By Reacting With Hydrogen Fluoride Patents (Class 570/164)
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Patent number: 10872780Abstract: Disclosed is the invention of a dry etching agent composition including: 1,3,3,3-tetrafluoropropene; and a hydrochlorofluorocarbon represented by CHxClyFz (wherein x, y and z are integers of 1 or greater and x+y+z=4), wherein a concentration of the hydrochlorofluorocarbon relative to 1,3,3,3-tetrafluoropropene is 3 volume ppm or greater to less than 10000 volume ppm, and a use of this dry etching agent composition. An object of the present invention is to suppress corrosion of storage container, pipes and an etching chamber by suppressing generation of acidic substances by improving storage stability of HFO-1234ze without losing excellent etching characteristics of HFO-1234ze.Type: GrantFiled: October 23, 2017Date of Patent: December 22, 2020Assignee: Central Glass Company, LimitedInventors: Hiroyuki Oomori, Akifumi Yao, Isamu Mori
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Patent number: 10550054Abstract: An azeotropic or quasi-azeotropic composition including hydrogen fluoride, 3,3,3-trifluoropropene and one or more (hydro)halogen-carbon compounds including between 1 and 3 carbon atoms. Also, a preferred azeotropic or quasi-azeotropic composition including hydrogen fluoride, 3,3,3-trifluoropropene, and one or more compounds selected from among 1,1,1,2,2-pentafluoropropane, 2,3,3,3-tetrafluoropropene, 1,3,3,3-tetrafluoropropene, 3,3,3-trifluoro-2-chloropropene, E-3,3,3-trifluoro-l-chloropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro, 1,1,1,2-tetrafluoropropane.Type: GrantFiled: February 24, 2014Date of Patent: February 4, 2020Assignee: ARKEMA FRANCEInventors: Philippe Bonnet, Bertrand Collier, Dominique Deur-Bert, Laurent Wendlinger
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Patent number: 10450248Abstract: A method for producing 1,3,3,3-tetrafluoropropene (HFO-1234ze, or 1234ze) from 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd, or 1233zd). In one embodiment, HFO-1233zd is subjected to a disproportionation reaction in the presence of a catalyst at an elevated temperature to produce HFO-1234ze as well as 3,3-dichloro-1,1-difluoropropene (HCFO-1232zc). The catalyst may be at least one of a chromium oxyfluoride catalyst, a chromium oxide catalyst, or a metal fluoride catalyst. The reaction may be conducted in the vapor phase at a temperature between 100° C. and 450° C. Advantageously, in the present method, substantially no hydrogen fluoride (HF) is used as a reactant, and substantially no HF is produced as a product.Type: GrantFiled: November 1, 2018Date of Patent: October 22, 2019Assignee: Honeywell International Inc.Inventors: Christian Jungong, Daniel C. Merkel, Haiyou Wang
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Patent number: 10343963Abstract: An azeotropic or quasi-azeotropic composition including hydrogen fluoride, E-3,3,3-trifluoro-1-chloropropene and optionally one or more (hydro)halogen-carbon compounds including between 1 and 3 carbon atoms. Also, a preferred azeotropic or quasi-azeotropic composition including hydrogen fluoride, E-3,3,3-trifluoro-1-chloropropene, and optionally 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, 1,3,3,3-tetrafluoropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro,1,1,1,2-tetrafluoropropane.Type: GrantFiled: August 13, 2018Date of Patent: July 9, 2019Assignee: ARKEMA FRANCEInventors: Philippe Bonnet, Bertrand Collier, Dominque Deur-Bert, Laurent Wendlinger
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Patent number: 10252913Abstract: An azeotropic or quasi-azeotropic composition including hydrogen fluoride, 2,3,3,3-tetrafluoropropene and one or more (hydro)halogen-carbon compounds including between 1 and 3 carbon atoms. Also a azeotropic or quasi-azeotropic composition including hydrogen fluoride, 2,3,3,3-tetrafluoropropene, and one or more organic compounds selected from among 1,1,1,2,2-pentafluoropropane, E-1,3,3,3-tetrafluoropropene, Z-1,3,3,3-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, 1,1,1,3,3-pentafluoropropene, Z-1,1,1,2,3-pentafluoropropene and 2-chloro,1,1,1,2-tetrafluoropropane.Type: GrantFiled: February 21, 2014Date of Patent: April 9, 2019Assignee: ARKEMA FRANCEInventors: Philippe Bonnet, Bertrand Collier, Dominique Deur-Bert, Laurent Wendlinger
