CN115557852A - Synthesis method of 1, 5-diazido-3-nitroazapentane - Google Patents
Synthesis method of 1, 5-diazido-3-nitroazapentane Download PDFInfo
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- CN115557852A CN115557852A CN202211115314.7A CN202211115314A CN115557852A CN 115557852 A CN115557852 A CN 115557852A CN 202211115314 A CN202211115314 A CN 202211115314A CN 115557852 A CN115557852 A CN 115557852A
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- nitroazapentane
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
- C07C243/02—N-nitro compounds
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C241/00—Preparation of compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
- C07C247/02—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton
- C07C247/04—Compounds containing azido groups with azido groups bound to acyclic carbon atoms of a carbon skeleton being saturated
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Abstract
The invention discloses a method for synthesizing 1, 5-diazido-3-nitroazapentane, which takes bis (2-chloroethyl) amine nitrate as a raw material and comprises the following steps: adding bis (2-chloroethyl) amine nitrate into concentrated nitric acid, dissolving, then dropwise adding acetic anhydride, after the addition is finished, carrying out heat preservation reaction at 40-60 ℃, then pouring the reaction solution into a large amount of ice water, continuously stirring, adding dichloromethane, extracting, washing and distilling to obtain the 1, 5-dichloroethyl-3-nitroazapentane. Adding dimethyl sulfoxide and water into a reaction bottle, adding 1, 5-dichloroethyl-3-nitroazapentane, then adding sodium azide into the reaction bottle, after the addition is finished, placing the reaction bottle into a microwave reactor, setting the microwave heating temperature to be 80-100 ℃ for reaction, cooling to room temperature after the reaction is finished, adding dichloromethane for extraction, washing and distilling to obtain the 1, 5-diazido-3-nitroazapentane. The invention has the characteristics of high reaction yield and high purity.
Description
Technical Field
The invention belongs to the field of energetic materials, and relates to a synthesis method of 1, 5-diazido-3-nitroazapentane.
Background
The 1, 5-diazide-3-nitro-3-aza pentane is a novel energetic plasticizer which contains azide and nitro-amino and has the nitrogen content of 56 percent, has the performance advantages of higher energy, lower explosion temperature, higher burning speed, low fuel gas molecular weight, strong plasticizing capacity on nitrocotton and the like, and can be used for high-energy low-ablation propellant, high-energy liquid propellant, pyrotechnic agent, gas generating agent and the like. The method for preparing 1, 5-diazido-3-nitroazapentane in the prior art has generally low reaction yield and purity.
Disclosure of Invention
Aiming at the defects in the prior art, the invention aims to provide a method for synthesizing 1, 5-diazido-3-nitroazapentane, so as to solve the problems of low reaction yield and purity and the like.
In order to solve the technical problems, the invention adopts the following technical scheme:
a method for synthesizing 1, 5-diazido-3-nitroazapentane comprises the following steps:
(1) Adding bis (2-chloroethyl) amine nitrate into concentrated nitric acid at the temperature of 20-30 ℃, dropwise adding acetic anhydride after dissolving, keeping the temperature at the temperature of 40-60 ℃ for 1-2 h after adding, then pouring the reaction solution into a large amount of ice water, continuously stirring, adding dichloromethane for extraction, washing and distilling to obtain 1, 5-dichloroethyl-3-nitroazapentane;
(2) Adding reaction solvents of dimethyl sulfoxide and water into a reaction bottle, heating to 50 ℃, adding 1, 5-dichloroethyl-3-nitroazapentane, then adding sodium azide into the reaction bottle, after the addition is finished, placing the reaction bottle into a microwave reactor, setting the microwave heating temperature to be 80-100 ℃, reacting for 2-4 h, cooling to room temperature, adding dichloromethane, extracting, washing and distilling to obtain the 1, 5-diazide-3-nitroazapentane.
The invention also comprises the following technical characteristics:
specifically, the structural formula of the 1, 5-diazido-3-nitroazapentane is shown as the formula (I):
the structural formula of the bis (2-chloroethyl) amine nitrate is shown as the formula (II):
specifically, the molar ratio of the bis (2-chloroethyl) amine nitrate to the concentrated nitric acid to the acetic anhydride is as follows: 1.5-2; the dosage of the reaction solvent is as follows: adding 3-5 g of reaction solvent into every 1g of 1, 5-dichloroethyl-3-nitroazapentane; the mass ratio of the dimethyl sulfoxide to the water is 1.1-0.3; the molar ratio of the 1, 5-dichloroethyl-3-nitroazapentane to the sodium azide is 1.
