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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
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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

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