Fluorine Is Sole Halogen Patents (Class 570/136)
  • Patent number: 10577295
    Abstract: The present invention relates, at least in part, to a process for making chlorotrifluoroethylene (CFO-1113) from 1,2-dichloro-1,1,2-trifluoroethane (HCFC-123a). In certain aspects, the process includes dehydrochlorinating 1,2-dichloro-1,1,2-trifluoroethane (HCFC-123a) in the presence of a catalyst selected from the group consisting of (i) one or more metal halides; (ii) one or more halogenated metal oxides; (iii) one or more zero-valent metals or metal alloys; (iv) combinations thereof.
    Type: Grant
    Filed: December 22, 2017
    Date of Patent: March 3, 2020
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou Wang, Hsueh Sung Tung
  • Patent number: 10370313
    Abstract: There is provided a method of efficiently manufacturing purified 1224yd containing 1224yd at a high concentration from a mixture containing 1224yd and a compound that forms an azeotropic composition or an azeotropic-like composition with 1224yd. A manufacturing method of purified 1224yd, includes making a first mixture of 1224yd and a compound (X1) forming an azeotropic composition or an azeotropic-like composition with 1224yd to be brought into contact with a first extraction solvent to obtain purified 1224yd not substantially containing the compound (X1).
    Type: Grant
    Filed: August 20, 2018
    Date of Patent: August 6, 2019
    Assignee: AGC Inc.
    Inventors: Tomoaki Taniguchi, Jumpei Nomura, Takayuki Sakai, Takashi Hayase
  • Patent number: 10358402
    Abstract: Provided is a process for producing fluorinated alkenes by providing a microwave plasma in a reactor chamber, introducing a protective gas feed into the reactor chamber, and contacting a conversion feed comprising at least one fluorinated linear or branched alkane with the plasma. Also provided are an apparatus and the use of the process and the apparatus.
    Type: Grant
    Filed: September 30, 2015
    Date of Patent: July 23, 2019
    Assignee: 3M INNOVATIVE PROPERTIES COMPANY
    Inventors: Tilman C. Zipplies, Klaus Hintzer, Monika A. Willert-Porada, Thorsten Gerdes, Jens Herdegen, Achim Schmidt-Rodenkirchen, Stephan Aschauer
  • Patent number: 10189756
    Abstract: The present invention provides adiabatic plug flow reactors suitable for the production of chlorinated and/or fluorinated propene and higher alkenes from the reaction of chlorinated and/or fluorinated alkanes and chlorinated and/or fluorinated alkenes. The reactors comprise one or more designs that minimize the production of by-products at a desired conversion.
    Type: Grant
    Filed: July 7, 2016
    Date of Patent: January 29, 2019
    Assignee: BLUE CUBE IP LLC
    Inventors: Max M. Tirtowidjojo, Hua Bai, Debashis Chakraborty, Juergen Eiffler, Heinz Groenewald, Kurt F. Hirsekorn, Manfred Kokott, William J. Kruper, Thomas U. Luebbe, Thomas J. Parsons, Avani Maulik Patel, Marcus Wobser
  • Patent number: 9902672
    Abstract: A hydrofluoroolefin is produced by reacting a chlorofluoroolefin with hydrogen in the presence of a platinum group metal catalyst supported on a carbon carrier to obtain a hydrofluoroolefin. The chlorofluoroolefin is represented by formula (1): CZX?CClY, where X is F or Cl, Y is F, Cl or H, and Z is F or CF3. The hydrofluoroolefin is represented by formula (2): CZX? ?CHY?, where X? is F when X is F, or X? is H when X is Cl, Y? is F when Y is F, or Y? is H when Y is Cl or H, and Z is the same as Z in the formula (1). The carbon carrier has acidic functional groups, and the total acidic functional group amount in the carbon carrier is at most 50 ?mol/g.
    Type: Grant
    Filed: February 6, 2017
    Date of Patent: February 27, 2018
    Assignee: ASAHI GLASS COMPANY, LIMITED
    Inventors: Xu Wang, Shinji Terazono, Masahiro Kanda, Satoshi Kawaguchi, Mitsugu Kasagawa
  • Patent number: 9884796
    Abstract: A process for the manufacture of halogenated olefins in semi-batch mode by dehydrohalogenation of halogenated alkanes in the presence of an aqueous base such as KOH which simultaneously neutralizes the resulting hydrogen halide. During the process, aqueous base is continuously added to the haloalkane which results in better yields, lower by-product formation and safer/more controllable operation.
