WO2004018413A1 - Procede de sechage d'un derive de l'acide 2-alcoxypropionique fluore - Google Patents

Procede de sechage d'un derive de l'acide 2-alcoxypropionique fluore Download PDF

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Publication number
WO2004018413A1
WO2004018413A1 PCT/JP2003/007590 JP0307590W WO2004018413A1 WO 2004018413 A1 WO2004018413 A1 WO 2004018413A1 JP 0307590 W JP0307590 W JP 0307590W WO 2004018413 A1 WO2004018413 A1 WO 2004018413A1
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WIPO (PCT)
Prior art keywords
drying
acid derivative
fluorinated
alkoxypropionic acid
water
Prior art date
Application number
PCT/JP2003/007590
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English (en)
Japanese (ja)
Inventor
Kenji Ishii
Noriyuki Shinoki
Takuya Arase
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Daikin Industries, Ltd.
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Publication date
Application filed by Daikin Industries, Ltd. filed Critical Daikin Industries, Ltd.
Priority to JP2004530522A priority Critical patent/JP4013953B2/ja
Priority to AU2003241665A priority patent/AU2003241665A1/en
Publication of WO2004018413A1 publication Critical patent/WO2004018413A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/42—Separation; Purification; Stabilisation; Use of additives
    • C07C303/44—Separation; Purification

