Substituting Halogen For A Different Halogen Patents (Class 570/170)
  • Patent number: 7348461
    Abstract: Methods and materials are provided for the production of essentially isomerically pure perhalogenated and partially halogenated compounds. One embodiment of the present invention provides a process for the production of essentially isomerically pure CFC-216aa. Other embodiments include processes for the production of CFC-217ba and HFC-227ea. Particular embodiments of the present invention provide separation techniques for the separation of chlorofluorocarbons from HF, from other chlorofluorocarbons, and the separation of isomers of halogenated compounds. Still other embodiments of the present invention provide catalytic synthetic techniques that demonstrate extended catalyst lifetime. In other embodiments, the present invention provides catalytic techniques for the purification of isomeric mixtures.
    Type: Grant
    Filed: October 31, 2003
    Date of Patent: March 25, 2008
    Assignee: Great Lakes Chemical Corporation
    Inventors: Yuichi Iikubo, Stephen Owens, Mitchel Cohn, Stephan M. Brandstadter, Vicki E. Hedrick, Janet K. Boggs, John Qian, Julie Sacarias
  • Patent number: 7335804
    Abstract: Provided are methods for producing hydrofluorocarbons via the selective reduction of a halocarbon blend comprising 1,3-dichloro-1,1,2,2,3-pentafluoropropane.
    Type: Grant
    Filed: November 3, 2005
    Date of Patent: February 26, 2008
    Assignee: Honeywell International Inc.
    Inventors: Haridasan Nair, Sudip Mukhopadhyay, Michael Van Der Puy
  • Patent number: 7329786
    Abstract: Methods and materials are provided for the production of essentially isomerically pure perhalogenated and partially halogenated compounds. One embodiment of the present invention provides a process for the production of essentially isomerically pure CFC-216aa. Other embodiments include processes for the production of CFC-217ba and HFC-227ea. Particular embodiments of the present invention provide separation techniques for the separation of chlorofluorocarbons from HF, from other chlorofluorocarbons, and the separation of isomers of halogenated compounds. Still other embodiments of the present invention provide catalytic synthetic techniques that demonstrate extended catalyst lifetime. In other embodiments, the present invention provides catalytic techniques for the purification of isomeric mixtures.
    Type: Grant
    Filed: September 28, 2001
    Date of Patent: February 12, 2008
    Assignee: Great Lakes Chemical Corporation
    Inventors: Yuichi Iikubo, Stephen Owens, Mitchel Cohn, Stephan M. Brandstadter, Vicki E. Hedrick, Janet K. Boggs, John Chengping Chien, Julie Sacarias, Vimal Sharma
  • Patent number: 7319175
    Abstract: Catalysts such as antimony halides, which are useful in fluorination reactions involving hydrogen fluoride, may be reduced during the reaction and require regeneration. Regenerative oxidation is usually carried out by introducing elemental halogen, preferably fluorine or chlorine, into the reaction mixture. In accordance with the invention elemental halogen is prevented from coming into contact with starting materials or intermediate products which are reactive therewith. This is preferably achieved by withdrawing part of the reaction mixture from the reactor, mixing the withdrawn part with chlorine or fluorine in order to regenerate the catalyst, and thereafter returning the withdrawn part to the reactor.
    Type: Grant
    Filed: October 27, 2005
    Date of Patent: January 15, 2008
    Assignee: Solvay Fluor und Derivate GmbH
    Inventors: Max Braun, Carsten Brosch
  • Patent number: 7223892
    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: June 28, 2006
    Date of Patent: May 29, 2007
    Assignee: Solvay S.A.
    Inventors: Alain Lambert, Vincent Wilmet
  • Patent number: 7214839
    Abstract: A manufacturing process for making hydrofluorocarbons (HFCs), by reacting a hydrochlorocarbon and HF in a liquid phase catalytic reactor using a large mole ratio of HF to hydrochlorocarbon to minimize formation of high boiling by-products and improve HF consumption and hydrofluorocarbon yields.
    Type: Grant
    Filed: May 23, 2003
    Date of Patent: May 8, 2007
    Assignee: Honeywell International Inc.
    Inventors: Hsueh Sung Tung, Chad L. Marks, Stephen A. Cottrell
  • Patent number: 7202388
    Abstract: Processes for preparing fluoroarenes are provided. The processes include contacting a compound having an unactivated aryl group with a source of fluoride or bifluoride in the presence of a transition metal a ligand.
    Type: Grant
    Filed: October 5, 2005
    Date of Patent: April 10, 2007
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Vladimir Grushin
  • Patent number: 7183449
    Abstract: Process for the treatment of by-products from a reaction for the production of organic compounds comprising a stage of evaporation of a liquid phase comprising heavy by-products on a surface, in order to form a concentrated phase comprising the bulk of the heavy by-products and a vapor phase essentially devoid of heavy by-products, and a stage of recovery of the solid phase from the surface.
