Fluorine Patents (Class 568/683)
  • Publication number: 20150122461
    Abstract: A working medium containing 2-methoxy-1,1,1,3,3,3-hexafluoropropane (HFE-356mmz) as a main component is disclosed. This working medium is a new working medium for a boiling-type cooler, which has a light burden on the environment such as the global warming potential, etc., is slightly flammable or flame retardant, has superior thermal and chemical stabilities, and a good compatibility with heat exchangers formed of various metal materials. This medium for the boiling-type cooler can be preferably used as a working medium for a cooler of a PCU (power control unit) of a car.
    Type: Application
    Filed: February 26, 2013
    Publication date: May 7, 2015
    Inventors: Yoshio Nishiguchi, Satoru Okamoto, Fuyuhiko Sakyu
  • Patent number: 8987524
    Abstract: A process for the manufacture of Sevoflurane CF3—CH(OCH2F)—CF3 which comprises (a) manufacturing a substituted malonic acid derivative of formula (I): R1OOC—CH(OCH2X)—COOR2 or of formula (II): R3HNOC—CH(OCH2X)—CONHR4, wherein X is OH or a leaving group which can be substituted by nucleophilic substitution and wherein R1, R2 R3, R4, equal to or different from each other, are independently selected from the group consisting of H, an alkyl group having from 1 to 10 carbon atoms which is optionally substituted by at least one halogen atom, an aralkyl group, and an aryl group; and (b) further reacting said malonic acid derivative as intermediate for the manufacture of Sevoflurane CF3—CH(OCH2F)—CF3.
    Type: Grant
    Filed: August 10, 2010
    Date of Patent: March 24, 2015
    Assignee: Solvay Fluor GmbH
    Inventor: Max Josef Braun
  • Patent number: 8981162
    Abstract: Provided is a method for preparing fluorine-containing vinyl ether. The method comprises: carrying out hydrolytic neutralization on a small molecular weight byproduct which is produced in the process of preparing perfluoropolyether or a perfluorinated surfactant by photooxidation of fluorine-containing olefin; and obtaining fluorine-containing vinyl ether by drying and cracking. The byproduct produced in the process of preparing perfluoropolyether or the perfluorinated surfactant is utilized, thereby solving the emission problem of industrial wastes, reducing environment pollution, and generating available fluorine-containing vinyl ether.
    Type: Grant
    Filed: August 15, 2012
    Date of Patent: March 17, 2015
    Assignee: Zhonghao Chenguang Research Institute of Chemical Industry Company Limited
    Inventors: Ming Zhang, Xucang Yang, Xiaofeng Peng
  • Publication number: 20140323672
    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: Application
    Filed: April 24, 2014
    Publication date: October 30, 2014
    Inventors: Istvan T. HORVATH, K. C. Lau, Matthew Y. Lui, Edwin Law, Kwun Chung Paul Wong
  • Patent number: 8865947
    Abstract: The present invention is directed to a process for preparation of fluorinated alcohols of Formula (I) RfCH2CH2OH??(I) by contacting a fluorinated iodide with an alkyl vinyl ether in the presence of an initiator and a base to generate an intermediate hemi-acetal or aldehyde or a mixture thereof, followed by hydrogenation of the hemi-acetal of Formula (II) RfCH2CH(OCxH2x+1)m(OH)p??(II) or aldehyde of Formula (III) RfCH2CHO??(III) or a mixture thereof, to yield a compound of Formula (I).
    Type: Grant
    Filed: December 6, 2012
    Date of Patent: October 21, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Kenneth Gene Moloy, Sheng Peng
  • Patent number: 8865946
    Abstract: There is provided according to the present invention a process for producing fluoromethyl hexafluoroisopropyl ether ((CF3)2CH—O—CH2F), including: reacting bisfluoromethyl ether with hexafluoroisopropyl alcohol in a solvent substantially immiscible with hydrogen fluoride in the presence of a catalytic amount of a strong acid selected from sulfuric acid and any other acids stronger in acidity than sulfuric acid. The process of the present invention enables industrial production of the fluoromethyl hexafluoroisopropyl ether without using hydrogen fluoride or a large amount of sulfuric acid and thereby without causing a large amount of waste as a by-product.
