Preparing Unsaturated Compound Patents (Class 570/153)
  • Patent number: 10392326
    Abstract: The present invention provides an economically advantageous method for efficiently producing a fluorine-containing compound while ensuring high conversion of the starting compound, reducing production of 245cb, and reducing equipment costs and energy costs.
    Type: Grant
    Filed: January 19, 2016
    Date of Patent: August 27, 2019
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Daisuke Karube, Takehiro Chaki
  • Patent number: 10377686
    Abstract: An efficient method for producing 1-chloro-2,3,3,3-tetorafluoropropene from 1,1-dichloro-2,3,3,3-tetrafluoropropene is provided. The method produces 1-chloro-2,3,3,3-tetorafluoropropene by reducing 1,1-dichloro-2,3,3,3-tetrafluoropropene with fewer over-reduced by-products, such as 2,3,3,3-tetrafluoropropene and 1,1,1,2-tetrafluoropropane. In the method, 1,1-dichloro-2,3,3,3-tetrafluoropropene reacts with hydrogen in a gas phase in the presence of a palladium catalyst-carrying carrier, in which a palladium catalyst having a specific surface area of 40 m2/g or less is carried on the carrier.
    Type: Grant
    Filed: August 20, 2018
    Date of Patent: August 13, 2019
    Assignee: AGC Inc.
    Inventors: Shingo Nomura, Hidekazu Okamoto, Hirokazu Takagi
  • Patent number: 10343148
    Abstract: A catalyst structure includes a plurality of metal oxides formed on a support, where the support includes zirconia and/or silica. The metal oxides include at least three metals selected from the group consisting of chromium, iron, nickel, and a platinum group metal. The catalyst structure can be used in an oxidative dehydrogenation (ODH) reaction process for converting an alkane to an olefin. In some embodiments, carbon dioxide utilized in the ODH reaction process is obtained from a flue gas derived from a fossil fuel burning power plant.
    Type: Grant
    Filed: December 1, 2016
    Date of Patent: July 9, 2019
    Assignee: SOUTHERN RESEARCH INSTITUTE
    Inventors: Amit Goyal, Jadid Samad
  • Patent number: 10258634
    Abstract: The invention relates to the field of medicine, in particular to the field of veterinary medicine. The invention relates to glucocorticoids, especially ciclesonide or a pharmaceutically acceptable derivative or salt thereof, for the treatment of airway disease in horses, such as pulmonary disease, preferably recurrent airway obstruction (RAO), Summer Pasture Associated Obstructive Pulmonary disease (SPAOPD), and inflammatory airway disease (IAD).
    Type: Grant
    Filed: October 13, 2016
    Date of Patent: April 16, 2019
    Assignee: Boehringer Ingelheim Vetmedica GmbH
    Inventors: Balazs Albrecht, Michael Aven, Janine Lamar, Ingo Lang
  • Patent number: 10189758
    Abstract: To provide a method for producing a hydrofluoroolefin, wherein formation of an over-reduced product having hydrogen added to an aimed hydrofluorolefin and an over-reduced product having some of fluorine atoms in the aimed product replaced with hydrogen atoms, as by-products, is suppressed. A method for producing a hydrofluoroolefin, which comprises reacting a specific chlorofluoroolefin with hydrogen in the presence of a catalyst supported on a carrier, to obtain a specific hydrofluoroolefin, wherein the catalyst is a catalyst composed of particles of an alloy containing at least one platinum group metal selected from the group consisting of palladium and platinum, and gold, and the proportion of the gold at the surface of the alloy particles is from 5 to 30 mass % per 100 mass % in total of the platinum group metal and the gold at the surface of the alloy particles.
    Type: Grant
    Filed: June 1, 2017
    Date of Patent: January 29, 2019
    Assignee: AGC Inc.
    Inventors: Xu Wang, Shinji Terazono, Yuki Hayasaka, Toshio Suzuki, Satoshi Kawaguchi, Mitsugu Kasagawa
  • Patent number: 9988327
    Abstract: A method for producing a hydrofluoroolefin is provided. The formation of by-products of an over-reduced product having hydrogen added to a material chlorofluoroolefin and an over-reduced product having not only chlorine atoms but also fluorine atoms in the chlorofluoroolefin replaced with hydrogen atoms is suppressed in the method. The method includes reacting a specific chlorofluoroolefin with hydrogen in the presence of a catalyst supported on a carrier to obtain the hydrofluoroolefin. The catalyst is a catalyst composed of an alloy containing at least one platinum group element of palladium and platinum, and at least one second element of manganese, copper, aluminum, gold, lithium, sodium, potassium, magnesium, silver, zinc, cadmium, indium, silicon, germanium, tin, lead, arsenic, antimony, and bismuth.
