CN112409299A - Continuous preparation method of hexafluoropropylene oxide - Google Patents
Continuous preparation method of hexafluoropropylene oxide Download PDFInfo
- Publication number
- CN112409299A CN112409299A CN201910780130.4A CN201910780130A CN112409299A CN 112409299 A CN112409299 A CN 112409299A CN 201910780130 A CN201910780130 A CN 201910780130A CN 112409299 A CN112409299 A CN 112409299A
- Authority
- CN
- China
- Prior art keywords
- solvent
- quartz glass
- hexafluoropropylene oxide
- perfluoropropene
- perfluoropolyether
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/48—Compounds containing oxirane rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
- C07D301/08—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/04—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen
- C07D301/08—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase
- C07D301/10—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with air or molecular oxygen in the gaseous phase with catalysts containing silver or gold
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Epoxy Compounds (AREA)
Abstract
The invention relates to a continuous preparation method of hexafluoropropylene oxide, which takes mixed gas of perfluoropropene and oxygen as raw material, and carries out oxidation reaction in a perfluorinated solvent under the combined catalysis of a solid metal catalyst and ultraviolet light. The method provided by the invention is simple to operate, the solid catalyst and the solvent can be reused, the reaction pressure is low, the safety is high, the product conversion rate is high, and the economic benefit is good.
Description
Technical Field
The invention belongs to the field of fluorine-containing fine chemicals, and particularly relates to a continuous preparation method of hexafluoropropylene oxide.
Background
Hexafluoropropylene oxide (HFPO), abbreviated as hexafluoropropylene oxide, also known as perfluoropropylene oxide, is the most important perfluoroepoxy compound. The compound was first synthesized by dupont at the end of the last 50 s. Hexafluoropropylene oxide can be initiated by anion to self-polymerize, or react with acyl fluoride to generate perfluoroalkyl perfluorovinyl ether (such as perfluoromethyl vinyl ether (PMVE), perfluoro-n-propyl vinyl ether (PPVE) and perfluorobutylene vinyl ether (PBVE)), and the perfluoroalkyl perfluorovinyl ether is copolymerized with tetrafluoroethylene or other fluoroolefin to prepare organic fluorine materials with excellent performance, such as perfluorolubricating oil, perfluoroheat-resistant medium, perfluoroion exchange resin, perfluoroplastic, perfluororubber, and the like. For example, PMVE, tetrafluoroethylene and a third monomer containing a crosslinking point are subjected to ternary polymerization together, so that fluoroether rubber with better low-temperature performance and heat resistance can be prepared; PPVE can be used for modifying polytetrafluoroethylene resin, and is copolymerized with tetrafluoroethylene to obtain soluble Polytetrafluoroethylene (PFA); the hexafluoropropylene oxide can be used for preparing PBVE for the transparent fluororesin; hexafluoropropylene oxide can also be used to prepare perfluoroalkylsulfonyl fluorovinyl ether (PSVE) for use in the preparation of ion exchange resin membranes. The hexafluoropropylene oxide is a raw material for preparing the hexafluoroacetone, the hexafluoroacetone and the phenol are added to obtain the bisphenol AF, the bisphenol AF is used as a vulcanizing agent of the fluororubber, and the permanent compression deformation of the fluororubber can be greatly reduced. In addition, the hexafluoropropylene oxide can be synthesized into other series of very useful fine chemical products, which enables the hexafluoropropylene oxide to become an important intermediate for preparing the organic fluorine material. Therefore, the preparation of hexafluoropropylene oxide is an important link in the synthesis of organic fluorine-containing materials.
The prior art discloses H2O2And perfluoropropene in aqueous-methanol solution of KOH at-40 ℃ in about 35% yield. The method has the advantages of high product purity, but low yield, large amount of cold energy required, and difficult recovery of residual liquid with three times of the product. The yield of hexafluoropropylene oxide decreases with increasing perfluoropropene conversion. Part of the products are destroyed into trifluoroacetic acid, perfluoropropionic acid and carbon dioxide, which affects the improvement of the yield.
