CN103880704A - Azide ester compound, synthetic method and application of compound - Google Patents

Azide ester compound, synthetic method and application of compound Download PDF

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Publication number
CN103880704A
CN103880704A CN201410107027.0A CN201410107027A CN103880704A CN 103880704 A CN103880704 A CN 103880704A CN 201410107027 A CN201410107027 A CN 201410107027A CN 103880704 A CN103880704 A CN 103880704A
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ester compound
nitrine
synthetic method
room temperature
reaction
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周新利
陆春华
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Nanjing University of Science and Technology
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Nanjing University of Science and Technology
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Abstract

The invention discloses an azide ester compound, a synthetic method and an application of the compound. The synthetic method is characterized by setting the molar ratio of trihydroxymethyl nitromethane and chloroacetic acid as 1:(2.5-4.5), adding a catalyst, refluxing, and separating water by a water separator in esterification reaction; in azide reaction, setting the molar ratio of tri(chloracetyloxyl methyl) nitromethane and sodium azide as 1:(2-6), taking a dimethyl sulfoxide aqueous solution as a solvent and tetrabutylammonium bromide as a phase transfer catalyst, stirring at room temperature and slowly heating to 30-70 DEG C to react to obtain a target product. Tri(chloracetyloxyl methyl) nitromethane provided by the invention is the azide ester compound which contains energy-containing functional groups: a nitryl group and two azide groups and is expected to make certain contribution to energy of an energetic material propellant system. Cheap p-toluenesulfonic acid in the esterification reaction is less in use level and high in activity and does not easily cause side reaction, so that the compound has certain economic and environment-friendly efficiencies. Meanwhile, the synthetic method is mild in reaction condition, easy in control of the reaction condition and low in equipment demand.

