CN106045981A - Preparation method for hectogram-scale energy-containing 4,5-di(tetrazolyl)triazole organic compound - Google Patents
Preparation method for hectogram-scale energy-containing 4,5-di(tetrazolyl)triazole organic compound Download PDFInfo
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Abstract
The invention discloses a preparation method for a hectogram-scale energy-containing 4,5-di(tetrazolyl)triazole organic compound. The preparation method comprises the following steps: (1) subjecting 4,5-dicyanotriazole and sodium azide to high-temperature reflux so as to prepare 4,5-di(tetrazolyl)triazole; (2) extracting 4,5-di(tetrazolyl)triazole from a reaction solution; and (3) carrying out aftertreatment. The hectogram-scale energy-containing 4,5-di(tetrazolyl)triazole organic compound prepared in the invention has good safety performance, small granularity and uniform particle size distribution and can be used as a component of an explosive, gunpowder or propellant; and the preparation method is simple in process flow, convenient to operate, mild in reaction conditions, good in security and high in product quality.
Description
Technical field
The present invention relates to energetic material field, be specifically related to a kind of hectogram level 4,5-bis-tetrazolium triazole is containing energy organic compound
Preparation method.
Background technology
Energetic material is the supporting body of modern weapons strength, in order to realize the needs of modern national defense cause and development in science and technology,
Design synthesis has higher energy density, more preferable explosion property, lower sensitivity and preferably chemical stability and heat are steady
Compound becomes the main target developing field into energetic material qualitatively.The energy density of traditional energetic material and safety
Can be opposition, contradiction, it tends to be difficult to obtain both perfect unities, such as trinitrotoluene (TNT), RDX (RDX), three ammonia
The straight chain compounds such as the ring-type energy-containing compounds such as base trinitrobenzene (TATB) and pentaerythritol tetranitrate (PETN) all exist
Deficiency in some structures and performance.
In recent years, high nitrogen compound receives much concern in the exploitation of novel energetic material.High-nitrogen energetic materials itself is general
All over having the positive enthalpy of formation that comparison is high, in its molecule, the low hydrocarbon architectural feature of high nitrogen is allowed to more easily reach oxygen balance and have
Higher unit mass gas production, and great majority do not contain nitro functions, sensitivity than relatively low, heat stability is relatively good, with
Time combustion product also with eco-friendly N2It is main.As a class material important in high nitrogen compound, tetrazolium nitrogen heterocycles spreads out
Biology has obtained studying widely, is synthesized 4 obtained the most recently, 5-bis-tetrazolium triazole molecule (Chem.Eur.J.2016,
22,1,768 1778.) in, nitrogen content is up to 75%, and heat is analyzed and shown its better heat stability, and discharge quantity is relatively big, calculates and shows it
Every explosive nature thereof is the most excellent, is the energy-containing compound of a kind of novelty.In consideration of it, the present invention uses simple and practical method to become
Merit is prepared for hectogram magnitude 4,5-bis-tetrazolium triazole, is expected in method application such as main explosive and propellants.
Currently, with respect to the 4 of hectogram magnitude, the preparation of 5-bis-tetrazolium triazole is reported without open source literature.
Summary of the invention
[solving the technical problem that]
Present invention aim to address above-mentioned prior art problem, it is provided that a kind of hectogram level 4,5-bis-tetrazolium triazole is containing having
The preparation method of machine compound.This preparation method is based on being 4,5-dicyano triazole and nitrine tube-nursery hectogram level 4,5-bis-or four
Azoles triazole is containing the preparation method of energy organic compound.This preparation method has preferably in green detonating charge and high explosive
Application prospect.
