Catalyst Utilized Patents (Class 570/165)
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Patent number: 11452990Abstract: A catalyst comprising one or more metal oxides, wherein the catalyst has a total pore volume equal to or greater than 0.3 cm3/g and a mean pore diameter greater than or equal to 90 ?, where in the pore volume is measured using N2 adsorption porosimetry and the mean pore diameter is measured using N2 BET adsorption porosimetry.Type: GrantFiled: September 7, 2017Date of Patent: September 27, 2022Assignee: MEXICHEM FLUOR S.A. DE C.V.Inventors: Claire Nicola Rees, Claire Elizabeth McGuinness, Andrew Paul Sharratt
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Patent number: 11312673Abstract: The present disclosure provides a method for producing HFC-143 that is not expensive, and that is more efficient than conventional methods. Specifically, the present disclosure provides a method for producing 1,1,2-trifluoroethane (HFC-143) that includes contacting at least one chlorine-containing compound selected from the group consisting of 1,1,2-trichloroethane (HCC-140), 1,2-dichloro-1-fluoroethane (HCFC-141), 1,1-dichloro-2-fluoroethane (HCFC-141a), (E,Z)-1,2-dichloroethylene (HCO-1130 (E,Z)), and (E,Z)-1-chloro-2-fluoroethylene (HCFO-1131 (E,Z)) with hydrogen fluoride to perform one or more fluorination reactions, thereby obtaining a reaction gas containing HFC-143, hydrogen chloride, and hydrogen fluoride.Type: GrantFiled: April 12, 2021Date of Patent: April 26, 2022Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Takehiro Chaki, Tsubasa Nakaue, Megumi Kushida, Kazuhiro Takahashi
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Patent number: 10906853Abstract: A new chromium-containing fluorination catalyst is described. The catalyst comprises an amount of zinc that promotes activity and from 0.1 to 8.0% by weight of the chromium in the catalyst based on the total weight of the chromium is present as chromium (VI). The use of the zinc-promoted, chromium-containing catalyst in a fluorination process in which a hydrocarbon or halogenated hydrocarbon is reacted with hydrogen fluoride in the vapor-phase at elevated temperatures is also described.Type: GrantFiled: November 17, 2017Date of Patent: February 2, 2021Assignee: Mexichem Amanco Holding S.A. De C.V.Inventor: Andrew P. Sharratt
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Patent number: 10189757Abstract: A chromia-based fluorination catalyst comprising at least one additional metal selected from zinc, nickel, aluminum and magnesium in which from 0.1 to 8.0% by weight of the catalyst is in the form of one or more crystalline compounds of chromium and/or one or more crystalline compounds of the at least one additional metal. The catalyst can be used in processes for producing a fluorinated hydrocarbon.Type: GrantFiled: September 13, 2017Date of Patent: January 29, 2019Assignee: Mexichem Amanco Holding S.A. de C.V.Inventors: Andrew P Sharratt, John D Scott
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Patent number: 9771309Abstract: A chromia-based fluorination catalyst comprising at least one additional metal selected from zinc, nickel, aluminum and magnesium in which from 0.1 to 8.0% by weight of the catalyst is in the form of one or more crystalline compounds of chromium and/or one or more crystalline compounds of the at least one additional metal. The catalyst can be used in processes for producing a fluorinated hydrocarbon.Type: GrantFiled: April 10, 2006Date of Patent: September 26, 2017Assignee: MEXICHEM AMANCO HOLDING S.A. DE C.V.Inventors: Andrew P Sharratt, John D Scott
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Patent number: 9233895Abstract: The invention relates to a process to produce HCFC-244bb from HCFO-1233xf wherein, in one embodiment, one or more co-feed species having a normal boiling point of between about ?80° C. to about 0° C., such as 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: GrantFiled: April 24, 2015Date of Patent: January 12, 2016Assignee: HONEYWELL INTERNATIONAL, INC.Inventors: Haluk Kopkalli, Daniel C. Merkel, Ron Joseph Roof
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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: 9018428Abstract: Disclosed is a reactor and agitator useful in a high pressure process for making 1-chloro-3,3,3-trifluoropropene (1233zd) from the reaction of 1,1,1,3,3-pentachloropropane (240fa) and HF, wherein the agitator includes one or more of the following design improvements: (a) double mechanical seals with an inert barrier fluid or a single seal; (b) ceramics on the rotating faces of the seal; (c) ceramics on the static faces of seal; (d) wetted o-rings constructed of spring-energized Teflon and PTFE wedge or dynamic o-ring designs; and (e) wetted metal surfaces of the agitator constructed of a corrosion resistant alloy.Type: GrantFiled: March 14, 2013Date of Patent: April 28, 2015Assignee: Honeywell International Inc.Inventor: Stephen A. Cottrell
