CN106432192A - Preparation method and performance of high-energy insensitive N-(3,5-binitro-1H-pyrazol-4-yl)-1H-tetrazole-5-amine ionic salt structure - Google Patents

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

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CN106432192A
CN106432192A CN201610543526.3A CN201610543526A CN106432192A CN 106432192 A CN106432192 A CN 106432192A CN 201610543526 A CN201610543526 A CN 201610543526A CN 106432192 A CN106432192 A CN 106432192A
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pyrazoles
tetrazole
dinitro
base
amine
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周智明
张曼
高会奇
李川
付伟
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Beijing Institute of Technology BIT
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C06—EXPLOSIVES; MATCHES
    • C06B—EXPLOSIVES OR THERMIC COMPOSITIONS; MANUFACTURE THEREOF; USE OF SINGLE SUBSTANCES AS EXPLOSIVES
    • C06B25/00—Compositions containing a nitrated organic compound
    • C06B25/34—Compositions containing a nitrated organic compound the compound being a nitrated acyclic, alicyclic or heterocyclic amine

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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

High-energy insensitive N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine ion Salt structure preparation method and performance
Technical field
The present invention relates to N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine and its system containing energy ion salt Preparation Method and performance measurement, belong to energetic material technical field.
Background technology
Azotic heterocyclic compound and its ion salt containing energy be constantly subjected to people as new high Energy Density Materials (HEDM) Very big concern.These heterocyclic compounds typically all have the very high positive enthalpy of formation, a large amount of N-N and C-N key from its structure； Meanwhile, intramolecular and intermolecular hydrogen bond improve density, thus improve detonation property and reducing sensitivity again.
Tetrazole ring nitrogen content height (79.98%N), heat endurance is good, therefore, can be used as the piece building high Energy Density Materials Section.At present it has been reported that containing can be in ion salt, the ion salt of thermal stability preferably (200 DEG C of decomposition temperature ＞) contains mostly Tetrazolium hoop truss.For example：The hydrazonium salt of cyano group tetrazolium, TKX-50, double ammonium salts of double tetrazolium furoxans and this problem are combined into 3- nitro -1- (2 hydrogen-tetrazolium -5- base) -1 hydrogen -1,2,4- triazole -5- amine etc..
4- amino -3,5- dinitro (LLM-116) is counted as the insensitive high energy explosive of a new generation, but its heat endurance is not Good (Td=178 DEG C), in order to inherit the excellent specific property of LLM-116 insensitiveness high energy, make up the bad defect of its heat endurance, design The armature segments of this high Energy Density Materials of tetrazole ring are incorporated in LLM-116, form the bicyclic rich nitridation of new N bridge Compound N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine, and corresponding containing energy ion salt is obtained.Design synthesis N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine decomposition temperature Td=279 DEG C, density p=1.86g cm-1, hit Hit sensitivity IS=35J, friction sensitivity FS=240 N, explosion velocity VD=9289m s-1, content=52.28%；Design is closed simultaneously Such becoming contains energy ion salt DSC decomposition temperature (Td=261-296 DEG C), the higher (ρ=1.79-1.84g cm of density-3), clash into Sensitivity is all higher than 40J, friction sensitivity (FS=84-360N), and explosion velocity is more than 9000m s-1(VD=9003-9364m s-1), nitrogenous Amount is high (51.09-60.86%), belongs to high-energy insensitive Material Field.
Content of the invention
The purpose of the present invention be design and provide N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine and It contains the preparation method of energy ion salt and Performance Evaluation, has obtained the rich nitrogen high-energy insensitive material that a class has excellent detonation property Material.
The purpose of the present invention is achieved through the following technical solutions：
The preparation method of N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine of the present invention, its structural response formula As indicated with 1：