The prior art discloses perfluoropropene and O2The method for preparing hexafluoropropylene oxide through reaction at 130-165 ℃ in the presence of high-pressure (0.1-5 MPa) inert solvent. The inert solvent is a liquid halogenated hydrocarbon. The method has high reaction pressure, needs solvent, has complex process, and the oxidation product contains perfluoropropene, oxygen, fluorophosgene, trifluoroacetyl fluoride and hexafluoroacetoneEtc., which need to be removed.
The prior art discloses the use of certain proportions of perfluoropropene and O2A process for producing hexafluoropropylene oxide by passing a mixture through a solid catalyst layer at an elevated temperature. The key to the method is the selection of the catalyst. The DuPont uses silica gel compounds, the reaction temperature is 140-280 ℃, the conversion rate is 31 percent, and the selectivity is 74 percent; the Asahi glass company of Japan uses silicic acid and alumina compound or ion exchange zeolite doped with copper compound, the reaction temperature is 250-350 ℃, the conversion rate is 31 percent, and the selectivity is 72 percent; dajin corporation used barium oxide, barium hydroxide or barium salt at 220 deg.C, 70% selectivity and 34% conversion. This process has a low conversion rate, and hexafluoropropylene oxide is cracked into trifluoroacetyl fluoride and TFE, and when the oxygen content is increased, equimolar molecules of trifluoroacetyl fluoride and fluorophosphone are formed. The preparation process of the high-efficiency catalyst required by the gas phase oxidation is complex, the steps are complicated, the screening workload is large, and the difficulty is high.
The prior art discloses a method for preparing hexafluoropropylene oxide by dissolving hypochlorite as an oxidant in a two-phase system consisting of a water phase and an organic phase and oxidizing perfluoropropene at 0 ℃ in the presence of a phase transfer catalyst. The phase transfer catalyst is one or more of quaternary ammonium salt, quaternary phosphonium salt, quaternary arsonium salt and lipophilic complex. The organic phase solvent is an aprotic inert solvent: f113, DG, acetonitrile, etc. In the process of reusing the phase transfer catalyst adopted by the method, the catalytic activity of the phase transfer catalyst is slowly reduced, and the perfluoropropene cannot keep higher conversion rate for a long time. In addition, the method also has the problem of more waste liquid.
The prior art also discloses the use of O2A method for preparing hexafluoropropylene oxide by irradiating a mixture with perfluoropropene. Ultraviolet light wavelength of 320nm, N2Or He is used as a diluent, and the reaction temperature is 110-120 ℃. The selectivity to hexafluoropropylene oxide was about 70% and the perfluoropropene conversion was about 9%. However, the method is not easy to control, the conversion rate of the perfluoropropene is low, a large amount of unconverted perfluoropropene needs to be recovered and treated, the operability is poor, and industrialization is difficult to realize.
Disclosure of Invention
The invention aims to overcome the defects of the prior art and provide a continuous preparation method of hexafluoropropylene oxide. The method provided by the invention is simple to operate, the solid catalyst and the solvent can be reused, the reaction pressure is low, the safety is high, the product conversion rate is high, and the economic benefit is good.
Specifically, the method for preparing hexafluoropropylene oxide provided by the invention takes the mixed gas of perfluoropropene and oxygen as the raw material, and carries out oxidation reaction in a perfluorinated solvent under the combined catalytic action of a solid metal catalyst and ultraviolet light.
The perfluorinated solvent used in the present invention is preferably a perfluoropolyether. The perfluoropolyether is a special perfluoropolymer compound, has only C, F, O elements in the molecule, and has the characteristics of heat resistance, oxidation resistance, radiation resistance, corrosion resistance, non-combustion and the like. According to the used monomers and polymerization methods, PFPEs with different molecular structures of K type, Y type, Z type and D type 4 can be obtained. The invention preferably adopts Y-type perfluoropolyether as solvent to prepare hexafluoropropylene oxide, and the structural formula of the Y-type perfluoropolyether is CF3O(C3F6O)m(CF2O)nCF3The polymer is formed by photo-oxidation of Hexafluoropropylene (HFP) under the action of ultraviolet light, and the molecular weight is generally 500-10000. The invention further preferably adopts Y-type perfluoropolyether with the molecular weight of 500-2500 as a solvent. The present invention has been found through extensive practice that the use of the above preferred solvents can promote the dissolution of the product therein, thereby improving the reaction efficiency and the yield of the product.
