CN110922304A - Production method of fluoroether - Google Patents
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- CN110922304A CN110922304A CN201911007363.7A CN201911007363A CN110922304A CN 110922304 A CN110922304 A CN 110922304A CN 201911007363 A CN201911007363 A CN 201911007363A CN 110922304 A CN110922304 A CN 110922304A
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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
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
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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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- 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
- C07C41/38—Separation; Purification; Stabilisation; Use of additives by liquid-liquid treatment
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- Y02P20/584—Recycling of catalysts
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Abstract
The invention discloses a method for producing fluoroether, which comprises the steps of reacting a raw material and fluoroolefin in the presence of a catalyst under the condition of solvent or no solvent to obtain fluoroether reaction liquid, wherein the raw material is alcohol or a phenol substance, concentrating the fluoroether reaction liquid to obtain concentrated liquid and clear liquid, and purifying and separating the clear liquid to obtain a fluoroether product. The invention solves the problems of catalyst recovery and reutilization, difficult solid-slag separation and the like, and has the advantages of high product purity, less three wastes, economy, environmental protection and the like.
Description
Technical Field
The invention relates to the technical field of fluoroethers, in particular to a production method of fluoroethers.
Background
Fluoroether is a novel ODS substitute, has zero ODP value, low GWP value and short atmospheric residence time, and is considered to be one of ideal substitutes for ODS. Besides excellent environmental properties, fluoroethers also have the characteristics of low toxicity, no corrosiveness, easiness in storage and transportation and the like, and are widely used in the fields of foaming agents, cleaning agents, solvents, battery electrolytes and the like. Therefore, the preparation method thereof becomes a hot point for research.
At present, there are a lot of reports on the synthesis method of fluoroether in the literature, and the reaction of alcohol and fluoroolefin in the presence of catalyst is mainly adopted to generate reaction liquid containing fluoroether, and the finished product is obtained through post-treatment. The catalyst is generally alkaline catalyst such as sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium alkoxide, potassium fluoride, triethylamine and the like, and the reaction can be carried out in the presence or absence of solvent, wherein the solvent is selected from water, acetonitrile, DMF, tert-butyl alcohol, 1, 4-dioxane, 2-methyltetrahydrofuran, tetraethylene glycol dimethyl ether and the like. The post-treatment process generally comprises directly rectifying or distilling the reaction liquid, or extracting or filtering and then rectifying or distilling. There is less literature relating to post-treatment processes such as catalyst recovery.
For example, chinese patent publication No. CN105906489A discloses a method for simultaneously preparing hydrofluoroether and fluorine-containing alkenyl ether, wherein fluorine-containing olefin reacts with alcohol in a solvent in the presence of a catalyst, the reaction pressure is controlled to be 0.2-1.5 MPa by adjusting the amount of fluorine-containing olefin introduced during the reaction, and the molar ratio of the alcohol to the solvent to the catalyst is 1: 0.5-3: 0.1-1.5, the reaction temperature is 50-150 ℃, and when the molar ratio of the introduced fluorine-containing olefin to the alcohol is 1.0-1.2: and (1) ending the reaction, and distilling and separating to respectively obtain hydrofluoroether and fluorine-containing alkene ether products.
For another example, chinese patent publication No. CN103254041A discloses a method for preparing hydrofluoroether, which comprises mixing a solvent, a catalyst, an olefin and an alcohol, and reacting, wherein the molar ratio of the solvent to the alcohol is 1-6: 1, the molar ratio of the catalyst to the alcohol is 0.01-0.15: 1, the mass ratio of the olefin to the alcohol is 0.5-5: 1, the reaction temperature is 20-60 ℃, the reaction pressure is 0.05-0.6 MPa, the reaction time is 0.5-3 h, and after the reaction is finished, the hydrofluoroether product is obtained by rectification.