    Type: Grant
    Filed: February 16, 2017
    Date of Patent: June 5, 2018
    Assignee: Asahi Glass Company, Limited
    Inventors: Shinji Terazono, Xu Wang, Masahiro Kanda, Satoshi Kawaguchi, Mitsugu Kasagawa
  • Patent number: 9944852
    Abstract: The present invention is a 1H-Heptafluorocyclopentene having a purity of 99.9 wt % or more and an organochlorine-based compound content of 350 ppm by weight or less. The present invention provides a high-purity 1H-Heptafluorocyclopentene that may be useful as a plasma reaction gas for semiconductors.
    Type: Grant
    Filed: February 19, 2014
    Date of Patent: April 17, 2018
    Assignee: ZEON CORPORATION
    Inventor: Tatsuya Sugimoto
  • Patent number: 9643904
    Abstract: A method for preparing 2,3,3,3-tetrafluoropropene, including: a) introducing hexafluoropropylene and hydrogen to a first reactor for reaction in the presence of a catalyst to obtain a first mixture; b) washing and drying the first mixture, and introducing the treated first mixture to a first distillation column to obtain 1,1,1,2,3,3-hexafluoropropane, 1,1,1,2,3-pentafluoropropene, and hexafluoropropylene; recycling the 1,1,1,2,3,3-hexafluoropropane to the first reactor, and introducing the 1,1,1,2,3-pentafluoropropene and the hexafluoropropylene to a second distillation column to yield hexafluoropropylene and 1,1,1,2,3-pentafluoropropene; and recycling the hexafluoropropylene to the first reactor; c) introducing the 1,1,1,2,3-pentafluoropropene and hydrogen to a second reactor in the presence of a catalyst to obtain a second mixture; and d) washing and drying the second mixture, and introducing the second mixture to a third distillation column to yield 1,1,1,2,3-pentafluoropropane; and recycling the 1,1,1,2,3
    Type: Grant
    Filed: December 13, 2016
    Date of Patent: May 9, 2017
    Assignees: ZHEJIANG QUZHOU JUXIN FLUORINE CHEMICAL CO., LTD., ZHEJIANG QUHUA FLUOR-CHEMISTRY CO., LTD.
    Inventors: Jun Lei, Aiguo Wang, Bo Yang, Yan Zhang, Huadong Zhou, Yang Zhao, Yi Zhu, Haili Xia, Haojin Shi
  • Patent number: 9328043
    Abstract: The present invention relates, in part, an improved process for the production of certain hydrofluoroolefins, particularly 2,3,3,3-tetrafluoropropene (1234yf). In certain non-limiting embodiments, the invention relates to methods for improving process efficiency during the fluorination of 1,1,2,3-tetrachloropropene, 2,3,3,3-tetrachloropropene, and/or 1,1,1,2,3-pentachloropropane to 2-chloro-3,3,3-trifluoropropene by separating and recycling unreacted HF, unreacted starting materials, and/or certain process intermediates from the 2-chloro-3,3,3-trifluoropropene product stream.
    Type: Grant
    Filed: February 25, 2013
    Date of Patent: May 3, 2016
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou Wang, Selma Bektesevic, Hsueh S. Tung, Haluk Kopkalli, Yuon Chiu
  • Patent number: 9249072
    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: Grant
    Filed: July 18, 2012
    Date of Patent: February 2, 2016
    Assignee: Mexichem Amanco Holding S.A. de C.V.
    Inventors: Andrew P. Sharratt, Claire E. McGuinness, Emma J. Hodgson
  • Patent number: 9139495
    Abstract: Methods for the manufacture of 1,1,1,2,3-pentachloropropane from 1,1,1,3-tetrachloropropane and chlorine are disclosed. Improved methods are provided for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,2,3-pentachloropropane. Methods are also disclosed for the manufacture of 1,1,2,3-tetrachloropropene from 1,1,1,3-tetrachloropropane and chlorine and for the manufacture of 1,1,2,3-tetrachloropropene from carbon tetrachloride, ethylene, and chlorine.
