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Process for the preparation of 1-chloro-1-fluoroethane and/or 1,1-difluoroethane

Assignee: Solvay SA
•
Filing: 1995-10-27
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Granted: 2004-10-26
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Expires: 2015-10-27
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Abstract

Abstract The invention relates to a process for the preparation of chloro-1-fluoroethane and 1,1-difluoroethane by reaction of vinyl chloride with hydrogen fluoride, in organic solvent consisting of at least one saturated halogen-containing hydrocarbon.

Inventors

  • 👤 Pascal Pennetreau
  • 👤 Francine Janssens

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 19:30
CPC Classifications
C; C07; C07C; C07C17/00; C07C17/07; C07C17/087; C07C17/093; C07C17/20; C07C17/21

Claims Analysis

Total Claims: 32
Claim 1
Independent Claim 73 words
A process for the manufacture of 1-chloro-1-fluoroethane, 1,1-difluoroethane or mixtures thereof, with reduced formation of heavy halogen-containing side products, by reacting hydrogen fluoride and vinyl chloride reactants in the liquid phase, comprising (a) introducing said reactants into a liquid reaction mixture containing an organic solvent consisting of at least one saturated organic halogenated hydrocarbon so as to provide for dilution of said reactants by the halogenated hydrocarbon at all times of the reaction.
Claim 2
Dependent Claim 73 words
A process for the manufacture of 1-chloro-1-fluoroethane, 1,1-difluoroethane or mixtures thereof, with reduced formation of heavy halogen-containing side products, by reacting hydrogen fluoride and vinyl chloride reactants in the liquid phase, comprising (a) introducing said reactants into a liquid reaction mixture containing an organic solvent consisting of at least one saturated organic halogenated hydrocarbon so as to provide for dilution of said reactants by the halogenated hydrocarbon at all times of the reaction.
Claim 3
Dependent Claim 26 words
The process according to claim 1 , wherein the saturated halogen-containing hydrocarbon is selected from chloro-, fluoro- or chlorofluorohydrocarbons containing from 1 to 8 carbon atoms.
Claim 4
Dependent Claim 19 words
The process according to claim 2 , wherein the saturated halogen-containing hydrocarbon of the process is used as solvent.
Claim 5
Dependent Claim 22 words
The process according to claim 1 , wherein the reaction mixture contains, at all times, at least 55% by weight of solvent.
Claim 6
Dependent Claim 48 words
The process according to claim 1 , wherein the introduction of the vinyl chloride and hydrogen fluoride is controlled so that, at all times, the vinyl chloride content is less than 15% and that of hydrogen fluoride is less than 30% of the weight of the reaction mixture.
Claim 7
Dependent Claim 29 words
The process according to claim 1 , wherein the molar ratio between the hydrogen fluoride and the vinyl chloride used is at least 1 and does not exceed 20.
Claim 8
Dependent Claim 44 words
The process according to claim 1 , wherein the reaction is carried out in the presence of a hydrofluorination catalyst chosen from derivatives of metals of groups IIIa, IVa, IVb, Va, Vb and VIb of the Periodic Table of the elements, and their mixtures.
Claim 9
Dependent Claim 39 words
The process according to claim 1 , wherein the reaction is performed at a temperature of at least 40° and not exceeding 130° C. and at a pressure at least equal to 2 bar and not exceeding 50 bar.
Claim 10
Dependent Claim 17 words
The process according to claim 1 , wherein the product is withdrawn continuously from the reaction mixture.
Claim 11
Dependent Claim 18 words
The process according to claim 9 , wherein the product is 1,1-difluoroethane, which is withdrawn in gaseous form.
Claim 12
Dependent Claim 59 words
A process for the manufacture of 1-chloro-1-fluoroethane, 1,1-difluoroethane or mixtures thereof y reaction between hydrogen fluoride and vinyl chloride, comprising: (a) providing at least prior to the reaction an organic solvent consisting of at least one saturated organic halogenated hydrocarbon; (b) introducing hydrogen fluoride and vinyl chloride reactants into the organic solvent; (c) recovering 1-chloro-1-fluoroethane, 1,1-difluoroethane or mixtures thereof.
Claim 13
Dependent Claim 59 words
A process for the manufacture of 1-chloro-1-fluoroethane, 1,1-difluoroethane or mixtures thereof y reaction between hydrogen fluoride and vinyl chloride, comprising: (a) providing at least prior to the reaction an organic solvent consisting of at least one saturated organic halogenated hydrocarbon; (b) introducing hydrogen fluoride and vinyl chloride reactants into the organic solvent; (c) recovering 1-chloro-1-fluoroethane, 1,1-difluoroethane or mixtures thereof.
Claim 14
Dependent Claim 22 words
