CN113214467B - Preparation method of bisphenol A polyoxypropylene ether - Google Patents
Preparation method of bisphenol A polyoxypropylene ether Download PDFInfo
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- CN113214467B CN113214467B CN202110627512.0A CN202110627512A CN113214467B CN 113214467 B CN113214467 B CN 113214467B CN 202110627512 A CN202110627512 A CN 202110627512A CN 113214467 B CN113214467 B CN 113214467B
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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
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C08G65/2612—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups containing aromatic or arylaliphatic hydroxyl groups
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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
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2669—Non-metals or compounds thereof
- C08G65/2672—Nitrogen or compounds thereof
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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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/584—Recycling of catalysts
Abstract
The invention provides a preparation method of bisphenol A polyoxypropylene ether, which takes bisphenol A as a raw material, takes liquefied propylene oxide as a solvent under the reaction conditions of high pressure and low temperature, and performs ring opening polymerization under the action of an amine catalyst to prepare the bisphenol A polyoxypropylene ether, and finally the prepared bisphenol A polyoxypropylene ether product has no odor, light color and low VOC content. The invention leads the epoxypropane raw material to be liquefied and dissolved with the bisphenol A by pressurizing, solves the problems of long melting time and dark color of the target product in a high-temperature melting method, does not need to introduce other organic solvents, and has simpler and easier process; the reaction product can be effectively separated through simple vacuum removal, does not need post-treatment and is easy for industrial application.
Description
Technical Field
The invention belongs to the technical field of fine chemical synthesis, and particularly relates to a preparation method of polyether from high-melting-point solid polyol, and more particularly relates to a preparation method of bisphenol A polyoxypropylene ether.
Background
Bisphenol A polyoxypropylene ether is prepared by ring-opening polymerization of bisphenol A as initiator and propylene oxide in the presence of catalyst. The aromatic ring and the carbon-oxygen chain structure in the molecule respectively endow the material with specific rigidity and toughness, thereby effectively improving the structure and the property of the polymer. For example, the synthetic surfactant with bisphenol A polyoxypropylene ether as a skeleton generates stronger synergistic effect than the conventional monomer surfactant, improves the washing effect, reduces irritants, and has high efficiency solubilization, emulsion stability, foam stability and the like. Similarly, the bisphenol A epoxy resin synthesized by taking bisphenol A polyoxypropylene ether as an intermediate has greatly improved mechanical property, corrosion resistance, chemical resistance and flame retardance. In addition, it can be used as monomer of synthetic resin, and also can be used as modifier of high-molecular polymer chain, and has important application in the fields of solvent-free paint, adhesive, glass impregnating agent and coating material, etc.
As bisphenol A is a high-melting-point solid alcohol (melting point 158 ℃), the conventional process is to add bisphenol A into a reactor, heat the bisphenol A to the melting point of the raw materials by steam or oil bath under the protection of inert gas, and then introduce epoxide into the reactor for reaction after the raw materials are melted. Kachikawa et al, Goto et al, reacted at 160 deg.C for 1-2h with triethylamine, N-dimethylammonium acetate, respectively, as catalysts to give bisphenol A polyether. Yamashita and the like select to react for 1h at the reaction temperature of 170 ℃ by taking quaternary ammonium salt as a catalyst to obtain a bisphenol A polyether product. However, the method has the problem that solid alcohol is heated unevenly in the melting process, bisphenol A with poor thermal stability can be degraded into a monofunctional derivative, the decomposed product is easy to carbonize, the color of the product is deepened rapidly, and the indexes of the finished product such as color, purity and the like are seriously influenced. Therefore, Carroll et al propose adding the solvent methyl isobutyl ketone, dissolving the starting solid alcohol, lowering the reaction temperature to limit the mono-functional degradation of the derivatives, and finally reacting at 120 ℃ for 4h with tri-n-propylamine as catalyst to obtain the product. Tanizaki and the like further provide that the bisphenol A polyether is prepared by taking toluene as a solvent and triethylamine as a catalyst for reaction for 4 hours at 115 ℃, the reaction selectivity is high, but a large amount of solvent needs to be removed after the reaction is finished to obtain the product, so that the production cost is greatly increased. In the synthesis process, the VOC organic matter residue caused by factors such as incomplete solvent removal, introduction of various auxiliary agents in post-treatment and the like can cause unpredictable harm to air quality and human bodies when the substances are used for preparing polyurethane products in the later period. Therefore, domestic bisphenol A polyether manufacturers are actively concerned about the reduction of VOC content.
