Substituting Halogen For A Different Halogen Patents (Class 570/170)
  • Patent number: 11236030
    Abstract: The present disclosure provides a method for producing fluoroolefin represented by formula (1): CX1X2?CX3X4, wherein X1, X2, X3, and X4 are the same or different, and represent a hydrogen atom or a fluorine atom, with high selectivity. Specifically, the present disclosure is a method for producing a fluoroolefin represented by formula (1) described above, the method comprising a dehydrofluorination step of bringing a fluorocarbon represented by formula (2): CX1X2FCX3X4H, wherein X1, X2, X3, and X4 are as defined above, into contact with a metal catalyst to perform dehydrofluorination, the dehydrofluorination step being performed in the gas phase in the presence of water, the concentration of the water being less than 500 ppm relative to the fluorocarbon represented by formula (2).
    Type: Grant
    Filed: April 22, 2019
    Date of Patent: February 1, 2022
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Takashi Usui, Tsubasa Nakaue, Takehiro Chaki, Yuzo Komatsu
  • Patent number: 10351493
    Abstract: The present invention relates to a method for preparing a polyinsaturated perfluorinated compound B from a polyinsaturated perhalogenated compound D having the formula CnX2(n?m+1), in which X is independently selected from one of the halogens, F, Cl, Br or I, provided at least one X is not fluorine; n is the number of carbon atoms and is at least higher than or equal to 4, m is the number of double carbon-carbon bonds and is higher than or equal to 2, wherein the method comprises a step in which compound D is fluorinated in the presence of a fluorinating agent of general formula AFp, in which A is hydrogen, an alkali metal or an alkaline earth metal, and p is 1 or 2, and in the presence of an aprotic organic polar solvent; the method being carried out with a molar ratio of AFp to compound D of less than 1.45*2(n?m+1).
    Type: Grant
    Filed: March 20, 2017
    Date of Patent: July 16, 2019
    Assignee: ARKEMA FRANCE
    Inventors: Grégory Schmidt, Rémy Teissier
  • Patent number: 9045386
    Abstract: The present invention relates to methods, process, and integrated systems for economically producing (E)-1-chloro-3,3,3-trifluoropropene via vapor phase and/or liquid processes.
    Type: Grant
    Filed: February 2, 2011
    Date of Patent: June 2, 2015
    Assignee: Honeywell International Inc.
    Inventors: Hsueh S. Tung, Robert Johnson, Konstantin A. Pokrovski, Daniel C. Merkel
  • Patent number: 8987532
    Abstract: Disclosed is a process for producing 1,2-dichloro-3,3,3-trifluoropropene, which is characterized by that 1-halogeno-3,3,3-trifluoropropene represented by the general formula [1]: (In the formula, X represents a fluorine atom, chlorine atom or bromine atom.) is reacted with chlorine in a gas phase in the presence of a catalyst. It is possible by this process to produce 1,2-dichloro-3,3,3-trifluoropropene in an industrial scale with good yield by using 1-halogeno-3,3,3-trifluoropropene, which is available with a low price, as the raw material.
    Type: Grant
    Filed: April 1, 2014
    Date of Patent: March 24, 2015
    Assignee: Central Glass Company, Limited
    Inventors: Satoru Okamoto, Yoshio Nishiguchi, Fuyuhiko Sakyu
  • Patent number: 8987535
    Abstract: The invention also relates a process for the manufacture of trans 1-chloro3,3,3-trifluoropropene. The process comprises an isomerization step from cis 1233zd to trans 1233zd.
    Type: Grant
    Filed: February 19, 2014
    Date of Patent: March 24, 2015
    Assignee: Arkema Inc.
    Inventors: Maher Y. Elsheikh, Anne Pigamo, Sri R. Seshadri
  • Patent number: 8987534
    Abstract: The invention also relates a process for the manufacture of trans 1-chloro3,3,3-trifluoropropene. The process comprises an isomerization step from cis 1233zd to trans 1233zd.
    Type: Grant
    Filed: January 29, 2014
    Date of Patent: March 24, 2015
    Assignee: Arkema Inc.
