Substituting Fluorine For A Different Halogen Patents (Class 570/160)
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Patent number: 12162813Abstract: 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: August 29, 2023Date of Patent: December 10, 2024Assignee: THE CHEMOURS COMPANY FC, LLCInventors: Xuehui Sun, Karl Robert Krause
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Patent number: 12116332Abstract: The present disclosure provides high purity E-1,3,3,3-tetrafluoropropene (HFO-1234ze). More specifically, the present disclosure provides E-1,3,3,3-tetrafluoropropene (HFO-234ze) in at least 99.99% purity, containing less than 3 ppm 1,1,3,3,3-pentafluoropropene (HFO-1225zc). The present disclosure further provides a method of making high purity E-1,3,3,3-tetrafluoropropene (HFO-1234ze).Type: GrantFiled: November 29, 2022Date of Patent: October 15, 2024Assignee: Honeywell International Inc.Inventors: Haiyou Wang, Gustavo Cerri, Mitchel Cohn, Selma Bektesevic
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Patent number: 11578022Abstract: The present invention pertains to a novel process of manufacturing the compound 2,3,3,3-tetrafluoropropene (1234yf). The compound 1234yf is the newest refrigerant with zero OPD (Ozone Depleting Potential) and zero GWP (Global Warming Potential). Thus, the invention relates to a process, involving a carbene generation route, for the manufacture of the compound 2,3,3,3-tetrafluoropropene (1234yf), of the compound 243db (2,3-dichloro-1,1,1-trifluoropropane), and optionally of the compound 2-chloro-1,1,1-trifluoropropene (1233xf) via carbene route and compound 243db (2,3-dichloro-1,1,1-trifluoropropane). The invention also relates to a process for the manufacture of the compound 2,3,3,3-tetrafluoropropene (1234yf), wherein the compound 243db (2,3-dichloro-1,1,1-trifluoropropane) serves as a starting material, for the manufacture of the compound 2,3,3,3-tetrafluoropropene (1234yf).Type: GrantFiled: June 21, 2021Date of Patent: February 14, 2023Inventors: Changyue Zhou, Yong Wang
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Patent number: 11339106Abstract: By fluorinating 1,2,3,3-tetrachloro-1-propene (1230xd) using hydrogen fluoride as a fluorinating agent, an efficient method for producing 1,2-dichloro-3,3-difluoro-1-propene (1232xd) is provided. Through this composition including 1232xd, there are also provided an environmentally friendly composition having excellent ability to dissolve various organic matters, a method for cleaning an article using the composition, a method for producing a lubricant solution using the composition, and a method for producing a component provided with a lubricant coating film.Type: GrantFiled: August 4, 2020Date of Patent: May 24, 2022Assignee: CENTRAL GLASS COMPANY, LIMITEDInventors: Masamune Okamoto, Kei Matsunaga, Hideaki Imura, Shota Kawano
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Patent number: 11261146Abstract: The present invention provides a process for preparation of 2,3,3,3-tetrafluoropropene and intermediates thereof. Owing to its low global warming potential and zero ozone depleting potential, it is been proposed as a replacement for existing chlorofluorocarbons and hydrofluorocarbons as refrigerant.Type: GrantFiled: October 3, 2019Date of Patent: March 1, 2022Assignee: SRF LIMITEDInventors: Sarathy Iyengar, Sridhar Jeyaraman, Karthic Natarajan, Nathan Rajamani, Rahul Saxena, Anurag Jain
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Patent number: 11192837Abstract: A process for producing 2,3,3,3-tetrafluoropropene comprises i) in a first adiabatic reactor comprising a fixed bed composed of an inlet and an outlet, bringing hydrofluoric acid into contact, in the gas phase with at least one chlorinated compound in order to produce a stream A comprising 2-chloro-3,3,3-trifluoropropene, ii) in a second adiabatic reactor comprising a fixed bed composed of an inlet and an outlet, bringing the stream A into contact, in the gas phase in the presence of a catalyst, with hydrofluoric acid, to produce a stream B comprising 2,3,3,3-tetrafluoropropene. The temperature at the inlet of the fixed bed of one of said first or second reactors is between 300° C. and 400° C. The longitudinal temperature difference between the inlet and the outlet of the fixed bed of the 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: 11186531Abstract: The present invention is to provide a method of producing an alkene that can further enhance the yield of an alkene, a reaction product, the method including bringing a gaseous halogenated alkane into contact with an alkaline aqueous solution in the presence of a phase-transfer catalyst. The objective above is achieved by a method of producing an alkene comprising bringing in the presence of a phase-transfer catalyst a liquid phase containing an alkaline aqueous solution and a water-insoluble solvent into contact with a gas phase containing a halogenated alkane that is soluble in the water-insoluble solvent.Type: GrantFiled: October 18, 2018Date of Patent: November 30, 2021Assignee: KUREHA CORPORATIONInventors: Kensuke Suzuki, Hiraku Tohmiya
