CN114213668A - Preparation method of HX-878 - Google Patents
Preparation method of HX-878 Download PDFInfo
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- CN114213668A CN114213668A CN202111532972.1A CN202111532972A CN114213668A CN 114213668 A CN114213668 A CN 114213668A CN 202111532972 A CN202111532972 A CN 202111532972A CN 114213668 A CN114213668 A CN 114213668A
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- China
- Prior art keywords
- reduced pressure
- tetraethylenepentamine
- solvent
- dropwise adding
- temperature
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/02—Polyamines
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The embodiment of the invention provides a preparation method of HX-878, which comprises the following steps: s1, dissolving tetraethylenepentamine and glycerol in a specific solvent, fully stirring at normal temperature to uniformly mix the materials, slowly dropwise adding acrylonitrile, controlling the reaction temperature within a certain range, and continuously preserving heat for a certain reaction time after dropwise adding; s2, distilling and recovering the solvent under the reduced pressure condition, and then carrying out reduced pressure distillation to remove trace water to obtain HX-878, wherein the HX-878 is qualified when the water content is less than or equal to 0.1%. The HX-878 prepared by the invention has high purity and yield.
Description
Technical Field
The invention relates to the technical field of fine chemical engineering, in particular to a preparation method of HX-878.
Background
The hydroxyl in the molecular structure of the polynitrile hydroxylamine polymer and the hydroxyl glue can enter a cross-linked network through chemical bonding, and a plurality of nitrile groups in the molecular structure can generate strong physical adsorption with the surface of nitramine oxidant particles. The bonding agent can be used as a nitramine or nitramine modified hydroxyl-terminated solid propellant bonding agent, can obviously improve the mechanical property of the propellant, and can also be compounded with other bonding agents for use in the bonding of hydroxyl-terminated adhesives and ammonium perchlorate composite solid propellants. However, HX-878 obtained by the conventional HX-878 preparation method has the problems of low purity and yield.
Disclosure of Invention
The embodiment of the invention provides a preparation method of HX-878, which aims to solve the problems of low purity and low yield of HX-878 obtained by the existing preparation method of HX-878.
The embodiment of the invention provides a preparation method of HX-878, which comprises the following steps:
s1, dissolving tetraethylenepentamine and glycerol in a specific solvent, fully stirring at normal temperature to uniformly mix the materials, slowly dropwise adding acrylonitrile, controlling the reaction temperature within a certain range, and continuously preserving heat for a certain reaction time after dropwise adding;
s2, distilling and recovering the solvent under the reduced pressure condition, and then carrying out reduced pressure distillation to remove trace water to obtain HX-878, wherein the HX-878 is qualified when the water content is less than or equal to 0.1%.
Further, in the step S1, the specific solvent is one or a mixture of toluene, cyclohexane, ethyl acetate and dichloroethane.
Furthermore, in the step S1, the reaction temperature is 0-90 ℃, the mass ratio of tetraethylenepentamine to glycerol is 1: 1-3.5: 1, and the reaction time is 0.5-3 hours.
Further, in step S2, the specific solvent is first recovered under normal pressure and then twice vacuum-dehydrated to obtain HX-878.
The invention has the following beneficial effects:
(1) the reaction condition is mild, the reaction can be carried out at normal temperature and normal pressure, the reaction time is short, the product viscosity is low, and the purity and the yield are high.
(2) The solvent is convenient to recycle and reuse, and no hazardous waste is generated in the preparation process.
(3) The process is suitable for industrial scale production.
Detailed Description
The technical solutions in the embodiments of the present invention will be clearly and completely described below with reference to the embodiments of the present invention, and it is obvious that the described embodiments are only a part of the embodiments of the present invention, and not all of the embodiments. All other embodiments, which can be derived by a person skilled in the art from the embodiments given herein without making any creative effort, shall fall within the protection scope of the present invention.
The invention will be further elucidated and described with reference to the embodiments of the invention described hereinafter.
Example 1
150g of toluene, 41.5g of tetraethylenepentamine and 14.5g of glycerol are added into a 500ml flask, the mixture is stirred uniformly, the temperature is raised to 40 ℃, 25.2g of acrylonitrile is slowly dripped, the dripping temperature is controlled between 40 ℃ and 60 ℃, the temperature is kept for 0.5 hour after the dripping is finished, and the toluene (toluene) is desolventized after the reaction is finished
And after distillation recovery, recycling), dehydrating for 2 hours in high vacuum, sampling and testing the water content (the water content is less than or equal to 0.1 percent, and determining that the dehydration is qualified) to obtain 75g of the product (HX-878).
Example 2
150g of cyclohexane, 50.5g of tetraethylenepentamine and 14.5g of glycerol are added into a 500ml flask, the mixture is stirred uniformly, the temperature is raised to 60 ℃, 25.2g of acrylonitrile is slowly dripped, the dripping temperature is controlled between 60 ℃ and 80 ℃, heat preservation is continued for 1 hour after the dripping is finished, after the reaction is finished, the solvent cyclohexane is removed (the cyclohexane can be recycled after being distilled and recovered), then high vacuum dehydration is carried out for 2 hours, and the water content (the water content is less than or equal to 0.1 percent and is regarded as qualified after the dehydration) is sampled and tested to obtain 85g of the product (HX-878).
