WO2008050760A1 - Procédé de production d'oxyde d'hexafluoropropylène - Google Patents
Procédé de production d'oxyde d'hexafluoropropylène Download PDFInfo
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- WO2008050760A1 WO2008050760A1 PCT/JP2007/070638 JP2007070638W WO2008050760A1 WO 2008050760 A1 WO2008050760 A1 WO 2008050760A1 JP 2007070638 W JP2007070638 W JP 2007070638W WO 2008050760 A1 WO2008050760 A1 WO 2008050760A1
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- organic phase
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- hexafluoropropylene
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- 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
- C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
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- 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
Definitions
- the present invention relates to a method for producing hexafluoropropylene oxide, and more particularly to a method for obtaining hexafluoropropylene oxide by oxidation of hexafluoropropylene.
- Hexafluoropropylene oxide is an important compound in the production of fluorine-containing compounds, for example, used as a raw material for perfluorovinyl ether. Hexafluoropropylene oxide oligomers are used as lubricants and heat transfer media.
- Patent Document 1 Japanese Patent Publication No. 45-11683
- Patent Document 2 Japanese Unexamined Patent Publication No. 2006-83152
- Patent Document 3 Japanese Patent Publication No. 64-11021
- Patent Document 4 Japanese Patent Publication No. 3-75546
- Patent Document 5 Japanese Patent No. 3785652
- Non-Patent Document 1 Hideho Okamoto, “Applicability of microreactor to green 'process”, Falmasia, 2005, Japan Pharmaceutical Association, Vol. 41, No. 7, p664
- the present invention relates to a process for producing hexafluoropropylene oxide, which comprises a higher HFP.
- An object of the present invention is to provide a novel production method capable of achieving O yield.
- HFP hexafluoropropylene oxide
- a quaternary ammonium salt in a two-phase system of an aqueous phase and an organic phase.
- a liquid phase reaction method has been proposed to oxidize with chlorate to obtain HFPO! (See Patent Documents 3 and 4).
- the inventors of the present invention pay particular attention to this method, and as a result of intensive studies, the present invention has been completed.
- an organic phase containing hexafluoropropylene and an aqueous phase containing an oxygen-containing oxidizing agent are brought into contact with each other through a minute space, and the hexafluoropropylene is converted into an acid.
- a method for producing hexafluoropropylene oxide which is reacted with an oxygen-containing oxidizing agent to obtain hexafluoropropylene oxide.
- a yield due to HFP 3 O is significantly higher than that of any conventional method. This is because the present invention is not bound by any theory, but is considered to be due to the following reasons.
- the oxidation reaction to obtain hexafluoropropylene oxide (HF PO) from hexafluoropropylene (HFP) is an exothermic reaction. Temperature control is possible, which suppresses side reactions, The selectivity of HFPO can be improved.
- the reaction to obtain HFPO from HFP involves diffusion, it can be made to react sufficiently in a shorter reaction time by allowing the reaction to proceed in a minute space.
- the reaction rate can be increased. Therefore, sufficient heat removal and strict temperature control are possible, so that the selectivity does not decrease even when the reaction rate increases, and the reaction time and residence time) can be shortened.
- HF PO can be discharged to the outside of the reaction system (microspace) instantly to prevent further reaction of the product (overreaction). As a result, the reaction with high selectivity and high conversion can be achieved. It can be realized and the yield of HFPO can be improved.
- the “microspace” means a flow path through which a fluid for reaction (in the present invention, including a liquid substance including an aqueous phase and an organic phase and an optionally present gas phase) flows. It means a space with a width of 3 cm or less, preferably 1 m or more and less than lcm (micro order or milliorder), and the width of the flow channel means the minimum distance between the opposing wall surfaces of the flow channel.
- Such “microspaces” are known as “microreactors” or “micromixers” in fields such as pharmaceutical and synthetic chemistry, for example! /, Each flow path or channel of a reactor or mixer. )! /, (See Non-Patent Document 1, for example).
- an organic phase containing hexafluoropropylene and an aqueous phase containing an oxygen-containing oxidizing agent are brought into contact in the presence of a phase transfer catalyst, and the hexafluoropropylene is oxidized with oxygen.
- the reaction is caused by the action of the agent and the phase transfer catalyst. This makes it possible to cause the reaction to occur more efficiently.
- the microspace is about 40-; a temperature of 100 ° C and about 0.
