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Preparation for fluro-halogenated ether

A substituted halogenated ether and fluorinated technology, which is applied in the field of preparation of fluorovinyl ether, can solve problems such as compound instability

Inactive Publication Date: 2006-10-18
SOLVAY SOLEXIS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantages of the method are those in the preparation of the above-mentioned fluorooxyhalogenated compounds
In particular, the disadvantage of this method is that since the fluorooxyhalo compound must be used immediately after synthesis, since such compounds are notoriously unstable, especially at the carbons of the perfluoroalkyl chain of the fluorooxyhalo compound When the number of atoms is greater than or equal to 2

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] CF 3 -CF 2 -CF 2 OCFCl-CF 2 Synthesis of Cl

[0049] 57g of CFCl=CFCl (CFC 1112) and 15g of CF 3 -CF 2 COF (perfluoropropionyl fluoride, PFPF) was added to a 50 ml glass reaction vial with a mechanical stirrer, and the solution was kept at -100°C.

[0050] Through a gas inlet, fluorine gas diluted with nitrogen gas (the molar ratio of fluorine gas / nitrogen gas is 1:5) was introduced for 6.5 hours. A mild exothermic reaction can be seen during the fluorine passage.

[0051] The gas from the reaction flask flows into a collector with fluorinated solvent maintained at -80°C.

[0052] After the reaction was completed, the solution discharged from the reaction bottle and collector was analyzed by gas chromatography.

[0053] The reaction equilibrium value of the material is 93.6%. Calculated based on the solution poured out from the reaction bottle and the compound of the fluorinated liquid in the collector, the conversion rates of olefins CFC 1112 and PFPF are 100%4...

Embodiment 2

[0061] Embodiment 2 (comparative test)

[0062] CF was synthesized according to the prior art 3 -CF 2 -CF 2 O-CFCl-CF 2 Cl

[0063] a) According to US Patent No. 4,827,024, the synthesis of fluorooxyhalogenated compound CF 3 -CF 2 -CF 2 OF

[0064] In the 500 milliliter tubular metal reactor that is filled with catalyst cesium fluoride (CsF) and is mixed with the copper wire that disperses reaction heat, feeds 2.7g Nl / h the fluorine gas (fluorine gas / nitrogen gas molar ratio) that has been diluted through nitrogen 1 / 10) and CF of 2.3Nl / h 3 -CF 2 -COF(PFPF). Conversion of PFPF to fluorooxyhalogenated compound CF 3 -CF 2 -CF 2 OF, 99.5% yield.

[0065] b) According to U.S. Patent No. 4,900,872, CF is synthesized by reaction between the obtained fluorooxyhalogenated compound and CFC 1112 3 -CF 2 -CF 2 O-CFCl-CF 2 Cl

[0066] The fluorooxyhalogenated compound obtained in process a) was added to a CFCl=CFCl (CFC 1112) containing 121.2g and 452g CF 2 Cl-CF 3 (CF...

Embodiment 3

[0069] Embodiment 3 (comparative test)

[0070] Synthetic CF 3 -CF 2 O-CFCl-CF 2 Cl(ethyl adduct)

[0071] a) Synthesis of fluorooxyhalogenated compounds

[0072] By the method of a) step of embodiment 2 (comparative test), but pass into the CF of 2.3Nl / h in the catalytic reactor 3 -COF(PFAF). Fluoroxyhalogenated compound CF 3 -CF 2 The yield of OF was 99.6%.

[0073] b) Synthesis of CF 3 -CF 2 O-CFCl-CF 2 Cl

[0074] 300 g of CFC 1112 were added to the CSTR reactor as in step b) of Example 2 (comparative test), but without solvent. The reaction mass balance was 90%.

[0075] The solution poured from the reactor was analyzed by gas chromatography, calculated according to the added fluorooxyhalogenated compound, the ethyl adduct CF 3 -CF 2 O-CFCl-CF 2 The yield of Cl was 75%. The remaining 25% of the oxyfluoride halogenated compounds decompose to form COF 2 .

[0076] The resulting ethyl adduct is recovered after distillation of the solution. The amount of r...

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PUM

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Abstract

A method for preparing (per)fluorohalogenated ethers having the general formula (I): (R) n C(F) m OCAF-CA'F 2 (I), wherein: A and A', the same or different from each other, are chlorine or bromine, or one is selected from A, A' and hydrogen, and the other is a halogen selected from chlorine and bromine; R = fluorine or fluoro, It is preferably a perfluorinated substituent, and the substituent is selected from the following groups: linear or branched C 1 -C 20 Alkyl, more preferably C 1 -C 10 ;C 3 -C 7 cycloalkyl; aryl, C 6 -C 10 Arylalkyl, alkylaryl; C 5 -C 10 A heterocycle or an alkyl heterocycle; when R is a fluoro or perfluoroalkyl group, a cycloalkyl group, an arylalkyl group, or an alkylaryl group, the chain may optionally contain one or more oxygen atoms; When R is fluorinated, it may optionally contain one or more hydrogen atoms and / or one or more halogen atoms different from fluorine; n is an integer and is 1 or 2; m=3-n; the method is by At a reaction temperature of -120°C to -20°C, the liquid carbonyl compound of formula (II): (R) p C(F) q (O)(II), wherein: p is an integer and is 1 or 2; q is an integer and is 0 or 1; R is as defined above; reacts with elemental fluorine and an alkene compound of formula (III): CAF=CA'F( III), wherein A and A' are as defined above.

Description

technical field [0001] The present invention relates to a preparation method of fluorovinyl ether. [0002] More specifically, the present invention relates to the preparation of fluorohalogenated ethers which are dehalogenated to give fluorovinyl ethers. The process of the invention leads to fluorohaloethers with improved selectivity. Background technique [0003] Fluorovinyl ethers are well known as a class of valuable monomers for the preparation of a wide variety of polymers ranging from fluorinated elastomers to heat-treatable semi-crystalline fluorinated polymers. [0004] The preparation of fluorohalogenated ethers based on the reaction of fluorooxyhalogenated compounds (hypofluorites) with olefins is known in the prior art. For the preparation of oxyfluorohalogenated compounds, the most common method is to use metal fluoride-based catalysts. [0005] In U.S. Patent No. 4827024, a method for preparing fluorine-oxyhalogenated compounds in a continuous manner is desc...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C43/12C07C37/14C07C41/06C07C303/02
CPCC07C41/06C07C43/123C07C43/126
Inventor V·托尔特利P·卡利尼
Owner SOLVAY SOLEXIS
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