Replacing Halogen With Hydrogen Patents (Class 570/176)
  • Patent number: 11912923
    Abstract: A process is disclosed for making CF3CF?CHF. The process involves reacting CF3CClFCCl2F with H2 in a reaction zone in the presence of a catalyst to produce a product mixture comprising CF3CF?CHF. The catalyst has a catalytically effective amount of palladium supported on a support selected from the group consisting of alumina, fluorided alumina, aluminum fluoride and mixtures thereof and the mole ratio of H2 to CF3CClFCCl2F fed to the reaction zone is between about 1:1 and about 5:1. Also disclosed are azeotropic compositions of CF3CClFCCl2F and HF and azeotropic composition of CF3CHFCH2F and HF.
    Type: Grant
    Filed: June 6, 2023
    Date of Patent: February 27, 2024
    Assignee: THE CHEMOURS COMPANY FC, LLC
    Inventors: Velliyur Nott Mallikarjuna Rao, Mario Joseph Nappa, Allen Capron Sievert
  • Patent number: 10633311
    Abstract: A hydrogenation process is disclosed. The process involves reacting a fluoroolefin with H2 in a reaction zone in the presence of a palladium catalyst to produce a hydrofluoroalkane product, wherein the palladium catalyst comprises palladium supported on a carrier wherein the palladium concentration is from about 0.001 wt % to about 0.2 wt % based on the total weight of the palladium and the carrier. Also disclosed is a palladium catalyst composition consisting essentially of palladium supported on ?-Al2O3 wherein the palladium concentration is from about 0.001 wt % to about 0.2 wt % based on the total weight of the palladium and the ?-Al2O3. Also disclosed is a hydrogenation process comprising reacting a fluoroolefin with H2 in a reaction zone in the presence of a palladium catalyst to produce a hydrofluoroalkane product, characterized by: the palladium catalyst consisting essentially of palladium supported on ?-Al2O3 wherein the palladium concentration is from about 0.001 wt % to about 0.
    Type: Grant
    Filed: March 4, 2019
    Date of Patent: April 28, 2020
    Assignee: THE CHEMOURS COMPANY FC, LLC
    Inventors: Patricia Cheung, Concetta Lamarca
  • Patent number: 9283546
    Abstract: The present disclosure relates to a novel photocatalyst composition and a process of using the photocatalyst for the photocatalytic degradation of methyl tertiary-butyl ether (MTBE) in water. Palladium doped nano zinc oxide photocatalyst was prepared by zinc nitrate hexahydrate and an ammonium carbonate and the photocatalyst composition demonstrated more than 90-99% degradation of MTBE at room temperatures in a photo catalytic reaction conducted in an oxygen saturated aqueous medium.
    Type: Grant
    Filed: July 24, 2013
    Date of Patent: March 15, 2016
    Assignee: Umm-Al-Qura University
    Inventors: Zaki S Seddigi, Saleh A Saleh
  • Publication number: 20150126785
    Abstract: The invention provides a process comprising contacting (1243zf) or (253fb) with hydrogen in the presence of a hydrogenation catalyst to produce a composition comprising 1,1,1-trifluoropropane (263fb).
    Type: Application
    Filed: July 18, 2012
    Publication date: May 7, 2015
    Applicant: MEXICHEM AMANCO HOLDING S.A. DE C.V.
    Inventors: Andrew P. Sharratt, Claire Elizabeth Mcguinness, Emma Jane Hodgson
  • Patent number: 8940948
    Abstract: Provided are methods for producing fluorinated organic compounds, which preferably comprises converting at least one compound of formula (I) CH2XCHZCF3 to at least one compound of formula (II) CHX?CZCF3 where X and Z are independently H or F, with the proviso that X and Z are not the same. The converting step comprises catalytically reacting at least one compound of formula (I), preferably via dehydrogenation or oxidative dehydrogenation. In another aspect, the inventive method of preparing fluorinated organic compounds comprises converting a reaction stream comprising at least one pentafluoropropene to a product stream comprising at least one pentafluoropropane and at least one compound of formula (I), separating out the compound of formula (I) from the product stream, and converting the compound of formula (I) separated from the product stream to at least one compound of formula (II), wherein the conversion the compound of formula (I) to 3,3,3-trifluoropropyne is substantially limited.
    Type: Grant
    Filed: July 17, 2013
    Date of Patent: January 27, 2015
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Publication number: 20150017064
    Abstract: A trifluoroethylene composition which is safe to handle and which can be safely stored and transported at pressures of up to 5.00 MPa. The composition comprises trifluoroethylene and HCl in a molar ratio trifluoroethylene:HCl from 10:90 to 63:37. When the composition is a compressed gas it has a pressure of from 0.50 to 5.00 MPa.
