Metal Oxide Containing Catalyst Patents (Class 570/169)
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Patent number: 7329786Abstract: 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: September 28, 2001Date of Patent: February 12, 2008Assignee: Great Lakes Chemical CorporationInventors: Yuichi Iikubo, Stephen Owens, Mitchel Cohn, Stephan M. Brandstadter, Vicki E. Hedrick, Janet K. Boggs, John Chengping Chien, Julie Sacarias, Vimal Sharma
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Patent number: 7312367Abstract: The invention provides an economic process for the manufacture of the hydrofluorocarbon 1,1,3,3,3-pentafluoropropene (HFC-1225zc). HFC-1225zc can be made from the dehydrochlorination of 1-chloro-1,1,3,3,3-pentafluoropropane (HCFC-235fa). Alternatively, HFC-1225zc can also be made from the dehydrofluorination of 1,1,1,3,3,3-hexafluoropropane (HFC-236fa). HFC-1225zc) is a compound that has the potential to be used as a low Global Warming Potential refrigerant, blowing agent, aerosol propellant, or solvent.Type: GrantFiled: June 14, 2006Date of Patent: December 25, 2007Assignee: Honeywell International Inc.Inventors: Hsueh Sung Tung, Daniel C. Merkel, Rajiv R. Singh
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Patent number: 7241928Abstract: A liquid phase process is disclosed for producing halogenated alkane adducts of the formula CAR1R2CBR3R4 (where A, B, R1, R2, R3, and R4 are as defined in the specification) which involves contacting a corresponding halogenated alkane, AB, with a corresponding olefin, CR1R2?CR3R4 in a dinitrile or cyclic carbonate ester solvent which divides the reaction mixture into two liquid phases and in the presence of a catalyst system containing (i) at least one catalyst selected from monovalent and divalent copper; and optionally (ii) a promoter selected from aromatic or aliphatic heterocyclic compounds which contain at least one carbon-nitrogen double bond in the heterocyclic ring. When hydrochlorofluorocarbons are formed, the chlorine content may be reduced by reacting the hydrochlorofluorocarbons with HF. New compounds disclosed include CF3CF2CCl2CH2CCl3, CF3CCl2CH2CH2Cl and CF3CCl2CH2CHClF. These compounds are useful as intermediates for producing hydrofluorocarbons.Type: GrantFiled: October 1, 2004Date of Patent: July 10, 2007Assignee: E. I. du Pont de Nemours and CompanyInventors: Velliyur N.Mallikarjuna Rao, Allen Capron Sievert
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Patent number: 7214839Abstract: A manufacturing process for making hydrofluorocarbons (HFCs), by reacting a hydrochlorocarbon and HF in a liquid phase catalytic reactor using a large mole ratio of HF to hydrochlorocarbon to minimize formation of high boiling by-products and improve HF consumption and hydrofluorocarbon yields.Type: GrantFiled: May 23, 2003Date of Patent: May 8, 2007Assignee: Honeywell International Inc.Inventors: Hsueh Sung Tung, Chad L. Marks, Stephen A. Cottrell
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Patent number: 7183448Abstract: A mixture comprising at least 1,1,1,3,3-pentafluoropropane and 1,1,1-trifluoro-3-chloro-2-propene is subjected to a distillation operation, and thereby, a distillate comprising an azeotropic composition consisting substantially of 1,1,1,3,3-pentafluoropropane and 1,1,1-trifluoro-3-chloro-2-propene is obtained and a bottom product comprising 1,1,1,3,3-pentafluoropropane or 1,1,1-trifluoro-3-chloro-2-propene which each is separated and purified.Type: GrantFiled: November 10, 1999Date of Patent: February 27, 2007Assignee: Daikin Industries, Ltd.Inventors: Tatsuo Nakada, Masayoshi Imoto, Takashi Shibanuma
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Patent number: 7138553Abstract: Tetrachloroethylene containing a stabilizer is contacted with a zeolite having an average pore size of 3.4 to 11 ? and/or a carbonaceous adsorbent having an average pore size of 3.4 to 11 ? in a liquid phase to obtain a high purity tetrachloroethylene. A halogenated alkene and/or a halogenated alkane are reacted with hydrogen fluoride in the presence of a fluorination catalyst to produce a first hydrofluorocarbon, a halogenated alkene and/or a halogenated alkane are reacted with hydrogen fluoride in the presence of a fluorination catalyst to produce a second hydrofluorocarbon, and the products are joined and then distilled to obtain the first and second hydrofluorocarbons.Type: GrantFiled: July 5, 2002Date of Patent: November 21, 2006Assignee: Showa Denko K.K.Inventors: Hiromoto Ohno, Toshio Ohi, Makoto Miyamura