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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: 8987533Abstract: A production method of 1-chloro-3,3,3-trifluoropropene according to the present invention includes reaction of 1,1,1,3,3-pentachloropropane with hydrogen fluoride, characterized in that the concentrations of respective catalytic components in the 1,1,1,3,3-pentachloropropane as the raw material is controlled to a predetermined level or less. By controlling the concentrations of the respective catalytic components in the 1,1,1,3,3-pentachloropropane to the predetermined level or less, it is possible to improve the problems of shortening of catalyst life, retardation of reaction and scaling or corrosion of equipment in the production of the 1-chloro-3,3,3-trifluoropropene. In addition, the 1,1,1,3,3-pentachloropropane can be obtained selectively with high yield by telomerization reaction of carbon tetrachloride and vinyl chloride. The present invention is thus useful as the method for industrially advantageous, high-yield production of the 1-chloro-3,3,3-trifluoropropene.Type: GrantFiled: November 22, 2012Date of Patent: March 24, 2015Assignee: Central Glass Company, LimitedInventors: Yasuo Hibino, Satoshi Yoshikawa, Fuyuhiko Sakyu
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Publication number: 20150057472Abstract: The invention relates to the use of a liquid-vapor separator such as a de-entrainer to remove an unvaporized portion of a feed, e.g. 1,1,2,3-tetrachloropropene (1230xa), to a catalytic vapor phase fluorination reaction where e.g. 2-chloro-3,3,3,-trifluoropropene (1233xf) is produced. The invention extends the life of the catalyst.Type: ApplicationFiled: April 18, 2014Publication date: February 26, 2015Applicant: Honeywell International Inc.Inventors: Selma Bektesevic, Haluk Kopkalli, Haiyou Wang
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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: 8779218Abstract: Process of catalytic fluorination in liquid phase of product 1,1,1,2,3-pentachloropropane or/and 1,1,2,2,3-pentachloropropane into product 2-chloro-3,3,3-trifluoropropene in presence of a catalyst.Type: GrantFiled: March 21, 2011Date of Patent: July 15, 2014Assignee: Arkema FranceInventors: Anne Pigamo, Laurent Wendlinger, Philippe Bonnet
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Patent number: 8772554Abstract: The present invention provides a method for efficiently preparing 2,3,3,3-tetrafluoropropene (HFO-1234yf) by a simple and economically advantageous method that is suitable for implementation on an industrial scale. The present invention provides a process for preparing 2,3,3,3-tetrafluoropropene, comprising the step of: (1) in a reactor, (1-1) reacting 1,1,1,2,3-penta-chloropropane with hydrogen fluoride in an amount of 10 to 100 mol per mole of the 1,1,1,2,3-pentachloropropane 1; (1-2) in the presence of chromic oxide represented by composition formula: CrOm (1.5<m<3) or fluorinated chromic oxide obtained by fluorinating the chromic oxide; (1-3) in the presence of oxygen in an amount of 0.02 to 1 mol per mole of the 1,1,1,2,3-pentachloropropane; and (1-4) in the gas phase within a temperature range of 320 to 390 degrees centigrade, thereby obtaining a reaction product containing 2,3,3,3-tetrafluoropropene.Type: GrantFiled: June 22, 2012Date of Patent: July 8, 2014Assignee: Daikin Industries, Ltd.Inventors: Masatoshi Nose, Yuzo Komatsu
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Patent number: 8697923Abstract: The invention provides a process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) comprising (a) contacting 1,1,1-trifluoro-2,3-difluoropropane (243db) with hydrogen fluoride (HF) in the presence of a zinc/chromia catalyst to produce a compound having the formula CF3CHFCH2X, wherein X is Cl or F, and (b) dehydrohalogenating the compound of formula CF3CHFCH2X to produce 1234yf.Type: GrantFiled: August 19, 2013Date of Patent: April 15, 2014Assignee: Mexichem Amanco Holding S.A. de C.V.Inventors: John W. Smith, Claire McGuiness, Andrew P. Sharratt
