Fluorine In Acid Moiety Patents (Class 560/227)
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Patent number: 6720447Abstract: The present invention relates to a novel process for the preparation of esters of the general formula I from compounds of the general formula II contained in aqueous solutions which comprises a) extracting the compounds of the general formula II directly or after liberation from their salts in the presence of a C1-C8-alcohol and a water-immiscible solvent and b) then esterifying with the C1-C8-alcohol in the presence of a catalyst and of an entraining agent under the conditions of an azeotropic distillation, where the process steps (a) and (b) can be carried out separately in terms of time and space or else in a successive continuous or batchwise sequence and where the variables and substituents in the formulae I and II have the following meanings: R1=F, Cl, —OH, —OC1-C10-alkyl, R2=H, C1-C10-alkyl; R3=C1-C8-alkyl, Q=—OH, —O−K+, where K+ is an alkali metal cation or alkaline earth metal cation, n&equType: GrantFiled: July 17, 2001Date of Patent: April 13, 2004Assignee: BASF AktiengesellschaftInventors: Klaus Ditrich, Ulrich Block
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Patent number: 6706193Abstract: Fluorinated emulsifiers can be recovered from an aqueous phase containing small amounts of fluoropolymer particles by treating the aqueous phase with a small amount of a nonionic surface-active agent, bringing the aqueous phase adjusted in this way into contact with an anionic exchanger resin, and liberating the adsorbed emulsifier from the exchanger resin. The finely divided fluoropolymer can be precipitated quantitatively in the untreated aqueous phase or the eluate using flocculating agents.Type: GrantFiled: December 11, 2001Date of Patent: March 16, 2004Assignee: 3M Innovative Properties CompanyInventors: Georg Burkard, Klaus Hintzer, Gernot Löhr
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Patent number: 6703521Abstract: Compounds of formula CH2Y—CH(COOR1)—O—CF2CF2—SO2F, usable in the synthesis of the fluorosulphonic vinylether —CF2═CF—O——CF2CF2—SO2F.Type: GrantFiled: December 27, 2002Date of Patent: March 9, 2004Assignee: Ausimont S.p.A.Inventors: Vito Tortelli, Sara Maculan
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Publication number: 20040024243Abstract: The present invention relates to a fluorination method for the synthesis of halofluoroorganic compounds which can be used, inter alia, as precursors in the synthesis of 2,3-unsaturated fluoroorganic carbonyl compounds comprising a fluorine substituent in the 2 position.Type: ApplicationFiled: February 5, 2003Publication date: February 5, 2004Inventors: Veronique Mathieu, Francine Janssens, James Franklin
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Patent number: 6683202Abstract: The invention discloses a novel ester compound of an unsaturated carboxylic acid represented by the general formula in which R1 is preferably a hydrogen atom or methyl group, R2 is preferably a trifluoromethyl group, R3 is a non-aromatic polycyclic hydrocarbon group or, preferably, an adamantyl group and R4 is preferably a hydrogen atom or methyl group. This unsaturated ester compound is polymerizable to give a (co)polymeric resin which can be used as a base resinous ingredient in a photoresist composition for light exposure with ultraviolet light of a very short wavelength by virtue of the high transparency to the short-wavelength light. A synthetic method for the preparation of the novel ester compound is disclosed.Type: GrantFiled: February 22, 2002Date of Patent: January 27, 2004Assignee: Tokyo Ohka, Kogyo Co., Ltd.Inventors: Toshiyuki Ogata, Kotaro Endo, Hiroshi Komano
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Publication number: 20030216595Abstract: The present invention provides a method for producing industrially useful fluorine-containing compounds such as a fluorinated ester compound and an acid fluoride compound.Type: ApplicationFiled: March 27, 2003Publication date: November 20, 2003Applicant: ASAHI GLASS COMPANY LIMITEDInventors: Takashi Okazoe, Kunio Watanabe, Shin Tatematsu, Koichi Yanase, Yasuhiro Suzuki, Daisuke Shirakawa
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Publication number: 20030208090Abstract: A liquid phase process is disclosed for producing halogenated alkane adducts of the formula CAR1R2CBR3R4 (where A, B, R1, R2, R3, and R4 are as defined in the specification) which involves contacting a corresponding halogenated alkane, AB, with a corresponding olefin, CR1R2═CR3R4 in a dinitrile or cyclic carbonate ester solvent which divides the reaction mixture into two liquid phases and in the presence of a catalyst system containing (i) at least one catalyst selected from monovalent and divalent copper; and optionally (ii) a promoter selected from aromatic or aliphatic heterocyclic compounds which contain at least one carbon-nitrogen double bond in the heterocyclic ring. When hydrochlorofluorocarbons are formed, the chlorine content may be reduced by reacting the hydrochlorofluorocarbons with HF.Type: ApplicationFiled: June 12, 2003Publication date: November 6, 2003Inventors: Ralph Thomas Baker, Ralph Newton Miller, Viacheslav Alexandrovich Petrov, Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
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Patent number: 6642409Abstract: A first process for producing an optically active perfluoroalklylcarbinol derivative includes (a) reacting an optically active imine with a compound that is a hemiacetal of a perfluoroalkylaldehyde or a hydrate of a perfinoroalkylaldehyde to obtain a condensate; and (b) hydrolyzing the condensate under an acid condition. A second process for increasing optical purity of an optically active 4,4,4-trifluoro-3-hydroxy-1-aryl-1-butanone derivative includes (a) precipitating a racemic crystal of the derivative, from the derivative; and (b) removing the racemic crystal from the derivative. A third process for increasing optical purity of the butanone derivative (includes recrystallizing the derivative. Novel compounds are optically active and inactive 4,4,4-trifluoro-3-hydroxybotanoic aryl ester derivatives.Type: GrantFiled: January 29, 2001Date of Patent: November 4, 2003Assignee: Central Glass Company, LimitedInventors: Akihiro Ishii, Masatomi Kanai, Takashi Hayami, Katsuyoshi Shibata, Masaki Matsui, Kazumasa Funabiki, Yokusu Kuriyama, Manabu Yasumoto
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Patent number: 6639100Abstract: A process for producing an optically active perfluoroalkylcarbinol by reacting an optically active imine with a hemiacetal or hydrate of a perfluoroalkylaldehyde to obtain a condensate, and hydrolyzing the condensate under acidic conditions. Optical purity of optically active 4,4,4-trifluoro-3-hydroxy-1-aryl-1-butanone compounds may be increased by precipitating and removing a racemic crystal, and also recrystallizing the compound. Novel compounds include optically active and inactive 4,4,4-trifluoro-3-hydroxybutanoic aryl esters. A process for producing optically active or incactive 4,4,4-trifluoro-3-hydroxybutyric acid aryl esters includes oxidizing an optically active or inactive 4,4,4-trifluoro-3-hydroxy-1-aryl-1-butanone. Optical purity of optically active aryl esters may be increased by recrystallization. Optically active 4,4,4-trifluoro-1,3-butanediol may be produced by reducing the optically active aryl ester with a hydride.Type: GrantFiled: August 7, 2002Date of Patent: October 28, 2003Assignee: Central Glass Company, LimitedInventors: Akihiro Ishii, Masatomi Kanai, Takashi Hayami, Katsuyoshi Shibata, Masaki Matsui, Kazumasa Funabiki, Yokusu Kuriyama, Manabu Yasumoto
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Publication number: 20030166969Abstract: A fluorinated polyvalent carbonyl compound is produced by an economically advantageous method from inexpensive materials without requiring a complicated synthetic process step. Namely, the present invention comprises reacting a polyvalent alcohol having at least two kinds of alcohol skeletons selected among a primary alcohol, a secondary alcohol and a tertiary alcohol, with an acid halide to obtain a polyvalent ester compound, fluorinating it in a liquid phase to obtain a perfluorinated polyvalent ester compound, and cleaving the ester bonds derived from primary and secondary alcohols in the perfluoropolyvalent ester compound to obtain a fluorinated polyvalent carbonyl compound.Type: ApplicationFiled: March 27, 2003Publication date: September 4, 2003Applicant: ASAHI GLASS COMPANY LIMITEDInventors: Takashi Okazoe, Kunio Watanabe, Daisuke Shirakawa, Masahiro Ito, Shin Tatematsu
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Patent number: 6583313Abstract: The methyl and ethyl esters of trifluoroacetic acid or chlorodifluoroacetic acid can be prepared in a technically simple manner from the corresponding acid chlorides and methanol or ethanol, respectively, in the presence of an “onium” salt of the acid as a catalyst. The alcohol is used in a stoichiometric excess, namely the molar ratio of alcohol to acid chloride is selected such that operation is in the region of a two-phase reaction. One of the phases is formed by the desired ester product, which is obtained in a high purity without any distillation.Type: GrantFiled: July 10, 1998Date of Patent: June 24, 2003Assignee: Solvay Fluor und Derivate GmbHInventors: Max Braun, Kerstin Eichholz, Werner Rudolph
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Patent number: 6452056Abstract: A fluorine-containing benzonitrile derivative (formula 1) is subjected to a reduction reaction to obtain a fluorine-containing benzylamine derivative (formula 2), and the amino group in said fluorine-containing benzylamine derivative is replaced with a hydroxyl group to obtain a fluorine-containing benzyl alcohol derivative (formula 3): wherein X is a halogen atom, when m is an integer of 2 or more, each X may be the same or different, and m is an integer of from 0 to 4.Type: GrantFiled: February 20, 2001Date of Patent: September 17, 2002Assignee: Asahi Glass Company, LimitedInventors: Tsuneo Kawanobe, Osamu Takazawa, Keisuke Yoshikawa, Hiroyuki Watanabe
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Patent number: 6437174Abstract: The present invention concerns a method for producing esters of 2-fluoro-iso butyric acid in which the corresponding 2-hydroxyisobutyric acid ester is reacted with hydrofluoric acid.Type: GrantFiled: March 29, 1999Date of Patent: August 20, 2002Assignee: Hoechst Schering AgrEvo GmbHInventors: Wolfgang Appel, Sergej Pasenok
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Patent number: 6436244Abstract: Fluorinated emulsifier acids bound to an anion exchanger resin can be eluted using a mixture of water, a compound of the formula M—X, in which M is an alkali metal or an alkylammonium ion, and X is hydroxyl, fluoride or chloride, and at least one organic solvent which completely dissolves the other components. For work-up of the eluent, this is advantageously subjected to steam distillation until all volatile constituents have been essentially removed, and the emulsifier acid is liberated from the steam distillation residue using a sufficiently strong acid. This emulsifier acid can advantageously be distilled off and collected as the ammonium salt in aqueous ammonia solution.Type: GrantFiled: June 30, 2000Date of Patent: August 20, 2002Assignee: Dyneon GmbHInventors: Stephan Führer, Gernot Löhr, Werner Schwertfeger
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Patent number: 6403346Abstract: Enzymatic processes can produce intermediates for manufacturing retiferol derivatives that are useful for treating or preventing hyperproliferative skin diseases and for reversing conditions associated with photodamage. These processes can use as a starting material trihydroxycyclohexane, which can be chemically modified by a process that includes an enzymatic step, typically involving lipases of EC-class 3.1.1.3 or 3.1.1.34.Type: GrantFiled: September 6, 2001Date of Patent: June 11, 2002Assignee: Basilea Pharmaceutica AGInventors: Hans Hilpert, Beat Wirz
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Patent number: 6376705Abstract: Esters and other carboxylic acid derivatives of 3,3,4,4-tetrahydroperfluoroalkylcarboxylic acids are made by the iron promoted reaction of an ester of bromodifluoroacetic acid or other carboxylic acid derivatives and a (perfluoroalkyl)ethylene. The resulting products may be converted to the corresponding alkali metal or ammonium carboxylate slits which are useful as surfactants in fluoroolefin polymerizations.Type: GrantFiled: May 22, 2000Date of Patent: April 23, 2002Assignee: E. I. du Pont de Nemours and CompanyInventor: Weiming Qiu
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Patent number: 6348622Abstract: There is provided a compound of the formula[I]: wherein R represents a hydrogen atom or a protective group for a hydroxyl group; and A represents a hydrogen atom, a halogen atom or a group of the formula A1: Q represents Q3: when A represents a halogen atom or a protective group for a hydroyl group, A represents Q4: wherein R1 and R2 represent a hydrogen atom or a protective group for a hydroxyl group; and when A represents a hydrogen atom, Q is Q2:Type: GrantFiled: February 9, 2000Date of Patent: February 19, 2002Assignee: Sumitomo Chemical Company, LimitedInventors: Toshiya Takahashi, Shinzo Seko, Takashi Miki
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Patent number: 6300532Abstract: A process for catalytic addition of haloalkanes to alkenes involving the step of reacting the haloalkane with the alkene in the presence of a catalyst. The catalyst is an organophosphite compound represented by the following formula: P(ORa)(ORb)(ORc), where Ra, Rb, and Rc are each an alkyl group or an aralkyl group.Type: GrantFiled: December 15, 1998Date of Patent: October 9, 2001Assignee: AlliedSignal Inc.Inventors: Michael Van Der Puy, Timothy Rech Demmin
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Patent number: 6291730Abstract: A liquid phase process is disclosed for producing halogenated alkane adducts of the formula: CAR1R2CBR3R4 (where A, B, R1, R2, R3, and R4 are as defined in the specification) which involves contacting a corresponding halogenated alkane, AB, with a corresponding olefin, CR1R2═C3R4 in a dinitrile or cyclic carbonate ester solvent which divides the reaction mixture into two liquid phases and in the presence of a catalyst system containing: (i) at least one catalyst selected from monovalent and divalent copper; and optionally (ii) a promoter selected from aromatic or aliphatic heterocyclic compounds which contain at least one carbon-nitrogen double bond in the heterocyclic ring. When hydrochlorofluorocarbons are formed, the chlorine content may be reduced by reacting the hydrochlorofluorocarbons with HF. New compounds disclosed include CF3CF2CCl2CH2CCl3, CF3CCl2CH2CH2Cl and CF3CCl2CH2CHClF. These compounds are useful as intermediates for producing hydrofluorocarbons.Type: GrantFiled: January 28, 1998Date of Patent: September 18, 2001Assignee: E. I. du Pont de Nemours and CompanyInventors: Ralph Thomas Baker, Viacheslav Alexandrovich Petrov, Velliyur Nott Mallikarjuna Rao, Allen Capron Sievert
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Patent number: 6291704Abstract: Vinyl ether compounds having the formula: R—O—X—O—CH═CH2 wherein R is a radical selected from R1—CnHm—, R1—CnHm—C(═O)—, R1—CnHm—CH[—O—X—O—CH═CH2—], R1—CnHm—CH[—O—X—O—CH═CH2—]C(═O)—, R1—CnHm—CH[—C(═O)—O—X—O—CH═CH2—], R1—CnHm—CH[—C(═O)—O—X—0—CH═CH2—]C(═O)—, R1—[CFCl—CF2—]pCH2— and HCFCl—CF2—, wherein R1 is hydrogen, an unsubstituted or substituted fluorinated aliphatic radical, an unsubstituted or substituted fluorinated cyclic aliphatic radical, an unsubstituted or substituted fluorinated aromatic radical, an unsubstituted or substituted fluorinated araliphatic radical, or an unsubstituted or substituted fluorinated heterocyclic radiType: GrantFiled: March 18, 1999Date of Patent: September 18, 2001Assignee: AlliedSignal Inc.Inventors: Russell F. Anderson, David E. Bradley, David Nalewajek, Haridasan K. Nair, Mariola J. Proszowski, Eugene V. Sitzman, Ellen L. Swan
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Patent number: 6278015Abstract: The present invention provides a process for preparing esters or thioesters of trifluoroacetic acid from trifluoroacetyl chloride and an alcohol or a thiol with the ester or thioester being present as the solvent. Esters and thioesters of trifluoroacetic acid are fine chemical intermediates which can be used in the manufacture of pharmaceuticals, agricultural chemicals, liquid crystals, dyes and industrial chemicals. Trifluoroacetate esters and thioesters can also be used as solvents in the manufacture of other fine chemicals, pharmaceuticals, agricultural chemicals, liquid crystals, industrial chemicals and dyes.Type: GrantFiled: July 17, 2000Date of Patent: August 21, 2001Assignee: Rohm and Haas CompanyInventors: Lori Ann Spangler, Fereydon Abdesaken, Joshua Anthony Chong
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Patent number: 6255524Abstract: An acid chloride can be produced at a high yield from a primary alcohol having a polyfluoroalkyl group and one methylene group by (1) a method in which RfCH2OH (wherein Rf is a polyfluoroalkyl group) is reacted with chlorine to produce RfCOCl, (2) a method in which RfCHO is reacted with chlorine to produce RfCOCl, and (3) a method for producing an acid chloride comprising (a) a step in which an aldehyde (RfCHO) is formed from an alcohol (RfCH2OH), (b) a step in which a monochloroester (RfCOOCHClRf) is formed from the aldehyde and an acid chloride (RfCOCl), and (c) a step in which the acid chloride (RfCOCl) is formed from the monochloroester.Type: GrantFiled: June 25, 1999Date of Patent: July 3, 2001Assignee: Daikin Industries Ltd.Inventors: Hirokazu Aoyama, Shoji Takagi, Shinichi Matsumura, Yoshinori Tanaka
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Patent number: 6252105Abstract: Organic compounds, e.g. fluorinated organic compounds such as fluorinated carboxylic acids or fluorinated carboxylic acid chlorides, may contain small amounts of carboxylic acid fluorides, hydrogen fluoride or hydrolyzable fluoride, which during the preparation of derivatives of the fluorinated organic compounds, for example by esterification, may yield corrosive fluorides or hydrogen fluoride. The invention is a method for the synthesis and/or purification of preferably fluorinated organic compounds such as carboxylic acids, carboxylic acid chlorides and derivatives such as esters thereof, starting from corresponding carboxylic acid chlorides containing acid fluorides or hydrolyzable fluoride, and alcohols under the catalytic action of “onium” salts of carboxylic acids, to obtain products which have a low fluoride content. Alternatively, an inorganic oxide adsorbent is utilized.Type: GrantFiled: July 6, 1999Date of Patent: June 26, 2001Assignee: Solvay Fluor und Derivate GmbHInventors: Max Braun, Johannes Eicher, Francine Janssens, Kerstin Eichholz, Stefan Palsherm
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Patent number: 6242645Abstract: Diaryl-, dialkoxyalkyl-, alkylalkoxyalkyl-, arylalkoxyalkyl- and cyclic aminosulfur trifluorides fluorinating agents are disclosed.Type: GrantFiled: March 23, 2000Date of Patent: June 5, 2001Assignee: Air Products and Chemicals, Inc.Inventors: Gauri Sankar Lal, Guido Peter Pez, Reno Joseph Pesaresi, Jr., Robert George Syvret
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Patent number: 6242658Abstract: 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: GrantFiled: August 6, 1999Date of Patent: June 5, 2001Assignee: E. I. duPont de Nemours and CompanyInventors: Ralph Thomas Baker, Richard Paul Beatty, Allen Capron Sievert, Robert Lewis Wallace, Jr.
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Patent number: 6222046Abstract: The invention has disclosed a trifluoroacetoxylation agent and a preparation process of the agent, which is safe and ease to handle, very useful in industry, and represented by the formula (1); wherein R1 to R4 are a substituted or unsubstituted, saturated or unsaturated alkyl group or a substituted or unsubstituted aryl group and can be the same or different, R1 and R2 or R3 and R4 can bond to form a ring containing a nitrogen atom or a nitrogen atom and other hetero atoms, and R1 and R3 can bond to form a ring containing a nitrogen atom or a nitrogen atom and other hetero atoms.Type: GrantFiled: August 9, 1999Date of Patent: April 24, 2001Assignee: Mitsui Chemicals, Inc.Inventors: Hidetoshi Hayashi, Hiroshi Sonoda, Kenichi Goto, Kouki Fukumura, Junko Naruse, Teruyuki Nagata
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Patent number: 6222064Abstract: A fluorination method of oxygen and halogen sites with diaryl-, dialkoxyalkyl-, alkylalkoxyalkyl-, arylalkoxyalkyl- and cyclic aminosulfur trifluorides fluorinating reagents is disclosed.Type: GrantFiled: January 14, 2000Date of Patent: April 24, 2001Assignee: Air Products and Chemicals, Inc.Inventors: Gauri Sankar Lal, Guido Peter Pez
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Patent number: 6187948Abstract: A fluorovinyl ether of the formula: R1CO(OCH2CF2CO)k—(OCH2CF2CF2)m[OCF(CF3)CF2]nOCF═CF2 wherein R1 is an C1-C8 aliphatic or halogenated C1-C8 aliphatic group or an aromatic group which may optionally have at least one substituent, k is an integer of at least 0, m is an integer of at least 1, and n is an integer of at least 0.Type: GrantFiled: July 15, 1998Date of Patent: February 13, 2001Assignee: Daikin Industries Ltd.Inventors: Yoshio Negishi, Takayuki Araki, Tetsuo Shimizu
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Patent number: 6133472Abstract: Fluorine containing oxyvinyl compounds characterized by having one or more oxyvinyl groups separated from fluorine containing groups by at least one alkylene group having 2-8 carbon atoms and by at least one oxygen atom in addition to the oxygen on the oxyvinyl. In general the compounds of the invention have the generic formula:Rz(L).sub.a (Ry).sub.b OROCH.dbd.CH.sub.2.Where L is .dbd.CHCOOROCH.dbd.CH.sub.2 ; a is number of 0 to about 1; R.sub.y is --CO--; b is a number of 0 to about 1; R is cycloalkane or (CH.sub.2).sub.x --, where x is a number of about 2 through about 10; R.sub.z is R.sub.f C.sub.n H.sub.m where R.sub.f is a fluorinated alkylene moiety of about 1 to about 12 carbon atoms which may be linear or branch chained and may contain a further --OROCH.dbd.CH.sub.2 group; n is an integer of about 1 through about 6; and m is an integer of n to 2n.Type: GrantFiled: January 20, 1998Date of Patent: October 17, 2000Assignee: AlliedSignal Inc.Inventors: David Nalewajek, David Bradley, John Schabel, Robert Blomquist
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Patent number: 6103677Abstract: A lubricant containing a fluorinated dicarboxylic acid of the formula: A.sup.1 --COO--R.sup.1 --Rf--R.sup.2 --OCO--A.sup.2 in which Rf is a divalent perfluoropolyether group; R.sup.1 and R.sup.2 are the same or different and represent a hydrocarbon group; and A.sup.1 and A.sup.2 are the same or different and represent an organic group having a carboxyl group, which allows two solid materials, for example, a magnetic recording medium and a magnetic head, to slide with low wearing at a low friction under various conditions.Type: GrantFiled: February 10, 1999Date of Patent: August 15, 2000Assignee: Hitachi Maxell, Ltd.Inventors: Takahiro Furutani, Sayaka Shinomoto, Tetsuo Mizumura
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Patent number: 6080886Abstract: A fluorination method of oxygen and halogen sites with diaryl-, dialkoxyalkyl-, alkylalkoxyalkyl-, arylalkoxyalkyl- and cyclic aminosulfur trifluorides fluorinating reagents is disclosed.Type: GrantFiled: September 29, 1997Date of Patent: June 27, 2000Assignee: Air Products and Chemicals, Inc.Inventors: Gauri Sankar Lal, Guido Peter Pez
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Patent number: 6075146Abstract: The invention relates to intermediates and processes for producing benzothiophenes employing hydroxylamines.Type: GrantFiled: July 28, 1998Date of Patent: June 13, 2000Assignee: Eli Lilly and CompanyInventor: Erik Christopher Chelius
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Patent number: 6049001Abstract: Novel fluorine-containing carboxylic acid compounds of formula (II) are provided that can be reacted together with a base to produce industrially useful 3-(2-chloro-2-fluorovinyl)-2,2-dimethyl cyclopropanecarboxylic acid compounds of formula (I). The fluorine-containing containing carboxylic acid compounds of formula (II), if so desired, can be produced by reacting together a carboxylic acid compound of formula (III) and trichlorofluoromethane. In each of the formulas (I), (II), and (III), R is a lower alkyl group or a hydrogen atom.Type: GrantFiled: July 28, 1999Date of Patent: April 11, 2000Assignee: Sumitomo Chemical Company, LimitedInventors: Ken Otaka, Noritada Matsuo
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Patent number: 6040487Abstract: A liquid phase process is disclosed for producing halogenated alkane adducts of the formula: CAR.sup.1 R.sup.2 CBR.sup.3 R.sup.4 (where, A, B, R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are defined in the specification) which involves contacting a corresponding halogenated alkane, AB, with a corresponding olefin, CR.sup.1 R.sup.2 .dbd.CR.sup.3 R.sup.4, in the presence of a catalyst system containing (i) at least one catalyst selected from monovalent and divalent copper, and (ii) a promoter selected from aromatic or aliphatic hetercyclic compounds which contain at least one carbon-nitrogen double bond in the heterocyclic ring. When hydrochlorofluorocarbons are formed, hydrofluorocarbons may be formed therefrom by reacting the hydrochlorofluorocarbons with HF.Type: GrantFiled: January 28, 1998Date of Patent: March 21, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Ralph Thomas Baker, Viacheslav Alexandrovich Petrov, Velliyurnott Mallikarjuna Rao
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Patent number: 6013795Abstract: Briefly, in one aspect, the present invention provides compositions of open-chain, .alpha.-branched fluoroalkylcarbonyl fluorides, and derivatives thereof.Type: GrantFiled: November 4, 1996Date of Patent: January 11, 2000Assignee: 3M Innovative Properties CompanyInventors: Anthony P. Manzara, Wei-Qiang Fan, Richard M. Stern, George G. I. Moore
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Patent number: 5973191Abstract: The present invention provides a compound of the formula ##STR1## wherein R is selected from the group consisting of CH.sub.3, CH.sub.2 CH.sub.3, (CH.sub.2).sub.2 CH.sub.3, (CH.sub.2).sub.3 CH.sub.3, (CH.sub.2).sub.4 CH.sub.3, (CH.sub.2).sub.5 CH.sub.3, (CH.sub.2).sub.6 CH.sub.3, (CH.sub.2).sub.2 O(CH.sub.2).sub.3 CH.sub.3, CH.sub.2 HC.dbd.CH(CH.sub.2).sub.3 CH.sub.3, CH.sub.2 C.tbd.C(CH.sub.2).sub.3 CH.sub.3, CH.sub.2 C.tbd.C(CH.sub.2).sub.2 CH.sub.3, CH.sub.2 C.tbd.CCH.sub.2 CH.sub.3, CH.sub.2 C.tbd.CCH.sub.3 and CH.sub.2 C.tbd.CH; and R' is selected from the group consisting of CH.sub.3, CF.sub.3, CH.sub.2 Cl and CH.sub.2 Br or a pharmaceutically acceptable salt or hydrate thereof. Also provided is a method of inhibiting the synthesis of prostaglandin endoperoxide syntase-2 (PGHS-2) in a mammal.Type: GrantFiled: December 30, 1996Date of Patent: October 26, 1999Assignee: Vanderbilt UniversityInventors: Lawrence J. Marnett, Amit S. Kalgutkar
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Patent number: 5965059Abstract: An optically active compound which itself generally exhibits no antiferroelectric liquid crystal phase, but which can be added to an antiferroelectric liquid crystal or composition thereof having a high threshold voltage to reduce the threshold voltage of the resulting composition. Also disclosed is an antiferroelectric liquid crystal composition containing the optically active compound, a process for reducing the threshold voltage of an antiferroelectric liquid crystal composition, a process for producing the optically active compound, and a process for producing an optically active carboxylic acid as an intermediate.Type: GrantFiled: March 19, 1998Date of Patent: October 12, 1999Assignee: Takasago International CorporationInventors: Shinya Yamada, Yukiharu Iwaya, Mamoru Yamada, Akio Yamaguchi, Hitoshi Kondo, Toshimitsu Hagiwara
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Patent number: 5811578Abstract: Fluorinated alkene compounds useful for and methods of controlling nematodes, insects, and acards that prey on agricultural crops. Polar compounds are particularly useful for systemic control of pests.Type: GrantFiled: August 20, 1997Date of Patent: September 22, 1998Assignee: Monsanto CompanyInventors: Dennis Paul Phillion, Peter Gerrard Ruminski, Gopichand Yalamanchili
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Patent number: 5786505Abstract: A method of selectively oxidizing an organic compound in a single vessel comprises: a) combining an organic compound, an acid solution in which the organic compound is soluble, a compound containing two oxygen atoms bonded to one another, and a metal ion reducing agent capable of reducing one of such oxygen atoms, and thereby forming a mixture; b) reducing the compound containing the two oxygen atoms by reducing one of such oxygen atoms with the metal ion reducing agent to, 1) oxidize the metal ion reducing agent to a higher valence state, and 2) produce an oxygen containing intermediate capable of oxidizing the organic compound; c) reacting the oxygen containing intermediate with the organic compound to oxidize the organic compound into an oxidized organic intermediate, the oxidized organic intermediate having an oxidized carbon atom; d) reacting the oxidized organic intermediate with the acid counter ion and higher valence state metal ion to bond the acid counter ion to the oxidized carbon atom and therebyType: GrantFiled: July 3, 1996Date of Patent: July 28, 1998Assignee: Battelle Memorial InstituteInventors: Donald M. Camaioni, Michael A. Lilga
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Patent number: 5780672Abstract: 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: GrantFiled: July 11, 1996Date of Patent: July 14, 1998Assignee: Hoechst AktiengesellschaftInventors: Sergej Pasenok, Wolfgang Appel
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Patent number: 5780673Abstract: A process for the preparation of alkyl halodifluoroacetates comprises reacting a 1,1-difluorotetrahaloethane with an alcohol, e.g., ethanol or isopropanol, in the presence of oxygen and a chemical free-radical initiator, e.g., an azo compound.Type: GrantFiled: May 29, 1997Date of Patent: July 14, 1998Assignee: Elf Atochem S.A.Inventors: Jean-Philippe Gillet, Christophe Ruppin
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Patent number: 5763552Abstract: A partially-fluorinated surfactant having internal methylene groups and having the formula R.sub.f --(CH.sub.2).sub.m --R'.sub.f --COOM wherein m is 1-3, R.sub.f is perfluoroalkyl or perfluoroalkoxy, containing 3-8 carbon atoms, R'.sub.f is linear or branched perfluoroalkylene containing 1-4 carbon atoms, and M is NH.sub.4, Li, Na, K, or H is useful in polymerization of fluorinated monomers. High molecular weight can be achieved in homopolymerization of tetrafluoroethylene.Type: GrantFiled: July 1, 1997Date of Patent: June 9, 1998Assignee: E. I. du Pont de Nemours and CompanyInventors: Andrew E. Feiring, Ming-Hong Hung, Jose M. Rodriguez-Parada, Roger J. Zipfel
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Patent number: 5753776Abstract: This invention pertains to a method for liquid phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: June 6, 1995Date of Patent: May 19, 1998Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy J. Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5723654Abstract: Alkyl 2-fluoro-isobutyrates are prepared by reacting the corresponding sulphonic esters with potassium fluoride in an acid amide as solvent and in the presence of a base.Type: GrantFiled: June 17, 1996Date of Patent: March 3, 1998Assignee: Bayer AktiengesellschaftInventor: Achim Bertsch
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Patent number: 5710279Abstract: The invention provides novel N-acyloxyalkyl-carboxamides of the general formula (I): ##STR1## in which R.sup.1 is alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, arylalkyl or heteroarylalkyl, each of which is optionally substituted,R.sup.2 is optionally substituted alkyl andR.sup.3 is hydrogen, halogen or optionally substituted alkyl,in the isolated and pure form, and a process for their preparation.Type: GrantFiled: September 5, 1996Date of Patent: January 20, 1998Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Werner Lindner
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Patent number: 5710317Abstract: A method for preparing difluoroacetic acid fluoride, which comprises reacting a 1-alkoxy-1,1,2,2-tetrafluoroethane of the formula HCF.sub.2 CF.sub.2 OR.sup.1 wherein R.sup.1 is a C.sub.1-4 alkyl group in a gas phase in the presence of a metal oxide catalyst.Type: GrantFiled: July 26, 1995Date of Patent: January 20, 1998Assignee: Asahi Glass Company Ltd.Inventors: Kazuya Oharu, Seisaku Kumai
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Patent number: 5708119Abstract: Bisperfluoroalkyl-substituted diols containing sulfide, sulfone or polysulfide linkages and a method for making them are described. These diols can react with isocyanates to form urethanes; diisocyanates to form polyturethanes; chloroformates to form carbonates; with carboxylic, sulfuric or phosphoric acids or derivatives to form carboxylate esters, sulfate esters, phosphate esters respectively. These diol compounds and their derivatives are useful for imparting oil and water repellency to substrates such as glass, wood, paper, leather, wool, cotton, polyester and other substrates.Type: GrantFiled: June 14, 1996Date of Patent: January 13, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Ted Deisenroth, Marlon Haniff
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Patent number: 5693251Abstract: An optically active phenol useful in the preparation of liquid crystalline compounds which is represented by the formula (V): ##STR1## wherein R.sub.2 represents an alkyl or alkoxyalkyl group having 1 to 20 carbon atoms optionally substituted by halogen atoms; Z' represents ##STR2## wherein q represents a number of 1 to 5 and * indicates asymmetric carbon atom; l represents a number of 2; t represents a number of 1 to 5; s represents a number of 0 or 1.Type: GrantFiled: November 23, 1994Date of Patent: December 2, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Takayuki Higashii, Isao Kurimoto, Shoji Toda, Masayoshi Minai, Takeshi Tani, Chizu Kawakami, Koichi Fujisawa
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Patent number: 5674949Abstract: This invention pertains to a method for liquid-phase fluorination for perfluorination of a wide variety of hydrogen-containing compounds.Type: GrantFiled: June 6, 1995Date of Patent: October 7, 1997Assignee: Exfluor Research CorporationInventors: Thomas R. Bierschenk, Timothy Juhlke, Hajimu Kawa, Richard J. Lagow
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Patent number: 5619023Abstract: For the preparation of alkyl halodifluoroacetates, a 1,1-difluorotetrahaloethane is reacted with an alcohol in the presence of air and/or oxygen and a free-radical initiator, such as for example an azo compound, e.g., azobis(isobutyronitrile).Type: GrantFiled: December 5, 1995Date of Patent: April 8, 1997Assignee: Elf Atochem S.A.Inventors: Gilles Drivon, Jean-Philippe Gillet, Christophe Ruppin, Alain Wattier