    Type: Grant
    Filed: June 21, 2002
    Date of Patent: February 27, 2007
    Assignee: Solvay S.A.
    Inventors: Lionel Casaubon Seignour, Philippe Krafft, Bruno Fouchet
  • Patent number: 7183448
    Abstract: A mixture comprising at least 1,1,1,3,3-pentafluoropropane and 1,1,1-trifluoro-3-chloro-2-propene is subjected to a distillation operation, and thereby, a distillate comprising an azeotropic composition consisting substantially of 1,1,1,3,3-pentafluoropropane and 1,1,1-trifluoro-3-chloro-2-propene is obtained and a bottom product comprising 1,1,1,3,3-pentafluoropropane or 1,1,1-trifluoro-3-chloro-2-propene which each is separated and purified.
    Type: Grant
    Filed: November 10, 1999
    Date of Patent: February 27, 2007
    Assignee: Daikin Industries, Ltd.
    Inventors: Tatsuo Nakada, Masayoshi Imoto, Takashi Shibanuma
  • Patent number: 7102041
    Abstract: A process for preparing a haloalkane comprising: (a) contacting a haloalkane starting material with an alkene in the presence of an effective amount of a catalyst complex under conditions effective to facilitate an addition reaction and to form a product stream comprising a haloalkane product from the addition reaction, wherein the catalyst complex has a boiling point higher than that of the haloalkane product; and (b) recovering the haloalkane product from the product stream.
    Type: Grant
    Filed: December 8, 2004
    Date of Patent: September 5, 2006
    Assignee: Honeywell International Inc.
    Inventor: Hsueh Sung Tung
  • Patent number: 7094936
    Abstract: Methods and materials are provided for the production and purification of halogenated compounds and intermediates in the production of 1,1,1,3,3-pentafluoropropane. In a preferred embodiment, the process steps include: (1) reacting carbon tetrachloride with vinyl chloride to produce 1,1,1,3,3-pentachloropropane; (2) dehydrochlorinating the 1,1,1,3,3-pentachloropropane with a Lewis acid catalyst to produce 1,1,3,3-tetrachloropropene; (3) fluorinating the 1,1,3,3-tetrachloropropene to produce 1-chloro-3,3,3-trifluoropropene; (4) fluorinating the 1-chloro-3,3,3-trifluoropropene to produce a product mixture containing 1,1,1,3,3-pentafluoropropane; and (5) separating 1,1,1,3,3-pentafluoropropane from by-products.
    Type: Grant
    Filed: October 16, 2003
    Date of Patent: August 22, 2006
    Assignee: Great Lakes Chemical Corporation
    Inventors: Stephen Owens, Andrew Jackson, Vimal Sharma, Mitchel Cohn, John Cheng-Ping Qian, Julia Ann Sacarias, Yuichi Iikubo
  • Patent number: 7094934
    Abstract: In a process for producing a hydrogen-containing fluorinated hydrocarbon in which a halogenated hydrocarbon reaction raw material, which includes a chlorinated alkene and/or a hydrogen-containing chlorinated alkane, is subjected to a fluorination reaction with hydrogen fluoride in a liquid phase in a reactor in the presence of a fluorination catalyst to obtain a reaction mixture which includes the hydrogen-containing fluorinated hydrocarbon, the reactor to be used has a portion which is able to contact with the reaction mixture, at least a part of this portion being made of an alloy material of 18 to 20% by weight of chromium, 18 to 20% by weight of molybdenum, 1.5 to 2.2% by weight of at least one element selected from niobium and tantalum and the balance of nickel.
    Type: Grant
    Filed: January 31, 2001
    Date of Patent: August 22, 2006
    Assignee: Daikin Industries, Ltd.
    Inventors: Noriaki Shibata, Tatsuo Nakada, Takashi Shibanuma
  • Patent number: 7084316
    Abstract: A process comprising bringing crude pentafluoroethane containing at least one compound selected from the group consisting of hydrofluorocarbons containing one carbon atom, hydrochlorofluorocarbons containing one carbon atom and hydrochlorocarbons containing one carbon atom, into contact with an adsorbent comprising a zeolite having an average pore size of 3 to 6 ? and a silica/aluminum ratio of 2.0 or less and/or a carbonaceous adsorbent having an average pore size of 3.5 to 6 ?, to reduce the content of the compound. The purified gas can be used as a low temperature refrigerant or an etching gas.
    Type: Grant
    Filed: June 30, 2003
    Date of Patent: August 1, 2006
    Assignee: Showa Denko K.K.
    Inventors: Hiromoto Ohno, Toshio Ohi
  • Patent number: 7071367
    Abstract: The present invention provides a process for the preparation of trifluoromethyl iodide. The process includes the step of: contacting in a reactor a compound represented by the formula: CF3—W and a compound represented by the formula: Z-I wherein W is selected from CF3, hydrogen and bromine; Z is selected from hydrogen, iodine and chlorine. The step of contacting is carried out, optionally in the presence of a catalyst and further optionally in the presence of air, at a temperature, pressure and for a length of time sufficient to produce the trifluoromethyl iodide.
