Fluorine In Acid Moiety Patents (Class 560/227)
  • Patent number: 5072030
    Abstract: Difluoropropionic acid and derivatives thereof are prepared by bringing elemental fluorine in the presence of a solvent into an addition reaction with appropriate acrylic acids or derivatives thereof. In this way, it is also possible to obtain novel fluorinated esters of 2,3-difluoropropionic acid.
    Type: Grant
    Filed: February 12, 1990
    Date of Patent: December 10, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dietmar Bielefeldt, Karl-Rudolf Gassen, Walter Lange
  • Patent number: 5068397
    Abstract: Tris-perfluoroalkyl terminated neopentyl alcohols of the formula (R.sub.f --E.sub.n --X--CH.sub.2).sub.3 CCH.sub.2 OH prepared from halogenated neopentyl alcohols and thiols of the formula R.sub.f --E.sub.n --SH, amines of the formula R.sub.f --E.sub.n --NH--R, alcohols of the formula R.sub.f --E.sub.n --OH, perfluoro-acids or amides, are described. The alcohols react with isocyanates to prepare urethanes; with acids or derivatives, to prepare esters or carbonates; with epoxides to form ethers. Further, they may be converted to halide intermediates. The products all contain the residue of at least one R.sub.f -neopentyl alcohol containing three perfluoroalkyl hetero groups.
    Type: Grant
    Filed: August 15, 1990
    Date of Patent: November 26, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Robert A. Falk, Kirkland P. Clark, Michael Jacobson, Athanasios Karydas, Juliana Rodgers
  • Patent number: 5068390
    Abstract: 1,1,1-trifluoro-2-propene compounds which are useful in the preparation of insecticidal, acaricidal and nematicidal arylpyrrole compounds are described. A method for the preparation of 1,1,1-trifluoro-2-propene compounds is presented.
    Type: Grant
    Filed: July 31, 1990
    Date of Patent: November 26, 1991
    Assignee: American Cyanamid Company
    Inventors: David G. Kuhn, Kenneth A. M. Kremer
  • Patent number: 5030792
    Abstract: This invention relates to a process for producing 1-octenes comprising reacting conjugated dienes and carboxylic acids in the presence of palladium, platinum or ruthenium catalysts to produce 2,7-alkadienyl esters, contacting the 2,7-alkadienyl esters with hydrogen to produce alkyl esters and subsequently pyrolyzing the alkyl esters to produce 1-octene and carboxylic acid.
    Type: Grant
    Filed: June 22, 1987
    Date of Patent: July 9, 1991
    Assignee: Shell Oil Company
    Inventor: Lynn H. Slaugh
  • Patent number: 5026898
    Abstract: A process for regioselectively preparing phosphorylated cyclitols, in particular phosphorylated inositols such as myo-inositol 1,4,5-tris(phosphate) and muo-inositol 1,3,4,5-tetrakis(phosphate). Novel cyclitols produced by means of this process are also described.
    Type: Grant
    Filed: January 31, 1990
    Date of Patent: June 25, 1991
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Frank W. Hobbs, James L. Meek
  • Patent number: 5025003
    Abstract: Compounds which are inhibitors of cholesterol biosynthesis (by inhibiting de novo squalene biosynthetis), and thus are useful as hypocholesterolemic agents and antiatherosclerotic agents, are provided which have the structure ##STR1## wherein R.sup.2 is a metal ion, lower alkyl or H; R.sup.3 is a metal ion or lower alkyl;R is R.sup.1 --(CH.sub.2).sub.n --, R.sup.1 --(CH.sub.2).sub.m --O-- orR.sup.1 --(CH.sub.2).sub.m --OCH.sub.2 --, wherein n is 1 to 4 and m is 0 to 3, andR.sup.1 is R.sup.5 --Q.sup.1 --Q.sup.2 --Q.sup.3 -- wherein R.sup.5, Q.sup.1, Q.sup.2 and Q.sup.3 are as defined herein.New intermediates, new methods of preparation and a method for using such compounds to inhibit cholesterol biosynthesis are also provided.