    Type: Application
    Filed: January 31, 2013
    Publication date: January 15, 2015
    Inventor: Emanuela Antenucci
  • Patent number: 8766021
    Abstract: In the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf), formation of HFC-254eb as an excessively reduced product is suppressed. A process for producing 2,3,3,3-tetrafluoropropene, which comprises reacting a raw material compound gas composed of at least one of 1,1-dichloro-2,3,3,3-tetrafluoropropene and 1-chloro-2,3,3,3-tetrafluoropropene, and hydrogen gas, in the presence of a catalyst, wherein the catalyst is a catalyst having palladium supported on active carbon, and the ratio of the number of moles of the hydrogen gas to the number of moles of chlorine atoms in the raw material compound gas (H2/Cl) is at most 0.7.
    Type: Grant
    Filed: June 23, 2011
    Date of Patent: July 1, 2014
    Assignee: Asahi Glass Company, Limited
    Inventors: Satoshi Kawaguchi, Hidekazu Okamoto, Yu Takeuchi, Hirokazu Takagi, Kunio Watanabe, Koichi Yanase
  • Patent number: 8674147
    Abstract: A process for the selective dehydrochlorination of a hydrochlorofluoroalkane by using chloride fluorides of Ba, Ca, or Sr as catalysts, wherein the hydrochlorofluoroalkane comprises a carbon atom or carbon atoms carrying at least one chlorine and at least one fluorine atom and further comprises at least one hydrogen atom on a carbon atom vicinal to the carbon atom or to the carbon atoms carrying the at least one chlorine and at least one fluorine atom.
    Type: Grant
    Filed: March 31, 2011
    Date of Patent: March 18, 2014
    Assignee: Solvay SA
    Inventors: Johannes Eicher, Ercan Uenveren, Erhard Kemnitz
  • Patent number: 8642820
    Abstract: To provide a process to produce 1,1-dichloro-2,3,3,3-tetrafluoropropene (CFO-1214ya) simply and economically without requiring purification of 1,1-dichloro-2,2,3,3,3-pentafluoropropane (HCFC-225ca) from the raw material component obtained as a mixture of isomers, i.e. dichloropentafluoropropane (HCFC-225) including HCFC-225ca and at the same time to produce simply and economically 2,3,3,3-tetrafluoropropene (HFO-1234yf) from 1-chloro-2,3,3,3-tetrafluoropropane (HCFC-244eb). A raw material composition comprising HCFC-244eb and HCFC-225 including HCFC-225ca is contacted with an alkali aqueous solution in the presence of a phase-transfer catalyst to produce CFO-1214ya from HCFC-225ca and at the same time to produce HFO-1234yf from HCFC-244eb.
    Type: Grant
    Filed: June 23, 2011
    Date of Patent: February 4, 2014
    Assignee: Asahi Glass Company, Limited
    Inventors: Ryuji Seki, Hidekazu Okamoto, Hirokazu Takagi, Satoshi Kawaguchi
  • Patent number: 8609908
    Abstract: To provide a process for producing, at a high content ratio, 1,1-dichloro-2,2,3,3,3-pentafluoropropane (HCFC-225ca) which is useful as e.g. a starting material to obtain 1,1-dichloro-2,3,3,3-tetrafluoropropene (CFO1214ya). The process for producing HCFC-225ca of the present invention comprises subjecting a raw material composed of dichloropentafluoropropane (HCFC-225) including 2,2-dichloro-1,1,1,3,3-pentafluoropropane (HCFC225aa) to an isomerization reaction at a temperature of at most 290° C. in a gas phase in the presence of a metal oxide catalyst thereby to isomerize HCFC-225aa to HCFC-225ca.
    Type: Grant
    Filed: June 23, 2011
    Date of Patent: December 17, 2013
    Assignee: Asahi Glass Company, Limited
    Inventor: Hidekazu Okamoto
  • Patent number: 8569553
    Abstract: The object is to provide a process whereby it is possible to produce 2,3,3,3-tetrafluoropropene at a high conversion ratio constantly for a long period of time. A process for producing 2,3,3,3-tetrafluoropropene, which comprises reacting a raw material compound of at least one of 1,1-dichloro-2,3,3,3-tetrafluoropropene and 1-chloro-2,3,3,3-tetrafluoropropene, and hydrogen, in the presence of a catalyst, wherein the catalyst is a noble metal catalyst supported on a metal oxide having a Hammett acidity function value (H0) of at least ?5.6.
    Type: Grant
    Filed: June 23, 2011
    Date of Patent: October 29, 2013
    Assignee: Asahi Glass Company, Limited
    Inventors: Hirokazu Takagi, Hidekazu Okamoto
  • Patent number: 8563790
    Abstract: There is provided according the present invention a process for producing 2-chloro-3,3,3-trifluoropropene, comprising: hydrogenating 1,2-dichloro-3,3,3-trifluoropropene with hydrogen (H2) in the presence of a catalyst having a transition metal and a poisoning substance supported on a support. The present production process is industrially advantageous as the target 2-chloro-3,3,3-trifluoropropene can be obtained with high selectivity and high yield under moderate reaction conditions and with easy waste treatment.
    Type: Grant
    Filed: July 16, 2010
    Date of Patent: October 22, 2013
    Assignee: Central Glass Company, Limited
    Inventors: Yasuo Hibino, Fumihiro Kawagoe, Fuyuhiko Sakyu
  • Patent number: 8530710
    Abstract: The object is to provide a process whereby it is possible to produce 2,3,3,3-tetrafluoropropene at a high conversion ratio constantly for a long period of time. A process for producing 2,3,3,3-tetrafluoropropene, which comprises reacting a raw material compound of at least one of 1,1-dichloro-2,3,3,3-tetrafluoropropene and 1-chloro-2,3,3,3-tetrafluoropropene, and hydrogen, in the presence of a noble metal catalyst supported on active carbon having an ash content of at most 3% as measured in accordance with ASTM D2866.
    Type: Grant
    Filed: June 23, 2011
    Date of Patent: September 10, 2013
    Assignee: Asahi Glass Company, Limited
    Inventors: Hirokazu Takagi, Hidekazu Okamoto, Satoshi Kawaguchi, Yu Takeuchi, Kunio Watanabe, Koichi Yanase, Shingo Nomura
  • Patent number: 8530711
    Abstract: The object is to provide a process for producing highly pure 2,3,3,3-tetrafluoropropene, whereby formation of 3,3,3-trifluoropropene is suppressed. A process for producing 2,3,3,3-tetrafluoropropene, which comprises reacting a raw material compound composed of 1,1-dichloro-2,3,3,3-tetrafluoropropene and/or 1-chloro-2,3,3,3-tetrafluoropropene, and hydrogen in a gas phase in a reactor having a catalyst layer packed with a catalyst-supporting carrier, while maintaining the maximum temperature of the catalyst layer to be at most 130° C., to obtain formed gas containing 2,3,3,3-tetrafluoropropene, and then, contacting the formed gas discharged from the reactor, with alkali at a temperature of at most 100° C.
    Type: Grant
    Filed: June 23, 2011
    Date of Patent: September 10, 2013
    Assignee: Asahi Glass Company, Limited
    Inventors: Satoshi Kawaguchi, Hidekazu Okamoto, Yu Takeuchi, Hirokazu Takagi, Kunio Watanabe, Koichi Yanase
  • Patent number: 8513474
    Abstract: Provided are methods for producing fluorinated organic compounds, which preferably comprises converting at least one compound of formula (I) CH2XCHZCF3 to at least one compound of formula (II) CHX?CZCF3 where X and Z are independently H or F, with the proviso that X and Z are not the same. The converting step comprises catalytically reacting at least one compound of formula (I), preferably via dehydrogenation or oxidative dehydrogenation. In another aspect, the inventive method of preparing fluorinated organic compounds comprises converting a reaction stream comprising at least one pentafluoropropene to a product stream comprising at least one pentafluoropropane and at least one compound of formula (I), separating out the compound of formula (I) from the product stream, and converting the compound of formula (I) separated from the product stream to at least one compound of formula (II), wherein the conversion the compound of formula (I) to 3,3,3-trifluoropropyne is substantially limited.
    Type: Grant
    Filed: June 24, 2010
    Date of Patent: August 20, 2013
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Patent number: 8471078
    Abstract: A method of providing a blend of tetra- and/or pentafluoroalkanes comprising hydrogenating a pentafluoropropene.
    Type: Grant
    Filed: January 23, 2009
    Date of Patent: June 25, 2013
    Assignee: Mexichem Amanco Holding S.A. de C.V.
    Inventors: Robert E. Low, Andrew P. Sharratt
  • Patent number: 8399721
    Abstract: Disclosed is a process for the preparation of fluorine-containing olefins comprising contacting a chlorofluoroalkene with hydrogen in the presence of a catalyst at a temperature sufficient to cause replacement of the chlorine substituents of the chlorofluoroalkene with hydrogen to produce a fluorine-containing olefin, wherein said catalyst is a composition comprising chromium, nickel and optionally an alkali metal selected from potassium and cesium. Also disclosed are catalyst compositions for the hydrodechlorination of chlorofluoroalkenes comprising copper, nickel, and an alkali metal selected from potassium and cesium, and methods of making such catalysts.
    Type: Grant
    Filed: December 18, 2009
    Date of Patent: March 19, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Ekaterina N. Swearingen
  • Patent number: 8399722
    Abstract: The object is to provide a process for producing highly pure 2,3,3,3-tetrafluoropropene, whereby formation of 3,3,3-trifluoropropene as a by-product is suppressed. A process for producing 2,3,3,3-tetrafluoropropene, which comprises introducing and reacting a raw material compound composed of at least one of 1,1-dichloro-2,3,3,3-tetrafluoropropene and 1-chloro-2,3,3,3-tetrafluoropropene, and hydrogen, in a catalyst layer packed with a catalyst-supporting carrier, wherein the temperature of the catalyst layer is controlled to be higher than the dew point of the raw material mixed gas comprising the raw material compound and the hydrogen, and the maximum temperature of the catalyst layer is maintained to be at most 130° C. during the reaction.
    Type: Grant
    Filed: June 23, 2011
    Date of Patent: March 19, 2013
    Assignee: Asahi Glass Company, Limited
    Inventors: Satoshi Kawaguchi, Hidekazu Okamoto, Yu Takeuchi, Hirokazu Takagi, Kunio Watanabe, Koichi Yanase
  • Publication number: 20130018211
    Abstract: A process for the selective dehydrochlorination of a hydrochlorofluoroalkane by using chloride fluorides of Ba, Ca, or Sr as catalysts, wherein the hydrochlorofluoroalkane comprises a carbon atom or carbon atoms carrying at least one chlorine and at least one fluorine atom and further comprises at least one hydrogen atom on a carbon atom vicinal to the carbon atom or to the carbon atoms carrying the at least one chlorine and at least one fluorine atom.
    Type: Application
    Filed: March 31, 2011
    Publication date: January 17, 2013
    Applicant: SOLVAY SA
    Inventors: Johannes Eicher, Ercan Uenveren, Erhard Kemnitz
  • Publication number: 20130006022
    Abstract: The present invention provides a method for producing a fluorine-containing alkane, which comprises reacting at least one fluorine-containing compound selected from the group consisting of chlorine-containing fluoroalkanes and fluorine-containing alkenes with hydrogen gas in the presence of catalysts, wherein two or more catalysts having different catalytic activities are used, and the fluorine-containing compound and hydrogen gas, which are starting materials, are sequentially brought into contact with the catalysts in the order of the catalyst having a lower catalytic activity followed by the catalyst having a higher catalytic activity. According to the present invention, in the method for producing a fluorine-containing alkane by using chlorine-containing fluoroalkane or fluorine-containing alkene as a starting material, and subjection it to a reduction reaction or a hydrogen addition reaction, the objective fluorine-containing alkane can be produced with high productivity.
    Type: Application
    Filed: February 18, 2011
    Publication date: January 3, 2013
    Applicant: DAIKIN INDUSTRIES, LTD.
    Inventors: Yuko Shiotani, Kakeru Hanabusa, Takehiro Chaki, Kazuhiro Takahashi
  • Patent number: 8338652
    Abstract: The present invention provides a simple and efficient process for producing 2,3,3,3-tetrafluoropropene(HFC-1234yf), the process being useful for industrial production. More specifically, the present invention relates to: a process for producing 2,3,3,3-tetrafluoropropene, comprising the steps of: (I) reacting a compound expressed by Formula (1): CF3CF2CH2X??(1) wherein X represents Cl, Br or I, with a base to produce a compound expressed by Formula (2): CF3CF?CHX??(2) wherein X is the same as above; and (II) reducing the compound expressed by Formula (2) with hydrogen in the presence of a catalyst to produce 2,3,3,3-tetrafluoropropene.
    Type: Grant
    Filed: September 10, 2008
    Date of Patent: December 25, 2012
    Assignee: Daikin Industries, Ltd.
    Inventors: Junpei Terada, Takuji Ishikawa
  • Patent number: 8236997
    Abstract: A process for the production of pentafluoroethane is described. The process comprises reacting perchloroethylene with hydrogen fluoride in the vapor phase in a first reactor or a first plurality of reactors in the presence of a fluorination catalyst to produce a composition comprising dichlorotrifluoroethane, hydrogen chloride, unreacted hydrogen fluoride and perchloroethylene. This composition is subjected to a separation step to yield a purified composition comprising at least 95 weight % of dichlorotrifluorethane and less than 0.5 weight % of compounds having the formula C2C16-XFX, where x is an integer of from 0 to 6, base the total weight of organic compounds in the composition. The composition from the separation step is then reacted with hydrogen fluoride in the vapor phase in a second reactor or a second plurality of reactors in the presence of a fluorination catalyst to produce a composition comprising pentafluoroethane and less than 0.
    Type: Grant
    Filed: December 18, 2006
    Date of Patent: August 7, 2012
    Assignee: Mexichem Amanco Holding S.A. de C.V.
    Inventors: Clive Robert Giddis, Paul Hendry Stewert
  • Publication number: 20120123173
    Abstract: There is provided according the present invention a process for producing 2-chloro-3,3,3-trifluoropropene, comprising: hydrogenating 1,2-dichloro-3,3,3-trifluoropropene with hydrogen (H2) in the presence of a catalyst having a transition metal and a poisoning substance supported on a support. The present production process is industrially advantageous as the target 2-chloro-3,3,3-trifluoropropene can be obtained with high selectivity and high yield under moderate reaction conditions and with easy waste treatment.
    Type: Application
    Filed: July 16, 2010
    Publication date: May 17, 2012
    Applicant: Central Glass Company, Limited
    Inventors: Yasuo Hibino, Fumihiro Kawagoe, Fuyuhiko Sakyu
  • Patent number: 8058489
    Abstract: A process is disclosed for making CF3CF?CHF or mixtures thereof with CF2?CFCHF2.
    Type: Grant
    Filed: November 15, 2007
    Date of Patent: November 15, 2011
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Patent number: 7981312
    Abstract: A process is disclosed for making CF3CF?CH2 or mixtures thereof with CHF?CFCHF2. The process involves contacting CCl3CF2CF3 and optionally CCl2FCF2CClF2 with H2 in the presence of a palladium catalyst supported on a support of alumina, fluorided alumina and/or aluminum fluoride, to produce a product mixture including CH2?CFCF3 (and when CCl2FCF2CClF2 is present, CHF?CFCHF2); recovering CH2?CFCF3 or a mixture thereof with CHF?CFCHF2 from the product mixture. The present invention also provides another process that involves reacting CCl3CF2CF3 and optionally CCl2FCF2CClF2 with H2 in the presence of a hydrogenation catalyst to form CH3CF2CF3 (and when CCl2FCF2CClF2 is present, CH2FCF2CHF2); dehydrofluorinating; and recovering CH2?CFCF3 or a mixture thereof with CHF?CFCHF2.
    Type: Grant
    Filed: October 31, 2007
    Date of Patent: July 19, 2011
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Velliyur Mallikarjuna Nott Rao, Allen Capron Sievert
  • Publication number: 20110172469
    Abstract: To provide a method for producing 1,1-dichloro-2,2,3,3,3-pentafluoropropane (HCFC-225ca) at a high content ratio, which is useful as e.g. a starting material to obtain 1,1-dichloro-2,3,3,3-tetrafluoropropene (R1214ya). The method comprises subjecting a starting material comprising one isomer or a mixture of at least two isomers of dichloropentafluoropropane (HCFC-225) and having a HCFC-225ca content of less than 60 mol %, to an isomerization reaction in the presence of a Lewis acid catalyst or a metal oxide catalyst so as to increase the HCFC-225ca content in the product to be higher than the content in the starting material.
    Type: Application
    Filed: March 21, 2011
    Publication date: July 14, 2011
    Applicant: ASAHI GLASS COMPANY LIMITED
    Inventor: Hidekazu OKAMOTO
  • Publication number: 20110060172
    Abstract: A support of metal oxyfluoride or metal halide for a metal-based hydrogenation catalyst useful in hydrogenating fluoroolefins is provided.
    Type: Application
    Filed: September 4, 2009
    Publication date: March 10, 2011
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: HAIYOU WANG, HSUEH S. TUNG
  • Publication number: 20110028770
    Abstract: An alpha-alumina support for a hydrogenation catalyst useful in hydrogenating fluoroolefins is provided.
    Type: Application
    Filed: August 3, 2009
    Publication date: February 3, 2011
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: HAIYOU WANG, HSUEH SUNG TUNG, DANIEL C. MERKEL
  • Patent number: 7872161
    Abstract: A process is disclosed for making CF3CF?CH2 The process involves (i) contacting CHCl2CF2CF3 in a reaction zone in the presence of a catalytically effective amount of a dehydrofluorination catalyst to produce CCl2?CFCF3; (ii) contacting CCl2?CFCF3 with H2 formed in (i) in a reaction zone in the presence of a catalyst comprising a catalytically effective amount of palladium supported on a support selected from the group consisting of alumina fluorided alumina, aluminum fluoride and mixtures thereof, to produce a product mixture comprising CF3CF?CH2, wherein the mole ratio of H2 to CCl2?CFCF3 fed to the reaction zone is between about 1:1 and about 4:1 and (iii) recovering CF3CF?CH2 from the product mixture formed in (ii).
    Type: Grant
    Filed: November 15, 2007
    Date of Patent: January 18, 2011
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Patent number: 7872162
    Abstract: Process for the obtention of HFC-227ea having a reduced content of organic impurities, comprising at least subjecting a crude HFC-227ea to two distillation steps at different pressures.
    Type: Grant
    Filed: December 1, 2008
    Date of Patent: January 18, 2011
    Assignee: Solvay S.A.
    Inventors: Thomas Müller, Dominique Balthasart, Bernd Kutzner
  • Patent number: 7795482
    Abstract: Disclosed herein is a process for the preparation of fluorine-containing olefins comprising contacting a chlorofluoroalkene with hydrogen in the presence of a catalyst at a temperature sufficient to cause replacement of the chlorine substituents with hydrogen. Also disclosed is a catalyst composition for the hydrodechlorination of chlorofluoroalkenes comprising copper metal deposited on a support.
    Type: Grant
    Filed: June 27, 2008
    Date of Patent: September 14, 2010
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Ekaterina N. Swearingen
  • Patent number: 7786333
    Abstract: A process for the production of fluorinated olefins, preferably fluorinated propenes, by contacting a feed stream containing a fluorinated olefin and hydrogen with a first amount of catalyst to produce the hydrofluorocarbon, wherein a first exit stream contains unreacted fluorinated olefin and hydrogen; contacting the first exit stream with a second amount of catalyst to produce a hydrofluorocarbon, wherein the second amount of catalyst is preferably greater than the first amount of catalyst; and contacting the hydrofluorocarbon with a catalyst for dehydrohalogenation to produce a product stream of fluorinated olefin.
    Type: Grant
    Filed: February 19, 2009
    Date of Patent: August 31, 2010
    Assignee: Honeywell International, Inc.
    Inventors: Michael Van Der Puy, George R. Cook, Peter H. Sheidle, Kevin D. Uhrich, Haiyou Wang, Hsueh Sung Tung
  • Patent number: 7659435
    Abstract: A process is disclosed for the manufacture of CF3CH2CHF2 and CF3CHFCH2F. The process involves (a) reacting hydrogen fluoride, chlorine, and at least one halopropene of the formula CX3CCl?CClX (where each X is independently F or Cl) to produce a product including both CF3CCl2CClF2 and CF3CClFCCl2F; (b) reacting CF3CCl2CClF2 and CF3CClFCCl2F produced in (a) with hydrogen to produce a product including both CF3CH2CHF2, and CF3CHFCH2F; and (c) recovering CF3CH2CHF2 and CF3CHFCH2F from the product produced in (b). 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 0.05 atom % of the chromium atoms in the alpha-chromium oxide lattice are replaced by divalent copper, and/or (ii) a chromium-containing composition of (i) which has been treated with a fluorinating agent.
    Type: Grant
    Filed: August 4, 2006
    Date of Patent: February 9, 2010
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, H. David Rosenfeld, Allen Capron Sievert, Shekhar Subramoney
  • Patent number: 7659436
    Abstract: A process for the manufacture of CF3CH2CHF2 and/or CF3CH2CF3 is disclosed. The process involves (a) reacting HF and at least one halopropene of the formula CX3CCI?CCIX (where each X is independently F or Cl) to produce a product including both CF3CCI?CF2 and CF3CHCICF3; (b) reacting CF3CCI?CF2 and/or CF3CHCICF3 produced in (a) with hydrogen to produce a product including CF3CH2CHF2 and/or CF3CH2CF3; and (c) recovering CF3CH2CHF2 and/or CF3CH2CF3 from the product produced in (b). In (a), the CF3CCI?CF2 and CF3CHCICF3 are produced in the presence of a fluorination catalyst comprising at least one chromium-containing component selected from (i) a crystalline alpha-chromium oxide where at least 0.05 atom % of the chromium atoms in the alpha-chromium oxide lattice are replaced by divalent copper, and (ii) a chromium-containing composition of (i) which has been treated with a fluorinating agent.
    Type: Grant
    Filed: August 4, 2006
    Date of Patent: February 9, 2010
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, H. David Rosenfeld, Allen Capron Sievert, Shekhar Subramoney
  • Patent number: 7629496
    Abstract: A process for the manufacture of 1,1,1,3,3-pentafluoropropane, which comprises reacting 1,1,1,3,3,3-hexafluoropropane with a source of hydrogen.
    Type: Grant
    Filed: March 22, 2007
    Date of Patent: December 8, 2009
    Assignee: Solvay (Societé Anonyme)
    Inventors: Johannes Eicher, Stefan Mross
  • Patent number: 7560602
    Abstract: A process for the production of fluorinated olefins, preferably fluorinated propenes, by contacting a feed stream containing a fluorinated olefin and hydrogen with a first amount of catalyst to produce the hydrofluorocarbon, wherein a first exit stream contains unreacted fluorinated olefin and hydrogen; contacting the first exit stream with a second amount of catalyst to produce a hydrofluorocarbon, wherein the second amount of catalyst is preferably greater than the first amount of catalyst; and contacting the hydrofluorocarbon with a catalyst for dehydrohalogenation to produce a product stream of fluorinated olefin.
    Type: Grant
    Filed: October 27, 2006
    Date of Patent: July 14, 2009
    Assignee: Honeywell International Inc.
    Inventors: Michael Van Der Puy, George R. Cook, Peter H. Scheidle, Kevin D. Uhrich, Haiyou Wang, Hsueh Sung Tung
  • Patent number: 7504358
    Abstract: A crystalline alpha-chromium oxide where from about 0.05 atom % to about 2 atom % of the chromium atoms in the alpha-chromium oxide lattice are substituted by nickel atoms, and optionally, additional chromium atoms in the alpha-chromium oxide lattice are substituted by trivalent cobalt atoms (provided that the total amount of the nickel atoms and the trivalent cobalt atoms in the alpha-chromium oxide lattice is no more than 6 atom %) is disclosed. Also disclosed is a chromium-containing catalyst composition comprising as a chromium-containing component the crystalline substituted alpha-chromium oxide; and a method for preparing a composition comprising the crystalline substituted alpha-chromium oxide.
