CN114853578A - Perfluoroalkyl ether and preparation method and application thereof - Google Patents
Perfluoroalkyl ether and preparation method and application thereof Download PDFInfo
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- CN114853578A CN114853578A CN202210711886.5A CN202210711886A CN114853578A CN 114853578 A CN114853578 A CN 114853578A CN 202210711886 A CN202210711886 A CN 202210711886A CN 114853578 A CN114853578 A CN 114853578A
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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
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/06—Halogens; Compounds thereof
- B01J27/08—Halides
- B01J27/12—Fluorides
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J27/00—Catalysts comprising the elements or compounds of halogens, sulfur, selenium, tellurium, phosphorus or nitrogen; Catalysts comprising carbon compounds
- B01J27/20—Carbon compounds
- B01J27/232—Carbonates
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M131/00—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen
- C10M131/08—Lubricating compositions characterised by the additive being an organic non-macromolecular compound containing halogen containing carbon, hydrogen, halogen and oxygen
- C10M131/10—Alcohols; Ethers; Aldehydes; Ketones
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- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D3/00—Other compounding ingredients of detergent compositions covered in group C11D1/00
- C11D3/16—Organic compounds
- C11D3/24—Organic compounds containing halogen
- C11D3/245—Organic compounds containing halogen containing fluorine
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- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/01—Products
- C25B3/07—Oxygen containing compounds
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- C—CHEMISTRY; METALLURGY
- C25—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES; APPARATUS THEREFOR
- C25B—ELECTROLYTIC OR ELECTROPHORETIC PROCESSES FOR THE PRODUCTION OF COMPOUNDS OR NON-METALS; APPARATUS THEREFOR
- C25B3/00—Electrolytic production of organic compounds
- C25B3/20—Processes
- C25B3/27—Halogenation
- C25B3/28—Fluorination
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
- C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
- C10M2211/042—Alcohols; Ethers; Aldehydes; Ketones
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- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/14—Electric or magnetic purposes
- C10N2040/16—Dielectric; Insulating oil or insulators
Abstract
The invention discloses perfluoroalkyl ether and a preparation method and application thereof, wherein the preparation method comprises the following steps: perfluoro-butyryl fluoride is used as a raw material, dimethyl carbonate or diethyl carbonate is used as an alkylating reagent, and the perfluoro-alkyl ether is generated under the action of a catalyst. The invention prepares perfluoroalkyl ether by a two-step method combining an electrochemical method and a chemical synthesis method. In the preparation process, no organic solvent is used, and low-toxicity and environment-friendly carbonate is used as an alkylating reagent to ensure that the product is nontoxic and easy to treat. The method has simple process, clear product and easy purification. The prepared product can be used as a cleaning agent and an insulating liquid.
Description
Technical Field
The invention belongs to the technical field of preparation of perfluoroalkyl ether, and relates to perfluoroalkyl ether and a preparation method and application thereof.
Background
With the rapid increase of economy, environmental problems have been the focus of widespread concern in countries around the world, and perchlorofluorocarbons (CFCs) and Hydrochlorofluorocarbons (HCFCs), which have been widely used, have been or will be eliminated due to their destructive effect on the ozone layer and severe greenhouse effect. The low-carbon hydrofluoroether has no damage to the ozone layer, has low GWP (global warming potential), and can well replace CFCs and HCFCs for application.
At present, reports on low-carbon hydrofluoroether perfluoroalkyl ether are few, and a synthesis process is complex and high-toxicity chemical raw materials are often used, for example, Chinese patent CN109503366A provides a method for preparing perfluoroisobutyl ether from hexafluoro dimer. Chinese patent CN1177374 mentions the two-step method of electrochemical and chemical synthesis for the synthesis of perfluoroalkyl ethers, but the patent does not describe the process of electrochemical preparation of intermediates, and the patent also uses dimethyl sulfate as a methylating agent.