    Type: Grant
    Filed: December 9, 2004
    Date of Patent: July 4, 2006
    Assignee: Honeywell International Inc.
    Inventors: Sudip Mukhopadhyay, Hsueh Sung Tung
  • Patent number: 7045668
    Abstract: A process for production of high-purity hexafluoroethane, wherein a mixed gas containing hexafluoroethane and chlorotrifluoromethane is reacted with hydrogen fluoride in a gas phase in the presence of a fluorination catalyst at 200-450° C., for fluorination of the chlorotrifluoromethane, or wherein pentafluoroethane containing chlorine compounds with 1-3 carbon atoms is reacted with hydrogen in a gas phase in the presence of a hydrogenation catalyst at 150-400° C., and the product is then reacted with fluorine in a gas phase in the presence of a diluent gas.
    Type: Grant
    Filed: August 6, 2002
    Date of Patent: May 16, 2006
    Assignee: Showa Denko K.K.
    Inventors: Hiromoto Ohno, Toshio Ohi
  • Patent number: 7009083
    Abstract: The invention relates to a process for the preparation of 1-chloro-1-fluoroethane and 1,1-difluoroethane by reaction of vinyl chloride with hydrogen fluoride, in an organic solvent consisting of at least one saturated halogen-containing hydrocarbon.
    Type: Grant
    Filed: August 2, 2004
    Date of Patent: March 7, 2006
    Assignee: Solvay (Societe Anonyme)
    Inventors: Pascal Pennetreau, Francine Janssens
  • Patent number: 6967260
    Abstract: Tetrafluoromethane containing ethylene compound, hydrocarbon compounds, carbon monoxide and/or carbon dioxide is contacted with zeolite having an average pore size of 3.4 to 11 ? and an Si/Al ratio of 1.5 or less and/or a carbonaceous adsorbent having an average pore size of 3.4 to 11 ?. Thus, high-purity tetrafluoromethane can be obtained which is advantageous in industry and provides good profitability.
    Type: Grant
    Filed: April 26, 2001
    Date of Patent: November 22, 2005
    Assignee: Showa Denko K.K.
    Inventors: Hiromoto Ohno, Toshio Ohi
  • Patent number: 6841705
    Abstract: A method of producing difluoromethane (HFC-32), which includes firstly reacting methylene chloride with hydrogen fluoride in gas phase at 280 to 340° C. in the presence of a fluorination catalyst to produce chlorofluoro methane, and secondly reacting the chlorofluoro methane with hydrogen fluoride in liquid phase at 60 to 80° C. in the presence of an antimony chloride catalyst. The method is advantageous in that HFC-32 is produced in high yield under mild reaction conditions using a relatively small amount of energy.
    Type: Grant
    Filed: February 24, 2003
    Date of Patent: January 11, 2005
    Assignee: Ulsan Chemical Co., Ltd.
    Inventors: Iikubo Yuichi, Hae Seok Ji, Ook Jae Cho
  • Patent number: 6806396
    Abstract: The present invention relates to the co-pyrolysis of fluoroform and chlorodifluoromethane to form a mixture of useful fluoroolefin and saturated HFCs, notably, tetrafluoroethylene and hexafluoropropylene and CF3CHF2 and CF3CHFCF3, respectively.
    Type: Grant
    Filed: December 16, 2002
    Date of Patent: October 19, 2004
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Peter Gideon Gelblum, Velliyur Nott Mallikarjuna Rao, Charles Joseph Noelke, Norman Herron
  • Patent number: 6759381
    Abstract: Provided are azeotropic and azeotrope-like mixtures of 1-chloro-1,3,3,3-tetrafluoropropane and 1,2-dichloro-3,3,3-trifluoropropene that are useful as an intermediate in the production of HFC-245fa. HFC-245fa is useful as a nontoxic, zero ozone depleting fluorocarbon useful as solvents, blowing agents, refrigerants, cleaning agents, aerosol propellants, heat transfer media, gaseous dielectrics, fire extinguishing compositions and power cycle working fluids.
    Type: Grant
    Filed: May 6, 2003
    Date of Patent: July 6, 2004
    Assignee: Honeywell International Inc.
    Inventors: Robert C. Johnson, Daniel C. Merkel, Hsuehsung Tung
  • Patent number: 6657094
    Abstract: There is provided a method of end-chlorination of a fluorine-containing compound which can easily provide a fluorine-containing monomer having a functional group such as nitrile group at relatively low cost. The method of chlorinating an end of a fluorine-containing compound having iodine atom at an end thereof comprises reacting a fluorine-containing organic compound having iodine atom at a molecular end thereof and represented by the formula (I): RfCX2I  (I) wherein Rf is an organic residue having fluorine atom, X is hydrogen atom or chlorine atom, with a chlorine gas at a temperature of from 150° C. to 180° C. under irradiation with light to cleave the C—I bond and replace iodine atom with chlorine atom.