Description

A kind of nitrine ester compound, synthetic method and application thereof
Technical field
The present invention relates to a kind of nitrine ester compound, synthetic method and application thereof, particularly three (nitrine acetyl-o-methyl) Nitromethane 99Min.s and synthetic, belong to organic chemistry filed.
Background technology
Organic azide is the energetic material of a class excellence, is widely used in containing all many-sides such as energy tamanori, energetic plasticiser, oxygenants, and be to improve the energy level of energetic material and the important channel of technical feature.
Conventional energetic plasticiser has the types such as nitrate esters energetic plasticiser, geminal dinitro class energetic plasticiser, nitrine class energetic plasticiser, nitre oxygen ethyl nitramine class energetic plasticiser at present.The shortcoming of nitrine ester plasticizer is that nitrogen content is low, little to the contribution of propelling agent maximum system energy.
Summary of the invention
The object of the present invention is to provide a kind of new nitrine ester compound and synthetic method thereof.
The technical scheme that realizes the object of the invention is: a kind of nitrine ester compound, has following structure:
Figure 2014101070270100002DEST_PATH_IMAGE001
The synthetic route of the nitrine ester compound of said structure is as follows:
A synthetic method for nitrine ester compound, comprises esterification and azido reaction, comprises following concrete steps:
In step 1, esterification, trishydroxymethylnitromethane and chloroacetic mol ratio are 1:2.5～4.5, add catalyzer, reflux, and fraction water device water-dividing;
In step 2, azido reaction, the mol ratio of three (chloroethene acyl-oxygen methyl) Nitromethane 99Min.s and sodiumazide is 1:2～6, dimethyl sulphoxide aqueous solution is solvent, Tetrabutyl amonium bromide is phase-transfer catalyst, and stirring at room temperature is slowly warming up to 30～70 ℃ of reactions.
The solvent of the esterification described in step 1 can adopt benzene, toluene or dimethylbenzene, and described catalyzer can be the vitriol oil, sodium pyrosulfate or tosic acid etc.
The mass concentration of the dimethyl sulphoxide aqueous solution described in step 2 is 90%, and the described stirring at room temperature time is 2h.
An application for nitrine ester compound, is applied to the nitrine ester compound of said structure in energetic material propelling agent system.
Compared with prior art, advantage of the present invention is:
1. three (nitrine acetyl-o-methyl) Nitromethane 99Min. there is not yet bibliographical information.
2. three (nitrine acetyl-o-methyl) Nitromethane 99Min., is two kinds of nitrine ester compounds containing energy functional group containing a nitro and three azido-s, and being expected to has certain contribution to the energy of energetic material propelling agent system.
The tosic acid of 3 cheapnesss is in esterification, and consumption is little, active high, is difficult for causing side reaction, therefore, has certain economy and the feature of environmental protection.
4. reaction conditions of the present invention is gentle and be easy to control, low for equipment requirements.
Accompanying drawing explanation
Fig. 1 is embodiment 1 three (chloroethene acyl-oxygen methyl) Nitromethane 99Min. 1h NMR.
Fig. 2 is the IR of embodiment 1 three (chloroethene acyl-oxygen methyl) Nitromethane 99Min..
Fig. 3 is embodiment's 9 three (nitrine acetyl-o-methyl) 1h NMR.
Fig. 4 is the IR of embodiment 9 three (nitrine acetyl-o-methyl).
Embodiment
Embodiment 1
The preparation of intermediate product three (chloroethene acyl-oxygen methyl) Nitromethane 99Min.
In 50 mL dimethylbenzene, add Tris Nitro 1.52g (commercially available, 0.01mol), Mono Chloro Acetic Acid 3.31g (0.035mol), tosic acid 0.03g (0.2mmol), mixture reflux is divided water reaction, separates until anhydrous.Pressure reducing and steaming dimethylbenzene, is cooled to room temperature, uses CH 2cl 2dissolve saturated Na 2cO 3aqueous solution regulator solution pH value is to neutral, and salt water washing three times, washes, anhydrous magnesium sulfate drying, and pressure reducing and steaming solvent, dehydrated alcohol recrystallization, obtains three (chloroethene acyl-oxygen methyl) Nitromethane 99Min., yield 88.9%.
Fig. 1 from accompanying drawing explanation can find out, δ 4.702 is-CH 2on the chemical shift of H; δ 4.445 is-CH 2the chemical shift of H on Cl.As can be seen from Figure 2,2953,2904 cm -1for-CH 2stretching vibration absorption peak; 1769cm -1for C=O stretching vibration peak; 788 cm -1for C-Cl stretching vibration peak; 1556 cm -1for-NO 2symmetrical stretching vibration absorption peak.