    Inventors: Maher Y. Elsheikh, Philippe Bonnet, John A. Wismer, Sri R. Seshadri
  • Patent number: 8895788
    Abstract: The invention relates to a process for manufacturing 1,1,1,2-tetrafluoropropene (1234yf, CF3—CF?CH2) from 1,1,3,3-tetrachlororopropene (1230za, CCl2?CH—CHCl2) and/or 1,1,1,3,3-pentachloropropane (240fa, CCl3CH2CHCl2). The process comprises a step of isomerization of 1,1,3,3-tetrafluoropropene (1230za) to 1,1,2,3-tetrachloropropene (1230xa) followed by conversion of the 1,1,2,3-tetrachloropropene (1230xa) to 1,1,1,2-tetrafluoropropene (1234yf) via a hydrofluorination process.
    Type: Grant
    Filed: January 21, 2014
    Date of Patent: November 25, 2014
    Assignee: Arkema Inc.
    Inventors: Maher Y. Elsheikh, Philippe Bonnet, John A. Wismer
  • Patent number: 8889924
    Abstract: The present invention provides a simple three step process for the production of 1,3,3,3-tetrafluoropropene (HFO-1234ze). In the first step, carbon tetrachloride is added to vinyl fluoride to afford the compound CCl3CH2CHClF (HCFC-241fb). HCFC-241fb is then fluorinated with anhydrous HF to afford CF3CH2CHClF (HCFC-244fa) in the second step. Dehydrochlorination of HCFC-244fa, in the third step, affords the desired product, CF3CH?CHF (HFO-1234ze). Following similar chemistry, vinyl chloride may be used in place of vinyl fluoride.
    Type: Grant
    Filed: February 4, 2013
    Date of Patent: November 18, 2014
    Assignee: Honeywell International Inc.
    Inventors: Haridasan K. Nair, Rajiv Ratna Singh, Andrew Joseph Poss, David Nalewajek
  • Patent number: 8877017
    Abstract: The present invention provides a novel method for separating hexafluoropropylene oxide (HFPO) from hexafluoropropylene (HFP), which is capable of reducing the burden on the environment. A mixture including HFPO and HFP is subjected to an extractive distillation operation using, as a solvent, at least one of a fluorine-containing saturated compound represented by the general formula CnHaFb (wherein n, a and b are integers which satisfy: n=3 to 8, 0?a?2n+1, and 1?b?2n+2) thereby separating into a first fraction including HFPO and a second fraction including HFP and the solvent. At least one of 1-bromopropane and 2-bromopropane may be u as the solvent in place of the fluorine-containing saturated compound.
    Type: Grant
    Filed: February 18, 2010
    Date of Patent: November 4, 2014
    Assignee: Daikin Industries, Ltd.
    Inventors: Hideki Nakaya, Kazuyoshi Ichihara, Yasuhide Senba, Mikio Nakagoshi, Kazunori Morimoto
  • Patent number: 8822741
    Abstract: A process for the fluorination of haloolefins with elemental fluorine in the presence of anhydrous HF proceeds with high yield and selectivity in the product deriving from the addition of fluorine to the carbon-carbon double bond.
    Type: Grant
    Filed: July 5, 2011
    Date of Patent: September 2, 2014
    Assignee: Solvay Specialty Polymers Italy S.p.A.
    Inventors: Vito Tortelli, Marco Galimberti
  • Patent number: 8779219
    Abstract: The present invention provides a process for preparing at least one chlorine-containing fluorocarbon compound selected from the group consisting of chlorine-containing fluoropropane compounds represented by Formula (1): CFnCl3-nCHClCH2—Cl, wherein n is 1 or 2, and chlorine-containing fluoropropene compounds represented by Formula (2): CFnCl3-nCCl?CH2, wherein n is 1 or 2, wherein the process includes the step of contacting at least one chlorine-containing compound selected from the group consisting of 1,1,1,2,3-pentachloropropane, 1,1,2,3-tetrachloropropene, and 2,3,3,3-tetrachloropropene with hydrogen fluoride in the absence of a catalyst while heating. According to the present invention, the chlorine-containing propane and propene compounds having 1 or 2 fluorine atoms can be prepared by an industrially applicable, simple and effective process.
    Type: Grant
    Filed: May 12, 2010
    Date of Patent: July 15, 2014
    Assignee: Daikin Industries, Ltd.