    Type: Grant
    Filed: March 22, 2002
    Date of Patent: December 2, 2003
    Assignee: Daikin Industries, Ltd.
    Inventors: Masaki Irie, Kazuyoshi Kawasaki, Mitsuru Kishine
  • Patent number: 6555086
    Abstract: Processes for separating and recovering hydrogen fluoride from a gaseous mixture of an organic compound and hydrogen fluoride are disclosed. The processes include contacting the gaseous mixture with a solution of an alkali metal fluoride in hydrogen fluoride, separating a gas phase depleted in hydrogen fluoride and containing the organic compound from a liquid phase, and recovering hydrogen fluoride from the liquid phase.
    Type: Grant
    Filed: October 7, 1999
    Date of Patent: April 29, 2003
    Assignee: Ineos Fluor Holdings Limited
    Inventors: Paul Nicholas Ewing, Charles John Shields, Robert Elliott Low
  • Patent number: 6521199
    Abstract: Hydrogen fluoride adducts and ammonium fluorides are used for fluorinating acid chlorides and halocarbon compounds such as chloroalkanes or chloronated ethers. The used adducts can be regenerated and then reused in the fluorination reactions.
    Type: Grant
    Filed: March 4, 2002
    Date of Patent: February 18, 2003
    Assignee: Solvay Fluor und Derivate GmbH
    Inventors: Max Braun, Stefan Palsherm
  • Publication number: 20020087039
    Abstract: A method of producing hydrofluorocarbons and/or hydrochlorofluorocarbons by using halogenated alkanes as a principal reactant.
    Type: Application
    Filed: December 29, 2000
    Publication date: July 4, 2002
    Inventors: Hsueh Sung Tung, Michael Van Der Puy
  • Patent number: 6403524
    Abstract: A chromia-based fluorination catalyst in which the chromia is at least partially crystalline and which may contain a zinc or a compound thereof, the production of the catalyst by sintering amorphous chromia and its use in fluorination processes.
    Type: Grant
    Filed: March 8, 1999
    Date of Patent: June 11, 2002
    Assignee: Imperial Chemical Industries PLC
    Inventors: John David Scott, Michael John Watson, Graham Ramsbottom
  • Patent number: 6395700
    Abstract: Compounds each having a —CH2—CHF— group and a number of carbon atoms of 4 or above are prepared by hydrogenating a compound having a —CCl═CF— group and a number of carbon atoms of 4 or above in the presence of a noble metal catalyst in a liquid or gas phase. The compound having a —CCl═CF— group and a number of carbon atoms of 4 or above is preferably a C4-C10 alicyclic one, and can be prepared by reacting a compound having a —CCl═CCl— group and a number of carbon atoms of 4 or above with a fluorinating agent.
    Type: Grant
    Filed: June 23, 2000
    Date of Patent: May 28, 2002
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Toshiro Yamada, Takashi Uruma, Tatsuya Sugimoto
  • Patent number: 6362379
    Abstract: A method is provided for preparation of chlorofluoroethers ClCF2CFClOR8f and Cl2CFCFClOR8f by direct fluorination of Cl2CHCH2OR8 and Cl3CCH2OR8, respectively, wherein R8 is a C1-C20 alkyl-or acyl-containing group optionally up to 5 ether oxygen atoms and optionally substituted by functional groups and R81, is the corresponding perfluoroalkyl or perfluoracyl-containing group.
    Type: Grant
    Filed: May 1, 2001
    Date of Patent: March 26, 2002
    Assignee: 3M Innovative Properties Company
    Inventors: George G. I. Moore, Fred B. McCormick, Mita Chattoraj, Elisa M. Cross, Junkang Jacob Liu, Ralph R. Roberts, Jay F. Schulz
  • Publication number: 20020035301
    Abstract: A method for efficiently extracting a reaction product containing a target aromatic fluorine compound formed by the halogen exchange reaction of an aromatic chlorine compound with a fluorinating agent quickly from the reaction vessel without suffering part of the reaction product to remain as a residue inside the reaction vessel is disclosed. Specifically, the reaction product is extracted from the reactor subsequently to the halogen exchange reaction at a temperature in the range of 20-250° C. By this method, the reaction product formed in consequence of the halogen exchange reaction can be efficiently extracted quickly from the reaction vessel, and that without suffering occurrence of a residue of the reaction product.
    Type: Application
    Filed: August 29, 2001
    Publication date: March 21, 2002
    Inventor: Kouichi Hirota
  • Patent number: 6316682
    Abstract: A method of producing 1,1,1,3,3-pentafluoropropane wherein 1,1,1,3,3-pentafluoropropane is obtained by reacting at least one selected from the group consisting of fluorinated and chlorinated propane and chlorinated propane expressed by a general formula of CX3CH2CHX2 (where X in this general formula indicates either a fluorine atom or a chlorine atom, but all of X's can never represent fluorine atoms at the same time) with a fluorinated antimony chloride. There is provided an economical and efficient method of producing 1,1,1,3,3-pentafluoropropane with high yield, which is an alternative compound to CFC's and HCFC's and is important in industry as a blowing agent, a refrigerant, a detergent, and a propellant that does not destroy the ozone in the ozone layer.
