Including Extraction With Organic Liquid Patents (Class 570/180)
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Patent number: 8951431Abstract: Provided are azeotropic and azeotrope-like compositions of 1,2,3,3,3-pentafluoropropene (HFO-1225ye) and water. Such azeotropic and azeotrope-like compositions are useful in isolating 1,2,3,3,3-pentafluoropropene from impurities during production. Azeotropes of the instant invention are similarly useful in final compositions or manufacturing final compositions, such as blowing agent, propellants, refrigerants, diluents for gaseous sterilization and the like.Type: GrantFiled: April 8, 2011Date of Patent: February 10, 2015Assignee: E I du Pont de Nemours and CompanyInventors: Ryan Hulse, Haluk Kopkalli, Hang T. Pham
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Patent number: 8871987Abstract: A process for separating cis-1,1,1,4,4,4-hexafluoro-2-butene from a first mixture comprising cis-1,1,1,4,4,4-hexafluoro-2-butene and at least one chlorofluoroolefin is disclosed. The process involves the steps of contacting the mixture with at least one extractive agent, to form another mixture, distilling the mixture; and recovering cis-1,1,1,4,4,4-hexafluoro-2-butene substantially free of chlorofluoroolefin.Type: GrantFiled: December 9, 2011Date of Patent: October 28, 2014Assignee: E I du Pont de Nemours and CompanyInventor: Jeffrey P. Knapp
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Patent number: 8747691Abstract: Provided are azeotropic and azeotrope-like compositions of trans-1,3,3,3-tetrafluoropropene (HFO-1234ze(E)) and water. Such azeotropic and azeotrope-like compositions are useful in isolating trans-1,3,3,3-tetrafluoropropene from impurities during production. Azeotropes of the instant invention are similarly useful in final compositions or for the manufacture of final compositions, such as blowing agent, propellants, refrigerants, diluents for gaseous sterilization and the like.Type: GrantFiled: April 8, 2011Date of Patent: June 10, 2014Assignee: Honeywell International Inc.Inventors: Ryan Hulse, Haluk Kopkalli, Hang T. Pham
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Patent number: 8692038Abstract: There is provided a fluorine-containing compound purification method for obtaining a high-purity fluorine-containing compound by efficiently separating and removing hydrogen chloride from a fluorine-containing compound that contains hydrogen chloride, i.e., from a crude fluorine-containing compound. The fluorine-containing compound purification method of the present invention comprises the following steps (1) and (2) in this order: step (1): a step of adding dimethyl ether to a crude fluorine-containing compound that contains a fluorine-containing compound and hydrogen chloride in a molar ratio (dimethyl ether (mol)/hydrogen chloride (mol)) of dimethyl ether to hydrogen chloride being 1.3 or more to prepare a mixture (1) of the crude fluorine-containing compound and dimethyl ether; and step (2): a step of separating and removing a mixture (2) of hydrogen chloride and dimethyl ether from the mixture (1).Type: GrantFiled: October 26, 2010Date of Patent: April 8, 2014Assignee: Showa Denko K.K.Inventors: Hiromoto Ohno, Toshio Ohi, Katsutoshi Morinaka
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Patent number: 8628644Abstract: The present invention relates to a process for separating close-boiling and azeotropic components of mixtures, wherein said mixtures contain at least one hydrofluorocarbon compound, using at least one ionic liquid.Type: GrantFiled: September 22, 2006Date of Patent: January 14, 2014Assignee: E I du Pont Nemours and CompanyInventors: Mark B. Shiflett, Akimichi Yokozeki
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Patent number: 8541634Abstract: Disclosed are azeotropic and azeotrope-like mixtures of (Z)-1-chloro-3,3,3-trifluoropropene (1233zd(Z)) and hydrogen fluoride. Such compositions are useful as an intermediate in the production of 1233zd(Z). The latter compound is useful as a nontoxic, zero ozone depleting fluorocarbon useful as a solvent, blowing agent, refrigerant, cleaning agent, aerosol propellant, heat transfer medium, dielectric, fire extinguishing composition and power cycle working fluid.Type: GrantFiled: January 14, 2013Date of Patent: September 24, 2013Assignee: Honeywell International Inc.Inventors: Ryan Hulse, Hang T Pham