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Publication number: 20140100393Abstract: The invention provides an improved process to manufacture 2-chloro-1,1,1,2-tetrafluoropropane (HCFC-244bb) by reacting 2-chloro-3,3,3,-trifluoropropene (HCFO-1233xf) with hydrogen fluoride, in the presence of a fluorination catalyst, where by using 2-chloro-3,3,3,-trifluoropropene (HCFO-1233xf) of high purity, the need to add an oxidizing agent (typically chlorine) to keep the catalyst active can be avoided. The HCFC-244bb is then used as an intermediate in the production of 2,3,3,3-tetrafluoropropene-1 (HFO-1234yf).Type: ApplicationFiled: June 28, 2010Publication date: April 10, 2014Applicant: HONEYWELL INTERNATIONAL INC.Inventors: Robert C. Johnson, Daniel C. Merkel
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Patent number: 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: 8633340Abstract: The invention provides a process for preparing 1,1,1-trifluoro-2,3-dichloropropane (243db), which process comprises contacting 3,3,3-trifluoropropene (1243zf) with chlorine in the presence of a catalyst, wherein the catalyst comprises activated carbon, alumina and/or an oxide of a transition metal.Type: GrantFiled: April 9, 2009Date of Patent: January 21, 2014Assignee: Mexichem Amanco Holding S.A. de C.V.Inventors: John W. Smith, Claire McGuiness, Andrew P. Sharratt
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Patent number: 8629307Abstract: The invention provides a process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) comprising (a) contacting 1,1,1-trifluoro-2,3-difluoropropane (243db) with hydrogen fluoride (HF) in the presence of a zinc/chromia catalyst to produce a compound having the formula CF3CHFCH2X, wherein X is Cl or F, and (b) dehydrohalogenating the compound of formula CF3CHFCH2X to produce 1234yf.Type: GrantFiled: December 12, 2012Date of Patent: January 14, 2014Assignee: Mexichem Amanco S.A. de C.V.Inventors: John W. Smith, Claire McGuiness, Andrew P. Sharratt
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Patent number: 8614361Abstract: The present invention provides an effective, selective, and industrially applicable process for producing 2,3,3,3-tetrafluoropropene. Specifically, the present invention provides a process for producing 2,3,3,3-tetrafluoropropene including reacting 2-chloro-3,3,3-trifluoropropene with hydrogen fluoride in the presence of oxygen and a catalyst comprising chromium oxide represented by the composition formula: CrOm (1.5<m<3), or fluorinated chromium oxide obtained by fluorinating the chromium oxide.Type: GrantFiled: April 22, 2010Date of Patent: December 24, 2013Assignee: Daikin Industries, Ltd.Inventors: Atsushi Suzuki, Masatoshi Nose, Tsuneo Yamashita
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Patent number: 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: 8552228Abstract: The invention provides a process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) comprising (a) contacting 1,1,1-trifluoro-2,3-difluoropropane (243db) with hydrogen fluoride (HF) in the presence of a zinc/chromia catalyst to produce a compound having the formula CF3CHFCH2X, wherein X is Cl or F, and (b) dehydrohalogenating the compound of formula CF3CHFCH2X to produce 1234yf.Type: GrantFiled: April 9, 2009Date of Patent: October 8, 2013Assignee: Mexichem Amanco Holdings S.A. de C.V.Inventors: John W. Smith, Claire McGuiness, Andrew P. Sharratt
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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: 8450537Abstract: A process is disclosed for making CF3CH2CHF2, CF3CH?CHF, and/or CF3CH?CHCl. This process involves reacting at least one starting material selected from the group consisting of halopropenes of the formula CX3CH?CH2 and halopropenes of the formula CX2?CHCH2X, wherein each X is independently F or Cl, with HF and Cl2 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. The molar ratio of HF to the total amount of starting materials fed to the reaction zone is at least stoichiometric, and the molar ratio of Cl2 to total amount of starting material fed to the reaction zone is 2:1 or less.Type: GrantFiled: October 23, 2012Date of Patent: May 28, 2013Assignee: E I du Pont de Nemours and CompanyInventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
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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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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: 20130102815Abstract: The invention provides a process for the preparation of 2,3,3,3-tetrafluoropropene (1234yf) comprising (a) contacting 1,1,1-trifluoro-2,3-difluoropropane (243db) with hydrogen fluoride (HF) in the presence of a zinc/chromia catalyst to produce a compound having the formula CF3CHFCH2X, wherein X is Cl or F, and (b) dehydrohalogenating theType: ApplicationFiled: December 12, 2012Publication date: April 25, 2013Applicant: Mexichem Amanco Holding S.A. de C.V.Inventor: Mexichem Amanco Holding S.A. de C.V.
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Patent number: 8415515Abstract: A process for the production of dichlorotrifluoroethane is described. The process comprises reacting perchloroethylene with hydrogen fluoride (HF) at elevated temperature in the vapour phase in at least one reactor in the presence of a fluorination catalyst. The process is operated so that 30 weight % or more of the perchloroethylene reactant that is fed to the at least one reactor remains unreacted having passed through the or each reactor. The dichlorotrifluoroethane may be purified and then used as it is or used to prepare pentafluoroethane.Type: GrantFiled: September 23, 2011Date of Patent: April 9, 2013Assignee: Mexichem Amanco Holding S.A. de C.V.Inventors: Clive R Giddis, Paul H Stewert
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Patent number: 8395001Abstract: To provide processes for efficiently and economically producing 2-chloro-1,1,1,2-tetrafluoropropane (R244bb) and 2,3,3,3-tetrafluoropropene (R1234yf) in an industrially practical manner. A process for producing 2-chloro-1,1,1,2-tetrafluoropropane, which comprises a chlorination step of reacting 1,2-dichloro-2-fluoropropane and chlorine in the presence of a solvent under irradiation with light to obtain 1,1,1,2-tetrachloro-2-fluoropropane, and a fluorination step of reacting the 1,1,1,2-tetrachloro-2-fluoropropane obtained in the chlorination step and hydrogen fluoride in the presence of a catalyst to obtain 2-chloro-1,1,1,2-tetrafluoropropane, and a process for producing 2,3,3,3-tetrafluoropropene, which comprises dehydrochlorinating it in the presence of a catalyst.Type: GrantFiled: June 10, 2011Date of Patent: March 12, 2013Assignee: Asahi Glass Company, LimitedInventors: Satoshi Kawaguchi, Takashi Okazoe, Hidekazu Okamoto
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Publication number: 20130060068Abstract: A process is disclosed for making CF3CH2CHF2, CF3CH?CHF, and/or CF3CH?CHCl. This process involves reacting at least one starting material selected from the group consisting of halopropenes of the formula CX3CH?CH2 and halopropenes of the formula CX2?CHCH2X, wherein each X is independently F or Cl, with HF and Cl2 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. The molar ratio of HF to the total amount of starting materials fed to the reaction zone is at least stoichiometric, and the molar ratio of Cl2 to total amount of starting material fed to the reaction zone is 2:1 or less.Type: ApplicationFiled: October 23, 2012Publication date: March 7, 2013Applicant: E I DU PONT DE NEMOURS AND COMPANYInventor: E I DU PONT DE NEMOURS AND COMPANY
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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: 8318992Abstract: A process is disclosed for making CF3CF2CH3, CF3CF?CH2 and/or CF3CCl?CH2. The process involves reacting at least one starting material selected from the group consisting of halopropanes of the formula CX3CH2CH2X, halopropenes of the formula CX3CH?CH2 and halopropenes of the formula CX2?CHCH2X, wherein each X is independently F or Cl, with HF and Cl2 in a reaction zone to produce a product mixture comprising HF, HCl, CF3CF2CH3, CF3CF?CH2, and CF3CCl?CH2; and recovering the CF3CF2CH3, CF3CF?CH2 and/or CF3CCl?CH2 from the product mixture. Also disclosed is a process for making CF3CH2CHF2, CF3CH?CHF, and/or CF3CH?CHCl.Type: GrantFiled: October 31, 2007Date of Patent: November 27, 2012Assignee: E I du Pont de Nemours and CompanyInventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