Disclosure of Invention
The invention aims to provide perfluoroalkyl ether and a preparation method and application thereof, wherein low-toxicity and environment-friendly dimethyl carbonate or diethyl carbonate is adopted to replace high-toxicity dimethyl sulfate or halogenated methane to be used as an alkylating reagent to synthesize the perfluoroalkyl ether, and a supported double-catalyst system is adopted to synthesize the perfluoroalkyl ether by using low-toxicity dimethyl carbonate (diethyl carbonate) as the alkylating reagent without using an organic solvent.
In order to solve the above problems, a first aspect of the present invention provides a method for preparing a perfluoroalkyl ether, wherein perfluorobutyryl fluoride is used as a raw material, carbonate ester is used as an alkylating agent, and the reaction is carried out under the action of a catalyst to generate the perfluoroalkyl ether.
Preferably, the preparation of the perfluorobutyryl fluoride comprises the steps of:
adding the mixed solution of butyryl chloride and anhydrous hydrogen fluoride into an electrolytic bath for electrolytic fluorination reaction; condensing the electrolytic mixed gas generated in the electrolytic process, separating the liquid at the lower layer of the electrolytic cell, and washing to obtain the perfluorobutyryl fluoride;
the reaction conditions of the electrolytic fluorination reaction are as follows:
the temperature is-5 ℃ to 0 ℃, the voltage is 5V to 7V, and the current is 3A to 4A.
Preferably, the catalyst is a supported dual catalyst.
Preferably, the preparation step of the catalyst comprises:
dissolving or dispersing the first catalyst and the second catalyst in water, adding a catalyst carrier, uniformly stirring and drying.
Preferably, the first catalyst is one or more of potassium fluoride, sodium fluoride and cesium fluoride;
the second catalyst hydrogen is one of potassium oxide, potassium carbonate or titanium dioxide;
the carrier of the catalyst is activated carbon;
the mass ratio of the first catalyst, the second catalyst and the catalyst carrier is 1: 1:1 to 4.
Preferably, the preparation method of the perfluoroalkyl ether specifically comprises the following steps:
adding the perfluorobutyryl fluoride, the alkylating agent and the catalyst into an autoclave, vacuumizing at low temperature, fully stirring and heating to a first temperature;
standing for reacting for the first time, cooling to room temperature, and separating liquid;
and taking the lower layer liquid, washing with water, drying and distilling to obtain the perfluoroalkyl ether.
Preferably, the molar ratio of the perfluorobutyryl fluoride to the alkylating agent is 1: 1-4;
the adding amount of the catalyst is 4-40% of the mass of the added perfluorobutyryl fluoride.
Preferably, the first temperature is in the range of 150 ℃ to 300 ℃ and the first time is in the range of 6h to 12 h.
The second aspect of the invention provides perfluoroalkyl ether prepared by the method.
In a third aspect, the invention provides an insulating liquid, which comprises the perfluoroalkyl ether prepared by the method.
The fourth aspect of the invention provides a cleaning agent, which comprises the perfluoroalkyl ether prepared by the method.
The technical scheme of the invention has the following beneficial technical effects:
the invention prepares perfluoroalkyl ether by a two-step method combining an electrochemical method and a chemical synthesis method. In the preparation process, no organic solvent is used, and dimethyl carbonate (diethyl carbonate) with low toxicity and environmental protection is used as an alkylating reagent to ensure that the product is nontoxic and easy to treat. The method has simple process, clear product and easy purification.
Drawings
FIG. 1 is a flow chart of a process for preparing a perfluoroalkyl ether of one embodiment of the invention;
FIG. 2 is a flow chart of a process for the preparation of a perfluoroalkyl ether according to another embodiment of the invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention will be described in further detail with reference to the accompanying drawings in conjunction with the following detailed description. It should be understood that the description is intended to be exemplary only, and is not intended to limit the scope of the present invention. Moreover, in the following description, descriptions of well-known structures and techniques are omitted so as to not unnecessarily obscure the concepts of the present invention.