The synthesis of reaction equation 1.N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine
N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine 1 of the present invention contains the preparation side of energy ion salt Method, its general structure is as shown in reaction equation 2：
Reaction equation 2.N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine contains can ion salt structure
N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine 1 of the present invention and its ion salt containing energy be to pass through Route shown in reaction equation 3 is realized：
Reaction equation 3.N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine contains can ion salt synthesis
Its concrete preparation process is as follows：
Add 3,4,5- trinitro- pyrazoles, 5- Aminotetrazole and water in heavy wall seal pipe, quick stirring is lower to add KOH to adjust Section pH value of solution=7, obtain yellow solution, airtight temperature reaction；Reaction finishes, and is adjusted to pH=1 with sulfuric acid, filter after cooling, Cold water washs, and is recrystallized to give yellow solid with water and methyl alcohol mixed liquor, i.e. N- (3,5- dinitro -1H- pyrazoles -4- base) -1H- Tetrazolium -5- amine.
The preparation of N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine salt 3 and 6：Compound 1 is dissolved in water It is added thereto to hydrazine hydrate and the 3,4,5- triamido -1,2,4- triazole of a mole equivalent afterwards.Stirring reaction 1-2h under room temperature, After reactant liquor concentrates, crude product recrystallization obtains final product product.
The preparation of N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine salt 2,4 and 5：
Compound 1 is dissolved in the Ba (OH) adding 0.5 molar equivalent after hot water2·8H2O, the reactant liquor stirring of gained is lower to be added Thermal response 1-2h, is subsequently adding in the corresponding sulfate solution of 1 molar equivalent, and reactant liquor continues lower heating response 2- of stirring 3h, concentrates filtrate after being filtered to remove a small amount of insoluble matter, gained solid appropriate solvent recrystallizes to obtain product；Reaction temperature 60-80 ℃.
It is an advantage of the invention that：
1) obtain new energy-containing compound N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine 1 and its corresponding 4 kinds contain can ion salt, density is high, ρ=1.79-1.86g cm-3, the high N=51.09-60.86%. of nitrogen content
2) ion salt containing energy in the present invention be computed its explosion velocity VD=9003-9364m s-1, quick-fried P=32.3- 38.6GPa, detonation property (V suitable with HMXD=9059m s-1, P=39.2GPa), it is high-energy-density explosive.
3) in the present invention containing can ion salt impact sensitivity after tested, impact sensitivity is all higher than 40J, belong to high-energy insensitive from Alite, is superior to HMX (7.4J).
4) novel compound of present invention and its ion salt friction sensitivity are more than 216N (removing ion salt 5, FS=84N).
5) such compound and its ion salt synthetic method are simple, mild condition, and yield is high, and with deionized water for reaction Solvent, environmental friendliness.
Specific embodiment
The preparation of embodiment 1 N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine (1)
Its structural formula is as follows：
To in 50mL heavy wall sealed glass tube, sequentially add 0.203g (1mmol) 3,4,5- trinitro- pyrazoles, 0.255g (3mmol) 5- Aminotetrazole, 0.224g (5mmol) KOH and 5mL water, airtight stirring, are warming up to 160 DEG C, react 30h, cooling After use 20%H2SO4Solution is acidified to pH=1, is filtrated to get yellow solid, obtains yellow crystals with after water/recrystallizing methanol 0.152g, yield 63%.Density p=1.86g cm-3, decomposition temperature Td=279 DEG C；IR(neat):3301,3211,3084, 2760,1624,1472,1327,1079,837,556cm-1；1H NMR(500MHz,D6-DMSO):δ=9.24 (s, 2NH), 7.11(t,NH)ppm；13C NMR(100MHz,D6-DMSO):δ=149.3,115.52,99.9ppm；MS(ESI):M/z (%): 240[M-H]-.
The preparation of embodiment 2 N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine hydroxylamine salt (2)
Its structural formula is as follows：