    Type: Grant
    Filed: November 26, 2014
    Date of Patent: September 22, 2015
    Assignee: Occidental Chemical Corporation
    Inventors: Richard L. Wilson, Rodney L. Klausmeyer, John Lee Dawkins, Daniel D. Rohrback, James S. Strathe, Lloyd B. Branam
  • Patent number: 9085504
    Abstract: Various compositions, including particularly solvent compositions, containing fluorinated olefins, including particularly tetra- and penta-fluorpropenes, in a variety of applications are disclosed.
    Type: Grant
    Filed: September 4, 2007
    Date of Patent: July 21, 2015
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Rajiv R. Singh, Raymond H. Thomas, Gary Knopeck
  • Patent number: 9040760
    Abstract: 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: Grant
    Filed: October 27, 2011
    Date of Patent: May 26, 2015
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Kazuhiro Takahashi, Yuzo Komatsu, Akinori Ueda
  • Patent number: 9029617
    Abstract: The present invention provides routes for making 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) from commercially available raw materials. More specifically, this invention provides several routes for forming HCFO-1233zd from 3,3,3-trifluoropropene (FC-1234zf).
    Type: Grant
    Filed: July 14, 2014
    Date of Patent: May 12, 2015
    Assignee: Honeywell International Inc.
    Inventors: Haridasan K. Nair, David Nalewajek, Andrew Joseph Poss, Yian Zhai
  • Patent number: 9018428
    Abstract: 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: Grant
    Filed: March 14, 2013
    Date of Patent: April 28, 2015
    Assignee: Honeywell International Inc.
    Inventor: Stephen A. Cottrell
  • Publication number: 20150105595
    Abstract: The present invention relates to an improved method for manufacturing 2-chloro-3,3,3,-trifluoropropene (HCFC-1233xf) by reacting 1,1,2,3-tetrachloropropene, 1,1,1,2,3-pentachloropropane, and/or 2,3,3,3-tetrachloropropene with hydrogen fluoride, in a vapor phase reaction vessel in the presence of a vapor phase fluorination catalyst and stabilizer. HCFC-1233xf is an intermediate in the production of 2,3,3,3-tetrafluoropropene (HFO-1234yf) which is a refrigerant with low global warming potential.
    Type: Application
    Filed: December 15, 2014
    Publication date: April 16, 2015
    Inventors: Daniel C. Merkel, Hsueh S. Tung
  • Patent number: 9000241
    Abstract: The disclosure describes a process for dehalogenation of chlorofluorocompounds. The process comprises contacting a saturated chlorofluorocompound with hydrogen in the presence of a catalyst at a temperature sufficient to remove chlorine and/or fluorine substituents to produce a fluorine containing terminal olefin.
    Type: Grant
    Filed: October 20, 2011
    Date of Patent: April 7, 2015
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Ekaterina N. Swearingen, Allen Capron Sievert, Xuehui Sun
  • 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
  • Publication number: 20150045590
    Abstract: The present invention provides routes for making 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) from commercially available raw materials. More specifically, this invention provides several routes for forming HCFO-1233zd from 3,3,3-trifluoropropene (FC-1234zf).
    Type: Application
    Filed: July 14, 2014
    Publication date: February 12, 2015
    Inventors: Haridasan K. Nair, David Nalewajek, Andrew Joseph Poss, Yian Zhai
  • Publication number: 20150011804
    Abstract: The present invention relates, in part, an improved process for the production of certain hydrofluoroolefins, particularly 2,3,3,3-tetrafluoropropene (1234yf). In certain non-limiting embodiments, the invention relates to methods for improving process efficiency during the fluorination of 1,1,2,3-tetrachloropropene, 2,3,3,3-tetrachloropropene, and/or 1,1,1,2,3-pentachloropropane to 2-chloro-3,3,3-trifluoropropene by separating and recycling unreacted HF, unreacted starting materials, and/or certain pro cess intermediates from the 2-chloro-3,3,3-trifluoropropene product stream.