The invention provides a preparation method of perfluoroalkyl ether, which takes perfluorobutyryl fluoride as a raw material and dimethyl carbonate or diethyl carbonate as an alkylating reagent to react under the action of a catalyst, and the generated product is perfluoroalkyl ether. As shown in fig. 1, three steps are included:
s1, preparing perfluorobutyryl fluoride;
s2, preparing a carbon-supported double catalyst;
s3, synthesizing perfluoroalkyl ether by using dimethyl carbonate or diethyl carbonate as an alkylating reagent.
The invention adopts carbonate (dimethyl carbonate or diethyl carbonate) with lower toxicity to replace dimethyl sulfate or methyl halide with high toxicity as an alkylating agent to synthesize the perfluoroalkyl ether without using an organic solvent.
The first embodiment of the present invention relates to an electrolytic fluorination apparatus in which nickel is selected as a cathode and iron is selected as an anode when perfluorobutyryl fluoride is prepared in step S1. Adding 1Kg of butyryl chloride into an electrolytic bath containing 1Kg to 3Kg of anhydrous hydrogen fluoride, simultaneously adding 60g to 90g of conductive substance, and carrying out electrolytic fluorination reaction under the reaction conditions of-5 ℃ to 0 ℃, 5V to 7V of voltage and 3A to 4A of current, wherein the conductive substance is preferably KF, LiF or NaF.
In the electrolytic process, generated gases such as hydrogen chloride, hydrogen fluoride, products and the like are subjected to reflux condensation treatment by using dry ice/acetone as a medium and cold hydrazine, so that the generated hydrogen fluoride and the products are condensed and refluxed to a reactor at a low temperature, wherein the condensation temperature is-40 ℃;
after condensation treatment, the residual hydrogen chloride and hydrogen are subjected to water washing and alkali washing to wash out corrosive hydrogen chloride, and the obtained clean hydrogen is collected or discharged out of the reactor to achieve harmless discharge.
Because the density of the reaction product in the electrolytic cell is high, the product can be discharged from the bottom of the reactor and then is further washed by water to obtain the perfluorobutyryl fluoride, and the yield is 40-50%.
A comparative experiment was conducted on the yield of perfluorobutyryl fluoride produced for step S1 to obtain data as shown in Table one:
table one: preparation of perfluorobutyryl fluoride
As can be seen from the above table, when the voltage is reduced to less than 5V, the electrofluorination efficiency is greatly reduced, resulting in a significant drop in yield; increasing the reaction current helps to increase the yield of perfluorobutyryl fluoride.
The second embodiment of the present invention relates to the step S2 of preparing the carbon-supported dual catalyst, in which the first catalyst and the second catalyst are dissolved or dispersed in water, and the catalyst carrier is added and stirred uniformly and then dried.
Selecting potassium fluoride as a first catalyst to catalyze perfluorobutyryl fluoride to generate fluoroalcohol salt; selecting potassium hydroxide as a second catalyst for catalyzing fluoroalcohol salts to generate perfluoroalkyl ether; the active carbon is selected as the catalyst load for increasing the specific surface area of the catalyst and improving the catalytic efficiency.
In this embodiment, potassium hydroxide and potassium fluoride are dissolved or dispersed in a proper amount of water to sufficiently dissolve or disperse the catalyst, activated carbon (100-200 mesh) is added to the water and uniformly stirred, and the mixture is placed in an oven at 100-200 ℃ to be dried. Wherein the mass ratio of the potassium hydroxide to the potassium fluoride to the activated carbon is 1: 1: 1-4, preferably 1: 1: 3.
in other embodiments of the present invention, the first catalyst may also be selected from sodium fluoride or cesium fluoride, or from a combination of any of alkali metal fluorides of potassium fluoride, sodium fluoride and cesium fluoride; meanwhile, potassium carbonate or titanium dioxide can be selected as a second catalyst.
Third embodiment of the present invention with respect to step S3, perfluoroalkyl ether was prepared using the materials prepared in steps S1, S2. The flow chart shown in fig. 2 includes the following steps:
s31, adding perfluorobutyryl fluoride, an alkylating agent and a catalyst into an autoclave, vacuumizing at low temperature, fully stirring and heating to a first temperature;
s32, standing for reacting for the first time, cooling to room temperature, and separating liquid;
and S33, taking the lower layer liquid, washing with water, drying and distilling to obtain the product perfluoroalkyl ether.
