Catalyst Utilized Patents (Class 570/156)
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Patent number: 8178466Abstract: The present disclosure provides methods for pre-treating activated carbon before it is used in a dehydrochlorination process. The methods can comprise mixing the activated carbon with an acid, an oxidizing agent in a liquid phase, or an oxidizing agent in a gas phase. Activated carbons undergoing one or more of these methods can exhibit improved stability during the dehydrochlorination process.Type: GrantFiled: January 14, 2011Date of Patent: May 15, 2012Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Hsueh S. Tung
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Publication number: 20120108859Abstract: The disclosure describes a process for dehalogenation of chlorofluorocompounds. The process comprises contacting a saturated chlorofluorocompound with hydrogen in the presence of a catalyst at a temperature sufficient to remove chlorine and/or fluorine substituents to produce a fluorine containing terminal olefin.Type: ApplicationFiled: October 20, 2011Publication date: May 3, 2012Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: MARIO JOSEPH NAPPA, Ekaterina N. Swearingen, Allen Capron Sievert, Xuehui Sun
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Patent number: 8163964Abstract: A process is disclosed for making CF3CF?CHF or a mixture thereof with CF2?CFCHF2. The process involves (i) contacting CH2ClCF2CF3, and optionally CH2FCF2CClF2, in a reaction zone in the presence of a catalytically effective amount of dehydrofluorination catalyst to produce CHCl?CFCF3, and, if CH2FCF2CClF2 is present, CHF?CFCClF2; (ii) contacting CHCl?CFCF3, and CHF?CFCClF2, if any, formed in (i) with hydrogen fluoride (HF) in a reaction zone, optionally in the presence of a fluorination catalyst, to produce a product mixture comprising CHF?CFCF3, and, if CHF?CFCClF2 is present, CF2?CFCHF2; and (iii) recovering CF3CF?CHF, or a mixture thereof with CF2?CFCHF2, from the product mixture formed in (ii); and optionally (iv) separating at least a portion of any CF3CF?CHF in the product mixture formed in (ii) from the CF2?CFCHF2 in the product mixture formed in (ii). Also disclosed is an azeotropic composition involving CHCl?CFCF3, CHF?CFCClF2 and HF.Type: GrantFiled: November 15, 2007Date of Patent: April 24, 2012Assignee: E. I. du Pont de Nemours and CompanyInventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
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Patent number: 8158836Abstract: The invention is directed to a process for preparing 2,3,3,3-tetrafluoropropene (1234yf), comprising: (i) contacting 1,1,2,3-tetrachloropropene (1230xa) with hydrogen fluoride HF in gas phase in the presence of a fluorination catalyst under conditions sufficient to produce a reaction mixture; (ii) separating the reaction mixture into a first stream comprising HCl, 2,3,3,3-tetrafluoropropene (1234yf) and a second stream comprising HF, 2-chloro-3,3,3-trifluoro-1-propene (1233xf) and 1,1,1,2,2-pentafluoropropane (245cb); (iii) recycling at least a part of the second stream at least in part back to step (i).Type: GrantFiled: December 23, 2010Date of Patent: April 17, 2012Assignee: Arkema FranceInventors: Anne Pigamo, Dominique Deur-Bert, Laurent Wendlinger
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Patent number: 8148586Abstract: A process is disclosed for making CF3CF?CHF. The process involves contacting at least one hexafluoropropane selected from the group consisting of CF3CF2CH2F and CF3CHFCHF2 with a chromium oxyfluoride catalyst in a reactor to obtain a product mixture comprising CF3CF?CHF, and recovering CF3CF?CHF from the product mixture. A process is disclosed for making CF3CH?CHF. The process involves contacting CF3CH2CHF2 with a chromium oxyfluoride catalyst in a reactor to obtain a product mixture comprising CF3CH?CHF, and recovering CF3CH?CHF from the product mixture. A process is disclosed for making CF3CF?CH2. The process involves contacting CF3CF2CH3 with a chromium oxyfluoride catalyst in a reactor to obtain a product mixture comprising CF3CF?CH2, and recovering CF3CF?CH2 from the product mixture.Type: GrantFiled: June 3, 2011Date of Patent: April 3, 2012Assignee: E. I. du Pont de Nemours and CompanyInventors: Mario Joseph Nappa, Velliyur Nott Mallikarjuna Rao
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Processes for the synthesis of 2-chloro-1,1,1,3,3,4,4,4-heptafluoro-2-butene and hexafluoro-2-butyne
Patent number: 8143462Abstract: Disclosed is a process comprising reacting CF3CCl2CF2CF3 (CFC-318ma) with hydrogen in the presence of a dehalogenation catalyst to produce CF3CCl?CFCF3 (CFC-1317mx). Also disclosed is a process comprising reacting CF3CCl?CFCF3 (CFC-1317mx) with hydrogen in the presence of a dehalogenation catalyst to produce CF3C?CCF3 (hexafluoro-2-butyne). Hexafluoro-2-butyne can be used to produce CF3CH?CHCF2CF3 (1,1,1,4,4,5,5,5-octafluoro-2-pentene).Type: GrantFiled: December 15, 2008Date of Patent: March 27, 2012Assignee: E.I. du Pont de Nemours and CompanyInventor: Mario Joseph Nappa -
