Catalyst Utilized Patents (Class 570/156)
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Patent number: 8829254Abstract: The present invention describes a process for making CF3CH?CHF (HFO-1234ze). The process involves the addition of carbon tetrachloride (CCl4) to 1,2-dichloroethylene to form CCl3CHClCHCl2. The compound CCl3CHClCHCl2 thus can then either be treated with HF to produce CF3CHClCHClF as the main product, or it can be converted to CCl2?CHCHCl2 (1230za) by dechlorination. CCl2?CHCHCl2 can be treated with HF such that the main product obtained is CF3CHClCHClF. CF3CH?CHCl may be produced as a by-product, but upon treatment with HF, it affords the compound CF3CHClCHClF. The desired compound, CF3CH?CHF (HFO-1234ze), is obtained as a trans/cis mixture by dehydrochlorination of CF3CH2CHClF or by dechlorination of CF3CHClCHClF.Type: GrantFiled: February 4, 2013Date of Patent: September 9, 2014Assignee: Honeywell International Inc.Inventors: Haridasan K. Nair, Rajiv Ratna Singh, David Nalewajek, Andrew Joseph Poss
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Publication number: 20140249336Abstract: This invention provides a process for producing 2-chloro-3,3,3-trifluoropropene, comprising: reacting anhydrous hydrogen fluoride with at least one chlorine-containing compound selected from the group consisting of chloropropanes and chloropropenes represented by specific formulas in a gas phase in the presence of a chromium atom-containing fluorination catalyst while heating, the reaction being carried out in the presence of molecular chlorine or with a water content in the reaction system of 300 ppm or less. This invention enables suppression of catalyst deterioration and efficient production of 2-chloro-3,3,3-trifluoropropene in a simple and economically advantageous manner on an industrial scale.Type: ApplicationFiled: October 23, 2012Publication date: September 4, 2014Inventors: Yuzo Komatsu, Masayuki Kishimoto
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Patent number: 8822740Abstract: The invention relates to a process for preparing 2,3,3,3-tetrafluoropropene (CF3CF?CH2), performed using the steps of dehydrohalogenating 1,1,1,2,2-pentafluoropropane (CH3CF2CF3, HFC-245ca) 1,1,1,2-tetrafluoro-2-chloropropane, 1,1,1,2,3-pentafluoropropane (CH2FCHFCF3, HFC-245eb) and/or 1,1,1,2-tetrafluoro-3-chloropropane in the presence of a base, and converting a trifluorodichloropropane or a difluorotrichloropropane or a fluorotetrachloropropane to CH3CF2CF3, 1,1,1,2-tetrafluoro-2-chloropropane, CH2FCHFCF3, and/or 1,1,1,2-tetrafluoro-3-chloropropane.Type: GrantFiled: June 13, 2013Date of Patent: September 2, 2014Assignee: Mexichem Amanco Holding S.A. de C.V.Inventors: Andrew Paul Sharratt, Robert Elliott Low, John Charles McCarthy
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Patent number: 8816140Abstract: The present invention provides a process for producing a fluorine-containing alkene of the general formula CF3(CX2)nCF?CH2, wherein X each independently represents F or Cl, and n is an integer of 0 to 2. The process includes a first reaction step of allowing a specific chlorine-containing compound to react with a fluorinating agent under increased pressure in a gas phase in the presence of at least one fluorination catalyst selected from the group consisting of chromium oxide and fluorinated chromium oxide, and a second reaction step of heating the product of the first reaction step in a gas phase under a pressure lower than the pressure in the first reaction step. The process of the present invention can produce a fluorine-containing alkene with a high selectivity with the use of a catalyst that can be easily handled, while suppressing production of by-products that cannot be easily converted into the target or separated.Type: GrantFiled: February 8, 2011Date of Patent: August 26, 2014Assignee: Daikin Industries, Ltd.Inventors: Daisuke Karube, Yuzo Komatsu, Atsushi Suzuki
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Patent number: 8791309Abstract: In accordance with the present invention, processes of synthesizing 3,3,3-trifluoropropyne from 1,3,3,3-tetrafluoropropene, 1-chloro-3,3,3-trifluoropropene, and/or 1,1,1,3,3-pentafluoropropane are provided.Type: GrantFiled: December 6, 2013Date of Patent: July 29, 2014Assignee: Honeywell International Inc.Inventors: Yian Zhai, Andrew J. Poss, Rajiv R. Singh, David Nalewajek
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Patent number: 8779218Abstract: Process of catalytic fluorination in liquid phase of product 1,1,1,2,3-pentachloropropane or/and 1,1,2,2,3-pentachloropropane into product 2-chloro-3,3,3-trifluoropropene in presence of a catalyst.Type: GrantFiled: March 21, 2011Date of Patent: July 15, 2014Assignee: Arkema FranceInventors: Anne Pigamo, Laurent Wendlinger, Philippe Bonnet