    Type: Grant
    Filed: April 16, 2013
    Date of Patent: February 6, 2018
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: George R. Cook, Haluk Kopkalli, Stephen A. Cottrell, Yuon Chiu, Peter Scheidle, Daniel C. Merkel
  • Patent number: 9758451
    Abstract: A subject-matter of the invention is a process for the preparation of 2,3,3,3-tetrafluoro-1-propene which comprises the following stages: (i) hydrogenation of hexafluoropropylene to give 1,1,1,2,3,3-hexafluoropropane; (ii) dehydrofluorination of the 1,1,1,2,3,3-hexafluoropropane obtained in the preceding stage to give 1,2,3,3,3-pentafluoro-1-propene; (iii) hydrogenation of the 1,2,3,3,3-pentafluoro-1-propene obtained in the preceding stage to give 1,1,1,2,3-pentafluoropropane; and (iv) dehydrofluorination of the 1,1,1,2,3-pentafluoropropane obtained in the preceding stage to give 2,3,3,3-tetrafluoro-1-propene. Stages (ii) and (iv) are carried out using a water and potassium hydroxide mixture with the potassium hydroxide representing between 58 and 86% by weight of the mixture and at a temperature of between 110 and 180° C.
    Type: Grant
    Filed: December 22, 2015
    Date of Patent: September 12, 2017
    Assignee: Arkema France
    Inventors: Anne Pigamo, Michel Devic, Laurent Wendlinger
  • Patent number: 9079818
    Abstract: Disclosed is a process for the synthesis of fluorinated olefins, and in particularly preferred embodiments tetrafluorinated olefins having F on an unsaturated, non-terminal carbon, such as 2,3,3,3-tetrafluoropropene. The preferred processes of the present invention in accordance with one embodiment generally comprise: (a) reacting a compound of formula (I) X1X2??(I) with a compound of formula (II) CX1X2X3CX1?CX1X2??(II) to produce a reaction product comprising a compound of formula (III) CF3CHX1CH2X2??(III), and (b) exposing said compound of formula (III) to reaction conditions effective to convert said compound of formula (III) to a compound of formula (IV) CF3CZ?CH2??(IV) wherein X1, X2, and X3 are each independently selected from the group consisting of hydrogen, chlorine, bromine, fluorine and iodine, provided that X1 and X2 in formula (I) are not both hydrogen and Z is Cl, I, Br, or F.
    Type: Grant
    Filed: October 12, 2008
    Date of Patent: July 14, 2015
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Sudip Mukhopadhyay, Cheryl L. Bortz, Barbara A. Light, Cheryl L. Cantlon, Robert C. Johnson
  • Patent number: 9040759
    Abstract: A process for making a fluorinated olefin having the step of dehydrochlorinating a hydrochlorofluorocarbon having at least one hydrogen atom and at least one chlorine atom on adjacent carbon atoms, preferably carried out in the presence of a catalyst selected from the group consisting of (i) one or more metal halides, (ii) one or more halogenated metal oxides, (iii) one or more zero-valent metals/metal alloys, (iv) a combination of two or more of the foregoing.
    Type: Grant
    Filed: July 2, 2008
    Date of Patent: May 26, 2015
    Assignee: HONEYWELL INTERNATIONAL INC.
    Inventors: Haiyou Wang, Hsueh Sung Tung, Sudip Mukhopadhyay
  • Patent number: 8999196
    Abstract: The invention is to provide a new liquid crystal compound having a high clearing point, a good compatibility with other compounds, a small viscosity, and a high stability to heat, light and so forth; compound (1) is provided: R1CF2nR2??(1) wherein, for example, R1 is alkyl having 4 to 10 carbons or —(CH2)2—CH?CH2, R2 is alkyl having 2 to 10 carbons, n is 8, and R1 and R2 are not allowed to be straight-chain alkyl having an identical number of carbons.
