.
The result of structural identification of the product of this example is the same as that of example 1, and the obtained substance was 2,2' -bis (2, 4, 6-trinitro) bistriazoloquinone.
Example 4
Bis-triazolobenzoquinone (0.152g, 0.8mmol) and N, N' -dimethylformamide (2.5 mL) were charged into a reaction flask at a temperature of 30 ℃, triethylamine (0.162g, 1.6 mmol) was added while stirring and the mixture was sufficiently stirred until bis-triazolobenzoquinone was completely dissolved, 2,4, 6-trinitrochlorobenzene (0.455g, 1.84mmol) was slowly added, and after completion of the addition, the mixture was stirred at 30 ℃ for reaction for 6 hours. After the reaction, the precipitated solid was filtered, and the solid was washed with water and acetone, respectively, and dried to obtain 0.480g of a product, with a yield of 98.0% and a purity of 95.7%.
The product structure identification result of this example is the same as that of example 1, and the obtained substance is 2,2' -bis (2, 4, 6-trinitro) bistriazoloquinone.
Example 5
Bis-triazolobenzoquinone (0.152g, 0.8mmol) and N, N' -dimethylformamide (3 mL) were charged into a reaction flask at a temperature of 10 ℃ and triethylamine (0.162g, 1.6 mmol) was added under stirring and sufficiently stirred until bis-triazolobenzoquinone was completely dissolved, and then 2,4, 6-trinitrochlorobenzene (0.475g, 1.92mmol) was slowly added and, after completion of the addition, the reaction was stirred at 10 ℃ for 3 hours. After the reaction was completed, the precipitated solid was filtered, and the solid was washed with water and acetone, respectively, and dried to obtain 0.463g of a product, yield 94.5%, purity 97.6%.
The product structure identification result of this example is the same as that of example 1, and the obtained substance is 2,2' -bis (2, 4, 6-trinitro) bistriazoloquinone.
Example 6
Bis-triazolobenzoquinone (0.152g, 0.8mmol) and N-methylpyrrolidone (3 mL) were charged into a reaction vessel at a temperature of 25 ℃, triethylamine (0.202g, 2.0 mmol) was added thereto under stirring until the bis-triazolobenzoquinone was completely dissolved, 2,4, 6-trinitrochlorobenzene (0.436 g, 1.76mmol) was slowly added thereto, and the reaction mixture was stirred at room temperature for 8 hours. After the reaction, the precipitated solid was filtered, and the solid was washed with water and acetone, respectively, and dried to obtain 0.473g of a product, with a yield of 96.6% and a purity of 98.9%.
The product structure identification result of this example is the same as that of example 1, and the obtained substance is 2,2' -bis (2, 4, 6-trinitro) bistriazoloquinone.
Example 7
Bis-triazolobenzoquinone (0.152g, 0.8mmol) and acetonitrile (3 mL) were charged into a reaction flask at a temperature of 25 ℃ and triethylamine (0.202g, 2.0 mmol) was added under stirring and stirred sufficiently until bis-triazolobenzoquinone was completely dissolved, and 2,4, 6-trinitrochlorobenzene (0.436 g, 1.76mmol) was slowly added thereto and, after completion of the addition, the reaction was stirred at room temperature for 8 hours. After the reaction is finished, the precipitated solid is filtered, and the solid is washed by water and acetone respectively, and then the product is dried to obtain 0.460g, the yield is 93.9 percent, and the purity is 97.3 percent.
The product structure identification result of this example is the same as that of example 1, and the obtained substance is 2,2' -bis (2, 4, 6-trinitro) bistriazoloquinone.
Claims (5)
1. A method for synthesizing 2,2' -bis (2, 4, 6-trinitro) bistriazoloquinone is characterized by comprising the following steps:
mixing bis-triazolobenzoquinone, a solvent, triethylamine and 2,4, 6-trinitrochlorobenzene, stirring and reacting for 3-12 h at 10-30 ℃, filtering precipitated solid, washing and drying the obtained solid to obtain 2,2' -bis (2, 4, 6-trinitro) bis-triazolobenzoquinone;
the mixing ratio of the bis-triazolobenzoquinone to the solvent is 1g: 10-20 mL; the molar ratio of the bis-triazolobenzoquinone to the triethylamine is 1: 2-5, wherein the molar ratio of the bis-triazolobenzoquinone to the 2,4, 6-trinitrochlorobenzene is 1:2 to 2.5;
the solvent is N, N' -dimethylformamide, acetonitrile or N-methylpyrrolidone.
2. The method for synthesizing 2,2' -bis (2, 4, 6-trinitro) bistriazoloquinone according to claim 1, wherein the mixing process of the bistriazoloquinone, the solvent, the triethylamine, and the 2,4, 6-trinitrochlorobenzene comprises: at 10-30 ℃, the bis-triazolobenzoquinone is firstly mixed with the solvent, triethylamine is added under the stirring state, the mixture is stirred until the bis-triazolobenzoquinone is completely dissolved, and then the 2,4, 6-trinitrochlorobenzene is slowly added.
3. The method for synthesizing 2,2' -bis (2, 4, 6-trinitro) bistriazoloquinone according to claim 1, wherein the reaction temperature is 25 ℃ and the reaction time is 8-10 hours.
4. The method for synthesizing 2,2' -bis (2, 4, 6-trinitro) bistriazoloquinone according to claim 1, wherein the mixing ratio of bistriazoloquinone to solvent is 1g: 18-20 mL, wherein the molar ratio of the bis-triazolobenzoquinone to the triethylamine is 1:2.5, the molar ratio of the bis-triazolobenzoquinone to the 2,4, 6-trinitrochlorobenzene is 1:2.2.
5. the method of synthesizing 2,2 '-bis (2, 4, 6-trinitro) bistriazoloquinone according to claim 1, wherein the solvent is N, N' -dimethylformamide.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106866561A (en) * | 2017-04-11 | 2017-06-20 | 中国工程物理研究院化工材料研究所 | Nitro or dinitrophenyl benzo [1,2,3] triazole, derivative and preparation method |
| CN114957125A (en) * | 2022-06-08 | 2022-08-30 | 西南科技大学 | Synthesis method of 4-nitro-5-nitramine pyrazole |
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Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106866561A (en) * | 2017-04-11 | 2017-06-20 | 中国工程物理研究院化工材料研究所 | Nitro or dinitrophenyl benzo [1,2,3] triazole, derivative and preparation method |
| CN114957125A (en) * | 2022-06-08 | 2022-08-30 | 西南科技大学 | Synthesis method of 4-nitro-5-nitramine pyrazole |
Non-Patent Citations (1)
| Title |
|---|
| BERLIN, JANE K.，等: "Picryl derivatives of benzo[1, 2-d:4, 5-d\']bistriazole and benzo[1, 2d:4, 5d\']bistriazole-4, 8-dione", 《JOURNAL OF HETEROCYCLIC CHEMISTRY》, vol. 12, no. 2, pages 235 - 237 * |
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