By Dehalogenation Or Dehydrohalogenation Of Adjacent Carbon Atoms In A Compound Patents (Class 570/155)
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Patent number: 11465955Abstract: The present disclosure provides a method for producing a reaction gas containing R-1132(E) with selectivity higher than that of known methods. Specifically, the present disclosure provides a method for producing a reaction gas containing (E)-1,2-difluoroethylene (R-1132(E)), (1) the method comprising a step of subjecting a starting material gas containing one or more fluoromethanes selected from the group consisting of chlorodifluoromethane (R-22), difluoromethane (R-32), and fluoromethane (R-41) to a reaction that involves thermal decomposition to obtain the reaction gas, and (2) the starting material gas having a water vapor content of 1 volume % or less.Type: GrantFiled: January 14, 2021Date of Patent: October 11, 2022Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Tatsuya Takakuwa, Osamu Yamamoto, Katsuki Fujiwara, Kei Kuramoto, Yuuta Hasumoto
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Patent number: 11198662Abstract: The present disclosure provides a method for producing fluoroolefin represented by formula (1): CX1X2?CX3X4, wherein X1, X2, X3, and X4 are the same or different, and represent a hydrogen atom or a fluorine atom, with high selectivity. Specifically, the present disclosure is a method for producing fluoroolefin represented by formula (1), wherein the method includes the step of performing dehydrofluorination by bringing a fluorocarbon represented by formula (2): CX1X2FCX3X4H, wherein X1, X2, X3, and X4 are as defined above, into contact with a base, and the dehydrofluorination step is performed in the liquid phase at a temperature of ?70° C. or higher to less than 120° C.Type: GrantFiled: April 3, 2019Date of Patent: December 14, 2021Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Tsubasa Nakaue, Takashi Usui, Takehiro Chaki
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Patent number: 10703693Abstract: A manufacturing method of 1-chloro-3,3,3-trifluoropropene (1233zd) is provided. This manufacturing method includes a reaction in which a halogenated hydrocarbon compound having a carbon number of 3 and represented by a general formula (1) is heated: CFaCl3-a—CH2—CHFbCl2-b??(1) In the formula, a is an integer from 0 to 2, b is 1 or 2 when a=0, b is 0 or 1 when a=1, and b is 0 when a=2.Type: GrantFiled: September 17, 2019Date of Patent: July 7, 2020Assignee: CENTRAL GLASS COMPANY, LIMITEDInventors: Masamune Okamoto, Kohei Sumida, Kei Matsunaga, Yoshio Nishiguchi, Satoru Okamoto
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Patent number: 10611710Abstract: The present invention provides a method for efficiently producing 1-chloro-1,2-difluoroethylene at low cost. Specifically, the present invention provides a method for producing 1-chloro-1,2-difluoroethylene, including the step of dehydrohalogenating chlorofluoroethane represented by formula (1) CFClX1—CHFX2 wherein X1 and X2 are different from each other and represent H, F, or Cl; and either X1 or X2 is H.Type: GrantFiled: July 11, 2017Date of Patent: April 7, 2020Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Daisuke Karube, Satoshi Ohishi
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Patent number: 10464869Abstract: 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 halogenated mono- and di-valent metal oxides, mono- and di-valent Lewis acid metal halides, zero-valent metals, and combinations of these.Type: GrantFiled: May 26, 2017Date of Patent: November 5, 2019Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Hsueh Sung Tung, Sudip Mukhopadhyay
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Patent number: 10266465Abstract: An azeotropic or quasi-azeotropic composition including hydrogen fluoride, 1,3,3,3-tetrafluoropropene and one or more (hydro)halogen-carbon compounds including between 1 and 3 carbon atoms. Also, a preferred azeotropic or quasi-azeotropic composition comprising hydrogen fluoride, 1,3,3,3-tetrafluoropropene, and one or more compounds selected from among 1,1,1,2,2-pentafluoropropane, 2,3,3,3-tetrafluoropropene, 3,3,3-trifluoropropene, 3,3,3-trifluoro-2-chloropropene, E-3,3,3-trifluoro-1-chloropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro, 1,1,1,2-tetrafluoropropane.Type: GrantFiled: July 6, 2018Date of Patent: April 23, 2019Assignee: ARKEMA FRANCEInventors: Philippe Bonnet, Bertrand Collier, Dominque Deur-Bert, Laurent Wendlinger
