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US4345092A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for alkyl perfluoro(4,7-dioxa-5-methyl-8-fluoroformylnonanoate

Assignee: EIDP Inc
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Filing: 1980-08-04
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Granted: 1982-08-17
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Expires: 2000-08-04
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Abstract

Abstract Improved process for making an alkyl perfluoro(4,7-dioxa-5-methyl-8-fluoroformylnonanoate) from hexafluorpropylene oxide and either a monoalkyl difluoromalonyl fluoride or an alkyl perfloro(4-oxa-5-fluoroformylhexanoate) in the presence of fluoride ion catalyst which comprises carrying out the reaction in the presence of a medium consisting essentially of two aprotic liquids, one of the liquids in major proportion and being a poor solvent for methyl perfluoro(4-oxa-5-fluoroformylhexanoate), and the other liquid in minor proportion, being a good solvent for the same compound and being a solvent for the fluoride ion catalyst to the extent of at least 0.001% by weight at 20° C. The product is an intermediate to a valuable fluorinated comonomer used for making fluorinated ion exchange resins.

Inventors

  • 👤 Paul R. Resnick

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-08 13:20
CPC Classifications
C; C07; C07C; C07C69/00; C07C69/66; C07C69/67; C07C69/708

Claims Analysis

Total Claims: 11
Claim 1
Independent Claim 186 words
In a process for preparing a product compound of the formula ##STR11## where R is alkyl of 1-6 carbon atoms, wherein a reactant of the formula ##STR12## where R is as defined above is contacted with hexafluoropropylene oxide in the presence of a fluoride compound which provides fluoride ion catalyst, the improvement comprising contacting said reactant with hexafluoropropylene oxide and said catalyst in the presence of a medium consisting essentially of two components, component A being 50 to 98% by volume of an aprotic liquid dinitrile in which methyl perfluoro (4-oxa-5-fluoroformylhexanoate) dissolves to the extent of less than 10 g/100 g of A at 20° C. or tetramethylenesulfone, and component B being 50 to 2% by volume of an aprotic liquid glyme, lactone or mononitrile in which said fluoride compound is soluble to the extent of at least 0.001% by weight at 20° C. and in which methyl perfluoro(4-oxa-5-fluoroformylhexanoate) dissolves to the extent of at least 10 g/100 g of B at 20° C., separating a heavier phase which contains said product compound from a lighter phase, and separating said product compound from said heavier phase.
Claim 2
Dependent Claim 186 words
In a process for preparing a product compound of the formula ##STR11## where R is alkyl of 1-6 carbon atoms, wherein a reactant of the formula ##STR12## where R is as defined above is contacted with hexafluoropropylene oxide in the presence of a fluoride compound which provides fluoride ion catalyst, the improvement comprising contacting said reactant with hexafluoropropylene oxide and said catalyst in the presence of a medium consisting essentially of two components, component A being 50 to 98% by volume of an aprotic liquid dinitrile in which methyl perfluoro (4-oxa-5-fluoroformylhexanoate) dissolves to the extent of less than 10 g/100 g of A at 20° C. or tetramethylenesulfone, and component B being 50 to 2% by volume of an aprotic liquid glyme, lactone or mononitrile in which said fluoride compound is soluble to the extent of at least 0.001% by weight at 20° C. and in which methyl perfluoro(4-oxa-5-fluoroformylhexanoate) dissolves to the extent of at least 10 g/100 g of B at 20° C., separating a heavier phase which contains said product compound from a lighter phase, and separating said product compound from said heavier phase.
Claim 3
Dependent Claim 56 words
The process of claim 1 wherein component A is such that methyl perfluoro(4-oxa-5-fluoroformylhexanoate) dissolves in it to the extent of no more than 6 g/100 g of A at 20° C., and component B is such that methyl perfluoro(4-oxa-5-fluoroformylhexanoate) dissolves in it to the extent of at least 20 g/100 g of B at 20° C.
Claim 4
Dependent Claim 27 words
The process of claim 2 wherein said medium consists of 85 to 98% by volume of component A and 15 to 2% by volume of component B.
Claim 5
Dependent Claim 30 words
The process of claim 3 wherein component B is such that methyl perfluoro(4-oxa-5-fluoroformylhexanoate) dissolves in it to the extent of at least 100 g/100 g of B at 20° C.
Claim 6
Dependent Claim 27 words
The process of claim 4 wherein said medium consists of 85 to 95% by volume of component A and 15 to 5% by volume of component B.
Claim 7
Dependent Claim 20 words
The process of claim 5 wherein component A is a dinitrile or tetramethylene sulfone, and component B is a glyme.
Claim 8
Dependent Claim 16 words
The process of claim 6 wherein component A is adiponitrile, and component B is bis[2-(2-methoxyethoxy)ethyl] ether.
Claim 9
Dependent Claim 70 words
The process of claim 1 wherein said fluoride compound is selected from the group consisting of potassium, rubidium and cesium fluorides, said component A is selected from the group consisting of malononitrile, succinonitrile, glutaronitrile, adiponitrile, methylmalononitrile, pimelonitrile, suberonitrile, phthalonitrile and tetramethylenesulfone, and said component B is selected from the group consisting of monoethyleneglycol dimethyl ether, diethyleneglycol dimethyl ether, triethyleneglycol dimethyl ether, tetraethyleneglycol dimethyl ether, 4-butyrolactone, 5-valerolactone, 6-caprolactone, acetonitrile and propionitrile.
Claim 10
Dependent Claim 12 words
The process of claim 7 wherein said fluoride compound is potassium fluoride.
Claim 11
Dependent Claim 15 words
The process of claim 1, 4, 7 or 9 wherein R is -CH 3 .

References Cited (Backward Citations)

US3674820A Cited
US4153804A Cited
US4131740A Cited
US4138426A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1985-08-16 1986-02-15 1986-08-17 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1989-08-16 1990-02-15 1990-08-17 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1993-08-16 1994-02-15 1994-08-17 $7700.00 Window Closed / Lapsed

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