Abstract: An improved process for the vapor phase fluorination, especially fluorination of 1,1,1-trifluoro-2-chloroethane (CFC-133a) with HF to produce 1,1,1,2-tetrafluoroethane (HFC-134a) employs a catalyst which preferably consists essentially of boehmite and Cr(OH)Cl.sub.2.2H.sub.2 O, combined and extruded to form particulates and then heated in nitrogen.
Type:
Grant
Filed:
June 23, 1993
Date of Patent:
August 2, 1994
Assignee:
Allied-Signal Inc.
Inventors:
Li Wang, Timothy J. Barder, Mark Kaiser, Russell W. Johnson, Blaise J. Arena
Abstract: Halogenated aromatics are prepared by heating halogenoformic acid esters to 80.degree. to 280.degree. C. in the presence of hydrogen fluoride or a catalytic amount of one or more Lewis acids from the group comprising aluminium halides, iron halides and antimony halides, and in the liquid phase.
Type:
Grant
Filed:
July 28, 1993
Date of Patent:
April 26, 1994
Assignee:
Bayer Aktiengesellschaft
Inventors:
Norbert Lui, Dietmar Bielefeldt, Albrecht Marhold
Abstract: A process for preparing fluorine-containing ethane derivatives using hydrogen fluoride and a catalytically active formulation comprising a tantalum fluorosulfonate compound or a niobium fluorosulfonate compound is described. The process is particularly suitable for preparing ethane derivatives which contain a CF.sub.3 group, for example for preparing CF.sub.3 CHCl.sub.2 (R123) from perchloroethylene.
Type:
Grant
Filed:
April 26, 1993
Date of Patent:
February 1, 1994
Assignee:
Solvay Fluor und Derivate GmbH
Inventors:
Johannes Eicher, Karl-Heinz Fazniewscy, Werner Rudolph
Abstract: The invention relates to a process for the reactivation of an activated charcoal catalyst employed in the preparation of 1,1,1,2,3,3,3-heptafluoropropane (R 227) in which the catalyst is heated to from 450.degree. to 900.degree. C. in a stream of inert gas or under reduced pressure.
Abstract: 1,1,1,2-tetrafluoroethane (HFA 134a) is manufactured from trichloroethylene by a two-stage process comprising reacting trichloroethylene with hydrogen fluoride under superatmospheric pressure in a first reaction zone to form 1,1,1-trifluoro-2-chloroethane (133a) and reacting the 1,1,1-trifluoro-2-chloroethane with hydrogen fluoride in a second reaction zone to form 1,1,1,2-tetrafluoroethane; the entire product stream from the 133a reaction zone together with additional HF of required is fed through the 134a reaction zone. The two reaction zones may be provided within a single reaction vessel.
Abstract: 1,1,1,2-tetrafluoroethane (HFA 134a) is manufactured from trichloroethylene by a two-stage process comprising reacting trichloroethylene with hydrogen fluoride in one reactor to form 1,1,1-trifluoro-2-chloroethane (133a) and reacting the 1,1,1-trifluoro-2-chloroethane with hydrogen fluoride in another reactor to form 1,1,1,2-tetrafluoroethane. The invention is characterised by reversing the reactor sequence and passing the entire product stream from the HFA 134a reactor together with trichloroethylene through the 133a reactor and separating 134a and hydrogen chloride from the recycle stream between the 133a reactor and the 134a reactor.
Abstract: Bismuth/alkaline earth metal catalysts which contain 0.005-0.8 g-atom of bismuth per mol of the alkaline earth metal compound employed and can furthermore contain promoters and/or inert additives, and lanthanide catalysts with or without catalyst supports can be employed as catalysts for halogen-fluorine exchange in organic compounds by means of hydrogen fluoride.
Abstract: A process for preparing fluorine-containing ethane derivatives using hydrogen fluoride and a catalytically active formulation comprising a tantalum fluorosulfonate compound or a niobium fluorosulfonate compound is described. The process is particularly suitable for preparing ethane derivatives which contain a CF.sub.3 group, for example for preparing C.sub.3 CHCl.sub.2 (R123) from perchloroethylene.
Type:
Grant
Filed:
September 8, 1992
Date of Patent:
July 13, 1993
Assignee:
Solvay Fluor und Derivate GmbH
Inventors:
Johannes Eicher, Karl-Heinz Fazniewscy, Werner Rudolph, Hans-Walter Swidersky
Abstract: The present invention relates to syntheses of perfluoropropane-- .e., octafluoropropane--from acyclic three-carbon hydrocarbons or partially or totally halogenated acyclic three-carbon hydrocarbons.
