CN114394887A - Phenyloxyethanol compound and preparation method thereof - Google Patents
Phenyloxyethanol compound and preparation method thereof Download PDFInfo
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- CN114394887A CN114394887A CN202210106060.6A CN202210106060A CN114394887A CN 114394887 A CN114394887 A CN 114394887A CN 202210106060 A CN202210106060 A CN 202210106060A CN 114394887 A CN114394887 A CN 114394887A
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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
Abstract
The invention provides a phenyl oxyethanol compound and a preparation method thereof, wherein the preparation method comprises the following steps: s1: adding a phenolic compound, ethylene carbonate, a benzene solvent and a catalyst into a reactor, placing the reactor under 600W of microwave, and stirring for reaction for 10-20 min to obtain a reaction solution; the catalyst comprises a base and a polar aprotic solvent; s2: and (3) washing the reaction solution to be neutral, cooling, and precipitating a solid to obtain the phenyloxyethanol compound. According to the preparation method of the phenyloxyethanol compound, benzene is used as a solvent, potassium carbonate and a polar aprotic solvent are used as catalysts, and compared with the traditional preparation method using DMF as a solvent, on the basis of ensuring the reaction activity, a large amount of water is not needed for washing DMF, so that the amount of waste water containing DMF can be reduced, and the pollution is reduced.
Description
Technical Field
The invention relates to the technical field of organic synthesis, in particular to a phenyl oxyethanol compound and a preparation method thereof.
Background
The fluorenyl product is an important intermediate of photoelectric materials, and materials such as epoxy resin, polycarbonate, polyimide and the like which are derived and synthesized by the fluorenyl product have excellent performances such as high refractive index, high thermal stability, good transparency and the like, and are widely applied to the fields of OLEDs, brightness enhancement films, polarizing films, reflective films, optical lenses and the like; and the phenyl oxyethanol compounds such as 2- (2-biphenyl) ethanol, 2- (2-naphthoxy) ethanol, 2-phenoxyethanol and the like are key intermediates of fluorenyl products, so that the preparation of the phenyl oxyethanol compounds is important for the development of photoelectric materials.
In the existing preparation method of the phenyloxyethanol compound, N-Dimethylformamide (DMF) is usually taken as a solvent, so that a large amount of DMF-containing wastewater is generated in the preparation process.
Disclosure of Invention
The invention solves the problem that a large amount of waste water containing DMF is generated in the prior preparation process of the phenyloxyethanol compound.
In order to solve the above problems, the present invention provides a method for preparing a phenyloxyethanol compound, comprising the steps of:
s1: adding a phenolic compound, ethylene carbonate, a benzene solvent and a catalyst into a reactor, placing the reactor under 600W of microwave, and stirring for reaction for 10-20 min to obtain a reaction solution;
the catalyst comprises a base and a polar aprotic solvent;
s2: and (3) washing the reaction solution to be neutral, cooling, and precipitating a solid to obtain the phenyloxyethanol compound.
Alternatively, the molar ratio of the phenolic compound to the ethylene carbonate in step S1 is in the range of 1: (1.2-1.3).
Alternatively, the molar ratio of the base to the phenolic compound in step S1 is 1: 5.
optionally, the amount of the polar aprotic solvent added in step S1 is 1 mL/(0.02-0.05) mol of the phenolic compound.
Optionally, the polar aprotic solvent is selected from at least one of DMAC, DMF, N-diethylformamide, N-diethylacetamide.
Alternatively, the base comprises potassium carbonate; the phenolic compound is at least one of 2-naphthol and 2-diphenol.
Optionally, the benzene-based solvent comprises toluene.
Another object of the present invention is to provide a phenoxyethanol compound prepared by the method for preparing a phenoxyethanol compound as described above.
Optionally, 2- (2-naphthoxy) ethanol is included, and the X-ray powder diffraction pattern of the 2- (2-naphthoxy) ethanol has 2θThe value was 8.108. + -. 0.20，8.563±0.20,12.128±0.20,12.810±0.20，16.147±0.20,17.057±0.20,18.346±0.20,18.801±0.20,19.256±0.20,20.167±0.20,20.773±0.20,21.380±0.20,26.158±0.20,30.026±0.20Characteristic diffraction peaks.
