Transition Metal Halide Containing Catalyst Patents (Class 570/168)
  • Patent number: 5750809
    Abstract: A production method in which reaction processes are divided into two regions comprising one reaction region where mainly perchloroethylene is made to react with HF in a vapor phase in the presence of a catalyst and the other reaction region where HCFC-123 (CF.sub.3 CHCl.sub.2) and/or HCFC-124 (CF.sub.3 CFHCl) is made to react with HF in a vapor phase in the presence of a catalyst, the former region being kept at a higher pressure and the latter region at a lower pressure during the reaction procedure. By this method it is possible to keep the conversion of perchloroethylene at a high level while securing the life of a catalyst, and it is also possible to raise the selectivity of HFC-125. This is a method of producing HFC-125 in which the content of CFC-115 is lowered to not more than 15 vol % of the total amount of HFC-125 and CFC-115, and then CFC-115 is made to react with hydrogen in the presence of a catalyst.
    Type: Grant
    Filed: September 5, 1995
    Date of Patent: May 12, 1998
    Assignee: Daikin Industries Ltd.
    Inventors: Takashi Shibanuma, Yukio Homoto, Satoshi Komatsu, Toshikazu Yoshimura
  • Patent number: 5744660
    Abstract: This invention relates to a process for the production of 1,1,2,2- and/or 1,1,1,2-tetrafluoroethanes, and in particular to a process for the production of 1,1,1,2-tetrafluoroethane.
    Type: Grant
    Filed: December 21, 1995
    Date of Patent: April 28, 1998
    Assignee: Imperial Chemical Industries PLC
    Inventors: Lisa Bradley, Leslie Burgess, Richard Llewellwyn Powell, Geoffrey James Moore, Paul Nicholas Ewing, Kenneth Taylor
  • Patent number: 5744658
    Abstract: A method of producing 1,1,1,2-tetrafluoroethane in two separation reaction zones involving (1) reaction of trichloroethylene and hydrogen fluoride to produce l,l,l-trifluoro-2-chloroethane and (2) reaction of the 1,1,1-trifluoro-2-chloroethane and hydrogen fluoride to produce 1,1,1,2-tetrafluoroethane wherein both reactions are carried out at superatmospheric pressure, reaction (2) is carried out at a temperature in the range of 250.degree.-450.degree. C., reaction (1) is carried out at a temperature in the range of 200.degree.-400.degree. C. but below that used in reaction (2) and unconverted 1,1,1-trifluoro-2-chloroethane is recycled for further reaction with hydrogen fluoride.
    Type: Grant
    Filed: July 18, 1996
    Date of Patent: April 28, 1998
    Assignee: Imperial Chemical Industries PLC
    Inventors: John David Scott, Rachel Anne Steven
  • Patent number: 5739406
    Abstract: Process for the hydrofluorination of chloro(fluoro)butane of general formula C.sub.4 H.sub.5 Cl.sub.x F.sub.5-x in which x=1 to 5, by means of hydrogen fluoride and in the presence of a catalyst chosen from the derivatives of metals of groups IIIa, IVa, IVb, Va, Vb and VIb of the Periodic Table of the elements.
    Type: Grant
    Filed: August 30, 1995
    Date of Patent: April 14, 1998
    Assignee: Solvay (Societe Anonyme)
    Inventors: Pascal Pennetreau, Francine Janssens
  • Patent number: 5731481
    Abstract: The invention relates to the manufacture of 1,1,1,2-tetrafluoroethane (F134a) by gas-phase catalytic fluorination of 1-chloro-2,2,2-trifluoroethane (F133a).A mixed catalyst is employed, composed of nickel and chromium oxides, halides and/or oxyhalides deposited on a support consisting of aluminium fluoride or of a mixture of aluminium fluoride and alumina.This mixed catalyst makes it possible to obtain an excellent selectivity for F134a with a high production efficiency.
    Type: Grant
    Filed: December 24, 1996
    Date of Patent: March 24, 1998
    Assignee: Societe Atochem
    Inventors: Bernard Cheminal, Eric Lacroix, Andre Lantz
  • Patent number: 5728904
    Abstract: This invention is related to the preparation of hydrofluorocarbons (HFCs). Specifically, it relates to the manufacture of 1,1,1,3,3-pentafluoropropane, CF.sub.3 CH.sub.2 CF.sub.2 H (HFC-245fa) by the steps comprising (1) the formation of CCl.sub.3 CH.sub.2 CCl.sub.3 by the reaction of CCl.sub.4 with vinylidene chloride; (2) the conversion of CCl.sub.3 CH.sub.2 CCl.sub.3 to CF.sub.3 CH.sub.2 CF.sub.2 Cl by reaction with HF in the presence of a fluorination catalyst, selected from TiCl.sub.4, SnCl.sub.4 or mixtures thereof; and (3) reduction of CF.sub.3 CH.sub.2 CF.sub.2 Cl to CF.sub.3l CH.sub.2 CF.sub.2 H.
