Fluorine Patents (Class 568/683)
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Publication number: 20100185020Abstract: The present invention provides a continuous process for the production of 1,2,2,2-tetrafluoroethyl difluoromethyl ether (desflurane) which comprises feeding continuously optimum molar quantities of 1-chloro-2,2,2-trifluoroethyl difluoromethyl ether (CF3CHClOCHF2, Isoflurane) and anhydrous hydrogen fluoride, in a reactor in the vapour phase over a fluorination catalyst system comprising a metal pentahalide absorbed on a supporting substrate at a temperature ranging from 100° C. to 180° C., and separating 1,2,2,2-tetrafluoroethyl difluoromethyl ether (desflurane) continuously from the reactor. The process of the present invention enables continuous removal of desflurane product thereby minimizing co-production of byproducts and resulting in high conversion efficiency and yield of desflurane.Type: ApplicationFiled: July 11, 2008Publication date: July 22, 2010Applicant: Piramal Healthcare LimitedInventors: Sivaramakrishnan Hariharan, Owen Chambers, Abhay Atmaram Upare, Damodharan Satagopan
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Patent number: 7750192Abstract: Crude sevoflurane product comprising unacceptably high levels of HFIP can be purified by combining the crude sevoflurane product with sufficient water to produce a multiphase mixture, fractionally distilling the multiphase mixture, removing sevoflurane from the distilling multiphase mixture as an azeotrope with water, and separating substantially pure sevoflurane from the azeotrope.Type: GrantFiled: August 2, 2006Date of Patent: July 6, 2010Assignee: Halocarbon Products CorporationInventors: Barry Jones, Joel Swinson
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Publication number: 20100151395Abstract: Disclosed are a protective film-removing solvent for re-moving a protective film laminated on a photoresist film, which contains at least a hydrofluoroether; and a method of photoresist patterning in liquid immersion lithography, using the protective film-removing solvent.Type: ApplicationFiled: February 16, 2010Publication date: June 17, 2010Inventors: Keita Ishiduka, Masaaki Yoshida, Satoshi Maemori
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Patent number: 7732647Abstract: A process for purifying crude fluoromethyl 1,1,1,3,3,3-hexafluoroisopropyl ether (sevoflurane). The crude sevoflurane is repeatedly washed with water under conditions and for a time sufficient to reduce the level of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) to no more than 200 ppm or no more than 100 ppm.Type: GrantFiled: December 27, 2007Date of Patent: June 8, 2010Assignee: Halocarbon Products CorporationInventors: Barry Jones, Joel Swinson, Paul Mazzell
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Publication number: 20100108094Abstract: The present invention relates to a solvent composition for removing radioactive substance, characterized by comprising at least one selected from hydrofluorocarbon, hydrofluoroether, and perfluoroketone as a medium for transporting the radioactive substance, and a method for removing a radioactive substance characterized by using the solvent composition for removing.Type: ApplicationFiled: July 29, 2005Publication date: May 6, 2010Inventors: Junichi Ishikawa, Hideaki Kikuchi, Kazuhito Nagashima
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Publication number: 20100108934Abstract: 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. Rf1 is selected from perfluorinated C1-C10 alkylene groups having from 1 to 10 carbon atoms and partially fluorinated C1-C10 alkylene groups, and derivatives thereof having catenated heteroatom(s). X represents H, F, or an HOCH2— group. Rf2 is selected from perfluorinated C1-C10 alkyl groups and partially fluorinated C1-C10 alkyl groups, and derivatives thereof having catenated heteroatom(s). Rf3 is a C1-C4 alkyl 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.Type: ApplicationFiled: November 3, 2008Publication date: May 6, 2010Inventors: Richard M. Flynn, Michael J. Bulinski, Michael G. Costello