In addition, the ring-opening polymerization of bisphenol a and propylene oxide needs to be carried out under the action of a catalyst, and usually, a KOH-type alkali metal-based catalyst is used, which contains metal elements, and the residual metal elements cause the generation of impurities such as aldehydes, peroxides and the like in polyether polyol, thereby not only increasing the odor and VOC of the product, but also causing the discoloration of the product. Further acid is needed for neutralization and removal, and the post-treatment step is complicated. Therefore, manufacturers have developed catalysts which do not contain metal elements, represented by amines, and polyether products produced by using the catalysts only need to be removed by simple vacuum without post-treatment. But the color of the product is not up to the standard due to the overhigh reaction temperature, and the application performance is seriously influenced.
The present application was made based on this.
Disclosure of Invention
Aiming at the defects in the existing bisphenol A polyoxypropylene ether synthesis method, the invention selects liquid propylene oxide raw material as solvent under the reaction conditions of high pressure and low temperature, and the bisphenol A polyoxypropylene ether with no odor, low VOC and good color is prepared by ring opening polymerization under the action of amine catalyst.
In order to achieve the purpose, the invention adopts the following technical scheme:
a process for preparing a bisphenol a polyoxypropylene ether, comprising:
bisphenol A is used as a raw material, under the reaction conditions of high pressure and low temperature, liquefied propylene oxide is used as a solvent, and ring opening polymerization is carried out under the action of an amine catalyst to obtain bisphenol A polyoxypropylene ether.
Specifically, the preparation method of the bisphenol A polyoxypropylene ether comprises the following steps:
s1, putting the bisphenol A into a high-pressure reaction kettle, replacing air in the high-pressure reaction kettle with nitrogen, and finally keeping the system at a negative pressure;
s2, adding the epoxypropane and the catalyst into the high-pressure reaction kettle at one time at room temperature;
s3, slowly raising the temperature of the reaction kettle to 50 ℃, and starting stirring simultaneously;
s4, after the bisphenol A is completely dissolved, heating to a set reaction temperature, controlling the pressure in the kettle within a required value range, and transferring heat released in the reaction;
and S5, carrying out pressure maintaining reaction and vacuum degassing to obtain the finished product bisphenol A polyoxypropylene ether.
In S1, the nitrogen was replaced by pumping, and the pump was stopped for the third time and continued to negative pressure (-0.095MPa), ensuring that no air was present.
In the S4, the reaction temperature is set to be 60-90 ℃, after the bisphenol A is completely dissolved, the temperature in the kettle is raised to be 60-90 ℃, and the pressure in the kettle naturally rises to be within the range of 0.6-1.6MPa at the moment, namely the saturated vapor pressure at the temperature. In S4, the high pressure of the closed system promotes the liquefaction of the propylene oxide, so that a uniform mixed system is formed among the bisphenol A, the propylene oxide and the catalyst, the reaction is fully carried out, the pressure range of the reaction temperature of 60-90 ℃ is 0.6-1.6MPa, preferably 1.0-1.6MPa, and the full catalytic reaction of the catalyst can be satisfied.
In the step S2, the amount of propylene oxide is: generally, the PO amount of 2 mol can mostly dissolve 1 mol of bisphenol A, and the dissolving time is long; on the other hand, 4 mol or more of PO can dissolve 1 mol of bisphenol A in 1 hour.
Preferably, the molar ratio of the bisphenol A to the propylene oxide is 1: 2-30, and the addition amount of the catalyst is 1-3 per mill of the total mass of the bisphenol A and the propylene oxide.
The structure of the catalyst in S4 is as follows:
wherein R is 1 、R 2 、R 3 All are electron-rich substituents, such as one or more of alkyl and phenyl.
The S5 includes: and after the pressure maintaining reaction is carried out for 1-2h, vacuum degassing is carried out at the temperature of 80 ℃ to obtain a finished product of bisphenol A polyoxypropylene ether.
