Unsaturated Patents (Class 570/135)
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Patent number: 5220082Abstract: 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: GrantFiled: June 25, 1992Date of Patent: June 15, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventor: Carl G. Krespan
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Patent number: 5177272Abstract: The invention relates to a process for preparing perhalogenated olefins which comprises reacting a perhalogenated alkane, having at least one atom of a halogen different from fluorine, with a tris-dialkylamino phosphine at temperature not higher than 60.degree. C.Type: GrantFiled: January 23, 1992Date of Patent: January 5, 1993Assignee: Ausimont S.p.A.Inventors: Vittorio Montanari, Darryl D. Desmarteau, Walter Navarrini
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Patent number: 5068415Abstract: The halogenotetrafluoropropionic acid 3-iodotetrafluoropropionic acid of the formula ICF.sub.2 CF.sub.2 COOH, it is prepared by reacting iodine, tetrafluoroethylene and ethylene in a one-pot reaction under specific conditions, reacting the resulting compound ICF.sub.2 CF.sub.2 CH.sub.2 CH.sub.2 I with a base in order to eliminate hydrogen iodide and oxidizing the compound ICF.sub.2 CF.sub.2 --CH.dbd.CH.sub.2 thus obtained to give 3-iodotetrafluoropropionic acid. The halogenotetrafluoropropionic acid is an advantageous starting compound for the preparation of valuable unsaturated compounds containing functional groups.Type: GrantFiled: September 4, 1987Date of Patent: November 26, 1991Assignee: Hoechst AktiengesellschaftInventors: Konrad von Werner, Anton Probst
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Patent number: 5026928Abstract: The present invention relates to the synthesis of new terminal olefins, perfluoro 2,4-dimethyl 3-ethylpentene and perfluoro 2-isopropyl 3,3-dimethylbutene, and to the subsequent fluorination thereof in order to obtain highly branched perfluoroalkanes, capable of providing perfluoroalkyl radicals, which are utilizable as initiators for the polymerization of ethylenically unsaturated monomers.Type: GrantFiled: April 14, 1989Date of Patent: June 25, 1991Assignee: Ausimont S.r.l.Inventors: Claudio Tonelli, Vito Tortelli
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Patent number: 5017718Abstract: 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: GrantFiled: January 26, 1984Date of Patent: May 21, 1991Assignee: Sagami Chemical Research CenterInventors: Iwao Ojima, Takamasa Fuchikami
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Patent number: 4997855Abstract: Nematodes and insects are controlled by application of vinyl fluorides of the formula ##STR1## where R is CH.sub.2 X--, CHX.sub.2 --, CX.sub.3 --, XCH.dbd.CH--, CH.sub.2 .dbd.CX-- or straight chain alkyl(C.sub.2 -C.sub.8);R.sup.1 is hydrogen, fluoro, chloro, bromo, CH.sub.2 Z--, CHZ.sub.2 -- or CZ.sub.3 --;R.sup.2, X and Z independently are hydrogen, fluoro, chloro or bromo; Y.sup.1, Y.sup.2, Y.sup.3, and Y.sup.4 independently are CH.sub.3 or any value of R.sup.2, X and Z; a is 0-12; n is 7-13; and n is greater than a.Particular species controlled are the root-knot, stunt, lesion, cyst and free-living nematodes, and the southern corn rootworm. The vinyl fluorides also have anthelmintic utility.Type: GrantFiled: September 15, 1988Date of Patent: March 5, 1991Assignee: FMC CorporationInventor: Clinton J. Peake
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Patent number: 4968851Abstract: A method of combating arthropods and nematodes which comprises applying thereto, to a habitat thereof or to an area from which they are to be excluded an arthropodicidally or nematocidally effective amount of at least one long-chain halogenoolefine of the formula (I) ##STR1## in which R represents a straight-chain or branched alkyl radical with 8 to 25 carbon atoms in the straight chain, the alkyl radical optionally being interrupted once or several times by a --C.tbd.C-- and/or ##STR2## in which Z and Z.sup.1 are identical or different and represent hydrogen or methyl andR.sup.1 represents hydrogen, alkyl or halogen.Those compounds are new wherein R has at least 12 carbon atoms in the straight chain.Type: GrantFiled: February 24, 1989Date of Patent: November 6, 1990Assignee: Bayer AktiengesellschaftInventors: Klaus Naumann, Benedikt Becker, Wolfgang Behrenz, Bernhard Homeyer, Wilhelm Stendel