The process according to claim 11 , wherein the reaction mixture contains, at all times, at least 55% by weight of solvent.
Claim 15
Dependent Claim 45 words
The process according to claim 11 , wherein the introduction of vinyl chloride and hydrogen fluoride is controlled so that, at all times, vinyl chloride content is less than 15% and hydrogen fluoride content is less than 30% of the weight of the reaction mixture.
Claim 16
Dependent Claim 26 words
The process according to claim 11 , wherein the molar ratio between hydrogen fluoride and vinyl chloride is at least 1 and does not exceed 20.
Claim 17
Dependent Claim 44 words
The process according to claim 11 , wherein the reaction is carried out in the presence of a hydrofluorination catalyst chosen from derivatives of metals of groups IIIa, IVa, IVb, Va, Vb, and VIb of the Periodic Table of the elements, and mixtures thereof.
Claim 18
Dependent Claim 38 words
The process according to claim 11 , wherein the reaction is performed at a temperature of at least 40° C. and not exceed 130° C. and at a pressure equal to 2 bar and not exceeding 50 bar.
Claim 19
Dependent Claim 14 words
The process according to claim 11 , wherein a desired product is continuously recovered.
Claim 20
Dependent Claim 16 words
The process according to claim 17 , wherein said product is 1,1-difluoroethane, withdrawn in gaseous form.
Claim 21
Dependent Claim 19 words
The process according to claim 1 , wherein said reaction is at a temperature between 80° and 110° C.
Claim 22
Dependent Claim 19 words
The process according to claim 11 , wherein said reaction is at a temperature between 80° and 110° C.
Claim 23
Dependent Claim 72 words
A process for the manufacture of 1-chloro-1-fluoro-ethane, 1,1-difluoroethane, or mixtures thereof, with reduced formation of heavy halogen-containing side products, comprising providing a liquid reaction mixture by providing an organic solvent and introducing the hydrogen fluoride and vinyl chloride into solvent wherein hydrogen fluoride and vinyl chloride are contacted with said reaction mixture under such conditions that the vinyl chloride content is maintained in the reaction mixture at less than 15% by weight.
Claim 24
Dependent Claim 72 words
A process for the manufacture of 1-chloro-1-fluoro-ethane, 1,1-difluoroethane, or mixtures thereof, with reduced formation of heavy halogen-containing side products, comprising providing a liquid reaction mixture by providing an organic solvent and introducing the hydrogen fluoride and vinyl chloride into solvent wherein hydrogen fluoride and vinyl chloride are contacted with said reaction mixture under such conditions that the vinyl chloride content is maintained in the reaction mixture at less than 15% by weight.
Claim 25
Dependent Claim 18 words
The process according to claim 21 , wherein said vinyl chloride content is at least 0.1% by weight.
Claim 26
Dependent Claim 26 words
The process according to claim 21 , wherein said vinyl chloride content is at least equal to 0.5% by weight and less than 10% by weight.
Claim 27
Dependent Claim 20 words
The process according to claim 21 , wherein said reaction mixture contains less than 30% by weight of hydrogen fluoride.
Claim 28
Dependent Claim 27 words
The process according to claim 21 , wherein the molar ratio between hydrogen fluoride and the vinyl chloride is at least 1 and does not exceed 20.
Claim 29
Dependent Claim 48 words
The process according to claim 21 , wherein the reaction is carried out in the presence of a hydrofluorination catalyst selected from the group consisting of derivatives of metals of Groups IIIa, IVa, IVb, Va, Vb, and VIb of the Periodic Table of the Elements, and their mixtures.
Claim 30
Dependent Claim 40 words
The process according to claim 21 , wherein the reaction is performed at a temperature of at least 40° C. and not exceeding 130° C. and at a pressure at least equal to 2 bar and not exceeding 50 bar.
Claim 31
Dependent Claim 29 words
The process according to claim 21 , wherein a desired product selected from group consisting of 1-chloro-1-1 fluoroethane, 1,1-difluoroethane, and mixtures thereof is withdrawn continuously from the reaction mixture.
Claim 32
Dependent Claim 16 words
The process according to claim 28 , wherein said desired product is 1,1-difluoroethane in gaseous form.

References Cited (Backward Citations)

DE859887C Cited
US2495407A Cited
GB921254A Cited
FR1396251A Cited
GB1036354A Cited
FR2019507A6 Cited
FR2365542A1 Cited
US5008474A Cited
WO1989012617A1 Cited
CN1069019A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 2007-10-26 2008-04-26 2008-10-26 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 2011-10-26 2012-04-26 2012-10-26 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 2015-10-26 2016-04-26 2016-10-26 $7700.00 Window Closed / Lapsed

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