CN116120540A - Method for preparing polyether-ether-ketone at low temperature - Google Patents
Method for preparing polyether-ether-ketone at low temperature Download PDFInfo
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- CN116120540A CN116120540A CN202310308769.9A CN202310308769A CN116120540A CN 116120540 A CN116120540 A CN 116120540A CN 202310308769 A CN202310308769 A CN 202310308769A CN 116120540 A CN116120540 A CN 116120540A
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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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/34—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives
- C08G65/38—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols
- C08G65/40—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from hydroxy compounds or their metallic derivatives derived from phenols from phenols (I) and other compounds (II), e.g. OH-Ar-OH + X-Ar-X, where X is halogen atom, i.e. leaving group
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/30—Hydrogen technology
- Y02E60/50—Fuel cells
Abstract
The invention provides a method for preparing polyether-ether-ketone at low temperature, belonging to the technical field of high polymer materials. The method uses p-difluorobenzene and 4,4' -dihydroxybenzophenone as raw materials to react in potassium hydroxide or sodium hydroxide aqueous solution, and the potassium hydroxide or sodium hydroxide is used as a reactant and a catalyst for nucleophilic reaction, so that the reaction can be carried out at a lower temperature without a large amount of organic solvents, and the method is beneficial to environmental protection. The method has very complete reaction process, and the purity of the prepared product can reach 99.9%.
Description
Technical Field
The invention belongs to the technical field of high polymer materials, and particularly relates to a method for preparing polyether-ether-ketone at low temperature.
Background
The polyether-ether-ketone is an aromatic linear polymer material, is a novel semi-crystalline aromatic thermoplastic engineering plastic which is successfully researched and developed in the last 70 th century, has high temperature resistance, chemical corrosion resistance, high strength, high modulus, high fracture toughness, excellent dimensional stability and other physical and chemical properties. The glass transition temperature (Tg) of the polyetheretherketone is 143 ℃, the melting point (Tm) is 334 ℃, and the maximum crystallinity theoretically achievable is 48%, typically 20% -30%. The density in the amorphous state was 1.265g/cm3, and the density at the maximum crystallinity was 1.32g/cm3. The crystal form of the material has outstanding heat resistance and mechanical properties, the continuous use temperature is 260 ℃, the instant use temperature can reach 300 ℃, and the material is not decomposed in a short time at 400 ℃. The polyether-ether-ketone has excellent comprehensive performance, so that the polyether-ether-ketone has wide application in various fields.
Polyetheretherketone is a high-end product in specialty engineering plastics, which was developed in 1978 by the company ICI of the imperial chemical industry in the United kingdom, after which PEEK from the company ICI had been converted to that from VICTREX in the United kingdom. In China, due to the excellent performance of PEEK, research thereof has been put into the seventy-fifteen national major technological project of attack and the "863 program". The current synthetic methods of polyether-ether-ketone are synthesized by gradual polymerization of alkylated bisphenol salts. Typical reaction is to use 4,4' -difluorobenzophenone and hydroquinone to react with sodium carbonate or potassium carbonate, the reaction is carried out in aprotic solvents such as diphenyl sulfone or sulfolane, the reaction temperature is above 300 ℃, the polyether-ether-ketone products on the market at present are all synthesized based on the method, and the reaction method has the defects of high reaction temperature, large amount of organic solvents of diphenyl sulfone, easy oxidation in the reaction process, inert gas protection, high price of raw materials and the like.
Disclosure of Invention
The object of the present invention is to provide a process for preparing polyetheretherketone at low temperature, which process is carried out at relatively low temperatures and does not require large amounts of organic solvents.
In order to achieve the above purpose, the present invention adopts the following technical scheme:
a method for preparing polyether-ether-ketone at low temperature, comprising:
taking p-difluorobenzene and 4,4' -dihydroxybenzophenone as raw materials, and reacting in an alkali solution to obtain polyether-ether-ketone; the reaction temperature is 40-80 ℃.
Preferably, the alkali solution is potassium hydroxide or sodium hydroxide.
Preferably, the concentration of the alkali solution is 10% -50%.
Preferably, the concentration of the alkali solution is 17% -34%.
Preferably, the reaction time is 1.5-2 hours.
Preferably, the molar ratio of the 4,4' -dihydroxybenzophenone to the p-difluorobenzene is 1:1.