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Publication number: 20120215040Abstract: There is provided a fluorine-containing compound purification method for obtaining a high-purity fluorine-containing compound by efficiently separating and removing hydrogen chloride from a fluorine-containing compound that contains hydrogen chloride, i.e., from a crude fluorine-containing compound. The fluorine-containing compound purification method of the present invention comprises the following steps (1) and (2) in this order: step (1): a step of adding dimethyl ether to a crude fluorine-containing compound that contains a fluorine-containing compound and hydrogen chloride in a molar ratio (dimethyl ether (mol)/hydrogen chloride (mol)) of dimethyl ether to hydrogen chloride being 1.3 or more to prepare a mixture (1) of the crude fluorine-containing compound and dimethyl ether; and step (2): a step of separating and removing a mixture (2) of hydrogen chloride and dimethyl ether from the mixture (1).Type: ApplicationFiled: October 26, 2010Publication date: August 23, 2012Applicant: SHOWA DENKO K.K.Inventors: Hiromoto Ohno, Toshio Ohi, Katsutoshi Morinaka
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Publication number: 20120165579Abstract: This invention relates to a process for separating 1,1,2,2-tetrafluoroethane or 1,1,1,2-tetrafluoroethane from a mixture comprising both 1,1,1,2-tetrafluoroethane and 1,1,2,2-tetrafluoroethane wherein at least one ionic liquid is used to enhance the efficiency of the separation.Type: ApplicationFiled: June 20, 2011Publication date: June 28, 2012Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: MARK BRANDON SHIFLETT, AKIMICHI YOKOZEKI, JEFFREY P. KNAPP
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Publication number: 20120046505Abstract: A process is disclosed for reducing the amount of monofluoroacetate. The process involves (a) contacting a hydrofluorocarbon with a reactant basic aqueous solution to produce an organic phase solution containing a hydrofluoroolefin and an aqueous phase solution containing a monofluoroacetate; and (b) heating the aqueous phase solution to an effective temperature to reduce the amount of monofluoroacetate in the aqueous phase solution, wherein fluoride concentration in the aqueous phase solution is substantially high. Another process is disclosed for reducing the amount of monofluoroacetate.Type: ApplicationFiled: May 7, 2010Publication date: February 23, 2012Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: Mario Joseph Nappa, Patricia Cheung, Karl R. Krause, Michael A. Sisk
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Publication number: 20110275723Abstract: Provided are azeotropic and azeotrope-like compositions of trans-1,3,3,3-tetrafluoropropene (HFO-1234ze(E)) and water. Such azeotropic and azeotrope-like compositions are useful in isolating trans-1,3,3,3-tetrafluoropropene from impurities during production. Azeotropes of the instant invention are similarly useful in final compositions or for the manufacture of final compositions, such as blowing agent, propellants, refrigerants, diluents for gaseous sterilization and the like.Type: ApplicationFiled: April 8, 2011Publication date: November 10, 2011Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Ryan Hulse, Haluk Kopkalli, Hang T. Pham
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Patent number: 7964760Abstract: This invention relates to a process for separating 1,1,2,2-tetrafluoroethane or 1,1,1,2-tetrafluoroethane from a mixture comprising both 1,1,1,2-tetrafluoroethane and 1,1,2,2-tetrafluoroethane wherein at least one ionic liquid is used to enhance the efficiency of the separation.Type: GrantFiled: May 21, 2008Date of Patent: June 21, 2011Assignee: E.I. du Pont de Nemours and CompanyInventors: Mark Brandon Shiflett, Akimichi Yokozeki, Jeffrey P. Knapp
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Publication number: 20090131728Abstract: A process for separating the diastereomers of a compound such as dihydrodecafluoropentane by using an ionic liquid to increase separation efficiency. The process may involve separation of the threo and erythro diastereomers of HFC-4310mee by liquid-liquid extraction wherein at least one ionic liquid is used as the extractant.Type: ApplicationFiled: May 14, 2008Publication date: May 21, 2009Inventors: Mark Brandon Shiflett, Akimichi Yokozeki
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Publication number: 20080293978Abstract: This invention relates to a process for separating 1,1,2,2-tetrafluoroethane or 1,1,1,2-tetrafluoroethane from a mixture comprising both 1,1,1,2-tetrafluoroethane and 1,1,2,2-tetrafluoroethane wherein at least one ionic liquid is used to enhance the efficiency of the separation.Type: ApplicationFiled: May 21, 2008Publication date: November 27, 2008Inventors: Mark Brandon Shiflett, Akimichi Yokozeki, Jeffrey P. Knapp
