WO2012105586A1 - Perfluorobutane sulfonyl fluoride, potassium perfluorobutane sulfonate salt, and method for producing perfluorobutane sulfonyl fluoride - Google Patents

Perfluorobutane sulfonyl fluoride, potassium perfluorobutane sulfonate salt, and method for producing perfluorobutane sulfonyl fluoride Download PDF

Info

Publication number
WO2012105586A1
WO2012105586A1 PCT/JP2012/052208 JP2012052208W WO2012105586A1 WO 2012105586 A1 WO2012105586 A1 WO 2012105586A1 JP 2012052208 W JP2012052208 W JP 2012052208W WO 2012105586 A1 WO2012105586 A1 WO 2012105586A1
Authority
WO
Grant status
Application
Patent type
Prior art keywords
perfluorobutane
sulfonyl fluoride
perfluoro
sulfolane
hydroxide
Prior art date
Application number
PCT/JP2012/052208
Other languages
French (fr)
Japanese (ja)
Inventor
博之 八柳
武志 神谷
常俊 本田
Original Assignee
三菱マテリアル株式会社
三菱マテリアル電子化成株式会社
Priority date (The priority date 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 date listed.)
Filing date
Publication date

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C303/00Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
    • C07C303/42Separation; Purification; Stabilisation; Use of additives
    • C07C303/44Separation; Purification

Abstract

This perfluorobutane sulfonyl fluoride has a perfluorosulfolane content of 100 ppm or less on a mass basis. This potassium perfluorobutane sulfonate salt has a potassium 1,1,2,2,3,3,4,4-octafluorobutane sulfonate salt content of 100 ppm or less on a mass basis. In this method for producing perfluorobutane sulfonyl fluoride, perfluorosulfolane is removed by adding an aqueous solution of an alkali metal hydroxide into the perfluorobutane sulfonyl fluoride.

Description

Perfluorobutane sulfonyl fluoride, potassium perfluorobutane sulfonate and a method for manufacturing perfluorobutane sulfonyl fluoride,

The present invention is highly pure perfluorobutane sulfonyl fluoride, and method of manufacturing the same, and a potassium perfluorobutane sulfonate salt prepared using perfluorobutane sulfonyl fluoride. More particularly, the method of manufacturing perfluorobutane sulfonyl fluoride to a perfluoro sulfolane as a by-product can be efficiently removed, perfluorobutane sulfonyl fluoride, and a perfluorobutane sulfonic acid potassium salt.
The present application, on February 4, 2011, claiming priority based on Japanese Patent Application No. 2011-022587, filed in Japan, the contents of which are incorporated here.

Perfluorobutane sulfonate (in CF 3 CF 2 CF 2 CF 2 SO 3 M, wherein, M is a cation) is a semiconductor and a photoacid generator for photolithography used during manufacturing, the flame retardant polycarbonate resin , used in the resin of the conductive agent and the like. The perfluorobutane sulfonate is prepared using perfluorobutane sulfonyl fluoride (CF 3 CF 2 CF 2 CF 2 SO 2 F) as a raw material. Perfluorobutane sulfonyl fluoride is produced by electrolytic fluorination of sulfolane (tetrahydrothiophene-1,1-dioxide). The electrochemical fluorination (ECF:, Electrochemical fluorination) is represented by the following reaction formula (1).

Figure JPOXMLDOC01-appb-C000001

However, in the course of the electrochemical fluorination, by the following reaction formula (2), perfluoro sulfolane (perfluoro tetrahydrothiophene-1,1-dioxide) is by-produced as an impurity, the impurity is present in the perfluorobutane sulfonyl fluoride It is contained several% by weight.

Figure JPOXMLDOC01-appb-C000002

To purify the perfluorobutane sulfonyl fluoride, first, a distillation. However, perfluorobutane sulfonyl fluoride and perfluoro sulfolane are both boiling points is substantially equal to about 65 ° C., there is a problem that it is difficult to remove by distillation perfluoro sulfolane.

As a method for removing a perfluoroalkyl sulfolane, a method of using a buffer solution of dipotassium hydrogenphosphate and potassium phosphate has been reported (Non-Patent Document 1). However, this method requires 4 days to remove the perfluoro sulfolane. Further, removal of perfluoroalkyl sulfolane also not sufficient, phosphorus due to a buffered aqueous solution to be used for further removal is mixed as a new impurity. For example, when used in photoresists for semiconductor lithography, since phosphorus as an impurity is not allowed, the removal method of using the aqueous buffer solution is not appropriate.

