Additional Diverse Halogen Containing Patents (Class 568/684)
  • Patent number: 9617359
    Abstract: Perfluoro-t-butoxyallyl ether and perfluoro-t-butoxypropargyl ether and methods for their synthesis are disclosed. Also disclosed are methods for making polymers from the perfluoro-t-butoxyallyl ether and perfluoro-t-butoxypropargyl ether.
    Type: Grant
    Filed: April 24, 2014
    Date of Patent: April 11, 2017
    Assignee: City University of Hong Kong
    Inventors: Istvan T. Horvath, K. C. Lau, Matthew Y. Lui, Edwin Law, Kwun Chung Paul Wong
  • Patent number: 9353038
    Abstract: A method for preparing a fluorinated vinyl ether compound comprising reacting a fluorinated ether substrate having (i) a hydrogen atom on a carbon atom that is alpha to an etheric oxygen and (ii) a fluorine atom on a carbon atom that is beta to the etheric oxygen, with an organolithium base to provide a reaction product comprising a fluorinated vinyl ether compound.
    Type: Grant
    Filed: April 20, 2009
    Date of Patent: May 31, 2016
    Assignees: BAXTER INTERNATIONAL, INC., BAXTER HEALTHCARE SA
    Inventors: Chialang Grand Huang, Linas V. Kudzma
  • Patent number: 8957258
    Abstract: The present invention provides a symmetrical ether compound which is chlorinated in the ? position and which is useful as an intermediate for medicine and pesticides and as a raw material or a synthetic intermediate for producing a fluorine-containing compound, in particular a bis(1,1-dichloro-3,3,3-trifluoropropyl)ether represented by formula [1] which is obtained by chlorinating a bis(3,3,3-trifluoropropyl)ether. This bis(1,1-dichloro-3,3,3-trifluoropropyl)ether is produced by chlorinating, preferably under ultraviolet light irradiation, a bis(3,3,3-trifluoropropyl)ether [1].
    Type: Grant
    Filed: January 21, 2013
    Date of Patent: February 17, 2015
    Assignee: Kanto Denka Kogyo Co., Ltd.
    Inventors: Toshiaki Okamoto, Chizuko Okazaki
  • Publication number: 20140336419
    Abstract: The present invention provides a symmetrical ether compound which is chlorinated in the ? position and which is useful as an intermediate for medicine and pesticides and as a raw material or a synthetic intermediate for producing a fluorine-containing compound, in particular a bis(1,1-dichloro-3,3,3-trifluoropropyl)ether represented by formula [1] which is obtained by chlorinating a bis(3,3,3-trifluoropropyl)ether. This bis(1,1-dichloro-3,3,3-trifluoropropyl)ether is produced by chlorinating, preferably under ultraviolet light irradiation, a bis(3,3,3-trifluoropropyl)ether.
    Type: Application
    Filed: January 21, 2013
    Publication date: November 13, 2014
    Inventors: Toshiaki Okamoto, Chizuko Okazaki
  • Publication number: 20140073139
    Abstract: The present invention is a plasma etching gas comprising a fluorocarbon having 3 or 4 carbon atoms, the fluorocarbon including at least one unsaturated bond and/or ether linkage, and including a bromine atom, and a plasma etching method comprising subjecting a silicon oxide film on a substrate to plasma etching through a mask using a process gas, the process gas being the plasma etching gas. This plasma etching gas exhibits excellent etching selectivity, and has a short atmospheric lifetime and a low environmental impact. This plasma etching method makes it possible to selectively subject a silicon oxide film to plasma etching at a high etching rate without causing an increase in surface roughness.
    Type: Application
    Filed: March 14, 2012
    Publication date: March 13, 2014
    Applicant: ZEON CORPORATION
    Inventor: Takefumi Suzuki
  • Publication number: 20110098511
    Abstract: There is provided a method of preparing a high purity fluorine-containing ether which inhibits a side reaction generating an unsaturated bond and assures low cost and simple steps. When preparing the fluorine-containing ether by allowing a fluorine-containing alkyl alcohol to react with a fluorinated olefin in the presence of a basic compound, a reaction is terminated at a stage before a conversion ratio of the fluorine-containing alkyl alcohol reaches 75%.
    Type: Application
    Filed: June 11, 2009
    Publication date: April 28, 2011
    Applicant: DAIKIN INDUSTRIES LTD.
