US6958424B1
Expired / Lapsed
US
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Process for fluoroalkenes
Assignee: Honeywell International Inc
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Filing: 2004-12-10
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Granted: 2005-10-25
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Expires: 2024-12-10
Abstract
Abstract Disclosed is a process for producing fluoroalkene of the formula R f —CH═CH 2 from a fluorohaloalkene having the formula R f —C(R 1 )═C(R 2 )H, wherein R f is fluorine or a substituted or unsubstituted C 1 –C 20 straight or branched-chain fluorinated alkyl and R 1 and R 2 are independently H, Cl, Br, or I, provided that at least one of R 1 or R 2 is Cl, Br, or I by reacting the fluorohaloalkene with a reducing agent, preferably a formate salt in the presence of a catalyst.
Inventors
- 👤 Haridasan K. Nair
- 👤 Andrew J. Poss
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-27 18:40
CPC Classifications
C; C07; C07C; C07C17/00; C07C17/23
Claims Analysis
Total Claims: 40
Claim 1
Independent Claim
219 words
A method of reducing environmentally undesirable emissions from a process that produces as a byproduct a chlorinated compound of formula (I) R f —C(R 1 )═C(R 2 )H (I) wherein R f is fluorine or substituted or unsubstituted C 1 –C 20 straight or branched-chain fluorinated alkyl; and R 1 and R 2 are independently H, Cl, Br, or I, provided that at least one of R 1 or R 2 is Cl, the method comprising the steps of: providing a waste by-product containing at least one compound of formula (I); exposing said waste by-product to reaction conditions effective to reduce at least a substantial portion of the compound of formula (I) contained in said waste by-product to at least one fluoroalkene having a lower degree of chlorination than said compound of formula (I) by contacting said waste by-product with at least one formate salt in the presence of a catalyst, said exposing step producing a reaction product stream comprising compound of formula (I) and said at least one fluoroalkene; separating at least a portion of said at least one fluoroalkene produced in said exposing step from said reaction product stream to produce a stream relatively rich in said compound of formula (I); and subjecting said stream relatively rich in the compound of formula (I) to said exposing step.
Claim 2
Independent Claim
219 words
A method of reducing environmentally undesirable emissions from a process that produces as a byproduct a chlorinated compound of formula (I) R f —C(R 1 )═C(R 2 )H (I) wherein R f is fluorine or substituted or unsubstituted C 1 –C 20 straight or branched-chain fluorinated alkyl; and R 1 and R 2 are independently H, Cl, Br, or I, provided that at least one of R 1 or R 2 is Cl, the method comprising the steps of: providing a waste by-product containing at least one compound of formula (I); exposing said waste by-product to reaction conditions effective to reduce at least a substantial portion of the compound of formula (I) contained in said waste by-product to at least one fluoroalkene having a lower degree of chlorination than said compound of formula (I) by contacting said waste by-product with at least one formate salt in the presence of a catalyst, said exposing step producing a reaction product stream comprising compound of formula (I) and said at least one fluoroalkene; separating at least a portion of said at least one fluoroalkene produced in said exposing step from said reaction product stream to produce a stream relatively rich in said compound of formula (I); and subjecting said stream relatively rich in the compound of formula (I) to said exposing step.
Claim 3
Dependent Claim
21 words
The method of claim 1 wherein the waste by-product is selected from the group consisting of 1,2-dichloro-3,3,3-trifluorpropene, 1-chloro-3,3,3-trifluorpropene, and mixtures thereof.
Claim 4
Dependent Claim
11 words
The method of claim 2 wherein the waste by-product is 1,2-dichloro-3,3,3-trifluorpropene.
Claim 5
Dependent Claim
16 words
The method of claim 1 wherein the reducing step is carried out in an ethereal solvent.
Claim 6
Dependent Claim
15 words
The method of claim 4 wherein the ethereal solvent is dioxane, tetrahydrofuran, or mixtures thereof.
Claim 7
Dependent Claim
11 words
The method of claim 5 wherein the ethereal solvent is tetrahydrofuran.
