Product Patents (Class 570/124)
  • Patent number: 6749756
    Abstract: A method of separating compounds that includes the steps of: tagging at least a first organic compound with a first tagging moiety to result in a first tagged compound; tagging at least a second organic compound with a second tagging moiety different from the first tagging moiety to result in a second tagged compound; and separating the first tagged compound from a mixture including the second tagged compound using a separation technique based upon differences between the first tagging moiety and the second tagging moiety. The present invention also provides a method for carrying out a chemical reaction including the steps of: tagging a plurality of compounds with different tagging moieties to create tagged compounds, conducting at least one chemical reaction on a mixture of the tagged compounds to produce a mixture of tagged products, and separating the mixture of tagged products by a separation technique based upon differences in the tagging moieties.
    Type: Grant
    Filed: February 18, 2000
    Date of Patent: June 15, 2004
    Assignee: University of Pittsburgh
    Inventors: Dennis P. Curran, Oscar de Frutos Garcia, Yoji Oderaotoshi
  • Patent number: 6710214
    Abstract: The present invention is to provide a method for producing a highly branched perfluoroolefin conveniently in a high yield, a novel highly branched perfluoroolefin, a method for producing a super-stable perfluoroalkyl radical and a novel super-stable perfluoroalkyl radical. The present invention is a production method of a perfluoroolefin which comprises reacting a hexafluoropropene trimer with a trialkylperfluoroalkylsilane in an aprotic polar solvent using a fluoride ion as a catalyst.
    Type: Grant
    Filed: November 12, 2002
    Date of Patent: March 23, 2004
    Assignees: National Institute of Advanced Industrial Science and Technology, Daikin Industries, Ltd.
    Inventors: Taizo Ono, Masakazu Nishida, Masaharu Okazaki, Kazumi Toriyama, Tetsuo Shimizu
  • Publication number: 20040033196
    Abstract: Fluoroalkanes such as fluoromethane labeled with 17F are produced by contacting 17F labeled F2 with alkanes, preferably methane, substituted or unsubstituted alkenes, or substituted or unsubstituted alkynes in the presence of a metal oxide catalyst, preferably a silver oxide catalyst, to produce the 17F labeled fluoroalkane. The 17F may be produced by irradiating 20Ne with protons, preferably having an energy of about 11 MeV and produced by a cyclotron. The 17F labeled fluoromethane or fluoroalkanes may be produced continuously. A method for determining the location of an 17F labeled tracer includes generating an 17F labeled fluoroalkane, administering the 17F labeled fluoroalkane to a test subject, and scanning the test subject with a radiosensitive detector such as a positron emission tomography scanner.
    Type: Application
    Filed: June 23, 2003
    Publication date: February 19, 2004
    Applicant: Wisconsin Alumni Research Foundation
    Inventors: Andrew D. Roberts, Robert J. Nickles
  • Patent number: 6689923
    Abstract: The present invention provides a perfluoroolefin-hydrocarbon hybrid compound represented by the following general formula (1): [(CF3)2CX][(CF3)2CY]C═C(CF3)Z   (1) wherein X, Y and Z may be the same or different, and independently represent F or R, excepting that all of X, Y and Z are F, wherein R represents straight chain or branched alkyl and aryl groups having from 1 to 15 carbon atoms. The present invention also provides a method of producing the above compound, and a method of producing a perfluoroalkyl radical by using the above compound as a starting material.
