US4091043A
Expired / Lapsed
US
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Process for the preparation of 1-chloro-1,1-difluoroethane and/or 1,1,1-trifluoroethane
Assignee: Daikin Industries Ltd
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Filing: 1976-12-21
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Granted: 1978-05-23
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Expires: 1996-12-21
Abstract
Abstract A process for preparing 1-chloro-1,1-difluoroethane and/or 1,1,1-trifluoroethane by fluorination of 1,1,1-trichloroethane with anhydrous hydrofluoric acid in the presence of antimony pentachloride in a halogenated hydrocarbon solvent which is capable of dissolving both the catalyst and 1,1,1-trichloroethane, is substantially inert in the reaction system and which has a boiling point of above 0° C and a melting point of below 60° C. By varying the mole ratio of hydrofluoric acid to 1,1,1-trichloroethane both fed together into a solution of the catalyst in the solvent, 1-chloro-1,1-difluoroethane and 1,1,1-trifluoroethane are obtained with a variety of desired ratios.
Inventors
- 👤 Yohnosuke Ohsaka
- 👤 Osamu Morimoto
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-01 09:00
CPC Classifications
C; C07; C07C; C07C17/00; C07C17/093; C07C17/20; C07C17/202; C07C17/206
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
109 words
A process for the fluorination of 1,1,1-trichloroethane comprising reacting 1,1,1-trichloroethane with anhydrous hydrofluoric acid in the presence of antimony pentachloride catalyst in a solvent which meets the following criteria: a. said solvent being capable of dissolving both antimony pentachloride and 1,1,1-trichloroethane; b. said solvent having a boiling point of at least 0° C and a melting point not higher than 60° C; c. said solvent neither reduces antimony pentachloride to a corresponding trivalent antimony compound, nor hydrolyzes antimony pentachloride nor produces a solid complex with antimony pentachloride; d. said solvent being less reactive with anhydrous hydrofluoric acid than methylchloroform or 1,1-dichloro-1-fluoroethane; and e. said solvent being non-reactive with methylchloroform.
Claim 2
Dependent Claim
109 words
A process for the fluorination of 1,1,1-trichloroethane comprising reacting 1,1,1-trichloroethane with anhydrous hydrofluoric acid in the presence of antimony pentachloride catalyst in a solvent which meets the following criteria: a. said solvent being capable of dissolving both antimony pentachloride and 1,1,1-trichloroethane; b. said solvent having a boiling point of at least 0° C and a melting point not higher than 60° C; c. said solvent neither reduces antimony pentachloride to a corresponding trivalent antimony compound, nor hydrolyzes antimony pentachloride nor produces a solid complex with antimony pentachloride; d. said solvent being less reactive with anhydrous hydrofluoric acid than methylchloroform or 1,1-dichloro-1-fluoroethane; and e. said solvent being non-reactive with methylchloroform.
Claim 3
Dependent Claim
32 words
The process as defined in claim 1, wherein said solvent is at least one halogenated hydrocarbon having 1 to 4 carbon atoms, said carbon atoms each having 0 to 2 hydrogen atoms.
Claim 4
Dependent Claim
55 words
The process as defined in claim 2, wherein said halogenated hydrocarbon is selected from the group consisting of carbon tetrachloride, chloroform, methylene chloride, trichlorofluoromethane, dichloromonofluoromethane, monochloromonofluoromethane, 1,1,2,2-tetrachloro-2,2-difluoroethane, 1,1,2-trichloro-1,2,2-trifluoroethane, 1,1,1-trichloro-2,2,2-trifluoroethane, 1,2-dichloro-1,2-difluoroethane, 1,1-dichloro-2,2-difluoroethane, 1,1,1,2-tetrachloro-1-fluoroethane, 1,1,2,2-tetrachloro-1-fluoroethane, 1,1,2-trichloro-1,2-difluoroethane, 1,1,2-trichloro-2,2-difluoroethane, 1,1,1-trichloro-2,2-difluoroethane, 1,2-dichloro-1,1,2-trifluoroethane, 1,1-dichloro-1,2,2-trifluoroethane, 1,1-dichloro-2,2,2-trifluoroethane, 1,2-dichloro-1,1,2,2-tetrafluoroethane, 1,1-dichloro-1,2,2,2-tetrafluoroethane, pentachloroethane, 1,2-dichloroethane, 1,1,2-trichloroethane, 1,1,2,2-tetrachloroethane, 1,2-dichloro-1,2,3,3,4,4-hexafluorocyclobutane, 1-chloro-1,2,2,3,3,4,4-heptafluorocyclobutane, 2,3-dichloro-1,1,1,4,4,4-hexafluoro-2-butene, 1,2-dibromo-1,1,2,2-tetrafluoroethane, 1,1,1-trifluoro-2-chloro-2-bromoethane, 1,2-dibromo-1,1,2-trifluoro-2-chloroethane, 1,1,2,2-tetrachloro-1,2-difluoroethane, 1,1,1,2-tetrachloroethane and 1,2,2,3-tetrachloro-1,1,3,3-tetrafluoropropane.