Optionally, 2- (2-biphenyl) ethanol is included, and the X-ray powder diffraction pattern of the 2- (2-biphenyl) ethanol has 2θValue 6.895. + -. 0.20,9.701±0.20,11.976±0.20,13.265±0.20,13.720±0.20,15.313±0.20,16.754±0.20,18.119±0.20,19.560±0.20,20.622±0.20,22.821±0.20,23.807±0.20,24.869±0.20,25.779±0.20,26.765±0.20,27.599±0.20,28.509±0.20,29.343±0.20,29.950±0.20，30.253±0.20,43.677±0.20Characteristic diffraction peaks.
Compared with the prior art, the preparation method of the phenyloxyethanol compound provided by the invention has the following advantages:
according to the preparation method of the phenyloxyethanol compound, benzene is used as a solvent, potassium carbonate and a polar aprotic solvent are used as catalysts, and compared with the traditional preparation method using DMF as a solvent, on the basis of ensuring the reaction activity, a large amount of water is not needed for washing DMF, so that the amount of waste water containing DMF can be reduced, and the pollution is reduced; meanwhile, benzene is used as a solvent, and after the reaction is finished, a product can be directly separated out through cooling, so that the post-treatment process is simplified.
Drawings
FIG. 1 is an X-ray powder diffraction pattern of 2- (2-naphthoxy) ethanol prepared in example 1 of the present invention;
FIG. 2 is an X-ray powder diffraction pattern of 2- (2-biphenylyl) ethanol prepared in example 2 of the present invention.
Detailed Description
The following describes embodiments of the present invention in detail. The embodiments described below are exemplary and are intended to be illustrative of the present invention and should not be construed as limiting the present invention, and all other embodiments that can be obtained by one of ordinary skill in the art based on the embodiments of the present invention without inventive step fall within the scope of the present invention.
In the existing preparation process of the phenyloxyethanol compound, N-Dimethylformamide (DMF) is usually taken as a solvent for reaction, toluene is used for extraction after the reaction is finished, and the DMF solvent needs to be washed by a large amount of water for removal, so that a large amount of DMF-containing wastewater is generated.
In order to solve the problem that a large amount of DMF-containing wastewater is generated in the existing preparation process of the phenyloxyethanol compound, the invention provides a preparation method of the phenyloxyethanol compound, which comprises the following steps:
s1: adding a phenolic compound, ethylene carbonate, a benzene solvent and a catalyst into a reactor, placing the reactor under 600W of microwave, and stirring for reaction for 10-20 min to obtain a reaction solution; wherein the catalyst comprises a base and a polar aprotic solvent;
s2: and (3) washing the reaction liquid to be neutral, cooling, and precipitating a solid to obtain the phenyloxyethanol compound.
Benzene is used as a solvent, an alkaline substance and a polar aprotic solvent are used as catalysts, so that a phenolic compound and ethylene carbonate react under the microwave reaction condition of 600W to generate a phenyloxyethanol compound; the reaction process is shown as the following formula:
the method is characterized in that an alkaline substance and a polar aprotic solvent are used for co-catalysis, and the carbonyl group in the polar aprotic solvent is utilized to promote the ring opening of the ethylene carbonate, so that the reaction activity of the ethylene carbonate is improved, and the reaction is promoted, wherein the specific catalysis principle is shown as the following formula:
according to the preparation method of the phenyloxyethanol compound, benzene is used as a solvent, potassium carbonate and a polar aprotic solvent are used as catalysts, and compared with the traditional preparation method using DMF as a solvent, on the basis of ensuring the reaction activity, a large amount of water is not needed for washing DMF, so that the amount of waste water containing DMF can be reduced, and the pollution is reduced; meanwhile, benzene is used as a solvent, and after the reaction is finished, a product can be directly separated out through cooling, so that the post-treatment process is simplified.
In addition, the fluorenyl product is applied to electronic products, so that the requirement on the chromaticity of the product is high, and the requirement on the chromaticity of the phenyl oxyethanol compound which is a key intermediate of the fluorenyl product is met; in the existing preparation process of the phenyloxyethanol compound, the reaction time is long, and the phenyloxyethanol compound is easy to wrap a solvent when being crystallized, so that the chromaticity of the phenyloxyethanol compound is influenced; according to the method, the polar aprotic solvent is added into the catalyst, so that the reaction activity is improved, the reaction time is shortened by combining a microwave reaction method, and the color of a reaction system is reduced, so that the high-purity low-chroma phenyloxyethanol compound is obtained.
In order to achieve the product yield and the economic efficiency of the reaction process, the molar ratio of the phenolic compound to the ethylene carbonate in the step S1 is preferably in the range of 1: (1.2-1.3); the molar ratio of base to phenolic compound is 1: 5; in the step S1, the addition amount of the polar aprotic solvent is 1 mL/(0.02-0.05) mol of the phenolic compound.
Specifically, the polar aprotic solvent is preferably selected from at least one of Dimethylacetamide (DMAC), DMF, N-diethylformamide, N-diethylacetamide.
It should be noted that the DMAC, DMF, N-diethylformamide, N-diethylacetamide added in the present application are catalytic, and different from the conventional preparation process of the phenoxyethanol compound, DMAC and DMF are used as solvents; according to the method, on the basis of taking benzene as a solvent, DMAC, DMF, N-diethylformamide, N-diethylacetamide and the like in catalytic amount are added to improve the reaction activity and shorten the reaction time.
The base in this application may be a carbonate salt, and is preferably potassium carbonate.
The phenolic compound is preferably selected from at least one of 2-naphthol and 2-biphenol; the benzene-based solvent includes toluene.
Another object of the present invention is to provide a phenyloxyethanol compound prepared by the method for preparing a phenyloxyethanol compound as described above.
According to the phenyl oxyethanol compound, benzene is used as a solvent in the preparation process, potassium carbonate and a polar aprotic solvent are used as catalysts, and compared with the traditional preparation method using DMF as a solvent, on the basis of ensuring the reaction activity, a large amount of water is not needed for washing DMF, so that the amount of waste water containing DMF can be reduced, and the pollution is reduced; meanwhile, benzene is used as a solvent, and after the reaction is finished, a product can be directly separated out through cooling, so that the post-treatment process is simplified; the prepared phenyl oxyethanol compound has high purity and low chroma, and meets the quality requirement of fluorenyl products.
In order to make the aforementioned objects, features and advantages of the present invention comprehensible, embodiments accompanied with figures are described in detail below.
Example 1
This example provides a preparation method of a phenyloxyethanol compound, which comprises the following steps:
s1: adding 28.8g (0.2mol) of 2-naphthol, 21.11g (0.24mol) of ethylene carbonate, 100mL of toluene, 10mL of DMAC and 5.52g (0.04mol) of potassium carbonate into a 500mL reaction bottle, placing the mixture in a 600W microwave reactor, reacting for 15min, stopping the reaction when the content of the 2-naphthol is less than 0.5% by HPLC analysis, and obtaining a reaction solution;
s2: adding 100mL of toluene, washing the reaction solution to be neutral by using water, separating an organic phase, concentrating to remove 50mL of toluene, cooling at room temperature to separate out crystals, and carrying out vacuum drying on the obtained solid at 60 ℃ for 12 hours to obtain 32.6g of white 2- (2-naphthoxy) ethanol with the yield of 86.7%.
The prepared 2- (2-naphthoxy) ethanol is detected to have the purity of 99.5 percent, the melting point of 73.6-75.6 ℃ and the chroma of 21APHA (30 percent acetone solution).
X-ray powder diffraction of the prepared 2- (2-naphthoxy) ethanol, as shown in FIG. 1, has 2θThe value was 8.108. + -. 0.20，8.563±0.20,12.128±0.20,12.810±0.20，16.147±0.20,17.057±0.20,18.346±0.20,18.801±0.20,19.256±0.20,20.167±0.20,20.773±0.20,21.380±0.20,26.158±0.20,30.026±0.20Characteristic diffraction peaks.
Example 2
This example provides a preparation method of a phenyloxyethanol compound, which comprises the following steps:
s1: adding 42.5g (0.25mol) of 2-biphenol, 28.6g (0.325mol) of ethylene carbonate, 150mL of toluene, 5mL of DMF (dimethyl formamide) and 6.9g (0.05mol) of potassium carbonate into a 500mL reaction bottle, placing the bottle in a 600W microwave reactor, reacting for 10min, stopping the reaction when the content of the 2-biphenol is less than 0.5% by HPLC (high performance liquid chromatography) analysis, and obtaining a reaction solution;
s2: adding 100mL of toluene, washing the reaction solution to be neutral by using water, separating an organic phase, concentrating to remove 140mL of toluene, placing at-10 ℃ to cool and separate out crystals, and carrying out vacuum drying on the obtained solid at 60 ℃ for 12 hours by suction filtration to obtain 45.3g of white 2- (2-biphenyl) ethanol with the yield of 84.67%.
The prepared 2- (2-biphenyl) ethanol is detected, the purity is 99.06%, the melting point is 74.9-76.2 ℃, and the chroma is 13APHA (30% acetone solution).