    Type: Application
    Filed: February 25, 2013
    Publication date: January 8, 2015
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou Wang, Selma Bektesevic, Hsueh S. Tung, Haluk Kopkalli, Yuon Chiu
  • Publication number: 20150008357
    Abstract: To provide a method for efficiently separating 2,3,3,3-tetrafluoropropene (HFO-1234yf) and chloromethane (R40) from a composition comprising HFO-1234yf and R40. An azeotrope-like composition comprising from 58 to 78 mol % of HFO-1234yf and from 22 to 42 mol % of R40, and a method for producing HFO-1234yf, which comprises steps of distilling an initial mixture containing HFO-1234yf in a content exceeding 63 mol % in the total amount of HFO-1234yf and R40, thereby to separate the initial mixture into a first fraction in which the content of HFO-1234yf in the total amount of HFO-1234yf and R40 is lower than the content of HFO-1234yf in the total amount of HFO-1234yf and R40 in the initial mixture, and a second fraction in which the content of HFO-1234yf in the total amount of HFO-1234yf and R40 is higher than the content of HFO-1234yf in the total amount of HFO-1234yf and R40 in the initial mixture, and then obtaining HFO-1234yf having a reduced R40 concentration, from the second fraction.
    Type: Application
    Filed: September 26, 2014
    Publication date: January 8, 2015
    Applicant: ASAHI GLASS COMPANY, LIMITED
    Inventors: Shoji Furuta, Tetsuo Otsuka
  • Publication number: 20140357907
    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: Application
    Filed: April 1, 2014
    Publication date: December 4, 2014
    Applicant: CENTRAL GLASS COMPANY, LIMITED
    Inventors: Satoru OKAMOTO, Yoshio NISHIGUCHI, Fuyuhiko SAKYU
  • Patent number: 8901360
    Abstract: Disclosed is a process for preparing cis-1,1,1,4,4,4-hexafluorobutene comprising the steps of (a) reacting CCl4 with a compound having the formula CF3CX?CXH, where each X is independently halogen or hydrogen, to form a compound having the formula CF3CXClCXHCCl3; (b) fluorinating the compound formed in step (a) to form a compound having the formula CF3CXHCXHCF3; (c) converting the compound formed in step (b) by a reaction selected from the group consisting of dehydrohalogenation, dehalogenation and both reactions, to form a compound having the formula CF3C?CCF3; and (d) catalytically reducing the compound formed in step (c) with hydrogen to form the compound having the formula:
    Type: Grant
    Filed: May 19, 2011
    Date of Patent: December 2, 2014
    Assignee: Honeywell International Inc.
    Inventors: Andrew Joseph Poss, David Nalewajek, Haridasan K. Nair, Michael Van Der Puy
  • Publication number: 20140249329
    Abstract: Methods of halogenating a carbon containing compound having an sp3 C—H bond are provided. Methods of fluorinating a carbon containing compound comprising halogenation with Cl or Br followed by nucleophilic substitution with F are provided. Methods of direct oxidative C—H fluorination of a carbon containing compound having an sp3 C—H bond are provided. The halogenated products of the methods are provided.
    Type: Application
    Filed: August 20, 2012
    Publication date: September 4, 2014
    Applicant: The Trustees of Princeton University
    Inventors: John T. Groves, Wei Liu
  • Patent number: 8779217
    Abstract: The invention relates to a method for preparing fluoropropenes of formula (I) CF3CF?CHR, where R is a hydrogen or a fluorine atom from at least one compound of formula (Ia) CF3CF?CFR, where R has the same meaning as in formula (I), said method including the following steps: (i) hydrogenating at least one compound of formula (Ia) in an adiabatic reactor in the presence of a catalyst with a superstoichiometric amount of hydrogen so as to produce a hydrofluoropropane; (ii) partially condensing the flow from the adiabatic reactor of step (i) so as to produce a gaseous phase fraction, including unreacted hydrogen and a portion of the formed hydrofluoropropane, which is recirculated to step (i), and a liquid phase fraction including the residue of the hydrofluoropropane; (iii) dehydrofluorinating hydrofluoropropane from the liquid fraction of step (ii) using potassium hydroxide in an aqueous reaction medium contained in an agitated reactor so as to produce the fluoropropene of formula (I); and (iv) purifying the fl
    Type: Grant
    Filed: May 21, 2010
    Date of Patent: July 15, 2014
    Assignee: Arkema France
    Inventors: Michel Devic, Nicolas Doucet, Laurent Wendlinger, Geraldine Cavallini, Pierre-Marie Sedat, Karine Avril
  • Patent number: 8766020
    Abstract: The present invention discloses a manufacturing process to produce high purity 1234yf from 245eb, which preferably includes the removal of impurities present in 245eb raw material, the dehydrofluorination of 245eb, and the removal of impurities present in final crude product. The disclosed manufacturing process allows the production of a 1234yf product with lower the levels of 1225ye and/or trifluoropropene, preferably in amounts of less than about 500, and 50 ppm, respectively.