    Type: Grant
    Filed: April 9, 2010
    Date of Patent: October 21, 2014
    Assignee: Central Glass Company, Limited
    Inventors: Yutaka Katsuhara, Hiroshi Takahashi, Michio Ishida
  • Patent number: 8846747
    Abstract: Provided are compounds which generally have a triketone structure. Examples of the compounds include derivatives of 1,3-cyclohexanedione, such as: 1,3-cyclohexanedione, 2-propanoyl-5-cyclohexyl-; 1,3-cyclohexanedione, 2-propanoyl-5-[4-fluorophenyl]-; 1,3-cyclohexanedione, 2-acetyl-5-[thien-2-yl]-; 1,3-cyclohexanedione, 2-acetyl-5-butyl-; and 1,3-cyclohexanedione, 2-propanoyl-5-[bicyclo[2.2.1]hept-2-en-5-yl]-. The compounds can be used to alter the lifespan of eukaryotic organisms and treat inflammation.
    Type: Grant
    Filed: November 17, 2010
    Date of Patent: September 30, 2014
    Assignees: University of Rochester, Southern Research Institute
    Inventors: David S. Goldfarb, Joseph A. Maddry, Lynn Rasmussen, Ellie Lucille White, Krister Wennerberg
  • Patent number: 8835696
    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: Grant
    Filed: June 11, 2009
    Date of Patent: September 16, 2014
    Assignee: Daikin Industries, Ltd.
    Inventors: Michiru Kagawa, Aoi Nakazono, Akiyoshi Yamauchi, Meiten Koh
  • Patent number: 8729313
    Abstract: The present invention provides a method for forming sevoflurane comprising (i) combining chlorosevo ether, a nucleophilic fluoride reagent, and a solvent comprising sevoflurane to form an initial reaction mixture and (ii) reacting the initial reaction mixture to form additional sevoflurane relative to the amount of sevoflurane present in the initial reaction mixture. The present disclosure is also directed to a method for forming sevoflurane, comprising: initiating a reaction between chlorosevo ether and a nucleophilic fluoride reagent in an initial reaction mixture further comprising a solvent comprising sevoflurane, thereby forming additional sevoflurane relative to the amount of sevoflurane present in the initial reaction mixture.
    Type: Grant
    Filed: August 15, 2011
    Date of Patent: May 20, 2014
    Assignees: Baxter International Inc., Baxter Healthcare SA
    Inventors: Linas Kudzma, Ronald Bell, Yongxian Zeng, Leonid A. Rozov
  • Publication number: 20140091379
    Abstract: A fluorocarbon coating comprises an amorphous structure with CF2 bonds present in an atomic percentage of at least about 15%, and having a refractive index of less than about 1.4. The fluorocarbon coating can be deposited on a substrate by placing the substrate in a process zone comprising a pair of process electrodes, introducing a deposition gas comprising a fluorocarbon gas into the process zone, and forming a capacitively coupled plasma of the deposition gas by coupling energy to the process electrodes.
    Type: Application
    Filed: September 28, 2013
    Publication date: April 3, 2014
    Applicant: Applied Materials, Inc.
    Inventors: Sum-Yee Betty TANG, Martin SEAMONS
  • Publication number: 20130317251
    Abstract: Process for the manufacture of a compound of formula R1OOC—CH(OCH2F)—COOR, (I) or R3HNOC—CH(OCH2F)—CONHR4(II) wherein R1, R2, R3, R4 are equal or different from each other and are independently selected from H; an alkyl group having from 1 to 10 carbon atoms which is optionally substituted by at least one halogen atom; an aralkyl group; or an aryl group, comprising reacting a compound of formula R1OOC—CH(OCH2X)—COOR2 (III) or R3HNOC—CH(OCH2X)—CONHR4(IV) wherein X is a leaving group that can be substituted by nucleophilic substitution, and wherein R1, R2, R3, R4 have the same meaning as above, with at least one source of nucleophilic fluorine.
