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Preparation method and performance of high-energy insensitive N-(3,5-binitro-1H-pyrazol-4-yl)-1H-tetrazole-5-amine ionic salt structure

A technology of trinitropyrazole and dinitro, applied in the directions of nitrated acyclic/alicyclic/heterocyclic amine explosive compositions, organic chemistry, etc., can solve problems such as poor thermal stability, achieve high yield, Simple synthetic method and mild conditions

Inactive Publication Date: 2017-02-22
BEIJING INSTITUTE OF TECHNOLOGYGY
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Problems solved by technology

[0004] 4-Amino-3,5-dinitro (LLM-116) is regarded as a new generation of insensitive high-energy explosives, but its thermal stability is poor (T d =178℃), in order to inherit the excellent characteristics of insensitivity and high energy of LLM-116 and make up for its poor thermal stability, the design introduces the skeleton structure segment of the tetrazole ring, a high energy density material, into LLM-116 to form a new The N-bridged bicyclic nitrogen-rich compound N-(3,5-dinitro-1H-pyrazol-4-yl)-1H-tetrazol-5-amine, and the corresponding energetic ion salt

Method used

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  • Preparation method and performance of high-energy insensitive N-(3,5-binitro-1H-pyrazol-4-yl)-1H-tetrazole-5-amine ionic salt structure
  • Preparation method and performance of high-energy insensitive N-(3,5-binitro-1H-pyrazol-4-yl)-1H-tetrazole-5-amine ionic salt structure
  • Preparation method and performance of high-energy insensitive N-(3,5-binitro-1H-pyrazol-4-yl)-1H-tetrazole-5-amine ionic salt structure

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Example 1 Preparation of N-(3,5-dinitro-1H-pyrazol-4-yl)-1H-tetrazol-5-amine (1)

[0028] Its structural formula is as follows:

[0029]

[0030] Into a 50mL thick-walled sealed glass tube, add 0.203g (1mmol) 3,4,5-trinitropyrazole, 0.255g (3mmol) 5-aminotetrazole, 0.224g (5mmol) KOH and 5mL water in sequence, seal Stir, heat up to 160°C, react for 30h, cool with 20% H 2 SO 4 The solution was acidified to pH=1, filtered to obtain a yellow solid, and recrystallized from water / methanol to obtain 0.152 g of a yellow crystal, with a yield of 63%. Density ρ = 1.86g cm -3 , decomposition temperature T d =279℃; IR(neat):3301,3211,3084,2760,1624,1472,1327,1079,837,556cm -1 ; 1 H NMR (500MHz,D 6 -DMSO): δ=9.24 (s, 2NH), 7.11 (t, NH) ppm; 13 C NMR (100MHz,D 6 -DMSO): δ=149.3, 115.52, 99.9ppm; MS (ESI): m / z (%): 240 [M-H] - .

Embodiment 2

[0031] Example 2 Preparation of N-(3,5-dinitro-1H-pyrazol-4-yl)-1H-tetrazolium-5-amine hydroxylamine salt (2)

[0032] Its structural formula is as follows:

[0033]

[0034] Dissolve 0.241g (1.0mmol) of 1 in 50mL of hot water and methanol mixture, add 0.158g (0.5mmol) of Ba(OH) 2 ·8H 2 O, after the reaction mixture was reacted at 60° C. for 2 h, 0.5 mmol of hydroxylamine sulfate was added thereto, the mixture continued to react for 2 h, and the insoluble matter was filtered, the filtrate was concentrated, and the resulting solid was recrystallized from water to obtain the product (0.213 g, 78%). Density: ρ=1.84g cm -3 ;Decomposition temperature: T d =296°C (DSC); IR (neat): 3393, 3246, 3077, 1631, 1474, 1327, 1080, 1008, 841, 730, 556cm -1 . 1 H NMR (500MHz, d 6 -DMSO): δ=14.86(s, NH), 9.24(s, NH), 7.11(t, NH 2 ) ppm; 13 C NMR (100MHz,D 6 -DMSO): δ=157.1,155.8,149.4,115.5ppm; Anal.calcd for C 4 h 6 N 10 o 5 (274.15)%: C 17.50, H 2.23, N51.12; found C 17.52, H ...

Embodiment 3

[0035] Example 3 Preparation of N-(3,5-dinitro-1H-pyrazol-4-yl)-1H-tetrazolium-5-amine hydrazine salt (3)

[0036] Its structural formula is as follows:

[0037]

[0038] Dissolve 0.241g (1.0mmol) 1 in hot water and methanol mixture, add 0.050g (1.0mmol) hydrazine hydrate (99%) to it, stir and react at room temperature for 2h, concentrate the reaction solution and recrystallize the crude product with water Yellow crystals (0.194 g, yield: 71%) were obtained. Density: ρ=1.84g·cm -3 . Decomposition temperature: T d = 290°C. IR(neat):3326,3301,3166,2918,2649,2077,1579,1456,1318,1104,1016,945,615cm -1 . 1 H NMR (500MHz,D 6 -DMSO): δ=6.63(s), ppm; 13 C NMR (100MHz,D 6 -DMSO): δ=155.8,149.4,115.5ppm; Anal.calcd for C 4 h 7 N 11 o 4 (273.17)%: C 17.57, H 2.54, N 56.45; found C 17.59, H 2.58, N 56.40.

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Abstract

The invention provides a preparation method and performance measurement of N-(3,5-binitro-1H-pyrazol-4-yl)-1H-tetrazole-5-amine (1) and energetic ionic salt thereof, and belongs to the technical field of energetic materials. The synthesis method comprises the steps of adding 3,4,5-trinitropyrazol, 5-amino tetrazole and water into a thick-wall sealed pipe, adjusting the pH to 7 by KOH, performing heating reaction for 48 hours, treating to obtain solid 1,1, and enabling reaction between the solid 1,1 and corresponding cationic sulfate to obtain a target product. The preparation method is simple in synthesis, stable in performance and easy in amplification. In the product, the density is high and is 1.79 to 1.86 g*cm<-3>, the decomposition temperature is high and is 279 to 296 DEG C, the impact sensitivity is 35 to 40 J, the friction sensitivity is 84 to 360 N, the detonation velocity exceeds 9,000 m*s<-1>, the nitrogen content is high and is 51.09 to 60.86 percent, the comprehensive performance is excellent, and a potential application value is achieved.

Description

technical field [0001] The invention relates to the preparation method and performance measurement of N-(3,5-dinitro-1H-pyrazol-4-yl)-1H-tetrazol-5-amine and its energetic ion salt, which belongs to energetic material technology field. Background technique [0002] Nitrogen-rich heterocycles and their energetic ion salts have been attracting great attention as new high-energy-density materials (HEDMs). These heterocyclic compounds generally have a high positive enthalpy of formation, which is derived from a large number of N-N and C-N bonds in their structure; at the same time, the intramolecular and intermolecular hydrogen bonds increase the density, thereby improving the detonation performance and reducing the sensitivity . [0003] The tetrazole ring has a high nitrogen content (79.98% N) and good thermal stability, therefore, it can be used as a segment for constructing high energy density materials. Among the reported energetic ionic salts, most of the ionic salts wi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D401/12C06B25/34
CPCC07D401/12C06B25/34
Inventor 周智明张曼高会奇李川付伟
Owner BEIJING INSTITUTE OF TECHNOLOGYGY
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