The perfluoropolyether solvent used in the present invention can be obtained by existing methods. For example, a method disclosed in patent document CN101648122A can be used, in which the obtained product is fluorinated and then perfluoropolyether having a molecular weight of 500 to 2500 is selected as a solvent.
As a preferable scheme of the invention, the Y-type perfluoropolyether can be prepared by adopting a method comprising the following steps: adding 0.3-0.7L of hexafluoropropylene with the temperature of-45 to-35 ℃ into a precooled reactor, introducing mixed gas of 18-22L/h (standard state) of metered oxygen and 2-3L/h (standard state) of chlorotrifluoroethylene into the bottom of the reactor, keeping the temperature of a reaction phase at-50 to-40 ℃ for 6-10 h, taking out a product at the bottom of a kettle, hydrolyzing the product, standing, layering and taking out an oil layer.
In order to ensure the reaction to be fully carried out, the temperature of the solvent adopted by the invention should be controlled to be 100-200 ℃, and preferably 110-130 ℃.
The reaction raw material adopted by the invention is a mixed gas of perfluoropropene gas and oxygen at room temperature. The gas is mixed according to the mol ratio of perfluoropropylene to oxygen of 1: (0.5-5) and the molar ratio of the two is 1: the effect is more preferable in the range of (1) to (2). The speed of introducing the mixed gas into the solvent is not suitable to be too fast, the gas amount introduced per minute is not suitable to exceed 5 per thousand of the solvent amount, and is preferably not more than 2 per thousand, and once the introduction speed is too fast, the conversion rate is directly too low.
The invention adopts a solid metal catalyst which is suspended in a solvent for catalyzing oxidation reaction. The solid metal catalyst is preferably a mixture of one or more of the metals Pt, Pd, Cu, Fe, Ag, more preferably a mixture of one or two of them. As a preferred embodiment of the present invention, the solid metal catalyst is Ag, or a mixture of Ag and Pt.
The solid metal catalyst should have a small particle size, for example, a particle size of less than 300. mu.m, preferably 50 to 200. mu.m, and more preferably 50 to 100. mu.m, so as to be suspended in a solvent and sufficiently dispersed.
The dosage of the solid metal catalyst is preferably 0.1-5%, more preferably 1-2% of that of the perfluoropolyether. In order to uniformly distribute the solid metal catalyst in the solvent, a stirring device can be introduced into the solvent, and the rotation speed is preferably 200-250 revolutions per minute.
The invention adopts solid metal catalyst and ultraviolet light to catalyze simultaneously. The wavelength of the ultraviolet light is preferably 200-380 nm, and more preferably 250-260 nm.
The method provided by the invention can control the pressure to be lower than 0.2Mpa, even lower than 0.1Mpa in the whole preparation process.
The method provided by the invention can be carried out in a circular quartz glass tube. Specifically, the quartz glass tube is provided with a quartz glass sleeve at the center, an ultraviolet lamp is arranged in the sleeve, and the size of the quartz glass tube can be adjusted according to the reaction amount. Generally, the thickness of the quartz glass is 1-3 mm, the inner diameter of the quartz glass tube is 30-60 mm, and the length of the quartz glass tube is 500-1000 mm. The inner diameter of the central quartz glass ultraviolet lamp sleeve is 20-30 mm, and the length of the central quartz glass ultraviolet lamp sleeve is 200-400 mm. The quartz glass tube is used for gas inlet, a bottom-inserted glass tube is adopted, a glass outlet for gas outlet is additionally arranged, and the outlet is connected to a low-temperature cold trap to collect products. Introducing the uncondensed tail gas in the cold trap into alkali liquor through a low-temperature condenser.
In the actual manufacturing process, a quartz glass tube was charged with a perfluorinated solvent and a solid metal catalyst was added. In order to uniformly distribute the metal catalyst in the solvent, a magnetic stirring rotor can be arranged at the bottom of the quartz glass tube, and the rotating speed of the rotor is not less than 200 revolutions per minute. The temperature of the perfluorinated solvent in the quartz glass tube can be controlled by adjusting the power of the ultraviolet lamp. In the actual production process, the mixed gas of hexafluoropropylene oxide and oxygen is continuously introduced into the solvent of the quartz glass reaction, the generated product flows out from the tail gas pipe, and the product is obtained by collecting through a condenser. The pressure in the whole reaction process is lower than 0.2MPa, even lower than 0.1MPa, and the safety is high.