Preferably, the molar ratio of the alkali in the alkali solution to the 4,4' -dihydroxybenzophenone is 2-2.5:1.
Preferably, the method specifically comprises the following steps: adding an alkali solution into a reaction container, maintaining the temperature of the alkali solution in the reaction container at 40-50 ℃, adding 4,4 '-dihydroxybenzophenone under stirring, raising the temperature in the reaction container to 55-80 ℃ after the 4,4' -dihydroxybenzophenone is completely dissolved, dropwise adding p-difluorobenzene, generating precipitate, and carrying out suction filtration, washing and drying after the dropwise adding is finished to obtain polyether-ether-ketone.
The beneficial effects of the invention are that
The invention provides a method for preparing polyether-ether-ketone at low temperature, which uses p-difluorobenzene and 4,4' -dihydroxybenzophenone as raw materials to react in potassium hydroxide or sodium hydroxide aqueous solution, wherein potassium hydroxide or sodium hydroxide is used as a reactant and a catalyst for nucleophilic reaction, so that the reaction can be carried out at a lower temperature without a large amount of organic solvents, and the method is beneficial to environmental protection. The method has complete reaction process, the purity of the prepared product can reach 99.9 percent, and the molecular weight of the minimum repeated unit of the generated polyether-ether-ketone is 288.
Detailed Description
The invention is described in further detail below in connection with specific examples, wherein the starting materials are all commercially available.
Example 1
500ml of distilled water is poured into a beaker, 123.4g of KOH (the excess amount of the KOH is 10 percent relative to the 4,4 '-dihydroxybenzophenone in terms of the molar ratio reaction) is weighed, KOH is slowly added into the beaker under the stirring condition, the temperature of KOH aqueous solution in the beaker is maintained to be 45 ℃ after the KOH is completely dissolved, 212.2g of 4,4' -dihydroxybenzophenone is slowly added under the stirring condition, after the solid in the beaker is completely dissolved, the temperature of the liquid in the beaker is raised to 65 ℃, 114.1g of p-difluorobenzene is slowly added into the beaker in a dropwise manner, precipitate is generated, and the liquid in the beaker is filtered after 1.5-2h of dropwise addition is completed. The suction filtration is washed by ethanol for three times, washed by distilled water for three times and dried. The physical properties of the precipitate were tested.
Example 2
500ml of distilled water is weighed and poured into a beaker, 134.6g of KOH (20% excess) is weighed, KOH is slowly added into the beaker under the stirring condition, after the KOH is completely dissolved, the temperature of a KOH aqueous solution in the beaker is maintained at 45 ℃, 212.2g of 4,4' -dihydroxybenzophenone is slowly added under the stirring condition, after the solid in the beaker is completely dissolved, the temperature of the liquid in the beaker is raised to 65 ℃, 114.1g of p-difluorobenzene is slowly added into the beaker in a dropwise manner, precipitates are generated, and after the dropwise addition is completed for 1.5-2 hours, the liquid in the beaker is filtered in a suction manner. The suction filtration is washed by ethanol for three times, washed by distilled water for three times and dried. The physical properties of the precipitate were tested.
Example 3
500ml of distilled water is weighed and poured into a beaker, 157.1g of KOH (40% excess) is weighed, KOH is slowly added into the beaker under the stirring condition, after the KOH is completely dissolved, the temperature of a KOH aqueous solution in the beaker is maintained to be 45 ℃, 212.2g of 4,4' -dihydroxybenzophenone is slowly added under the stirring condition, after the solid in the beaker is completely dissolved, the temperature of the liquid in the beaker is raised to 65 ℃, 114.1g of p-difluorobenzene is slowly added into the beaker in a dropwise manner, precipitates are generated, and after the dropwise addition is completed for 1.5-2 hours, the liquid in the beaker is filtered in a suction manner. The suction filtration is washed by ethanol for three times, washed by distilled water for three times and dried. The physical properties of the precipitate were tested.