Further, as disclosed in chinese patent publication No. CN1832909A, a process for producing a fluorinated alkyl ether is provided which can achieve a satisfactory reaction rate even under mild reaction conditions and can efficiently carry out subsequent steps such as distillation after the reaction. Specifically, an aprotic polar solvent, a fluorinated ether, a catalyst, a fluorinated alkanol and a fluorinated alkene are introduced into a reaction vessel, and then the fluorinated alkanol and the fluorinated alkene are reacted with each other to produce a fluorinated alkyl ether, wherein the mass ratio of the aprotic polar solvent to the fluorinated ether introduced into the reaction vessel is 5/95 to 80/20.
Also for example, Chinese patent publication No. CN104045524A relates to the technical field of hydrofluoroether production, in particular to a method for cleanly producing hydrofluoroether, which comprises the following steps: adding a fluorine-containing sodium alkoxide catalyst into a fluorine-containing alcohol solution, adding fluorinated olefin, heating and stirring for reaction to obtain a mixed solution; carrying out post-treatment on the mixed solution to obtain hydrofluoroether; the post-treatment method is rectification.
Another example is Chinese patent publication No. CN1636951A related to Rf-CH2-O-CF2-CHR1R2A process for producing a fluorinated ether compound, which comprises: in the presence of an alkaline compound and at least one substance selected from secondary alcohols and tertiary alcohols, reacting a compound consisting of Rf-CH2Fluorinated alcohols represented by OH with CF2＝CR1R2The fluorine-containing olefin compound represented by (1) is reacted. This patent does not describe a post-treatment method.
For another example, chinese patent publication No. CN103739450A relates to a method for preparing hydrofluoroether. The method comprises the following steps: (1) dissolving an alkaline compound in fluoroalkyl alcohol, adding a solvent, adding fluorinated olefin, heating and stirring for reaction to obtain a mixed solution; (2) and (3) washing the mixed solution obtained in the step (1), standing for layering, taking the organic phase solution of the lower layer, and rectifying to obtain the hydrofluoroether product.
The defects of the prior art are as follows: in the existing production technology for synthesizing fluoroether, the side reaction that the product fluoroether is dehydrofluorinated to generate the alkenyl ether is generated, the alkenyl ether and fluoroolefin generated by the side reaction are easy to hydrolyze in the presence of an alkaline catalyst to generate fluoride salt substances, the fluoride salt substances and other solid byproducts and the alkaline catalyst form fine particle solid residues in a precipitation form after the reaction is finished, and the problems of filter cloth blockage, filter penetration, difficult filtration, long filtration time and the like can occur in direct filtration. Meanwhile, unreacted alkaline catalyst in the solid slag is difficult to recycle, so that the production cost and the difficulty in treating the three wastes are increased. The filtered catalyst can further enable the product fluoroether to undergo dehydrofluorination reaction to generate the alkenyl ether in the subsequent rectification and purification process, thereby not only reducing the yield, but also influencing the purity of the product.
Disclosure of Invention
Aiming at the defects of difficult filtration, difficult recovery of the catalyst, easy production of by-product of vinyl ether in subsequent purification treatment and the like in the prior art, the invention provides the production method of the fluoroether, which has high yield and product purity, is environment-friendly and economic and can recycle the catalyst.
In order to achieve the purpose, the invention adopts the technical scheme that: a process for preparing fluoroether includes such steps as reacting raw material (alcohol or phenol) with fluoroolefin in the presence of catalyst in the presence or absence of solvent to obtain fluoroether reaction liquid, concentrating to obtain concentrated liquid and clear liquid, and purifying and separating the clear liquid to obtain fluoroether product.
In a preferred embodiment of the present invention, the raw material alcohol or phenol may be added to the concentrated solution, followed by extraction and filtration to obtain a residue and a filtrate containing the catalyst. The specification of the filtering cloth is preferably 500-1000 meshes.
In a preferred embodiment of the present invention, the catalyst-containing filtrate may be recycled.
