CN106699523A - Synthetic method of o-phenyl phenoxyethanol - Google Patents
Synthetic method of o-phenyl phenoxyethanol Download PDFInfo
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- CN106699523A CN106699523A CN201510778349.2A CN201510778349A CN106699523A CN 106699523 A CN106699523 A CN 106699523A CN 201510778349 A CN201510778349 A CN 201510778349A CN 106699523 A CN106699523 A CN 106699523A
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- carbonate
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- phenoxyethanol
- ethylene carbonate
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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
- C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
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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 discloses a synthetic method of o-phenyl phenoxyethanol, and belongs to the field of organic synthesis. The synthetic method comprises the following steps: adding o-phenylphenol, ethylene carbonate and a carbonate catalyst into a reactor, carrying out catalytic reaction at the reaction temperature of 60 to 200 DEG C for 0.5 to 10 hours, after cooling, filtering and recycling the carbonate catalyst from the reaction system so as to obtain the o-phenyl phenoxyethanol, wherein the mass ratio of o-phenylphenol to ethylene carbonate is 1:(0.7 to 2), and the mass of the carbonate catalyst is 0.1% to 15% of the total mass of o-phenylphenol and ethylene carbonate. According to the method provided by the invention, the reaction is carried out by adopting a melting method, dangerous ethylene oxide does not need to be used, a solvent does not need to be used neither, and then the subsequent process of washing and alkali washing and solvent distillation is avoided, so that the method is short in synthetic route and simple in operation, zero emission of pollutants is realized, and the method is safer and more environmentally friendly. Moreover, the carbonate catalyst is filtered and recycled, so that the carbonate catalyst is cyclically utilized, and the energy consumption is effectively reduced.
Description
Technical field
The present invention relates to organic synthesis field, more particularly to a kind of synthetic method of adjacent phenyl Phenoxyethanol.
Background technology
Adjacent phenyl Phenoxyethanol is a kind of fine chemical material and intermediate, is usually used in medicine, agricultural chemicals, sterilization
The synthesis of agent, preservative and functional high molecule material, for example its can be used to synthesize common optics raw material：
0-phenyl phenoxyethyl acrylate (O-PhenylphenoxyethylAcrylate, OPPEA).So, have
Necessity provides a kind of synthetic method of adjacent phenyl Phenoxyethanol.
Prior art provides a kind of synthetic method of adjacent phenylphenoxy ethanol, comprises the following steps：(1)
O-phenyl phenol through melting is added into reactor, while addition catalyst, catalyst and o-phenyl phenol
Mol ratio is 0.01-0.02: 1；(2) material in reactor is being evacuated to below -0.09mPa, 80 DEG C
Heated 30-60 minutes at -90 DEG C, removing institute water content；(3) negative pressure in reactor is made after vacuumizing, then
It is 0 to be filled with nitrogen to pressure, so displacement 3 times, and makes pressure in kettle be 0；(4) in a nitrogen atmosphere,
Oxirane is gradually added reactor, controlling reaction temperature is 85-105 DEG C, keeps reacting kettle inner pressure to exist
0.3-0.5mPa scopes, oxirane is 1: 1 with the mol ratio of o-phenyl phenol；(5) oxirane is finished
Afterwards, maintenance reaction temperature, makes reacting kettle inner pressure be down to 0, then again insulation reaction 20-40 minutes, drop
Temperature obtains crude product to discharging after 75-85 DEG C；(6) above ethoxylation crude product is post-processed, that is, is entered
Row recrystallization, alkali cleaning, wash and dry finished product.
Inventor has found that prior art at least has problems with：
The method synthetic route that prior art is provided is long, cumbersome, and course of reaction needs to pressurize and use
The oxirane of toxicity, security is poor.
