CN102211983A - Preparation method of perfluoromethyl vinyl ether - Google Patents
Preparation method of perfluoromethyl vinyl ether Download PDFInfo
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- CN102211983A CN102211983A CN2011100886856A CN201110088685A CN102211983A CN 102211983 A CN102211983 A CN 102211983A CN 2011100886856 A CN2011100886856 A CN 2011100886856A CN 201110088685 A CN201110088685 A CN 201110088685A CN 102211983 A CN102211983 A CN 102211983A
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Abstract
The invention relates to a preparation method of perfluoromethyl vinyl ether, and belongs to the field of fluorine-containing plastics. The preparation method comprises the following steps of: preparing CF3OK by using potassium fluoride, carbonyl fluoride and tetrafluoroethylene as initial raw materials and using acetonitrile as a solvent in the absence of a catalyst, and reacting the CF3OK with tetrafluoroethylene in the presence of a little amount of water to prepare the perfluoromethyl vinyl ether serving as a target product. The reaction temperature is normal temperature in the whole process, the reaction of the first step is under normal pressure, and the reaction of the second step does not need external pressure, so the reaction conditions are easily realized and easily controlled; moreover, the equipment used in the preparation process has simple structure, so the cost of the whole production process is low; the intermediate products do not need high-purity separation, so the middle separation step is reduced, and the synthesis cost is reduced; meanwhile, the acetonitrile solvent can be recycled and is not released to the air space, so the method has no pollution and is environment-friendly; therefore, the method can be applied to large-scale industrialized production.
Description
Technical field
The invention belongs to extraordinary fluorine-containing comonomer field, be specifically related to carbonyl fluoride (COF
2), Potassium monofluoride (KF) and tetrafluoroethylene (TFE) be the method for feedstock production perfluoro methyl vinyl ether (PMVE).
Background technology
Perfluoro methyl vinyl ether (PMVE) can be used as the production preparation process that raw material is applied to various fluoropolymers such as fluoroplastics, viton, is the important monomer of modification viton and modification fluoroplastics preparation.For example: PMVE can form viton with tetrafluoroethylene generation copolymerization, and this kind viton has that tetrafluoroethylene is heat-resisting, the reagent of anti-number of chemical corrosive advantage; Under the condition of contacted hot steam, but this kind viton stable existence 1 year; In the alkali lye environment, also can surpass 3000 hours duration of service continuously, so be widely used in the sealing article (fluid machinery, 34,52 (2006)) under the continuous duty.In addition, this kind viton has very low ventilation property, and anti-creep is suitable for making under the extensive chemical corrosive environment sealing member that uses, diaphragm, flexible pipe etc.Because perfluor ether elastomerics has excellent physicals and anti-various pharmaceutical chemicals, and Applicable temperature scope extremely wide (45～316 ℃), so be widely used in chemical industry, oil, machinofacture, Aeronautics and Astronautics, electronic instrument, shipbuilding and various types of vehicles, can satisfy many rigorous environment conditional request (Chinese rubber, 17,23 (2001)).
At present, about the existing many reports of the synthetic method of PMVE.For example, the U.S., Russia and China have reported respectively and have utilized carbonyl fluoride (COF
2) react with Propylene oxide hexafluoride (HFPO), obtain acyl fluorides ether; Acyl fluorides ether and K then
2CO
3Or Na
2CO
3Salify promptly obtains to contain fluorovinyl ether to the carboxylate salt pyrolysis, and this kind method is the main method of present industrial production PMVE.Yet this method can't be stopped the generation of Tetrafluoroethane base ether in preparation process, and to K
2CO
3Or Na
2CO
3, the water-content in the solvent, catalyzer has very strict requirement, and reacted solvent and catalyzer be difficult to reclaim and use, and causes a large amount of solvents, catalyzer waste, and cause certain environmental problem (Russ.J.Appl.Chem., 2005,1640-1645; CA101659602A; UA3114778; Journal of Polymer Science, Part A:Polymer Chem., 1968,398-405).In addition, United States Patent (USP) (UA 3321532) has been reported with metal oxide (SiO
2, CaO, ZnO etc.) and be catalyzer, remove the method that the acyl fluorides base obtains containing fluorovinyl ether by acyl fluorides ether at 300 ℃ of high temperature pyrolysis; Contain a small amount of Tetrafluoroethane base ether by product in the product that this method obtains, this by product ether be difficult to separate with usual way, so that the cost of subsequent treatment process significantly improves.In addition, document and patent report are arranged, with carbonyl fluoride and CFCl=CFCl is the synthetic PMVE of raw material, this method catalyst pretreatment and activatory technological process more complicated, time is longer, and target product needs the cryogenic condensation backflow to collect manufacturing cost higher relatively (WO 2009/150091, Journal of Polymer Science, Part A:General Papers 1965,4065-4074 and Chinese patent CA1775722A).The raw materials used HFPO of above method, the CFCl=CFCl large-scale industrial production of all being unrealized costs an arm and a leg.