    Type: Grant
    Filed: November 30, 1998
    Date of Patent: November 13, 2001
    Assignee: Daikin Industries, Ltd.
    Inventors: Tatsuo Nakada, Takashi Shibanuma, Yamamoto Akinori
  • Publication number: 20010034465
    Abstract: A process for producing a fluorinated organic compound comprising: (a) reacting an organic starting material with a fluorination agent in the presence of a liquid fluorination catalyst under conditions which are effective to vaporize one or more chlorinated organic by-products and to produce a gaseous product stream containing said fluorinated organic compound and said one or more chlorinated organic by-products; and (b) recovering said fluorinated organic compound from said product stream, and a system for performing the aforementioned process and recovering the chlorinated by-product.
    Type: Application
    Filed: March 6, 2001
    Publication date: October 25, 2001
    Inventors: Charles F. Swain, Stephen A. Cottrell, Clifford S. Riegel, Curtis A. Brescher
  • Patent number: 6297405
    Abstract: A process for the preparation of aromatic aldehydes containing fluorine, and more particularly, to a formylation process for fluorinated aromatic derivatives through the reaction of fluorinated benzenes with carbon monoxide and aluminum chloride at a relatively low pressure, a low temperature, and in the presence of at most a catalytic amount of an acid (such as aqueous hydrochloric acid) is herein disclosed. The resultant fluorinated benzaldehydes are useful as precursors to the formation of a number of different compounds, such as dyestuffs, flavorings, fragrances, herbicidal compounds, nucleating agents, polymer additives, and the like. The inventive method provides a very cost effective and safe procedure for producing such fluorinated benzaldehydes in very high yields. The particular novel multi-substituted benzaldehydes are also encompassed within this invention.
    Type: Grant
    Filed: September 1, 2000
    Date of Patent: October 2, 2001
    Assignee: Milliken & Company
    Inventors: John David O. Anderson, Walter Scrivens
  • Patent number: 6239319
    Abstract: The present invention provides a new industrial process for producing perfluoroalkanes in order to overcome the problems of processes for producing perfluoroalkanes in the prior art. The process of the present invention is a process for producing a perfluoroalkane corresponding to a general formula Rf-F (wherein Rf- is a perfluoroalkyl group represented by F(CF2)n— and n is an integer of 2 to 10) by contacting a perfluoroalkyl iodide with gaseous fluorine to cause a reaction therebetween, wherein the contact is made in the presence of the liquid compound which is at least one liquid which is substantially inert to the perfluoroalkyl iodide and gaseous fluorine under the condition of the process and which is selected from a perfluoro-compound, a chlorofluoro-compound, and hydrogen fluoride.
    Type: Grant
    Filed: August 23, 1999
    Date of Patent: May 29, 2001
    Assignee: Daikin Industries Ltd.
    Inventors: Tatsuya Otsuka, Tatsuya Hirata, Kyohiro Kan, Hirokazu Aoyama
  • Patent number: 6198011
    Abstract: A method of fluorinating an organic compound comprising reacting an organic compound with a fluorinating agent characterized in that a perfluorocarbon compound is present in the reaction medium. The perfluorocarbon compound may replace an amount of a solvent which would otherwise be required for the reaction to proceed efficiently. The perfluorocarbon compound is readily recoverable after reaction and may be re-used in subsequent reactions. Additives to the reaction medium, such as 18-crown-6, may increase the amoun of solvent which may be replaced. The method is beneficial where solvent consumption would otherwise be large, or where solvent recovery would otherwise be difficult.
    Type: Grant
    Filed: March 25, 1999
    Date of Patent: March 6, 2001
    Assignee: F2 Chemicals Ltd.
    Inventors: Richard D. Chambers, Andrew R. Edwards
  • Patent number: 6184425
    Abstract: The present invention relates to a process for preparing fluorine-containing compounds by reacting a compound which contains fluorine-exchangeable halogen with a fluoride or a mixture of fluorides with the formula I MeF  (I), in which Me is an alkaline earth metal ion, NH4+-ion or alkali metal ion, in the presence of a compound or a mixture of compounds of the formula (II) in which A1, A2, A3, A4, A5, A6, A7, A8 independently of one another are identical or different and are a straight-chain or branched alkyl or alkenyl having 1 to 12 carbon atoms, cycloalkyl having 4 to 8 carbon atoms, an aryl having 6 to 12 carbon atoms, or an aralkyl having 7 to 12 carbon atoms, or A1 A2, A3A4, A5A6, and A7A8 independently of one another are identical or different and are connected to one another directly or by way of O or N—A9 to form a ring having 3 to 7 ring members, A9 is an alkyl having 1 to 4 carbon atoms and B− is a monovalent acid radical or the equivalent of a polyval
    Type: Grant
    Filed: July 7, 1999
    Date of Patent: February 6, 2001
    Assignee: Aventis Research & Technologies GmbH & Co.
