US4035388A
Expired / Lapsed
US
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Process for preparing perfluoro-alkoxy-propionic acid fluorides
Assignee: Hoechst AG
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Filing: 1975-12-22
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Granted: 1977-07-12
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Expires: 1995-12-22
Abstract
Abstract Perfluoro carbonyl compounds react with hexafluoro propene epoxide in the presence of dimethylamino-difluoro-phosphorane producing perfluorinated carboxylic acid fluorides with ether linkages. Among the carbonyl compounds which can be used are perfluorinated ketones, acid fluorides of the formula R.sub.F -- COF and R.sub.F -- OCF(CF.sub.3) -- COF (r f being a perfluoro-alkyl radical having from 1 to 4 carbon atoms) and perfluoro-2-oxo-3,6-dimethyl-1,4-dioxane.
Inventors
- 👤 Thomas Martini
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 23:45
CPC Classifications
C; C07; C07D; C07D319/00; C07D319/10; C07D319/12; C07C; C07C51/00; C07C51/58; C07C51/62
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
145 words
A process for preparing perfluoro-α-alkoxypropionic acid fluorides of the general formula ##STR11## wherein R 1 stands for a perfluoroalkyl radical having from 1 to 9 carbon atoms or for the radical ##STR12## and wherein n is 0, 1 or 2, which comprises that perfluorocarbonyl compounds of the general formula R.sup.2 -- CO-- R.sup.3 II, wherein R 2 represents fluorine or R F 2 , R 3 represents fluorine or R F 3 or (R 2 being fluorine) also R F 3 -- OC F (CF 3 )--, R f 2 and R F 3 represent identical or different perfluoroalkyl radicals having from 1 to 4 carbon atoms or R 2 and R 3 combined with the CO group give the compound perfluoro-2-oxo-3,6-dimethyl-1,4-dioxane, are reacted with hexafluoropropene epoxide in the presence of tris-dimethylamino-difluoro-phosphorane in an aprotic polar solvent, at a temperature of -50° to +10° C.
Claim 2
Dependent Claim
145 words
A process for preparing perfluoro-α-alkoxypropionic acid fluorides of the general formula ##STR11## wherein R 1 stands for a perfluoroalkyl radical having from 1 to 9 carbon atoms or for the radical ##STR12## and wherein n is 0, 1 or 2, which comprises that perfluorocarbonyl compounds of the general formula R.sup.2 -- CO-- R.sup.3 II, wherein R 2 represents fluorine or R F 2 , R 3 represents fluorine or R F 3 or (R 2 being fluorine) also R F 3 -- OC F (CF 3 )--, R f 2 and R F 3 represent identical or different perfluoroalkyl radicals having from 1 to 4 carbon atoms or R 2 and R 3 combined with the CO group give the compound perfluoro-2-oxo-3,6-dimethyl-1,4-dioxane, are reacted with hexafluoropropene epoxide in the presence of tris-dimethylamino-difluoro-phosphorane in an aprotic polar solvent, at a temperature of -50° to +10° C.
Claim 3
Dependent Claim
21 words
The process of claim 1, which comprises that the process is carried out at a temperature of -40° to -20° C.
Claim 4
Dependent Claim
19 words
The process of claim 1, which comprises that perfluoro-n-propionic acid fluoride is reacted to yield perfluoro-α -(n-propoxy)-propionic acid fluoride.
Claim 5
Dependent Claim
19 words
The process of claim 1, which comprises that perfluoro-α -(n-propoxy)-propionic acid fluoride is reacted to yield perfluoro-α-[2-(n-propoxy)-propoxy]-propionic acid fluoride.
Claim 6
Dependent Claim
39 words
The process according to claim 4, which comprises that the perfluoro-α-(n-propoxy)-propionic acid fluoride employed is prepared in situ from hexafluoropropene epoxide in the presence of tris-dimethyl-amino-difluorophosphorane in an aprotic polar solvent at a temperature of -50° to +10° C.
Claim 7
Dependent Claim
19 words
The process according to claim 1, which comprises that perfluoro-2-oxo-3,6-dimethyl-1,4-dioxane is reacted with hexafluoropropene-epoxide to yield perfluoro-α-(3,6-dimethyl-1,4-dioxanyl-2-oxy)-propionic acid fluoride.
Claim 8
Dependent Claim
39 words
The process according to claim 6, which comprises that perfluoro-2-oxo-3,6-dimethyl-1,4-dioxane is prepared in situ from perfluoropyruvic acid fluoride and hexafluoropropene epoxide in the presence of tris-dimethylamino-difluorosphosphorane in an aprotic polar solvent, at a temperature of -50° to +10° C.
Claim 9
Dependent Claim
24 words
The process according to claim 7, which comprises that a molar ratio of hexafluoropropene epoxide/perfluoropyruvic acid fluoride of from 1 to 5 is used.
Claim 10
Dependent Claim
52 words
The process according to claim 1, wherein R 1 stands for a perfluoro-alkyl radical having from 1 to 9 carbon atoms or for the radical. ##STR13## and wherein R 3 stands for R F 3 or (R 2 being fluorine) stands also for R F 3 -- OC F (CF 3 )--.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-07-11 | 1981-01-10 | 1981-07-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-07-11 | 1985-01-10 | 1985-07-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-07-11 | 1989-01-10 | 1989-07-12 | $7700.00 | Window Closed / Lapsed |