[technical scheme]
In order to reach above-mentioned technique effect, the present invention takes techniques below scheme:
A kind of hectogram level 4,5-bis-tetrazolium triazole is containing the preparation method of energy organic compound, and it comprises the following steps:
(1) a certain amount of 4 are weighed, 5-dicyano triazole, nitrine reagent and zinc halide salts, after mix homogeneously, mixture is turned
Move in the flask with condensation reflux unit, after adding solvent and isopropanol in flask, stir, be then heated to anti-
Answer liquid to reflux, maintain the reflux for 48～52h；
(2) reactant liquor after backflow being cooled to room temperature, then with after base extraction 0.5～3h, filter, filtrate continues to use
Acid solution processes 0.5～3h, obtains filtering residue；Filtering residue repeats the base extraction of this step and acid solution processes at least one times, obtains crude product
4,5-bis-tetrazolium triazole；
(3) crude product 4,5-bis-tetrazolium triazole, after dehydrated alcohol rinses and drains, is vacuum dried, obtains described hundred
Gram level 4,5-bis-tetrazolium triazole is containing can organic compound；
The molecular structural formula of described 4,5-dicyano triazole is:
The molecular structural formula of 4,5-bis-tetrazolium triazole is:
According to the present invention further technical scheme, in step (1), described nitrine reagent is nitrine sodium salt, nitrine
Potassium salt or TMSA.
According to the present invention further technical scheme, in step (1), described zinc halide salts is zinc bromide or zinc chloride
Salt.
According to the present invention further technical scheme, in step (1), described solvent is deionized water, oxolane
Or acetonitrile.
According to the present invention further technical scheme, in step (2), described alkali liquor is that the sodium hydroxide of 1M is water-soluble
Liquid, described acid solution is the aqueous hydrochloric acid solution of 1M；The reacting liquid pH value controlling base extraction is 13～14, after controlling acid solution process
In the range of the reacting liquid pH value obtained is 2～3.
According to the present invention further technical scheme, in step (3), described vacuum drying refer to temperature be 40～
Carry out under the vacuum environment of 60 DEG C is dried.
According to the present invention further technical scheme, described 4,5-dicyano triazole in terms of cyano group, nitrine reagent
In terms of azido group, its 4,5-dicyano triazole is 1:3 with the ratio of the amount of the material of nitrine reagent；Described nitrine reagent and halogenation
The ratio of the amount of the material of zinc salt is 1:1.
According to the present invention further technical scheme, when solvent is water, described solvent with the volume ratio of isopropanol is
5:1；When solvent is oxolane or acetonitrile, described solvent is 26:1 with the volume ratio of isopropanol.
Will be described in detail the present invention below.
In the present invention, described zinc halide salts uses as catalyst.Mainly 4,5-dicyano triazole and nitrine
Reaction between reagent.The present invention points out by 4,5-dicyano triazole, nitrine reagent and catalyst mix after be transferred to
In the flask of condensation reflux unit, wherein, the reaction of 4,5-dicyano triazoles and nitrine reagent is that therefore back flow reaction must pacify
Dress condensing unit avoids reaction solution to evaporate completely.
In the present invention, add solvent primarily serves the purpose of reactant 4,5-dicyano triazole, nitrine reagent and zinc halide salts
A kind of good reaction environment is provided；The purpose of addition isopropanol and stirring is for reaction system and preferably disperses.Favorably
Reaction between reactant；The optimum degree of stirring is to can see that to produce whirlpool in the middle of reactant liquor, and visible reactant liquor
Surface produces ripple due to stirring.Stirring the most acutely can make reactant liquor splash, and is unfavorable for reaction and the stability of reactant.
In step (3), by crude product 4, it is to remove isopropanol and that 5-bis-tetrazolium triazole is rinsed through dehydrated alcohol
A little byproducts of reaction, vacuum drying main purpose is to remove the volatilizable material such as water and dehydrated alcohol, carrying further
The purity of high product.
[beneficial effect]
The present invention compared with prior art, has a following beneficial effect:
The hectogram level 4 that the present invention prepares, 5-bis-tetrazolium triazole organic compound has good security performance, simultaneously
Product granularity is less, even particle size distribution, can be as the composition of explosive, gunpowder and propellant；The preparation side of the present invention
Method technological process is simple, easy to operate, and reaction condition is gentle, and safety is good, and product quality is high.
Accompanying drawing explanation
Fig. 1 is the TG-DSC figure of the 4,5-bis-tetrazolium triazole that preparation method of the present invention prepares.
