Substituting Halogen For A Different Halogen Patents (Class 570/170)
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Patent number: 7348461Abstract: 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: March 25, 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: 7335804Abstract: Provided are methods for producing hydrofluorocarbons via the selective reduction of a halocarbon blend comprising 1,3-dichloro-1,1,2,2,3-pentafluoropropane.Type: GrantFiled: November 3, 2005Date of Patent: February 26, 2008Assignee: Honeywell International Inc.Inventors: Haridasan Nair, Sudip Mukhopadhyay, Michael Van Der Puy
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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: 7319175Abstract: Catalysts such as antimony halides, which are useful in fluorination reactions involving hydrogen fluoride, may be reduced during the reaction and require regeneration. Regenerative oxidation is usually carried out by introducing elemental halogen, preferably fluorine or chlorine, into the reaction mixture. In accordance with the invention elemental halogen is prevented from coming into contact with starting materials or intermediate products which are reactive therewith. This is preferably achieved by withdrawing part of the reaction mixture from the reactor, mixing the withdrawn part with chlorine or fluorine in order to regenerate the catalyst, and thereafter returning the withdrawn part to the reactor.Type: GrantFiled: October 27, 2005Date of Patent: January 15, 2008Assignee: Solvay Fluor und Derivate GmbHInventors: Max Braun, Carsten Brosch
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Patent number: 7223892Abstract: 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: June 28, 2006Date of Patent: May 29, 2007Assignee: Solvay S.A.Inventors: Alain Lambert, Vincent Wilmet
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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: 7202388Abstract: Processes for preparing fluoroarenes are provided. The processes include contacting a compound having an unactivated aryl group with a source of fluoride or bifluoride in the presence of a transition metal a ligand.Type: GrantFiled: October 5, 2005Date of Patent: April 10, 2007Assignee: E. I. du Pont de Nemours and CompanyInventor: Vladimir Grushin
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Process for the treatment of the by-products from a reaction for the production of organic compounds
Patent number: 7183449Abstract: Process for the treatment of by-products from a reaction for the production of organic compounds comprising a stage of evaporation of a liquid phase comprising heavy by-products on a surface, in order to form a concentrated phase comprising the bulk of the heavy by-products and a vapor phase essentially devoid of heavy by-products, and a stage of recovery of the solid phase from the surface.Type: GrantFiled: June 21, 2002Date of Patent: February 27, 2007Assignee: Solvay S.A.Inventors: Lionel Casaubon Seignour, Philippe Krafft, Bruno Fouchet -
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: 7102041Abstract: A process for preparing a haloalkane comprising: (a) contacting a haloalkane starting material with an alkene in the presence of an effective amount of a catalyst complex under conditions effective to facilitate an addition reaction and to form a product stream comprising a haloalkane product from the addition reaction, wherein the catalyst complex has a boiling point higher than that of the haloalkane product; and (b) recovering the haloalkane product from the product stream.Type: GrantFiled: December 8, 2004Date of Patent: September 5, 2006Assignee: Honeywell International Inc.Inventor: Hsueh Sung Tung
