Preparing Unsaturated Compound Patents (Class 570/153)
  • Patent number: 5243104
    Abstract: Chlorotrifluoroethylene is prepared in high yield by reacting tetrafluoroethylene with hydrogen chloride in the presence of a metallic catalyst without using 1,1,2-trichlorotrifluoroethylene, which destroys the ozone layer.
    Type: Grant
    Filed: May 22, 1992
    Date of Patent: September 7, 1993
    Assignee: Daikin Industries Limited
    Inventors: Fumihiko Yamaguchi, Tatsuya Otsuka, Koutarou Nakagawa
  • Patent number: 5177275
    Abstract: Substrate compounds are reacted by passing them through an eductor with fluorine gas optionally in the presence of a liquid medium and preferably in a loop reactor with cooling means thereby providing rapid but controlled reaction suitable for industrial scale production. Vinylidene chloride, for example, smoothly produces dichlorodifluoroethane and dichlorotrifluoroethane in good yield.
    Type: Grant
    Filed: May 1, 1989
    Date of Patent: January 5, 1993
    Assignee: PCR Group, Inc.
    Inventors: Keith B. Baucom, Adam C. Alty, Earl J. Kimmel
  • Patent number: 5162594
    Abstract: This invention concerns a process for the production of polyfluoroolefins by the catalytic addition of polyfluoroallylic fluorides to fluoroethylenes. 1:1 and 1:2 Adducts such as F-pentene-2 and F-heptene-3 can be formed selectively and reduced further to dihydro- or trihydropolyfluoroalkanes, which are useful as HFC cleaning agents.
    Type: Grant
    Filed: October 4, 1991
    Date of Patent: November 10, 1992
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Carl G. Krespan
  • Patent number: 5157166
    Abstract: This invention relates to a process for making di-fluoro analogs of squalene.
    Type: Grant
    Filed: March 2, 1992
    Date of Patent: October 20, 1992
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Esa T. Jarvi, Michael L. Edwards, James R. McCarthy
  • Patent number: 5146017
    Abstract: A process is described for the reaction of at least one partly fluorinated alkene with catalysts containing tungsten complex compounds, at 10.degree. to 200.degree. C., if appropriate in the presence of at least one inert solvent. A mixture of a partly fluorinated alkene with another partly fluorinated alkene or with a non-fluorinated alkene can also be employed for the reaction. Longer-chain partly fluorinated compounds are thereby obtained which contain at least one internal C.dbd.C double bond. Ethylene or a short-chain alkene is furthermore produced and is separated off from the reaction mixture. The longer-chain partly fluorinated compounds are valuable intermediates and can be hydrogenated to give, for example, highly heat-resistant special lubricants.
    Type: Grant
    Filed: October 15, 1991
    Date of Patent: September 8, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Konrad V. Werner, Karin Weiss
  • Patent number: 5136113
    Abstract: Catalytic hydrogenolysis of fluorohalocarbons (e.g., CFCs) and fluorohalohydrocarbons (e.g., HCFCs), using catalysts of Re, Co, Ni, Ru, Rh, Pd, Os, Ir, and/or Pt on a carbon having low ash content. Preferred catalysts use carbon which is acid-washed, first with an acid other than hydrofluoric acid and then with hydrofluoric acid; and also have a low content of phosphorus, sulfur, potassium, sodium and iron.
    Type: Grant
    Filed: July 23, 1991
    Date of Patent: August 4, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: V. N. M. Rao
  • Patent number: 5118888
    Abstract: Process for the preparation of 1,2-difluoro-ethylene and 1-chloro-1,2-difluoroethylene by catalytic hydrogenation of 1,2-dichloro-difluoro-ethylene.
    Type: Grant
    Filed: May 29, 1990
    Date of Patent: June 2, 1992
    Assignee: Ausimont S.p.A.
    Inventors: Claudio Gervasutti, Giorgio Guglielmo, Luigi Marangoni
  • Patent number: 5045634
    Abstract: A process for fluorination by contacting a haloolefin with molten alkali metal acid fluoride to provide a fluorinated saturated or unsaturated hydrocarbon having at least one more fluorine than the starting haloolefin.
    Type: Grant
    Filed: June 28, 1990
    Date of Patent: September 3, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Richard E. Fernandez, William H. Gumprecht, Kaplan, Ralph B.
  • Patent number: 5017718
    Abstract: A process for preparing a perfluoroalkyl-substituted compound is disclosed. The process comprises reacting a halopolyfluoroalkane having 1 to 20 carbon atoms with a compound selected from the group consisting of (1) a substituted or unsubstituted ethylene, (2) a substituted or unsubstituted acetylene and (3) a substituted or unsubstituted allylsilane, in the presence of a metal-carbonyl complex of the metal of the Group VIII of the Periodic Table. Alternatively, the reaction between the halopolyfluoroalkane and the substituted or unsubstituted allylsilane is effected under radical generating condition.
    Type: Grant
    Filed: January 26, 1984
    Date of Patent: May 21, 1991
    Assignee: Sagami Chemical Research Center
    Inventors: Iwao Ojima, Takamasa Fuchikami
  • Patent number: 4973773
    Abstract: Preparation of high yields of tetrafluoroethylene by preferably contacting pentafluoroethane and/or trifluoromethane with hot gas, preferably argon (.gtoreq.2000.degree. K.) followed by rapid cooling of the reaction mixture, in less than one second, i.e., 0.001 to 0.1 second, to a temperature .gtoreq.800.degree. K.
    Type: Grant
    Filed: March 21, 1989
    Date of Patent: November 27, 1990
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Brian S. Malone
  • Patent number: 4906416
    Abstract: A process for preparing perfluoroalkanecarboxylic acids, wherein a perfluoroiodoalkane, R.sub.F I, is reacted with trichloroethylene in an acidic solvent in the presence of zinc, and the 2-perfluoroalkyl-1,1-dichloroethylene thus obtained is oxidized with the aid of permanganate, R.sub.F representing a straight chain or branched perfluoro radical containing one to 20 carbon atoms, together with certain novel perfluoroalkyldichloroethylenes having four or more carbon atoms so obtained.
    Type: Grant
    Filed: February 8, 1985
    Date of Patent: March 6, 1990
    Assignee: Atochem
    Inventors: Hubert Blancou, Auguste Commeyras, Robert Teissedre
  • Patent number: 4898645
    Abstract: A process is described for the production of pure tetrafluoroethylene from a gas formed in the pyrolysis of a fluorocarbon compound having 1 to 4 carbon atoms, which can contain a hydrogen atom and a chlorine atom. The pyrolysis gas, after hydrogen chloride or hydrogen fluoride and also if necessary steam have been separated off, is condensed under pressure and distilled in a plurality of columns, in the first column the low boilers being distilled off, preferably with a reflux ratio of 6 to 15 kg per kg of tetrafluoroethylene produced, and in the second column tetrafluoroethylene, preferably with a reflux ratio of 3 to 5 kg per kg of tetrafluoroethylene produced. Per kg of tetrafluoroethylene produced, from 0.6 to 2 kg of difluoromonochloromethane are fed into the second column as a distillation aid. The novel process makes it possible to produce pure tetrafluoroethylene at comparatively reduced energy and apparatus costs.
    Type: Grant
    Filed: August 30, 1988
    Date of Patent: February 6, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Voigt, Reinhold Freudenreich
  • Patent number: 4820883
    Abstract: A method for preparing an unsaturated fluorocarbon by defluorinating a perfluoroalkene employing activated carbon.
    Type: Grant
    Filed: November 24, 1987
    Date of Patent: April 11, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Frank J. Weigert
  • Patent number: 4814522
    Abstract: Catalyzed halogen exchange between perhaloolefins to form products of the formulas:R.sup.1 R.sup.2 C=CR.sup.3 R.sup.8andR.sup.5 R.sup.6 C=CR.sup.7 R.sup.4wherein R.sup.1, R.sup.2, R.sup.3, R.sup.5, Rhu 6l , and R.sup.7 are individually selected from the group F, Cl, Br, C.sub.1 to C.sub.4 perfluoroalkyl, and pentafluorophenyl; or R.sup.1 and R.sup.3, R.sup.2 and R.sup.3, R.sup.5 and R.sup.7, R.sup.6 and R.sup.7 together, with the proviso that both groups are in the cis configuration, are selected from the group perfluoroalkylene of 2 to 4 carbons ando--C.sub.6 F.sub.4 (--)CF.sub.2 --,R.sup.8 =F, R.sup.4 =Cl or Br; and wherein none of the fluoroolefins simultaneously contains both Cl and Br.
    Type: Grant
    Filed: January 11, 1988
    Date of Patent: March 21, 1989
    Assignee: E. I. DuPont DeNemours and Company
    Inventor: Frank J. Weigert
  • Patent number: 4788352
    Abstract: C.sub.4 to C.sub.7 trifluoroalkene compounds and a method for their preparation by the contact of C.sub.3 or C.sub.4 trifluoroalkenes with C.sub.2 to C.sub.4 olefins in the presence of a homogeneous palladium (II) catalyst.
    Type: Grant
    Filed: October 20, 1987
    Date of Patent: November 29, 1988
    Assignee: Shell Oil Company
    Inventor: Edgar J. Smutny
  • Patent number: 4760208
    Abstract: A process for coupling two low molecular weight telomers of chlorotrifluoroethylene comprises reacting the telomers in a solvent with an amount of iron sufficient to form a coupled olefin. The olefin can then be fluorinated using a suitable fluorinating agent, such as chlorine trifluoride, to form a saturated product. Preferably, the solvent for the coupling reaction is acetonitrile, and the reaction is conducted under reflux conditions. A small amount of FeCl.sub.2 can optionally be added to the reaction mixture as an initiator for the reaction.
    Type: Grant
    Filed: June 9, 1983
    Date of Patent: July 26, 1988
    Assignee: Occidental Chemical Corporation
    Inventor: Mohan S. Saran
  • Patent number: 4739123
    Abstract: Process for preparing 2-trifluoro-methyl-3,3,3-trifluoropropene.
    Type: Grant
    Filed: October 21, 1986
    Date of Patent: April 19, 1988
    Assignee: Daiken Industries, Ltd.
    Inventors: Yasuhisa Furutaka, Masayuki Yamana, Tsunetoshi Honda
  • Patent number: 4705904
    Abstract: A vapor phase synthesis of hexafluoroisobutylene, which comprises contacting in the vapor phase in a catalyst zone, B, of a reactor hexafluoropropylene oxide with a fluorinated catalyst such as fluorinated silica-alumina at a temperature of about 400.degree.-600.degree. C. for a residence time sufficient to form a vapor stream comprising hexafluoroacetone which is thereafter directly contacted in a heating zone of the reactor with a vapor stream comprising a keytone-generating compound such as acetic anhydride at a temperature of about 500.degree.-700.degree. C. for a residence time sufficient to form a stream comprising hexafluoroisobutylene, substantially-free of perfluoroisobutylene and recovering the hexafluoroisobutylene product is disclosed.
    Type: Grant
    Filed: January 17, 1986
    Date of Patent: November 10, 1987
    Assignee: Allied Corporation
    Inventors: John H. Bonfield, Harry E. Ulmer
  • Patent number: 4691067
    Abstract: A process for coupling two low molecular weight telomers of chlorotrifluoroethylene comprises reacting the telomers with hydrogen in the presence of an effective amount of a catalyst to form a coupled olefin. The catalyst comprises palladium, platinum, rhodium, ruthenium, Raney nickel, Raney cobalt, and mixtures thereof, either supported or unsupported. The olefin can be fluorinated using a suitable fluorinating agent, such as chlorine trifluoride, to form a saturated telomer.
    Type: Grant
    Filed: June 9, 1983
    Date of Patent: September 1, 1987
    Assignee: Occidental Chemical Corporation
    Inventor: Johny S. Ng
  • Patent number: 4668832
    Abstract: Halogenated, unsaturated alcohols are dehydrated by contacting the alcohol and a carrier gas with a silica alumina catalyst to form dienes of the formula: ##STR1## wherein each X is independently hydrogen, fluorine chlorine, or bromine with the proviso that no more than one of them is hydrogen, and each R is independently hydrogen, alkyl, aralkyl, alkaryl, or aryl.
    Type: Grant
    Filed: October 8, 1985
    Date of Patent: May 26, 1987
    Assignee: The Dow Chemical Company
    Inventor: William J. Kruper, Jr.
  • Patent number: 4634778
    Abstract: Process for preparing chlorinated ethylenic derivatives of the formula ##STR1## in which R.sub.1 represents acetyl, formyl optionally in the form of an acetal, hydroxy optionally as an ether or ester, alkyloxycarbonyl, alkyl of 1 to 12 carbon atoms substituted by one or more acetyl, formyl optionally in the form of an acetal, hydroxy optionally in the form of an ether or ester, or alkyloxycarbonyl, alkenyl of 2 to 12 carbon atoms containing one or more double bonds optionally substituted by one or more of acetyl, formyl optionally in the form of an acetal, hydroxy optionally in the form of an ether or ester, or alkyloxycarbonyl, or R.sub.1 represents 3-sulpholenyl or a radical of formula ##STR2## in which R.sub.2 denotes a hydrogen or acetyl, by reacting chlorine in a nonpolar aprotic solvent with a compound of general formula ##STR3## in which R.sub.1 is defined as above. The products of formula I, some of which are new, are useful as intermediates in the synthesis of terpene products such as vitamin E.
    Type: Grant
    Filed: November 16, 1984
    Date of Patent: January 6, 1987
    Assignee: Rhone-Poulenc Sante
    Inventors: Gerard Mignani, Didier Morel, Pierre Chabardes
  • Patent number: 4587366
    Abstract: A process is described for preparing fluoroalkyl-substituted iodoalkanes by reacting a fluorinated alkyl iodide with a substituted or unsubstituted alkene under heat in the presence of a catalyst. The catalyst is at least one metal which, in the periodic table of the elements, has one of the atomic numbers 24 to 30, 42 to 48 or 74 to 79 and is in finely divided form. The products of the process according to the invention are addition compounds of the fluorinated alkyl iodide with the substituted or unsubstituted alkene and, in known processes, can be used as useful intermediates for preparing fluorine-containing polymers, textile finishes, fire-extinguishing agents or surfactants.
    Type: Grant
    Filed: October 19, 1984
    Date of Patent: May 6, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Konrad von Werner
  • Patent number: 4377716
    Abstract: Hexafluoro-2,3-bis(trifluoromethyl)-2-butene may be prepared by heating 2,2,4,4-tetrakis-(trifluoromethyl)-1,3-dithietane at elevated temperatures in the presence of activated carbon. The activated carbon serves as a desulphurization catalyst.
    Type: Grant
    Filed: December 14, 1981
    Date of Patent: March 22, 1983
    Assignee: Allied Corporation
    Inventors: Louis G. Anello, Richard F. Sweeney
  • Patent number: 4365102
    Abstract: A method of manufacturing CF.sub.4 and/or C.sub.2 F.sub.6 characterized by employing a mixed gas of tetrafluoroethylene and carbon dioxide at a mol ratio of less than 4:1 and heating it to a temperature exceeding 900.degree. C.
    Type: Grant
    Filed: September 29, 1980
    Date of Patent: December 21, 1982
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Maurice J. Couture, Dan Hayashi
  • Patent number: 4269780
    Abstract: A process for forming non-polymeric disproportionation products of non-conjugated olefins using catalysts comprising (1) at least one of certain neutral carbene complexes, and (2) at least one of certain compounds of Groups IVa, IVb, Vb, VIb, VIIb, VIII, and Ib of the Periodic Table of the Elements.
    Type: Grant
    Filed: December 6, 1979
    Date of Patent: May 26, 1981
    Assignee: Phillips Petroleum Company
    Inventor: Dennis S. Banasiak