The content of the invention
Embodiment of the present invention technical problem to be solved is, there is provided a kind of synthetic route is short, operation letter
The synthetic method of the adjacent phenyl Phenoxyethanol of list and safety and environmental protection.Concrete technical scheme is as follows：
A kind of synthetic method of adjacent phenyl Phenoxyethanol, including：To addition o-phenyl phenol, carbon in reactor
Vinyl acetate and carbonate catalyst, catalytic reaction 0.5-10 hours under 60 DEG C -200 DEG C of reaction temperature,
After cooling down, the carbonate catalyst is recovered by filtration from reaction system, obtains adjacent phenyl Phenoxyethanol；
The o-phenyl phenol is 1 with the mass ratio of ethylene carbonate:0.7-2, the matter of the carbonate catalyst
It is the 0.1%-15% of the o-phenyl phenol and the ethylene carbonate gross mass to measure.
Specifically, preferably, the o-phenyl phenol is 1 with the mass ratio of ethylene carbonate:0.8-1.5；
The quality of the carbonate catalyst is the o-phenyl phenol and the ethylene carbonate gross mass
0.5%-10%.
Preferably, the o-phenyl phenol is 1 with the mass ratio of ethylene carbonate:0.9-1.2；
The quality of the carbonate catalyst is the o-phenyl phenol and the ethylene carbonate gross mass
1%-8%.
Specifically, preferably, the carbonate catalyst is selected from potassium carbonate, sodium carbonate, calcium carbonate
It is at least one.
Specifically, the reaction temperature is 80 DEG C -180 DEG C.
Preferably, the reaction temperature is 100 DEG C -160 DEG C.
Specifically, preferably, the time of the catalytic reaction is 1-5 hours.
Specifically, preferably, being recovered by filtration from the reaction system by the way of heat-insulating pressurizing described
Carbonate catalyst.
Specifically, it is 70-100 DEG C in temperature, and pressure is when being less than or equal to 4kg, from the reaction
The carbonate catalyst is recovered by filtration in system.
The beneficial effect that technical scheme provided in an embodiment of the present invention is brought is：
The synthetic method of adjacent phenyl Phenoxyethanol provided in an embodiment of the present invention, by adjacent to being added in reactor
Phenylphenol, ethylene carbonate and carbonate catalyst, make reaction former under 60 DEG C -200 DEG C of reaction temperature
Material passes through carbonate catalyst catalytic reaction 0.5-10 hours in the molten state, to synthesize adjacent phenyl benzene oxygen second
Alcohol.After to reaction system cooling down, carbonate catalyst is recovered by filtration therefrom, purity can be obtained
Adjacent phenyl Phenoxyethanol finished product more than or equal to 95%.It can be seen that, method provided in an embodiment of the present invention passes through
Reacted using fusion method, without the oxirane using danger, and solvent need not be used, and then keep away
Exempted from follow-up washing alkali cleaning, solvent still-process, its not only synthetic route it is short, it is simple to operate, and realize
Zero release of pollutant, more safety and environmental protection.In addition, being recovered by filtration by carbonate catalyst, make
It is recycled, and effectively reduces energy consumption.
Specific embodiment
To make the object, technical solutions and advantages of the present invention clearer, below will be to embodiment of the present invention
It is described in further detail.
A kind of synthetic method of adjacent phenyl Phenoxyethanol is the embodiment of the invention provides, including：To in reactor
O-phenyl phenol, ethylene carbonate and carbonate catalyst are added, is urged under 60 DEG C -200 DEG C of reaction temperature
Change reaction 0.5-10 hours, after cooling down, carbonate catalyst is recovered by filtration from reaction system, obtain
Adjacent phenyl Phenoxyethanol.Wherein, o-phenyl phenol and the mass ratio of ethylene carbonate are 1:0.7-2, carbonate
The quality of catalyst is the 0.1%-15% of o-phenyl phenol and ethylene carbonate gross mass.