    Type: Grant
    Filed: August 23, 2012
    Date of Patent: April 7, 2015
    Assignees: JNC Corporation, JNC Petrochemical Corporation
    Inventors: Hiroyuki Tanaka, Sayaka Fujimori
  • Patent number: 9000238
    Abstract: The present disclosure relates to a process for separating a fluoroolefin from a mixture comprising hydrogen fluoride and fluoroolefin, comprising azeotropic distillation both with and without an entrainer. In particular are disclosed processes for separating any of HFC-1225ye, HFC-1234ze, HFC-1234yf or HFC-1243zf from HF.
    Type: Grant
    Filed: August 16, 2012
    Date of Patent: April 7, 2015
    Assignee: E I du Pont de Nemours and Company
    Inventors: Jeffrey P. Knapp, Barry Asher Mahler, Donald J. Toton
  • Publication number: 20150051426
    Abstract: To provide a method for stably storing tetrafluoropropene filled in a container for e.g. storage or transportation, without occurrence of reaction such as polymerization. A method for storing tetrafluoropropene in a gaseous-liquid state composed of a gas phase and a liquid phase in a closed container, wherein the oxygen concentration (content) in the above gas phase is adjusted to at least 3 vol ppm and less than 3,000 vol ppm at a temperature of 25° C.
    Type: Application
    Filed: October 27, 2014
    Publication date: February 19, 2015
    Applicant: ASAHI GLASS COMPANY, LIMITED
    Inventors: Masato Fukushima, Masaaki Tsuzaki, Maki Shigematsu
  • Patent number: 8936757
    Abstract: Apparatuses and processes are provided for stripping gaseous hydrocarbons from particulate material. One process comprises the step of contacting particles containing hydrocarbons with a stripping vapor in countercurrent flow to remove at least a portion of the hydrocarbons with the stripping vapor to form stripped particles. Contacting the particles includes advancing the particles down a sloping element of a structured packing toward a reinforcing rod that is disposed along a lower channel portion of the sloping element. The particles are advanced over the reinforcing rod. The particles are contacted with the stripping vapor that is rising up adjacent to the lower channel portion.
    Type: Grant
    Filed: December 28, 2011
    Date of Patent: January 20, 2015
    Assignee: UOP LLC
    Inventors: Erick D. Gamas-Castellanos, Mitchell John Kowalczyk
  • 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: 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
  • Publication number: 20140316169
    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: Application
    Filed: June 30, 2014
    Publication date: October 23, 2014
    Inventors: HAIYOU WANG, HSUEH SUNG TUNG, RAJIV R. SINGH, IAN SHANKLAND
  • Publication number: 20140306146
    Abstract: The present invention is an etching gas comprising an unsaturated fluorohydrocarbon represented by CxHyFz (wherein x=3, 4, or 5, y+z?2x, and y>z) and a method comprising selectively etching a silicon nitride film relative to a silicon oxide film or a silicon film using the etching gas. According to the present invention, a silicon nitride film stacked on a silicon oxide film or a silicon film can be highly selectively etched.
    Type: Application
    Filed: March 27, 2012
    Publication date: October 16, 2014
    Applicant: ZEON CORPORATION
    Inventors: Azumi Ito, Atsuyo Yamazaki
  • Patent number: 8816138
    Abstract: The present invention provides a method for producing 3-chloro-pentafluoropropene at a high yield through one reaction step of chlorinating perfluoroallyl fluorosulfate. The present invention directs to a method for producing 3 -chloro-pentafluoropropene, including the step of bringing perfluoroallyl fluorosulfate and an onium chloride compound into contact with each other to produce the 3-chloro-pentafluoropropene.
    Type: Grant
    Filed: March 28, 2011
    Date of Patent: August 26, 2014
    Assignee: Daikin Industries, Ltd.
    Inventors: Shinsuke Ohshita, Yuichi Hashikawa, Masahiro Kondo, Takashi Yoshimura, Noriyuki Shinoki, Emi Mantani
  • Patent number: 8759281
    Abstract: The present invention relates to fluorocarbon vectors for the delivery of antigens to immunoresponsive target cells. It further relates to fluorocarbon vector-antigen constructs and the use of such vectors associated with antigens as vaccines and immunotherapeutics in animals.
    Type: Grant
    Filed: January 20, 2012
    Date of Patent: June 24, 2014
    Assignee: Immune Targeting Systems Ltd.