Michael er cable Vogel (Michael A.K.Vogel), and two others, Shinretto (SYNLETT), (the United States), 2007, Vol. 18, p. 2907-2911

The present invention is to purify the perfluorobutane sulfonyl fluoride, to remove the perfluoro sulfolane, and aims to obtain a perfluorobutane sulfonyl fluoride with high purity. Therefore, the present invention has an object to provide a highly pure perfluorobutane sulfonyl fluoride, pure perfluorobutane sulfonic acid potassium salt and highly pure perfluorobutane sulfonyl fluoride manufacturing method of.

High purity perfluorobutanesulfonyl fluoride of the present invention, potassium perfluorobutane sulfonate, and the gist of the production method of perfluorobutane sulfonyl fluoride shown below.
(1) The content of perfluoro sulfolane is, perfluorobutanesulfonyl, characterized in that at 100ppm or less by weight fluoride.
(2) 1,1,2,2,3,3,4,4 content of octafluorobutane sulphonic acid potassium salt, perfluorobutane sulfonic acid potassium salt, characterized in that at 100ppm or less by weight.
(3) during perfluorobutane sulfonyl fluoride, perfluoro butane sulfonyl fluoride method for producing characterized in that the removal of the aqueous solution perfluoro sulfolane by adding an alkali metal hydroxide.
(4) the alkali metal hydroxide is sodium lithium hydroxide, hydroxide, potassium hydroxide, rubidium hydroxide, and at least one selected from the group consisting of cesium hydroxide (3) perfluoro according method for producing butane sulfonyl fluoride.
(5) the perfluoroalkyl sulfolane: 1 moles method of the alkali metal additive amount of the hydroxide is a ratio of 1 to 3 moles (3) or (4) perfluorobutane sulfonyl fluoride according.
(6) an aqueous solution of the alkali metal hydroxide with respect to 100 parts by weight, the amount of the alkali metal hydroxide is 0.1 to 20 parts by mass The above (3) to according to any one of (5) manufacturing method of perfluorobutane sulfonyl fluoride.

According to an aspect of the present invention (1), it can provide a high purity perfluorobutanesulfonyl fluoride. In the conventional manufacturing method, it is difficult to manufacture in this way a highly pure perfluorobutane sulfonyl fluoride.

According to aspect (3) of the present invention, a perfluorobutane sulfonyl fluoride with high purity, for example, can be easily produced in a short time of about 1-2 hours.

It will be specifically described based on an embodiment of the present invention. The unit% showing the content unless otherwise indicated, are by weight.

[Perfluorobutane sulfonyl fluoride, potassium perfluorobutane sulfonate]
Perfluorobutane sulfonyl fluoride of the present embodiment, the content of the perfluoro sulfolane, characterized in that at 100ppm or less by weight. Further, potassium perfluorobutane sulfonate salts of the present embodiment, 1,1,2,2,3,3,4,4-octafluoro-butane sulfonic acid potassium salt prepared using perfluorobutane sulfonyl fluoride as a raw material content, characterized in that at 100ppm or less by weight.

Perfluoro sulfolane in perfluorobutane sulfonyl fluoride is generated in the above-mentioned reaction formula (2).

Perfluorobutane sulfonyl fluoride, for example, when reacted with potassium hydroxide to produce a perfluorobutane sulfonic acid potassium salt, also react with potassium hydroxide perfluoro sulfolane present in the perfluorobutane sulfonyl fluoride. At this time, by the following reaction formula (3), one CF 2 -S bond in perfluoro sulfolane impurities generated by cleavage. The impurity 1,1,2,2,3,3,4,4 a octafluorobutane acid potassium salt (HCF 2 CF 2 CF 2 CF 2 SO 3 K).

Figure JPOXMLDOC01-appb-C000003

1,1,2,2,3,3,4,4 potassium octafluorobutane sulfonate in the potassium perfluorobutane sulfonate is derived from perfluoro sulfolane present in the perfluorobutane sulfonyl fluoride as a raw material . Therefore, by suppressing the formation of perfluoro sulfolane in perfluorobutane sulfonyl fluoride, 1,1,2,2,3,3,4,4-octafluoro-butane sulfonic acid potassium salt in the potassium perfluorobutane sulfonate it is possible to prevent the formation of.