    Inventors: Masatoshi Nose, Tsuneo Yamashita, Atsushi Suzuki
  • Patent number: 8754273
    Abstract: Disclosed is a process for making the compound 1,1,2-trichloro-3,3,3-trifluoropropane (233da) by the catalytic fluorination of 1,1,1,2,3,3-hexachloropropane. 233da is a starting material used in the production cis-1-chloro-3,3,3-trifluoropropene (cis-1233zd).
    Type: Grant
    Filed: November 12, 2012
    Date of Patent: June 17, 2014
    Assignee: Honeywell International Inc.
    Inventors: Yian Zhai, Andrew Joseph Poss, Rajiv Ratna Singh
  • Patent number: 8642818
    Abstract: The invention relates to a process for manufacturing 1,1,1,2-tetrafluoropropene (1234yf, CF3—CF?CH2) from 1,1,3,3-tetrachlororopropene (1230za, CCl2?CH—CHCl2) and/or 1,1,1,3,3-pentachloropropane (240fa, CCl3CH2CHCl2). The process comprises an isomerization step of 1-chloro-3,3,3 trifluoropropene (1233zd, CF3—CH?CHCl) to 2-chloro-3,3,3 trifluoropropene (1233xf or CF3—CCl?CH2).
    Type: Grant
    Filed: November 12, 2009
    Date of Patent: February 4, 2014
    Assignee: Arkema Inc.
    Inventors: Maher Y. Elsheikh, Philippe Bonnet, John A. Wismer
  • Patent number: 8642819
    Abstract: The present invention provides a process for the manufacture of trans 1-chloro-3,3,3-trifluoropropene (E-1233zd). The first step of the process comprises the fluorination of 1,1,3,3-tetrachlororopropene (1230za, CCh?CH—CHCh) and/or 1,1,1,3,3-pentaachloropropane (240fa) to a mixture of cis 1233zd (Z-1233zd) and trans 1233zd (E-1233zd). The second step of the process comprises a separation of the mixture formed in the first step to isolate cis 1233zd (Z-1233zd) from the mixture. The third step of the process comprises isomerization of cis 1233zd (Z-1233zd) to trans 1233zd (E-1233zd).
    Type: Grant
    Filed: November 12, 2009
    Date of Patent: February 4, 2014
    Assignee: Arkema Inc.
    Inventors: Maher Y. Elsheikh, Philippe Bonnet, John A. Wismer
  • Patent number: 8614360
    Abstract: The invention relates to new processes for preparation of 18F-fluoroalkyl halides suitable for use in labelling of Positron Emission Tomography (PET) radiotracers. The process of preparation comprises the step of reacting a 18F-fluoroacylhalide with Wilkinson's catalyst.
    Type: Grant
    Filed: December 8, 2006
    Date of Patent: December 24, 2013
    Assignee: Hammersmith Imanet Limited
    Inventor: Erik Arstad
  • Patent number: 8546623
    Abstract: The invention relates to a process for preparing a C3-6 hydrofluoroalkene comprising dehydrohalogenating a C3-6 hydrohalofluoroalkane in the presence of a zinc/chromia catalyst.
    Type: Grant
    Filed: October 3, 2007
    Date of Patent: October 1, 2013
    Assignee: Mexichem Amanco Holding S.A. de C.V.
    Inventors: Andrew Paul Sharratt, Leslie Seddon
  • Patent number: 8541634
    Abstract: Disclosed are azeotropic and azeotrope-like mixtures of (Z)-1-chloro-3,3,3-trifluoropropene (1233zd(Z)) and hydrogen fluoride. Such compositions are useful as an intermediate in the production of 1233zd(Z). The latter compound is useful as a nontoxic, zero ozone depleting fluorocarbon useful as a solvent, blowing agent, refrigerant, cleaning agent, aerosol propellant, heat transfer medium, dielectric, fire extinguishing composition and power cycle working fluid.
    Type: Grant
    Filed: January 14, 2013
    Date of Patent: September 24, 2013
    Assignee: Honeywell International Inc.
    Inventors: Ryan Hulse, Hang T Pham
  • Patent number: 8519200
    Abstract: Provided are azeotropic or azeotrope-like mixtures of 1,1,3,3-tetrachloro-1-fluoropropane (HCFC-241fa) and hydrogen fluoride. Such compositions are useful as an intermediate in the production of HFC-245fa and HCFO-1233zd.