Compared with the prior art, the method for preparing hexafluoropropylene oxide provided by the invention can be continuously carried out, is simple to operate, can reuse the solid catalyst and the solvent, is more environment-friendly, has low reaction pressure and high safety, and has good economic benefit for preparing hexafluoropropylene oxide.
Detailed Description
Preferred embodiments of the present invention will be described in detail with reference to the following examples.
The perfluoropolyether solvent used in the following examples was prepared as follows: a stainless steel reactor with a built-in ultraviolet lamp and a volume of 2L, wherein the reactor is provided with a reflux facility at the temperature of-70 ℃; adding 0.5L of hexafluoropropylene precooled to-40 ℃ into the precooled reactor; introducing metered oxygen (O) into the bottom of the reactor2)20L/h (standard state) of mixed gas and 2.5L/h (standard state) of chlorotrifluoroethylene, keeping the temperature of a reaction phase at about minus 45 ℃, maintaining for 8h, and taking out a bottom product of the kettle. Hydrolyzing, standing, layering and taking oil layer to obtain 572g of product, detecting the acid value of the product to be 65.5, and the peroxide content to be52ppm, molecular weight 1100 by nuclear magnetic fluorine spectroscopy.
Example 1
This example provides a process for the preparation of hexafluoropropylene oxide.
The preparation process is carried out in the following equipment: quartz glass tube (inner diameter 50mm, length 400mm), built-in ultraviolet lamp jacket (inner diameter 30mm, length 200mm), configuration plug-in bottom breather pipe, tail gas pipe joint cold trap (-50 ℃) collect the product, the tail gas that does not congeal in the cold trap passes through low temperature condenser (-50 ℃) and lets in alkali lye. The bottom of the quartz glass tube is provided with a magnetic stirring rotor.
The preparation method specifically comprises the following steps: adding 0.4L of perfluoropolyether and 2g of Cu powder catalyst with the particle size of 200 mu m into a quartz glass tube, starting magnetic stirring and uniformly mixing, starting an ultraviolet lamp at the rotating speed of 200 rpm/min, heating the perfluoropolyether in the quartz glass tube to 120 ℃, and then introducing: 1 mixed gas of perfluoropropene and oxygen, the gas flow rate is controlled at 5 g/min, the pressure is 0.1Mpa, and the gas is continuously introduced for 1 hour to obtain 300g of product.
The resulting product was tested to have 37% HFPO content, 44% HFP content, and 19% other products.
Example 2
This example provides a process for the preparation of hexafluoropropylene oxide.
The equipment used was the same as in example 1.
The preparation method specifically comprises the following steps: adding 0.4L of perfluoropolyether and 2g of Pd powder catalyst with the particle size of 100 mu m into a quartz glass tube, starting stirring and mixing uniformly, rotating at 200 rpm/min, starting an ultraviolet lamp, heating the perfluoropolyether in the quartz glass tube to 120 ℃, and then introducing: 1 mixed gas of perfluoropropene and oxygen, the gas flow rate is controlled at 5 g/min, the pressure is 0.1Mpa, and the gas is continuously introduced for 1 hour to obtain 300g of product.
The resulting product was tested to have 42% HFPO, 40% HFP, and 18% other products.
Example 3
This example provides a process for the preparation of hexafluoropropylene oxide.
The equipment used was the same as in example 1.
The preparation method specifically comprises the following steps: adding 0.45L of perfluoropolyether and 2g of Ag and Pt powder mixed catalyst with the particle size of 100 mu m into a quartz glass tube, starting stirring and mixing uniformly, starting an ultraviolet lamp at the rotating speed of 200 rpm/min, heating the perfluoropolyether in the quartz glass tube to 120 ℃, and then introducing: 1 mixed gas of perfluoropropene and oxygen, the gas flow rate is controlled at 2 g/min, the pressure is 0.1Mpa, and the gas is continuously introduced for 3 hours to obtain 350g of product.
The detection shows that the HFPO content of the obtained product is 65%, the HFP content is 13% and other products are 22%.
Example 4
This example provides a process for the preparation of hexafluoropropylene oxide.
