Catalyst Utilized Patents (Class 570/156)
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Patent number: 11691935Abstract: The production method according to the present disclosure comprises obtaining a product containing the fluoroethane from a fluoroethylene by a reaction in the presence of catalysts. Each catalyst is formed by supporting a noble metal on a carrier. A reactor for performing the reaction is filled with a catalyst having a noble metal concentration of C1 mass % based on the entire catalyst and a catalyst having a noble metal concentration of C2 mass % based on the entire catalyst to form an upstream portion and a downstream portion, respectively; and C1<C2. The reaction is performed by bringing the fluoroethylene represented by formula (3) and hydrogen gas into contact with the upstream portion and the downstream portion in this order.Type: GrantFiled: June 17, 2021Date of Patent: July 4, 2023Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Tomoyuki Iwamoto, Takashi Usui, Takehiro Chaki, Tsubasa Nakaue, Kazuhiro Takahashi
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Patent number: 11377408Abstract: 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: October 8, 2019Date of Patent: July 5, 2022Assignee: The Boeing CompanyInventors: Kimberly-Alice D. Gregersen, James Craig Moreland, Ekaterina A. Badaeva, Andrew M. Zweig
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Patent number: 11358919Abstract: The invention relates to a process comprising contacting a composition comprising a (hydro)halocarbon and a compound of formula Rf—C?CX with a basic solution comprising an hydroxide, an alkoxide and/or an amide to reduce the concentration of Rf—C?CX, wherein Rf is a perfluorinated alkyl group and X is H, F, Cl, Br, or I. The invention further relates to process for preparing a (hydro)halocarbon comprising (i) converting a starting material, optionally in the presence of HF and/or a catalyst, to a composition comprising the (hydro)halocarbon and a compound of formula Rf—C?CX, wherein Rf is a perfluorinated alkyl group and X is H, F, Cl, Br, or I; (ii) contacting the composition with a basic solution comprising an hydroxide, an alkoxide and/or an amide to reduce the concentration of the compound of formula Rf—C?CX; and (iii) recovering the (hydro)halocarbon.Type: GrantFiled: September 11, 2020Date of Patent: June 14, 2022Assignee: Mexichem Fluor S.A. de C.V.Inventor: Andrew Paul Sharratt
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Patent number: 11332423Abstract: This invention relates to a method for preparing 1,2-difluoroethylene and/or 1,1,2-trifluoroethane, comprising a step of performing at least one fluorination reaction by bringing at least one halide selected from the group consisting of haloethanes represented by general formula (1) CHX1X2CH2X3 (wherein X1, X2, and X3 are the same or different, and represent Cl, Br, or F) and haloethylenes represented by general formula (2) CHX4?CHX5 (wherein X4 and X5 are the same or different, and represent Cl, Br or F, with the proviso that the case in which X4 and X5 are both F is excluded).Type: GrantFiled: April 25, 2019Date of Patent: May 17, 2022Assignee: DAIKIN INDUSTRIES, LTD.Inventor: Yuzo Komatsu
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Patent number: 11192839Abstract: The present invention relates to a process for producing 2-chloro-3,3,3-trifluoropropene, comprising the steps: i) providing a stream A comprising at least one chlorinated compound selected from the group consisting of 2,3-dichloro-1,1,1-trifluoropropane, 1,1,1,2,3-pentachloropropane, 1,1,2,3-tetrachloropropene and 2,3,3,3-tetrachloropropene; and ii) in an adiabatic reactor comprising a fixed bed composed of an inlet and an outlet, bringing said stream A into contact, in the presence or absence of a catalyst, with HF in order to produce a stream B comprising 2-chloro-3,3,3-trifluoropropene, characterized in that the temperature at the inlet of the fixed bed of said adiabatic reactor is between 300° C. and 400° C. and the longitudinal temperature difference between the inlet of the fixed bed and the outlet of the fixed bed of said reactor is less than 20° C.Type: GrantFiled: June 6, 2019Date of Patent: December 7, 2021Assignee: Arkema FranceInventors: Bertrand Collier, Dominique Deur-Bert, Anne Pigamo, Audrey Riehl, Laurent Wendlinger
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Patent number: 11084768Abstract: A process for the production of 2,3,3,3-tetrafluoropropene including the stages: i) in a first reactor, bringing a stream A including 2-chloro-3,3,3-trifluoropropene into contact with hydrofluoric acid in the gas phase in the presence of a catalyst in order to produce a stream B including 2,3,3,3-tetrafluoropropene, HCl, HF and unreacted 2-chloro-3,3,3-trifluoropropene; and ii) in a second reactor, bringing hydrofluoric acid into contact, in the gas phase in the presence or not of a catalyst, with a stream including at least one chlorinated compound selected from the group of 1,1,1,2,3-pentachloropropane, 2,3-dichloro-1,1,1-trifluoropropane, 2,3,3,3-tetrachloropropene and 1,1,2,3-tetrachloropropene, in order to produce a stream C including 2-chloro-3,3,3-trifluoropropene, wherein the stream B obtained in stage i) feeds the second reactor used for stage ii); and wherein the electrical conductivity of the stream A provided in stage i) is less than 15 mS/cm.Type: GrantFiled: March 4, 2019Date of Patent: August 10, 2021Assignee: ARKEMA FRANCEInventors: Laurent Wendlinger, Dominique Deur-Bert, Anne Pigamo
