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US4357282A
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Preparation of fluorocarbonyl compounds
Assignee: EIDP Inc
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Filing: 1981-04-03
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Granted: 1982-11-02
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Expires: 2001-04-03
Abstract
Abstract Fluorinated carbonyl compounds are prepared by contacting a fluorinated methyl or ethyl ether containing at least one methoxylated carbon atom-containing group selected from: --CF 2 OR 3 , ═CFOR 3 , ##STR1## wherein R 3 is CH 3 or C 2 H 5 , with a catalyst selected from: SbX 5 , TaX 5 , NbX 5 , AsX 5 , BiX 5 , TiX 4 , ZrX 4 , HfX 4 , FeX 3 , mixtures of SbX 3 and SbX 5 , ZM'X' 6 , and mixtures of ZM'X' 6 and M'X 5 where X, independently, is F, Cl, Br or I, X' is F or Cl; and Z is H, NO, O 2 , alkali metal or NY 4 where Y, independently, is H or alkyl of 1 to 6 carbon atoms, and M' is Sb or As at a temperature of -20° to 200° C.
Inventors
- 👤 Daniel G. Anderson
- 👤 David C. England
- 👤 Alwin S. Milian, Jr.
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-28 22:22
CPC Classifications
C; C07; C07C; C07C51/00; C07C51/58; C07C41/00; C07C41/01; C07C41/16; C07C41/18; C07C45/00; C07C45/51; C07C45/87; C07C45/89; C07C49/00; C07C49/88
Claims Analysis
Total Claims: 14
Claim 1
Independent Claim
151 words
A method of preparing fluorinated carbonyl compounds which comprises contacting a fluorinated methyl or ethyl ether containing at least one methoxylated carbon atom-containing group selected from the group consisting of ##STR60## wherein R 3 is CH 3 or C 2 H 5 , with a catalyst selected from the group consisting of SbX 5 , TaX 5 , NbX 5 , AsX 5 , BiX 5 , TiX 4 , ZrX 4 , HfX 4 , FeX 3 , mixtures of SbX 3 and SbX 5 , ZM'X' 6 , and mixtures of ZM'X' 6 and M'X 5 where M' is Sb or As; X, independently, is F, Cl, Br or I; X' is F or Cl; and Z is H, NO, O 2 , alkali metal or NY 4 were Y, independently, is H or alkyl of 1 to 6 carbon atoms at a temperature of -20° to 200° C.
Claim 2
Independent Claim
151 words
A method of preparing fluorinated carbonyl compounds which comprises contacting a fluorinated methyl or ethyl ether containing at least one methoxylated carbon atom-containing group selected from the group consisting of ##STR60## wherein R 3 is CH 3 or C 2 H 5 , with a catalyst selected from the group consisting of SbX 5 , TaX 5 , NbX 5 , AsX 5 , BiX 5 , TiX 4 , ZrX 4 , HfX 4 , FeX 3 , mixtures of SbX 3 and SbX 5 , ZM'X' 6 , and mixtures of ZM'X' 6 and M'X 5 where M' is Sb or As; X, independently, is F, Cl, Br or I; X' is F or Cl; and Z is H, NO, O 2 , alkali metal or NY 4 were Y, independently, is H or alkyl of 1 to 6 carbon atoms at a temperature of -20° to 200° C.
Claim 3
Dependent Claim
20 words
The method of claim 1 in which the contacting is carried out at a temperature of -10° to 150° C.
Claim 4
Dependent Claim
13 words
The method of claim 2 in which the catalyst is SbF 5 .
Claim 5
Dependent Claim
13 words
The method of claim 2 in which the catalyst is SbCl 5 .
Claim 6
Dependent Claim
19 words
The method of claim 2 in which the catalyst is a mixture of SbF 5 and HSbF 6 .
Claim 7
Dependent Claim
13 words
The method of claim 2 in which the catalyst is TiCl 4 .
Claim 8
Dependent Claim
137 words
The method of claim 2 in which the fluorinated methyl or ethyl ether is a saturated terminal ether of the formula ##STR61## wherein X 1 is --H or --F; Y is --F or --CF 3 ; r is 0 or 1; s is 1 or 2 and r+s=2; R 1 is --F, --Cl, --Br, --SO 2 F, --COF, --OCH 3 , --CN, --CO 2 H, --CO 2 CH 3 , --OC 6 F 5 , --OR, --SR, or --R, where R is a perfluorinated alkyl of 1 to 8 carbon atoms, linear or branched, interruptable with ether oxygen or keto groups, and optionally contains functional substituents selected from the group consisting of --F, --Cl, --Br, --SO 2 F, --COF, --OCH 3 , --CN, --CO 2 H, --CO 2 CH 3 , and --OC 6 F 5 .
Claim 9
Dependent Claim
22 words
The method of claim 2 in which the fluorinated ether is R 3 O 2 CCF 2 CF 2 OR 3 .
Claim 10
Dependent Claim
18 words
The method of claim 2 in which the fluorinated ether is NCCF 2 CF 2 OR 3 .
Claim 11
Dependent Claim
110 words
The method of claim 2 in which the fluorinated ether is an internally unsaturated terminal ether of the formula ##STR62## wherein R 1 is --F, --Cl, --Br, --SO 2 F, --COF, --OCH 3 , --CN, --CO 2 H, --CO 2 CH 3 , --OC 6 F 5 , --OR, --SR, or --R; and R is a perfluorinated alkyl of 1 to 8 carbon atoms, linear or branched, interruptable with ether oxygen or keto groups, and which optionally contains functional substituents selected from the group consisting of --F, --Cl, --Br, --SO 2 F, --COF, --OCH 3 , --CN, --CO 2 H, --CO 2 CH 3 , --OC 6 F 5 .
Claim 12
Dependent Claim
139 words
The method of claim 2 in which the fluorinated ether is an unsaturated internal ether of the formula ##STR63## wherein X 2 and X 3 are the same or different and are selected from --H, --F, or --Cl; R 1 is --F, --Cl, --Br, --SO 2 F, --COF, --OCH 3 , --CN, --CO 2 H, --CO 2 CH 3 , --OC 6 F 5 , --OR, --SR or --R, where R is a perfluorinated alkyl of 1 to 8 carbon atoms, linear or branched, interruptable with ether oxygen or keto groups, and which optionally contains functional substituents selected from the group consisting of --F, --Cl, --Br, --SO 2 F, --COF, --OCH 3 , --CN, --CO 2 H, --CO 2 CH 3 , --OC 6 F 5 ; and R 2 is a perfluoroalkyl of 1 to 8 carbon atoms.
Claim 13
Independent Claim
62 words
A method of preparing the carbonyl compound, R 3 O 2 CCF 2 COF, wherein R 3 is CH 3 or C 2 H 5 , by contacting a fluorinated methyl or ethyl ether, R 3 O 2 CCF 2 CF 2 OR 3 , with AlCl 3 , AlBr 3 or AlI 3 at a temperature of 60° to 140° C.
Claim 14
Independent Claim
62 words
A method of preparing the carbonyl compound, R 3 O 2 CCF 2 COF, wherein R 3 is CH 3 or C 2 H 5 , by contacting a fluorinated methyl or ethyl ether, R 3 O 2 CCF 2 CF 2 OR 3 , with AlCl 3 , AlBr 3 or AlI 3 at a temperature of 60° to 140° C.
References Cited (Backward Citations)
GB1143930A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-11-01 | 1986-05-03 | 1986-11-02 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-11-01 | 1990-05-03 | 1990-11-02 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-11-01 | 1994-05-03 | 1994-11-02 | $7700.00 | Window Closed / Lapsed |