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Patent number: 7129383Abstract: A process for the preparation of 2-chloro-1,1,1,3,3,3-heptafluoropropane is disclosed which involves (a) contacting a mixture comprising hydrogen fluoride, chlorine, and at least one starting material selected from the group consisting of halopropenes of the formula CX3CCI?CX2 and halopropanes of the formula the CX3CCIYCX3, wherein each X is independently F or Cl, and Y is H, Cl or F (provided that the number of X and Y which are F totals no more than six) with a chlorofluorination catalyst in a reaction zone to produce a product mixture comprising CF3CCIFCF3, HCI, HF. and underfluorinated halogenated hydrocarbon intermediates. The process is characterized by said chlorofluorination catalyst comprising at least one chromium-containing component selected from (i) a crystalline alpha-chromium oxide where at least 0.Type: GrantFiled: August 21, 2003Date of Patent: October 31, 2006Assignee: E. I. du Pont de Nemours and CompanyInventors: Mario J. Nappa, Velliyur Nott Mallikarjuna Rao, H. David Rosenfeld, Sekhar Subramoney, Munirpallam A. Subramanian, Allen C. Sievert
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Patent number: 7091388Abstract: The invention provides an economic process for the manufacture of the hydrofluorocarbon 1,1,3,3,3-pentafluoropropene (HFC-1225zc). HFC-1225zc can be made from the dehydrochlorination of 1-chloro-1,1,3,3,3-pentafluoropropane (HCFC-235fa). Alternatively, HFC-1225zc can also be made from the dehydrofluorination of 1,1,1,3,3,3-hexafluoropropane (HFC-236fa). HFC-1225zc) is a compound that has the potential to be used as a low Global Warming Potential refrigerant, blowing agent, aerosol propellant, or solvent.Type: GrantFiled: September 26, 2003Date of Patent: August 15, 2006Assignee: Honeywell International Inc.Inventors: Hsueh Sung Tung, Daniel C. Merkel, Rajiv R. Singh
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Patent number: 7074973Abstract: A process for the preparation of pentafluoroethane is disclosed which involves contacting a mixture comprising hydrogen fluoride and at least one starting material selected from haloethanes of the formula CX3CHX2 and haloethanes of the formula CX2?CX2, where each X is independently selected from the group consisting of F and Cl (provided that no more than four of X are F), with a fluorination catalyst in a reaction zone to produce a product mixture comprising HF, HCl, pentafluoroethane, underfluorinated halogenated hydrocarbon intermediates and less than 0.2 mole percent chloropentafluoroethane based on the total moles of halogenated hydrocarbons in the product mixture. The process is characterized by the fluorination catalyst comprising (i) a crystalline cobalt-substituted alpha-chromium oxide where from about 0.05 atom % to about 6 atom % of the chromium atoms in the alpha-chromium oxide lattice are replaced by trivalent cobalt (Co+3) and/or (ii) a fluorinated crystalline oxide of (i).Type: GrantFiled: August 21, 2003Date of Patent: July 11, 2006Assignee: E. I. du Pont de Nemours and CompanyInventors: Mario J. Nappa, Velliyur Nott Mallikarjuna Rao, H. David Rosenfeld, Shekhar Subramoney, Munirpallam A. Subramanian, Allen C. Sievert
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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: 7067706Abstract: Process for the preparation of a hydro(chloro)fluoroalkane according to which a halogenated precursor of the hydro(chloro)fluoroalkane is reacted with hydrogen fluoride in the presence of a catalyst comprising chromium (Cr) and at least one other metal selected from the group consisting of aluminium, barium, bismuth, calcium, cerium, copper, iron, magnesium, strontium, vanadium and zirconium.Type: GrantFiled: April 9, 2001Date of Patent: June 27, 2006Assignee: Solvay (Societe Anonyme)Inventors: Vincent Wilmet, Francine Janssens
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Patent number: 7064240Abstract: The process for producing perfluorocarbons according to the present invention is characterized in that in the production of a perfluorocarbon by contacting an organic compound with a fluorine gas, the organic compound is contacted with the fluorine gas at a temperature of from 200 to 500° C. and the content of an oxygen gas within the reaction system is controlled to 2% by volume or less based on the gas components in the reaction starting material, whereby a perfluorocarbon reduced in the content of impurities is produced. According to the process for producing perfluorocarbons of the present invention, high-purity perfluorocarbons extremely suppressed in the production of impurities such as oxygen-containing compound can be obtained. The perfluorocarbons obtained by the production process of the present invention contain substantially no oxygen-containing compound and therefore, can be effectively used as an etching or cleaning gas for use in the process for producing a semiconductor device.Type: GrantFiled: February 21, 2002Date of Patent: June 20, 2006Assignee: Showa Denko K.K.Inventors: Hiromoto Ohno, Toshio Ohi
