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Process for preparing (per)fluorohaloethers

A technology of fluorinated and fluoropolyether, which is applied in the field of preparing fluorinated vinyl ethers with fluorosulfonic acid groups, can solve the problems of catalyst poisoning and activity reduction, and achieve high productivity, simplified methods, and equipment parts Effect

Active Publication Date: 2009-12-09
SOLVAY SOLEXIS
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0017] Another disadvantage of the above method involves catalyst poisoning
The applicant has tested the method for preparing hypofluorite in the prior art using the above-mentioned catalyst, and the test shows that the catalytic system is used in a batch and continuous manner, and its activity decreases rapidly within a certain period of time

Method used

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  • Process for preparing (per)fluorohaloethers

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0050] Embodiment 1 (comparative example)

[0051] Synthesis of FSO according to prior art 2 -CF 2 -CF 2 O-CFCl-CF 2 Cl

[0052] Fluorine diluted with 1.5Nl / h nitrogen (fluorine / nitrogen molar ratio 1 / 14) and 1.1Nl / h SO 2 F-CF 2 - The COF is fed into a 500cc metal reactor filled with catalyst CsF mixed with copper wire to disperse the heat of reaction. Conversion of acyl fluoride to hypofluorite SO 2 F-CF 2 -CF 2 The yield of OF was 99.5%. The hypofluorite prepared in this way is diluted with nitrogen again (hypofluorite / nitrogen molar ratio 1 / 35), and then sent to a tank containing 69g CFCl=CFCl (CFC 1112) and 453g CF 2 Cl-CF 3 (CFC 115) In the CSTR type reactor (continuous stirred tank reactor) used as the reaction solvent, the temperature was kept at -85°C.

[0053] After 4 hours the autoclave was opened and the resulting solution was analyzed by gas chromatography.

[0054] The reaction mass balance was 97.1%. The conversion rate of hypofluorite is 100%, its ...

Embodiment 2

[0057] Synthetic FSO 2 -CF 2 -CF 2 O-CFCl-CF 2 Cl

[0058] 441g CF 2 Cl-CF 3 (CFC 115) was added to the CSTR reactor of Example 1, and the temperature was maintained at -80°C. Then feed 3.9Nl / h of nitrogen-diluted fluorine (fluorine / nitrogen molar ratio 1 / 5), 3.1Nl / h of CFCl=CFCl (CFC 1112) and 3.9Nl / h of SO 2 F-CF 2 -COF.

[0059] The reaction was carried out for 3 hours, then the autoclave was opened: the mass balance was 97.4%. The initial product of the reaction was distilled in a metal column, and the fractions obtained were analyzed by gas chromatography and 19 F NMR analysis. CFC 1112 was completely converted and the conversion of acid fluoride was 57.8%.

[0060] Isolated 52.7g fluorosulfonic acid adduct FSO 2 -CF 2 -CF 2 O-CFCl-CF 2 Cl. The selectivity was 49.8%.

[0061] 39.6 g of acid fluoride were recovered.

[0062] The main reaction also occurs the fluorination of CFC 1112 to CFC 114 and to CF 2 Cl-CFCl-CFCl-CF 2 Fluorinated dimerization of Cl...

Embodiment 3

[0065] Preparation of FSO by Excessive Acyl Fluoride 2 -CF 2 -CF 2 O-CFCl-CF 2 Cl

[0066] Repeat Example 2 under the same conditions, add 128.9g SO to the CSTR reactor 2 F-CF 2 -COF and 311.1g solvent (CFC 115), feed 3.9Nl / h of nitrogen-diluted fluorine (fluorine / nitrogen molar ratio 1 / 5), 3.1Nl / h of CFCl=CFCl (CFC 1112) and 3.9 SO of Nl / h 2 F-CF 2 -COF.

[0067] The reaction mass balance was 97.6%.

[0068] Similar to Example 2, the initial product of the reaction is distilled in a metal column, and the cut obtained is passed through gas chromatography and 19 F NMR analysis. CFC 1112 was completely converted, and the conversion of the charged acid fluoride was 29%.

[0069] Isolated 34.2 g of fluorosulfonic acid adduct FSO 2 -CF 2 -CF 2 O-CFCl-CF 2 Cl. Selectivity was 65.0%.

[0070] 39.6 g of acid fluoride were recovered.

[0071] In addition to the main reaction also occurs the fluorination of CFC 1112 to CFC 114 and to CF 2 Cl-CFCl-CFCl-CF 2 Fluorinate...

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Abstract

A kind of is used for preparing -SO with general formula (I) 2 Method for (per)fluorinated haloether of F group: FSO 2 -R-CF 2 OCAF-CA'F 2 (I) in which: -A and A', the same or different from each other, are Cl or Br; -R has the following meaning: (per)fluorinated, preferably perfluorinated, optionally with one or more oxygen The substituting group of atom; The method is by the carbonyl compound FSO of formula (II) 2 -R-COF (II) wherein R is as defined above; in the liquid phase reacts with elemental fluorine and an alkene compound of formula (III): CAF=CA'F (III) wherein A and A' are as defined above, the reaction is at -120 °C to -20 °C, optionally in the presence of solvent inert components under the reaction conditions. The description of this industrial invention is carried out in the name of SOLVAY SOLEXIS S.p.A. of Italy, whose head office is at Milano, Via Turati, 12.

Description

technical field [0001] The present invention relates to a method for preparing 2 F) Process for fluorinating vinyl ethers. [0002] More specifically, the present invention relates to the preparation of 2 A process for F-based fluorinated haloethers by dehalogenation to the corresponding fluorinated vinyl ethers, which increases selectivity and reduces the formation of non-recyclable by-products. [0003] This fluorosulfonic acid vinyl ether can form a class for obtaining -SO 2 Monomer of F-group polymers used in electrochemical applications as membranes in chlorine-based soda cells, fuel cells or as acid catalysts in organic synthesis. Background technique [0004] obtained in the prior art with -SO 2 Methods for the fluorinated haloethers of F groups are known. [0005] USP 4,358,412 describes fluorosulfonic acid vinyl ether CF 2 = CF-O-CF 2 CF 2 SO 2 Synthesis of F, in which the first step is via the acyl fluoride FOC-CF 2 -SO 2 The reaction of F with perfluoro...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C303/02C07C309/82C07C303/22
CPCC07C303/22C07C309/82
Inventor V·托尔特利P·卡利尼S·米利范提
Owner SOLVAY SOLEXIS
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