CN114436980A - Fluoro geminal dinitromethyl substituted triazole and pyrazole, and preparation method and application thereof - Google Patents
Fluoro geminal dinitromethyl substituted triazole and pyrazole, and preparation method and application thereof Download PDFInfo
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- CN114436980A CN114436980A CN202210075831.XA CN202210075831A CN114436980A CN 114436980 A CN114436980 A CN 114436980A CN 202210075831 A CN202210075831 A CN 202210075831A CN 114436980 A CN114436980 A CN 114436980A
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- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
The invention belongs to the field of energetic materials, and particularly relates to two novel high-energy low-melting-point compounds, namely 1-fluoro geminal dinitromethyl-3-nitro-1, 2, 4-triazole and 1-fluoro geminal dinitromethyl-3, 4-dinitropyrazole, wherein the 1-fluoro geminal dinitromethyl-3-nitro-1, 2, 4-triazole and 1-fluoro geminal dinitromethyl-3, 4-dinitropyrazole are prepared by one-step reaction, the reaction condition is mild, the operation is simple and convenient, and the yield is up to 85%; the used Selectfluor reagent has low price and low preparation cost. Wherein, 1-fluoro geminal dinitromethyl-3-nitro1,2, 4-triazole has a relatively ideal melting point (74 ℃), and is suitable for casting explosive carriers; the density of the product is up to 1.919 g/cm3The detonation performance is excellent (the detonation velocity is 8761 m/s, the detonation pressure is 34.3 Gpa), and the material is a novel energetic material with high energy and low melting point.
Description
Technical Field
The invention belongs to the field of energetic materials, and particularly relates to two novel high-energy low-melting-point compounds 1-fluoro geminal dinitromethyl-3-nitro-1, 2, 4-triazole and 1-fluoro geminal dinitromethyl-3, 4-dinitropyrazole, and preparation methods and applications of the two novel high-energy low-melting-point compounds. The invention has better application prospect in the field of fusion cast explosives.
Background
The fusion cast explosive is a mixed explosive which has wide application range and can be cast in a molten state. And the carrier is one of the important components of the fused cast explosive (accounting for about 70% of the filling amount in the warhead), and the performance of the carrier has an important influence on the performance of the fused cast explosive. 2,4, 6-trinitrotoluene (TNT) is the most common fusion-cast explosive carrier, but has the defects of poor vulnerability, oil leakage in long-term storage, low detonation performance and the like, and is difficult to meet the development requirements of the current weaponry. Therefore, designing and synthesizing novel fusion-cast explosive carriers are always one of the key and hot research directions in the field of energetic materials.
Currently, many novel fusion-cast explosive carriers have been reported at home and abroad, such as 2, 4-Dinitroanisole (DNAN), 3, 4-Dinitropyrazole (DNP), 3, 4-bis (3 '-nitrofurazanyl-4' -) furazan (BNTF), 1-methyl-2, 4, 5-trinitroimidazole (MTNI), 1,3, 3-Trinitroazetidine (TNAZ), and the like. However, the research and application of fluorine-containing cast explosive carriers are very few, so the invention designs a novel low-melting-point compound which takes 1,2, 4-triazole ring or pyrazole as a framework and takes nitro and fluoro geminal dinitromethyl as energy-containing groups, and 1-fluoro geminal dinitromethyl-3-nitro-1, 2, 4-triazole and 1-fluoro geminal dinitromethyl-3, 4-dinitropyrazole are synthesized in one step through fluorination reaction. The potential value of the fusion-cast explosive carrier is researched and evaluated through the structural characterization and thermal analysis. This is the first report of the synthesis of this compound.
Disclosure of Invention
The invention aims to provide a preparation method of novel high-energy fluorinated geminal dinitromethyl substituted triazole and pyrazole, wherein 1-fluorinated geminal dinitromethyl-3-nitro-1, 2, 4-triazole can be used as a novel fusion cast explosive carrier, and provides a novel method and important parameters for production application research of fusion cast explosives.
