Patent US3926989A successfully refreshed from Google Patents.
US3926989A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for the preparation of aryl-1,1,2,2-tetrafluoroethyl ethers
Assignee: Hoechst AG
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Filing: 1971-06-14
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Granted: 1975-12-16
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Expires: 1991-06-14
Abstract
Abstract Phenols react with tetrafluoroethylene at normal or reduced pressure when using about 0.05 to about 0.5 mole of an alkali metal hydroxide per each equivalent of phenolic hydroxy group as a catalyst and a water-miscible polar inert solvent to yield aryl-1,1,2,2-tetrafluoroethyl ethers. The products are useful as intermediates in the synthesis of dyestuffs and plant-protecting agents.
Inventors
- 👤 Siegfried Rebsdat
- 👤 Helmut Hahn
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 21:08
CPC Classifications
C; C07; C07C; C07C47/00; C07C47/52; C07C47/575; C07C45/00; C07C45/61; C07C45/67; C07C45/68; C07C45/70; C07C45/71
Claims Analysis
Total Claims: 10
Claim 1
Independent Claim
153 words
IN A PROCESS FOR THE PREPARATION OF AN ARYL-1,2,2-TETRAFLUOROETHYL ETHER BY REACTING A PHENOL WITH TETRAFLUORETHYLENE IN AN ORGANIC SOLVENT IN THE PRESENCE OF AN ALKALINE CATALYST AT ELEVATED TEMPERATURES, THE IMMPROVEMENT COMPRISING REACTING A PHENOLIC COMPOUND SELECTED FROM THE GROUP CONSISTING OF PHENOL, NAPHTHOL AND PHENOL SUBSTITUTED BY 1 TO 3 SUBSTITUTENTS SELECTED FROM THE GROUP CONSISTING OF ALKYL OF 1 TO 20 CARBON ATOMS, ALKOXY OF 1 TO 6 CARBON ATOMS, HYDROXY, FORMYL, AMINO, MONOALKYLAMINO OF 1 TO 4 CARBON ATOMS, DIALKYLAMINO OF 1 TO 4 CARBON ATOMS IN ACH ALKYL MOIETY, PIPERIDINO, MORPHOLINO AND ALKANOYLAMINO OF 1 TO 5 CARBON ATOMS IN THE ALKANE MOIETY, WITH TETRAFLUOROETHYLENE IN A WATER-MISCIBLE POLAR INERT SOLVENT WITH ABOUT 0.05 TO ABOUT 0.5 MOL OF POTASSIUM HYDROXIDE PER EACH EQUIVALENT OF PHENOLIC HYDROXY GROUP AT A TEMPERATURE OF ABOUT 50* TO ABOUT 150*C AND A PRESSURE VARYING BETWEEN ATMOSHERIC PRESSURE AND SLIGHTLY SUBATMOSPHERIC PRESSURE.
Claim 2
Dependent Claim
153 words
IN A PROCESS FOR THE PREPARATION OF AN ARYL-1,2,2-TETRAFLUOROETHYL ETHER BY REACTING A PHENOL WITH TETRAFLUORETHYLENE IN AN ORGANIC SOLVENT IN THE PRESENCE OF AN ALKALINE CATALYST AT ELEVATED TEMPERATURES, THE IMMPROVEMENT COMPRISING REACTING A PHENOLIC COMPOUND SELECTED FROM THE GROUP CONSISTING OF PHENOL, NAPHTHOL AND PHENOL SUBSTITUTED BY 1 TO 3 SUBSTITUTENTS SELECTED FROM THE GROUP CONSISTING OF ALKYL OF 1 TO 20 CARBON ATOMS, ALKOXY OF 1 TO 6 CARBON ATOMS, HYDROXY, FORMYL, AMINO, MONOALKYLAMINO OF 1 TO 4 CARBON ATOMS, DIALKYLAMINO OF 1 TO 4 CARBON ATOMS IN ACH ALKYL MOIETY, PIPERIDINO, MORPHOLINO AND ALKANOYLAMINO OF 1 TO 5 CARBON ATOMS IN THE ALKANE MOIETY, WITH TETRAFLUOROETHYLENE IN A WATER-MISCIBLE POLAR INERT SOLVENT WITH ABOUT 0.05 TO ABOUT 0.5 MOL OF POTASSIUM HYDROXIDE PER EACH EQUIVALENT OF PHENOLIC HYDROXY GROUP AT A TEMPERATURE OF ABOUT 50* TO ABOUT 150*C AND A PRESSURE VARYING BETWEEN ATMOSHERIC PRESSURE AND SLIGHTLY SUBATMOSPHERIC PRESSURE.
Claim 3
Dependent Claim
25 words
The process as claimed in claim 1, wherein the phenolic compound is phenol, naphthol or phenol substituted by lower alkyl, amino, formyl, hydroxy or acetamino.
Claim 4
Dependent Claim
13 words
The process as claimed in claim 1, wherein the solvent is dimethyl formamide.
Claim 5
Dependent Claim
12 words
The process as claimed in claim 1, wherein the solvent is dimethylsulfoxide.
Claim 6
Dependent Claim
14 words
The process as claimed in cliam 1, wherein the solvent is phosphoric acid tris-(dimethylamide).
Claim 7
Dependent Claim
23 words
The process as claimed in claim 1, wherein the reaction mixture contains about 10 to about 30 percent by weight of phenolic compound.
Claim 8
Dependent Claim
23 words
The process as claimed in claim 1, wherein the reaction mixture contains about 15 to about 20 percent by weight of phenolic compound.
Claim 9
Dependent Claim
30 words
The process as claimed in claim 1, wherein the alkali metal hydroxide is used in an amount of about 0.1 to 0.3 mol per each equivalent of phenolic hydroxy group.
Claim 10
Dependent Claim
21 words
The process as claimed in claim 1, wherein the temperature is in the range of about 70* to about 130* C.
References Cited (Backward Citations)
FR2005876A1
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-12-15 | 1979-06-16 | 1979-12-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-12-15 | 1983-06-16 | 1983-12-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-12-15 | 1987-06-16 | 1987-12-16 | $7700.00 | Window Closed / Lapsed |