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Publication number: 20140179961Abstract: In accordance with the present invention, processes of synthesizing 3,3,3-trifluoropropyne from 1,3,3,3-tetrafluoropropene, 1-chloro-3,3,3-trifluoropropene, and/or 1,1,1,3,3-pentafluoropropane are provided.Type: ApplicationFiled: December 6, 2013Publication date: June 26, 2014Applicant: Honeywell International Inc.Inventors: Yian Zhai, Andrew J. Poss, Rajiv R. Singh, David Nalewajek
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Patent number: 8754272Abstract: Disclosed is a process for the preparation of cis-1-chloro-3,3,3-trifluoropropene (cis-1233zd) comprising the steps of (a) providing CF3CHClCHCl2 (233da), and (b) treating the 233da with a dechlorinating agent to produce a mixture of compounds including cis-1-chloro-3,3,3-trifluoropropene, preferably wherein the amount of the cis-isomer generated in the reaction is not less than 30%.Type: GrantFiled: November 12, 2012Date of Patent: June 17, 2014Assignee: Honeywell International Inc.Inventors: Yian Zhai, Andrew Joseph Poss, Michael Van Der Puy, Rajiv Ratna Singh
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Publication number: 20140155659Abstract: Process of catalytic fluorination in liquid phase of product 1,1,1,2,3-pentachloropropane or/and 1,1,2,2,3-pentachloropropane into product 2-chloro-3,3,3-trifluoropropene in presence of a catalyst.Type: ApplicationFiled: November 15, 2010Publication date: June 5, 2014Applicant: Arkema FranceInventors: Laurent Wendlinger, Anne Pigamo, Phillipe Bonnet
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Publication number: 20140114096Abstract: A vapor phase process is disclosed for making internal fluorobutenes. The process involves contacting a halobutane starting material selected from the group consisting of CF2HCHClCH2CCl2H, CF2HCHClCH2CCl3, CF3CHClCH2CCl2H, CF3CHClCH2CCl3, CF3CHClCHClCCl2H, CF3CHClCHClCCl3, CF3CCl2CH2CCl2H, CF3CCl2CH2CCl3, CF3CCl2CHClCCl2H, CF3CCl2CHClCCl3, CF3CClFCHClCCl2H, CF3CClFCHClCCl3, CF3CClFCH2CCl2H, CF3CClFCH2CCl3, CF3CClFCHFCCl2H, CF3CClFCHFCCl3, CF3CClHCHFCCl2H and CF3CClHCHFCCl3, with HF in a reaction zone in the presence of a chromium oxyfluoride catalyst to produce a product mixture comprising an internal fluorobutene. Another vapor phase process is disclosed for making internal fluoropentenes.Type: ApplicationFiled: November 7, 2011Publication date: April 24, 2014Applicant: E I DU PONT DE NEMOURS AND COMPANYInventors: Mario Joseph Nappa, Ekaterina N Swearingen
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Patent number: 8697923Abstract: The invention provides a process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) comprising (a) contacting 1,1,1-trifluoro-2,3-difluoropropane (243db) with hydrogen fluoride (HF) in the presence of a zinc/chromia catalyst to produce a compound having the formula CF3CHFCH2X, wherein X is Cl or F, and (b) dehydrohalogenating the compound of formula CF3CHFCH2X to produce 1234yf.Type: GrantFiled: August 19, 2013Date of Patent: April 15, 2014Assignee: Mexichem Amanco Holding S.A. de C.V.Inventors: John W. Smith, Claire McGuiness, Andrew P. Sharratt
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Publication number: 20140100394Abstract: Processes for the production of chlorinated propenes are provided. The present processes make use of a feedstream comprising 1,2-dichloropropane, a by-product in the production of chlorohydrin, as a low cost starting material, alone or in combination with 1,2,3-trichloropropane. Selectivity of the process is enhanced over conventional processes employing successive chlorinations and/or dehydrochlorinations, by conducting at least one chlorination in the presence of an ionic chlorination catalyst. The present processes may also generate anhydrous HCl as a byproduct that can be removed from the process and used as a feedstock for other processes, providing further time and cost savings.Type: ApplicationFiled: May 18, 2012Publication date: April 10, 2014Applicant: DOW GLOBAL TECHNOLOGIES, LLCInventors: Max M. Tirtowidjojo, William J. Kruper, JR., Barry B. Fish, David S. Laitar