Example 3
150g of dichloroethane, 41.5g of tetraethylenepentamine and 41.5g of glycerol are added into a 500ml flask, the mixture is uniformly stirred, the temperature is raised to 50 ℃, 25.2g of acrylonitrile is slowly dripped, the dripping temperature is controlled between 50 and 70 ℃, the temperature is kept for 2 hours after the dripping is finished, the dichloroethane as a solvent is removed after the reaction is finished (the dichloroethane can be recycled after being distilled and recovered), then the dehydration is carried out for 2 hours under high vacuum, and the water content (the water content is less than or equal to 0.1 percent and is regarded as qualified), is tested by sampling, and 110g of the product (HX-878) is obtained.
Example 4
150g of ethyl acetate, 41.5g of tetraethylenepentamine and 20.5g of glycerol are added into a 500ml flask, the mixture is stirred uniformly, the temperature is raised to 40 ℃, 25.2g of acrylonitrile is slowly dripped, the dripping temperature is controlled between 40 ℃ and 60 ℃, heat preservation is continuously carried out for 0.5 hour after the dripping is finished, the ethyl acetate serving as a solvent is removed after the reaction is finished (the ethyl acetate can be recycled after being distilled and recovered), then high-vacuum dehydration is carried out for 2 hours, and the water content is tested by sampling (the water content is less than or equal to 0.1 percent and is considered as qualified in dehydration), so that 80.5g of the product (HX-878) is obtained.
In the example of the invention, the HX-878 product index obtained is as follows:
| serial number | Index name | Index (I) |
| 1 | Appearance of the product | Yellowish viscous liquid |
| 2 | Water,% (m/m) | ≤0.1 |
| 3 | Total amine content (eq./100g) | 0.8-1.20 |
| 4 | Hydroxyl number (eq./100g) | 0.4-0.6 |
| 5 | Viscosity (25 ℃ C.), mPas | 30000-60000 |
In the embodiment of the invention, a certain amount of specific solvent, tetraethylenepentamine and glycerol are added into a reaction kettle, acrylonitrile is slowly dripped after the specific solvent, the tetraethylpentamine and the glycerol are uniformly mixed at normal temperature, and the solvent is removed under reduced pressure after the reaction is finished, so that the HX-878 product is obtained.
The invention has the following beneficial effects:
(1) the reaction condition is mild, the reaction can be carried out at normal temperature and normal pressure, the reaction time is short, the product viscosity is low, the purity and the yield are high, and the reaction weight yield can reach 92.6%.
(2) The solvent is convenient to recycle and reuse, and no hazardous waste is generated in the preparation process.
(3) The process is suitable for industrial scale production.
The above disclosure is only for the purpose of illustrating the preferred embodiments of the present invention, and it is therefore to be understood that the invention is not limited by the scope of the appended claims.
Claims (4)
1. A method for preparing HX-878, comprising the following steps:
s1, dissolving tetraethylenepentamine and glycerol in a specific solvent, fully stirring at normal temperature to uniformly mix the materials, slowly dropwise adding acrylonitrile, controlling the reaction temperature within a certain range, and continuously preserving heat for a certain reaction time after dropwise adding;
s2, distilling and recovering the solvent under the reduced pressure condition, and then carrying out reduced pressure distillation to remove trace water to obtain HX-878, wherein the HX-878 is qualified when the water content is less than or equal to 0.1%.
2. The HX-878 production method according to claim 1, wherein in the S1 step, the specific solvent is one or a mixture of toluene, cyclohexane, ethyl acetate and dichloroethane.
3. The HX-878 production method of claim 2, wherein in the S1 step, the reaction temperature is 0-90 ℃, the mass ratio of tetraethylenepentamine to glycerin is 1: 1-3.5: 1, and the reaction time is 0.5-3 hours.
4. The HX-878 production method according to claim 2, wherein in the S2 step, the specific solvent is first recovered under normal pressure, and then the trace amount of water is removed under vacuum twice, thereby obtaining HX-878.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111532972.1A CN114213668A (en) | 2021-12-15 | 2021-12-15 | Preparation method of HX-878 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202111532972.1A CN114213668A (en) | 2021-12-15 | 2021-12-15 | Preparation method of HX-878 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN114213668A true CN114213668A (en) | 2022-03-22 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202111532972.1A Withdrawn CN114213668A (en) | 2021-12-15 | 2021-12-15 | Preparation method of HX-878 |
Country Status (1)
| Country | Link |
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| CN (1) | CN114213668A (en) |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4000023A (en) * | 1968-12-09 | 1976-12-28 | Aerojet-General Corporation | Bonding agents for polyurethane |
| US4493741A (en) * | 1983-04-25 | 1985-01-15 | The United States Of America As Represented By The Secretary Of The Army | Amine salts as bonding agents |
| US5472532A (en) * | 1993-06-14 | 1995-12-05 | Thiokol Corporation | Ambient temperature mix, cast, and cure composite propellant formulations |
| CN102757362A (en) * | 2012-07-20 | 2012-10-31 | 苏州大学 | Acrylate monomer and preparation method thereof |
-
2021
- 2021-12-15 CN CN202111532972.1A patent/CN114213668A/en not_active Withdrawn
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4000023A (en) * | 1968-12-09 | 1976-12-28 | Aerojet-General Corporation | Bonding agents for polyurethane |
| US4493741A (en) * | 1983-04-25 | 1985-01-15 | The United States Of America As Represented By The Secretary Of The Army | Amine salts as bonding agents |
| US5472532A (en) * | 1993-06-14 | 1995-12-05 | Thiokol Corporation | Ambient temperature mix, cast, and cure composite propellant formulations |
| CN102757362A (en) * | 2012-07-20 | 2012-10-31 | 苏州大学 | Acrylate monomer and preparation method thereof |
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| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
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| WW01 | Invention patent application withdrawn after publication | ||
| WW01 | Invention patent application withdrawn after publication |
Application publication date: 20220322 |