    Inventors: Alexander Kolomeitsev, Sergej Pasenok
  • Patent number: 6165931
    Abstract: A process is disclosed for increasing the fluorine content of a saturated or olefinic halogenated hydrocarbon starting material of the formula C.sub.n H.sub.a Cl.sub.b F.sub.c, wherein n is an integer from 1 to 6, a is an integer from 0 to to 12, b is an integer from 0 to 13 and c is an integer from 0 to 13. The process involves contacting the starting material in the vapor phase at a temperature in the range of about 150.degree. C. to about 500.degree. C. with HF and a catalytic metal supported on a trivalent lanthanum compound support (the catalytic metal being chromium, cobalt, nickel, zinc, magnesium, copper, silver and/or gold). Certain catalytic compositions including catalytic metal (e.g., chromium, nickel, cobalt, zinc and/or magnesium) supported on a support at trivalent lanthanum compound containing fluoride anion are also disclosed. The atomic ratio of catalytic metal to lanthanum in the compositions is from about 1:1 to 1:999.
    Type: Grant
    Filed: April 11, 1997
    Date of Patent: December 26, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: V. N. Mallikarjuna Rao
  • Patent number: 6114589
    Abstract: The invention relates to a process for the preparation of fluorinated compoundsAz.sub.x ArF.sub.w Cl.sub.(y-w) R.sub.z (1)in which Az is a radical --F, --Cl, --Br, --NO.sub.2, --CN, --CF.sub.3, --CCl.sub.3, --CHO, --CO(C.sub.n H.sub.2n+1), --COX or --SO.sub.2 X, where X is F, Cl or Br, x is an integer from 1 to 3, Ar is a phenyl radical, pyridyl radical or naphthyl, w is an integer from 1 to y, y is an integer from 1 to 5, R is H, an alkyl radical or an alkoxy radical having from 1 to 10 carbon atoms, z is an integer from 1 to 5, (x+y+z) is the number of all substitutable valences on the radical Ar, which comprises reacting a compoundAz.sub.x ArCl.sub.y R.sub.z (2),with an alkali metal fluoride in the presence of a component a) or a mixture of component a) and at least one of components b), c), d) and/or e), component a) being one or more quaternary ammonium compounds which contain one or more radicals --(C.sub.m H.sub.2m O)R.sup.
    Type: Grant
    Filed: October 13, 1998
    Date of Patent: September 5, 2000
    Assignee: Clariant GmbH
    Inventors: Thomas Schach, Thomas Wessel, Maren Gutermuth
  • Patent number: 6077819
    Abstract: A process is disclosed for recovering HF from a product mixture comprising HF and at least one compound having the formula CF.sub.3 CCl.sub.2+x F.sub.1-x (where x is 0 or 1). The process includes the steps of distilling the product mixture to remove all products which have a lower boiling point than the lowest boiling azeotrope containing HF and said at least one compound; and distilling said azeotrope to recover HF as an azeotropic composition containing HF and said at least one compound. Also disclosed are azeotrope and azeotrope-like compositions which consist essentially of hydrogen fluoride in combination with from about 10 to 27 mole percent CCl.sub.3 CF.sub.3 or from about 35 to 56 mole percent CCl.sub.2 FCF.sub.3.
    Type: Grant
    Filed: November 1, 1993
    Date of Patent: June 20, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Barry A. Mahler, Ralph N. Miller, V. N. Mallikarjuna Rao
  • Patent number: 6028026
    Abstract: This invention provides a crystalline chromium fluoride having a cubic crystal structure (i.e., chromium trifluoride having an X-ray diffraction powder pattern as shown in Table I); and a catalytic composition comprising cubic chromium trifluoride. This invention also provides a process for changing the fluorine content of halogenated hydrocarbons containing from one to six carbon atoms, in the presence of a chromium-containing catalyst. The process is characterized by the chromium-containing catalyst comprising cubic chromium trifluoride.
    Type: Grant
    Filed: August 20, 1998
    Date of Patent: February 22, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: V. N. Mallikarjuna Rao, Munirpallam A. Subramanian
  • Patent number: 5969198
    Abstract: A process for preparing 1,1,1,3,3-pentafluoropropane from a hydrochlorocarbon of the formula C.sub.3 H.sub.y Cl.sub.x, wherein x is an integer from 3 to 5, y is an integer from 1 to 3, x+y=4, 6, or 8, and x-y=2 is provided.
    Type: Grant
    Filed: June 27, 1997
    Date of Patent: October 19, 1999
    Assignee: AlliedSignal Inc.
