CN105037330A - Synthesis method of 4,5-di(1H-5-tetrazol)-1,2,3-triazole - Google Patents
Synthesis method of 4,5-di(1H-5-tetrazol)-1,2,3-triazole Download PDFInfo
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- CN105037330A CN105037330A CN201510351214.8A CN201510351214A CN105037330A CN 105037330 A CN105037330 A CN 105037330A CN 201510351214 A CN201510351214 A CN 201510351214A CN 105037330 A CN105037330 A CN 105037330A
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- triazole
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
Abstract
The invention discloses a synthesis method of 4,5-di(1H-5-tetrazol)-1,2,3-triazole. The synthesis method comprises the following steps: adding zinc chloride and 4,5-dicyano-1,2,3-triazole into water at the temperature of 10 to 30 DEG C while stirring is carried out; adding sodium azide in batches; heating till the temperature is 85 to 100 DEG C after the addition of sodium azide is finished; carrying out a reaction for 3.5 to 6.5 hours; cooling to 25 DEG C after the reaction is finished; adjusting the pH to be 1 to 2 with concentrated hydrochloric acid of which the mass fraction is 36 percent; filtering; washing filter cake with water; washing with ethyl alcohol; drying to obtain 4,5-di(1H-5-tetrazol)-1,2,3-triazole, wherein the molar ratio of zinc chloride to 4,5-dicyano-1,2,3-triazole is 1 to (0.5 to 2.0); the molar ratio of 4,5-dicyano-1,2,3-triazole to sodium azide is 1:(2.0 to 4.0); the molar ratio of 4,5-dicyano-1,2,3-triazole to water is 1:(250 to 350). The synthesis method is mainly applied to the field of high-energy insensitive high explosive or gas-generating agents.
Description
Technical field
The present invention relates to a kind of synthetic method of 4,5-bis-(1H-5-tetrazyl)-1,2,3-triazoles, belong to energetic material field.
Background technology
High nitrogen stell is the study hotspot of current energetic material, not only has higher density, higher positive Enthalpies of Formation and lower sensitivity, also has the features such as energy level is high, gas production rate is large, detonation product is clean simultaneously.Containing a large amount of C-N, C=N, N-N and N=N keys in this type of molecular structure of compounds, a large amount of nitrogen is discharged during decomposition, produce higher-energy, stimulate insensitive to shock, friction etc., therefore can be used for the low sense explosive of high energy, gas-evolution agent, burning ratemodifier, low characteristic signal propellant, flame formula inhibitor and pyrotechnic composition etc., become the field of countries in the world energetic material investigator common concern.4,5-bis-(1H-5-tetrazyl)-1,2,3-triazoles (being called for short LLM-137), be a kind of high nitrogen class energetic material of excellent performance, its nitrogen content is up to being 75.1%, insensitive to spark, and characteristic drop height reaches 167.5cm, extremely insensitiveness; In addition, LLM-137 decomposition temperature is 313 DEG C, and show excellent thermostability, its over-all properties is better than 3,4-bis-(amino furazan base) furoxan (BAFF), is a kind of insensitive energetic material of green of excellent property.
2012, Pagoria, P.Proc.15thSeminaronNewTrendsinResearchofEnergeticMateri als.April18-April20.2012, pp.54-64 disclosed the synthetic method of LLM-137, and its synthetic route is as follows:
The method with 4,5-bis-(1H-5-tetrazyl)-1,2,3-triazoles for raw material, with NaN
3at ZnBr
2generation 4,5-bis-(1H-5-tetrazyl)-1,2,3-triazoles (being called for short LLM-137) is reacted under catalysis.But the method does not report concrete synthetic method and yield, and catalyst Z nBr
2price is relatively high, also without the characterization data of 4,5-bis-(1H-5-tetrazyl)-1,2,3-triazoles.
Summary of the invention
Technical problem to be solved by this invention overcomes the deficiencies in the prior art, provides the synthetic method of 4,5-bis-(1H-5-tetrazyl)-1,2,3-triazoles that cost is lower, yield is higher.
The synthetic route of 4,5-bis-(1H-5-tetrazyl) of the present invention-1,2,3-triazoles is as follows:
Synthetic route of the present invention with 4,5-bis-(1H-5-tetrazyl)-1,2,3-triazoles for raw material, at ZnCl
24,5-bis-(1H-5-tetrazyl)-1,2,3-triazoles is obtained under katalysis.