0.241g (1.0mmol) 1 is dissolved in the water and methyl alcohol mixed liquor of 50mL heat, is added thereto to 0.158g (0.5mmol)Ba(OH)2·8H2O, after reaction 2h at 60 DEG C of this reactant mixture, is added thereto to 0.5mmol HAS, mixes Compound filters insoluble matter after continuing reaction 2h, concentrates filtrate, the solid of gained through water recrystallization obtain final product product (0.213g, 78%).Density：ρ=1.84g cm-3；Decomposition temperature：Td=296 DEG C (DSC)；IR(neat):3393,3246,3077,1631, 1474,1327,1080,1008,841,730,556cm-1.1H NMR(500MHz,d6-DMSO):δ=14.86 (s, NH), 9.24 (s,NH),7.11(t,NH2)ppm；13C NMR(100MHz,D6-DMSO):δ=157.1,155.8,149.4,115.5ppm； Anal.calcd for C4H6N10O5(274.15) %:C 17.50,H 2.23,N51.12；found C 17.52,H 2.21,N 51.09.
The preparation of embodiment 3 N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine hydrazonium salt (3)
Its structural formula is as follows：
0.241g (1.0mmol) 1 is dissolved in after hot water and methyl alcohol mixed liquor and is added thereto to 0.050g (1.0mmol) water Close hydrazine (99%), stirring reaction 2h under room temperature, reactant liquor concentrate after crude product water recrystallization after obtain citrine body (0.194g, Yield：71%).Density：ρ=1.84g cm-3.Decomposition temperature：Td=290 DEG C.IR(neat):3326,3301,3166, 2918,2649,2077,1579,1456,1318,1104,1016,945,615cm-1.1H NMR(500MHz,D6-DMSO):δ= 6.63(s),ppm；13C NMR(100MHz,D6-DMSO):δ=155.8,149.4,115.5ppm；Anal.calcd for C4H7N11O4(273.17) %:C 17.57,H 2.54,N56.45；found C 17.59,H 2.58,N 56.40.
The preparation of embodiment 4 N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine diaminourea guanidinesalt (4)
HAS, with embodiment 2, is only changed to diaminoguanidine sulfate by condition, and yield is 73%.
Its structural formula is as follows：
Decomposition temperature：Td=285 DEG C；Density：ρ=1.79g cm-3；IR(neat):3473,3439,3313,3193, 2964,1665,1613,1332,946,854cm-1.1H NMR(500MHz,D6-DMSO):δ=8.76 (s, 2H, 2NH), 7.26 (s,2H,2NH),4.61(s,4H,2NH2)ppm；13C NMR(100MHz,D6-DMSO):δ=1160.2,159.3,147.6, 121.7,ppm.Anal.calcd for C5H10N14O4(330.22) %:C18.22,H 3.02,N59.42；found C 18.19,H 3.05,N 59.38.
The preparation of embodiment 5 N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine triamido guanidinesalt (5)
Hydroxylamine sulfate, with embodiment 2, is only changed to triaminoguanidine sulfate by condition, and yield is 70%.
Its structural formula is as follows：
Density：ρ=1.81g cm-3；Decomposition temperature：Td=287 DEG C；IR(neat):3326,3306,3150,3086, 1692,1666,1442,1347,1309,1001,855,759cm-1.1H NMR (500MHz,D6-DMSO):δ=8.54 (s, 3NH,),6.62(d,6NH2)ppm；13C NMR(100MHz,D6-DMSO):δ=160.2,159.5,147.0, 123.6ppm.Anal.calcd for C5H11N15O4(345.24) %:C 17.36,H 3.20,N 60.90；found C17.39,H 3.21,N 60.86.
Embodiment 6 N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine 3,4,5- triamido -1,2,4- three The preparation of azoles salt (6)
Its structural formula is as follows：
241mg (1.0mmol) 1 is dissolved in after water and methyl alcohol mixed liquor be added thereto to 1.0mmol 3,4,5- triamido- 1,2,4- triazole, stirring reaction 2h under room temperature, obtain final product product after crude product water recrystallization after reactant liquor concentration.Yield：70%.
Density：ρ=1.82g cm-3；Decomposition temperature：Td=261 DEG C (DSC)；1H NMR([D6]DMSO,500MHz,25 ℃,TMS):δ=9.24 (s, 2H), 7.11 (s, 4H), 5.60 (s, 2H).13C NMR([D6]DMSO,100MHz,25℃):δ= 155.7,150.4,149.3,115.5ppm.IR(neat):3392,3309,3110,3086,1707,1672,1531,1487, 1347,1189,989,847,cm-1.Anal.calcd for C6H9N15O4(355.23) %:C19.30,H 2.53,N59.20； found C 20.29,H 2.55,N 59.14.
Table 1 be involved in the present invention containing can the physicochemical property of ion salt and detonation parameter, the involved enthalpy of formation, using literary composition Offer J.Phys.Chem.C., the method in 2010,114,13142-13152 calculates；Density Measuring Instrument (Micromeritics AccupycⅡ1340gas pycnometer)；Drop hammer collision sensitivity instrument (BFH-10)；Friction sensitivity instrument BAM Friction Apparatue(FSKM-10)；Differential calorimetric scan instrument (plum Teller-support benefit DSC-1)；Gaussian 03 software program；Quick-fried Hong performance software for calculation EXPLO5 (6.01 version).
Table 1 contains physicochemical property and the detonation parameter of energy ion salt
aDecomposition temperature [DEG C]；bActual density [g cm-3]；cMole lattice energy [kJ mol-1]；dMole generation of cation Enthalpy [kJ mol-1]；eMole enthalpy of formation [the kJ mol of salt-1]；fCO2Oxygen balance, is C for molecular formulaaHbNcOdMolecule (no Containing the crystallization water) its computing formula be OB (%)=1600 [(d-2a-b/2)/Mw]；gImpact sensitivity [J]；hDetonation pressure calculated value [GPa]；iDetonation velocity calculating value [m s-1]；jFriction sensitivity [N]；kN content [%].