The preparation process is carried out in the following equipment: quartz glass tube (inner diameter 60mm, length 500mm), built-in ultraviolet lamp jacket (inner diameter 30mm, length 300mm), configuration plug-in bottom breather pipe, tail gas pipe joint cold trap (-50 ℃) collect the product, the tail gas that does not congeal in the cold trap passes through low temperature condenser (-50 ℃) and lets in alkali lye. The bottom of the quartz glass tube is provided with a magnetic stirring rotor.
The preparation process specifically comprises the following steps: adding 1.1L of perfluoropolyether and 5g of Ag powder catalyst with the particle size of 50 mu m into a quartz glass tube, starting stirring and mixing uniformly, rotating at 200 rpm/min, starting an ultraviolet lamp, heating the perfluoropolyether in the quartz glass tube to 120 ℃, and then introducing the catalyst according to the molar ratio of 1: 1 mixed gas of perfluoropropene and oxygen, the gas flow rate is controlled at 4 g/min, the pressure is 0.1Mpa, and the gas is continuously introduced for 2 hours to obtain 422g of product.
The resulting product was tested to have an HFPO content of 68%, an HFP content of 12%, and other products of 20%.
Although the invention has been described in detail hereinabove by way of general description, specific embodiments and experiments, it will be apparent to those skilled in the art that many modifications and improvements can be made thereto based on the invention. Accordingly, such modifications and improvements are intended to be within the scope of the invention as claimed.
Claims (10)
1. A continuous process for preparing hexafluoropropylene oxide features that the mixed gas of perfluoropropene and oxygen is used as raw material and under the co-catalysis of solid metal catalyst and ultraviolet light, the oxidizing reaction is carried out in perfluoro solvent.
2. The method according to claim 1, wherein the perfluorinated solvent is a perfluoropolyether, preferably a Y-type perfluoropolyether, more preferably a Y-type perfluoropolyether having a molecular weight of 500-2500.
3. The method according to claim 1 or 2, wherein the temperature of the solvent is 100 to 200 ℃, preferably 110 to 130 ℃.
4. The process of claim 1, wherein the molar ratio of perfluoropropene to oxygen is 1: (0.5 to 5), preferably 1: (1-2).
5. A method as claimed in claim 1 or 4, characterized in that the mass of the gas mixture introduced per minute does not exceed 5% by mass, preferably 2% by mass, of the solvent.
6. The method according to claim 1, wherein the solid metal catalyst is a mixture of one or more of the metals Pt, Pd, Cu, Fe, Ag, preferably Ag or a mixture of Ag and Pt.
7. The process according to claim 1 or 6, wherein the solid metal catalyst has a particle size of less than 300 μm, preferably 50 to 200 μm, more preferably 50 to 100 μm.
8. The method of claim 1, wherein the solvent is stirred during the reaction, preferably at a speed of 200 to 250 rpm.
9. The method according to claim 1, wherein the wavelength of the ultraviolet light is 200 to 380nm, preferably 250 to 260 nm.
10. The method according to claim 1, wherein the production process is carried out in a quartz glass tube;
the center of the quartz glass tube is provided with a quartz glass sleeve with a built-in ultraviolet lamp, the bottom of the quartz glass sleeve is provided with a glass air inlet tube, the top of the quartz glass sleeve is provided with a glass air outlet tube, and a cold trap is introduced to collect products.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910780130.4A CN112409299A (en) | 2019-08-22 | 2019-08-22 | Continuous preparation method of hexafluoropropylene oxide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910780130.4A CN112409299A (en) | 2019-08-22 | 2019-08-22 | Continuous preparation method of hexafluoropropylene oxide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN112409299A true CN112409299A (en) | 2021-02-26 |
Family
ID=74778975
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910780130.4A Pending CN112409299A (en) | 2019-08-22 | 2019-08-22 | Continuous preparation method of hexafluoropropylene oxide |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112409299A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116854572A (en) * | 2023-08-30 | 2023-10-10 | 哲弗智能系统（上海）有限公司 | Preparation method of perfluoro hexanone |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB931587A (en) * | 1961-05-18 | 1963-07-17 | Du Pont | Fluorocarbon epoxides |
| CN102675255A (en) * | 2012-04-18 | 2012-09-19 | 金华永和氟化工有限公司 | Preparation method for hexafluoropropylene oxide |
| CN104650010A (en) * | 2015-03-20 | 2015-05-27 | 山西福诺欧新材料科技股份有限公司 | Method for preparing hexafluoropropylene oxide |
| CN109678700A (en) * | 2018-12-24 | 2019-04-26 | 天津市长芦化工新材料有限公司 | The method that comprehensive utilization dioxygen oxidation method prepares the by-product generated in HFPO |
-
2019
- 2019-08-22 CN CN201910780130.4A patent/CN112409299A/en active Pending
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB931587A (en) * | 1961-05-18 | 1963-07-17 | Du Pont | Fluorocarbon epoxides |
| CN102675255A (en) * | 2012-04-18 | 2012-09-19 | 金华永和氟化工有限公司 | Preparation method for hexafluoropropylene oxide |
| CN104650010A (en) * | 2015-03-20 | 2015-05-27 | 山西福诺欧新材料科技股份有限公司 | Method for preparing hexafluoropropylene oxide |
| CN109678700A (en) * | 2018-12-24 | 2019-04-26 | 天津市长芦化工新材料有限公司 | The method that comprehensive utilization dioxygen oxidation method prepares the by-product generated in HFPO |
Non-Patent Citations (1)
| Title |
|---|
| 赵明强，等: "全氟聚醚的研究进展", 《山东化工》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116854572A (en) * | 2023-08-30 | 2023-10-10 | 哲弗智能系统（上海）有限公司 | Preparation method of perfluoro hexanone |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101228117B (en) | Fluorosulfonyl group-containing compound, method for production and polymer thereof | |
| US8557474B2 (en) | Fluorosulfonyl group-containing monomer and its polymer, and sulfonic acid group-containing polymer | |
| JP4788267B2 (en) | Polymer having fluorosulfonyl group and 1,3-dioxolane structure and use thereof | |
| EP1734603A1 (en) | Electrolyte material for solid polymer type fuel cell, electrolyte membrane and membrane electrode assembly | |
| EP2300502A1 (en) | Method for manufacturing fluoropolymers | |
| CN111138651B (en) | Synthetic method of perfluoropolyether peroxide | |
| JPH0764931B2 (en) | Copolymer of difluoromethylene oxide and tetrafluoroethylene oxide | |
| JP5598332B2 (en) | Method for producing fluorine-containing polymer particles | |
| CN103619890A (en) | Method for producing fluorine-containing copolymer | |
| CN112409299A (en) | Continuous preparation method of hexafluoropropylene oxide | |
| EP2785748B1 (en) | Process for reducing unstable end-groups in fluorinated polymers | |
| WO2007088929A1 (en) | Process for production of perfluoropolyether carboxylic acid fluoride | |
| CN116903848A (en) | Method for quenching residual halogenated alkane in nucleophilic polymerization reaction | |
| WO2013031848A1 (en) | Method for decomposing fluorinated organic compound | |
| KR102592427B1 (en) | Method for producing fluorinated copolymer containing perfluoro sulfonyl fluoride group and copolymer prepared therefrom | |
| US10738003B2 (en) | Process and device for preparing environmentally-friendly insulating gas perfluoroalkylnitrile | |
| JP2006173098A (en) | Method for manufacturing electrolyte material for polymer electrolyte fuel cell, membrane for polymer electrolyte fuel cell, and electrode coupling | |
| EP2725050A1 (en) | Method for producing polyphenylene ether ether ketone | |
| EP3643728A1 (en) | Method for producing fluorine-containing polymer, fluorine-containing polymer having functional group and electrolyte membrane | |
| JP5842919B2 (en) | Method for producing organic compound having sulfo group, method for producing liquid composition, and method for hydrolyzing organic compound having fluorosulfonyl group | |
| JPS60156632A (en) | Manufacture of vinyl chloride ether monomer and intermediate | |
| KR102031804B1 (en) | Method of perparing heptafluoroisopropyl trifluorovinyl ether | |
| CN114507340B (en) | Perfluoropolyether and preparation method thereof | |
| CN111099974A (en) | Preparation method of perfluoro-1, 3-bisethyleneoxypropane | |
| CN111378064A (en) | Preparation method of perfluorosulfonyl fluororesin |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20210226 |