Patent number: 8133406Abstract: A process is disclosed for making CF3CF?CH2 or mixtures thereof with CHF2CF?CHF. This process involves (a) reacting CHCl2CF2CF3, and optionally CHClFCF2CClF2, with H2 in the presence of a catalytically effective amount of a hydrogenation catalyst to form CH3CF2CF3 and, when CHClFCF2CClF2 is present, CH2FCF2CHF2; (b) dehydrofluorinating CH3CF2CF3, and optionally any CH2FCF2CHF2, from (a) to form a product mixture including CF3CF?CH2 and, if CH2FCF2CHF2 is present, CHF2CF?CHF; and optionally (c) recovering CF3CF?CH2, or a mixture thereof with CHF2CF?CHF from the product mixture formed in (b) and/or (d) separating at least a portion of any CHF2CF?CHF in the product mixture formed in (b) from the CF3CF?CH2 in the product mixture formed in (b).Type: GrantFiled: October 31, 2007Date of Patent: March 13, 2012Assignee: E.I. du Pont de Nemours and CompanyInventors: Mario Joseph Nappa, Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
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Publication number: 20120059201Abstract: Disclosed is a process for the preparation of 3,3,3-trifluoropropene comprising the steps of; (1) fluorination of 240fa to form 245fa; (2) conversion of 245fa to a cis/trans mixture of 1234ze; (3) hydrogenation of the cis/trans mixture of 1234ze to form 254fb; and (4) dehydrofluorination of 254fb to produce 3,3,3-trifluoropropene. Alternatively or additionally, a second process for the preparation of the desired compound comprises the following steps; (1) fluorination of HCC-240fa to form HCFC-244fa; (2) conversion of 244fa to a cis/trans mixture of HFO-1234ze; (3) hydrogenation of the cis/trans mixture of 1234ze to form HFC-254fb; and (4) dehydrofluorination of 254fb to produce 3,3,3-trifluoropropene.Type: ApplicationFiled: September 3, 2010Publication date: March 8, 2012Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung
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Publication number: 20120059200Abstract: Disclosed is an integrated manufacturing process to co-produce (E)1-chloro-3,3,3-trifluoropropene, (E)1,3,3,3-tetrafluoropropene, and 1,1,1,3,3-pentafluoro-propane starting from a single chlorinated hydrocarbon feed stock, 240fa. The process includes a combined liquid or vapor phase reaction/purification operation which directly produces (E)1-chloro-3,3,3-trifluoropropene (1233zd(E)) from 240fa. In the second liquid phase fluorination reactor 1233zd(E) is contacted with HF in the presence of catalyst to produce 1,1,1,3,3-pentafluoropropane (245fa) with high conversion and selectivity. A third reactor is used for dehydrofluorination of 245fa to produce (E)1,3,3,3-tetrafluoropropene (1234ze(E)) by contacting in the liquid phase with a caustic solution or in the vapor phase using a dehydrofluorination catalyst. This operation may be followed by one or more purification processes to recover the 1234ze(E) product.Type: ApplicationFiled: August 29, 2011Publication date: March 8, 2012Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Haiyou Wang, Hsueh Sung Tung, Ian Shankland
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Publication number: 20120053370Abstract: 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: ApplicationFiled: September 6, 2011Publication date: March 1, 2012Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Daniel C. Merkel, Rajiv R. Singh, Hsueh Sung Tung
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Publication number: 20120053371Abstract: Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CF3CF?CH2 (1234yf). In certain preferred embodiments the processes comprise first exposing a compound of Formula (IA) C(X)2?CClC(X)3??(IA) where each X is independently F, Cl or H, preferably CCl2?CClCH2Cl, to one or more sets of reaction conditions, but preferably a substantially single set of reaction conditions, effective to produce at least one chlorofluoropropane, preferably in accordance with Formula (IB): CF3CClX?C(X?)3??Formula (IB) where each X? is independently F, Cl or H, and then exposing the compound of Formula (IB) to one or more sets of reaction conditions, but preferably a substantially single set of reaction conditions, effective to produce a compound of Formula (II) CF3CF?CHZ??(II) where Z is H, F, Cl, I or Br.Type: ApplicationFiled: November 2, 2011Publication date: March 1, 2012Applicant: HONEYWELL INTERNATIONAL INC.Inventors: ROBERT C. JOHNSON, HSUEH S. TUNG, DANIEL C. MERKEL
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Patent number: 8119845Abstract: The present invention relates to an improved method for manufacturing 2-chloro-3,3,3,-trifluoropropene (HCFC-1233xf) by reacting 1,1,2,3-tetrachloropropene, 1,1,1,2,3-pentachloropropane, and/or 2,3,3,3-tetrachloropropene with hydrogen fluoride, in a vapor phase reaction vessel in the presence of a vapor phase fluorination catalyst and stabilizer. HCFC-1233xf is an intermediate in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf) which is a refrigerant with low global warming potential.Type: GrantFiled: September 13, 2010Date of Patent: February 21, 2012Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Hsueh S. Tung
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Patent number: 8115037Abstract: There is provided a method for producing 1,3,3,3-tetrafluoropropene. This method includes dehydrofluorinating 1,1,1,3,3-pentafluoropropane in gas phase in the presence of a zirconium compound-carried catalyst in which a zirconium compound is carried on a metal oxide or activated carbon.Type: GrantFiled: December 12, 2008Date of Patent: February 14, 2012Assignee: Central Glass Company, LimitedInventors: Fuyuhiko Sakyu, Yasuo Hibino
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Publication number: 20120004475Abstract: Disclosed herein are processes for the production of hydrofluoroolefins including 2,3,3,4,4,4-hexafluoro-1-butene by dehydrofluorination. Also disclosed herein are processes for separation of hydrofluoroolefins from hydrofluorocarbons and from hydrogen fluoride.Type: ApplicationFiled: September 14, 2011Publication date: January 5, 2012Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: RALPH NEWTON MILLER, MARIO JOSEPH NAPPA, VELLIYUR NOTT MALLIKARJUNA RAO, ALLEN CAPRON SIEVERT
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Publication number: 20110319680Abstract: In the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf), formation of HFC-254eb as an excessively reduced product is suppressed. A process for producing 2,3,3,3-tetrafluoropropene, which comprises reacting a raw material compound gas composed of at least one of 1,1-dichloro-2,3,3,3-tetrafluoropropene and 1-chloro-2,3,3,3-tetrafluoropropene, and hydrogen gas, in the presence of a catalyst, wherein the catalyst is a catalyst having palladium supported on active carbon, and the ratio of the number of moles of the hydrogen gas to the number of moles of chlorine atoms in the raw material compound gas (H2/Cl) is at most 0.7.Type: ApplicationFiled: June 23, 2011Publication date: December 29, 2011Applicant: ASAHI GLASS COMPANY, LIMITEDInventors: Satoshi KAWAGUCHI, Hidekazu OKAMOTO, Yu TAKEUCHI, Hirokazu TAKAGI, Kunio WATANABE, Koichi YANASE
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Publication number: 20110319679Abstract: The object is to provide a process whereby it is possible to produce 2,3,3,3-tetrafluoropropene at a high conversion ratio constantly for a long period of time. A process for producing 2,3,3,3-tetrafluoropropene, which comprises reacting a raw material compound of at least one of 1,1-dichloro-2,3,3,3-tetrafluoropropene and 1-chloro-2,3,3,3-tetrafluoropropene, and hydrogen, in the presence of a catalyst, wherein the catalyst is a noble metal catalyst supported on a metal oxide having a Hammett acidity function value (H0) of at least ?5.6.Type: ApplicationFiled: June 23, 2011Publication date: December 29, 2011Applicant: ASAHI GLASS COMPANY, LIMITEDInventors: Hirokazu Takagi, Hidekazu Okamoto
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Publication number: 20110319678Abstract: To provide a process to produce 1,1-dichloro-2,3,3,3-tetrafluoropropene (CFO-1214ya) simply and economically without requiring purification of 1,1-dichloro-2,2,3,3,3-pentafluoropropane (HCFC-225ca) from the raw material component obtained as a mixture of isomers, i.e. dichloropentafluoropropane (HCFC-225) including HCFC-225ca and at the same time to produce simply and economically 2,3,3,3-tetrafluoropropene (HFO-1234yf) from 1-chloro-2,3,3,3-tetrafluoropropane (HCFC-244eb). A raw material composition comprising HCFC-244eb and HCFC-225 including HCFC-225ca is contacted with an alkali aqueous solution in the presence of a phase-transfer catalyst to produce CFO-1214ya from HCFC-225ca and at the same time to produce HFO-1234yf from HCFC-244eb.Type: ApplicationFiled: June 23, 2011Publication date: December 29, 2011Applicant: Asahi Glass Company, LimitedInventors: Ryuji SEKI, Hidekazu Okamoto, Hirokazu Takagi, Satoshi Kawaguchi
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Patent number: 8080696Abstract: The present invention provides a method for producing an olefin represented by General Formula (II): RfCF?CH2 (II) (wherein Rf is defined as below), wherein the method includes the step of contacting a fluorohalide represented by General Formula (I): RfCF2CH2X (I) (wherein Rf is H(CF2)n (n=1 to 8) or F(CF2)n (n=1 to 8), and X is Br or I) with a metal in a reaction medium of a polar organic solvent, or a mixed solvent of water and a polar organic solvent to conduct a dehalogenation reaction. The production method of the present invention provides olefins in a highly selective manner at a low cost and high yield under relatively mild reaction conditions.Type: GrantFiled: October 26, 2007Date of Patent: December 20, 2011Assignee: Daikin Industries, Ltd.Inventors: Akinari Sugiyama, Takehiro Chaki