Specifically, the molar ratio of the bis (2-chloroethyl) amine nitrate to the concentrated nitric acid to the acetic anhydride is as follows: 1.8; the dosage of the reaction solvent is as follows: adding 4g of reaction solvent into 1g of 1, 5-dichloroethyl-3-nitroazapentane; the mass ratio of the dimethyl sulfoxide to the water is 1; the molar ratio of the 1, 5-dichloroethyl-3-nitroazapentane to the sodium azide is 1.
Specifically, the method comprises the following steps:
(1) Adding bis (2-chloroethyl) amine nitrate into concentrated nitric acid at the temperature of 20-30 ℃, dropwise adding acetic anhydride after dissolving, keeping the temperature for 1h at the temperature of 55-60 ℃ after adding, then pouring the reaction liquid into a large amount of ice water, continuously stirring, adding dichloromethane for extraction, washing and distilling to obtain 1, 5-dichloroethyl-3-nitroazapentane;
(2) Adding dimethyl sulfoxide and water into a reaction bottle, heating to 50 ℃, adding 1, 5-dichloroethyl-3-nitroazapentane, then adding sodium azide into the reaction bottle, after the addition is finished, putting the reaction bottle into a microwave reactor, setting the microwave heating temperature to 90-95 ℃, reacting for 3 hours, cooling to room temperature, adding dichloromethane for extraction, washing and distilling to obtain 1, 5-diazido-3-nitroazapentane.
Compared with the prior art, the invention has the following technical effects:
(1) The reaction yield of the 1, 5-dichloroethyl-3-nitroazapentane is 74-77%, and the reaction yield is improved; the purity of the 1, 5-dichloroethyl-3-nitroazapentane is 98.1-98.5%, and the product purity is improved.
(2) The reaction yield of the 1, 5-diazido-3-nitroazapentane is 87.5-90.3 percent, and the reaction yield is improved; the purity of the 1, 5-diazido-3-nitro-aza-pentane is 98.5-99.7%, and the product purity is improved.
(3) According to the invention, nitrate is adopted to increase the concentration of nitroxyl cation in the reaction system on one hand, and on the other hand, the nitration reaction is facilitated through the ionic bond effect, so that the yield and the purity of the reaction are improved; meanwhile, during nitration, no hydrochloric acid gas is generated, so that corrosion to a metal reaction container is avoided.
Detailed Description
The invention provides a synthetic method of 1, 5-diazido-3-nitroazapentane, which comprises the following steps:
the method comprises the following steps:
(1) Adding bis (2-chloroethyl) amine nitrate into concentrated nitric acid at the temperature of 20-30 ℃, dropwise adding acetic anhydride after dissolving, keeping the temperature at the temperature of 40-60 ℃ for 1-2 h after adding the materials, then pouring the reaction solution into a large amount of ice water, continuously stirring, adding dichloromethane for extraction, washing and distilling to obtain 1, 5-dichloroethyl-3-nitroazacyclopentane;
(2) Adding reaction solvents of dimethyl sulfoxide and water into a reaction bottle, heating to 50 ℃, adding 1, 5-dichloroethyl-3-nitroazapentane, then adding sodium azide into the reaction bottle, after the addition is finished, placing the reaction bottle into a microwave reactor, setting the microwave heating temperature to be 80-100 ℃, reacting for 2-4 h, cooling to room temperature, adding dichloromethane, extracting, washing and distilling to obtain the 1, 5-diazide-3-nitroazapentane.
The structural formula of the 1, 5-diazido-3-nitroazapentane is shown as the formula (I);
the structural formula of the bis (2-chloroethyl) amine nitrate is shown as (II);
in the nitration reaction stage, the molar ratio of the bis (2-chloroethyl) amine nitrate to the concentrated nitric acid to the acetic anhydride is as follows: 1.5-2;
in the stage of the azide reaction, the dosage of the reaction solvent is as follows: 1g of 1, 5-dichloroethyl-3-nitroazapentane, adding 3g to 5g of reaction solvent, wherein the mass ratio of dimethyl sulfoxide to water is 1; the mol ratio of the 1, 5-dichloroethyl-3-nitroazapentane to the sodium azide is 1.