Specifically, dimethyl carbonate is selected as an alkylating reagent, perfluorobutyryl fluoride prepared in the step S1, dimethyl carbonate and an activated carbon catalyst loaded with potassium hydroxide and potassium fluoride prepared in the step S2 are added into an autoclave, the autoclave is vacuumized at the temperature of-20 ℃ and then started, the mixture is stirred for 2 to 4 hours, and the temperature is increased to 150 to 300 ℃, preferably 200 to 250 ℃, and the catalytic rate of the catalyst is highest;
after the operation is finished, the reaction time is controlled to be 6-12 h, preferably 9-10 h; after full reaction, cooling the reaction product to room temperature and carrying out liquid separation operation by utilizing different densities of the products;
separating liquid, taking the lower layer liquid, washing with water, drying, and rectifying by a rectifying tower to obtain perfluorobutyl methyl ether, wherein the structural formula is as follows:
the yield is about 60-85%.
Further, the molar ratio of the perfluorobutyryl fluoride to dimethyl carbonate participating in the reaction is 1: 1-4, preferably 1: 1-2; the amount of the catalyst added is 4-40%, preferably 10-30% of that of the perfluorobutyryl fluoride, so as to ensure sufficient reaction and high yield.
In another preferred embodiment of the present invention, diethyl carbonate can be further selected as an alkylating agent to obtain perfluorobutyl ether, the structure of which is shown in the following formula:
a comparative experiment was performed with respect to the yield of the preparation of the perfluoroalkyl ether of step S3, to obtain data as shown in table two, in which the catalyst was an activated carbon catalyst loaded with potassium hydroxide and potassium fluoride; the mass ratio of potassium hydroxide, potassium fluoride and active carbon is 1: 1: 3.
table two: preparation of perfluoroalkyl ethers
As can be seen from the above table, when the amount of dimethyl carbonate or diethyl carbonate is too small, the perfluorobutyryl fluoride cannot be completely converted, while the amount of dimethyl carbonate or diethyl carbonate is too large, an excessive amount of raw material is generated, which increases the subsequent treatment cost; too little catalyst can reduce the yield of the perfluoroalkyl ether.
The invention synthesizes the perfluorobutyryl fluoride through a two-step method, namely a first step through an electrochemical method; the second step is to synthesize perfluoroalkyl ether by self-synthesis of activated carbon supported catalyst and dimethyl carbonate (diethyl carbonate) as alkylating agent. The selected alkylating reagent has low toxicity, the synthesis conditions are easy to control, and the preparation of the perfluoroalkyl ether can be better realized.
The fourth embodiment of the present invention provides an insulating liquid comprising the perfluoroalkyl ether prepared by the above method.
The fifth embodiment of the present invention provides a cleaning agent comprising the perfluoroalkyl ether prepared by the above method.
It is to be understood that the above-described embodiments of the present invention are merely illustrative of or explaining the principles of the invention and are not to be construed as limiting the invention. Therefore, any modification, equivalent replacement, improvement and the like made without departing from the spirit and scope of the present invention should be included in the protection scope of the present invention. Further, it is intended that the appended claims cover all such variations and modifications as fall within the scope and boundaries of the appended claims or the equivalents of such scope and boundaries.
Claims (10)
1. A preparation method of perfluoroalkyl ether is characterized in that perfluorobutyryl fluoride is used as a raw material, carbonate is used as an alkylating reagent, and the reaction is carried out under the action of a catalyst to generate the perfluoroalkyl ether.
2. The process for the preparation of perfluoroalkyl ethers according to claim 1, characterized in that said preparation of perfluorobutyryl fluoride comprises the steps of:
adding the mixed solution of butyryl chloride and anhydrous hydrogen fluoride into an electrolytic bath for electrolytic fluorination reaction; condensing the electrolytic mixed gas generated in the electrolytic process, separating the liquid at the lower layer of the electrolytic cell, and washing to obtain the perfluorobutyryl fluoride;
the reaction conditions of the electrolytic fluorination reaction are as follows:
the temperature is-5 ℃ to 0 ℃, the voltage is 5V to 7V, and the current is 3A to 4A.