    Type: Grant
    Filed: July 28, 2009
    Date of Patent: July 1, 2014
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung, Rajiv R. Singh, Ian Shankland
  • Patent number: 8742181
    Abstract: A process for isomerizing a (hydrohalo)fluoroalkene, the process comprising contacting the (hydrohalo)fluoroalkene with a catalyst a catalyst which is a chromia-containing catalyst supported on AlF3 or fluorinated alumina.
    Type: Grant
    Filed: November 21, 2012
    Date of Patent: June 3, 2014
    Assignee: Mexichem Amanco Holding S.A. de C.V.
    Inventors: Andrew Paul Sharratt, John Charles McCarthy
  • Patent number: 8680345
    Abstract: Disclosed is a method for the production of 1233xf comprising the continuous low temperature liquid phase reaction of 1,1,1,2,3-pentachloropropane and anhydrous HF, without the use of a catalyst, wherein the reaction takes place in one or more reaction vessels, each one in succession converting a portion of the original reactants fed to the lead reaction vessel and wherein the reactions are run in a continuous fashion.
    Type: Grant
    Filed: December 7, 2011
    Date of Patent: March 25, 2014
    Assignee: Honeywell International Inc.
    Inventors: Daniel C. Merkel, Hsueh Sung Tung, Konstantin A. Pokrovski, Haiyou Wang, Selma Bektesevic
  • Patent number: 8653309
    Abstract: Trans-1233zd, the trans-isomer of 1-chloro-3,3,3-trifluoropropene (HCFO-1233zd) can be used as blowing agents, solvents, cleaning agents, as well as monomers of macromolecule compounds, and can be prepared through the dehydrochlorination of 1,1,1-trifluoro-3,3-dichloropropane (HCFC-243fa) with the help of a catalyst. The present invention is directed to an integrated process is proposed to produce trans-1233zd from 243fa, which is consisted of the following four major unit operations: (1) Catalytic dehydrochlorination of 243fa into trans/cis-1233zd, (2) HCl recovery, (3) Catalytic isomerization of cis-1233zd into trans-1233zzd, and (4) Isolation of trans-1233zd.
    Type: Grant
    Filed: April 20, 2011
    Date of Patent: February 18, 2014
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Publication number: 20140031595
    Abstract: The present invention provides continuous, gas phase, free radical processes for the production of chlorinated and/or fluorinated propenes or higher alkenes from the reaction of chlorinated and/or fluorinated alkanes and chlorinated and/or fluorinated alkenes, wherein wherein at least a portion of any intermediate boiler by-products generated by the process are removed from the process
    Type: Application
    Filed: October 4, 2013
    Publication date: January 30, 2014
    Applicant: DOW GLOBAL TECHNOLOGIES, LLC
    Inventors: Max Markus Tirtowidjojo, Patrick Ho-Sing Au-Yeung, Debashis Chakraborty, Juergen Eiffler, Heinz Groenewald, Kurt Frederick Hirsekorn, Manfred Kokott, William J. Kruper, JR., Thomas Ulrich Luebbe, Holger Meeman, Shirley Shaw Sexton, Peter Wenzel, Marcus Wobser
  • Patent number: 8633340
    Abstract: 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: Grant
    Filed: April 9, 2009
    Date of Patent: January 21, 2014
    Assignee: Mexichem Amanco Holding S.A. de C.V.