Detailed description of the invention
Below in conjunction with embodiments of the invention, the invention will be further elaborated.
Embodiment 1:
(1) the 4,5-dicyano triazole of 70g, 149g TMSA and the 130g bromine as catalyst are weighed
Change zinc salt, be transferred in the 5L jacket reactor with condensation reflux unit cleaning, in reactor, add the tetrahydrochysene furan of 1.3L
Mutter and 50ml isopropanol use mechanical agitation oar to stir, stirring speed 500～800rpm.Reacting by heating liquid starts back to 65 DEG C
Stream, keeps stable reaction 48 hours.
(2), after reactant liquor is cooled to room temperature, the NaOH base extraction first by 800ml 1M makes to react in suspension
4,5-bis-tetrazolium triazole is dissolved, and filters out insoluble matter and impurity, then processes filtrate by the HCl acid solution of about 500ml 1M and makes
Being dissolved in therein 4,5-bis-tetrazolium triazole separates out, and filters insoluble matter, reuses acid & alkali liquid and repeats process once, obtains thick
Product 4,5-bis-tetrazolium triazole.
(3) crude product 4,5-bis-tetrazolium triazole uses 100ml dehydrated alcohol to rinse and drain, is placed in vacuum drying oven and is heated to
40 DEG C～60 DEG C are dried purification.I.e. obtain desired end product 4,5-bis-tetrazolium triazole.
Embodiment 2
(1) the 4,5-dicyano triazole of 70g, 149g TMSA and the 80g chlorine as catalyst are weighed
Change zinc salt, be transferred in the 5L jacket reactor with condensation reflux unit cleaning, in reactor, add the tetrahydrochysene furan of 1.3L
Mutter and 50ml isopropanol use mechanical agitation oar to stir, stirring speed 500～800rpm.Reacting by heating liquid starts back to 65 DEG C
Stream, keeps stable reaction 48 hours.
(2), after reactant liquor is cooled to room temperature, the NaOH base extraction first by 800ml 1M makes to react in suspension
4,5-bis-tetrazolium triazole is dissolved, and filters out insoluble matter and impurity, then processes filtrate by the HCl acid solution of about 500ml 1M and makes
Being dissolved in therein 4,5-bis-tetrazolium triazole separates out, and filters insoluble matter, reuses acid & alkali liquid and repeats process once, obtains thick
Product 4,5-bis-tetrazolium triazole.
(3) crude product 4,5-bis-tetrazolium triazole uses 100ml dehydrated alcohol to rinse and drain, is placed in vacuum drying oven and is heated to
40 DEG C～60 DEG C are dried purification.I.e. obtain desired end product 4,5-bis-tetrazolium triazole.
Embodiment 3
(1) the 4,5-dicyano triazole of 70g, 149g TMSA and the 130g bromine as catalyst are weighed
Change zinc salt, be transferred to in the clean 5L jacket reactor of condensation reflux unit, add in reactor 1.3L acetonitrile and
50ml isopropanol also uses mechanical agitation oar to stir, stirring speed 500～800rpm.Reacting by heating liquid starts backflow to 81 DEG C, protects
Hold stable reaction 48 hours.
(2), after reactant liquor is cooled to room temperature, the NaOH base extraction first by 800ml 1M makes to react in suspension
4,5-bis-tetrazolium triazole is dissolved, and filters out insoluble matter and impurity, then processes filtrate by the HCl acid solution of about 500ml 1M and makes
Being dissolved in therein 4,5-bis-tetrazolium triazole separates out, and filters insoluble matter, reuses acid & alkali liquid and repeats process once, obtains thick
Product 4,5-bis-tetrazolium triazole.