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Patent number: 7405334Abstract: The present invention relates to processes for reducing the concentration of acidic impurities HF, HCl, HBr, HI, HNO3 and H2SO4 in fluorinated hydrocarbons. The process involves: (i) contacting the fluorinated hydrocarbon with a phosphorous oxyacid salt, and (ii) recovering the fluorinated hydrocarbon having reduced concentration of, or substantially free of, said acidic contaminant, provided that said fluorinated hydrocarbon is not CF3CH2CF3 or CF3CHFCF3.Type: GrantFiled: May 23, 2003Date of Patent: July 29, 2008Assignee: E. I. du Pont de Nemours and CompanyInventors: Velliyur Nott Mallikarjuna Rao, Allen C. Sievert
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Patent number: 7361795Abstract: The invention relates to azeotropic and azeotrope-like mixtures of 1,1,1,3,3-pentafluorobutane (HFC-365) and hydrogen fluoride and a process for separating the azeotrope-like mixtures. The compositions of the invention are useful as an intermediate in the production of HFC-365. The latter is useful as a nontoxic, zero ozone depleting fluorocarbon useful as a solvent, blowing agent, refrigerant, cleaning agent and aerosol to propellant.Type: GrantFiled: October 14, 2003Date of Patent: April 22, 2008Assignee: Honeywell International, Inc.Inventors: Hang T. Pham, Rajiv R. Singh, Hsueh S. Tung
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Patent number: 7335805Abstract: Methods and materials are provided for the production of essentially isomerically pure perhalogenated and partially halogenated compounds. One embodiment of the present invention provides a process for the production of essentially isomerically pure CFC-216aa. Other embodiments include processes for the production of CFC-217ba and HFC-227ea. Particular embodiments of the present invention provide separation techniques for the separation of chlorofluorocarbons from HF, from other chlorofluorocarbons, and the separation of isomers of halogenated compounds. Still other embodiments of the present invention provide catalytic synthetic techniques that demonstrate extended catalyst lifetime. In other embodiments, the present invention provides catalytic techniques for the purification of isomeric mixtures.Type: GrantFiled: October 31, 2003Date of Patent: February 26, 2008Assignee: Great Lakes Chemical CorporationInventors: Yuichi Iikubo, Stephen Owens, Mitchel Cohn, Stephan M. Brandstadter, Vicki E. Hedrick, Janet K. Boggs, John Qian, Julie Sacarias
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Patent number: 7157550Abstract: A purification process of thermoprocessable tetrafluoroethylene (TFE) copolymers comprising the following steps: A) the polymer latex is transformed into gel form, under mechanical stirring, by addition of an acid electrolyte having pH values?2; B) washing of the polymer gel with aqueous solutions having pH from 1 to 7.Type: GrantFiled: March 3, 2004Date of Patent: January 2, 2007Assignee: Ausimont S.p.A.Inventors: Hua Wu, Vincenzo Arcella
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Patent number: 7151197Abstract: Methods and materials are provided for the production of essentially isomerically pure perhalogenated and partially halogenated compounds. One embodiment of the present invention provides a process for the production of essentially isomerically pure CFC-216aa. Other embodiments include processes for the production of CFC-217ba and HFC-227ea. Particular embodiments of the present invention provide separation techniques for the separation of chlorofluorocarbons from HF, from other chlorofluorocarbons, and the separation of isomers of halogenated compounds. Still other embodiments of the present invention provide catalytic synthetic techniques that demonstrate extended catalyst lifetime. In other embodiments, the present invention provides catalytic techniques for the purification of isomeric mixtures.Type: GrantFiled: October 31, 2003Date of Patent: December 19, 2006Assignee: Great Lakes Chemical CorporationInventors: Yuichi Iikubo, Stephen Owens, Mitchel Cohn, Stephan M. Brandstadter, Vicki E. Hedrick, Janet K. Boggs, John Qian, Julie Sacarias
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Patent number: 7074434Abstract: Process for the separation of a mixture comprising at least one hydrofluoroalkane and hydrogen fluoride, according to which a hydrofluoroalkane/hydrogen fluoride mixture is reacted with at least one chlorinated or chlorofluorinated precursor of the hydrofluoroalkane. Process for the preparation of a hydrofluoroalkane comprising such a separation, in combination with a catalytic reaction stage. Azeotropic compositions.Type: GrantFiled: October 29, 2002Date of Patent: July 11, 2006Assignee: Solvay (Societe Anonyme)Inventors: Alain Lambert, Vincent Wilmet
