CN115340501B - Energetic ionic salt based on bitriazole compounds and synthesis method thereof - Google Patents

Energetic ionic salt based on bitriazole compounds and synthesis method thereof Download PDF

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CN115340501B
CN115340501B CN202110526553.0A CN202110526553A CN115340501B CN 115340501 B CN115340501 B CN 115340501B CN 202110526553 A CN202110526553 A CN 202110526553A CN 115340501 B CN115340501 B CN 115340501B
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杨红伟
姚文静
程广斌
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Nanjing University of Science and Technology
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    • C07D249/02Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/081,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/101,2,4-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 discloses energetic ionic salt based on a bitriazole compound and a synthesis method thereof. The method comprises the following steps: (1) 5- (5-nitro-2H-1, 2, 3-triazole-4-carboxylic acid and 1, 3-diaminoguanidine hydrochloride undergo a cyclization reaction to prepare 5- (5-nitro-2H-1, 2, 3-triazole-4-yl) -4H-1,2, 4-triazole-3, 4-diamine; (2) And (3) selecting ammonia water with high nitrogen content, hydrazine hydrate and hydroxylamine water solution, and respectively carrying out salt forming reaction to obtain corresponding energetic ion salt. The energetic ionic salt synthesized by the invention has good detonation performance and positive formation enthalpy; (3) 5- (5-nitro-2H-1, 2, 3-triazole-4-yl) -4H-1,2, 4-triazole-3, 4-diamine is subjected to nitration reaction to prepare N- (3-amino-5- (5-nitro-2H-1, 2, 3-triazole-4-yl) -4H-1,2, 4-triazole-4-yl) nitramide. The method has the advantages of simple synthesis process, mild reaction conditions, high safety, economic and easily obtained raw materials, high product yield, realization of large-scale production and wide application in the field of energetic materials.

Description

Energetic ionic salt based on bitriazole compounds and synthesis method thereof
Technical Field
The invention belongs to the field of energetic materials, and relates to energetic ionic salt based on a bitriazole compound and a synthesis method thereof.
Background
The new energetic materials have great potential in the fields of explosives, propellants, pyrotechnic technology, etc., and their design and research has been the focus of attention of many research groups worldwide. In the past two centuries, the development of energetic materials has undergone three phases. The first generation energetic materials such as TNT, TATB and the like are based on benzene skeleton design and have low knocking performance. The second generation energetic materials are derived from cyclic and aliphatic nitrosamine structures such as RDX and HMX, and although enhancing the knocking properties of the compounds, stability is reduced. Third generation compounds have high knock performance and high sensitivity based on cage-like nitrosamine structures, such as CL-20. Obviously, the advent of each generation has greatly facilitated the rapid development of energetic materials. However, during the course of the study, there is always a serious discrepancy between high energy and low sensitivity. In order to develop new generation of high energy compounds, many characteristics should be considered, including high energy, low sensitivity, good thermal stability, environmental friendliness and transportation safety. Therefore, new energy molecular skeleton studies have to be considered. The nitrogen-rich heterocyclic backbones have been found to play a key role in novel high energy density materials because they store significant energy in the N-N and n=n bonds of the heterocyclic backbones and have positive heat of formation.
Nitrogen-rich heterocyclic compounds have attracted considerable attention in the development of new energetic compounds. Wherein the triazole molecular skeleton exhibits a high nitrogen content, a high density and a high enthalpy of formation, and is therefore generally selected as a possible building block for the nitrogen-rich heterocyclic compound structure. Triazole molecular skeleton includes 1,2, 3-triazole and 1,2, 4-triazole, 1,2, 3-triazole is compared with 1,2, 4-triazole (delta) due to N-N-N (N3) structure f H m =182kJ mol -1 ) With higher heat of formation. By introducing 1,2, 3-triazole into the energetic molecule, the detonation properties of the energetic compound can be improved, and in addition to the heterocyclic skeleton, the amino groups attached to the backbone are also important for the properties of the compound. And the amino group is introduced to promote the formation of intramolecular and intermolecular hydrogen bonds, so that the density and stability of the compound can be improved, and the problem of low sensitivity of the compound is further improved.