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Patent number: 7094936Abstract: Methods and materials are provided for the production and purification of halogenated compounds and intermediates in the production of 1,1,1,3,3-pentafluoropropane. In a preferred embodiment, the process steps include: (1) reacting carbon tetrachloride with vinyl chloride to produce 1,1,1,3,3-pentachloropropane; (2) dehydrochlorinating the 1,1,1,3,3-pentachloropropane with a Lewis acid catalyst to produce 1,1,3,3-tetrachloropropene; (3) fluorinating the 1,1,3,3-tetrachloropropene to produce 1-chloro-3,3,3-trifluoropropene; (4) fluorinating the 1-chloro-3,3,3-trifluoropropene to produce a product mixture containing 1,1,1,3,3-pentafluoropropane; and (5) separating 1,1,1,3,3-pentafluoropropane from by-products.Type: GrantFiled: October 16, 2003Date of Patent: August 22, 2006Assignee: Great Lakes Chemical CorporationInventors: Stephen Owens, Andrew Jackson, Vimal Sharma, Mitchel Cohn, John Cheng-Ping Qian, Julia Ann Sacarias, Yuichi Iikubo
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Patent number: 7094934Abstract: In a process for producing a hydrogen-containing fluorinated hydrocarbon in which a halogenated hydrocarbon reaction raw material, which includes a chlorinated alkene and/or a hydrogen-containing chlorinated alkane, is subjected to a fluorination reaction with hydrogen fluoride in a liquid phase in a reactor in the presence of a fluorination catalyst to obtain a reaction mixture which includes the hydrogen-containing fluorinated hydrocarbon, the reactor to be used has a portion which is able to contact with the reaction mixture, at least a part of this portion being made of an alloy material of 18 to 20% by weight of chromium, 18 to 20% by weight of molybdenum, 1.5 to 2.2% by weight of at least one element selected from niobium and tantalum and the balance of nickel.Type: GrantFiled: January 31, 2001Date of Patent: August 22, 2006Assignee: Daikin Industries, Ltd.Inventors: Noriaki Shibata, Tatsuo Nakada, Takashi Shibanuma
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Patent number: 7084316Abstract: A process comprising bringing crude pentafluoroethane containing at least one compound selected from the group consisting of hydrofluorocarbons containing one carbon atom, hydrochlorofluorocarbons containing one carbon atom and hydrochlorocarbons containing one carbon atom, into contact with an adsorbent comprising a zeolite having an average pore size of 3 to 6 ? and a silica/aluminum ratio of 2.0 or less and/or a carbonaceous adsorbent having an average pore size of 3.5 to 6 ?, to reduce the content of the compound. The purified gas can be used as a low temperature refrigerant or an etching gas.Type: GrantFiled: June 30, 2003Date of Patent: August 1, 2006Assignee: Showa Denko K.K.Inventors: Hiromoto Ohno, Toshio Ohi
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Patent number: 7071367Abstract: The present invention provides a process for the preparation of trifluoromethyl iodide. The process includes the step of: contacting in a reactor a compound represented by the formula: CF3—W and a compound represented by the formula: Z-I wherein W is selected from CF3, hydrogen and bromine; Z is selected from hydrogen, iodine and chlorine. The step of contacting is carried out, optionally in the presence of a catalyst and further optionally in the presence of air, at a temperature, pressure and for a length of time sufficient to produce the trifluoromethyl iodide.Type: GrantFiled: December 9, 2004Date of Patent: July 4, 2006Assignee: Honeywell International Inc.Inventors: Sudip Mukhopadhyay, Hsueh Sung Tung
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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: 7009083Abstract: The invention relates to a process for the preparation of 1-chloro-1-fluoroethane and 1,1-difluoroethane by reaction of vinyl chloride with hydrogen fluoride, in an organic solvent consisting of at least one saturated halogen-containing hydrocarbon.Type: GrantFiled: August 2, 2004Date of Patent: March 7, 2006Assignee: Solvay (Societe Anonyme)Inventors: Pascal Pennetreau, Francine Janssens
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Patent number: 6967260Abstract: Tetrafluoromethane containing ethylene compound, hydrocarbon compounds, carbon monoxide and/or carbon dioxide is contacted with zeolite having an average pore size of 3.4 to 11 ? and an Si/Al ratio of 1.5 or less and/or a carbonaceous adsorbent having an average pore size of 3.4 to 11 ?. Thus, high-purity tetrafluoromethane can be obtained which is advantageous in industry and provides good profitability.Type: GrantFiled: April 26, 2001Date of Patent: November 22, 2005Assignee: Showa Denko K.K.Inventors: Hiromoto Ohno, Toshio Ohi