    Type: Grant
    Filed: February 26, 2003
    Date of Patent: February 10, 2004
    Assignee: National Institute of Advanced Industrial Science and Technology
    Inventors: Masakazu Nishida, Taizo Ono
  • Patent number: 6670514
    Abstract: Compounds of the formula (I) in which: R1 is H, F, CF3, OCF3, OCF2H, OCFH2, an alkyl radical or an alkenyl radical; R2 is H, an alkyl radical or alkyloxy radical or an alkenyl or alkenyloxy radical; G2—G1 is —CH═CH—, —CH2CH2—, —CF═CH—, —CH═CF—, —CF═CF—, —CH2—, —CF2—; M1, M2 are each, independently of one another, —C(═O)O—, —OC(═O)—, —CH2O—, —OCH2—, —OCF2—, —CF2O—, —C≡C—, —CH2CH2—, —CF2CF2— or a single bond; A1, A2 are each, independently of one another, phenylene-1,4-diyl, unsubstituted, monosubstituted or disubstituted by F, cyclohexane-1,4-diyl, 1,3-dioxan-2,5-diyl; m, n are each, independently of one another, zero or 1; m+n=0 or 1; The invention furthermore provides a liquid-crystal mixture comprising one or more compounds of the formula (I
    Type: Grant
    Filed: August 8, 2002
    Date of Patent: December 30, 2003
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Rainer Wingen, Barbara Hornung, Wolfgang Schmidt
  • Publication number: 20030216594
    Abstract: According to the invention there is proposed a process for the preparation of 4,4,4-trifluoro-3-methylamino-crotonic acid esters by dehydrating trifluoroacetoacetic acid esters and methylamine in the presence of an inert reaction medium and of a C1-C4carboxylic acid, in which process the reaction is carried out at a temperature of from 75 to 100° C. without isolation of intermediates and the water that forms during the reaction is removed continuously from the reaction medium.
    Type: Application
    Filed: March 23, 2001
    Publication date: November 20, 2003
    Inventors: Reinhard Georg Hanreich, Herng-Tay Wu, Michael Allen Oliver, Dean Kent Hoglen
  • Patent number: 6506806
    Abstract: A composition for reducing surface tension comprising from about 0.1% to about 0.5% by weight of a hydrocarbon surfactant and from 0.0001% to about 0.3% by weight of a fluorocarbon surfactant, provided that the hydrocarbon surfactant is present at less than or equal to 0.08% by weight when the fluorocarbon surfactant is present at greater than or equal to 0.
    Type: Grant
    Filed: May 15, 2001
    Date of Patent: January 14, 2003
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Charles Kenneth Taylor, Kai Volker Schubert, Richard David Koehler
  • Patent number: 6392097
    Abstract: Processes for the preparation of parylene dimers, and more particularly to processes for the preparation of derivatives of octafluoro-[2,2]paracylophane, otherwise known as AF4.
    Type: Grant
    Filed: March 20, 2001
    Date of Patent: May 21, 2002
    Assignee: Specialty Coating Systems, Inc.
    Inventors: William R. Dolbier, Jr., Jian-Xin Duan, Alex J. Roche
  • Patent number: 6388146
    Abstract: The polymerizable compound of this invention is represented by general formula (I): where R is H, R′, R′O, R′COO, or R′OCO, R′ is a linear or branched alkyl group or alkenyl group having 1 to about 15 carbon atoms, A1 and A2 are independently a cyclohexane ring or a benzene ring which may include a substituent represented by formula (II) below; X is H or CH3; and Y1, Y2, Y3, and Y4 are independently H, F, Cl, CH3, CH3O, CF3, or CF3O wherein at least two of Y1, Y2, Y3, and Y4 are H and, if both A1 and A2 are cyclohexane rings, at least one of Y1, Y2, Y3, and Y4 is not H: where Y5, Y6, Y7, and Y8 are independently H, F, Cl, CH3, CH3O, CF3, or CF3O, at least two of Y5, Y6, Y7, and Y8 are H.
    Type: Grant
    Filed: January 27, 1999
    Date of Patent: May 14, 2002
    Assignees: Sharp Kabushiki Kaisha, Kanto Kagaku Kabushiki Kaisha
    Inventors: Noriaki Onishi, Aya Miyazaki, Hoyo Mizobe, Masahiko Yoshida, Kenji Suzuki
  • Patent number: 6383454
    Abstract: A process for fluorinating a hydrocarbon substrate is by mixing it with an inert diluent and mixing the diluted substrate with a gaseous fluorinating reagent to form a foam reaction mixture. The fluorinating reagent reacts with the substrate in the form to foam product. The foam is separated into a liquid component which contains product and a gas component. Product is withdrawn from the liquid component which is then returned to the diluting step. Fluorinating reagent is fed into the gas component which is then recirculated to the mixing step. An installation for fluorinating a hydrocarbon substrate includes, in sequence as a circuit, a dilution stage, a mixing stage, a reaction stage and a separation stage. Liquid returning means feeds liquid from the separation stage to the dilution stage, and gas recirculation means feeds gas from the separation stage to the mixing stage.
