Methods of making fluorinated ethers, fluorinated ethers,...

Details Methods of making fluorinated ethers, fluorinated ethers,... Methods of making fluorinated ethers, fluorinated ethers,...

2011-08-02

2011-08-02

Eashoo, Mark (Department: 1767)

Compositions

Fire-extinguishing

C568S677000, C568S681000, C568S683000

Reexamination Certificate

active

07988877

ABSTRACT:
A method of making a fluorinated ether includes combining, in a polar aprotic solvent: a fluorinated alcohol represented by the formula X—Rf1CH2OH, and a fluorinated sulfonate ester represented by the formula Rf2CH2OS(═O)2Rf3, and base; and obtaining a fluorinated ether represented by the formula Y—Rf1CH2OCH2Rf2—Y. Rf1is selected from perfluorinated C1-C10alkylene groups having from 1 to 10 carbon atoms and partially fluorinated C1-C10alkylene groups, and derivatives thereof having catenated heteroatom(s). X represents H, F, or an HOCH2— group. Rf2is selected from perfluorinated C1-C10alkyl groups and partially fluorinated C1-C10alkyl groups, and derivatives thereof having catenated heteroatom(s). Rf3is a C1-C4alkyl group. Y represents H, F, or an Rf2CH2OCH2— group. A variant method, useful for preparing symmetric fluorinated ethers, is also disclosed. The present disclosure also provides fluorinated ethers preparable according to the methods. Use of fluorinated ethers in various applications is also disclosed.

REFERENCES:
patent: 3903012 (1975-09-01), Brandreth
patent: 4169807 (1979-10-01), Zuber
patent: 5089152 (1992-02-01), Flynn et al.
patent: 5125089 (1992-06-01), McCambridge
patent: 5125978 (1992-06-01), Flynn et al.
patent: 5182342 (1993-01-01), Feiring et al.
patent: 5210106 (1993-05-01), Dams et al.
patent: 5474657 (1995-12-01), Hansen
patent: 5539008 (1996-07-01), Dams et al.
patent: 5718293 (1998-02-01), Flynn et al.
patent: 5839311 (1998-11-01), Grenfell et al.
patent: 5925611 (1999-07-01), Flynn et al.
patent: 6023002 (2000-02-01), Behr et al.
patent: 6046368 (2000-04-01), Lamanna et al.
patent: 6080448 (2000-06-01), Leiner et al.
patent: 6399729 (2002-06-01), Farnham et al.
patent: 6759374 (2004-07-01), Milbrath et al.
patent: 7128133 (2006-10-01), Costello et al.
patent: 7390427 (2008-06-01), Costello et al.
patent: 2007/0051916 (2007-03-01), Flynn et al.
patent: 2007/0054186 (2007-03-01), Costello et al.
patent: 2008/0139683 (2008-06-01), Flynn et al.
patent: 2 312 097 (2007-12-01), None
“Organic Chemistry” (Brown and Foote, 2nd Edition, 1998, Saunders Publishing, pp. 291-292).
Rakhimov et al., “Synthesis of Di(polyfluoroalkyl) Ethers”, Russian Journal of Applied Chemistry, vol. 77, No. 9, 2004, pp. 1561-1563.
Research Disclosure, “Hydrofluoroethers as Fluoromonomer Reaction Media”, No. 405, Jan. 1998, pp. 81-82.
Rakhimov et al., “Reaction of Polyfluorinated Alcohols with Thionyl Chloride”, Russian Journal of Organic Chemistry, vol. 35, No. 3, 1999, pp. 794-795.
L. Z. Gandel'sman et al., “1,1-Dihydropolyfluoroalkylation of N-Alkylanilines,” Journal of Organic Chemistry of the USSR, vol. 14, No. 4, Part 2, Apr. 1978, 4 pages.
Johncock, “Sulphur-Oxygen Versus Carbon-Oxygen Scission in Trifluoromethanesulphonates”, Journal of Fluorine Chemistry, vol. 4, 1974, pp. 25-33.
Burdon et al., “Trifluoromethanesulphonate Esters and Their Alkylating Properties”, Tetrahedron, vol. 21, 1965, pp. 1-4.
“Hydrofluoroacetal Compounds and Processes for their Preparation and Use”, U.S. Appl. No. 12/164,369, filed Jun. 30, 2008.
Hals, Lyle J., et al., “Fluorine Compounds, Organic: Fluoro Ethers and Amines”, Database CA [Online], XP002581100 retrieved from STN Database accession No. 65:72826, Chemical Abstracts Service, Columbus, Ohio, US, 1966, abstract.
Henne, A., L., et al., “Fluorinated Ethers”, Journal of the American Chemical Society, 1950, vol. 72, pp. 4378-4380.
Beilstein Database [Online], Beilstein Institute for Organic Chemistry, Database Accession No. BRN 1824673 Abstract & Journal of Organic Chemistry, Frankfurt-Main, DE, 1960, vol. 25, pp. 1682-1683.
PCT International Searching Authority, “Invitation to Pay Additional Fees and, Where Applicable, Protest Fee”, International Application Number: PCT/US2009/060326, Applicant's Reference: 64680WO003, May 5, 2010.
PCT Written Opinion of the International Searching Authority, PCT/US2009/060326, mailed Dec. 27, 2010, 11 pages.
PCT International Search Report, PCT/US2009/060326, mailed Dec. 27, 2010, 5 pages.

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