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Preparation method and performance calculation for 2-(dinitromethyl)-3-nitro-1,3-diazacyclo-pent-1-ene ionic salt containing energy

A technology of dinitromethyl and dinitromethylene, applied in the direction of nitrated acyclic/alicyclic/heterocyclic amine explosive composition, preparation of urea derivatives, chemical instruments and methods, etc., can solve the problem of nitrogen content Low temperature, poor thermal stability, high detonation velocity, etc., to achieve the effect of simple synthesis method, easy industrialization, and mild conditions

Inactive Publication Date: 2013-03-06
BEIJING INSTITUTE OF TECHNOLOGYGY
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Problems solved by technology

Among them, hydrazine salt has a very high detonation velocity of 9482m s -1 , higher than the detonation velocity of HMX (1,3,5,7-tetranitro-1,3,5,7-tetraazacyclooctane) (9320m s -1 ), but its stability and sensitivity are not high (Chem.Eur.J.2011, 17, 4613-4618)
Among the energetic ionic salts of 5-dinitromethyltetrazole as anion, the disemicarbazide salt has a higher detonation velocity of 9188 m s -1 , higher than RDX (8977m s -1 ), the thermal stability of this type of salt is not high (J.Mater.Chem., 2007, 17, 3819-3826)
[0009] 2-(Dinitromethylene)-1-nitro-1,3-diazacyclopentane is one of the derivatives of FOX-7, and its thermal stability is poor (decomposition at 121°C), and the nitrogen content not tall

Method used

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  • Preparation method and performance calculation for 2-(dinitromethyl)-3-nitro-1,3-diazacyclo-pent-1-ene ionic salt containing energy
  • Preparation method and performance calculation for 2-(dinitromethyl)-3-nitro-1,3-diazacyclo-pent-1-ene ionic salt containing energy
  • Preparation method and performance calculation for 2-(dinitromethyl)-3-nitro-1,3-diazacyclo-pent-1-ene ionic salt containing energy

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Add 219mg (1.0mmol) 2-(dinitromethylene)-1-nitro-1,3-diazacyclopentane and 2mL methanol to a 25mL one-necked flask to dissolve into a yellow clear liquid, then stir at room temperature 0.075mL (1.0mmol) 25% ammonia water was added thereto, and the reaction was stirred at room temperature, and a light yellow solid precipitate was separated out. The reaction mixture was stirred at room temperature for 1h, and the light yellow precipitate was filtered and washed twice with dichloromethane and petroleum ether respectively, and the solid After drying in a desiccator at room temperature for 2 hours, 224 mg of the product 2-(dinitromethyl)-3-nitro-1,3-diazacyclopent-1-enyl ammonium salt was obtained, with a yield of 95%.

[0028] The reaction conditions not mentioned in the following examples are the same as in Example 1.

[0029] Its structural formula is as follows:

[0030]

[0031] Decomposition temperature: 158.1°C (DSC). Density is 1.79g cm -3 . 1 H NMR (400MHz, d...

Embodiment 2

[0033] The conditions are the same as in Example 1, except that ammonia water is changed to hydrazine hydrate, and the product 2-(dinitromethyl)-3-nitro-1,3-diazacyclopent-1-ene hydrazine salt yield is 246mg, producing The rate is 98%.

[0034] Its structural formula is as follows:

[0035]

[0036] Decomposition temperature: 143.2°C (DSC). Density is 1.77g cm -3 . 1 HNMR (400MHz, d 6 -DMSO): δ=3.95(t, 2H), 4.19(t, 2H), 7.08(s, 5H) ppm; 13 C NMR (100MHz, d 6-DMSO): δ=48.50, 51.58, 124.42, 148.79ppm; IR (KBr pellet): 3297, 2981, 1614, 1572, 1516, 1498, 1364, 1337, 1287, 1257, 1206, 1169, 1119, 1035, 1007 , 942, 842, 781, 752, 681cm -1 ;elemental analysis(%) calcd for C 4 h 9 N 7 o 6 : C 19.13, H 3.61, N 39.04; found: C 18.86, H 3.36, N 38.96.

Embodiment 3

[0038] Condition is the same as embodiment 1, only changes ammoniacal liquor into the guanidine dissolved in a small amount of methanol, product 2-(dinitromethyl)-3-nitro-1,3-diazacyclopent-1-ene guanidine salt output is 267 mg, 96% yield.

[0039] Its structural formula is as follows:

[0040]

[0041] Decomposition temperature: 173.3°C (DSC). Density is 1.76g cm -3 . 1 H NMR (400MHz, d 6 -DMSO): δ=3.95(t, 2H), 4.20(t, 2H), 6.99(s, 6H) ppm; 13 C NMR (100MHz, d 6 -DMSO): δ=48.11, 51.54, 125.65, 148.33, 158.36ppm; IR (KBr pellet): 3335, 3286, 3135, 1643, 1565, 1535, 1491, 1376, 1241, 1215, 1128, 1004, 533cm -1 ;elemental analysis(%) calcd for C 5 h 10 N 8 o 6 : C 21.59, H 3.62, N 40.28; found: C 19.67, H 3.87, N 41.08.

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Abstract

The invention provides a preparation method and performance calculation for a 2-(dinitromethyl)-3-nitro-1,3-diazacyclo-pent-1-ene ionic salt containing energy, which belongs to the technical field of energy materials. A synthetic method for the 2-(dinitromethyl)-3-nitro-1,3-diazacyclo-pent-1-ene ionic salt comprises the following steps: dissolving 2-(dinitromethylene)-1-nitro-1,3-diazacyclopentane in methanol to obtain a yellow clear liquid; adding a cationic compound or a methanol solution thereof with an amount equivalent to one molar Eq; and subjecting an obtained precipitate to filtration, washing and drying to obtain a target product. The synthetic method provided by the invention is simple and has mild conditions and high yield; a pure product can be prepared without complex purifying of the target product; and industrialization of the synthetic method is easy. 8 salts prepared in the invention have density in a range of 1.64 to 1.79 g / cm<3>, detonation velocity in a range of 7949 to 9004 m / s, detonation pressure of 25.2 to 35.5 GPa and a degree of percussion sensitivity in a range of 5.5 to 13 J, and detonation performances of a part of the salts are better than those of RDX. The ionic salt containing energy can be used as a substitute for a nitramine explosive, e.g., RDX.

Description

technical field [0001] The invention relates to a preparation method and performance calculation of 2-(dinitromethyl)-3-nitro-1,3-diazacyclopent-1-ene energetic ion salts, and belongs to the technical field of energetic materials. Background technique [0002] Precise strike, high-efficiency damage, light miniaturization and high survivability are the goals pursued by modern weapons, which makes energetic materials used as weapon energy carriers must meet the requirements of high energy density, low vulnerability and environmental adaptability (Acta Pyrodynamics , 2005, 28, 9-13). However, these properties are always contradictory to some extent: materials with good stability and low sensitivity usually have low energy, and when the energy is high, the sensitivity and stability will become worse. At present, the development of new high-energy-density materials (HEDMs) with high energy and low sensitivity has received more and more attention (J.Am.Chem.Soc.2010, 132, 11904-1...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D233/20C07C279/02C07C277/00C07C281/00C07C281/16C07D249/14C07C275/14C07C273/18C06B25/34
Inventor 周智明宋靳红曹丹黄海丰梁丽轩王凯
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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