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Process for producing a fluorine atom-containing sulfonyl fluoride compound

a technology of sulfonyl fluoride and compound, which is applied in the preparation of carboxylic compounds, organic chemistry, chemistry apparatus and processes, etc., can solve the problems unable to achieve the reduction of the price, and limited compound (i) , to achieve the effect of reducing the pri

Inactive Publication Date: 2010-03-30
AGC INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This process enables the efficient and cost-effective production of fluorine atom-containing sulfonyl fluoride compounds with diverse molecular structures, improving the membrane characteristics of ion-exchange membranes and reducing production challenges.

Problems solved by technology

However, the conventional synthetic process was a disadvantageous process for practical industrial application, since a due care is required for handling SO3.
Further, reduction of the price can hardly be accomplished because the difficulty in synthesis is high.
In addition, the obtainable compound (i) is limited to a compound having a side chain (—CF3), whereby there has been a problem from the viewpoint of the membrane characteristics of the ion-exchange membrane prepared from a derivative of the compound (i).

Method used

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  • Process for producing a fluorine atom-containing sulfonyl fluoride compound
  • Process for producing a fluorine atom-containing sulfonyl fluoride compound
  • Process for producing a fluorine atom-containing sulfonyl fluoride compound

Examples

Experimental program
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Effect test

example 1

Production of FSO2CH2CH2OCH2CH2OH

[0154]Into a round flask, HO(CH2)2OH (140.9 g) and a methanol solution of sodium methylate (28 wt %, 96.4 g) were charged and stirred, and heated under reduced pressure to distill off methanol thereby to obtain a solution of HOCH2CH2ONa. It was confirmed by GC that no methanol remained in the reaction solution. Into a four necked flask, FSO2CH2CH2Cl (50 g) and THF (100 mL) were charged and stirred under cooling with ice bath, and the previously obtained solution of HOCH2CH2ONa was dropwise added thereto over a period of 2.5 hours, while maintaining the internal temperature to be at most 10° C. After completion of the dropwise addition, it was stirred at room temperature for 2 hours and then added to water (400 mL), and dichloromethane (183 g) was added. The obtained crude liquid was subjected to liquid separation, and the obtained aqueous layer was extracted with dichloromethane (124 g). The separated aqueous layer was further extracted with dichloro...

example 2

Production of FSO2CH2CH2OCH2CH2OCOCF(CF3)OCF2CF2CF3(esterification step)

[0157]FSO2CH2CH2OCH2CH2OH (47.1 g) having a purity of 64%, obtained in Example 1, and triethylamine (19.5 g) were put into a flask and stirred under cooling with ice bath. FCOCF(CF3)OCF2CF2CF3(64.1 g) was dropwise added thereto over a period of 40 minutes, while maintaining the internal temperature to be at most 10° C. After completion of the dropwise addition, it was stirred for two hours at room temperature and then added to ice water (100 mL).

[0158]The obtained crude liquid was subjected to liquid separation, and the lower layer was washed twice with water (100 mL) and dried over magnesium sulfate, followed by filtration to obtain a crude liquid. The crude liquid was purified by silica gel column chromatography (developing solvent: dichloropentafluoropropane (tradename: AK-225)) to obtain FSO2CH2CH2OCH2CH2OCOCF(CF3)OCF2CF2CF3(21.2 g). The GC purity was 88%.

[0159]1H-NMR (300.4 MHz, CDCl3, TMS) δ (ppm): 3.57 to...

example 3

Production of FSO2CF2CF2OCF2CF2OCOCF(CF3)OCF2CF2CF3(fluorination step)

[0161]Into a 500 mL autoclave made of nickel, R-113(313 g) was added, stirred and maintained at 25° C. At the gas outlet of the autoclaves a cooler maintained at 20° C., a packed layer of NaF pellets and a cooler maintained at −10° C., were installed in series. Further, a liquid-returning line was installed to return a condensed liquid from the cooler maintained at −10° C. to the autoclave. After supplying nitrogen gas for 1.0 hour, fluorine gas diluted to 20% by nitrogen gas (hereinafter referred to as diluted fluorine gas) was supplied for one hour at a flow rate of 7.78 L / hr. Then, while supplying the diluted fluorine gas at the same flow rate, a solution obtained by dissolving FSO2CH2CH2OCH2CH2OCOCF(CF3)OCF2CF2CF3 (7.01 g) obtained in Example 2, in R-113(140 g), was supplied over a period of 5.5 hours.

[0162]Then, while supplying the diluted fluorine gas at the same flow rate and maintaining the pressure of the...

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Abstract

The present invention provides a process whereby fluorine atom-containing sulfonyl fluoride compound(s) useful as e.g. materials for ion-exchange membranes, can be produced efficiently and at low cost without structural limitations while solving the difficulties in production. Namely, the present invention provides a process which comprises reacting XSO2RA-E1 (1) with RB-E2 (2) to form XSO2RA-E-RB (3), then reacting (3) with fluorine in a liquid phase to form FSO2RAF-EF-RBF (4), and further, decomposing the compound to obtain FSO2RAF-EF1 (5), wherein RA is a bivalent organic group, E1 is a monovalent reactive group, RB is a monovalent organic group, E2 is a monovalent reactive group which is reactive with E1, E is a bivalent connecting group formed by the reaction of E1 with E2, RAF is a bivalent organic group formed by the fluorination of RA, etc., RBF is the same group as RB, etc., EF is a bivalent connecting group formed by the fluorination of E, etc., EF1 is a monovalent group formed by the decomposition of EF, and X is a halogen atom.

Description

CROSS-RELATED APPLICATIONS[0001]This application is a Divisional Application of 10 / 442,227, filed May 21, 2003, now U.S. Pat. No. 6,790,982 which is a continuation of PCT / JP01 / 10407, filed on November 28, 2001.[0002]More than one reissue application has been filed for the reissue of U.S. Pat. No. 7,105,697. The reissue applications are U.S. application Ser. No. 11 / 812,533 (the parent reissue application), U.S. Ser. No. 12 / 234,109(the present application), and U.S. Ser. No. 12 / 234,140. U.S. Ser. No. 12 / 234,109 and U.S. Ser. No. 12 / 234,140 are divisional reissues of U.S. Pat. No. 7,105,697 and were filed based on U.S. Ser. No. 11 / 812,533, the parent broadening reissue application of U.S. Pat. No. 7,105,697.<?insert-end id="INS-S-00001" ?>TECHNICAL FIELD[0003]The present invention relates to a process for producing fluorine atom-containing sulfonyl fluoride compounds useful as e.g. materials for ion-exchange resins, and novel chemical substances useful as intermediates in the pro...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C07C69/66C07C309/00C07C69/63C07C51/60C07C303/22C07C309/82
CPCC07C51/60C07C303/22C07C309/82C07C59/135
Inventor ITO, MASAHIROWATANABE, KUNIOOKAZOE, TAKASHIKANEKO, ISAMUSHIRAKAWA, DAISUKE
Owner AGC INC