The literature (From N-nitroto N-nitroamino: preparation of high-performance energetic materials by introducing nitrogen-rotations [ J ]. Angew.chem.int. Ed.2015,54, 14513-14517) reports a compound 2,2' -dinitroamino-5, 5' -dinitro-3, 3' -bi-1, 2,4 triazole having a thermal decomposition temperature of 121 ℃, an impact sensitivity of 3J, and a friction sensitivity of 40N. The compound has lower thermal stability and sensitivity, causes great difficulty in storage and transportation, has great potential safety hazard in the actual production process, and limits practical application.
Disclosure of Invention
In order to solve the existing stability problem of the bitriazole compound, the invention aims to provide an energetic ionic salt based on the bitriazole compound.
The technical solution for realizing the purpose of the invention is as follows: a 5- (5-nitro-2H-1, 2, 3-triazol-4-yl) -4H-1,2, 4-triazole-3, 4-diamine energetic ion salt (formula 1,2, 3), having the following structure:
an N- (3-amino-5- (5-nitro-2H-1, 2, 3-triazol-4-yl) -4H-1,2, 4-triazol-4-yl) nitroamide energetic ion salt (formula 4, 5) having the following structure:
the synthesis method of the 5- (5-nitro-2H-1, 2, 3-triazole-4-yl) -4H-1,2, 4-triazole-3, 4-diamine energetic ion salt (formula 1,2, 3) comprises the following steps:
(1) A step of subjecting 5-nitro-2H-1, 2, 3-triazole-4-carboxylic acid (a) and 1, 3-diaminoguanidine hydrochloride (b) to ring closure reaction under a polyphosphoric acid reaction system to prepare 5- (5-nitro-2H-1, 2, 3-triazol-4-yl) -4H-1,2, 4-triazole-3, 4-diamine (c),
(2) A step of preparing a target product by respectively salifying 5- (5-nitro-2H-1, 2, 3-triazole-4-yl) -4H-1,2, 4-triazole-3, 4-diamine (c) with aqueous ammonia, hydrazine hydrate or hydroxylamine solution,
preferably, in step (1), the ratio of the polyphosphoric acid reaction system is 1.5g: 0.5-5.5 ml of phosphorus pentoxide and orthophosphoric acid.
Preferably, in step (1), the molar ratio of 5-nitro-2H-1, 2, 3-triazole-4-carboxylic acid to 1, 3-diaminoguanidine hydrochloride is 1:0.8 to 5.0.
Preferably, in step (1), the reaction temperature is 100 to 150 ℃.
Preferably, in the step (2), the reaction system solvent is any one of absolute methanol, water, absolute ethanol and acetonitrile; the reaction temperature is 20-100 ℃.
The synthesis method of the N- (3-amino-5- (5-nitro-2H-1, 2, 3-triazole-4-yl) -4H-1,2, 4-triazole-4-yl) nitro amide energetic ion salt (formula 4, 5) comprises the following steps:
(1) A step of subjecting 5-nitro-2H-1, 2, 3-triazole-4-carboxylic acid (a) and 1, 3-diaminoguanidine hydrochloride (b) to ring closure reaction under a polyphosphoric acid reaction system to prepare 5- (5-nitro-2H-1, 2, 3-triazol-4-yl) -4H-1,2, 4-triazole-3, 4-diamine (c),
(2) A step of subjecting 5- (5-nitro-2H-1, 2, 3-triazol-4-yl) -4H-1,2, 4-triazol-3, 4-diamine (c) to a nitration reaction with a nitrating agent to prepare N- (3-amino-5- (5-nitro-2H-1, 2, 3-triazol-4-yl) -4H-1,2, 4-triazol-4-yl) nitramide (d),
(3) A step of salifying N- (3-amino-5- (5-nitro-2H-1, 2, 3-triazole-4-yl) -4H-1,2, 4-triazole-4-yl) nitroamide (d) with hydrazine hydrate or hydroxylamine aqueous solution respectively to prepare a target product,
preferably, in step (1), the ratio of the polyphosphoric acid reaction system is 1.5g: 0.5-5.5 ml of phosphorus pentoxide and orthophosphoric acid.
Preferably, in step (1), the molar ratio of 5-nitro-2H-1, 2, 3-triazole-4-carboxylic acid to 1, 3-diaminoguanidine hydrochloride is 1:0.8 to 5.0.
Preferably, in step (1), the reaction temperature is 100 to 150 ℃.
Preferably, in step (2), the nitrifying reagent is 100% HNO 3 、98%H 2 SO 4 /HNO 3 And 98% HNO 3 Any one of them; the feed ratio of 5- (5-nitro-2H-1, 2, 3-triazol-4-yl) -4H-1,2, 4-triazole-3, 4-diamine to the nitrating agent was 1g: 5-25 ml; the reaction temperature is-15 ℃ to-5 ℃.
Preferably, in the step (3), the reaction system solvent is any one of absolute methanol, water, absolute ethanol and acetonitrile; the reaction temperature is 20-100 ℃.
Compared with the prior art, the invention has the innovation points that:
(1) The invention synthesizes a novel high-energy low-sense energetic compound based on the combination of 1,2, 3-triazole and 1,2, 4-triazole molecular frameworks. Compared with the reported bi-1, 2, 4-triazole compounds, the heat stability, the impact sensitivity and the friction sensitivity are all improved.
(2) The synthesis of the energetic ion salt further improves the detonation performance of the compound.
(3) According to the invention, by comparing different nitrifying agents with the feeding amount, the optimal nitrifying agent is determined, and the yield of the target compound is maximally improved.
Drawings
FIG. 1 is a single crystal diagram of 5- (5-nitro-2H-1, 2, 3-triazol-4-yl) -4H-1,2, 4-triazole-3, 4-diamine hydrazine salt.
Detailed Description
The synthetic route of the energetic ion salt is shown as follows:
example 1
Polyphosphoric acid reaction system: phosphorus pentoxide (5.0 g,35.0 mmol) was slowly melted in phosphoric acid (15.0 g,153.0 mmol) and the solution temperature was heated to 50 ℃.
A mixture of 5-nitro-2H-1, 2, 3-triazole-4-carboxylic acid (1.57 g,10.0mmol,1.0 times the equivalent) and diaminoguanidine monohydrochloride (1.88 g,15.0mmol,1.5 times the equivalent) was slowly added to the polyphosphoric acid reaction system. The viscous mixture was then gradually raised to 120 ℃. The mixture was stirred at 120 ℃ for 10h and then cooled to room temperature. The reaction solution was poured into ice water (20.0 mL), and then adjusted to ph=2 with concentrated sodium hydroxide solution. The precipitate was filtered, washed with a large amount of water and dried in vacuo to give 5- (5-nitro-2H-1, 2, 3-triazol-4-yl) -4H-1,2, 4-triazole-3, 4-diamine (c) as a white powder in 61.9% yield.
1 H NMR(500MHz,DMSO-d 6 ):δ=8.19(s,2H),5.86(s,2H)ppm. 13 C NMR(125MHz,DMSO-d 6 ):δ=152.80,151.57,144.75,125.87ppm.IR(KBr):v=3431,3318,3218,1683,1633,1504,1380,1251,1196,1132,996,908,809,776,680,649cm -1 ;elemental analysis calcd(%)for C 4 H 5 N 9 O 2 (211):C 22.75,H 2.39,N 59.70;found:C 22.72,H 2.38,N 59.70。
Example 2
To a suspension of 0.21g (1.0 mmol) of 5- (5-nitro-2H-1, 2, 3-triazol-4-yl) -4H-1,2, 4-triazole-3, 4-diamine (c) in water was slowly added dropwise aqueous ammonia, hydrazine hydrate, hydroxylamine solution, respectively, with stirring at 25 ℃. The reaction solution was slowly raised to 75 ℃ and held at 75 ℃ for 2 hours, then cooled to room temperature, a large amount of solid precipitated, the precipitate was filtered, washed with a small amount of water, and dried in air for 48 hours. The related energetic ion salt (1-3) is obtained in turn. Wherein, 5- (5-nitro-2H-1, 2, 3-triazole-4-yl) -4H-1,2, 4-triazole-3, 4-diamine hydrazine salt (2) is recrystallized, and the obtained crystal structure is shown in figure 1.
5- (5-nitro-2H-1, 2, 3-triazol-4-yl) -4H-1,2, 4-triazole-3, 4-diamine salt (1):
1 H NMR(d 6 -DMSO,25℃):δ=7.20(s),5.73(s,2H),5.30(s,2H)ppm. 13 C NMR(d 6 -DMSO,25℃):δ=155.22,152.04,143.79,129.65ppm.IR(KBr):v=3405,2395,2017,1740,1583,1313,1276,1162,1214,1121,1065,1028,973,849,776,739,712,641,502,458cm -1 ;elemental analysis calcd(%)for C 4 H 8 N 10 O 2 (228):C 21.06,H 3.53,N 63.39;found:C 21.04,H 3.55,N63.39。
5- (5-nitro-2H-1, 2, 3-triazol-4-yl) -4H-1,2, 4-triazole-3, 4-diamine hydrazinium salt (2):
1 H NMR(500MHz,DMSO-d 6 ):δ=7.10(s),5.73(s,2H),5.30(s,2H)ppm. 13 C NMR(125MHz,DMSO-d 6 ):δ=155.06,152.00,143.76,129.60ppm.IR(KBr):v=3405,3266,3192,1654,1614,1553,1494,1448,1357,1257,1193,1126,1024,967,826,762,703cm -1 ;elemental analysis calcd(%)for C 4 H 9 N 11 O 2 (243):C 19.76,H 3.73,N 63.36;found:C 19.75,H 3.72,N 63.36。
5- (5-nitro-2H-1, 2, 3-triazol-4-yl) -4H-1,2, 4-triazole-3, 4-diamine hydroxylamine salt (3):
1 H NMR(500MHz,DMSO-d 6 ):δ=9.11(s),6.20(s,2H),5.41(s,2H)ppm. 13 C NMR(125MHz,DMSO-d 6 ):δ=154.22,152.13,143.93,128.69ppm.IR(KBr):v=3426,3321,3119,1671,1626,1502,1454,1362,1239,1186,1101,1030,987,814,791,697cm -1 .elemental analysis calcd(%)for C 4 H 8 N 10 O 3 (244):C 19.68,H 3.30,N 57.36;found:C 19.66,H 3.73,N 57.35。
example 3
To 15mL of 100wt% nitric acid was slowly added 1.57g of 5- (5-nitro-2H-1, 2, 3-triazol-4-yl) -4H-1,2, 4-triazole-3, 4-diamine (c), and the mixture was reacted at-15℃for 20 hours. 100mL of ice water quench the reaction solution, a large amount of solid is separated out, and the N- (3-amino-5- (5-nitro-2H-1, 2, 3-triazole-4-yl) -4H-1,2, 4-triazole-4-yl) nitramide (d) is obtained after filtration, and the yield is 1.98g (yield: 89%).
1 H NMR(500MHz,DMSO-d 6 ):δ=8.39(s,2H)ppm. 13 C NMR(125MHz,DMSO-d 6 ):δ=151.68,149.46,140.31,126.35ppm.IR(KBr):v=3433,3327,3239,1684,1544,1514,1436,1351,1289,1253,1148,1072,975,897,825,769,714cm -1 ;elemental analysis calcd(%)for C 4 H 4 N 10 O 4 (256):C 18.76,H 1.57,N 54.68;found:C 18.73,H 1.56,N 54.68。
Example 4
This example is essentially the same as example 3, except that the nitrating reagent is 98wt% H 2 SO 4 /HNO 3 The desired product (d) was obtained in a yield of 72%.
Example 5
This example is essentially the same as example 3, except that the nitrifying agent is 98wt% HNO 3 The desired product (d) was obtained in a yield of 63%.
Example 6
To a suspension of 0.26g (1.0 mmol) of the compound (d) in methanol at 25℃were slowly added dropwise hydrazine hydrate and hydroxylamine aqueous solution, respectively, with stirring. The reaction solution was stirred at room temperature for 2 hours, the precipitate was filtered, washed with a small amount of water, and dried in air for 48 hours. The relevant energetic ion salts (4, 5) are obtained in turn
N- (3-amino-5- (5-nitro-2H-1, 2, 3-triazol-4-yl) -4H-1,2, 4-triazol-4-yl) nitroamid dihydrazide salt (4)
1 H NMR(500MHz,DMSO-d 6 ):δ=6.75(s)ppm. 13 C NMR(125MHz,DMSO-d 6 ):δ=157.09,152.35,143.48,128.36ppm.IR(KBr):v=3310,3232,2809,1573,1455,1420,1355,1207,1168,1133,1024,991,960,919,858,782,740cm -1 ;elemental analysis calcd(%)for C 4 H 12 N 14 O 4 (320):C 15.00,H 3.78,N 61.24;found:C 15.03,H 3.75,N 61.25。
N- (3-amino-5- (5-nitro-2H-1, 2, 3-triazol-4-yl) -4H-1,2, 4-triazol-4-yl) nitroamide dihydroxyamine salt (5)
1 H NMR(500MHz,DMSO-d 6 ):δ=9.13(s)ppm. 13 C NMR(125MHz,DMSO-d 6 ):δ=152.66,149.90,143.87,126.42ppm.IR(KBr):v=3520,3356,3024,2808,1447,1363,1312,1174,1129,1034,932,882,789,741cm -1 ;elemental analysis calcd(%)for C 4 H 10 N 12 O 6 (322):C14.91,H 3.13,N 52.17;found:C 14.93,H 3.14,N 52.18。
The properties of each energetic ionic salt are given in table 1 below.
TABLE 1 Properties of the Compounds
a Rate of thermal decomposition: 5 ℃ min -1b Enthalpy of formation; c impact sensitivity; d friction sensitivity; e explosion velocity; f detonation pressure; g density.
In summary, the invention provides a synthesis method of energetic ionic salt of a compound based on the combination of 1,2, 3-triazole and 1,2, 4-triazole, and optimizes the reaction conditions, and simultaneously adopts different nitrifying reagents in the nitrifying process, so that the nitrifying conditions are optimized, and the yield of a target product is improved to the greatest extent.

Claims (10)

1. Energetic ionic salt based on bitriazole compound, characterized in that the energetic ionic salt is named as 5- (5-nitro-2H-1, 2, 3-triazole-4-yl) -4H-1,2, 4-triazole-3, 4-diamine and has the following structure:
2. energetic ionic salt based on bitriazole compound, characterized in that the energetic ionic salt is named as N- (3-amino-5- (5-nitro-2H-1, 2, 3-triazole-4-yl) -4H-1,2, 4-triazole-4-yl) nitramide, and has the following structure:
3. the method for synthesizing energetic ionic salts according to claim 1, comprising at least:
(1) A step of carrying out ring closure reaction on 5-nitro-2H-1, 2, 3-triazole-4-carboxylic acid a and 1, 3-diaminoguanidine hydrochloride b under a polyphosphoric acid reaction system to prepare 5- (5-nitro-2H-1, 2, 3-triazole-4-yl) -4H-1,2, 4-triazole-3, 4-diamine c,
(2) A step of preparing a target product by respectively generating salt reaction of 5- (5-nitro-2H-1, 2, 3-triazole-4-yl) -4H-1,2, 4-triazole-3, 4-diamine c and aqueous ammonia, hydrazine hydrate or hydroxylamine solution,
4. a process according to claim 3, wherein in step (1), the polyphosphoric acid reaction system is present in a proportion of 1.5g: 0.5-5.5 ml of a mixed system of phosphorus pentoxide and orthophosphoric acid; the molar ratio of the 5-nitro-2H-1, 2, 3-triazole-4-carboxylic acid to the 1, 3-diaminoguanidine hydrochloride is 1:0.8 to 5.0.
5. A process according to claim 3, wherein in step (1) the reaction temperature is from 100 to 150 ℃.
6. The method according to claim 3, wherein in the step (2), the reaction system solvent is any one of absolute methanol, water, absolute ethanol and acetonitrile; the reaction temperature is 20-100 ℃.
7. The method for synthesizing energetic ionic salts according to claim 2, comprising at least:
(1) A step of carrying out ring closure reaction on 5-nitro-2H-1, 2, 3-triazole-4-carboxylic acid a and 1, 3-diaminoguanidine hydrochloride b under a polyphosphoric acid reaction system to prepare 5- (5-nitro-2H-1, 2, 3-triazole-4-yl) -4H-1,2, 4-triazole-3, 4-diamine c,
(2) A step of subjecting 5- (5-nitro-2H-1, 2, 3-triazol-4-yl) -4H-1,2, 4-triazol-3, 4-diamine c to a nitration reaction with a nitrating agent to prepare N- (3-amino-5- (5-nitro-2H-1, 2, 3-triazol-4-yl) -4H-1,2, 4-triazol-4-yl) nitroamide d,
(3) A step of preparing a target product by respectively salifying N- (3-amino-5- (5-nitro-2H-1, 2, 3-triazole-4-yl) -4H-1,2, 4-triazole-4-yl) nitroamide d with hydrazine hydrate or hydroxylamine aqueous solution,
8. the method of claim 7, wherein in step (1), the polyphosphoric acid reaction system is present in a ratio of 1.5g: 0.5-5.5 ml of a mixed system of phosphorus pentoxide and orthophosphoric acid; the molar ratio of the 5-nitro-2H-1, 2, 3-triazole-4-carboxylic acid to the 1, 3-diaminoguanidine hydrochloride is 1:0.8 to 5.0; the reaction temperature is 100-150 ℃.
9. The process of claim 7 wherein the feed ratio of 5- (5-nitro-2H-1, 2, 3-triazol-4-yl) -4H-1,2, 4-triazole-3, 4-diamine to the nitrating agent is 1g: 5-25 ml; the reaction temperature is-15 ℃ to-5 ℃.
10. The method according to claim 7, wherein in the step (3), the reaction system solvent is any one of absolute methanol, water, absolute ethanol and acetonitrile; the reaction temperature is 20-100 ℃.
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Title
5,5′-二氨基-4,4′-二硝胺基-3,3′-联-1,2,4-三唑三氨基胍盐(TAGAT)的 晶体结构及爆轰性能;薛钰冰,等;《含能材料》;第28卷(第7期);638-643 *
Energetic Materials Based on 5,5’-Diamino-4,4’-dinitramino-3,3’-bi- 1,2,4-triazole;Thomas M. Klapotke,等;《Chem. Asian J.》;第11卷;844-851,figure2,scheme1,table1 *
Thermal stabilization of energetic materials by the aromatic nitrogen-rich 4,4’,5,5‘-tetraamino-3,3’-bi- 1,2,4-triazolium cation;Thomas M. Klapotke, 等;《J. Mater. Chem. A》;第3卷;2658–2668,scheme1,table2 *

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