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Patent number: 11124467Abstract: Provided is a method for producing HCFC and/or HFC by subjecting a halogenated hydrocarbon and anhydrous hydrogen fluoride to a fluorination reaction in the presence of a catalyst, whereby efficient production can be achieved, without the need to stop the production every time catalytic activity is regenerated or recovered, and without making facilities excessive. Provided as a solution therefor is a method comprising (A) subjecting a halogenated hydrocarbon and anhydrous hydrogen fluoride to a fluorination reaction in at least two reactors each in the presence of a catalyst to thereby obtain HCFC and/or HFC; and (B) while halting the reaction in at least one of the reactors, obtaining HCFC and/or HFC by the reaction in at least one other reactor.Type: GrantFiled: April 20, 2017Date of Patent: September 21, 2021Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Kazuhiro Takahashi, Shuuzou Kida, Tatsuya Takakuwa, Masanobu Nishitsuji
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Patent number: 11059767Abstract: The present invention relates to a process for the gas-phase production of 2,3,3,3-tetrafluoropropene, comprising the steps: i) providing a composition A comprising 2-chloro-3,3,3-trifluoropropene and/or 2,3-dichloro-1,1,1-trifluoropropane and/or 2-chloro-1,1,1,2-tetrafluoropropane or a composition B comprising 1,1,1,2,2-pentafluoropropane and/or 1,1,1,2,3-pentafluoropropane; ii) placing said composition A in contact with hydrofluoric acid in the presence of a catalytic composition comprising a chromium-based catalyst or placing said composition B in contact with a catalytic composition comprising a chromium-based catalyst to produce a composition C comprising 2,3,3,3-tetrafluoropropene, characterized in that step ii) is performed at a temperature of between 310° C. and 450° C. and in that the temperature of step ii) is controlled so as not to exceed 450° C.; and when said catalyst is deactivated, the temperature of step ii) is increased in increments from 0.5° C. to 20° C.Type: GrantFiled: July 16, 2018Date of Patent: July 13, 2021Assignee: Arkema FranceInventors: Bertrand Collier, Dominique Deur-Bert, Anne Pigamo, Laurent Wendlinger
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Patent number: 11034635Abstract: The present invention relates to a process for producing 2,3,3,3-tetrafluoropropene, comprising the steps of: a) providing a stream A comprising at least one of the compounds selected from the group consisting of 2-chloro-3,3,3-trifluoropropene and 2,3-dichloro-1,1,1-trifluoropropane; b) in a reactor, bringing said stream A into contact with HF in the presence or absence of a fluorination catalyst in order to produce a stream B comprising 2,3,3,3-tetrafluoropropene; characterized in that the electrical conductivity of said stream A provided in step a) is less than 15 mS/cm.Type: GrantFiled: March 4, 2019Date of Patent: June 15, 2021Assignee: ARKEMA FRANCEInventors: Laurent Wendlinger, Dominique Deur-Bert, Anne Pigamo
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Patent number: 10947173Abstract: The present invention relates to a process for purifying a stream including 1,1,1,2,2-pentafluoropropane, comprising the steps of i) providing a stream A comprising 1,1,1,2,2-pentafluoropropane and at least one of the compounds selected from the group consisting of 2-chloro-1,1,1,3,3-pentafluoropropane, 1,2-dichloro-3,3,3-trifluoropropene, 2-chloro-1,3,3,3-tetrafluoropropene; ii) purification, preferably by distillation, of the stream A provided in i) in order to form a first stream A1 comprising 1,1,1,2,2-pentafluoropropane, preferably recovered at the top of the distillation column, and a second stream A2 comprising said at least one of the compounds selected from the group consisting of 2-chloro-1,1,1,3,3-pentafluoropropane, 1,2-dichloro-3,3,3-trifluoropropene, 2-chloro-1,3,3,3-tetrafluoropropene, preferably recovered at the bottom of the distillation column.Type: GrantFiled: April 20, 2018Date of Patent: March 16, 2021Assignee: Arkema FranceInventors: Dominique Deur-Bert, Dominique Garrait, Anne Pigamo, Laurent Wendlinger
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Patent number: 10927060Abstract: 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 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 stage i) is carried out at a temperature which is lower than or equal to the temperature at which stage ii) is carried out.Type: GrantFiled: July 16, 2018Date of Patent: February 23, 2021Assignee: Arkema FranceInventors: Bertrand Collier, Dominique Deur-Bert, Anne Pigamo, Laurent Wendlinger
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Patent number: 10766838Abstract: Disclosed is a process for producing highly pure chlorinated alkane in which a chlorinated alkene is contacted with chlorine in a reaction zone to produce a reaction mixture containing the chlorinated alkane and the chlorinated alkene, and extracting a portion of the reaction mixture from the reaction zone, wherein the molar ratio of chlorinated alkane:chlorinated alkene in the reaction mixture extracted from the reaction zone does not exceed 95:5.Type: GrantFiled: March 18, 2019Date of Patent: September 8, 2020Assignee: SPOLEK PRO CHEMICKOU A HUTNI VYROBU A.S.Inventors: Zdenek Ondrus, Pavel Kubicek, Karel Filas, Petr Sladek
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Patent number: 10689316Abstract: The present invention provides a process for preparing 3,3,3-trifluoropropene (1243zf), the process comprising: (a)fluorinating CCl3CH2CH2CI (250fb) to produce a reaction product comprising CF3CH2CH2CI (253fb) in the liquid phase in a first reactor, using HF as the fluorinating agent; and (b)(i) dehydrohalogenating 253fb to produce 1243zf in the vapour phase in the presence of a catalyst in a second reactor; or (b)(ii) dehydrohalogenating 253fb to produce 1243zf in a second reactor, wherein the reaction product comprising 253fb produced in step (a) has subjected to one or more purification steps before step (b). The present invention also provides an azeotropic or near-azeotropic composition comprising HF and 253fb.Type: GrantFiled: July 14, 2016Date of Patent: June 23, 2020Assignee: MEXICAN FLUOR S.A. DE C.V.Inventors: Emma Jayne Hodgson, Claire Elizabeth McGuinness, Clive Robert Giddis, James Henry Murray, Clare Mary Skae, Gary Lloyd
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Patent number: 10640438Abstract: The present invention concerns a method for preparing tetrafluoropropene utilising three reactors and comprising the steps of (a) implementing, in the first and second reactors, at least one step of reacting, in the gas phase, a compound B in the presence of hydrofluoric acid and a catalyst, in alternation with a step of regenerating the catalyst by bringing it into contact with a regeneration flow comprising an oxidising agent, (b) implementing, in the third reactor, a preliminary step of producing the compound B, in alternation with a step of regenerating the preliminary catalyst with a regeneration flow comprising an oxidising agent. The step of regenerating the preliminary catalyst in the third reactor is implemented in the absence of a step of reacting the compound B in the presence of hydrofluoric acid in said first and second reactors. The present invention also concerns a facility configured to implement the present method.Type: GrantFiled: May 17, 2017Date of Patent: May 5, 2020Assignee: Arkema FranceInventors: Dominique Deur-Bert, Dominique Garrait, Anne Pigamo, Laurent Wendlinger
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Patent number: 10633309Abstract: The present invention concerns a method for preparing tetrafluoropropene utilising three reactors each comprising a catalytic bed containing a catalyst or a preliminary catalyst, and comprising the implementation, separately in each of the reactors, of catalytic reactions or reactions regenerating the catalyst, the quantity of catalyst or preliminary catalyst in the catalytic bed of one of the reactors representing between 90% and 110% of the quantity of catalyst or preliminary catalyst contained in the catalytic bed of one of the other two reactors. The present invention also concerns a facility configured to implement the present method.Type: GrantFiled: May 17, 2017Date of Patent: April 28, 2020Assignee: ARKEMA FRANCEInventors: Dominique Deur-Bert, Dominique Garrait, Anne Pigamo, Laurent Wendlinger
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Patent number: 10590050Abstract: Disclosed is a method for co-producing various alkenyl halides and hydrofluoroalkanes: cis-1-chloro-3,3,3-trifluoropropene is introduced into a first reactor to carry out an isomerization reaction in the presence of a first catalyst, and the reaction product is rectified to obtain a product trans-1-chloro-3,3,3-trifluoropropene; and 30-70 wt % of trans-1-chloro-3,3,3-trifluoropropene and hydrogen fluoride are mixed and then introduced into a second reactor to carry out a reaction in the presence of a second catalyst to obtain a second reactor reaction product; the second reactor reaction product is introduced into a phase separator for separation, and the obtained organic phase is rectified to obtain the products trans-1,3,3,3-tetrafluoropropene, cis-1,3,3,3-tetrafluoropropene and 1,1,1,3,3-pentafluoropropane. The invention has the advantages of simple process, high efficiency, high operation flexibility, less investment and low energy consumption.Type: GrantFiled: June 25, 2018Date of Patent: March 17, 2020Assignee: Zhejiang Quhua Fluor-Chemistry Co LtdInventors: Jiangyong Hong, Bo Yang, Yan Zhang, Guojun Yu, Yang Zhao, Hao Ouyang, Haitao Gong
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Patent number: 10584270Abstract: Disclosed are compositions comprising HCFC-243db, HCFO-1233xf, HCFC-244db and/or HFO-1234yf and at least one additional compound. For the composition comprising 1234yf, the additional compound is selected from the group consisting of HFO-1234ze, HFO-1243zf, HCFC-243db, HCFC-244db, HFC-245cb, HFC-245fa, HCFO-1233xf, HCFO-1233zd, HCFC-253fb, HCFC-234ab, HCFC-243fa, ethylene, HFC-23, CFC-13, HFC-143a, HFC-152a, HFC-236fa, HCO-1130, HCO-1130a, HFO-1336, HCFC-133a, HCFC-254fb, CHF?CHCl, HFO-1141, HCFO-1242zf, HCFO-1223xd, HCFC-233ab, HCFC-226ba, and HFC-227ca. Compositions comprising HCFC-243db, HCFO-1233xf, and/or HCFC-244db are useful in processes to make HFO-1234yf. Compositions comprising HFO-1234yf are useful, among other uses, as heat transfer compositions for use in refrigeration, air-conditioning and heat pump systems.Type: GrantFiled: January 10, 2019Date of Patent: March 10, 2020Assignee: THE CHEMOURS COMPANY FC, LLCInventors: Barry Asher Mahler, Mario Joseph Nappa
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Patent number: 10508067Abstract: A process for the manufacture of halogenated olefins in semi-batch mode by dehydrohalogenation of halogenated alkanes in the presence of an aqueous base such as KOH which simultaneously neutralizes the resulting hydrogen halide. During the process, aqueous base is continuously added to the haloalkane which results in better yields, lower by-product formation and safer/more controllable operation.Type: GrantFiled: February 5, 2018Date of Patent: December 17, 2019Assignee: Honeywell International Inc.Inventors: George R. Cook, Haluk Kopkalli, Stephen A. Cottrell, Yuon Chiu, Peter Scheidle, Daniel C. Merkel
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Patent number: 10487028Abstract: The invention relates to a method for producing 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) from at least one compound A selected from the group consisting of halopropane of formulae CX3CHClCH2X or CX3CFClCH3, or halopropenes of formula CQX2CCNCH2 and CX2?CClCH2X where X independently represents a fluorine or chlorine atom, characterised in that it comprises bringing said at least one compound A into contact with HF in a gaseous phase in the presence of a fluorination catalyst AlF3 or fluorine-bearing alumina in order to form a gaseous flow B comprising 2-chloro-3,3,3-trifluoropropene (HCFO-1233xf) et 3,3,3-trifluoropropene (HFO-1243zf).Type: GrantFiled: January 13, 2017Date of Patent: November 26, 2019Assignee: Arkema FranceInventors: Dominique Deur-Bert, Dominique Garrait, Anne Pigamo, Laurent Wendlinger
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Patent number: 10427998Abstract: The present invention relates to compositions based on F-1230za (1,1,3,3-tetrachloropropene), or on a mixture consisting of F-1230za and F-1230zd (1,3,3,3-tetrachloropropene), the manufacture thereof, and also the use thereof in particular for the production of F-1233zdE (trans-1-chloro-3,3,3-trifluoropropene), F-1234zeE (trans-1,3,3,3-tetrafluoropropene), and/or F-245fa (1,1,1,3,3-pentafluoropropane).Type: GrantFiled: May 4, 2016Date of Patent: October 1, 2019Assignee: ARKEMA FRANCEInventors: Anne Pigamo, Bertrand Collier
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Patent number: 10407369Abstract: The invention relates to a process for producing 2,3,3,3-tetrafluoropropene performed using a starting composition, comprising the steps of placing the starting composition in contact with HF, in the presence of a catalyst, to produce a composition A comprising 2,3,3,3-tetrafluoropropene (1234yf), intermediate products B consisting of 2-chloro-3,3,3-trifluoropropene (1233xf), 1,1,1,2,2-pentafluoropropane (245cb), and side products C consisting of E-1-chloro-3,3,3-trifluoro-1-propene (1233zdE), trans-1,3,3,3-tetrafluoro-1-propene (1234zeE) and 1,1,1,3,3-pentafluoropropane (245fa); recovery of said composition A and purification thereof to form and recover a first stream comprising 2,3,3,3-tetrafluoropropene (1234yf) and one or more streams comprising 2-chloro-3,3,3-trifluoropropene (1233xf) and/or 1,1,1,2,2-pentafluoropropane (245cb); recycling into step a) of said one or more streams comprising 2-chloro-3,3,3-trifluoropropene (1233xf) and/or 1,1,1,2,2-pentafluoropropane (245cb).Type: GrantFiled: December 14, 2016Date of Patent: September 10, 2019Assignee: ARKEMA FRANCEInventors: Bertrand Collier, Dominique Deur-Bert, Joaquin Lacambra, Laurent Wendlinger
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Patent number: 10407368Abstract: The present invention provides a method for producing a fluorine-containing haloolefin compound, the method easily inhibiting catalyst deactivation, and the method being capable of inhibiting a decrease in conversion and selectivity in the reaction, even when the reaction is continued for a long period of time. The present invention is a method for producing a fluorine-containing haloolefin compound via a step of fluorinating a C3 halogenated hydrocarbon. The method comprises a step of removing a stabilizer contained in the C3 halogenated hydrocarbon before the fluorination step.Type: GrantFiled: October 8, 2015Date of Patent: September 10, 2019Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Daisuke Karube, Masayuki Kishimoto, Yuzo Komatsu
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Patent number: 10173952Abstract: This invention provides a method for stably producing 2,3,3,3-tetrafluoropropene for a long period of time wherein unreacted materials are reused after distillation without liquid-liquid separation to suppress catalyst deactivation.Type: GrantFiled: June 16, 2015Date of Patent: January 8, 2019Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Tatsuya Takakuwa, Kazuhiro Takahashi, Daisuke Karube, Takehiro Chaki, Masayuki Kishimoto, Yuzo Komatsu
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Patent number: 9359273Abstract: The present invention relates, in part, to the discovery that the presence of impurities in 1,1,2,3-tetrachloropropene (1230xa) results in catalyst instability during the fluorination of 1230xa to 2-chloro-3,3,3-trifluoropropene. By substantially removing the impurities, it is shown that the catalyst life is extended and results in improved operation efficiency of the fluorination reaction. Such steps similarly result in an overall improvement in the production of certain hydrofluoroolefins, particularly 2,3,3,3-tetrafluoropropene (1234yf).Type: GrantFiled: October 11, 2012Date of Patent: June 7, 2016Assignee: HONEYWELL INTERNATIONAL INC.Inventors: Selma Bektesevic, Daniel C. Merkel, Mario Joseph Nappa, Xuehui Sun, Hsueh Sung Tung, Haiyou Wang
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Patent number: 9334207Abstract: Disclosed is an integrated manufacturing process to co-produce (E)1-chloro-3,3,3-trifluoropropene, (E)1,3,3,3-tetrafluoropropene, and 1,1,1,3,3-pentafluoro-propane starting from a single chlorinated hydrocarbon feed stock, 240fa. The process includes a combined liquid or vapor phase reaction/purification operation which directly produces (E)1-chloro-3,3,3-trifluoropropene (1233zd(E)) from 240fa. In the second liquid phase fluorination reactor 1233zd(E) is contacted with HF in the presence of catalyst to produce 1,1,1,3,3-pentafluoropropane (245fa) with high conversion and selectivity. A third reactor is used for dehydrofluorination of 245fa to produce (E)1,3,3,3-tetrafluoropropene (1234ze(E)) by contacting in the liquid phase with a caustic solution or in the vapor phase using a dehydrofluorination catalyst. This operation may be followed by one or more purification processes to recover the 1234ze(E) product.Type: GrantFiled: August 29, 2011Date of Patent: May 10, 2016Assignee: Honeywell International Inc.Inventors: Konstantin A. Pokrovski, Daniel C. Merkel, Haiyou Wang, Hsueh Sung Tung, Ian Shankland
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Patent number: 9315431Abstract: 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: October 8, 2014Date of Patent: April 19, 2016Assignee: ARKEMA FRANCEInventor: Anne Pigamo
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Patent number: 9272968Abstract: This invention relates to a process for the suppression of 3,3,3-trifluoropropyne during the manufacture of fluorocarbons, fluoroolefins, hydrochlorofluoroolefins. More particularly, this invention is directed to a process to suppress the formation of 3,3,3-trifluoropropyne during processes for the manufacture of HCFO-1233zd(E), HCFO-1233zd(Z), HFO-1234ze(E), and/or HFO-1234ze(Z).Type: GrantFiled: March 14, 2013Date of Patent: March 1, 2016Assignee: Honeywell International Inc.Inventors: Haluk Kopkalli, Jeffrey A. Ball, Yuon Chiu, Hsueh Sung Tung, Konstantin A. Pokrovski, Daniel C. Merkel
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Patent number: 9181153Abstract: The present invention provides a process for purifying a (E)-1-chloro-3,3,3-trifluoropropene composition (OF-1233E composition) in which at hydrogen fluoride and 2-chloro-1,1,1,3,3-pentafluoropropane are contained by bringing the (E)-1-chloro-3,3,3-trifluoropropene composition into contact with a weak base and a method for producing (E)-1-chloro-3,3,3-trifluoropropene composition by distilling the (E)-1-chloro-3,3,3-trifluoropropene composition obtained by such a purification process. This makes it possible to efficiently produce OF-1233E by removing the hydrogen fluoride from the OF-1233E composition, without generating any new component difficult to separate by distillation, and subjecting the resulting composition to distillation.Type: GrantFiled: October 3, 2012Date of Patent: November 10, 2015Assignee: Central Glass Company, LimitedInventors: Masamune Okamoto, Hideaki Imura, Naoto Takada, Tatsuya Hayasaka
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Patent number: 9115044Abstract: Provided is a method for producing trans-1-chloro-3,3,3-trifluoropropene usable as a raw material for a foaming agent for a hard polyurethane foam, a solvent, a cleaning agent, a cooling medium, a working fluid, a propellant, a fluorinated resin, etc., the method involving a step of bringing cis-1-chloro-3,3,3-trifluoropropene into contact with a catalyst, wherein the catalyst includes a fluorinated metal oxide or a metal fluoride each produced by applying a fluorination treatment to a metal oxide containing one kind or two or more kinds of metals and containing aluminum atoms that make up 50 at. % or more of metal atoms to thereby substitute some or all of oxygen atoms in the metal oxide with fluorine atom(s), wherein the fluorinated metal oxide or the metal fluoride is a compound produced through a drying treatment at 400 to 600° C.Type: GrantFiled: November 8, 2012Date of Patent: August 25, 2015Assignee: Central Glass Company, LimitedInventors: Satoru Okamoto, Fuyuhiko Sakyu
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Patent number: 9061956Abstract: The present invention relates to a method for manufacturing 2,3,3,3-tetrafluoropropene from halopropanes having the formula CX3CHCICH2X and halopropenes having the formulas CX3CCI?CH2CCIX2CCI?CH2 and CX2?CCICH2X, where X is independently a fluorine or chlorine atom. The invention specifically relates to a method including at least one step during which 2-chloro-3,3,3-trifluoro-1-propene, optionally mixed with at least one halopropane having the formula CX3CHCICH2X and/or at least one halopropene having the formulas CCIX2CCI?CH2 and CX2?CCICH2X, where X is independently a fluorine or chlorine atom, reacts with HF in the gaseous phase in the presence of a fluoridation catalyst at a temperature of between 320 and 420° C. with a molar ratio of oxygen to 2-chloro-3,3,3-trifluoro-1-propene of more than 1 but no more than 2.5, and a molar ratio of HF to the total amount of organic compounds to be reacted of between 5 and 40.Type: GrantFiled: September 20, 2012Date of Patent: June 23, 2015Assignee: Arkema FranceInventors: Anne Pigamo, Nicolas Doucet, Laurent Wendlinger
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Publication number: 20150148571Abstract: The present invention provides a process for producing a fluoroolefin by reacting, in a gas phase, a fluorinating agent and a chlorine-containing alkene or a chlorine-containing alkane in the presence of at least one catalyst selected from the group consisting of chromium oxide, at least part of which is crystallized, and fluorinated chromium oxide obtained by fluorinating the chromium oxide. According to the present process, a target fluoroolefin can be obtained at a high conversion rate of the starting material and with high selectivity.Type: ApplicationFiled: July 10, 2013Publication date: May 28, 2015Inventors: Takehiro Chaki, Daisuke Karube, Masami Nishiumi
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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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Publication number: 20150105596Abstract: This invention relates to methods and systems for producing hydrochlorofluoro-olefins, particularly 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) by the fluorination of a starting material selected from the group consisting of 1,1,1,3,3-pentachloropropane (HCC-240fa), 1,1,3,3-tetrachloropropene, and 1,1,1,3-tetrachloropropene, alone or in combination, in an ionic liquid.Type: ApplicationFiled: October 7, 2014Publication date: April 16, 2015Inventors: Haiyou Wang, Hsueh Sung Tung
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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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Publication number: 20150080619Abstract: The invention concerns a method for producing 2,3,3,3-tetrafluoropropene comprising: a fluoridation reaction of a halopropane and/or halopropene into 2,3,3,3-tetrafluoropropene by means of hydrogen fluoride; the recovery of a gas stream resulting from the reaction; the cooling and partial condensation of the gas stream resulting from the reaction into a partially condensed stream; the separation of the partially condensed stream into a gas fraction and a liquid fraction; the compression of the gas fraction into a compressed gas fraction; the compression of the liquid fraction into a compressed liquid fraction; the distillation of the compressed gas fraction and compressed liquid fraction in order to provide a stream of 2,3,3,3-tetrafluoropropene, a stream of hydrochloric acid, and a stream of unreacted hydrogen fluoride. The invention also concerns an installation suitable for implementing said method.Type: ApplicationFiled: January 11, 2013Publication date: March 19, 2015Inventors: Dominique Deur-Bert, Bertrand Collier, Laurent Wendlinger
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Publication number: 20150057473Abstract: 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: ApplicationFiled: March 21, 2013Publication date: February 26, 2015Applicant: DAIKIN INDUSTRIES, LTD.Inventors: Masayuki Kishimoto, Yuzo Komatsu
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Patent number: 8933280Abstract: The present invention provides continuous, gas phase, free radical processes for the production of chlorinated and/or fluorinated propenes or higher alkenes from the reaction of chlorinated and/or fluorinated alkanes and chlorinated and/or fluorinated alkenes, wherein wherein at least a portion of any intermediate boiler by-products generated by the process are removed from the process.Type: GrantFiled: October 4, 2013Date of Patent: January 13, 2015Assignee: Dow Global Technologies LLCInventors: Max Markus Tirtowidjojo, Patrick Ho-Sing Au-Yeung, Debashis Chakraborty, Juergen Eiffler, Heinz Groenewald, Kurt Frederick Hirsekorn, Manfred Kokott, William J. Kruper, Jr., Thomas Ulrich Luebbe, Holger Meeman, Shirley Shaw Sexton, Peter Wenzel, Marcus Wobser
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Publication number: 20140364658Abstract: The present invention relates to a method for preparing fluorinated olefin compounds, in particular (chloro)fluoropropenes and (chloro)fluorobutenes, and specifically, the fluorinated compound 2,3,3,3-tetrafluoro-1-propene, including at least one step of fluorination, in the gaseous phase, with HF and at least one compound selected from the halopropenes having formula the CX3CHClCH2X and the halopropenes having the formulas CX3CC1?CH2, CClX2CCl?CH2 and CX2?CClCH2X, where X is, independently, a fluorine or chlorine atom, in the presence of oxygen and a fluorination catalyst suspended in a fluidized-bed reactor.Type: ApplicationFiled: November 29, 2012Publication date: December 11, 2014Inventor: Jean-Luc Dubois
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Patent number: 8907146Abstract: Disclosed is a process in which the fluorination of an organic reactant comprising 1,1,1,3,3-pentachloropropane (240fa) with anhydrous HF is conducted in the presence of an effective amount of a phase-transfer catalyst which facilitates the reaction between these incompatible reaction components to produce 1-chloro-3,3,3-trifluoro-propene (1233zd). Other organic reactant materials include 1,1,3,3-tetrachloropropene (HCO-1230za), 1,3,3,3-tetrachloropropene (HCO-1230zd), and various mixtures with or without 240fa.Type: GrantFiled: January 30, 2014Date of Patent: December 9, 2014Assignee: Honeywell International Inc.Inventors: Hsueh Sung Tung, Haiyou Wang, Daniel C. Merkel, Stephen A. Cottrell, Konstantin A. Pokrovski, Ian Shankland
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Publication number: 20140350312Abstract: Provided are a fluorination catalyst for preparing 2,3,3,3-tetrafluoropropene and a method using the catalyst for preparing 2,3,3,3-tetrafluoropropene. The catalyst has the following structural formula: Crx(Y,Z)0.005-0.5O0.1-10F1.0-3.0, where Y is one or a combination of two or more among Al, Zn, and Mg, and where Z is a rare earth element having an oxygen-storing/releasing function. The catalyst has in preparing 2,3,3,3-tetrafluoropropene the advantages of increased raw material conversion rate, great product selectivity, and extended catalyst service life.Type: ApplicationFiled: September 11, 2012Publication date: November 27, 2014Applicant: SINOCHEM LANTIAN CO., LTD.Inventors: Gang Yang, Lei Xu, Huie Yang, En Jiang, Jianping Fan, Xintang Zhao, Changhua Zeng, Wenqing Zhang, Yunlong Lei, Zhong Li, Shukang Chen
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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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Publication number: 20140316170Abstract: The present invention relates, in part, to the discovery that the presence of impurities in 1,1,2,3-tetrachloropropene (1230xa) results in catalyst instability during the fluorination of 1230xa to 2-chloro-3,3,3-trifluoropropene. By substantially removing the impurities, it is shown that the catalyst life is extended and results in improved operation efficiency of the fluorination reaction. Such steps similarly result in an overall improvement in the production of certain hydrofluoroolefins, particularly 2,3,3,3-tetrafluoropropene (1234yf).Type: ApplicationFiled: October 11, 2012Publication date: October 23, 2014Inventors: Selma BEKTESEVIC, Daniel C. MERKEL, Mario Joseph NAPPA, Xuehui SUN, Hsueh Sung TUNG, Haiyou WANG