Type:
Grant
Filed:
January 28, 1992
Date of Patent:
June 15, 1993
Assignee:
E. I. Du Pont de Nemours and Company
Inventors:
James L. Webster, Steven H. Swearingen, Douglas W. Bruhnke, Leo E. Manzer, Elrey L. McCann
Abstract: A method of preparing fluorine-containing ethane derivatives using a catalyst mixture which comprises a metal halide and a sulfonic acid derivative is described. The method is particularly well suited for preparing CF.sub.3 CHCl.sub.2 (R123) from perchloroethylene and for preparing CF.sub.3 CH.sub.2 F (R134a) from trifluoroethylene.
Type:
Grant
Filed:
July 14, 1992
Date of Patent:
May 25, 1993
Assignee:
Kali-Chemie AG
Inventors:
Johannes Eicher, Karlheinz Fazniewscy, Werner Rudolph, Hans-Walter Swidersky
Abstract: This invention provides an improved process for the manufacture of 1,1,1,2-tetrafluoroethane by the reaction of HF and trichloroethylene in the presence of a catalyst to form a mixture comprising 2-chloro-1,1,1-trifluoroethane and 1,1,1,2-tetrafluoroethane and, optionally, other organic by-products. The improvement resides in conducting the reaction in a single reaction zone while recovering the 1,1,1,2-tetrafluoroethane from the mixture and recycling the 2-chloro-1,1,1-trifluoroethane and, optionally, other organic by-products from the mixture to the reaction along with trichloroethylene and HF.
Abstract: Hexafluoropropanes of the formula CF.sub.3 -CHX-CF.sub.3 where X is hydrogen or chlorine are prepared by reacting hexachloropropene with hydrogen fluoride in the gas phase in the presence of a catalyst.
Type:
Grant
Filed:
December 5, 1991
Date of Patent:
December 15, 1992
Assignee:
Bayer Aktiengesellschaft
Inventors:
Karl-Rudolf Gassen, Dietmar Bielefeldt, Albrecht Marhold, Hans-Helmut Schwarz
Abstract: 1-Chloro-1,1-difluoroethane is prepared by reacting hydrogen fluoride with vinylidene chloride, in a liquid medium containing preferably at least 40 mol % 1,1-dichloro-1-fluoroethane.
Type:
Grant
Filed:
December 4, 1990
Date of Patent:
October 27, 1992
Assignee:
Solvay S.A.
Inventors:
Rene Walraevens, James Franklin, Jean-Marie Yernaux
Abstract: The present invention relates to multistep syntheses of hexafluoropropylene from hexachloropropylene. In all these syntheses the first step is a fluorination of the starting material; later steps convert the initial products to CF.sub.3 --CFCl--CF.sub.3, which is dehalogenated to the desired product.
Type:
Grant
Filed:
December 19, 1989
Date of Patent:
November 26, 1991
Assignee:
E. I. Du Pont de Nemours and Company
Inventors:
James L. Webster, Swiatoslaw Trofimenko, Paul R. Resnick, Douglas W. Bruhnke, Jan J. Lerou, William H. Manogue, Leo E. Manzer, Elrey L. McCann, Steven H. Swearingen, James A. Trainham, Cristobal Bonifaz
Abstract: The present invention relates to multistep syntheses of hexafluoropropylene from acyclic three-carbon hydrocarbons or partially halogenated acyclic three-carbon hydrocarbons. In all these syntheses the first step is a vapor-phase chlorofluorination of the starting material to one or more saturated chlorofluorocarbons. Novel catalysts are also provided.
Type:
Grant
Filed:
December 19, 1989
Date of Patent:
October 15, 1991
Assignee:
E. I. Du Pont de Nemours and Company
Inventors:
James L. Webster, Elrey L. McCann, Douglas W. Bruhnke, Jan J. Lerou, William H. Manogue, Leo E. Manzer, Steven H. Swearingen, Swiatoslaw Trofimenko, Cristobal Bonifaz
Abstract: The present invention relates to multistep syntheses of hexafluoropropylene from propane, propylene or partially halogenated acyclic three-carbon hydrocarbons. In all these syntheses the first step is a vapor-phase chlorofluorination of the starting material to the unsaturated chlorofluorocarbon CF.sub.3 CClCCl.sub.2.
Type:
Grant
Filed:
December 19, 1989
Date of Patent:
August 27, 1991
Assignee:
E. I. Du Pont de Nemours and Company
Inventors:
James L. Webster, Elrey L. McCann, Douglas W. Bruhnke, Jan J. Lerou, Leo E. Manzer, William H. Manogue, Paul R. Resnick, Swiatoslaw Trofimenko
Abstract: 1,1-Dichloro-1-fluoroethane and 1-chloro-1,1-difluoroethane are prepared from the liquid phase fluorination of 1,1,1-trichloroethane by HF in the presence of a homogenous catalyst. 1,1-Dichloro-1-fluoroethane or 1-chloro-1,1-difluoroethane are selectively produced substantially free of vinylidene chloride.