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Patent number: 4906416Abstract: 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: GrantFiled: February 8, 1985Date of Patent: March 6, 1990Assignee: AtochemInventors: Hubert Blancou, Auguste Commeyras, Robert Teissedre
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Patent number: 4876405Abstract: A process for preparing fluoroethylenes and chlorofluoroethylenes starting from chlorofluoroethanes and hydrogen, carried out in gas phase at a temperature ranging from 150.degree. to 600.degree. C., in the presence of a hydrogenation catalyst, wherein the chlorofluoroethanes have at least one chlorine atom on each carbon atom, and the catalyst is selected preferably from palladium, nickel, chromium, cobalt, platinum, copper and mixtures thereof, and it is utilized either as such or inert materials.Type: GrantFiled: July 13, 1987Date of Patent: October 24, 1989Assignee: Ausimont S.p.A.Inventor: Claudio Gervasutti
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Patent number: 4837369Abstract: 3-Fluoro-2-(fluoromethyl)-propene is prepared in a simple manner and in good yields by reacting 3-chloro-2-(chloromethyl)-propene with a fluorinating agent. The present invention also relates to 3-fluoro-2-(chloromethyl)-propene, an intermediate product in this process.Type: GrantFiled: February 25, 1987Date of Patent: June 6, 1989Assignee: Bayer AktiengesellschaftInventors: Hermann Hagemann, Bernd Baasner
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Patent number: 4760208Abstract: 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: GrantFiled: June 9, 1983Date of Patent: July 26, 1988Assignee: Occidental Chemical CorporationInventor: Mohan S. Saran
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Patent number: 4668710Abstract: Included are trihalovinyl polyol ethers. The compositions have pendant 1,2,2-trihaloethenyl moieties. The compositions may be low viscosity oils or highly polymeric such as incorporated with a urethane or other polymers. One of the uses of the compositions is as flame retardants which may have high thermal stability and scorch resistance.Type: GrantFiled: December 23, 1985Date of Patent: May 26, 1987Assignee: The Dow Chemical CompanyInventors: Chester E. Pawloski, William J. Kruper, Jr.
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Patent number: 4604480Abstract: A method for the preparation of a first sulfone compound of the formula: ##STR1## wherein R.sub.a is ##STR2## where R.sub.b is Br and R.sub.c is H except that R.sub.b and R.sub.c together may be an electron pair when R.sub.6 is a radical of the formula: ##STR3## wherein X.sub.1 is independently chlorine, bromine or iodine and R.sub.1 and R.sub.2 are independently at each occurrence hydrogen or, substituted or unsubstituted, phenyl or alkyl where the substituents are halogen or alkoxy or additional --SO.sub.2 Br groups; provided that, each carbon atom of R.sub.1 or R.sub.2 which contains --SO.sub.2 Br also contains an X.sub.1 group and wherein R.sub.3 through R.sub.9 are independently --OZ,--C.sub.6 M.sub.5,--Z,--SiZ.sub.3 or --X.sub.2, where Z is hydrogen or substituted or unsubstituted phenyl, alkyl, alkenyl or alkynyl; X.sub.2 is chlorine, bromine, iodine or fluorine; M is independently at each occurrence Z or X.sub.2 ; R.sub.3 and R.sub.4 may together be an electron pair; two or more of R.sub.3, R.sub.Type: GrantFiled: August 15, 1983Date of Patent: August 5, 1986Assignee: The Research Foundation of State University of New YorkInventors: Eric Block, Mohammad Aslam
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Patent number: 4496483Abstract: S-(2-Halo-2-propen-l-yl) N-(hexamethyleneimino)thiolcarbamates in which the halo is preferably bromo or chloro. The compounds have biological activity and may be used, for example, as selective pre-emergence herbicides.Type: GrantFiled: September 12, 1983Date of Patent: January 29, 1985Assignee: United States Borax & Chemical CorporationInventor: Don L. Hunter
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Patent number: 4393227Abstract: Olefinic compounds are made from their vicinally chlorinated organic precursors by dechlorination with metallic magnesium in the presence of a mercury-based promoter, which may be a water-soluble mercury salt or metallic mercury, and of a catalytic amount of iodine. This process is particularly suitable for dechlorinating 4,5-dichloro-dioxolanes to the corresponding dioxoles. 4,5-Difluoro-2,2 bis(trifluoromethyl)-1,3-dioxole, which can be made by this process in a reproducible manner from 4,5-dichloro-4,5-difluoro-2,2-bis(trifluoromethyl)-1,3-dioxolane, is a useful monomer for making amorphous homopolymers and copolymers with tetrafluoroethylene, which are well suited for wire coating, finishes, and transparent glazing for corrosive service.Type: GrantFiled: August 12, 1981Date of Patent: July 12, 1983Assignee: E. I. Du Pont de Nemours and CompanyInventor: Edward N. Squire
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Patent number: 4345084Abstract: Unsaturated eicosanoic acids and derivatives thereof which inhibit the synthesis of SRS-A are useful for treating and preventing asthma and allergic responses caused by SRS-A as well as useful in inhibiting inflammation.Type: GrantFiled: June 29, 1981Date of Patent: August 17, 1982Assignee: Hoffmann-La Roche Inc.Inventors: Ka-Kong Chan, George W. Holland, Perry Rosen
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Patent number: 4292454Abstract: Disclosed is a process for the coupling of a Grignard reagent RMgX with an allylic halide in the presence of a dipolar aprotic solvent wherein the improvement, for obtaining improved yield and selectivity, comprises adding a catalyst to said Grignard or allylic halide and then carrying out the coupling reaction by the addition of the Grignard reagent to the allylic halide, said reaction being characterized by the displacement at the gamma position (relative to the halide) of the allylic halide with R of the Grignard reagent, migration of the allylic double bond in the direction of the halogen atom and loss of halogen. The present invention also resides in the discovery of certain novel procedures for the synthesis of Vitamin E. Specific embodiments of this aspect of the invention reside in the syntheses of 6,7-dehydrophytol, 10,11-dihydrofarnesene, phytone, hexahydropseudoionone, and related compounds as precursors for Vitamin E.Type: GrantFiled: March 18, 1980Date of Patent: September 29, 1981Assignee: SCM CorporationInventors: Carlos G. Cardenas, Zia Ud Din
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Patent number: 4289646Abstract: 1,1-Difluoro-2-chloroethylene is used as the propellant in an aerosol spray can. It is reasonably stable and non-flammable but will in time degrade in the atmosphere.Type: GrantFiled: October 11, 1979Date of Patent: September 15, 1981Assignee: Bayer AktiengesellschaftInventors: Karl-Heinz Mitschke, Hans Niederprum
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Patent number: 4285778Abstract: 2,2-Dichloro-5-methyl-1,1,1-trifluorohex-4-ene, an intermediate in the synthesis of pyrethroid insecticides, is obtained by continuous distillation, preferably under sub-atmospheric pressure, of a mixture of 5-methyl-2,2,4-trichloro-1,1,1-trifluorohexane, dimethylformamide and lithium bromide, precipitating the chlorofluorocarbons from the distillate with water and separating the desired product from starting material by a further distillation.Type: GrantFiled: May 15, 1980Date of Patent: August 25, 1981Assignee: Imperial Chemical Industries LimitedInventors: John Crosby, Bernard W. H. Terry
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Patent number: 4259263Abstract: A halogenated hydrocarbon having the general formula: ##STR1## wherein Y represents fluorine, chlorine, bromine or --(CF.sub.2).sub.m W, R represents hydrogen or lower alkyl, R.sup.1 represents lower alkyl, X represents chlorine, bromine or iodine, W represents hydrogen, fluorine or chlorine and m is 1 or 2, is prepared by heating a compound having the general formula: ##STR2## wherein R, R.sup.1, X, Y, W and m have the meanings given above and Z represents chlorine, bromine or iodine, in a polar aprotic solvent together with an alkanolamine, optionally in the presence of a copper salt.Type: GrantFiled: October 1, 1979Date of Patent: March 31, 1981Assignee: Imperial Chemical Industries LimitedInventor: John Crosby