Purification Or Recovery Patents (Class 568/682)
  • 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: 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
  • 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
  • Patent number: 8163138
    Abstract: A method for processing effluent from a chloromethylation of a vinyl aromatic polymer wherein the effluent includes catalyst and volatile organics, and wherein the method includes the steps of: 1) deactivating at least a portion of the catalyst; 2) distilling the effluent; 3) adding caustic to the effluent; and 4) distilling the effluent.
    Type: Grant
    Filed: May 23, 2007
    Date of Patent: April 24, 2012
    Assignee: Dow Global Technologies LLC
    Inventors: William I. Harris, Bruce S. Holden, Doreen C. Keptner, David C. McDonald
  • Publication number: 20120083629
    Abstract: The present invention provides a method for efficiently producing a highly pure fluoroether containing remarkably low concentration of a fluorine-containing alkyl alcohol. The method is suited for scale-up and specifically includes performing countercurrent separation of a crude solution of fluoroether including a fluorine-containing alkyl alcohol as an impurity using water.
    Type: Application
    Filed: June 15, 2010
    Publication date: April 5, 2012
    Applicant: DAIKIN INDUSTRIES, LTD.
    Inventors: Michiru Kagawa, Aoi Nakazono, Yasuhide Senba, Hitoshi Motoyama, Toru Yoshizawa, Meiten Koh
  • 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
  • Publication number: 20110282104
    Abstract: Disclosed are compositions comprising a compound having the formula CF3(CF2)xCF?CFCF(OR)(CF2)yCF3, wherein R is CH3 or C2H5or mixtures thereof, and wherein x and y are independently 0, 1, 2 or 3, and wherein x+y=1, 2 or 3. Also disclosed are unsaturated fluoroethers selected from the group consisting of CF3(CF2)xCF?CFCF(OR)(CF2)yCF3, CF3(CF2)xC(OR)?CFCF2(CF2)yCF3, CF3CF?CFCF(OR)(CF2)x(CF2)yCF3, CF3(CF2)xCF?C(OR)CF2(CF2)yCF3, and mixtures thereof, wherein R can be either CH3, C2H5 or mixtures thereof, and wherein x and y are independently 0, 1, 2 or 3, and wherein x+y=0, 1, 2 or 3. Also disclosed herein are novel methods of making a composition comprising at least one of the compounds described.
    Type: Application
    Filed: July 21, 2011
    Publication date: November 17, 2011
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: JOAN ELLEN BARTELT, Robert D. Lousenberg
  • 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
  • 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: 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: 20100280283
    Abstract: Processes for preparing commercial quantities of a stable, pharmaceutically acceptable sevoflurane substantially free of impurities are claimed. In another embodiment, a process for removing reactive metal salts from the surface of metallic equipment used in the distillation of sevoflurane and rendering a non-inert metallic surface of the metallic equipment inert.
    Type: Application
    Filed: July 9, 2010
    Publication date: November 4, 2010
    Applicant: HALOCARBON PRODUCTS CORPORATION
    Inventors: Barry Jones, Joel Swinson, Paul Mazzell
  • 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
  • Patent number: 7732647
    Abstract: 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: Grant
    Filed: December 27, 2007
    Date of Patent: June 8, 2010
    Assignee: Halocarbon Products Corporation
    Inventors: Barry Jones, Joel Swinson, Paul Mazzell
  • Publication number: 20090275785
    Abstract: Processes for preparing commercial quantities of a stable, pharmaceutically acceptable sevoflurane substantially tree of impurities are claimed. In another embodiment, a process for removing reactive metal, salts from the surface of metallic equipment used in the distillation of sevoflurane and rendering a non-inert metallic surface of the metallic equipment inert.