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Patent number: 7651627Abstract: The present invention provides an apparatus comprising a device and a mechanism for heat transfer comprising a hydrofluoroether heat-transfer fluid wherein the heat transfer fluid is represented by the following structure: Rf—O—Rh—O—Rf? wherein O is oxygen; Rf and Rf? are, independently, a fluoroaliphatic group, wherein each Rf and Rf? contain 1 hydrogen atom; Rh is independently a linear, branched or cyclic alkylene group having from 2 to about 8 carbon atoms and at least 4 hydrogen atoms, and wherein the hydrofluoroether compound is free of —O—CH2—O—. Another embodiment of the present invention is a method therefor.Type: GrantFiled: May 13, 2008Date of Patent: January 26, 2010Assignee: 3M Innovative Properties CompanyInventors: Michael G. Costello, Richard M. Flynn, Frederick E. Behr
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Publication number: 20100010255Abstract: The present invention provides a novel ?-fluoromethoxycarboxylic ester represented by Formula (1): (CF3)2C(OCH2F)COOR wherein R is a hydrocarbon group that may have a substituent; a process for producing 1,1,1,3,3,3-hexafluoroisopropyl fluoromethyl ether, the process including hydrolyzing and decarboxylating the ?-fluoromethoxycarboxylic ester; and a process for producing an ?-fluoromethoxycarboxylic ester represented by Formula (1): (CF3)2C (OCH2F)COOR, the process including reacting an ?-hydroxycarboxylic ester represented by Formula (2): (CF3)2C(OH)COOR with a halofluoromethane in the presence of an alkaline compound. According to the present invention, 1,1,1,3,3,3-hexafluoroisopropyl fluoromethyl ether (sevoflurane), which is known as an anesthetic compound, can be efficiently produced at low cost.Type: ApplicationFiled: June 27, 2007Publication date: January 14, 2010Applicant: Daikin Industries LTdInventors: Tatsuya Ohtsuka, Yoshichika Kuroki, Atsukhi Suzuki
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Publication number: 20100004490Abstract: The present invention refers to a process for the preparation of chloromethyl 2,2,2-trifluoro-1-(trifluoromethyl) ethyl ether (sevochlorane), which consists of reacting hexafluoroisopropanol with: a formaldehyde equivalent selected between paraformaldehyde or 1,3,5-trioxane, a chlorinating agent selected from the group consisting of oxalyl chloride, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride, sulfuryl chloride and thionyl chloride, and a strong acid selected from the group consisting of concentrated or fuming sulfuric acid. Said process provides sevochlorane in high purity and yield, which can be converted to sevoflurane by known means.Type: ApplicationFiled: September 29, 2006Publication date: January 7, 2010Applicant: Cr1stalia Productos Quimicos Farmaceuticos LTDAInventors: Ogari Pacheco, Antonio Carlos Teixeira, Edson Luiz Lima, Maria Alice Böckelmann
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Publication number: 20090326083Abstract: The present disclosure provides a compound according to the formula: Rf1[CH(—O—CH(3-m)Rf2m)(—O—CF2—CFH—Rf3)]n ??[I] wherein n is 1 or 2, wherein m is 1, 2 or 3, wherein, when n is 1, Rf1 is selected from the group consisting of highly fluorinated alkyl groups which are linear, branched, cyclic, or a combination thereof, which may optionally be substituted, and which may optionally contain one or more catenated heteroatoms; wherein, when n is 2, Rf1 is selected from the group consisting of highly fluorinated alkylene groups which are linear, branched, cyclic, or a combination thereof, which may optionally be substituted, and which may optionally contain one or more catenated heteroatoms; wherein each Rf2 is independently selected from the group consisting of alkyl groups which are linear, branched, cyclic, or a combination thereof, which may optionally be substituted, and which may optionally contain one or more catenated heteroatoms; wherein at least one Rf2 is highly fluorinated; wherein each Rf3 is indepType: ApplicationFiled: June 30, 2008Publication date: December 31, 2009Inventors: Richard M. Flynn, Michael G. Costello
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Publication number: 20090171128Abstract: A process for purifying crude fluoromethyl 1,1,1,3,3,3-hexafluoroisopropyl ether (sevoflurane). The crude sevoflurane is repeatedly washed with water under conditions and for a time sufficient to reduce the level of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) to no more than 200 ppm or no more than 100 ppm.Type: ApplicationFiled: December 27, 2007Publication date: July 2, 2009Inventors: Barry Jones, Joel Swinson, Paul Mazzell
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Publication number: 20090156861Abstract: The present invention provides a process for producing 1,1,1,3,3,3-hexafluoro-2-methoxypropane, wherein a novel compound, 2-methoxy-2-trifluoromethyl-3,3,3-trifluoropropionic acid or a salt thereof is decarboxylated, or wherein an olefin compound represented by chemical formula (4): CF2?C(CF3)(OCH3) is reacted with a fluorinating agent; and a process for producing 2-methoxy-2-trifluoromethyl-3,3,3-trifluoropropionic acid or a salt thereof by reacting a hydroxycarboxylic ester with a methylating agent and then hydrolyzing the reaction product, or hydrolyzing the hydroxycarboxylic ester and then reacting the resulting product with a methylating agent. In accordance with the invention, 1,1,1,3,3,3-hexafluoro-2-methoxypropane, which is useful as a raw material for, for example, the anesthetic Sevoflurane, can be produced efficiently and at low cost.Type: ApplicationFiled: May 31, 2007Publication date: June 18, 2009Applicant: DAIKIN INDUSTRIES, LTD.Inventors: Tatsuya Ohtsuka, Yoshihiro Yamamoto, Yoshichika Kuroki, Atsushi Suzuki, Akinari Sugiyama
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Publication number: 20090043133Abstract: A compound comprising Formula I, or a mixture thereof, Rf—OCFHCF2O—[CH2CH2O]x—[C3H7O]y-A ??Formula I wherein Rf is CnF2n+1, n is 1 to about 6, x is a mixture of positive integers and is 4 or greater, y is 0 to about 4, provided that the ratio of y to x is equal to or less than 0.25, A is RfOCHFCF2 or CmH2m+1, and m is 0 to about 24 and its use in lowering surface tension and imparting improved surface effects is disclosed.Type: ApplicationFiled: August 6, 2007Publication date: February 12, 2009Inventors: Peter Michael Murphy, Andrew Edward Feiring, Stephan James McLain, Jessica Sinks
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Publication number: 20090018350Abstract: A fluorine-containing ether compound with a fluorine content increased, the fluorine content being enhanced by fluorinating a polymer including a repeating unit represented by the following Formula (I): wherein Rh1 represents a divalent linkage group; Rf2 represents an perfluoroalkylene group; each of Rf3 and Rf4 independently represents a fluorine atom, a perfluoroalkyl group or a perfluoroalkoxy group, and any two of Rf2, Rf3 and Rf4 may be combined with each other to form a ring.Type: ApplicationFiled: April 9, 2008Publication date: January 15, 2009Applicant: FUJIFILM CorporationInventors: Takayuki ITO, Toshimitsu Sakuma
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Publication number: 20080306309Abstract: An azeotrope comprising desflurane (CF3CFHOCF2H) and hydrogen fluoride (HF). The azeotrope can be prepared by fractionally distilling a crude mixture of desflurane and HF. Purer desflurane can be readily and easily separated from the azeotrope. It is emphasized that this abstract is provided to comply with the rules requiring an abstract which will allow a searcher or other reader quickly to ascertain the subject matter of the technical disclosure. It is submitted with the understanding that it will not be used to interpret or limit the scope or meaning of the appended issued claims.Type: ApplicationFiled: February 9, 2006Publication date: December 11, 2008Applicant: HALOCARBON PRODUCTS CORPORATIONInventors: Paul Mazzell, Barry Jones, Neville Pavri, Joel Swinson
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Publication number: 20080149878Abstract: The present invention relates to the use of end groups Y, where Y stands for CF3O— or F5S—, as hydrophobic end group in surface-active compounds, corresponding novel compounds, and processes for the preparation of these compounds.Type: ApplicationFiled: December 22, 2005Publication date: June 26, 2008Inventors: Peer Kirsch, Klaus-Dieter Franz, Andreas Ruhl