Compared with the prior art, the invention has the following advantages:
the invention liquefies the propylene oxide raw material by pressurizing (0.6-1.6MPa) to be used as a solvent to dissolve the bisphenol A, and carries out ring-opening polymerization at the temperature of 60-90 ℃, thereby successfully solving the problems of long melting time of the high-melting point raw material bisphenol A and dark target product color caused by a high-temperature method;
(2) the method does not need to introduce other organic solvents, reduces a series of complicated steps such as solvent removal and the like, has simple and easy process, and obviously reduces the VOC content of the product;
(3) the reaction product can be effectively separated through simple vacuum removal, does not need post-treatment and is easier for industrialized application.
Detailed Description
The present invention is described in more detail below with reference to examples. These examples are merely illustrative of the best mode of carrying out the invention and do not limit the scope of the invention in any way.
Example 1
Putting 228g of bisphenol A into a high-pressure reaction kettle with a high-pressure kettle controller, vacuumizing by using a vacuum pump, replacing air in the high-pressure reaction kettle with nitrogen for three times, and finally keeping the system at a negative pressure; under the condition of room temperature, 116g of propylene oxide and 0.344g of triethylamine catalyst are mixed and then added into a high-pressure reaction kettle, the temperature of the reaction kettle is slowly raised to 50 ℃, and stirring is started simultaneously; after bisphenol A is completely dissolved, the temperature is raised to the set reaction temperature of 80 ℃, and the pressure in the kettle is controlled within the required value range (1.0-1.2 MPa). In the reaction, the released heat is removed by cooling water; and (5) continuously carrying out pressure maintaining reaction for 1-2h, carrying out vacuum degassing for 30min, and discharging to obtain a finished product.
The molar ratio of the bisphenol A to the propylene oxide is 1: 2; the addition amount of the catalyst is 3 per mill of the total mass of the bisphenol A and the propylene oxide.
Example 2
Putting 228g of bisphenol A into a high-pressure reaction kettle with a high-pressure kettle controller, vacuumizing by using a vacuum pump, replacing air in the high-pressure reaction kettle with nitrogen for three times, and finally keeping the system at a negative pressure; under the condition of room temperature, 580g of propylene oxide and 2.424g of triethylamine catalyst are mixed and then added into a high-pressure reaction kettle, the temperature of the reaction kettle is slowly raised to 50 ℃, and stirring is started simultaneously; after bisphenol A is completely dissolved, heating to the set reaction temperature of 80 ℃, controlling the pressure in the kettle within the required value range (1.0-1.2MPa), and removing the released heat in the reaction by using cooling water; and (5) continuously carrying out pressure maintaining reaction for 1-2h, carrying out vacuum degassing for 30min, and discharging to obtain a finished product.
The molar ratio of the bisphenol A to the propylene oxide is 1: 10; the addition amount of the catalyst is 3 per mill of the total mass of the bisphenol A and the propylene oxide.
Example 3
Putting 228g of bisphenol A into a high-pressure reaction kettle with a high-pressure kettle controller, vacuumizing by using a vacuum pump, replacing air in the high-pressure reaction kettle with nitrogen for three times, and finally keeping the system at a negative pressure; under the condition of room temperature, 1160g of propylene oxide and 4.164g of triethylamine catalyst are mixed and then added into a high-pressure reaction kettle, the temperature of the reaction kettle is slowly raised to 50 ℃, and stirring is started simultaneously; after bisphenol A is completely dissolved, heating to the set reaction temperature of 80 ℃, controlling the pressure in the kettle within the required value range (1.0-1.2MPa), and removing the released heat in the reaction by using cooling water; and (5) continuously carrying out pressure maintaining reaction for 1-2h, carrying out vacuum degassing for 30min, and discharging to obtain a finished product.
The molar ratio of the bisphenol A to the propylene oxide is 1: 20. The adding amount of the catalyst is 3 per mill of the total mass of the bisphenol A and the propylene oxide.
Example 4
Putting 228g of bisphenol A into a high-pressure reaction kettle with a high-pressure kettle controller, vacuumizing by using a vacuum pump, replacing air in the high-pressure reaction kettle with nitrogen for three times, and finally keeping the system at a negative pressure; under the condition of room temperature, 1740g of propylene oxide and 5.904g of triethylamine catalyst are mixed and then added into a high-pressure reaction kettle, the temperature of the reaction kettle is slowly raised to 50 ℃, and stirring is started simultaneously; after bisphenol A is completely dissolved, heating to the set reaction temperature of 80 ℃, controlling the pressure in the kettle within the required value range (1.0-1.2MPa), and removing the released heat in the reaction by using cooling water; and (5) continuously carrying out pressure maintaining reaction for 1-2h, carrying out vacuum degassing for 30min, and discharging to obtain a finished product.