    Type: Grant
    Filed: July 15, 1996
    Date of Patent: March 17, 1998
    Assignee: AlliedSignal Inc.
    Inventors: Michael Van Der Puy, Richard E. Eibeck, Lois A. S. Ellis, G. V. Bindu Madhavan
  • Patent number: 5723700
    Abstract: There is a method for concurrently producing 1,1,1,2-tetrafluoroethane and pentafluoroethane, which comprises (A) reacting 1,1,1-trifluoro-2-chloroethane, hydrogen fluoride and chlorine in a first reactor in the presence of flurorination catalyst at a temperature in the range of from 300.degree. C. to 450.degree. C.; (B) transfering the products of step (A) together with trichloroethylene to a second reactor and reacting them at a temperature in the range of from 200.degree. C. to 400.degree. C.; (C) separating 1,1,1,2-tetrafluoroethane and pentafluoroethane from the resultant products; and (D) feeding the remaining products from step (C) back to the first reactor, wherein the molar ratio of chlorine/1,1,1-trifluoro-2-chloroethanethe in step (A) is in the range of from 0.001 to 0.
    Type: Grant
    Filed: September 5, 1996
    Date of Patent: March 3, 1998
    Assignee: Korea Institute of Science and Technology
    Inventors: Byung Gwon Lee, Hoon Sik Kim, Honggon Kim, Sang Deuk Lee, Moon Jo Chung
  • Patent number: 5714651
    Abstract: A method for extending the life of catalyst used to fluorinate olefins, e.g. a supported Lewis acid catalyst in the catalytic hydrofluorination of vinylidene chloride by conducting the hydrofluorination in the presence of a polymerization inhibitor for the vinylidene chloride.
    Type: Grant
    Filed: December 28, 1995
    Date of Patent: February 3, 1998
    Assignee: Elf Atochem North America, Inc.
    Inventors: Maher Yousef Elsheikh, Michael Sheppard Bolmer
  • Patent number: 5714653
    Abstract: Difluoromethane is produced by reaction, in the liquid phase, between dichloromethane and hydrogen fluoride, in the presence of a titanium or tin halide.
    Type: Grant
    Filed: March 18, 1996
    Date of Patent: February 3, 1998
    Assignee: Solvay
    Inventors: Vincent Wilmet, Francine Janssens
  • Patent number: 5714650
    Abstract: A process is disclosed for producing 1,1-difluoroethane (HFC-152a) in a liquid phase by contacting chloroethene and hydrogen fluoride in the presence of a tin tetrahalide catalyst. The ability to reduce tar formation and increase volumetric productivity is also disclosed.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: February 3, 1998
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Klaus Guenter Wuttke
  • Patent number: 5710352
    Abstract: A method for the preparation of 1,1,1,3,3-pentafluoropropane (HFC-245fa) and 1-chloro-3,3,3-trifluoropropene (HCFC-1233). 1,1,1,3,3-pentachloropropane (HCC-240fa) is fluorinated with HF in a vapor phase in the presence of a vapor phase catalyst. The HCFC-1233 and any co-produced 1,3,3,3-tetrafluoropropene (HFC-1234) are recycled for further fluorination by HF for a greater than 99% HCC-240fa conversion.
    Type: Grant
    Filed: September 19, 1996
    Date of Patent: January 20, 1998
    Assignee: AlliedSignal Inc.
    Inventor: Hsueh Sung Tung
  • Patent number: 5710353
    Abstract: An object is to effectively preparing a fluorinated compound by developing a catalyst which is effective in the fluorination of a halogenated alkane or alkene with hydrogen fluoride by a gas phase fluorination or addition of hydrogen fluoride. To this end, a catalyst which comprises a least one element selected from the group consisting of Ti, V, Zr, Mo, Ge, Sn and Pb, and alumina, aluminum fluoride or partially fluorinated alumina is used. This catalyst is prepared by an impregnation method to support the above element on alumina and the like, or a precipitation method in which the catalyst is co-precipitated from a solution containing an aluminum compound and a compound of the above element.
    Type: Grant
    Filed: June 15, 1995
    Date of Patent: January 20, 1998
    Assignee: Daikin Industries, Ltd.
    Inventors: Takashi Shibanuma, Yasufu Yamada, Toshikazu Yoshimura, Hiroshi Momota
  • Patent number: 5705717
    Abstract: Fluorination processes using hydrogen fluoride-containing fluorinating agents that are safely and easily handled, transported, and stored and that also exhibit good reactivity are provided. More particularly, the invention provides processes for producing fluorinated products using fluorinating agents comprising hydrogen fluoride and a carrier that may be an acid salt or a water-soluble polymer.
    Type: Grant
    Filed: March 7, 1996
    Date of Patent: January 6, 1998
    Assignee: AlliedSignal Inc.