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Patent number: 7045668Abstract: A process for production of high-purity hexafluoroethane, wherein a mixed gas containing hexafluoroethane and chlorotrifluoromethane is reacted with hydrogen fluoride in a gas phase in the presence of a fluorination catalyst at 200-450° C., for fluorination of the chlorotrifluoromethane, or wherein pentafluoroethane containing chlorine compounds with 1-3 carbon atoms is reacted with hydrogen in a gas phase in the presence of a hydrogenation catalyst at 150-400° C., and the product is then reacted with fluorine in a gas phase in the presence of a diluent gas.Type: GrantFiled: August 6, 2002Date of Patent: May 16, 2006Assignee: Showa Denko K.K.Inventors: Hiromoto Ohno, Toshio Ohi
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Patent number: 6930215Abstract: 1,1,1,3,3-pentafluoropropane is produced by reaction between 1,1,1,3,3-pentachloropropane and hydrogen fluoride in the presence of a hydrofluorination catalyst. The 1,1,1,3,3-pentachloropropane may advantageously be obtained by reaction between vinyl chloride and tetrachloromethane in the presence of a telomerization catalyst and of a nitrile.Type: GrantFiled: July 3, 2003Date of Patent: August 16, 2005Assignee: Solvey (Societe Anonyme)Inventors: Vincent Wilmet, Francine Janssens, Jean-Paul Schoebrechts
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Patent number: 6927312Abstract: Disclosed are improved fluorination processes and fluorine-containing compositions which involve introducing to one or more fluorination process compositions a water reactive agent in an amount and under conditions effective to decrease the amount of water in that composition. The water reactive agent is preferably introduced to the fluorination reaction process at a location proximate to the site of the fluorination reaction, or upstream of the fluorination reaction, in amounts and under conditions effective to produce a relatively lower concentration of water in the composition, and preferably throughout the fluorination process.Type: GrantFiled: November 12, 2003Date of Patent: August 9, 2005Assignee: Honeywell International Inc.Inventors: Jason T. Stuck, Hsueh Sung Tung, Michael Van Der Puy, Timothy R. Demmin, Franklin S. Wong, Andrew J. Poss, Matthew H. Luly
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Patent number: 6900362Abstract: A process for the production of HFC-227ea from HF and HFP is provided. This process takes advantage of an azeotropic composition of HF and HFC-227ea in order to produce HFC-227ea essentially free of HF and recycle unreacted HF back to the reactor. The recycle of said azeotropic composition, also allows the use of HFC-227ea as a diluent to aid in control of reactor temperature for a highly exothermic reaction.Type: GrantFiled: October 31, 2002Date of Patent: May 31, 2005Assignee: E. I. du Pont de Nemours and CompanyInventors: Ralph Newton Miller, Mario J. Nappa, Donald J. Toton
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Patent number: 6881698Abstract: The ionic liquids according to the invention result from the reaction of a halogenated or oxyhalogenated Lewis acid based on titanium, niobium, tantalum, tin or antimony with an organic salt of formula X+A? in which A? is a halide anion and X+ a quaternary ammonium, quaternary phosphonium or ternary sulphonium cation. These liquids can be used in particular in the liquid-phase fluorination using HF of saturated or unsaturated compounds having C—Cl groups.Type: GrantFiled: April 24, 2001Date of Patent: April 19, 2005Assignee: AtofinaInventors: Phillippe Bonnet, Eric Lacroix, Jean-Pierre Schirmann