1,1,2,2,3,3,4,4 content of octafluorobutane sulphonic acid potassium salt, if it is 100ppm or less, potassium perfluorobutane sulfonate, the impurity content to be used in semiconductor manufacture it is useful as a small raw material for photoacid generator for photolithography with. Here, 1,1,2,2,3,3,4,4 quantification of octafluorobutane sulphonic acid potassium salt is performed by @ 19 F-NMR and LC-MS. Furthermore, when analyzing perfluoro sulfolane is performed by gas chromatography (GC).

Manufacturing method of perfluorobutane sulfonyl fluoride]
Manufacturing method of perfluorobutane sulfonyl fluoride of the present embodiment, in the perfluorobutane sulfonyl fluoride, characterized by purifying by adding an aqueous solution of an alkali metal hydroxide. According to the manufacturing method (Purification Method), the content of perfluoro sulfolane in perfluorobutane sulfonyl fluoride, 1 to 2 hours, it is possible to 100ppm or less. Hereinafter, the perfluorobutane sulfonyl fluoride containing a perfluoroalkyl sulfolane as an impurity, the reaction that occurs by adding an aqueous solution of an alkali metal hydroxide, alkali metal, the case of using potassium.

And perfluorobutane sulfonyl fluoride, perfluoro sulfolane are both water-insoluble. Here, the addition of an aqueous solution of potassium hydroxide, at reaction temperatures 0 ~ 50 ° C. (preferably 20 ~ 30 ° C.), perfluorobutane sulfonyl fluoride does not react with potassium hydroxide, no change. On the other hand, perfluoro sulfolane is reacted with potassium hydroxide, by the above reaction formula (3), the water-soluble 1,1,2,2,3,3,4,4 octafluoro-butane sulfonic acid potassium salt is produced It is dissolved in an aqueous solution of potassium hydroxide. Scheme (3) reacting the completion, further 1,1,2,2,3,3,4,4 octafluoro-butane sulfonic acid potassium salt, after it has finished dissolved in an aqueous solution of potassium hydroxide, and perfluorobutane sulfonyl fluoride, an aqueous solution of potassium hydroxide containing 1,1,2,2,3,3,4,4 octafluoro-butane sulfonic acid potassium salt, layers separated. Perfluorobutane sulfonyl fluoride in the lower layer, an aqueous solution of potassium hydroxide in the upper layer, split. Therefore, by only the lower layer separated, pure perfluorobutane sulfonyl fluoride is obtained.

Alkali metal hydroxide, preferably lithium hydroxide, sodium hydroxide, potassium hydroxide, is at least one selected from the group consisting of rubidium hydroxide, and cesium hydroxide, in combination with two or more it may be.

Aqueous solution of alkali metal hydroxide with respect to 100 parts by weight, the amount of alkali metal hydroxide is preferably 0.1 to 20 parts by weight, and more preferably 1 to 5 parts by weight. The ratio of the alkali metal hydroxide is less than 0.1 part by weight, not observed purification effect. If the ratio of the alkali metal hydroxide is more than 20 parts by mass is not preferable because the decomposition of perfluorobutane sulfonyl fluoride occurs.

In the removal of perfluoro sulfolane, perfluoro sulfolane: relative to 1 mol, the amount of alkali metal hydroxide (ratio) is preferably from 1 to 10 moles, more preferably 2 to 5 moles. If the ratio of the alkali metal hydroxide is less than 1 mol, the reaction formula (3) reaction purifying effect does not complete is not obtained for. Be greater than the ratio of 10 moles of alkali metal hydroxide, remarkable effect can not be obtained.

Addition of an aqueous solution of an alkali metal hydroxide to perfluorobutane sulfonyl fluoride may be a known method is not particularly limited. However, in order to retrieve the perfluorobutane sulfonyl fluoride of the lower separated after purification easy it is preferably carried out in for example a separatory funnel and the like. An example of conditions of the reaction, while stirring the appropriate mixed solution, at room temperature, and then be reacted for 1-2 hours. The reaction conditions, the amount of perfluoro sulfolane that is contained in the perfluorobutane sulfonyl fluoride, the size of the batch to react (the amount of raw material), the intensity or the like of agitation, may be appropriately determined.

Manufacturing method of perfluorobutane sulfonic acid potassium salt]
Perfluorobutane sulfonyl fluoride as a raw material, potassium perfluorobutane sulfonate can be prepared by the following reaction formula (4).
C 4 F 9 SO 2 F + 2KOH → C 4 F 9 SO 3 K + KF + H 2 O (4)

Specifically, by reacting perfluorobutanesulfonyl fluoride with aqueous potassium hydroxide, the resulting perfluorobutane sulfonate potassium salt is cooled and crystallized. Then, filtered crystallization has been perfluorobutane sulfonate potassium salt, and dried. It can be obtained potassium perfluorobutane sulfonate as described above.