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Patent number: 8309774Abstract: The invention is directed to a process for preparing 2,2,2,3-tetrafluoropropene (1234yf), comprising: (i) contacting 1,1,2,3-tetrachloropropene (1230xa) 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, 2,2,2,3-tetrafluoropropene (1234yf) and a second stream comprising HF, 2-chloro-3,3,3-trifluoro-1-propene (1233xf) and 1,1,1,2,2-pentafluoropropane (245cb); (iii) recycling at least a part of the second stream at least in part back to step (i).Type: GrantFiled: March 9, 2012Date of Patent: November 13, 2012Assignee: Arkema FranceInventors: Anne Pigamo, Dominique Deur-Bert, Laurent Wendlinger
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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
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Patent number: 8158836Abstract: The invention is directed to a process for preparing 2,3,3,3-tetrafluoropropene (1234yf), comprising: (i) contacting 1,1,2,3-tetrachloropropene (1230xa) 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, 2,3,3,3-tetrafluoropropene (1234yf) and a second stream comprising HF, 2-chloro-3,3,3-trifluoro-1-propene (1233xf) and 1,1,1,2,2-pentafluoropropane (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: April 17, 2012Assignee: Arkema FranceInventors: Anne Pigamo, Dominique Deur-Bert, Laurent Wendlinger
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Patent number: 8110713Abstract: The present invention relates to a process for producing pentafluoroethane. More particularly, the subject of the invention is a continuous process for producing pentafluoroethane comprising (i) a step of fluorinating perchloroethylene (PER) with hydrofluoric acid, in the gas phase, in the presence of a catalyst, (ii) a step of separating the products issuing from step (i) in order to give a fraction of light products and a fraction of heavy products, comprising hydrofluoric acid, unreacted perchloroethylene and under-fluorinated products, and (iii) a step of pretreating the fraction of heavy products before recycling to step (i).Type: GrantFiled: May 21, 2007Date of Patent: February 7, 2012Assignee: Arkema FranceInventors: Béatrice Boussand, Sylvain Perdrieux
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Publication number: 20120016166Abstract: A process for the production of dichlorotrifluoroethane is described. The process comprises reacting perchloroethylene with hydrogen fluoride (HF) at elevated temperature in the vapour phase in at least one reactor in the presence of a fluorination catalyst. The process is operated so that 30 weight % or more of the perchloroethylene reactant that is fed to the at least one reactor remains unreacted having passed through the or each reactor. The dichlorotrifluoroethane may be purified and then used as it is or used to prepare pentafluoroethane.Type: ApplicationFiled: September 23, 2011Publication date: January 19, 2012Applicant: Mexichem Amanco S.A. de C.V.Inventors: Clive Robert GIDDIS, Paul Hendry Stewert
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Publication number: 20120016165Abstract: A process for the production of dichlorotrifluoroethane is described. The process comprises reacting perchloroethylene with hydrogen fluoride in the vapour phase at elevated temperature in at least one reactor in the presence of a fluorination catalyst to produce a composition comprising dichlorotrifluoroethane, hydrogen chloride, unreacted perchloroethylene and unreacted hydrogen fluoride. The composition that is produced is subjected to a separation step to recover a first fraction comprising dichlorotrifluoroethane and a second fraction comprising perchloroethylene and hydrogen fluoride. The second fraction is further separated into a hydrogen fluoride-rich fraction and a perchloroethylene-containing, organic-rich fraction which are then recycled. The dichlorotrifluoroethane that is recovered may be used to prepare pentafluoroethane.Type: ApplicationFiled: September 23, 2011Publication date: January 19, 2012Applicant: Mexichem Amanco S.A. de C.V.Inventors: CLIVE ROBERT GIDDIS, PAUL HENDRY STEWERT