- Hexafluoropropylene is a gas at normal temperature and pressure (boiling point: 29.4 ° C), so when supplying the organic phase to the microspace, this pre-adjustment makes it possible to obtain more HFP. It can be dissolved in the organic phase, allowing the liquid phase reaction to proceed efficiently.
- the reaction time in the minute space can be about 0.01 to 1000 seconds. Such a reaction time is extremely shorter than a reaction time in a normal reaction space volume generally used in the past.
- phase transfer catalyst used in the preferred embodiment of the present invention! /, The embodiment! /, Has an affinity for both the aqueous phase and the organic phase, so that the aqueous phase and the organic phase are separated.
- Any substance can be used as long as it can move in any form, and promotes the reaction by transferring the nucleophilic part of the oxygen-containing oxidant distributed mainly in the aqueous phase to the organic phase.
- the "oxygen-containing oxidant" used in the present invention may be any oxidant containing an oxygen atom and capable of oxidizing HFP to HFPO.
- FIG. 1 is a schematic diagram of an apparatus used for producing HFPO in Example 1 of the present invention.
- FIG. 2 is a reaction schematic diagram in Example 1 of the present invention.
- FIG. 3 is a schematic diagram of an apparatus used for producing HFPO in Example 2 of the present invention. It is.
- Organic solvent tank (Organic solvent includes phase transfer catalyst)
- Aqueous solution tank (aqueous solution contains oxygen-containing oxidant)
- an aqueous phase containing an oxygen-containing oxidant and an organic phase containing hexafluoropropylene (HFP) are prepared, and a phase transfer catalyst is prepared.
- hypochlorite for example, hypochlorite, chlorite, chlorate, perchlorate, ozone water, hydrogen peroxide solution and the like can be used.
- hypochlorite is preferred because it produces hypochlorite ions under the reaction conditions and reacts with HFP to form chlorine ions, which does not oxidize and forms salts.
- Hypochlorite includes alkali metal salts and alkaline earth metal salts, among which sodium salts are industrially mass-produced for uses such as bleaching agents and fungicides, and are inexpensive. It is more preferable because it is available at Oxygen-containing oxidizing agents can be used with alkalis such as sodium hydroxide and potassium oxide. By adding potassium to make it alkaline, it is possible to prevent the decomposition of the oxidant by the acid as the reaction proceeds.
- aqueous phase solvent an aqueous substance capable of dissolving the oxygen-containing oxidizing agent, generally water, can be used.
- the concentration of the oxygen-containing oxidant in the aqueous phase is, for example, about;! To 2 Owt%, preferably about 515wt% at the time of supplying the microspace (or at the beginning of the reaction).
- organic solvent for the organic phase an inert solvent that is substantially immiscible or poorly miscible with the aqueous phase can be used.
- organic solvents include aliphatic hydrocarbons, alicyclic hydrocarbons, aromatic hydrocarbons, chlorinated hydrocarbons, fluorinated hydrocarbons (CFC HCFC HFC), perfluorocarbons.
- examples include polyethers.
- a halogen-containing compound such as chlorinated hydrocarbons, fluorinated hydrocarbons, perfluoropolyether and a mixture thereof. That is, fluorine-based hydrocarbons (black-mouthed fluorocarbon (CFC), hide-opened fluorocarbon (HCFC), hide-opened fluorocarbon (HFC)) and perfluoropolyether are more preferred.
- Aliphatic hydrocarbons, alicyclic hydrocarbons, and aromatic hydrocarbons are not particularly limited.
- hexane, heptane, isoheptane, octane, isooctane, methylcyclopentane, cyclohexane, methylcyclohexane. , Toluene and the like are preferable.
- CFCs examples include 1,1,2 trichloro 1,2,2 trifluoroethane (CFC-113).
- HCFCs include difluorochloromethane (HCFC-22), 1,1-dichloro-1-1-fluoroethane (HCFC-141b), 1,1-dichloro-1-2,2,2-trifluoroethane (HCFC 123), Examples include 1-chloro 1, 1-difluoroethane (HCFC-142b) and diclonal pentafluoropropane (HCFC-225).
- Fluoroaliphatic hydrocarbons represented by 2), and more specifically, C F H C F H C F H C F H C F H C F H C F H C F H C F H C F H C F H
- HCF Hexafnorolepentane
- HFC particularly 1, 1, 1, 3, 3-pentafluorobutane, is more preferable.
- perfonoreo mouth polyethers examples include compounds represented by the following general formula (I).