    Type: Grant
    Filed: February 23, 2012
    Date of Patent: August 27, 2013
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Konstantin A. Pokrovski, Hang T. Pham, Hsueh Sung Tung, Ryan Hulse
  • Publication number: 20130150634
    Abstract: Disclosed is a process for making the compound 1,1,2-trichloro-3,3,3-trifluoro-propane (233da) by the catalytic fluorination of 1,1,1,2,3,3-hexachloropropane. 233da is a starting material used in the production cis-1-chloro-3,3,3-trifluoropropene (cis-1233zd).
    Type: Application
    Filed: November 12, 2012
    Publication date: June 13, 2013
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventor: Honeywell International Inc.
  • Patent number: 8450537
    Abstract: 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: Grant
    Filed: October 23, 2012
    Date of Patent: May 28, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Patent number: 8426656
    Abstract: The disclosed integrated manufacturing process includes a combined liquid phase reaction and purification operation which directly produces trans-1-chloro-3,3,3-trifluoropropene and 3-chloro-1,1,1,3-tetrafluoropropane which is a precursor to the manufacture of trans-1,3,3,3-tetrafluoropropene. The mixture of co-products is easily separated by conventional distillation and 3-chloro-1,1,1,3-tetrafluoropropane is then dehydrochlorinated to produce trans-1,3,3,3-tetrafluoropropene by contacting in the liquid phase with a caustic solution or in the vapor phase using a dehydrochlorination catalyst.
    Type: Grant
    Filed: April 5, 2010
    Date of Patent: April 23, 2013
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Robert Johnson, Hsueh Sung Tung, Haiyou Wang, Konstantin A. Pokrovski
  • Publication number: 20130096353
    Abstract: To provide a process for producing a fluoroalkyl iodide, whereby the selectivity for a fluoroalkyl iodide having a desired degree of polymerization is high and the productivity is high. A process for producing a fluoroalkyl iodide (2) represented by RfCF2CF2I (wherein Rf is a fluoroalkyl group having at most 4 carbon atoms), which comprises reacting a fluoroalkyl iodide (1) represented by RfI with tetrafluoroethylene in the presence of a radical initiator, wherein a first reaction step of supplying and reacting tetrafluoroethylene and a radical initiator to the fluoroalkyl iodide (1), is followed by repeating (n?1) times (provided that n is an integer of at least 3) a subsequent reaction step of supplying and reacting a radical initiator, or a radical initiator and tetrafluoroethylene, to a reaction mixture (1) formed in the first reaction step.
    Type: Application
    Filed: December 4, 2012
    Publication date: April 18, 2013
    Applicant: Asahi Glass Company, Limited
    Inventor: Asahi Glass Company, Limited
  • Patent number: 8395001
    Abstract: 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: Grant
    Filed: June 10, 2011
    Date of Patent: March 12, 2013
    Assignee: Asahi Glass Company, Limited
    Inventors: Satoshi Kawaguchi, Takashi Okazoe, Hidekazu Okamoto
  • Patent number: 8378158
    Abstract: Disclosed are azeotropic and azeotrope-like mixtures of (Z)-1-chloro-3,3,3-trifluoropropene (1233zd(Z)) and hydrogen fluoride. Such compositions are useful as an intermediate in the production of 1233zd(Z). The latter compound is useful as a nontoxic, zero ozone depleting fluorocarbon useful as a solvent, blowing agent, refrigerant, cleaning agent, aerosol propellant, heat transfer medium, dielectric, fire extinguishing composition and power cycle working fluid.
    Type: Grant
    Filed: October 5, 2011
    Date of Patent: February 19, 2013
    Assignee: Honeywell International Inc.
    Inventors: Ryan Hulse, Hang T. Pham
  • Publication number: 20130035526
    Abstract: A method for producing a tetrafluoroolefin, such as 2,3,3,3-tetrafluoropropene (HFO-1234yf), comprises contacting 1,1,1,2-tetrachloro-2-fluoropropane (HCFC-241bb) with or without a catalyst under conditions effective to convert the 1,1,1,2-tetrachloro-2-fluoropropane (HCFC-241bb) to the tetrafluoroolefin, optionally, via an intermediate. The conversion may be a one-step fluorination or a two-step fluorination and dehydrochlorination process. The 1,1,1,2-tetrachloro-2-fluoropropane (HCFC-241bb) may also be obtained by dehydrochlorinating 1,2,3-trichloropropane (HCC-260da) to form 2,3-dichloropropene (HCO-1250xf); fluorinating 2,3-dichloropropene (HCO-1250xf) to form 1,2-dichloro-2-fluoropropane (HCFC-261bb); and chlorinating 1,2-dichloro-2-fluoropropane (HCFC-261bb) to form 1,1,1,2-tetrachloro-2-fluoropropane (HCFC-241bb).
    Type: Application
    Filed: April 8, 2011
    Publication date: February 7, 2013
    Applicant: Arkema Inc.
    Inventors: Maher Y. Elsheikh, Philippe Bonnet, Benjamin Bin Chen
  • Patent number: 8367879
    Abstract: A method of catalytically converting 2,2, dichlorohexafluoropropane (HFC-216aa) into 2 chloro 1,1,1,2,3,3,3 heptafluoropropane (HFC-217ba) including the step of exposing the 2,2 dichlorohexafluoropropane to a chromium-containing catalyst comprising a metal oxide, a halogenated metal oxide or a metal oxyhalide, which chromium-containing catalyst comprises 0.01% to 5.0% by weight zinc or a compound of zinc.
    Type: Grant
    Filed: November 10, 2008
    Date of Patent: February 5, 2013
    Assignee: Mexichem Amanco Holding S.A. de C.V.
    Inventors: Andrew P. Sharratt, John C. McCarthy
  • Patent number: 8318992
    Abstract: 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: Grant
    Filed: October 31, 2007
    Date of Patent: November 27, 2012
    Assignee: E I du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Patent number: 8309774
    Abstract: 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: Grant
    Filed: March 9, 2012
    Date of Patent: November 13, 2012
    Assignee: Arkema France
    Inventors: Anne Pigamo, Dominique Deur-Bert, Laurent Wendlinger
  • Patent number: 8158836
    Abstract: 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: Grant
    Filed: December 23, 2010
    Date of Patent: April 17, 2012
    Assignee: Arkema France
    Inventors: Anne Pigamo, Dominique Deur-Bert, Laurent Wendlinger
  • Publication number: 20120053371
    Abstract: Disclosed are processes for the production of fluorinated olefins, preferably adapted to commercialization of CF3CF?CH2 (1234yf). In certain preferred embodiments the processes comprise first exposing a compound of Formula (IA) C(X)2?CClC(X)3??(IA) where each X is independently F, Cl or H, preferably CCl2?CClCH2Cl, to one or more sets of reaction conditions, but preferably a substantially single set of reaction conditions, effective to produce at least one chlorofluoropropane, preferably in accordance with Formula (IB): CF3CClX?C(X?)3??Formula (IB) where each X? is independently F, Cl or H, and then exposing the compound of Formula (IB) to one or more sets of reaction conditions, but preferably a substantially single set of reaction conditions, effective to produce a compound of Formula (II) CF3CF?CHZ??(II) where Z is H, F, Cl, I or Br.
    Type: Application
    Filed: November 2, 2011
    Publication date: March 1, 2012
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: ROBERT C. JOHNSON, HSUEH S. TUNG, DANIEL C. MERKEL
  • Patent number: 8053613
    Abstract: A process is disclosed for making CH2ClCF2CClF2. The process involves reacting CH2ClF with CClF?CF2 in an addition reaction zone in the presence of an aluminum halide composition having a bulk formula of AlClxBryF3-x-y wherein the average value of x is 0 to 3, the average value of y is 0 to 3?x, provided that the average values of x and y are not both 0. Also disclosed is a process for making CH2FCF2CF3 that involves reacting the CH2ClCF2CClF2 with HF in a fluorination reaction zone in the presence of a fluorination catalyst. Also disclosed is a process for making CHF?CFCF3 that involves dehydrofluorinating the CH2FCF2CF3.
    Type: Grant
    Filed: September 5, 2007
    Date of Patent: November 8, 2011
    Assignee: E.I. du Pont de Nemours and Company
    Inventor: Allen Capron Sievert
  • Patent number: 8034985
    Abstract: A process for the preparation of a fluoroiodoalkane compound represented by the formula: CF3(CF2)n—Y, wherein n is 0 or 1. The process includes contacting A, B and C. A is represented by the formula: CF3(CF2)n—Y, wherein n is 0 or 1, and Y is selected from the group consisting of: H, Cl, Br, and COOH. B is a source of iodine, and C is a catalyst containing elements with d1s1 configuration and lanthanide elements. The process occurs at a temperature, and for a contact time, sufficient to produce the fluoroiodoalkane compound.