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Patent number: 10160703Abstract: 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: November 9, 2015Date of Patent: December 25, 2018Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Daniel C. Merkel, Stephen A. Cottrell, Robert C. Johnson
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Patent number: 10112879Abstract: 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-1233x1) 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: February 21, 2017Date of Patent: October 30, 2018Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Daniel C. Merkel, Stephen A. Cottrell, Robert C. Johnson
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Patent number: 10093601Abstract: Compounds with fire extinguishing properties having the formula: wherein R1 is —CR5R6R7 or —CR5R6CR8R9R10 as well as fire extinguishing units including one or more of the compounds.Type: GrantFiled: June 29, 2015Date of Patent: October 9, 2018Assignee: The Boeing CompanyInventors: Kimberly-Alice D. Gregersen, James Craig Moreland, Ekaterina A. Badaeva, Andrew M. Zweig
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Patent number: 10087127Abstract: The present invention relates, in part, to the discovery that the presence of HF in a HCFC-244bb feedstream in a reaction for the preparation of HFO-1234yf results in selectivity changeover from HFO-1234yf to HCFO-1233xf. By substantially removing HF, it is shown that the selectivity to HFO-1234yf via dehydrochlorination of HCFC-244bb is improved.Type: GrantFiled: November 14, 2016Date of Patent: October 2, 2018Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Haiyou Wang, Hsueh Sung Tung
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Patent number: 10059647Abstract: Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CF3CF?CH2 (1234yf). Three steps may be used in preferred embodiments in which a feedstock such as CCl2?CClCH2Cl (which may be purchased or synthesized from 1,2,3-trichloropropane) is fluorinated (preferably with HF in gas-phase in the presence of a catalyst) to synthesize a compound such as CF3CCl?CH2, preferably in a 80-96% selectivity. The CF3CCl?CH2 is preferably converted to CF3CFClCH3 (244-isomer) using a SbCl5 as the catalyst which is then transformed selectively to 1234yf, preferably in a gas-phase catalytic reaction using activated carbon as the catalyst. For the first step, a mixture of Cr2O3 and FeCl3/C is preferably used as the catalyst to achieve high selectivity to CF3CCl?CH2 (96%). In the second step, SbCl5/C is preferably used as the selective catalyst for transforming 1233xf to 244-isomer, CF3CFClCH3.Type: GrantFiled: May 5, 2014Date of Patent: August 28, 2018Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Sudip Mukhopadhyay, Hsueh S. Tung, Michael Van Der Puy, Daniel C. Merkel, Jing Ji Ma, Cheryl L. Bortz, Barbara A. Light, Steven D. Phillips, Rajesh K. Dubey
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Patent number: 10059648Abstract: Provided is an efficient method for producing a fluorine-containing compound without the need for a rectification column involving numerous stages, extractive distillation, etc. The method for producing a fluorine-containing compound includes the step of supplying a composition containing a mixture to a dehydrohalogenation step, the mixture being at least one member selected from the group consisting of mixtures of at least one fluoroolefin and at least one hydrofluorocarbon, the boiling points of which are close to each other, azeotropic mixtures of at least one fluoroolefin and at least one hydrofluorocarbon, and pseudo-azeotropic compounds of at least one fluoroolefin and at least one hydrofluorocarbon.Type: GrantFiled: May 18, 2016Date of Patent: August 28, 2018Assignee: DAIKIN INDUSTRIES, LTD.Inventor: Shun Ohkubo