    Inventors: Alagappan Thenappan, Michael Van Der Puy, Hsueh S. Tung
  • Patent number: 5919728
    Abstract: A fluorination catalyst based on of an amorphous Cr (III) compound and on a compound of another metal selected from Mg, Ca, Sr, Ba, Sc, Ti and Zr, wherein the atomic ratio of Cr/other metal is between 50:1 and 1:1, said compounds are supported on a AlF.sub.3 support and being prepared by impregnating the support with a concentrated aqueous solution containing a soluble Cr (III) salt and a soluble salt of the other metal. The catalyst can be used in gaseous phase reactions.
    Type: Grant
    Filed: April 15, 1997
    Date of Patent: July 6, 1999
    Assignee: Ausimont S.P.A.
    Inventors: Francesco Rinaldi, Paolo Cuzzato, Letanzio Bragante
  • Patent number: 5866730
    Abstract: A process is disclosed for enriching the amount of CFC-114 relative to the amount of CFC-114a from an initial mixture containing both isomers, by contacting said initial mixture with hydrogen chloride in the vapor phase at an elevated temperature in the presence of a catalyst to produce a product mixture containing C.sub.2 Cl.sub.2 F.sub.3 and chlorination products of CCl.sub.2 FCF.sub.3 wherein the weight ratio of CClF.sub.2 CClF.sub.2 to the total C.sub.2 Cl.sub.2 F.sub.4 is higher than the weight ratio of CClF.sub.2 CClF.sub.2 to the total C.sub.2 Cl.sub.2 F.sub.4 in the initial mixture. The chlorination products of CFC-114a (e.g., CCl.sub.3 CF.sub.3) in the product mixture may then be separated from the C.sub.2 Cl.sub.2 F.sub.4 therein (e.g., by distillation).
    Type: Grant
    Filed: April 2, 1993
    Date of Patent: February 2, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: V. N. Mallikarjuna Rao
  • Patent number: 5849963
    Abstract: According to the method for producing difluoromethane and 1,1,1,2-tetrafluoroethane, having the steps of:(1) reacting methylene chloride and 1,1,2-trichloroethylene with hydrogen fluoride in a vapor phase In the presence of a fluorinating catalyst and 1,1,1,2-tetrafluoroethane in a first reactor; and(2) reacting 1,1,1-trifluorochloroethane with hydrogen fluoride in a vapor phase in the presence of a fluorinating catalyst in a second reactor, and supplying the reaction mixture from the second reactor to the first reactor, HFC-32 can be obtained in high conversion and high selectivity by fluorinating HCC-30 using commonly a large (excess) amount of HF which is required for producing HFC-134a.
    Type: Grant
    Filed: June 7, 1996
    Date of Patent: December 15, 1998
    Assignee: Daikin Industries, Ltd.
    Inventors: Yukio Homoto, Kunitada Tanaka, Takashi Shibanuma, Satoshi Komatsu, Satoshi Koyama
  • Patent number: 5847242
    Abstract: A process is disclosed for changing the fluorine content of halogenated hydrocarbons containing from 1 to 6 carbon atoms, in the presence of a multiphase catalyst, which is characterized by preparing certain single phase solid catalyst precursors containing two metal components (e.g., a divalent component of Mn, Co, Zn, Mg and/or Cd and a trivalent component of Al, Ga, Cr and/or V) which have structures that collapse at about 600.degree. C. or less; and producing said catalyst by heating the precursor to produce a multiphase composition wherein a phase containing one of the metal components is homogeneously dispersed with a phase containing the other metal component, and at least when the precursor contains no fluoride, contacting said multiphase composition with a vaporizable fluorine-containing fluorination compound at a temperature of from about 200.degree. C. to 450.degree. C. Also disclosed are single phase fluoride compositions having the formula MM'F.sub.5 (H.sub.2 O).sub.
    Type: Grant
    Filed: November 21, 1996
    Date of Patent: December 8, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Velliyur Nott Mallikarjuna Rao, Munirpallam A. Subramanian
  • Patent number: 5841006
    Abstract: Process for preparing pentafluoroethane (125) containing amounts of 115 lower than 0.02% by weight wherein pentafluoroethane is obtained by a dismutation process of tetrafluorochloroethane CF.sub.3 CHClF (HCFC-124) in gaseous phase in the presence of a chrome oxide catalyst (CR.sub.2 O.sub.3) supported on a AlF.sub.3 support, wherein one operates at temperatures from 140.degree.-180.degree. C. for contact times comprised between 15-30 seconds, from >180.degree. C. to 240.degree. C. for contact times between 5 to 15 seconds, from >240.degree. C. to 260.degree. C. for contact times between 1 to 5 seconds, from >260.degree. to 300.degree. C. for contact times between 0.1 to 1 second.
    Type: Grant
    Filed: November 26, 1996
    Date of Patent: November 24, 1998
    Assignee: Ausimont S.p.A.
    Inventor: Paolo Cuzzato
  • Patent number: 5785822
    Abstract: The present invention provides a method for separating dichlorodifluoromethane from difluoromethane. More specifically, a process is provided for separating dichlorodifluoromethane and difluoromethane using azeotropic distillation.