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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: 6806396Abstract: The present invention relates to the co-pyrolysis of fluoroform and chlorodifluoromethane to form a mixture of useful fluoroolefin and saturated HFCs, notably, tetrafluoroethylene and hexafluoropropylene and CF3CHF2 and CF3CHFCF3, respectively.Type: GrantFiled: December 16, 2002Date of Patent: October 19, 2004Assignee: E. I. du Pont de Nemours and CompanyInventors: Peter Gideon Gelblum, Velliyur Nott Mallikarjuna Rao, Charles Joseph Noelke, Norman Herron
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Patent number: 6759381Abstract: Provided are azeotropic and azeotrope-like mixtures of 1-chloro-1,3,3,3-tetrafluoropropane and 1,2-dichloro-3,3,3-trifluoropropene that are useful as an intermediate in the production of HFC-245fa. HFC-245fa is useful as a nontoxic, zero ozone depleting fluorocarbon useful as solvents, blowing agents, refrigerants, cleaning agents, aerosol propellants, heat transfer media, gaseous dielectrics, fire extinguishing compositions and power cycle working fluids.Type: GrantFiled: May 6, 2003Date of Patent: July 6, 2004Assignee: Honeywell International Inc.Inventors: Robert C. Johnson, Daniel C. Merkel, Hsuehsung Tung
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Patent number: 6657094Abstract: There is provided a method of end-chlorination of a fluorine-containing compound which can easily provide a fluorine-containing monomer having a functional group such as nitrile group at relatively low cost. The method of chlorinating an end of a fluorine-containing compound having iodine atom at an end thereof comprises reacting a fluorine-containing organic compound having iodine atom at a molecular end thereof and represented by the formula (I): RfCX2I (I) wherein Rf is an organic residue having fluorine atom, X is hydrogen atom or chlorine atom, with a chlorine gas at a temperature of from 150° C. to 180° C. under irradiation with light to cleave the C—I bond and replace iodine atom with chlorine atom.Type: GrantFiled: March 22, 2002Date of Patent: December 2, 2003Assignee: Daikin Industries, Ltd.Inventors: Masaki Irie, Kazuyoshi Kawasaki, Mitsuru Kishine
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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: 6521199Abstract: Hydrogen fluoride adducts and ammonium fluorides are used for fluorinating acid chlorides and halocarbon compounds such as chloroalkanes or chloronated ethers. The used adducts can be regenerated and then reused in the fluorination reactions.Type: GrantFiled: March 4, 2002Date of Patent: February 18, 2003Assignee: Solvay Fluor und Derivate GmbHInventors: Max Braun, Stefan Palsherm
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Publication number: 20020087039Abstract: A method of producing hydrofluorocarbons and/or hydrochlorofluorocarbons by using halogenated alkanes as a principal reactant.Type: ApplicationFiled: December 29, 2000Publication date: July 4, 2002Inventors: Hsueh Sung Tung, Michael Van Der Puy
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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: 6395700Abstract: Compounds each having a —CH2—CHF— group and a number of carbon atoms of 4 or above are prepared by hydrogenating a compound having a —CCl═CF— group and a number of carbon atoms of 4 or above in the presence of a noble metal catalyst in a liquid or gas phase. The compound having a —CCl═CF— group and a number of carbon atoms of 4 or above is preferably a C4-C10 alicyclic one, and can be prepared by reacting a compound having a —CCl═CCl— group and a number of carbon atoms of 4 or above with a fluorinating agent.Type: GrantFiled: June 23, 2000Date of Patent: May 28, 2002Assignee: Nippon Zeon Co., Ltd.Inventors: Toshiro Yamada, Takashi Uruma, Tatsuya Sugimoto