    Inventors: Michiru Kagawa, Aoi Nakazono, Akiyoshi Yamauchi, Meiten Koh
  • Publication number: 20110082312
    Abstract: The present invention relates to a process for the preparation of compounds containing CF3O groups using compounds containing at least one group Y, in which Y=—Hal, —OSO2(CF2)zF, —OSO2CzH2z+1 (z=1-10), —OSO2F, —OSO2Cl, —OC(O)CF3— or —OSO2Ar, to a process for the preparation of compounds containing CF3O groups using KOCF3 and/or RbOCF3, and to novel compounds containing CF3O groups, and to the use thereof.
    Type: Application
    Filed: May 4, 2009
    Publication date: April 7, 2011
    Applicant: MERCK PATENT GESELLSCHAFT MIT DESCHRANKTER HAFTUNG
    Inventors: Nikolai (Mykola) Ignatyev, Wolfgang Hierse, Martin Seidel, Andreas Bathe, Jens Schroeter, Karsten Koppe, Thorsten Meier, Peter Barthen, Walter Frank
  • Publication number: 20100249302
    Abstract: Provided is a liquid composition including a perfluorochloroether solvent that contains a perfluorochloroether compound having a (chlorine content/fluorine content) value within the range of from 1.2 to 4.5; and an organic compound that has a fluorine content of from 0 to 79% by weight and that is dissolved in the perfluorochloroether solvent, wherein the (chlorine content/fluorine content) value is a value defined by the following formula: (chlorine content/fluorine content)value=(number of chlorine atoms in perfluorochloroether×atomic weight of chlorine atom)/(number of fluorine atoms in perfluorochloroether×atomic weight of fluorine atom).
    Type: Application
    Filed: March 30, 2010
    Publication date: September 30, 2010
    Applicant: FUJIFILM CORPORATION
    Inventors: Hiroki SUGIURA, Masayuki HARADA, Takayuki ITO
  • Patent number: 7375254
    Abstract: Provided is a process of obtaining 1,1,1,3,3,3-hexafluoro-2-propanol (“HFIP”) from a composition comprising an HFIP hydrolyzable precursor. The HFIP hydrolyzable precursor is a compound, other than sevoflurane itself, that has an intact 1,1,1,3,3,3-hexafluoroisopropoxy moiety[(CF3)2CHO—], and contains one or more moieties susceptible to acidic hydrolysis, such that HFIP is released upon such treatment. The process is useful, among other things, for recovering HFIP from waste streams associated with the synthesis of the inhalation anesthetic, fluoromethyl 2,2,2-trifluoro-1-(trifluoromethyl)ethyl ether (“sevoflurane”). The process includes heating the composition with a strong protic acid to a temperature effective to hydrolyze at least some of the HFIP hydrolyzable precursor to HFIP, and then isolating the HFIP from the heated composition.
    Type: Grant
    Filed: May 24, 2005
    Date of Patent: May 20, 2008
    Assignee: Baxter International Inc.
    Inventors: Leonid A. Rozov, Ralph A. Lessor
  • Patent number: 7319173
    Abstract: A process for preparing (per)fluorohalogenethers having general formula: wherein: A and A?, equal to our different from each other, are selected among Cl, Br, H; m=1, 2; n=0, 1; R1 is a fluorinated substituent, preferably perfluorinated, selected from the following groups: C1-C20 linear or branched alkylic; C3-C7 cycloalkylic; aromatic, C6-C10 arylalkyl; heterocyclic or C5-C10-alkylheterocyclic; preferably perfluoroalkyl; R? is as defined in the application; by reaction of carbonyl compounds having formula: wherein: R1 and n are as above; u=0, 1; R? is as defined in the application; in liquid phase, with elemental fluorine and with olefinic compounds of formula: CAF?CA?F2??(III) wherein A and A? are as above, at temperatures from ?120° C. to ?20° C., preferably from ?100° C. to ?40° C., optionally in the presence of an inert solvent under the reaction conditions.
    Type: Grant
    Filed: January 28, 2005
    Date of Patent: January 15, 2008
    Assignee: Solvay Solexis S.p.A.
    Inventors: Vito Tortelli, Stefano Millefanti, Pierangelo Calini
  • Patent number: 7288682
    Abstract: A process for separating bifunctional perfluoropolyethers (PFPEs) having two terminations —CH2OH from their mixtures with monofunctional PFPEs with one termination —CH2OH, of general formula X1—O—Rf—Y ??(I) wherein Rf is a perfluoropolyoxyalkylene chain having a number average molecular weight of 500-10,000; X1 and Y are end groups selected from —CFXCH2OH (wherein X is F or CF3), —CF3, —CF2Cl, —CF2CF2Cl, —C3F6Cl, —CF2Br, —CF2CF3, wherein at least one of the two end groups is —CFXCH2OH, said process comprising the steps of: a) addition of the PFPE mixture to an adsorbing solid phase, under stirring; b) filtration of the mixture obtained in a): c) addition to the solid phase filtered in b), of a PFPE mixture having an average functionality higher than that of the PFPE mixture of the liquid filtered in b); c2) filtration of the mixture obtained in c); and subsequent treatment of the solid phase separated in c2) with a polar solvent obtaining a liquid containing the PFPE having high functionality.