- the molecular weight of the compound represented by the general formula (I) is preferably about 100 to 100000, more preferably about 250 to 50,000, more preferably about 500 to 10,000, more preferably 10,000.
- R, R, R, R and R are each independently a fluorine atom or a perfluoroalkyl.
- 1, m, n each independently represents 0 or a natural number, and at least one of 1, m, n is not 0. )
- perfluoropolyether a compound represented by the following general formula (II) or a compound represented by the following general formula (III) may be used.
- the solubility of HFP in an organic solvent may depend on the temperature and pressure conditions, although it depends on the type of organic solvent used. Prior to supplying the organic phase containing HFP to the micro space, this organic phase (with HFP and organic solvent coexisting) is substantially equivalent to the temperature and pressure conditions in the micro space. Alternatively, it is preferable to apply conditions closer to this (also referred to as preliminary adjustment in this specification).
- the organic phase is suitably maintained in advance at a temperature of about 40 to; a temperature of about 100 ° C, preferably about 10 to 50 °, a pressure of about 0.2;! To 20 MPa, preferably about 0.2 to 5 MPa. Can do.
- This preconditioning condition is preferably a temperature and pressure condition that makes the HFP substantially liquid.
- HFP is a gas at normal temperature and pressure (boiling point: 29.4 ° C)
- the organic phase when supplied to the microspace, it is preliminarily attached to the temperature and pressure conditions at which the HFP is substantially in a liquid state. More preferably, it is preferred to dissolve substantially all of the HFP in the organic phase.
- the reaction time (residence time) in the micro space is extremely short, and the redistribution of the HFP from the organic phase to the gas phase is negligible.
- the pressure condition may be different from the temperature and pressure conditions of the microspace in which the organic phase is to be supplied.
- the HFP concentration in the organic phase is, for example, about 0.5 to 100 wt%, preferably about 1 to 50 wt%, more preferably about 2 to 20 wt%, when supplying the microspace (or at the beginning of the reaction). .
- phase transfer catalyst for example, quaternary ammonium salts, quaternary phosphoyu salts, and macrocyclic ethers can be used. Of these, quaternary ammonium salts are preferred because they have excellent affinity for both organic and aqueous phases, have a wide variety of commercially available reagents, and are relatively inexpensive.
- the quaternary ammonium salt is represented by the following formula (wherein Rl, R2, R3, and R4 are hydrocarbon groups such as alkyl groups, and X- is an anion).
- Rl, R2, R3, R4 are hydrocarbon groups such as alkyl groups, and X- is an anion.
- the type and number of carbon chains of this hydrocarbon group (Rl, R2, R3, R4) can be arbitrarily selected.
- (X_) type can also be selected arbitrarily.
- This selection can be appropriately made based on the type and amount (or concentration) of the oxygen-containing oxidizing agent used in the reaction system, the type and amount of the solvent, the temperature and pressure of the reaction, and the like.
- tri-n-octylmethylammonium chloride (TOMAC), tetrabutylammonium hydrogensulfate (TBAS), tetrabutylammonium bromide (TBAB) can be used as quaternary ammonium salts.
- TOMAC tri-n-octylmethylammonium chloride
- TBAS tetrabutylammonium hydrogensulfate
- TBAB tetrabutylammonium bromide
- S The reaction of the present invention has a high partition to the organic phase in which HFP is present, and quaternary ammonium salts, especially TOMAC are preferred! /.
- the quaternary phosphonium salt is represented by the following formula (wherein R5, R6, R7 and R8 are hydrocarbon groups, for example, alkyl groups, and Y— is an anion).
- R5, R6, R7 and R8 are hydrocarbon groups, for example, alkyl groups, and Y— is an anion).
- the type and number of carbon chains of the hydrocarbon group (R5, R6, R7, R8) can be arbitrarily selected, and the anion (Y type can also be arbitrarily selected).
- This selection can also be made appropriately based on the type and amount (or concentration) of the oxygen-containing oxidizing agent used in the reaction system, the type and amount of the solvent, the temperature and pressure of the reaction, and the like.
- the 4th For example, tetra-n-butylphosphonium bromide, tetra-n-butylphosphonium bromide, n-amyltriphenylphosphonium bromide, benzyltriphenylphosphonium chloride, etc. are particularly preferred.
- the phase transfer catalyst may be supplied to the microspace in any form as long as it exists when the aqueous phase and the organic phase are brought into contact with each other, but is generally added to the aqueous phase or the organic phase.