    Inventors: Michael Van Der Puy, Jeffrey Warren Mckown, Hang Thanh Pham, Andrew Joseph Poss, Rajiv Ratna Singh
  • Patent number: 5672785
    Abstract: A process for producing 1,1-dichloro-1,2,2,2-tetrafluoroethane, which comprises isomerizing 1,1,2-trichloro-1,2,2-trifluoroethane to form 1,1,1-trichloro-2,2,2-trifluoroethane, followed by fluorination with hydrofluoric acid.
    Type: Grant
    Filed: February 17, 1995
    Date of Patent: September 30, 1997
    Assignee: Asahi Glass Company Ltd.
    Inventors: Shinsuke Morikawa, Shunichi Samejima, Masaru Yoshitake, Shin Tatematsu
  • Patent number: 5672789
    Abstract: A catalyst for fluorination of 1,1-dichloro-1-fluoroethane which is obtained by mixing chromic hydroxide and an aqueous solution of magnesium chloride, reacting the mixture with an aqueous solution of HF and then calcining the resulting product and a process for preparing 1,1,1,-trifluoroethane by reacting 1,1-dichloro-1-fluoroethane with HF in the presence of the above catalyst are provided.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: September 30, 1997
    Assignee: Korea Institute of Science and Technology
    Inventors: Hoon Sik Kim, Byung Gwon Lee, Honggon Kim, Hyunjoo Lee
  • Patent number: 5672786
    Abstract: A process for the production of difluoromethane comprising (a) contacting dichloromethane with hydrogen fluoride in the presence of a fluorination catalyst to produce a product stream comprising difluoromethane, monochloromonofluoromethane and unreacted starting materials and (b) separating difluoromethane from the product stream from step (a), wherein sufficient hydrogen fluoride is employed in the process such that during step (b) the molar ratio of hydrogen fluoride to monochloromonofluoromethane is at least about 100:1.
    Type: Grant
    Filed: September 6, 1995
    Date of Patent: September 30, 1997
    Assignee: Imperial Chemical Industries PLC
    Inventors: David William Bonniface, John David Scott, Michael John Watson
  • Patent number: 5672788
    Abstract: A process is disclosed for producing 1,1-difluoroethane (CH.sub.3 CHF.sub.2 or HFC-152a) in a two-step reaction in a manner that reduces formation of high boiling materials. The first step comprises adding at least one of HCl or HF to chloroethene (CH.sub.2 .dbd.CHCl) in order to obtain at least one of 1,1-dichloroethane (CH.sub.3 CHF.sub.2) or 1-chloro-1-fluoroethane (CH.sub.3 CHClF). The second step comprises converting 1,1-dichloroethane or 1-chloro-1-fluoroethane to 1,1-difluoroethane.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: September 30, 1997
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Mario Joseph Nappa, Klaus Guenter Wuttke
  • Patent number: 5659094
    Abstract: A process for co-production of 1,1,1,2-tetrafluoroethane (HFC-134a;CF.sub.3 CH.sub.2 F), pentafluoroethane (HFC-125; CF.sub.3 CHF.sub.2) and 1,1,1 -trifluoroethane (HFC-143a; CF.sub.3 CH.sub.3) by a two-step gaseous reaction comprising the steps of a) reacting 1,1,1-trifluoro-2-chloroethane (CFCH.sub.2 Cl, HCFC-133a) with HF in a first reactor to prepare 1,1,1,2-tetrafluoroethane (HFC-134a; CF.sub.3 CH.sub.2 F), pentafluoroethane (HFC-125; CF.sub.3 CHF.sub.2) and 1,1,1-trifluoroethane (HFC-143a; CF.sub.3 CH.sub.3); b) adding trichloroethylene (TCE:CCl.sub.2 CHCl) to the reaction product of step a) in a second reactor to prepare HCFC-133a; separating HCl, HFC-134a, HFC-125 and HFC-143a from the reaction product of step b) and recycling HCFC-133a to the first reactor, and the stages being performed in the presence of fluorization catalyst obtained by calcining a reaction product which is obtained by reacting ethanol with a mixture of calcium fluoride(CaF.sub.
    Type: Grant
    Filed: January 25, 1996
    Date of Patent: August 19, 1997
    Assignee: Korea Institute of Science and Technology
    Inventors: Hoon Sik Kim, Byung Gwon Lee, Honggon Kim, Moon Jo Chung
  • Patent number: 5654494
    Abstract: This invention relates to a process for producing 1,1,1,2-tetrafluoroethane (HFC-134a). The process reacts, 1,1,1-trifluoro-2-chloroethane (HCFC-133a) and hydrogen fluoride in a first reactor. The product resulting from the first reaction step is brought to a second reactor together with trichloroethylene and hydrogen fluoride. The second reaction is conducted at a higher temperature than the first reactor. Optionally, HCl is removed prior to removal of the crude HFC-134a product. Unreacted HCFC-133a, trichloroethylene and hydrogen fluoride may be recycled back to the first reactor.
    Type: Grant
    Filed: August 18, 1995
    Date of Patent: August 5, 1997
    Assignee: AlliedSignal Inc.