    Type: Grant
    Filed: July 8, 2005
    Date of Patent: October 30, 2007
    Assignee: Solvay Solexis S.p.A.
    Inventors: Alexandre Tchistiakov, Simonetta Fontana, Claudio Tonelli
  • Patent number: 7247757
    Abstract: A method of producing a fluorine-containing vinyl ether compound, which contains the step of: fluorinating a compound of formula (I-1) or (I-2): wherein R is a straight-chain, branched-chain or cyclic alkyl group that may have a substituent and/or an unsaturated bond; X11 is a halogen atom other than a fluorine atom; X12, X13, and X14 each independently are a halogen atom; X21 is a halogen atom other than a fluorine atom; and X22 and X23 each independently are a halogen atom.
    Type: Grant
    Filed: October 5, 2005
    Date of Patent: July 24, 2007
    Assignee: Fujifilm Corporation
    Inventors: Takayuki Ito, Yushi Kaneko
  • Patent number: 7230147
    Abstract: The invention concerns a method for functionalizing a double bond and, more particularly, a double bond bearing a metalloid atom. Said functionalization is produced by the action of perhalogenated sulphonyl chloride on the carbon bearing sulphur in the presence of a free radical initiator, preferably by homolytic cleavage. The invention is useful in organic synthesis.
    Type: Grant
    Filed: June 11, 2004
    Date of Patent: June 12, 2007
    Assignee: Shasun Pharma Solutions Limited
    Inventor: Nicolas Roques
  • Patent number: 7193118
    Abstract: A method for producing a fluoroalkyl ether, which comprises reacting a fluoroalkyl alcohol with a fluorinated olefin in the presence of a solvent and a catalyst, wherein the fluoroalkyl alcohol and the fluorinated olefin are continuously supplied into a reactor, a reaction product containing the fluoroalkyl ether is continuously withdrawn from the reactor, and the reaction is carried out while the concentration of the fluoroalkyl alcohol present in the reactor is maintained to be at most 7 mass % based on the total organic component present in the reactor. According to the present invention, a fluoroalkyl ether having a high purity can be produced in an industrial scale and at a high reaction rate.
    Type: Grant
    Filed: December 5, 2005
    Date of Patent: March 20, 2007
    Assignee: Asahi Glass Company, Limited
    Inventors: Hidekazu Okamoto, Masazumi Nagai, Kazuya Oharu
  • Patent number: 7109383
    Abstract: The invention relates to a fluorine-containing allyl ether compound represented by the formula 1, wherein R represents an organic group containing at least one fluorine atom and an alicyclic structure. The invention further relates to a fluorine-containing copolymer containing a first unit derived from the fluorine-containing allyl ether represented by the formula 1; and a second unit derived from a vinyl monomer.
    Type: Grant
    Filed: September 26, 2003
    Date of Patent: September 19, 2006
    Assignee: Central Glass Company, Limited
    Inventors: Satoru Kobayashi, Katsunori Kawamura, Kazuhiro Yamanaka, Haruhiko Komoriya, Kazuhiko Maeda
  • Patent number: 7102031
    Abstract: It is an object to obtain from a mixture of a specific diene compound (1) and a compound (2) with the same molecular weight and molecular formula hard to separate by distillation, the diene compound (1) in high purity without using any special reagent or complicated technique. Namely, the present invention provides a method of inducing the Claisen rearrangement reaction of the compound (2) in a mixture containing CR1R2?CR3CFR4CR5R6OCR7?CR8R9 (1) and CFR1R2CR3?CR4CR5R6OCR7?CR8R9 (2), and separating the diene compound (1) from a Claisen rearrangement reaction product; or converting the Claisen rearrangement reaction product into a derivative and then separating the diene compound (1) from the derivative of the Claisen rearrangement reaction product. Wherein, R1 to R9 each represent a fluorine atom or the like.