Preferably, the method comprises the following steps:
(1) Adding bis (2-chloroethyl) amine nitrate into concentrated nitric acid at the temperature of 20-30 ℃, dropwise adding acetic anhydride after dissolving, keeping the temperature for 1h at the temperature of 55-60 ℃ after adding materials, then pouring reaction liquid into a large amount of ice water, continuously stirring, adding dichloromethane for extraction, washing and distilling to obtain 1, 5-dichloroethyl-3-nitroazapentane, wherein the molar ratio of the bis (2-chloroethyl) amine nitrate to the concentrated nitric acid to the acetic anhydride is as follows: 1.8;
(2) Adding dimethyl sulfoxide and water into a reaction bottle, heating to 50 ℃, adding 1, 5-dichloroethyl-3-nitroazapentane, then adding sodium azide into the reaction bottle, after the addition is finished, placing the reaction bottle into a microwave reactor, setting the microwave heating temperature to 90-95 ℃, reacting for 3 hours, cooling to room temperature, adding dichloromethane for extraction, washing and distilling to obtain 1, 5-diazide-3-nitroazapentane, wherein the dosage of a reaction solvent is as follows: 1g of 1, 5-dichloroethyl-3-nitroazapentane, adding 4g of a reaction solvent, wherein the mass ratio of dimethyl sulfoxide to water is 1; the molar ratio of 1, 5-dichloroethyl-3-nitroazapentane to sodium azide was 1.
The following embodiments of the present invention are provided, and it should be noted that the present invention is not limited to the following embodiments, and all equivalent changes based on the technical solutions of the present invention are within the protection scope of the present invention.
Example 1:
this example provides a method for synthesizing 1, 5-diazido-3-nitroazapentane, which comprises the following steps:
adding 45.1g (0.22 mol) of bis (2-chloroethyl) amine nitrate into 16.8ml (0.4 mol) of concentrated nitric acid at the temperature of 20-30 ℃, dropwise adding 42.84g (0.42 mol) of acetic anhydride after dissolving, preserving heat for 1h at the temperature of 55-60 ℃ after adding, then pouring the reaction solution into a large amount of ice water, continuously stirring, adding dichloromethane for extraction, washing and distilling to obtain 31.68g of 1, 5-dichloroethyl-3-nitroazapentane, wherein the yield is 77%, and the purity is 98.4%.
Adding 62.33g of dimethyl sulfoxide and 12.47g of water into a reaction bottle, heating to 50 ℃, adding 18.7g (0.1 mol) of 1, 5-dichloroethyl-3-nitroazapentane, then adding 14.95g (0.23 mol) of sodium azide into the reaction bottle, after the addition is finished, putting the reaction bottle into a microwave reactor, setting the microwave heating temperature to 90-95 ℃, reacting for 3h, cooling to room temperature, adding dichloromethane, extracting, washing and distilling to obtain 18.02g of 1, 5-diazide-3-nitroazapentane, wherein the yield is 90.1%, and the purity is 99.5%.
Structural characterization of 1, 5-diazido-3-nitroazapentane:
IR(KBr,cm -1 )ν:2942m,2105s,1516s,1454m,1263s,961w,778m。
1 HNMR(500MHz,CDCl 3 )δ:4.060(2H,t),3.773(2H,t)。
elemental analysis: molecular formula C 4 H 8 N 8 O 2 The theoretical value is as follows: c,24.00; h,4.03; n,55.99;
measured value: c,24.15; h,4.10; n,56.34.
The above characterization data demonstrate that the compound synthesized is 1, 5-diazido-3-nitroazapentane.