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Publication number: 20140316171Abstract: The invention relates to a process for manufacturing 1,1,1,2-tetrafluoropropene (1234yf, CF3-CF?CH2) from 1,1,3,3-tetrachlororopropene (1230za, CCl2CH—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: ApplicationFiled: January 21, 2014Publication date: October 23, 2014Applicant: Arkema Inc.Inventors: Maher Y. ELSHEIKH, Philippe Bonnet, John A. Wismer
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Publication number: 20140309463Abstract: The present invention relates, in part, to the discovery that, during the fluorination of certain fluoroolefin starting re-agents, particularly, 1,1,2,3-tetrachloropropene (1230xa), oligomerization/polymerization of such starting reagents reduces the conversion process and leads to increased catalyst deactivation. The present invention also illustrates that providing one or more organic co-feed to the fluooelefin starting stream reduces such oligomerization/polymerization and improves catalystic stability.Type: ApplicationFiled: November 2, 2012Publication date: October 16, 2014Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Selma Bektesevic, Daniel C. Merkel, Mario Joseph Nappa, Xuehui Sun, Hsueh Sung Tung, Haiyou Wang
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Patent number: 8859829Abstract: The present invention relates in part to a method of stabilizing chloropropenes, such as 1,1,2,3-tetrachloropropene, otherwise known to decompose and degrade, and to the resulting stabilized chloropropene, using a morpholine compound and/or a trialkyl phosphate compound as defined herein. Such stabilized chloropropenes are useful in the manufacture of hydrofluoroolefins such as 2,3,3,3-tetrafluoroprop-1-ene (1234yf).Type: GrantFiled: March 11, 2014Date of Patent: October 14, 2014Assignee: Honeywell International Inc.Inventors: Haluk Kopkalli, Haiyou Wang, Hsueh Sung Tung, Daniel C. Merkel
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Publication number: 20140303412Abstract: This invention provides a process for producing a fluoroolefin comprising reacting, in a vapor phase, a fluorinating agent and a chlorine-containing alkene or a chlorine-containing alkane in the presence of at least one catalyst selected from the group consisting of chromium oxide containing a Group 5 element and fluorinated chromium oxide containing a Group 5 element. According to the process of the present invention, the target fluoroolefin can be obtained with high starting material conversion and good selectivity.Type: ApplicationFiled: January 24, 2013Publication date: October 9, 2014Inventors: Daisuke Karube, Takehiro Chaki, Masami Nishiumi, Takashi Shibanuma, Masashi Arai
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Publication number: 20140296585Abstract: The present invention relates to a method for separating a composition containing 2,3,3,3-tetrafluoropropene and hydrofluoric acid, and for recovering the thus-separated 2,3,3,3-tetrafluoropropene and hydrofluoric acid. The invention also relates to a method for manufacturing and purifying 2,3,3,3-tetrafluoropropene using a hydrofluorination reaction of the saturated or unsaturated compound having three carbon atoms and including at least one chlorine atom in the presence of a fluorination catalyst.Type: ApplicationFiled: June 14, 2012Publication date: October 2, 2014Inventors: Dominique Deur-Bert, Bertrand Collier
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Publication number: 20140275650Abstract: The present invention relates in part to a method of stabilizing chloropropenes, such as 1,1,2,3-tetrachloropropene, otherwise known to decompose and degrade, and to the resulting stabilized chloropropene, using a morpholine compound and/or a trialkyl phosphate compound as defined herein. Such stabilized chloropropenes are useful in the manufacture of hydrofluoroolefins such as 2,3,3,3-tetrafluoroprop-1-ene (1234yf).Type: ApplicationFiled: March 11, 2014Publication date: September 18, 2014Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Haluk KOPKALLI, Haiyou WANG, Hsueh SUNG TUNG, Daniel C. MERKEL
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Publication number: 20140275652Abstract: 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: ApplicationFiled: March 11, 2014Publication date: September 18, 2014Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Haiyou Wang, Selma Bektesevic, Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski