CN113024358A - Method for catalytically synthesizing phenyl diether fluorene by ethylene oxide - Google Patents
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/02—Preparation of ethers from oxiranes
- C07C41/03—Preparation of ethers from oxiranes by reaction of oxirane rings with hydroxy groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/34—Separation; Purification; Stabilisation; Use of additives
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Abstract
The invention relates to the technical field of catalytic synthesis preparation of phenyl diether fluorene, in particular to a method for catalytic synthesis of phenyl diether fluorene by ethylene oxide, which has the advantages of mild reaction conditions, simple post-treatment, convenient operation, high purity and yield of the obtained product, less pollution to the external environment in the production process and suitability for industrial production; the method comprises the following steps: s1, preparing a reaction base solution; s2, preparing a reaction solution; s3, adding a catalyst; s4, catalyzing reaction; s5, reactant treatment: standing and cooling the reaction solution obtained after the reaction to 0-10 ℃ for precipitation, performing centrifugal treatment, separating the solid from the mother solution, and distilling and recovering the mother solution; s6, primary recrystallization treatment: adding a recrystallization solvent into the separated solid, heating to dissolve, standing, cooling to 0-10 ℃ to separate out, performing centrifugal treatment, recovering mother liquor, and drying the separated solid to obtain white solid phenyl diether fluorene; and S7, secondary recrystallization treatment.
Description
Technical Field
The invention relates to the technical field of catalytic synthesis preparation of phenyl diether fluorene, in particular to a method for catalytic synthesis of phenyl diether fluorene by ethylene oxide.
Background
Phenyl diether fluorene, scientific name: 9, 9-bis [ 3-phenyl-4- (2-hydroxyethoxy) phenyl ] fluorene, molecular formula: C41H34O4 is a white powder solid, and a resin synthesized from phenyl diether fluorene as a raw material monomer has characteristics of high heat resistance, high refractive index and the like, and can meet the increasing requirements of people on electronic products such as cameras, mobile phones, flat panels, notebooks and the like. It can be seen that phenyl diether fluorene is a precious organic chemical material, and its application is very interesting in korea, japan and usa, and there is a great worldwide demand. The phenyl diether fluorene is an indispensable novel material, and meanwhile, the development of the phenyl diether fluorene and downstream products thereof has a good development prospect in China, and the development of functional polymer materials and related fields in China can be promoted. Therefore, the development of the technology is enhanced, the development of national defense science and technology in China can be promoted, and the development of economy in China can be accelerated.
Patent documents CN107935827A and CN108350163A provide a method for synthesizing phenyl diether fluorene by using fluorenone and phenoxyethanol under the action of a catalyst, in the method, water is generated in the reaction process, and if industrial production is carried out, more waste water is generated, so that the environment is easily polluted to a certain extent; secondly, patent documents CN109071391A, CN109195936A and CN107848933A provide a method for synthesizing phenyl diether fluorene by using phenyl bisphenol fluorene and ethylene carbonate and potassium carbonate as a catalyst, and the method has more post-treatment steps and troublesome operation of the obtained product; the method for synthesizing phenyl diether fluorene reported in Japanese patent JP2009256342A has low yield of products obtained by one-step reaction. Therefore, the method for synthesizing phenyl diether fluorene has a great promotion space, and is a problem to be solved urgently by the technical personnel in the field.
Disclosure of Invention
In order to solve the technical problems, the invention provides the method for synthesizing the phenyl diether fluorene under the catalysis of the ethylene oxide, which has the advantages of mild reaction conditions, simple post-treatment, convenient operation, high purity and high yield of the obtained product, and less pollution to the external environment in the production process, and is suitable for industrial production.