- the concentration of the phase transfer catalyst in the aqueous phase or the organic phase is, for example, about 0.5 to 20 wt%, preferably about;
- the aqueous phase containing the oxygen-containing oxidant prepared as described above and the organic phase containing HFP are supplied to the micro space together with the phase transfer catalyst.
- the minute space is sufficient if the width of the flow path through which the reaction fluid (water phase and organic phase and optionally a gas phase) flows is 3 cm or less.
- the width of the flow path is about 1 m to l cm, preferably about 10 to 5000 m.
- the length and cross-sectional area of the flow path is not particularly limited, for example, the cross-sectional area of the channel is about 3 ⁇ 1 X 10_ 6 ⁇ 7. 9 X 10- ⁇ m 2 possible.
- a reactor or reaction tube having at least one minute space with an equivalent diameter of 20 111 to 2000 111), a so-called “microreactor” or “micro-mouth mixer” can be used.
- aqueous phase containing the oxygen-containing oxidant and the organic phase containing hexafluoropropylene (HFP) flow and contact with each other in the micro space together with the phase transfer catalyst, and during this time, the HFP interacts with the oxygen-containing oxidant. Reacts in the presence of a transfer catalyst to produce hexafluoropropylene oxide (HF PO).
- HFP hexafluoropropylene oxide
- the contact between the organic phase and the aqueous phase in the minute space is not particularly limited, but the laminar flow state is preferable. Laminar flow can be judged based on the Reynolds number, depending on the structure of the device used.
- the temperature and pressure in the micro space are not particularly limited as long as the reaction for obtaining HFPO from HFP proceeds, but is about 40 to 100 ° C, preferably about 10 to 50 ° C, and about 0 Can be suitably maintained at a pressure of 20 to 20 MPa, preferably at a pressure of about 0.2 to 5 MPa.
- the volume ratio of the organic phase / water phase in the micro space (or the ratio of the supply flow rate of the organic phase / water phase) can be appropriately set according to the specific situation. 10, preferably about 0.2-5.
- reaction time and residence time in a micro-space are very short compared to the conventional method.
- ⁇ , ⁇ column free approx. 0.01-; 1000 less, special approx. 0. 01 ⁇ ; 100 less, more or less about 0. 01— 5
- the organic phase and the aqueous phase after the reaction are extracted from the micro space in an arbitrary form, for example, in a mixed state or a separated state. Since HFPO is distributed in the organic phase, the FPO produced by the reaction can be recovered from the organic phase after the reaction. In particular, since HFPO is gasified by depressurization, it can be easily recovered from the organic phase.
- the organic phase after the reaction may be subjected to post-treatment as necessary to remove unnecessary substances such as unreacted HFP, side reaction products and solvent! /.
- distillation is a force that is widely used industrially as a general separation operation
- the unreacted HFP that is the main component of the reaction mixture and the boiling point of the target product HFPO is 29.4 ° respectively. C and 27.4 ° C.
- extractive distillation is preferred to obtain high purity HFPO by separating HFP and HFPO (see Patent Document 5).
- the separated HFP may be reused as a reaction raw material.
- extractive distillation it is preferable to use a solvent that can be used as an extractive distillation solvent as the solvent used in the organic phase.
- the effectiveness of extractive distillation solvents can be evaluated by the relative volatility of HFP and HFPO.
- the relative volatility can be measured by a method well known in the art or a method described in Patent Document 5.
- the relative volatility of HFPO with respect to HFP should be greater than 1, but in general it is preferably 1.1 or higher.
- HCFC-141b 1, 1-dichloro-1-1-fluoroethane (HCFC-141b), 2,2-dichloro opening—1, 1,1-trifunoleoleotane (HCFC-123), 1,2-dichloro- 1, 1, 2—Trif Norolethan (HCFC—123a), 3,3-dichloro-1,1,1,1,2,2-pentafunoleorov. Mouth bread (HCFC—225ca), 1,3-dichloro-1,1,2,2,3-pentafluoropropane (HCFC—225cb) and the like can be used.
- Such solvents include CH CI, CHC1, CC1, CH
- Hexafluoropropylene oxide is produced as described above.
- the process for producing hexafluoropropylene oxide can be carried out continuously.
- the yield of HFPO can be significantly improved as compared with the conventional production method.
- the present embodiment relates to an example in which the internal space of a narrow tube 21 (shown by a dotted line in the figure) is used as a minute space.