    Type: Grant
    Filed: May 23, 1996
    Date of Patent: July 28, 1998
    Assignee: AlliedSignal Inc.
    Inventors: Gustavo Cerri, Kin Ching Kong, Charles Francis Swain, Rajat Subhra Basu
  • Patent number: 5763698
    Abstract: The fluorine content of an acyclic saturated compound of the formula C.sub.n F.sub.a X.sub.b H.sub.c (wherein each X is independently selected from the group consisting of Cl and Br, and wherein n is 1 to 6, a is 1 to 13, b is 0 to 12, c is 1 to 9, and a+b+c equals 2n+2) is reduced by reacting the acyclic saturated compound with HCl in the vapor phase at an elevated temperature in the presence of a catalyst, the mole ratio of HCl to the acyclic saturated compound being at least about 1:1.
    Type: Grant
    Filed: November 3, 1995
    Date of Patent: June 9, 1998
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Leo Ernest Manzer, V. N. Mallikarjuna Rao, Steven Henry Swearingen
  • Patent number: 5734073
    Abstract: A method of halogenating an aromatic compound which comprises the steps of reacting an halogenating agent with the aromatic compound in the presence of fluorine and an acid, wherein the halogenating agent is at least one of an iodinating agent, a brominating agent and an chlorinating agent.
    Type: Grant
    Filed: April 18, 1996
    Date of Patent: March 31, 1998
    Assignee: BNFL Fluorochemicals Ltd
    Inventors: Richard Dickinson Chambers, Christopher John Skinner, Malcolm John Atherton, John Stewart Moilliet
  • Patent number: 5714655
    Abstract: 2,2,3-trichloro-1,1,1,3,3-pentafluoropropane is used as a raw material, to which not less than 4.5 equivalent parts of hydrogen are added to effect a hydrogenation reaction in the presence of a noble metal catalyst, particularly a palladium catalyst, by the vapor phase method to manufacture 1,1,1,3,3-pentafluoropropane. Further, propane, propene, and hexachloropropene, etc. are chlorofluorinated in the presence of a metal catalyst to produce 2,2,3-trichloro-1,1,1,3,3-pentafluoropropane, then this compound is reduced with hydrogen in the presence of a noble metal catalyst to produce 1,1,1,3,3-pentafluoropropane. 2,2,3-trichloro-1,1,1,3,3-pentafluoropropane and 1,1,1,3,3-pentafluoropropane can thus be efficiently and economically produced.
    Type: Grant
    Filed: December 8, 1995
    Date of Patent: February 3, 1998
    Assignee: Daikin Industries, Ltd.
    Inventors: Akinori Yamamoto, Eiji Seki, Hirokazu Aoyama, Seiji Takubo, Tatsuo Nakada
  • Patent number: 5714654
    Abstract: A method is proposed for producing 1,1,1,3,3-pentafluoropropane, in which 1,1,3,3,3-pentafluoropropene is reduced at a temperature between 40.degree. C. and 300.degree. C. by reacting it with hydrogen in a gas phase in the presence of a palladium catalyst. Further, a method is proposed for producing 1,1,1,3,3-pentafluoropropane and/or 1,1,3,3,3-pentafluoropropene, in which the raw material 2-chloro-1,1,3,3,3-pentafluoropropene is hydrogenated especially at a temperature between 30.degree. C. and 450.degree. C. in the presence of a catalyst composed of at least one metal selected from palladium, platinum and rhodium. Further, a method is proposed of producing 1,1,3,3,3-pentafluoropropene, in which 1,1,1,3,3-pentafluoro-2,3-dichloropropane is dechlorinated by using hydrogen in the presence of a metal oxide catalyst. Based on these production methods, 1,1,1,3,3-pentafluoropropane and/or 1,1,3,3,3-pentafluoropropene can thus be produced with high yield rates.
    Type: Grant
    Filed: December 8, 1995
    Date of Patent: February 3, 1998
    Assignee: Daikin Industries Ltd.
    Inventors: Akinori Yamamoto, Eiji Seki, Hirokazu Aoyama, Tatsuo Nakada
  • Patent number: 5688379
    Abstract: The present invention provides a process for preparing a perfluoroalkyl bromide characterized by reacting a perfluoroalkyl iodide represented by the formula C.sub.n F.sub.2n+1 I wherein n is an integer of 6 to 10 with bromine in a light-transmitting reactor with exposure to light and heating at 120.degree. to 180.degree. C. while simultaneously removing IBr resulting as a by-product by separation of a layer.
    Type: Grant
    Filed: October 24, 1995
    Date of Patent: November 18, 1997
    Assignee: Daikin Industries, Ltd.
    Inventors: Yasuhisa Furutaka, Tatsuo Nakada, Kazuhiro Shimokawa, Yorisato Hisanaga, Souichi Ueda