CN106084100A - A kind of preparation method of polyethylene tetrazolium - Google Patents
A kind of preparation method of polyethylene tetrazolium Download PDFInfo
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Abstract
The present invention relates to the preparation method of a kind of polyethylene tetrazolium, belong to polymer synthesis techniques field.The method step is as follows: the most successively by the mixed solution of polyacrylonitrile, ammonium chloride, Hydrazoic acid,sodium salt addition water and DMF, be then heated to 100～150 DEG C, the lower back flow reaction 4～7h of stirring；In reacted mixed solution, add dilute hydrochloric acid solution, stir and separate out completely to white precipitate, the precipitation of precipitation is washed with water and is dried, obtains polyethylene tetrazolium.The method of the invention avoids intermediate product generation jelly deposited phenomenon, beneficially uniform stirring in preparation process, the carrying out of the heat and mass transport in promotion course of reaction；The method technique is simple, and reaction condition is gentle, and product yield is high.
Description
Technical field
The present invention relates to the preparation method of a kind of polyethylene tetrazolium, belong to polymer synthesis techniques field.
Background technology
Polyethylene tetrazolium is that a kind of nitrogen content is high, sensitivity is low, the high energy binding agent of good security, at gas-forming agent, fire
The fields such as arrow propellant, pyrotechnic composition have wide application.The main preparation methods of polyethylene tetrazolium is that polyacrylonitrile is with folded at present
[3+2] cyclization reaction method of nitride, the method has cyclization efficiency height, product yield advantages of higher.Li upstarts etc. are published in
Article " Resultful synthesis of on " reactive&functional polymers "
Polyvinyltetrazole from polyacrylonitrile " describe and with polyacrylonitrile, Hydrazoic acid,sodium salt and ammonium chloride be
Raw material, with the method that DMF (DMF) is solvent synthesizing polyethylene tetrazolium, but the method is in building-up process
It is attended by jelly natural sedimentation phenomenon, is unfavorable for stirring and mass-and heat-transfer.United States Patent (USP) US3096312 describes with polypropylene
Nitrile or its copolymer and Hydrazoic acid,sodium salt are raw material, with ammonium chloride as catalyst, by annulation by azido group and itrile group ring
Change the method forming tetrazole ring, with DMF as solvent in this patent, building-up process exists jelly deposited phenomenon voluntarily, and
Due to polymer different solubility in DMF, the form causing product is the most different.United States Patent (USP) US7776169 describes
With polyacrylonitrile and Hydrazoic acid,sodium salt as raw material, with zinc bromide as catalyst, by height in the aqueous solution containing surfactant
The method of platen press synthesizing polyethylene tetrazolium, the method do not uses organic solvent, it is to avoid organic solvent in storage, use and reclaim
Present in potential safety hazard and injury that environment is likely to result in, but this synthesis technique equipment is complicated, and technique needs to use high temperature
And high pressure, condition is harsh, and scale of investment is bigger.
Summary of the invention
For defect present in prior art, it is an object of the invention to provide the preparation side of a kind of polyethylene tetrazolium
Method, the method uses the mixed solution of water and DMF as reaction solution, it is to avoid intermediate product precipitates, and is conducive to uniformly stirring
Mix, promote the carrying out of heat and mass transport in course of reaction；The method technique is simple, and product yield is high.
It is an object of the invention to be achieved through the following technical solutions.
A kind of preparation method of polyethylene tetrazolium, specifically comprising the following steps that successively successively by polypropylene of described preparation method
Nitrile, ammonium chloride, Hydrazoic acid,sodium salt add in the mixed solution of water and DMF, are then heated to 100～150 DEG C, the lower back flow reaction of stirring
4～7h；In reacted mixed solution, add dilute hydrochloric acid solution, stir and separate out precipitation that is complete, that will separate out to white precipitate
Wash with water and be dried, obtain polyethylene tetrazolium；
Wherein, water is 1～3:4 with the volume ratio of DMF, and the concentration in DMF of the itrile group in polyacrylonitrile is 1～3mol/
L, the mol ratio of the itrile group in polyacrylonitrile and Hydrazoic acid,sodium salt is 1:1～1.5, the mol ratio of ammonium chloride and Hydrazoic acid,sodium salt be 1～
2:1；Described dilute hydrochloric acid solution is the aqueous hydrochloric acid solution that concentration is not higher than 1mol/L.
Beneficial effect:
Preparation method of the present invention uses the mixed solution of water and DMF as reaction solution, it is to avoid in preparation process
Intermediate product generation jelly deposited phenomenon, it is the most transparent or semitransparent solution that reaction terminates rear reaction system, favorably
The carrying out of the heat and mass transport in uniform stirring, promotion course of reaction；The method technique is simple, and reaction condition is gentle, product
Yield is high.
