By Reacting With Hydrogen Fluoride Patents (Class 570/164)
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Patent number: 8153018Abstract: Disclosed are compositions and systems having utility in numerous situations, including in particular solvent cleaning systems, as well as refrigerant lubricants and/or compatibilizing agents, and to methods which utilize such compositions and systems. More particularly, the present invention in preferred aspects is directed to solvents, blowing agents, heat transfer fluids and compatibilizing agents comprising the compound 3-chloro-1,1,1,6,6,6-hexafluoro-2,4-hexadiene. In particular, this invention provides a method for the production of the compound of Formula I, 3-chloro-1,1,1,6,6,6- hexafluoro-2,4-hexadiene,comprising reacting 1,1,1,3,3-pentachloropropane with hydrogen fluoride in the presence of a catalyst, in a reactor.Type: GrantFiled: September 30, 2011Date of Patent: April 10, 2012Assignee: Honeywell International Inc.Inventors: Robert C. Johnson, Hsueh Sung Tung
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Publication number: 20120065435Abstract: A process for dehydrating a hydrofluorocarbon or hydrochlorofluorocarbon, which can be done by simple equipment, and a continuous process of producing 1,3,3,3-tetrafluoropropene using the dehydration process. The dehydration process includes cooling the hydrofluorocarbon or hydrochlorofluorocarbon in gaseous form containing water with a heat exchanger, thereby condensing and liquefying the hydrofluorocarbon or hydrochlorofluorocarbon while freezing and solidifying the water.Type: ApplicationFiled: July 22, 2011Publication date: March 15, 2012Applicant: Central Glass Company, LimitedInventors: Yoshio NISHIGUCHI, Yasuo HIBINO
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Publication number: 20120065434Abstract: The present invention provides a process for preparing at least one chlorine-containing fluorocarbon compound selected from the group consisting of chlorine-containing fluoropropane compounds represented by Formula (1): CFnCl3-nCHClCH2—Cl, wherein n is 1 or 2, and chlorine-containing fluoropropene compounds represented by Formula (2): CFnCl3-nCCl?CH2, wherein n is 1 or 2, wherein the process includes the step of contacting at least one chlorine-containing compound selected from the group consisting of 1,1,1,2,3-pentachloropropane, 1,1,2,3-tetrachloropropene, and 2,3,3,3-tetrachloropropene with hydrogen fluoride in the absence of a catalyst while heating. According to the present invention, the chlorine-containing propane and propene compounds having 1 or 2 fluorine atoms can be prepared by an industrially applicable, simple and effective process.Type: ApplicationFiled: May 12, 2010Publication date: March 15, 2012Inventors: Masatoshi Nose, Tsuneo Yamashita, Atsushi Suzuki
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Patent number: 8067649Abstract: Disclosed is a process for producing tetrafluoropropene comprising: (a) catalytically fluorinating at least one tetrafluoropropene in a first reactor to produce HCFO-1233xf; (b) reacting said HCFO-1233xf with hydrogen fluoride in a second reactor to produce HCFC-244bb; (c) recycling at least a portion of said HCFC-244bb back to said first reactor as recycled HCFC-244bb; and (d) catalytically dehydrochlorinating said recycled HCFC-244bb in said first reactor to produce HFO-1234yf.Type: GrantFiled: May 14, 2009Date of Patent: November 29, 2011Assignee: Honeywell International Inc.Inventors: Haluk Kopkalli, Yuon Chiu, Hsueh Sung Tung
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Patent number: 8058487Abstract: The present invention relates to a continuous process for the fluorination of perchloroethylene (PER) in the gas phase in a single stage with hydrofluoric acid (HF) in the presence of a catalyst to give, as major product, pentafluoroethane. The process is characterized in that it is carried out at a temperature of between 280 and 430° C. and with an HF/PER molar ratio of greater than or equal to 20.Type: GrantFiled: November 30, 2006Date of Patent: November 15, 2011Assignee: Arkema FranceInventors: Beatrice Boussand, Michel Devic