Definitions

  • the present invention relates to a method for removing water from a mixture of a fluorinated 2-alkoxypropionic acid derivative and water without denaturing the fluorinated propionic acid derivative.
  • Water-soluble fluorinated vinyl ethers having a terminal hydrophilic group can be used as such or after protecting the terminal hydrophilic group by fluorination or esterification or amidation / diimidation. It can be used to obtain a copolymer by polymerizing with a compound.
  • the obtained copolymer can have a salt-forming hydrophilic group, its use as an ion-exchange membrane in salt electrolysis, chemical sensors, separation membranes, fuel cells, etc. is being studied. It can be used as a polymer super-strong acid catalyst as it is, or for lithium batteries.
  • the mixture of the fluorinated 2-alkoxypropionic acid derivative and water tends to generate by-products in the drying step, and the once-formed by-product is fluorinated 2-alkoxypropionic acid. Since it is a salt of an organic compound similar in properties to the derivative, it is difficult to separate and purify the fluorinated 2-alkoxypropionic acid derivative from by-products by ordinary distillation and recrystallization methods. There has been a need for a method for removing water without altering the 2-alkoxypropionic acid derivative.
  • an object of the present invention is to efficiently remove water from a mixture of a fluorinated 2-alkoxypropionic acid derivative and water without denaturing a fluorinated 2-alkoxypropionic acid derivative. 0 near to provide a drying method that can
  • the present invention has the following general formula (I)
  • ⁇ represents an alkoxyl group, a halogen atom, 1 OM 1 or 1 OM 2 1/2
  • M 1 represents an alkali metal, a quaternary nitrogen or a hydrogen atom
  • M 2 represents an alkaline earth metal.
  • X represents a halogen atom
  • Y 1 and Y 2 are the same or different and each represents a fluorine atom, an elementary silicon atom, a perfluoroalkyl group or a cyclofluoroalkyl group
  • n represents an integer of 0 to 3.
  • Y 1 may be the same or different
  • m represents an integer of 1 to 5.
  • a fluorine-containing 2-alkoxypropionic acid derivative (hereinafter, referred to as “compound (I)”) represented by) is subjected to a drying step (2) after the drying step (1), followed by drying.
  • a method for drying a fluorine-containing 2-alkoxypropionic acid derivative comprising: The step (1) is performed at 90 ° C. or less until the amount of water exceeds 0.3% by mass and equal to or less than 10% by mass. Perform at 100 ° C or more until the amount becomes less than mass% And a method for drying a fluorinated 2-alkoxypropionic acid derivative.
  • the method for drying a fluorinated 2-alkoxypropionic acid derivative of the present invention is characterized by drying the above compound (I).
  • the compound (I) forms a mixture with water before being dried by the drying step (1) and the drying step (2) described below by the method for drying a fluorinated 2-alkoxypropionic acid derivative of the present invention. ing.
  • compound (I) mono-water mixture a mixture comprising the above compound (I) and water is referred to as "compound (I) mono-water mixture”.
  • the above “compound (I) mono-water mixture” is the one before the drying step (1), the one during the drying step (1), and the one before the drying step (2). It is a concept that includes things inside.
  • the compound (I) mono-water mixture may be a compound that is not dissolved in a liquid containing water as a main component of the compound (I), for example, an aqueous dispersion of the compound (I) or water. It may be an aqueous solution of the above compound (I) dissolved in a solvent containing as a main component.
  • the compound (I) -one water mixture is, for example, A in the above general formula (I) is 1 OM 1 or 1 OM 2 1/2 described later, it is dissolved in water or a solvent containing water as a main component. It may be an aqueous solution of the above compound (I), and preferably an aqueous solution of the above compound (I) dissolved in water.
  • the above-mentioned compound (I) mono-water mixture may be obtained by dissolving a low boiling organic solvent such as an alcohol which can be evaporated under the conditions in the method for drying a fluorinated 2-alkoxypropionic acid derivative of the present invention.
  • a low boiling organic solvent such as an alcohol which can be evaporated under the conditions in the method for drying a fluorinated 2-alkoxypropionic acid derivative of the present invention.
  • an alkoxyl group, a halogen atom is also one OM 1 shows an OM 2 1/2.
  • the alkoxyl group is not particularly limited, and includes, for example, a methoxy group, an ethoxy group, a propoxy group, an isopropoxy group and the like.
  • the halogen atom is any one of a fluorine atom, a chlorine atom, a bromine atom and an iodine atom. It may be.
  • M 1 represents an alkali metal, a quaternary nitrogen or a hydrogen atom.
  • the alkali metal may be any of Li, Na, K and Cs, but is preferably Na which is industrially inexpensive.
  • the above “quaternary nitrogen” is an atom consisting of a nitrogen atom and three groups to which this nitrogen atom is covalently bonded other than the oxygen atom [1 O—] in —OM 1 described above.
  • the quaternary nitrogen is not particularly limited, and examples thereof include NRiRSRSR 4 (R ⁇ R 2 , R 3 and R 4 are the same or different and represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms).
  • a salt may be formed with a hydroxide ion or the like, or the salt may be in an ionized state.
  • M 1 may be any of an alkali metal, a quaternary nitrogen or a hydrogen atom, but is preferably an alkali metal.
  • the M 2 represents an alkaline earth metal.
  • the alkaline earth metal may be any of Be, Mg, Ca and the like.
  • A is preferably one OM1 or _OM21 / 2 .
  • the compound (I) when in the above-mentioned A gar OM 1 or one OM 2 1/2, when cormorants row pyrolysis below as a post-step, decarboxylation proceeds easily.