    Type: Grant
    Filed: August 21, 2003
    Date of Patent: March 17, 2009
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, H. David Rosenfeld, Allen C. Sievert, Shekhar Subramoney, Munirpallam Appadorai Subramanian
  • Patent number: 7470828
    Abstract: Provided are methods for producing hydrofluorocarbons via the selective reduction of a halocarbon blend comprising 1,3-dichloro-1,1,2,2,3-pentafluoropropane.
    Type: Grant
    Filed: October 10, 2007
    Date of Patent: December 30, 2008
    Assignee: Honeywell International Inc.
    Inventors: Haridasan Nair, Sudip Mukhopadhyay, Michael Van Der Puy
  • Patent number: 7459591
    Abstract: Process for the obtention of HFC-227ea having a reduced content of organic impurities, comprising at least subjecting a crude HFC-227ea to two distillation steps at different pressures.
    Type: Grant
    Filed: July 24, 2007
    Date of Patent: December 2, 2008
    Assignee: Solvay S.A.
    Inventors: Thomas Müller, Dominique Balthasart, Bernd Kutzner
  • Patent number: 7335804
    Abstract: Provided are methods for producing hydrofluorocarbons via the selective reduction of a halocarbon blend comprising 1,3-dichloro-1,1,2,2,3-pentafluoropropane.
    Type: Grant
    Filed: November 3, 2005
    Date of Patent: February 26, 2008
    Assignee: Honeywell International Inc.
    Inventors: Haridasan Nair, Sudip Mukhopadhyay, Michael Van Der Puy
  • Patent number: 7329786
    Abstract: Methods and materials are provided for the production of essentially isomerically pure perhalogenated and partially halogenated compounds. One embodiment of the present invention provides a process for the production of essentially isomerically pure CFC-216aa. Other embodiments include processes for the production of CFC-217ba and HFC-227ea. Particular embodiments of the present invention provide separation techniques for the separation of chlorofluorocarbons from HF, from other chlorofluorocarbons, and the separation of isomers of halogenated compounds. Still other embodiments of the present invention provide catalytic synthetic techniques that demonstrate extended catalyst lifetime. In other embodiments, the present invention provides catalytic techniques for the purification of isomeric mixtures.
    Type: Grant
    Filed: September 28, 2001
    Date of Patent: February 12, 2008
    Assignee: Great Lakes Chemical Corporation
    Inventors: Yuichi Iikubo, Stephen Owens, Mitchel Cohn, Stephan M. Brandstadter, Vicki E. Hedrick, Janet K. Boggs, John Chengping Chien, Julie Sacarias, Vimal Sharma
  • Patent number: 7285692
    Abstract: A process is disclosed for the manufacture of CF3CH2CHF2 and CF3CHFCH2F. The process involves (a) reacting hydrogen fluoride, chlorine, and at least one halopropene of the formula CX3CCl?CClX (where each X is independently F or Cl) to produce a product including both CF3CCl2CClF2 and CF3CClFCCl2F; (b) reacting CF3CCl2CClF2 and CF3CClFCCl2F produced in (a) with hydrogen to produce a product including both CF3CH2CHF2, and CF3CHFCH2F; and (c) recovering CF3CH2CHF2 and CF3CHFCH2F from the product produced in (b). In (a), the CF3CCl2CClF2 and CF3CClFCCl2F are produced in the presence of a chlorofluorination catalyst including a ZnCr2O4/crystalline ?-chromium oxide composition, a ZnCr2O4/crystalline ?-chromium oxide composition which has been treated with a fluorinating agent, a zinc halide/?-chromium oxide composition and/or a zinc halide/?-chromuim oxide composition which has been treated with a fluorinating agent.
    Type: Grant
    Filed: October 13, 2004
    Date of Patent: October 23, 2007
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen C. Sievert
  • Patent number: 7285690
    Abstract: A process for the manufacture of CF3CH2CHF2 and CF3CH2CF3 is disclosed. The process involves (a) reacting HF and at least one halopropene of the formula CX3CCI=CCIX (where each X is independently F or CI) to produce a product including both CF3CCI=CF2 and CF3CHCICF3; (b) reacting CF3CCI=CF2 and CF3CHCICF3 produced in (a) with hydrogen to produce a product including both CF3CH2CHF2 and CF3CH2CF3; and (c) recovering CF3CH2CHF2 and CF3CH2CF3 from the product produced in (b). In (a), the CF3CCI=CF2 and CF3CHCICF3 are produced in the presence of a fluorination catalyst including a ZnCr2O4/crystalline ?-chromium oxide composition, a ZnCr2O4/crystalline ?-chromium oxide composition which has been treated with a fluorinating agent, a zinc halide/?-chromium oxide composition and/or a zinc halide/?-chromium oxide composition which has been treated with a fluorinating agent.