Detailed description of the invention
Below in conjunction with detailed description of the invention, the present invention will be further described.
In following example:
Polyacrylonitrile: molecular weight is 8.4 × 104G/mol, Jilin Chemical group of CNPC produces.
Embodiment 1
The mixed solution of 100mL DMF and 50mL distilled water is added in there-necked flask, then it is poly-to be successively sequentially added into 10.6g
Acrylonitrile, 21.4g ammonium chloride, 15.6g Hydrazoic acid,sodium salt, mix homogeneously post-heating to 120 DEG C, reacts 7h, course of reaction under stirring
Middle without Precipitation；Pour in the beaker of 1000mL after reacted mixed solution is cooled down again, then add in beaker
500mL concentration is the aqueous hydrochloric acid solution of 0.5mol/L, stirs to white precipitate precipitation completely；The precipitation distillation washing that will separate out
Wash 3 times, be then placed in the drying baker of 120 DEG C being dried 24h, obtain 19.68g polyethylene tetrazolium.
Polyethylene tetrazolium prepared by this enforcement of 0.243g is dissolved in 25mL DMF solution, adds thymol blue
Ethanol solution be indicator, titrate with the sodium hydroxide solution of 0.5mol/L, to solution by light yellow transfer to light blue
Stopping titration, the volume of titrimetric standard solution consumption is 4.9mL, then be calculated itrile group and change into the conversion ratio of tetrazol group and be
96.8%.
Embodiment 2
The mixed solution of 100mL DMF and 25mL distilled water is added in there-necked flask, then it is poly-to be successively sequentially added into 10.6g
Acrylonitrile, 21.4g ammonium chloride, 15.6g Hydrazoic acid,sodium salt, mix homogeneously post-heating to 150 DEG C, reacts 7h, course of reaction under stirring
Middle without Precipitation；Pour in the beaker of 1000mL after reacted mixed solution is cooled down again, then add in beaker
400mL concentration is the aqueous hydrochloric acid solution of 0.7mol/L, stirs to white precipitate precipitation completely；The precipitation distillation washing that will separate out
Wash 3 times, be then placed in the drying baker of 120 DEG C being dried 24h, obtain 21.47g polyethylene tetrazolium.
Polyethylene tetrazolium prepared by this enforcement of 0.192g is dissolved in 25mL DMF solution, adds thymol blue
Ethanol solution be indicator, titrate with the sodium hydroxide solution of 0.5mol/L, to solution by light yellow transfer to light blue
Stopping titration, the volume of titrimetric standard solution consumption is 3.70mL, then be calculated itrile group and change into the conversion ratio of tetrazol group
It is 92.5%.
Embodiment 3
The mixed solution of 100mL DMF and 75mL distilled water is added in there-necked flask, then it is poly-to be successively sequentially added into 10.6g
Acrylonitrile, 21.4g ammonium chloride, 15.6g Hydrazoic acid,sodium salt, mix homogeneously post-heating to 105 DEG C, reacts 7h, course of reaction under stirring
Middle without Precipitation；Pour in the beaker of 2000mL after reacted mixed solution is cooled down again, then add in beaker
800mL concentration is the aqueous hydrochloric acid solution of 0.3mol/L, stirs to white precipitate precipitation completely；The precipitation distillation washing that will separate out
Wash 3 times, be then placed in the drying baker of 120 DEG C being dried 24h, obtain 21.11g polyethylene tetrazolium.
Polyethylene tetrazolium prepared by this enforcement of 0.214g is dissolved in 25mL DMF solution, adds thymol blue
Ethanol solution be indicator, titrate with the sodium hydroxide solution of 0.5mol/L, to solution by light yellow transfer to light blue
Stopping titration, the volume of titrimetric standard solution consumption is 4.20mL, then be calculated itrile group and change into the conversion ratio of tetrazol group
It is 94.7%.
Embodiment 4
The mixed solution of 100mL DMF and 50mL distilled water is added in there-necked flask, then it is poly-to be successively sequentially added into 10.6g
Acrylonitrile, 21.4g ammonium chloride, 15.6g Hydrazoic acid,sodium salt, mix homogeneously post-heating to 130 DEG C, reacts 4h, course of reaction under stirring
Middle without Precipitation；Pour in the beaker of 2000mL after reacted mixed solution is cooled down again, then add in beaker
1500mL concentration is the aqueous hydrochloric acid solution of 0.2mol/L, stirs to white precipitate precipitation completely；By the precipitation distilled water of precipitation
Wash 3 times, be then placed in the drying baker of 120 DEG C being dried 24h, obtain 19.95g polyethylene tetrazolium.