  • X may be any of a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
  • Y 1 and Y 2 in the general formula (I) are the same or different and each represent a fluorine atom, a chlorine atom, a perfluoroalkyl group or a cyclofluoroalkyl group.
  • the above-mentioned perfluoroalkyl group is not particularly limited, and examples thereof include a trifluoromethyl group and a pentafluoroethyl group.
  • Said Y 1 is preferably a triflate Ruo Russia methyl, said Y 2 is preferably a fluorine atom.
  • N in the above general formula (I) represents an integer of 0 to 3.
  • the n Y 1 's may be the same or different.
  • n is preferably 0 or 1, and 0 More preferably, there is.
  • M in the above general formula (I) represents an integer of 1 to 5.
  • the m Y 2 may be different or may be identical derconnection. The larger m is, the stronger the strength as an acid is, but the number of hydrophilic groups per unit mass of the compound (I) is reduced. Therefore, the m is preferably 2.
  • Z in the general formula (I) represents a hydrophilic group.
  • the M 3 are, same as M 1 described above, preferably an inexpensive N a for industrial, said M 3 are preferably the same kind of metal as the M 1.
  • the M 4 is preferably a metal of the same kind as the above M 2.
  • the substituted ammonium group forms a salt with a conjugate base of a monovalent or divalent or higher valent mineral acid or fatty acid.
  • the conjugate base often exists in an ionized state from the substituted ammonium group.
  • the mineral acid is not particularly limited, and examples thereof include hydrochloric acid, phosphoric acid, sulfuric acid, and nitric acid.
  • the fatty acid is not particularly limited and includes, for example, formic acid, acetic acid, propionic acid and the like.
  • Z in the general formula (I) is preferably an S0 3 M 3 or one S0 3 M 4 1/2.
  • A is 1 OM 1 or 1 OM 2 1/2
  • Y 1 is a trifluoromethyl group
  • A is one OM, M 1 is Na, X is a fluorine atom, This is a more preferable method when n is 0, Y 2 is a fluorine atom, m is 2, Z is —S 0 3 M 3 , and M 3 is Na.
  • the method for obtaining the above compound (I) is not particularly limited, and for example, known methods and the like can be used.
  • the above compounds (I) for example, the following general formula
  • the above compound (a) can be produced by a conventionally known method.
  • sulfur trioxide with tetrafluoroethylene [TFE]
  • TFE tetrafluoroethylene
  • the neutralizing reagent is not particularly limited as long as it is a base, but is preferably an alkali metal hydroxide, and particularly preferably industrially inexpensive NaOH.
  • the neutralizing reagent is usually used after being dissolved in a solvent for the neutralizing reagent.
  • the solvent for the neutralizing reagent is usually water and Z or a water-soluble organic solvent, and water and alcohol are preferable.
  • the neutralization is preferably performed using at least 4 equivalents of an alkali metal hydroxide per 1 mol of the compound (a). When the amount of the neutralizing reagent is less than 4 equivalents relative to 1 mol of the compound (a), all of the S0 2 A 2 groups of the compound (a) do not become one S0 3 M 3 group.
  • n is 0 in the general formula for the compound (a)
  • a cyclic by-product may be generated during the subsequent thermal decomposition.
  • the neutralizing reagent be as small as possible within the above range.
  • the neutralization is performed by reacting at a temperature of 90 ° C. or lower for 1 to 48 hours in the presence of the neutralizing reagent. If the neutralization temperature exceeds 90 ° C., the compound (I) may be thermally decomposed. A preferred lower limit is 0 ° C, and a preferred upper limit is 80 ° C. If the reaction time of the neutralization is less than 1 hour, the neutralization may be insufficient. If the reaction time exceeds 48 hours, the neutralization reaction reaches an equilibrium state and the reaction does not proceed. The preferred lower limit is 3 hours and the preferred upper limit is 24 hours.
  • the reaction rate of conversion from one SO 2 A 2 group to one S0 3 M 3 salt It is preferable to continue stirring for several hours after the neutralization reaction system changes to neutral. Thereafter, if the neutralization reaction system has changed to acidic, it is preferable to adjust the neutralization reaction system to be neutral by adding a neutralization reagent.
  • the compound (I) When the compound (I) is obtained by the above-mentioned neutralization or saponification, it is obtained as a mixture of water in which the above-mentioned neutralization reagent is dissolved and water generated by the neutralization.
  • the compound (I) may be used as an aqueous solution as long as it is a mixture with water before drying, regardless of whether the compound (I) is formed through the above-described neutralization or saponification. It may be present or may not be dissolved in a liquid containing water as a main component.
  • the method for drying a fluorinated 2-alkoxypropionic acid derivative of the present invention is characterized in that the compound (I) is dried by performing a drying step (2) after the drying step (1).
  • drying the compound (I) means removing water from a mixture of the compound (I) and water.
  • the drying step (1) is performed at 90 ° C or less until the water content exceeds 0.3% by mass and is 10% by mass or less.
  • the above compound (I) has the following general formula
  • water in the drying step (1) and the drying step (2) described later means the amount of water in the compound (I) -one water mixture.
  • the drying step (1) is preferably performed at 60 ° C. or higher as long as the temperature is within the above range. If the temperature is lower than 60 ° C, drying may take a long time.
  • the drying step (1) is more preferably performed at a temperature of 70 ° C. or higher as long as the temperature is within the above range from the viewpoint of efficient drying. .