    Inventors: Dominique Bonnet, Carlton B. Brown, Bertrand Georges, Philip J. Sizer
  • Patent number: 8696926
    Abstract: A process is disclosed for making CF3CH2CHF2, CF3CH?CHF and/or CF3CH?CHCl. The process involves reacting at least one starting material selected from the group consisting of halopropanes of the formula CX3CHClCH2X, halopropenes of the formula CX3CCl?CH2 and halopropenes of the formula CX2?CClCH2X, wherein each X is independently F or Cl, with HF 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. Also disclosed is a process for making CF3CF2CH3 and/or CF3CF?CH2. In each of the processes the molar ratio of HF to total amount of starting material fed to the reaction zone is at least stoichiometric. Also disclosed is an azeotropic composition comprising CF3CCl?CH2, and HF. Also disclosed is an azeotropic composition comprising CF3CF2CH3, and HF.
    Type: Grant
    Filed: November 29, 2012
    Date of Patent: April 15, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Patent number: 8692037
    Abstract: Disclosed are compositions comprising HFC-245eb and at least one additional compound selected from the group consisting of HFO-1234ze, HFC-245fa, HFC-236cb, HFC-236ea, HFC-236fa, HFC-227ea, HFC-227ca, HFO-1225yc, HFO-1225zc, HFO-1225ye, methane, ethane, propane, HFC-23, HFC-143a, HFC-134, HFC-134a, FC-1216, HFO-1234yf, HFC-254eb, HFO-1243zf, and HFC-254fb. Compositions comprising HFC-245eb are useful in processes to make HFO-1234yf. Also disclosed are compositions comprising HFO-1234yf and at least one additional compound selected from the group consisting of HFO-1234ze, HFC-254eb, HFC-254fb, HFO-1243zf, HFCHFC-245eb, HFC-245fa, HFC-245cb, HFC-236cb, HFC-236ea, HFC-236fa, HFC-227ea, HFC-227ca, HFO-1225yc, HFO-1225zc, HFO-1225ye, methane, ethane, propane, HFC-23, HFC-134, HFC-134a, HFO-1132a and FC-1216. Compositions comprising HFO-1234yf are useful as heat transfer compositions for use in refrigeration, air-conditioning and heat pump systems.
    Type: Grant
    Filed: November 14, 2012
    Date of Patent: April 8, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Barry Asher Mahler, Mario Joseph Nappa, Jeffrey P Knapp
  • Publication number: 20140077123
    Abstract: To provide a working medium for heat cycle which has less influence over the ozone layer, which has less influence over global warming and which provides a heat cycle system excellent in the cycle performance (the efficiency and the capacity), and a heat cycle system excellent in the cycle performance (the efficiency and the capacity). A working medium for heat cycle comprising 1,2-difluoroethylene is employed for a heat cycle system (such as a Rankine cycle system, a heat pump cycle system, a refrigerating cycle system 10 or a heat transport system).
    Type: Application
    Filed: November 19, 2013
    Publication date: March 20, 2014
    Applicant: ASAHI GLASS COMPANY, LIMITED
    Inventor: Masato FUKUSHIMA
  • Publication number: 20140070132
    Abstract: To provide a working medium for heat cycle, of which combustibility is suppressed, which has less influence over the ozone layer, which has less influence over global warming and which provides a heat cycle system excellent in the cycle performance (capacity), and a heat cycle system, of which the safety is secured, and which is excellent in the cycle performance (capacity). A working medium for heat cycle comprising 1,1,2-trifluoroethylene is employed for a heat cycle system (such as a Rankine cycle system, a heat pump cycle system, a refrigerating cycle system 10 or a heat transport system).
    Type: Application
    Filed: November 19, 2013
    Publication date: March 13, 2014
    Applicant: ASAHI GLASS COMPANY, LIMITED
    Inventor: Masato FUKUSHIMA
  • Patent number: 8633339
    Abstract: Disclosed herein are blowing agents comprising fluorocarbons and/or hydrofluorocarbons useful in foamable compositions. Also disclosed are methods for forming a foam comprising the aforementioned blowing agents.