Specifically, the chemical structural formula of the adjacent phenyl Phenoxyethanol synthesized by the embodiment of the present invention is as follows：
The synthetic method of adjacent phenyl Phenoxyethanol provided in an embodiment of the present invention, by adjacent to being added in reactor
Phenylphenol, ethylene carbonate and carbonate catalyst, make reaction former under 60 DEG C -200 DEG C of reaction temperature
Material passes through carbonate catalyst catalytic reaction 0.5-10 hours in the molten state, to synthesize adjacent phenyl benzene oxygen second
Alcohol.After to reaction system cooling down, carbonate catalyst is recovered by filtration therefrom, purity can be obtained
Adjacent phenyl Phenoxyethanol finished product more than or equal to 95%.It can be seen that, method provided in an embodiment of the present invention passes through
Reacted using fusion method, without the oxirane using danger, and solvent need not be used, and then keep away
Exempted from follow-up washing alkali cleaning, solvent still-process, its not only synthetic route it is short, it is simple to operate, and realize
Zero release of pollutant, more safety and environmental protection.In addition, being recovered by filtration by carbonate catalyst, make
It is recycled, and effectively reduces energy consumption.In sum, adjacent phenyl benzene oxygen second provided in an embodiment of the present invention
The synthetic method of alcohol, simple and easy to apply, with low cost, safety and environmental protection is of far-reaching significance, beneficial to large-scale promotion
Use.
It will be appreciated by persons skilled in the art that because method provided in an embodiment of the present invention is to reaction pressure
Excessive demand is had no, the use of common reactor is to be capable of achieving the present invention.
Specifically, it is pure that the o-phenyl phenol that the embodiment of the present invention is used is chemistry with ethylene carbonate.In order to
Both conversion ratio is improved, while avoid the waste of ethylene carbonate, o-phenyl phenol and ethylene carbonate
Mass ratio is 1:0.8-1.5, preferably 1:0.9-1.2.For example, the matter of o-phenyl phenol and ethylene carbonate
Amount ratio can be 1:0.8、1:0.85、1:0.9、1:0.95、1:1.0、1:1.05、1:1.1、1:1.15 etc..
Research finds that the use of carbonate catalyst can promote o-phenyl phenol with ethylene carbonate in melting
Converted under state, beneficial to Fast back-projection algorithm neighbour's phenyl Phenoxyethanol.Preferably, carbonate catalyst choosing
At least one from potassium carbonate, sodium carbonate, calcium carbonate.When the consumption of carbonate catalyst is too low, meeting
Cause to extend the reaction time, and influence the yield of adjacent phenyl Phenoxyethanol；And work as the consumption of carbonate catalyst
When too high, the colourity of adjacent phenyl Phenoxyethanol finished product can be caused to deepen, reduce its quality.Based on this, this hair
Bright embodiment limits the quality of carbonate catalyst as o-phenyl phenol and ethylene carbonate gross mass
0.5%-10%, preferably 1%-8%, for example its can for 0.8%, 1%, 1.2%, 1.6%, 2%, 2.5%,
3%th, 3.5%, 4%, 4.5%, 5%, 5.5%, 6%, 6.5%, 7%, 7.5% etc..
Because the fusing point of o-phenyl phenol is at 58 DEG C, reaction system will be made to be changed into solid-liquid two-phase less than this temperature,
Substantially can not react, and be higher than that 200 DEG C of temperature can cause ethylene carbonate to decompose in advance, the adjacent benzene of influence
The yield of base Phenoxyethanol.Meanwhile, in order to ensure reaction rate and adjacent phenyl Phenoxyethanol finished product higher
Low colourity, the embodiment of the present invention limit the reaction temperature of o-phenyl phenol and ethylene carbonate catalytic reaction as
60 DEG C -200 DEG C, more preferably preferably 80 DEG C -180 DEG C, 100 DEG C -160 DEG C.For example, this is anti-
Answer temperature can for 85 DEG C, 90 DEG C, 95 DEG C, 100 DEG C, 105 DEG C, 110 DEG C, 115 DEG C, 120 DEG C, 125 DEG C,
130℃、135℃、140℃、145℃、150℃、155℃、160℃、165℃、170℃、175℃
Deng.