Example 4
500ml of distilled water is weighed and poured into a beaker, 168.3g of KOH (50% excess) is weighed, KOH is slowly added into the beaker under the stirring condition, after the KOH is completely dissolved, the temperature of a KOH aqueous solution in the beaker is maintained to be 45 ℃, 212.2g of 4,4' -dihydroxybenzophenone is slowly added under the stirring condition, after the solid in the beaker is completely dissolved, the temperature of the liquid in the beaker is raised to 65 ℃, 114.1g of p-difluorobenzene is slowly added into the beaker in a dropwise manner, precipitates are generated, and after the dropwise addition is completed for 1.5-2 hours, the liquid in the beaker is filtered in a suction manner. The suction filtration is washed by ethanol for three times, washed by distilled water for three times and dried. The physical properties of the precipitate were tested.
Example 5
500ml of distilled water is weighed and poured into a beaker, 88g of NaOH (10% excess) is weighed, naOH is slowly added into the beaker under the stirring condition, after the NaOH is completely dissolved, the temperature of an aqueous solution of NaOH in the beaker is maintained to be 45 ℃, 212.2g of 4,4' -dihydroxybenzophenone is slowly added under the stirring condition, after the solid in the beaker is completely dissolved, the temperature of the liquid in the beaker is raised to 65 ℃, 114.1g of p-difluorobenzene is slowly added into the beaker in a dropwise manner, precipitate is generated, and after the dropwise addition of 1.5-2h, the liquid in the beaker is filtered in a suction manner. The suction filtration is washed by ethanol for three times, washed by distilled water for three times and dried. The physical properties of the precipitate were tested.
Example 6
500ml of distilled water is weighed and poured into a beaker, 96g of NaOH (20% excess) is weighed, naOH is slowly added into the beaker under the stirring condition, after the NaOH is completely dissolved, the temperature of an aqueous solution of NaOH in the beaker is maintained to be 45 ℃, 212.2g of 4,4' -dihydroxybenzophenone is slowly added under the stirring condition, after the solid in the beaker is completely dissolved, the temperature of the liquid in the beaker is raised to 65 ℃, 114.1g of p-difluorobenzene is slowly added into the beaker in a dropwise manner, precipitate is generated, and after the dropwise addition of 1.5-2h, the liquid in the beaker is filtered in a suction manner. The suction filtration is washed by ethanol for three times, washed by distilled water for three times and dried. The physical properties of the precipitate were tested.
Example 7
500ml of distilled water is weighed and poured into a beaker, 112g of NaOH (40% excess) is weighed, naOH is slowly added into the beaker under the stirring condition, after the NaOH is completely dissolved, the temperature of an aqueous solution of NaOH in the beaker is maintained to be 45 ℃, 212.2g of 4,4' -dihydroxybenzophenone is slowly added under the stirring condition, after the solid in the beaker is completely dissolved, the temperature of the liquid in the beaker is raised to 65 ℃, 114.1g of p-difluorobenzene is slowly added into the beaker in a dropwise manner, precipitate is generated, and after the dropwise addition of 1.5-2h, the liquid in the beaker is filtered in a suction manner. The suction filtration is washed by ethanol for three times, washed by distilled water for three times and dried. The physical properties of the precipitate were tested.
Example 8
500ml of distilled water is weighed and poured into a beaker, 120g of NaOH (50% excess) is weighed, naOH is slowly added into the beaker under the stirring condition, after the NaOH is completely dissolved, the temperature of an aqueous solution of NaOH in the beaker is maintained to be 45 ℃, 212.2g of 4,4' -dihydroxybenzophenone is slowly added under the stirring condition, after the solid in the beaker is completely dissolved, the temperature of the liquid in the beaker is raised to 65 ℃, 114.1g of p-difluorobenzene is slowly added into the beaker in a dropwise manner, precipitate is generated, and after the dropwise addition of 1.5-2h, the liquid in the beaker is filtered in a suction manner. The suction filtration is washed by ethanol for three times, washed by distilled water for three times and dried. The physical properties of the precipitate were tested.
Example 9
Weighing 1000ml of distilled water, pouring the distilled water into a beaker, weighing 112g of NaOH, slowly adding NaOH into the beaker under the stirring condition, maintaining the temperature of an aqueous solution of NaOH in the beaker to be 45 ℃ after the NaOH is completely dissolved, slowly adding 212.2g of 4,4' -dihydroxybenzophenone under the stirring condition, heating the liquid in the beaker to 65 ℃ after the solid in the beaker is completely dissolved, slowly dripping 114.1g of p-difluorobenzene into the beaker, generating precipitate, and carrying out suction filtration on the liquid in the beaker after 1.5-2h of dripping is completed. The suction filtration is washed by ethanol for three times, washed by distilled water for three times and dried. The physical properties of the precipitate were tested.