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Patent number: 8067650Abstract: This invention relates a process for the manufacture of the HFO trans-1,3,3,3-tetrafluoropropene (HFO trans-1234ze). More particularly, the invention pertains to a process for the manufacture of the HFO trans-1234ze by first dehydrofluorinating 1,1,1,3,3-pentafluoropropane to thereby produce a mixture of cis-1,3,3,3-tetrafluoropropene, trans-1,3,3,3-tetrafluoropropene and hydrogen fluoride. Then optionally recovering hydrogen fluoride and then recovering trans-1,3,3,3-tetrafluoropropene.Type: GrantFiled: July 10, 2007Date of Patent: November 29, 2011Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Hsueh Sung Tung
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Publication number: 20110288350Abstract: Disclosed is a process for the preparation of fluorine-containing olefins comprising contacting a chlorofluoroalkane with hydrogen in the presence of a catalyst at a temperature sufficient to cause replacement of the chlorine substituents of the chlorofluoroalkane with hydrogen to produce a fluorine-containing olefin. Also disclosed are catalyst compositions for the hydrodechlorination of chlorofluoroalkanes comprising copper metal deposited on a support, and comprising palladium deposited on calcium fluoride, poisoned with lead and reducing the in the presence or absence of a dehydrochlorination catalyst under conditions effective to form a product stream comprising cis-1,1,1,4,4,4-hexafluoro-2-butene (HFO-1336).Type: ApplicationFiled: May 19, 2011Publication date: November 24, 2011Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Andrew Joseph Poss, Michael Van Der Puy, Rajiv Ratna Singh, David Nalewajek, Haridasan K. Nair
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Publication number: 20110288348Abstract: Disclosed is a process for making hexafluoro-2-butyne comprising the steps of: (a) providing a composition comprising CF3CX?CXCF3, where X=halogen; and (b) treating CF3CX?CXCF3 with a dehalogenation catalyst in the presence of a halogen acceptor compound Y, where Y is not hydrogen. The halogen acceptor compound Y is a material capable of being halogenated, preferably a compound having a multiple bond, such as an alkyne, alkene, allene, or carbon monoxide. Another suitable material capable of being halogenated is a cyclopropane. A catalyst effectively transfers halogen from CF3CX?CXCF3 to the halogen acceptor compound. Since Y is not hydrogen, the formation of CF3CX?CHCF3 is greatly reduced or eliminated.Type: ApplicationFiled: May 19, 2011Publication date: November 24, 2011Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Andrew Joseph Poss, David Nalewajek, Haridasan K. Nair, Michael Van Der Puy, Rajiv Ratna Singh
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Publication number: 20110288349Abstract: The present invention provides a method for the preparation of suitable chlorofluorocarbon and hydrochlorofluorocarbon materials or chlorofluorocarbon and hydrochlorofluorocarbon alkene and alkyne intermediates which serve as useful feedstock for fluorination and reduction to cis-1,1,1,4,4,4-hexafluoro-2-butene. Also presented is a continuous process for the production of cis-1,1,1,4,4,4-hexafluoro-2-butene from the alkene and alkyne intermediates.Type: ApplicationFiled: May 19, 2011Publication date: November 24, 2011Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Andrew Joseph Poss, David Nalewajek, Michael Van Der Puy, Haridasan K. Nair
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Patent number: 8058489Abstract: A process is disclosed for making CF3CF?CHF or mixtures thereof with CF2?CFCHF2.Type: GrantFiled: November 15, 2007Date of Patent: November 15, 2011Assignee: E.I. du Pont de Nemours and CompanyInventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
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Patent number: 8053611Abstract: A process is disclosed for the manufacture of 1,1,1,3,3,3-hexafluoropropane and 1,1,1,2,3,3-hexafluoropropane, hexafluoropropene and/or 1,1,1,2,3,3,3-heptafluoropropane. The process involves (a) reacting HF, Cl2, and at least one halopropene of the formula CX3CCl?CClX (where each X is independently F or Cl) to produce a product comprising CF3CCl2CF3 and CF3CClFCClF2; (b) reacting CF3CCl2CF3 and CF3CClFCClF2 produced in (a) with hydrogen, optionally in the presence of HF, to produce a product comprising CF3CH2CF3 and at least one of CHF2CHFCF3, CF3CF?CF2 and CF3CFHCF3; and (c) recovering from the product produced in (b), CF3CH2CF3 and at least one of CHF2CHFCF3, CF3CF?CF2 and CF3CFHCF3. In (a), the CF3CCl2CF3 and CF3CClFCClF2 are produced in the presence of a chlorofluorination catalyst including (i) a crystalline alpha-chromium oxide where at least 0.Type: GrantFiled: August 4, 2006Date of Patent: November 8, 2011Assignee: E. I. du Pont de Nemours and CompanyInventors: Velliyur Nott Mallikarjuna Rao, H. David Rosenfeld, Allen Capron Sievert, Shekhar Subramoney