    Inventors: John W. Smith, Claire McGuiness, Andrew P. Sharratt
  • Publication number: 20140018582
    Abstract: The present disclosure relates to processes for reducing the concentration of RfC?CX impurities in fluoroolefins. The process involves: contacting a mixture comprising at least one fluoroolefin and at least one RfC?CX impurity with at least one amine to reduce the concentration of the at least one RfC?CX impurity in the mixture; wherein Rf is a perfluorinated alkyl group, and X is H, F, Cl, Br or I. The present disclosure also relates to processes for making at least one hydrotetrafluoropropene product selected from the group consisting of CF3CF?CH2, CF3CH?CHF, and mixtures thereof and reducing the concentration of CF3C?CH impurity generated during the process. The present disclosure also relates to processes for making at least one hydrochlorotrifluoropropene product selected from the group consisting of CF3CCl?CH2, CF3CH?CHCl, and mixtures thereof and reducing the concentration of CF3C?CH impurity generated during the process.
    Type: Application
    Filed: June 6, 2013
    Publication date: January 16, 2014
    Inventors: Xuehui SUN, Mario Joseph NAPPA
  • Publication number: 20140012049
    Abstract: Disclosed are processes for producing halogenated olefins, and preferably tetrafluorinated propene(s), from one or more alkanes having both fluorine substituents and non-fluorine substituents, preferably with a high degree of conversion and selectivity. Preferably the process comprises the use of a catalyzed reaction in which the catalyst is selected from the group consisting of activated carbons, halogentated mono- and di-valent metal oxides, mono- and di-valent Lewis acid metal halides, zero-valent metals, and combinations of these.
    Type: Application
    Filed: August 16, 2013
    Publication date: January 9, 2014
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: HAIYOU WANG, HSUEH SUNG TUNG, SUDIP MUKHOPADHYAY
  • Publication number: 20140012050
    Abstract: 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: Application
    Filed: August 19, 2013
    Publication date: January 9, 2014
    Applicant: Mexichem Amanco Holding S.A. de C.V.
    Inventors: John W. Smith, Claire McGuiness, Andrew P. Sharratt
  • Patent number: 8623233
    Abstract: Azeotropic or azeotrope-like compositions are disclosed. The azeotropic or azeotrope-like compositions are mixtures of Z-1,1,1,4,4,4-hexafluoro-2-butene, trans-1,2-dichloroethylene and 1,1,1,3,3-pentafluorobutane. Also disclosed is a process of preparing a thermoplastic or thermoset foam by using such azeotropic or azeotrope-like compositions as blowing agents. Also disclosed is a process of producing refrigeration by using such azeotropic or azeotrope-like compositions. Also disclosed is a process of using such azeotropic or azeotrope-like compositions as solvents. Also disclosed is a process of producing an aerosol product by using such azeotropic or azeotrope-like compositions. Also disclosed is a process of using such azeotropic or azeotrope-like compositions as heat transfer media. Also disclosed is a process of extinguishing or suppressing a fire by using such azeotropic or azeotrope-like compositions. Also disclosed is a process of using such azeotropic or azeotrope-like compositions as dielectrics.
    Type: Grant
    Filed: January 10, 2011
    Date of Patent: January 7, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Mark L. Robin, Joan Ellen Bartelt
  • Publication number: 20140005446
    Abstract: A production method of 1-chloro-3,3,3-trifluoropropene according to the present invention includes bringing a composition containing a compound of the general formula (1): CF3—CH2—CHClX (where X is a fluorine atom or a chlorine atom) into contact with a solid catalyst in the presence of hydrogen chloride. In this production method, the composition containing ozone depleting HCFC such as 3-chloro-1,1,1,3-tetraluoforpropane or 3,3-dichloro-1,1,1-trifluoropropane can be efficiently converted to the 1-chloro-3,3,3-trifluoropropene, which has less influence on the global environment and is useful as a solvent, a cleaning agent, a coolant, a working fluid, a propellant, a raw material for fluorinated resins etc.
    Type: Application
    Filed: June 27, 2013
    Publication date: January 2, 2014
    Applicant: Central Glass Company, Limited
    Inventors: Hideaki IMURA, Naoto TAKADA
  • Patent number: 8618338
    Abstract: In this invention we are disclosing a process for the synthesis of hydrocchlorofluoro olefins (HCFO) and/or hydrofluoroolefins (HFO). The process is based on the gas phase, noncatalytic fluorination of hydrochlorofluoropropenes to form hydrofluoropropenes.
    Type: Grant
    Filed: November 16, 2011
    Date of Patent: December 31, 2013
    Assignee: Arkema Inc.
