US4078007A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Fluorine substitution in 1,1,1-trihalomethanes
Assignee: Halocarbon Products Corp
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Filing: 1976-08-10
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Granted: 1978-03-07
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Expires: 1996-08-10
Abstract
Abstract Fluorine is substituted for other halogen atoms on the 1-carbon atom of a compound which contains a 1,1,1-trihalomethyl group (trichloromethyl) by contacting said compound or a precursor thereof with liquid HF in the presence of a mixture of antimony pentahalide with at least an approximately equimolar amount of antimony trihalide. The antimony halides may be added as the chlorides and in situ converted to fluorides and/or chlorofluorides, which are believed to be the essential agents. Additional starting material and antimony pentahalide may be added in the course of the reaction which proceeds stepwise. When the reactant is 1,1,1,3-tetrachloropropane the reaction can be continued to produce 3-chloro-1,1,1-trifluoropropane which, upon reaction with alkali, yields 3,3,3-trifluoropropane, of known utility in making fluorosilicones. The reaction is also useful in the production of 2-chloro-1,1,1-trifluoroethane from 2-chloro-1,1,1-trihaloethanes and/or precursors thereof such as trichloroethylene, as well as in the production of trifluoromethane and chlorotrifluoromethane from chloroform and carbon tetrachloride, respectively.
Inventors
- 👤 Louis L. Ferstandig
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 09:33
CPC Classifications
C; C07; C07C; C07C21/00; C07C21/02; C07C21/18; C07C17/00; C07C17/093; C07C17/20; C07C17/202; C07C17/206; C07C17/208
Claims Analysis
Total Claims: 18
Claim 1
Independent Claim
82 words
A process for substituting fluorine in place of other halogen atoms on the 1-carbon atom of a 1,1,1-trihaloalkane comprising contacting said 1,1,1-trihaloalkane with liquid HF in the presence of mixture of antimony pentahalide with at least an approximately equimolar amount of antimony trihalide at a temperature from about room temperature to about 85° C and a pressure from about 20 to 100 psig, the halogen atoms of the antimony trihalide and pentahalide being selected from the group consisting of chlorine and fluorine.
Claim 2
Dependent Claim
82 words
A process for substituting fluorine in place of other halogen atoms on the 1-carbon atom of a 1,1,1-trihaloalkane comprising contacting said 1,1,1-trihaloalkane with liquid HF in the presence of mixture of antimony pentahalide with at least an approximately equimolar amount of antimony trihalide at a temperature from about room temperature to about 85° C and a pressure from about 20 to 100 psig, the halogen atoms of the antimony trihalide and pentahalide being selected from the group consisting of chlorine and fluorine.
Claim 3
Dependent Claim
15 words
The process according to claim 1, wherein the reaction is effected in a steel reactor.
Claim 4
Dependent Claim
36 words
The process according to claim 1, wherein the halogen substituted by fluorine is chlorine and the reaction is conducted at a temperature and pressure such that hydrogen chloride which is formed distills off, leaving HF behind.
Claim 5
Dependent Claim
27 words
The process according to claim 1, wherein the mixture of antimony pentahalide and trihalide is formed in situ by mixing liquid HF with antimony pentachloride and trichloride.
Claim 6
Dependent Claim
29 words
The process according to claim 1, wherein the 1,1,1-trihalomethane starting material is added and, after the reaction slows down, additional antimony pentachloride is added, followed by further starting material.
Claim 7
Dependent Claim
51 words
The process according to claim 1, wherein the mixture of the antimony pentahalide and antimony trihalide employed in the fluorination is produced in situ by starting with a mass richer in pentahalide than is to be employed in subsequent fluorination, and reducing some of the pentahalide to form the desired mixture.
Claim 8
Dependent Claim
50 words
The process according to claim 1, wherein the mixture of antimony pentahalide and antimony trihalide employed in the fluorination is produced in situ by starting with a mass richer in trihalide than is to be employed in subsequent fluorination, and oxidizing some of the trihalide to form the desired mixture.
Claim 9
Dependent Claim
50 words
The process according to claim 1, wherein the reaction mass is distilled to separate a distillate of HF and organic material from residual antimony salts, the distillate is cooled to cause separation into a lower organic layer and an upper HF layer, and the layers are separated from one another.
Claim 10
Dependent Claim
44 words
The process according to claim 1, wherein the reaction mixture is refluxed and the reflux condensate stratifies into a lower organic layer and an upper HF layer, the lower organic layer being removed and the upper HF layer being returned to the reaction mixture.
Claim 11
Dependent Claim
23 words
The process according to claim 1, wherein the HF is present in at least about three times the molar amount of the 1,1,1-trihaloalkane.
Claim 12
Dependent Claim
32 words
The process according to claim 1, wherein the mixture of antimony pentahalide and trihalide is formed in situ by adding to the liquid HF the corresponding mixture of antimony pentachloride and trichloride.
Claim 13
Dependent Claim
26 words
The process according to claim 11, wherein the 1,1,1-trihaloalkane is added and, after the reaction slows down, additional antimony pentachloride is added, followed by further 1,1,1-trihaloalkane.
Claim 14
Dependent Claim
20 words
The process according to claim 1, wherein the 1,1,1-trihaloalkane is 1,1,1,3-tetrachloropropane and the reaction is continued until 3-chloro-1,1,1-trifluoropropane is produced.
Claim 15
Dependent Claim
20 words
The process according to claim 1, wherein the 1,1,1-trihaloalkane is 1,2-dichloro-1,1-difluoroethane and the reaction is continued until 2-chloro-1,1,1-trifluoroethane is produced.
Claim 16
Dependent Claim
24 words
The process according to claim 1, wherein the 1,1,1-trihaloalkane is produced in situ from 1,1,2-trichloroethylene and the reaction is continued until 2-chloro-1,1,1-trifluoroethane is produced.
Claim 17
Dependent Claim
20 words
The process according to claim 1, wherein the 1,1,1-trihaloalkane is chlorodifluoromethane and the reaction is continued until trifluoromethane is produced.
Claim 18
Dependent Claim
12 words
The process according to claim 1, wherein the 1,1,1-trihalomethane is carbon tetrachloride.
References Cited (Backward Citations)
No citation records indexed.
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-03-06 | 1981-09-05 | 1982-03-07 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-03-06 | 1985-09-05 | 1986-03-07 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-03-06 | 1989-09-05 | 1990-03-07 | $7700.00 | Window Closed / Lapsed |