    Type: Application
    Filed: May 1, 2008
    Publication date: November 5, 2009
    Inventors: Barry Jones, Joel Swinson, Paul Mazzell
  • Publication number: 20080214875
    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, and removing substantially pure sevoflurane from the distilling multiphase mixture. 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: Application
    Filed: August 2, 2006
    Publication date: September 4, 2008
    Applicant: HALOCARBON PRODUCT CORPORATION
    Inventors: Barry Jones, Joel Swinson
  • 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: 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: 7230142
    Abstract: 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: Grant
    Filed: March 3, 1999
    Date of Patent: June 12, 2007
    Assignee: Central Glass Company, Limited
    Inventors: Toshikazu Kawai, Matsue Kawamura
  • Patent number: 7230143
    Abstract: 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: Grant
    Filed: January 4, 2005
    Date of Patent: June 12, 2007
    Assignee: Halocarbon Products Corporation
    Inventors: Barry Jones, Ashot Khrimian, Joel Swinson, Paul Cross
  • Patent number: 7153397
    Abstract: 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: Grant
    Filed: December 21, 2001
    Date of Patent: December 26, 2006
    Assignee: Ineos Fluor Holdings Limited
    Inventors: Andrew Paul Sharratt, Lee Colin Draper
  • Patent number: 7067690
    Abstract: Process for modifying the relative ratios of the components of a liquid starting mixture of specific diastereoisomers, containing at least two asymmetric carbon atoms comprising contacting said liquid mixture with a Lewis acid compound capable of co-ordinating a compound having at least two Lewis basic functionalities and subjecting the resulting mixture to conditions such that a reaction product, having a molar ratio between its diastereoisomeric components different from the corresponding molar ratio in the said liquid starting mixture, becomes separated from the said liquid mixture, said process being carried out using an amount of said Lewis acid not enough to co-ordinate the total amount of the diastereoisomeric components of the liquid starting mixture. This method shows an excellent balance of efficiency and easiness of procedure that cannot be reached with the physical methods of diastereoisomers separation known in the art.
    Type: Grant
    Filed: December 20, 2002
    Date of Patent: June 27, 2006
    Assignee: Basell Poliolefine Italia S.p.A.
    Inventors: Giampiero Morini, Fabrizio Piemontesi, Antonio Cristofori, Stefania Milani
  • Patent number: 7034190
    Abstract: 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: Grant
    Filed: December 21, 2001
    Date of Patent: April 25, 2006
    Assignee: Ineos Fluor Holdings Limited
    Inventors: Andrew Paul Sharratt, Lee Colin Draper
  • Patent number: 7019178
    Abstract: 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: Grant
    Filed: December 21, 2001
    Date of Patent: March 28, 2006
    Assignee: Ineos Fluor Holdings Limited
    Inventors: Andrew P. Sharratt, Stuart Corr
  • 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: 6566559
    Abstract: Process for the production of unsaturated ethers, in particular isopropenyl methyl ether (IPM), by pyrolysis of a ketal-containing or acetal-containing mixture, in particular dimethoxypropane (DMP), in the liquid phase in the presence of an organic carboxylic acid, according to the following reaction scheme: wherein R1=H or alkyl with 1-8 C atoms; R2=H, CH3—, C2H5—, or Cl—; R3=alkyl with 1-8 C atoms; R4=H, CH3—, C2H5—, or C3H7—, and R1 and R4 may be joined to form a 5-, 6-, or 7-membered ring. DMP is produced by the process from acetone and methanol by reaction in an acidic heterogeneous ion exchanger, the product being isolated by extraction with aqueous alkaline solution. In particular the process involves combining the IPM reaction product with the DMP reaction product, which permits the execution of a stable recycling process in which the methanol-containing streams of the IPM and DMP stages can be simultaneously extracted.
    Type: Grant
    Filed: June 1, 2001
    Date of Patent: May 20, 2003
    Assignee: Degussa AG
    Inventors: Steffen Krill, Stephan Kretz, Volker Häfner, Georg Markowz
  • Patent number: 6555086
    Abstract: 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: Grant
    Filed: October 7, 1999
    Date of Patent: April 29, 2003
    Assignee: Ineos Fluor Holdings Limited
    Inventors: Paul Nicholas Ewing, Charles John Shields, Robert Elliott Low
  • Patent number: 6448451
    Abstract: The invention provides a process for purifying methyl 2,2,2-trifluoro-1-(trifluoromethyl)ethyl ether, comprising: passing a composition comprising methyl 2,2,2-trifluoro-1-(trifluoromethyl)ethyl ether and dimethyl ether through an evaporation zone; evaporating dimethyl ether by passing a gas stream through the composition; and removing the gas comprising dimethyl ether from the composition.
    Type: Grant
    Filed: June 5, 2001
    Date of Patent: September 10, 2002
    Assignee: Baxter International, Inc.
    Inventors: Ralph Rudzinski, Ralph Lessor
  • Patent number: 6315869
    Abstract: A perfluorovinyl ether of the formula: RfO(CF2CFXO)nCF═CF2  (1) in which Rf is a perfluoralkyl group, X is a fluorine atom or a trifluoromethyl group, and n is a number of 0 to 20 containing impurities is purified by removing a hydrogen fluoride adduct of the perfluorovinyl ether (1) through distillation, the perfluorovinyl ether (1) is distilled in the presence of a ketone or an ether having a lower boiling point than that of the perfluorovinyl ether (1) while refluxing such a solvent. This method can remove the hydrogen fluoride adduct of a perfluorovinyl ether as an impurity and provide a high purity perfluorovinyl ether.