    Type: Grant
    Filed: September 18, 1989
    Date of Patent: June 18, 1991
    Assignee: E. R. Squibb & Sons, Inc.
    Inventor: Scott A. Biller
  • Patent number: 5021453
    Abstract: Compounds of formula (I) and (II): ##STR1## are HMG-CoA reductase inhibitors.
    Type: Grant
    Filed: June 6, 1990
    Date of Patent: June 4, 1991
    Assignee: Merck & Co., Inc.
    Inventors: Henry Joshua, Kenneth E. Wilson, Michael S. Schwartz, Ta J. Lee, Gerald E. Stokker
  • 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: 5013475
    Abstract: An optically active ester compound useful as a component of a ferroelectric liquid crystal composition is represented by the following formula: ##STR1## wherein R is C.sub.1-18 alkyl or C.sub.1-18 alkoxyl; R' is C.sub.1-18 alkyl or C.sub.
    Type: Grant
    Filed: October 27, 1989
    Date of Patent: May 7, 1991
    Assignee: Adeka Argus Chemical Co., Ltd.
    Inventors: Toshihiro Shibata, Masaki Kimura, Norio Kurosawa
  • Patent number: 5004569
    Abstract: The invention relates to a process for the production of carboxylic acid esters from carboxylic acids and alcohols which is characterized in that neutral phosphites containing oxetane groups are used as esterification catalysts.
    Type: Grant
    Filed: December 6, 1988
    Date of Patent: April 2, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Helmut-Martin Meier, Klaus Kircher, Klaus Berg
  • Patent number: 4983747
    Abstract: Disclosed is a process for the preparation of a perfluoroorganic compound, which comprises fluorinating a partially fluorinated or unfluorinated organic compound having carbon-to-fluorine bonds under mild conditions and then, contacting the resulting reaction mixture with a fluorine gas at a temperature of 110.degree. to 180.degree. C.
    Type: Grant
    Filed: March 15, 1990
    Date of Patent: January 8, 1991
    Assignee: Tokuyama Soda Kabushiki Kaisha
    Inventors: Masakatsu Nishimura, Naoya Okada, Yasuo Murata, Yasuhiko Hirai
  • Patent number: 4980501
    Abstract: A process for the production of secondary-butyl perfluoroester is provided by reacting ethylene with a perfluorocarboxylic acid in the presence of oxygen.
    Type: Grant
    Filed: March 19, 1990
    Date of Patent: December 25, 1990
    Assignee: National Distillers and Chemical Corporation
    Inventor: John A. Scheben
  • Patent number: 4973426
    Abstract: An optically active compound having particularly a specific feature of increasing spontaneous polarization value as one of important specific features for ferroelectric liquid crystal compositions, and a ferroelectric liquid crystal composition containing the compound are provided, which compound is expressed by the formula ##STR1## wherein R.sup.1 represents a linear or branched chain alkyl, alkoxy, alkanoyl, alkoxycarbonyl or alkoxycarbonyloxy each of 1 -15C, H, halogen or -CN; R.sup.2 represents an optically active group having 2-20 skeletal atoms, ##STR2## wherein X represents H, halogen or -CN; l represents an integer of 1-10; m is 0 or 1; and * indicates asymmetric C.
    Type: Grant
    Filed: February 25, 1988
    Date of Patent: November 27, 1990
    Assignee: Chisso Corporation
    Inventors: Kouji Ohno, Shinichi Saito, Hiromichi Inoue, Kazutoshi Miyazawa, Makoto Ushioda
  • Patent number: 4956123
    Abstract: Fluorine-containing aromatic derivatives are produced by the reaction of di(haloacyl)peroxide represented by the general formula: ##STR1## (wherein X stands for a fluorine, chlorine, or hydrogen atom and n for an integer of the value of 1 to 10) with aromatic unsaturated monomers represented by the general formula: ##STR2## (wherein Y stands for hydrogen atom, methyl, ethyl, propyl, acetyl, propionyl, acetyloxy, propionyloxy, methoxy, ethoxy, propoxy, vinyl, isopropenyl, or nitro group, or a halogen atom, R.sup.1 for hydrogen atom, methyl, ethyl, propyl, or butyl group, R.sup.2 for hydrogen atom, methyl or phenyl group, and m for an integer of the value of 1 to 5).