    Type: Grant
    Filed: June 10, 2004
    Date of Patent: September 5, 2006
    Assignee: Asahi Glass Company, Limited
    Inventors: Masao Iwaya, Hidekazu Okamoto, Kazuya Oharu
  • Patent number: 6987204
    Abstract: Provided is a process of obtaining 1,1,1,3,3,3-hexafluoro-2-propanol (“HFIP”) from a composition comprising an HFIP hydrolyzable precursor. The HFIP hydrolyzable precursor is a compound, other than sevoflurane itself, that has an intact 1,1,1,3,3,3-hexafluoroisopropoxy moiety[(CF3)2CHO—], and contains one or more moieties susceptible to acidic hydrolysis, such that HFIP is released upon such treatment. The process is useful, among other things, for recovering HFIP from waste streams associated with the synthesis of the inhalation anesthetic, fluoromethyl 2,2,2-trifluoro-1-(trifluoromethyl)ethyl ether (“sevoflurane”). The process includes heating the composition with a strong protic acid to a temperature effective to hydrolyze at least some of the HFIP hydrolyzable precursor to HFIP, and then isolating the HFIP from the heated composition.
    Type: Grant
    Filed: January 12, 2004
    Date of Patent: January 17, 2006
    Assignee: Baxter International Inc.
    Inventors: Leonid A. Rozov, Ralph A. Lessor
  • Patent number: 6849194
    Abstract: Highly fluorinated, saturated, and unsaturated fluoroethers are efficient, economical, non-ozone-depleting fire extinguishing agents used alone or in blends with other fire extinguishing agents in total flooding and portable systems. Methods for producing ethers, halogenated ether intermediates, and fluoroethers are disclosed. Novel fluoroether compositions are disclosed. Fluoroether extinguishing mixtures, methods, and systems are disclosed.
    Type: Grant
    Filed: May 12, 2003
    Date of Patent: February 1, 2005
    Assignee: PCBU Services, Inc.
    Inventors: Mark Robin, Thomas F. Rowland, John Chien, Janet Boggs, Mitchel Cohn, Vicki Hedrick, Stephan Brandstadter
  • Patent number: 6835856
    Abstract: A process for preparing (per)fluorohalogenethers having general formula (I): (R)nC(F)mOCAF—CA′F2  (I) wherein: A and A′, equal to or different the one from the other, are Cl or Br or one is selected from A and A′ and hydrogen and the other is halogen selected from Cl, Br; R═F, or a fluorinated, preferably perfluorinated, substituent, selected from the following groups: linear or branched C1-C20 alkyl more preferably C1-C10; C3-C7 cycloalkyl; aromatic, C6-C10 arylalkyl, alkylaryl; C5-C10 heterocyclic or alkylheterocyclic; when R is fluorinated or perfluorinated alkyl, cycloalkyl, arylalkyl, alkylaryl, it can optionally contain in the chain one or more oxygen atoms; when R is fluorinated it can optionally contain one or more H atoms and/or one or more halogen atoms different from F: n is an integer and is 1 or 2; m=3-n; by reaction of carbonyl compounds having formula (II): (R)pC(F)q(O)  (II) wherein: p is an integer and is 1 or 2; q is an integer a
    Type: Grant
    Filed: August 5, 2003
    Date of Patent: December 28, 2004
    Assignee: Solvay Solexis S.p.A.
    Inventors: Vito Tortelli, Pierangelo Calini
  • Patent number: 6770776
    Abstract: Fluorocarbon compounds are synthesized by reacting a substrate hydrocarbyl compound containing at least one sp3-hybridized halophoric carbon atom bearing at least two halogen atom substituents, at least one of which is a halogen atom having an atomic number greater than that of fluorine and the at least one halophoric carbon atom being bonded to at least one chalcogen, with at least one reactant which comprises a complex of a Bronstedt base with a defined amount n of hydrofluoric acid, n being at least 3 and not greater than 20.
    Type: Grant
    Filed: September 25, 2001
    Date of Patent: August 3, 2004
    Assignee: Rhone-Poulenc Chimie
    Inventors: Robert Janin, Laurent Saint-Jalmes
  • Publication number: 20040087817
    Abstract: A method for the preparation of sevoflurane which comprises (a) providing a liquid mixture of (CF3)2CHOCH2Cl, hydrogen fluoride, and an amine and (b) reacting the mixture, to form (CF3)2CHOCH2F.
    Type: Application
    Filed: August 20, 2003
    Publication date: May 6, 2004
    Applicant: Medeva Pharmaceuticals PA, Inc.
    Inventor: Ross C. Terrell
  • Patent number: 6653512
    Abstract: Described are compositions comprising perfluoroalkyl haloalkyl ethers and, optionally, surfactant; uses for perfluoroalkyl haloalkyl ether compounds and compositions thereof, optionally comprising surfactant; and perfluoroalkyl haloalkyl ethers.