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Patent number: 7390427Abstract: The present invention provides an apparatus comprising a device and a mechanism for heat transfer comprising a hydrofluoroether heat-transfer fluid wherein the heat transfer fluid is represented by the following structure: Rf—O—Rh—O—Rf? wherein O is oxygen; Rf and Rf? are, independently, a fluoroaliphatic group, wherein each Rf and Rf? contain 1 hydrogen atom; Rh is independently a linear, branched or cyclic alkylene group having from 2 to about 8 carbon atoms and at least 4 hydrogen atoms, and wherein the hydrofluoroether compound is free of —O—CH2—O—. Another embodiment of the present invention is a method therefor.Type: GrantFiled: September 28, 2006Date of Patent: June 24, 2008Assignee: 3M Innovative Properties CompanyInventors: Michael G. Costello, Richard M. Flynn, Frederick E. Behr
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Publication number: 20080139683Abstract: A hydrofluoroether compound comprises two terminal, independently fluoroalkyl or perfluoroalkyl groups and an intervening oxytetrafluoroethylidene moiety (—OCF(CF3)—) bonded through its central carbon atom to an alkoxy- or fluoroalkoxy-substituted fluoromethylene moiety (—CF(OR)—), each of the terminal groups optionally comprising at least one catenated heteroatom.Type: ApplicationFiled: December 6, 2006Publication date: June 12, 2008Inventors: Richard M. Flynn, Michael G. Costello, Daniel R. Vitcak
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Publication number: 20080132731Abstract: A process for preparing fluorinated ethers, such as desflurane, comprises reacting the corresponding chlorinated ether, such as isoflurane, with anhydrous hydrogen fluoride in the vapor phase in the presence of chromia catalyst. It is emphasized that this abstract is provided to comply with the rules requiring an abstract which will allow a searcher or other reader quickly to ascertain the subject matter of the technical disclosure. It is submitted with the understanding that it will not be used to interpret or limit the scope or meaning of the appended issued claims.Type: ApplicationFiled: January 6, 2006Publication date: June 5, 2008Applicant: HALOCARBON PRODUCTS CORPORATIONInventors: Joel Swinson, Barry Jones, Danny Graham, Neville Pavri
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Patent number: 7375254Abstract: 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: GrantFiled: May 24, 2005Date of Patent: May 20, 2008Assignee: Baxter International Inc.Inventors: Leonid A. Rozov, Ralph A. Lessor
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Patent number: 7288682Abstract: 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: GrantFiled: July 8, 2005Date of Patent: October 30, 2007Assignee: Solvay Solexis S.p.A.Inventors: Alexandre Tchistiakov, Simonetta Fontana, Claudio Tonelli
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Patent number: 7247757Abstract: 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: GrantFiled: October 5, 2005Date of Patent: July 24, 2007Assignee: Fujifilm CorporationInventors: Takayuki Ito, Yushi Kaneko
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Patent number: 7230142Abstract: A process for purifying fluoromethyl 1,1,1,3,3,3-hexafluoroisopropyl ether containing at least 1,1,1,3,3,3-hexafluoroisopropyl alcohol. The purifying process comprises the treatment of causing fluoromethyl 1,1,1,3,3,3-hexafluoroisopropyl ether containing at least 1,1,1,3,3,3-hexafluoroisopropyl alcohol, to contact with a basic aqueous solution. The basic aqueous solution contains a basic substance in an amount providing a chemical equivalent ratio of the basic substance to 1,1,1,3,3,3-hexafluoroisopropyl alcohol being within a range of not less than 1.Type: GrantFiled: March 3, 1999Date of Patent: June 12, 2007Assignee: Central Glass Company, LimitedInventors: Toshikazu Kawai, Matsue Kawamura