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Patent number: 7015368Abstract: A purification process of thermoprocessable tetrafluoroethylene (TFE) copolymers comprising the following steps: A) the polymer latex is transformed into gel form, under mechanical stirring, by addition of an acid electrolyte having pH values ?2; B) washing of the polymer gel with aqueous solutions having pH from 1 to 7.Type: GrantFiled: July 26, 2002Date of Patent: March 21, 2006Assignee: Ausimont S.p.A.Inventors: Hua Wu, Vincenzo Arcella
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Patent number: 6710216Abstract: In a closed-loop biomass extraction apparatus (10), strategies for purifying HFC solvents used therein include: (i) contacting an adsorbent and a desiccant, e.g. in a container (26) with contaminated HFC solvent branched from the main flow loop; and, optionally, (ii) washing contaminated HFC solvent with water, e.g. in a vessel (34) to separate a co-solvent or entrainer, such as ethanol, thereform.Type: GrantFiled: September 5, 2000Date of Patent: March 23, 2004Assignee: Imperial Chemical Industries PLCInventors: Stuart Corr, Paul A. Dowdle, Robert E. Low, James David Morrison, Frederick Thomas Murphy
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Patent number: 6673264Abstract: The invention relates to azeotropic and azeotrope-like mixtures of 1,1,1,3,3-pentafluorobutane (HFC-365) and hydrogen fluoride and a process for separating the azeotrope-like mixtures. The compositions of the invention are useful as an intermediate in the production of HFC-365. The latter is useful as a nontoxic, zero ozone depleting fluorocarbon useful as a solvent, blowing agent, refrigerant, cleaning agent and aerosol to propellant.Type: GrantFiled: June 3, 2002Date of Patent: January 6, 2004Assignee: Honeywell International Inc.Inventors: Hang T. Pham, Rajiv R. Singh, Hsueh S. Tung
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Patent number: 6642415Abstract: Fluorinated emulsifiers, in particular, perfluorooctanoic acid are bound to anionic exchange resins for the purification of aqueous effluent from the production of fluoropolymers. Said emulsifiers may be quantitatively eluted from the exchanger with a water-miscible organic solvent, containing a small amount of ammonia. It is of advantage to distil off the ammonia containing solvent, recycle the emulsifier to a further polymerization and recycle the ammoniacal solvent for elution. Addition of alkalis improves the elution efficiency.Type: GrantFiled: April 12, 2002Date of Patent: November 4, 2003Assignee: 3M Innovative Properties CompanyInventors: Stephan Führer, Klaus Hintzer, Gernot Löhr, Werner Schwertfeger
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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
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Patent number: 6500994Abstract: A process for purification of 1,1,1,3,3-pentafluorobutane (HFC-365mfc) containing a decreased amount of hydrogen chloride, hydrogen fluoride and/or unsaturated impurities. To this end crude 1,1,1,3,3-pentafluorobutane is treated in the liquid phase with a solid, inorganic sorption agent and/or with diatomic molecules which and to C—C multiple bonds. The product to be purified is preferably treated with elemental fluorine. The contents of hydrogen chloride and hydrogen can each be decreased to below 1 ppm. The content of unsaturated (chlorine)-fluorine-compounds can be decreased to below 20 ppm, and the content of unsaturated C2 compounds can be decreased to below 10 ppm. It has also been discovered that fluorotrichloroethylene can be used as a control substance to monitor the purification of 1,1,1,3,3-pentafluorobutane.Type: GrantFiled: June 8, 2001Date of Patent: December 31, 2002Assignee: Solvay Fluor und Derivate GmbHInventors: Carsten Brosch, Heinz Gress, Matthias Rieland