- the thin tube 21 was a SUS tube having a nominal inner diameter of 250 111 and a length of 1.5 m.
- the thin tube 21 can be controlled by heating using a heating jacket 21a.
- the inlet side of this narrow tube 21 is connected to a SUS T-type connector 21b (applicable outer diameter 1/16 inch, manufactured by Swagelok), and two kinds of fluids, an organic phase and an aqueous phase, are connected from lines 9 and 19, respectively. It was configured so that it could be supplied to the narrow tube 21.
- a line 23 is connected to the outlet side of the thin tube 21, and a SUS tube having a nominal inner diameter of 500 mm is used for the line 23.
- a nut etc. were used suitably for the connection part.
- the HFP tank 1 from the HFP and the organic solvent tank 3 from the organic solvent were drawn into the pump chamber 7 a of the syringe pump 7 from the line 5.
- This organic solvent contains 1, 1-Dichloro 1 Fluoroethane (HCFC—141b) was used, and tri-octylmethylammonium chloride (TOMAC: (CH) CH NC1) was used as the phase transfer catalyst.
- the organic phase at the time of supply to the capillary tube 21 was about 5 ° C and about 2 MPa. At this time, substantially all of the HFP was liquefied, and the HFP concentration in the organic phase was about 1. lwt%.
- the concentration of TOMAC (phase transfer catalyst) in the organic phase is substantially equivalent to the concentration in the organic solvent used.
- the aqueous solution was drawn from the aqueous solution tank 13 into the pump chamber 17 a of the syringe pump 17 through the line 15.
- This aqueous solution is obtained by dissolving sodium hypochlorite (NaCIO) as an oxygen-containing oxidant in water at about 10 wt%.
- NaCIO sodium hypochlorite
- This aqueous solution was pushed out of the syringe chamber 17a and supplied as a thin tube 21 aqueous phase through a line 19.
- the aqueous phase at the time of supply to the capillary 21 was approximately room temperature (approximately 20 ° C) and approximately 2 MPa.
- the concentration of NaCIO (oxygen-containing oxidizer) in the aqueous phase is the same as that in the aqueous solution used.
- the supply flow rate of the organic phase was about lmL / min, and the supply flow rate of the aqueous phase was about 250 ⁇ L / min.
- the organic phase and the aqueous phase supplied to the narrow tube 21 flow in a minute space in the narrow tube 21 in a laminar flow state while contacting each other in the presence of the catalyst.
- the thin tube 21 was heated to about 45 ° C. by the heating jacket 21a, and the pressure was adjusted by the back pressure valve 25 existing in the downstream line 23.
- the inside of the narrow tube 21 was maintained at about 45 ° C. and about 2 MPa.
- the reaction mixture (the mixture of the organic phase and the aqueous phase after the reaction) was extracted from capillary tube 21 through line 23 to recovery tank 27.
- Line 23 was maintained at about 0 ° C with an ice bath (in the figure, the cooling area around line 23 is shaded).
- the residence time of the fluid (including the organic and aqueous phases and optionally a gas phase) in the capillary 21 was about 1.1 seconds.
- the line 23 is maintained at a low temperature of about 0 ° C., it can be considered that the reaction does not substantially occur in the line 23. Therefore, you can consider the residence time of the fluid in the narrow tube 21 as the reaction time! /.
- the recovered reaction mixture was allowed to stand to separate into an organic phase and an aqueous phase.
- the obtained organic phase was analyzed by gas chromatography.
- the conversion of HFP was 99% and the selectivity of HFPO was about 94%. From these, the yield was about 92%.
- Example 2 The same apparatus as in Example 1 was used except that a SUS tube having a nominal inner diameter of 500 m and a length of 4 m was used as the thin tube 21. Then, a mixture of the components shown in Table 1 was used as the organic phase, this organic phase was supplied at the supply flow rate shown in Table 1, and an aqueous sodium hypochlorite solution of about 1 Owt% as in Example 1 was used as the aqueous phase. However, the same operation as in Example 1 was performed except that the supply flow rate was about 24 ml / min. Table 2 shows the results of analysis of the organic phase obtained by gas chromatography.
- the present embodiment relates to a unit that uses a unit space in micromixer 31 as a minute space.
- micromixer 31 As the micromixer 31, SSIMM (Standard Slit Interdigital Micro Mixer, manufactured by IMM, nominal slit width: 40 m) was used.
- tetraptyl ammonium hydrogen sulfate (T BAS) was used as a phase transfer catalyst instead of TOMAC.