As the raw material alcohol in the present invention, aliphatic hydrocarbon alcohol, cyclic hydrocarbon alcohol, and monohydric alcohol or polyhydric alcohol containing a functional group such as halogen, a double bond, a triple bond, a nitro group, an amino group, a cyano group, an aldehyde group, a ketone group or an ether group can be used. In a preferred embodiment of the present invention, the alcohol is preferably methanol, ethanol, ethylene glycol, propylene glycol, isopropyl alcohol, butanol, cyclohexyl alcohol, ethylene glycol monomethyl ether, allyl alcohol, glycerol, trifluoroethanol, difluoroethanol, tetrafluoropropanol, 2,3,3,4,4,5, 5-octafluoropentanol, pentafluoropropanol, perfluorobutyl ethanol, perfluorohexyl ethanol, or perfluoroethyl ethanol.
In a preferred embodiment of the present invention, the phenolic substance is preferably phenol, hydroxybenzaldehyde, pentafluorophenol or naphthol.
The fluoroolefin of the present invention may be a fluorohydrocarbon containing or not containing other halogen atoms, or a fluorohydrocarbon containing oxygen, sulfur, nitrogen, etc. In a preferred embodiment of the present invention, the fluoroolefin is preferably hexafluoropropylene, tetrafluoroethylene, trifluoroethylene, vinylidene fluoride, chlorotrifluoroethylene, trifluorobromoethylene, trifluoromethoxytrifluoroethylene, 1-bis (trifluoromethoxy) difluoroethylene, phenoxytrifluoroethylene, or trifluoromethyl trifluorovinyl ether.
The catalyst of the present invention may be an inorganic base or an organic base, and as a preferred embodiment of the present invention, the catalyst is preferably potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate, potassium tert-butoxide, tetramethylammonium hydroxide, trimethylamine, or triethylamine.
As a preferred embodiment of the present invention, the solvent is preferably N, N-dimethylformamide, N-dimethylacetamide, sulfolane, acetonitrile, tetrahydrofuran, methyltetrahydrofuran, dioxane, methyl tert-butyl ether, cyclohexanone, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, tetraethylene glycol dimethyl ether.
In a preferred embodiment of the invention, the molar ratio of the alcohol or the phenolic substance to the fluoroolefin is 1: 0.8-2, the addition amount of the alcohol or the phenolic substance is 1-10 times of the mass of the catalyst, the reaction temperature is-20-150 ℃, and the reaction pressure is 0-1.5 MPa.
In a preferred embodiment of the present invention, the mass of the concentrated solution is preferably 5 to 50% of the mass of the fluoroether reaction solution.
Aiming at the defects of difficult filtration, difficult catalyst recovery, easy byproduct vinyl ether generation in subsequent purification treatment and the like in the prior art, the inventor conducts a great deal of research and unexpectedly finds that the reason for difficult solid residue filtration is that solid residue particles formed in a precipitation form after the reaction of the solid byproduct and the alkaline catalyst are fine and have certain viscosity, and the solid residue particles are easy to block filter cloth. Meanwhile, the inventor finds that the raw material alcohol or the phenolic substance can dissolve the catalyst, or effective components in the catalyst are extracted into the raw material alcohol or the phenolic substance, so that the aim of separating and recycling the catalyst is fulfilled. Through this idea, the present invention has been achieved. The method provided by the invention can realize the recovery and reutilization of the catalyst, solves the problems of difficult solid-slag separation, easy production of vinyl ether byproducts in the separation and purification process and the like, and has the advantages of economy, environmental protection, high product purity and the like.