    Type: Application
    Filed: February 7, 2012
    Publication date: November 28, 2013
    Applicant: SOLVAY SA
    Inventors: Max Josef Braun, Uta Claassen
  • Publication number: 20130265692
    Abstract: A dielectric insulation medium including a hydrofluoro monoether, the hydrofluoro monoether containing at least three carbon atoms. The insulation medium according has high insulation capabilities, in particular a high dielectric strength, and at the same time a low GWP. The invention further includes an insulation medium which is chemically and thermally stable also at temperatures above 140° C., which is non-toxic or has a low toxicity level, and which in addition is non-corrosive and non-explosive.
    Type: Application
    Filed: June 14, 2013
    Publication date: October 10, 2013
    Inventors: Navid Mahdizadeh, Thomas Alfred Paul, Judith Marold, Markus Bujotzek, Patrick Stoller, Max-Steffen Claessens, Per Skarby
  • Patent number: 8535559
    Abstract: Nitrogen-containing fluorochemical ketones are provided that can be useful in apparatuses that includes a device and a mechanism for transferring heat. The provided fluorochemical ketones are stable at temperatures above 170° C., are environmentally friendly, and are economical to produce. The provided apparatuses can be useful for vapor phase soldering of electronic devices.
    Type: Grant
    Filed: March 26, 2010
    Date of Patent: September 17, 2013
    Assignee: 3M Innovative Properties Company
    Inventors: Richard M. Flynn, Michael G. Costello, Michael J. Bulinski, Daniel R. Vitcak, Phillip E. Tuma
  • Patent number: 8530704
    Abstract: The present invention provides a preparation method of fluoromethyl 1,1,1,3,3,3-hexafluoroisopropyl ether by reacting CH2FX with 1,1,1,3,3,3-hexafluoroisopropanol in the presence of acid-binding agent. The reaction can be also preformed in the presence of solvent and/or phase-transfer catalyst. The present method has the advantages of simple reaction, manageable control condition, high material conversion and product yield, and the product can be easily separated. The obtained fluoromethyl 1,1,1,3,3,3-hexafluoroisoprophyl ether can be used as a safe inhalation anesthetics.
    Type: Grant
    Filed: August 25, 2009
    Date of Patent: September 10, 2013
    Assignee: Zhejiang Lantian Environmental Protection Hi-tech Co., Ltd.
    Inventors: Xu Weiguo, Hua Li
  • Publication number: 20130104756
    Abstract: Different solvents for a dampening fluid are disclosed. The solvent is a volatile hydrofluoroether liquid or a volatile silicone liquid. Such liquids have a lower heat of vaporization, a lower surface tension, and better kinematic viscosity compared to water, which is the conventional solvent used in dampening fluids. The dampening fluids, which are relatively nonpolar, can be used in a combination with polar inks to form a new type of digital lithographic printing system.
    Type: Application
    Filed: October 28, 2011
    Publication date: May 2, 2013
    Applicants: Xerox Corporation, Palo Alto Research Center Incorporated
    Inventors: Timothy D. Stowe, Eric Peeters, Chu-Heng Liu
  • Publication number: 20130079558
    Abstract: Disclosed are processes for reacting a perfluorinated olefin with an alcohol, an alkali metal hydroxide, and water in the presence of a phase transfer catalyst to form a reaction product mixture that separates into an aqueous phase and an organic phase. Alcohol may be present in an effective amount sufficient to form a third phase comprising at least 50% of the phase transfer catalyst. The third phase can be separated from the organic phase. Also disclosed are methods for recovering and recycling the phase transfer catalyst used in the reaction.
    Type: Application
    Filed: September 26, 2012
    Publication date: March 28, 2013
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventor: E I DU PONT DE NEMOURS AND COMPANY
  • Publication number: 20130046117
    Abstract: The present invention provides a method for forming sevoflurane comprising (i) combining chlorosevo ether, a nucleophilic fluoride reagent, and a solvent comprising sevoflurane to form an initial reaction mixture and (ii) reacting the initial reaction mixture to form additional sevoflurane relative to the amount of sevoflurane present in the initial reaction mixture. The present disclosure is also directed to a method for forming sevoflurane, comprising: initiating a reaction between chlorosevo ether and a nucleophilic fluoride reagent in an initial reaction mixture further comprising a solvent comprising sevoflurane, thereby forming additional sevoflurane relative to the amount of sevoflurane present in the initial reaction mixture.