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Patent number: 7230143Abstract: A method in which organic matter found in a crude sevoflurane may be separated, identified, and quantified using a CARBOWAX™ (polyethylene glycol) capillary gas chromatographic column or an alkyl polysiloxane capillary gas chromatographic column. Also provided is a process control method for the production of sevoflurane, wherein the content of a particular component in one of the following steps is determined, and in that, assuming this as a variable, the treatment condition of the step is adjusted: 1) a step of extracting, or cooling to form two layers, and/or distilling a mixture of crude sevoflurane and hydrogen fluoride (HF) in order to isolate the majority of the sevoflurane and 2) an optional step of purifying the crude sevoflurane and 3) a step of distilling crude sevoflurane. Also provided is a method for determining the impurity level of a purified sevoflurane that is acceptable for use in human/animal anesthesia.Type: GrantFiled: January 4, 2005Date of Patent: June 12, 2007Assignee: Halocarbon Products CorporationInventors: Barry Jones, Ashot Khrimian, Joel Swinson, Paul Cross
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Patent number: 7230147Abstract: 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: GrantFiled: June 11, 2004Date of Patent: June 12, 2007Assignee: Shasun Pharma Solutions LimitedInventor: Nicolas Roques
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Patent number: 7202386Abstract: 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: GrantFiled: August 20, 2003Date of Patent: April 10, 2007Assignee: Minrad Inc.Inventor: Ross C. Terrell
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Patent number: 7193118Abstract: 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: GrantFiled: December 5, 2005Date of Patent: March 20, 2007Assignee: Asahi Glass Company, LimitedInventors: Hidekazu Okamoto, Masazumi Nagai, Kazuya Oharu
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Patent number: 7193119Abstract: To provide a process for producing a fluorinated alkyl ether, whereby a sufficient reaction rate can be attained even under mild reaction conditions, and a post-process such as distillation after the reaction can be efficiently carried out. A process for producing a fluorinated alkyl ether, which comprises introducing an aprotic polar solvent, a fluorinated ether, a catalyst, a fluorinated alkyl alcohol and a fluorinated olefin into a reactor, and then, reacting the fluorinated alkyl alcohol with the fluorinated olefin, characterized in that the ratio of the two components of the aprotic polar solvent and the fluorinated ether introduced into the reactor is the aprotic polar solvent/the fluorinated ether=5/95 to 80/20 by mass ratio.Type: GrantFiled: February 7, 2006Date of Patent: March 20, 2007Assignee: Asahi Glass Company, LimitedInventors: Masazumi Nagai, Hidekazu Okamoto, Kazuya Oharu
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Patent number: 7153397Abstract: A process for the purification of fluoromethyl hexafluoroisopropyl ether which comprises contacting a crude composition comprising fluoromethyl hexafluoroisopropyl ether and hexafluoroisopropyl alcohol with a modifier in the presence of which the vapor pressure of the ether and/or the alcohol is modified whereby the difference in vapor pressure of the ether and the alcohol increases relative to the difference in vapor pressure of the ether and alcohol in the absence of the modifier and separating the ether from the alcohol.Type: GrantFiled: December 21, 2001Date of Patent: December 26, 2006Assignee: Ineos Fluor Holdings LimitedInventors: Andrew Paul Sharratt, Lee Colin Draper
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Patent number: 7141704Abstract: Process for obtaining hydrofluoroethers of formula (I): A-(Rf)n0—CF(Rf1)—O—Rh??(I) wherein a mono- or bifunctional carbonyl compound of formula (IV): B—Rf—C(O)Rf1??(IV) is reacted with at least one equivalent of a fluoroformate of formula (III) R—OC(O)F??(III) in the presence of an ion fluoride compound (catalyst) and of a dipolar aprotic organic compound, liquid and inert under the reaction conditions.Type: GrantFiled: March 26, 2004Date of Patent: November 28, 2006Assignee: Solvay Solexis S.P.A.Inventors: Walter Navarrini, Marco Galimberti, Giovanni Fontana
