Patent US4316986A successfully refreshed from Google Patents.
US4316986A
Expired / Lapsed
US
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Preparation of difluoromalonyl fluoride
Assignee: EIDP Inc
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Filing: 1980-09-23
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Granted: 1982-02-23
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Expires: 2000-09-23
Abstract
Abstract Carboxylic ester and acyl fluoride groups are interchanged in the presence of a metal fluoride catalyst or a metal fluoride/strong sulfonic acid catalyst combination to produce fluorinated mono- and diacyl fluorides.
Inventors
- 👤 David C. England
- 👤 Robert L. Kraft
- 👤 Carl G. Krespan
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 10:04
CPC Classifications
C; C07; C07C; C07C59/00; C07C59/125; C07C59/135; C07C51/00; C07C51/58; C07C51/60
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
205 words
A carboxylic ester/acyl fluoride interchange reaction process comprising the sequence: RX--CO.sub.2 CH.sub.3 +R'X'--COF.sup.catalyst RX--COF+R'X'CO.sub.2 CH.sub.3 wherein X is methylene or substituted methylene selected from the group consisting of --CF 2 --, --CFH--, --CFCl--, --CFBr--, --CFI--, and --C(CF 3 )F--; X' is substituted methylene selected from the group consisting of --CF 2 --, --CFH--, --CFCl--, --CFBr--, --CFI--, and --C(CF 3 )F--; R and R' are the same or different and are selected from the group consisting of hydrogen, halogen, and halogen-substituted and unsubstituted alkyl, alkoxy, alkaryl, aralkyl, aryloxy and polyether alkyl of up to 18 carbon atoms; R and X taken together can be R F COF; R' and X' taken together can be R F CO 2 CH 3 ; and R F is a single bond or a linear or branched perfluoroalkylene group of up to 18 carbon atoms; and wherein the catalyst is one or more metal fluorides selected from the group consisting of SbF 5 , TaF 5 , NbF 5 , AsF 5 , BiF 5 , TiF 4 , ZrF 4 and mixtures of SbF 5 and HF wherein HSbF 6 is present, and combinations of one or more of said metal fluorides with one or more strong sulfonic acids.
Claim 2
Dependent Claim
205 words
A carboxylic ester/acyl fluoride interchange reaction process comprising the sequence: RX--CO.sub.2 CH.sub.3 +R'X'--COF.sup.catalyst RX--COF+R'X'CO.sub.2 CH.sub.3 wherein X is methylene or substituted methylene selected from the group consisting of --CF 2 --, --CFH--, --CFCl--, --CFBr--, --CFI--, and --C(CF 3 )F--; X' is substituted methylene selected from the group consisting of --CF 2 --, --CFH--, --CFCl--, --CFBr--, --CFI--, and --C(CF 3 )F--; R and R' are the same or different and are selected from the group consisting of hydrogen, halogen, and halogen-substituted and unsubstituted alkyl, alkoxy, alkaryl, aralkyl, aryloxy and polyether alkyl of up to 18 carbon atoms; R and X taken together can be R F COF; R' and X' taken together can be R F CO 2 CH 3 ; and R F is a single bond or a linear or branched perfluoroalkylene group of up to 18 carbon atoms; and wherein the catalyst is one or more metal fluorides selected from the group consisting of SbF 5 , TaF 5 , NbF 5 , AsF 5 , BiF 5 , TiF 4 , ZrF 4 and mixtures of SbF 5 and HF wherein HSbF 6 is present, and combinations of one or more of said metal fluorides with one or more strong sulfonic acids.
Claim 3
Dependent Claim
14 words
A process according to claim 1: 2FOC--R.sub.F --CO.sub.2 CH.sub.3.sup.catalyst R.sub.F (COF).sub.2 +R.sub.F (CO.sub.2 CH.sub.3).sub.2.
Claim 4
Dependent Claim
91 words
A process according to claim 1 wherein X is selected from the group consisting of --CF 2 --, --CFH--, and --CFCl--; R is selected from the group consisting of hydrogen, fluorine, and perfluoroalkyl; X' is --CF 2 -- or --C(CF 3 )F--; R' is CF 3 CF 2 CF 2 O(CF(CF 3 )CF 2 O) n wherein n is 0 to 10; R and X taken together are R F COF; R' and X' taken together are R F CO 2 CH 2 ; and R F is --CF 2 --.
Claim 5
Dependent Claim
30 words
A process according to claim 1, 2, or 3 wherein the strong sulfonic acid is selected from the group consisting of fluorosulfonic acid, trifluoromethane sulfonic acid and perfluorosulfonic acid resin.
Claim 6
Dependent Claim
34 words
A process according to claim 1 wherein R is --COF, X is --CF 2 --, R' is CF 3 CF 2 CF 2 O(CF(CF 3 )CF 2 O)--, and X' is --CF(CF 3 )--.
Claim 7
Dependent Claim
36 words
A process according to claim 1 wherein R is CF 3 , X is --CFH--, R' is CF 3 CF 2 CF 2 O--CF(CF 3 )CF 2 O-- 2 , and X' is --CF(CF 3 )--.
Claim 8
Dependent Claim
36 words
A process according to claim 1 wherein R is Cl, X is --CF 2 --, R' is CF 3 CF 2 CF 2 O(CF(CF 3 )CF 2 O) 2 , and X' is --CF(CF 3 )--.
Claim 9
Dependent Claim
37 words
A process according to claim 1 wherein R is H and X is --CH 2 --, R' is CF 3 CF 2 CF 2 O--CF(CF 3 )CF 2 O-- 2 , and X' is --CF(CF 3 )--.
Claim 10
Dependent Claim
13 words
A process according to claim 2 wherein R F is --CF 2 --.
Claim 11
Dependent Claim
19 words
A process according to claim 9 wherein the catalyst is a combination of fluorosulfonic acid and SbF 5 .
References Cited (Backward Citations)
US3250807A
Cited
US4154753A
Cited
US3557165A
Cited
US3948761A
Cited
US4127731A
Cited
US4201876A
Cited
US4131740A
Cited
US4151200A
Cited
US4122115A
Cited
US4247713A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1985-02-22 | 1985-08-24 | 1986-02-23 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-02-22 | 1989-08-24 | 1990-02-23 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-02-22 | 1993-08-24 | 1994-02-23 | $7700.00 | Window Closed / Lapsed |