    Type: Grant
    Filed: February 15, 2007
    Date of Patent: October 11, 2011
    Assignee: Honeywell International, Ltd.
    Inventors: Shuwu Yang, HsuehSung Tung
  • Patent number: 8003832
    Abstract: The process for recovering pentafluoroethane of the invention includes bringing a mixed gas containing pentafluoroethane and a non-condensable gas into contact with a chlorinated solvent, and allowing the chlorinated solvent to absorb pentafluoroethane contained in the mixed gas. The process for the production of pentafluoroethane of the invention uses the recovering process.
    Type: Grant
    Filed: July 27, 2006
    Date of Patent: August 23, 2011
    Assignee: Showa Denko K.K.
    Inventors: Kazunari Kaga, Hiromoto Ohno
  • Patent number: 7943015
    Abstract: A photochemical reaction apparatus including a reactor and a light source situated so that light from the light source is directed through a portion of the reactor wall is disclosed. The apparatus is characterized by the portion of the reaction wall comprising a copolymer of a perfluoro (alkyl vinyl ether). The perfluoro (alkyl vinyl ether) is selected from the group consisting of CF30CF?CF2, C2F5OCF?CF2, C3F7OCF?F2, and mixture thereof. Also disclosed is a photochemical reaction process wherein light from a light source is directed through said reactor wall to interact with reactants in said reactor. A process for increasing the fluorine content of at least one compound selected from hydrocarbons and halohydrocarbons, comprising: (a) photochlorinating said at least one compound; and (b) reacting the halogenated hydrocarbon produced in (a) with HF.
    Type: Grant
    Filed: December 19, 2005
    Date of Patent: May 17, 2011
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Publication number: 20110112321
    Abstract: An alkali metal fluoride dispersion essentially consisting of an alkali metal fluoride and an aprotic organic solvent obtainable by conducting the following Step (A), subsequently conducting the following Step (B) at least once, and then conducting the following Step(C); Step (A): a step of separating a liquid phase from an alkali metal fluoride dispersion comprising at least one alcohol solvent selected from the group consisting of methanol, ethanol and isopropanol and an alkali metal fluoride, and mixing the separated liquid phase with an aprotic organic solvent having a boiling point of 85° C.
    Type: Application
    Filed: August 27, 2008
    Publication date: May 12, 2011
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventor: Koji Hagiya
  • Patent number: 7868213
    Abstract: A method for producing 1,4-bis(bromodifluoromethyl)tetrafluorobenzene (BFTFB) is disclosed. The target compound is predicted as a very potent monomer for low dielectric constant material. This method comprises the following steps: (a) mixing 1,4-bis(bromodifluoromethyl)tetrafluorobenzene (DFMTFB), a bromination agent, and a solvent (with or without) to form a mixture; (b) heating the mixture under UV radiation; and (c) purifying the resultant to obtain 1,4-bis(bromodifluoromethyl)tetrafluorobenzene (BFTFB) with high purity.
    Type: Grant
    Filed: July 29, 2008
    Date of Patent: January 11, 2011
    Assignees: Yuan-Shin Materials Technology Corp, Chung-Shan Institute of Science and Technology, Armaments Bureau. M.N.D.
    Inventors: Chuan-Yu Chou, Po-Chen Chang, Chun-Hsu Lin, Shieh-Jun Wang
  • Publication number: 20100312026
    Abstract: A method of catalytically converting 2,2, dichlorohexafluoropropane (HFC-216aa) into 2 chloro 1,1,1,2,3,3,3 heptafluoropropane (HFC-217ba) including the step of exposing the 2,2 dichlorohexafluoropropane to a chromium-containing catalyst comprising a metal oxide, a halogenated metal oxide or a metal oxyhalide, which chromium-containing catalyst comprises 0.01% to 5.0% by weight zinc or a compound of zinc.