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Patent number: 8058486Abstract: A method for preparing 2,3,3,3-tetrafluoroprop-1-ene comprising (a) providing a starting composition comprising at least one compound having a structure selected from Formulae I, II and III: CX2?CCl—CH2X??(Formula I) CX3—CCl?CH2??(Formula II) CX3—CHCl—CH2X??(Formula III) wherein X is independently selected from F, Cl, Br, and I, provided that at least one X is not fluorine; (b) contacting said starting composition with a first fluorinating agent to produce a first intermediate composition comprising 2-chloro-3,3,3-trifluoropropene and a first chlorine-containing byproduct; (c) contacting said first intermediate composition with a second fluorinating agent to produce a second intermediate composition comprising 2-chloro-1,1,1,2-tetrafluoropropane and a second chlorine-containing byproduct; and (d) catalytically dehydrochlorinating at least a portion of said 2-chloro-1,1,1,2-tetrafluoropropane to produce a reaction product comprising 2,3,3,3-tetrafluoroprop-1-ene.Type: GrantFiled: March 13, 2009Date of Patent: November 15, 2011Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski, Selma Bektesevic, Robert C. Johnson, Haiyou Wang
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Patent number: 7829748Abstract: The invention provides an economic process for the manufacture of 1,3,3,3-tetrafluoropropene (HFO-1234ze) by a two stage process. A vapor phase hydrofluorination of 1-chloro-3,3,3-trifluoropropene (HCFC-1233zd) into 1-chloro-1,3,3,3-tetrafluoropropane (HCFC-244fa) and/or 1,1,1,3,3-pentafluoropropane (HFC-245fa) is conducted, followed by the thermal dehydrochlorination of HCFC-244fa and dehydro fluorination of HFC-245fa into HFO-1234ze in the presence of a catalyst which comprises one or more of alkali metal halides, alkaline earth metal halides, halogenated metal oxides, zero oxidation state metals, zinc halides, palladium halides, and activated carbon.Type: GrantFiled: September 21, 2009Date of Patent: November 9, 2010Assignee: Honeywell International Inc.Inventors: Hsuehsung Tung, Robert C. Johnson, Daniel C. Merkel, Haiyou Wang
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Patent number: 7781626Abstract: The invention relates to azeotropic and azeotrope-like mixtures of 1,1,1,3,3-pentafluorobutane (HFC-365) and hydrogen fluoride and a process for separating the azeotrope-like mixtures. The compositions of the invention are useful as an intermediate in the production of HFC-365. The latter is useful as a nontoxic, zero ozone depleting fluorocarbon useful as a solvent, blowing agent, refrigerant, cleaning agent and aerosol to propellant.Type: GrantFiled: August 21, 2007Date of Patent: August 24, 2010Assignee: Honeywell International IncInventors: Hang T. Pham, Rajiv R. Singh, Hsueh S. Tung
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Publication number: 20100130798Abstract: The production process for 1,2,3,4-tetrachlorohexafluorobutane of the present invention is characterized in that 1,2,3,4-tetrachlorobutane is reacted with fluorine in the presence of a solvent containing hydrogen fluoride. The 1,2,3,4-tetrachlorobutane may be obtained by chlorination of 3,4-dichlorobutene-1. Further, the present invention provides as well a process of refining 1,2,3,4-tetrachlorohexafluorobutane obtained in the manner described above. According to the present invention, 1,2,3,4-tetrachlorohexafluorobutane which is useful, for example, as a synthetic raw material for hexafluoro-1,3-butadiene used as an etching gas for semiconductors can industrially efficiently be produced by using 1,2,3,4-tetrachlorobutane which is a by-product of chloroprene and which has so far been disposed.Type: ApplicationFiled: March 26, 2008Publication date: May 27, 2010Applicant: SHOWA DENK K.K.Inventors: Hiromoto Ohno, Toshio Ohi, Nobutoshi Sasaki, Kiyoshi Nomura
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Publication number: 20100121118Abstract: The process for producing a fluorine-containing compound such as 1,2,3,4-tetrachclorohexafluorobutane of the present invention is characterized in that a halogenated hydrocarbon compound such as 1,2,3,4-tetrachlorobutane is brought into contact with fluorine gas in a liquid phase or in a solid-liquid coexistence state in the absence of a solvent and a catalyst. According to the present invention, a fluorine-containing compound is readily produced from a halogenated hydrocarbon compound using neither a reaction solvent nor a reaction catalyst.Type: ApplicationFiled: April 14, 2008Publication date: May 13, 2010Applicant: SHOWA DENKO K.K.Inventors: Hiromoto Ohno, Toshio Ohi
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Patent number: 7714177Abstract: Disclosed is a process for the synthesis of 1,3,3,3-tetrafluoropropene comprising: a) reacting a compound of the formula (I) CHFX2 with a compound of formula (II) CH2?CF2 to produce a reaction product comprising a compound of formula (III) CHXFCH2CXF2, wherein each X is independently selected from the group consisting of chlorine, bromine and iodine; and (b) exposing said compound of formula (III) to reaction conditions effective to convert said compound to 1,3,3,3-tetrafluoropropene.Type: GrantFiled: January 7, 2008Date of Patent: May 11, 2010Assignee: Honeywell International Inc.Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Hsueh S. Tung, Michael Van Der Puy