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Patent number: 7128133Abstract: The present invention provides an apparatus comprising a device and a mechanism for heat transfer comprising a hydrofluoroether heat-transfer fluid wherein the heat transfer fluid is represented by the following structure: Rf—O—Rh—O—Rf? wherein: O is oxygen; Rf and Rf? are, independently, a fluoroaliphatic group, wherein each Rf and Rf? contain 1 hydrogen atom; Rh is independently a linear, branched or cyclic alkylene group having from 2 to about 8 carbon atoms and at least 4 hydrogen atoms, and wherein the hydrofluoroether compound is free of —O—CH2—O—. Another embodiment of the present invention is a method therefor.Type: GrantFiled: December 16, 2003Date of Patent: October 31, 2006Assignee: 3M Innovative Properties CompanyInventors: Michael G. Costello, Richard M. Flynn, Frederick E. Behr
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Patent number: 7125834Abstract: This invention provides the following: an amphiphilic functional substance with lipophilicity, affinity for supercritical CO2, and if necessary hydrophilicity comprising an oligoolefin chain and a perfluoroalkyl group(s) at a single end thereof or at both ends thereof with or without the intervention of a poly(oxyalkylene) chain, which enables the utilization of supercritical CO2 as a reaction medium; a photopolymerizable functional substance comprising an oligoolefin chain and a reversible photopolymerization/dissociation group(s) at a single end thereof or at both ends thereof and a functional substance comprising a photo- and/or thermodissociable polymer obtained by photopolymerization of the aforementioned photopolymerizable functional substance, which can be utilized as recycle polymers; a hydrolyzable functional substance comprising a polymer obtained by chain-elongating plural oligoolefin chains through ester linkages, which can be utilized as a recycle polymer; and a functional substance capable of foType: GrantFiled: November 22, 2001Date of Patent: October 24, 2006Assignee: San-Ei Kougyou CorporationInventor: Takashi Sawaguchi
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Patent number: 7102031Abstract: 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: GrantFiled: June 10, 2004Date of Patent: September 5, 2006Assignee: Asahi Glass Company, LimitedInventors: Masao Iwaya, Hidekazu Okamoto, Kazuya Oharu
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Patent number: 7091374Abstract: Fluorinated compounds and emulsions including the compounds. The compositions are useful as oxygen carriers and surfactants. In one embodiment, the fluorinated compound is pH sensitive. In one embodiment, the fluorinated compound is a vitamin E derivative. In one embodiment, the fluorinated compound is a vitamin K derivative.Type: GrantFiled: April 23, 2004Date of Patent: August 15, 2006Assignee: Sonus Pharmaceuticals, Inc.Inventors: Yuehua Zhang, Manjari Lal, Andrew Leo, Nagesh Palepu
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Patent number: 7060850Abstract: The present invention includes methods and compositions for increasing the fluorous nature of an organic compound by reacting it with at least one fluorous compound to produce a fluorous tagged organic compound. The increased fluorous nature of the fluorous tagged organic compound can then be utilized to separate the fluorous organic compound from untagged reagents, reactants, catalysts and/or products derived therefrom. The resultant fluorous tagged organic compound can be subjected to subsequent chemical transformations, wherein the fluorous nature of the tagged compound is utilized to increase the ease of separation of the fluorous tagged organic compound from untagged reagents, reactants, catalysts and/or products derived therefrom, after each chemical transformation.Type: GrantFiled: July 11, 2003Date of Patent: June 13, 2006Assignee: Fluorous Technologies IncorporatedInventors: Wei Zhang, Zhiyong Luo, Tadamichi Nagashima, Christine Hiu-Tung Chen, Marvin S. Yu
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Patent number: 7034190Abstract: A process for the production of fluoromethylhexafluoroisopropylether which comprises contacting bis(fluoromethyl)ether with hexafluoroisopropyl alcohol in which the molar ratio of the ether to alcohol is in excess of 2:1. The reaction takes place in the presence of a molar ratio of acid to hexafluoroisopropyl alcohol of 2:1 to 10:1.Type: GrantFiled: December 21, 2001Date of Patent: April 25, 2006Assignee: Ineos Fluor Holdings LimitedInventors: Andrew Paul Sharratt, Lee Colin Draper