Claims (6)

1. can be used for N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine in energetic material field and its containing can be from Alite, it has following structure：
.
2. N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine according to claim 1 belongs to new structure Energy-containing compound.
3. the synthetic method of N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine according to claim 1, It is characterized in that：
Add 3,4,5- trinitro- pyrazoles, 5- Aminotetrazole and water in heavy wall seal pipe, quick stirring lower addition alkali adjusts molten Liquid pH=7, obtains yellow solution, airtight temperature reaction；Reaction finishes, and is adjusted to pH=1 with sulfuric acid, filter, cold water after cooling Washing, is recrystallized to give yellow solid with water and methyl alcohol mixed liquor, i.e. N- (3,5- dinitro -1H- pyrazoles -4- base) -1H- four Azoles -5- amine.
4. the synthetic method of N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine according to claim 3, It is characterized in that：
In course of reaction, 3,4,5- trinitro- pyrazoles and the mol ratio of 5- Aminotetrazole are 1:1-1:3；Alkali used when adjusting PH=7 For potassium hydroxide, NaOH or sodium carbonate；Reaction time is 20-48h；Reaction temperature 100-160 DEG C.
5. N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine according to claim 1 contains energy ion salt Synthetic method it is characterised in that：
(1) N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine with corresponding alkali in water, anti-in methyl alcohol or ethanol After answering 2-3h, revolving removes solvent and obtains final product the corresponding ion salt containing energy；(2) N- (3,5- dinitro -1H- pyrazoles -4- base) -1H- four Azoles -5- amine and 0.5 mole of Ba (OH)2·8H2React filtration BaSO after 2-3h again in water with corresponding sulfate after O mixing4Heavy Concentrate filtrate behind shallow lake and obtain final product the corresponding ion salt containing energy；(3) N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine with React in water after 2-3h with corresponding sulfate or hydrochloride again after equimolar NaOH or potassium hydroxide mixing, revolving Remove part water, recrystallizing to contain accordingly can ion salt.
6. N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine according to claim 5 contains energy ion salt Synthetic method it is characterised in that：
When N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine and alkali direct reaction, reaction dissolvent can be water, Methyl alcohol or ethanol；It is N- (3,5- dinitro -1H- pyrazoles -4- base) -1H-TETRAZOLE -5- amine during by displacement reaction preparation ion salt Barium salt, sylvite or sodium salt；Reaction time is 2-3h, reaction temperature 50-80 DEG C.
CN201610543526.3A 2016-07-11 2016-07-11 Preparation method and performance of high-energy insensitive N-(3,5-binitro-1H-pyrazol-4-yl)-1H-tetrazole-5-amine ionic salt structure Pending CN106432192A (en)

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CN108299442A (en) * 2018-03-15 2018-07-20 西安近代化学研究所 1,4- dinitro amido -3,6- binitropyrazoles [4,3-c] and pyrazoles dicyandiamidines salt compound
CN108383843A (en) * 2018-03-15 2018-08-10 西安近代化学研究所 1,4- dinitro amido -3,6- binitropyrazoles [4,3-c] and pyrazoles diamino tetrazolium salt compound
CN108299442B (en) * 2018-03-15 2019-12-10 西安近代化学研究所 1, 4-dinitroamino-3, 6-dinitropyrazolo [4,3-c ] pyrazolecarboxylamido urea salt compound
CN108218877B (en) * 2018-03-15 2019-12-10 西安近代化学研究所 1, 4-dinitroamino-3, 6-dinitropyrazolo [4,3-c ] pyrazolemicarbazide salt compound
CN108440563A (en) * 2018-03-22 2018-08-24 中国工程物理研究院化工材料研究所 Two furazano piperazine bistetrazoles ion salt containing energy and its synthetic method
CN114105878A (en) * 2021-11-29 2022-03-01 安徽理工大学 3-amino-5-hydrazinopyrazole energetic ionic salt and preparation method thereof
CN114105878B (en) * 2021-11-29 2023-10-13 安徽理工大学 3-Amino-5-hydrazinopyrazole energetic ion salt and preparation method thereof
CN115322174A (en) * 2022-08-26 2022-11-11 北京理工大学 Iodine-enriched energetic compound and preparation method and application thereof
CN115322174B (en) * 2022-08-26 2024-01-26 北京理工大学 Iodine-enriched energetic compound and preparation method and application thereof
CN115894453A (en) * 2022-11-01 2023-04-04 南京理工大学 Imidazole compound, energetic ionic salt thereof and preparation method
CN115894453B (en) * 2022-11-01 2024-04-02 南京理工大学 Pyrazole compound, energetic ionic salt thereof and preparation method thereof

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