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Patent number: 10047326Abstract: An azeotropic-like composition containing 2-chloro-1,3,3,3-tetrafluoropropene and 1-chloro-3,3,3-trifluoropropene is provided. The azeotropic-like composition according to the present invention is non-flammable, has little influence on the environment, and has substantially the same composition ratio in the liquid phase and the gas phase. By use of an azeotropic-like composition according to the present invention, a washing detergent, a solvent, a silicone solvent, a foaming agent, a coolant, a heating medium for a heat pump, and a high temperature working fluid that are non-flammable, have little influence on the environment, and have substantially the same composition ratio in a liquid phase and a gas phase thereof may be provided.Type: GrantFiled: March 31, 2017Date of Patent: August 14, 2018Assignee: CENTRAL GLASS COMPANY, LIMITEDInventors: Masahiko Tani, Hideaki Imura, Yoshio Nishiguchi, Naoto Takada
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Patent number: 9790149Abstract: A process for preparing 2,3,3,3-tetrafluoropropene (CF3CF?CH2). 3,3,3-trifluoro-2-chloropropene (CF3CCl?CH2) is fluorinated with HF in the vapour phase in the presence of a chromia-containing catalyst to produce an intermediate composition 1,1,1,2,2-pentafluoropropane (CF3CF2CH3), which is dehydrofluorinated to produce CF3CF?CH2.Type: GrantFiled: January 4, 2017Date of Patent: October 17, 2017Assignee: MEXICHEM AMANCO HOLDING S.A. DE C.V.Inventors: Andrew P Sharratt, Leslie R Seddon
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Patent number: 9783471Abstract: The present invention concerns a method of producing at least one compound of formula (II): CF3—CX(Z)n-CHX(Z)n in which X represents, independently, a hydrogen, fluorine or chlorine atom, Z represents, independently, a hydrogen or fluorine atom, and n=0 or 1, from at least one compound of formula (I): CX(Y)2-CX(Y)m-CHmXY in which X and Y represent, independently, a hydrogen, fluorine or chlorine atom and m=0 or 1. The method comprises at least one step during which at least one compound of formula (I) reacts with HF in the gaseous phase in the presence of a fluorination catalyst in order to give at least one compound of formula (II), characterized in that the catalyst is made from chromium oxyfluoride containing at least nickel as the co-metal and at least one rare earth metal.Type: GrantFiled: September 17, 2014Date of Patent: October 10, 2017Assignee: Arkema FranceInventor: Laurent Wendlinger
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Patent number: 9758450Abstract: The invention relates to a separation process whereby 2-chloro-3,3,3-trifluoropropene (1233xf) is separated from a mixture containing other fluorinated organics and high boiling materials such as dimers using azeotropes of HF formed by adding appropriate amounts to the mixture which facilitate separation by, e.g. distillation.Type: GrantFiled: April 8, 2016Date of Patent: September 12, 2017Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Haiyou Wang, Selma Bektesevic, Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski
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Patent number: 9663424Abstract: 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: August 16, 2013Date of Patent: May 30, 2017Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Haiyou Wang, Hsueh Sung Tung, Sudip Mukhopadhyay
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Patent number: 9586876Abstract: The present invention discloses a manufacturing process to produce high purity 1234yf from 245eb, which preferably includes the removal of impurities present in 245eb raw material, the dehydrofluorination of 245eb, and the removal of impurities present in final crude product. The disclosed manufacturing process allows the production of a 1234yf product with lower the levels of 1225ye and/or trifluoropropene, preferably in amounts of less than about 500, and 50 ppm, respectively.Type: GrantFiled: June 30, 2014Date of Patent: March 7, 2017Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Haiyou Wang, Hsueh Sung Tung, Rajiv R. Singh, Ian Shankland
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Patent number: 9573867Abstract: 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: January 4, 2016Date of Patent: February 21, 2017Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Daniel C. Merkel, Hsueh S. Tung