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Patent number: 8053613Abstract: A process is disclosed for making CH2ClCF2CClF2. The process involves reacting CH2ClF with CClF?CF2 in an addition reaction zone in the presence of an aluminum halide composition having a bulk formula of AlClxBryF3-x-y wherein the average value of x is 0 to 3, the average value of y is 0 to 3?x, provided that the average values of x and y are not both 0. Also disclosed is a process for making CH2FCF2CF3 that involves reacting the CH2ClCF2CClF2 with HF in a fluorination reaction zone in the presence of a fluorination catalyst. Also disclosed is a process for making CHF?CFCF3 that involves dehydrofluorinating the CH2FCF2CF3.Type: GrantFiled: September 5, 2007Date of Patent: November 8, 2011Assignee: E.I. du Pont de Nemours and CompanyInventor: Allen Capron Sievert
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Publication number: 20110270000Abstract: The current invention relates to a process for making a tetrafluoropropene using a tetrafluorochloropropane and/or a pentafluoropropane as starting or intermediate reagents. More specifically, though not exclusively, the present invention relates to a novel method for preparing a tetrafluoropropene by dehydrohalogenating a starting or intermediate tetrafluorochloropropane and/or pentafluoropropane material in the presence of a caustic solution at a temperature range greater than 40° C. and less than or equal to 80° C.Type: ApplicationFiled: March 28, 2011Publication date: November 3, 2011Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Selma Bektesevic, Hsueh S. Tung, Haiyou Wang, Daniel C. Merkel, Robert C. Johnson
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Publication number: 20110251442Abstract: To provide a simple and economical process for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene, which does not require purification of the raw material component obtained in the form of a mixture of isomers, and a process for producing 2,3,3,3-tetrafluoropropene from the product thereby obtained. A process for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene, characterized by bringing a mixture of dichloropentafluoropropane isomers which contains 1,1-dichloro-2,2,3,3,3-pentafluoropropane into contact with an aqueous alkali solution in the presence of a phase transfer catalyst, and thereby selectively dehydrofluorinating only the 1,1-dichloro-2,2,3,3,3-pentafluoropropane in the mixture, and a process for producing 2,3,3,3-tetrafluoropropene from the 1,1-dichloro-2,3,3,3-tetrafluoropropene thereby obtained.Type: ApplicationFiled: June 20, 2011Publication date: October 13, 2011Applicant: ASAHI GLASS COMPANY, LIMITEDInventors: Hidekazu OKAMOTO, Yasuyuki SASAO
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Patent number: 8034984Abstract: 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: September 22, 2010Date of Patent: October 11, 2011Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Rajiv R. Singh, Hsueh S. Tung
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Publication number: 20110245548Abstract: The present invention achieves a catalyst life improvement for the catalyzed vapor phase fluorination of a chlorocarbon in the presence of one catalyst and an oxygen feed. Specifically, in one non-limiting embodiment, the instant invention provides the conversion of 1,1,2,3-tetrachloropropene and/or 1,1,1,2,3-pentachloropropane to 2-chloro-3,3,3-trifluoropropene by introduction of a catalyst and oxygen co-feed to the fluorination reactor.Type: ApplicationFiled: March 8, 2011Publication date: October 6, 2011Applicant: HONEYWELL INTERNATIONAL INC.Inventors: DANIEL C. MERKEL, KONSTANTIN A. POKROVSKI, HSUEH S. TUNG
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Publication number: 20110245549Abstract: The disclosed integrated manufacturing process includes a combined liquid phase reaction and purification operation which directly produces trans-1-chloro-3,3,3-trifluoropropene and 3-chloro-1,1,1,3-tetrafluoropropane which is a precursor to the manufacture of trans-1,3,3,3-tetrafluoropropene. The mixture of co-products is easily separated by conventional distillation and 3-chloro-1,1,1,3-tetrafluoropropane is then dehydrochlorinated to produce trans-1,3,3,3-tetrafluoropropene by contacting in the liquid phase with a caustic solution or in the vapor phase using a dehydrochlorination catalyst.Type: ApplicationFiled: April 5, 2010Publication date: October 6, 2011Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Daniel C. Merkel, Robert Johnson, Hsueh Sung Tung, Haiyou Wang, Konstantin A. Pokrovski
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Publication number: 20110237843Abstract: Hexafluoro-2-butene (HFO-1336) is a low global warming potential blowing agent, refrigerant and solvent. This invention provides methods for making the compound, including the cis-isomer, from the readily available raw materials, carbon tetrachloride and ethylene. The trans-isomer formed in the process can be isomerized into cis-isomer by the use of an isomerization catalyst.Type: ApplicationFiled: March 11, 2011Publication date: September 29, 2011Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Hsueh Sung Tung, Haiyou Wang