    Inventors: Hsueh Sung Tung, Paul Gene Clemmer, Gustavo Cerri, Yuon Chiu, Stanley Michael Jaskot, Nemesio Rogelio Viso, Addison Miles Smith, Jeffrey Warren McKown, Jay Philip Friedenson
  • Patent number: 5639924
    Abstract: Process for synthesizing 1,1,1-trifluoroethane (143a) in the gaseous phase by reacting 1,1-defluoro-1-chloroethane in gaseous phase in the presence of a Cr catalyst. The process may be run isothermally or adiabatically, without co-feeding air or other oxygen containing gas, in the presence or absence of a Ni, Co, Zn or Mn cocatalyst for the Cr catalyst. The catalyst may be unsupported or supported with a support preferably selected from activated carbon, alumina and fluorided alumina. The formation of olefin byproduct can be kept to less than 10 ppm in accordance with the process of the invention.
    Type: Grant
    Filed: November 29, 1994
    Date of Patent: June 17, 1997
    Assignee: Elf Atochem North America, Inc.
    Inventors: Maher Yousef Elsheikh, Michael Sheppard Bolmer, Jean Pierre Schirmann, John Aloysius Wismer, Wayne E. Brooks
  • Patent number: 5629461
    Abstract: There is provided a method of producing 1,1,2,2,3-pentafluoropropane by reacting 1-chloro-2,2,3,3-tetrafluoropropane with hydrogen fluoride in the presence of fluorinated catalyst. By this method, 1,1,2,2,3-pentafluoropropane can be obtained industrially and economically at high yield.
    Type: Grant
    Filed: June 27, 1995
    Date of Patent: May 13, 1997
    Assignee: Daikin Industries, Ltd.
    Inventors: Takashi Yasuhara, Akinori Yamamoto, Hirokazu Aoyama, Eiji Seki
  • Patent number: 5623092
    Abstract: A chromium-containing fluorination catalyst which comprises an activity-promoting amount of zinc or a compound of zinc, a process for increasing the activity of a chromium-containing fluorination catalyst by introducing an activity promoting amount of zinc or a compound of zinc to the catalyst and a process for the production of fluorinated hydrocarbons, in particular 1,1,1,2-tetrafluoroethane which comprises reacting a hydrocarbon or a halogenated hydrocarbon, in particular 1-chloro-2,2,2-trifluoroethane with hydrogen fluoride in the vapour phase in the presence of the zinc-promoted chromium-containing catalyst.
    Type: Grant
    Filed: January 25, 1995
    Date of Patent: April 22, 1997
    Assignee: Imperial Chemical Industries PLC
    Inventors: John D. Scott, Michael J. Watson
  • Patent number: 5616820
    Abstract: The invention relates to a process for the manufacture of 1,1,1,2-tetrafluoro-2-chloroethane and of pentafluoroethane.The process, which consists of the gas phase catalytic fluorination of at least one pentahaloethane of formula C.sub.2 HX.sub.2-n F.sub.3+n in which X denotes a chlorine or bromine atom and n the number 0 or 1 by means of hydrofluoric acid, is characterized in that there is used a mixed catalyst composed of oxides, halides and/or oxyhalides of nickel and chromium deposited on a support consisting of aluminium fluoride or a mixture of aluminium fluoride and alumina.
    Type: Grant
    Filed: June 28, 1995
    Date of Patent: April 1, 1997
    Assignee: Elf Atochem S.A.
    Inventors: Bernard Cheminal, Eric Lacroix, Andr e Lantz
  • Patent number: 5616819
    Abstract: A process is disclosed for the preparation of a fluorinated aliphatic olefin having the formulaCH.sub.a F.sub.3-a --CH.sub.2 --CH.sub.b F.sub.3-bwherein a is 0 or the integer 1 or 2 and b is 0 or the integer 1, 2 or 3.In the first step of the process, a chlorinated olefinic hydrocarbon of the formulaCH.sub.c Cl.sub.2-c .dbd.CH--CH.sub.d Cl.sub.3-dwherein c is 0 or the integer 1 and d is 0 or the integer 1 or 2 is reacted with anhydrous hydrogen fluoride for a period of time and at a temperature sufficient to form a chlorofluoro olefin of the formulaCH.sub.e Cl.sub.2-e .dbd.CH--CH.sub.f F.sub.3-fwherein e is 0 or the integer 1 and f is 0 or the integer 1 or 2.The chlorofluoro olefin produced in the first step is then reacted with anhydrous hydrogen fluoride in a second reaction. This second reaction is catalyzed with at least one compound that is a metal oxide or metal halide. Mixtures of said metal oxides, metal halides and metal oxides with metal halides may also be used.
    Type: Grant
    Filed: August 28, 1995
    Date of Patent: April 1, 1997
    Assignee: LaRoche Industries Inc.
    Inventors: C. Bradford Boyce, Randolph K. Belter
  • Patent number: 5608126
    Abstract: A process for preparing 1,1,1,3,3-pentafluoropropane, which comprises reacting 1,1-difluoroethylene with dichlorofluoromethane in the presence of a Lewis acid catalyst to form 1,2,2-trihydrodichlorotrifluoropropane and fluorinating the 1,2,2-trihydrodichlorotrifluoropropane with hydrogen fluoride.