In actual production, the method for producing a fluoroether of the present invention can be divided into steps such as reaction, concentration, extraction, and filtration, or units having reaction, concentration, extraction, and filtration functions. In the reaction step, alcohol or phenolic substance reacts with fluoroolefin in the presence of a catalyst to generate fluoroether reaction liquid; concentrating the fluoroether reaction solution in a concentration process to obtain a concentrated solution and a clear solution; the concentrated solution enters an extraction process, a certain amount of raw material alcohol or phenolic substances are added into the concentrated solution, and the catalyst in the solid residue of the concentrated solution is extracted; then solid residue and extract liquid containing the catalyst are obtained by filtering and separating in the filtering procedure, and the extract liquid containing the catalyst returns to the reactor to continue the reaction, thereby realizing the recovery and the reutilization of the catalyst.
The concentration step is to make the fluoroether reaction liquid generated in the reaction step undergo the processes of membrane permeation, evaporation concentration, sedimentation separation and centrifugal sedimentation to make the clear liquid containing fluoroether and concentrated liquid containing catalyst solid residue undergo the process of primary separation. Depending on the separation method, the composition of the concentrated solution may be the same as or different from that of the fluoroether reaction solution before concentration. The mass ratio of the concentrated solution containing the catalyst solid residue to the mass of the fluoroether reaction solution before concentration has no special requirement, and is selected to be 5-50%, preferably 10-40% in view of economical efficiency, and the lower ratio is also allowed by the process.
In the extraction step, the raw alcohol or phenol is added to the concentrated solution to dissolve the catalyst in the solid residue in the concentrated solution containing the alcohol or phenol, and the amount of the raw alcohol or phenol added is preferably 1 to 10 times the mass of the catalyst in view of the dissolution effect.
In the filtering step, any operation capable of separating the solid residue containing no catalyst from the extract containing alcohol and catalyst is within the scope of the present invention, and the filtering operation may be performed by, but not limited to, centrifugation, suction filtration, filter pressing, membrane filtration, and the like. The separated alcohol or phenol-containing substance and the extract of the catalyst are returned to the reaction step, and accordingly, the amount of the catalyst used can be reduced.
Compared with the prior art, the invention has the following advantages:
1. the method is economic and environment-friendly, can extract the catalyst into raw material alcohol or phenolic substances, realizes the recovery and the reutilization of the catalyst, greatly reduces the using amount of the catalyst and reduces the production cost; meanwhile, the phenomenon that the catalyst is easy to generate dehydrofluorination reaction on the product to generate vinyl ether at the rectification temperature is obviously reduced, the generation amount of byproducts is reduced, and the discharge of three wastes is greatly reduced;
2. the method has high yield and product purity, remarkably reduces the phenomenon that the catalyst is easy to generate dehydrofluorination reaction on the product to generate the vinyl ether at the rectification temperature, reduces the impurity content in the product, improves the product purity and the reaction yield, and ensures that the product purity is over 99.6 percent, wherein the impurity content of the vinyl ether in the product is below 0.05 percent by weight (percent by mass);
3. the method has the advantages of simple process and high efficiency, solves the problems of difficult solid-slag separation, easy production of alkene ether byproducts in the separation and purification process and the like in the prior art through conventional operations such as reaction, concentration, extraction, filtration and the like, shortens the filtration time, has no percolation phenomenon during filtration, improves the filtration efficiency, obviously simplifies the process, and improves the production efficiency.
Detailed Description
Example 1
(a) A reaction process:
50kg of N, N-dimethylformamide, 20kg of phenol and 4kg of potassium carbonate catalyst are added into a 200L pressure reaction kettle, the gas in the kettle is replaced by nitrogen, the mixture is stirred, the temperature is raised to 90 ℃, hexafluoropropylene is introduced, the pressure is maintained at 0.4MPa for reaction, after 3.51kg of hexafluoropropylene (1.1 times of the mole number of phenol) is introduced, the reaction is stopped, the temperature is kept for 1h, the reaction solution is cooled, and the reaction solution is sent to a concentration process. The reaction mixture was sampled and analyzed, and the yield of 1,1,2,3, 3-hexafluoropropoxybenzene was 91%.