(3) crude product 4,5-bis-tetrazolium triazole uses 100ml dehydrated alcohol to rinse and drain, is placed in vacuum drying oven and is heated to
40 DEG C～60 DEG C are dried purification.I.e. obtain desired end product 4,5-bis-tetrazolium triazole.
Embodiment 4
(1) the 4,5-dicyano triazole of 70g, 149g TMSA and the 80g chlorine as catalyst are weighed
Change zinc salt, be transferred to in the clean 5L jacket reactor of condensation reflux unit, add in reactor 1.3L acetonitrile and
50ml isopropanol also uses mechanical agitation oar to stir, stirring speed 500～800rpm.Reacting by heating liquid starts backflow to 65 DEG C, protects
Hold stable reaction 48 hours.
(2), after reactant liquor is cooled to room temperature, the NaOH base extraction first by 800ml 1M makes to react in suspension
4,5-bis-tetrazolium triazole is dissolved, and filters out insoluble matter and impurity, then processes filtrate by the HCl acid solution of about 500ml 1M and makes
Being dissolved in therein 4,5-bis-tetrazolium triazole separates out, and filters insoluble matter, reuses acid & alkali liquid and repeats process once, obtains thick
Product 4,5-bis-tetrazolium triazole.
(3) crude product 4,5-bis-tetrazolium triazole uses 100ml dehydrated alcohol to rinse and drain, is placed in vacuum drying oven and is heated to
40 DEG C～60 DEG C are dried purification.I.e. obtain desired end product 4,5-bis-tetrazolium triazole.
Embodiment 5
(1) the 4 of 70g are weighed, 5-dicyano triazole, 84.5g nitrine sodium salt and the 130g bromination zinc salt as catalyst,
Be transferred to in the clean 5L jacket reactor of condensation reflux unit, add in reactor 1.5L deionized water and
100ml isopropanol also uses mechanical agitation oar to stir, stir speed (S.S.) 500～800rpm.Reacting by heating liquid starts back to 100 DEG C
Stream, keeps stable reaction 48 hours.
(2), after reactant liquor is cooled to room temperature, the NaOH base extraction first by 800ml 1M makes to react in suspension
4,5-bis-tetrazolium triazole is dissolved, and filters out insoluble matter and impurity, then processes filtrate by the HCl acid solution of about 500ml 1M and makes
Being dissolved in therein 4,5-bis-tetrazolium triazole separates out, and filters insoluble matter, reuses acid & alkali liquid and repeats process once, obtains thick
Product 4,5-bis-tetrazolium triazole.
(3) crude product 4,5-bis-tetrazolium triazole uses 100ml dehydrated alcohol to rinse and drain, is placed in vacuum drying oven and is heated to
40 DEG C～60 DEG C are dried purification.I.e. obtain desired end product 4,5-bis-tetrazolium triazole.
Embodiment 6
(1) the 4 of 70g are weighed, 5-dicyano triazole, 84.5g nitrine sodium salt and the 80g chlorination zinc salt as catalyst,
Be transferred to in the clean 5L jacket reactor of condensation reflux unit, add in reactor 1.5L deionized water and
100ml isopropanol also uses mechanical agitation oar to stir, stir speed (S.S.) 500～800rpm.Reacting by heating liquid starts back to 100 DEG C
Stream, keeps stable reaction 48 hours.
(2), after reactant liquor is cooled to room temperature, the NaOH base extraction first by 800ml 1M makes to react in suspension
4,5-bis-tetrazolium triazole is dissolved, and filters out insoluble matter and impurity, then processes filtrate by the HCl acid solution of about 500ml 1M and makes
Being dissolved in therein 4,5-bis-tetrazolium triazole separates out, and filters insoluble matter, reuses acid & alkali liquid and repeats process once, obtains thick
Product 4,5-bis-tetrazolium triazole.
(3) crude product 4,5-bis-tetrazolium triazole uses 100ml dehydrated alcohol to rinse and drain, is placed in vacuum drying oven and is heated to
40 DEG C～60 DEG C are dried purification.I.e. obtain desired end product 4,5-bis-tetrazolium triazole.
Embodiment 7
(1) the 4 of 70g are weighed, 5-dicyano triazole, 105g nitrine potassium salt and the 130g bromination zinc salt as catalyst,
Be transferred to in the clean 5L jacket reactor of condensation reflux unit, add in reactor 1.5L deionized water and
100ml isopropanol also uses mechanical agitation oar to stir, stir speed (S.S.) 500～800rpm.Reacting by heating liquid starts back to 100 DEG C
Stream, keeps stable reaction 48 hours.