The molar ratio of the bisphenol A to the propylene oxide is 1: 30. The addition amount of the catalyst is 3 per mill of the total mass of the bisphenol A and the propylene oxide.
Example 5 (temperature 60 ℃ C.)
Putting 228g of bisphenol A into a high-pressure reaction kettle with a high-pressure kettle controller, vacuumizing by using a vacuum pump, replacing air in the high-pressure reaction kettle with nitrogen for three times, and finally keeping the system at a negative pressure; under the condition of room temperature, 580g of propylene oxide and 2.424g of triethylamine catalyst are mixed and then added into a high-pressure reaction kettle, the temperature of the reaction kettle is slowly raised to 50 ℃, and stirring is started simultaneously; after bisphenol A is completely dissolved, keeping the reaction temperature at 60 ℃, controlling the pressure in the kettle within a required value range (0.6-0.8MPa), and removing the released heat by using cooling water in the reaction; and (5) continuously carrying out pressure maintaining reaction for 1-2h, carrying out vacuum degassing for 30min, and discharging to obtain a finished product.
The molar ratio of the bisphenol A to the propylene oxide is 1: 10. The addition amount of the catalyst is 3 per mill of the total mass of the bisphenol A and the propylene oxide.
Example 6
Putting 228g of bisphenol A into a high-pressure reaction kettle with a high-pressure kettle controller, vacuumizing by using a vacuum pump, replacing air in the high-pressure reaction kettle with nitrogen for three times, and finally keeping the system at a negative pressure; under the condition of room temperature, 580g of propylene oxide and 2.424g of triethylamine catalyst are mixed and then added into a high-pressure reaction kettle, the temperature of the reaction kettle is slowly raised to 50 ℃, and stirring is started at the same time; after bisphenol A is completely dissolved, keeping the reaction temperature at 70 ℃, controlling the pressure in the kettle within a required value range (0.8-1.0MPa), and removing the released heat by using cooling water in the reaction; and (5) continuously carrying out pressure maintaining reaction for 1-2h, carrying out vacuum degassing for 30min, and discharging to obtain a finished product.
The molar ratio of the bisphenol A to the propylene oxide is 1: 10. The adding amount of the catalyst is 3 per mill of the total mass of the bisphenol A and the propylene oxide.
Example 7
Putting 228g of bisphenol A into a high-pressure reaction kettle with a high-pressure kettle controller, vacuumizing by using a vacuum pump, replacing air in the high-pressure reaction kettle with nitrogen for three times, and finally keeping the system at a negative pressure; under the condition of room temperature, 580g of propylene oxide and 2.424g of triethylamine catalyst are mixed and then added into a high-pressure reaction kettle, the temperature of the reaction kettle is slowly raised to 50 ℃, and stirring is started simultaneously; after bisphenol A is completely dissolved, heating to the set reaction temperature of 90 ℃, controlling the pressure in the kettle within the required value range (1.4-1.6MPa), and removing the released heat in the reaction by using cooling water; and (5) continuously carrying out pressure maintaining reaction for 1-2h, carrying out vacuum degassing for 30min, and discharging to obtain a finished product.
The molar ratio of the bisphenol A to the propylene oxide is 1: 10. The addition amount of the catalyst is 3 per mill of the total mass of the bisphenol A and the propylene oxide.
Example 8
Putting 228g of bisphenol A into a high-pressure reaction kettle with a high-pressure kettle controller, vacuumizing by using a vacuum pump, replacing air in the high-pressure reaction kettle with nitrogen for three times, and finally keeping the system at a negative pressure; under the condition of room temperature, 580g of propylene oxide and 0.808g of triethylamine catalyst are mixed and then added into a high-pressure reaction kettle, the temperature of the reaction kettle is slowly raised to 50 ℃, and stirring is started simultaneously; after bisphenol A is completely dissolved, heating to the set reaction temperature of 80 ℃, controlling the pressure in the kettle within the required value range (1.0-1.2MPa), and removing the released heat in the reaction by using cooling water; and (5) continuously carrying out pressure maintaining reaction for 1-2h, carrying out vacuum degassing for 30min, and discharging to obtain a finished product.