In order to solve the problems of the technologies described above, the synthetic method of 4,5-bis-(1H-5-tetrazyl) of the present invention-1,2,3-triazoles, its structural formula is as shown in (I):
With 4, 5-bis-(1H-5-tetrazyl)-1, 2, 3-triazole is raw material, its structural formula is as shown in (II), synthetic method of the present invention comprises the following steps: under stirring, temperature 10 DEG C ~ 30 DEG C, by zinc chloride and 4, 5-dicyano-1, 2, 3-triazole is added to the water, add sodiumazide more in batches, add post-heating and be warming up to 85 DEG C ~ 100 DEG C reaction 3.5h ~ 6.5h, be down to 25 DEG C after reaction terminates and be that the concentrated hydrochloric acid of 36% is to pH=1 ~ 2 with massfraction, subsequent filtration, filter cake is through washing, ethanol is washed, drying step obtains 4, 5-bis-(1H-5-tetrazyl)-1, 2, 3-triazole, wherein zinc chloride and 4, 5-dicyano-1, 2, the mol ratio of 3-triazole is 1:0.5 ~ 2.0, 4, 5-dicyano-1, 2, the mol ratio of 3-triazole and sodiumazide is 1:2.0 ~ 4.0.
The present invention preferred 4, 5-bis-(1H-5-tetrazyl)-1, 2, the synthetic method of 3-triazole, comprise the following steps: under stirring, temperature 25 DEG C, by 6.82g (50mmol) zinc chloride and 6.00g (50mmol) 4, 5-dicyano-1, 2, 3-triazole joins in 250mL water, add 9.75g (150mmol) sodiumazide more in batches, add post-heating and be warming up to 95 DEG C of reaction 4.5h, be down to 25 DEG C after reaction terminates and be that the concentrated hydrochloric acid of 36% is to pH=1 ~ 2 with massfraction, subsequent filtration, filter cake is through washing, ethanol is washed, drying step obtains 4, 5-bis-(1H-5-tetrazyl)-1, 2, 3-triazole.
Advantage of the present invention:
(1) 4,5-bis-(1H-5-tetrazyl)-1,2,3-triazoles synthetic methods of the present invention, with 4,5-dicyano-1,2,3-triazoles for raw material, at ZnCl
24,5-bis-(1H-5-tetrazyl)-1,2,3-triazoles is generated under katalysis, yield is higher, and yield is up to 96%, and purity is 98.9%, and in documents unexposed 4, the concrete synthetic method of 5-bis-(1H-5-tetrazyl)-1,2,3-triazoles, processing condition and yield; (2) 4,5-bis-(1H-5-tetrazyl)-1,2,3-triazoles synthetic methods of the present invention, with ZnCl
2for catalyzer, relatively inexpensive (100g, 378 yuan, lark prestige reagent Science and Technology Ltd.), and in documents, 4,5-bis-(1H-5-tetrazyl)-1,2,3-triazoles synthetic methods use ZnBr
2(100g, 826 yuan, lark prestige reagent Science and Technology Ltd.) is catalyzer.
Embodiment
Below in conjunction with embodiment, the present invention is described in further details.
Embodiment 1
Under stirring, temperature 25 DEG C, by 6.82g (50mmol) zinc chloride and 6.00g (50mmol) 4,5-dicyano-1,2,3-triazole joins in 250mL water, then adds 9.75g (150mmol) sodiumazide in batches, adds post-heating and is warming up to 95 DEG C of reaction 4.5h, be down to 25 DEG C after reaction terminates and be that the concentrated hydrochloric acid of 36% is to pH=1 ~ 2 with massfraction, subsequent filtration, filter cake through washing, ethanol washes, drying step obtains 4,5-bis-(1H-5-tetrazyl)-1,2,3-triazole 9.86g, yield 96.2%, purity 98.9%;
Structural Identification:
Decomposition point: 312 DEG C ~ 313 DEG C;
Infrared spectra: IR (KBr, cm
-1) ν: 3555,3331,3088,2951,2466,1901,1633,1605,1513,1494,1430,1346,1246,1188,1117,1025,989,900,717,671,577,510;
Nuclear magnetic spectrum: δ: 7.57 (s, 2H, NH);
13cNMR (CDCl
3, 125MHz), δ: 148.84,131.93;
Ultimate analysis: structural formula C
4h
3n
11
Theoretical value: C23.42, H1.47, N75.11
Measured value: C23.29, H1.38, N74.95;
The material that said structure appraising datum proved step obtains is 4,5-bis-(1H-5-tetrazyl)-1,2,3-triazoles really;
Embodiment 2