(2), after reactant liquor is cooled to room temperature, the NaOH base extraction first by 800ml 1M makes to react in suspension
4,5-bis-tetrazolium triazole is dissolved, and filters out insoluble matter and impurity, then processes filtrate by the HCl acid solution of about 500ml 1M and makes
Being dissolved in therein 4,5-bis-tetrazolium triazole separates out, and filters insoluble matter, reuses acid & alkali liquid and repeats process once, obtains thick
Product 4,5-bis-tetrazolium triazole.
(3) crude product 4,5-bis-tetrazolium triazole uses 100ml dehydrated alcohol to rinse and drain, is placed in vacuum drying oven and is heated to
40 DEG C～60 DEG C are dried purification.I.e. obtain desired end product 4,5-bis-tetrazolium triazole.
Embodiment 8
(1) the 4 of 70g are weighed, 5-dicyano triazole, 105g nitrine potassium salt and the 80g chlorination zinc salt as catalyst, turn
Move to, in the 5L jacket reactor with condensation reflux unit cleaning, in reactor, add deionized water and the 100ml of 1.5L
Isopropanol also uses mechanical agitation oar to stir, stir speed (S.S.) 500～800rpm.Reacting by heating liquid starts backflow to 100 DEG C, keeps
Stable reaction 48 hours.
(2), after reactant liquor is cooled to room temperature, the NaOH base extraction first by 800ml 1M makes to react in suspension
4,5-bis-tetrazolium triazole is dissolved, and filters out insoluble matter and impurity, then processes filtrate by the HCl acid solution of about 500ml 1M and makes
Being dissolved in therein 4,5-bis-tetrazolium triazole separates out, and filters insoluble matter, reuses acid & alkali liquid and repeats process once, obtains thick
Product 4,5-bis-tetrazolium triazole.
(3) crude product 4,5-bis-tetrazolium triazole uses 100ml dehydrated alcohol to rinse and drain, is placed in vacuum drying oven and is heated to
40 DEG C～60 DEG C are dried purification.I.e. obtain desired end product 4,5-bis-tetrazolium triazole.
The desired end product 4 obtained in above-mentioned 8 embodiments, the TG-DSC figure of 5-bis-tetrazolium triazole is as it is shown in figure 1, thus
Visible, what the preparation method of the present invention prepared contains energy coordination polymer 4, and 5-bis-tetrazolium triazole has good energy and heat
Stability, can be as the composition of explosive, gunpowder and propellant.
Although reference be made herein to invention has been described for the explanatory embodiment of the present invention, and above-described embodiment is only this
Bright preferably embodiment, embodiments of the present invention are also not restricted to the described embodiments, it should be appreciated that people in the art
Member can be designed that a lot of other amendments and embodiment, and these amendments and embodiment will fall in principle disclosed in the present application
Within scope and spirit.
Claims (8)
1. a hectogram level 4,5-bis-tetrazolium triazole is containing the preparation method of energy organic compound, it is characterised in that it includes following step
Rapid:
(1) a certain amount of 4 are weighed, 5-dicyano triazole, nitrine reagent and zinc halide salts, after mix homogeneously, mixture is transferred to
In flask with condensation reflux unit, after adding solvent and isopropanol in flask, stir, be then heated to reactant liquor
Backflow, maintains the reflux for 48～52h；
(2) reactant liquor after backflow being cooled to room temperature, then with after base extraction 0.5～3h, filter, filtrate continues to use acid solution
Process 0.5～3h, obtain filtering residue；Filtering residue repeats the base extraction of this step and acid solution processes at least one times, obtains crude product 4,5-
Two tetrazolium triazoles；
(3) crude product 4,5-bis-tetrazolium triazole, after dehydrated alcohol rinses and drains, is vacuum dried, obtains described hectogram level 4,5-bis-
Tetrazolium triazole is containing energy organic compound；
The molecular structural formula of described 4,5-dicyano triazole is:
The molecular structural formula of 4,5-bis-tetrazolium triazole is:
Hectogram level 4 the most according to claim 1,5-bis-tetrazolium triazole is containing the preparation method of energy organic compound, its feature
Being in step (1), described nitrine reagent is nitrine sodium salt, nitrine potassium salt or TMSA.