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Publication number: 20110237845Abstract: A process is disclosed for making CF3CF?CHF. The process involves contacting at least one hexafluoropropane selected from the group consisting of CF3CF2CH2F and CF3CHFCHF2 with a chromium oxyfluoride catalyst in a reactor to obtain a product mixture comprising CF3CF?CHF, and recovering CF3CF?CHF from the product mixture. A process is disclosed for making CF3CH?CHF. The process involves contacting CF3CH2CHF2 with a chromium oxyfluoride catalyst in a reactor to obtain a product mixture comprising CF3CH?CHF, and recovering CF3CH?CHF from the product mixture. A process is disclosed for making CF3CF?CH2. The process involves contacting CF3CF2CH3 with a chromium oxyfluoride catalyst in a reactor to obtain a product mixture comprising CF3CF?CH2, and recovering CF3CF?CH2 from the product mixture.Type: ApplicationFiled: June 3, 2011Publication date: September 29, 2011Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: MARIO Joseph NAPPA, Velliyur Nott Mallikarjuna Rao
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Publication number: 20110237844Abstract: Hexafluoro-2-butene (HFO-1336) is a low global warming potential blowing agent, refrigerant and solvent. This invention provides a method for making the compound, including the cis-isomer, from the readily available raw materials, carbon tetrachloride and 3,3,3-trifluoropropene. The trans-isomer formed in the process can be isomerized into cis-isomer by the use of an isomerization catalyst.Type: ApplicationFiled: March 11, 2011Publication date: September 29, 2011Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Hsueh Sung Tung, Haiyou Wang
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Publication number: 20110224465Abstract: This invention achieves a catalyst life improvement for the catalyzed vapor phase reaction of 1,1,1,3,3-pentachloropropane with hydrogen fluoride to form 1-chloro-3,3,3-trifluoropropene by introducing an oxygen co-feed into the fluorination reactor. By introduction of an oxygen co-feed to the reactor feed, the catalyst life was extended a minimum of two-fold (2×).Type: ApplicationFiled: March 10, 2010Publication date: September 15, 2011Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung
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Patent number: 8017817Abstract: A process for the manufacture of CF3CH?CF2 and CF3CF?CHF is disclosed. The process involves (a) reacting HF and chlorine and at least one halopropene of the formula CX3CCI?CCIX (where each X is independently F or Cl) to produce a product including both CF3CCI2CF3 and CF3CCIFCCIF2; (b) reacting CF3CCI2CF3 and CF3CCIFCCIF2 produced in (a) with hydrogen to produce a product including both CF3CH2CF3 and CF3CHFCHF2; (c) dehydrofluorinating CF3CH2CF3 and CF3CHFCHF2 produced in (b) to produce a product including both CF3CH?CF2 and CF3CF?CHF; and (d) recovering CF3CH?CF2 and CF3CF?CHF from the product produced in (c). In (a), both CF3CCI2CF3 and CF3CCIFCCIF2 are produced in the presence of a chlorofluorination catalyst consisting of (i) compositions comprising a crystalline alpha-chromium oxide where at least 0.05 atom % of the chromium atoms in the alpha-chromium oxide lattice are replaced by copper, and (H) compositions of (i) which have been treated with a fluorinating agent.Type: GrantFiled: August 4, 2006Date of Patent: September 13, 2011Assignee: E.I. du Pont de Nemours and CompanyInventors: Velliyur Nott Mallikarjuna Rao, H. David Rosenfeld, Allen Capron Sievert, Shekhar Subramoney
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Publication number: 20110215273Abstract: A hydrofluoroolefin and hydrofluoroolefin isomers and a process for manufacture them comprising eliminating HF from a fluorinated precursor compound are described. The fluorinated precursor compound may be provided by fluorinating a chlorinated precursor. The fluorinated precursor compound may be a fluorinated alkane. The hydroolefines are suitable as blowing agents, heat transfer fluids, or drying agents or degreasing solvents.Type: ApplicationFiled: November 13, 2009Publication date: September 8, 2011Applicant: SOLVAY FLUOR GMBHInventors: Ercan Uenveren, Johannes Eicher, Wolfgang Kalbreyer
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Patent number: 8013194Abstract: A method for producing 1,1,1,2-tetrafluoropropene and/or 1,1,1,2,3-pentafluoropropene using a single set of four unit operations, the unit operations being (1) hydrogenation of a starting material comprising hexafluoropropene and optionally recycled 1,1,1,2,3-pentafluoropropene; (2) separation of the desired intermediate hydrofluoroalkane, such as 1,1,1,2,3,3-hexafluoropropane and/or 1,1,1,2,3-pentafluoropropane; (3) dehydrofluorination of the intermediate hydrofluoroalkane to produce the desired 1,1,1,2-tetrafluoropropene and/or 1,1,1,2,3-pentafluoropropene, followed by another separation to isolate the desired product and, optionally, recycle of the 1,1,1,2,3-pentafluoropropene.Type: GrantFiled: March 11, 2009Date of Patent: September 6, 2011Assignee: Honeywell International Inc.Inventors: Yuon Chiu, Stephen A. Cottrell, Hsueh Sung Tung, Haluk Kopkalli, Gustavo Cerri