  • the drying time in the drying step (1) is preferably several seconds to 50 hours, although it depends on the drying temperature, the air volume during drying, the charged amount, and the like. If it exceeds 50 hours, it is not preferable in terms of economy.
  • the temperature is further lowered in order to precipitate a solid.
  • the solid is mainly composed of the compound (I).
  • the temperature is preferably lowered by 1 ° C. or more from the temperature before the temperature lowering, and more preferably to a temperature at which the solid precipitates.
  • the surface during which the drying of the compound (I) monohydrate mixture contained in the container or the like is to be performed is referred to as “on the way”, which is the time to perform the cooling.
  • the state of high viscosity is preferable, and the “state of high viscosity” is, for example, a state in which fluidity is extremely reduced.
  • the surface of the compound (I) mono-aqueous mixture has a high viscosity, if the temperature is lowered to a temperature at which a solid precipitates, the water evaporates from the gap between the solids, so It can be dried.
  • drying is performed at a constant temperature, the surface of the above-mentioned compound (I) mono-water mixture is in a high-viscosity state, and no solid is formed, so the inside may not be dried.
  • the temperature is preferably returned to the temperature before the cooling and drying is continued.
  • the process of once lowering the temperature and then raising it again may be repeated.
  • the method for lowering the temperature is not particularly limited, and examples thereof include a method of taking out from a dryer and the like.
  • the drying step (1) it is preferable to further perform mechanical pulverization of the precipitated solid and / or stirring of the compound (I) -aqueous mixture whose surface has a high viscosity.
  • the compound having a high water content is obtained by mechanically pulverizing the surface of the above-mentioned compound (I) mono-aqueous mixture from which a solid is precipitated and stirring the mixture or stirring the above-mentioned compound (I) mono-aqueous mixture having a high viscosity.
  • the above compound (I) It can be exposed on the surface of an object to promote the evaporation of water.
  • the solid on the surface may be cracked by cooling, the solid may be cracked by mechanical force, or both may be used in combination.
  • the above-mentioned grinding and the above-mentioned stirring may be carried out by a human using a spatula or the like, or a mixer such as a mixer with a conical screw capable of heating and flowing moisture and having a stirrer therein, a kind of kneader, etc. May be used.
  • the solid deposited on the container wall surface due to the above-mentioned temperature drop may be scraped off.
  • the drying step (2) is performed at a temperature of 100 ° C. or more until the water content becomes 0.2% by mass or less.
  • the temperature is lower than 100 ° C, the above compound (I) has a high hygroscopicity, so the water content is 0.2 mass. It is difficult to make it less than / 0 .
  • a more preferred lower limit is 110 ° C.
  • a preferred upper limit is 200 ° C. When the temperature exceeds 200 ° C, the compound (I) is easily decomposed.
  • the drying time in the drying step (2) depends on the drying temperature, but is preferably several seconds to 20 hours. Exceeding 20 hours is not preferable in terms of economy.
  • the dryer used in the drying step (1) and the drying step (2) is not particularly limited, and includes, for example, a circulating hot air dryer, an infrared dryer, a vacuum dryer, a rotary dryer, a dryer with a stirrer, Spray dryers and the like can be mentioned. However, care should be taken when drying the above compound (I) with the above vacuum dryer because foaming may occur because the above compound (I) has a surfactant-like molecular structure. .
  • the compound (I) When the compound (I) is to be dried by the hot air circulating dryer or the rotary dryer, the surface of the compound (I) -one water mixture becomes a high viscosity state in the drying step (1), (I) Since the inside of the one-water mixture may not be sufficiently dried, it is preferable to perform the above-mentioned temperature lowering or stirring.
  • the method for drying a fluorinated 2-alkoxypropionic acid derivative according to the present invention is characterized in that drying is performed in two stages of the drying step (1) and the drying step (2).
  • drying step (1) it is difficult to reduce the water content to 3% by mass or less, for example, 0.2% by mass or less, even if dried for a long time at a temperature of 90 ° C or less, for example, 80 ° C.
  • the water content is increased by raising the temperature to a temperature of 100 ° C. or higher, preferably 110 ° C. to 200 ° C. Efficient drying in a relatively short time until is reduced to 0.1% by mass or less be able to.
  • the compound (I) is dried using the method for drying a fluorinated 2-alkoxypropionic acid derivative of the present invention, and then thermally decomposed by heating, for example, to form a water-soluble fluorinated butyl ether such as sodium butyl ether sulfonate.
  • a water-soluble fluorinated butyl ether such as sodium butyl ether sulfonate.
  • the reaction time of the thermal decomposition depends on the temperature at which the thermal decomposition is performed, but is preferably 10 to 600 minutes after the reaction temperature is reached. If the reaction time is less than 10 minutes, thermal decomposition may be insufficient. A more preferred lower limit is 30 minutes, and a more preferred upper limit is 300 minutes.
  • the organic solvent (A) is an organic solvent having a coordinating ability to the alkali metal or alkaline earth metal ion of the fluorinated 2-alkoxypropionic acid derivative.
  • a solvent comprising an aprotic organic polar solvent is preferable.
  • aprotic organic polar solvent examples include ether solvents, sulfolane, hexamethylphosphoric triamide, acetonitrile, dimethylformamide, dimethylsulfoxide, tetramethylurea, and the like.