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Publication number: 20140100393Abstract: The invention provides an improved process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) by reacting 2-chloro-3,3,3,-trifluoropropene (HCFO-1233xf) with hydrogen fluoride, in the presence of a fluorination catalyst, where by using 2-chloro-3,3,3,-trifluoropropene (HCFO-1233xf) of high purity, the need to add an oxidizing agent (typically chlorine) to keep the catalyst active can be avoided. The HCFC-244bb is then used as an intermediate in the production of 2,3,3,3-tetrafluoropropene-1 (HFO-1234yf).Type: ApplicationFiled: June 28, 2010Publication date: April 10, 2014Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Robert C. Johnson, Daniel C. Merkel
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Patent number: 8691720Abstract: A process for making a fluorinated olefin and/or catalyst composition. The process has the step of dehydrochlorinating a hydrochlorofluorocarbon having at least one hydrogen atom and at least one chlorine atom on adjacent carbon atoms in the presence of a catalytically effective amount of a catalyst composition. The catalyst composition is represented by the following: n wt. % MX/M?OyFz, wherein 0<y<1 and 0<z<2 and wherein y+z/2=1; M is an alkali metal ion selected from the group consisting of Li+, Na+, K+, Rb+, and Cs+; X is a halogen ion selected from the group consisting of F?, Cl?, Br?, and I?, M? is a bivalent metal ion; wherein n is a weight percentage of about 0.05% to about 50% MX based on the total weight of the MX and M?OyFz, and wherein y and z are the mole fractions of oxygen and fluorine in M?OyFz, respectively.Type: GrantFiled: October 12, 2011Date of Patent: April 8, 2014Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Hsueh Sung Tung
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Publication number: 20140066670Abstract: Disclosed is a reactor and agitator useful in a high pressure process for making 1-chloro-3,3,3-trifluoropropene (1233zd) from the reaction of 1,1,1,3,3-pentachloropropane (240fa) and HF, wherein the agitator includes one or more of the following design improvements: (a) double mechanical seals with an inert barrier fluid or a single seal; (b) ceramics on the rotating faces of the seal; (c) ceramics on the static faces of seal; (d) wetted o-rings constructed of spring-energized Teflon and PTFE wedge or dynamic o-ring designs; and (e) wetted metal surfaces of the agitator constructed of a corrosion resistant alloy.Type: ApplicationFiled: March 14, 2013Publication date: March 6, 2014Applicant: HONEYWELL INTERNATIONAL INC.Inventor: Stephen A. Cottrell
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Patent number: 8664455Abstract: The invention provides an improved process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) by reacting 2-chloro-3,3,3,-trifluoropropene (HCFO-1233xf) with hydrogen fluoride, in a liquid phase reaction in the presence of hydrogen chloride and a liquid phase fluorination catalyst. The hydrogen chloride is added into the reaction from an external source at a pressure of about 100 psig or more. The HCFC-244bb is an intermediate in the production of 2,3,3,3-tetrafluoropropene-1 (HFO-1234yf).Type: GrantFiled: July 30, 2009Date of Patent: March 4, 2014Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Stephen A. Cottrell, Robert C. Johnson
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Patent number: 8664457Abstract: A production method of 3,3,3-trifluoropropene includes the step of hydrogenating 1-chloro-3,3,3-trifluoropropene with hydrogen (H2) in a gas phase in the presence of either of: (A) a catalyst having carried on a carrier at least one kind of transition metal selected from the group consisting of ruthenium, nickel, rhodium, iridium, iron, osmium and cobalt, or an oxide of said transition metal; (B) an oxide catalyst of copper and manganese; and (C) a catalyst having carried on a carrier palladium and at least one kind of element selected from the group consisting of bismuth, zinc, copper, silver, lanthanum, lead, zirconium, niobium, hafnium, magnesium, tin and arsenic.Type: GrantFiled: January 18, 2011Date of Patent: March 4, 2014Assignee: Central Glass Company, LimitedInventors: Fuyuhiko Sakyu, Yasuo Hibino
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Patent number: 8664456Abstract: Disclosed is an integrated process to co-produce trans-1-chloro-3,3,3-trifluoro-propene (1233zd (E)), trans-1,3,3,3-tetrafluoropropene (1234ze (E)), and 1,1,1,3,3-pentafluoropropane (245fa). Overall the co-production is a three-step process. The chemistry involves the steps of: (1) the reaction of 1,1,1,3-tetrachloropropene and/or 1,1,3,3-tetrachloropropene with anhydrous HF in excess in a liquid-phase catalyzed reactor in such a way as to co-produce primarily 1233zd (E) and 244fa (plus by-product HCl); an optionally (2) the 244fa stream can then be used to directly produce any (or all) of the following desired products; (a) the 244fa stream can be dehydrochlorinated to produce the desired second product 1234ze (E); and/or (b) the 244fa stream can be dehydrofluorinated to produce 1233zd (E) if more of that product is desired; and/or (c) the 244fa stream can be further fluorinated to form 245fa.Type: GrantFiled: March 28, 2012Date of Patent: March 4, 2014Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung
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Patent number: 8653309Abstract: Trans-1233zd, the trans-isomer of 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) can be used as blowing agents, solvents, cleaning agents, as well as monomers of macromolecule compounds, and can be prepared through the dehydrochlorination of 1,1,1-trifluoro-3,3-dichloropropane (HCFC-243fa) with the help of a catalyst. The present invention is directed to an integrated process is proposed to produce trans-1233zd from 243fa, which is consisted of the following four major unit operations: (1) Catalytic dehydrochlorination of 243fa into trans/cis-1233zd, (2) HCl recovery, (3) Catalytic isomerization of cis-1233zd into trans-1233zzd, and (4) Isolation of trans-1233zd.Type: GrantFiled: April 20, 2011Date of Patent: February 18, 2014Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Hsueh Sung Tung
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Patent number: 8648221Abstract: Disclosed is an integrated process to co-produce trans-1-chloro-3,3,3-trifluoro-propene (1233zd(E)), trans-1,3,3,3-tetrafluoropropene (1234ze(E)), and 1,1,1,3,3-pentafluoropropane (245fa). Overall the co-production is a three-step process. The chemistry involves the steps of: (1) the reaction of 240fa with anhydrous HF in excess in a liquid-phase catalyzed reactor in such a way as to co-produce primarily 1233zd(E) and 244fa (plus byproduct HCl); (2) the 244fa stream can then be used to directly produce any of the three desired products; (3a) the 244fa stream can be dehydrochlorinated to produce the desired second product 1234ze(E); and/or (3b) the 244fa stream can be dehydrofluorinated to produce 1233zd(E) if more of that product is desired; and/or (3c) the 244fa stream can be further fluorinated to form 245fa.Type: GrantFiled: December 9, 2011Date of Patent: February 11, 2014Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Haiyou Wang, Konstantin A. Pokrovski, Hsueh Sung Tung, Ian Shankland
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Patent number: 8642820Abstract: 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: GrantFiled: June 23, 2011Date of Patent: February 4, 2014Assignee: Asahi Glass Company, LimitedInventors: Ryuji Seki, Hidekazu Okamoto, Hirokazu Takagi, Satoshi Kawaguchi
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Publication number: 20140031595Abstract: The present invention provides continuous, gas phase, free radical processes for the production of chlorinated and/or fluorinated propenes or higher alkenes from the reaction of chlorinated and/or fluorinated alkanes and chlorinated and/or fluorinated alkenes, wherein wherein at least a portion of any intermediate boiler by-products generated by the process are removed from the processType: ApplicationFiled: October 4, 2013Publication date: January 30, 2014Applicant: DOW GLOBAL TECHNOLOGIES, LLCInventors: Max Markus Tirtowidjojo, Patrick Ho-Sing Au-Yeung, Debashis Chakraborty, Juergen Eiffler, Heinz Groenewald, Kurt Frederick Hirsekorn, Manfred Kokott, William J. Kruper, JR., Thomas Ulrich Luebbe, Holger Meeman, Shirley Shaw Sexton, Peter Wenzel, Marcus Wobser
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Patent number: 8633340Abstract: The invention provides a process for preparing 1,1,1-trifluoro-2,3-dichloropropane (243db), which process comprises contacting 3,3,3-trifluoropropene (1243zf) with chlorine in the presence of a catalyst, wherein the catalyst comprises activated carbon, alumina and/or an oxide of a transition metal.Type: GrantFiled: April 9, 2009Date of Patent: January 21, 2014Assignee: Mexichem Amanco Holding S.A. de C.V.Inventors: John W. Smith, Claire McGuiness, Andrew P. Sharratt
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Patent number: 8629307Abstract: The invention provides a process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) comprising (a) contacting 1,1,1-trifluoro-2,3-difluoropropane (243db) with hydrogen fluoride (HF) in the presence of a zinc/chromia catalyst to produce a compound having the formula CF3CHFCH2X, wherein X is Cl or F, and (b) dehydrohalogenating the compound of formula CF3CHFCH2X to produce 1234yf.Type: GrantFiled: December 12, 2012Date of Patent: January 14, 2014Assignee: Mexichem Amanco S.A. de C.V.Inventors: John W. Smith, Claire McGuiness, Andrew P. Sharratt