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Patent number: 7629495Abstract: A process for the manufacture of 1,1,1,3,3-pentafluoropropane which comprises adding hydrogen fluoride to 1,1,1,3-tetrafluoropropene in the substantial absence of metal catalyst. Another embodiment provides for the manufacture of 1,1,1,3,3-pentafluoropropane which comprises adding hydrogen fluoride to 1,1,1,3-tetrafluoropropene in the presence of an amine hydrofluoride complex and a metal catalyst.Type: GrantFiled: March 22, 2007Date of Patent: December 8, 2009Assignee: Solvay (Societé Anonyme)Inventors: Johannes Eicher, Stefan Mross
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Publication number: 20090287027Abstract: Provided is a process for purifying an organic feedstock comprising (a) distilling a raw organic feedstock comprising hydrogen fluoride, 2-chloro-1,1,1,2-tetrafluoropropane, and 2-chloro-3,3,3-trifluoropropene to produce a first distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a first bottoms stream rich in hydrogen fluoride; (b) cooling said first distillate stream to produce an intermediate composition comprising an organic layer rich in 2-chloro-1,1,1,2-tetrafluoropropane and 2-chloro-3,3,3-trifluoropropene, and an acid layer rich in hydrogen fluoride; and, optionally but preferably, (c) distilling said organic layer to produce a second distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a second bottoms stream comprising a purified organic feedstock substantially free of hydrogen fluoride.Type: ApplicationFiled: May 12, 2009Publication date: November 19, 2009Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung
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Patent number: 7592494Abstract: The invention provides an economic process for the manufacture of 1,3,3,3-tetrafluoropropene (HFC-1234ze) by a two stage process. A hydrofluorination of 1-chloro-3,3,3-trifluoropropene (HCFC-1233zd) into 1-chloro-1,3,3,3-tetrafluoropropane (HCFC-244fa) and 1,1,1,3,3-pentafluoropropane (HFC-245fa) is conducted, followed by the dehydrochlorination of HCFC-244fa and dehydrofluorination of HFC-245fa into HFC-1234ze.Type: GrantFiled: July 25, 2003Date of Patent: September 22, 2009Assignee: Honeywell International Inc.Inventors: Hsueh Sung Tung, Robert C. Johnson, Daniel C. Merkel
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Patent number: 7566809Abstract: 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: May 25, 2007Date of Patent: July 28, 2009Assignee: Solvay S.A.Inventors: Alain Lambert, Vincent Wilmet
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Patent number: 7524999Abstract: A process for the preparation of 1,1,1,3,3,3-hexafluoropropane is disclosed. The process involves (a) contacting at least one halopropane of the formula CF3CH2CHyX3-y (where each X is independently F, Cl or Br, and y is 3, 2, or 1) with Cl?2#191 in the presence of light or a free radical initiator to produce a mixture comprising CF3CH2CCIyX3-y; (b) contacting the CF3CH2CCIyX3-y produced in step (a) with HF, optionally in the presence of a fluorination catalyst, to produce a product mixture comprising CF3CH2CF3; and (c) recovering CF3CH2CF3 from the mixture produced in step (b).Type: GrantFiled: December 19, 2005Date of Patent: April 28, 2009Assignee: E. I. du Pont de Nemours and CompanyInventors: Mario Joseph Nappa, Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
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Patent number: 7504358Abstract: A crystalline alpha-chromium oxide where from about 0.05 atom % to about 2 atom % of the chromium atoms in the alpha-chromium oxide lattice are substituted by nickel atoms, and optionally, additional chromium atoms in the alpha-chromium oxide lattice are substituted by trivalent cobalt atoms (provided that the total amount of the nickel atoms and the trivalent cobalt atoms in the alpha-chromium oxide lattice is no more than 6 atom %) is disclosed. Also disclosed is a chromium-containing catalyst composition comprising as a chromium-containing component the crystalline substituted alpha-chromium oxide; and a method for preparing a composition comprising the crystalline substituted alpha-chromium oxide.Type: GrantFiled: August 21, 2003Date of Patent: March 17, 2009Assignee: E. I. du Pont de Nemours and CompanyInventors: Velliyur Nott Mallikarjuna Rao, H. David Rosenfeld, Allen C. Sievert, Shekhar Subramoney, Munirpallam Appadorai Subramanian
