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Process for producing fluoroolefins

a technology of fluoroolefins and halools, which is applied in the field of process for producing fluoroolefins or fluorohalools, can solve the problems of poor results obtained

Inactive Publication Date: 2003-03-27
HONEYWELL INT INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The authors note that poor results were obtained in the case of dehydrochlorination (page 197) and that C.sub.8 and C.sub.10 polyglycols having terminal hydroxyl groups were particularly effective compared to other phase transfer catalysts such as tetraalkylammonium salts, benzyltriethylammonium chloride and crown ethers.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

Dehydrofluorination of CF.sub.3CH.sub.2CF.sub.2H (HFC-245fa)

[0032] To 100 mL aqueous solution of KOH (20 wt. %) containing the crown ether, 18-crown-6 (0.050 g, 0.2 mmol), at about 0.degree. C. in an autoclave / pressure bottle was added CF.sub.3CH.sub.2CF.sub.2H (5.93 g, 44 mmol). The stirred reaction mixture was brought to room temperature (about 20-25.degree. C.) gradually and stirred for an additional time period of about 2 hours. The volatile product, CF.sub.3CH.dbd.CFH, (3.76 g, 33 mmol, 75% yield) formed by the reaction was collected in a cold trap at about -78.degree. C.

example 2

Dehydrofluorination of CF.sub.3CH.sub.2CF.sub.2H (HFC-245fa)

[0033] (A) In the Absence of Crown Ether

[0034] To 20 mL aqueous solution of KOH (50 wt. %) at about 0.degree. C. in an autoclave / pressure bottle was added CF.sub.3CH.sub.2CF.sub.2H (5.93 g, 44 mmol). The stirred reaction mixture in the sealed reaction vessel / pressure bottle was brought to room temperature and stirred for 24 hours. Gas chromatographic analysis of the volatile material from the reaction vessel indicated only the unreacted starting material.

[0035] (B) In the Presence of Crown Ether

[0036] The reaction in (A) was repeated as above except that the crown ether, 18-crown-6, (0.025 g, 0.1 mmol) was added to the reaction mixture. Under these conditions, CF.sub.3CH.dbd.CFH (67% yield) (85% conversion) was obtained.

example 3

Dehydrochlorination of CF.sub.3CH.sub.2CF.sub.2Cl (HCFC-235fa)

[0037] To 100 mL aqueous solution of KOH (20 wt. %) containing the crown ether, 18-crown-6, (0.084 g, 0.31 mmol), at about 0.degree. C. in an autoclave / pressure bottle was added CF.sub.3CH.sub.2CF.sub.2Cl (6.4 g, 38.7 mmol). The stirred reaction mixture in the sealed autoclave / pressure bottle was brought to room temperature gradually and stirred additionally for about 1 hour. Gas chromatographic analysis (retention time 1.9 min for CF.sub.3CH.dbd.CF.sub.2) indicated 93% conversion. The volatile material, CF.sub.3CH.dbd.CF.sub.2, (3.47 g, 26 mmol, 67% yield) formed during the reaction was collected in a cold trap at about -78.degree. C.

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Abstract

A process for producing a fluoroolefin of the formula: CF.sub.3CY.dbd.CX.sub.nH.sub.p 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); n and 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: CF.sub.3C(R.sup.1.sub.aR.sup.2.sub.b) C(R.sup.3.sub.cR.sup.4.sub.d), wherein R.sup.1, R.sup.2, R.sup.3, and R.sup.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.sup.1, R.sup.2, R.sup.3, and R.sup.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 15-crown-5; 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 producing fluoroolefins or fluorohaloolefins or fluorine-containing olefins, sometimes referred to hereinafter for convenience as fluoroolefins or fluorine-containing olefins, useful as intermediates for making industrial chemicals, in good yield, on an industrial scale and using commercially and readily available starting materials. More particularly, the present invention relates to a process for producing fluoroolefins, for example, 1,1,1,3,3-pentafluoropropene (also designated as "HFC-1225zc"), by the dehydrohalogenation of a halofluorocarbon, for example, 1-chloro-1,1,3,3,3-pentafluoropropane (also designated as "HCFC-235fa"). which halofluorocarbon can be produced by photochlorinating 1,1,3,3,3-pentafluoropropane (also designated as "HFC-245fa").[0002] The production of fluoroolefins such as CF.sub.3CH.dbd.CH.sub.2 by catalytic vapor phase fluorination of various saturated and unsaturated halogen-...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07B61/00C07C17/04C07C17/25C07C21/18
CPCC07C17/04C07C17/25C07C19/14C07C21/18
Inventor NAIR, HARIDASAN K.PUY, MICHAEL VAN DERNALEWAJEK, DAVIDDEMMIN, TIMOTHY R.POSS, ANDREW J.BRADLEY, DAVID E.SHANKLAND, IAN R.
Owner HONEYWELL INT INC
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