  • a glyme solvent is preferred.
  • diethylene glycol dimethyl ether is more preferred.
  • a water-soluble fluorinated vinyl ether such as a fluorinated sulfoalkyl bier ether represented by the following formula is obtained.
  • the water-soluble fluorinated vinyl ether forms a mixture with the organic solvent (A) and the inorganic salt.
  • the inorganic salt is formed by the thermal decomposition It is a by-product generated, and examples thereof include sodium fluoride, potassium fluoride, and cesium fluoride. Therefore, the water-soluble fluorinated bier ether is preferably purified so as to remove the organic solvent (A) and the inorganic salt.
  • the above-mentioned purification can be preferably applied.
  • the above-mentioned water-soluble fluorine-containing ether is mixed with an organic solvent (B) by mixing an aqueous solution comprising the above-mentioned organic solvent (A) and an inorganic salt to remove the above-mentioned organic solvent (A).
  • the mixture obtained by the first purification is mixed with an organic solvent (C) and the inorganic salt is separated by filtration (hereinafter, referred to as "second purification"). It is preferable to perform this.
  • the organic solvent (B) is separated into two phases when mixed with an equal amount of water at 25 ° C, and is an organic solvent in which the solubility of the water-soluble fluorinated vinyl ether is 10% by mass or less. Yes, for example, those having a relative dielectric constant of 4 to 10 are preferable.
  • the organic solvent (C) is an organic solvent that does not dissolve the inorganic salt but dissolves the water-soluble fluorinated butyl ether, and includes, for example, ketones such as acetone; esters such as ethyl acetate; Alcohols are preferred.
  • the amount of the organic solvent (C) depends on the solubility of the mixture of the water-soluble fluorinated beer ether and the inorganic salt in the organic solvent (C). Preferably it is ⁇ 100 parts by weight. A more preferred lower limit is 500 parts by weight, and a more preferred upper limit is 500 parts by weight.
  • the purification of the water-soluble fluorinated vinyl ether it is preferable to perform drying during the purification after the first purification. By performing the drying during the purification, the crystals of the inorganic salt can be grown, and the second purification can be facilitated.
  • the drying at the time of each purification is preferably performed at a drying temperature of 25 to 200 ° C.
  • the water-soluble fluorinated bierether obtained by the above thermal decomposition can be used as it is or after the terminal hydrophilic group is protected by fluorination or esterification or amidation / imidation, as a monomer. It can be used to obtain a copolymer with an olefin such as yne.
  • the water-soluble fluorinated vinyl ether is chlorinated after the purification, It is preferable to obtain a fluorine-containing vinyl ether having a black end and fluorinating the same to obtain a fluorine-containing vinyl ether having a fluorine terminal.
  • the chlorination is preferably performed by reacting the water-soluble fluorinated vinyl ether with a chlorinating reagent.
  • the chlorinating reagent includes PC 1 5, PC 1 3, S0 2 C 1 or the like, PC 1 5 is preferred.
  • PC 1 5 for use as the chlorinating reagent it is preferable to use the water-soluble fluorine-containing vinyl ether 1 mol per 1 equivalent or more.
  • the fluorinated vinyl ether having a chloro terminal obtained by performing the above chlorination can be fluorinated by reacting with a conventionally known method, for example, NaF, KF or the like in a sulfolane solvent.
  • copolymer of the water-soluble fluorinated vinyl ether obtained by the above-mentioned thermal decomposition and an olefin such as fluoroolefin is suitably used for ion exchange membranes, catalysts, lithium batteries and the like.
  • the pressure was increased to 0.2 MPa, an exothermic reaction started immediately. Therefore, the reaction was continued for 3 hours under a pressure of 1 to 0.2 MPa while adjusting the temperature to 20 to 40 ° C. After that, the reaction was interrupted and the residual gas was released because the pressure drop rate became low.
  • the powder A (1 g) was dispersed in 14 g of ethylene glycol dimethyl ether, the supernatant was measured by Karl Fischer titration, and the water content in ethylene glycol dimethyl ether measured separately was subtracted. Powder water The minute was 0.5% by mass.
  • Powder A (1.2 kg) obtained by drying the above compound (i) at 80 ° C for 36 hours is further charged into a hot air circulating drier maintained at 120 ° C, and dried for 12 hours. I got body B. Thereafter, the water content of the powder B was measured by the same method as that for the powder A, and it was 0.1% by mass.
  • the compound obtained by a two-step drying process as described above the powder (i) was dissolved in water, 19 F- was measured NMR (reference material: CFC 1 3) between the roller, the compound (i one C (O) CF1 (CF 3 ) O- underlined from fluorine atom of ⁇ _ 1 26. 5 p pm near the peak and the following compound in) (ii) CF 3 CFHOCF 2 CF 2 S0 3 Na
  • Example 120 Drying was performed in the same manner as in Example 1 except that drying at 20 ° C. was omitted, and the water content was measured in the same manner as in Example 1.
  • the water content of the powder of the compound (i) was 0.5% by mass, and it was confirmed that the compound (ii) was not formed at all. Comparative Example 2
  • Example 1 After drying at 80 ° C for 12 hours and stirring at 80 ° C, the whole became a syrup. The resultant was further dried for 24 hours, and the water content was measured in the same manner as in Example 1. The water content was 0.8% by mass, and it was confirmed that the compound (ii) was not formed at all.
  • Reference Example 1 The thermal decomposition of a fluorinated 2-alkoxypropionic acid derivative and the purification of the water-soluble fluorinated butyl ether obtained by this thermal decomposition