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Patent number: 6858762Abstract: A liquid phase process is disclosed for producing halogenated alkane adducts of the formula CAR1R2CBR3R4 (where A, B, R1, R2, R3, and R4 are as defined in the specification) which involves contacting a corresponding halogenated alkane, AB, with a corresponding olefin, CR1R2?CR3R4 in a dinitrile or cyclic carbonate ester solvent which divides the reaction mixture into two liquid phases and in the presence of a catalyst system containing (i) at least one catalyst selected from monovalent and divalent copper; and optionally (ii) a promoter selected from aromatic or aliphatic heterocyclic compounds which contain at least one carbon-nitrogen double bond in the heterocyclic ring. When hydrochlorofluorocarbons are formed, the chlorine content may be reduced by reacting the hydrochlorofluorocarbons with HF. New compounds disclosed include CF3CF2CCl2CH2CCl3, CF3CCl2CH2CH2Cl and CF3CCl2CH2CHClF. These compounds are useful as intermediates for producing hydrofluorocarbons.Type: GrantFiled: June 12, 2003Date of Patent: February 22, 2005Assignee: E. I. du Pont de Nemours and CompanyInventors: Ralph Thomas Baker, Ralph Newton Miller, Viacheslav Alexandrovich Petrov, Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
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Patent number: 6849772Abstract: 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: GrantFiled: October 7, 2002Date of Patent: February 1, 2005Assignee: Solvay (Societe Anonyme)Inventors: Charles-Marie Anciaux, Vincent Wilmet, Dominique Lecroc
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Patent number: 6844475Abstract: A process for producing 1-chloro-3,3,3-trifluoropropene (HCFC-1233zd) from 1,1,1-3,3-pentachloropropane (HCC-240fa) by its reaction with hydrogen fluoride, the reactants are reacted in a liquid phase reaction at a temperature of less than 150° C. in the presence of a Lewis acid catalyst or mixture of Lewis acid catalysts, and hydrogen chloride and HCFC-1233zd formed in the reaction are continuously removed and the HCFC-12333zd is isolated.Type: GrantFiled: August 8, 2003Date of Patent: January 18, 2005Assignee: Honeywell International Business MachinesInventors: Hseuh Sung Tung, Kevin D. Ulrich, Daniel C. Merkel
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Patent number: 6841706Abstract: Hydrofluorination catalyst based on a chromium oxide which is poor in ammonium salts.Type: GrantFiled: October 11, 1999Date of Patent: January 11, 2005Assignee: Solvay (Societe Anonyme)Inventors: Vincent Wilmet, Georges Lejeune
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Patent number: 6841705Abstract: A method of producing difluoromethane (HFC-32), which includes firstly reacting methylene chloride with hydrogen fluoride in gas phase at 280 to 340° C. in the presence of a fluorination catalyst to produce chlorofluoro methane, and secondly reacting the chlorofluoro methane with hydrogen fluoride in liquid phase at 60 to 80° C. in the presence of an antimony chloride catalyst. The method is advantageous in that HFC-32 is produced in high yield under mild reaction conditions using a relatively small amount of energy.Type: GrantFiled: February 24, 2003Date of Patent: January 11, 2005Assignee: Ulsan Chemical Co., Ltd.Inventors: Iikubo Yuichi, Hae Seok Ji, Ook Jae Cho
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Patent number: 6755942Abstract: The invention relates to azeotropic compositions of halogenated propanes with HF.Type: GrantFiled: August 14, 2000Date of Patent: June 29, 2004Assignee: E. I. du Pont de Nemours and CompanyInventors: Ralph Thomas Baker, Ralph Newton Miller, Viacheslav Alexandrovich Petrov, Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
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Patent number: 6723887Abstract: A process for vapor phase fluorination of methylene chloride with anhydrous hydrogen fluoride (AHF) in the presence of a coprecipitated chromia-alumina impregnated with zinc salt as catalyst, removing HCl and heavier components by distillation, subjecting HFC-32 rich cut to a further step of fluorination in the presence of a fluorination catalyst.Type: GrantFiled: July 12, 2002Date of Patent: April 20, 2004Assignee: SFR LimitedInventors: Rajasekaran Ramanathan, Rajdeep Anand, Anurag Jain, Jampani Madhusudana Rao
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Patent number: 6720464Abstract: Octafluoropropane is produced by a process comprising a step (1) of reacting hexafluoropropene with hydrogen fluoride in a gas phase at a temperature of from 150 to 450° C. in the presence of a fluorination catalyst to obtain 2H-heptafluoropropane and a step (2) of reacting 2H-heptafluoropropane obtained in step (1) with fluorine gas in a gas phase at a temperature of from 250 to 500° C. in the absence of a catalyst to obtain octafluoropropane. High-purity octafluoropropane is obtained which can be used in a process for producing a semiconductor device.Type: GrantFiled: April 29, 2002Date of Patent: April 13, 2004Assignee: Showa Denko K.K.Inventors: Hiromoto Ohno, Toshio Ohi