Embodiment 2
The preparation of intermediate product three (chloroethene acyl-oxygen methyl) Nitromethane 99Min.
In 50 mL dimethylbenzene, add Tris Nitro 1.52g (0.01mol), Mono Chloro Acetic Acid 3.31g (0.035mol), tosic acid 0.03g (0.2mmol), mixture reflux is divided water reaction, separates until anhydrous.Pressure reducing and steaming dimethylbenzene, is cooled to room temperature, uses CH 2cl 2dissolve saturated Na 2cO 3aqueous solution regulator solution pH value is to neutral, and salt water washing three times, washes, anhydrous magnesium sulfate drying, and pressure reducing and steaming solvent, dehydrated alcohol recrystallization, obtains three (chloroethene acyl-oxygen methyl) Nitromethane 99Min., yield 88.9%.
Embodiment 3
The preparation of intermediate product three (chloroethene acyl-oxygen methyl) Nitromethane 99Min.
In 50 mL dimethylbenzene, add Tris Nitro 1.52g (0.01mol), Mono Chloro Acetic Acid 2.36g (0.025mol), tosic acid 0.03g (0.2mmol), mixture reflux is divided water reaction, separates until anhydrous.Pressure reducing and steaming dimethylbenzene, is cooled to room temperature, uses CH 2cl 2dissolve saturated Na 2cO 3aqueous solution regulator solution pH value is to neutral, and salt water washing three times, washes, anhydrous magnesium sulfate drying, and pressure reducing and steaming solvent, dehydrated alcohol recrystallization, obtains three (chloroethene acyl-oxygen methyl) Nitromethane 99Min., yield 73.8%.
Embodiment 4
The preparation of intermediate product three (chloroethene acyl-oxygen methyl) Nitromethane 99Min.
In 50 mL dimethylbenzene, add Tris Nitro 1.52g (0.01mol), Mono Chloro Acetic Acid 4.26g (0.045mol), tosic acid 0.03g (0.2mmol), mixture reflux is divided water reaction, separates until anhydrous.Pressure reducing and steaming dimethylbenzene, is cooled to room temperature, uses CH 2cl 2dissolve saturated Na 2cO 3aqueous solution regulator solution pH value is to neutral, and salt water washing three times, washes, anhydrous magnesium sulfate drying, and pressure reducing and steaming solvent, dehydrated alcohol recrystallization, obtains three (chloroethene acyl-oxygen methyl) Nitromethane 99Min., yield 88.6%.
Embodiment 5
The preparation of intermediate product three (chloroethene acyl-oxygen methyl) Nitromethane 99Min.
In 50 mL dimethylbenzene, add Tris Nitro 1.52g (0.01mol), Mono Chloro Acetic Acid 3.31g (0.035mol), vitriol oil 0.2mmol, mixture reflux is divided water reaction, separates until anhydrous.Pressure reducing and steaming dimethylbenzene, is cooled to room temperature, uses CH 2cl 2dissolve saturated Na 2cO 3aqueous solution regulator solution pH value is to neutral, and salt water washing three times, washes, anhydrous magnesium sulfate drying, and pressure reducing and steaming solvent, dehydrated alcohol recrystallization, obtains three (chloroethene acyl-oxygen methyl) Nitromethane 99Min., yield 65.1%.
Embodiment 6
The preparation of intermediate product three (chloroethene acyl-oxygen methyl) Nitromethane 99Min.
In 50 mL dimethylbenzene, add Tris Nitro 1.52g (0.01mol), Mono Chloro Acetic Acid 3.31g (0.035mol), sodium pyrosulfate 0.2mmol, mixture reflux is divided water reaction, separates until anhydrous.Pressure reducing and steaming dimethylbenzene, is cooled to room temperature, uses CH 2cl 2dissolve saturated Na 2cO 3aqueous solution regulator solution pH value is to neutral, and salt water washing three times, washes, anhydrous magnesium sulfate drying, and pressure reducing and steaming solvent, dehydrated alcohol recrystallization, obtains three (chloroethene acyl-oxygen methyl) Nitromethane 99Min., yield 79.5%.
Embodiment 7
The preparation of intermediate product three (chloroethene acyl-oxygen methyl) Nitromethane 99Min.
In 50 mL benzene, add Tris Nitro 1.52g (0.01mol), Mono Chloro Acetic Acid 3.31g (0.035mol), tosic acid 0.03g (0.2mmol), mixture reflux is divided water reaction, separates until anhydrous.Pressure reducing and steaming dimethylbenzene, is cooled to room temperature, uses CH 2cl 2dissolve saturated Na 2cO 3aqueous solution regulator solution pH value is to neutral, and salt water washing three times, washes, anhydrous magnesium sulfate drying, and pressure reducing and steaming solvent, dehydrated alcohol recrystallization, obtains three (chloroethene acyl-oxygen methyl) Nitromethane 99Min., yield 66.5%.
Embodiment 8
The preparation of intermediate product three (chloroethene acyl-oxygen methyl) Nitromethane 99Min.