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Patent number: 6437168Abstract: A method for efficiently extracting a reaction product containing a target aromatic fluorine compound formed by the halogen exchange reaction of an aromatic chlorine compound with a fluorinating agent quickly from the reaction vessel without suffering part of the reaction product to remain as a residue inside the reaction vessel is disclosed. Specifically, the reaction product is extracted from the reactor subsequently to the halogen exchange reaction at a temperature in the range of 20-250° C. By this method, the reaction product formed in consequence of the halogen exchange reaction can be efficiently extracted quickly from the reaction vessel, and that without suffering occurrence of a residue of the reaction product.Type: GrantFiled: August 29, 2001Date of Patent: August 20, 2002Assignee: Nippon Shokubai Co., Ltd.Inventor: Kouichi Hirota
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Patent number: 6403849Abstract: A method for obtaining purified perfluorocarbon compositions, and purified compositions containing such perfluorocarbons.Type: GrantFiled: September 26, 2000Date of Patent: June 11, 2002Assignee: 3M Innovative Properties CompanyInventors: Zai-Ming Qiu, Zhongxing Zhang
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Patent number: 6399841Abstract: Hydrogen fluoride is separated from its mixtures with 1,1,1,3,3-pentafluorobutane by extraction using an organic solvent containing a 1,1,1,3,3-chloro(fluoro)butane.Type: GrantFiled: September 24, 2001Date of Patent: June 4, 2002Assignee: Solvay (Societe Anonyme)Inventors: Alain Lambert, Vincent Wilmet
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Publication number: 20020040172Abstract: The invention relates to the purification of pentafluoroethane (F125) containing chloropentafluoroethane (F115) by liquid/liquid extraction or by extractive distillation.Type: ApplicationFiled: June 26, 2001Publication date: April 4, 2002Inventors: Emmanuel Guiraud, Cathy Descamps
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Publication number: 20020010373Abstract: The invention relates to a process for purifying a crude 1,1,1,5,5,5-hexafluoroacetylacetone dihydrate containing an impurity. The process includes bringing the crude 1,1,1,5,5,5-hexafluoroacetylacetone dihydrate into contact with a poor solvent in which 1,1,1,5,5,5-hexafluoroacetylacetone dihydrate is substantially insoluble, thereby removing the impurity from the crude 1,1,1,5,5,5-hexafluoroacetylacetone dihydrate. Alternatively, the process includes precipitating crystals of 1,1,1,5,5,5-hexafluoroacetylacetone dihydrate from a solution of the crude 1,1,1,5,5,5-hexafluoroacetylacetone dihydrate. Thus, it is possible to produce 1,1,1,5,5,5-hexafluoroacetylacetone dihydrate of high purity. This product makes it easy to produce 1,1,1,5,5,5-hexafluoroacetylacetone of high purity.Type: ApplicationFiled: December 21, 2000Publication date: January 24, 2002Inventors: Takeo Komata, Nariaki Ii, Yoshiki Hirotsu
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Publication number: 20020007099Abstract: 1,1-Difluoroethane containing less than 10 mg/kg of vinyl chloride is obtained by treatment, with hydrogen fluoride, of a crude 1,1-difluoroethane containing less than 1 mol of hydrogen chloride per mole of 1,1-difluoroethane.Type: ApplicationFiled: November 30, 1998Publication date: January 17, 2002Inventors: CHARLES-MARIE ANCIAUX, VINCENT WILMET, DOMINIQUE LECROC
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Patent number: 6328907Abstract: There is provided an azeotropic mixture consisting substantially of 1,1,1, 3,3-pentafluoropropane and hydrogen fluoride. Further, there is provided a process of separating/purifying R-245fa and/or HF from a mixture comprising R-245fa and HF wherein the mixture comprising 1,1,1,3,3-pentafluoropropane and hydrogen fluoride is subjected to a distillation step so that a distillate is obtained which comprises the azeotropic mixture consisting substantially of 1,1,1,3,3-pentafluoropropane and hydrogen fluoride, and a bottom product is obtained which comprises separated/purified 1,1,1,3,3-pentafluoropropane or hydrogen fluoride.Type: GrantFiled: July 23, 1998Date of Patent: December 11, 2001Assignee: Daikin Industries, Ltd.Inventors: Tatsuo Nakada, Noriaki Shibata, Takashi Shibanuma
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Patent number: 6307115Abstract: The invention relates to the purification of pentafluoroethane (F125) containing chloropentafluoroethane (F115) by liquid/liquid extraction or by extractive distillation. Perchloroethylene is used as extraction agent.Type: GrantFiled: November 13, 1997Date of Patent: October 23, 2001Inventors: Emmanuel Guiraud, Cathy Descamps