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Patent number: 6362379Abstract: A method is provided for preparation of chlorofluoroethers ClCF2CFClOR8f and Cl2CFCFClOR8f by direct fluorination of Cl2CHCH2OR8 and Cl3CCH2OR8, respectively, wherein R8 is a C1-C20 alkyl-or acyl-containing group optionally up to 5 ether oxygen atoms and optionally substituted by functional groups and R81, is the corresponding perfluoroalkyl or perfluoracyl-containing group.Type: GrantFiled: May 1, 2001Date of Patent: March 26, 2002Assignee: 3M Innovative Properties CompanyInventors: George G. I. Moore, Fred B. McCormick, Mita Chattoraj, Elisa M. Cross, Junkang Jacob Liu, Ralph R. Roberts, Jay F. Schulz
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Publication number: 20020035301Abstract: 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: ApplicationFiled: August 29, 2001Publication date: March 21, 2002Inventor: Kouichi Hirota
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Patent number: 6316682Abstract: A method of producing 1,1,1,3,3-pentafluoropropane wherein 1,1,1,3,3-pentafluoropropane is obtained by reacting at least one selected from the group consisting of fluorinated and chlorinated propane and chlorinated propane expressed by a general formula of CX3CH2CHX2 (where X in this general formula indicates either a fluorine atom or a chlorine atom, but all of X's can never represent fluorine atoms at the same time) with a fluorinated antimony chloride. There is provided an economical and efficient method of producing 1,1,1,3,3-pentafluoropropane with high yield, which is an alternative compound to CFC's and HCFC's and is important in industry as a blowing agent, a refrigerant, a detergent, and a propellant that does not destroy the ozone in the ozone layer.Type: GrantFiled: November 30, 1998Date of Patent: November 13, 2001Assignee: Daikin Industries, Ltd.Inventors: Tatsuo Nakada, Takashi Shibanuma, Yamamoto Akinori
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Publication number: 20010034465Abstract: 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: ApplicationFiled: March 6, 2001Publication date: October 25, 2001Inventors: Charles F. Swain, Stephen A. Cottrell, Clifford S. Riegel, Curtis A. Brescher
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Patent number: 6297405Abstract: A process for the preparation of aromatic aldehydes containing fluorine, and more particularly, to a formylation process for fluorinated aromatic derivatives through the reaction of fluorinated benzenes with carbon monoxide and aluminum chloride at a relatively low pressure, a low temperature, and in the presence of at most a catalytic amount of an acid (such as aqueous hydrochloric acid) is herein disclosed. The resultant fluorinated benzaldehydes are useful as precursors to the formation of a number of different compounds, such as dyestuffs, flavorings, fragrances, herbicidal compounds, nucleating agents, polymer additives, and the like. The inventive method provides a very cost effective and safe procedure for producing such fluorinated benzaldehydes in very high yields. The particular novel multi-substituted benzaldehydes are also encompassed within this invention.Type: GrantFiled: September 1, 2000Date of Patent: October 2, 2001Assignee: Milliken & CompanyInventors: John David O. Anderson, Walter Scrivens
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Patent number: 6239319Abstract: The present invention provides a new industrial process for producing perfluoroalkanes in order to overcome the problems of processes for producing perfluoroalkanes in the prior art. The process of the present invention is a process for producing a perfluoroalkane corresponding to a general formula Rf-F (wherein Rf- is a perfluoroalkyl group represented by F(CF2)n— and n is an integer of 2 to 10) by contacting a perfluoroalkyl iodide with gaseous fluorine to cause a reaction therebetween, wherein the contact is made in the presence of the liquid compound which is at least one liquid which is substantially inert to the perfluoroalkyl iodide and gaseous fluorine under the condition of the process and which is selected from a perfluoro-compound, a chlorofluoro-compound, and hydrogen fluoride.Type: GrantFiled: August 23, 1999Date of Patent: May 29, 2001Assignee: Daikin Industries Ltd.Inventors: Tatsuya Otsuka, Tatsuya Hirata, Kyohiro Kan, Hirokazu Aoyama
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Patent number: 6198011Abstract: A method of fluorinating an organic compound comprising reacting an organic compound with a fluorinating agent characterized in that a perfluorocarbon compound is present in the reaction medium. The perfluorocarbon compound may replace an amount of a solvent which would otherwise be required for the reaction to proceed efficiently. The perfluorocarbon compound is readily recoverable after reaction and may be re-used in subsequent reactions. Additives to the reaction medium, such as 18-crown-6, may increase the amoun of solvent which may be replaced. The method is beneficial where solvent consumption would otherwise be large, or where solvent recovery would otherwise be difficult.Type: GrantFiled: March 25, 1999Date of Patent: March 6, 2001Assignee: F2 Chemicals Ltd.Inventors: Richard D. Chambers, Andrew R. Edwards
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Patent number: 6184425Abstract: The present invention relates to a process for preparing fluorine-containing compounds by reacting a compound which contains fluorine-exchangeable halogen with a fluoride or a mixture of fluorides with the formula I MeF (I), in which Me is an alkaline earth metal ion, NH4+-ion or alkali metal ion, in the presence of a compound or a mixture of compounds of the formula (II) in which A1, A2, A3, A4, A5, A6, A7, A8 independently of one another are identical or different and are a straight-chain or branched alkyl or alkenyl having 1 to 12 carbon atoms, cycloalkyl having 4 to 8 carbon atoms, an aryl having 6 to 12 carbon atoms, or an aralkyl having 7 to 12 carbon atoms, or A1 A2, A3A4, A5A6, and A7A8 independently of one another are identical or different and are connected to one another directly or by way of O or N—A9 to form a ring having 3 to 7 ring members, A9 is an alkyl having 1 to 4 carbon atoms and B− is a monovalent acid radical or the equivalent of a polyvalType: GrantFiled: July 7, 1999Date of Patent: February 6, 2001Assignee: Aventis Research & Technologies GmbH & Co.Inventors: Alexander Kolomeitsev, Sergej Pasenok
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Patent number: 6165931Abstract: A process is disclosed for increasing the fluorine content of a saturated or olefinic halogenated hydrocarbon starting material of the formula C.sub.n H.sub.a Cl.sub.b F.sub.c, wherein n is an integer from 1 to 6, a is an integer from 0 to to 12, b is an integer from 0 to 13 and c is an integer from 0 to 13. The process involves contacting the starting material in the vapor phase at a temperature in the range of about 150.degree. C. to about 500.degree. C. with HF and a catalytic metal supported on a trivalent lanthanum compound support (the catalytic metal being chromium, cobalt, nickel, zinc, magnesium, copper, silver and/or gold). Certain catalytic compositions including catalytic metal (e.g., chromium, nickel, cobalt, zinc and/or magnesium) supported on a support at trivalent lanthanum compound containing fluoride anion are also disclosed. The atomic ratio of catalytic metal to lanthanum in the compositions is from about 1:1 to 1:999.Type: GrantFiled: April 11, 1997Date of Patent: December 26, 2000Assignee: E. I. du Pont de Nemours and CompanyInventor: V. N. Mallikarjuna Rao
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Patent number: 6114589Abstract: The invention relates to a process for the preparation of fluorinated compoundsAz.sub.x ArF.sub.w Cl.sub.(y-w) R.sub.z (1)in which Az is a radical --F, --Cl, --Br, --NO.sub.2, --CN, --CF.sub.3, --CCl.sub.3, --CHO, --CO(C.sub.n H.sub.2n+1), --COX or --SO.sub.2 X, where X is F, Cl or Br, x is an integer from 1 to 3, Ar is a phenyl radical, pyridyl radical or naphthyl, w is an integer from 1 to y, y is an integer from 1 to 5, R is H, an alkyl radical or an alkoxy radical having from 1 to 10 carbon atoms, z is an integer from 1 to 5, (x+y+z) is the number of all substitutable valences on the radical Ar, which comprises reacting a compoundAz.sub.x ArCl.sub.y R.sub.z (2),with an alkali metal fluoride in the presence of a component a) or a mixture of component a) and at least one of components b), c), d) and/or e), component a) being one or more quaternary ammonium compounds which contain one or more radicals --(C.sub.m H.sub.2m O)R.sup.Type: GrantFiled: October 13, 1998Date of Patent: September 5, 2000Assignee: Clariant GmbHInventors: Thomas Schach, Thomas Wessel, Maren Gutermuth
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Patent number: 6077819Abstract: A process is disclosed for recovering HF from a product mixture comprising HF and at least one compound having the formula CF.sub.3 CCl.sub.2+x F.sub.1-x (where x is 0 or 1). The process includes the steps of distilling the product mixture to remove all products which have a lower boiling point than the lowest boiling azeotrope containing HF and said at least one compound; and distilling said azeotrope to recover HF as an azeotropic composition containing HF and said at least one compound. Also disclosed are azeotrope and azeotrope-like compositions which consist essentially of hydrogen fluoride in combination with from about 10 to 27 mole percent CCl.sub.3 CF.sub.3 or from about 35 to 56 mole percent CCl.sub.2 FCF.sub.3.Type: GrantFiled: November 1, 1993Date of Patent: June 20, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Barry A. Mahler, Ralph N. Miller, V. N. Mallikarjuna Rao
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Patent number: 6028026Abstract: This invention provides a crystalline chromium fluoride having a cubic crystal structure (i.e., chromium trifluoride having an X-ray diffraction powder pattern as shown in Table I); and a catalytic composition comprising cubic chromium trifluoride. This invention also provides a process for changing the fluorine content of halogenated hydrocarbons containing from one to six carbon atoms, in the presence of a chromium-containing catalyst. The process is characterized by the chromium-containing catalyst comprising cubic chromium trifluoride.Type: GrantFiled: August 20, 1998Date of Patent: February 22, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: V. N. Mallikarjuna Rao, Munirpallam A. Subramanian
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Patent number: 5969198Abstract: A process for preparing 1,1,1,3,3-pentafluoropropane from a hydrochlorocarbon of the formula C.sub.3 H.sub.y Cl.sub.x, wherein x is an integer from 3 to 5, y is an integer from 1 to 3, x+y=4, 6, or 8, and x-y=2 is provided.Type: GrantFiled: June 27, 1997Date of Patent: October 19, 1999Assignee: AlliedSignal Inc.Inventors: Alagappan Thenappan, Michael Van Der Puy, Hsueh S. Tung
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Patent number: 5919728Abstract: A fluorination catalyst based on of an amorphous Cr (III) compound and on a compound of another metal selected from Mg, Ca, Sr, Ba, Sc, Ti and Zr, wherein the atomic ratio of Cr/other metal is between 50:1 and 1:1, said compounds are supported on a AlF.sub.3 support and being prepared by impregnating the support with a concentrated aqueous solution containing a soluble Cr (III) salt and a soluble salt of the other metal. The catalyst can be used in gaseous phase reactions.Type: GrantFiled: April 15, 1997Date of Patent: July 6, 1999Assignee: Ausimont S.P.A.Inventors: Francesco Rinaldi, Paolo Cuzzato, Letanzio Bragante
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Patent number: 5866730Abstract: A process is disclosed for enriching the amount of CFC-114 relative to the amount of CFC-114a from an initial mixture containing both isomers, by contacting said initial mixture with hydrogen chloride in the vapor phase at an elevated temperature in the presence of a catalyst to produce a product mixture containing C.sub.2 Cl.sub.2 F.sub.3 and chlorination products of CCl.sub.2 FCF.sub.3 wherein the weight ratio of CClF.sub.2 CClF.sub.2 to the total C.sub.2 Cl.sub.2 F.sub.4 is higher than the weight ratio of CClF.sub.2 CClF.sub.2 to the total C.sub.2 Cl.sub.2 F.sub.4 in the initial mixture. The chlorination products of CFC-114a (e.g., CCl.sub.3 CF.sub.3) in the product mixture may then be separated from the C.sub.2 Cl.sub.2 F.sub.4 therein (e.g., by distillation).Type: GrantFiled: April 2, 1993Date of Patent: February 2, 1999Assignee: E. I. du Pont de Nemours and CompanyInventor: V. N. Mallikarjuna Rao
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Patent number: 5849963Abstract: According to the method for producing difluoromethane and 1,1,1,2-tetrafluoroethane, having the steps of:(1) reacting methylene chloride and 1,1,2-trichloroethylene with hydrogen fluoride in a vapor phase In the presence of a fluorinating catalyst and 1,1,1,2-tetrafluoroethane in a first reactor; and(2) reacting 1,1,1-trifluorochloroethane with hydrogen fluoride in a vapor phase in the presence of a fluorinating catalyst in a second reactor, and supplying the reaction mixture from the second reactor to the first reactor, HFC-32 can be obtained in high conversion and high selectivity by fluorinating HCC-30 using commonly a large (excess) amount of HF which is required for producing HFC-134a.Type: GrantFiled: June 7, 1996Date of Patent: December 15, 1998Assignee: Daikin Industries, Ltd.Inventors: Yukio Homoto, Kunitada Tanaka, Takashi Shibanuma, Satoshi Komatsu, Satoshi Koyama
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Patent number: 5847242Abstract: 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, which is characterized by preparing certain single phase solid catalyst precursors containing two metal components (e.g., a divalent component of Mn, Co, Zn, Mg and/or Cd and a trivalent component of Al, Ga, Cr and/or V) which have structures that collapse at about 600.degree. C. or less; and producing said catalyst by heating the precursor to produce a multiphase composition wherein a phase containing one of the metal components is homogeneously dispersed with a phase containing the other metal component, and at least when the precursor contains no fluoride, contacting said multiphase composition with a vaporizable fluorine-containing fluorination compound at a temperature of from about 200.degree. C. to 450.degree. C. Also disclosed are single phase fluoride compositions having the formula MM'F.sub.5 (H.sub.2 O).sub.Type: GrantFiled: November 21, 1996Date of Patent: December 8, 1998Assignee: E. I. du Pont de Nemours and CompanyInventors: Velliyur Nott Mallikarjuna Rao, Munirpallam A. Subramanian
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Patent number: 5841006Abstract: Process for preparing pentafluoroethane (125) containing amounts of 115 lower than 0.02% by weight wherein pentafluoroethane is obtained by a dismutation process of tetrafluorochloroethane CF.sub.3 CHClF (HCFC-124) in gaseous phase in the presence of a chrome oxide catalyst (CR.sub.2 O.sub.3) supported on a AlF.sub.3 support, wherein one operates at temperatures from 140.degree.-180.degree. C. for contact times comprised between 15-30 seconds, from >180.degree. C. to 240.degree. C. for contact times between 5 to 15 seconds, from >240.degree. C. to 260.degree. C. for contact times between 1 to 5 seconds, from >260.degree. to 300.degree. C. for contact times between 0.1 to 1 second.Type: GrantFiled: November 26, 1996Date of Patent: November 24, 1998Assignee: Ausimont S.p.A.Inventor: Paolo Cuzzato
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Patent number: 5785822Abstract: The present invention provides a method for separating dichlorodifluoromethane from difluoromethane. More specifically, a process is provided for separating dichlorodifluoromethane and difluoromethane using azeotropic distillation.Type: GrantFiled: May 23, 1996Date of Patent: July 28, 1998Assignee: AlliedSignal Inc.Inventors: Gustavo Cerri, Kin Ching Kong, Charles Francis Swain, Rajat Subhra Basu