Claim 5
Dependent Claim
35 words
The process as defined in claim 1, wherein said solvent is at least one hydrocarbon selected from the group consisting of chloroform, 1,1,2-trichloro-1,2,2-trifluoroethane, 1,1,2,2-tetrachloro-1,2-difluoroethane, 1,1,1,2-tetrachloroethane, methylene chloride, 1,2-dichloro-1,1,2,2-tetrafluoroethane, trichlorofluoromethane, dichlorofluoromethane, 1,2-dichloroethane, pentachloroethane, 1,1,2,2-tetrachloroethane, 1,2,2,3-tetrachloro-1,1,3,3-tetrafluoropropane, 2,3-dichloro-1,1,1,4,4,4-hexafluoro-2-butene.
Claim 6
Dependent Claim
31 words
The process as defined in claim 1, wherein said catalyst is used in an amount of between 1 and 60% based on the total moles of said catalyst and said solvent.
Claim 7
Dependent Claim
22 words
The process as defined in claim 1, wherein the mole ratio of anhydrous hydrofluoric acid to 1,1,1-trichloroethane ranges from 1.8 to 3.5.
Claim 8
Dependent Claim
22 words
The process as defined in claim 1, wherein said reaction is performed at a temperature of between 0° C. and 80° C.
Claim 9
Dependent Claim
56 words
The process as defined in claim 1, which comprises providing in a reactor a solution of said catalyst in said solvent, bringing simultaneously both anhydrous hydrofluoric acid and 1,1,1-trichloroethane into direct contact with said solution, and recovering a product comprising at least one component selected from 1-chloro-1,1-difluoroethane and 1,1,1-trifluoroethane from the gas emitted from the reactor.
Claim 10
Dependent Claim
32 words
The process as defined in claim 8, wherein the content of said catalyst in the solution ranges from 1 to 60% based on the total moles of said catalyst and said solvent.
Claim 11
Dependent Claim
22 words
The process as defined in claim 8, wherein the mole ratio of anhydrous hydrofluoric acid to 1,1,1-trichloroethane ranges from 1.8 to 3.5.
Claim 12
Dependent Claim
27 words
The process as defined in claim 8, wherein said contacting is by feeding a mixture of anhydrous hydrofluoric acid and 1,1,1-trichloroethane into said solution in the reactor.
Claim 13
Dependent Claim
46 words
The process as defined in claim 8, wherein said recovering step comprises introducing said gas into a first separation zone to separate said gas into a lower boiling point phase and a higher boiling point phase and recovering said product from said lower boiling point phase.
Claim 14
Dependent Claim
55 words
The process as defined in claim 12, wherein said recovering of said product from said lower boiling point phase comprises introducing said lower boiling point phase into a second separation zone to separate said lower boiling point phase into a condensed liquid phase and a gas phase and recovering said product from said gas phase.
Claim 15
Dependent Claim
18 words
The process as defined in claim 12, further comprising recycling said higher boiling point phase into the reactor.
Claim 16
Dependent Claim
19 words
The process as defined in claim 13, further comprising recycling said condensed liquid phase into the first separation zone.
References Cited (Backward Citations)
US2005710A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-05-22 | 1981-11-21 | 1982-05-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-05-22 | 1985-11-21 | 1986-05-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-05-22 | 1989-11-21 | 1990-05-23 | $7700.00 | Window Closed / Lapsed |