The invention is realized by the following technical scheme: two fluorinated geminal dinitromethyl substituted triazoles and pyrazoles respectively having the following structural formulae:
the invention further provides two methods for preparing fluoro geminal dinitromethyl substituted triazoles and pyrazoles, wherein:
the preparation method of the 1-fluorinated geminal dinitromethyl-3-nitro-1, 2, 4-triazole comprises the following steps:
dispersing potassium salt of 1-gem-dinitromethyl-3-nitro-1, 2, 4-triazole in acetonitrile, adding a fluorination reagent, reacting at a certain temperature for 3-4 h, filtering, evaporating filtrate to dryness, extracting with diethyl ether, drying diethyl ether phase with anhydrous sodium sulfate, filtering, evaporating to dryness, and cooling to obtain a light yellow 1-fluoro gem-dinitromethyl-3-nitro-1, 2, 4-triazole crystal;
the preparation method of the 1-fluoro geminal dinitromethyl-3, 4-dinitropyrazole comprises the following steps:
dispersing potassium salt of 1-geminal dinitromethyl-3, 4-dinitropyrazole in acetonitrile, adding a fluorinating agent, reacting at a certain temperature, filtering, evaporating filtrate to dryness, extracting with diethyl ether, drying diethyl ether phase with anhydrous sodium sulfate, filtering, evaporating to dryness, and cooling to obtain light yellow-green 1-fluoro geminal dinitromethyl-3, 4-dinitropyrazole.
The specific synthetic routes of the two fluoro geminal dinitromethyl substituted triazoles and pyrazoles are shown as follows:
as a further improvement of the technical scheme of the preparation method, the acetonitrile is anhydrous acetonitrile, and at least 7 ml of anhydrous acetonitrile is needed for every 1mmol of potassium salt.
As a further improvement of the preparation process of the invention, every 1mmol of potassium salt is reacted with at least 1.2 times the equivalent of fluorinating agent.
As a further improvement of the technical scheme of the preparation method, the fluorination reagent is a Selectfluor reagent or xenon difluoride.
As a further improvement of the technical scheme of the preparation method, when the potassium salt reacts with the fluorinating reagent, the reaction temperature is 15-25 ℃, and the reaction time is 3-4 h.
As a further improvement of the technical scheme of the preparation method, the temperature of the cooled precipitated crystals is 4-10 ℃.
The invention further provides application of two fluoro geminal dinitromethyl substituted triazoles and pyrazoles as energetic materials.
The invention also provides application of the 1-fluoro geminal dinitromethyl-3-nitro-1, 2, 4-triazole as a fusion cast explosive carrier.
Compared with the prior art, the two fluoro geminal dinitromethyl substituted triazoles and pyrazoles have the following advantages that:
the method only prepares the 1-fluoro geminal dinitromethyl-3-nitro-1, 2, 4-triazole and the 1-fluoro geminal dinitromethyl-3, 4-dinitropyrazole by one-step reaction, and has the advantages of mild reaction conditions, simple and convenient operation and high yield up to 85 percent; the used Selectfluor reagent has low price and low preparation cost. Wherein, the 1-fluoro geminal dinitromethyl-3-nitro-1, 2, 4-triazole has ideal melting point (74 ℃), and is suitable for casting explosive carriers; the density of the product is up to 1.919 g/cm3The detonation performance is excellent (the detonation velocity is 8761 m/s, the detonation pressure is 34.3 Gpa), and the material is a novel high-energy low-melting-point energetic material. The density of the 1-fluoro geminal dinitromethyl-3, 4-dinitropyrazole is 1.83 g/cm3The detonation velocity is 8714 m/s, the detonation pressure is 33.2 Gpa, and the material is a novel high-energy low-melting-point energetic material.