    Type: Grant
    Filed: November 1, 2006
    Date of Patent: January 21, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: Joseph Anthony Creazzo, Mario Joseph Nappa, Allen Capron Sievert, Ekaterina N. Swearingen
  • Patent number: 8604257
    Abstract: Disclosed is a process for the preparation of fluorine-containing olefins comprising contacting a chlorofluoroalkane with hydrogen in the presence of a catalyst at a temperature sufficient to cause replacement of the chlorine substituents of the chlorofluoroalkane with hydrogen to produce a fluorine-containing olefin. Also disclosed are catalyst compositions for the hydrodechlorination of chlorofluoroalkanes comprising copper metal deposited on a support, and comprising palladium deposited on calcium fluoride, poisoned with lead and reducing the in the presence or absence of a dehydrochlorination catalyst under conditions effective to form a product stream comprising cis-1,1,1,4,4,4-hexafluoro-2-butene (HFO-1336).
    Type: Grant
    Filed: May 19, 2011
    Date of Patent: December 10, 2013
    Assignee: Honeywell International Inc.
    Inventors: Andrew Joseph Poss, Michael Van Der Puy, Rajiv Ratna Singh, David Nalewajek, Haridasan K. Nair
  • Patent number: 8558041
    Abstract: The present invention provides isothermal multitube reactors suitable for the production of chlorinated and/or fluorinated propene and higher alkenes from the reaction of chlorinated and/or fluorinated alkanes and chlorinated and/or fluorinated alkenes. The reactors utilize a feed mixture inlet temperature at least 20° C. different from a desired reaction temperature.
    Type: Grant
    Filed: October 8, 2010
    Date of Patent: October 15, 2013
    Assignee: Dow Global Technologies, LLC
    Inventors: Max M. Tirtowidjojo, Hua Bai, Debashis Chakraborty, Juergen Eiffler, Heinz Groenewald, Kurt F. Hirsekorn, Manfred Kokott, William J. Kruper, Jr., Thomas U. Luebbe, Avani M. Patel, Shirley S. Sexton, Peter Wenzel, Marcus Wobser
  • Patent number: 8558040
    Abstract: Disclosed herein are blowing agents comprising fluorocarbons and/or hydrofluorocarbons useful in foamable compositions. Also disclosed are methods for forming a foam comprising the aforementioned blowing agents.
    Type: Grant
    Filed: November 1, 2006
    Date of Patent: October 15, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventors: Joseph Anthony Creazzo, Mario Joseph Nappa, Allen Capron Sievert, Ekaterina N. Swearingen
  • Patent number: 8552227
    Abstract: A dehydrofluorination process is disclosed for making hydrofluoroolefins of the structure RfCH?CHRf, wherein each Rf is independently a perfluoroalkyl group or a perfluoroalkyl group having a terminal hydrogen. The process involves reacting RfCH2CHFRf with a basic aqueous solution to produce a product mixture comprising RfCH?CHRf.
    Type: Grant
    Filed: December 10, 2009
    Date of Patent: October 8, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventors: Allen Capron Sievert, Norman A. Carlson
  • Patent number: 8530709
    Abstract: The present invention provides a method for the preparation of suitable chlorofluorocarbon and hydrochlorofluorocarbon materials or chlorofluorocarbon and hydrochlorofluorocarbon alkene and alkyne intermediates which serve as useful feedstock for fluorination and reduction to cis-1,1,1,4,4,4-hexafluoro-2-butene. Also presented is a continuous process for the production of cis-1,1,1,4,4,4-hexafluoro-2-butene from the alkene and alkyne intermediates.
    Type: Grant
    Filed: May 19, 2011
    Date of Patent: September 10, 2013
    Assignee: Honeywell International Inc.
    Inventors: Andrew Joseph Poss, David Nalewajek, Michael Van Der Puy, Haridasan K. Nair
  • Patent number: 8530708
    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: Grant
    Filed: October 27, 2006
    Date of Patent: September 10, 2013
    Assignee: Honeywell International Inc.