3. A process for the preparation of perfluoroalkyl ethers according to claim 1, characterized in that the catalyst is a supported dual catalyst.
4. A process for the preparation of a perfluoroalkyl ether according to claim 1 or 3, characterized in that the preparation of the catalyst comprises:
dissolving or dispersing a first catalyst and a second catalyst in water, adding a catalyst carrier, uniformly stirring and drying;
the first catalyst is an alkali metal fluoride; preferably, the alkali metal fluoride comprises: one or more of potassium fluoride, sodium fluoride, or cesium fluoride;
the second catalyst is one of potassium hydroxide, potassium carbonate or titanium dioxide;
the carrier of the catalyst is activated carbon;
the mass ratio of the first catalyst, the second catalyst and the carrier of the catalyst is 1: 1:1 to 4.
5. A process for the preparation of a perfluoroalkyl ether according to claim 1, characterized in that it comprises in particular:
adding the perfluorobutyryl fluoride, the alkylating agent and the catalyst into an autoclave, vacuumizing at low temperature, fully stirring and heating to a first temperature;
standing for reacting for the first time, cooling to room temperature, and separating liquid;
and taking the lower layer liquid, washing with water, drying and distilling to obtain the perfluoroalkyl ether.
6. A process for the preparation of a perfluoroalkyl ether according to claim 5, characterized in that the molar ratio of perfluorobutanoic fluoride to alkylating agent is 1: 1-4;
the adding amount of the catalyst is 4-40% of the mass of the added perfluorobutyryl fluoride;
the first temperature range is 150-300 ℃, and the first time range is 6-12 h.
7. A process for the preparation of perfluoroalkyl ethers according to claim 1 or 5, characterized in that the alkylating agent is dimethyl carbonate or diethyl carbonate.
8. A perfluoroalkyl ether characterized by being prepared by the process as claimed in any one of claims 1 to 7.
9. An insulating liquid comprising the perfluoroalkyl ether according to claim 8.
10. A cleaning agent comprising the perfluoroalkyl ether according to claim 8.
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Citations (8)
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| US6046368A (en) * | 1998-03-17 | 2000-04-04 | 3M Innovative Properties Company | Catalytic process for making hydrofluoroethers |
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| KR20080110204A (en) * | 2007-06-15 | 2008-12-18 | 한국과학기술연구원 | Method for preparing of hydrofluoroethers using supported catalysts |
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| CN110002968A (en) * | 2019-04-28 | 2019-07-12 | 北京宇极科技发展有限公司 | The preparation method of fluorine-containing ether |
| CN111777496A (en) * | 2020-07-23 | 2020-10-16 | 浙江诺亚氟化工有限公司 | Preparation method of isolated hydrofluoroether |
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| CN113735690A (en) * | 2021-08-27 | 2021-12-03 | 中船重工（邯郸）派瑞特种气体有限公司 | Preparation method of hydrofluoroether cleaning agent |
-
2022
- 2022-06-22 CN CN202210711886.5A patent/CN114853578A/en active Pending
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| US6159917A (en) * | 1998-12-16 | 2000-12-12 | 3M Innovative Properties Company | Dry cleaning compositions containing hydrofluoroether |
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| CN110002968A (en) * | 2019-04-28 | 2019-07-12 | 北京宇极科技发展有限公司 | The preparation method of fluorine-containing ether |
| CN111777496A (en) * | 2020-07-23 | 2020-10-16 | 浙江诺亚氟化工有限公司 | Preparation method of isolated hydrofluoroether |
| CN112028750A (en) * | 2020-08-27 | 2020-12-04 | 上海应用技术大学 | Perfluoroalkyl ether and preparation and application thereof |
| CN113735690A (en) * | 2021-08-27 | 2021-12-03 | 中船重工（邯郸）派瑞特种气体有限公司 | Preparation method of hydrofluoroether cleaning agent |
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