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In order to more clearly illustrate the embodiments of the present invention or the technical solutions in the prior art, the drawings used in the description of the embodiments or the prior art will be briefly described below, and it is obvious that the drawings in the following description are some embodiments of the present invention, and other drawings can be obtained by those skilled in the art without creative efforts.
FIG. 1 is a single crystal structure of 1-fluorinated geminal dinitromethyl-3-nitro-1, 2, 4-triazole prepared in example 1.
FIG. 2 shows an IR spectrum of 1-fluorinated geminal dinitromethyl-3-nitro-1, 2, 4-triazole obtained in example 1.
FIG. 3 is an IR spectrum of 1-fluorinated geminal dinitromethyl-3, 4-dinitropyrazole obtained in example 3.
Detailed Description
The technical solutions of the present invention are described clearly and completely below, and it is obvious that the described embodiments are some, not all embodiments of the present invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
EXAMPLE 11 Synthesis of fluoro geminal dinitromethyl-3-nitro-1, 2, 4-triazole
512 mg of potassium salt of 1-geminal dinitromethyl-3-nitro-1, 2, 4-triazole (2 mmol) is dispersed in 14 mL of anhydrous acetonitrile, 921 mg of Selectfluor reagent (2.6 mmol) is added after uniform ultrasonic dispersion, and the mixture is filtered after reaction at 20 ℃ for 3 h. The filtrate was evaporated to dryness and extracted with ether. And drying the ether phase by using anhydrous sodium sulfate, filtering by using a filter head, evaporating the filtrate to dryness, and finally putting the filtrate into an upper layer (4-10 ℃) of a refrigerator to cool overnight to obtain 401 mg of light yellow 1-fluoro geminal dinitromethyl-3-nitro-1, 2, 4-triazole crystal. (yield 85%).
In the invention, the potassium salt of the 1-geminal dinitromethyl-3-nitro-1, 2, 4-triazole is self-made in a laboratory, and the specific preparation method can refer to V.V. Semenov, S.A. Shevelev, A.B. Bruskin, et al, Russ. chem. Bull., 2009, 58(10), 2077.
Structure identification, density detection and detonation performance calculation of the product:
melting point: 74 ℃; decomposition temperature: 167 deg.C.
Nuclear magnetic resonance1H NMR ([D6]DMSO, 150 MHz, 25℃, TMS): δ= 9.88 (s, br) ppm. 13C NMR ([D6]DMSO, 600 MHz, 25℃): δ= 163.61, 151.47 ppm.
Infrared raySpectrum (KBr): 3160, 3028, 2959, 2906, 2743, 2677, 2642, 2436, 1760, 1617, 1578, 1518, 1444, 1381, 1349, 1314, 1235, 1200, 1048, 1008, 948, 884, 831, 791, 701, 646, 591, 519, 480, 417 cm-1。
Elemental analysis: molecular formula C3HFN6O6Theoretical value C, 15.26, H, 0.43 and N, 35.60. Found C, 15.28, H, 0.45, N, 35.61.
Single crystal density 1.919 g/cm3。
The detonation velocity was 8761 m/s and detonation pressure was 34.3 GPa (Gaussian16 and EXPLO5 software).
The above structural identification data confirm that the resulting species is indeed 1-fluoro geminal dinitromethyl-3-nitro-1, 2, 4-triazole.
Example Synthesis of 21-fluorinated geminal dinitromethyl-3-nitro-1, 2, 4-triazole
512 mg of 1-geminal dinitromethyl-3-nitro-1, 2, 4-triazole potassium salt (2 mmol) is dispersed in 14 ml of anhydrous acetonitrile, 440 mg of xenon difluoride (2.6 mmol) is added after uniform ultrasonic dispersion, and the mixture is filtered after reaction for 4 hours at 20 ℃. The filtrate was evaporated to dryness and extracted with ether. And drying the ether phase by using anhydrous sodium sulfate, filtering by using a filter head, evaporating the filtrate to dryness, and finally putting the filtrate into an upper layer (4-10 ℃) of a refrigerator to cool overnight to obtain 373 mg of light yellow 1-fluoro geminal dinitromethyl-3-nitro-1, 2, 4-triazole crystals. (yield 79%).