    Type: Grant
    Filed: January 14, 1999
    Date of Patent: November 25, 2003
    Assignee: 3M Innovative Properties Company
    Inventors: Frederick E. Behr, Richard M. Flynn
  • Publication number: 20020156329
    Abstract: A fluorine-containing diene represented by the formula 1:
    Type: Application
    Filed: May 15, 2002
    Publication date: October 24, 2002
    Applicant: ASAHI GLASS COMPANY, LIMITED
    Inventors: Kimiaki Kashiwagi, Hidenobu Murofushi, Norihide Sugiyama, Masakuni Sato, Atsushi Watakabe
  • Patent number: 6316636
    Abstract: Fluorocarbon compounds are synthesized by reacting a substrate hydrocarbyl compound containing at least one sp3-hybridized halophoric carbon atom bearing at least two halogen atom substituents, at least one of which is a halogen atom having an atomic number greater than that of fluorine and the at least one halophoric carbon atom being bonded to at least one chalcogen, with at least one reactant which comprises a complex of a Bronstedt base with a defined amount n of hydrofluoric acid, n being at least 3 and not greater than 20.
    Type: Grant
    Filed: February 28, 1996
    Date of Patent: November 13, 2001
    Assignee: Rhone-Poulenc Chimie
    Inventors: Robert Janin, Laurent Saint-Jalmes
  • Patent number: 6300526
    Abstract: Hydro-2,2-difluoroalkylvinylethers having the formula CF2═CH—O—RA  (I) wherein RA is a radical containing fluorine, optionally containing halogens such as Cl, Br, I, hydrogen, functional groups CM, COOR′, CON(R′)2, SO2OR′, m wherein R′ is a C1-C5 alkyl, RA being selected from the following: a linear or branched, saturated or unsaturated C2-C20 fluoroalkyl, or a saturated or unsaturated C4-C6 fluorinated cyclic group wherein optionally from 1 to 2 carbon atoms are substituted with oxygen atoms, or a linear, branched saturated or unsaturated, C3-C15 fluorooxyalkyl group, containing one or Core oxygen atoms.
    Type: Grant
    Filed: July 29, 1999
    Date of Patent: October 9, 2001
    Assignee: Austmont S.p.A.
    Inventors: Walter Navarrini, Antonio Russo
  • Patent number: 6300532
    Abstract: A process for catalytic addition of haloalkanes to alkenes involving the step of reacting the haloalkane with the alkene in the presence of a catalyst. The catalyst is an organophosphite compound represented by the following formula: P(ORa)(ORb)(ORc), where Ra, Rb, and Rc are each an alkyl group or an aralkyl group.
    Type: Grant
    Filed: December 15, 1998
    Date of Patent: October 9, 2001
    Assignee: AlliedSignal Inc.
    Inventors: Michael Van Der Puy, Timothy Rech Demmin
  • Patent number: 6288127
    Abstract: The present invention relates to an anesthetic composition containing a fluoroether compound and a physiologically acceptable Lewis acid inhibitor. This composition exhibits improved stability and does not readily degrade in the presence of a Lewis acid.
    Type: Grant
    Filed: November 23, 1999
    Date of Patent: September 11, 2001
    Assignee: Abbott Laboratories & Central Glass Co LTD
    Inventors: Christopher Bieniarz, Steve H. Chang, Keith R. Cromack, Shuyen L. Huang, Toshikazu Kawai, Manami Kobayashi, David Loffredo, Rajagopalan Raghavan, Earl R. Speicher, Honorate A. Stelmach
  • Patent number: 6271422
    Abstract: A method for fluoromethylation of an alcohol via halogenative decarboxylation. The method includes the step of reacting an alcohol of the formula R1C(CX3)2OH with an alpha-haloester of the formula X2CH2CO2R2 to form an alpha-alkoxy ester, wherein R1 is selected from the group consisting of hydrogen and alkyl groups, wherein R2 is selected from the group consisting of hydrogen and alkyl groups, wherein X, at each occurrence, is independently selected from the group consisting of hydrogen, bromine, fluorine, and chlorine, and wherein X2 is selected from the group consisting of bromine and chlorine. The resulting alpha-alkoxy ester is saponified to form an alpha-alkoxy acid which is heated at reflux with lead tetraacetate and a chlorinating agent to form a chloride compound of the formula R1C(CX3)2OCH2Cl. The chloride compound is converted to a fluoride compound of the formula R1C(CX3)2OCH2F with a fluorinating agent.