    Inventors: Haiyou Wang, Hsueh Sung Tung, Sudip Mukhopadhyay
  • Patent number: 8524835
    Abstract: Disclosed is a peroxide-crosslinkable fluoroelastomer obtained by copolymerization of 0.1 to 20 mol % of a mixture of fluoroolefin iodides represented by the general formulae: CnF2n+1CF2CH?CF(CF2CF2)mI [Ia] and CnF2n+1CF?CHCF2(CF2CF2)mI [Ib], wherein n is an integer of 0 to 5, and m is an integer of 1 to 3. The peroxide-crosslinkable fluoroelastomer is copolymerized with a monomer having a side chain containing a peroxide-crosslinkable halogen atom, and has excellent vulcanizate physical properties and improved compression set characteristics when subjected to peroxide crosslinking.
    Type: Grant
    Filed: August 17, 2009
    Date of Patent: September 3, 2013
    Assignee: Unimatec Co., Ltd.
    Inventors: Daisuke Murai, Mitsuru Maeda, Seiichiro Murata
  • Publication number: 20130217784
    Abstract: Disclosed are the use of fluorine substituted olefins, including tetra- and penta-fluoropropenes, in a variety of applications, including in methods of depositing catalyst on a solid support, methods of sterilizing articles, cleaning methods and compositions, methods of applying medicaments, fire extinguishing/suppression compositions and methods, flavor formulations, fragrance formulations and inflating agents.
    Type: Application
    Filed: March 15, 2013
    Publication date: August 22, 2013
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventor: HONEYWELL INTERNATIONAL INC.
  • Patent number: 8454738
    Abstract: Disclosed is a mold-releasing agent comprising, as active ingredients, a graft copolymer (A) in which a polyalkylene glycol or an alkyl ether thereof is graft-copolymerized with a polyfluoro-1-alkene represented by the general formula: CnF2n+1(CH2CF2)a(CF2CF2)bCH?CH2 (wherein n is an integer of 1 to 6, a is an integer of 1 to 4, and b is an integer of 1 to 3), and a polyfluoroalkylphosphonic acid represented by the general formula: CnF2n+1(CH2CF2)a(CF2CF2)b(CH2CH2)cP(O)(OH)2 (wherein n is an integer of 1 to 6, a is an integer of 1 to 4, and b is an integer of 1 to 3, and c is an integer of 1 to 3) or a salt thereof (B). The mold-releasing agent comprises, as an active ingredient, a compound having a perfluoroalkyl group containing 6 or less carbon atoms, which is said to have low bioaccumulation potential, and having mold release performance equivalent to or more than that of a mold-releasing agent comprising a compound having a perfluoroalkyl group containing 8 or more carbon atoms as an active ingredient.
    Type: Grant
    Filed: June 3, 2010
    Date of Patent: June 4, 2013
    Assignee: Unimatec Co., Ltd.
    Inventors: Yoshiyama Kaneumi, Seiichiro Murata, Katsuyuki Sato
  • Patent number: 8445735
    Abstract: Described is a method for producing fluoropropenes of formula CF3CX?CX2 wherein each X is F or H, at least one X is H, and at least one X is F, comprising pyrolyzing a hydrofluorochloropropane of formula CF3CXYCX2Y, wherein each X is F or H, at least one X is H, and at least one X is F, and one Y is Cl and the other Y is H, in the gas-phase in a reaction vessel, maintained at a temperature high enough to effect the pyrolysis of said hydrofluorochloropropane to said fluoropropene, wherein the selectivity for the production of the fluoropropene is at least 80%, in he absence of a catalyst.
    Type: Grant
    Filed: May 23, 2012
    Date of Patent: May 21, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventor: Mario Joseph Nappa
  • Publication number: 20130105724
    Abstract: The invention relates to a stable composition (CS) comprising at least x wt.-% 2,3,3,3-tetrafluoropropene (99.8?x<100), at most y wt.-% unsaturated compound(s) (Ia) (0<y?0.2) selected from among 3,3,3-trifluoropropene (HFO-1243zf) and the positional isomers of 2,3,3,3-tetrafluoropropene, such as 1,3,3,3-tetrafluoropropene (isomers Z and E) and 1,1,2,3-tetrafluoropropene, and, optionally, at most 500 ppm of 3,3,3-trifluoropropyne and/or at most 200 ppm 1,1,1,2,3-pentafluoropropene (HFO-1225ye).