Example 31 Synthesis of fluoro geminal dinitromethyl-3, 4-dinitropyrazole
600 mg of potassium salt of 1-geminal dinitromethyl-3, 4-dinitropyrazole (2 mmol) is dispersed in 14 mL of anhydrous acetonitrile, after uniform ultrasonic dispersion, 921 mg of Selectfluor reagent (2.6 mmol) is added, and after reaction at 20 ℃ for 3 h, filtration is carried out. The filtrate was evaporated to dryness and extracted with ether. And drying the ether phase by using anhydrous sodium sulfate, filtering by using a filter head, evaporating the filtrate to dryness, and finally putting the filtrate into an upper layer (4-10 ℃) of a refrigerator to cool overnight to obtain 482 mg of light yellow-green 1-fluoro geminal dinitromethyl-3, 4-dinitropyrazole crystals. (yield 86%).
In the invention, the potassium salt of the 1-geminal dinitromethyl-3, 4-dinitropyrazole is self-made in laboratories, and the specific preparation method can refer to V.V. Semenov, S.A. Shevelev, A.B. Bruskin, et al, Russ. chem. Bull, 2009, 58(10) and 2077.
Structure identification, density detection and detonation performance calculation of the product:
melting point: 47 ℃; decomposition temperature: 205 deg.c.
Nuclear magnetism1H NMR ([D6]DMSO, 150 MHz, 25℃, TMS): δ= 10.18 (s, br) ppm. 13C NMR ([D6]DMSO, 600 MHz, 25℃): δ= 163.40, 150.10, 138.41, 129.82 ppm.
Infrared spectrum (KBr): 3670, 3146, 2913, 1569, 1538, 1444, 1407, 1363, 1331, 1306, 1232, 1169, 1117, 1032, 967, 922, 857, 828, 806, 793, 745, 588, 505, 420 cm-1。
Elemental analysis: molecular formula C4HFN6O8Theoretical value C, 17.15, H, 0.36 and N, 30.01. Found C, 17.18, H, 0.34, N, 30.05.
The measured density is 1.83 g/cm3。
The detonation velocity 8714 m/s and detonation pressure 33.2 Gpa (Gaussian16 and EXPLO5 software) were calculated.
The above structural identification data confirmed that the substance was indeed 1-fluoro geminal dinitromethyl-3, 4-dinitropyrazole.
Example Synthesis of 41-fluoro geminal dinitromethyl-3, 4-dinitropyrazole
600 mg of potassium salt (2 mmol) of 1-geminal dinitromethyl-3, 4-dinitropyrazole is taken and dispersed in 14 ml of anhydrous acetonitrile, 440 mg of xenon difluoride (2.6 mmol) is added after uniform ultrasonic dispersion, and the mixture is filtered after reaction for 4 h at 20 ℃. The filtrate was evaporated to dryness and extracted with ether. And drying the ether phase by using anhydrous sodium sulfate, filtering by using a filter head, evaporating the filtrate to dryness, and finally putting the filtrate into an upper layer (4-10 ℃) of a refrigerator to cool overnight to obtain 437 mg of light yellow green 1-fluoro geminal dinitromethyl-3, 4-dinitropyrazole crystals. (yield 78%).
Finally, it should be noted that: the above embodiments are only used to illustrate the technical solution of the present invention, and not to limit the same; while the invention has been described in detail and with reference to the foregoing embodiments, it will be understood by those skilled in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some or all of the technical features may be equivalently replaced; and the modifications or the substitutions do not make the essence of the corresponding technical solutions depart from the scope of the technical solutions of the embodiments of the present invention.
