Process for preparing fluorohalogenethers

A technology for fluorohalogenated hydrocarbons and fluorohalogenated olefins, which can be used in the preparation of ethers, the preparation of ethers by the addition of unsaturated compounds, and the preparation of dehalogenation, which can solve problems such as high loss of CFC112

Active Publication Date: 2007-06-27
SOLVAY SOLEXIS
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Therefore, from an industrial point of view, CFC 112a must be reduced to very low values,

Method used

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  • Process for preparing fluorohalogenethers
  • Process for preparing fluorohalogenethers
  • Process for preparing fluorohalogenethers

Examples

Experimental program
Comparison scheme
Effect test

Embodiment A

[0108] CF 3 Synthesis of OF

[0109] 10 l / h of gaseous fluorine, 5 l / h of CO and 10 l / h of nitrogen were allowed to flow simultaneously in an AISI 316 steel pipe (inner diameter 2.17 mm and length 100 mm). The reaction was initiated by heating the gas mixing zone at 100°C for several minutes. During the whole time, the reactor was cooled with air circulation so as to keep the temperature below 300°C; at the reactor outlet, the temperature was 250°C. Under these conditions, CO and F 2 Conversion to COF in greater than 95% yield (determined by IR analysis of effluent gas mixture) 2 .

[0110] Let the gas mixture, after cooling to 100°C, flow through a catalyst bed consisting of 300g of finely ground anhydrous CsF with a particle size less than or equal to 0.1mm, and 300g of acicular copper with a diameter of 0.2mm and a length of 6 to 7mm. Mix composition. The catalyst was put into a tubular reactor (inner diameter 55 mm, length 250 mm). The reaction temperature in gas wa...

Embodiment 1

[0112] Addition of fluorine to trichloroethylene

[0113] By 25.5g trichlorethylene (TCE) and 475g CF 3 O-CFCl-CF 2 The solution consisting of the Cl reaction solvent was introduced into a 400cc AISI 316 reactor equipped with a mechanical stirrer.

[0114] The solution was cooled by a cryostat to maintain a temperature of -70°C, and under stirring, 1 mole of fluorine was diluted with nitrogen at a molar ratio of 1 / 2 and sent through the bubbler inlet. Simultaneously, 1.07 mol TCE was fed by the pump. These reactants were fed over 8 h, during which time the temperature was maintained at -70°C.

[0115] At the end of the reaction, 633 g of solution were withdrawn and analyzed by GC / MS (Gas Chromatography-Mass Spectrometry). The conversion of TCE is equal to 75%, producing CFC 122a (CHClF-CCl 2 The selectivity of F) is 56.7%.

Embodiment 2

[0117] The CFC 122a obtained in Example 1 (CHClF-CCl 2 F) Dehydrochlorination

[0118] 90 g of CFC 122a with a purity of 94% obtained in Example 1, 5 g of tetrabutylammonium hydroxide were introduced into a 250 mL four-neck reactor equipped with a magnetic stirrer, dropping funnel, thermometer and water condenser. A 20% aqueous solution of 26 g NaOH was added under stirring, and the heat of reaction was controlled at 30° C. using water and an ice bath. When the base addition was complete, the mixture was allowed to stir for an additional 40 min at 30°C. It was cooled to 10°C: the final mixture showed 2 separated phases. The reaction mixture was poured into a separatory funnel maintained at 10 °C. 72 g of an organic phase with a higher density, consisting of the compound (65 g) CFC 1112 (FCCl=CCIF), with a purity of 99%, were isolated. The conversion rate is 100%, and the yield is 98%.

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Abstract

A process for preparing perfluorovinylethers having general formula: R f O-CF=CF 2 (IA) wherein R f is a C 1 -C 3 alkyl perfluorinated substituent; comprising the following steps: 1a) fluorination with fluorine of olefins of formula: CY''Y=CY'Cl (II) wherein Y, Y' and Y'', equal to or different from each other, are H, Cl, Br, with the proviso that Y, Y' and Y'' are not contemporaneously hydrogen; and obtainment of fluorohalogencarbons of formula: FCY''Y-CY'ClF (III) wherein Y, Y' and Y'' are as above; 2a) dehalogenation or dehydrohalogenation of the fluorohalogencarbons (III) and obtainment of fluorohalogen olefins of formula: FCY I =CY II F (IV) wherein Y I and Y II , equal to or different from each other, have the meaning of H, Cl, Br with the proviso that Y I and Y II are not both H; 3a) reaction between a hypofluorite of formula R f OF and a fluorohalogenolefin (IV), obtaining the fluorohalogenethers of formula: RfO-CFY I -CF 2 Y II (I) wherein Y I , Y II , equal to or different from each other, are Cl, Br, H with the proviso that Y I and Y II cannot be contemporaneously equal to H; 4a) dehalogenation or dehydrohalogenation of the compounds (I) and obtainment of the perfluorovinylethers (IA).

Description

technical field [0001] The present invention relates to a method for preparing fluorohalogenated ethers, and more particularly, the present invention relates to a fluorohalogenated ether which can be produced by dehalogenation or dehydrohalogenation to produce perfluorovinyl ethers. More specifically, the present invention relates to a process for the preparation of perfluorovinyl ethers, preferably perfluoromethyl vinyl ether, perfluoroethyl vinyl ether and perfluoropropyl vinyl ether, with improved yield and selectivity, and employs precursors that do not belong to the class of chlorofluorocarbons (CFCs) and, additionally, are obtainable under conditions that do not require costly separation processing to remove hydrogenation by-products. Background technique [0002] Perfluorovinyl ethers are well known as useful monomers for the preparation of a wide variety of polymers ranging from fluorinated elastomers to fluorinated thermally processable semi-crystalline polymers. ...

Claims

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Application Information

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IPC IPC(8): C07C43/17C07C41/05C07C41/24
CPCC07C17/04C07C43/17C07C17/25C07C41/06C07C17/23C07C41/24C07C19/12C07C19/14C07C21/18C07C43/123
Inventor V·托特利P·卡利尼A·佐姆帕托里E·安特努茨
Owner SOLVAY SOLEXIS
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