    Type: Grant
    Filed: September 14, 1988
    Date of Patent: September 11, 1990
    Assignee: Nippon Oils & Fats Company, Ltd.
    Inventors: Hideo Sawada, Michio Kobayashi, Masato Yoshida
  • Patent number: 4952580
    Abstract: Polyhaloalkene compounds of the formula: ##STR1## wherein X is sulfur, oxygen, or nitrogen, Y.sup.1 and Y.sup.2 are fluorine, Z is hydrogen or the same as Y.sup.1 and Y.sup.2, and n is 1-4; provided that:(A) when X is sulfur, Z is fluorine and R is thienyl or substituted thienyl, thianaphthyl or substituted thianaphthyl, thiazolinyl or substituted thiazolinyl, oxadiazolyl or substituted oxadiazolyl, 3,4,4-trifluoro-3-butenyloxycarbonylmethyl, thiadiazolyl substituted by halogen or R.sup.2 S, wherein R.sup.2 is 3,4,4-trifluoro-3-butenyl or R.sup.2 is phenylmethyl or phenylthiomethyl each optionally substituted by halogen or nitro; or R is thiadiazolyl substituted by R.sup.3, wherein R.sup.3 is substituted aryl, arylalkyl, aryloxyalkyl, alkylthio, haloalkylthio, haloarylthio, cyanoalkylthio, arylalkylthio, aryloxyalkylthio, arylthioalkylthio, heterocycloalkylthio, alkenylthio, haloalkenylthio, halocycloalkylalkenylthio, wherein said aryl or heterocyclic groups of R.sup.
    Type: Grant
    Filed: November 9, 1988
    Date of Patent: August 28, 1990
    Assignee: FMC Corporation
    Inventors: Anthony J. Martinez, Thomas G. Cullen
  • Patent number: 4948912
    Abstract: The present invention comprises a haloacetoxyalkyl ether having the formula: ##STR1## wherein R is H or a C.sub.1 -C.sub.4 substituted or unsubstituted alkyl group, R' is H or a C.sub.1 -C.sub.3 group, and X is chlorine or fluorine; aroyloxymethyl ethers having the formula:R--COOCH.sub.2 --O--CH.sub.2 --OOC--Rwherein the R is p-NO.sub.2 C.sub.6 H.sub.4, halogen substituted C.sub.6 H.sub.4, or other aromatics; the method of making such ethers and monoquaternary salts; and the method of alkylating amines, pyridines, or acetals or pyridine derivatives with such ethers to form quaternary ammonium salts; particularly HI-6, HGG-12, Toxogonin, and SAS-128.
    Type: Grant
    Filed: September 8, 1986
    Date of Patent: August 14, 1990
    Assignee: Southwest Research Institute
    Inventors: Robert E. Lyle, Jr., Donald J. Mangold, Nollie F. Swynnerton
  • Patent number: 4946992
    Abstract: Heteroatom containing perfluoroalkyl terminated neopentyl glycols of the formulas HO[--CH.sub.2 C(CH.sub.2 X--E--R.sub.f).sub.2 CH.sub.2 O].sub.1-3 --H or HO[--CH.sub.2 C(CH.sub.2 X--R.sub.f).sub.2 CH.sub.2 O].sub.1-3 --H are prepared from halogenated neopentyl glycols or oxetanes and thiols of the formula R.sub.f --E--SH, amines of the formuls R.sub.f --E--NH--R, alcohols of the formula R.sub.f --E--OH or perfluoro-amides, wherein R.sub.f is a straight or branched chain perfluoroalkyl of 1 to 18 carbon atoms or said perfluoroalkyl substituted by perfluoroalkoxy of 2 to 6 carbon atoms.The polymeric reaction products of said fluorinated diols, and optionally other diols with isocyanates to prepare polyurethanes; with amines and isocyanated to prepare polyureas/polyurethanes; with acids or derivatives to prepare polyesters or polycarbonates are disclosed. These include polymeric, random or block urethane, and/or urea, and/or ester compositions containing the residue of at least one R.sub.