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Publication number: 20140012048Abstract: A dehydrochlorination process is disclosed. The process involves contacting RfCHClCH2Cl with a carbon catalyst in a reaction zone to produce a product mixture comprising RfCCl?CH2, wherein Rf is a perfluorinated alkyl group.Type: ApplicationFiled: February 16, 2012Publication date: January 9, 2014Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: Xuehui Sun, Mario Joseph Nappa
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Publication number: 20140012049Abstract: Disclosed are processes for producing halogenated olefins, and preferably tetrafluorinated propene(s), from one or more alkanes having both fluorine substituents and non-fluorine substituents, preferably with a high degree of conversion and selectivity. Preferably the process comprises the use of a catalyzed reaction in which the catalyst is selected from the group consisting of activated carbons, halogentated mono- and di-valent metal oxides, mono- and di-valent Lewis acid metal halides, zero-valent metals, and combinations of these.Type: ApplicationFiled: August 16, 2013Publication date: January 9, 2014Applicant: HONEYWELL INTERNATIONAL INC.Inventors: HAIYOU WANG, HSUEH SUNG TUNG, SUDIP MUKHOPADHYAY
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Publication number: 20140005447Abstract: A production method of 1-chloro-3,3,3-trifluoropropene according to the present invention includes bringing a raw material composition containing 1,3,3,3-tetrafluoropropene and an acid composition containing hydrogen chloride into contact with each other in gas phase in the presence of a catalyst. This production method allows not only use of hydrogen chloride containing hydrogen fluoride, which has been generated during a preceding step (production of 1,1,1,3,3-pentafluoropropane as a raw material or analogues thereof), but also use of any of trans and cis isomers of the 1,1,1,3,3-pentafluoropropane for production of the 1-chloro-3,3,3-trifluoropropene. It is thus possible to efficiently produce the 1-chloro-3,3,3-trifluoropropene, which is known as an environment-adaptive chlorofluorocarbon. As the catalyst, preferred is an alumina catalyst treated by contact with hydrogen fluoride.Type: ApplicationFiled: June 27, 2013Publication date: January 2, 2014Applicant: Central Glass Company, LimitedInventors: Masamune OKAMOTO, Hideaki IMURA, Naoto TAKADA
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Patent number: 8614361Abstract: The present invention provides an effective, selective, and industrially applicable process for producing 2,3,3,3-tetrafluoropropene. Specifically, the present invention provides a process for producing 2,3,3,3-tetrafluoropropene including reacting 2-chloro-3,3,3-trifluoropropene with hydrogen fluoride in the presence of oxygen and a catalyst comprising chromium oxide represented by the composition formula: CrOm (1.5<m<3), or fluorinated chromium oxide obtained by fluorinating the chromium oxide.Type: GrantFiled: April 22, 2010Date of Patent: December 24, 2013Assignee: Daikin Industries, Ltd.Inventors: Atsushi Suzuki, Masatoshi Nose, Tsuneo Yamashita
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Patent number: 8609908Abstract: To provide a process for producing, at a high content ratio, 1,1-dichloro-2,2,3,3,3-pentafluoropropane (HCFC-225ca) which is useful as e.g. a starting material to obtain 1,1-dichloro-2,3,3,3-tetrafluoropropene (CFO1214ya). The process for producing HCFC-225ca of the present invention comprises subjecting a raw material composed of dichloropentafluoropropane (HCFC-225) including 2,2-dichloro-1,1,1,3,3-pentafluoropropane (HCFC225aa) to an isomerization reaction at a temperature of at most 290° C. in a gas phase in the presence of a metal oxide catalyst thereby to isomerize HCFC-225aa to HCFC-225ca.Type: GrantFiled: June 23, 2011Date of Patent: December 17, 2013Assignee: Asahi Glass Company, LimitedInventor: Hidekazu Okamoto
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Patent number: 8609907Abstract: One or more hydrochlorofluoroalkenes can be produced by dehydrofluorination of a hydrochlorofluoroalkane over a X-ray amorphous high surface metal fluoride or a X-ray amorphous or weakly crystalline metal oxide fluoride wherein the metal is selected from the 2nd, 3rd or 4th main group or any subgroup of the periodic system of elements. High-surface aluminum fluoride or aluminum oxide fluoride are especially suitable as catalysts. For example, CF3CH2CHClF is reacted to produce CF3CH?CHCl, and CF3CH2CClFCH3 is reacted to form CF3CH2CCl?CH2 and/or CF3CH?CClCH3.Type: GrantFiled: November 20, 2009Date of Patent: December 17, 2013Assignee: Solvay Fluor GmbHInventors: Johannes Eicher, Wolfgang Kalbreyer, Ercan Uenveren
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Patent number: 8604257Abstract: 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: GrantFiled: May 19, 2011Date of Patent: December 10, 2013Assignee: 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: 20130267740Abstract: The present invention provides a process for preparing 2,3,3,3-tetrafluoropropene, comprising the following steps: (a) catalytic reaction of 1,1,1,2,3-pentachloropropane and/or 1,1,2,2,3-pentachloropropane with HF into product 2-chloro-3,3,3-trifluoropropene; (b) catalytic reaction of the thus-obtained 2-chloro-3,3,3-trifluoropropene into 2,3,3,3-tetrafluoropropene.Type: ApplicationFiled: October 22, 2010Publication date: October 10, 2013Applicant: ARKEMA FRANCEInventors: Laurent Wendlinger, Philippe Bonnet, Anne Pigamo, Nicolas Doucet
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Patent number: 8552228Abstract: The invention provides a process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) comprising (a) contacting 1,1,1-trifluoro-2,3-difluoropropane (243db) with hydrogen fluoride (HF) in the presence of a zinc/chromia catalyst to produce a compound having the formula CF3CHFCH2X, wherein X is Cl or F, and (b) dehydrohalogenating the compound of formula CF3CHFCH2X to produce 1234yf.Type: GrantFiled: April 9, 2009Date of Patent: October 8, 2013Assignee: Mexichem Amanco Holdings S.A. de C.V.Inventors: John W. Smith, Claire McGuiness, Andrew P. Sharratt
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Publication number: 20130261354Abstract: Disclosed is an integrated process to co-produce trans-1-chloro-3,3,3-trifluoro-propene (1233zd (E)), trans-1,3,3,3-tetrafluoropropene (1234ze (E)), and 1,1,1,3,3-pentafluoropropane (245fa). Overall the co-production is a three-step process. The chemistry involves the steps of: (1) the reaction of 1,1,1,3-tetrachloropropene and/or 1,1,3,3-tetrachloropropene with anhydrous HF in excess in a liquid-phase catalyzed reactor in such a way as to co-produce primarily 1233zd (E) and 244fa (plus by-product HCl); an optionally (2) the 244fa stream can then be used to directly produce any (or all) of the following desired products; (a) the 244fa stream can be dehydrochlorinated to produce the desired second product 1234ze (E); and/or (b) the 244fa stream can be dehydrofluorinated to produce 1233zd (E) if more of that product is desired; and/or (c) the 244fa stream can be further fluorinated to form 245fa.Type: ApplicationFiled: March 28, 2012Publication date: October 3, 2013Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung
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Publication number: 20130261353Abstract: 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 starting feed material or a mixture of unsaturated hydrochloro-carbon feed materials comprising 1,1,1,3-tetrachloropropene and/or 1,1,3,3-tetrachloro-propene. The process includes a combined liquid or vapor phase reaction/purification operation which directly produces (E) 1-chloro-3,3,3-trifluoro-propene (1233zd (E)) from these feed materials, which may also include 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-tetrafluoro-propene (1234ze (E)) by contacting in the liquid phase with a caustic solution or in the vapor phase using a dehydrofluorination catalyst.Type: ApplicationFiled: March 28, 2012Publication date: October 3, 2013Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Haiyou Wang, Hsueh Sung Tung
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Patent number: 8546623Abstract: The invention relates to a process for preparing a C3-6 hydrofluoroalkene comprising dehydrohalogenating a C3-6 hydrohalofluoroalkane in the presence of a zinc/chromia catalyst.Type: GrantFiled: October 3, 2007Date of Patent: October 1, 2013Assignee: Mexichem Amanco Holding S.A. de C.V.Inventors: Andrew Paul Sharratt, Leslie Seddon
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Publication number: 20130253235Abstract: 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: May 7, 2013Publication date: September 26, 2013Applicant: HONEYWELL INTERNATIONAL INC.Inventors: ROBERT C. JOHNSON, HSUEH S. TUNG, DANIEL C. MERKEL
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Patent number: 8541634Abstract: Disclosed are azeotropic and azeotrope-like mixtures of (Z)-1-chloro-3,3,3-trifluoropropene (1233zd(Z)) and hydrogen fluoride. Such compositions are useful as an intermediate in the production of 1233zd(Z). The latter compound is useful as a nontoxic, zero ozone depleting fluorocarbon useful as a solvent, blowing agent, refrigerant, cleaning agent, aerosol propellant, heat transfer medium, dielectric, fire extinguishing composition and power cycle working fluid.Type: GrantFiled: January 14, 2013Date of Patent: September 24, 2013Assignee: Honeywell International Inc.Inventors: Ryan Hulse, Hang T Pham
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Patent number: 8536387Abstract: Process for preparing perfluoro-1,3-butadiene, comprising the following steps: A) preparation of fluoro-halo-butanes of formula: CF2YI—CFYII—CFYII—CF2YI??(V) in which YI and YII, which may be identical or different, may be H, Cl or Br, with the condition that YI and YII are not simultaneously hydrogen; starting with a chloroolefin having the formula: CY?Y?CY?Cl??(II) in which Y, Y?, Y?, which may be identical or different, are H, Cl or Br, with the condition that Y, Y?, Y? are not simultaneously hydrogen; and performing the following steps: a fluorodimerization, and a fluorination with elemental fluorine, the order of the two steps also possibly being inverted, a dehalogenation or dehydrohalogenation step being performed between the two steps, B) dehalogenation or dehydrohalogenation of the fluoro-halo compounds of formula (V) to give the compound perfluoro-1,3-butadiene.Type: GrantFiled: December 24, 2008Date of Patent: September 17, 2013Assignee: Solvay Solexis. S.p.A.Inventors: Vito Tortelli, Stefano Millefanti, Serena Carella
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Patent number: 8536388Abstract: 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: GrantFiled: April 9, 2009Date of Patent: September 17, 2013Assignee: Mexichem Amanco Holding S.A. de C.V.Inventors: John W. Smith, Claire E McGuiness, Andrew Paul Sharratt
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Patent number: 8530708Abstract: Disclosed are processes for producing halogenated olefins, and preferably tetrafluorinated propene(s), from one or more alkanes having both fluorine substituents and non-fluorine substituents, preferably with a high degree of conversion and selectivity. Preferably the process comprises the use of a catalyzed reaction in which the catalyst is selected from the group consisting of activated carbons, halogentated mono- and di-valent metal oxides, mono- and di-valent Lewis acid metal halides, zero-valent metals, and combinations of these.Type: GrantFiled: October 27, 2006Date of Patent: September 10, 2013Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Hsueh Sung Tung, Sudip Mukhopadhyay
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Patent number: 8530709Abstract: 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: GrantFiled: May 19, 2011Date of Patent: September 10, 2013Assignee: Honeywell International Inc.Inventors: Andrew Joseph Poss, David Nalewajek, Michael Van Der Puy, Haridasan K. Nair
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Patent number: 8524955Abstract: 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: GrantFiled: May 19, 2011Date of Patent: September 3, 2013Assignee: 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: 20130217928Abstract: This invention provides a process for producing 2,3,3,3-tetrafluoropropene, the process comprising: (1) a first reaction step of reacting hydrogen fluoride with at least one chlorine-containing compound selected from the group consisting of a chloropropane represented by Formula (1): CClX2CHClCH2Cl, wherein each X is the same or different and is CI or F, a chloropropene represented by Formula (2): CClY2CCl?CH2, wherein each Y is the same or different and is CI or F, and a chloropropene represented by Formula (3): CZ2?CClCH2Cl, wherein each Z is the same or different and is CI or F in a gas phase in the absence of a catalyst while heating; and (2) a second reaction step of reacting hydrogen fluoride with a reaction product obtained in the first reaction step in a gas phase in the presence of a fluorination catalyst while heating. According to the process of this invention, 2,3,3,3-tetrafluoropropene (HFO-1234yf) can be obtained with high selectivity, and catalyst deterioration can be suppressed.Type: ApplicationFiled: October 27, 2011Publication date: August 22, 2013Applicant: DAIKIN INDUSTRIES, LTD.Inventors: Kazuhiro Takahashi, Yuzo Komatsu, Akinori Ueda
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Publication number: 20130217927Abstract: The invention relates to a process for preparing 2,3,3,3-tetrafluoropropene (CF3CF?CH2), performed using the steps of dehydrohalogenating 1,1,1,2,2-pentafluoropropane (CH3CF2CF3, HFC-245ca) 1,1,1,2-tetrafluoro-2-chloropropane, 1,1,1,2,3-pentafluoropropane (CH2FCHFCF3, HFC-245eb) and/or 1,1,1,2-tetrafluoro-3-chloropropane in the presence of a base, and converting a trifluorodichloropropane or a difluorotrichloropropane or a fluorotetrachloropropane to CH3CF2CF3, 1,1,1,2-tetrafluoro-2-chloropropane, CH2FCHFCF3, and/or 1,1,1,2-tetrafluoro-3-chloropropane.Type: ApplicationFiled: April 1, 2013Publication date: August 22, 2013Applicant: MEXICHEM AMANCO HOLDING S.A. DE C.V.Inventors: Andrew Paul Sharratt, Robert Elliott Low, John Charles Mccarthy
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Patent number: 8513474Abstract: Provided are methods for producing fluorinated organic compounds, which preferably comprises converting at least one compound of formula (I) CH2XCHZCF3 to at least one compound of formula (II) CHX?CZCF3 where X and Z are independently H or F, with the proviso that X and Z are not the same. The converting step comprises catalytically reacting at least one compound of formula (I), preferably via dehydrogenation or oxidative dehydrogenation. In another aspect, the inventive method of preparing fluorinated organic compounds comprises converting a reaction stream comprising at least one pentafluoropropene to a product stream comprising at least one pentafluoropropane and at least one compound of formula (I), separating out the compound of formula (I) from the product stream, and converting the compound of formula (I) separated from the product stream to at least one compound of formula (II), wherein the conversion the compound of formula (I) to 3,3,3-trifluoropropyne is substantially limited.Type: GrantFiled: June 24, 2010Date of Patent: August 20, 2013Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Hsueh Sung Tung
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Publication number: 20130211155Abstract: The present invention describes a process for making CF3CH?CHF (HFO-1234ze). The process involves the addition of carbon tetrachloride (CCl4) to 1,2-dichloroethylene to form CCl3CHClCHCl2. The compound CCl3CHClCHCl2 thus can then either be treated with HF to produce CF3CHClCHClF as the main product, or it can be converted to CCl2?CHCHCl2 (1230za) by dechlorination. CCl2?CHCHCl2 can be treated with HF such that the main product obtained is CF3CHClCHClF. CF3CH?CHCl may be produced as a by-product, but upon treatment with HF, it affords the compound CF3CHClCHClF. The desired compound, CF3CH?CHF (HFO-1234ze), is obtained as a trans/cis mixture by dehydrochlorination of CF3CH2CHClF or by dechlorination of CF3CHClCHClF.Type: ApplicationFiled: February 4, 2013Publication date: August 15, 2013Applicant: HONEYWELL INTERNATIONAL INC.Inventor: Honeywell International Inc.
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Publication number: 20130211156Abstract: The present invention provides a simple three step process for the production of 1,3,3,3-tetrafluoropropene (HFO-1234ze). In the first step, carbon tetrachloride is added to vinyl fluoride to afford the compound CCl3CH2CHClF (HCFC-241fb). HCFC-241fb is then fluorinated with anhydrous HF to afford CF3CH2CHClF (HCFC-244fa) in the second step. Dehydrochlorination of HCFC-244fa, in the third step, affords the desired product, CF3CH?CHF (HFO-1234ze). Following similar chemistry, vinyl chloride may be used in place of vinyl fluoride.Type: ApplicationFiled: February 4, 2013Publication date: August 15, 2013Applicant: HONEYWELL INTERNATIONAL INC.Inventor: HONEYWELL INTERNATIONAL INC.
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Patent number: 8487144Abstract: 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: GrantFiled: September 4, 2009Date of Patent: July 16, 2013Assignee: Central Glass Company, Ltd.Inventors: Hideo Hamasaki, Yasuo Hibino
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Publication number: 20130150632Abstract: Disclosed is a process for the preparation of cis-1-chloro-3,3,3-trifluoropropene (cis-1233zd) comprising the steps of (a) providing CF3CHClCHCl2 (233da), and (b) treating the 233da with a dechlorinating agent to produce a mixture of compounds including cis-1-chloro-3,3,3-trifluoropropene, preferably wherein the amount of the cis-isomer generated in the reaction is not less than 30%.Type: ApplicationFiled: November 12, 2012Publication date: June 13, 2013Applicant: HONEYWELL INTERNATIONAL INC.Inventor: Honeywell International Inc.