    Type: Grant
    Filed: July 13, 2001
    Date of Patent: May 7, 2002
    Assignee: South Africa Nuclear Energy Corporation Ltd.
    Inventors: Driekus Van Der Westhuizen, Petrus Johannes Venter
  • Publication number: 20020035300
    Abstract: A process is disclosed for producing the pentafluoropropenes of the formula CF 3 CX═CF 2 , where X is H or Cl. The process involves hydrodehalogenating CF 3 CCl 2 CF 3 with hydrogen at an elevated temperature in the vapor phase over a catalyst comprising an elemental metal, metal oxide, metal halide and/or metal oxyhalide (the metal being copper, nickel, chromium and the halogen of said halides and said oxyhalides being fluorine and/or chlorine).
    Type: Application
    Filed: August 19, 1999
    Publication date: March 21, 2002
    Inventors: V.N. MALLIKARJUNA RAO, ALLEN CAPRON SIEVERT
  • Patent number: 6252099
    Abstract: A process is disclosed for increasing the fluorine content of an olefinic compound of the formula CnHmF2n−m, where n is an integer from 2 to 6 and m is an integer from 1 to 2n. The process involves (a) contacting the olefinic compound with a metal fluoride composition of the formula (AgF)(MF2)x where M is selected from the group consisting of Mn, Fe, Co, Ni, Cu, Zn and mixtures thereof and x is a number from 0 to 1, at a temperature above 200° C. sufficient to transfer F from the metal fluoride composition to the olefinic compound, thereby producing a chemically reduced metal fluoride composition comprising metallic silver; (b) oxidizing the reduced metal fluoride composition from (a) in the presence of HF to regenerate the metal fluoride composition of the formula ((AgF)(MF2)x; and (c) recycling regenerated metal fluoride composition of (b) to (a).
    Type: Grant
    Filed: March 27, 2000
    Date of Patent: June 26, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Munirpallam A. Subramanian
  • Patent number: 6242658
    Abstract: Processes involving certain nickel metallacycles with phosphite ligands are disclosed as useful for the manufacture of selected substituted hydrocarbons. Also disclosed are selected compounds including both nickel and phosphite ligands.
    Type: Grant
    Filed: August 6, 1999
    Date of Patent: June 5, 2001
    Assignee: E. I. duPont de Nemours and Company
    Inventors: Ralph Thomas Baker, Richard Paul Beatty, Allen Capron Sievert, Robert Lewis Wallace, Jr.
  • Patent number: 6242645
    Abstract: Diaryl-, dialkoxyalkyl-, alkylalkoxyalkyl-, arylalkoxyalkyl- and cyclic aminosulfur trifluorides fluorinating agents are disclosed.
    Type: Grant
    Filed: March 23, 2000
    Date of Patent: June 5, 2001
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gauri Sankar Lal, Guido Peter Pez, Reno Joseph Pesaresi, Jr., Robert George Syvret
  • Patent number: 6229057
    Abstract: There is provided a process for the preparation of 1,1,1-trichlorotrifluororethane in which 1,1-dichloro-2,2,2-trifluoroethane is subjected to chlorination by bringing the 1,1-dichloro-2,2,2-trifluoroethane into contact with chlorine within a reaction vessel characterised in that the process is conducted in the liquid phasein the presence of a chemical free radical initiator under a pressure of from 1 to 20 bar and at a temperature within the range 50 to 120° C., and the product is separated from the reaction mixture by fractional distillation. The product is useful in the manufacture of insecticides.
    Type: Grant
    Filed: January 11, 1996
    Date of Patent: May 8, 2001
    Assignee: Zeneca Limited
    Inventors: Alan Raymond Jackson, Sean James Doyle, Keith Moorhouse, Thomas Gray
  • Patent number: 6222064
    Abstract: A fluorination method of oxygen and halogen sites with diaryl-, dialkoxyalkyl-, alkylalkoxyalkyl-, arylalkoxyalkyl- and cyclic aminosulfur trifluorides fluorinating reagents is disclosed.
    Type: Grant
    Filed: January 14, 2000
    Date of Patent: April 24, 2001
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gauri Sankar Lal, Guido Peter Pez
  • Patent number: 6194619
    Abstract: A catalyic process is disclosed for producing fluorine-substituted hydrocarbon products of the formulae RCH2CF2R and RFC═CHR at an elevated temperature, from compounds of the formula RCHFCHFR, where each R is independently selected from the group consisting of —CF3, —CF2CF3 and —CF2CF2CF3 or where both R groups of a formula together are —(CF2)2—, —(CF2)3— or —(CF2)4—. Suitable catalysts include carbon catalysts and catalysts containing at least one compound of a selected metal (e.g., Na, K, Rb, Cs, Y, La, Ce, Pr, Nd, Sm, Cr, Fe, Co, Rh, Ni, Cu, and/or Zn) supported on carbon. The saturated gem-dihydro- products may also be produced by hydrofluorinating the corresponding olefinic product over such catalysts at an elevated temperature, and can be combined with various other miscible solvents to form compositions useful for cleaning.
    Type: Grant
    Filed: September 10, 1993
    Date of Patent: February 27, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: V. N. Mallikarjuna Rao, Frank Julian Weigert, Carl G. Krespan
  • 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: 6166156
    Abstract: Halofluorinated alkylene monomers are made by a method comprising the steps of: (a) subjecting a first polymer which is the reaction product of a fluorinated vinyl monomer and a vinyl comonomer to dehydrohalogenation to form a second polymer; (b) treating the second polymer with an oxidizing agent to form an oxidation product consisting of a .alpha., .omega.-dicarboxylic acid or an ester derivative thereof; and (c) treating said oxidation product with a reducing agent to form a reduction product consisting of a a .alpha., .omega.-diol. Preferably, the first polymer has a structure of --[CH.sub.2 CYZ(CF.sub.2 CFX).sub.n ].sub.m -- wherein X and Y=F, Cl or Br; X and Y may be the same or different; Z=H, F, Cl, Br, alkyl or perfluoroalkyl containing from about 1 to about 10 carbon atoms; n=an integer larger than about 1; and m is an integer between about 2 and about 10.sup.5. The .alpha., .omega.-dicarboxylic acids and .alpha., .omega.-diols produced herein can be directly used as polycondensation monomers.
    Type: Grant
    Filed: November 12, 1998
    Date of Patent: December 26, 2000
    Inventors: Chengjiu Wu, Baopei Xu, James T. Yardley
  • Patent number: 6127585
    Abstract: Processes are disclosed for decreasing the chlorine to carbon ratio for halogenated hydrocarbons containing chlorine and from 1 to 6 carbon atoms, in the presence of a multiphase catalyst. The processes each involve (1) preparing a single phase solid catalyst precursor which has a structure that collapses at a temperature of about 400.degree. C. or less and has the formula (NH.sub.3).sub.6 Ru.sub.l-r-s Co.sub.r Cr.sub.s MF.sub.6, where r+s is in the range of 0.00 to 0.99, and M is at least one trivalent metal selected from the group consisting of Al, Cr, Fe, V, Sc and Ga; and (2) producing the multiphase catalyst by heating the single phase solid catalyst precursor to about 400.degree. C. or less in an non-oxidizing atomsphere to produce a multiphase composition wherein a phase containing ruthenium is homogeneously dispersed with a phase containing metal fluoride.Also disclosed are single phase fluoride compositions having the formula (NH.sub.3).sub.6 Ru.sub.l-r-s Co.sub.r Cr.sub.s MF.sub.
    Type: Grant
    Filed: May 27, 1998
    Date of Patent: October 3, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Timothy C. Duzick, Velliyur Nott Mallikarjuna Rao, Munirpallam A. Subramanian
  • Patent number: 6120697
    Abstract: A method of etching comprising subjecting a material under plasma etching conditions to an etching composition comprising at least an etchant compound having the formula C.sub.X H.sub.C F.sub.Zwherein: x=3, 4 or 5;2x.gtoreq.z.gtoreq.y;and y+z=2x+2; andfurther including an etching composition which includes said etchant compound and a second material different from the etchant compound that enhances or modifies plasma etching.
    Type: Grant
    Filed: December 31, 1997
    Date of Patent: September 19, 2000
    Assignee: AlliedSignal Inc
    Inventors: Timothy R. Demmin, Matthew H. Luly, Mohammed A. Fathimulla
  • Patent number: 6096926
    Abstract: The subject-matter of the present invention is a process of use in perfluoroalkylation and a reactant for making use of this process. This process is defined in that it comprises a stage in which a material of formula RfH and a base (or a species capable of generating a base) are brought into contact, in a polar and anhydrous medium, with a substrate carrying at least one electrophilic functional group. Application to organic synthesis.
    Type: Grant
    Filed: February 22, 1999
    Date of Patent: August 1, 2000
    Assignee: Rhodia Chimie
    Inventors: Nicolas Roques, James Russel
  • Patent number: 6040485
    Abstract: The invention relates to novel fluorinated organic compounds having the following molecular structure: ##STR1## where R.sub.F is a fluorinated carbon chain, R.sub.1H is hydrogen or a saturated hydrogenated carbon chain, R.sub.2H is hydrogen or a saturated hydrogenated carbon chain, R.sub.1H and R.sub.2H being not simultaneously hydrogen, the group ##STR2## comprising a principal chain and at least one linear or cyclic branch. These compounds may be prepared by reacting a phosphine with a halide under heating, and then hot reacting in a solvent the resulting phosphonium salt with a branched aldehyde or a ketone. These compounds have an excellent stability, a good biocompatibility and a high capacity to solubilize gases and particularly oxygen, such properties allowing their use in applications of the ophthalmological type or as an organ preservation medium.
    Type: Grant
    Filed: February 26, 1998
    Date of Patent: March 21, 2000
    Assignee: Chauvin Opsia
    Inventors: Isabelle Lattes, Bernard Feurer, Brigitte Guidetti, Viviane Payrou
  • Patent number: 5981422
    Abstract: Stoichiometric and catalytic chemical transformations may be carried out in solution using novel fluorous multiphase systems (FMS). The term "fluorous" is defined as a carbon-fluorine bond rich organic molecule which is generated by replacing hydrogen atoms bonded to carbon atoms with fluorine. The novel complexes suitable for use as fluorous catalysts and reagents in the present invention contain sufficient number of fluorous moieties to render them preferentially soluble in the appropriate fluorous solvent without impairing the ability of the catalyst or reagent to be effective or participate in the corresponding reaction.
    Type: Grant
    Filed: August 26, 1997
    Date of Patent: November 9, 1999
    Assignee: Exxon Research and Engineering Co.
    Inventors: Istvan Tamas Horvath, Jozsef Rabai
  • Patent number: 5780672
    Abstract: A process for the preparation of compounds of the formula (1) in which R.sup.1, R.sup.2 and R.sup.3 are as defined in the specification, which includes reacting alcohols or carboxylic acids of the formula (2) in which R.sup.1, R.sup.2 and R.sup.3 are as defined in the specification, with a fluorinating agent of the formula (3) as defined in the specification.
    Type: Grant
    Filed: July 11, 1996
    Date of Patent: July 14, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Sergej Pasenok, Wolfgang Appel
  • 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: 5665270
    Abstract: An optically active compound derived from a novel trifluorolactic acid, useful as a component of a ferroelectric liquid crystal composition, and a liquid crystal composition. A compound represented by general formula (I), wherein R.sup.1 represents C.sub.1 to C.sub.18 alkyl, alkoxy, C.sub.2 to C.sub.18 alkanoyl, alkanoyloxy or alkoxycarbonyl; R.sup.2 represents optionally alkoxy-substituted alkyl (where the total number of the carbon atoms is 1 to 15); A, B and C represent each independently the group (a) or (b); v and w represent each independently --COO--, --OCO--, --CH.sub.2 O--, --OCH.sub.2 --, --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH--, --C.dbd.C-- or a single bond; and x and y together represent any of the following combinations: --COO-- and --COO--; --COO-- and --CO--; --COO-- and --CH.sub.2 O--; --COO-- and --CH.sub.2 OCO--; --COO-- and --CH.sub.2 OCOO--; --O-- and --CH.sub.2 O--; --O-- and --CH.sub.2 OCO--; and --O-- and --CH.sub.2 OCOO--.
    Type: Grant
    Filed: May 4, 1994
    Date of Patent: September 9, 1997
    Assignee: Chisso Corporation
    Inventors: Masatoshi Fukushima, Shinichi Saito
  • Patent number: 5648566
    Abstract: Monomers of the formula (I) (for example, 3,3,4,4,5,5,6,6-octafluoromethylenecyclopentane) are described, as well as copolymers prepared from them and from one or more monomers copolymerizable with them. ##STR1## wherein n=3 to 5 The compounds are suitable for the production of a multiplicity of thermoplastically processable copolymers having various sets of properties which permit applications both as compact moulded parts and as coatings.
    Type: Grant
    Filed: May 31, 1995
    Date of Patent: July 15, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ralf Kruger, Michael Negele, Norbert Lui, Albrecht Marhold
  • Patent number: 5600036
    Abstract: 2-Trifluoromethyl-4-chloro-benzalchloride and 2-methyl-3-nitro-5-chlorobenzotrifluoride, are intermediates in a process of preparing 2-methyl-3-aminobenzo-trifluoride. In this process, 2-trifluoromethyl-4-chlorobenzal-chloride is prepared by chlorinating o-trifluoromethylbenzalhalide, and 2-methyl-3-nitro-5-chlorobenzotrifluoride is prepared at first by hydrogenating the 2-trifluoro-methyl-4-chlorobenzalhalide to form a 2-methyl-5-monochlorobenzotrifluoride and then by nitrating the 2-methyl-5-monochlorobenzotrifluoride. Following this process, 2-methyl-3-aminobenzotrifluoride (MA-BTF) is prepared by hydrogenating the 2-methyl-3-nitro-5-chlorobenzotrifluoride. The thus prepared 2-methyl-3-aminobenzotrifluoride is useful as an intermediate in preparing medicines, agricultural chemicals and other chemical products.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: February 4, 1997
    Assignee: Central Glass Company, Limited
    Inventors: Takayuki Nishimiya, Masatomi Kanai, Toshikazu Kawai
  • Patent number: 5498807
    Abstract: The invention relates to a process for the preparation of aromatic fluoro compounds of the formula IF.sub.n ArR.sup.1 R.sup.2 R.sup.3 (I)in which Ar is phenyl, naphthyl or pyridyl, R.sup.1, R.sup.2 and R.sup.3 independently of one another are hydrogen, halide, (C.sub.1 -C.sub.4)-alkyl, phenyl, NR.sub.2, OR, CN, COH or COR, where R is hydrogen or (C.sub.1 -C.sub.6)-alkyl, and n=1, 2, 3, 4 or 5,which comprises reacting aromatic fluoro compounds of the formula IIX.sub.m F.sub.n ArR.sup.1 R.sup.2 R.sup.3 (II)in which Ar, R.sup.1, R.sup.2, R.sup.3 and n have the abovementioned meaning, each X is a chlorine or bromine atom and m=1, 2, 3, 4 or 5, with hydrogen in the presence of a palladium catalyst, a water-insoluble amine which also does not form water-soluble hydrohalides, and if desired an inert solvent.
    Type: Grant
    Filed: November 9, 1994
    Date of Patent: March 12, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Thomas Schach, Theodor Papenfuhs
  • Patent number: 5495034
    Abstract: A method for the preparation of .alpha.-substituted .omega.-dihydroperluoroalkane derivatives of the general formula H(CF.sub.2 CF.sub.2).sub.n R wherein R=H or COOH, and n=1-10 is characterized by oxidizing .alpha., .alpha., .omega.-trihydroperfluoroalcohols with an oxygen gas or an oxygen-containing gas in the presence of a homogeneous copper catalyst and an alkaline agent in an organic solvent with subsequent isolation of the desired product.
    Type: Grant
    Filed: July 15, 1994
    Date of Patent: February 27, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Irina P. Skibida, Andrei M. Sakharov, Jury L. Bakhmutov, Vladimir F. Denisenkow, Nina P. Martynova
  • Patent number: 5350878
    Abstract: This invention provides 1) novel reactive fluorinated compounds derived from a specified class of telomers or cotelomers of fluoroolefins; and 2) stable products and stable polymers thereof obtained by reaction or polycondensation of the novel reactive fluorinated compounds with specified classes of hydrogenated aliphatic, alicyclic, aromatic reactive compounds, telechelic oligomers and block polymers wherein said stable products and polymers contain hetero atoms such as oxygen, sulfur or nitrogen and are characterized by high thermal and chemical resistance.
    Type: Grant
    Filed: February 10, 1993
    Date of Patent: September 27, 1994
    Assignee: Dow Corning Corporation
    Inventor: Gerardo Caporiccio
  • Patent number: 5306849
    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
  • Patent number: 5288932
    Abstract: The present invention relates to a method for the production of substituted or unsubstituted chloromethyl and bromomethyl cyclopropane having a degree of purity above 85%, particularly above 90%, by reacting a hydroxymethyl cyclopropane of the formula ##STR1## where R is H, or one or two R groups are alkyl of from 1 to 10 carbon atoms or phenyl, with methane sulfonic acid chloride or methane sulfonic acid bromide in the presence of a trialkylamine and, if necessary, an organic solvent, preferably an organic solvent containing oxygen, at a temperature of from -20.degree. C. to +30.degree. C. over a period of time of from 1 to 30 hours, then heating the reaction mixture to a temperature of from 40.degree. to 80.degree. C., or to reflux temperature, without isolating the intermediate mesylate.
    Type: Grant
    Filed: March 30, 1993
    Date of Patent: February 22, 1994
    Assignee: Huels Aktiengesellschaft
    Inventor: Manfred Kaufhold
  • Patent number: 5276221
    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: January 25, 1993
    Date of Patent: January 4, 1994
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Carl G. Krespan
  • Patent number: 5268516
    Abstract: The invention relates to a continuous process for the preparation of perfluoroalkyl iodides containing from 4 to 12 carbon atoms by thermal telomerization of tetrafluoroethylene by pentafluoroethyl iodide or heptafluoroisopropyl iodide in a tubular reactor.According to the invention, 30 to 75% of the tetrafluoroethylene is supplied at the head of the reactor; the remainder is introduced at a point in the reactor located between the 2/5 and 3/4 of the length of the tube.The proportion of undesirable heavy telomers is reduced in this way.
    Type: Grant
    Filed: January 13, 1993
    Date of Patent: December 7, 1993
    Assignee: Elf Atochem S.A.
    Inventors: Rene Bertocchio, Georges Lacote, Christophe Verge
  • Patent number: 5220082
    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: June 25, 1992
    Date of Patent: June 15, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Carl G. Krespan
  • Patent number: 5108556
    Abstract: A process for preparing tertiary perfluoroamines is provided. The process comprises electrochemically fluorinating a tertiary thioamide precursor, said thioamide precursor having at least one thioamide moiety, ##STR1## and terminal portions which can be alkyl or cycloalkyl having 1 to 12 carbon atoms, aryl having 6 to 12 carbon atoms, or combinations thereof, with the proviso that when more than one thioamide moiety is present, the thioamide moieties are bonded together by alkylene, cycloalkylene or arylene groups. Also provided are tertiary thioamides and tertiary perfluoroamines.
    Type: Grant
    Filed: September 14, 1990
    Date of Patent: April 28, 1992
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Jack E. Richman
  • Patent number: 5084199
    Abstract: The compound 1,1,2,2,3,3-hexafluorocyclopentane and mixtures thereof with alcohols, ethers, esters, ketones, nitromethane, and halogenated hydrocarbons are disclosed; as is a process for cleaning a solid surface which comprises treating the surface with said compound or said mixtures. Binary mixtures of 1,1,2,2,3,3-hexafluorocyclopentane either with about 27 to 35 weight percent methanol, or with about 21 to 29 weight percent ethanol are disclosed as azeotrope or azeotrope-like compositions and are particularly suited for use where solvent recovery and reuse is practiced.
    Type: Grant
    Filed: October 9, 1990
    Date of Patent: January 28, 1992
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Robert D. Anton
  • Patent number: 4966988
    Abstract: A method is provided for forming (3-trifluoromethylphenyl)acetonitrile through the intermediate .alpha.,.alpha.,.alpha.-trifluoro-.alpha.'-chloro-m-xylene. This intermediate is formed by selective chlorination of .alpha.,.alpha.,.alpha.'-trichloro-m-xylene under conditions which maximize yield and minimize the formation of undesired, non-recyclable chlorinated by-products.
    Type: Grant
    Filed: February 17, 1989
    Date of Patent: October 30, 1990
    Assignee: Chevron Research Company
    Inventors: William L. Schinski, Peter Denisevich, Jr.
  • Patent number: 4954666
    Abstract: This invention relates to a process for preparing fluorinated C.sub.4 to C.sub.6 hydrocarbons by catalytically hydrogenating, in the presence of a base, at least partially halogenated olefins. This invention also relates to certain novel cyclic fluorinated C.sub.5 and C.sub.6 hydrocarbons prepared by the process of this invention. This invention further relates to the use of fluorinated C.sub.4 to C.sub.6 hydrocarbons as propellant gas or as working fluid for heat pump systems.
    Type: Grant
    Filed: December 21, 1989
    Date of Patent: September 4, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dietmar Bielefeldt, Albrecht Marhold, Michael Negele
  • Patent number: 4739057
    Abstract: A process for converting organic hydroxyl-containing compounds to halides which comprises reacting the hydroxyl-containing compound with a phosphorushalide reagent of formula: R.sub.n PX.sub.5-n wherein n is selected from 1, 2 and 3; R is selected from the group consisting of C-6 to C-10 aryl and substituted aryl wherein the substituents are selected from the group consisting of straight and branched chain alkyl, alkoxy, and haloalkyl, halogen, sulfonate and mixtures thereof; and X is a halogen. It is preferred to carry out the reaction in the presence of an arylphosphorusoxydihalide solvent. The use of an arylphosphorustetrahalide and particularly phenylphosphorustetrachloride is preferred. The arylphoshorustetrahalide can be prepared in situ by contacting a solution of the corresponding arylphosphorusdihalide in an arylphosphorusoxydihalide solvent with a halogen. The process can further comprise the step of heating the reaction mixture. Maintaining a reaction temperature of from about 0.degree. C.
    Type: Grant
    Filed: June 30, 1986
    Date of Patent: April 19, 1988
    Assignee: Stauffer Chemical Co.
    Inventors: Andrea Leone-Bay, Elliott Bay, Peter E. Timony
  • Patent number: 4731450
    Abstract: A process for the perfluoroalkylation of aromatic derivatives. In a first stage, an aromatic derivative, sulfur dioxide and a metal selected from the group consisting of zinc, aluminum, manganese, cadmium, magnesium, tin, iron, nickel and cobalt, are brought into contact in a solvent, preferably a polar aprotic solvent. In a second stage, a perfluoroalkyl bromide or iodide is added to react with the aromatic derivative.
    Type: Grant
    Filed: May 21, 1986
    Date of Patent: March 15, 1988
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventors: Claude Wakselman, Marc Tordeux
  • Patent number: 4243615
    Abstract: A process for preparing a novel chemical compound poly-dicarbon monofluoride represented by the formula (C.sub.2 F).sub.n and having a crystalline structure of packing form featured by its layer structure stacked with an interlayer spacing of about 9.0 A. Such process consists in that a particulate carbon material having a specific crystallinity is reacted with fluorine at 300.degree. to 500.degree. C. According to the process, the desired product can be obtained in a yield as high as 100% with respect to not only the carbon material employed but also the fluorine employed.
    Type: Grant
    Filed: June 29, 1979
    Date of Patent: January 6, 1981
    Assignees: Watanabe Applied Science Research Institute, Nobuatsu Watanabe
    Inventors: Nobuatsu Watanabe, Yasushi Kita
  • Patent number: RE30667
    Abstract: A novel chemical compound poly-dicarbon monofluoride represented by the formula (C.sub.2 F).sub.n and having a crystalline structure of packing form .[.featured by its layer structure as shown in FIG. 12 hereof.]. stacked with an interlayer spacing of about 9.0 A. Such new compound can be produced under relatively mild reaction conditions and obtained in a yield as large as 100% with respect to not only the carbon material employed but also the fluorine employed. The new compound is black under the formation conditions and of low crystallinity, but it can be easily converted to that of high crystallinity and white color by heat treatment in a fluorine atmosphere. The new compound has a wide variety of uses, for example, as lubricants, stain-resistant and water-repellent materials, cathode materials in high energy primary cells, etc.
    Type: Grant
    Filed: July 6, 1979
    Date of Patent: July 7, 1981
    Assignees: Nobuatsu Watanabe, Applied Science Research Institute
    Inventors: Nobuatsu Watanabe, Yasushi Kita