The molar ratio of the bisphenol A to the propylene oxide is 1: 10. The addition amount of the catalyst is 1 per mill of the total mass of the bisphenol A and the propylene oxide.
Example 9
Putting 228g of bisphenol A into a high-pressure reaction kettle with a high-pressure kettle controller, vacuumizing by using a vacuum pump, replacing air in the high-pressure reaction kettle with nitrogen for three times, and finally keeping the system at a negative pressure; under the condition of room temperature, 580g of propylene oxide and 1.616g of triethylamine catalyst are mixed and then added into a high-pressure reaction kettle, the temperature of the reaction kettle is slowly raised to 50 ℃, and stirring is started simultaneously; after bisphenol A is completely dissolved, heating to the set reaction temperature of 80 ℃, controlling the pressure in the kettle within the required value range (1.0-1.2MPa), and removing the released heat in the reaction by using cooling water; and (5) continuously carrying out pressure maintaining reaction for 1-2h, carrying out vacuum degassing for 30min, and discharging to obtain a finished product.
The molar ratio of the bisphenol A to the propylene oxide is 1: 10. The addition amount of the catalyst is 2 per mill of the total mass of the bisphenol A and the propylene oxide.
Claims (5)
1. A preparation method of bisphenol A polyoxypropylene ether is characterized by comprising the following steps: the method comprises the following steps:
bisphenol A is taken as a raw material, under the reaction conditions of high pressure and low temperature, liquefied propylene oxide is taken as a solvent, and ring opening polymerization is carried out under the action of an amine catalyst to obtain bisphenol A polyoxypropylene ether;
the method specifically comprises the following steps:
s1, putting the bisphenol A into a high-pressure reaction kettle, replacing air in the high-pressure reaction kettle with nitrogen, and finally keeping the system at a negative pressure;
s2, adding the propylene oxide and the amine catalyst into the high-pressure reaction kettle at one time at room temperature;
s3, slowly raising the temperature of the reaction kettle to 50 ℃, and starting stirring simultaneously;
s4, after the bisphenol A is completely dissolved, heating to the set reaction temperature of 60-90 ℃, controlling the pressure in the kettle to be 0.6-1.6MPa, and transferring the heat released in the reaction;
and S5, carrying out pressure maintaining reaction and vacuum degassing to obtain the finished product bisphenol A polyoxypropylene ether.
2. The process for producing a bisphenol A polyoxypropylene ether according to claim 1, wherein: the molar ratio of the bisphenol A to the propylene oxide is 1: 2-30.
3. The process for producing a bisphenol A polyoxypropylene ether according to claim 1, wherein: the addition amount of the catalyst is 1-3 per mill of the total mass of the bisphenol A and the propylene oxide.
4. The process for producing a bisphenol A polyoxypropylene ether according to claim 1, wherein: the S5 includes: and after the pressure maintaining reaction for 1-2h, vacuum degassing at 80 ℃ to obtain the finished product of bisphenol A polyoxypropylene ether.
5. The process for producing a bisphenol A polyoxypropylene ether according to claim 1, wherein: the structural formula of the catalyst is as follows:
wherein R is 1 、R 2 、R 3 All are electron rich substituents.
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| JP2019218434A (en) * | 2018-06-15 | 2019-12-26 | 第一工業製薬株式会社 | Method of producing polyoxyalkylene polyol |
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| JPS60243036A (en) * | 1985-03-28 | 1985-12-03 | Takemoto Oil & Fat Co Ltd | Treatment of addition product of bisphenol and alkylene oxide |
| PL273517A1 (en) * | 1988-07-04 | 1990-01-08 | Inst Ciezkiej Syntezy Orga | Method for manufacturing oxyalkylene derivatives of bisphenol a |
| JP2004123615A (en) * | 2002-10-03 | 2004-04-22 | Sanyo Chem Ind Ltd | Bisphenol a dioxyethylene ether and production method therefor |
| CN103641696A (en) * | 2013-11-27 | 2014-03-19 | 浙江合诚化学有限公司 | Method for synthesizing dihydroxypropyl bisphenol A ether through one-step process |
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