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Patent number: 6706935Abstract: A method is disclosed for increasing in a composition the mole fraction of a compound selected from the group CF3CHCl2, CF3CHF2 and CF3CHClF relative to the total mole fraction of the other two compounds of the group. The method comprises (a) providing a gaseous composition comprising at least one compound of said group provided that (i) if the selected compound is either CF3CHCl2 or CF3CHF2, said gaseous composition comprises CF3CHFCl and the mole fraction of the selected compound relative to the other two compounds in said gaseous composition is less than its equilibrium amount at 50° C., and (ii) if the selected compound is CF3CHFCl, said gaseous composition comprises both CF3CHCl2 and CF3CHF2 and the mole fraction of the selected compound relative to the other two compounds in said gaseous composition is less than its equilibrium amount at 500° C.Type: GrantFiled: February 6, 2003Date of Patent: March 16, 2004Assignee: E. I. du Pont de Nemours and CompanyInventors: Leo Ernest Manzer, Frank Julian Weigert
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Patent number: 6686509Abstract: A method for producing an &agr;,&agr;-difluorocycloalkane at high purity with good efficiency, which comprises a step of treating a fluorocycloalkene with hydrogen fluoride wherein the fluorocycloalkene has one fluorine atom directly bonded to a carbon atom of carbon—carbon unsaturated double bond, more preferably, a step of directly adding the hydrogen fluoride to a reaction mixture obtained by treating the cycloalkanone with the de-oxygen fluorinating agent.Type: GrantFiled: September 24, 2002Date of Patent: February 3, 2004Assignee: Mitsui Chemicals, Inc.Inventors: Kouki Fukumura, Hiroshi Sonoda, Hidetoshi Hayashi, Masahiko Kusumoto
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Patent number: 6639115Abstract: The invention relates to the synthesis of difluoromethane by gas-phase catalytic fluorination of methylene chloride. To lengthen the lifetime of the catalyst the operation is carried out in the presence of chlorine.Type: GrantFiled: January 18, 2001Date of Patent: October 28, 2003Assignee: AtofinaInventors: Benoit Requieme, Sylvain Perdrieux, Bernard Cheminal, Eric Lacroix, Andre Lantz
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Patent number: 6635790Abstract: The subject of the invention is a continuous process for the manufacture of difluoromethane (F32) from methylene chloride (F30) and hydrogen fluoride in the presence of chlorine, in the gas phase, over a fluorination catalyst. According to the invention, the gas flow exiting from the reactor is subjected to a distillation in order to separate, at the top, a flow containing virtually all the HCl and at least 90% of the F32 produced by the reaction and, at the bottom, a flow containing at least 90% of the unconverted reactants (F31, F30 and HF) and the latter flow is recycled directly to the reactor, without any purification operation.Type: GrantFiled: January 28, 2000Date of Patent: October 21, 2003Assignee: AtofinaInventors: Dominique Garrait, Emmanuel Guiraud
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Publication number: 20030144561Abstract: Process for the preperation of a hydrodhlorofluoroalkane according to which a halogenated precursor of the hydrochlorofluoroalkane is reated with hydrogen fluoride in the presence of a catalyst comprising chromiun (Cr) and another metal.Type: ApplicationFiled: November 25, 2002Publication date: July 31, 2003Inventors: Vincent Wilmet, Georges Lejeune
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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: 6489523Abstract: The present invention intends to provide a process for producing CF3CF3 with good profitability using CF3CHF2 containing a compound having chlorine atom within the molecule, and use thereof. In the process of the present invention, a gas mixture containing CF3CHF2 and a compound having chlorine atom within the molecule is reacted with hydrogen fluoride in the presence of a fluorination catalyst, thereby converting CClF2CF3 as a main impurity into CF3CF3, and CF3CHF2 containing CF3CF3 is reacted with fluorine gas in the gaseous phase in the presence of a diluting gas.Type: GrantFiled: January 14, 2002Date of Patent: December 3, 2002Assignee: Showa Denko K.K.Inventors: Hiromoto Ohno, Kazunari Kaga, Toshio Ohi