Polyethylene tetrazolium prepared by this enforcement of 0.191g is dissolved in 25ml DMF solution, adds thymol blue
Ethanol solution be indicator, titrate with the sodium hydroxide solution of 0.5mol/L, to solution by light yellow transfer to light blue
Stopping titration, the volume of titrimetric standard solution consumption is 3.62ml, then be calculated itrile group and change into the conversion ratio of tetrazol group
It is 90.5%.
Embodiment 5
The mixed solution of 100mL DMF and 50mL distilled water is added in there-necked flask, then it is poly-to be successively sequentially added into 10.6g
Acrylonitrile, 21.4g ammonium chloride, 15.6g Hydrazoic acid,sodium salt, mix homogeneously post-heating to 130 DEG C, reacts 5h, course of reaction under stirring
Middle without Precipitation；Pour in the beaker of 1000mL after reacted mixed solution is cooled down again, then add in beaker
500mL concentration is the aqueous hydrochloric acid solution of 0.6mol/L, stirs to white precipitate precipitation completely；The precipitation distillation washing that will separate out
Wash 3 times, be then placed in the drying baker of 120 DEG C being dried 24h, obtain 21.06g polyethylene tetrazolium.
Polyethylene tetrazolium prepared by this enforcement of 0.177g is dissolved in 25ml DMF solution, adds thymol blue
Ethanol solution be indicator, titrate with the sodium hydroxide solution of 0.5mol/L, to solution by light yellow transfer to light blue
Stopping titration, the volume of titrimetric standard solution consumption is 2.65ml, then be calculated itrile group and change into the conversion ratio of tetrazol group
It is 94.4%.
Embodiment 6
The mixed solution of 100mL DMF and 50mL distilled water is added in there-necked flask, then it is poly-to be successively sequentially added into 10.6g
Acrylonitrile, 21.4g ammonium chloride, 15.6g Hydrazoic acid,sodium salt, mix homogeneously post-heating to 110 DEG C, lower back flow reaction 6h of stirring, reaction
During without Precipitation；Pour into again after reacted mixed solution is cooled down in the beaker of 1000mL, then add in beaker
Enter the aqueous hydrochloric acid solution that 500mL concentration is 0.7mol/L, stir to white precipitate precipitation completely；By the precipitation distilled water of precipitation
Wash 3 times, be then placed in the drying baker of 120 DEG C being dried 24h, obtain 19.68g polyethylene tetrazolium.
Polyethylene tetrazolium prepared by this enforcement of 0.201g is dissolved in 25mL DMF solution, adds thymol blue
Ethanol solution be indicator, titrate with the sodium hydroxide solution of 0.5mol/L, to solution by light yellow transfer to light blue
Stopping titration, the volume of titrimetric standard solution consumption is 3.84mL, then be calculated itrile group and change into the conversion ratio of tetrazol group
It is 91.7%.
Embodiment 7
The mixed solution of 100mL DMF and 50mL distilled water is added in there-necked flask, then it is poly-to be successively sequentially added into 10.6g
Acrylonitrile, 16.05g ammonium chloride, 15.6g Hydrazoic acid,sodium salt, mix homogeneously post-heating to 120 DEG C, lower back flow reaction 5h of stirring, reaction
During without Precipitation；Pour into again after reacted mixed solution is cooled down in the beaker of 1000mL, then add in beaker
Enter the aqueous hydrochloric acid solution that 500mL concentration is 0.7mol/L, stir to white precipitate precipitation completely；By the precipitation distilled water of precipitation
Wash 3 times, be then placed in the drying baker of 120 DEG C being dried 24h, obtain 19.50g polyethylene tetrazolium.
Polyethylene tetrazolium prepared by this enforcement of 0.206g is dissolved in 25mL DMF solution, adds thymol blue
Ethanol solution be indicator, titrate with the sodium hydroxide solution of 0.5mol/L, to solution by light yellow transfer to light blue
Stopping titration, the volume of titrimetric standard solution consumption is 4.08mL, then be calculated itrile group and change into the conversion ratio of tetrazol group
It is 92.7%.
Embodiment 8
The mixed solution of 100mL DMF and 50mL distilled water is added in there-necked flask, then it is poly-to be successively sequentially added into 10.6g
Acrylonitrile, 12.84g ammonium chloride, 15.6g Hydrazoic acid,sodium salt, mix homogeneously post-heating to 120 DEG C, reacts 5h, course of reaction under stirring
Middle without Precipitation；Pour in the beaker of 1000mL after reacted mixed solution is cooled down again, then add in beaker
600mL concentration is the aqueous hydrochloric acid solution of 0.4mol/L, stirs to white precipitate precipitation completely；The precipitation distillation washing that will separate out
Wash 3 times, be then placed in the drying baker of 120 DEG C being dried 24h, obtain 18.73g polyethylene tetrazolium.