The invention relates to a method for synthesizing phenyl diether fluorene by ethylene oxide catalysis, which comprises the following steps:
s1, preparing a reaction base liquid: adding absolute ethyl alcohol and ethylene glycol dimethyl ether in a ratio of 1:1 into a reactor, and stirring and mixing uniformly to obtain a reaction base solution;
s2, preparation of a reaction solution: adding phenyl bisphenol fluorene into a reactor containing reaction base liquid, heating, starting stirring, and fully dissolving the phenyl bisphenol fluorene into the reaction base liquid to obtain reaction liquid consisting of absolute ethyl alcohol, ethylene glycol dimethyl ether and phenyl bisphenol fluorene;
s3, adding a catalyst: adding solid alkali into the obtained reaction solution, and stirring and mixing uniformly to obtain a mixed solution;
s4, catalytic reaction: slowly introducing ethylene oxide into the obtained mixed solution, stirring and mixing the mixed solution while introducing the ethylene oxide, controlling the temperature to be 30-80 ℃, introducing the ethylene oxide for 10-90 min, and stirring and reacting for 4-15 h after the introduction of the ethylene oxide is finished;
s5, reactant treatment: standing and cooling the reaction solution obtained after the reaction to 0-10 ℃ for precipitation, performing centrifugal treatment, separating the solid from the mother solution, and distilling and recovering the mother solution;
s6, primary recrystallization treatment: adding a recrystallization solvent into the separated solid, heating to dissolve, standing, cooling to 0-10 ℃ to separate out, performing centrifugal treatment, recovering mother liquor, and drying the separated solid to obtain white solid phenyl diether fluorene;
s7, secondary recrystallization treatment: and adding a recrystallization solvent into the obtained crude solid phenyl diether fluorene, heating for dissolving, carrying out thermal filtration, standing, cooling to 0-10 ℃ for precipitation, carrying out centrifugal treatment again, recovering mother liquor, and drying the separated solid to obtain the crude solid phenyl diether fluorene.
Furthermore, the reaction base liquid can also be composed of one or more of toluene, xylene, absolute ethyl alcohol, ethylene glycol anisole and ethylene glycol monomethyl ether, and the absolute ethyl alcohol and the ethylene glycol dimethyl ether are preferably selected.
Furthermore, the adding ratio of the phenyl bisphenol fluorene in the S2 to the reaction base liquid composed of absolute ethyl alcohol and ethylene glycol dimethyl ether is 1: 0.5-5.0.
Furthermore, the adding mass ratio of the solid alkali and the phenyl bisphenol fluorene in the S3 is 1: 500-1000.
Further, the solid base in S3 is one or more of potassium hydroxide, sodium hydroxide, triethylamine, tributylamine, tetrabutylammonium bromide and hexadecyltrimethylammonium bromide, and sodium hydroxide is preferred.
Furthermore, the adding mass ratio of ethylene oxide to phenyl bisphenol fluorene in S4 is 1: 2-30.
Further, the mass ratio of the solid separated in S6 and S7 to the added recrystallization solvent is 1:1 to 5.
Further, the recrystallization solvent used in S6 is one or more of toluene, N-dimethylformamide, butanone, absolute ethanol, acetone, ethylene glycol dimethyl ether, and toluene and absolute ethanol are preferred.
Further, the recrystallization solvent used in S7 is one or more of toluene, N-dimethylformamide, butanone, absolute ethanol, acetone, ethylene glycol dimethyl ether, and toluene is preferably used.
Compared with the prior art, the invention has the beneficial effects that:
the invention relates to a method for synthesizing phenyl diether fluorene by ethylene oxide catalysis, which adopts solid alkali as a catalyst and anhydrous ethanol and ethylene glycol dimethyl ether as a reaction solvent, fully reacts the phenyl bisphenol fluorene with the ethylene oxide under mild conditions, after the reaction is finished, a crude product is precipitated by standing and cooling, and is centrifuged, the obtained reaction liquid can be recycled, the obtained solid is subjected to secondary recrystallization treatment by using a recrystallization solvent, the product is precipitated by standing and cooling, and is centrifuged, the separated mother liquor can be recycled, so that the waste of resources is reduced, the utilization rate is improved, and the separated solid is dried to obtain the white phenyl diether fluorene solid with the purity of more than 99.0 percent;
the method has the advantages of low reaction temperature, low pressure, simple post-treatment and operation process, high yield of more than 90 percent and high product purity of more than 99.0 percent, and simultaneously, the consumption of the catalyst for the reaction is little, so that the method has little pollution to the environment and is suitable for industrialization;
compared with the prior production technology, the method of the invention directly uses bisphenol fluorene and ethylene oxide as raw materials, uses solid alkali as a catalyst, uses absolute ethyl alcohol and ethylene glycol dimethyl ether as reaction solvents, greatly reduces the production cost, also can diversify the products of factories, has high yield, does not generate waste gas and waste residue, and greatly reduces the pollution to the environment.
Detailed Description
The following examples are given to further illustrate the embodiments of the present invention. The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention.
The invention relates to a method for synthesizing phenyl diether fluorene by ethylene oxide catalysis, which has a chemical reaction equation as follows:
example 1
230g of phenyl bisphenol fluorene, 230g of absolute ethyl alcohol, 230g of ethylene glycol dimethyl ether and 7.7g of sodium hydroxide are added into a 1-liter high-pressure reaction kettle, the reaction kettle is installed, stirring cooling water is introduced, stirring is started, heating is started, the temperature is controlled to be 40-55 ℃, 42.3g of ethylene oxide is introduced, the introduction time is 15 minutes, and after the introduction is finished, the temperature is controlled to be 55-75 ℃ and the reaction is carried out for 10 hours. After the reaction is finished, pouring the reaction liquid into a 1L beaker, stirring, cooling and precipitating, then carrying out suction filtration and drying, recovering absolute ethyl alcohol and ethylene glycol dimethyl ether for next use, recrystallizing the solid with 390g of toluene and 70g of absolute ethyl alcohol, heating to 85 ℃ for dissolution, standing, cooling and precipitating, carrying out suction filtration and drying, obtaining a crude product, heating and dissolving with 750g of toluene, cooling, crystallizing, carrying out suction filtration and drying. 240g of phenyl diether fluorene white solid is obtained, the yield is 88.6%, the purity of the obtained product is 98.71% by liquid chromatography, and the Hazen color is less than 15.
Example 2
Adding 240g of phenyl bisphenol fluorene into a 1-pressure-rising reaction kettle, adding 240g of absolute ethyl alcohol, 240g of ethylene glycol dimethyl ether and 1.6g of sodium hydroxide, installing the reaction kettle, introducing stirring cooling water, starting stirring, starting heating, controlling the temperature to be 40-55 ℃, starting introducing 44.2g of ethylene oxide, introducing for 25 minutes, controlling the temperature to be 55-75 ℃ after introducing, and reacting for 10 hours. After the reaction is finished, pouring the reaction liquid into a 1L beaker, stirring, cooling and precipitating, then carrying out suction filtration and drying, recovering absolute ethyl alcohol and ethylene glycol dimethyl ether for next use, recrystallizing the solid with 410g of toluene and 70g of absolute ethyl alcohol, heating to 85 ℃ for dissolution, standing, cooling and precipitating, carrying out suction filtration and drying, obtaining a crude product, heating and dissolving with 790g of toluene, cooling, crystallizing, carrying out suction filtration and drying. 260g of phenyl diether fluorene white solid is obtained with a yield of 91.87%, and the product obtained by liquid chromatography is 99.01% pure and has a Hazen color of less than 15%.
Example 3
Adding 240g of phenyl bisphenol fluorene into a 1-liter high-pressure reaction kettle, adding 240g of absolute ethyl alcohol, 240g of ethylene glycol dimethyl ether and 1.6g of sodium hydroxide, installing the reaction kettle, introducing stirring cooling water, starting stirring, starting heating, controlling the temperature to be 40-55 ℃, starting introducing 44.2g of ethylene oxide, introducing for 20 minutes, controlling the temperature to be 55-75 ℃ after introducing, and reacting for 11 hours. After the reaction is finished, pouring the reaction liquid into a 1L beaker, stirring, cooling, precipitating, then carrying out suction filtration and drying to obtain 230g of a product, recovering absolute ethyl alcohol and ethylene glycol dimethyl ether for next use, recrystallizing the solid with 375g of toluene and 63g of absolute ethyl alcohol, heating to 85 ℃ for dissolution, standing, cooling, precipitating, carrying out suction filtration and drying to obtain a crude product, heating and dissolving with 750g of toluene, cooling, crystallizing, carrying out suction filtration and drying. 240g of phenyl diether fluorene white solid is obtained, the yield is 85.00%, the purity of the obtained product is 98.94% by liquid chromatography, and the Hazen color is less than 15.
Example 4
Adding 180 g of phenyl bisphenol fluorene into a 1L high-pressure reaction kettle, adding 270g of absolute ethyl alcohol, 270g of ethylene glycol dimethyl ether and 1.2g of sodium hydroxide, installing the reaction kettle, introducing stirring cooling water, starting stirring, starting heating, controlling the temperature to be 40-55 ℃, starting introducing 33.1g of ethylene oxide, introducing the ethylene oxide for 10 minutes, controlling the temperature to be 55-75 ℃ after introducing, and reacting for 8 hours. After the reaction is finished, pouring the reaction liquid into a 1L beaker, stirring, cooling and precipitating, then carrying out suction filtration and drying, recovering absolute ethyl alcohol and ethylene glycol dimethyl ether for next use, recrystallizing the solid with 345g of toluene and 58g of absolute ethyl alcohol, heating to 85 ℃ for dissolution, standing, cooling and precipitating, carrying out suction filtration and drying, obtaining a crude product, heating and dissolving with 630g of toluene, cooling, crystallizing, carrying out suction filtration and drying. 205g of phenyl bisether fluorene are obtained as a white solid in an yield of 96.69%, the purity of the product is 99.47% by liquid chromatography, and the Hazen color is less than 15.
Example 5
Adding 180 g of phenyl bisphenol fluorene into a 1L high-pressure reaction kettle, adding 270g of absolute ethyl alcohol, 270g of ethylene glycol dimethyl ether and 1.2g of sodium hydroxide, installing the reaction kettle, introducing stirring cooling water, starting stirring, starting heating, controlling the temperature to be 40-55 ℃, starting introducing 33.1g of ethylene oxide, introducing for 10 minutes, controlling the temperature to be 55-75 ℃ after introducing, and reacting for 10 hours. After the reaction is finished, pouring the reaction liquid into a 1L beaker, stirring, cooling, precipitating, then carrying out suction filtration and drying, recovering absolute ethyl alcohol and ethylene glycol dimethyl ether for next use, recrystallizing the solid with 322.5g of toluene and 54g of absolute ethyl alcohol, heating to 85 ℃ for dissolution, standing, cooling, precipitating, carrying out suction filtration and drying, obtaining a crude product, heating and dissolving with 615g of toluene, cooling, crystallizing, carrying out suction filtration and drying. 195g of phenyl diether fluorene white solid is obtained with a yield of 91.98%, and the product obtained by liquid chromatography has a purity of 99.38% and a Hazen color of less than 15%.
In the above examples, the reactants and the reaction products were detected by hplc, and the products prepared in each example were compared to obtain the following results:
in the process of catalytically synthesizing the phenyl diether fluorene by adopting the embodiment, the reaction condition is mild, the reaction pressure is lower, the post-treatment is simple, the operation is convenient, the purity of the obtained product is high, the yield is high, no waste gas or waste residue is generated in the production process, the pollution to the external environment is less, the mother liquor can be recycled, the utilization rate of resources is improved, and the method is suitable for industrial production.
The above description is only a preferred embodiment of the present invention, and it should be noted that, for those skilled in the art, several modifications and variations can be made without departing from the technical principle of the present invention, and these modifications and variations should also be regarded as the protection scope of the present invention.
Claims (8)
1. A method for synthesizing phenyl diether fluorene by ethylene oxide catalysis is characterized by comprising the following steps:
s1, preparing a reaction base liquid: adding absolute ethyl alcohol and ethylene glycol dimethyl ether in a ratio of 1:1 into a reactor, and stirring and mixing uniformly to obtain a reaction base solution;
s2, preparation of a reaction solution: adding phenyl bisphenol fluorene into a reactor containing reaction base liquid, heating, starting stirring, and fully dissolving the phenyl bisphenol fluorene into the reaction base liquid to obtain reaction liquid consisting of absolute ethyl alcohol, ethylene glycol dimethyl ether and phenyl bisphenol fluorene;
s3, adding a catalyst: adding solid alkali into the obtained reaction solution, and stirring and mixing uniformly to obtain a mixed solution;
s4, catalytic reaction: slowly introducing ethylene oxide into the obtained mixed solution, stirring and mixing the mixed solution while introducing the ethylene oxide, controlling the temperature to be 30-80 ℃, introducing the ethylene oxide for 10-90 min, and stirring and reacting for 4-15 h after the introduction of the ethylene oxide is finished;
s5, reactant treatment: standing and cooling the reaction solution obtained after the reaction to 0-10 ℃ for precipitation, performing centrifugal treatment, separating the solid from the mother solution, and distilling and recovering the mother solution;
s6, primary recrystallization treatment: adding a recrystallization solvent into the separated solid, heating to dissolve, standing, cooling to 0-10 ℃ to separate out, performing centrifugal treatment, recovering mother liquor, and drying the separated solid to obtain white solid phenyl diether fluorene;
s7, secondary recrystallization treatment: and adding a recrystallization solvent into the obtained crude solid phenyl diether fluorene, heating for dissolving, carrying out thermal filtration, standing, cooling to 0-10 ℃ for precipitation, carrying out centrifugal treatment again, recovering mother liquor, and drying the separated solid to obtain the crude solid phenyl diether fluorene.
2. The method for catalytic synthesis of phenyl diether fluorene by ethylene oxide according to claim 1, wherein the reaction base solution further comprises one or more of toluene, xylene, absolute ethyl alcohol, ethylene glycol anisole and ethylene glycol methyl ether.
3. The method for catalytic synthesis of phenyl diether fluorene by ethylene oxide according to claim 1, wherein the addition ratio of the phenyl bisphenol fluorene in S2 to the reaction base liquid consisting of absolute ethanol and ethylene glycol dimethyl ether is 1: 0.5-5.0.
4. The method for catalytic synthesis of phenyl diether fluorene by ethylene oxide according to claim 1, further comprising the step of adding solid base and phenyl bisphenol fluorene in the S3 in a mass ratio of 1: 500-1000.
5. The method for the catalytic synthesis of phenyl diether fluorene from ethylene oxide according to claim 4, wherein the solid base in S3 is one or more of potassium hydroxide, sodium hydroxide, triethylamine, tributylamine, tetrabutylammonium bromide and hexadecyltrimethylammonium bromide.
6. The method for catalytic synthesis of phenyl diether fluorene by ethylene oxide according to claim 1, wherein the addition mass ratio of ethylene oxide to phenyl bisphenol fluorene in S4 is 1: 2-30.
7. The method for catalytically synthesizing phenyl bisether fluorene from ethylene oxide according to claim 1, wherein the mass ratio of the solid separated in S6 and S7 to the added recrystallization solvent is 1: 1-5.
8. The method for the catalytic synthesis of phenyl diether fluorene from ethylene oxide according to claim 7, wherein the recrystallization solvent used in S6 and S7 is one or more of toluene, N-dimethylformamide, butanone, anhydrous ethanol, acetone, ethylene glycol dimethyl ether and toluene.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN113548947A (en) * | 2021-07-01 | 2021-10-26 | 万华化学集团股份有限公司 | Method for preparing phenyl diether fluorene |
| CN117209365A (en) * | 2023-09-15 | 2023-12-12 | 信诺立兴(沧州渤海新区)化工有限公司 | Low metal ion granular phenyl diether fluorene and preparation method thereof |
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