    Type: Application
    Filed: June 20, 2011
    Publication date: May 2, 2013
    Applicant: Arkema France
    Inventor: Beatrice Boussand
  • 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
  • Patent number: 8426657
    Abstract: The present invention relates to compositions and processes of using perfluoropolyether to maintain or improve the oil return, lubrication, cooling capacity, or energy efficiency of a refrigeration, air conditioning or heat transfer system.
    Type: Grant
    Filed: September 23, 2011
    Date of Patent: April 23, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventors: Thomas J. Leck, Thomas Frank Saturno, Gregory A. Bell
  • Publication number: 20130091843
    Abstract: Aspects of the present invention are directed to working fluids and their use in processes wherein the working fluids comprise compounds having the structure of formula (I): wherein R1, R2, R3, and R4 are each independently selected from the group consisting of: H, F, Cl, Br, and C1-C6 alkyl, at least C6 aryl, at least C3 cycloalkyl, and C6-C15 alkylaryl optionally substituted with at least one F, Cl, or Br, wherein formula (I) contains at least one F and optionally at least one Cl or Br, provided that if any R is Br, then the compound does not have hydrogen. The working fluids are useful in Rankine cycle systems for efficiently converting waste heat generated from industrial processes, such as electric power generation from fuel cells, into mechanical energy or further to electric power. The working fluids of the invention are also useful in equipment employing other thermal energy conversion processes and cycles.
    Type: Application
    Filed: November 30, 2012
    Publication date: April 18, 2013
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventor: Honeywell International Inc.
  • Patent number: 8415439
    Abstract: The present invention provides an ETFE-type copolymer having a high melt tension and excellent blow moldability. An ethylene-tetrafluoroethylene copolymer which comprises ethylene units, tetrafluoroethylene units and units of a monomer (A) having at least two copolymerizable double bonds and which has a ratio (X/W) of its melt tension (XmN) to a load (Wkg) applied for the measurement of the melt tension being at least 0.8.
    Type: Grant
    Filed: April 13, 2010
    Date of Patent: April 9, 2013
    Assignee: Asahi Glass Company, Limited
    Inventors: Shintaro Fukunaga, Atsushi Funaki
  • Patent number: 8398882
    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 CX3CHClCH2X, halopropenes of the formula CClX2CCl?CH2 and halopropenes of the formula CX2?CClCH2X, wherein each X is independently F or Cl, with HF 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.
    Type: Grant
    Filed: October 31, 2007
    Date of Patent: March 19, 2013
    Assignee: E I du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
  • Patent number: 8395000
    Abstract: Disclosed are methods for producing fluorinated organic compounds, including hydrofluoropropenes, which preferably comprises converting at least one compound of formula (I): CF3CHXCH2X??(I) to at least one compound of formula (II) CF3CZCHZ??(II). where X is independently Cl, Br, I or F, and Z independently is H or F. In certain preferred embodiments, each Z is different.
    Type: Grant
    Filed: February 8, 2010
    Date of Patent: March 12, 2013
    Assignee: Honeywell International Inc.
    Inventors: Sudip Mukhopadhyay, Haridasan K. Nair, Hsueh S. Tung, Michael Van Der Puy, Daniel C. Merkel, Rajesh K. Dubey, Jing Ji Ma
  • Publication number: 20130048913
    Abstract: The invention is to provide a new liquid crystal compound having a high clearing point, a good compatibility with other compounds, a small viscosity, and a high stability to heat, light and so forth; compound (1) is provided: R1?CF2?nR2??(1) wherein, for example, R1 is alkyl having 4 to 10 carbons or —(CH2)2—CH?CH2, R2 is alkyl having 2 to 10 carbons, n is 8, and R1 and R2 are not allowed to be straight-chain alkyl having an identical number of carbons.
    Type: Application
    Filed: August 23, 2012
    Publication date: February 28, 2013
    Applicants: JNC PETROCHEMICAL CORPORATION, JNC CORPORATION
    Inventors: Hiroyuki TANAKA, Sayaka FUJIMORI
  • Patent number: 8377187
    Abstract: Disclosed is a graft copolymer in which a polyalkylene glycol or an alkyl ether thereof is graft-copolymerized with a polyfluoro-1-alkene represented by the general formula: CnF2n+(CH2CF2)a(CF2CF2)bCH?CH2 (wherein n is an integer of 1 to 6, a is an integer of 1 to 4, and b is an integer of 1 to 3). The graft copolymer is an oligomer compound having a perfluoroalkyl group containing 6 or less carbon atoms, which is said to have low bioaccumulation potential, and having, when used as an active ingredient of a mold-releasing agent, mold release performance equivalent to that of a compound having a perfluoroalkyl group containing 8 or more carbon atoms.