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Patent number: 11028029Abstract: The present invention relates to a process for the production of 2,3,3,3-tetrafluoropropene comprising the stages: i) in a first reactor, bringing 2-chloro-3,3,3-trifluoropropene into contact with hydrofluoric acid in the gas phase in the presence of a catalyst, in order to produce a stream A comprising 2,3,3,3-tetrafluoropropene, HF and unreacted 2-chloro-3,3,3-trifluoropropene; and ii) in a second reactor, bringing hydrofluoric acid into contact, in the gas phase in the presence or absence of a catalyst, with at least one chlorinated compound selected from the group consisting of 1,1,1,2,3-pentachloropropane, 2,3-dichloro-1,1,1-trifluoropropane, 2,3,3,3-tetrachloropropene and 1,1,2,3-tetrachloropropene, in order to produce a stream B comprising 2-chloro-3,3,3-trifluoropropene, characterized in that the stream A obtained in stage i) feeds said second reactor used for stage ii); and in that the pressure at the inlet of said first reactor of stage i) is greater than the pressure at the inlet of said second reaType: GrantFiled: November 8, 2018Date of Patent: June 8, 2021Assignee: Arkema FranceInventors: Bertrand Collier, Dominique Deur-Bert, Anne Pigamo, Laurent Wendlinger
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Patent number: 11028027Abstract: The present invention relates to a process for the production of 2-chloro-3,3,3-trifluoropropene comprising the stages of: a) providing a stream A comprising at least one of the compounds selected from the group consisting of 2,3-dichloro-1,1,1-trifluoropropane, 1,1,1,2,3-pentachloropropane, 1,1,2,3-tetrachloropropene and 2,3,3,3-tetrachloropropene; b) in a reactor, bringing said stream A into contact with HF in the presence or absence of a catalyst in order to produce a stream B comprising 2-chloro-3,3,3-trifluoropropene; characterized in that the electrical conductivity of said stream A provided in stage a) is less than 15 mS/cm.Type: GrantFiled: March 4, 2019Date of Patent: June 8, 2021Assignee: ARKEMA FRANCEInventors: Laurent Wendlinger, Dominique Deur-Bert, Anne Pigamo
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Patent number: 10934233Abstract: The present invention relates to a process for the preparation of haloethylenes, and preferably perhaloethylenes, by the gas-phase dechlorination of haloethanes in the presence of a catalyst and optionally in the presence of an alkene or an alkane. In particular aspects, the invention relates to a gas-phase process for preparing chlorotrifluoroethylene (CTFE). More particularly, the present invention relates to a gas-phase process for preparing CTFE from 1,1,2-trichloro-1,2,2-trifluoroethane (CFC-113) by dechlorination in the presence of an alkene or an alkane and a catalyst.Type: GrantFiled: February 5, 2019Date of Patent: March 2, 2021Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Haridasan K. Nair, Rajiv Ratna Singh, Glenn Matthies
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Patent number: 10927061Abstract: The present specification relates to a dehydrohalogenation process comprising contacting a halofluoroalkane of formula RCXYCZQT with a caustic agent optionally in the presence of an amine in an aqueous solvent in the absence of a catalyst while providing mixing with power input ranging from about 0.1 to about 50 HP/1000 gallons to produce a product comprising a fluoroolefin of formula RCX?CZQ, wherein R is perfluorinated alkyl group and X, Z and Q are independently H or halogen, and one of Y and T is H and the other is halogen.Type: GrantFiled: September 9, 2016Date of Patent: February 23, 2021Assignee: THE CHEMOURS COMPANY FC, LLCInventors: Xuehui Sun, Karl Krause
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Patent number: 10919824Abstract: The present invention relates to a process for modifying the fluorine distribution in a hydrocarbon compound in the presence of a catalyst, characterized by the use, as catalyst, of a solid composition comprising at least one component containing chromium oxyfluoride or fluoride of empirical formula CrxM(1-x)OrFs, where 2r+s is greater than or equal to 2.9 and less than 6, M is a metal chosen from columns 2 to 12 of the Periodic Table of the Elements, x has a value from 0.9 to 1, s is greater than 0 and less than or equal to 6 and r is greater than or equal to 0 and less than 3, the said solid composition having a crystallinity of less than 20% by weight. The present invention also relates to the solid composition per se.Type: GrantFiled: August 28, 2017Date of Patent: February 16, 2021Assignee: ARKEMA FRANCEInventors: Dominique Garrait, Anne Pigamo, Laurent Wendlinger
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Patent number: 10899686Abstract: The present invention provides an integrated process for preparing 2,3,3, 3-tetrafluoropropene (1234yf), the process comprising: (a) vapour phase catalytic fluorination of a first composition comprising 3,3,3-trifluoro-2-chloro-prop-1-ene (CF3C—CNCH2, 1233xf) with hydrogen fluoride (HF) in a fluorination reactor to produce a fluorination product stream comprising 1,1,2,2-pentafluoropropane (245cb), HF and HCI; (b) vapour phase catalytic dehydrofluorination composition comprising 245cb in a dehydrofluorination reactor to produce a dehydrofluorination product stream comprising 1234yf and HF; wherein the fluorination product stream and the dehydrofluorination product stream are combined and subjected to (c) purification to produce a composition comprising 245cb and a 1234yf product stream.Type: GrantFiled: July 14, 2016Date of Patent: January 26, 2021Assignee: MEXICHEM FLUOR S.A. DE C.V.Inventors: Sheryl Louise Johnson, Stephen Andrew Flaherty, James Henry Murray, Fiona Louise Smith, Jonathan Junhay Man, Clive Robert Giddis
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Patent number: 10843988Abstract: A method for manufacturing 1-chloro-3,3,3-trifluoropropene (1230zd) is provided. The method includes contacting a halogenated hydrocarbon compound having a carbon number of 3 and represented by a general formula (1) with a metal catalyst in a gas phase. 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 16, 2019Date of Patent: November 24, 2020Assignee: CENTRAL GLASS COMPANY, LIMITEDInventors: Masamune Okamoto, Satoru Okamoto
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Patent number: 10669219Abstract: The present invention provides a process for preparing 1,1,1,2,2-pentafluoropropane (245cb), the process comprising gas phase catalytic dehydrochlorination of a composition comprising 1,1,1-trifluoro-2,3-dichloropropane (243db) to produce an intermediate composition comprising 3,3,3-trifluoro-2-chloro-prop-1-ene (CF3CCI?CH2, 1233xf), hydrogen chloride (HCI) and, optionally, air; and gas phase catalytic fluorination with hydrogen fluoride (HF) of the intermediate composition to produce a reactor product composition comprising 245cb, HF, HCI and air; wherein the process is carried out with a co-feed of air.Type: GrantFiled: July 14, 2016Date of Patent: June 2, 2020Assignee: MEXICHEM FLUOR S.A. DE C.V.Inventors: Sheryl Louise Johnson, Stephen Andrew Flaherty, Clive Robert Giddis
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Patent number: 10611708Abstract: A method for producing 1,2-dichloro-3,3,3-trifluoropropene according to the present invention includes the step of reacting 1,1,2,3,3-pentachloropropene with a fluorinating agent where hydrogen fluoride is used as the fluorinating agent.Type: GrantFiled: April 10, 2017Date of Patent: April 7, 2020Assignee: Central Glass Company, LimitedInventors: Kei Matsunaga, Hideaki Imura, Masatomi Kanai, Masahiko Tani, Naoto Takada, Kohei Sumida, Satoru Okamoto
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Patent number: 10590049Abstract: The present invention provides a method for producing tetrafluoropropene represented by formula (1) by bringing monochlorotrifluoropropene represented by formula (2) into contact with anhydrous hydrogen fluoride in the presence of a catalyst, the method being capable of maintaining the conversion of the starting material and the selectivity for the target product within an excellent range, while reducing degradation of the catalyst to maintain the reaction for a long time.Type: GrantFiled: February 3, 2017Date of Patent: March 17, 2020Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Shun Ohkubo, Takashi Usui, Takehiro Chaki, Daisuke Karube
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Patent number: 10577296Abstract: The present application provides a process of preparing 3,3,3-trifluoroprop-1-ene, comprising reacting 3-chloro-1,1,1-trifluoropropane with a base in an aqueous solvent component in the absence of a phase transfer catalyst.Type: GrantFiled: March 9, 2018Date of Patent: March 3, 2020Assignee: THE CHEMOURS COMPANY FC, LLCInventors: Xuehui Sun, Karl Robert Krause
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Patent number: 10351495Abstract: A process is provided comprising contacting and reacting the compound CF3CF2CHXCl, wherein X is H or Cl, or the compound CF3CF?CXCl, wherein X is H or Cl, with hydrogen in the presence of a catalyst consisting essentially of Cu, Ru, Cu—Pd, Ni—Cu, and Ni—Pd, to obtain as a result thereof reaction product comprising hydrofluoropropenes or intermediates convertible to said hydrofluoropropenes, notably CF3CF?CH2 and CF3CH?CHF.Type: GrantFiled: October 17, 2017Date of Patent: July 16, 2019Assignee: THE CHEMOURS COMPANY FC, LLCInventor: Xuehui Sun
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Patent number: 10207971Abstract: The invention relates to a composition comprising at least 99% by weight of 1,1,1,2,3-pentachloropropane, and comprising at least one compound chosen from a list of additional compounds consisting of trichloropropanes, tetrachloropropanes, pentachloropropanes other than 1,1,1,2,3-pentachloropropane, hexachloropropanes, heptachloropropanes, dichloropropenes, trichloropropenes, tetrachloropropenes, pentachloropropenes and hexachloropropene, said compound being present in the composition in a weight content of less than or equal to 500 ppm. The invention also relates to the use of this composition for manufacturing 2,3,3,3-tetrafluoropropene.Type: GrantFiled: October 7, 2015Date of Patent: February 19, 2019Assignee: ARKEMA FRANCEInventors: Dominique Deur-Bert, Laurent Wendlinger, Bertrand Collier
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Patent number: 10202321Abstract: Disclosed is a method of simultaneously preparing 1,1,1-trifluoro-2-chloropropene and 1,1,1,2-tetrafluoropropene, the method including i) a step of elevating a temperature of a reactor charged with a gas phase catalyst up to a reaction temperature; ii) a step of feeding 1,1,1-trifluoro-2,3-dichloropropane and 2-chloro-1,1,1,2-tetrafluoropropane into the reactor, the temperature of which has been elevated; iii) a step of performing dehydrochlorination while maintaining the temperature of the reactor; and iv) a step of performing washing and distillation after the dehydrochlorination. In accordance with the present disclosure, a high-efficient gas-phase process of continuously, simultaneously preparing 1,1,1-trifluoro-2-chloropropene and 1,1,1,2-tetrafluoropropene is provided.Type: GrantFiled: May 3, 2018Date of Patent: February 12, 2019Assignee: FOOSUNG CO., LTD.Inventors: Ook Jae Cho, Bong Seok Kim, Dong Hyuk Park, Su Jin Park, Jin A Jung, Dae Woo Kim
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Patent number: 10183903Abstract: The present invention discloses a method for preparing 2,3,3,3-tetrafluoropropene using methylmagnesium chloride, comprising the following steps: 1) preparing 1,1,2-trifluoropropene (CH3CF?CF2); 2) preparing 1,1,1,2,2-pentafluoropane (CF3CF2CH3); 3) preparing 2,3,3,3-tetrafluoropropene (CF3CF?CH2). In the present invention, using a Grignard reagent, namely methylmagnesium chloride, and tetrafluoroethylene as starting raw materials, 2,3,3,3-tetrafluoropropene is prepared by three steps of nucleophilic addition-elimination, fluorine addition, and dehydrofluorination in sequence. The process flow is relatively short, and the product yield is high.Type: GrantFiled: December 24, 2015Date of Patent: January 22, 2019Assignee: JUHUA GROUP TECHNOLOGY CENTERInventors: Hongfeng Li, Shuhua Wang, Xiaobo Xu, Liyong Ma
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Patent number: 10138403Abstract: There are provided a composition for a heat cycle system containing a working medium for heat cycle that has a low global warming potential and high stability, which can be used as a substitute for HFC-134a and HFC-245fa, and a heat cycle system using this composition. The composition for a heat cycle system contains: a working medium for heat cycle containing 1-chloro-2,3,3,3-tetrafluoropropene; and a stabilizer suppressing deterioration of the working medium for heat cycle such as an oxidation resistance improver, a heat resistance improver, or a metal deactivator, and the heat cycle system uses this composition for a heat cycle system.Type: GrantFiled: October 24, 2017Date of Patent: November 27, 2018Assignee: AGC Inc.Inventors: Mai Tasaka, Masato Fukushima, Hiroaki Mitsuoka
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Patent number: 10118879Abstract: A method for conversion of a composition containing HCFO-1233zd(Z) and HCFC-244fa to form HCFO-1233zd(E) by reacting a mixture including HCFO-1233zd(Z) and HCFC-244fa in a vapor phase in the presence of a catalyst to simultaneously isomerize HCFO-1233zd(Z) to form HCFO-1233zd(E) and dehydrohalogenate HCFC-244fa to form HCFO-1233zd(E). The catalyst may be a chromium-based catalyst such as chromium trifluoride, chromium oxyfluoride, or chromium oxide, for example.Type: GrantFiled: October 26, 2017Date of Patent: November 6, 2018Assignee: Honeywell International Inc.Inventors: Christian Jungong, Daniel C. Merkel
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Patent number: 10081749Abstract: A composition is provided containing HFO-1123 having a low GWP, which is useful as a heat transfer composition, an aerosol sprayer, a foaming agent, a blowing agent, a solvent or the like. A composition containing HFO-1123, and at least one first compound selected from the group consisting of HFO-1132, HFO-1132a, CFO-1113, HCFO-1122, HCFO-1122a, HFC-143 and methane.Type: GrantFiled: September 11, 2015Date of Patent: September 25, 2018Assignee: AGC Inc.Inventors: Tomoaki Taniguchi, Hidekazu Okamoto, Shoji Furuta, Yu Takeuchi
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Patent number: 10053404Abstract: 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: April 11, 2016Date of Patent: August 21, 2018Assignee: Arkema FranceInventors: Dominique Deur-Bert, Bertrand Collier, Laurent Wendlinger
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Patent number: 9994503Abstract: A method for producing 1,1,1,2-tetrafluoropropene and/or 1,1,1,2,3-pentafluoropropene using a single set of four unit operations, the unit operations being (1) hydrogenation of a starting material comprising hexafluoropropene and optionally recycled 1,1,1,2,3-pentafluoropropene; (2) separation of the desired intermediate hydrofluoroalkane, such as 1,1,1,2,3,3-hexafluoropropane and/or 1,1,1,2,3-pentafluoropropane; (3) dehydrofluorination of the intermediate hydrofluoroalkane to produce the desired 1,1,1,2-tetrafluoropropene and/or 1,1,1,2,3-pentafluoropropene, followed by another separation to isolate the desired product and, optionally, recycle of the 1,1,1,2,3-pentafluoropropene.Type: GrantFiled: April 4, 2016Date of Patent: June 12, 2018Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Yuon Chiu, Stephen A. Cottrell, Hsueh Sung Tung, Haluk Kopkalli, Gustavo Cerri
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Patent number: 9890097Abstract: Disclosed are the combinations containing Z and E stereoisomers of hydrofluoroolefins where the more toxic isomer is less than about 30% weight of the combination (vs the sum of Z+E), to minimize the toxicity impact in the applications they will be used for such as cooling and heat fluids, foams blowing agents or solvents. Also disclosed are means to obtain combinations containing Z and E stereoisomers of hydrofluoroolefins.Type: GrantFiled: September 30, 2015Date of Patent: February 13, 2018Assignee: Arkema Inc.Inventors: Philippe Bonnet, Maher Y. Elsheikh
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Patent number: 9878969Abstract: Disclosed is a process for the preparation of 1,3,3,3-tetrafluoropropene, comprising: (a) a compound having the formula CF3-xClxCHClCHF2-yCly and in the presence of a compound catalyst, undergoes, through n serially-connected reactors, gas-phase fluorination with hydrogen fluoride, producing 1,2,3-trichloro-1,1,3-trifluoropropane, and 1,2-dichloro-1,1,3,3-tetrafluoropropane; in said formula, x=1, 2 or 3; y=1 or 2, and 3?x+y?5; (b) 1,2,3-trichloro-1,1,3-trifluoropropane, and 1,2-dichloro-1,1,3,3-tetrafluoropropane undergo, in the presence of a dehalogenation catalyst, gas-phase dehalogenation with hydrogen, producing 3-chloro-1,3,3-trifluoropropene, and 1,1,3,3-tetrafluoropropene; (c) 3-chloro-1,3,3-trifluoropropene and 1,1,3,3-tetrafluoropropene undergo, in the presence of a fluorination catalyst, gas-phase fluorination with hydrogen fluoride, producing 1,3,3,3-tetrafluoropropene. The present invention is primarily used to produce 1,3,3,3-tetrafluoropropene.Type: GrantFiled: February 5, 2015Date of Patent: January 30, 2018Assignee: Xi'an Modern Chemistry Research InstituteInventors: Jian Lv, Hui Ma, Yujie Gu, Bo Wang, Yue Qin, Zhenhua Zhang, Zhijun Hao, Chunying Li, Fengxian Li, Jing Lv, Yanbo Bai
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Process for the joint preparation of 1, 3, 3, 3-tetrafluoropropene and 2, 3, 3, 3-tetrafluoropropene
Patent number: 9873649Abstract: A process for the joint preparation of 1,3,3,3-tetrafluoropropene and 2,3,3,3-tetrafluoropropene, comprising: (a) starting materials comprising at least one compound having the structure of formula I, II or III are reacted with hydrogen fluoride, producing 1,2,3-trichloro-3,3-difluoropropene, 1,2,3-trichloro-1,1,2-trifluoropropane, and 1,2,3-trichloro-1,1,3-trifluoropropane; in the compounds of said formulae CF2-mClm?CCl—CHF2-nCln (Formula I), CF3-pClpCHCl?CH2Cl (Formula II), and CF3-xClxCF2-yClyCHF2-zClz (Formula III), m=0, 1, 2; n=1, 2; p=2, 3; x=1, 2, 3; y=1, 2; z=1, 2 and 4?x+y+z?6; (b) the 1,2,3-trichloro-3,3-difluoropropene, 1,2,3-trichloro-1,1,2-trifluoropropane and 1,2,3-trichloro-1,1,3-trifluoropropane undergo dechlorination, producing 3-chloro-3,3-difluoropropyne, 3-chloro-2,3,3-trifluoropropene and 3-chloro-1,3,3-trifluoropropene; and (c) the 3-chloro-3,3-difluoropropyne, 3-chloro-2,3,3-trifluoropropene and 3-chloro-1,3,3-trifluoropropene are reacted with hydrogen fluoride, simultaneously yieldingType: GrantFiled: February 5, 2015Date of Patent: January 23, 2018Assignee: Xi'an Modern Chemistry Research InstituteInventors: Jian Lv, Hui Ma, Bo Wang, Wei Zhang, Zhiqiang Yang, Yujie Gu, Wei Mao, Jijun Zeng, Xiaobo Tang, Zhenhua Zhang -
Patent number: 9809515Abstract: A method for producing a tetrafluoroolefin, such as 2,3,3,3-tetrafluoropropene (HFO-1234yf), comprises dehydrofluorinating a pentafluoroalkane in a gas phase in the presence of a catalyst comprising chromium oxyfluoride. In a preferred embodiment, 2,3,3,3-tetrafluoropropene (HFO-1234yf) is produced by forming a catalyst comprising chromium oxyfluoride by calcining CrF3.xH2O, where x is 1-10, in the presence of a flowing gas comprising nitrogen to form a calcined chromium oxyfluoride, and dehydrofluorinating 1,1,1,2,2-pentafluoropropane (HFC-245cb) in a gas phase in the presence of the catalyst to form the 2,3,3,3-tetrafluoropropene (HFO-1234yf).Type: GrantFiled: September 29, 2016Date of Patent: November 7, 2017Assignee: Arkema Inc.Inventors: Maher Y. Elsheikh, Philippe Bonnet, Olga C. N. Keeley, Benjamin Bin Chen