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Patent number: 8058485Abstract: A process for the production of dichlorotrifluoroethane is described. The process comprises reacting perchloroethylene with hydrogen fluoride in the vapor phase at elevated temperature in at least one reactor in the presence of a fluorination catalyst to produce a composition comprising dichlorotrifluoroethane, hydrogen chloride, unreacted perchloroethylene and unreacted hydrogen fluoride. The composition that is produced is subjected to a separation step to recover a first fraction comprising dichlorotrifluoroethane and a second fraction comprising perchloroethylene and hydrogen fluoride. The second fraction is further separated into a hydrogen fluoride-rich fraction and a perchloroethylene-containing, organic-rich fraction which are then recycled. The dichlorotrifluoroethane that is recovered may be used to prepare pentafluoroethane.Type: GrantFiled: December 18, 2006Date of Patent: November 15, 2011Assignee: Mexichem Amanco S.A. de C.V.Inventors: Clive Robert Giddis, Paul Hendry Stewert
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Patent number: 8058487Abstract: The present invention relates to a continuous process for the fluorination of perchloroethylene (PER) in the gas phase in a single stage with hydrofluoric acid (HF) in the presence of a catalyst to give, as major product, pentafluoroethane. The process is characterized in that it is carried out at a temperature of between 280 and 430° C. and with an HF/PER molar ratio of greater than or equal to 20.Type: GrantFiled: November 30, 2006Date of Patent: November 15, 2011Assignee: Arkema FranceInventors: Beatrice Boussand, Michel Devic
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Patent number: 8053611Abstract: A process is disclosed for the manufacture of 1,1,1,3,3,3-hexafluoropropane and 1,1,1,2,3,3-hexafluoropropane, hexafluoropropene and/or 1,1,1,2,3,3,3-heptafluoropropane. The process involves (a) reacting HF, Cl2, and at least one halopropene of the formula CX3CCl?CClX (where each X is independently F or Cl) to produce a product comprising CF3CCl2CF3 and CF3CClFCClF2; (b) reacting CF3CCl2CF3 and CF3CClFCClF2 produced in (a) with hydrogen, optionally in the presence of HF, to produce a product comprising CF3CH2CF3 and at least one of CHF2CHFCF3, CF3CF?CF2 and CF3CFHCF3; and (c) recovering from the product produced in (b), CF3CH2CF3 and at least one of CHF2CHFCF3, CF3CF?CF2 and CF3CFHCF3. In (a), the CF3CCl2CF3 and CF3CClFCClF2 are produced in the presence of a chlorofluorination catalyst including (i) a crystalline alpha-chromium oxide where at least 0.Type: GrantFiled: August 4, 2006Date of Patent: November 8, 2011Assignee: E. I. du Pont de Nemours and CompanyInventors: Velliyur Nott Mallikarjuna Rao, H. David Rosenfeld, Allen Capron Sievert, Shekhar Subramoney
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Patent number: 8049045Abstract: A process for the production of dichlorotrifluoroethane is described. The process comprises reacting perchloroethylene with hydrogen fluoride (HP) at elevated temperature in the vapor phase in at least one reactor in the presence of a fluorination catalyst. The process is operated so that 30 weight % or more of the perchloroethylene reactant that is fed to the at least one reactor remains unreacted having passed through the or each reactor. The dichlorotrifluoroethane may be purified and then used as it is or used to prepare pentafluoroethane.Type: GrantFiled: December 18, 2006Date of Patent: November 1, 2011Assignee: Mexichem Amanco S.A. de C.V.Inventors: Clive Robert Giddis, Paul Hendry Stewert