    Inventors: Maher Y. Elsheikh, Philippe Bonnet, Benjamin Bin Chen
  • Publication number: 20130317262
    Abstract: To provide a method for purifying R-1234yf, whereby it is possible to efficiently remove even impurities such as R-1243zf, etc. which are difficult to separate by distillation purification, from a mixture containing R-1234yf as the main component and various impurities, such as a gas formed by reacting R-1214ya with hydrogen. The method for purifying R-1234yf comprises a step of bringing a mixture which contains R-1234yf as the main component and also contains hydrohaloalkene impurities other than R-1234yf and hydrohaloalkane impurities, into contact with a solvent that has an extraction/removal index (r), as represented by the formula r=[4×(?D?17.2)2+(?P?8.3)2+(?H?2.6)2]1/2, of at most 6.5, so as to remove at least a part of the hydrohaloalkene impurities and hydrohaloalkane impurities.
    Type: Application
    Filed: August 5, 2013
    Publication date: November 28, 2013
    Applicant: ASAHI GLASS COMPANY, LIMITED
    Inventors: Kazuyoshi KURASHIMA, Kunio Watanabe, Hiroshi Yamamoto
  • Publication number: 20130303808
    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: Application
    Filed: July 17, 2013
    Publication date: November 14, 2013
    Inventors: HAIYOU WANG, HSUEH SUNG TUNG
  • Publication number: 20130296617
    Abstract: Disclosed are the combinations containing Z and E stereoisomers of hydrofluoroolefins where the more toxic isomer is less than about 30% weight of the combination (vs the sum of Z+E), to minimize the toxicity impact in the applications they will. be used for such as cooling and heat fluids, foams blowing agents or solvents. Also disclosed are means to obtain combinations containing Z and E stereoisomers of hydrofluoroolefins.
    Type: Application
    Filed: July 11, 2013
    Publication date: November 7, 2013
    Applicant: Arkema Inc.
    Inventors: Philippe Bonnet, Maher Y. Elsheikh
  • Publication number: 20130281700
    Abstract: The invention relates to palladium(0)-tris{tri-[3,5-bis(trifluoromethyl)-phenyl]-phosphine} complex of formula (I), as well as to its preparation and use. This compound is outstandingly stable, and can be used as catalyst with excellent results.
    Type: Application
    Filed: June 14, 2013
    Publication date: October 24, 2013
    Applicants: CHINOIN GYOGYSZER-ES VEGYESZETI TER-MEKEK GYARA ZRT, H4SEP KFT
    Inventors: Zoltán DALICZEK, Tibor SOÓS, Zoltán FINTA, Géza Timári, Gábor Vlád
  • Patent number: 8563789
    Abstract: In this invention we are disclosing a process for the synthesis of hydrocchlorofluoro olefins (HCFO) and/or hydrofluoroolefins (HFO). The process is based on the steps of fluorination of hydrochloropropenes or hydrochloropropanes to form hydrochlorofluoropropenes and/or hydrofluoropropenes, followed by gas phase, catalytic fluorination of the hydrochlorofluoropropenes to form hydrofluoropropenes.
    Type: Grant
    Filed: November 16, 2011
    Date of Patent: October 22, 2013
    Assignee: Arkema Inc.
    Inventors: Maher Y. Elsheikh, Philippe Bonnet, Benjamin Bin Chen
  • Patent number: 8524955
    Abstract: Disclosed is a process for making hexafluoro-2-butyne comprising the steps of: (a) providing a composition comprising CF3CX?CXCF3, where X=halogen; and (b) treating CF3CX?CXCF3 with a dehalogenation catalyst in the presence of a halogen acceptor compound Y, where Y is not hydrogen. The halogen acceptor compound Y is a material capable of being halogenated, preferably a compound having a multiple bond, such as an alkyne, alkene, allene, or carbon monoxide. Another suitable material capable of being halogenated is a cyclopropane. A catalyst effectively transfers halogen from CF3CX?CXCF3 to the halogen acceptor compound. Since Y is not hydrogen, the formation of CF3CX?CHCF3 is greatly reduced or eliminated.
    Type: Grant
    Filed: May 19, 2011
    Date of Patent: September 3, 2013
    Assignee: Honeywell International Inc.