    Type: Application
    Filed: November 10, 2008
    Publication date: December 9, 2010
    Inventors: Andrew P. Sharratt, John C. McCarthy
  • Patent number: 7829748
    Abstract: The invention provides an economic process for the manufacture of 1,3,3,3-tetrafluoropropene (HFO-1234ze) by a two stage process. A vapor phase hydrofluorination of 1-chloro-3,3,3-trifluoropropene (HCFC-1233zd) into 1-chloro-1,3,3,3-tetrafluoropropane (HCFC-244fa) and/or 1,1,1,3,3-pentafluoropropane (HFC-245fa) is conducted, followed by the thermal dehydrochlorination of HCFC-244fa and dehydro fluorination of HFC-245fa into HFO-1234ze in the presence of a catalyst which comprises one or more of alkali metal halides, alkaline earth metal halides, halogenated metal oxides, zero oxidation state metals, zinc halides, palladium halides, and activated carbon.
    Type: Grant
    Filed: September 21, 2009
    Date of Patent: November 9, 2010
    Assignee: Honeywell International Inc.
    Inventors: Hsuehsung Tung, Robert C. Johnson, Daniel C. Merkel, Haiyou Wang
  • Patent number: 7786334
    Abstract: A process is described for the preparation of 2-chloro-1,1,1-difluoroethane by the reaction of 1,2-dichloro-1,1-difluoroethane with hydrogen fluoride. in the presence of a fluorination catalyst. The process utilizes a rate enhancing reagent that is trichloroethylene, is 1-fluoro-1,2,3-trichloroethane or an aromatic rate enhancing reagent having the formula where R is C1 to C6 linear or branched alkyl substituted with at least one halo group, halo or nitro and R? is C1 to C6 linear or branched alkyl substituted with at least one halo group.
    Type: Grant
    Filed: March 20, 2009
    Date of Patent: August 31, 2010
    Inventor: Randolph K. Belter
  • Patent number: 7649121
    Abstract: Methods and systems for producing halogenated hydrocarbon compounds with an inorganic fluoride (e.g., germanium tetrafluoride (GeF4)) are disclosed herein.
    Type: Grant
    Filed: September 11, 2007
    Date of Patent: January 19, 2010
    Assignee: International Isotopes Inc.
    Inventor: Bamidele Omotowa
  • Patent number: 7645912
    Abstract: Methods and systems for producing hydrofluorocarbon with an inorganic fluoride (e.g., germanium tetrafluoride (GeF4)) are disclosed herein.
    Type: Grant
    Filed: September 11, 2007
    Date of Patent: January 12, 2010
    Assignee: International Isotopes, Inc.
    Inventor: Bamidele Omotowa
  • Patent number: 7642387
    Abstract: Methods and systems for producing halocarbon with an inorganic fluoride (e.g., germanium tetrafluoride (GeF4)) are disclosed herein.
    Type: Grant
    Filed: September 11, 2007
    Date of Patent: January 5, 2010
    Assignee: International Isotopes, Inc.
    Inventor: Bamidele Omotowa
  • Patent number: 7638659
    Abstract: Methods and systems for producing chlorofluorocarbon with an inorganic fluoride (e.g., germanium tetrafluoride (GeF4)) are disclosed herein.
    Type: Grant
    Filed: September 11, 2007
    Date of Patent: December 29, 2009
    Assignee: International Isotopes, Inc.
    Inventor: Bamidele Omotowa
  • Publication number: 20090247794
    Abstract: 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: Application
    Filed: October 5, 2007
    Publication date: October 1, 2009
    Applicant: SOLVAY (SOCIETE ANONYME)
    Inventors: Veronique Mathieu, Francine Janssens
  • Patent number: 7592494
    Abstract: The invention provides an economic process for the manufacture of 1,3,3,3-tetrafluoropropene (HFC-1234ze) by a two stage process. A hydrofluorination of 1-chloro-3,3,3-trifluoropropene (HCFC-1233zd) into 1-chloro-1,3,3,3-tetrafluoropropane (HCFC-244fa) and 1,1,1,3,3-pentafluoropropane (HFC-245fa) is conducted, followed by the dehydrochlorination of HCFC-244fa and dehydrofluorination of HFC-245fa into HFC-1234ze.
    Type: Grant
    Filed: July 25, 2003
    Date of Patent: September 22, 2009
    Assignee: Honeywell International Inc.