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Patent number: 6303838Abstract: Disclosed are processes for separating 1,1,1,3,3-pentafluoropropane (HFC-245fa) from hydrogen fluoride (HF) by distillation, wherein hydrocarbons, chloroflurocarbons, hydrochlorofluorocarbons and fluorocarbons are used as entraining agents. The processes comprise: contacting a first mixture comprising HFC-245fa and HF with an entraining agent selected from the group consisting of hydrocarbons, chlorofluorocarbons, hydrochlorofluorocarbons and fluorocarbons to form a second mixture, distilling the second mixture and thereby separating the HFC-245fa from HF and entraining agent, and recovering HFC-245fa substantially-free of HF.Type: GrantFiled: March 31, 2000Date of Patent: October 16, 2001Assignee: E.I. du Pont de Nemours and CompanyInventors: Sara W. Boehmer, Barry Asher Mahler, Ralph Newton Miller
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Patent number: 6297412Abstract: A process for purifying difluoromethane, which comprises subjecting a mixture comprising difluoromethane and hydrogen fluoride to extraction treatment with at least one extractant selected from the following (a) and (b) to separate it by liquid separation into an extractant layer comprising the difluoromethane and the extractant as the main components, and a hydrogen fluoride layer comprising the hydrogen fluoride as the main component, and separating the difluoromethane from the extractant layer: (a) Dichloromethane (b) Chlorofluoromethane.Type: GrantFiled: February 21, 2001Date of Patent: October 2, 2001Assignee: Asahi Glass Company, LimitedInventors: Takaaki Yokoyama, Koichi Yanase, Yasuhiro Suzuki
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Patent number: 6294055Abstract: Process for the separation of hydrogen fluoride from its mixtures with a hydrofluoroalkane containing from 3 to 6 carbon atoms, by extraction using an organic solvent.Type: GrantFiled: September 11, 1998Date of Patent: September 25, 2001Assignee: Solvay S.A.Inventors: Ralf Herkelmann, Carsten Brosch, Vincent Wilmet
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Publication number: 20010021793Abstract: A process for purifying difluoromethane, which comprises subjecting a mixture comprising difluoromethane and hydrogen fluoride to extraction treatment with at least one extractant selected from the following (a) and (b) to separate it by liquid separation into an extractant layer comprising the difluoromethane and the extractant as the main components, and a hydrogen fluoride layer comprising the hydrogen fluoride as the main component, and separating the difluoromethane from the extractant layer:Type: ApplicationFiled: February 21, 2001Publication date: September 13, 2001Applicant: Asahi Glass Company, LimitedInventors: Takaaki Yokoyama, Koichi Yanase, Yasuhiro Suzuki
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Publication number: 20010004961Abstract: Process for the separation of hydrogen fluoride from its mixtures with a hydrofluoroalkane containing from 3 to 6 carbon atoms, by extraction using an organic solvent.Type: ApplicationFiled: September 11, 1998Publication date: June 28, 2001Inventors: RALF HERKELMANN, CARSTEN BROSCH, VINCENT WILMET
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Patent number: 6191328Abstract: HFC-245fa is effectively separated from the mixture comprising 1,1,1,3,3-pentafluoropropane (HFC-245fa) and HF through a purification process comprising contacting at least one extraction agent selected from the group consisting of (a) a compound corresponds to the general formula (I): CxFyHz, (b) a compound corresponds to the general formula (II): R1R2R3N, (c) an compound corresponds to the general formula (III): R4OR5 and (d) a compound corresponds to the general formula (IV): ClClmHn with a mixture comprising 1,1,1,3,3-pentafluoropropane and hydrogen fluoride so as to form a liquid mixture and separating the liquid mixture into two liquid layers, followed by obtaining an extraction agent phase including HFC-245fa and the extraction agent as the main components, and separatively recovering HFC-245fa from the extraction agent phase.Type: GrantFiled: December 22, 1998Date of Patent: February 20, 2001Assignee: Daikin Industries, Ltd.Inventors: Keisuke Kitano, Tatsuo Nakada, Takashi Shibanuma
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Patent number: 6175045Abstract: There is provided a process of effectively separating pentafluoroethane (HFC-125) from a mixture of HFC-125 and chloropentafluoroethane (CFC-115). When the mixture of HFC-125 and CFC-115 is subjected to an extractive distillation to obtain a concentrated HFC-125, ethyleneglycol-based compounds (3) having a general formula: R1O(CH2CH2O)nR2 wherein R1 and R2 may be the same or different and are each independently selected from the group consisting of hydrogen and an alkyl group having 1 to 4 carbon atoms, and n is an integer with a value from 1 to 3 is used as an extractant, whereby CFC-115 is obtained as a distillate product (4) and a mixture of HFC-125 and the extractant as a bottom product (5) is obtained. Then, the extractant is separated from HFC-125 by distilling the mixture and re-used in the extractive distillation.Type: GrantFiled: November 22, 1999Date of Patent: January 16, 2001Assignee: Daikin Industries Ltd.Inventors: Satoru Kohno, Takashi Shibanuma