    Type: Grant
    Filed: June 23, 1995
    Date of Patent: March 4, 1997
    Assignee: AG Technology Co., Ltd.
    Inventors: Shinsuke Morikawa, Hidekazu Okamoto, Keiichi Ohnishi, Shin Tatematsu
  • Patent number: 5600038
    Abstract: Process for adiabatically hydrofluorinating hydrochlorocarbons and hydrochlorofluorocarbons in the gaseous phase in the presence of a catalyst that is active at the initial reaction temperature and remains highly selective at the maximum reaction temperature, e.g., a Cr catalyst. The molar ratio of HF to starting compound is at least about 2.5:1. The initial reaction temperature is selected such that the HF in the feed is partially associated but not completely (HF).sub.6. The catalyst may be unsupported or supported.
    Type: Grant
    Filed: March 24, 1995
    Date of Patent: February 4, 1997
    Assignee: Elf Atochem North America, Inc.
    Inventors: John A. Wismer, Maher Y. Elsheikh, Michael S. Bolmer, Jean P. Schirmann
  • Patent number: 5600039
    Abstract: The subject of the invention is a continuous process for the preparation of 1,1,1,2-tetrafluoroethane (134a) from 2-chloro-1,1,1-trifluoroethane (133a) and hydrofluoric acid in the gaseous phase in the presence of a chromium-based catalysts.According to the invention, the flow of gas leaving the reactor is subjected to a distillation in order to separate at the top a flow containing almost all the HC1 and at least 90% of the 134a produced by the reaction and at the bottom a flow containing at least 90% of the unconverted reactants (133a and HF), and the latter flow is recycled directly to the reactor, without any purifying operation.
    Type: Grant
    Filed: December 23, 1994
    Date of Patent: February 4, 1997
    Assignee: d'Elf Atochem S.A.
    Inventors: Jean-Michel Galland, Emmanuel Guiraud, Jean-Pierre Schirmann
  • Patent number: 5574191
    Abstract: 1,1,1-Trifluoroethane is produced, in addition to 1,1,-dichloro-1-fluoroethane and/or 1-chloro-1,1-difluoroethane, by hydrofluorination in the liquid phase, using hydrogen fluoride, vinylidene fluoride and at least one chloro compound chosen from vinylidene chloride and 1,1,1-trichloroethane.
    Type: Grant
    Filed: September 25, 1995
    Date of Patent: November 12, 1996
    Assignee: Solvay (Soci et e Anonyme)
    Inventors: Dominique Balthasart, Pascal Pennetreau
  • Patent number: 5574192
    Abstract: This invention is related to the preparation of hydrofluorocarbons (HFCs). Specifically, it relates to the fluorination of a compound of the formula:CF.sub.y Cl.sub.3-y CH.sub.2 CHF.sub.w Cl.sub.2-wwherein w=0 or 1, and y=0-3, with hydrogen fluoride in the presence of a fluorination catalyst under conditions sufficient to produce a compound of the formula CF.sub.3 CH.sub.2 CF.sub.2 H.CF.sub.3 CH.sub.2 CF.sub.2 H or HFC 245fa may be used as a blowing agent, a propellant, and a heat transfer agent.
    Type: Grant
    Filed: August 25, 1995
    Date of Patent: November 12, 1996
    Assignee: AlliedSignal Inc.
    Inventors: Michael VanDerPuy, Alagappan Thenappan
  • Patent number: 5569795
    Abstract: A fluorination catalyst comprising indium, chromium, oxygen and fluorine as essential constituent elements thereof. The catalyst is prepared by fluorinating a catalyst precursor comprising indium and chromium elements by bringing it into contact with hydrogen fluoride or a fluorine-containing halogenated hydrocarbon at a temperature of 300.degree. to 500.degree. C. A halogenated hydrocarbon is fluorinated by bringing it into contact with hydrogen fluoride in a gaseous phase in the presence of the catalyst.
    Type: Grant
    Filed: November 7, 1995
    Date of Patent: October 29, 1996
    Assignee: Showa Denko K. K.
    Inventors: Katsuyuki Tsuji, Kimitaka Oshiro, Tetsuo Nakajo
  • Patent number: 5569794
    Abstract: An improved process for producing hydrofluorocarbons and hydrochlorofluorocarbons by reacting anhydrous hydrogen fluoride in the vapor phase and in the presence of a fluorination catalyst with an admixture of perchloroethylene and a phenolic inhibitor. The phenolic component is effective to inhibit the formation of an oxidation product in the perchloroethylene while not substantially degrading the fluorination catalyst during the fluorination process. In another embodiment, substantially all of any oxidation inhibitor is removed from the perchloroethylene in-line prior to reacting the hydrogen fluoride with the perchloroethylene.
    Type: Grant
    Filed: August 30, 1995
    Date of Patent: October 29, 1996
    Assignee: AlliedSignal Inc.