Claims (9)
1. Two fluoro geminal dinitromethyl substituted triazoles and pyrazoles respectively have the following structural formulas:
2. the two processes for the preparation of fluorinated geminal dinitromethyl substituted triazoles and pyrazoles according to claim 1, wherein,
the preparation method of the 1-fluorinated geminal dinitromethyl-3-nitro-1, 2, 4-triazole comprises the following steps:
dispersing potassium salt of 1-gem-dinitromethyl-3-nitro-1, 2, 4-triazole in acetonitrile, adding a fluorination reagent, reacting at a certain temperature for 3-4 h, filtering, evaporating filtrate to dryness, extracting with diethyl ether, drying diethyl ether phase with anhydrous sodium sulfate, filtering, evaporating to dryness, and cooling to obtain a light yellow 1-fluoro gem-dinitromethyl-3-nitro-1, 2, 4-triazole crystal;
the preparation method of the 1-fluoro geminal dinitromethyl-3, 4-dinitropyrazole comprises the following steps:
dispersing potassium salt of 1-geminal dinitromethyl-3, 4-dinitropyrazole in acetonitrile, adding a fluorinating agent, reacting at a certain temperature, filtering, evaporating filtrate to dryness, extracting with diethyl ether, drying diethyl ether phase with anhydrous sodium sulfate, filtering, evaporating to dryness, and cooling to obtain light yellow-green 1-fluoro geminal dinitromethyl-3, 4-dinitropyrazole.
3. The process for the preparation of two fluorinated geminal dinitromethyl substituted triazoles and pyrazoles according to claim 2 wherein the acetonitrile is anhydrous acetonitrile, requiring at least 7 ml per 1mmol of potassium salt.
4. The process for the preparation of two fluorinated geminal dinitromethyl substituted triazoles and pyrazoles according to claim 2, characterized in that at least 1.2 times equivalent of the fluorination reagent is reacted per 1mmol of potassium salt.
5. The method of preparing two fluoro-geminal dinitromethyl substituted triazoles and pyrazoles according to claim 2, wherein the fluorinating agent is a Selectfluor reagent or xenon difluoride.
6. The preparation method of two fluoro geminal dinitromethyl substituted triazoles and pyrazoles according to claim 2, wherein the reaction temperature is 15-25 ℃ and the reaction time is 3-4 h when potassium salt reacts with a fluorinating reagent.
7. The method for preparing two fluoro-geminal dinitromethyl-substituted triazoles and pyrazoles according to claim 2, wherein the temperature for cooling to precipitate crystals is 4 to 10 ℃.
8. Use of two fluorinated geminal dinitromethyl substituted triazoles and pyrazoles according to claim 1 as energetic materials.
9. Use of 1-fluoro geminal dinitromethyl-3-nitro-1, 2, 4-triazole according to claim 1 as a carrier for fusion cast explosives.
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| CN116003333A (en) * | 2022-12-06 | 2023-04-25 | 西安近代化学研究所 | 2-gem dinitropyrazine hydrazine salt compound, preparation method and application |
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| CN105669574A (en) * | 2016-01-12 | 2016-06-15 | 西安近代化学研究所 | 3-fluorodinitromethyl-1, 2, 4-triazole compound |
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| CN105669574A (en) * | 2016-01-12 | 2016-06-15 | 西安近代化学研究所 | 3-fluorodinitromethyl-1, 2, 4-triazole compound |
Non-Patent Citations (4)
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| IGOR L. DALINGER ET AL.: "Novel highly energetic pyrazoles: N-fluorodinitromethyl and N-[(difluoroamino)dinitromethyl] derivatives", 《MENDELEEV COMMUN》 * |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN116003333A (en) * | 2022-12-06 | 2023-04-25 | 西安近代化学研究所 | 2-gem dinitropyrazine hydrazine salt compound, preparation method and application |
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