CN105111156B - 2 amino, 5,5 ' dinitro, 3,3 ' double (1,2,4 triazole) compounds - Google Patents
2 amino, 5,5 ' dinitro, 3,3 ' double (1,2,4 triazole) compounds Download PDFInfo
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- CN105111156B CN105111156B CN201510603835.0A CN201510603835A CN105111156B CN 105111156 B CN105111156 B CN 105111156B CN 201510603835 A CN201510603835 A CN 201510603835A CN 105111156 B CN105111156 B CN 105111156B
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- 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
- C07D249/14—Nitrogen atoms
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a kind of dinitro 3 of 2 amino 5,5 ', 3 ' double (1,2,4 triazole) compounds, its structural formula is such as shown in (I)：
Description
Technical field
The present invention relates to a kind of energetic material, and in particular to a kind of 2- amino -5,5 '-dinitro -3, and 3 '-bis- (1,2,4-
Triazole) compound.
Background technology
In recent years, energetic material of the rich nitrogen energy-containing compound as a kind of unique properties, because of the end of its burning or blast
Product is mainly that build environment is friendly, free of contamination nitrogen, and is usually applied to the research fields such as explosive, propellant.It is such
Contain substantial amounts of N-N and N=N keys in molecular structure of compounds, a large amount of nitrogen can be discharged during decomposition, produce higher-energy；It is right
The stimulation such as heat, friction, electric spark is insensitive, and has the characteristics that with higher density, the hot big, better heat stability of positive generation,
Therefore, energetic material researcher in countries in the world generates larger concern to such compound.Part has been filtered out simultaneously contains energy
Compound carries out its explorative research research in fields such as the low sense explosive of high energy, gas-forming agents.Such as Alexander
A.Dippold et al. exists《Insensitive Nitrogen-Rich Energetic Compounds Based on the 5,
5’-Dinitro-3,3’-bi-1,2,4-triazol-2-ide Anion》, Eur.J.Inorg.Chem.2012,3474-3484
One is disclosed herein 5,5 '-dinitro -3, the structure of 3 '-bis- (1,2,4- triazole) compounds and the calculating performance of the compound,
Its structure is such as shown in (II)：
The calculating performance of the compound：Nitrogen content is 49.6%, explosion velocity 8413m/s, detonation pressure 32.0GPa, generation heat
For 285.0kJ/mol.But compound generation heat is smaller, energy is relatively low.
The content of the invention
The technical problems to be solved by the invention are to overcome the shortcomings of background technology and defect, there is provided one kind generation heat compared with
2- amino -5,5 '-dinitro -3,3 '-bis- (1,2,4- triazoles) compound high, energy is larger.
The synthetic route of 2- amino -5,5 '-dinitro -3,3 '-bis- (1,2,4- triazoles) compound of the present invention is as follows：
With 5,5 '-dinitro -3,3 '-bis- (1,2,4- triazole) mono-sodium salts are raw material, and aminating reaction occurs with hydroxylamine acid
It is bis- (1,2,4- triazoles) to generate the 2--dinitros -3,3 '-of amino -5,5 '.
2- amino -5 of the present invention, 5 '-dinitro -3,3 '-bis- (1,2,4- triazole) compounds, its structural formula such as (I) institute
Show：
2- amino -5 of the present invention, 5 '-dinitro -3, the synthetic method of 3 '-bis- (1,2,4- triazoles), including following step
Suddenly：
Under 20~25 DEG C of stirrings, successively by 0.5g (2.02mmol) 5,5 '-dinitro -3,3 '-bis- (1,2,4- triazoles)
Mono-sodium salt, 0.4g (3.77mol) sodium carbonate are added in 10.0mL water, are heated to 70 DEG C, and 2.0mL is added dropwise and contains 0.46g
The hydroxylamine acid aqueous solution of (4.03mmol) hydroxylamine acid, after being added dropwise, 0.7g (8.33mol) sodium acid carbonate is added portionwise,
In 70~75 DEG C of reaction 2.5h of temperature, reaction solution is cooled to 20~25 DEG C, pH value is adjusted with 36%~38% (quality) concentrated hydrochloric acid
To 4~5, reacting liquid filtering, filter cake is through washing, dry 2- amino -5,5 '-dinitro -3,3 '-bis- (1,2,4- triazoles).