Polyethylene tetrazolium prepared by this enforcement of 0.252g is dissolved in 25mL DMF solution, adds thymol blue
Ethanol solution be indicator, titrate with the sodium hydroxide solution of 0.5mol/L, to solution by light yellow transfer to light blue
Stopping titration, the volume of titrimetric standard solution consumption is 5.10mL, then be calculated itrile group and change into the conversion ratio of tetrazol group
It is 92.8%.
Embodiment 9
The mixed solution of 100mL DMF and 50mL distilled water is added in there-necked flask, then it is poly-to be successively sequentially added into 10.6g
Acrylonitrile, 12.84g ammonium chloride, 14.30g Hydrazoic acid,sodium salt, mix homogeneously post-heating to 110 DEG C, reacts 7h under stirring, reacted
Without Precipitation in journey；Pour in the beaker of 1000mL after reacted mixed solution is cooled down again, then add in beaker
400mL concentration is the aqueous hydrochloric acid solution of 0.7mol/L, stirs to white precipitate precipitation completely；The precipitation distillation washing that will separate out
Wash 3 times, be then placed in the drying baker of 120 DEG C being dried 24h, obtain 19.75g polyethylene tetrazolium.
Polyethylene tetrazolium prepared by this enforcement of 0.245g is dissolved in 25mL DMF solution, adds thymol blue
Ethanol solution be indicator, titrate with the sodium hydroxide solution of 0.5mol/L, to solution by light yellow transfer to light blue
Stopping titration, the volume of titrimetric standard solution consumption is 4.95mL, then be calculated itrile group and change into the conversion ratio of tetrazol group
It is 96.9%.
Embodiment 10
The mixed solution of 100mL DMF and 50mL distilled water is added in there-necked flask, then it is poly-to be successively sequentially added into 10.6g
Acrylonitrile, 12.84g ammonium chloride, 13.00g Hydrazoic acid,sodium salt, mix homogeneously post-heating to 120 DEG C, reacts 7h under stirring, reacted
Without Precipitation in journey；Pour in the beaker of 1000mL after reacted mixed solution is cooled down again, then add in beaker
800mL concentration is the aqueous hydrochloric acid solution of 0.3mol/L, stirs to white precipitate precipitation completely；The precipitation distillation washing that will separate out
Wash 3 times, be then placed in the drying baker of 120 DEG C being dried 24h, obtain 18.83g polyethylene tetrazolium.
Polyethylene tetrazolium prepared by this enforcement of 0.210g is dissolved in 25mL DMF solution, adds thymol blue
Ethanol solution be indicator, titrate with the sodium hydroxide solution of 0.5mol/L, to solution by light yellow transfer to light blue
Stopping titration, the volume of titrimetric standard solution consumption is 4.15mL, then be calculated itrile group and change into the conversion ratio of tetrazol group
It is 94.8%.
Embodiment 11
The mixed solution of 100mL DMF and 50mL distilled water is added in there-necked flask, is more successively sequentially added into 15.90g
Polyacrylonitrile, 32.10g ammonium chloride, 23.40g Hydrazoic acid,sodium salt, mix homogeneously post-heating to 150 DEG C, reacts 7h, reaction under stirring
During without Precipitation；Pour into again after reacted mixed solution is cooled down in the beaker of 1000mL, then add in beaker
Enter the aqueous hydrochloric acid solution that 500mL concentration is 0.5mol/L, stir to white precipitate precipitation completely；By the precipitation distilled water of precipitation
Wash 3 times, be then placed in the drying baker of 120 DEG C being dried 24h, obtain 35.80g polyethylene tetrazolium.
Polyethylene tetrazolium prepared by this enforcement of 0.221g is dissolved in 25mL DMF solution, adds thymol blue
Ethanol solution be indicator, titrate with the sodium hydroxide solution of 0.5mol/L, to solution by light yellow transfer to light blue
Stopping titration, the volume of titrimetric standard solution consumption is 4.22mL, then be calculated itrile group and change into the conversion ratio of tetrazol group
It is 91.6%.