Claim 8
Dependent Claim
31 words
The method of claim 1 wherein the formate salt is selected from the group consisting of sodium formate, potassium formate, lithium formate, cesium formate, ammonium formate, triethylamonium formate, and mixtures thereof.
Claim 9
Dependent Claim
12 words
The method of claim 7 wherein the formate salt is ammonium formate.
Claim 10
Dependent Claim
42 words
The method of claim 1 wherein the catalyst is a palladium catalyst selected from the group consisting of tris(dibenzlideneacetone)dipalladium(0), Pd 2 (dba) 3 , tris(dibenzlideneacetone)dipalladium(0)chloroform complex, Pd 2 (dba) 3 —CHCl 3 or tetrakis(triphenylphosphine)palladium(0), Pd(PPh 3 ) 4 , and mixtures thereof.
Claim 11
Dependent Claim
15 words
The method of claim 9 wherein the palladium catalyst is Pd(PPh 3 ) 4 .
Claim 12
Dependent Claim
15 words
The method of claim 10 wherein the palladium catalyst is Pd 2 (dba) 3 .
Claim 13
Dependent Claim
32 words
The method of claim 1 wherein the formate salt is ammonium formate; and the catalyst is selected from the group consisting of Pd(PPh 3 ) 4 and Pd 2 (dba) 3 .
Claim 14
Independent Claim
94 words
A method for producing a fluoroalkene of the formula R f —CH═CH 2 from a fluorohaloalkene of formula (I) R f —C(R 1 )═C(R 2 )H (I) wherein R f is fluorine or a substituted or unsubstituted C 1 –C 20 straight or branched-chain fluorinated alkyl; and R 1 and R 2 are independently H, Cl, Br, or I, provided that at least one of R 1 or R 2 is Cl, Br, or I, comprising the steps of: contacting the fluorohaloalkene with at least one formate salt in the presence of a catalyst.
Claim 15
Independent Claim
94 words
A method for producing a fluoroalkene of the formula R f —CH═CH 2 from a fluorohaloalkene of formula (I) R f —C(R 1 )═C(R 2 )H (I) wherein R f is fluorine or a substituted or unsubstituted C 1 –C 20 straight or branched-chain fluorinated alkyl; and R 1 and R 2 are independently H, Cl, Br, or I, provided that at least one of R 1 or R 2 is Cl, Br, or I, comprising the steps of: contacting the fluorohaloalkene with at least one formate salt in the presence of a catalyst.
Claim 16
Dependent Claim
20 words
The method of claim 13 wherein the fluorohaloalkene is selected from the group consisting of 1,2-dichloro-3,3,3-trifluorpropene, 1-chloro-3,3,3-trifluorpropene, and mixtures thereof.
Claim 17
Dependent Claim
10 words
The method of claim 14 wherein the fluorohaloalkene is 1,2-dichloro-3,3,3-trifluorpropene.
Claim 18
Dependent Claim
16 words
The method of claim 13 wherein the contacting step is carried out in an ethereal solvent.
Claim 19
Dependent Claim
15 words
The method of claim 16 wherein the ethereal solvent is dioxane, tetrahydrofuran, or mixtures thereof.
Claim 20
Dependent Claim
11 words
The method of claim 17 wherein the ethereal solvent is tetrahydrofuran.
Claim 21
Dependent Claim
31 words
The method of claim 13 wherein the formate salt is selected from the group consisting of sodium formate, potassium formate, lithium formate, cesium formate, ammonium formate, triethylamonium formate, and mixtures thereof.
Claim 22
Dependent Claim
12 words
The method of claim 19 wherein the formate salt is ammonium formate.
Claim 23
Dependent Claim
42 words
The method of claim 13 wherein the catalyst is a palladium catalyst selected from the group consisting of tris(dibenzlideneacetone)dipalladium(0), Pd 2 (dba) 3 , tris(dibenzlideneacetone)dipalladium(0)chloroform complex, Pd 2 (dba) 3 .CHCl 3 or tetrakis(triphenylphosphine)palladium(0), Pd(PPh 3 ) 4 , and mixtures thereof.