(b) A concentration process:
and circulating the reaction solution in a ceramic membrane filter, obtaining a concentrated solution containing catalyst solid residues and a filtrate containing no solid residues when the mass of the concentrated solution is 20% of the total mass of the reaction solution, and rectifying the filtrate containing no solid residues to obtain 1,1,2,3, 3-hexafluoropropoxybenzene with the purity of 99.6%, wherein the content of the impurity vinyl ether in the product is 0.03 wt%. Adding 5kg of phenol into the concentrated solution containing the solid residues of the catalyst, stirring for 1h, extracting the catalyst, passing the obtained extract through a centrifuge filled with 1000-mesh filter cloth to obtain filter residues and filtrate containing the catalyst, and circularly conveying the filtrate containing the catalyst to a reaction kettle to participate in the next batch of reaction.
Example 2
(a) A reaction process:
1000g of methanol and 200g of sodium hydroxide serving as a catalyst are added into a 5L pressure reaction kettle, the gas in the kettle is replaced by nitrogen, the mixture is stirred, the temperature is raised to 40 ℃, tetrafluoroethylene is introduced to maintain the pressure at 0.2MPa for reaction, when the introduction amount of the tetrafluoroethylene reaches 2800g (0.9 time of the mole number of the methanol), the reaction is stopped, the temperature is kept for 1.5h, the reaction solution is cooled, and the reaction solution is sent to a concentration process. The reaction mixture was sampled and analyzed, and the yield of methyl-1, 1,2, 2-tetrafluoroethyl ether was 92%.
(b) A concentration process:
and (3) distilling the synthesized reaction liquid, stopping distilling when the mass of the concentrated solution is 40% of the total mass of the reaction liquid to obtain a concentrated solution containing catalyst solid residues and a fraction containing no solid residues, and performing extractive distillation on the fraction containing no solid residues to obtain methyl-1, 1,2, 2-tetrafluoroethyl ether with the purity of 99.9%, wherein the content of the impurity vinyl ether in the product is 0.01 wt%. Adding 1000g of methanol into the concentrated solution containing the catalyst solid residue, stirring for 1.5h, extracting the catalyst, passing the obtained extract through a centrifuge filled with 600-mesh filter cloth to obtain filter residue and filtrate containing the catalyst, wherein the filtrate containing the catalyst can be circularly sent to a reaction kettle to participate in the next batch of reaction.
Example 3
(a) A reaction process:
adding 400g of dioxane, 600g of trifluoroethanol and 60g of catalyst tetramethylammonium hydroxide into a 2L pressure reaction kettle, replacing gas in the kettle with nitrogen, stirring, heating to 60 ℃, introducing tetrafluoroethylene to maintain the pressure at 0.6MPa for reaction, stopping the reaction when the introduction amount of the tetrafluoroethylene reaches 630g (1.05 times of the molar number of the trifluoroethanol), preserving the temperature for 1.7h, cooling to obtain a reaction solution, and sending the reaction solution to a concentration process. The reaction solution was sampled and analyzed, and the yield of 2,2, 2-trifluoroethyl-1, 1,2, 2-tetrafluoroethyl ether was 98%.
(b) A concentration process:
and (2) circulating the reaction solution in a ceramic membrane filter, and when the mass of the concentrated solution is 10% of the total mass of the reaction solution, obtaining a concentrated solution containing catalyst solid residues and a filtrate containing no solid residues, and rectifying the filtrate containing no solid residues to obtain 2,2, 2-trifluoroethyl-1, 1,2, 2-tetrafluoroethyl ether with the purity of 99.9%, wherein the content of the impurity vinyl ether in the product is 0.05 wt%. Adding 200g of trifluoroethanol into the concentrated solution containing the catalyst solid residue, stirring for 1.7h, extracting the catalyst, passing the obtained extract through a vacuum filter press with 500-mesh filter cloth to obtain filter residue and filtrate containing the catalyst, and circularly conveying the filtrate containing the catalyst to a reaction kettle to participate in the next batch of reaction.