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Patent number: 10077221Abstract: An azeotropic or quasi-azeotropic composition including hydrogen fluoride, E-3,3,3-trifluoro-1-chloropropene and optionally one or more (hydro)halogen-carbon compounds including between 1 and 3 carbon atoms. Also, a preferred azeotropic or quasi-azeotropic composition including hydrogen fluoride, E-3,3,3-trifluoro-1-chloropropene, and optionally 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, 1,3,3,3-tetrafluoropropene, trifluoropropyne, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropane, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro,1,1,1,2-tetrafluoropropane.Type: GrantFiled: February 21, 2014Date of Patent: September 18, 2018Assignee: ARKEMA FRANCEInventors: Philippe Bonnet, Bertrand Collier, Dominique Deur-Bert, Laurent Wendlinger
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Patent number: 10029963Abstract: 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-pentafluoropropene, 1,1,1,3,3-pentafluoropropene, 1,1,1,2,3-pentafluoropropene and 2-chloro, 1,1,1,2-tetrafluoropropane.Type: GrantFiled: February 24, 2014Date of Patent: July 24, 2018Assignee: ARKEMA FRANCEInventors: Philippe Bonnet, Bertrand Collier, Dominique Deur-Bert, Laurent Wendlinger
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Patent number: 9914680Abstract: Provided is a process for making 2-chloro-1,1,1,2-tetrafluoropropane. The process has the step of hydrofluorinating 2-chloro-3,3,3-trifluoropropene in the presence of a catalyst selected from the group consisting of SbCl3, SbCl5, SbF5, TiCl4, SnCl4, Cr2O3, and fluorinated Cr2O3.Type: GrantFiled: May 5, 2015Date of Patent: March 13, 2018Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Daniel C. Merkel, Robert C. Johnson, Hsueh Sung Tung
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Patent number: 9682905Abstract: 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: January 30, 2015Date of Patent: June 20, 2017Assignee: Honeywell International Inc.Inventors: Stephen A. Cottrell, Hsueh Sung Tung, Konstantin A. Pokrovski
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Patent number: 9593058Abstract: An object of the present invention is to provide a production method that makes it possible to produce 1,1-dibromo-1-fluoroethane easily and sustainably. The present invention provides a method for producing 1,1-dibromo-1-fluoroethane, the method comprising step A of reacting 1,1-dibromoethylene with hydrogen fluoride to obtain 1,1-dibromo-1-fluoroethane.Type: GrantFiled: September 3, 2014Date of Patent: March 14, 2017Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Atsushi Shirai, Masatoshi Nose, Yosuke Kishikawa, Tatsuya Ohtsuka, Sumi Ishihara
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Patent number: 9255045Abstract: A production process for the production of E-1-chloro-3,3,3-trifluoropropene, the process including at least one stage during which 1,1,3,3 -tetrachloropropene reacts with anhydrous hydrofluoric acid in the liquid phase, in the absence of a catalyst, with an HF/1,1,3,3-tetrachloropropene molar ratio between 3 and 20 inclusive, at a temperature between 50° C. and 150° C. inclusive and an absolute pressure of between 1 and 20 bar inclusive.Type: GrantFiled: January 13, 2014Date of Patent: February 9, 2016Assignee: ARKEMA FRANCEInventors: Anne Pigamo, John Wismer, Bertrand Collier, Philippe Bonnet
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Patent number: 9227894Abstract: 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: January 30, 2015Date of Patent: January 5, 2016Assignee: Honeywell International Inc.Inventors: 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: 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: 8921621Abstract: A process for the manufacture of 1-chloro-3,3,3-trifluoropropene (HCFC-1233zd) at commercial scale from the reaction of HCC-240 and HF is disclosed. In one embodiment, HCC-240fa and HF are fed to a reactor operating at high pressure. Several different reactor designs useful in this process include; a stirred-tank reactor (batch and/or continuous flow); a plug flow reactor; a static mixer used as a reactor; at least one of the above reactors operating at high pressure; optionally combined with a distillation column running at a lower pressure; and combinations of the above; and/or with a distillation column. The resulting product stream consisting of 1233zd, HCl, HF, and other byproducts is partially condensed to recover HF by phase separation. The recovered HF phase is recycled to the reactor. The HCl is scrubbed from the vapor stream and recovered as an aqueous solution.Type: GrantFiled: February 4, 2013Date of Patent: December 30, 2014Assignee: Honeywell International Inc.Inventors: Stephen A. Cottrell, Hsueh Sung Tung, Konstantin A. Pokrovski, Haiyou Wang, Daniel C. Merkel
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Patent number: 8912369Abstract: A production method of 1-chloro-3,3,3-trifluoropropene according to the present invention includes bringing a composition containing a compound of the general formula (1): CF3—CH2—CHClX (where X is a fluorine atom or a chlorine atom) into contact with a solid catalyst in the presence of hydrogen chloride. In this production method, the composition containing ozone depleting HCFC such as 3-chloro-1,1,1,3-tetraluoforpropane or 3,3-dichloro-1,1,1-trifluoropropane can be efficiently converted to the 1-chloro-3,3,3-trifluoropropene, which has less influence on the global environment and is useful as a solvent, a cleaning agent, a coolant, a working fluid, a propellant, a raw material for fluorinated resins etc.Type: GrantFiled: June 27, 2013Date of Patent: December 16, 2014Assignee: Central Glass Company, LimitedInventors: Hideaki Imura, Naoto Takada
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Patent number: 8895788Abstract: The invention relates to a process for manufacturing 1,1,1,2-tetrafluoropropene (1234yf, CF3—CF?CH2) from 1,1,3,3-tetrachlororopropene (1230za, CCl2?CH—CHCl2) and/or 1,1,1,3,3-pentachloropropane (240fa, CCl3CH2CHCl2). The process comprises a step of isomerization of 1,1,3,3-tetrafluoropropene (1230za) to 1,1,2,3-tetrachloropropene (1230xa) followed by conversion of the 1,1,2,3-tetrachloropropene (1230xa) to 1,1,1,2-tetrafluoropropene (1234yf) via a hydrofluorination process.Type: GrantFiled: January 21, 2014Date of Patent: November 25, 2014Assignee: Arkema Inc.Inventors: Maher Y. Elsheikh, Philippe Bonnet, John A. Wismer
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Publication number: 20140343331Abstract: The invention relates to a process to produce HCFC-244bb from HCFO-1233xf wherein, in one embodiment, co-feed species HFC-245cb is added to the reaction at a pressure of at least about 100 psig; and in another embodiment it is added to maintain a mole ratio of HFC-245cb to HCFO-1233xf of between about 0.005:1 to about 1:1. The HFC-245cb may be added as recycled by-product of the reaction and/or added as fresh feed. The HFC-245cb provides elevated pressures to the reaction thereby facilitating reactor operation, mixing and HCFC-244bb product removal. Other co-feed species are also disclosed.Type: ApplicationFiled: March 13, 2014Publication date: November 20, 2014Applicant: HONEWELL INTERNATIONAL, INC.Inventors: Haluk Kopkalli, Daniel C. Merkel, Ron Joseph Roof
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Patent number: 8889925Abstract: 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: GrantFiled: March 10, 2010Date of Patent: November 18, 2014Assignee: Arkema FranceInventor: Anne Pigamo
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Patent number: 8877989Abstract: A process for dehydrating a hydrofluorocarbon or hydrochlorofluorocarbon, which can be done by simple equipment, and a continuous process of producing 1,3,3,3-tetrafluoropropene using the dehydration process. The dehydration process includes cooling the hydrofluorocarbon or hydrochlorofluorocarbon in gaseous form containing water with a heat exchanger, thereby condensing and liquefying the hydrofluorocarbon or hydrochlorofluorocarbon while freezing and solidifying the water.Type: GrantFiled: July 22, 2011Date of Patent: November 4, 2014Assignee: Central Glass Company, LimitedInventors: Yoshio Nishiguchi, Yasuo Hibino
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Publication number: 20140275654Abstract: The present invention provides a process for preparing at least one chlorine-containing fluorocarbon compound selected from the group consisting of chlorine-containing fluoropropane compounds represented by Formula (1): CFnCl3-nCHClCH2Cl, wherein n is 1 or 2, and chlorine-containing fluoropropene compounds represented by Formula (2): CFnCl3-nCCl?CH2, wherein n is 1 or 2, wherein the process includes the step of contacting at least one chlorine-containing compound selected from the group consisting of 1,1,1,2,3-pentachloropropane, 1,1,2,3-tetrachloropropene, and 2,3,3,3-tetrachloropropene with hydrogen fluoride in the absence of a catalyst while heating. According to the present invention, the chlorine-containing propane and propene compounds having 1 or 2 fluorine atoms can be prepared by an industrially applicable, simple and effective process.Type: ApplicationFiled: May 29, 2014Publication date: September 18, 2014Applicant: DAIKIN INDUSTRIES, LTD.Inventors: Masatoshi NOSE, Tsuneo YAMASHITA, Atsushi SUZUKI
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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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Patent number: 8822741Abstract: A process for the fluorination of haloolefins with elemental fluorine in the presence of anhydrous HF proceeds with high yield and selectivity in the product deriving from the addition of fluorine to the carbon-carbon double bond.Type: GrantFiled: July 5, 2011Date of Patent: September 2, 2014Assignee: Solvay Specialty Polymers Italy S.p.A.Inventors: Vito Tortelli, Marco Galimberti
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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: 8779219Abstract: The present invention provides a process for preparing at least one chlorine-containing fluorocarbon compound selected from the group consisting of chlorine-containing fluoropropane compounds represented by Formula (1): CFnCl3-nCHClCH2—Cl, wherein n is 1 or 2, and chlorine-containing fluoropropene compounds represented by Formula (2): CFnCl3-nCCl?CH2, wherein n is 1 or 2, wherein the process includes the step of contacting at least one chlorine-containing compound selected from the group consisting of 1,1,1,2,3-pentachloropropane, 1,1,2,3-tetrachloropropene, and 2,3,3,3-tetrachloropropene with hydrogen fluoride in the absence of a catalyst while heating. According to the present invention, the chlorine-containing propane and propene compounds having 1 or 2 fluorine atoms can be prepared by an industrially applicable, simple and effective process.Type: GrantFiled: May 12, 2010Date of Patent: July 15, 2014Assignee: Daikin Industries, Ltd.Inventors: Masatoshi Nose, Tsuneo Yamashita, Atsushi Suzuki
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Patent number: 8680346Abstract: 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: GrantFiled: September 11, 2009Date of Patent: March 25, 2014Assignee: Arkema FranceInventors: Anne Pigamo, Michel Devic, Laurent Wendlinger
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Patent number: 8680345Abstract: Disclosed is a method for the production of 1233xf comprising the continuous low temperature liquid phase reaction of 1,1,1,2,3-pentachloropropane and anhydrous HF, without the use of a catalyst, wherein the reaction takes place in one or more reaction vessels, each one in succession converting a portion of the original reactants fed to the lead reaction vessel and wherein the reactions are run in a continuous fashion.Type: GrantFiled: December 7, 2011Date of Patent: March 25, 2014Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski, Haiyou Wang, Selma Bektesevic
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Patent number: 8653311Abstract: The present invention relates to an azeotropic or azeotrope-like mixture consisting essentially of 1,1,1,2,3,3-hexafluoropropane, hexafluoropropene and hydrogen fluoride.Type: GrantFiled: April 11, 2013Date of Patent: February 18, 2014Assignee: Honeywell International Inc.Inventors: Ryan Hulse, Hang T. Pham, Rajiv R. Singh, Hsueh S. Tung, Daniel C. Merkel, Konstantin A. Pokrovski
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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: 8618340Abstract: Disclosed is a process for the manufacture of HFO-1234yf from TCP in three integrated steps that include hydrofluorination of TCP (tetrachloropropene) to HCFC-1233xf in the vapor phase followed by hydrofluorination of HCFC-1233xf to HCFC-244bb in the liquid phase which is then followed by dehydrochlorination in liquid or vapor phase to produce HFO-1234yf. The vapor phase hydrofluorination is carried out at a higher pressure than the liquid phase hydrofluorination, thereby eliminating the need for compression and/or intermediate recovery. Also, any HCl generated from this reaction is fed to the liquid phase hydrofluorination section to promote agitation and mixing. This results in a more economical process from an initial capital and operating cost versus conducting the 3-steps sequentially.Type: GrantFiled: November 3, 2009Date of Patent: December 31, 2013Assignee: Honeywell International Inc.Inventors: Haluk Kopkalli, Yuon Chiu, Stephen A. Cottrell, Hsueh Sung Tung, Kevin Uhrich
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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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Patent number: 8575407Abstract: A support of metal oxyfluoride or metal halide for a metal-based hydrogenation catalyst useful in hydrogenating fluoroolefins is provided.Type: GrantFiled: March 20, 2012Date of Patent: November 5, 2013Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Hsueh Sung Tung
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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: 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: 8519200Abstract: Provided are azeotropic or azeotrope-like mixtures of 1,1,3,3-tetrachloro-1-fluoropropane (HCFC-241fa) and hydrogen fluoride. Such compositions are useful as an intermediate in the production of HFC-245fa and HCFO-1233zd.Type: GrantFiled: February 23, 2012Date of Patent: August 27, 2013Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hang T. Pham, Hsueh Sung Tung, Ryan Hulse
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Patent number: 8481793Abstract: The invention provides a method for separating halocarbons. In particular, a method for separating 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) from 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) based on differences in melting points of these compounds. More particularly the invention pertains to a method for separating HCFC-244bb from HCFO-1233xf which are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).Type: GrantFiled: July 26, 2012Date of Patent: July 9, 2013Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Hsueh S. Tung, Konstantin A. Pokrovski
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Patent number: 8461401Abstract: 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: GrantFiled: March 11, 2011Date of Patent: June 11, 2013Assignee: Honeywell International Inc.Inventors: Hsueh Sung Tung, Haiyou Wang
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Patent number: 8445736Abstract: A one reactor, gas phase catalyzed process for the fluorination of 1,1,2,3-tetrachloropropene (1230xa) to produce 1,1,1,2-tetrafluoropropene (1234yf) is disclosed. The process of the present invention is a catalytic, gas phase fluorination using a high pressure activated catalyst which is supported or unsupported. Fluorination products of the formula CF3R, where R is selected from —CCl?CH2, —CF?CH2, —CF2—CH3, —CFCl—CH3 and mixtures thereof are produced. Co-produced materials are separated from the desired product and recycled to the same reactor.Type: GrantFiled: June 23, 2009Date of Patent: May 21, 2013Assignee: Arkema Inc.Inventors: Maher Y. Elsheikh, Philippe Bonnet
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Publication number: 20130116483Abstract: A process for the fluorination of haloolefins with elemental fluorine in the presence of anhydrous HF proceeds with high yield and selectivity in the product deriving from the addition of fluorine to the carbon-carbon double bond.Type: ApplicationFiled: July 5, 2011Publication date: May 9, 2013Applicant: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.Inventors: Vito Tortelli, Marco Galimberti
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Patent number: 8436218Abstract: The present invention relates to an azeotropic or azeotrope-like mixture consisting essentially of 1,1,1,2,3,3-hexafluoropropane, hexafluoropropene and hydrogen fluoride.Type: GrantFiled: May 27, 2010Date of Patent: May 7, 2013Assignee: Honeywell International Inc.Inventors: Ryan Hulse, Hang T. Pham, Rajiv Ratna Singh, Hsueh Sung Tung, Daniel C. Merkel, Konstantin A. Pokrovski
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Publication number: 20130102814Abstract: A process is disclosed for making CF3CH2CHF2, CF3CH?CHF and/or CF3CH?CHCl. The process involves reacting at least one starting material selected from the group consisting of halopropanes of the formula CX3CHClCH2X, halopropenes of the formula CX3CCl?CH2 and halopropenes of the formula CX2?CClCH2X, wherein each X is independently F or Cl, with HF in a reaction zone to produce a product mixture comprising HF, HCl, CF3CH2CHF2, CF3CH?CHF and CF3CH?CHCl; and recovering the CF3CH2CHF2, CF3CH?CHF and/or CF3CH?CHCl from the product mixture. Also disclosed is a process for making CF3CF2CH3 and/or CF3CF?CH2.Type: ApplicationFiled: November 29, 2012Publication date: April 25, 2013Applicant: E I Du Pont De Nemours and CompanyInventor: E I Du Pont De Nemours and Company
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Patent number: 8426655Abstract: 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: GrantFiled: March 11, 2011Date of Patent: April 23, 2013Assignee: Honeywell International Inc.Inventors: Hsueh Sung Tung, Haiyou Wang
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Patent number: 8378158Abstract: 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: October 5, 2011Date of Patent: February 19, 2013Assignee: Honeywell International Inc.Inventors: Ryan Hulse, Hang T. Pham
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Publication number: 20130023703Abstract: A process for the selective dehydrofluorination of hydrochlorofluoroalkanes and novel hydrochlorofluoroalkenes is described wherein an effective amount of a catalytically active metal compound is applied which is selected from the group consisting of AlF3??, MgAlxF2+3x?? and MgZryF2+4y??, wherein x and y have, independently of one another, values in the range of from 0 to 0.33 and ? has a value in the range of from 0 to 0.1. Certain hydrofluorochloroalkenes are also described, as well as their use as intermediates in chemical reactions.Type: ApplicationFiled: March 31, 2011Publication date: January 24, 2013Applicant: SOLVAY SAInventors: Johannes Eicher, Ercan Uenveren, Erhard Kemnitz
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Patent number: 8344191Abstract: The present invention provides a process for producing 2,3,3,3-tetrafluoropropene represented by the formula CF3CF?CH2, comprising contacting a fluorine-containing propane represented by the formula CF2XCFYCH2Z, wherein X is Cl, Br, or I; one of Y and Z is H, and the other is F, Cl, Br, or I, with at least one catalyst selected from the group consisting of chromium oxides, fluorinated chromium oxides, and iron fluorides in a gas phase. According to the process of the invention, 2,3,3,3-tetrafluoropropene can be easily produced under economically advantageous conditions.Type: GrantFiled: July 24, 2009Date of Patent: January 1, 2013Assignee: Daikin Industries, Ltd.Inventors: Masatoshi Nose, Daisuke Karube, Akinari Sugiyama, Takashi Shibanuma, Takehiro Chaki
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Patent number: 8252965Abstract: The invention provides a method for separating halocarbons. In particular, a method for separating 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) from 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) based on differences in melting points of these compounds. More particularly the invention pertains to a method for separating HCFC-244bb from HCFO-1233xf which are useful as intermediates in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf).Type: GrantFiled: August 12, 2009Date of Patent: August 28, 2012Assignee: Honeywell International Inc.Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski
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Publication number: 20120190901Abstract: Provided is a process for purifying an organic feedstock comprising (a) distilling a raw organic feedstock comprising hydrogen fluoride, 2-chloro-1,1,1,2-tetrafluoropropane, and 2-chloro-3,3,3-trifluoropropene to produce a first distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a first bottoms stream rich in hydrogen fluoride; (b) cooling said first distillate stream to produce an intermediate composition comprising an organic layer rich in 2-chloro-1,1,1,2-tetrafluoropropane and 2-chloro-3,3,3-trifluoropropene, and an acid layer rich in hydrogen fluoride; and, optionally but preferably, (c) distilling said organic layer to produce a second distillate stream comprising an azeotrope-like composition of 2-chloro-1,1,1,2-tetrafluoropropane, 2-chloro-3,3,3-trifluoropropene, and hydrogen fluoride, and a second bottoms stream comprising a purified organic feedstock substantially free of hydrogen fluoride.Type: ApplicationFiled: March 19, 2012Publication date: July 26, 2012Applicant: HONEYWELL INTERNATIONAL INC.Inventors: DANIEL C. MERKEL, KONSTANTIN A. POKROVSKI, HSUEH SUNG TUNG
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Patent number: 8207383Abstract: The present invention provides a process for preparing 1234yf, comprising: (i) contacting 1233xf 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, unreacted 1233xf and 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: June 26, 2012Assignee: Arkema FranceInventors: Dominique Deur-Bert, Laurent Wendlinger, Anne Pigamo
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Patent number: 8207384Abstract: 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: GrantFiled: December 23, 2010Date of Patent: June 26, 2012Assignee: Arkema FranceInventors: Laurent Wendlinger, Anne Pigamo, Dominique Deur-Bert