    Type: Application
    Filed: August 15, 2011
    Publication date: February 21, 2013
    Applicants: BAXTER HEALTHCARE S.A., BAXTER INTERNATIONAL INC.
    Inventors: Linas Kudzma, Ronald Bell, Yongxian Zeng, Leonid A. Rozov
  • Patent number: 8378149
    Abstract: 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 vapor 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: Grant
    Filed: July 11, 2008
    Date of Patent: February 19, 2013
    Assignee: Piramal Enterprises Limited
    Inventors: Sivaramakrishnan Hariharan, Owen Chambers, Abhay Atmaram Upare, Damodharan Satagopan
  • Publication number: 20120298333
    Abstract: An apparatus is provided that includes a device and a mechanism for heat transfer that includes a provided hydrofluoroether having high temperature stability. Also provided is a method of transferring heat and a composition that includes a provided hydrofluoroether.
    Type: Application
    Filed: August 13, 2012
    Publication date: November 29, 2012
    Inventors: Richard M. Flynn, Michael G. Costello, Michael J. Bulinski
  • Patent number: 8283500
    Abstract: 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: Grant
    Filed: February 9, 2006
    Date of Patent: October 9, 2012
    Assignee: Halocarbon Products Corporation
    Inventors: Paul Mazzell, Barry Jones, Neville Pavri, Joel Swinson
  • Publication number: 20120248376
    Abstract: Processes for synthesizing, recharging, reprocessing and chemical doping of hydrogen storage materials utilizing supercritical fluids. The processes include dissolution or suspension of the material in a supercritical fluid mixed with hydrogen.
    Type: Application
    Filed: May 8, 2012
    Publication date: October 4, 2012
    Applicant: UNIVERSITY OF NEW BRUNSWICK
    Inventor: Sean McGrady
  • Patent number: 8217126
    Abstract: Disclosed herein are novel fluoroolefins of formula Rf—O—(CF2CF2)n(CH2CF2)m—CH?CH2, wherein n is 1 or 2, m is 0 or 1 and Rf is a C1-C8 fluoroalkyl or fluoroalkoxy group. The fluoroolefins may be oxidized to manufacture fluorinated carboxylic acids. Also disclosed are fluoropolymers comprising copolymerized units of the fluoroolefins of the invention and at least one other fluoromonomer.
    Type: Grant
    Filed: October 14, 2008
    Date of Patent: July 10, 2012
    Assignee: E I du Pont de Nemours and Company
    Inventors: Ming-Hong Hung, Sheng Peng
  • Publication number: 20120157708
    Abstract: A process for the manufacture of Sevoflurane CF3—CH(OCH2F)—CF3 which comprises (a) manufacturing a substituted malonic acid derivative of formula (I): R1OOC—CH(OCH2X)—COOR2 or of formula (II): R3HNOC—CH(OCH2X)—CONHR4, wherein X is OH or a leaving group which can be substituted by nucleophilic substitution and wherein R1, R2 R3, R4, equal to or different from each other, are independently selected from the group consisting of H, an alkyl group having from 1 to 10 carbon atoms which is optionally substituted by at least one halogen atom, an aralkyl group, and an aryl group; and (b) further reacting said malonic acid derivative as intermediate for the manufacture of Sevoflurane CF3—CH(OCH2F)—CF3.
    Type: Application
    Filed: August 10, 2010
    Publication date: June 21, 2012
    Applicant: SOLVAY FLUOR GMBH
    Inventor: Max Josef Braun
  • Publication number: 20120107749
    Abstract: There are provided a method of forming a resist pattern, comprising the steps of forming a resist film containing a specific calixarene derivative on a substrate; forming a pattern latent image by selectively exposing the resist film to a high-energy beam; and developing the latent image by removing parts not exposed to the high-energy beam of the resist film with a developer containing at least one fluorine-containing solvent selected form the group consisting of a fluorine-containing alkyl ether and a fluorine-containing alcohol, and the fluorine-containing solvent as a resist developer.