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Patent number: 5763698Abstract: The fluorine content of an acyclic saturated compound of the formula C.sub.n F.sub.a X.sub.b H.sub.c (wherein each X is independently selected from the group consisting of Cl and Br, and wherein n is 1 to 6, a is 1 to 13, b is 0 to 12, c is 1 to 9, and a+b+c equals 2n+2) is reduced by reacting the acyclic saturated compound with HCl in the vapor phase at an elevated temperature in the presence of a catalyst, the mole ratio of HCl to the acyclic saturated compound being at least about 1:1.Type: GrantFiled: November 3, 1995Date of Patent: June 9, 1998Assignee: E. I. du Pont de Nemours and CompanyInventors: Leo Ernest Manzer, V. N. Mallikarjuna Rao, Steven Henry Swearingen
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Patent number: 5734073Abstract: A method of halogenating an aromatic compound which comprises the steps of reacting an halogenating agent with the aromatic compound in the presence of fluorine and an acid, wherein the halogenating agent is at least one of an iodinating agent, a brominating agent and an chlorinating agent.Type: GrantFiled: April 18, 1996Date of Patent: March 31, 1998Assignee: BNFL Fluorochemicals LtdInventors: Richard Dickinson Chambers, Christopher John Skinner, Malcolm John Atherton, John Stewart Moilliet
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Patent number: 5714655Abstract: 2,2,3-trichloro-1,1,1,3,3-pentafluoropropane is used as a raw material, to which not less than 4.5 equivalent parts of hydrogen are added to effect a hydrogenation reaction in the presence of a noble metal catalyst, particularly a palladium catalyst, by the vapor phase method to manufacture 1,1,1,3,3-pentafluoropropane. Further, propane, propene, and hexachloropropene, etc. are chlorofluorinated in the presence of a metal catalyst to produce 2,2,3-trichloro-1,1,1,3,3-pentafluoropropane, then this compound is reduced with hydrogen in the presence of a noble metal catalyst to produce 1,1,1,3,3-pentafluoropropane. 2,2,3-trichloro-1,1,1,3,3-pentafluoropropane and 1,1,1,3,3-pentafluoropropane can thus be efficiently and economically produced.Type: GrantFiled: December 8, 1995Date of Patent: February 3, 1998Assignee: Daikin Industries, Ltd.Inventors: Akinori Yamamoto, Eiji Seki, Hirokazu Aoyama, Seiji Takubo, Tatsuo Nakada
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Patent number: 5714654Abstract: A method is proposed for producing 1,1,1,3,3-pentafluoropropane, in which 1,1,3,3,3-pentafluoropropene is reduced at a temperature between 40.degree. C. and 300.degree. C. by reacting it with hydrogen in a gas phase in the presence of a palladium catalyst. Further, a method is proposed for producing 1,1,1,3,3-pentafluoropropane and/or 1,1,3,3,3-pentafluoropropene, in which the raw material 2-chloro-1,1,3,3,3-pentafluoropropene is hydrogenated especially at a temperature between 30.degree. C. and 450.degree. C. in the presence of a catalyst composed of at least one metal selected from palladium, platinum and rhodium. Further, a method is proposed of producing 1,1,3,3,3-pentafluoropropene, in which 1,1,1,3,3-pentafluoro-2,3-dichloropropane is dechlorinated by using hydrogen in the presence of a metal oxide catalyst. Based on these production methods, 1,1,1,3,3-pentafluoropropane and/or 1,1,3,3,3-pentafluoropropene can thus be produced with high yield rates.Type: GrantFiled: December 8, 1995Date of Patent: February 3, 1998Assignee: Daikin Industries Ltd.Inventors: Akinori Yamamoto, Eiji Seki, Hirokazu Aoyama, Tatsuo Nakada
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Patent number: 5688379Abstract: The present invention provides a process for preparing a perfluoroalkyl bromide characterized by reacting a perfluoroalkyl iodide represented by the formula C.sub.n F.sub.2n+1 I wherein n is an integer of 6 to 10 with bromine in a light-transmitting reactor with exposure to light and heating at 120.degree. to 180.degree. C. while simultaneously removing IBr resulting as a by-product by separation of a layer.Type: GrantFiled: October 24, 1995Date of Patent: November 18, 1997Assignee: Daikin Industries, Ltd.Inventors: Yasuhisa Furutaka, Tatsuo Nakada, Kazuhiro Shimokawa, Yorisato Hisanaga, Souichi Ueda