Perfluorobutane sulfonyl fluoride: relative to 1 mol, the molar ratio of potassium hydroxide is preferably 2 to 3 moles, 2 moles being particularly preferred.

Aqueous solution of potassium hydroxide with respect to 100 parts by weight, the amount of potassium hydroxide is preferably 20 to 70 parts by mass, particularly preferably 20 parts by mass.

The reaction temperature of the reaction formula (4) is 50 ~ 100 ° C., particularly preferably from 80 ° C.. The reaction time of reaction formula (4) is 10 to 50 hours, thereby to complete the reaction.

The resulting perfluorinated sulfonic acid potassium salt was cooled, the method is crystallized perfluorosulfonic acid potassium salt, and filtered crystallization has been perfluorobutane sulfonate potassium salt, a method of drying may be a known method, in particular but it is not limited.

Above, it is possible to manufacture a perfluorobutane sulfonic acid potassium salt of the present embodiment.

The following examples, but the present embodiment will be described in detail, the present embodiment is not limited thereto.

Example 1
Perfluorobutanesulfonyl containing perfluoro sulfolane 1 wt% fluoride: a 50 g, was placed in a polyethylene bottle 100 cm 3. Next, 1 wt% aqueous potassium hydroxide solution: put 21g. Was stirred at room temperature for 1 hour, then separated the lower layer, perfluorobutane sulfonyl fluoride: was obtained 49 g.

The resulting perfluorobutane sulfonyl fluoride and gas chromatography (GC) analysis. As a result, the content of perfluoro sulfolane was less than 100 ppm. Incidentally, 100 ppm is the detection lower limit of perfluoro sulfolane in GC.

Example 2
1 wt% aqueous solution of potassium hydroxide: except for using 11g, the same procedure as in Example 1, perfluorobutane sulfonyl fluoride: was obtained 49 g. The resulting perfluorobutane sulfonyl fluoride and GC analysis. As a result, the content of perfluoro sulfolane was less than 100 ppm.

Example 3
1 wt% aqueous solution of potassium hydroxide except that 31g was used, the same procedure as in Example 1, perfluorobutane sulfonyl fluoride: was obtained 49 g. The resulting perfluorobutane sulfonyl fluoride and GC analysis. As a result, the content of perfluoro sulfolane was less than 100 ppm.

Example 4
Instead of 1 wt% aqueous solution of potassium hydroxide, 1% by weight sodium hydroxide aqueous solution: except for using 15 g, in the same manner as in Example 1, perfluorobutane sulfonyl fluoride: was obtained 49 g. The resulting perfluorobutane sulfonyl fluoride and GC analysis. As a result, the content of perfluoro sulfolane was less than 100 ppm.

[Example 5]
1 wt% aqueous solution of potassium hydroxide: except for using 42g, the same procedure as in Example 1, perfluorobutane sulfonyl fluoride: was obtained 49 g. The resulting perfluorobutane sulfonyl fluoride and GC analysis. As a result, the content of perfluoro sulfolane was less than 100 ppm.

[Reference Example 1]
1 wt% aqueous solution of potassium hydroxide: except for using 9g, the same procedure as in Example 1, perfluorobutane sulfonyl fluoride: was obtained 49 g. The resulting perfluorobutane sulfonyl fluoride and GC analysis. As a result, the content of perfluoro sulfolane was 3000 ppm.

Comparative Example 1
Instead of 1 wt% aqueous solution of potassium hydroxide, 1 wt% potassium carbonate (K 2 CO 3) solution: except that 21g was used, in the same manner as in Example 1, perfluorobutane sulfonyl fluoride: was obtained 50 g. The resulting perfluorobutane sulfonyl fluoride and GC analysis. As a result, the content of perfluoro sulfolane was 1%.

Comparative Example 2
Instead of 1 wt% aqueous solution of potassium hydroxide, 10 wt% sulfuric acid: except for using 21g, in the same manner as in Example 1, perfluorobutane sulfonyl fluoride: was obtained 50 g. The resulting perfluorobutane sulfonyl fluoride and GC analysis. As a result, the content of perfluoro sulfolane was 1%.