    Type: Grant
    Filed: June 1, 2000
    Date of Patent: August 7, 2001
    Assignee: Abbott Laboratories
    Inventors: Christopher Bieniarz, Kornepati V. Ramakrishna, Christopher Behme
  • Patent number: 6245949
    Abstract: A method for fluoromethylating halogenated alcohols. The method includes the step of providing an alpha-halogenated alcohol of the formula R1C(CX3)2OH, wherein R1 is selected from the group consisting of hydrogen and alkyl groups. The alpha-halogenated alcohol is reacted with a first compound of the formula CH2(OR2)2 in the presence of an acid catalyst to form an acetal. The resulting acetal is then chlorinated with a chlorinating agent to form a chloride compound of the formula R1C(CX3)2OCH2Cl. The chloride compound is then converted to a fluoride compound of the formula R1C(CX3)2OCH2F using a fluorinating agent.
    Type: Grant
    Filed: June 1, 2000
    Date of Patent: June 12, 2001
    Assignee: Abbott Laboratories
    Inventors: Christopher Bieniarz, Kornepati V. Ramakrishna
  • Patent number: 6100434
    Abstract: A method for synthesizing fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether. The method includes the step of combining in the presence of aluminum trichloride a quantity of hexafluoroisopropanol and a quantity of either 1,3,5-trioxane or paraformaldehyde to produce sevochlorane. The resulting sevochlorane is then combined with an alkali metal fluoride to produce fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether.
    Type: Grant
    Filed: March 26, 1999
    Date of Patent: August 8, 2000
    Assignee: Abbott Laboratories
    Inventors: Christopher Bieniarz, Kornepati V. Ramakrishna, Christopher Behme
  • Patent number: 6072088
    Abstract: A compound having the formula:CF.sub.3 CH.sub.2-w (H.sub.1-x CH.sub.2-y R.sub.m R'.sub.n CH.sub.1-z).sub.p H.sub.2-q CF.sub.3wherein w=0, 1 or 2; x=0 or 1; y=0, 1 or 2; m=0, 1 or 2; n=0 or 1; z=0 or 1; p=1 or 2; and q=0, 1 or 2; with the provisos that 1.ltoreq.w+x.ltoreq.2, 1.ltoreq.q+z.ltoreq.2, and p.multidot.y=p(m+2n)+(p-1)(x+z)+q+w+x+z-2; and wherein R includes the halogens having an atomic number greater than 9, and radicals having a valence of 1, and wherein R' is a group having a valence of 2, and a process for preparing the compound.
    Type: Grant
    Filed: August 10, 1999
    Date of Patent: June 6, 2000
    Assignee: Alliedsignal Inc.
    Inventor: Michael Van Der Puy
  • Patent number: 5990176
    Abstract: The present invention relates to an anesthetic composition containing a fluoroether compound and a physiologically acceptable Lewis acid inhibitor. This composition exhibits improved stability and does not readily degrade in the presence of a Lewis acid.
    Type: Grant
    Filed: January 27, 1997
    Date of Patent: November 23, 1999
    Assignees: Abbott Laboratories, Central Glass Company Ltd.
    Inventors: Christopher Bieniarz, Steve H. Chang, Keith R. Cromack, Shuyen L. Huang, Toshikazu Kawai, Manami Kobayashi, David Loffredo, Rajagopalan Raghavan, Earl R. Speicher, Honorate A. Stelmach
  • Patent number: 5886239
    Abstract: A method of preparing fluoromethyl 2,2,2-trifluoro-1-(trifluoromethyl)ethyl ether (sevoflurane) and structurally related monofluoromethyl ethers in which the monochloromethyl ether precursor thereof is reacted with a sterically hindered tertiary amine hydrofluoride salt.
    Type: Grant
    Filed: November 21, 1997
    Date of Patent: March 23, 1999
    Assignee: Baxter International Inc.
    Inventors: Linas V. Kudzma, Ralph A. Lessor, Leonid A. Rozov, Keith Ramig
  • Patent number: 5877357
    Abstract: The invention relates to a process for preparing perhaloethers from perhaloolefins and to a few "per se" new classes of perhaloethers thereby obtained.The process consists in reacting a perhalomonoolefin with a fluoroxy compound R.sub.x --OF (wherein R.sub.x represents a perhalogenated alkyl radical) at a temperature not exceeding 20.degree. C. in a liquid reaction medium and in the presence of inert gases.
    Type: Grant
    Filed: April 7, 1997
    Date of Patent: March 2, 1999
    Assignee: Ausimont S.p.A.