Example 10
400ml of distilled water is weighed and poured into a beaker, 112g of NaOH is weighed, naOH is slowly added into the beaker under the stirring condition, after the NaOH is completely dissolved, the temperature of an aqueous solution of NaOH in the beaker is maintained to be 45 ℃, 212.2g of 4,4' -dihydroxybenzophenone is slowly added under the stirring condition, after the solid in the beaker is completely dissolved, the temperature of the liquid in the beaker is raised to 65 ℃, 114.1g of p-difluorobenzene is slowly added into the beaker in a dropwise manner, precipitate is generated, and after the dropwise addition is completed for 1.5-2h, the liquid in the beaker is filtered in a suction manner. The suction filtration is washed by ethanol for three times, washed by distilled water for three times and dried. The physical properties of the precipitate were tested.
Example 11
300ml of distilled water is weighed and poured into a beaker, 112g of NaOH is weighed, naOH is slowly added into the beaker under the stirring condition, after the NaOH is completely dissolved, the temperature of an aqueous solution of NaOH in the beaker is maintained to be 45 ℃, 212.2g of 4,4' -dihydroxybenzophenone is slowly added under the stirring condition, after the solid in the beaker is completely dissolved, the temperature of the liquid in the beaker is raised to 65 ℃, 114.1g of p-difluorobenzene is slowly added into the beaker in a dropwise manner, precipitate is generated, and after the dropwise addition is completed for 1.5-2h, the liquid in the beaker is filtered in a suction manner. The suction filtration is washed by ethanol for three times, washed by distilled water for three times and dried. The physical properties of the precipitate were tested.
Comparative example 1
1000ml of distilled water was weighed into a beaker, 177.84g Ca (OH) was weighed 2 In the stirring processUnder stirring, ca (OH) was slowly added to the beaker 2 To be fully added with Ca (OH) 2 The bottom of the back beaker is provided with sediment, ca (OH) 2 The reaction was continued for 1 hour with the addition of 212.2g of 4,4' -dihydroxybenzophenone slowly while maintaining the temperature of the aqueous solution in the beaker at 45℃without complete dissolution, and a large amount of solid precipitate remained in the beaker and the reaction was incomplete. The temperature of the liquid in the beaker is raised to 65 ℃, 114.1g of p-difluorobenzene is slowly added dropwise into the beaker, and after the dropwise addition is completed for 1.5-2 hours, the liquid in the beaker is filtered by suction. The suction filtration is washed by ethanol for three times, washed by distilled water for three times and dried. Physical Properties of the precipitate were tested, and the precipitate contained a large amount of Ca (OH) 2 And 4,4' -difluorobenzophenone, demonstrating that the reaction did not proceed.
Comparative example 2
500ml of distilled water is poured into a beaker, 157.1g of KOH (40% excess) is weighed, KOH is slowly added into the beaker under the stirring condition, after the KOH is completely dissolved, the temperature of a KOH aqueous solution in the beaker is maintained to be 25 ℃, 212.2g of 4,4' -dihydroxybenzophenone is slowly added under the stirring condition, after the solid in the beaker is dissolved, the temperature of the liquid in the beaker is raised to 35 ℃, 114.1g of p-difluorobenzene is slowly added into the beaker in a dropwise manner, after the dropwise addition is completed for 1.5-2h, the liquid in the beaker is filtered in a suction manner, no solid is left on filter paper, and the reaction is proved to be not carried out.
Comparative example 3
500ml of distilled water is poured into a beaker, 157.1g of KOH (40% excess) is weighed, KOH is slowly added into the beaker under the stirring condition, after the KOH is completely dissolved, the temperature of a KOH aqueous solution in the beaker is maintained to be 45 ℃, 212.2g of 4,4' -dihydroxybenzophenone is slowly added under the stirring condition, after the solid in the beaker is completely dissolved, the temperature of the liquid in the beaker is raised to 85 ℃, 114.1g of p-difluorobenzene is slowly added into the beaker in a dropwise manner, precipitates are generated, after the dropwise addition is completed for 1.5-2h, the liquid in the beaker is filtered, and sticky solids are left on filter paper. The solid is washed by ethanol for three times, dried after being washed by distilled water for three times, and still has partial caking and cannot be dispersed in ethanol and water. The melting point of the precipitate was 319.73 ℃ and the melting point range of the polyetheretherketone was not reached, demonstrating that the precipitate was not pure polyetheretherketone but a mixture.