Further, in order to ensure o-phenyl phenol with ethylene carbonate while having conversion ratio higher, and
Avoid long-time unnecessary from reacting, that is, after preventing from exceeding certain reaction time, can not only improve conversion
Rate and easily cause the colourity of adjacent phenyl Phenoxyethanol and deepen, the embodiment of the present invention is by phenylphenol and ethylene
The time of alkene ester catalysis reaction is defined to 0.5-10 hours, preferably 1-5 hours.For example, the catalytic reaction
Time can for 1.5 hours, 2 hours, 2.5 hours, 3 hours, 3.5 hours, 4 hours, 4.5 hours,
5 hours etc..
After after catalytic reaction receiving, cooling down (can for example be cooled to 70-100 DEG C) is carried out to reaction system,
Then, carbonate catalyst is recovered by filtration from reaction system, you can obtain adjacent phenyl Phenoxyethanol finished product.
In order to ensure that carbonate catalyst can be separated substantially entirely with adjacent phenyl Phenoxyethanol, it is preferred to use insulation
The mode of pressurization carries out this and process is recovered by filtration.Specifically, it is 70-100 DEG C in temperature, and pressure is low
When 4kg, carbonate can be recovered by filtration from reaction system using common candle filter and urge
Agent.
Hereinafter the present invention will be further described through by specific embodiment.
In specific examples below, the unreceipted condition person of involved operation, according to normal condition or
The condition of manufacturer's suggestion is carried out.Raw materials used unreceipted production firm and specification person are can be by purchased in market
The conventional products of acquisition.
In following embodiment, the yield (also being understood as purity herein) of adjacent phenyl Phenoxyethanol finished product
It is to be calculated based on o-phenyl phenol, using the adjacent phenyl Phenoxyethanol obtained by high effective liquid chromatography for measuring
The yield of finished product；The acetone soln that mass concentration is 50% adjacent phenyl Phenoxyethanol is prepared, by colorimetric cylinder
In contrasted to obtain the chromatic value of the acetone soln with the standard curve that is obtained by APHA standard samples,
And then thus judge the colourity of adjacent phenyl Phenoxyethanol finished product.
Embodiment 1
To o-phenyl phenol, ethylene carbonate and potassium carbonate catalyst is added in reactor, it is catalyzed at 100 DEG C
Reaction 10 hours, after cooling down, insulation is recovered by filtration potassium carbonate from reaction system, and to adjacent phenyl benzene
Oxyethanol crude product carries out washing and drying, obtains the adjacent phenyl Phenoxyethanol finished product of desired white crystalline.Its
In, o-phenyl phenol is 1 with the mass ratio of ethylene carbonate:0.9, the quality of potassium carbonate catalyst is adjacent phenyl
The 1% of phenol and ethylene carbonate gross mass.
The yield and colourity of the adjacent phenyl Phenoxyethanol finished product obtained to the present embodiment are measured respectively, as a result
Show, the yield of adjacent phenyl Phenoxyethanol finished product is 96.77%, and colourity is less than 30.
Embodiment 2
To o-phenyl phenol, ethylene carbonate and sodium carbonate catalyst is added in reactor, it is catalyzed at 132 DEG C
Reaction 6 hours, after cooling down, insulation is recovered by filtration sodium carbonate from reaction system, and to adjacent phenyl benzene
Oxyethanol crude product carries out washing and drying, obtains the adjacent phenyl Phenoxyethanol finished product of desired white crystalline.Its
In, o-phenyl phenol is 1 with the mass ratio of ethylene carbonate:1.2, the quality of sodium carbonate for o-phenyl phenol and
The 5% of ethylene carbonate gross mass.
The yield and colourity of the adjacent phenyl Phenoxyethanol finished product obtained to the present embodiment are measured respectively, as a result
Show, the yield of adjacent phenyl Phenoxyethanol finished product is 98.61%, and colourity is less than 30.
Embodiment 3
To o-phenyl phenol, ethylene carbonate and potassium carbonate catalyst is added in reactor, it is catalyzed at 140 DEG C
Reaction 3 hours, after cooling down, insulation is recovered by filtration potassium carbonate from reaction system, and to adjacent phenyl benzene
Oxyethanol crude product carries out washing and drying, obtains the adjacent phenyl Phenoxyethanol finished product of desired white crystalline.Its
In, o-phenyl phenol is 1 with the mass ratio of ethylene carbonate:1.0, the quality of potassium carbonate for o-phenyl phenol and
The 10% of ethylene carbonate gross mass.
The yield and colourity of the adjacent phenyl Phenoxyethanol finished product obtained to the present embodiment are measured respectively, as a result
Show, the yield of adjacent phenyl Phenoxyethanol finished product is 97.56%, and colourity is 30-50.
Embodiment 4
To o-phenyl phenol, ethylene carbonate and potassium carbonate catalyst is added in reactor, it is catalyzed at 160 DEG C
Reaction 1 hour, after cooling down, insulation is recovered by filtration potassium carbonate from reaction system, and to adjacent phenyl benzene
Oxyethanol crude product carries out washing and drying, obtains the adjacent phenyl Phenoxyethanol finished product of desired white crystalline.Its
In, o-phenyl phenol is 1 with the mass ratio of ethylene carbonate:1.5, the quality of potassium carbonate catalyst is adjacent phenyl
The 15% of phenol and ethylene carbonate gross mass.
The yield and colourity of the adjacent phenyl Phenoxyethanol finished product obtained to the present embodiment are measured respectively, as a result
Show, the yield of adjacent phenyl Phenoxyethanol finished product is 99.20%, and colourity is 50-60.
Embodiment 5
To o-phenyl phenol, ethylene carbonate and calcium carbonate catalyst is added in reactor, it is catalyzed at 100 DEG C
Reaction 10 hours, after cooling down, insulation is recovered by filtration calcium carbonate from reaction system, and to adjacent phenyl benzene
Oxyethanol crude product carries out washing and drying, obtains the adjacent phenyl Phenoxyethanol finished product of desired white crystalline.Its
In, o-phenyl phenol is 1 with the mass ratio of ethylene carbonate:1.3, the quality of calcium carbonate for o-phenyl phenol and
The 10% of ethylene carbonate gross mass.
The yield and colourity of the adjacent phenyl Phenoxyethanol finished product obtained to the present embodiment are measured respectively, as a result
Show, the yield of adjacent phenyl Phenoxyethanol finished product is 98.76%, and colourity is 30-50.
Embodiment 6
To o-phenyl phenol, ethylene carbonate and sodium carbonate catalyst is added in reactor, it is catalyzed at 140 DEG C
Reaction 3 hours, after cooling down, insulation is recovered by filtration sodium carbonate from reaction system, and to adjacent phenyl benzene
Oxyethanol crude product carries out washing and drying, obtains the adjacent phenyl Phenoxyethanol finished product of desired white crystalline.Its
In, o-phenyl phenol is 1 with the mass ratio of ethylene carbonate:1.1, the quality of sodium carbonate for o-phenyl phenol and
The 5% of ethylene carbonate gross mass.
The yield and colourity of the adjacent phenyl Phenoxyethanol finished product obtained to the present embodiment are measured respectively, as a result
Show, the yield of adjacent phenyl Phenoxyethanol finished product is 97.87%, and colourity is less than 30.
Embodiment 7
To o-phenyl phenol, ethylene carbonate and sodium carbonate catalyst is added in reactor, it is catalyzed at 115 DEG C
Reaction 4 hours, after cooling down, insulation is recovered by filtration sodium carbonate from reaction system, and to adjacent phenyl benzene
Oxyethanol crude product carries out washing and drying, obtains the adjacent phenyl Phenoxyethanol finished product of desired white crystalline.Its
In, o-phenyl phenol is 1 with the mass ratio of ethylene carbonate:1.25, the quality of sodium carbonate for o-phenyl phenol and
The 5% of ethylene carbonate gross mass.
The yield and colourity of the adjacent phenyl Phenoxyethanol finished product obtained to the present embodiment are measured respectively, as a result
Show, the yield of adjacent phenyl Phenoxyethanol finished product is 95.68%, and colourity is less than 30.
Embodiment 8
To o-phenyl phenol, ethylene carbonate and calcium carbonate catalyst is added in reactor, it is catalyzed at 135 DEG C
Reaction 8 hours, after cooling down, insulation is recovered by filtration calcium carbonate from reaction system, and to adjacent phenyl benzene
Oxyethanol crude product carries out washing and drying, obtains the adjacent phenyl Phenoxyethanol finished product of desired white crystalline.Its
In, o-phenyl phenol is 1 with the mass ratio of ethylene carbonate:1.5, the quality of calcium carbonate for o-phenyl phenol and
The 10% of ethylene carbonate gross mass.
The yield and colourity of the adjacent phenyl Phenoxyethanol finished product obtained to the present embodiment are measured respectively, as a result
Show, the yield of adjacent phenyl Phenoxyethanol finished product is 98.12%, and colourity is 30-50.
Embodiment 9
To o-phenyl phenol, ethylene carbonate and potassium carbonate catalyst is added in reactor, it is catalyzed at 100 DEG C
Reaction 20 hours, after cooling down, insulation is recovered by filtration potassium carbonate from reaction system, and to adjacent phenyl benzene
Oxyethanol crude product carries out washing and drying, obtains the adjacent phenyl Phenoxyethanol finished product of desired white crystalline.Its
In, o-phenyl phenol is 1 with the mass ratio of ethylene carbonate:0.7, the quality of potassium carbonate catalyst is adjacent phenyl
The 0.1% of phenol and ethylene carbonate gross mass.
The yield and colourity of the adjacent phenyl Phenoxyethanol finished product obtained to the present embodiment are measured respectively, as a result
Show, the yield of adjacent phenyl Phenoxyethanol finished product is 95.77%, and colourity is less than 30.
Embodiment 10
To o-phenyl phenol, ethylene carbonate and sodium carbonate catalyst is added in reactor, it is catalyzed at 200 DEG C
Reaction 0.5 hour, after cooling down, insulation is recovered by filtration sodium carbonate from reaction system, and to adjacent phenyl benzene
Oxyethanol crude product carries out washing and drying, obtains the adjacent phenyl Phenoxyethanol finished product of desired white crystalline.Its
In, o-phenyl phenol is 1 with the mass ratio of ethylene carbonate:0.8, the quality of sodium carbonate for o-phenyl phenol and
The 0.5% of ethylene carbonate gross mass.
The yield and colourity of the adjacent phenyl Phenoxyethanol finished product obtained to the present embodiment are measured respectively, as a result
Show, the yield of adjacent phenyl Phenoxyethanol finished product is 95.02%, and colourity is 70-80.
Embodiment 11
To o-phenyl phenol, ethylene carbonate and calcium carbonate catalyst is added in reactor, it is catalyzed at 180 DEG C
Reaction 1 hour, after cooling down, insulation is recovered by filtration calcium carbonate from reaction system, and to adjacent phenyl benzene
Oxyethanol crude product carries out washing and drying, obtains the adjacent phenyl Phenoxyethanol finished product of desired white crystalline.Its
In, o-phenyl phenol is 1 with the mass ratio of ethylene carbonate:1.5, the quality of calcium carbonate for o-phenyl phenol and
The 1% of ethylene carbonate gross mass.
The yield and colourity of the adjacent phenyl Phenoxyethanol finished product obtained to the present embodiment are measured respectively, as a result
Show, the yield of adjacent phenyl Phenoxyethanol finished product is 96.11%, and colourity is 70-80.
Embodiment 12
To o-phenyl phenol, ethylene carbonate and potassium carbonate catalyst is added in reactor, it is catalyzed at 80 DEG C
Reaction 10 hours, after cooling down, insulation is recovered by filtration potassium carbonate from reaction system, and to adjacent phenyl benzene
Oxyethanol crude product carries out washing and drying, obtains the adjacent phenyl Phenoxyethanol finished product of desired white crystalline.Its
In, o-phenyl phenol is 1 with the mass ratio of ethylene carbonate:2, the quality of potassium carbonate catalyst is adjacent phenyl benzene
The 10% of phenol and ethylene carbonate gross mass.
The yield and colourity of the adjacent phenyl Phenoxyethanol finished product obtained to the present embodiment are measured respectively, as a result
Show, the yield of adjacent phenyl Phenoxyethanol finished product is 97.01%, and colourity is 30-50.
Embodiment 13
To o-phenyl phenol, ethylene carbonate and potassium carbonate catalyst is added in reactor, it is catalyzed at 160 DEG C
Reaction 1 hour, after cooling down, insulation is recovered by filtration potassium carbonate from reaction system, and to adjacent phenyl benzene
Oxyethanol crude product carries out washing and drying, obtains the adjacent phenyl Phenoxyethanol finished product of desired white crystalline.Its
In, o-phenyl phenol is 1 with the mass ratio of ethylene carbonate:1.5, the quality of potassium carbonate catalyst is adjacent phenyl
The 8% of phenol and ethylene carbonate gross mass.
The yield and colourity of the adjacent phenyl Phenoxyethanol finished product obtained to the present embodiment are measured respectively, as a result
Show, the yield of adjacent phenyl Phenoxyethanol finished product is 96.89%, and colourity is 50-60.
Embodiment 14
To o-phenyl phenol, ethylene carbonate and potassium carbonate catalyst is added in reactor, it is catalyzed at 200 DEG C
Reaction 5 hours, after cooling down, insulation is recovered by filtration potassium carbonate from reaction system, and to adjacent phenyl benzene
Oxyethanol crude product carries out washing and drying, obtains the adjacent phenyl Phenoxyethanol finished product of desired white crystalline.Its
In, o-phenyl phenol is 1 with the mass ratio of ethylene carbonate:0.7, the quality of potassium carbonate catalyst is adjacent phenyl
The 1% of phenol and ethylene carbonate gross mass.
The yield and colourity of the adjacent phenyl Phenoxyethanol finished product obtained to the present embodiment are measured respectively, as a result
Show, the yield of adjacent phenyl Phenoxyethanol finished product is 96.77%, and colourity is 70-80.
Embodiment 15
To o-phenyl phenol, ethylene carbonate and potassium carbonate catalyst is added in reactor, it is catalyzed at 90 DEG C
Reaction 8 hours, after cooling down, insulation is recovered by filtration potassium carbonate from reaction system, and to adjacent phenyl benzene
Oxyethanol crude product carries out washing and drying, obtains the adjacent phenyl Phenoxyethanol finished product of desired white crystalline.Its
In, o-phenyl phenol is 1 with the mass ratio of ethylene carbonate:0.8, the quality of potassium carbonate catalyst is adjacent phenyl
The 0.8% of phenol and ethylene carbonate gross mass.
The yield and colourity of the adjacent phenyl Phenoxyethanol finished product obtained to the present embodiment are measured respectively, as a result
Show, the yield of adjacent phenyl Phenoxyethanol finished product is 96.23%, and colourity is less than 30.
Embodiment 16
To o-phenyl phenol, ethylene carbonate and potassium carbonate catalyst is added in reactor, it is catalyzed at 180 DEG C
Reaction 1 hour, after cooling down, insulation is recovered by filtration potassium carbonate from reaction system, and to adjacent phenyl benzene
Oxyethanol crude product carries out washing and drying, obtains the adjacent phenyl Phenoxyethanol finished product of desired white crystalline.Its
In, o-phenyl phenol is 1 with the mass ratio of ethylene carbonate:0.9, the quality of potassium carbonate catalyst is adjacent phenyl
The 0.9% of phenol and ethylene carbonate gross mass.
The yield and colourity of the adjacent phenyl Phenoxyethanol finished product obtained to the present embodiment are measured respectively, as a result
Show, the yield of adjacent phenyl Phenoxyethanol finished product is 97.22%, and colourity is 70-80.
By various embodiments above as can be seen that course of reaction provided in an embodiment of the present invention need not pressurize, close
Shorter into route, process is simple is easy to control, not dangerous without solvent, safe and reliable, adjacent phenyl
Up to more than 95%, colourity is below 80 to the yield of Phenoxyethanol finished product, with superior market using preceding
Scape.
Presently preferred embodiments of the present invention is the foregoing is only, the protection domain being not intended to limit the invention is all
Within the spirit and principles in the present invention, any modification, equivalent substitution and improvements made etc., all should include
Within protection scope of the present invention.
Claims (9)
1. a kind of synthetic method of adjacent phenyl Phenoxyethanol, including：To in reactor add o-phenyl phenol,
Ethylene carbonate and carbonate catalyst, catalytic reaction 0.5-10 hours under 60 DEG C -200 DEG C of reaction temperature,
After cooling down, the carbonate catalyst is recovered by filtration from reaction system, obtains adjacent phenyl Phenoxyethanol；
The o-phenyl phenol is 1 with the mass ratio of ethylene carbonate:0.7-2, the matter of the carbonate catalyst
It is the 0.1%-15% of the o-phenyl phenol and the ethylene carbonate gross mass to measure.
2. synthetic method according to claim 1, it is characterised in that the o-phenyl phenol and carbonic acid
The mass ratio of vinyl acetate is 1:0.8-1.5；
The quality of the carbonate catalyst is the o-phenyl phenol and the ethylene carbonate gross mass
0.5%-10%.
3. synthetic method according to claim 2, it is characterised in that the o-phenyl phenol and carbonic acid
The mass ratio of vinyl acetate is 1:0.9-1.2；
The quality of the carbonate catalyst is the o-phenyl phenol and the ethylene carbonate gross mass
1%-8%.
4. synthetic method according to claim 1, it is characterised in that the carbonate catalyst is selected from
At least one in potassium carbonate, sodium carbonate, calcium carbonate.
5. synthetic method according to claim 1, it is characterised in that the reaction temperature is 80 DEG C
-180℃。
6. synthetic method according to claim 5, it is characterised in that the reaction temperature is 100 DEG C
-160℃。
7. synthetic method according to claim 1, it is characterised in that the time of the catalytic reaction is
1-5 hours.
8. synthetic method according to claim 1, it is characterised in that by the way of heat-insulating pressurizing from
The carbonate catalyst is recovered by filtration in the reaction system.
9. synthetic method according to claim 8, it is characterised in that in temperature be 70-100 DEG C, with
And pressure be less than or equal to 4kg when, the carbonate catalyst is recovered by filtration from the reaction system.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN114276220A (en) * | 2020-09-27 | 2022-04-05 | 上海抚佳精细化工有限公司 | Preparation method of o-phenylphenoxyethanol |
| CN114394887A (en) * | 2022-01-28 | 2022-04-26 | 江苏锐鸣材料科技有限公司 | Phenyloxyethanol compound and preparation method thereof |
| CN115166093A (en) * | 2022-07-13 | 2022-10-11 | 佳化化学科技发展（上海）有限公司 | Content detection method of OPPEA |
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| US4341905A (en) * | 1979-07-18 | 1982-07-27 | The Dow Chemical Company | Inorganic halide salt catalysts for hydroxyalkylation of phenols or thiophenols |
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| CN114276220A (en) * | 2020-09-27 | 2022-04-05 | 上海抚佳精细化工有限公司 | Preparation method of o-phenylphenoxyethanol |
| CN114394887A (en) * | 2022-01-28 | 2022-04-26 | 江苏锐鸣材料科技有限公司 | Phenyloxyethanol compound and preparation method thereof |
| CN115166093A (en) * | 2022-07-13 | 2022-10-11 | 佳化化学科技发展（上海）有限公司 | Content detection method of OPPEA |
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