    Type: Grant
    Filed: May 21, 1999
    Date of Patent: November 13, 2001
    Assignee: Daikin Industries, Ltd.
    Inventors: Shigeru Morita, Toshihiko Amano
  • Patent number: 6245953
    Abstract: In a method for recovering a fluorine-containing solvent from the mixture comprising the fluorine-containing solvent and dyes, (i) a method for recovering a fluorine-containing solvent by distillation; and (ii) a method for recovering a fluorine-containing solvent comprising the steps of adding to the mixture the second solvent which uniformly mixes with the fluorine-containing solvent but does not dissolve the dyes; separating a precipitate from the resulting mixture; and separating the second solvent.
    Type: Grant
    Filed: November 22, 1999
    Date of Patent: June 12, 2001
    Assignee: Daikin Industries, Ltd.
    Inventors: Fumihiko Yamaguchi, Toshiyuki Katsube
  • Patent number: 6198009
    Abstract: Perfluoropropylvinylether (FPVE) purification process with C1-C10 alcohols or mixtures thereof.
    Type: Grant
    Filed: April 2, 1999
    Date of Patent: March 6, 2001
    Assignee: Ausimont S.p.A.
    Inventors: John W. Blanke, Julio A. Abusleme
  • 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: 5951829
    Abstract: A method of separating heteropoly compounds from mixtures of polyethers, polyesters and/or polyether esters, a protic component and heteropoly compounds, wherein the protic component is removed from the mixture and subsequently separating off the heteropoly compound as a separate phase. The polymer phase which remains is preferably brought into further contact with a solid adsorbent that is capable of adsorbing heteropoly compounds.
    Type: Grant
    Filed: March 27, 1997
    Date of Patent: September 14, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans-Jurgen Weyer, Rolf Fischer, Gerhard Jeschek, Herbert Muller
  • Patent number: 5763684
    Abstract: The present invention relates to a method of removing bisfluoromethyl ether contained in fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether in a simple, effective manner, and is characterized in that fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether containing bisfluoromethyl ether is brought into contact with zeolite.
    Type: Grant
    Filed: September 16, 1997
    Date of Patent: June 9, 1998
    Assignee: Central Glass Co., Ltd.
    Inventors: Toshikazu Kawai, Mineo Watanabe, Manami Kobayashi
  • Patent number: 5705710
    Abstract: This invention relates to a method of synthesizing 1,1,1,3,3,3-hexafluoroisopropyl ether compounds from the reaction of methoxymalanonitrile with a bromine trifluoride composition.
    Type: Grant
    Filed: January 15, 1997
    Date of Patent: January 6, 1998
    Assignee: University of Iowa Research Foundation
    Inventors: Max T. Baker, John H. Tinker, Jan A. Ruzicka
  • Patent number: 5684210
    Abstract: It is possible to obtain fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether which has a high purity and in which an impurity making the purification by distillation difficult has been removed, by contacting a crude fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether with a Bronsted acid(s), a Lewis acid(s) or an acid(s) fixed to a resin or the like.
    Type: Grant
    Filed: November 10, 1995
    Date of Patent: November 4, 1997
    Assignee: Central Glass Company, Limited
    Inventors: Toshikazu Kawai, Takaaki Yoshimura, Mineo Watanabe, Manami Kumakura
  • Patent number: 5684211
    Abstract: The present invention provides a method of purifying fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether by adding a compound selected from hydroxides of, hydrogenphosphates of, phosphates of, hydrogencarbonates of, borates of or sulfites of alkali metals, or alkali metal salts of acetic acid or of phthalic acid, or boric acid to fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether, add then by distillation. It is possible to effectively suppress the decomposition, at the time of distillation, of fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether that is used as a pharmaceutical and particularly as an inhalation anesthetic and thus to obtain fluoromethyl-1,1,1,3,3,3-hexafluoroisopropyl ether of high purity.
    Type: Grant
    Filed: November 16, 1995
    Date of Patent: November 4, 1997
    Assignee: Central Glass Company, Limited
    Inventors: Toshikazu Kawai, Takaaki Yoshimura, Manami Kumakura, Mineo Watanabe
  • Patent number: 5600022
    Abstract: In a reaction for introducing chloromethyl groups into an aromatic crosslinked copolymer by reacting chloromethyl methyl ether to the aromatic crosslinked copolymer in the presence of a chloromethylation reaction catalyst, a method for recovering chloromethyl methyl ether from the reaction mixture, which comprises the following steps 1) a step of adding to the reaction mixture an aqueous acid solution which is capable of dissolving the chloromethylation reaction catalyst without decomposing chloromethyl methyl ether, and an extraction solvent which is inert to and miscible with chloromethyl methyl ether and which is capable of swelling the chloromethylated aromatic crosslinked copolymer, 2) a step of contacting hydrogen chloride gas to the reaction mixture and the extract solution from the step 1 to convert decomposition products of chloromethyl methyl ether, to chloromethyl methyl ether, 3) a step of separating the resulting mixture from the step 2 into an extraction solvent layer containing chloromethyl met
    Type: Grant
    Filed: December 27, 1994
    Date of Patent: February 4, 1997
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Kiyoto Ando, Akihiko Tsukada, Hiroshi Arataki, Youichi Tamura
  • Patent number: 5352785
    Abstract: A process for the purification of a perfluorochemical composition comprises continuously mixing the perfluorochemical composition, comprising a liquid mixture of inert perfluorochemicals (e.g., perfluoroalkanes, perfluoroethers, perfluoroaminoethers, or perfluoroalkyl tertiary amines) and isomeric fluorohydrochemicals, with a stabilization composition comprising water-miscible alkanol and an aqueous solution of base (such as potassium hydroxide) made by dissolving the base in an amount of water sufficient to dissolve or disperse the fluoride salt by-products of the subsequent reaction of the base with the fluorohydrochemicals to form fluoroolefins, the amount of the alkanol in the stabilization composition being in stoichiometric excess of the amount needed to completely convert the fluoroolefins to alkoxyvinyl ethers. The process can be utilized to purify the product mixtures resulting from fluorination methods such as direct fluorination or ECF.
    Type: Grant
    Filed: March 30, 1993
    Date of Patent: October 4, 1994
    Assignee: Minnesota Mining and Manufacturing Company
    Inventors: Thomas C. Herzberg, Robert B. Fletcher, Randall F. Henderson
  • Patent number: 5230778
    Abstract: A method for the separation of Isoflurane from its admixture with other compounds produced in the chlorination of 2-difluoromethoxy-1,1,1-trifluoroethane including subjecting the mixture to distillation, distilling off the Isoflurane and effecting said distillation as an extractive distillation employing an extractive solvent which retards the vapor pressure of Isoflurane.
    Type: Grant
    Filed: May 1, 1992
    Date of Patent: July 27, 1993
    Assignees: Gavlin Associates, Halocarbon Product Corporation
    Inventors: Gilbert Gavlin, Boris Goltsin
  • Patent number: 5166453
    Abstract: A purification method of a fluorine-containing alkylethylene comprises reacting the fluorine-containing alkylethylene with powdered metallic zinc in the presence of an aqueous acetic acid solution. By this method, fluorine-containing alkyl iodide and fluorine-containing alkylethyl iodide, contained as impurities in the fluorine-containing alkylethylene, can be removed effectively, for example, to a level of 1 ppm or below.
    Type: Grant
    Filed: July 3, 1991
    Date of Patent: November 24, 1992
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Takashi Matsuda, Hirofumi Kishita, Shinichi Sato, Koichi Yamaguchi, Kouji Takano, Shuji Suganuma
  • Patent number: 4940797
    Abstract: A process is described for the improved synthesis of the optically pure C.sub.10 -C.sub.18 fragment of the macrolide structure of the immunosuppressant FK-506. This compound is also useful as an intermediate for preparing FK-506 derivatives.
    Type: Grant
    Filed: March 23, 1989
    Date of Patent: July 10, 1990
    Assignee: Merck & Co., Inc.
    Inventors: Todd K. Jones, Sander G. Mills, Richard Desmond
  • Patent number: 4792638
    Abstract: The present invention relates to an isolation process of 2-chloroethylvinyl ether from a thermal decomposition product of 1,1-di(2-chloroethoxy)ethane, and comprises the azeotropic distillation of 2-chloroethyl vinyl ether and 2-chloroethanol from the product, the reaction of the 2-chloroethanol in the azeptrope with the 2-chloroethyl vinyl ether to 1-1-di(2-chloroethoxy)ethane without the separation from the product, and the purification of 2-chloroethyl vinyl ether by the rectification of the above reaction mixture.