Under stirring, temperature 25 DEG C, by 3.41g (25mmol) zinc chloride and 6.00g (50mmol) 4, 5-dicyano-1, 2, 3-triazole joins in 200mL water, add 9.75g (150mmol) sodiumazide more in batches, add post-heating and be warming up to 95 DEG C of reaction 4.5h, be down to 25 DEG C after reaction terminates and be that the concentrated hydrochloric acid of 36% is to pH=1 ~ 2 with massfraction, subsequent filtration, filter cake is through washing, ethanol is washed, drying step obtains 4, 5-bis-(1H-5-tetrazyl)-1, 2, 3-triazole 6.29g, yield 61.4%, purity 97.1%, dec, : 312 DEG C ~ 313 DEG C,
Embodiment 3
Under stirring, temperature 25 DEG C, by 5.45g (40mmol) zinc chloride and 6.00g (50mmol) 4, 5-dicyano-1, 2, 3-triazole joins in 250mL water, add 9.75g (150mmol) sodiumazide more in batches, add post-heating and be warming up to 95 DEG C of reaction 4.5h, be down to 25 DEG C after reaction terminates and be that the concentrated hydrochloric acid of 36% is to pH=1 ~ 2 with massfraction, subsequent filtration, filter cake is through washing, ethanol is washed, drying step obtains 4, 5-bis-(1H-5-tetrazyl)-1, 2, 3-triazole 9.26g, yield 90.3%, purity 98.3%, dec, : 312 DEG C ~ 313 DEG C,
Embodiment 4
Under stirring, temperature 25 DEG C, by 5.45g (70mmol) zinc chloride and 6.00g (50mmol) 4, 5-dicyano-1, 2, 3-triazole joins in 330mL water, add 9.75g (150mmol) sodiumazide more in batches, add post-heating and be warming up to 95 DEG C of reaction 4.5h, be down to 25 DEG C after reaction terminates and be that the concentrated hydrochloric acid of 36% is to pH=1 ~ 2 with massfraction, subsequent filtration, filter cake is through washing, ethanol is washed, drying step obtains 4, 5-bis-(1H-5-tetrazyl)-1, 2, 3-triazole 9.72g, yield 94.8%, purity 98.6%, dec, : 312 DEG C ~ 313 DEG C,
Embodiment 5
Under stirring, temperature 25 DEG C, by 6.82g (50mmol) zinc chloride and 6.00g (50mmol) 4, 5-dicyano-1, 2, 3-triazole joins in 250mL water, add 6.50g (100mmol) sodiumazide more in batches, add post-heating and be warming up to 95 DEG C of reaction 4.5h, be down to 25 DEG C after reaction terminates and be that the concentrated hydrochloric acid of 36% is to pH=1 ~ 2 with massfraction, subsequent filtration, filter cake is through washing, ethanol is washed, drying step obtains 4, 5-bis-(1H-5-tetrazyl)-1, 2, 3-triazole 9.56g, yield 93.3%, purity 98.4%, dec, : 312 DEG C ~ 313 DEG C,
Embodiment 6
Under stirring, temperature 25 DEG C, by 6.82g (50mmol) zinc chloride and 6.00g (50mmol) 4, 5-dicyano-1, 2, 3-triazole joins in 350mL water, add 7.80g (120mmol) sodiumazide more in batches, add post-heating and be warming up to 95 DEG C of reaction 4.5h, be down to 25 DEG C after reaction terminates and be that the concentrated hydrochloric acid of 36% is to pH=1 ~ 2 with massfraction, subsequent filtration, filter cake is through washing, ethanol is washed, drying step obtains 4, 5-bis-(1H-5-tetrazyl)-1, 2, 3-triazole 9.70g, yield 94.6%, purity 98.6%, dec, : 312 DEG C ~ 313 DEG C,
Embodiment 7
Under stirring, temperature 25 DEG C, by 6.82g (50mmol) zinc chloride and 6.00g (50mmol) 4, 5-dicyano-1, 2, 3-triazole joins in 250mL water, add 11.0g (170mmol) sodiumazide more in batches, add post-heating and be warming up to 95 DEG C of reaction 4.5h, be down to 25 DEG C after reaction terminates and be that the concentrated hydrochloric acid of 36% is to pH=1 ~ 2 with massfraction, subsequent filtration, filter cake is through washing, ethanol is washed, drying step obtains 4, 5-bis-(1H-5-tetrazyl)-1, 2, 3-triazole 9.77g, yield 95.3%, purity 98.8%, dec, : 312 DEG C ~ 313 DEG C,
Embodiment 8
Under stirring, temperature 25 DEG C, by 6.82g (50mmol) zinc chloride and 6.00g (50mmol) 4, 5-dicyano-1, 2, 3-triazole joins in 250mL water, add 13.0g (200mmol) sodiumazide more in batches, add post-heating and be warming up to 95 DEG C of reaction 4.5h, be down to 25 DEG C after reaction terminates and be that the concentrated hydrochloric acid of 36% is to pH=1 ~ 2 with massfraction, subsequent filtration, filter cake is through washing, ethanol is washed, drying step obtains 4, 5-bis-(1H-5-tetrazyl)-1, 2, 3-triazole 9.75g, yield 95.1%, purity 98.8%, dec, : 312 DEG C ~ 313 DEG C,
