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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: 2004-04-14
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 (the molar ratio of fluorine / nitrogen 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 by 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% and 61.25% respect...

Embodiment 2

[0060] Embodiment 2 (comparative test)

[0061] CF was synthesized according to the prior art 3 -CF 2 -CF 2 O-CFCl-CF 2 Cl

[0062] a) According to US Patent No. 4,827,024, the synthesis of fluorooxyhalogenated compound CF 3 -CF 2 -CF 2 OF

[0063] In the 500 milliliter tubular metal reactor that is filled with catalyst cesium fluoride (CsF) and is mixed with the copper wire that disperses the heat of reaction, feeds 2.7gNl / h the fluorine that passes nitrogen (fluorine / nitrogen molar ratio is 1 / 10) and a 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.

[0064] 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

[0065] 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 (CFC 115) In a CSTR ...

Embodiment 3

[0068] Embodiment 3 (comparative test)

[0069] Synthetic CF 3 -CF 2 O-CFCl-CF 2 Cl(ethyl adduct)

[0070] a) Synthesis of fluorooxyhalogenated compounds

[0071] 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%.

[0072] b) Synthesis of CF 3 -CF 2 O-CFCl-CF 2 Cl

[0073] 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%.

[0074] 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 .

[0075] The resulting ethyl adduct is recovered after distillation of the solution. The amount of...

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PUM

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Abstract

A process for preparing (per) fluorohalogenethers having general formula (I): (R)nC(F)mOCAF-CA'F2 wherein: A and A', equal to or different the one from the other, are Cl or Br or one is selected from A and A' and hydrogen and the other is halogen selected from Cl, Br; R = F, or a fluorinated, preferably perfluorinated, substituent, selected from the following groups: linear or branched C1-C20 alkyl more preferably C1-C10; C3-C7 cycloalkyl; aromatic, C6-C10 arylalkyl, alkylaryl; C5-C10 heterocyclic or alkylheterocyclic; when R is fluorinated or perfluorinated alkyl, cycloalkyl, arylalkyl, alkylaryl, it can optionally contain in the chain one or more oxygen atoms; when R is fluorinated it can optionally contain one or more H atoms and / or one or more halogen atoms different from F: n is an integer and is 1 or 2; m = 3-n; by reaction of carbonyl compounds having formula (II): (R)pC(F)q(O) wherein: p is an integer and is 1 or 2; q is an integer and is zero or 1, R is as above; in liquid phase with elemental fluorine and with olefinic compounds having formula (III): CAF=CA'F wherein A and A' are as above, at temperatures in the range from -120 DEG C to -20 DEG C.

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 4,827,024, a method for preparing fluorine-oxyhalogenated compounds in a continuous manner is descri...

Claims

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Application Information

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IPC IPC(8): C07C37/14C07C41/06C07C43/12C07C303/02
CPCC07C43/123C07C41/06C07C43/126
Inventor V·托尔特利P·卡利尼
Owner SOLVAY SOLEXIS
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