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Patent number: 9540295Abstract: The present invention relates, in part, to the discovery that high temperatures during the fluorination of 1,1,2,3-tetrachloropropene (HCO-1230xa) to 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) results in catalyst instability, reduced selectivity of the conversion, and/or the formation of one or more undesirable by-products. By controlling the reaction temperature, it is shown that the catalyst life may be extended and the selectivity of the reaction improved. Such control similarly results in an overall improvement in the production of certain hydrofluoroolefins, particularly 2,3,3,3-tetrafluoropropene (HFO-1234yf).Type: GrantFiled: September 29, 2012Date of Patent: January 10, 2017Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Selma Bektesevic, Hsueh Sung Tung, Haiyou Wang
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Patent number: 9440896Abstract: Disclosed is a process for producing hexafluoro-2-butyne comprising, reacting HCFC-336 with an aqueous solution of an alkali metal hydroxide in the presence of a quaternary alkylammonium salt which comprises at least one alkyl group of at least 8 carbons, and recovering the hexafluoro-2-butyne, wherein the conversion of dichloro-1,1,1,4,4,4-hexafluorobutane is at least 50% per hour. Also disclosed is a process for producing hexafluoro-2-butyne comprising, reacting HCFC-336 with an aqueous solution of an alkali metal hydroxide in the presence of a quaternary alkylammonium salt having alkyl groups of from four to ten carbon atoms, and mixtures thereof, and a non-ionic surfactant, and recovering the hexafluoro-2-butyne, and wherein the conversion of dichloro-1,1,1,4,4,4-hexafluorobutane to hexafluoro-2-butyne is at least 20% per hour.Type: GrantFiled: September 27, 2013Date of Patent: September 13, 2016Assignee: THE CHEMOURS COMPANY FC, LLCInventors: Sheng Peng, Mario Joseph Nappa
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Patent number: 9416074Abstract: The present invention relates, in part, to the discovery that the presence of impurities in a reactor for dehydrochlorinating HCFC-244bb to HFO-1234yf results in a reduced conversion rate and/or a selectivity changeover from HFO-1234yf to HCFO-1233xf. By substantially removing such impurities, it is shown that the conversion rate may be improved and selectivity to HFO-1234yf via dehydrochlorination of HCFC-244bb is also improved.Type: GrantFiled: October 10, 2012Date of Patent: August 16, 2016Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Haiyou Wang, Hsueh Sung Tung, Daniel C. Merkel
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Patent number: 9353030Abstract: Disclosed is a one step process for making of 1,1,1,4,4,4-hexafluoro-2-butene. More specifically, the present invention provides a process for making hexafluoro-2-butene, continuously, from 2-chloro-3,3,3-trifluoropronene using Fe2O3/NiO impregnated carbon catalyst at 600° to 650° C.Type: GrantFiled: June 12, 2015Date of Patent: May 31, 2016Assignee: Honeywell International Inc.Inventors: Haridasan K. Nair, David Nalewajek, Glenn Matthies
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Patent number: 9334208Abstract: The present invention provides a process for preparing 2,3,3,3-tetrafluoropropene from 1,1,1,2,3-pentachloropropane and/or 1,1,2,2,3-pentachloropropane, 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 a reaction mixture comprising HCl, 2-chloro-3,3,3-trifluoropropene, 2,3,3,3-tetrafluoropropene, unreacted HF, and optionally 1,1,1,2,2-pentafluoropropane; (b) separating the reaction mixture into a first stream comprising HCl and 2,3,3,3-tetrafluoropropene and a second stream comprising HF, 2-chloro-3,3,3-trifluoropropene and optionally 1,1,1,2,2-pentafluoropropane; (c) catalytic reaction of the second stream into a reaction mixture comprising 2,3,3,3-tetrafluoropropene, HCl, unreacted 2-chloro-3,3,3-trifluoropropene, unreacted HF and optionally 1,1,1,2,2-pentafluoropropane and (d) feeding the reaction mixture of step (c) directly without separation to step (a).Type: GrantFiled: December 14, 2011Date of Patent: May 10, 2016Assignee: Arkema FranceInventors: Dominique Deur-Bert, Bertrand Collier, Laurent Wendlinger