    Type: Grant
    Filed: October 13, 2004
    Date of Patent: October 23, 2007
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen C. Sievert
  • Patent number: 7285691
    Abstract: A process is disclosed for the manufacture of 1,1,1,3,3,3-hexafluoropropane (HFC-236fa) and at least one 1,1,1,2,3,3-hexafluoropropane (HFC-236ea) and 1,1,1,2,3,3,3-heptafluoropropane (HFC-227ea). The process involves (a) reacting HF, Cl2, and at least one halopropene of the formula CX3CCl=CX2 (where each X is independently F or Cl) to produce a product including both CF3CCl2CF3 and CF3CClFCClF2; (b) reacting CF3CCl2CF3 and CF3CClFCClF2 produced in (a) with hydrogen to produce a product comprising CF3CH2CF3 and at least one compound selected from the group consisting of CHF2CHFCF3, and CF3CHFCF3; and (c) recovering from the product produced in (b), CF3CH2CF3 and at least one compound selected from the group consisting of CHF2CHFCF3 and CF3CHFCF3.
    Type: Grant
    Filed: October 13, 2004
    Date of Patent: October 23, 2007
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen C. Sievert
  • Patent number: 7247759
    Abstract: Fluorination reactions in which an organic compound to be fluorinated is contacted with elemental fluorine and HF is produced as a byproduct are disclosed, wherein the elemental fluorine is contacted with the organic compound in the presence of a fluoride-adsorbing composition so that the amount of HF or another hydrogen-containing byproduct is reduced or eliminated. Reactor embodiments for the fluorination reactions are also disclosed.
    Type: Grant
    Filed: January 4, 2006
    Date of Patent: July 24, 2007
    Assignee: Honeywell International Inc.
    Inventor: Matthew H Luly
  • Patent number: 6878853
    Abstract: This invention discloses a process for preparing a dihalogenated adamantane by reacting an adamantane optionally substituted with alkyl at 1-position with a halosulfonic acid, comprising the first stage of monohalogenation conducted at ?5 to 15° C. and then the second stage of dihalogenation conducted at 17 to 35° C., preferably in the absence of an organic solvent.
    Type: Grant
    Filed: November 11, 2002
    Date of Patent: April 12, 2005
    Assignee: Tokuyama Corporation
    Inventors: Norihiro Tanaka, Masao Yamaguchi
  • Patent number: 6784327
    Abstract: A process for the production of a fluorinated organic compound, characterized by fluorinating an organic compound having a hydrogen atoms using IF5; and a novel fluorination process for fluorinating an organic compound having a hydrogen atoms by using a fluorinating agent containing IF5 and at least one member selected from the group consisting of acids, bases, salts and additives.
    Type: Grant
    Filed: December 10, 2002
    Date of Patent: August 31, 2004
    Assignee: Daikin Industries, Ltd.
    Inventors: Norihiko Yoneda, Tsuyoshi Fukuhara, Kazuhiro Shimokawa, Kenji Adachi, Satoshi Oishi
  • Patent number: 6700026
    Abstract: A method for preparing difluoromethane (CF2H2, HFC-32) by the use of reaction of dichlorodifluoromethane (CF2Cl2, CFC-12) and/or monochlorodifluoromethane (CF2ClH, HCFC-22) with hydrogen in the presence of a palladium-based catalyst can give difluoromethane at a high conversion and a high selectivity.
    Type: Grant
    Filed: November 18, 1996
    Date of Patent: March 2, 2004
    Assignee: Daikin Industries Ltd.
    Inventors: Masaru Ichikawa, Ryuichirou Ohnishi
  • Patent number: 6583328
    Abstract: A method for the production of 1,1,1,3,3-pentafluoropropene, and particularly to a method characterized by high conversion, yield and selectivity by contacting 2,2-dichloro-1,1,1,3,3,3-hexafluoropropane with hydrogen in the presence of a metal-containing catalyst. The 1,1,1,3,3-pentafluoropropene then can be reacted with hydrogen in the presence of a metal-containing catalyst to produce 1,1,1,3,3-pentafluoropropane.
    Type: Grant
    Filed: April 5, 1999
    Date of Patent: June 24, 2003
    Assignee: PCBU Services, Inc.
    Inventors: John Cheng-Ping Qian, Julia Ann Sacarias
  • Patent number: RE45076
    Abstract: Disclosed herein is a process for the preparation of fluorine-containing olefins comprising contacting a chlorofluoroalkene with hydrogen in the presence of a catalyst at a temperature sufficient to cause replacement of the chlorine substituents with hydrogen. Also disclosed is a catalyst composition for the hydrodechlorination of chlorofluoroalkenes comprising copper metal deposited on a support.
    Type: Grant
    Filed: September 7, 2012
    Date of Patent: August 12, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Ekaterina N Swearingen