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Patent number: 9802878Abstract: A method to stably produce trifluoroethylene with a high selectivity by reacting 1,1,1,2-tetrafluoroethane with a solid reactant and suppressing the formation of by-products such as polymer carbon is provided. In the method, a material gas containing 1,1,1,2-tetrafluoroethane passes through a layer consisting of a particulate solid reactant having an average particle size of from 1 ?m to 5,000 ?m to bring the solid reactant and 1,1,1,2-tetrafluoroethane into contact with each other in a state where the layer consisting of the solid reactant is fluidized.Type: GrantFiled: July 25, 2016Date of Patent: October 31, 2017Assignee: Asahi Glass Company, LimitedInventors: Masahiko Nakamura, Hidekazu Okamoto
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Patent number: 9724684Abstract: A dehydrochlorination process is disclosed. The process involves contacting RfCHClCH2Cl with a chromium oxyfluoride catalyst in a reaction zone to produce a product mixture comprising RfCCl?CH2, wherein Rf is a perfluorinated alkyl group.Type: GrantFiled: February 16, 2012Date of Patent: August 8, 2017Assignee: THE CHEMOURS COMPANY FC, LLCInventor: Mario Joseph Nappa
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Patent number: 9701599Abstract: The invention relates to a process to prepare 2-chloro-3,3,3-trifluoropropene (HCO-1233xf) or 2-chloro-1,1,12-tetrafluoropropane (HCFC-244bb) using dichloro-trifluoropropanes and/or trichloro-difluoropropanes, and to prepare 2-chloro-3,3,3-trifluoropropene (HCO-1233xf) using various 242 and 243 isomers.Type: GrantFiled: June 23, 2016Date of Patent: July 11, 2017Assignee: HONEYWELL INTERNATIONAL. INC.Inventors: Haiyou Wang, Hsueh Sung Tung, Selma Bektesevic
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Patent number: 9676687Abstract: The invention relates to a process to prepare tetrahalopropenes, such as 2-chloro-3,3,3-trifluoropropene (1233xf). The process comprises atomizing a feed material, such as 1,1,2,3-tetrachloropropene (1230xa) and the like, and mixing it with superheated HF to form a vaporized composition of feed material and HF with substantially instantaneous contact with a vapor phase fluorination catalyst. The invention extends catalyst life and forestalls catalyst deactivation.Type: GrantFiled: April 27, 2016Date of Patent: June 13, 2017Assignee: HONEYWELL INTERNATIONAL. INC.Inventors: Daniel C. Merkel, Hsueh Sung Tung, Haiyou Wang, Haluk Kopkalli, Yuon Chiu
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Patent number: 9643903Abstract: Disclosed is process for the production of (E) 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E)) by conducting a continuous reaction without the use of a catalyst. Also disclosed is an integrated system for producing hydrofluoro olefins, particularly 1233zd(E). The manufacturing process includes six major unit operations: (1) a fluorination reaction of HCC-240fa (in continuous or semi-batch mode) using HF with simultaneous removal of by-product HCl and the product 1233zd(E); (2) recycle of unreacted HCC-240fa and HF together with under-fluorinated by-products back to (1); (3) separation and purification of by-product HCl; (4) separation of excess HF back to (1); (5) purification of final product, 1233zd(E); and (6) isomerization of by-product 1233zd(Z) to 1233zd(E) to maximize the process yield.Type: GrantFiled: March 4, 2014Date of Patent: May 9, 2017Assignee: Honeywell International Inc.Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Hsueh Sung Tung
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Patent number: 9567274Abstract: Process of catalytic fluorination in liquid phase of product 2-chloro-3,3,3-trifluoropropene into product 2-chloro-1,1,1,2-tetrafluoropropane, with an ionic liquid based catalyst. Process for manufacturing 2,3,3,3-tetrafluoropropene.Type: GrantFiled: December 28, 2015Date of Patent: February 14, 2017Assignee: Arkema FranceInventors: Anne Pigamo, Laurent Wendlinger, Philippe Bonnet
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Patent number: 9567275Abstract: The invention relates to a process for preparing a C3-6 (hydro)fluoroalkene comprising dehydrohalogenating a C3-6 hydro(halo)fluoroalkane in the presence of a zinc/chromia catalyst, wherein the C3-6 (hydro)fluoroalkene produced is isomerized in the presence of the zinc/chromia catalyst.Type: GrantFiled: October 6, 2015Date of Patent: February 14, 2017Assignee: MEXICHEM AMANCO HOLDING S.A. DE C.V.Inventors: Andrew Paul Sharratt, Leslie Richard Seddon
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Patent number: 9512053Abstract: Processes for the production of chlorinated propenes are provided. The processes make use of 1,2-dichloropropane as a starting material and subject a feedstream comprising the same to an ionic chlorination process. At least a portion of any tri- and tetrachlorinated propanes not amenable to ionic chlorination conditions are removed from the ionic chlorination product stream, or, are subjected to chemical base dehydrochlorination step. In this way, recycle of intermediates not amenable to ionic chlorination reactions is reduced or avoided, as is the buildup of these intermediates within the process. Selectivity and, in some embodiments, yield of the process is thus enhanced.Type: GrantFiled: December 18, 2013Date of Patent: December 6, 2016Assignee: BLUE CUBE IP LLCInventors: Max M. Tirtowidjojo, David S. Laitar, Barry B. Fish, Matthew L. Grandbois
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Patent number: 9492816Abstract: A method for producing a tetrafluoroolefin, such as 2,3,3,3-tetrafluoropropene (HFO-1234yf), comprises dehydrofluorinating a pentafluoroalkane in a gas phase in the presence of a catalyst comprising chromium oxyfluoride. In a preferred embodiment, 2,3,3,3-tetrafluoropropene (HFO-1234yf) is produced by forming a catalyst comprising chromium oxyfluoride by calcining CrF3?xH2O, where x is 1-10, in the presence of a flowing gas comprising nitrogen to form a calcined chromium oxyfluoride, and dehydrofluorinating 1,1,1,2,2-pentafluoropropane (HFC-245cb) in a gas phase in the presence of the catalyst to form the 2,3,3,3-tetrafluoropropene (HFO-1234yf).Type: GrantFiled: May 3, 2011Date of Patent: November 15, 2016Assignee: Arkema Inc.Inventors: Maher Y. Elsheikh, Philippe Bonnet, Olga C. N. Keeley, Benjamin Bin Chen
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Patent number: 9458070Abstract: Disclosed is an HFO-1234ze preparation process. The present invention is realized by loading two fluorination catalysts into the same reactor, and controlling the temperature in each section. The preparation process of the present invention is of moderate reaction condition, stable catalyst activity, and simple process.Type: GrantFiled: December 17, 2013Date of Patent: October 4, 2016Assignees: SINOCHEM MODERN ENVIRONMENTAL PROTECTION CHEMICALS (XI'AN) CO., LTD., Sinochem Lantian Co., Ltd.Inventors: Lei Xu, Gang Yang, Huie Yang, Shukang Chen, Zhixia Zhao
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Patent number: 9447003Abstract: The present invention relates to the preparation of trifluoroethylene (VF3 or TrFE) by hydrogenolyzis of chlorotrifluoroethylene (CTFE) in the gaseous phase over a group VIII metal catalyst deposited on a support. This method can be used to obtain VF3 in an economical manner in conditions which minimize the risk of explosion of this molecule. Using a catalyst containing a group VIII metal and, more specifically, containing Pd deposited on a support and a specific series of steps of separation and purification makes it possible to obtain excellent CTFE conversion rates and high selectivity in VF3 at atmospheric pressure and at low temperatures.Type: GrantFiled: February 22, 2013Date of Patent: September 20, 2016Assignee: ARKEMA FRANCEInventors: Philippe Leduc, Thierry Lannuzel, Dominique Garrait, Serge Hub, Emmanuel Guiraud, Fabrice Domingues Dos Santos
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Patent number: 9403742Abstract: A catalytic process for the synthesis of trifluoroethylene from chlorotrifluoroethylene which comprises contacting chlorotrifluoroethylene with hydrogen in the presence of a catalyst consisting of palladium or platinum supported on extruded activated carbon.Type: GrantFiled: June 20, 2014Date of Patent: August 2, 2016Assignee: SOLVAY SPECIALTY POLYMERS ITALY S.P.A.Inventors: Stefano Millefanti, Vito Tortelli, Giuseppe Marchionni
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Patent number: 9399609Abstract: The present process relates to a method for minimizing the formation of 1,1,1,2,2-pentafluoropropane in a liquid phase reaction of 2-chloro-3,3,3-trifluoropropene and HF in the presence of a hydrofluorination catalyst comprising: (a) reacting HF with sufficient amount of 2-chloro-3,3,3-trifluoropropene in the presence of a hydrofluorination catalyst under conditions effective to form 2-chloro-1,1,1,2-tetrafluoropropane, the hydrofluorination catalyst being present in sufficient amounts to catalyze said reaction and the 2-chloro-1,1,1,2-tetrafluoropropane being formed with both a conversion of greater than 80% and a 1,1,1,2,2-pentafluoropropane selectivity lower than 20%; and (b) maintaining the 2-chloro-1,1,1,2-tetrafluoropropane being formed with both a conversion of about 80% or more and a 1,1,1,2,2-pentafluoropropane selectivity of about 20% or less by adding said hydrofluorination catalyst to the reactor in small increments.Type: GrantFiled: March 11, 2014Date of Patent: July 26, 2016Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Haiyou Wang, Daniel C. Merkel, Hsueh Sung Tung, Haluk Kopkalli
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Patent number: 9394217Abstract: The invention relates to a process to produce 244bb from 1233xf in multiple reaction zones whereby the 1233xf starting material is at least 95% converted to 244bb and by-product such as 245cb forms in amounts less than about 2%.Type: GrantFiled: March 12, 2014Date of Patent: July 19, 2016Assignee: HONEYWELL INTERNATIONAL, INC.Inventors: Yuon Chiu, Haluk Kopkalli, Robert A. Smith, Daniel C. Merkel