    Type: Grant
    Filed: April 14, 1989
    Date of Patent: August 7, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Robert A. Falk, Kirtland P. Clark, Athanasios Karydas, Michael Jacobson
  • Patent number: 4927954
    Abstract: A continuous process for efficiently co-producing secondary alcohols of long-chain olefins and lower carboxylic acid esters, comprising (I) performing an acid/olefin reaction in the presence of a heterogeneous catalyst such as Amberlyst 15, and (II) performing an ester-exchange reaction in the presence of, e.g., titanium alcoholate. A desirable feature of the process is the ability to produce co-products of choice.
    Type: Grant
    Filed: April 19, 1989
    Date of Patent: May 22, 1990
    Assignee: Union Carbide Chemicals and Plastics Company, Inc.
    Inventors: Robert J. Knopf, Louis F. Theiling Jr., Leroy P. Berti
  • Patent number: 4916256
    Abstract: Process for the production of alkyl trifluoroacetates by esterification of trifluoroacetyl chloride with alkyl alcohols, wherein the trifluoroacetyl chloride/alcohol molecular ratio is greater than 1; alkyl trifluoroacetate is recovered by condensation at temperatures lower than -30.degree. C.
    Type: Grant
    Filed: August 18, 1988
    Date of Patent: April 10, 1990
    Assignee: Ausimont, S.p.A.
    Inventors: Saverio Grego, Adriano Checchin, Giorgio Guglielmo
  • Patent number: 4879407
    Abstract: A process for the preparation of ethyl trifluoroacetate, in which:in a first stage, trifluoroacetic acid is brought into contact with a slight excess of ethanol in the presence of concentrated sulfuric acid and a solvent, the solvent having a boiling point higher than that of trifluoroacetic acid and specific gravity relative to water less than 1 and which solvent does not form an azeotrope with ethyl trifluoroacetate, and then carrying out a phase separation and removing the sulfuric layer, followed, if required, by an additional stage in which concentrated sulfuric acid is added to complete the esterification;in a second stage, an additional quantity of sulfuric acid and trifluoroacetic acid is introduced and a phase separation is then carried out to remove the sulfuric layer; andin a third stage, the mixture obtained in the second stage is distilled to recover ethyl trifluoroacetate.
    Type: Grant
    Filed: October 16, 1987
    Date of Patent: November 7, 1989
    Assignee: Rhone-Poulenc Chimie
    Inventor: Louis Amiet
  • Patent number: 4866189
    Abstract: There is provided a novel and efficient stereoselective total synthesis of epipodoplyllotoxin and related epipodophyllotoxin compounds of the general formula ##STR1## wherein R.sup.1 and R.sup.2 each are independently hydrogen or (lower)-alkoxy, or R.sup.1 and R.sup.2, taken together, is methylenedioxy; R.sup.4 and R.sup.6 each are independently hydrogen or (lower)alkoxy; and R.sup.5 is hydrogen or a phenol-protecting group; or an acid addition salt thereof. The present invention also provides novel intermediates and processes for the preparation of said intermediates, which are then converted into known antineoplastic agents.
    Type: Grant
    Filed: September 16, 1988
    Date of Patent: September 12, 1989
    Assignee: Bristol-Myers Company
    Inventors: Dolatrai M. Vyas, Paul M. Skonezny
  • Patent number: 4855487
    Abstract: An improved process for preparing a fluorine-containing carboxylic acid ester useful as an intermediate for producing a fluorine-containing carboxylic acid is disclosed. The process comprises reacting a fluorine-containing alkyl halide with carbon monoxide and an alcohol in the presence of a transition metal catalyst of the Group VIII of the Periodic Table and a base, and provides the desired carbonylated compound in high yield.