Example 4
(a) A reaction process:
400g of sulfolane, 400g of 2,2,3,3,4,4,5, 5-octafluoropentanol and 50g of potassium hydroxide serving as a catalyst are added into a 2L pressure reaction kettle, the gas in the kettle is replaced by nitrogen, the mixture is stirred, the temperature is raised to 60 ℃, trifluoromethyl trifluorovinyl ether is introduced, the pressure is maintained at 0.3MPa for reaction, after the introduction amount of the trifluoromethyl trifluorovinyl ether reaches 429g (1.5 times of the mole number of the 2,2,3,3,4,4,5, 5-octafluoropentanol), the temperature is kept for 2h, and the reaction solution is obtained after cooling and sent to a concentration process. The reaction mixture was sampled and analyzed, and the yield of 2-trifluoromethoxy-1, 1, 2-trifluoroethyl-2, 2,3,3,4,4,5, 5-octafluoropentyl ether was 93%.
(b) A concentration process:
and settling the reaction liquid for 48 hours to obtain clear liquid with an upper layer containing no solids and concentrated liquid with a lower layer containing catalyst solid residues, wherein the lower layer accounts for 30 percent of the total mass of the reaction liquid, extracting the clear liquid with the upper layer containing no solids, and rectifying to obtain the 2-trifluoromethoxy-1, 1, 2-trifluoroethyl-2, 2,3,3,4,4,5, 5-octafluoropentyl ether with the purity of 99.9 percent, wherein the content of the impurity vinyl ether in the product is 0.04 percent by weight. Adding 400g of 2,2,3,3,4,4,5, 5-octafluoropentanol into the lower concentrated solution containing the catalyst solid residues, stirring for 2h, extracting the catalyst in the concentrated solution, passing the obtained extract through a vacuum suction filter with 800-mesh filter cloth to obtain filter residues and filtrate containing the catalyst, and circularly conveying the filtrate containing the catalyst to a reaction kettle to participate in the next batch of reaction.
Examples 5 to 7
The procedure and reaction parameters were the same as in example 3, except that different solvents, alcohols and fluoroolefins were used. The results of the tests are shown in the following table.
Catalyst-containing filtrate recycling test
The implementation steps and reaction parameters were unchanged, the filtrates containing the catalyst obtained in examples 1-7 were respectively recycled to the reaction kettle to participate in the next batch of reaction, and the catalyst amounts were measured, the implementation conditions are shown in the following table.
Comparative example 1
The same procedure and reaction parameters as in example 3 were used, except that: the reaction solution is directly filtered in vacuum, and the filtered reaction solution is rectified and purified to obtain a product with the yield of 95 percent and the purity of 99.5 percent.
The implementation steps and reaction parameters are unchanged, filtrate obtained by vacuum filtration in the comparative example 1 is circularly sent to a reaction kettle to participate in the next batch of reaction, and the dosage of the catalyst is measured. The implementation is shown in the following table.
As can be seen from the table: in comparative example 1, the catalyst is difficult to recover, the next batch of reaction catalyst is large in dosage, the filtration time is long, the filter cake is not easy to be drained, the filtrate is turbid, and solid penetrates through the filter cake. The filtered alkaline catalyst is easy to generate dehydrofluorination reaction on the product to generate the vinyl ether at the rectification temperature, so that the purity of the product is reduced. Compared with the comparative example 1, the example 3 has the advantages of short filtering time, no penetration, transparent filtrate, recoverable catalyst, high product purity and the like.
Claims (10)
1. A method for producing fluoroether comprises the steps of reacting a raw material and fluoroolefin in the presence of a catalyst under the condition of solvent or no solvent to obtain fluoroether reaction liquid, wherein the raw material is alcohol or a phenolic substance.