    Type: Grant
    Filed: March 23, 1988
    Date of Patent: December 20, 1988
    Assignee: Nisso Maruzen Chemical Co., Ltd.
    Inventors: Tsuyoshi Matsumoto, Toshiyuki Fukudome, Masaaki Tsuchida
  • Patent number: 4501869
    Abstract: An easily cross linkable fluorine-containing polymer comprising: (1) a polymeric chain comprising one or more polymer segments, at least one polymer segment of which consists of units of at least one fluorine-containing ethylenically unsaturated compound having 2 to 8 carbon atoms, or units of said fluorine-containing ethylenically unsaturated compound and at least one other monomer selected from the group consisting a fluorine-free ethylenically unsaturated compound having 2 to 4 carbon atoms and a fluorine-containing diene having 4 to 8 carbon atoms, (2) at least one bromine atom liberated from a brominated compound of the formula: RBr.sub.x (wherein R is a saturated hydrocarbon residue and x is a number corresponding to the bonding valency of the residue R) in an amount of 0.
    Type: Grant
    Filed: July 26, 1983
    Date of Patent: February 26, 1985
    Assignee: Daikin Kogyo Co., Ltd.
    Inventors: Masayoshi Tatemoto, Masahiko Oka, Hideo Kano, Masayasu Tomoda, Yutaka Ueta
  • Patent number: 4469898
    Abstract: A method of synthesizing fluoromethylhexafluoroisopropyl ether, comprising mixing hexafluoroisopropyl alcohol, formaldehyde, hydrogen fluoride, and a protonating, dehydrating and fluoride ion-generating agent under conditions suitable to generate fluoromethylhexafluoroisopropyl ether, and then recovering the fluoromethylhexafluoroisopropyl ether.
    Type: Grant
    Filed: December 6, 1982
    Date of Patent: September 4, 1984
    Assignee: Baxter Travenol Laboratories, Inc.
    Inventors: Clifford L. Coon, Robert L. Simon
  • Patent number: 4334105
    Abstract: Methods for the dehalogenation of various haloethers are disclosed, comprising providing a haloether having the formula CX'.sub.3 -[CY.sub.2 ].sub.n -O-CZ.sub.2 -CX.sub.3 in which X', Y, Z and X are specifically disclosed combinations of hydrogen, fluorine chlorine and bromine such that the molecule includes at least one reducible group, but where both portions of any ethyl groups present are not reducible. Dehalogenation of these haloethers is carried out by contacting same with a hydrogen donor comprising an amine, preferably a primary or secondary amine or a primary, secondary or tertiary alkanol amine. The amine is preferably used in combination with a catalyst, such as a varivalent metal or a salt thereof, such as copper or a copper salt.
    Type: Grant
    Filed: August 8, 1980
    Date of Patent: June 8, 1982
    Assignee: Airco, Inc.
    Inventors: Ross C. Terrell, Kirsten Hansen
  • Patent number: 4328376
    Abstract: The method of removing fluorinated olefin byproduct formed during the synthesis of a fluoromethylhexafluoroisopropyl ether product or the like comprises: adding ammonia or an amine to the mixture to react with the fluorinated olefin byproduct, and thereafter distilling the fluoromethylhexafluoroisopropyl ether product to remove it from the byproduct.
    Type: Grant
    Filed: March 31, 1980
    Date of Patent: May 4, 1982
    Assignee: Baxter Travenol Laboratories, Inc.
    Inventors: Arthur Berger, Robert L. Simon
  • Patent number: T107801
    Abstract: A process for rapidly curing a fluoroelastomer which comprises mixing and heating a fluoroelastomer copolymer whose interpolymerized units consist essentially of vinylidene fluoride, at least one other fluorine-containing monomer copolymerizable therewith, said monomer being a compound which contains 2-7 carbon atoms, contains no bromine, and contains at least as many fluorine atoms as carbon atoms and contains up to 3 mole percent of units derived from a bromine-containing olefin; a quaternary phosphonium compound; a bisphenol or an ammonium or phosphonium salt thereof; and a dialkylaminopyridine or a diazabicyclo compound having the formula ##STR1## where n is 2-8 or 0.2-0.8 parts by weight per hundred parts fluoroelastomer of a carboxylic acid salt of (a) or (b).
    Type: Grant
    Filed: October 9, 1984
    Date of Patent: May 5, 1987
    Inventor: Arthur Nersasian