In 50 mL toluene, add Tris Nitro 1.52g (0.01mol), Mono Chloro Acetic Acid 3.31g (0.035mol), tosic acid 0.03g (0.2mmol), mixture reflux is divided water reaction, separates until anhydrous.Pressure reducing and steaming dimethylbenzene, is cooled to room temperature, uses CH 2cl 2dissolve saturated Na 2cO 3aqueous solution regulator solution pH value is to neutral, and salt water washing three times, washes, anhydrous magnesium sulfate drying, and pressure reducing and steaming solvent, dehydrated alcohol recrystallization, obtains three (chloroethene acyl-oxygen methyl) Nitromethane 99Min., yield 75.2%.
Embodiment 9
The preparation of product nitrine ester three (nitrine acetyl-o-methyl)
Three (chloroethene acyl-oxygen methyl) Nitromethane 99Min.s of embodiment 1 gained and the mol ratio of sodiumazide are 1:4,90% DMSO aqueous solution 30mL, Tetrabutyl amonium bromide and three (chloroethene acyl-oxygen methyl) Nitromethane 99Min. mol ratio is 2:100, stirring at room temperature 2h, slowly be warming up to 50 ℃, when reaction 15h, be cooled to room temperature, pour in trash ice, stir, dichloromethane extraction, salt water washing three times, washing, anhydrous magnesium sulfate drying, pressure reducing and steaming methylene dichloride, obtains three (nitrine acetyl-o-methyls), yield 85.2%.
Fig. 3 from accompanying drawing explanation can find out, δ 4.154 is-CH 2n 3on the chemical shift of H; δ 4.717 is-CH 2the chemical shift of H on OOC.As can be seen from Figure 4,2966,2919cm -1for C-H stretching vibration peak; 2102 cm -1for-N 3stretching vibration peak; 1753cm -1for C=O stretching vibration peak, three (nitrine acetyl-o-methyl) Nitromethane 99Min., be two kinds of nitrine ester compounds containing energy functional group containing a nitro and three azido-s, inference theoretically, is expected to providing certain energy to energetic material propelling agent system.
Embodiment 10
The preparation of product nitrine ester three (nitrine acetyl-o-methyl)
Three (chloroethene acyl-oxygen methyl) Nitromethane 99Min.s of embodiment 1 gained and the mol ratio of sodiumazide are 1:2,90% DMSO aqueous solution 30mL, Tetrabutyl amonium bromide and three (chloroethene acyl-oxygen methyl) Nitromethane 99Min. mol ratio is 2:100, stirring at room temperature 2h, slowly be warming up to 50 ℃, when reaction 15h, be cooled to room temperature, pour in trash ice, stir, dichloromethane extraction, salt water washing three times, washing, anhydrous magnesium sulfate drying, pressure reducing and steaming methylene dichloride, obtains three (nitrine acetyl-o-methyls), yield 62.8%.
Embodiment 11
The preparation of product nitrine ester three (nitrine acetyl-o-methyl)
Three (chloroethene acyl-oxygen methyl) Nitromethane 99Min.s of embodiment 1 gained and the mol ratio of sodiumazide are 1:6,90% DMSO aqueous solution 30mL, Tetrabutyl amonium bromide and three (chloroethene acyl-oxygen methyl) Nitromethane 99Min. mol ratio is 2:100, stirring at room temperature 2h, slowly be warming up to 50 ℃, when reaction 15h, be cooled to room temperature, pour in trash ice, stir, dichloromethane extraction, salt water washing three times, washing, anhydrous magnesium sulfate drying, pressure reducing and steaming methylene dichloride, obtains three (nitrine acetyl-o-methyls), yield 85.5%.
Embodiment 12
The preparation of product nitrine ester three (nitrine acetyl-o-methyl)
Three (chloroethene acyl-oxygen methyl) Nitromethane 99Min.s of embodiment 1 gained and the mol ratio of sodiumazide are 1:4,90% DMSO aqueous solution 30mL, Tetrabutyl amonium bromide and three (chloroethene acyl-oxygen methyl) Nitromethane 99Min. mol ratio is 2:100, stirring at room temperature 2h, slowly be warming up to 30 ℃, when reaction 15h, be cooled to room temperature, pour in trash ice, stir, dichloromethane extraction, salt water washing three times, washing, anhydrous magnesium sulfate drying, pressure reducing and steaming methylene dichloride, obtains three (nitrine acetyl-o-methyls), yield 62.1%.
Embodiment 13
The preparation of product nitrine ester three (nitrine acetyl-o-methyl)
Three (chloroethene acyl-oxygen methyl) Nitromethane 99Min.s of embodiment 1 gained and the mol ratio of sodiumazide are 1:4,90% DMSO aqueous solution 30mL, Tetrabutyl amonium bromide and three (chloroethene acyl-oxygen methyl) Nitromethane 99Min. mol ratio is 2:100, stirring at room temperature 2h, slowly be warming up to 70 ℃, when reaction 15h, be cooled to room temperature, pour in trash ice, stir, dichloromethane extraction, salt water washing three times, washing, anhydrous magnesium sulfate drying, pressure reducing and steaming methylene dichloride, obtains three (nitrine acetyl-o-methyls), yield 74.5%.