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Patent number: 6156944Abstract: A process for the separation of mixtures containing halocarbons and hydrogen fluoride. Either water alone or a blend comprising water and hydrogen fluoride is added to a mixture comprising a halocarbon and hydrogen fluoride to thereby form a first phase rich in the halocarbon and a second phase rich in hydrogen fluoride and water. The most preferred halocarbon is 1,1,1,3,3-pentafluoropropane. Preferably, the first and second phases are then separated. Optionally, the second phase rich in hydroger fluoride and water is also separated.Type: GrantFiled: March 3, 1998Date of Patent: December 5, 2000Assignee: Honeywell International Inc.Inventors: Hang T. Pham, Rajiv R. Singh, Charles F. Swain, Michael Van Der Puy
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Patent number: 6013846Abstract: An azeotrope containing HF and 1233zd is provided, as are methods for separating this azeotrope from mixtures of HF and 1233zd which are HF-rich or 1233zd-rich and methods for making use of the azeotrope and separation methods to improve processes for preparing 1233zd, an intermediate used in the preparation of 245fa. 245fa is a known foam blowing agent and refrigerant.Type: GrantFiled: March 5, 1998Date of Patent: January 11, 2000Assignee: Elf Atochem North America, Inc.Inventors: John A. Wismer, Michael S. Bolmer, Bin Chen
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Patent number: 5973215Abstract: A process is disclosed for the liquid phase separation and recovery of hydrogen fluoride from a mixture comprising hydrogen fluoride and a fluorinated organic hydrocarbon. The process requires that the mixture be treated with a sufficient amount of a coupled phase-separating agent comprising an organic or inorganic salt, an alkanolamine or mixtures thereof and a substituted or unsubstituted aromatic compound to form a first and a second phase. The first phase that is formed is a hydrogen fluoride-rich phase that additionally contains substantially all of said salt, said alkanolamine or mixtures thereof from the coupled phase-separating agent. The second phase comprises substantially all of said aromatic compound and the fluorinated organic hydrocarbon. It is substantially free of hydrogen fluoride. The phases are separated from each other.Type: GrantFiled: March 16, 1998Date of Patent: October 26, 1999Assignee: LaRoche Industries IncInventor: Randolph K. Belter
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Patent number: 5874657Abstract: The present invention relates to processes for separating 1,1-difluoroethane (HFC-152a) from vinyl chloride by using extractive distillation with an extractive agent selected from the aliphatic hydrocarbons, chlorocarbons and alcohols.Type: GrantFiled: October 29, 1997Date of Patent: February 23, 1999Assignee: E. I. du Pont de Nemours and CompanyInventors: Ralph Newton Miller, Barry Asher Mahler
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Patent number: 5874658Abstract: A method is disclosed for separating a mixture of at least one hydrofluorocarbon from hydrogen fluoride. The method comprising treating said mixture with a compound selected from the group consisting of an alkanolamine of formulaNH.sub.a (CH.sub.b R.sub.c).sub.dwhere R is C.sub.1 to C.sub.6 linear or branched alkylene substituted with at least one hydroxy group, wherein a and d are the integers 1 or 2 and a+d=3 and b is 0 or the integer 1 or 2 and b+c=3, C.sub.6 to C.sub.10 aryl unsubstituted or substituted with halo or halo-substituted C.sub.1 to C.sub.6, alkyl, sulfuric acid and sulfuric acid admixed with at least one alkali metal sulfate. The hydrofluorocabon and HF form two separate phases by this treatment. The phases are readily separated.Type: GrantFiled: September 12, 1997Date of Patent: February 23, 1999Assignee: LaRoche Industries Inc.Inventor: Randolph K. Belter