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Publication number: 20090062576Abstract: A process for the manufacture of 1,1,1,3,3-pentafluoropropane which comprises adding hydrogen fluoride to 1,1,1,3-tetrafluoropropene in the substantial absence of metal catalyst. Another embodiment provides for the manufacture of 1,1,1,3,3-pentafluoropropane which comprises adding hydrogen fluoride to 1,1,1,3-tetrafluoropropene in the presence of an amine hydrofluoride complex and a metal catalyst.Type: ApplicationFiled: March 22, 2007Publication date: March 5, 2009Applicant: SOLVAY (SOCIETE ANONYME)Inventors: Johannes Eicher, Stefan Mross
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Publication number: 20080154064Abstract: A method of fluorination comprising reacting monosaccharides, oligosaccharides, polysaccharides, composite saccharides formed by bonding of these saccharides with proteins and lipids and saccharides having polyalcohols, aldehydes, ketones and acids of the polyalcohols, and derivatives and condensates of these compounds with a fluorinating agent represented by general formula (I) thermally or under irradiation with microwave or an electromagnetic wave having a wavelength around the microwave region. In accordance with the method, the fluorination at a selected position can be conducted safely at a temperature in the range of 150 to 200° C. where the reaction is difficult in accordance with conventional methods. The above method comprising the irradiation with microwave or an electromagnetic wave having a wavelength around the microwave region can be applied to substrates other than saccharides.Type: ApplicationFiled: February 7, 2008Publication date: June 26, 2008Inventors: Shoji Hara, Tsuyoshi Fukuhara
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Patent number: 7361795Abstract: The invention relates to azeotropic and azeotrope-like mixtures of 1,1,1,3,3-pentafluorobutane (HFC-365) and hydrogen fluoride and a process for separating the azeotrope-like mixtures. The compositions of the invention are useful as an intermediate in the production of HFC-365. The latter is useful as a nontoxic, zero ozone depleting fluorocarbon useful as a solvent, blowing agent, refrigerant, cleaning agent and aerosol to propellant.Type: GrantFiled: October 14, 2003Date of Patent: April 22, 2008Assignee: Honeywell International, Inc.Inventors: Hang T. Pham, Rajiv R. Singh, Hsueh S. Tung
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Patent number: 7345209Abstract: Disclosed is a process for the synthesis of 1,3,3,3-tetrafluoropropene that comprises, in one preferred embodiment, providing a compound of the formula CF3CH2CHFX, wherein X is a selected from the group consisting of chlorine, bromine and iodine, and exposing said compound to reaction conditions effective to convert said compound to 1,3,3,3-tetrafluoropropene. Other processes for forming 1,3,3,3-tetrafluoropropene are also disclosed.Type: GrantFiled: April 29, 2005Date of Patent: March 18, 2008Assignee: Honeywell International Inc.Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Hsueh S. Tung, Michael Van Der Puy
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Patent number: 7317071Abstract: Processes for producing a fluoromonomer from a fluoropolymer, among which one that can be carried out more simply is a process wherein thermal decomposition of a fluoropolymer is preformed by means of a rotary kiln (5) so as to produce a fluoromonomer, the process comprising feeding a fluoropolymer and steam (3) into a rotary kiln and heating the fluoropolymer.Type: GrantFiled: February 27, 2003Date of Patent: January 8, 2008Assignee: Daikin Industries, Ltd.Inventors: Takuya Ichida, Yukio Homoto
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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: 7230146Abstract: Dehydrohalogenation processes for the preparation of fluoropropenes from corresponding halopropanes, in which the fluoropropenes have the formula CF3CY?CXNHP, wherein X and Y are independently hydrogen or a halogen selected from fluorine, chlorine, bromine and iodine; and N and P are independently integers equal to 0, 1 or 2, provided that (N+P)=2.Type: GrantFiled: October 27, 2003Date of Patent: June 12, 2007Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Rajiv R. Singh, Hsueh Sung Tung
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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: 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: 7176338Abstract: The invention relates to a process for preparing 1,1,1-trifluoro-2,2-dichloroethane (F123). This process consists in placing 1,1,1-trifluoro-2-chloroethane (F133a) in contact with chlorine in the presence of hydrogen fluoride and a fluorination catalyst. F133a may be obtained by fluorination of trichloroethylene, and the F123 may be subsequently fluorinated to F125.Type: GrantFiled: April 1, 2004Date of Patent: February 13, 2007Assignee: AtofinaInventors: Béatrice Boussand, Eric Jorda