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Publication number: 20110207974Abstract: 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: ApplicationFiled: May 14, 2009Publication date: August 25, 2011Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Haluk Kopkalli, Yuon Chiu, Hsueh Sung Tung
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Patent number: 7981312Abstract: A process is disclosed for making CF3CF?CH2 or mixtures thereof with CHF?CFCHF2. The process involves contacting CCl3CF2CF3 and optionally CCl2FCF2CClF2 with H2 in the presence of a palladium catalyst supported on a support of alumina, fluorided alumina and/or aluminum fluoride, to produce a product mixture including CH2?CFCF3 (and when CCl2FCF2CClF2 is present, CHF?CFCHF2); recovering CH2?CFCF3 or a mixture thereof with CHF?CFCHF2 from the product mixture. The present invention also provides another process that involves reacting CCl3CF2CF3 and optionally CCl2FCF2CClF2 with H2 in the presence of a hydrogenation catalyst to form CH3CF2CF3 (and when CCl2FCF2CClF2 is present, CH2FCF2CHF2); dehydrofluorinating; and recovering CH2?CFCF3 or a mixture thereof with CHF?CFCHF2.Type: GrantFiled: October 31, 2007Date of Patent: July 19, 2011Assignee: E. I. du Pont de Nemours and CompanyInventors: Mario Joseph Nappa, Velliyur Mallikarjuna Nott Rao, Allen Capron Sievert
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Patent number: 7982073Abstract: A process is disclosed for making CF3CF?CHF. The process involves contacting at least one hexafluoropropane selected from the group consisting of CF3CF2CH2F and CF3CHFCHF2 with a chromium oxyfluoride catalyst in a reactor to obtain a product mixture comprising CF3CF?CHF, and recovering CF3CF?CHF from the product mixture. A process is disclosed for making CF3CH?CHF. The process involves contacting CF3CH2CHF2 with a chromium oxyfluoride catalyst in a reactor to obtain a product mixture comprising CF3CH?CHF, and recovering CF3CH?CHF from the product mixture. A process is disclosed for making CF3CF?CH2. The process involves contacting CF3CF2CH3 with a chromium oxyfluoride catalyst in a reactor to obtain a product mixture comprising CF3CF?CH2, and recovering CF3CF?CH2 from the product mixture.Type: GrantFiled: July 11, 2007Date of Patent: July 19, 2011Assignee: E. I. du Pont de Nemours and CompanyInventors: Mario Joseph Nappa, Velliyur Nott Mallikarjuna Rao
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Publication number: 20110172470Abstract: There is provided according to the present invention a process for producing 1-chloro-3,3,3-trifluoropropene or 1,3,3,3-tetrafluoropropene, including: reacting 1,1,1,3,3-pentafluoropropane with hydrogen chloride in a gas phase in the presence of a solid catalyst. By the use of a specific solid catalyst such as a catalyst in which chromium is supported on alumina or activated carbon or an alumina catalyst, the 1-chloro-3,3,3-trifluoropropene or 1,3,3,3-tetrafluoropropene can be obtained with high yield from the 1,1,1,3,3-pentafluoropropane, which can be commercially available or prepared on an industrial scale.Type: ApplicationFiled: September 4, 2009Publication date: July 14, 2011Applicant: Central Glass Company, LimitedInventors: Hideo Hamasaki, Yasuo Hibino
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Publication number: 20110163253Abstract: A process for making CHF?CFCF3 is disclosed. The process involves (a) reacting CCl2FCF2CF3 with H2 in the presence of a catalytically effective amount of hydrogenation catalyst to form CH2FCF2CF3; and (b) dehydrofluorinating CH2FCF2CF3 from (a) to form CHF?CFCF3. Also disclosed are compositions including CCl3CF2CF3 and HF, wherein the HF is present in an effective amount to form an azeotropic combination with the CCl3CF2CF3; and compositions including CCl2FCF2CF3 and HF, wherein the HF is present in an effective amount to form an azeotropic combination with the CCl2FCF2CF3.Type: ApplicationFiled: March 14, 2011Publication date: July 7, 2011Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventor: ALLEN CAPRON SIEVERT
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Patent number: 7973202Abstract: The present invention aims to reduce an amount of by-products generated in a reaction step for obtaining fluorine-containing olefin, and thereby to obtain fluorine-containing olefin as a target substance with a higher selectivity than that in the conventional method. In a reaction step for generating fluorine-containing olefin by a dehydrohalogenation reaction from fluorine-containing halogenated propane expressed by a general formula CF3CH(2-n)XnCH(3-m)Xm (wherein n=0, 1 or 2; m=1, 2 or 3; and n+m?3; and X is selected from F, Cl and Br, independently), fluorochromium oxide having a fluorine content not less than 30% by weight is used as a catalyst.Type: GrantFiled: November 11, 2008Date of Patent: July 5, 2011Assignee: Daikin Industries, Ltd.Inventors: Kazuhiro Takahashi, Masatoshi Nose, Takehiro Chaki
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Publication number: 20110160498Abstract: The subject of the invention is a process for the preparation of 2,3-dichloro-1,1,1-trifluoropropane by chlorination of 3,3,3-trifluoropropene at a pressure greater than 2 bar. Application in the synthesis of 1234yf.Type: ApplicationFiled: September 11, 2009Publication date: June 30, 2011Inventors: Anne Pigamo, Michel Devic, Laurent Wendlinger