Claim 24
Dependent Claim
15 words
The method of claim 21 wherein the palladium catalyst is Pd(PPh 3 ) 4 .
Claim 25
Dependent Claim
15 words
The method of claim 21 wherein the palladium catalyst is Pd 2 (dba) 3 .
Claim 26
Dependent Claim
32 words
The method of claim 13 wherein the formate salt is ammonium formate; and the catalyst is selected from the group consisting of Pd(PPh 3 ) 4 and Pd 2 (dba) 3 .
Claim 27
Independent Claim
48 words
A method for continuous production of 3,3,3-trifluoropropene comprising: providing a fluorochloroalkene selected from the group consisting of 1,2-dichloro-3,3,3-trifluorpropene, 1-chloro-3,3,3-trifluorpropene, and mixtures thereof; contacting the fluorochloroalkene with at least one formate salt and a catalyst; separating 3,3,3-trifluoropropene from any unreacted fluorochloroalkene; and recycling the unreacted fluorochloroalkene to the reactor.
Claim 28
Independent Claim
48 words
A method for continuous production of 3,3,3-trifluoropropene comprising: providing a fluorochloroalkene selected from the group consisting of 1,2-dichloro-3,3,3-trifluorpropene, 1-chloro-3,3,3-trifluorpropene, and mixtures thereof; contacting the fluorochloroalkene with at least one formate salt and a catalyst; separating 3,3,3-trifluoropropene from any unreacted fluorochloroalkene; and recycling the unreacted fluorochloroalkene to the reactor.
Claim 29
Dependent Claim
15 words
The method of claim 25 wherein the reaction is carried out in an ethereal solvent.
Claim 30
Dependent Claim
15 words
The method of claim 26 wherein the ethereal solvent is dioxane, tetrahydrofuran, or mixtures thereof.
Claim 31
Dependent Claim
11 words
The method of claim 25 wherein the ethereal solvent is tetrahydrofuran.
Claim 32
Dependent Claim
31 words
The method of claim 25 wherein the formate salt is selected from the group consisting of sodium formate, potassium formate, lithium formate, cesium formate, ammonium formate, triethylamonium formate, and mixtures thereof.
Claim 33
Dependent Claim
42 words
The method of claim 25 wherein the catalyst is a palladium catalyst selected from the group consisting of tris(dibenzlideneacetone)dipalladium(0), Pd 2 (dba) 3 , tris(dibenzlideneacetone)dipalladium(0)chloroform complex, Pd 2 (dba) 3 .CHCl 3 or tetrakis(triphenylphosphine)palladium(0), Pd(PPh 3 ) 4 , and mixtures thereof.
Claim 34
Dependent Claim
15 words
The method of claim 30 wherein the palladium catalyst is Pd(PPh 3 ) 4 .
Claim 35
Dependent Claim
15 words
The method of claim 30 wherein the palladium catalyst is Pd 2 (dba) 3 .
Claim 36
Dependent Claim
32 words
The method of claim 25 wherein the formate salt is ammonium formate; and the catalyst is selected from the group consisting of Pd(PPh 3 ) 4 and Pd 2 (dba) 3 .
Claim 37
Dependent Claim
13 words
The method of claim 25 wherein the separating step is performed by distillation.
Claim 38
Dependent Claim
18 words
The method of claim 25 further comprising the step of removing carbon dioxide prior to the separating step.
Claim 39
Dependent Claim
27 words
The method of claim 25 wherein the providing step comprises generating a byproduct stream of fluorochloroalkenes selected from the group consisting of 1,2-dichloro-3,3,3-trifluorpropene, 1-chloro-3,3,3-trifluorpropene, and mixtures thereof.
Claim 40
Dependent Claim
16 words
The method of claim 36 wherein the providing step comprises generating a byproduct stream of 1,2-dichloro-3,3,3-trifluoropropene.
References Cited (Backward Citations)
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