    Inventors: Hsueh Sung Tung, Robert C. Johnson, Daniel C. Merkel
  • Patent number: 7566809
    Abstract: Process for the separation of a mixture comprising at least one hydrofluoroalkane and hydrogen fluoride, according to which a hydrofluoroalkane/hydrogen fluoride mixture is reacted with at least one chlorinated or chlorofluorinated precursor of the hydrofluoroalkane. Process for the preparation of a hydrofluoroalkane comprising such a separation, in combination with a catalytic reaction stage. Azeotropic compositions.
    Type: Grant
    Filed: May 25, 2007
    Date of Patent: July 28, 2009
    Assignee: Solvay S.A.
    Inventors: Alain Lambert, Vincent Wilmet
  • Patent number: 7544846
    Abstract: A method for producing 1,4-bis(difluoromethyl)tetrafluorobenzene is disclosed, which has the following steps: (a) mixing 1,4-bis(dichloromethyl)tetrafluorobenzene, a catalyst, an aprotic polar solvent, and an alkali metal fluoride to form a reaction mixture; (b) heating the reaction mixture; and (c) purifying the resultant to obtain 1,4-bis(difluoromethyl)tetrafluorobenzene.
    Type: Grant
    Filed: July 29, 2008
    Date of Patent: June 9, 2009
    Assignees: Yuan-Shin Materials Technology Corp., Chung-Shan Institute of Science and Technology, Armaments Bureau, M.N.D.
    Inventors: Chun-Hsu Lin, Chac-Chou Tu, Chan-Yuan Ho, Chuan-Yu Chou, Wei-Hsiung Ou, Shieh-Jun Wang
  • Patent number: 7524999
    Abstract: A process for the preparation of 1,1,1,3,3,3-hexafluoropropane is disclosed. The process involves (a) contacting at least one halopropane of the formula CF3CH2CHyX3-y (where each X is independently F, Cl or Br, and y is 3, 2, or 1) with Cl?2#191 in the presence of light or a free radical initiator to produce a mixture comprising CF3CH2CCIyX3-y; (b) contacting the CF3CH2CCIyX3-y produced in step (a) with HF, optionally in the presence of a fluorination catalyst, to produce a product mixture comprising CF3CH2CF3; and (c) recovering CF3CH2CF3 from the mixture produced in step (b).
    Type: Grant
    Filed: December 19, 2005
    Date of Patent: April 28, 2009
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Publication number: 20090005617
    Abstract: The invention relates to a device and a process for nucleophilic fluorination of a substance, especially for synthesis of an 18F-labeled substance for examination using a positron emission tomograph. The device comprises an anion exchange device (102) for extraction of [18F]fluoride ions by means of adsorption from a target fluid, whereby the anion exchange device (102) can be charged via a supply device (101) with the target fluid; and a measurement device (104) with a measurement chamber (103) for measuring initial radioactivity of the [18F]fluoride ions, the anion exchange device (102) being arranged at least partially in the measurement chamber (103) of the measurement device (104). (FIG.
    Type: Application
    Filed: May 7, 2004
    Publication date: January 1, 2009
    Inventors: Peter Maeding, Frank Fuechtner
  • Patent number: 7405333
    Abstract: A improved process is described for the preparation of a substantially pure, liquefied stream of 1,1,1,2-tetrafluoroethane by the catalyzed reaction of trichloroethylene with hydrogen fluoride to form the intermediate 2-chloro-1,1,1-trifluoroethane and then reacting said intermediate 2-chloro-1,1,1-trifluoroethane with hydrogen fluoride, in the presence of a hydrofluorination catalyst to form a reaction stream containing 1,1,1,2-tetrafluoroethane. The improvement comprises liquefying the by-product hydrogen chloride formed in the preparation of the intermediate 2-chloro-1,1,1-trifluoroethane and countercurrently passing said liquefied hydrogen chloride thru the reaction stream containing 1,1,1,2-tetrafluoroethane thereby forming a substantially pure, liquefied stream of 1,1,1,2-tetrafluoroethane and an effluent comprising gaseous hydrogen chloride.
    Type: Grant
    Filed: December 17, 2007
    Date of Patent: July 29, 2008
    Assignee: Norphlet Chemicals, Inc.
    Inventor: Ronnie D. Jackson