Embodiment 12
The mixed solution of 100mL DMF and 50mL distilled water is added in there-necked flask, then it is poly-to be successively sequentially added into 5.3g
Acrylonitrile, 10.7g ammonium chloride, 7.8g Hydrazoic acid,sodium salt, mix homogeneously post-heating to 100 DEG C, reacts 7h, in course of reaction under stirring
Without Precipitation；Pour in the beaker of 1000mL after reacted mixed solution is cooled down again, in beaker, then add 500mL
Concentration is the aqueous hydrochloric acid solution of 0.5mol/L, stirs to white precipitate precipitation completely；The precipitation distilled water wash 3 that will separate out
Secondary, it is then placed in the drying baker of 120 DEG C being dried 24h, obtains 11.25g polyethylene tetrazolium.
Polyethylene tetrazolium prepared by this enforcement of 0.171g is dissolved in 25mL DMF solution, adds thymol blue
Ethanol solution be indicator, titrate with the sodium hydroxide solution of 0.5mol/L, to solution by light yellow transfer to light blue
Stopping titration, the volume of titrimetric standard solution consumption is 2.40mL, then be calculated itrile group and change into the conversion ratio of tetrazol group
It is 89.6%.
In sum, these are only presently preferred embodiments of the present invention, be not intended to limit protection scope of the present invention.
All within the spirit and principles in the present invention, any modification, equivalent substitution and improvement etc. made, should be included in the present invention's
Within protection domain.
Claims (1)
1. the preparation method of a polyethylene tetrazolium, it is characterised in that: specifically comprising the following steps that the most successively of described preparation method
By in the mixed solution of polyacrylonitrile, ammonium chloride, Hydrazoic acid,sodium salt addition water and DMF, it is then heated to 100～150 DEG C, under stirring
Back flow reaction 4～7h；In reacted mixed solution, add dilute hydrochloric acid solution, stir to white precipitate precipitation completely, will analysis
The precipitation gone out washes with water and is dried, and obtains polyethylene tetrazolium；
Wherein, water is 1～3:4 with the volume ratio of DMF, and the concentration in DMF of the itrile group in polyacrylonitrile is 1～3mol/L, poly-
Itrile group in acrylonitrile is 1:1～1.5 with the mol ratio of Hydrazoic acid,sodium salt, and ammonium chloride is 1～2:1 with the mol ratio of Hydrazoic acid,sodium salt,
Described dilute hydrochloric acid solution is the aqueous hydrochloric acid solution that concentration is not higher than 1mol/L.
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Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US3096312A (en) * | 1960-08-26 | 1963-07-02 | Ronald A Henry | Polymers and copolymers of 5-vinyltetrazole |
| RU1781232C (en) * | 1990-08-09 | 1992-12-15 | Институт Органической Химии Ан Армсср | Process for producing poly-5-vinyltetrazole |
| US20070040167A1 (en) * | 2005-06-01 | 2007-02-22 | Miller Cory G | Water-based synthesis of poly(tetrazoles) and articles formed therefrom |
| WO2008059318A2 (en) * | 2005-07-31 | 2008-05-22 | Automotive Systems Laboratory, Inc. | Water-based synthesis of poly(tetrazoles) and articles formed therefrom |
| RU2423389C1 (en) * | 2010-07-08 | 2011-07-10 | Государственное образовательное учреждение высшего профессионального образования Иркутский государственный университет | Method of producing tetrazole-containing polymers |
| RU2560726C1 (en) * | 2014-07-30 | 2015-08-20 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Иркутский государственный университет" | Method of obtaining tetrazole-containing paired polymers |
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2016
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| Publication number | Priority date | Publication date | Assignee | Title |
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| US3096312A (en) * | 1960-08-26 | 1963-07-02 | Ronald A Henry | Polymers and copolymers of 5-vinyltetrazole |
| RU1781232C (en) * | 1990-08-09 | 1992-12-15 | Институт Органической Химии Ан Армсср | Process for producing poly-5-vinyltetrazole |
| US20070040167A1 (en) * | 2005-06-01 | 2007-02-22 | Miller Cory G | Water-based synthesis of poly(tetrazoles) and articles formed therefrom |
| WO2008059318A2 (en) * | 2005-07-31 | 2008-05-22 | Automotive Systems Laboratory, Inc. | Water-based synthesis of poly(tetrazoles) and articles formed therefrom |
| RU2423389C1 (en) * | 2010-07-08 | 2011-07-10 | Государственное образовательное учреждение высшего профессионального образования Иркутский государственный университет | Method of producing tetrazole-containing polymers |
| RU2560726C1 (en) * | 2014-07-30 | 2015-08-20 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Иркутский государственный университет" | Method of obtaining tetrazole-containing paired polymers |
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| 哈恒欣等: "聚-5-乙烯四唑的合成与性能研究", 《含能材料》 * |
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