Embodiment 9
Under stirring, temperature 25 DEG C, by 6.82g (50mmol) zinc chloride and 6.00g (50mmol) 4,5-dicyano-1,2,3-triazole joins in 250mL water, then adds 9.75g (150mmol) sodiumazide in batches, adds post-heating and is warming up to 70 DEG C of reaction 4.5h, be down to 25 DEG C after reaction terminates and be that the concentrated hydrochloric acid of 36% is to pH=1 ~ 2 with massfraction, subsequent filtration, filter cake through washing, ethanol washes, drying step obtains 4,5-bis-(1H-5-tetrazyl)-1,2,3-triazole 4.86g, yield 47.4%, purity 97.6%;
Embodiment 10
Under stirring, temperature 25 DEG C, by 6.82g (50mmol) zinc chloride and 6.00g (50mmol) 4,5-dicyano-1,2,3-triazole joins in 250mL water, then adds 9.75g (150mmol) sodiumazide in batches, adds post-heating and is warming up to 90 DEG C of reaction 4.5h, be down to 25 DEG C after reaction terminates and be that the concentrated hydrochloric acid of 36% is to pH=1 ~ 2 with massfraction, subsequent filtration, filter cake through washing, ethanol washes, drying step obtains 4,5-bis-(1H-5-tetrazyl)-1,2,3-triazole 9.83g, yield 95.9%, purity 98.7%;
Embodiment 11
Under stirring, temperature 25 DEG C, by 6.82g (50mmol) zinc chloride and 6.00g (50mmol) 4,5-dicyano-1,2,3-triazole joins in 250mL water, then adds 9.75g (150mmol) sodiumazide in batches, adds post-heating and is warming up to 100 DEG C of reaction 4.5h, be down to 25 DEG C after reaction terminates and be that the concentrated hydrochloric acid of 36% is to pH=1 ~ 2 with massfraction, subsequent filtration, filter cake through washing, ethanol washes, drying step obtains 4,5-bis-(1H-5-tetrazyl)-1,2,3-triazole 9.84g, yield 96.0%, purity 98.8%;
Embodiment 12
Under stirring, temperature 25 DEG C, by 6.82g (50mmol) zinc chloride and 6.00g (50mmol) 4,5-dicyano-1,2,3-triazole joins in 230mL water, then adds 9.75g (150mmol) sodiumazide in batches, adds post-heating and is warming up to 95 DEG C of reaction 3.5h, be down to 25 DEG C after reaction terminates and be that the concentrated hydrochloric acid of 36% is to pH=1 ~ 2 with massfraction, subsequent filtration, filter cake through washing, ethanol washes, drying step obtains 4,5-bis-(1H-5-tetrazyl)-1,2,3-triazole 8.99g, yield 87.7%, purity 98.1%;
Embodiment 13
Under stirring, temperature 25 DEG C, by 6.82g (50mmol) zinc chloride and 6.00g (50mmol) 4,5-dicyano-1,2,3-triazole joins in 250mL water, then adds 9.75g (150mmol) sodiumazide in batches, adds post-heating and is warming up to 95 DEG C of reaction 5.5h, be down to 25 DEG C after reaction terminates and be that the concentrated hydrochloric acid of 36% is to pH=1 ~ 2 with massfraction, subsequent filtration, filter cake through washing, ethanol washes, drying step obtains 4,5-bis-(1H-5-tetrazyl)-1,2,3-triazole 9.86g, yield 96.2%, purity 98.5%;
Embodiment 14
Under stirring, temperature 30 DEG C, by 8.18g (60mmol) zinc chloride and 6.00g (50mmol) 4,5-dicyano-1,2,3-triazole joins in 250mL water, then adds 10.4g (160mmol) sodiumazide in batches, adds post-heating and is warming up to 95 DEG C of reaction 5.0h, be down to 25 DEG C after reaction terminates and be that the concentrated hydrochloric acid of 36% is to pH=1 ~ 2 with massfraction, subsequent filtration, filter cake through washing, ethanol washes, drying step obtains 4,5-bis-(1H-5-tetrazyl)-1,2,3-triazole 9.82g, yield 95.8%, purity 98.9%;
Embodiment 15
Under stirring, temperature 20 DEG C, by 6.13g (45mmol) zinc chloride and 6.00g (50mmol) 4,5-dicyano-1,2,3-triazole joins in 250mL water, then adds 9.04g (139mmol) sodiumazide in batches, adds post-heating and is warming up to 90 DEG C of reaction 6.5h, be down to 25 DEG C after reaction terminates and be that the concentrated hydrochloric acid of 36% is to pH=1 ~ 2 with massfraction, subsequent filtration, filter cake through washing, ethanol washes, drying step obtains 4,5-bis-(1H-5-tetrazyl)-1,2,3-triazole 9.85g, yield 96.1%, purity 98.7%.