    Type: Grant
    Filed: July 10, 1987
    Date of Patent: August 8, 1989
    Assignee: Sagami Chemical Research Center
    Inventors: Takamasa Fuchikami, Hisao Urata, Yoshimitsu Ishii, Yoshiko Obata
  • Patent number: 4836958
    Abstract: The instant invention relates to fluorinated cationic compounds of the formula ##STR1## wherein R.sub.f is a perfluoroalkyl or perfluoroalkoxy-perfluoroalkyl group;R.sub.1 is alkylene optionally interrupted by --O--, --S--, --SO.sub.2 --, --SO.sub.2 NR'--, --CO.sub.2 --, --NR'--, or --CONR'-- where R' is hydrogen or lower alkyl;m is 0, 1 or 2;R.sub.2 is linear or branched alkylene;R.sub.3, R.sub.4, and R.sub.5 independently of one another represent alkyl or arylalkyl groups which are unsubstituted or substituted by hydroxyl, lower alkoxy, halogen, cyano or by polyalkyleneoxy, or R.sub.3 and R.sub.4 together with the nitrogen atom to which they are attached represent a 5- or 6-membered heterocyclic radical or R.sub.3, R.sub.4 and R.sub.5 together with nitrogen atom that links them represent a substituted or unsubstituted pyridine ring; andA.sup..crclbar. represents the anion of an organic or inorganic acid; and their particular use as surfactants.
    Type: Grant
    Filed: July 31, 1986
    Date of Patent: June 6, 1989
    Assignee: Ciba-Geigy Corporation
    Inventor: Athanasios Karydas
  • Patent number: 4835305
    Abstract: A trifluoroacrylate has been prepared by reacting hexafluoropropene with halogen fluorosulfate (halogen X:Cl, Br or I), eliminating the fluorosulfate CF.sub.3 --CFX--CF.sub.2 --OSO.sub.2 F to give the acid fluoride CF.sub.3 --CFX--COF, esterifying the acid fluoride and dehalogenating the product using a metal component.
    Type: Grant
    Filed: April 13, 1988
    Date of Patent: May 30, 1989
    Assignee: Hoechst Aktiengelselschaft
    Inventors: Peter Blickle, Klaus Hintzer, Werner Schwertfeger, Dieter Ulmschneider
  • Patent number: 4778915
    Abstract: The invention relates to fluoroacrylic monomers of formula: ##STR1## in which R.sub.f denotes a perfluoroalkyl radical, R is hydrogen or a methyl radical, R' denotes an alkyl or cycloalkyl radical, or --NR'-- denotes a 1, 4-piperazinylene radical, W and Z denote divalent connecting groups, Q is oxygen or sulphur or an --NR"-- group, R" denoting hydrogen an alkyl radical, and A is a C.sub.2 or C.sub.3 alkylene group. The polymers (homo- or copolymers) derived from these monomers may be used for the water-repellency and oil-repellency treatment of various substrates, particularly leather.
    Type: Grant
    Filed: October 16, 1986
    Date of Patent: October 18, 1988
    Assignee: Atochem
    Inventors: Marie-Jose Lina, Andre Dessaint
  • Patent number: 4766238
    Abstract: A novel fluorine-containing compound of the formula:(CF.sub.3).sub.2 CHCO.sub.2 CClX.sup.1 X.sup.2 (I)wherein X.sup.1 and X.sup.2 are, the same or different, each a hydrogen atom or a chlorine atom, which is useful as the starting material for production of 2-trifluoromethyl-3,3,3-trifluoropropene.
    Type: Grant
    Filed: September 3, 1987
    Date of Patent: August 23, 1988
    Assignee: Daikin Industries, Ltd.
