US3897502A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Process for making fluorinated ethers
Assignee: Anaquest Inc
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Filing: 1973-08-23
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Granted: 1975-07-29
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Expires: 1993-08-23
Abstract
Abstract A method is disclosed for partially fluorinating an alkane or a cycloalkane polyfluoroether feedstock in the liquid phase by contacting it with molecular fluorine at a temperature of about 40*C. to 0*C. Degradation, polymerization, excessive fluorination or combinations of these effects of prior art processes are avoided by the use of the present invention while relatively high yields can be obtained.
Inventors
- 👤 James P Russell
- 👤 Alex J Szur
- 👤 Ross C Terrell
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 19:44
CPC Classifications
C; C07; C07C; C07C41/00; C07C41/01; C07C41/18; C07C41/22; C07D; C07D317/00; C07D317/08; C07D317/10; C07D317/32; C07D317/42
Claims Analysis
Total Claims: 13
Claim 1
Independent Claim
232 words
A METHOD FOR PARTIALLY FLOURINATING A POLYFLUOROETHER FEEDSTOCK SELECTED FROM THE GROUP CONSISTING OF DIMETHYL DIOXALANE AND A STANDARD ALKANE CONTAINING FROM 2 TO ABOUT 16 CARBON ATOMS, SAID POLYFLUOROETHER FEEDSTOCK HAVING AT LEAST TWO FLUORINE ATOMS, AT LEAST TWO HYDROGEN ATOMS AND ONE OR TWO ETHER OXYGEN ATOMS PER MOLECULE AND HAVING AS MANY HALOGEN ATOMS OF ATOMIC NUMBER 9 TO 35 AS CARBON ATOMS IN THE MOLECULE, THE RATIO OF HALOGEN ATOMS TO CARBON ATOMS IN THE MOLECULE OF THE POLYFLUOROETHER FEEDSTOCK BEING NO MORE THAN 2:1, SAID METHOD BEING SELECTIVE TOWARD THE PRODUCTION OF A FURTHER FLUORINATED POLYFLUOROETHER HAVING AT LEAST ONE HYDROGEN ATOM AND THE SAME CARBON SKELETAL STRUCTURE IN ITS MOLECULE AS SAID POLYFLUOROETHER FEEDSTOCK, COMPRISING CONTACTING SAID POLYFLUOROETHER FEEDSTOCK WITH A MIXTURE OF MOLECULAR FLUORINE AND INERT GAS IN A REACTION ZONE UNDER REACTION CONDITIONS AT WHICH THE POLYFLUOROETHER FEEDSTOCK IS IN THE LIQUID PHASE, THE AMOUNT OF INERT GAS IN SAID MIXTURE BEING SUFFICIENT TO MODERATE THE REACTION SO THAT IT IS CONTROLLABLE AND THE MIXTURE CONTAINS ABOUT 5 TO 75 VOLUME PERCENT MOLECULAR FLUORINE BASED ON THE TOTAL FLUORINE AND INERT GAS CHARGED TO THE REACTION ZONE, THE REACTION TEMPERATURE BEING IN THE RANGE OF ABOUT -40* TO 0*C, TO PREPARE A FURTHER FLUORINATED POLYFLUOROETHER PRODUCT HAVING AT LEAST ONE HYDROGEN ATOM AND THE SAME CARBON SKELETON IN ITS MOLECULE AS SAID POLYFLUOROETHER FEEDSTOCK.
Claim 2
Independent Claim
232 words
A METHOD FOR PARTIALLY FLOURINATING A POLYFLUOROETHER FEEDSTOCK SELECTED FROM THE GROUP CONSISTING OF DIMETHYL DIOXALANE AND A STANDARD ALKANE CONTAINING FROM 2 TO ABOUT 16 CARBON ATOMS, SAID POLYFLUOROETHER FEEDSTOCK HAVING AT LEAST TWO FLUORINE ATOMS, AT LEAST TWO HYDROGEN ATOMS AND ONE OR TWO ETHER OXYGEN ATOMS PER MOLECULE AND HAVING AS MANY HALOGEN ATOMS OF ATOMIC NUMBER 9 TO 35 AS CARBON ATOMS IN THE MOLECULE, THE RATIO OF HALOGEN ATOMS TO CARBON ATOMS IN THE MOLECULE OF THE POLYFLUOROETHER FEEDSTOCK BEING NO MORE THAN 2:1, SAID METHOD BEING SELECTIVE TOWARD THE PRODUCTION OF A FURTHER FLUORINATED POLYFLUOROETHER HAVING AT LEAST ONE HYDROGEN ATOM AND THE SAME CARBON SKELETAL STRUCTURE IN ITS MOLECULE AS SAID POLYFLUOROETHER FEEDSTOCK, COMPRISING CONTACTING SAID POLYFLUOROETHER FEEDSTOCK WITH A MIXTURE OF MOLECULAR FLUORINE AND INERT GAS IN A REACTION ZONE UNDER REACTION CONDITIONS AT WHICH THE POLYFLUOROETHER FEEDSTOCK IS IN THE LIQUID PHASE, THE AMOUNT OF INERT GAS IN SAID MIXTURE BEING SUFFICIENT TO MODERATE THE REACTION SO THAT IT IS CONTROLLABLE AND THE MIXTURE CONTAINS ABOUT 5 TO 75 VOLUME PERCENT MOLECULAR FLUORINE BASED ON THE TOTAL FLUORINE AND INERT GAS CHARGED TO THE REACTION ZONE, THE REACTION TEMPERATURE BEING IN THE RANGE OF ABOUT -40* TO 0*C, TO PREPARE A FURTHER FLUORINATED POLYFLUOROETHER PRODUCT HAVING AT LEAST ONE HYDROGEN ATOM AND THE SAME CARBON SKELETON IN ITS MOLECULE AS SAID POLYFLUOROETHER FEEDSTOCK.