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Patent number: 9359274Abstract: Provided is a method for causing a dehydrofluorination reaction of 1,1,1,3,3-pentafluoropropane in the gas phase and in the presence of a catalyst thereby producing 1,3,3,3-tetrafluoropropene. In this method, the reaction is carried out at a pressure inside the reaction system of from 0.001 to 90 kPa (absolute pressure) at a reaction temperature ranging from 250 to 600° C.Type: GrantFiled: June 27, 2013Date of Patent: June 7, 2016Assignee: Centeral Glass Company, LimitedInventors: Satoshi Yoshikawa, Fuyuhiko Sakyu, Naoto Takada
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Patent number: 9302963Abstract: A method for producing 1,1,1,2-tetrafluoropropene and/or 1,1,1,2,3-pentafluoropropene using a single set of four unit operations, the unit operations being (1) hydrogenation of a starting material comprising hexafluoropropene and optionally recycled 1,1,1,2,3-pentafluoropropene; (2) separation of the desired intermediate hydrofluoroalkane, such as 1,1,1,2,3,3-hexafluoropropane and/or 1,1,1,2,3-pentafluoropropane; (3) dehydrofluorination of the intermediate hydrofluoroalkane to produce the desired 1,1,1,2-tetrafluoropropene and/or 1,1,1,2,3-pentafluoropropene, followed by another separation to isolate the desired product and, optionally, recycle of the 1,1,1,2,3-pentafluoropropene.Type: GrantFiled: August 9, 2012Date of Patent: April 5, 2016Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Yuon Chiu, Stephen A. Cottrell, Hsueh Sung Tung, Haluk Kopkalli, Gustavo Cerri
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Patent number: 9296670Abstract: A method for forming 2,3,3,3-tetrafluoropropene (HFO-1234yf) comprising providing a dehydrochlorination starting material having relatively low concentrations of 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf), especially and preferable less than about 8.0% when the dehydrochlorination reaction utilizes no substantial amount of catalyst or catalyst comprising austenitic nickel-based materials.Type: GrantFiled: February 8, 2013Date of Patent: March 29, 2016Assignee: THE CHEMOURS COMPANY FC, LLCInventors: Haiyou Wang, Hsueh S. Tung, Haluk Kopkalli, Yuon Chiu, Gustavo Cerri, Jeffrey Ball, Philip L. Da Prato, Xuehui Sun, Mario Joseph Nappa
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Patent number: 9255047Abstract: A subject-matter of the invention is a process for the preparation of 2,3,3,3-tetrafluoro-1-propene which comprises the following stages: (i) hydrogenation of hexafluoropropylene to give 1,1,1,2,3,3-hexafluoropropane; (ii) dehydrofluorination of the 1,1,1,2,3,3-hexafluoropropane obtained in the preceding stage to give 1,2,3,3,3-pentafluoro-1-propene; (iii) hydrogenation of the 1,2,3,3,3-pentafluoro-1-propene obtained in the preceding stage to give 1,1,1,2,3-pentafluoropropane; and (iv) dehydrofluorination of the 1,1,1,2,3-pentafluoropropane obtained in the preceding stage to give 2,3,3,3-tetrafluoro-1-propene. Stages (ii) and (iv) are carried out using a water and potassium hydroxide mixture with the potassium hydroxide representing between 58 and 86% by weight of the mixture and at a temperature of between 110 and 180° C.Type: GrantFiled: August 19, 2009Date of Patent: February 9, 2016Assignee: Arkema FranceInventors: Anne Pigamo, Michel Devic, Laurent Wendlinger
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Patent number: 9233897Abstract: Disclosed is an HFO-1234ze and HFC-245fa co-production preparation method. The HFO-1234ze and HFC-245fa are prepared through a two-stage gas phase fluorination reaction by using 1,1,1,3,3-pentachloropropane (HCC-240fa) as a raw material. With the processing method of the present invention, HFO-1234ze and HFC-245fa can be prepared at the same time, and the alkene is unlikely to polymerize or carbonize during the reaction, thus being suitable for industrialized promotion.Type: GrantFiled: December 17, 2013Date of Patent: January 12, 2016Assignees: SINOCHEM MODERN ENVIRONMENTAL PROTECTION CHEMICALS (XI'AN) CO., LTD., SINOCHEM LANTIAN CO., LTD.Inventors: Gang Yang, Huie Yang, Lei Xu, Hua Chai, Xintang Zhao, Wenqing Zhang, Changhua Zeng, Jianping Fan, Shaohua Yan, Kunfeng Liu, Zhong Li, Shukang Chen
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Patent number: RE46928Abstract: Provided are azeotropic and azeotrope-like compositions of 1,2,3,3,3-pentafluoropropene (HFO-1225ye) and water. Such azeotropic and azeotrope-like compositions are useful in isolating 1,2,3,3,3-pentafluoropropene from impurities during production. Azeotropes of the instant invention are similarly useful in final compositions or manufacturing final compositions, such as blowing agent, propellants, refrigerants, diluents for gaseous sterilization and the like.Type: GrantFiled: February 10, 2017Date of Patent: July 3, 2018Assignee: THE CHEMOURS COMPANY FC, LLCInventors: Ryan Hulse, Haluk Kopkalli, Hang T. Pham