Summary of the invention
The purpose of this invention is to provide a kind of is raw material with carbonyl fluoride, metal fluoride (MF) and tetrafluoroethylene (TFE), under relative mild conditions, with the novel method of the synthetic perfluoro methyl vinyl ether (PMVE) of pattern of the cost of cheapness, safety.This method need not catalyzer and raw material is easy to get, so have extremely strong industrial application value.
The manufacture method of perfluoro methyl vinyl ether is characterized in that: with structural formula is CF
3The trifluoromethoxy salt of OM and tetrafluoroethylene react and make, and described reaction conditions is: under normal temperature, secluding air condition, in being dissolved with the trifluoromethoxy salts solution, add the water of trace, stir adding tetrafluoroethylene reaction in solution down, described CF
3The mol ratio of OM and water is 1: 0.005～0.01.
The solvent of described trifluoromethoxy salts solution is a polar aprotic solvent.
Described polar aprotic solvent is an acetonitrile.
Described M is basic metal or alkaline-earth metal.
Described M is potassium or sodium.
Described oxygen content is lower than 1ppm.
Described CF
3The mol ratio of OM and tetrafluoroethylene is controlled at 1: 1.0～1.2.
The time of described reaction is 24～72 hours.
Described perfluoro methyl vinyl ether is to derive the gas of producing in the reactor by gas collector, carries out rectifying separation then and obtains.
Described trifluoromethoxy salt makes by the following method: adopt carbonyl fluoride, metal fluoride (MF) to react and obtain.
Described reaction conditions is: under the room temperature, feed carbonyl fluoride gas in the solution that is dissolved with metal fluoride, the mol ratio of metal oxide and carbonyl fluoride is 1: 2.0.
The solvent of described metal fluoride solution is a polar aprotic solvent, and the mol ratio of metal fluoride and polar aprotic solvent is 1: 8～12.
The pressure that described carbonyl fluoride gas feeds is 1～5 normal atmosphere, and the reaction times is 3～5 hours.
Adopt nitrogen purging after reaction when described trifluoromethoxy salt prepares is finished,, be communicated with COF on the described reaction vessel to take away gas and the liquid in the reaction vessel
2Retrieving arrangement, water washing device and alkaline cleaner.
The mixture that obtains after described reaction is finished is directly used in the preparation of perfluoro methyl vinyl ether.
Need do before the described metal fluoride reaction except that water treatment.
Described water-eliminating method, is dried metal fluoride under 250～300 ℃ of conditions for by retort furnace, and drying time is 2～3 hours, to remove the crystal water in the metal fluoride.
The present invention adopts CF
3OK under the condition that has less water to exist, in the condition of normal temperature and secluding air (because reaction raw materials has tetrafluoroethylene, when aerobic exists, explosive) following and tetrafluoroethylene reacts, preparation target product perfluoro methyl vinyl ether, reaction conditions are realized easily, also control easily; In addition, the employed simple in equipment of this preparation process is so the cost of whole process of production is lower.Raw material CF of the present invention
3OK can adopt other method to obtain, preferred the inventive method.Entire reaction course is as follows:
The present invention prepares PMVE by two-step approach, and the first step is with COF
2And metal fluoride (MF) is raw material, under normal temperature and pressure conditions, and preparation trifluoromethoxy salt; Second step reacted under normal temperature condition for tetrafluoroethylene and trifluoromethyl oxygen base salt, was prepared into PMVE, and concrete detailed operation steps is as follows:
1, CF
3The preparation of OK:, dry KF under 250～300 ℃ of conditions by retort furnace (1), and drying time is 2～3 hours, removes the crystal water among the KF; (2) accurate a certain amount of KF of weighing puts into reactor, and the inlet of reactor connects COF
2Steel cylinder, outlet connects COF successively
2Retrieving arrangement, water washing device and alkaline cleaner, the volume of acetonitrile be overall reactor long-pending 1/2～2/3, the mol ratio of KF and acetonitrile is preferably 1: 8～1: 12, the stirring and dissolving time is preferably 10～15 minutes; (3) under stirring and room temperature situation, open COF
2The valve of steel cylinder after the reducing valve decompression, reacts the COF of KF and adding in the acetonitrile solution that carbonyl fluoride is passed into KF at the uniform velocity
2Mol ratio is 1: 2.0; (4) stop to feed carbonyl fluoride, use nitrogen instead reactor is purged, remove the COF in the reactor
2, promptly obtain CF
3The acetonitrile solution of OK can be directly used in next step reaction;
2, CF
3OCF=CF
2Preparation: (5) are CF
3The acetonitrile solution of OK joins in the closed reactor, and adds the deionized water of magnetic stir bar and trace, CF in reactor
3The mol ratio of OK and water is 1: 0.005～1: 0.01; Then reactor is connected on the vacuum line, uses liquid nitrogen that reactor is cooled off, vacuumize (vacuum tightness is lower than 0.01Pa), to remove the air in the reactor; (6), in reactor, accurately add a certain amount of tetrafluoroethylene, CF by vacuum line
3The mol ratio of OK and tetrafluoroethylene is controlled at 1: 1.0～1.2; (7) reactor is placed allow it slowly be warming up to room temperature under the room temperature condition, reactor is stirred tetrafluoroethylene and CF by magnetic stirring apparatus
3OK reacted in closed reactor 24～72 hours; (8) derive the gas of producing in the reactor by gas collector, carry out rectifying separation then, promptly obtain target product CF
3OCF=CF
2
Preparation method of the present invention is a starting raw material with Potassium monofluoride, carbonyl fluoride and tetrafluoroethylene, is solvent with the acetonitrile, under the situation of catalyst-free effect, and preparation CF
3OK, then under the condition that has less water to exist and tetrafluoroethylene react preparation target product perfluoro methyl vinyl ether; Because whole process reaction temperature is a normal temperature, and the reaction pressure of the first step is a normal pressure; The reaction in second step also need not the external world and exerts pressure, so compared with prior art, these reaction conditionss are realized easily, also control easily; In addition, the employed simple in equipment of this preparation process is so the cost of whole process of production is lower; In preparation process, intermediate product does not need high purity separation, so reduced the intermediary separating step, has reduced synthetic cost, and simultaneously, in building-up process, the solvent acetonitrile recycling use does not enter airspace, thus pollution-free, environmental friendliness; Therefore, this method can be applied to large-scale industrial production.
Embodiment
Embodiment 1:
Under (1) 250 ℃ of condition, in retort furnace KF is dried, the time is 3 hours; (2) by the method for weighing, the KF of 80mmol is put into the tetrafluoroethylene reactor of 150ml, and add the acetonitrile of 500mmol, the inlet of reactor connects COF
2Steel cylinder, stirring and dissolving 10 minutes; (3) reactor inlet, be connected with carbonyl fluoride, outlet connects the acetonitrile receiving flask successively, carbonyl fluoride receiving flask, emptying behind washing and the alkaline cleaner; Open carbonyl fluoride steel cylinder switch, by reducing valve, with the flow of 0.5mmol/min, under agitation condition, carbonyl fluoride is joined in the acetonitrile solution, the feeding time is 3 hours, and the add-on of carbonyl fluoride is 90mmol; (4) stop to feed carbonyl fluoride, the flow of using nitrogen 1.5mmol/min instead purges 10min to reactor, removes the COF in the reactor
2, promptly obtain CF
3The acetonitrile solution of OK; (5) CF of transfer 10mmol
3The OK acetonitrile solution and adds the deionized water of magnetic stir bar and 0.05mmol in reactor in closed reactor; Then reactor is connected on the vacuum line,, vacuumizes and remove air in the reactor using liquid nitrogen that reactor is carried out under the refrigerative condition; (6), in reactor, accurately add the tetrafluoroethylene of 10mmol by vacuum line; (7) at ambient temperature, reactor is stirred tetrafluoroethylene and CF by magnetic stirring apparatus
3OK reacted in closed reactor 24 hours; (8) derive the gas of producing in the reactor by gas collector, promptly obtain target product CF
3OCF=CF
2By chromatograph the ultimate aim product of present embodiment is analyzed, drawn that PMVE content is 54.97% in the final synthetic product of present embodiment.
Embodiment 2:
Under (1) 300 ℃ of condition, in retort furnace KF is dried, the time is 2.5 hours; (2) by the method for weighing, the KF of 100mmol is put into the tetrafluoroethylene reactor of 150ml, and add the acetonitrile of 500mmol, the inlet of reactor connects COF
2Steel cylinder, stirring and dissolving 15 minutes; (3) reactor inlet, be connected with carbonyl fluoride, outlet connects the acetonitrile receiving flask successively, carbonyl fluoride receiving flask, emptying behind washing and the alkaline cleaner; Open carbonyl fluoride steel cylinder switch, by reducing valve, with the flow of 0.4mmol/min, under agitation condition, carbonyl fluoride is joined in the acetonitrile solution, the feeding time is 5 hours, and the add-on of carbonyl fluoride is 120mmol; (4) stop to feed carbonyl fluoride, the flow of using nitrogen 1.5mmol/min instead purges 15min to reactor, removes the COF in the reactor
2, promptly obtain CF
3The acetonitrile solution of OK; (5) CF of transfer 10mmol
3The OK acetonitrile solution and adds the deionized water of magnetic stir bar and 0.02mmol in reactor in closed reactor; Then reactor is connected on the vacuum line,, vacuumizes and remove air in the reactor using liquid nitrogen that reactor is carried out under the refrigerative condition; (6), in reactor, accurately add the tetrafluoroethylene of 12mmol by vacuum line; (7) at ambient temperature, reactor is stirred tetrafluoroethylene and CF by magnetic stirring apparatus
3OK reacted in closed reactor 72 hours; (8) derive the gas of producing in the reactor by gas collector, carry out rectifying separation then, promptly obtain target product CF
3OCF=CF
2Derive the gas of producing in the reactor by gas collector, carry out rectifying separation then, promptly obtain target product CF
3OCF=CF
2By chromatograph the crude product of present embodiment is analyzed, drawn that PMVE content is 72.5% in the final synthetic product of present embodiment.
Claims (16)
1. the manufacture method of perfluoro methyl vinyl ether, it is characterized in that: with structural formula is CF
3The trifluoromethoxy salt of OM and tetrafluoroethylene react and make, and described reaction conditions is: under normal temperature, secluding air condition, in being dissolved with the trifluoromethoxy salts solution, add the water of trace, stir adding tetrafluoroethylene reaction in solution down, described CF
3The mol ratio of OM and water is 1: 0.005～0.01.
2. preparation method according to claim 1, described M are basic metal or alkaline-earth metal.
3. preparation method according to claim 2, described M are potassium or sodium.
4. preparation method according to claim 1, wherein the solvent of trifluoromethoxy salts solution is a polar aprotic solvent.
5. preparation method according to claim 4, described polar aprotic solvent is an acetonitrile.
6. preparation method according to claim 1, described CF
3The mol ratio of OM and tetrafluoroethylene is 1: 1.0～1.2, and the time of described reaction is 24～72 hours.
7. preparation method according to claim 1, described perfluoro methyl vinyl ether is to derive the gas of producing in the reactor by gas collector, carries out rectifying separation then and obtains.
8. preparation method according to claim 1, described trifluoromethoxy salt makes by the following method: employing carbonyl fluoride and metal fluoride react and obtain.
9. preparation method according to claim 8, the reaction conditions when wherein trifluoromethoxy salt prepares is: under the room temperature, feed carbonyl fluoride gas in the solution that is dissolved with metal fluoride, the mol ratio of metal fluoride and carbonyl fluoride is 1: 2.
10. preparation method according to claim 9, the pressure that described carbonyl fluoride gas feeds is 1～5 normal atmosphere, its reaction times is 3～5 hours.
11. preparation method according to claim 8, the solvent of metal fluoride solution was a polar aprotic solvent when wherein trifluoromethoxy salt prepared, and the mol ratio of metal fluoride and polar aprotic solvent is 1: 8～1: 12.
12. preparation method according to claim 11 adopts nitrogen purging after wherein trifluoromethoxy salt preparation feedback is finished, take away gas in the reaction vessel with nitrogen, is communicated with COF on the described reaction vessel
2Retrieving arrangement, water washing device and alkaline cleaner.
13. preparation method according to claim 12, the mixture that obtains after described reaction is finished is directly used in the preparation of perfluoro methyl vinyl ether.
14. preparation method according to claim 9 need do except that water treatment before the described metal fluoride reaction.
15. preparation method according to claim 14, described water-eliminating method, is dried metal fluoride under 250～300 ℃ of conditions for by retort furnace, and drying time is 2～3 hours, to remove the crystal water in the metal fluoride.
16. preparation method according to claim 1, described secluding air condition are that oxygen content is lower than 1ppm.
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Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105367392A (en) * | 2014-08-12 | 2016-03-02 | 中化近代环保化工(西安)有限公司 | Perfluoromethyl vinyl ether preparation method |
| CN107286060A (en) * | 2017-06-22 | 2017-10-24 | 山东华夏神舟新材料有限公司 | End group is the preparation method of the perfluoroalkyl vinyl ether of sulfonyl fluoride group |
| CN109956855A (en) * | 2017-12-25 | 2019-07-02 | 中蓝晨光化工研究设计院有限公司 | A kind of preparation method of high-purity perfluoro methyl vinyl ether |
| WO2022010204A1 (en) * | 2020-07-07 | 2022-01-13 | 한국화학연구원 | Method for preparing perfluoromethylvinyl ether having high conversion rate |
| KR20220005775A (en) * | 2020-07-07 | 2022-01-14 | 한국화학연구원 | Method for preparing perfluoropropyl vinyl ether with high conversion rate |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3291843A (en) * | 1963-10-08 | 1966-12-13 | Du Pont | Fluorinated vinyl ethers and their preparation |
| JPH03264545A (en) * | 1990-03-15 | 1991-11-25 | Nippon Mektron Ltd | Fluorine-containing allyl ether and production thereof |
| US20110082312A1 (en) * | 2008-05-19 | 2011-04-07 | Merck Patent Gesellschaft Mit Deschrankter Haftung | Production of compounds comprising cf30 groups |
-
2011
- 2011-04-08 CN CN 201110088685 patent/CN102211983B/en active Active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3291843A (en) * | 1963-10-08 | 1966-12-13 | Du Pont | Fluorinated vinyl ethers and their preparation |
| JPH03264545A (en) * | 1990-03-15 | 1991-11-25 | Nippon Mektron Ltd | Fluorine-containing allyl ether and production thereof |
| US20110082312A1 (en) * | 2008-05-19 | 2011-04-07 | Merck Patent Gesellschaft Mit Deschrankter Haftung | Production of compounds comprising cf30 groups |
Non-Patent Citations (3)
| Title |
|---|
| MING-H. HUNG等: "Synthesis of Perfluorovinyl Ether Monomers", 《J.ORG.CHEM.》, vol. 59, no. 15, 31 July 1994 (1994-07-31) * |
| WALTER NAVARRINIA等: "New perfluorovinylethers through the bis(fluoroxy)difluoromethane (BDM) chemistry", 《JOURNAL OF FLUORINE CHEMISTRY》, vol. 125, no. 2, 29 February 2004 (2004-02-29), XP004486522, DOI: doi:10.1016/j.jfluchem.2003.07.011 * |
| 王家浚等: "相转移法催化合成原乙酸三甲酯", 《天津化工》, vol. 17, no. 6, 20 December 2003 (2003-12-20) * |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105367392A (en) * | 2014-08-12 | 2016-03-02 | 中化近代环保化工(西安)有限公司 | Perfluoromethyl vinyl ether preparation method |
| CN105367392B (en) * | 2014-08-12 | 2017-10-03 | 中化近代环保化工(西安)有限公司 | A kind of preparation method of perfluoro methyl vinyl ether |
| CN107286060A (en) * | 2017-06-22 | 2017-10-24 | 山东华夏神舟新材料有限公司 | End group is the preparation method of the perfluoroalkyl vinyl ether of sulfonyl fluoride group |
| CN109956855A (en) * | 2017-12-25 | 2019-07-02 | 中蓝晨光化工研究设计院有限公司 | A kind of preparation method of high-purity perfluoro methyl vinyl ether |
| CN109956855B (en) * | 2017-12-25 | 2022-04-15 | 中蓝晨光化工研究设计院有限公司 | Preparation method of high-purity perfluoromethyl vinyl ether |
| WO2022010204A1 (en) * | 2020-07-07 | 2022-01-13 | 한국화학연구원 | Method for preparing perfluoromethylvinyl ether having high conversion rate |
| KR20220005777A (en) | 2020-07-07 | 2022-01-14 | 한국화학연구원 | Method for preparing perfluoromethyl vinyl ether with high conversion rate |
| KR20220005775A (en) * | 2020-07-07 | 2022-01-14 | 한국화학연구원 | Method for preparing perfluoropropyl vinyl ether with high conversion rate |
| KR102477162B1 (en) | 2020-07-07 | 2022-12-13 | 한국화학연구원 | Method for preparing perfluoromethyl vinyl ether with high conversion rate |
| KR102477300B1 (en) * | 2020-07-07 | 2022-12-13 | 한국화학연구원 | Method for preparing perfluoropropyl vinyl ether with high conversion rate |
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