    Type: Application
    Filed: May 20, 2010
    Publication date: May 3, 2012
    Applicant: TOKUYAMA CORPORATION
    Inventors: Seiji Tono, Yuki Chikashige
  • Publication number: 20120041237
    Abstract: There is provided according to the present invention a process for producing fluoromethyl hexafluoroisopropyl ether ((CF3)2CH—O—CH2F), including: reacting bisfluoromethyl ether with hexafluoroisopropyl alcohol in a solvent substantially immiscible with hydrogen fluoride in the presence of a catalytic amount of a strong acid selected from sulfuric acid and any other acids stronger in acidity than sulfuric acid. The process of the present invention enables industrial production of the fluoromethyl hexafluoroisopropyl ether without using hydrogen fluoride or a large amount of sulfuric acid and thereby without causing a large amount of waste as a by-product.
    Type: Application
    Filed: April 9, 2010
    Publication date: February 16, 2012
    Applicant: Central Glass Company, Limited
    Inventors: Yutaka Katsuhara, Hiroshi Takahashi, Michio Ishida
  • Publication number: 20120022296
    Abstract: A method for the preparation of (CF3)2CHOCH2F (Sevoflurane) is presented, which comprises providing a mixture of (CF3)2CHOCH2Cl, potassium fluoride, water, and a phase transfer catalyst and reacting the mixture to form (CF3)2CHOCH2F.
    Type: Application
    Filed: September 27, 2011
    Publication date: January 26, 2012
    Inventors: Ross C. Terrell, Joshua A. Levinson, Charles W. Young
  • Patent number: 8071816
    Abstract: 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 indepe
    Type: Grant
    Filed: June 30, 2008
    Date of Patent: December 6, 2011
    Assignee: 3M Innovative Properties Company
    Inventors: Richard M. Flynn, Michael G. Costello
  • Patent number: 8058482
    Abstract: A method for the preparation of (CF3)2CHOCH2F (Sevoflurane) is presented, which comprises providing a mixture of (CF3)2CHOCH2Cl, potassium fluoride, water, and a phase transfer catalyst and reacting the mixture to form (CF3)2CHOCH2F.
    Type: Grant
    Filed: November 17, 2005
    Date of Patent: November 15, 2011
    Assignee: Piramal Critical Care, Inc.
    Inventors: Ross C. Terrell, Joshua A. Levinson, Charles W. Young
  • Patent number: 8044247
    Abstract: The present invention refers to a process for the preparation of fluoromethyl 2,2,2-trifluoro-1-(trifluoromethyl)ethyl ether (sevoflurane) which includes a step that consists of reacting hexafluoroisopropanol with a formaldehyde equivalent selected among 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 resulting in the formation of the intermediate sevochlorane which is converted to sevoflurane in a second step which consists of reacting sevochlorane with an alkali metal fluoride, or a linear or branched chain tetra-alkyl quarternary ammonium fluoride in the presence of a sub-stoichiometric quantity of an alkali metal iodide, or a linear or branched alkyl chain tetra-alkyl quarternary ammonium iodide, preferably in a solvent.
    Type: Grant
    Filed: September 29, 2006
    Date of Patent: October 25, 2011
    Assignee: Cristália Produtos Químicos Farmacêuticos Ltda.
    Inventors: Ogari Pacheco, Antonio Carlos Teixeira, Edson Luiz Lima, Maria Alice Böckelmann
  • Publication number: 20110257073
    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. 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: Application
    Filed: June 27, 2011
    Publication date: October 20, 2011
    Inventors: Richard M. Flynn, Michael J. Bulinski, Michael G. Costello
  • Publication number: 20110257440
    Abstract: The present invention provides a preparation method of fluoromethyl 1,1,1,3,3,3-hexafluoroisopropyl ether by reacting CH2FX with 1,1,1,3,3,3-hexafluoroisopropanol in the presence of acid-binding agent. The reaction can be also preformed in the presence of solvent and/or phase-transfer catalyst. The present method has the advantages of simple reaction, manageable control condition, high material conversion and product yield, and the product can be easily separated. The obtained fluoromethyl 1,1,1,3,3,3-hexafluoroisoprophyl ether can be used as a safe inhalation anesthetics.