- T BAS tetraptyl ammonium hydrogen sulfate
- the organic phase and the aqueous phase are supplied to the micromixer 31.
- the inside of the micromixer 31 is provided with a plurality of slits (nominal width 40 m) separated by corrugated vertical walls and alternately closed at the left and right ends. It is supplied to the slits alternately (striped) from the left and right directions, and then rises vertically in the slits. After exceeding the upper end of the slits, they contact each other in a laminar flow state, and then mix in a mixed state. It comes out of Sir 31.
- the organic phase and the aqueous phase flow in multiple layers that are alternately overlapped, and a pair of layers of the organic phase and the aqueous phase is a unit space, and this unit space is a minute space. Therefore, the organic phase and the aqueous phase supplied to the micromixer 31 flow through a plurality of micro spaces in the micromixer 31 in a laminar flow state while contacting each other in the presence of the catalyst.
- the micromixer 31 was heated to about 35 ° C. by the heating jacket 31a, and the pressure was adjusted by the back pressure valve 25 existing in the downstream line 23 in the same manner as in Example 1. Thereby, the inside of the micromixer 31 was maintained at about 35 ° C. and about 2 MPa.
- HFP was reacted with NaCIO by the catalytic action of TBAS to generate HFPO.
- the residence time of the fluid (including the organic and aqueous phases and optionally the gas phase) in the micromixer 31 was 1 second or less. Therefore, you can safely assume that the reaction time is less than 1 second.
- the recovered reaction mixture was allowed to stand to separate into an organic phase and an aqueous phase.
- the obtained organic phase was analyzed by gas chromatography, the conversion of HFP was about 100% and the selectivity for HFPO was about 85%. From these, the yield was about 85%.
- This comparative example relates to a batch reaction in a milliliter order reactor without using a minute space.
- a 200 mL capacity pressure vessel was used for the reactor.
- Hexafluoropropylene oxide obtained by the production method of the present invention can be used for the production of a fluorine-containing compound, for example, perfluorovinyl ether, and the lubricating oil is heated in the form of an oligomer. It can be used as a medium.
- a fluorine-containing compound for example, perfluorovinyl ether
- the lubricating oil is heated in the form of an oligomer. It can be used as a medium.
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Priority Applications (3)
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JP2008540996A JPWO2008050760A1 (ja) | 2006-10-24 | 2007-10-23 | ヘキサフルオロプロピレンオキシドの製造方法 |
US12/447,130 US20100016615A1 (en) | 2006-10-24 | 2007-10-23 | Process for production of hexafluoropropylene oxide |
EP07830372A EP2090572A1 (en) | 2006-10-24 | 2007-10-23 | Process for production of hexafluoropropylene oxide |
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JP2006288467 | 2006-10-24 | ||
JP2006-288467 | 2006-10-24 |
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EP (1) | EP2090572A1 (ja) |
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WO2010106865A1 (ja) * | 2009-03-18 | 2010-09-23 | ダイキン工業株式会社 | ヘキサフルオロプロピレンオキシドとヘキサフルオロプロピレンの分離方法 |
WO2010106942A1 (ja) | 2009-03-17 | 2010-09-23 | ダイキン工業株式会社 | ヘキサフルオロプロピレンオキシドの製造方法 |
WO2017002938A1 (ja) * | 2015-06-30 | 2017-01-05 | エム・テクニック株式会社 | 有機化合物の製造方法 |
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- 2007-10-23 CN CNA2007800396613A patent/CN101528719A/zh active Pending
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US9169225B2 (en) | 2009-03-17 | 2015-10-27 | Daikin Industries, Ltd. | Method for producing hexafluoropropylene oxide |
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EP2409970A4 (en) * | 2009-03-17 | 2012-08-29 | Daikin Ind Ltd | PROCESS FOR PREPARING HEXAFLUORO PROPYLENE OXIDE |
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US20120016142A1 (en) * | 2009-03-17 | 2012-01-19 | Kazuyoshi Ichihara | Method for producing hexafluoropropylene oxide |
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WO2017002938A1 (ja) * | 2015-06-30 | 2017-01-05 | エム・テクニック株式会社 | 有機化合物の製造方法 |
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Also Published As
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EP2090572A1 (en) | 2009-08-19 |
JPWO2008050760A1 (ja) | 2010-02-25 |
CN101528719A (zh) | 2009-09-09 |
US20100016615A1 (en) | 2010-01-21 |
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