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Patent number: 7019178Abstract: A process for the purification of fluoromethyl hexafluoroisopropyl ether involving contacting a crude composition containing impure fluoromethyl hexafluoroisopropyl ether with an adsorbent having pores with a range of pore sizes whereby the difference between the smallest and largest pore size is at least 1 nm. The adsorbent suitably is a form of silica, alumina, or carbon.Type: GrantFiled: December 21, 2001Date of Patent: March 28, 2006Assignee: Ineos Fluor Holdings LimitedInventors: Andrew P. Sharratt, Stuart Corr
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Patent number: 6987204Abstract: 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: GrantFiled: January 12, 2004Date of Patent: January 17, 2006Assignee: Baxter International Inc.Inventors: Leonid A. Rozov, Ralph A. Lessor
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Patent number: 6911513Abstract: A novel fluoropolymer which can be an optical resin material having a low refractive index and excellent heat resistance, and a novel fluorinated diene compound having two unsaturated bonds, capable of presenting such a fluoropolymer, are presented. Further, by virtue of the low refractive index and excellent heat resistance, the polymer presents a high performance optical transmitter and a plastic optical fiber. A fluorinated diene compound represented by CF2?CFCF(ORf)CF2OCF?CF2 (wherein Rf is a perfluoroalkyl group such as a trifluoromethyl group), and a fluoropolymer thereof. Further, an optical transmitter made by using such a fluoropolymer, and a plastic optical fiber having a core comprising such a fluoropolymer and a fluorinated low molecular weight compound contained therein as a refractive index-increasing agent.Type: GrantFiled: April 29, 2004Date of Patent: June 28, 2005Assignee: Asahi Glass Company, LimitedInventors: Kimiaki Kashiwagi, Gen Ogawa, Takashi Okazoe, Kunio Watanabe, Eisuke Murotani, Kazuya Oharu
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Patent number: 6849194Abstract: 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: GrantFiled: May 12, 2003Date of Patent: February 1, 2005Assignee: PCBU Services, Inc.Inventors: Mark Robin, Thomas F. Rowland, John Chien, Janet Boggs, Mitchel Cohn, Vicki Hedrick, Stephan Brandstadter
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Patent number: 6800786Abstract: Provided is a method for the preparation of desflurane wherein isoflurane is reacted with 0.7-1.2 mol. % of antimony pentachloride and 1.3-2.2 molar equivalents of hydrogen fluoride. Typically, the method is conducted by addition of hydrogen fluoride to a mixture of isoflurane and antimony pentachloride. After the addition of hydrogen fluoride is completed, the reaction is preferably maintained at temperatures of about 9-18° C. for about 6 to 7 hours, before being quenched.Type: GrantFiled: August 21, 2003Date of Patent: October 5, 2004Assignee: Baxter International, Inc.Inventors: Leonid A. Rozov, Ralph A. Lessor
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Patent number: 6770776Abstract: 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: GrantFiled: September 25, 2001Date of Patent: August 3, 2004Assignee: Rhone-Poulenc ChimieInventors: Robert Janin, Laurent Saint-Jalmes
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Patent number: 6756458Abstract: A novel polymer useful as an optical resin material excellent in heat resistance, a novel monomer for obtaining the polymer, etc., are provided. A fluorinated diene represented by CF2═CF(CF2)nC(CF3)ROCF═CF2 (wherein R is a fluorine atom or a trifluoromethyl group, and n is an integer of from 1 to 3), and a polymer thereof.Type: GrantFiled: December 2, 2002Date of Patent: June 29, 2004Assignee: Asahi Glass Company, LimitedInventors: Kimiaki Kashiwagi, Gen Ogawa, Masakuni Sato, Kazuya Oharu, Isamu Kaneko, Norihide Sugiyama, Shin Tatematsu