Hectogram level 4 the most according to claim 1,5-bis-tetrazolium triazole is containing the preparation method of energy organic compound, its feature
Being in step (1), described zinc halide salts is zinc bromide or chlorination zinc salt.
Hectogram level 4 the most according to claim 1,5-bis-tetrazolium triazole is containing the preparation method of energy organic compound, its feature
Being in step (1), described solvent is deionized water, oxolane or acetonitrile.
Hectogram level 4 the most according to claim 1,5-bis-tetrazolium triazole is containing the preparation method of energy organic compound, its feature
Being in step (2), described alkali liquor is the sodium hydrate aqueous solution of 1M, and described acid solution is the aqueous hydrochloric acid solution of 1M；Control
The reacting liquid pH value of base extraction is 13～14, in the range of the reacting liquid pH value controlling to obtain after acid solution processes is 2～3.
Hectogram level 4 the most according to claim 1,5-bis-tetrazolium triazole is containing the preparation method of energy organic compound, its feature
Being in step (3), described vacuum drying refers to that carry out under the vacuum environment that temperature is 40～60 DEG C is dried.
Hectogram level 4 the most according to claim 1,5-bis-tetrazolium triazole is containing the preparation method of energy organic compound, its feature
Be described 4,5-dicyano triazole in terms of cyano group, nitrine reagent in terms of azido group, its 4,5-dicyano triazole is with folded
The ratio of the amount of the material of nitrogen reagent is 1:3；Described nitrine reagent is 1:1 with the ratio of the amount of the material of zinc halide salts.
Hectogram level 4 the most according to claim 4,5-bis-tetrazolium triazole is containing the preparation method of energy organic compound, its feature
Being when solvent is water, described solvent is 5:1 with the volume ratio of isopropanol；When solvent is oxolane or acetonitrile, described
Solvent is 26:1 with the volume ratio of isopropanol.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN106883424A (en) * | 2017-02-28 | 2017-06-23 | 中国工程物理研究院化工材料研究所 | The alkaline-earth metal containing energy has machine frame and preparation method thereof |
| CN106905539A (en) * | 2017-02-28 | 2017-06-30 | 中国工程物理研究院化工材料研究所 | Metal organic frame containing energy and preparation method thereof |
| CN110606851A (en) * | 2019-10-14 | 2019-12-24 | 中国工程物理研究院化工材料研究所 | Insensitive high-energy energetic compound with excellent thermal stability and preparation method thereof |
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| CN105037330A (en) * | 2015-06-23 | 2015-11-11 | 西安近代化学研究所 | Synthesis method of 4,5-di(1H-5-tetrazol)-1,2,3-triazole |
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106883424A (en) * | 2017-02-28 | 2017-06-23 | 中国工程物理研究院化工材料研究所 | The alkaline-earth metal containing energy has machine frame and preparation method thereof |
| CN106905539A (en) * | 2017-02-28 | 2017-06-30 | 中国工程物理研究院化工材料研究所 | Metal organic frame containing energy and preparation method thereof |
| CN106905539B (en) * | 2017-02-28 | 2019-11-05 | 中国工程物理研究院化工材料研究所 | Metal-organic framework containing energy and preparation method thereof |
| CN106883424B (en) * | 2017-02-28 | 2019-12-24 | 中国工程物理研究院化工材料研究所 | Energetic alkaline earth metal-organic frame and preparation method thereof |
| CN110606851A (en) * | 2019-10-14 | 2019-12-24 | 中国工程物理研究院化工材料研究所 | Insensitive high-energy energetic compound with excellent thermal stability and preparation method thereof |
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Application publication date: 20161026 |