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne un procédé de séchage d'un dérivé de l'acide 2-alcoxypropionique fluoré, selon lequel on soumet séquentiellement à une étape de séchage (1) et à une étape de séchage (2) un dérivé de l'acide 2-propionique représenté par la formule générale (1), (dans laquelle A représente un alcoxy, etc.; X représente un atome halogène; Y1 et Y2 peuvent être identiques ou différents l'un de l'autre et représenter un atome de fluor, etc.; n est un entier de 0 à 3; m est un entier de 1 à 5; et Z représente un groupe hydrophile), lequel procédé est caractérisé en ce que l'étape de séchage (1) s'effectue à une température inférieure ou égale à 90 °C jusqu'à l'obtention d'une teneur en eau comprise entre 0,3 % massique et 10 % massique maximum, tandis que l'étape de séchage (2) s'effectue à une température supérieure ou égale à 100 °C jusqu'à l'obtention d'une teneur en eau inférieure ou égale à 0,2 % massique.
PCT/JP2003/007590 2002-06-14 2003-06-16 Procede de sechage d'un derive de l'acide 2-alcoxypropionique fluore WO2004018413A1 (fr)

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JP2004530522A JP4013953B2 (ja) 2002-06-14 2003-06-16 含フッ素２−アルコキシプロピオン酸誘導体乾燥方法
AU2003241665A AU2003241665A1 (en) 2002-06-14 2003-06-16 Method of drying fluorinated 2-alkoxypropionic acid derivative

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111072627A (zh) * 2019-12-26 2020-04-28 浙江巨化技术中心有限公司 一种全氟烷基磺内酯的合成方法
JP2021031397A (ja) * 2019-08-16 2021-03-01 旭化成株式会社 スルホン酸基含有モノマーの製造方法

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6274677B1 (en) * 1997-03-31 2001-08-14 Daikin Industries Ltd. Process for the producing perfluorovinyl ethersulfonic acid derivatives and copolymer of the same

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6274677B1 (en) * 1997-03-31 2001-08-14 Daikin Industries Ltd. Process for the producing perfluorovinyl ethersulfonic acid derivatives and copolymer of the same

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2021031397A (ja) * 2019-08-16 2021-03-01 旭化成株式会社 スルホン酸基含有モノマーの製造方法
JP7258694B2 (ja) 2019-08-16 2023-04-17 旭化成株式会社 スルホン酸基含有モノマーの製造方法
CN111072627A (zh) * 2019-12-26 2020-04-28 浙江巨化技术中心有限公司 一种全氟烷基磺内酯的合成方法

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