    Type: Grant
    Filed: June 3, 2010
    Date of Patent: February 19, 2013
    Assignee: Unimatec Co., Ltd.
    Inventors: Yoshiyama Kaneumi, Seiichiro Murata, Katsuyuki Sato
  • Publication number: 20130037279
    Abstract: Disclosed herein are flame suppression compounds and methods of use thereof. The compounds include unsaturated fluorocarbons appropriate for use in fire protection applications.
    Type: Application
    Filed: October 15, 2012
    Publication date: February 14, 2013
    Applicant: E I DU PONT DE NEMOURS AND COMPANY
    Inventor: E I DU PONT DE NEMOURS AND COMPANY
  • Patent number: 8357828
    Abstract: To provide a simple and economical process for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene, which does not require purification of the raw material component obtained in the form of a mixture of isomers, and a process for producing 2,3,3,3-tetrafluoropropene from the product thereby obtained. A process for producing 1,1-dichloro-2,3,3,3-tetrafluoropropene, characterized by bringing a mixture of dichloropentafluoropropane isomers which contains 1,1-dichloro-2,2,3,3,3-pentafluoropropane into contact with an aqueous alkali solution in the presence of a phase transfer catalyst, and thereby selectively dehydrofluorinating only the 1,1-dichloro-2,2,3,3,3-pentafluoropropane in the mixture, and a process for producing 2,3,3,3-tetrafluoropropene from the 1,1-dichloro-2,3,3,3-tetrafluoropropene thereby obtained.
    Type: Grant
    Filed: June 20, 2011
    Date of Patent: January 22, 2013
    Assignee: Asahi Glass Company, Limited
    Inventors: Hidekazu Okamoto, Yasuyuki Sasao
  • Patent number: 8350101
    Abstract: The present invention relates to the method for obtaining vinylidene fluoride and the subject matter thereof is more particularly the production of vinylidene fluoride by pyrolysis of 1,2-dichloro-2,2-difluoroethane in the presence of hydrogen at a temperature of greater than or equal to 400° C.
    Type: Grant
    Filed: August 20, 2009
    Date of Patent: January 8, 2013
    Assignee: Arkema France
    Inventors: Sylvain Perdrieux, Serge Hub
  • Patent number: 8344190
    Abstract: Process for producing fluorinated olefins from fluorinated materials, the process comprising thermally decomposing the fluoropolymers into fluoroolefins in a reactor having a feeding zone where the fluorinated materials are fed into the reactor and a decomposition zone where the fluorinated materials are thermally decomposed and wherein the thermal decomposition is carried out in the presence of microwave irradiation.
    Type: Grant
    Filed: September 30, 2009
    Date of Patent: January 1, 2013
    Assignee: 3M Innovative Properties Company
    Inventors: Klaus Hintzer, Gunther J. Kaempf, Thomas Kolbeck, Tilman C. Zipplies, Monika A. Willert-Porada, Thorsten Gerdes, Achim Schmidt-Rodenkirchen
  • Patent number: 8293953
    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: Grant
    Filed: March 21, 2011
    Date of Patent: October 23, 2012
    Assignee: Asahi Glass Company, Limited
    Inventor: Hidekazu Okamoto
  • Patent number: 8288492
    Abstract: Oligomers of perfluoro(methyl vinyl ether) with vinylidene fluoride or tetrafluoroethylene are disclosed that contain 40-90 mole percent copolymerized units of vinylidene fluoride or tetrafluoroethylene and 10-60 mole percent copolymerized units of perfluoro(methyl vinyl ether), said oligomers having two functional endgroups and having a number average molecular weight between 1000 and 25,000.
    Type: Grant
    Filed: September 12, 2008
    Date of Patent: October 16, 2012
    Assignees: E I du Pont de Nemours and Company
    Inventors: Ming-Hong Hung, Bruno Ameduri, Cyrille Andre Jean-Marie Boyer
  • 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