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Publication number: 20040073054Abstract: The present invention includes methods and compositions for increasing the fluorous nature of an organic compound by reacting it with at least one fluorous compound to produce a fluorous tagged organic compound. The increased fluorous nature of the fluorous tagged organic compound can then be utilized to separate the fluorous organic compound from untagged reagents, reactants, catalysts and/or products derived therefrom. The resultant fluorous tagged organic compound can be subjected to subsequent chemical transformations, wherein the fluorous nature of the tagged compound is utilized to increase the ease of separation of the fluorous tagged organic compound from untagged reagents, reactants, catalysts and/or products derived therefrom, after each chemical transformation.Type: ApplicationFiled: July 11, 2003Publication date: April 15, 2004Inventors: Wei Zhang, Zhiyong Luo, Tadamichi Nagashima, Christine Hiu-Tung Chen, Marvin S. Yu
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Publication number: 20040030146Abstract: A process for preparing (per)fluorohalogenethers having general formula (I):Type: ApplicationFiled: August 5, 2003Publication date: February 12, 2004Applicant: Solvay Solexis S.p.A.Inventors: Vito Tortelli, Pierangelo Calini
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Patent number: 6677492Abstract: 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: GrantFiled: July 3, 2002Date of Patent: January 13, 2004Assignee: Abbott LaboratoriesInventors: Christopher Bieniarz, Steve H. Chang, Keith R. Cromack, Shuyen L. Huang, Toshikazu Kawai, Manami Kobayashi, David Loffredo, Rajagopalan Raghavan, Earl R. Speicher, Honorats A. Stelmach
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Patent number: 6670511Abstract: A fluorine-containing diene represented by the formula 1: CF2═CF(CF2)nCXYOCF═CF2 Formula 1 wherein each of X and Y which are independent of each other, is an atom selected from a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom and an iodine atom, provided that X and Y are not simultaneously hydrogen atoms or fluorine atoms, and n is an integer of from 1 to 3.Type: GrantFiled: May 15, 2002Date of Patent: December 30, 2003Assignee: Asahi Glass Company LimitedInventors: Kimiaki Kashiwagi, Hidenobu Murofushi, Norihide Sugiyama, Masakuni Sato, Atsushi Watakabe
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Publication number: 20030220527Abstract: A process for preparing perfluoropolyoxyalkylenes having —OCF2H, —OCF2CF2H and —OCF(CF3)H end groups and a number average molecular weight from 120 to 3,000, by decarboxylation of the corresponding perfluoropolyoxyalkylenes having —OCF2COOH, —OCF2CF2COOH, —OCF(CF3)COOH end groups, in the presence of catalytic amounts of salts formed by perfluoropolyoxyalkylenes having end groups selected from —OCF2COOZ, —OCF2CF2COOZ and —OCF(CF3)COOZ, wherein Z is a monovalent cation of the group Ia or Ib or Z is —NR4+ wherein R is hydrogen or a C1-C4 alkyl, using ratios between Z and the —COOH equivalents of the perfluoropolyoxyalkylenes to be decarboxylated from 0.01 to 0.08, at a temperature between 120° C. and 180° C., in the presence of water, at pH <5 and at a pressure comprised between 2 and 80 atmospheres.Type: ApplicationFiled: May 21, 2003Publication date: November 27, 2003Applicant: Solvay Solexis S.p.A.Inventors: Giuseppe Marchionni, Gianfranco Spataro
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Publication number: 20030209685Abstract: 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: ApplicationFiled: May 12, 2003Publication date: November 13, 2003Inventors: Mark Robin, Thomas F. Rowland, John Chien, Janet Boggs, Mitchel Cohn, Vicki Hedrick, Stephan Brandstadter
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Patent number: 6555086Abstract: Processes for separating and recovering hydrogen fluoride from a gaseous mixture of an organic compound and hydrogen fluoride are disclosed. The processes include contacting the gaseous mixture with a solution of an alkali metal fluoride in hydrogen fluoride, separating a gas phase depleted in hydrogen fluoride and containing the organic compound from a liquid phase, and recovering hydrogen fluoride from the liquid phase.Type: GrantFiled: October 7, 1999Date of Patent: April 29, 2003Assignee: Ineos Fluor Holdings LimitedInventors: Paul Nicholas Ewing, Charles John Shields, Robert Elliott Low