X-ray powder diffraction of the prepared 2- (2-biphenyl) ethanol, shown in FIG. 2, having 2θValue 6.895. + -. 0.20,9.701±0.20,11.976±0.20,13.265±0.20,13.720±0.20,15.313±0.20,16.754±0.20,18.119±0.20,19.560±0.20,20.622±0.20,22.821±0.20,23.807±0.20,24.869±0.20,25.779±0.20,26.765±0.20,27.599±0.20,28.509±0.20,29.343±0.20,29.950±0.20，30.253±0.20,43.677±0.20Characteristic diffraction peaks.
Comparative example 1
The comparative example provides a preparation method of a phenyloxyethanol compound, the preparation process comprising:
a500 mL reaction flask was charged with 28.8g (0.2mol) of 2-naphthol, 21.11g (0.24mol) of ethylene carbonate, 100mL of toluene, and 5.52g (0.04mol) of potassium carbonate, and the mixture was placed in a 600W microwave reactor and reacted for 30min, and the HPLC analysis showed that the 2-naphthol content was 77.3%, and a large amount of 2-naphthol was not reacted, thereby terminating the reaction.
Comparing the comparative example with example 1, the reaction activity is obviously reduced under the condition of not adding polar aprotic solvent; therefore, the application proves that when the phenyl oxyethanol compound is prepared from the ethylene carbonate, a proper amount of polar aprotic solvent is added, the microwave is used for replacing the traditional heating mode, the reaction time can be shortened, the three wastes are greatly reduced, and the high-purity low-chroma phenyl oxyethanol compound is obtained.
Although the present disclosure has been described above, the scope of the present disclosure is not limited thereto. Those skilled in the art can make various changes and modifications without departing from the spirit and scope of the present disclosure, and such changes and modifications will fall within the scope of the present invention.
Claims (10)
1. A preparation method of a phenyloxyethanol compound is characterized by comprising the following steps:
s1: adding a phenolic compound, ethylene carbonate, a benzene solvent and a catalyst into a reactor, placing the reactor under 600W of microwave, and stirring for reaction for 10-20 min to obtain a reaction solution;
the catalyst comprises a base and a polar aprotic solvent;
s2: and (3) washing the reaction solution to be neutral, cooling, and precipitating a solid to obtain the phenyloxyethanol compound.
2. The method for producing a phenyloxyethanol compound according to claim 1, wherein the molar ratio of the phenolic compound to the ethylene carbonate in step S1 is in the range of 1: (1.2-1.3).
3. The method for producing a phenyloxyethanol compound according to claim 1, wherein the molar ratio of the base to the phenolic compound in step S1 is 1: 5.
4. the method for producing a phenyloxyethanol compound according to claim 1, wherein the amount of the polar aprotic solvent added in step S1 is 1mL/(0.02 to 0.05) mol of the phenolic compound.
5. The method for producing a phenyloxyethanol compound according to any one of claims 1 to 4, wherein the polar aprotic solvent is at least one selected from DMAC, DMF, N-diethylformamide and N, N-diethylacetamide.
6. The method for producing a phenyloxyethanol compound according to claim 5, wherein the base comprises potassium carbonate; the phenolic compound is at least one of 2-naphthol and 2-diphenol.
7. The method for producing a phenyloxyethanol compound according to claim 5, wherein the benzene-based solvent comprises toluene.
8. A phenyloxyethanol compound characterized by being produced by the method for producing a phenyloxyethanol compound according to any one of claims 1 to 7.
9. The phenylethanol compound of claim 8 comprising 2- (2-naphthoxy) ethanol, wherein said 2- (2-naphthoxy) ethanol has an X-ray powder diffraction pattern of 2θThe value was 8.108. + -. 0.20，8.563±0.20,12.128±0.20,12.810±0.20，16.147±0.20,17.057±0.20,18.346±0.20,18.801±0.20,19.256±0.20,20.167±0.20,20.773±0.20,21.380±0.20,26.158±0.20,30.026±0.20Characteristic diffraction peaks.
10. The phenylethanol compound of claim 8, comprising 2- (2-biphenyl) ethanol, wherein said 2- (2-biphenyl) ethanol has an X-ray powder diffraction pattern of 2θValue 6.895. + -. 0.20,9.701±0.20,11.976±0.20,13.265±0.20,13.720±0.20,15.313±0.20,16.754±0.20,18.119±0.20,19.560±0.20,20.622±0.20,22.821±0.20,23.807±0.20,24.869±0.20,25.779±0.20,26.765±0.20,27.599±0.20,28.509±0.20,29.343±0.20,29.950±0.20，30.253±0.20,43.677±0.20Characteristic diffraction peaks.
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