Example 2:
this example provides a method for synthesizing 1, 5-diazido-3-nitroazapentane, which comprises the following steps:
adding 45.1g (0.22 mol) of bis (2-chloroethyl) amine nitrate into 14.7ml (0.35 mol) of concentrated nitric acid at the temperature of between 20 and 30 ℃, dripping 44.88g (0.44 mol) of acetic anhydride after dissolving, preserving heat for 1.5 hours at the temperature of between 40 and 45 ℃ after adding, then pouring reaction liquid into a large amount of ice water, continuously stirring, adding dichloromethane for extraction, washing and distilling to obtain 30.44g of 1, 5-dichloroethyl-3-nitroazapentane, wherein the yield is 74 percent and the purity is 97.2 percent.
Adding 59.5g of dimethyl sulfoxide and 5.95g of water into a reaction bottle, heating to 50 ℃, adding 18.7g (0.1 mol) of 1, 5-dichloroethyl-3-nitroazapentane, then adding 13.65g (0.21 mol) of sodium azide into the reaction bottle, after the addition is finished, putting the reaction bottle into a microwave reactor, setting the microwave heating temperature to 85-90 ℃, reacting for 4h, cooling to room temperature, adding dichloromethane for extraction, washing and distilling to obtain 17.92g of 1, 5-diazido-3-nitroazapentane, wherein the yield is 89.6%, and the purity is 98.5%.
Example 3:
this example provides a method for synthesizing 1, 5-diazido-3-nitroazapentane, which comprises the following steps:
adding 45.1g (0.22 mol) of bis (2-chloroethyl) amine nitrate into 13.86ml (0.33 mol) of concentrated nitric acid at the temperature of 20-30 ℃, dropwise adding 40.8g (0.40 mol) of acetic anhydride after dissolving, preserving heat for 2 hours at the temperature of 45-50 ℃ after adding, then pouring the reaction solution into a large amount of ice water, continuously stirring, adding dichloromethane for extraction, washing and distilling to obtain 31.27g1, 5-dichloroethyl-3-nitroazapentane, wherein the yield is 76%, and the purity is 98.5%.
Adding 71.92g of dimethyl sulfoxide and 21.58g of water into a reaction bottle, heating to 50 ℃, adding 18.7g (0.1 mol) of 1, 5-dichloroethyl-3-nitroazapentane, then adding 14.3g (0.22 mol) of sodium azide into the reaction bottle, after the addition is finished, putting the reaction bottle into a microwave reactor, setting the microwave heating temperature to 90-95 ℃, reacting for 3h, cooling to room temperature, adding dichloromethane, extracting, washing and distilling to obtain 17.5g of 1, 5-diazide-3-nitroazapentane, wherein the yield is 87.5%, and the purity is 99.1%.
Example 4:
this example provides a method for synthesizing 1, 5-diazido-3-nitroazapentane, which comprises the following steps:
adding 45.1g (0.22 mol) of bis (2-chloroethyl) amine nitrate into 15.54ml (0.37 mol) of concentrated nitric acid at the temperature of between 20 and 30 ℃, dripping 42.84g (0.42 mol) of acetic anhydride after dissolving, preserving heat for 1.5 hours at the temperature of between 50 and 55 ℃ after adding, then pouring the reaction solution into a large amount of ice water, continuously stirring, adding dichloromethane for extraction, washing and distilling to obtain 31.01g of 1, 5-dichloroethyl-3-nitroazapentane, wherein the yield is 75.4 percent and the purity is 97.8 percent.
Adding 70.63g of dimethyl sulfoxide and 12.12g of water into a reaction bottle, heating to 50 ℃, adding 18.7g (0.1 mol) of 1, 5-dichloroethyl-3-nitroazapentane, then adding 15.6g (0.24 mol) of sodium azide into the reaction bottle, after the addition is finished, putting the reaction bottle into a microwave reactor, setting the microwave heating temperature to 95-100 ℃, reacting for 2h, cooling to room temperature, adding dichloromethane for extraction, washing and distilling to obtain 17.78g of 1, 5-diazido-3-nitroazapentane, wherein the yield is 88.9%, and the purity is 99.2%.