2. The method of claim 1, wherein the concentrated solution is extracted by adding a starting alcohol or a phenol, and filtered to obtain a residue and a filtrate containing a catalyst.
3. The process for producing a fluoroether according to claim 2, wherein said filtrate containing a catalyst is recycled.
4. The method for producing a fluoroether according to claim 1, wherein the alcohol is methanol, ethanol, ethylene glycol, propylene glycol, isopropyl alcohol, butanol, cyclohexyl alcohol, ethylene glycol monomethyl ether, allyl alcohol, glycerin, trifluoroethanol, difluoroethanol, tetrafluoropropanol, 2,3,3,4,4,5, 5-octafluoropentanol, pentafluoropropanol, perfluorobutyl ethanol, perfluorohexyl ethanol, perfluoroethyl ethanol.
5. The method of claim 1, wherein the phenolic compound is phenol, hydroxybenzaldehyde, pentafluorophenol, or naphthol.
6. The process for producing a fluoroether according to claim 1, wherein said fluoroolefin is hexafluoropropylene, tetrafluoroethylene, trifluoroethylene, vinylidene fluoride, chlorotrifluoroethylene, trifluorobromoethylene, trifluoromethoxytrifluoroethylene, 1-bis (trifluoromethoxy) difluoroethylene, phenoxytrifluoroethylene, or trifluoromethyl trifluorovinyl ether.
7. The process for producing a fluoroether of claim 1, wherein said catalyst is potassium hydroxide, sodium hydroxide, potassium carbonate, sodium carbonate, potassium tert-butoxide, tetramethylammonium hydroxide, trimethylamine, or triethylamine.
8. The method of claim 1, wherein the solvent is selected from the group consisting of N, N-dimethylformamide, N-dimethylacetamide, sulfolane, acetonitrile, tetrahydrofuran, methyltetrahydrofuran, dioxane, methyl tert-butyl ether, cyclohexanone, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, and tetraethylene glycol dimethyl ether.
9. The method for producing a fluoroether according to claim 1, wherein the molar ratio of the alcohol or the phenol to the fluoroolefin is 1: 0.8-2, the amount of the alcohol or the phenol added is 1-10 times the mass of the catalyst, the reaction temperature is-20-150 ℃, and the reaction pressure is 0-1.5 MPa.
10. The method for producing a fluoroether according to claim 1, wherein the mass of the concentrated solution is 5 to 50% of the mass of the fluoroether reaction solution.
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| CN112142572A (en) * | 2020-09-18 | 2020-12-29 | 浙江巨化技术中心有限公司 | Continuous production method for synthesizing hydrofluoroether |
| CN112341319A (en) * | 2020-10-16 | 2021-02-09 | 浙江巨化技术中心有限公司 | Comprehensive utilization method of fluorine-containing vinyl ether byproduct in hydrofluoroether production process |
| CN113620787A (en) * | 2021-07-12 | 2021-11-09 | 浙江诺亚氟化工有限公司 | Synthetic method of fluorine-containing aromatic ether |
| CN113929562A (en) * | 2021-10-28 | 2022-01-14 | 衢州氟硅技术研究院 | Preparation method of fluoroether |
| CN116178117A (en) * | 2023-03-02 | 2023-05-30 | 宁德时代新能源科技股份有限公司 | Fluoroether and preparation method thereof, electrolyte, battery and electricity utilization device |
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| CN113620787A (en) * | 2021-07-12 | 2021-11-09 | 浙江诺亚氟化工有限公司 | Synthetic method of fluorine-containing aromatic ether |
| CN113929562A (en) * | 2021-10-28 | 2022-01-14 | 衢州氟硅技术研究院 | Preparation method of fluoroether |
| CN116178117A (en) * | 2023-03-02 | 2023-05-30 | 宁德时代新能源科技股份有限公司 | Fluoroether and preparation method thereof, electrolyte, battery and electricity utilization device |
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