    Inventor: Hsueh S. Tung
  • Patent number: 5569793
    Abstract: The invention relates to continuous production of 1,1,1-chlorodifluoroethane from 1,1,1-trichloroethane and hydrofluoric acid by reaction in liquid phase in the presence of at least one fluorination catalyst. According to the invention, the process is carried out under an absolute pressure of between 6 and 30 bars and at a temperature of between 50.degree. and 120.degree. C., the content of catalyst(s) in the reaction mixture, expressed as a percentage by weight of metal, being between 0.05 and 10% and the content of organohalogenated by-products not belonging to series 140 in the reaction mixture being controlled at a value below 40% by weight. This process makes it possible, at the same time, to obtain a high degree of conversion of hydrofluoric acid, to minimize the coproduction of 1,1,1-trifluoroethane and organohalogenated by-products and to facilitate the recovery of the hydrochloric acid formed.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: October 29, 1996
    Assignee: Societe Atochem
    Inventors: Michel Bergougnan, Jean-Michel Galland, Sylvain Perdrieux
  • Patent number: 5565393
    Abstract: Process is disclosed for preparing a highly fluorinated alkane by contacting halogenated alkenes or alkanes with hydrogen fluoride in the presence of a catalyst which produces a super acid environment. Also, performing the fluorination process by using equipment having a corrosion resistant surface. The corrosion resistant surface may be provided by explosively cladding a corrosion resistant material onto a base metal.
    Type: Grant
    Filed: September 26, 1994
    Date of Patent: October 15, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Vinci M. Felix, Richard E. Fernandez, Charles C. Seastrom
  • Patent number: 5563304
    Abstract: CF.sub.3 CHFCHF.sub.2 production is disclosed which involves reacting CF.sub.3 CF.dbd.CHF with HF at an elevated temperature over a catalyst selected from the group consisting of aluminum fluoride, fluorided alumina, metals supported on aluminum fluoride, metals supported on fluorided alumina and catalysts comprising trivalent chromium. Also disclosed is enrichment of CF.sub.3 CF.dbd.CHF from a starting mixture containing CF.sub.3 CF.dbd.CHF and CF.sub.3 CH.dbd.CF.sub.2 which involves reacting said starting mixture with HF at an elevated temperature over a catalyst consisting essentially carbon, a catalyst consisting essentially of metal halides supported on carbon, a catalyst consisting essentially of Cr.sub.2 O.sub.3, or mixtures thereof (provided that when Cr.sub.2 O.sub.3 is present the temperature is about 250.degree. C. or less) to produce a product mixture containing CF.sub.3 CH.sub.2 CF.sub.3 and unreacted CF.sub.3 CF.dbd.CHF wherein the mole ratio of CF.sub.3 CF.dbd.CHF to CF.sub.3 CH.dbd.CF.sub.
    Type: Grant
    Filed: May 26, 1994
    Date of Patent: October 8, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: V. N. Mallikarjuna Rao, Francis J. Walczak
  • Patent number: 5559276
    Abstract: A method of producing 1,1,1,2-tetrafluoroethane in two separation reaction zones involving (1) reaction of trichloroethylene and hydrogen fluoride to produce 1,1,1-trifluoro-2-chloroethane and (2) reaction of the 1,1,1- trifluoro-2-chloroethane and hydrogen fluoride to produce 1,1,1,2-tetrafluoroethane wherein both reactions are carried out at superatmospheric pressure, reaction (2) is carried out at a temperature in the range of 250.degree.-450.degree. C., reaction (1) is carried out at a temperature in the range of 200.degree.-400.degree. C. but below that used in reaction (2) and unconverted 1,1,1-trifluoro-2-chloroethane is recycled for further reaction with hydrogen fluoride.
    Type: Grant
    Filed: September 15, 1994
    Date of Patent: September 24, 1996
    Assignee: Imperial Chemical Industries PLC
    Inventors: John D. Scott, Rachel A. Steven
  • Patent number: 5545775
    Abstract: 1,1-difluoroethane is produced by the reaction of 1,2-dichloroethane with anhydrous hydrogen fluoride in a liquid phase and in the presence of a Lewis acid. Preferably the Lewis acid is tin, antimony, titanium, molybdenum, tungsten, niobium or tantalum halide or a mixture thereof.
    Type: Grant
    Filed: August 25, 1995
    Date of Patent: August 13, 1996
    Assignee: AlliedSignal Inc.
    Inventors: Alagappan Thenappan, Charles F. Swain, Matthew H. Luly
  • Patent number: 5545773
    Abstract: In an improved process and plant for carrying out liquid phase fluorination in the presence of a catalyst, consisting in reacting hydrofluoric acid and an organic starting material in a reaction zone, and in separating, in a separating zone, reactional mixture and at least one light fraction containing the desired fluorinated organic products and at least a first part of the sub-fluorinated organic products formed, and a heavy fraction that includes the remainder of the sub-fluorinated organic products formed, and further comprising partial condensation of the said light fraction in order to obtain a gaseous phase containing the desired fluorinated organic products and a liquid phase containing said first part of the said sub-fluorinated organic products, said heavy fraction being returned to said reaction zone and said liquid phase being returned as a reflux to the top of the separation zone, intermediate recovery is carried out at, or in the proximity of, the lower portion of said separation zone.