Comparative example 4
500ml of distilled water is weighed and poured into a beaker, 101g of KOH (10% of the shortage) is weighed, KOH is slowly added into the beaker under the stirring condition, after the KOH is completely dissolved, the temperature of a KOH aqueous solution in the beaker is maintained to be 45 ℃, 212.2g of 4,4' -dihydroxybenzophenone is slowly added under the stirring condition, after the solid in the beaker is completely dissolved, the temperature of the liquid in the beaker is raised to 65 ℃, 114.1g of p-difluorobenzene is slowly added into the beaker in a dropwise manner, precipitates are generated, and after the dropwise addition is completed for 1.5-2 hours, the liquid in the beaker is filtered in a suction manner. The suction filtration is washed by ethanol for three times, washed by distilled water for three times and dried. The physical properties of the precipitate were tested. When the amount of potassium carbonate is insufficient, the reaction is insufficient, the yield is lower than 60%, and the purity of the generated polyether-ether-ketone is low.
The samples of the above examples were tested for melting point and viscosity as shown in the following table:
melting point (. Degree. C.) | Viscosity (Pa, S) | |
Example 1 | 345.73 | 212.4 |
Example 2 | 343.97 | 290.5 |
Example 3 | 346.13 | 174.2 |
Example 4 | 347.84 | 112.8 |
Example 5 | 347.15 | 121.4 |
Example 6 | 346.29 | 185.3 |
Example 7 | 343.62 | 310.3 |
Example 8 | 347.53 | 118.7 |
Example 9 | 348.48 | 87.2 |
Example 10 | 344.0 | 273.6 |
Example 11 | 343.17 | 342.5 |
Comparative example 4 | 324.34 | 65.8 |
According to the invention, polyether-ether-ketone with certain molecular weight is prepared at relatively low reaction temperature by the method for preparing polyether-ether-ketone by the embodiment and analyzing and testing results, the reaction is complete due to the fact that the excessive potassium hydroxide or sodium hydroxide is different, in addition, the reaction process is influenced by the concentration of the aqueous solution of potassium hydroxide or the concentration of the aqueous solution of sodium hydroxide, the length of a molecular chain is determined, and the molecular weight of the polyether-ether-ketone can be controlled.
Claims (8)
1. A method for preparing polyether-ether-ketone at low temperature, which is characterized by comprising the following steps:
taking p-difluorobenzene and 4,4' -dihydroxybenzophenone as raw materials, and reacting in an alkali solution to obtain polyether-ether-ketone; the reaction temperature is 40-80 ℃.
2. The method for preparing polyether-ether-ketone at low temperature according to claim 1, wherein the alkaline solution is potassium hydroxide or sodium hydroxide.
3. The method for preparing polyether-ether-ketone at low temperature according to claim 1, wherein the concentration of the alkali solution is 10% -50%.
4. A method for preparing polyetheretherketone at low temperature as claimed in claim 3, wherein the concentration of the alkaline solution is 17% -34%.
5. The method for preparing polyether-ether-ketone at low temperature according to claim 1, wherein the reaction time is 1.5-2h.
6. The method for preparing polyether-ether-ketone at low temperature according to claim 1, wherein the molar ratio of 4,4' -dihydroxybenzophenone to p-difluorobenzene is 1:1.
7. The method for preparing polyether-ether-ketone at low temperature according to claim 1, wherein the molar ratio of the alkali in the alkali solution to the 4,4' -dihydroxybenzophenone is (2-2.5): 1.
8. The method for preparing polyether-ether-ketone at low temperature according to claim 1, wherein the method specifically comprises the following steps: adding an alkali solution into a reaction container, maintaining the temperature of the alkali solution in the reaction container at 40-50 ℃, adding 4,4 '-dihydroxybenzophenone under stirring, raising the temperature in the reaction container to 55-80 ℃ after the 4,4' -dihydroxybenzophenone is completely dissolved, dropwise adding p-difluorobenzene, generating precipitate, and carrying out suction filtration, washing and drying after the dropwise adding is finished to obtain polyether-ether-ketone.
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