Claim 3
Dependent Claim
50 words
The method defined in claim 1 wherein the polyfluoroether feedstock has 2 to 5 carbon atoms in the molecule and the total amount of halogen atoms of atomic number 9 to 35 in the molecule of the polyfluoroether feedstock constitutes about 50 to 75 weight percent of such ether feedstock.
Claim 4
Dependent Claim
20 words
The method defined in claim 1 wherein the polyfluoroether feedstock is a difluoromethyl ether of the saturated alkane polyfluoroether feedstock.
Claim 5
Dependent Claim
26 words
The method defined in claim 1 wherein the polyfluoroether feedstock has the structure CHF2CF2(CF2CF2)nCH2OR, in which R is lower alkyl and n is 0 to 4.
Claim 6
Independent Claim
264 words
A method for partially fluorinating a polyfluoroether feedstock selected from the group consisting of dimethyl dioxalane and a saturated alkane containing from 2 to about 16 carbon atoms, said polyfluoroether feedstock having at least two fluorine atoms, at least two hydrogen atoms and one or two ether oxygen atoms per molecule and having as many halogen atoms of atomic number 9 to 35 as carbon atoms in the molecule, the ratio of halogen atoms to carbon atoms in the molecule of the polyfluoroether feedstock being no more than 2:1, said method being selective toward the production of a further fluorinated polyfluoroether having at least one hydrogen atom and the same carbon skeletal structure in its molecule as saiD polyfluoroether feedstock, comprising contacting said polyfluoroether feedstock with a mixture of molecular fluorine and inert gas in a reaction zone under reaction conditions at which the polyfluoroether feedstock is in the liquid phase, the amount of inert gas in said mixture being sufficient to moderate the reaction so that it is controllable and the mixture contains about 5 to 75 volume percent molecular fluorine based on the total fluorine and inert gas charged to the reaction zone, the reaction temperature being in the range of about -40* to 0* C., to prepare a further fluorinated polyfluoroether product having at least one hydrogen atom and the same carbon skeleton in its molecule as said polyfluoroether feedstock, said reaction being conducted in the presence of a solvent for said polyfluoroether feedstock and said further fluorinated polyfluoroether product, which solvent is liquid and essentially inert under said reaction conditions.
Claim 7
Independent Claim
264 words
A method for partially fluorinating a polyfluoroether feedstock selected from the group consisting of dimethyl dioxalane and a saturated alkane containing from 2 to about 16 carbon atoms, said polyfluoroether feedstock having at least two fluorine atoms, at least two hydrogen atoms and one or two ether oxygen atoms per molecule and having as many halogen atoms of atomic number 9 to 35 as carbon atoms in the molecule, the ratio of halogen atoms to carbon atoms in the molecule of the polyfluoroether feedstock being no more than 2:1, said method being selective toward the production of a further fluorinated polyfluoroether having at least one hydrogen atom and the same carbon skeletal structure in its molecule as saiD polyfluoroether feedstock, comprising contacting said polyfluoroether feedstock with a mixture of molecular fluorine and inert gas in a reaction zone under reaction conditions at which the polyfluoroether feedstock is in the liquid phase, the amount of inert gas in said mixture being sufficient to moderate the reaction so that it is controllable and the mixture contains about 5 to 75 volume percent molecular fluorine based on the total fluorine and inert gas charged to the reaction zone, the reaction temperature being in the range of about -40* to 0* C., to prepare a further fluorinated polyfluoroether product having at least one hydrogen atom and the same carbon skeleton in its molecule as said polyfluoroether feedstock, said reaction being conducted in the presence of a solvent for said polyfluoroether feedstock and said further fluorinated polyfluoroether product, which solvent is liquid and essentially inert under said reaction conditions.
Claim 8
Dependent Claim
39 words
The method defined in claim 5 wherein said solvent is an alkane or alkyl ether which is perhalogenated or contains only one hydrogen atom in its molecule and is substituted only with one or both of fluorine or chlorine.
Claim 9
Dependent Claim
19 words
The method defined in claim 6 wherein the polyfluoroether feedstock has 2 to 5 carbon atoms in the molecule.
Claim 10
Dependent Claim
58 words
The method defined in claim 7 wherein the total amount of halogen atoms of atomic number 9 to 35 in the molecule of the polyfluoroether feedstock constitutes about 50 to 75 weight percent of the polyfluoroether feedstock molecule and wherein at least two carbon atoms in the molecule of the polyfluoroether feedstock bear at least one hydrogen atom.
Claim 11
Dependent Claim
26 words
The method defined in claim 6 wherein the polyfluoroether feedstock has the structure CHF2CF2(CF2CF2)nCH2OR, in which R is lower alkyl and n is 0 to 4.
Claim 12
Dependent Claim
12 words
The method defined in claim 5 wherein said solvent has the structure
Claim 13
Dependent Claim
26 words
The method defined in claim 10 wherein said polyfluoroether feedstock has the structure CHF2CF2(CF2CF2)nCH2OR, in which R is lower alkyl and n is 0 to 4.
References Cited (Backward Citations)
US3242218A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1978-07-28 | 1979-01-27 | 1979-07-29 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1982-07-28 | 1983-01-27 | 1983-07-29 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1986-07-28 | 1987-01-27 | 1987-07-29 | $7700.00 | Window Closed / Lapsed |