Claims (5)
1. A method for synthesizing 1, 5-diazido-3-nitroazapentane is characterized by comprising the following steps:
(1) Adding bis (2-chloroethyl) amine nitrate into concentrated nitric acid at the temperature of 20-30 ℃, dropwise adding acetic anhydride after dissolving, keeping the temperature at the temperature of 40-60 ℃ for 1-2 h after adding, then pouring the reaction solution into a large amount of ice water, continuously stirring, adding dichloromethane for extraction, washing and distilling to obtain 1, 5-dichloroethyl-3-nitroazapentane;
(2) Adding reaction solvents of dimethyl sulfoxide and water into a reaction bottle, heating to 50 ℃, adding 1, 5-dichloroethyl-3-nitroazapentane, then adding sodium azide into the reaction bottle, after the addition is finished, placing the reaction bottle into a microwave reactor, setting the microwave heating temperature to be 80-100 ℃, reacting for 2-4 h, cooling to room temperature, adding dichloromethane, extracting, washing and distilling to obtain the 1, 5-diazide-3-nitroazapentane.
3. the method for synthesizing 1, 5-diazido-3-nitroazapentane according to claim 1, wherein the molar ratio of the bis (2-chloroethyl) amine nitrate, the concentrated nitric acid and the acetic anhydride is as follows: 1.5-2; the dosage of the reaction solvent is as follows: adding 3-5 g of reaction solvent into every 1g of 1, 5-dichloroethyl-3-nitroazapentane; the mass ratio of the dimethyl sulfoxide to the water is 1.1-0.3; the molar ratio of the 1, 5-dichloroethyl-3-nitroazapentane to the sodium azide is 1.
4. The method for synthesizing 1, 5-diazido-3-nitroazapentane according to claim 3, wherein the molar ratio of the bis (2-chloroethyl) amine nitrate to the concentrated nitric acid to the acetic anhydride is: 1.8; the dosage of the reaction solvent is as follows: adding 4g of reaction solvent into 1g of 1, 5-dichloroethyl-3-nitroazapentane; the mass ratio of the dimethyl sulfoxide to the water is 1; the molar ratio of the 1, 5-dichloroethyl-3-nitroazapentane to the sodium azide is 1.
5. A process for the synthesis of 1, 5-diazido-3-nitroazapentane as claimed in claim 1, comprising the steps of:
(1) Adding bis (2-chloroethyl) amine nitrate into concentrated nitric acid at the temperature of 20-30 ℃, dropwise adding acetic anhydride after dissolving, keeping the temperature for 1h at the temperature of 55-60 ℃ after adding, then pouring the reaction liquid into a large amount of ice water, continuously stirring, adding dichloromethane for extraction, washing and distilling to obtain 1, 5-dichloroethyl-3-nitroazapentane;
(2) Adding dimethyl sulfoxide and water into a reaction bottle, heating to 50 ℃, adding 1, 5-dichloroethyl-3-nitroazapentane, then adding sodium azide into the reaction bottle, after the addition is finished, placing the reaction bottle into a microwave reactor, setting the microwave heating temperature to 90-95 ℃, reacting for 3 hours, cooling to room temperature, adding dichloromethane, extracting, washing and distilling to obtain the 1, 5-diazido-3-nitroazapentane.
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Citations (4)
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US3883374A (en) * | 1969-08-20 | 1975-05-13 | Us Navy | Double-base propellant containing organic azide |
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CN108586282A (en) * | 2018-04-04 | 2018-09-28 | 西安近代化学研究所 | The synthetic method of 1,3- diazido -2- propyl alcohol |
CN114956916A (en) * | 2022-05-23 | 2022-08-30 | 西安近代化学研究所 | Polyazido glycidyl ether compound and preparation method thereof |
-
2022
- 2022-09-14 CN CN202211115314.7A patent/CN115557852A/en active Pending
Patent Citations (4)
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US3883374A (en) * | 1969-08-20 | 1975-05-13 | Us Navy | Double-base propellant containing organic azide |
US4482404A (en) * | 1982-04-08 | 1984-11-13 | The United States Of America As Represented By The Secretary Of The Air Force | Azido nitramino ether containing solid propellants |
CN108586282A (en) * | 2018-04-04 | 2018-09-28 | 西安近代化学研究所 | The synthetic method of 1,3- diazido -2- propyl alcohol |
CN114956916A (en) * | 2022-05-23 | 2022-08-30 | 西安近代化学研究所 | Polyazido glycidyl ether compound and preparation method thereof |
Non-Patent Citations (1)
Title |
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