Abstract: Chromium(III) oxide and hydroxide aerogels are produced by the reaction of chromium(VI) oxide with a solvent which is reducing to chromium(VI), such as methanol, heating the solution to hypercritical conditions, and venting the solvent hypercritically. The product aerogels exhibit surface areas above 400 m.sup.2 /g, pore volumes of at least 2 cm.sup.3 /g and a substantially uniform pore size distribution. Also disclosed is a unique process which employs high pore volume, high surface area chromium(III) oxide or hydroxide as a fluorination catalyst. More particularly, reaction of C.sub.2 Cl.sub.3 F.sub.3 with HF over these catalysts produced high yields of C.sub.2 Cl.sub.2 F.sub.4 and C.sub.2 ClF.sub.5.
Type:
Grant
Filed:
December 12, 1988
Date of Patent:
March 27, 1990
Assignee:
Allied-Signal Inc.
Inventors:
Emery J. Carlson, John N. Armor, William J. Cunningham, Addison M. Smith
Abstract: This invention relates to improved catalysts for gaseous phase fluoridation of aliphatic chlorinated and chlorofluorinated hydrocarbons by hydrofluoric acid. The catalysts comprise chromium salts or oxides complexed with aluminum phosphate and are characterized by a total specific surface area greater than about 200 m.sup.2 /g, but less than about 1000 m.sup.2 /g a surface area of pores of 40 to 50 .ANG. in radius above about 5 m.sup.2 /g, but less than about 150 m.sup.2 /g, a surface area of pores greater than or equal to 250 .ANG. in radius above about 2 m.sup.2 /g. but less than about 60 m.sup.2 /g. This invention also relates to gaseous phase fluoridation processes for chlorinated or chlorofluorinated derivatives utilizing these catalysts in fluidized bed reactors.
Abstract: The invention relates to a process for the manufacture of 1-chloro-1,1-difluoroethane in the liquid phase by reacting hydrofluoric acid with 1,1,1-trichloroethane and/or 1,1-dichloro-1-fluoroethane.The selectively is improved by using a perfluoroalkanesulphonic acid, in particular trifluoromethanesulphonic acid, as a catalyst.
Abstract: A process for producing a hydrocarbon fluoride at a high selectivity with minimum formation of by-products is disclosed, which comprises reacting a hydrogen-containing hydrocarbon halide with anhydrous hydrogen fluoride in a liquid phase in the presence of a reaction product of (i) at least one of (a) an oxygen-containing compound selected from the group consisting of H.sub.2 O, H.sub.2 O.sub.2 and an oxygen-containing organic compound, and (b) a nitrogen-containing compound selected from the group consisting of NH.sub.3 and a nitrogen-containing organic compound, (ii) a tin compound selected from the group consisting of a stannic halide, a stannic oxyhalide and an organotin compound, and (iii) anhydrous hydrogen fluoride.
Abstract: A process for the preparation of compounds containing a difluoromethylene or trifluoromethyl group. A compound containing a carbonyl group, preferbly an acid, acid halide, amide, ketone or any compound containing a perhaloalkylcarbonyl moiety is placed, in anhydrous liquid hydrofluoric acid, in contact with boron trifluoride in a quantity such that the absolute pressure of boron trifluoride in the reaction system is at least one bar for a time sufficient to convert the carbonyl group to a difluormethylene or trifluoromethyl group.The compounds obtained are useful as synthesis intermediates in the pharmaceutical, plant-protection and dye industries, as anesthetics or as heat-transfer and lubricating fluids.
Abstract: This invention relates to a continuous gaseous-phase process for the preparation of trichlorotrifluoroethane, dichlorotetrafluoroethane and monochloropentafluoroethane, in predetermined proportions, from tetrachloroethylene, chlorine and hydrofluoric acid in the presence of a catalyst. The process is characterized by the combination of two chlorination-fluorination reactors in sequence, a parallel fluorination-dismutation reactor, and a separation unit for extracting the desired products and recycling recovered hydrofluoric acid and non-fluorinated or insufficiently fluorinated products. The process advantageously yields dichlorotetrafluoroethane containing less than 7% asymmetric isomer, and trichlorotrifluoroethane containing less than 2% asymmetric isomer.
