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Process for producing fluoroolefins

A technology selected from fluorine-containing olefins, which is applied to the preparation of fluorinated olefins or fluorinated halogenated olefins or fluorinated olefins. The compound includes the field of general formulas, which can solve the problems of low product yield and prolonged reaction time.

Inactive Publication Date: 2005-03-02
HONEYWELL INT INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

For example, there is evidence that in some cases dehydrohalogenation was unsuccessful, in another case protracted reaction times were required (three days), or relatively low product yields were obtained (40%, 65%)

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] CF 3 CH 2 CF 2 Dehydrofluorination of H(HFC-245fa)

[0041] To a 100 ml aqueous solution of potassium hydroxide (20 wt %) containing the crown ether 18-crown-6 (0.050 g, 0.2 mmol) in an autoclave / bottle was added CF at about 0°C 3 CH 2 CF 2 H (5.93 g, 44 mmol). The stirred reaction mixture was gradually warmed to room temperature (about 20-25° C.) and stirred for about 2 more hours. The volatile product CF formed by the reaction was collected in a cold trap at about -78 °C 3 CH=CFH (3.76 g, 33 mmol, 75% yield).

Embodiment 2

[0043] CF 3 CH 2 CF 2 Dehydrofluorination of H(HFC-245fa)

[0044] (A) In the absence of crown ethers

[0045] CF 3 CH 2 CF 2 H (6.0 g, 44 mmol). The stirred reaction mixture was sealed in a reaction vessel / pressure bottle and allowed to warm to room temperature and stirred for 24 hours. Analysis of volatiles in the reaction vessel by gas chromatography showed unreacted starting material.

[0046] (B) In the presence of crown ethers

[0047] Reaction (A) was repeated as above except that crown ether 18-crown-6 (0.025 g, 0.1 mmol) was added to the reaction mixture. Under these conditions, obtaining CF 3 CH=CFH (67% yield) (85% conversion).

Embodiment 3

[0049] CF 3 CH 2 CF 2 Dehydrochlorination of Cl(HCFC-235fa)

[0050] To a 100 ml aqueous solution of potassium hydroxide (20 wt %) containing the crown ether 18-crown-6 (0.084 g, 0.31 mmol) in an autoclave / bottle was added CF at about 0°C 3 CH 2 CF 2 Cl (6.4 g, 38.7 mmol). The stirred reaction mixture in a sealed autoclave / bottle was gradually warmed to room temperature and stirred for about another 1 hour. Gas chromatography analysis (retention time 1.9 minutes, for CF 3 CH=CF 2 ) showed 93% conversion. The volatile species CF formed during the reaction were collected in a cold trap at about -78 °C 3 CH=CF 2 (3.47g, 26mmol, 67% yield).

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PUM

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Abstract

A process for producing a fluoroolefin of the formula: CF3CY=CXnHp wherein Y is a hydrogen atom or a halogen atom (i.e., fluorine, chlorine, bromine or iodine); X is a hydrogen atom or a halogen atom (i.e., fluorine, chlorine, bromine or iodine); nand p are integers independently equal to 0, 1 or 2, provided that (n + p) = 2; comprising contacting, in the presence of a phase transfer catalyst, a compound of the formula: CF3C (R<l>aR<2>b) C (R<3>CR<4>d) , wherein R<1>, R<2>, R<3>, and R<4> are independently a hydrogen atom or a halogen selected from the group consisting of fluorine, chlorine, bromine and iodine, provided that at least one of R<1>, R<2>, R<3>, and R<4> is halogen and there is at least one hydrogen and one halogen on adjacent carbon atoms; a and b are independently = 0, 1 or 2 and (a+b) = 2; and c and d are independently = 0, 1, 2 or 3 and (c+d) = 3; and at least one alkali metal hydroxide. The alkali metal hydroxide can be, for example, potassium or sodium hydroxide and the phase transfer catalyst can be, for example, at least one: crown ether such as 18-crown-6 and ls-crown-S; or onium salt such as, quaternary phosphonium salt and quaternary ammonium salt. The olefin is useful, for example, as an intermediate for producing other industrial chemicals and as a monomer for producing oligomers and polymers.

Description

Background of the invention [0001] The present invention relates to a process for the preparation of fluoroalkenes or fluorohaloalkenes or fluoroalkenes, sometimes hereinafter referred to for convenience as fluoroalkenes or fluoroalkenes, which are useful intermediates for the preparation of industrial chemicals and are produced on an industrial scale in high yields and the starting materials used are readily available commercially. More specifically, the present invention relates to a process for the preparation of fluoroalkenes such as 1,1,1,3,3-pentafluoropropene (also denoted "HFC-1225zc") by, for example, 1-chloro-1, 1,3,3,3-Pentafluoropropane (also denoted as "HCFC-235fa") by dehydrohalogenation of halogenated fluorocarbons prepared by 1,1,3,3, 3-Pentafluoropropane (also represented by "HFC-235fa") is prepared by photosensitive chlorination. [0002] such as CF 3 CH=CH 2 The preparation of fluoroalkenes can be carried out by catalytic vapor phase of various saturated...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07B61/00C07C17/04C07C17/25C07C21/18
CPCC07C17/25C07C17/04C07C19/14C07C21/18
Inventor N·K·哈里达森I·R·尚克兰德D·E·布拉德利A·J·波斯T·R·德明D·纳尔瓦杰克M·范德普伊
Owner HONEYWELL INT INC
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