    Inventors: Andrew Joseph Poss, David Nalewajek, Haridasan K. Nair, Michael Van Der Puy, Rajiv Ratna Singh
  • Patent number: 8524104
    Abstract: Fire extinguishing compositions and methods of extinguishing a fire comprising compounds of formula (I) where Rf is a fluorocarbon group. The compounds and compositions described herein are useful as intermediates in the preparation of or as additives to AFFF (aqueous film forming foam) formulations used for the extinguishment of fuel and solvent fires.
    Type: Grant
    Filed: August 27, 2009
    Date of Patent: September 3, 2013
    Assignee: Ansul, Incorporated
    Inventor: Jeffrey D. Michael
  • Publication number: 20130217928
    Abstract: 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: Application
    Filed: October 27, 2011
    Publication date: August 22, 2013
    Applicant: DAIKIN INDUSTRIES, LTD.
    Inventors: Kazuhiro Takahashi, Yuzo Komatsu, Akinori Ueda
  • Patent number: 8461401
    Abstract: Hexafluoro-2-butene (HFO-1336) is a low global warming potential blowing agent, refrigerant and solvent. This invention provides a method for making the compound, including the cis-isomer, from the readily available raw materials, carbon tetrachloride and 3,3,3-trifluoropropene. The trans-isomer formed in the process can be isomerized into cis-isomer by the use of an isomerization catalyst.
    Type: Grant
    Filed: March 11, 2011
    Date of Patent: June 11, 2013
    Assignee: Honeywell International Inc.
    Inventors: Hsueh Sung Tung, Haiyou Wang
  • Publication number: 20130123448
    Abstract: A method for capturing certain fluorinated vinyl monomers from a gaseous mixture using ionic liquids is described. The gaseous mixture is contacted with at least one ionic liquid, whereby at least a portion of the fluorinated vinyl monomer is absorbed by the ionic liquid. The method is useful for reducing emissions of fluorinated vinyl monomers and for increasing the product yields in the manufacture of polymers from these monomers.
    Type: Application
    Filed: May 9, 2012
    Publication date: May 16, 2013
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventors: CHARLES JOSEPH NOELKE, Mark Brandon Shiflett
  • Patent number: 8436216
    Abstract: A process is disclosed for making 1,1,1,4,4,4-hexafluoro-2-butene. The process involves reacting 2,2-dichloro-1,1,1-trifluoroethane with copper in the presence of an amide solvent and 2,2?-bipyridine. A process is also disclosed for making 1,1,1,4,4,4-hexafluoro-2-butene. The process involves reacting 2,2-dichloro-1,1,1-trifluoroethane with copper in the presence of an amide solvent and a Cu(I) salt. A process is further disclosed for making 1,1,1,4,4,4-hexafluoro-2-butene. The process involves reacting 2,2-dichloro-1,1,1-trifluoroethane with copper in the presence of an amide solvent, 2,2?-bipyridine and a Cu(I) salt.
    Type: Grant
    Filed: March 18, 2009
    Date of Patent: May 7, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventors: Xuehui Sun, Mario Joseph Nappa, Win-Chung Lee
  • Patent number: 8436217
    Abstract: Disclosed is a fully integrated process for making 1,1,1,3,3-pentafluoropropane (HFC-245fa), trans-1-chloro-3,3,3-trifluoropropene (HCFO-1233zd(E)), and trans-1,3,3,3-tetrafluoropropene (HFO-1234ze(E)).
    Type: Grant
    Filed: April 25, 2011
    Date of Patent: May 7, 2013
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Daniel C. Merkel, Konstantin A. Pokrovski, Hsueh Sung Tung, Ian Shankland
  • Publication number: 20130098396
    Abstract: Disclosed are compositions comprising unsaturated hydrofluorocarbons, an alkene with the formula of 1,1,1,4,4,5,5,6,6,6-decafluorohex-2-ene and its isomers (the “153-10 isomers”). The invention further relates to use of said compositions in methods to clean, degrease, deflux, dewater, deposit fluorolubricant, carrier fluid applications and heat transfer applications. The invention further relates to novel 153-10 isomer mixtures, their method of making and their use as cleaning compositions and in the methods listed above.
    Type: Application
    Filed: October 8, 2012
    Publication date: April 25, 2013
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventor: E I DU PONT DE NEMOURS AND COMPANY