Comparative Example 3
Instead of 1 wt% potassium hydroxide aqueous solution, a mixed aqueous solution 21g of 0.5 wt% dipotassium hydrogen phosphate and potassium phosphate 0.5% by weight, in the same manner as in Example 1, perfluorobutane sulfonyl fluoride : to give a 50g. The resulting perfluorobutane sulfonyl fluoride and GC analysis. As a result, the content of perfluoro sulfolane was 9500Ppm.

Example 6
20 wt% aqueous potassium hydroxide: and 15 g, perfluorobutane sulfonyl fluoride of less than 100ppm perfluoro sulfolane content in Example 1: 8 g, was placed in a 100 cm 3 flask. The mixture was stirred for 24 hours at 80 ° C.. Then cooled to 20 ° C., crystals were filtered. The obtained crystals were dried under reduced pressure, perfluorobutane sulfonic acid potassium salt: to give a 8 g. The content of the obtained in perfluorobutane sulfonate potassium salt 1,1,2,2,3,3,4,4-octafluoro-butane sulfonic acid potassium salt was 100ppm or less.

Comparative Example 4
As perfluorobutanesulfonyl fluoride, except that perfluoro sulfolane content produced in Comparative Example 1 was used as the 10000 ppm, in the same manner as in Example 6, potassium perfluorobutane sulfonate: was obtained 8 g. Content of the resulting perfluorobutane sulfonic acid potassium salt 1,1,2,2,3,3,4,4-octafluoro-butane sulfonic acid potassium salt was 9000 ppm.

As described above, in all of Examples 1-5, the content of perfluoro sulfolane in perfluorobutane sulfonyl fluoride was less than 100 ppm. In contrast, perfluoro sulfolane: relative to 1 mol, the amount of potassium hydroxide in Reference Example 1 is about 0.84 moles, content of perfluoro sulfolane in perfluorobutane sulfonyl fluoride was 3000 ppm. Further, in all of Comparative Examples 1 to 3 not using an aqueous solution of an alkali metal hydroxide, a content of perfluoro sulfolane of about 1% in Bae Le perfluorobutane sulfonyl fluoride, it can be removed perfluoro sulfolane There was no. Incidentally, perfluoro sulfolane: 1 ratio of potassium hydroxide to moles is Example 1, about 1.95, Example 2, about 1.05, Example 3, about 2.89, Example in 4 approximately 3.95 it is.

In Example 6 perfluoroalkyl sulfolane content using perfluorobutane sulfonyl fluoride of less than 100 ppm, 1,1,2,2,3,3,4,4 content of octafluorobutane sulphonic acid potassium salt It was 100ppm or less. In contrast, in Comparative Example 4 perfluoroalkyl sulfolane content using perfluorobutane sulfonyl fluoride of 10000 ppm, 1,1,2,2,3,3,4,4-containing octafluorobutane acid potassium salt the amount was 9000ppm.

The manufacturing method of perfluorobutane sulfonyl fluoride of the present embodiment, a short time can be removed perfluoro sulfolane, it is possible to obtain a perfluorobutane sulfonyl fluoride with high purity. Therefore, in the present embodiment can provide a highly pure perfluorobutane sulfonyl fluoride, and pure perfluorobutane sulfonate synthesized from the perfluorobutane sulfonyl fluoride. Perfluorobutane sulfonate of the present embodiment is a high purity, raw materials and of the photoacid generator for photolithography used in manufacturing semiconductors, a flame retardant polycarbonate resin, for applications such as resin conductive agent, it is very useful.

Claims (6)

  1. The content of perfluoro sulfolane is, perfluorobutanesulfonyl, characterized in that at 100ppm or less by weight fluoride.
  2. 1,1,2,2,3,3,4,4 content of octafluorobutane sulphonic acid potassium salt, perfluorobutane sulfonic acid potassium salt, characterized in that at 100ppm or less by weight.
  3. During perfluorobutane sulfonyl fluoride, perfluoro butane sulfonyl fluoride method for producing characterized in that the removal of the aqueous solution perfluoro sulfolane by adding an alkali metal hydroxide.
  4. Wherein the alkali metal hydroxide is lithium hydroxide, sodium hydroxide, potassium hydroxide, perfluorobutanesulfonyl fluorimeter according to claim 3 is at least one selected from the group consisting of rubidium hydroxide, and cesium hydroxide manufacturing method of de.
  5. The perfluoro sulfolane: relative to 1 mole, perfluorobutane sulfonyl fluoride method as claimed in claim 3 addition amount is a ratio of 1 to 10 moles of the alkali metal hydroxide.
  6. The alkali metal hydroxide aqueous solution with respect to 100 parts by weight, perfluorobutane sulfonyl fluoride method as claimed in claim 3 amount of the alkali metal hydroxide is 0.1 to 20 parts by weight.
PCT/JP2012/052208 2011-02-04 2012-02-01 Perfluorobutane sulfonyl fluoride, potassium perfluorobutane sulfonate salt, and method for producing perfluorobutane sulfonyl fluoride WO2012105586A1 (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
JP2011-022587 2011-02-04
JP2011022587 2011-02-04