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Publication number: 20110237846Abstract: To provide processes for efficiently and economically producing 2-chloro-1,1,1,2-tetrafluoropropane (R244bb) and 2,3,3,3-tetrafluoropropene (R1234yf) in an industrially practical manner. A process for producing 2-chloro-1,1,1,2-tetrafluoropropane, which comprises a chlorination step of reacting 1,2-dichloro-2-fluoropropane and chlorine in the presence of a solvent under irradiation with light to obtain 1,1,1,2-tetrachloro-2-fluoropropane, and a fluorination step of reacting the 1,1,1,2-tetrachloro-2-fluoropropane obtained in the chlorination step and hydrogen fluoride in the presence of a catalyst to obtain 2-chloro-1,1,1,2-tetrafluoropropane, and a process for producing 2,3,3,3-tetrafluoropropene, which comprises dehydrochlorinating it in the presence of a catalyst.Type: ApplicationFiled: June 10, 2011Publication date: September 29, 2011Applicant: ASAHI GLASS COMPANY, LIMITEDInventors: Satoshi KAWAGUCHI, Takashi OKAZOE, Hidekazu OKAMOTO
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Publication number: 20110224466Abstract: A new chromium-containing fluorination catalyst is described. The catalyst comprises an amount of zinc that promotes activity and from 0.1 to 8.0% by weight of the chromium in the catalyst based on the total weight of the chromium is present as chromium (VI). The use of the zinc-promoted, chromium-containing catalyst in a fluorination process in which a hydrocarbon or halogenated hydrocarbon is reacted with hydrogen fluoride in the vapour-phase at elevated temperatures is also described.Type: ApplicationFiled: September 4, 2009Publication date: September 15, 2011Inventor: Andrew P. Sharratt
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Patent number: 7947856Abstract: A telomerisation process is described whereby haloalkanes like tetrachloromethane are added to halogenated olefins like 2-chloroprop-1-ene in the presence of an iron catalyst and a phosphite. The reaction products, e.g. 1,1,1,3,3-pentachlorobutane, can be fluorinated.Type: GrantFiled: October 5, 2007Date of Patent: May 24, 2011Assignee: SOLVAY (Societe Anonyme)Inventors: Veronique Mathieu, Francine Janssens
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Publication number: 20110118514Abstract: A process is disclosed for the manufacture of 1,1,1,3,3,3-hexafluoropropane and 1,1,1,2,3,3-hexafluoropropane, hexafluoropropene and/or 1,1,1,2,3,3,3-heptafluoropropane. The process involves (a) reacting HF, Cl2, and at least one halopropene of the formula CX3CCI?CCIX (where each X is independently F or CI) to produce a product comprising CF3CCI2CF3 and CF3CCIFCCIF2; (b) reacting CF3CCI2CF3 and CF3CCIFCCIF2 produced in (a) with hydrogen, optionally in the presence of HF, to produce a product comprising CF3CH2CF3 and at least one of CHF2CHFCF3, CF3CF?CF2 and CF3CFHCF3; and (c) recovering from the product produced in (b), CF3CH2CF3 and at least one of CHF2CHFCF3, CF3CF?CF2 and CF3CFHCF3. In (a), the CF3CCI2CF3 and CF3CCIFCCIF2 are produced in the presence of a chlorofluorination catalyst including (i) a crystalline alpha-chromium oxide where at least 0.Type: ApplicationFiled: August 4, 2006Publication date: May 19, 2011Inventors: Velliyur Nott Mallikarjuna Rao, H. David Rosenfeld, Allen Capron Sievert, Shekhar Subramoney
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Patent number: RE49849Abstract: A process is disclosed for making CF3CF2CH3, CF3CF?CH2 and/or CF3CCl?CH2. The process involves reacting at least one starting material selected from the group consisting of halopropanes of the formula CX3CH2CH2X, halopropenes of the formula CX3CH?CH2 and halopropenes of the formula CX2?CHCH2X, wherein each X is independently F or Cl, with HF and Cl2 in a reaction zone to produce a product mixture comprising HF, HCl, CF3CF2CH3, CF3CF?CH2, and CF3CCl?CH2; and recovering the CF3CF2CH3, CF3CF?CH2 and/or CF3CCl?CH2 from the product mixture. Also disclosed is a process for making CF3CH2CHF2, CF3CH?CHF, and/or CF3CH?CHCl.Type: GrantFiled: November 25, 2014Date of Patent: February 27, 2024Assignee: THE CHEMOURS COMPANY FC, LLCInventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert