Antimony Halide Containing Catalyst Patents (Class 570/167)
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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: 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: 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: 6891074Abstract: A process for the production of a hydrofluoroalkane, which process comprises contacting a hydrochlorofluoroethane of formula CClXYCFHZ, wherein X and Y are each independently chlorine or fluorine and Z is chlorine, fluorine or hydrogen, in the liquid phase with hydrogen fluoride and a fluorination catalyst and recovering a hydrofluoroalkane from the resulting products.Type: GrantFiled: September 3, 2001Date of Patent: May 10, 2005Assignee: Ineos Fluor Holdings LimitedInventors: Clive Robert Giddis, Paul Hendry Stewart
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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: 6846963Abstract: In a process for producing 1,1,1,3,3-pentafluoropropane which has a liquid-phase reaction step for fluorination of 1,1,1,3,3-pentahalopropane (wherein at least one of halogen atoms is not fluorine) with HF in the presence of antimony pentahalide catalyst in a reactor to obtain a reaction mixture comprising 1,1,1,3,3-pentafluoropropane and the antimony pentahalide catalyst, the fluorination is conducted at a reaction temperature less than 50° C.Type: GrantFiled: February 11, 2004Date of Patent: January 25, 2005Assignee: Daikin Industries, Ltd.Inventors: Tatsuo Nakada, Seiji Takubo, Toshikazu Yoshimura, Takashi Shibanuma
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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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Publication number: 20040171896Abstract: Highly fluorinated antimony, especially in the form of a hydrogen fluoride addition compound, can be used as an isomerization catalyst for the isomerization of certain halocarbon compounds or halogenated hydrocarbon compounds. For example, 1,1,1-trifluoro-2,2-dichoroethane can be produced from 1,1,2-trifluoro-1,2-dichloroethane. The method also is suitable for the purification of certain halocarbon or halogenated hydrocarbon compounds which are contaminated by isomerizable compounds.Type: ApplicationFiled: March 3, 2004Publication date: September 2, 2004Applicant: Solvay Fluor und Derivate GmbHInventors: Max Braun, Carsten Brosch
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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: 6730817Abstract: 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: June 8, 1998Date of Patent: May 4, 2004Assignee: Solvay (Societe Anonyme)Inventors: Vincent Wilmet, Francine Janssens, Jean-Paul Schoebrechts
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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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Publication number: 20040049088Abstract: Catalysts which are useful in the fluorination of halogenated hydrocarbons by HF in the gas phase are obtained by simple impregnation of a bulk chromium oxide with a solution of a nickel derivative, the chromium oxide used exhibiting a BET specific surface of greater than 150 m2/g and a pore volume of greater than 0.15 ml/g.Type: ApplicationFiled: September 10, 2003Publication date: March 11, 2004Inventors: Eric Lacroix, Jean-Pierre Schirmann
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Patent number: 6689924Abstract: A process for the catalytic fluorination of hydrochlorocarbons and hydrochlorofluorocarbons in the liquid phase. The process is useful for fluorinating hydrochloropropanes, hydrochlorofluoropropanes, hydrochloropropenes and hydrochlorofluoropropenes and most particularly useful for fluorinating 1,1,1,3,3-pentachloropropane to 1,1,1,3,3-pentafloropropane.Type: GrantFiled: December 20, 1999Date of Patent: February 10, 2004Assignee: Honeywell International Inc.Inventors: Alagappan Thenappan, Hsueh S. Tung, Robert L. Bell
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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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Patent number: 6630610Abstract: A process for producing a fluorinated organic compound comprising: (a) reacting an organic starting material with a fluorination agent in the presence of a liquid fluorination catalyst under conditions which are effective to vaporize one or more chlorinated organic by-products and to produce a gaseous product stream containing said fluorinated organic compound and said one or more chlorinated organic by-products; and (b) recovering said fluorinated organic compound from said product stream, and a system for performing the aforementioned process and recovering the chlorinated by-product.Type: GrantFiled: March 6, 2001Date of Patent: October 7, 2003Assignee: AlliedSignal Inc.Inventors: Charles F. Swain, Stephen A. Cottrell, Clifford Scott Riegel, Curtis A. Brescher
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Patent number: 6596910Abstract: Disclosed is an improved HFC manufacturing processes of the type which produces an intermediate product stream that includes a mixture of HF and at least one compound, usually an HCFC, which is relatively resistant to further fluorination. The improvement involves separating the unreactive compound(s) from the product stream, preferably using liquid:liquid phase separation, and substantially avoiding recycle of the unreactive compound to the fluorination reaction. The separated unreactive compound(s) are substantially free of HF.Type: GrantFiled: January 25, 2002Date of Patent: July 22, 2003Assignee: Honeywell International Inc.Inventors: Hsueh Sung Tung, Clayton Herbert Carson, Hang Thanh Pham
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Patent number: 6548712Abstract: The invention relates to a process for producing 1,1,1,5,5,5-hexafluoroacetylacetone. This process includes (a) hydrolyzing a metal complex of 1,1,1,5,5,5-hexafluoroacetylacetone into a 1,1,1,5,5,5-hexafluoroacetylacetone hydrate; and (b) dehydrating the hydrate into the 1,1,1,5,5,5-hexafluoroacetylacetone with high purity from a material containing a metal complex of 1,1,1,5,5,5-hexafluoroacetylacetone.Type: GrantFiled: March 15, 2001Date of Patent: April 15, 2003Assignee: Central Glass Company, LimitedInventors: Takeo Komata, Nariaki II
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Patent number: 6538165Abstract: According to a process for producing difluoromethane and difluorochloromethane, which comprises fluorinating dichloromethane and trichloromethane with hydrogen fluoride in a liquid phase in the presence of a catalyst in one reaction apparatus under the conditions that a reaction pressure is from 1 to 20 kg/cm2 and a reaction temperature is from 50 to 150° C., difluoromethane and difluorochloroethane can be simultaneously or alternatively produced in an economical/safe manner by one reaction apparatus.Type: GrantFiled: August 8, 1997Date of Patent: March 25, 2003Assignee: Daikin Industries Ltd.Inventors: Takehide Tsuda, Takashi Shibanuma
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Patent number: 6528691Abstract: A gas phase process for the preparation of 245fa is provided, wherein 1233zd is contacted with HF in the presence of a supported antimony catalyst.Type: GrantFiled: May 14, 1999Date of Patent: March 4, 2003Assignee: Atofina Chemicals, Inc.Inventors: Maher Y. Elsheikh, Bin Chen
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Patent number: 6521802Abstract: The present invention provides a process for preparing a fluorine-containing halogenated hydrocarbon compound by fluorinating, in a reaction field where an antimony halide compound represented by the general formula: SbClpF5−p (I) wherein p is a value within a range from 0 to 2, and hydrogen fluoride and a halogenated hydrocarbon compound as a raw material exist, the halogenated hydrocarbon compound in a molar ratio of the antimony halide compound to hydrogen fluoride within a range from 40/60 to 90/10. According to this process, a fluorine-containing halogenated hydrocarbon compound (HFC), which is important as a substitute compound of CFC or HCFC, can be prepared economically advantageously with good selectivity while suppressing a corrosive action of a reaction vessel.Type: GrantFiled: May 29, 2002Date of Patent: February 18, 2003Assignee: Daikin Industries, Ltd.Inventors: Seiji Takubo, Noriaki Shibata, Tatsuo Nakada, Takashi Shibanuma
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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: 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: 6407296Abstract: A process is disclosed for producing difluoromethane by fluorinating dichloromethane with hydrogen fluoride in a liquid phase in the presence of a catalyst, wherein the reaction is conducted at a temperature within the range from 80 to 150° C. under a pressure within the range from 8 to 80 kg/cm2 using a mixture of antimony pentafluoride and antimony trifluoride, or antimony pentafluoride as the fluorinating catalyst. The process economically and safely produces difluoromethane from dichloromethane and hydrogen fluoride.Type: GrantFiled: December 23, 1996Date of Patent: June 18, 2002Assignee: Daikin Industries Ltd.Inventors: Yasufu Yamada, Takashi Shibanuma, Takehide Tsuda
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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: 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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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: 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
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Patent number: 6300530Abstract: Catalyst comprising a supported Cr(III) amorphous compound, characterized in that the support is formed by an aluminum trifluoride (AlF3) having an high surface area obtainable by alumina fluorination with gaseous HF at an initial temperature lower than 300° C., the temperature is rised with a temperature gradient≦100° C./hour up to the final temperature>320° C. and <450° C., the fluorination is continued at the final temperature until feeding a HF molar amount at least equal to the stoichiometric with respect to the alumina, the fluorination being carried out until a fluorinated alumina with a fluorine content not lower than 95% of the stoichiometric is obtained.Type: GrantFiled: May 5, 1999Date of Patent: October 9, 2001Assignee: Ausimont S.p.A.Inventor: Paolo Cuzzato
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Patent number: 6291728Abstract: A manufacturing method for 1,1,1,3,3-pentafluoropropane, wherein 1,1,1,3,3-pentafluoropropane (HFC-245fa) is obtained by reacting halogenated propane, for example, 1,1,1,3,3-pentachloropropane and so on, which is represented by the general formula: CX3CH2CHX2 [In the general formula, X is fluorine atom (F) or chlorine atom (Cl), and all of X can not be fluorine atoms at the same time], with anhydrous hydrofluoric acid (HF) under the presence of antimony catalyst. HFC-245fa can be obtained with high yield and economical advantages through simple process.Type: GrantFiled: March 27, 1998Date of Patent: September 18, 2001Assignee: Daikin Industries, Ltd.Inventors: Hirokazu Aoyama, Tatsuo Nakada, Akinori Yamamoto
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Patent number: 6274780Abstract: A process is disclosed for changing the fluorine content of halogenated hydrocarbons containing from 1 to 6 carbon atoms, in the presence of a multiphase catalyst. The process involves producing the catalyst by heating a single phase solid catalyst precursor having the formula (NH3)6Cr2−xMxF6 (where x is in the range of 0.1 to 1 and M is at least one metal selected from the group consisting of Al, Sc, V, Fe, Ga and In) to about 400° or less to produce a multiphase composition wherein a phase containing crystalline M fluoride is homogeneously dispersed with a phase containing chromium fluoride. Also disclosed are multiphase catalyst compositions consisting essentially of chromium fluoride and a crystalline fluoride of at least one metal selected from the above group (provided the atom percent of Cr is at least equal to the atom percent of the crystalline fluoride metals). Phases of the crystalline fluorides are homogeneously dispersed with phases of the chromium fluoride.Type: GrantFiled: July 9, 1996Date of Patent: August 14, 2001Assignee: E. I. du Pont de Nemours and CompanyInventors: V. N. Mallikarjuna Rao, Munirpallam A. Subramanian
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Patent number: 6268540Abstract: The present invention provides catalysts and processes for the fluorination of hydrohalomethanes. In particular, the invention provides a process for the fluorination of hydrohalomethanes using hydrogen fluoride and a Lewis Acid catalyst. More specifically, catalysts and a process for the fluorination of dichloromethane are provided.Type: GrantFiled: June 24, 1996Date of Patent: July 31, 2001Assignee: AlliedSignal Inc.Inventors: Alagappan Thenappan, Addison Miles Smith, Jeffrey Warren McKown, Robert Louis Bell
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Patent number: 6242659Abstract: 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: June 14, 1996Date of Patent: June 5, 2001Assignee: Elf Atochem, S.A.Inventors: Benoit Requieme, Sylvain Perdrieux, Bernard Cheminal, Eric Lacroix, Andre Lantz
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Patent number: 6235951Abstract: The present invention relates to a method for producing 1,1,1,3,3-pentafluoropropane. This method includes the steps of (a) adding hydrogen fluoride to 1-chloro-3,3,3-trifluoropropene in the presence of an addition catalyst to obtain 1,1,1,3-tetrafluoro-3-chloropropane; and (b) disproportionating the 1,1,1,3-tetrafluoro-3-chloropropane into the 1,1,1,3,3-pentafluoropropane and 1,1,1-trifluoro-3,3-dichloropropane, in the presence of a disproportionation catalyst. This method is a useful method for producing 1,1,1,3,3-pentafluoropropane in an industrial scale, because its steps (a) and (b) are respectively superior in selectivity and yield. According to the invention, 1-chloro-3,3,3-trifluoropropene may be produced by a method including a step of reacting 1,1,1,3,3-pentachloropropane with hydrogen fluoride in a gas phase in the presence of a fluorination catalyst. This method is useful, because yield of 1-chloro-3,3,3-trifluoropropene is high.Type: GrantFiled: November 20, 1996Date of Patent: May 22, 2001Assignee: Central Glass Company, LimitedInventors: Fuyuhiko Sakyu, Satoshi Yoshikawa, Yasuo Hibino, Yoshihiko Gotoh, Ryouichi Tamai
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Patent number: 6218586Abstract: The invention relates to a method for preparing a fluorinated product that is a first perhalogenated five-membered cyclic compound (e.g., 1,2-dichlorohexafluorocyclopentene and 1,1-dichlorooctafluorocyclopentane). This method includes reacting in a gas phase a starting material that is a second perhalogenated five-membered cyclic compound having at least one unsaturated bond, at substantially the same time with chlorine and hydrogen fluoride, in the presence of a fluorination catalyst containing an activated carbon optionally carrying thereon a metal compound, thereby to decrease the number of the at least one unsaturated bond and to increase the number of fluorine atoms of the second compound. The method is appropriate for the production of the first perhalogenated five-membered cyclic compound in an industrial scale.Type: GrantFiled: November 5, 1999Date of Patent: April 17, 2001Assignees: Central Glass Company, Limited, Nippon Zeon Co., Ltd.Inventors: Naoto Takada, Masatomi Kanai, Hideaki Imura, Takeo Komata
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Patent number: 6198010Abstract: The present invention relates to a method for producing 1,1,1,3,3-pentafluoropropane. This method includes a first step of fluorinating 1-chloro-3,3,3-trifluoropropene in a liquid phase by hydrogen fluoride in the presence of an antimony compound as a catalyst, or a second step of fluorinating 1-chloro-3,3,3-trifluoropropene in a gas phase by hydrogen fluoride in the presence of a fluorination catalyst. If the first step is taken, 1,1,1,3,3-pentafluoropropane can be produced with a high yield. If the second step is taken, 1,1,1,3,3-pentafluoropropane can continuously be easily produced. Therefore, the second step is useful for an industrial scale production thereof. According to the invention, 1-chloro-3,3,3-trifluoropropene may be produced by a method including a step of reacting 1,1,1,3,3-pentachloropropane with hydrogen fluoride in a gas phase in the presence of a fluorination catalyst. This method is useful, because yield of 1-chloro-3,3,3-trifluoropropene is high.Type: GrantFiled: October 6, 1998Date of Patent: March 6, 2001Assignee: Central Glass Company, LimitedInventors: Satoshi Yoshikawa, Ryouichi Tamai, Fuyuhiko Sakyu, Yasuo Hibino, Yoshihiko Gotoh
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Patent number: 6165426Abstract: Disclosed is a method of removing a soluble antimony compound from a liquid in which it is dissolved. The liquid is contacted with a hydrated compound, particularly a hydrated compound that forms carbonate ions, bicarbonate ions, or both in the liquid, such as carbonic acid or hydrates of sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, ammonium carbonate, or ammonium bicarbonate. An antimony compound is formed that is insoluble in the liquid and it is separated from the liquid.Type: GrantFiled: July 16, 1999Date of Patent: December 26, 2000Assignee: Occidental Chemical CorporationInventor: Sanjay K. Mandal
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Patent number: 6166275Abstract: A liquid phase fluorination process for producing difluoromethane without corrosion is provided. In the process of this invention, methylene chloride and hydrogen fluoride are reacted in a reactor made of fluorinated polymer to produce a reaction product while a vaporized and superheated recycle stream of process reactants is fed into the reactor.Type: GrantFiled: September 17, 1999Date of Patent: December 26, 2000Inventors: Gustavo Cerri, Maurice William Hunt, David William Keeler, Frank Peter Young
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Patent number: 6127587Abstract: The present invention provides a process for the preparation of 1,1-difluoro-1,4-dichlorobutane by reacting 1,1,1,4-tetrachlorobutane or 1,1,4-trichlorobut-1-ene with hydrogen fluoride in the vapor phase.Type: GrantFiled: September 10, 1999Date of Patent: October 3, 2000Assignee: Zeneca LimitedInventor: Alfred Glyn Williams
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Patent number: 6124511Abstract: A method for producing a hydrogen-containing fluorinated alkane, which comprises fluorinating at least one halogenated hydrocarbon selected from a chlorinated ethylene and a hydrogen-containing chlorinated alkane by hydrogen fluoride in the presence of a fluorination catalyst, in a reaction system where a corrosion-resistant metal material containing at least 10 wt % of aluminum, is present.Type: GrantFiled: July 30, 1997Date of Patent: September 26, 2000Assignee: Asahi Glass Company Ltd.Inventors: Keiichi Ohnishi, Hidekazu Okamoto