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Patent number: 7145046Abstract: Inorganic and organic compounds containing fluorine can be produced, for example, from corresponding chlorine-containing compounds by chlorine/fluorine exchange using fluorinating agents. Monocyclic or bicyclic compounds containing at least two nitrogen atoms, at least one of which is incorporated into the ring system, can be used as catalysts or fluorinating agents for chlorine/fluorine exchange reactions to produce sulfurylchlorofluoride, sulfurylfluoride or a carboxylic acid fluoride. It is likewise possible to carry out HF addition to unsaturated carbon-carbon bonds or chlorine/fluorine exchange at carbon atoms. For example, monochloro or dichloro malonic acid esters can be converted to difluoro malonic acid esters. Work-up of the reaction mixture can be simplified by using suitable solvents which force the reaction mixture to exist in two phases.Type: GrantFiled: August 1, 2003Date of Patent: December 5, 2006Assignee: Solvay Fluor und Derivate GmbHInventors: Max Braun, Carsten Brosch
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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: 7112708Abstract: A process for the production of difluoromethane (HFC-32), 1,1,1-trifluoroethane (HFC-143a) and 1,1-difluoroethane (HFC-152a).Type: GrantFiled: April 1, 2004Date of Patent: September 26, 2006Assignee: Honeywell International Inc.Inventors: Daniel C Merkel, Hsuehsung Tung, Ian Shankland
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Patent number: 7109386Abstract: Process for the preparation of a halogenated olefin by reaction of an alkyne and/or of an allene compound with a hydrogen halide in a liquid medium comprising at least one hydrohalogenation catalyst comprising at least one palladium compound.Type: GrantFiled: March 20, 2002Date of Patent: September 19, 2006Assignee: Solvay (Societe Anonyme)Inventor: Véronique Mathieu
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Patent number: 7102040Abstract: The invention provides an apparatus useful in fluorinating organic compounds, or more particularly to a reactor system suitable for the fluorination of organic compounds on a commercial scale. The apparatus is also useful in chemical reactions including heating or cooling.Type: GrantFiled: April 4, 2003Date of Patent: September 5, 2006Assignee: Honeywell International Inc.Inventors: Yuon Chiu, Merwyn E. Howells, Stephen A. Cottrell
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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: 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: 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: 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: 7071368Abstract: A process for producing 1,1,1-trifluoroethane (HFC-143a) which process comprises reacting hydrogen fluoride with vinylidene chloride along with one or more of 1,1,-dichloro-1-fluoroethane (HCFC-141b), 1-chloro-1,1-difluoroethane (HCFC-142b) and 1,1,1-trichloroethane (HCC-140a) in the presence of pentavalent antimony as a fluorination catalyst under conditions to produce 1,1,1-trifluoroethane (HFC-143a), generally in yields of 90% or more.Type: GrantFiled: February 9, 2005Date of Patent: July 4, 2006Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Hsueh Sung Tung, Robert C. Johnson
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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: 7067707Abstract: Process for the manufacture of pentafluoroethane, according to which tetrafluoroethylene is subjected to reaction with an organic nitrogenous base hydrofluoride at a temperature of greater than 100° C. and not exceeding 160° C.Type: GrantFiled: August 22, 2003Date of Patent: June 27, 2006Assignee: Solvay (Societe Anonyme)Inventors: Eberhard Piepho, Vincent Wilmet, Olivier Buyle
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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: 7053252Abstract: The invention relates to a process for preparing 1,1,1-trifluoro-2,2-dichloroethane (F123). This process consists in placing 1,1,1-trifluoro-2-chloroethane (F133a) in contact with chlorine in the presence of hydrogen fluoride and a fluorination catalyst. F133a may be obtained by fluorination of trichloroethylene, and the F123 may be subsequently fluorinated to F125.Type: GrantFiled: August 2, 2002Date of Patent: May 30, 2006Assignee: AtofinaInventors: Béatrice Boussand, Eric Jorda
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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: 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: 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: 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