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Publication number: 20110160499Abstract: The invention provides a process for preparing 1234yf, comprising: (i) contacting 243db with hydrogen fluoride HF in gas phase in the presence of a fluorination catalyst under conditions sufficient to produce a reaction mixture; (ii) separating the reaction mixture into a first stream comprising HCl, 1234yf and a second stream comprising HF, 1233xf and 245cb; (iii) recycling at least a part of the second stream at least in part back to step (i).Type: ApplicationFiled: December 23, 2010Publication date: June 30, 2011Applicant: Arkema FranceInventors: Laurent Wendlinger, Anne Pigamo, Dominique Deur-Bert
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Patent number: 7964759Abstract: Disclosed is a method for producing 3,3,3-trifluoropropyne, which is characterized in that a base is reacted with (Z)-1-halogeno-3,3,3-trifluoropropene represented by formula [1]. It is possible by this production method to obtain 3,3,3-trifluoropropyne with high yield. Furthermore, since waste disposal is also easy, it is a production method that is industrially advantageous.Type: GrantFiled: April 4, 2008Date of Patent: June 21, 2011Assignee: Central Glass Company, LimitedInventors: Akira Ishihara, Yasuo Hibino
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Patent number: 7951981Abstract: A process for producing a perfluoroalkyne compound includes an addition reaction step of adding Cl2, Br2, or I2 to a compound shown by the formula (1) CH3C?CR1 to obtain a compound shown by the formula (2) CH3CX2CX2R1, a fluorination reaction step of reacting the compound shown by the formula (2) with fluorine gas to obtain a compound shown by the formula (3) CF3CX2CX2R2, and a dehalogenation reaction step of contacting the compound shown by the formula (3) with a metal or an organometallic compound to obtain a perfluoroalkyne compound shown by the formula (4) CF3C?CR2. According to the present invention, a perfluoroalkyne compound can be produced at high productivity and high yield using starting raw materials which are environmentally friendly and industrially available. In the above formulas, R1 represents a methyl group or an ethyl group, X represents Cl, Br, or I, and R2 represents a trifluoromethyl group or a pentafluoroethyl group.Type: GrantFiled: March 30, 2007Date of Patent: May 31, 2011Assignee: Zeon CorporationInventor: Tatsuya Sugimoto
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Publication number: 20110124930Abstract: The present invention provides a process for its preparation comprising (a) converting 1,1,1-trifluoro-2,3-dichloropropane (243db) to 3,3,3-trifluoro-2-chloro-prop-1-ene (CF3CCI?CH2) in the presence of a first catalyst in a first reactor, (b) contacting CF3CCI?CH2 with a fluorinating agent in the presence of a second catalyst in a second reactor to produce a compound of formula CF3CFXCH3, wherein X?Cl or F, and (c) dehydrohalogenating the compound of formula CF3CFXCH3 to produce 2,3,3,3-tetrafluoropropene (1234yf).Type: ApplicationFiled: April 9, 2009Publication date: May 26, 2011Inventors: John W. Smith, Claire Mcguiness, Andrew P. Sharratt
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Publication number: 20110112339Abstract: The present disclosure provides methods for pre-treating activated carbon before it is used in a dehydrochlorination process. The methods can comprise mixing the activated carbon with an acid, an oxidizing agent in a liquid phase, or an oxidizing agent in a gas phase. Activated carbons undergoing one or more of these methods can exhibit improved stability during the dehydrochlorination process.Type: ApplicationFiled: January 14, 2011Publication date: May 12, 2011Applicant: HONEYWELL INTERNATIONAL INC.Inventors: HAIYOU WANG, HSUEH SUNG TUNG
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Publication number: 20110077435Abstract: A polyfluoro-1-alkene represented by the general formula: CF3(CF2)nCH2(CF2)mCH?CH2[I], wherein n is an integer of 0 to 5, and m is an integer of 1 to 7, is produced by reacting a polyfluoroalkyl iodide represented by the general formula: CF3(CF2)nCH2(CF2)m(CH2CH2)I [II], wherein n is an integer of 0 to 5, and m is an integer of 1 to 7, with an inorganic basic compound in the presence of a phase transfer catalyst. Alternatively, the polyfluoro-1-alkene is produced by reacting the polyfluoroalkyl iodide [II] with a nitrogen-containing organic basic compound, and is obtained product [I] as one fraction thereof. By the copolymerization of the polyfluoro-1-alkene with other fluorinated olefin monomers, a fluorine-containing copolymer having excellent light transmittance in the visible light range is formed.Type: ApplicationFiled: June 12, 2009Publication date: March 31, 2011Applicant: UNIMATEC CO., LTD.Inventors: Katsuyuki Sato, Seiichiro Murata, Akihiko Ikeda, Yoshiyama Kaneumi