Claims (7)

1. a nitrine ester compound, is characterized in that, has following structure:
Nitrine ester compound according to claim 1, is characterized in that, described compound is prepared by following concrete steps:
In step 1, esterification, trishydroxymethylnitromethane and chloroacetic mol ratio are 1:2.5～4.5, add catalyzer, reflux, and fraction water device water-dividing;
In step 2, azido reaction, the mol ratio of three (chloroethene acyl-oxygen methyl) Nitromethane 99Min.s and sodiumazide is 1:2～6, dimethyl sulphoxide aqueous solution is solvent, Tetrabutyl amonium bromide is phase-transfer catalyst, and stirring at room temperature is slowly warming up to 30～70 ℃ of reactions.
2. nitrine ester compound according to claim 2, is characterized in that, the solvent of the esterification described in step 1 adopts the one in benzene, toluene or dimethylbenzene, and described catalyzer is selected from the vitriol oil, sodium pyrosulfate or tosic acid a kind of.
3. nitrine ester compound according to claim 2, is characterized in that, the mass concentration of the dimethyl sulphoxide aqueous solution described in step 2 is 90%, and the described stirring at room temperature time is 2h.
4. a synthetic method for nitrine ester compound, is characterized in that, comprises esterification and azido reaction, specifically comprises the following steps:
In step 1, esterification, trishydroxymethylnitromethane and chloroacetic mol ratio are 1:2.5～4.5, add catalyzer, reflux, and fraction water device water-dividing;
In step 2, azido reaction, the mol ratio of three (chloroethene acyl-oxygen methyl) Nitromethane 99Min.s and sodiumazide is 1:2～6, dimethyl sulphoxide aqueous solution is solvent, Tetrabutyl amonium bromide is phase-transfer catalyst, and stirring at room temperature is slowly warming up to 30～70 ℃ of reactions.
5. the synthetic method of nitrine ester compound according to claim 5, it is characterized in that, the solvent of the esterification described in step 1 adopts the one in benzene, toluene or dimethylbenzene, and described catalyzer is selected from the vitriol oil, sodium pyrosulfate or tosic acid a kind of.
6. the synthetic method of nitrine ester compound according to claim 5, is characterized in that, the mass concentration of the dimethyl sulphoxide aqueous solution described in step 2 is 90%, and the described stirring at room temperature time is 2h.
7. an application for nitrine ester compound, is applied to nitrine ester compound claimed in claim 1 in energetic material propelling agent system.
CN201410107027.0A 2014-03-21 2014-03-21 Azide ester compound, synthetic method and application of compound Pending CN103880704A (en)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104496845A (en) * 2014-12-13 2015-04-08 西安近代化学研究所 Synthesis method of tri(azidoacetyloxymethyl)nitromethane
CN107312114A (en) * 2016-04-27 2017-11-03 北京理工大学 A kind of azide polymer with polynorbornene backbone structure and preparation method thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1216766A (en) * 1998-10-06 1999-05-19 中国人民解放军第二军医大学 Method for preparing beta-thymidine
US20050033040A1 (en) * 2003-08-08 2005-02-10 Samsung Electronics Co., Ltd. Self-dispersible bipyridine-based metal complex and ink composition comprising the same
CN103012194A (en) * 2012-11-16 2013-04-03 南京理工大学 Nitrine ester compound and synthesis method thereof
CN103641723A (en) * 2013-12-13 2014-03-19 南京理工大学 2,3-Dihydroxymethyl-2,3-dinitro-1,4-butanediol tetraacetate and synthetic method thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN1216766A (en) * 1998-10-06 1999-05-19 中国人民解放军第二军医大学 Method for preparing beta-thymidine
US20050033040A1 (en) * 2003-08-08 2005-02-10 Samsung Electronics Co., Ltd. Self-dispersible bipyridine-based metal complex and ink composition comprising the same
CN103012194A (en) * 2012-11-16 2013-04-03 南京理工大学 Nitrine ester compound and synthesis method thereof
CN103641723A (en) * 2013-12-13 2014-03-19 南京理工大学 2,3-Dihydroxymethyl-2,3-dinitro-1,4-butanediol tetraacetate and synthetic method thereof

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DREES, DETLEF等: "Synthesis and characterization of azido plasticizer", 《PROPELLANTS, EXPLOSIVES, PYROTECHNICS》 *
KESHAVARZ, MOHAMMAD HOSSEIN等: "A simple accurate model for prediction of deflagration temperature of energetic compounds", 《JOURNAL OF THERMAL ANALYSIS AND CALORIMETRY》 *

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN104496845A (en) * 2014-12-13 2015-04-08 西安近代化学研究所 Synthesis method of tri(azidoacetyloxymethyl)nitromethane
CN107312114A (en) * 2016-04-27 2017-11-03 北京理工大学 A kind of azide polymer with polynorbornene backbone structure and preparation method thereof
CN107312114B (en) * 2016-04-27 2020-11-13 北京理工大学 Azide polymer with polynorbornene main chain structure and preparation method thereof

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Application publication date: 20140625