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Patent number: 9302962Abstract: A method of producing a fluoropropane of formula CF3CH?CHF, comprising contacting a mixture of 1,1,1,3,3-pentafluoropropane and Z-1,3,3,3-tetrafluoropropene in the gas phase with a catalyst comprising at least one catalyst selected from the group consisting of fluorinated Cr2O3 or Cr/Ni on fluoride alumina, in the presence of an oxygen containing gas, to form a mixture comprising Z-1,3,3,3-tetrafluoropropane, E-1,3,3,3,-tetrafluoropropene, hydrogen fluoride, and optionally unreacted 1,1,1,3,3-pentafluoropropane, separating the E-1,3,3,3-tetrafluoropropene from the Z-isomer and any unreacted 1,1,1,3,3-pentafluoropropane, if present, and recovering said E-1,3,3,3-tetrafluoropropene.Type: GrantFiled: August 6, 2015Date of Patent: April 5, 2016Assignee: THE CHEMOURS COMPANY FC, LLCInventors: Sheng Peng, Mario Joseph Nappa
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Patent number: 9296669Abstract: Disclosed is a process for passivating a surface of a dehydrochlorination reactor comprising: stopping a flow of hydrochlorofluoropropane to a reactor, passing a gas mixture comprising hydrogen gas through the reactor at a temperature of at least 25° C. for a period of time sufficient to restore the selectivity of a dehydrochlorination reaction, stopping the flow of the hydrogen gas mixture, and resuming the flow of hydrochlorofluoropropane to the dehydrochlorination reaction.Type: GrantFiled: January 8, 2013Date of Patent: March 29, 2016Assignee: E.I. DU PONT DE NEMOURS AND COMPANYInventors: Xuehui Sun, Mario Joseph Nappa, Haiyou Wang, Haluk Kopkalli
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Patent number: 9227893Abstract: 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: December 15, 2014Date of Patent: January 5, 2016Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Daniel C. Merkel, Hsueh S. Tung
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Patent number: 9174896Abstract: 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: GrantFiled: November 7, 2011Date of Patent: November 3, 2015Assignee: THE CHEMOURS COMPANY FC, LLCInventors: Mario Joseph Nappa, Ekaterina N Swearingen
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Patent number: 9162945Abstract: Provided is a process for preparing 2-chloro-3,3,3-trifluoropropene, wherein at least one chlorine-containing compound selected from the group consisting of chloropropane represented by formula (1): CX3CHClCH2Cl, wherein each X is the same or different and each represents Cl or F, chloropropene represented by formula (2): CClY2CCl?CH2, wherein each Y is the same or different and each represents Cl or F, and chloropropene represented by formula (3): CZ2?CClCH2Cl, wherein each Z is the same or different and each represents Cl or F, is used as a starting compound, and said at least one chlorine-containing compound is reacted with hydrogen fluoride while being heated in a gaseous state in the presence of 50 ppm or more of water relative to the chlorine-containing compound. The process of the present invention makes it possible to produce 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) in a manner that is easily conducted, economically advantageous, and suitable for industrial scale production.Type: GrantFiled: March 21, 2013Date of Patent: October 20, 2015Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Masayuki Kishimoto, Yuzo Komatsu
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Patent number: 9102580Abstract: The present disclosure provides a fluorination process which involves reacting a hydrohaloalkene of the formula RfC—Cl?CH2 with HF in a reaction zone in the presence of a fluorination catalyst selected from the group consisting of TaF5 and TiF4 to produce a product mixture containing a hydrohaloalkane of the formula RfCFClCH3, wherein Rf is a perfluorinated alkyl group.Type: GrantFiled: November 9, 2012Date of Patent: August 11, 2015Assignee: THE CHEMOURS COMPANY FC, LLCInventors: Mario Joseph Nappa, Andrew Jackson, Daniel C. Merkel
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Patent number: 9067856Abstract: 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: GrantFiled: August 12, 2014Date of Patent: June 30, 2015Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Robert C. Johnson, Hsueh S. Tung, Daniel C. Merkel
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Patent number: 9061957Abstract: Disclosed is a method for producing fluorinated organic compounds, including reacting CF2?CFCl with CH2FCl under conditions effective to produce a product composition including CF3CClFCH2Cl. The present invention also relates to the production of hydrofluoropropenes, which preferably comprises converting at least one compound of formula (I): CF3CFnCHmXa?m??(I) to at least one compound of formula (II) CF3CZCHZ??(II). where each X is independently Cl, F, I or Br; each Z is independently H or F; n is 1 or 2; m is 1, 2 or 3, provided that when n is 1, m is 1 or 2; a is 2 or 3, and a?m?0. Certain embodiments include the step of reacting fluorinated C2 olefin, such as tetrafluoroethylene, with a C1 addition agent under conditions effective to produce a compound of formula (I).Type: GrantFiled: January 22, 2013Date of Patent: June 23, 2015Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Rajesh K. Dubey, Rajiv R. Singh, George A. Shia
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Patent number: 9056808Abstract: Processes for the production of chlorinated propenes are provided. The present processes make use of 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. The present processes can 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. Finally, the processes are advantageously conducted in the liquid phase, thereby presenting additional savings as compared to conventional, gas phase processes.Type: GrantFiled: May 18, 2012Date of Patent: June 16, 2015Assignee: Dow Global Technologies, LLCInventors: Max M. Tirtowidjojo, William J. Kruper, Jr., Barry B. Fish, David S. Laitar
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Publication number: 20150148570Abstract: The present invention is directed to processes for the production of 1233zd from 240fa and HF, with or without a catalyst, at a commercial scale. The 240fa and HF are fed to a reactor operating at high pressure. The resulting product stream comprising 1233zd, HCl, HF, and other byproducts is treated to one or more purification techniques including phase separation and one or more distillations to provide purified 1233zd, which meets commercial product specifications, i.e., having a GC purity of 99.5% or greater.Type: ApplicationFiled: January 30, 2015Publication date: May 28, 2015Inventors: Stephen A. Cottrell, Hsueh Sung Tung, Konstantin A. Pokrovski
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Patent number: 9040760Abstract: 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: GrantFiled: October 27, 2011Date of Patent: May 26, 2015Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Kazuhiro Takahashi, Yuzo Komatsu, Akinori Ueda
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Patent number: 9035112Abstract: Disclosed is a process for producing 2-chloro-1,3,3,3-tetrafluoropropene (1224), including a first step of separating 2,3-dichloro-1,1,1,3-tetrafluoropropane (234da) into erythro form and threo form, and a second step of bringing the separated erythro form or threo form in contact with a base to obtain 2-chloro-1,3,3,3-tetrafluoropropene (1224). The first step is a step of separating 234da by distillation to achieve a separation into a fraction containing mainly erythro form and a fraction containing mainly threo form. In the second step, 1224 cis form is obtained from the erythro form, and 1224 trans form is obtained from the threo form. By this process, it is possible to selectively and efficiently produce cis form or trans form of 2-chloro-1,3,3,3-tetrafluoropropene (1224).Type: GrantFiled: May 8, 2014Date of Patent: May 19, 2015Assignee: Central Glass Company, Ltd.Inventors: Hideaki Imura, Yoshio Nishiguchi, Masamune Okamoto, Tatsuya Hayasaka, Minako Oomura, Satoru Okamoto, Naoto Takada
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Patent number: 9029616Abstract: The present invention provides routes for making 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) from commercially available raw materials. More specifically, this invention provides routes for HCFO-1233zd from inexpensive and commercially available trifluoromethane (HFC-23).Type: GrantFiled: July 14, 2014Date of Patent: May 12, 2015Assignee: Honeywell International Inc.Inventors: Haridasan K. Nair, Andrew Joseph Poss, David Nalewajek, Yian Zhai
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Patent number: 9018428Abstract: 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: GrantFiled: March 14, 2013Date of Patent: April 28, 2015Assignee: Honeywell International Inc.Inventor: Stephen A. Cottrell
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Patent number: 9018429Abstract: The subject of the invention is a process for the preparation of fluoroolefin compounds.Type: GrantFiled: January 12, 2010Date of Patent: April 28, 2015Assignee: Arkenna FranceInventors: Pierre-Marie Sedat, Jean-Michel Bossoutrot
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Patent number: 9012702Abstract: A dehydrochlorination process is disclosed. The process involves contacting RfCFClCH2X with a catalyst in a reaction zone to produce a product mixture comprising RfCF?CHX, wherein said catalyst comprises MY supported on carbon, and wherein Rf is a perfluorinated alkyl group, X ?H, F, Cl, Br or I, M=K, Na or Cs, and Y?F, Cl or Br.Type: GrantFiled: February 10, 2012Date of Patent: April 21, 2015Assignee: E. I. du Pont de Nemours and CompanyInventors: Xuehui Sun, Mario Joseph Nappa
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Patent number: 9000240Abstract: The present invention is directed to processes for the production of 1233zd from 240fa and HF, with or without a catalyst, at a commercial scale. The 240fa and HF are fed to a reactor operating at high pressure. The resulting product stream comprising 1233zd, HCl, HF, and other byproducts is treated to one or more purification techniques including phase separation and one or more distillations to provide purified 1233zd, which meets commercial product specifications, i.e., having a GC purity of 99.5% or greater.Type: GrantFiled: May 15, 2012Date of Patent: April 7, 2015Assignee: Honeywell International Inc.Inventors: Stephen A. Cottrell, Hsueh Sung Tung, Konstantin A. Pokrovski
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Publication number: 20150094502Abstract: The present invention provides a process of fluorination in liquid phase in a solvent medium of a compound of formula (II) CX1X2=CZCX3X4X5, in which Z represents H, Cl or F, and each X1 represents independently hydrogen or chlorine, given that at least one of the X1 represents a chlorine.Type: ApplicationFiled: October 8, 2014Publication date: April 2, 2015Applicant: ARKEMA FRANCEInventor: Anne PIGAMO
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Patent number: 8987536Abstract: The present disclosure relates to processes for reducing the concentration of RfC?CX impurities in fluoroolefins. The process involves: contacting a mixture comprising at least one fluoroolefin and at least one RfC?CX impurity with at least one amine to reduce the concentration of the at least one RfC?CX impurity in the mixture; wherein Rf is a perfluorinated alkyl group, and X is H, F, Cl, Br or I. The present disclosure also relates to processes for making at least one hydrotetrafluoropropene product selected from the group consisting of CF3CF?CH2, CF3CH?CHF, and mixtures thereof and reducing the concentration of CF3C?CH impurity generated during the process. The present disclosure also relates to processes for making at least one hydrochlorotrifluoropropene product selected from the group consisting of CF3CCl?CH2, CF3CH?CHCl, and mixtures thereof and reducing the concentration of CF3C?CH impurity generated during the process.Type: GrantFiled: June 6, 2013Date of Patent: March 24, 2015Assignee: E I du Pont de Nemours and CompanyInventors: Xuehui Sun, Mario Joseph Nappa
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Publication number: 20150080618Abstract: A production method of cis-1,3,3,3-tetrafluoropropene according to the present invention includes the steps of: subjecting 1,1,1,3,3-pentafluoropropane to dehydrofluorination to form a reaction mixture (A) containing cis-1,3,3,3-tetrafluoropropene, trans-1,3,3,3-tetrafluoropropene and unreacted 1,1,1,3,3-pentafluoropropane; distilling the reaction mixture (A) to separate the trans-1,3,3,3-tetrafluoropropene from the reaction mixture (A) and collect a reaction mixture (B) containing the cis-1,3,3,3-tetrafluoropropene and the 1,1,1,3,3-pentafluoropropane; and reacting the reaction mixture (B) with a base and thereby obtaining the cis-1,3,3,3-tetrafluoropropene from the reaction mixture (B). This production method enables efficient production of high-purity cis-1,3,3,3-tetrafluoropropene and thus has industrial advantages.Type: ApplicationFiled: April 2, 2013Publication date: March 19, 2015Inventors: Satoshi Yoshikawa, Satoru Okamoto, Yoshio Nishiguchi, Fuyuhiko Sakyu
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Patent number: 8975454Abstract: The instant invention relates to a process and method for manufacturing 2,3,3,3-tetrafluoropropene by dehydrohalogenating a reactant stream of 2-chloro-1,1,1,2-tetrafluoropropane that is substantially free from impurities, particularly halogenated propanes, propenes, and propynes.Type: GrantFiled: October 25, 2011Date of Patent: March 10, 2015Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh S. Tung, Haiyou Wang
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Publication number: 20150057471Abstract: The use of sulfuryl chloride, either alone or in combination with chlorine, as a chlorinating agent is disclosed.Type: ApplicationFiled: May 18, 2012Publication date: February 26, 2015Applicant: DOW GLOBAL TECHNOLOGIES LLCInventors: Max M Tirtowidjojo, Matthew Lee Grandbois, John D. Myers, William J. Kruper, JR.
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Publication number: 20150045588Abstract: The present invention provides routes for making 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) from commercially available raw materials. More specifically, this invention provides routes for HCFO-1233zd from inexpensive and commercially available trifluoromethane (HFC-23).Type: ApplicationFiled: July 14, 2014Publication date: February 12, 2015Inventors: Haridasan K. Nair, Andrew Joseph Poss, David Nalewajek, Yian Zhai
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Publication number: 20150038749Abstract: Disclosed is a process for producing 2-chloro-1,3,3,3-tetrafluoropropene (1224), including a first step of separating 2,3-dichloro-1,1,1,3-tetrafluoropropane 234da) into erythro form and threo form, and a second step of bringing the separated erythro form or threo form in contact with a base to obtain 2-chloro-1,3,3,3-tetrafluoropropene (1224). The first step is a step of separating 234da by distillation to achieve a separation into a fraction containing mainly erythro form and a fraction containing mainly threo form. In the second step, 1224 cis form is obtained from the erythro form, and 1224 trans form is obtained from the threo form. By this process, it is possible to selectively and efficiently produce cis form or trans form of 2-chloro-1,3,3,3-tetrafluoropropene (1224).Type: ApplicationFiled: May 8, 2014Publication date: February 5, 2015Applicant: Central Glass Company, LimitedInventors: Hideaki IMURA, Yoshio NISHIGUCHI, Masamune OKAMOTO, Tatsuya HAYASAKA, Minako OOMURA, Satoru OKAMOTO, Naoto TAKADA
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Patent number: 8940948Abstract: 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: July 17, 2013Date of Patent: January 27, 2015Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Hsueh Sung Tung
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Patent number: 8936757Abstract: Apparatuses and processes are provided for stripping gaseous hydrocarbons from particulate material. One process comprises the step of contacting particles containing hydrocarbons with a stripping vapor in countercurrent flow to remove at least a portion of the hydrocarbons with the stripping vapor to form stripped particles. Contacting the particles includes advancing the particles down a sloping element of a structured packing toward a reinforcing rod that is disposed along a lower channel portion of the sloping element. The particles are advanced over the reinforcing rod. The particles are contacted with the stripping vapor that is rising up adjacent to the lower channel portion.Type: GrantFiled: December 28, 2011Date of Patent: January 20, 2015Assignee: UOP LLCInventors: Erick D. Gamas-Castellanos, Mitchell John Kowalczyk