Publications (1)

Publication Number Publication Date
WO2012105586A1 true true WO2012105586A1 (en) 2012-08-09

Family

ID=46602793

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2012/052208 WO2012105586A1 (en) 2011-02-04 2012-02-01 Perfluorobutane sulfonyl fluoride, potassium perfluorobutane sulfonate salt, and method for producing perfluorobutane sulfonyl fluoride

Country Status (2)

Country Link
JP (1) JP6023432B2 (en)
WO (1) WO2012105586A1 (en)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002038288A (en) * 2000-06-28 2002-02-06 Bayer Ag Method for producing completely fluorinated organic compound with electrochemical fluorination
JP2009179836A (en) * 2008-01-30 2009-08-13 Mitsubishi Materials Corp Method of absorbing perfluoroalkane sulfonyl fluoride

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2319078B2 (en) * 1973-04-16 1976-06-24 A process for the manufacture of practically fluoride-free perfluoroalkanesulfonates
JP3030661B2 (en) * 1991-03-06 2000-04-10 株式会社トーケムプロダクツ Method of extracting the perfluoroalkylsulfonic acid fluoride
JP2001322975A (en) * 2000-05-16 2001-11-20 Dainippon Ink & Chem Inc Method for producing perfluoroalkylsulfonic acid salt

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2002038288A (en) * 2000-06-28 2002-02-06 Bayer Ag Method for producing completely fluorinated organic compound with electrochemical fluorination
JP2009179836A (en) * 2008-01-30 2009-08-13 Mitsubishi Materials Corp Method of absorbing perfluoroalkane sulfonyl fluoride

Also Published As

Publication number Publication date Type
JP2012176944A (en) 2012-09-13 application
JP6023432B2 (en) 2016-11-09 grant

Similar Documents

Publication Publication Date Title
US20040116742A1 (en) Selective reaction of hexafluoropropylene oxide with perfluoroacyl fluorides
JPH0881436A (en) Production of sulfonimide
US20090105502A1 (en) Methods for producing perfluoroalkanedi(sulfonyl chloride)
US20060276671A1 (en) Manufacture of hydrofluoroalkanesulfonic acids
WO2009123328A1 (en) Sulfonylimide salt and method for producing the same
JP2010168308A (en) Fluorosulfonylimides and method for producing the same
WO2010014665A1 (en) Methods for producing arylsulfur pentafluorides
US20010021790A1 (en) Process for producing sulfonylimide compound
US6252105B1 (en) Synthesis of low-fluoride organic compounds
US7268238B2 (en) Manufacturing method and apparatus of 4-fluoroethylene carbonate
US5728884A (en) Process for the work-up of complex amine hydrofluroides
JP2006131588A (en) Method for producing a fluorine-containing sulfinate
RU2309935C1 (en) Method for combined preparing chloroform and alkylene carbonates
WO2006018991A1 (en) PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE α-FLUORO- CARBOXYLIC ESTER DERIVATIVES
JP2007039376A (en) Method for producing hydrofluoroether (hfe)
US20010031891A1 (en) Process for producing perfluoroalkanesulfinate
JP2004269491A (en) Method for producing perfluoroalykylimide compound
US20130020537A1 (en) Method for producing methanesulfonic acid alkyl ester solution
WO2003053920A1 (en) Crystals of bicalutamide and process for their production
US6794519B2 (en) Process for the production of sulfonic esters
WO2006055748A2 (en) Method for the preparation of sevoflurane
JP2008162902A (en) Method for producing difluoroacetic acid ester
US20060205983A1 (en) Process for production of 1,2,2,2-tetrafluoro ethyl difluoro methyl ether
JP2009179836A (en) Method of absorbing perfluoroalkane sulfonyl fluoride
JP2014062036A (en) Method for producing lithium difluorophosphate

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 12742656

Country of ref document: EP

Kind code of ref document: A1

NENP Non-entry into the national phase in:

Ref country code: DE

122 Ep: pct app. not ent. europ. phase

Ref document number: 12742656

Country of ref document: EP

Kind code of ref document: A1