Claims (2)
1. the synthetic method of one kind 4,5-bis-(1H-5-tetrazyl)-1,2,3-triazoles, 4,5-bis-(1H-5-tetrazyl)-1,2,3-triazoles structural formula is as shown in (I):
With 4, 5-dicyano-1, 2, 3-triazole is raw material, its structural formula is as shown in (II), comprise the following steps: under stirring, temperature 10 DEG C ~ 30 DEG C, by zinc chloride and 4, 5-dicyano-1, 2, 3-triazole is added to the water, add sodiumazide more in batches, add post-heating and be warming up to 85 DEG C ~ 100 DEG C reaction 3.5h ~ 6.5h, be down to 25 DEG C after reaction terminates and be that the concentrated hydrochloric acid of 36% is to pH=1 ~ 2 with massfraction, subsequent filtration, filter cake is through washing, ethanol is washed, dry, obtain 4, 5-bis-(1H-5-tetrazyl)-1, 2, 3-triazole, wherein zinc chloride and 4, 5-dicyano-1, 2, the mol ratio of 3-triazole is 1:0.5 ~ 2.0, 4, 5-dicyano-1, 2, the mol ratio of 3-triazole and sodiumazide is 1:2.0 ~ 4.0, 4, 5-dicyano-1, 2, the mol ratio of 3-triazole and water is 1:250 ~ 350.
2. according to claim 14, 5-bis-(1H-5-tetrazyl)-1, 2, the synthetic method of 3-triazole, comprise the following steps: under stirring, temperature 25 DEG C, by 6.82g (50mmol) zinc chloride and 6.00g (50mmol) 4, 5-dicyano-1, 2, 3-triazole joins in 250mL water, add 9.75g (150mmol) sodiumazide more in batches, add post-heating and be warming up to 95 DEG C of reaction 4.5h, be down to 25 DEG C after reaction terminates and be that the concentrated hydrochloric acid of 36% is to pH=1 ~ 2 with massfraction, subsequent filtration, filter cake is through washing, ethanol is washed, dry, obtain 4, 5-bis-(1H-5-tetrazyl)-1, 2, 3-triazole, wherein zinc chloride and 4, 5-dicyano-1, 2, the mol ratio of 3-triazole is 1:1, 4, 5-dicyano-1, 2, the mol ratio of 3-triazole and sodiumazide is 1:3, 4, 5-dicyano-1, 2, the mol ratio of 3-triazole and water is 1:278.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106045981A (en) * | 2016-08-12 | 2016-10-26 | 中国工程物理研究院化工材料研究所 | Preparation method for hectogram-scale energy-containing 4,5-di(tetrazolyl)triazole organic compound |
| CN114644601A (en) * | 2020-12-17 | 2022-06-21 | 南京理工大学 | High nitrogen compound and synthesis method thereof |
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| CN102993114A (en) * | 2012-10-11 | 2013-03-27 | 南通市华峰化工有限责任公司 | Method for producing 1H-tetrazole-5-acetic acid |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106045981A (en) * | 2016-08-12 | 2016-10-26 | 中国工程物理研究院化工材料研究所 | Preparation method for hectogram-scale energy-containing 4,5-di(tetrazolyl)triazole organic compound |
| CN114644601A (en) * | 2020-12-17 | 2022-06-21 | 南京理工大学 | High nitrogen compound and synthesis method thereof |
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