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Patent number: 6479718Abstract: An improved liquid phase process is provided for the fluorination of perchloroethylene to 1,1-dichloro-2,2,2-trifluoroethane in the presence of an antimony catalyst.Type: GrantFiled: March 28, 2002Date of Patent: November 12, 2002Assignee: Atofina Chemicals, Inc.Inventors: Maher Y. Elsheikh, Jonathan M. Tracy, John A. Wismer
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Patent number: 6472573Abstract: A method of preparation for 1,1,1,3,3-pentafluoropropane (HFC-245fa) wherein the first process gives mainly 1,3,3,3-tetrafluoropropene (1234ze) by reacting 1-chloro-3, 3,3,-trifluoropropene (1233zd) with hydrogen fluoride in the gas phase and subsequently the second process gives 1,1,1,3,3-pentafluoropropane (HFC-245fa) by reacting 1,3,3,3-tetrafluoropropene (1234ze), separated as a component that does not contain hydrogen chloride from crude products obtained by the first process, with hydrogen fluoride in the gas phase. To provide a process that is capable of preparing economically HFC-245fa which does not require the separation of HFC-245fa and 1233zd.Type: GrantFiled: August 2, 2000Date of Patent: October 29, 2002Assignee: Daikin Industries, Ltd.Inventors: Akinori Yamamoto, Noriaki Shibata, Tatsuo Nakada, Takashi Shibanuma
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Patent number: 6452057Abstract: Halohydrocarbons comprising at least 3 carbon atoms are obtained by batchwise reaction between a haloalkane and an olefin in the presence of a catalyst and a co-catalyst. The addition of at least some of the co-catalyst is carried out gradually. At least some of the co-catalyst is recovered with a view to its re-use.Type: GrantFiled: September 29, 2000Date of Patent: September 17, 2002Assignee: Solvay (Societe Anonyme)Inventors: Alain Lambert, Véronique Mathieu, Charles-Marie Anciaux
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Patent number: 6437201Abstract: An improved process for the manufacture of CF3CHF2 by contacting 1,2-dichloro-1,1,2-trifluoroethane (CClF2CHClF) or 1-chloro-1,1,2,2-tetrafluoroethane (CHF2CClF2) or mixtures of CF3CHCl2 and CClF2CHClF or mixtures of CF3CHClF and CHF2CClF2 with HF in the presence of a Cr2O3 catalyst prepared by pyrolysis of ammonium dichromate, the reaction being conducted under controlled conditions whereby the production of CF3CHF2 is maximized, and the formation of chloropentafluoroethane (CF3CClF2) and other perhalo derivatives is minimized. The subject hydrogen-containing compound is useful as a blowing agent, propellant, refrigerant, fire extinguishing agent, or sterilant carrier gas.Type: GrantFiled: April 24, 1997Date of Patent: August 20, 2002Assignee: Ineos Fluor Holdings LimitedInventors: Paul Nicholas Ewing, Richard Llewellyn Powell, Michael Anthony Davies, Christopher John Skinner
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Patent number: 6433233Abstract: A method of preparing pentafluoroethane wherein chlorine-containing carbon compounds are fluorinated in the presence of chromium catalysts that are in an amorphous state and wherein the main component is chromium compounds with the addition of at least one metal element selected from the group composed of indium, gallium, cobalt, nickel, zinc and aluminum and the average valence of the chromium in said chromium compounds is not less than +3.5 but not more than +5.0. And said chromium catalysts and a preparation method thereof. A method of preparing pentafluoroethane wherein the total yield of chlorofluoroethane by-products can be decreased without significantly deteriorating the generation activity of the pentafluoroethane and compounds which can be recycled in the reaction system. And to provide catalysts for this fluorination and a preparation method thereof.Type: GrantFiled: June 12, 2000Date of Patent: August 13, 2002Assignee: Daikin Industries, Ltd.Inventors: Takashi Kanemura, Takashi Shibanuma
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Patent number: 6417413Abstract: A process for preparing halogenated ethanes, particularly pentafluoroethane, from a mixture produced by the reaction of perchloroethylene, hydrogen fluoride and a recycle stream. The preferred process utilizes phase separation techniques to ensure that less than the azzeotropic amount of HF is included in the product stream, thereby minimizing the hydrogen fluoride that is carried off with the desired products after they are separated from the reaction mixture, and at the same time prevents undesirable byproducts from being recycled to the reaction.Type: GrantFiled: November 3, 1999Date of Patent: July 9, 2002Assignee: AlliedSignal Inc.Inventors: Gustavo Cerri, Yuon Chiu, Biju Z. Perincheril
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Patent number: 6403847Abstract: One or more materials selected from 1,1,1,3,3-pentachloropropane, 1,1,3,3-tetrachloropropene and 1,3,3,3-tetrachloropropene are used as the specific materials described above. Before submitting the materials and HF to a fluorination reaction, almost all water is removed from them. To continuously manufacture useful intended products efficiently as well as to prevent deactivation of the catalyst and the accumulation of organic substances with high boiling points when manufacturing said useful 1,1,1,3,3-pentafluoropropane and/or 1-chloro-3,3,3-trifluoropropene, by fluorinating the specific materials with HF in the presence of a catalyst.Type: GrantFiled: March 20, 2001Date of Patent: June 11, 2002Assignee: Daikin Industries Ltd.Inventors: Tatsuo Nakada, Takashi Shibanuma, Noriaki Shibata
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Patent number: 6403524Abstract: A chromia-based fluorination catalyst in which the chromia is at least partially crystalline and which may contain a zinc or a compound thereof, the production of the catalyst by sintering amorphous chromia and its use in fluorination processes.Type: GrantFiled: March 8, 1999Date of Patent: June 11, 2002Assignee: Imperial Chemical Industries PLCInventors: John David Scott, Michael John Watson, Graham Ramsbottom
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Patent number: 6395941Abstract: In order to remove the impurities (in particular 1-chloro-2,2-difluoroethylene) present in crude 1,1,1,2-tetrafluoroethane (F134a), a gaseous mixture of crude F134a and hydrofluoric acid is treated in the gas phase, in the presence of a fluorination catalyst, at a temperature of between 200 and 380° C. and under a pressure between atmospheric pressure and 2.5 MPa, the HF/F134a molar ratio being between 0.05 and 0.5.Type: GrantFiled: July 3, 1997Date of Patent: May 28, 2002Assignee: Elf Atochem, S.A.Inventors: Bernard Cheminal, Andre Lantz
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Patent number: 6392106Abstract: A process for producing 1,1,1,2,2-pentafluoroethane by fluorinating with hydrogen fluoride at least one of 2,2-dichloro-1,1,1-trifluoroethane and 2-chloro-1,1,1,2-tetrafluoroethane as a starting material, the process being characterized by separating the reaction mixture resulting from the fluorination into a product portion A mainly containing 1,1,1,2,2-pentafluoroethane and a product portion B mainly containing 2,2-dichloro-1,1,1-trifluoroethane, 2-chloro-1,1,1,2-tetrafluoroethane and hydrogen fluoride, removing a fraction mainly containing 2,2-dichloro-1,1,1,2-tetrafluoroethane from the product portion B, and recycling the rest of the product portion B as part of feedstocks for fluorination. According to the process of the invention, the amount of CFC-115 contained in the target HFC-125 can be remarkably reduced through a simplified procedure.Type: GrantFiled: April 5, 2000Date of Patent: May 21, 2002Assignee: Daikin Industries, Ltd.Inventors: Satoru Kono, Toshikazu Yoshimura, Takashi Shibanuma
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Patent number: 6369285Abstract: Halohydrocarbons containing at least 3 carbon atoms are obtained by reaction between a haloalkane and an olefin in the presence of a catalyst in a reaction medium which is essentially free of water.Type: GrantFiled: September 29, 2000Date of Patent: April 9, 2002Assignee: Solvay (Societe Anonyme)Inventors: Véronique Mathieu, Charles-Marie Anciaux
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Publication number: 20020040171Abstract: A process for the production of a hydrofluoroalkane, particularly 1,1,1,2-tetrafluoroethane or pentafluoroethane, which comprises contacting a hydrochlorofluoroethane or a hydrochlorofluoroethene with hydrogen fluoride and a fluorination catalyst and recovering a hydrofluoroalkane from the resulting products, the hydrochlorofluoroethane having the formula CClXYCFHZ and the hydrochlorofluoroethene having the formula CClA-CFZ wherein X and Y are each independently chlorine or fluorine, Z is chlorine or hydrogen and A is chlorine or fluorine provided that where each of X and Y is fluorine then Z is hydrogen. A preferred embodiment of the process is the production of 1,1,1,2-tetrafluoroethane from the hydrochlorofluoroethene CCl2═CFH.Type: ApplicationFiled: April 24, 1997Publication date: April 4, 2002Inventors: PAUL NICHOLAS EWING, RICHARD LLEWELLYN POWELL, MICHAEL ANTHONY DAVIES, CHRISTOPHER JOHN SKINNER
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Patent number: 6362383Abstract: Improved process for the catalytic hydro-fluorination of saturated or unsaturated organic compounds corresponding to the general formula CwHxClyFz (I) in which w is an integer between 1 and 6, x is an integer between 0 and (2w+1) or between 0 and (2w−1), y is an integer between 1 and (2w+1) or between 1 and (2w−1), z is an integer between 0 and (2w+1) or between 0 and (2w−1) and the sum (x+y+z) is equal to (2w+2), comprising a continuous feed of hydrogen chloride. Process for preparing 1,1,1,3,3-pentafluoropropane starting with 1,1,1,3,3-pentachloropropane, comprising two catalytic reaction steps, in which hydrogen chloride is preferably fed continuously into the reaction medium of at least one of the two reaction steps.Type: GrantFiled: September 29, 2000Date of Patent: March 26, 2002Assignee: Solvay (Societe Anonyme)Inventors: Vincent Wilmet, Francine Janssens
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Patent number: 6350926Abstract: The present invention provides the novel chlorofluorohydrocarbon 1,1-difluoro-1,4-dichlorobutane, and a process for its preparation comprising reacting 1,1,1,4-tetrachlorobutane or 1,1,4-trichlorobut-1-ene with hydrogen fluoride in the liquid or vapour phase. The product has useful solvent properties and is also useful in synthetic chemistry for the introduction of fluorocarbon functionality.Type: GrantFiled: December 14, 1999Date of Patent: February 26, 2002Assignee: Syngenta LimitedInventor: Alfred Glyn Williams
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Patent number: 6339178Abstract: The subject of the invention is the manufacture of 1,1,1-trifluoroethane by fluorination or 1-chloro-1,1-difluoroethane with anhydrous hydrofluoric acid. The reaction is carried out in the liquid phase and in the presence of a fluorination catalyst.Type: GrantFiled: June 22, 2000Date of Patent: January 15, 2002Assignee: AtofinaInventors: Andre Lantz, Sylvain Perdrieux, Dominique Garrait, Laurent Wendlinger
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Patent number: 6337299Abstract: A fluorination catalyst comprising chromium oxide having a specific surface area of from 170 m2/g to 300 m2/g, which can catalyze the fluorination of a halogenated hydro-carbon with hydrogen fluoride and has a high activity and a long catalyst life.Type: GrantFiled: April 27, 1993Date of Patent: January 8, 2002Assignee: Daikin Industries Ltd.Inventors: Takashi Shibanuma, Yoshio Iwai, Satoshi Koyama
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Patent number: 6329559Abstract: A process is disclosed for the manufacture of CF3CF═CF2, and optionally a least one compound selected from CF3CH2CF3 and CF3CHFCHF2. The process involves contacting a reactor feed including a precursor stream of at least one halogenated propane of the formula CX3CH2CHyX(3−y) and/or halogenated propene of the formula CX3CH═CHyX(2−y), where each X is Cl or F and y is 0, 1 or 2 (provided that the average fluorine content of the precursor stream is no more than 5 fluorine substituents per molecule) with HF and Cl2 in a chlorofluorination reaction zone containing a fluorination catalyst and operating at a temperature between about 150° C. and 400° C.Type: GrantFiled: November 27, 2000Date of Patent: December 11, 2001Assignee: E. I. du Pont de Nemours and CompanyInventors: Allen Capron Sievert, V. N. Mallikarjuna Rao, Francis J. Walczak
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Patent number: 6329560Abstract: A method for producing a hydrogen-containing fluorinated hydrocarbon includes supplying HF to a gap between an inner reactor made of a material resistant to the reaction and an outer container made of a material resistant to HF; supplying HF to the inner reactor; supplying a halogenated hydrocarbon selected from a chlorinated alkene and a hydrogen-containing chlorinated alkane to the inner reactor; and reacting HF with halogenated hydrocarbon in the presence of a fluorination catalyst in the inner reactor to obtain the reaction product containing the hydrogen-containing fluorinated hydrocarbon.Type: GrantFiled: January 12, 2001Date of Patent: December 11, 2001Assignee: Daikin Industries, Ltd.Inventors: Tatsuo Nakada, Noriaki Shibata, Takashi Shibanuma