Type:
Grant
Filed:
November 25, 1981
Date of Patent:
August 12, 1986
Assignee:
PCUK Products Chimiques Ugine Kuhlmann
Inventors:
Michel Abel, Francois Fine, Louis Foulletier, Yvan Verot
Abstract: This invention relates to improved catalysts for gaseous phase fluorination of aliphatic chlorinated and chlorofluorinated hydrocarbons by hydrofluoric acid. The catalysts are characterized by an active carbon support having a total specific surface area greater than about 1000 m.sup.2 /g but less than about 2000 m.sup.2 /g, a surface area of pores of 40 to 50 .ANG. in radius above about 5 m.sup.2 /g but less than about 15 m.sup.2 /g, a surface area of pores greater than or equal to 250 .ANG. in radius above about 2 m.sup.2 /g but less than about 6 m.sup.2 /g, which has been impregnated with an aqueous chromium trioxide solution and dried. This invention also relates to gaseous phase fluorination processes for chlorinated or chlorofluorinated derivatives utilizing these catalysts in fluidized bed reactors.
Abstract: This invention relates to catalysts for gaseous phase fluorination of aliphatic chlorinated derivatives by hydrofluoric acid. The catalysts comprise chromium oxide microspheres obtained by a sol-gel process. This invention also relates to gaseous phase fluorination processes for aliphatic chlorinated derivatives utilizing these catalysts.
Abstract: This invention relates to improved catalysts for gaseous phase fluorination of aliphatic chlorinated and chlorofluorinated derivatives by hydrofluoric acid. The catalysts are characterized by an active carbon support having a total specific surface area greater than about 1000 m.sup.2 /g but less then about 2000 m.sup.2 /g, a surface area of pores of 40 to 50 .ANG. in radius above about 5 m.sup.2 /g but less then about 15 m.sup.2 /g, a surface area of pores greater than or equal to 250 .ANG. in radius above about 2 m.sup.2 /g but less than about 6 m.sup.2 /g, which has been impregnated with an aqueous chromium sulfate solution and dried. This invention also relates to gaseous phase fluorination processes for chlorinated or chlorofluorinated derivatives utilizing these catalysts in fluidized bed reactors.
Abstract: 1-Fluoro-1,1,2-trichloroethane is produced by a process which comprises the reaction of trichloroethylene with hydrogen fluoride using about 1.5 to 3.5 moles of hydrogen fluoride per mole of trichloroethylene, and conducting the reaction in the presence of a catalyst selected from the group consisting of CF.sub.3 SO.sub.3 H, TiCl.sub.4, MoCl.sub.5, WF.sub.6, NbCl.sub.5 and SnCl.sub.4 at a temperature in the range of 50.degree. to 150.degree. C. with a residence time of one quarter hour to five hours. The resulting product is relatively pure of overfluorinated by-products so as to be useful as a degreasing solvent.
Abstract: 1-Fluoro-1,1,2-trichloroethane is produced by a process which comprises the reaction of trichloroethylene with hydrogen fluoride using about 1.5 to 3.5 moles of hydrogen fluoride per mole of trichloroethylene, and conducting the reaction in the presence of a catalyst selected from the group consisting of CF.sub.3 SO.sub.3 H, TiCl.sub.4, MoCl.sub.5, WF.sub.6, NbCl.sub.5 and SnCl.sub.4 at a temperature in the range of 50.degree. to 150.degree. C. with a residence time of one quarter hour to five hours. The resulting product is relatively pure of overfluorinated by-products so as to be useful as a degreasing solvent.
Abstract: A process for the preparation of an optionally substituted trifluoromethyl-naphthalene which comprises contacting a compound of the formula ##STR1## in which R.sup.1 denotes hydrogen, alkyl, aralkyl, aryl, aryloxy, arylthio, polyhalogenoalkoxy, polyhalogenoalkylthio, halogen, nitro, halogenocarbonyl, halogenosulphonyl, alkylsulphonyl or arylsulphonyl, it being possible for the aromatic nuclei contained in the substituents R.sup.1 to be in turn substituted by halogen, alkyl, polyhalogenoalkoxy or polyhalogenoalkylthio,R.sup.2 represents hydrogen, halogen or alkyl andR.sup.3, R.sup.4, R.sup.5 and R.sup.6 denote hydrogen, orR.sup.3 and R.sup.4 or R.sup.4 and R.sup.5 in each case together denote a fused-on aromatic ring, and wherein, in the case where R.sup.3 and R.sup.4 together form a fused-on aromatic ring,R.sup.5 and R.sup.6 independently of one another can also denote, in addition to hydrogen, halogen, nitro, halogenocarbonyl or halogenosulphonyl, and wherein, in the case where R.sup.4 and R.sup.