    Type: Grant
    Filed: July 25, 1994
    Date of Patent: August 13, 1996
    Assignee: Elf Atochem S.A.
    Inventor: Bernard Berthe
  • Patent number: 5545778
    Abstract: A process for the preparation of one or more of CHClFCF.sub.3 (HCFC-124), CHF.sub.2 CClF.sub.2 (HCFC-124a) and CHF.sub.2 CF.sub.3 (HFC-125) by reaction of perchloroethylene with hydrogen fluoride in a single stage reaction vessel in the presence of a fluorination catalyst. These compounds are useful in a variety of industrial applications including blowing agents, refrigerants, sterilant gases and solvent applications. Distilling the reaction product produces a distillate comprising HCl, CHClFCF.sub.3, CHF.sub.2 CClF.sub.2 and CHF.sub.2 CF.sub.3 and a minor amount of HF which distillate is scrubbed to remove the acids. The bottoms product comprises perchloroethylene, hydrogen fluoride and organic by-products which is phase separated to sequester the hydrogen fluoride from the mixture of perchloroethylene and organic by-products. The hydrogen fluoride and mixture of perchloroethylene with organic by-products are then preferably re-mixed at a controlled rate and recycled to the reaction vessel.
    Type: Grant
    Filed: May 25, 1994
    Date of Patent: August 13, 1996
    Assignee: AlliedSignal Inc.
    Inventors: Hsueh S. Tung, Addison M. Smith, Charles F. Swain
  • Patent number: 5545774
    Abstract: A process is disclosed for producing 1,1,1,3,3,3-hexafluoropropane. The process involves contacting 1,1,1,3,3,3-hexachloropropane with hydrogen fluoride in the vapor phase at a temperature of from about 250.degree. C. to 400.degree. C. in the presence of a catalyst of trivalent chromium supported on carbon. The carbon has an ash content sufficiently low to produce CF.sub.3 CH.sub.2 CF.sub.3 with a selectivity of at least about 70 percent based upon the amount of 1,1,1,3,3,3-hexachloropropane reacted with HF.
    Type: Grant
    Filed: December 8, 1994
    Date of Patent: August 13, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: V. N. Mallikarjuna Rao
  • Patent number: 5532418
    Abstract: A method of producing 1,1,1,2,3,3-hexafluoropropane in a characteristic process in which tetrafluorochloropropene is first obtained from the dechlorofluorination (removing ClF) of 1,1,1,2,2-pentafluoro-3,3-dichloropropane and/or 1,1,2,2,3-pentafluoro-1,3-dichloropropane by hydrogen in the presence of a metal oxide catalyst and then the product olefin is fluorinated in the presence of a catalyst. By this method, 1,1,1,2,3,3-hexafluoropropane, which is useful as an action fluid and so on and has a property to help preserving the environment, and an intermediate in its synthesis can be easily produced at low cost.
    Type: Grant
    Filed: March 1, 1995
    Date of Patent: July 2, 1996
    Assignee: Daikin Industries Ltd.
    Inventors: Tatsuo Nakada, Hirokazu Aoyama
  • Patent number: 5481028
    Abstract: A process for the preparation of perfluoroalkyl iodides, especially perfluoroethyl iodide, by reaction of perfluorinated compounds which contain a carbon carbon double bond with ICl in HF solvent in the presence of Lewis acid catalysts. The compounds are used as telogens for the telomerization of tetrafluoroethylene to long-chain perfluoroalkyl iodides.
    Type: Grant
    Filed: August 12, 1994
    Date of Patent: January 2, 1996
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Viacheslav A. Petrov, Carl G. Krespan
  • Patent number: 5475166
    Abstract: In a process for preparing 1,1,1-trifluorochloroethane by reacting, in a gas phase, trichloroethylene and hydrogen fluoride, when the reactant gases are diluted with a gas which is inactive to the reaction, it is very easy to control a reaction temperature, and when a generated gas from the reaction of 1,1,1-trifluorochloroethane and hydrogen fluoride is used as a diluent gas, generation of 1,1-difluoroethylene is suppressed to a very low level while not influencing the reaction between trichloroethylene and hydrogen fluoride.
    Type: Grant
    Filed: July 29, 1994
    Date of Patent: December 12, 1995
    Assignee: Daikin Industries, Ltd.