Advantages of the present invention
2- amino -5 of the present invention, 5 '-dinitro -3,3 '-bis- (1,2,4- triazole) compound generation heat are higher, and it is generated
Heat is 490.7kJ/mol, the 5 of documents, 5 '-dinitro -3, the generation heat of 3 '-bis- (1,2,4- triazoles) is 285.0kJ/
mol；2- amino -5 of the present invention, 5 '-dinitro -3,3 '-bis- (1,2,4- triazole) compound energy are higher, and calculating its explosion velocity is
8900.4m/s, detonation pressure 35.9GPa, quick-fried heat are 5666.9kJ/kg, the 5 of documents, 5 '-dinitro -3,3 '-bis- (1,2,
4- triazoles) calculating explosion velocity be 8413.0m/s, detonation pressure 32.0GPa, quick-fried heat is 4888.0kJ/kg.
Embodiment
The present invention is described in further detail with reference to embodiments.
Embodiment 1
The synthesis of 2- amino -5,5 '-dinitro -3,3 '-bis- (1,2,4- triazoles)
Under 20~25 DEG C of stirrings, successively by 0.5g (2.02mmol) 5,5 '-dinitro -3,3 '-bis- (1,2,4- triazoles)
Mono-sodium salt, 0.4g (3.77mol) sodium carbonate are added in 10.0mL water, are heated to 70 DEG C, and 2.0mL is added dropwise and contains 0.46g
The hydroxylamine acid aqueous solution of (4.03mmol) hydroxylamine acid, after being added dropwise, 0.7g (8.33mol) sodium acid carbonate is added portionwise,
In 70~75 DEG C of reaction 2.5h of temperature, reaction solution is cooled to 20~25 DEG C, pH value is adjusted with 36%~38% (quality) concentrated hydrochloric acid
To 4~5, reacting liquid filtering, filter cake is through washing, dry 2- amino -5,5 '-dinitro -3,3 '-bis- (1,2,4- triazoles)
0.146g, yield 30.1%.
Structural Identification：
Infrared spectrum：IR(KBr,cm-1),υ：3567(-NH),3446,3384(-NH2),1553,1529,1388,1312
(-NO2), 1647,1042,839 (triazole rings)
Nuclear magnetic spectrum：1HNMR(DMSO-d6,500MHz),δ：3.393(s,1H,NH),7.926(s,2H,NH2)；13CNMR
(DMSO-d6,125MHz),δ：144.15,151.76,157.74,166.21
Elementary analysis：Molecular formula C4H3N9O4
Theoretical value：C 19.92,H 1.25,N 52.28
Measured value：C 19.87,H 1.29,N 52.32
Mass spectrum：(APCI)m/z：240[M-H]-。
It is strictly 2- amino -5,5 '-dinitro -3,3 '-bis- (1,2,4- tri- that said structure appraising datum, which confirms to obtain material,
Azoles).
The performance of 2- amino -5,5 '-dinitro -3,3 '-bis- (1,2,4- triazoles)
(1) physical and chemical performance
Outward appearance：Pale pink solid
Solubility：It is soluble in N,N-dimethylformamide, acetone, acetonitrile, methanol, ethanol etc.；It is slightly soluble in dichloromethane, second
Ether, petroleum ether, hexamethylene etc.
Density：1.88g/cm3The program B3LYP methods of Gaussian 09
Nitrogen content：52.3%
(2) detonation property
The purposes of 2- amino -5,5 '-dinitro -3,3 '-bis- (1,2,4- triazoles)
2- amino -5,5 '-dinitro -3,3 '-bis- (1,2,4- triazoles) compound of the present invention has nitrogen content height, generation
The features such as hot big, energy is high, energetic material field can be applied to as high energy material component.
Claims (1)
1. a kind of 2- amino -5,5 '-dinitro -3,3 '-bis- (1,2,4- triazole) compounds, its structural formula is such as shown in (I)：
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| CN105111156B true CN105111156B (en) | 2018-01-23 |
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