    Type: Application
    Filed: August 25, 2009
    Publication date: October 20, 2011
    Applicant: ZHEJIANG LANTIAN ENVIRONMENTAL PROTECTION HI-TECH CO.,LTD.
    Inventors: Weiguo Xu, Hua LI
  • Patent number: 8039678
    Abstract: 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: Grant
    Filed: September 29, 2006
    Date of Patent: October 18, 2011
    Assignee: Cristalia Produtos Quimicos Farmaceuticos Ltda.
    Inventors: Ogari Pacheco, Antonio Carlos Teixeira, Edson Luiz Lima, Maria Alice Böckelmann
  • Publication number: 20110251432
    Abstract: The invention relates to new processes for preparation of 18F-labelled alkylation reagents that can be used in the alkylation of amines that are suitable for use in labelling of Positron Emission Tomography (PET) radiotracers.
    Type: Application
    Filed: August 27, 2008
    Publication date: October 13, 2011
    Inventors: Bengt Langstrom, Tor Kihlberg
  • Patent number: 8022245
    Abstract: 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: Grant
    Filed: June 27, 2007
    Date of Patent: September 20, 2011
    Assignee: Daikin Industries, Ltd.
    Inventors: Tatsuya Ohtsuka, Yoshichika Kuroki, Atsushi Suzuki
  • Patent number: 8013182
    Abstract: The present invention provides a process for producing a novel compound, i.e., ?-chloromethoxycarboxylic acid ester represented by General Formula (1): (CF3)2C(OCH2Cl)COOR, wherein R is a hydrocarbon group which may be substituted with at least one atom selected from the group consisting of halogen, oxygen, nitrogen, and sulfur atoms, comprising reacting an ?-methoxycarboxylic acid ester represented by General Formula (2): (CF3)2C(OCH3)COOR, wherein R is as defined above, with molecular chlorine; and a process for producing 1,1,1,3,3,3-hexafluoroisopropyl fluoromethyl ether represented by a chemical formula (CF3)2CH(OCH2F), comprising fluorinating and decarboxylating the ?-chloromethoxycarboxylic acid ester. According to the present invention, 1,1,1,3,3,3-hexafluoroisopropyl fluoromethyl ether (sevoflurane), which is known as a compound having an anesthetic property, can be produced efficiently and at a low cost.
    Type: Grant
    Filed: November 6, 2008
    Date of Patent: September 6, 2011
    Assignee: Daikin Industries, Ltd.
    Inventors: Yoshihiro Yamamoto, Tatsuya Ohtsuka
  • Patent number: 7988877
    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. 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: Grant
    Filed: November 3, 2008
    Date of Patent: August 2, 2011
    Assignee: 3M Innovative Properties Company
    Inventors: Richard M. Flynn, Michael J. Bulinski, Michael G. Costello
  • Patent number: 7985877
    Abstract: 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: Grant
    Filed: May 31, 2007
    Date of Patent: July 26, 2011
    Assignee: Daikin Industries, Ltd.
    Inventors: Tatsuya Ohtsuka, Yoshihiro Yamamoto, Yoshichika Kuroki, Atsushi Suzuki, Akinari Sugiyama
  • Publication number: 20110178284
    Abstract: A protective group represented by the following general formula (I) (the oxygen atom attached with * represents oxygen atom of 2?-hydroxyl group of a ribonucleoside, a ribonucleotide or a derivative thereof; R1 and R2 both represent hydrogen atom, or represent a halogen atom, a C1-6 alkyl group, or a C1-6 halo-substituted alkyl group; R3 and R4 represent hydrogen atom, a halogen atom, a C1-6 alkyl group, or a C1-6 halo-substituted alkyl group; and R5 and R6 represent a halogen atom, a C1-6 halo-substituted alkyl group, cyano group, nitro group, or the like), which is stable under the reaction conditions of the nucleic acid synthetic cycles and has little steric hindrance, and can be removed under mild conditions using fluoride ions as a base.
    Type: Application
    Filed: September 15, 2010
    Publication date: July 21, 2011
    Applicant: CHIRALGEN, LTD.
    Inventors: Takeshi WADA, Mamoru SHIMIZU
  • Patent number: 7964552
    Abstract: This invention relates to surfactant compositions comprising a fluorosurfactant and a siloxane surfactant wherein the fluorosurfactant exhibits a disproportionate effect upon the resulting surfactant composition's ability to lower equilibrium surface tension. The fluorosurfactants and siloxane surfactants identified by the present invention exhibit a desirable disproportionate effect from the fluorosurfactant acting upon the resulting surfactant composition's ability to lower equilibrium surface tension. Because of this disproportionate effect, surfactant compositions of the present invention with no more than 21 weight percent fluorosurfactant have nearly identical ability to lower equilibrium surface tensions compared with surfactant compositions having higher amounts of fluorosurfactant.
    Type: Grant
    Filed: November 13, 2007
    Date of Patent: June 21, 2011
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Axel Hans-Joachim Herzog, Shaun Raymond Rinehimer
  • Publication number: 20110136713
    Abstract: Hydrofluoro alcohols of formula (I): A—(Rf)a—CFX—O—RhO—(CFX—(Rf)a*—CFX—O—RhO—)nH in which: Rh is a hydrocarbon-based chain; X is F or a C1-C6 (per)fluoroalkyl; a or a* is 0 or 1; Rf is a (per)fluoro(poly)oxyalkylene chain or a (per)fluoroalkyl chain; A is selected from the group consisting of —F, —Cl, and —H (possible only when a=1) or is HO—Rh—O—CFX—; n is an integer from 0 to 200, with the condition that n=0 when A is selected from the group consisting of —F, —Cl, and —H.
    Type: Application
    Filed: August 7, 2009
    Publication date: June 9, 2011
    Applicant: SOLVAY SOLEXIS S.P.A.
    Inventors: Giuseppe Marchionni, Ugo De Patto, Marco Avataneo
  • Publication number: 20110105803
    Abstract: The present invention provides a method of synthesizing sevoflurane, which comprises the following steps: taking hexafluoro isopropanol as the starting material and reacting it with trioxymethylene (or paraformaldehyde) in the presence of acid to generate dihexafluoro isopropanol formal derivatives, adding anhydrous aluminum trihalide to generate halomethyl 2,2,2-trifluoro-1-(trifluoromethyl)ethyl ether, then reacting the halomethyl compound with metal fluoride to form the sevoflurane. The method is of low cost, and the reaction condition is easy to implement, and produces sevoflurane in large scale.
    Type: Application
    Filed: July 2, 2009
    Publication date: May 5, 2011
    Inventor: Zhiquan Zhao
  • 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: 20110082313
    Abstract: Halogenated ?-fluoroethers (or bis-derivatives thereof) can be produced by reacting a halogenated hemiacetal (or bis-derivative thereof) with sulfuryl fluoride (S2F2) in the presence of an organic base. The reaction is conducted preferably in the presence of “a salt or complex of an organic base with hydrogen fluoride”, whereby the objective dehydroxyfluorination can proceed extremely favorably. It is still preferable to use as the starting substrate a halogenated hemiacetal prepared from fluoral or 3,3,3-trifluoropyruvic acid ester. Thus, industrially important halogenated ?-fluoroethers can be industrially produced with high selectivity and in high yield.
    Type: Application
    Filed: May 14, 2009
    Publication date: April 7, 2011
    Applicant: CENTRAL GLASS COMPANY, LIMITED
    Inventors: Akihiro Ishii, Manabu Yasumoto
  • Publication number: 20110034414
    Abstract: The present invention relates to fluoroalkyloxy alkanes having formula (I): RF—R1—O—R2 wherein: RF is a linear or branched perfluoroalkyl group, having from 1 to 12, preferably from 2 to 8, carbon atoms; R1 is a linear or branched, non-fluorinated alkylene group, having from 1 to 6, preferably from 2 to 4, carbon atoms, —R2 is a linear or branched, non-fluorinated alkyl group, having from 1 to 12, preferably from 2 to 8, carbon atoms, possibly containing at least one ether bond —O— along the chain. The present invention further relates to a process for preparation and use thereof, possibly in mixture with at least one silicone oil, as medicaments in ophthalmology, in particular as tamponade liquids in an operation for the treatment of retinal detachment.
    Type: Application
    Filed: April 28, 2008
    Publication date: February 10, 2011
    Applicant: AL.CHI.MI.A. S.R.L.
    Inventors: Lino Conte, Mauro Beccaro, Enrico Bettini, Paolo Signori, Alessandro Zaggia
  • Publication number: 20100312019
    Abstract: Methyl fluoroalkyl ether can be produced by the reaction of a fluoroalkyl alcohol with chloromethane. The process involves reacting an alkoxide of a fluoroalkyl alcohol with chloromethane.
    Type: Application
    Filed: June 8, 2009
    Publication date: December 9, 2010
    Inventors: Serguei V. Kovalenko, Joel Swinson
  • Patent number: 7816409
    Abstract: The present invention has as objective the stabilization of a fluoroether compound against degradation by acid substances. The stabilizers proposed are selected among propylene glycol, polyethylene glycol, hexylene glycol, 1,3-butylene glycol and a saturated cyclic alcohol preferably menthol and are used for preparing stable pharmaceutical compositions of a fluoroether compound. Method for stabilizing a fluoroether compound and use of stabilizers agents for precluding the degradation of a fluoroether are also described.
    Type: Grant
    Filed: August 20, 2004
    Date of Patent: October 19, 2010
    Assignee: Cristalia Productos Quimicos Farmaceuticos LTDA
    Inventors: Ogari Pacheco, Elisa Russo, Valter Russo, José Antônio Martins, Maria Alice Bockelmann, Simone Rosatto
  • Publication number: 20100234634
    Abstract: The present invention provides a process for producing a novel compound, i.e., ?-chloromethoxycarboxylic acid ester represented by General Formula (1): (CF3)2C(OCH2Cl)COOR, wherein R is a hydrocarbon group which may be substituted with at least one atom selected from the group consisting of halogen, oxygen, nitrogen, and sulfur atoms, comprising reacting an ?-methoxycarboxylic acid ester represented by General Formula (2): (CF3)2C(OCH3)COOR, wherein R is as defined above, with molecular chlorine; and a process for producing 1,1,1,3,3,3-hexafluoroisopropyl fluoromethyl ether represented by a chemical formula (CF3)2CH(OCH2F), comprising fluorinating and decarboxylating the ?-chloromethoxycarboxylic acid ester. According to the present invention, 1,1,1,3,3,3-hexafluoroisopropyl fluoromethyl ether (sevoflurane), which is known as a compound having an anesthetic property, can be produced efficiently and at a low cost.
    Type: Application
    Filed: November 6, 2008
    Publication date: September 16, 2010
    Inventors: Yoshihiro Yamamoto, Tatsuya Ohtsuka
  • Publication number: 20100234605
    Abstract: New methods for producing difluoromethylene-containing compounds with phenylsulfur trifluoride or a primary alkyl-substituted phenylsulfur trifluoride are disclosed. Also, new methods for producing trifluoromethyl-containing compounds with phenylsulfur trifluoride or primary alkyl-substituted phenylsulfur trifluoride are also disclosed.
    Type: Application
    Filed: December 9, 2008
    Publication date: September 16, 2010
    Applicant: IM&T RESEARCH, INC.
    Inventors: Teruo Umemoto, Rajendra P. Singh
  • Publication number: 20100185020
    Abstract: 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: Application
    Filed: July 11, 2008
    Publication date: July 22, 2010
    Applicant: Piramal Healthcare Limited
    Inventors: Sivaramakrishnan Hariharan, Owen Chambers, Abhay Atmaram Upare, Damodharan Satagopan
  • Patent number: 7750192
    Abstract: 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: Grant
    Filed: August 2, 2006
    Date of Patent: July 6, 2010
    Assignee: Halocarbon Products Corporation
    Inventors: Barry Jones, Joel Swinson