    Inventors: Satoshi Koyama, Yukio Homoto, Naoki Esaka
  • Patent number: 5475167
    Abstract: A process is disclosed for the preparation of pentafluoroethane from chlorotetrafluoroethane (the yield of pentafluoroethane is at least 50 mole percent based upon the amount of chlorofluoroethane reacted with HF) with particularly low levels of chlorofluoroethanes. The process involves providing sufficient pretreatment (where necessary) of a Cr.sub.2 O.sub.3 catalyst with at least one agent selected from the group consisting of CO, H.sub.2, H.sub.2 O and mixtures thereof in the gaseous state such that the total chlorofluoroethane content of said product stream is less than 1 mole percent. Certain high surface area catalysts may be used without such pretreatment.
    Type: Grant
    Filed: February 17, 1995
    Date of Patent: December 12, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Mario J. Nappa, V. N. Mallikarjuna Rao, William R. Williams
  • Patent number: 5461177
    Abstract: A halocarbon product made from the reaction of excess hydrogen fluoride with a halocarbon, containing excess hydrogen fluoride as an azeotrope is purified by fluorination in the presence of additional halocarbon or halo-olefin.
    Type: Grant
    Filed: February 2, 1994
    Date of Patent: October 24, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Leo E. Manzer, V. N. M. Rao
  • Patent number: 5453551
    Abstract: The invention relates to the purification of pentafluoroethane (F125) containing chloropentafluoroethane (F15).The F-125-F115 mixture to be purified is subjected to a fluorination stage to convert F115 into hexafluoroethane (F116) which is then separated from F125, for example by distillation.
    Type: Grant
    Filed: February 17, 1994
    Date of Patent: September 26, 1995
    Assignee: Elf Atochem S.A.
    Inventors: Eric Lacroix, Andre Lantz, Bernard Cheminal
  • Patent number: 5449842
    Abstract: A novel gas phase process for the production of 1,1-dichloro-1-fluoroethane from vinylidene chloride and hydrogen fluoride is provided. The process is characterized by high conversion of vinylidene chloride to product, with a high selectivity for 1,1-dichloro-1-fluoroethane. The process may also be operated to selectively form 1-chloro-1,1-difluoroethane. Few volatile by-products and substantially no tar or oligomeric material is formed. Catalyst performance remains constant over extended periods of time.
    Type: Grant
    Filed: August 23, 1993
    Date of Patent: September 12, 1995
    Assignee: Atochem North America, Inc.
    Inventor: Maher Y. Elsheikh
  • Patent number: 5449843
    Abstract: A more efficient reaction mechanism is provided for producing 1,1-dichloro-1-fluoroethane (HCFC-141b) by reacting vinylidene chloride with hydrogen fluoride in the liquid phase in the presence of a catalyst and a sulfone solvent or a nitroalkane or nitroarene solvent. In particular, by using a titanium tetrafluoride catalyst in conjunction with tetramethylene sulfone solvent, most all the vinylidene chloride reagent can be converted to HCFC-141b to the virtual exclusion of unwanted, closely associated byproducts like 1,1-difluoro-1-chloroethane (HCFC-142b) and 1,1,1-trifluoroethane (HFC-143a), while reducing the production of tars to a minimum.
    Type: Grant
    Filed: August 8, 1994
    Date of Patent: September 12, 1995
    Assignee: LaRoche Industries, Inc.
    Inventors: Betty J. Achord, C. Bradford Boyce
  • Patent number: 5446218
    Abstract: A single step, vapor phase process for the chlorofluorination of methane forms trifluoromethane and/or tetrafluoromethane in high yield. A Cr.sub.2 O.sub.3 catalyst is preferred.
    Type: Grant
    Filed: March 15, 1994
    Date of Patent: August 29, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: James L. Webster, Jan J. Lerou
  • Patent number: 5414165
    Abstract: A process is disclosed for producing 1,1,1,3,3,3-hexafluoropropane with high selectivity. 1,1,1,3,3,3-hexachloropropane is contacted with hydrogen fluoride in the vapor phase at a temperature of from about 200.degree. C. to 400.degree. C. in the presence of a catalyst comprising trivalent chromium, to produce a fluorinated product containing CF.sub.3 CH.sub.2 CF.sub.3 and its haloprecursors (i.e., compounds which may be recycled for further reaction with HF) with a total selectivity of at least about 95 percent; and a sufficient amount of said haloprecursors is reacted with hydrogen fluoride in the vapor phase at a temperature of from 200.degree. C. to 400.degree. C. in the presence of a catalyst comprising trivalent chromium to provide an overall selectivity to 1,1,1,3,3,3-hexafluoropropane of at least about 95 percent based upon the amount of 1,1,1,3,3,3-hexachloropropane initially reacted with HF.
    Type: Grant
    Filed: July 29, 1994
    Date of Patent: May 9, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Mario J. Nappa, Allen C. Sievert
  • Patent number: 5407877
    Abstract: A process for the reactivation of a chromium-based fluorination catalyst, in particular chromia, by contacting the deactivated chromium-based fluorination catalyst with an atmosphere containing water vapour at elevated temperature, preferably above 300.degree. C.
    Type: Grant
    Filed: December 2, 1992
    Date of Patent: April 18, 1995
    Assignee: Imperial Chemical Industries PLC
    Inventor: John D. Scott