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Patent number: 5852223Abstract: The purification of pentafluoroethane (HFC-125) which is composed of a process A, in which an unpurified mixture (1), containing at least chloropentafluoroethane (CFC-115) and pentafluoroethane (HFC-125) is reacted with hydrogen (4) in the presence of a catalyst in gas phase to reduce the said chloropentafluoroethane (CFC-115); and a process B, in which a reaction mixture produced by the preceding reaction is separated into a first mixture (3) composed mainly of hydrogen and a second mixture (2), composed mainly of pentafluoroethane (HFC-125). In this method, purification is performed by adding the said first mixture (3) to the said unpurified mixture (1) in a state that the hydrogen chloride is removed from the first mixture (3) in process B until the level of hydrogen chloride drops to 0.Type: GrantFiled: January 28, 1997Date of Patent: December 22, 1998Assignee: Daikin Industries, Ltd.Inventors: Satoru Kohno, Takashi Shibanuma
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Patent number: 5744662Abstract: A process for separating and purifying dichlorodifluoromethane and 1,1,1,2 tetrafluoroethane from a feed of their mixtures by liquid-liquid extraction with extracting solvent containing paraffinic or naphthalenic mineral oils or a mixture thereof, with or without a stripping agent such as ethylene glycol or triethylene glycol or a mixture thereof.Type: GrantFiled: April 17, 1996Date of Patent: April 28, 1998Inventor: Mohamad Karim Moallemi
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Patent number: 5744669Abstract: A process for the conversion of a halogenated organic stream containing trace quantities of organic nitrates to produce a stream comprising hydrogenated hydrocarbonaceous compounds free from organic nitrates and halogenated organic compounds by means of contacting the feed stream and hydrogen with a selective hydrogenation catalyst in a first hydrogenation zone at hydrogenation conditions to convert the organic nitrates into water-soluble nitrogen compounds while effectively minimizing the production of hydrogen halide compounds. The resulting effluent from the first hydrogenation zone is contacted with an aqueous scrubbing solution to recover at least a portion of the water-soluble nitrogen compounds in order to produce a stream containing halogenated organic compounds and essentially free of nitrogen compounds which is then introduced into a second hydrogenation zone operated at selected hydrogenation conditions to produce water-soluble hydrogen halide compounds and hydrogenated hydrocarbonaceous compounds.Type: GrantFiled: January 30, 1997Date of Patent: April 28, 1998Assignee: UOPInventors: Tom N. Kalnes, George R. Hibel, Chwu-Ching Jan
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Patent number: 5696309Abstract: Disclosed is a method of chlorinating vinylidene chloride contained in a solution 1,1 -dichloro-1-fluoroethane to provide a chlorinated compound having a boiling point different from the 1,1-dichloro-1-fluoroethane to permit separation therefrom. The method comprises providing a solution containing 1,1-dichloro-1-fluoroethane and vinylidene chloride; introducing chlorine to the solution; and contacting the chlorine containing solution with a metal oxide to effect chlorination of the vinylidene chloride to produce one of 1,1,1,2-tetrachloroethane, trichloroethylene and pentachloroethane.Type: GrantFiled: April 17, 1995Date of Patent: December 9, 1997Assignee: LaRoche Industries, Inc.Inventors: Andrew Jackson, C. Bradford Boyce
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Patent number: 5684219Abstract: A process is disclosed for the preparation of a fluorinated aliphatic olefin having the formulaCH.sub.a F.sub.3-a --CH.sub.2 --CH.sub.b F.sub.3-bwherein a is 0 or the integer 1 or d and b is 0 or the integer 1, 2 or 3.In the first step of the process, a chlorinated olefinic hydrocarbon of the formulaCH.sub.c Cl.sub.2-c .dbd.CH--CH.sub.d Cl.sub.3-dwherein c is 0 or the integer 1 and d is 0 or the integer 1 or 2 is reacted with anhydrous hydrogen fluoride for a period of time and at a temperature sufficient to form a chlorofluoro olefin of the formulaCH.sub.e Cl.sub.2-e .dbd.CH--CH.sub.f F.sub.3-fwherein e is 0 or the integer 1 and f is 0 or the integer 1 or 2.The chlorofluoro olefin produced in the first step is then reacted with anhydrous hydrogen fluoride in a second reaction. This second reaction is catalyzed with at least one compound that is a metal oxide or metal halide. Mixtures of said metal oxides, metal halides and metal oxides with metal halides may also be used.Type: GrantFiled: November 5, 1996Date of Patent: November 4, 1997Assignee: LaRoche Industries Inc.Inventors: C. Bradford Boyce, Randolph Kenneth Belter