    Inventors: Antonio Marraccini, Antonio Pasquale, Tiziana Fiorani, Walter Navarrini
  • Patent number: 5753776
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: May 19, 1998
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5693747
    Abstract: Bisperfluoroalkyl-substituted diols containing sulfide, sulfone or polysulfide linkages and a method for making them are described. These diols can react with isocyanates to form urethanes; diisocyanates to form polyurethanes; chloroformates to form carbonates; with carboxylic, sulfuric or phosphoric acids or derivatives to form carboxylate esters, sulfate esters, phosphate esters respectively. These diol compounds and their derivatives are useful for imparting oil and water repellency to substrates such as glass, wood, paper, leather, wool, cotton, polyester and other substrates.
    Type: Grant
    Filed: July 3, 1996
    Date of Patent: December 2, 1997
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Ted Deisenroth, Marlon Haniff
  • Patent number: 5639921
    Abstract: A process for producing difluoromethyl ethers and esters by reacting an ether or an acid with a cadmium, zinc or bismuth compound containing the CF.sub.3 group and selected from the group consisting of Cd(CF.sub.3).sub.2, Zn(CF.sub.3).sub.2, Bi(CF.sub.3).sub.3, CdHal(CF.sub.3), ZnHal(CF.sub.3), BiHal(CF.sub.3).sub.2 and BiHal.sub.2 (CF.sub.3) in the presence of a Lewis acid.
    Type: Grant
    Filed: June 15, 1995
    Date of Patent: June 17, 1997
    Assignee: Solvay Fluor und Derivate GmbH
    Inventors: Dieter Naumann, Wieland Tyrra, Regina Moeckel
  • Patent number: 5621144
    Abstract: New compounds are described typically having the formula CH.sub.3 C(CH.sub.2 R).sub.3 or ZCH.sub.2 C(CH.sub.2 R).sub.3 where R is a fluorohydrocarbon or perfluorocarbon group, preferably containing 4-16 carbon atoms and more F atoms that H atoms. Z is a hydrophilic group which may make the compound self-emulsifiable. The compounds are useful as oxygen transport agents in vivo, for which purpose aqueous emulsions are used, as a blood substitute.
    Type: Grant
    Filed: January 9, 1995
    Date of Patent: April 15, 1997
    Assignee: Isis Innovation Limited
    Inventor: Stephen R. Cooper
  • Patent number: 5571870
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: May 10, 1994
    Date of Patent: November 5, 1996
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5536885
    Abstract: Disclosed herein is a process for making perfluoro(alkyl vinyl ethers) by fluorination with elemental fluorine of selected novel partially fluorinated (di) chloroethyl ethers, followed by dehalogenation to the corresponding perfluoro(alkyl vinyl ether). The perfluoro(alkyl vinyl ethers) are useful as monomers for molding resins and elastomers.
    Type: Grant
    Filed: June 7, 1994
    Date of Patent: July 16, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Ming-Hong Hung, Shlomo Rozen
  • Patent number: 5523496
    Abstract: Perfluoropolyethers and perhalogenated chlorofluoroether polymers are disclosed that can be prepared by fluorinating polymers made by the polymerization of acetals, ketals, polyacetals, polyketals and orthoesters with elemental fluorine.
    Type: Grant
    Filed: April 5, 1994
    Date of Patent: June 4, 1996
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5481046
    Abstract: Iodine terminated liquid telechelic telomers of chlorotrifluoroethylene (CTFE) containing an average of more than 1 CTFE unit per molecule are novel compounds. The telomers can be prepared by a photochemically initiated reaction between liquified CTFE and either elemental iodine or the telogen ICF.sub.2 CFClI at temperatures below about 50.degree. C.
    Type: Grant
    Filed: July 5, 1994
    Date of Patent: January 2, 1996
    Assignee: Dow Corning Corporation
    Inventors: Richard D. Chambers, Martin P. Greenhall, Antony P. Wright
  • Patent number: 5481028
    Abstract: A process for the preparation of perfluoroalkyl iodides, especially perfluoroethyl iodide, by reaction of perfluorinated compounds which contain a carbon carbon double bond with ICl in HF solvent in the presence of Lewis acid catalysts. The compounds are used as telogens for the telomerization of tetrafluoroethylene to long-chain perfluoroalkyl iodides.
    Type: Grant
    Filed: August 12, 1994
    Date of Patent: January 2, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Viacheslav A. Petrov, Carl G. Krespan
  • Patent number: 5461117
    Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.
    Type: Grant
    Filed: June 13, 1994
    Date of Patent: October 24, 1995
    Assignee: Exfluor Research Corporation
    Inventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
  • Patent number: 5457242
    Abstract: A process for preparing the novel compound 2-bromo, 1', 2'-dichloroperfluoro diethyl ether of formula:BrCFhd 2--CF.sub.2 --O--CFCl--CF.sub.2 Clwhere BrCF.sub.2 --CF.sub.2 OF is reacted with the olefin CFCl.dbd.CFCl, with bromohypofluorite being introduced into the reaction mixture in the form of a solution in an inert solvent based on chlorofluorohydrocarbon.
    Type: Grant
    Filed: November 8, 1993
    Date of Patent: October 10, 1995
    Assignee: Ausimont S.r.l.
    Inventors: Pierangelo Calini, Guglielmo Gregorio, Giorgio Guglielmo
  • Patent number: 5455371
    Abstract: A process for producing difluoromethyl ethers and esters by reacting an ether or an acid with a cadmium, zinc or bismuth compound containing the CF.sub.3 group and selected from the group consisting of Cd(CF.sub.3).sub.2, Zn(CF.sub.3).sub.2,Bi(CF.sub.3).sub.3, CdHal(CF.sub.3), ZnHal(CF.sub.3), BiHal(CF.sub.3).sub.2 and BiHal.sub.2 (CF.sub.3) in the presence of a Lewis acid.
    Type: Grant
    Filed: June 15, 1993
    Date of Patent: October 3, 1995
    Assignee: Solvay Fluor und Derivative GmbH
    Inventors: Dieter Naumann, Wieland Tyrra, Regina Moeckel
  • Patent number: 5446211
    Abstract: The synthesis of fluorinated dimethyl ethers of the formula CF.sub.2 HOCCl.sub.x F.sub.y H.sub.3-(x+y) wherein x is 0, 1 or 2; y is 1, 2 or 3; and wherein (x+y) is 1, 2 or 3. The process involves chlorination of methyl difluoromethyl ether in the presence of a solvent to form a chlorinated reaction product of the formula CF.sub.2 HOCH.sub.3-z Cl.sub.z wherein z is 1, 2 or 3. The process may also be carried out in the presence of oxygen in order to inhibit the formation of CF.sub.2 HOCCl.sub.3. The resulting compound(s) is then fluorinated with HF before or after separation, to give a fluorinated reaction product including the aforementioned fluorinated dimethyl ethers.
    Type: Grant
    Filed: April 1, 1994
    Date of Patent: August 29, 1995
    Assignee: Hampshire Chemical Corp.
    Inventors: Gerald J. O'Neill, Robert J. Bulka
  • Patent number: 5420359
    Abstract: Normally liquid chlorofluoroether compositions consisting or consisting essentially of one or a selected mixture of perhalogenated chlorofluoroether compounds are provided by direct fluorination of the corresponding chloroether or chlorofluoroether precursors. The compositions are useful, for example, as heat transfer agents, blood substitutes, and solvents.
    Type: Grant
    Filed: October 7, 1993
    Date of Patent: May 30, 1995
    Assignees: Minnesota Mining and Manufacturing Company, HemaGen/PFC
    Inventors: George G. I. Moore, Richard M. Flynn, Robert J. Kaufman, Thomas J. Richard
  • Patent number: 5416244
    Abstract: An improved process for the production of isoflurane is disclosed. Isoflurane is formed by the exhaustive chlorination of 2,2,2-trifluoroethyl difluoromethyl ether with chlorine gas. The reaction mixture, preferably without purification or refining, is treated with UV light in the presence of isopropanol to reduce 1,1-dichloro-2,2,2-trifluoroethyl difluoromethyl ether, the other major component thereof, to isoflurane. Isoflurane is thereby obtained in yields of at least 80%.
    Type: Grant
    Filed: September 30, 1991
    Date of Patent: May 16, 1995
    Assignee: Ohmeda Pharmaceutical Products Division Inc.
    Inventors: Leonid A. Rozov, Fernando Quiroz, Gerald G. Vernice
  • Patent number: RE35568
    Abstract: The present invention is directed to a method for replacing a carboxylic acid group with a fluorine .[.group.]. in a halogenated aliphatic carboxylic acid compound having the formula, R-COOH, to prepare a fluorinated product having the formula, R-F, wherein R is a halogenated aliphatic group including straight- and branched-chain aliphatic groups selected from the group consisting of halogenated aliphatic and .Iadd.halogenated .Iaddend.alkoxy-substituted .[.halogenated.]. aliphatic groups, wherein the method comprises the step of (a) reacting the halogenated aliphatic carboxylic acid compound with bromine trifluoride, and (b) recovering the fluorinated product.
    Type: Grant
    Filed: November 16, 1994
    Date of Patent: July 22, 1997
    Assignee: Ohmeda Pharmaceutical Products Division Inc.
    Inventors: Donald F. Halpern, Mark L. Robin