    Inventors: Yasuhisa Furutaka, Masayuki Yamana, Tsunetoshi Honda
  • Patent number: 4730082
    Abstract: A process for the preparation of methyltrifluoroacetate. Trifluoroacetic acid is contacted with an excess of methanol and distilled to form a methyltrifluoroacetate/methanol azeotrope. The azeotrope is contacted with trifluoroacetic acid in the presence of a catalytic quantity of a strong acid followed by distillation to obtain methyltrifluoroacetate. The methyltrifluoroacetate can be used as a synthesis intermediate in the pharmaceutical industry.
    Type: Grant
    Filed: June 12, 1986
    Date of Patent: March 8, 1988
    Assignee: Rhone-Poulenc Specialties Chimiques
    Inventor: Louis Amiet
  • Patent number: 4727199
    Abstract: Active-hydrogen compounds, for example, primary and secondary alcohols or diols, are alkoxylated, for example, ethoxylated, using solid anion-bound metal oxide catalysts, such as, zirconium oxysulfate catalyst. Hydrous zicronium oxide is treated with solutions of sulfate phosphate, nitrate or tetrafluoroborate and calcined in air at 300.degree. to 950.degree. C. to produce highly active heterogeneous alkoxylation catalysts. The amorphous catalysts afford narrow molecular weight products. The catalyst can be removed from the product by filtration and reused with no significant loss in activity. Reaction temperatures of 50.degree. to 140.degree. C. are employed for alkoxylation.
    Type: Grant
    Filed: July 10, 1985
    Date of Patent: February 23, 1988
    Assignee: Union Carbide Corporation
    Inventor: Stephen W. King
  • Patent number: 4719052
    Abstract: 2,2,3-trifluoropropionyl fluoride is prepared by opening the ring of tetrafluorooxetane in the presence of a catalyst. Analogously, a novel 2,2-difluoropropionic acid derivative of the formula:XCH.sub.2 CF.sub.2 COY (I)wherein X is chlorine, bromine, iodine, a group of the formula:R.sub.1 O-- (II)orR.sub.2 COO-- (III)wherein R.sub.1 R.sub.2 are each an aliphaic or halogenated aliphatic hydrocarbon group having 1 to 8 carbon atoms or an aromatic hydrocarbon group having 6 to 8 carbon atoms optionally bearing at least one substituent, or a group of the formula:X'CH.sub.2 CF.sub.2 CF.sub.2 O-- (IV)wherein X' is fluorine, chlorine, bromine, iodine, the group of the formula: R.sub.1 O--or R.sub.2 COO--; and Y is fluorine or a group of the formula:--OR.sub.3 (V)wherein R.sub.
    Type: Grant
    Filed: December 20, 1984
    Date of Patent: January 12, 1988
    Assignee: Daikin Industries Ltd.
    Inventors: Yohnosuke Ohsaka, Takashi Tohzuka, Shoji Takaki, Yoshio Negishi, Satoru Kohno
  • Patent number: 4713469
    Abstract: A fluorine-containing multifunctional ester compound represented by the formula ##STR1## wherein A is halogen atom, NO.sub.2 or N.sub.3, B is halogen atom or SR.sup.2, R.sup.1 is lower aliphatic group, aromatic group or aralkyl, R.sup.2 is lower aliphatic group or aromatic group.
    Type: Grant
    Filed: March 27, 1986
    Date of Patent: December 15, 1987
    Assignee: Daikin Industries, Ltd.
    Inventors: Yoshio Takeuchi, Toru Koizumi, Kozo Hori
  • Patent number: 4701551
    Abstract: A process for preparing trifluoroacetic or trichloroacetic acid esters, wherein trifluoroacetic or trichloroacetic acid is brought together with a non-perfluorinated alcohol in liquid hydrofluoric acid and wherein the ester obtained is separated by decantation. The trifluoroacetic or trichloroacetic acid esters are used as synthesis intermediates in the pharmaceutical or the plant-protection industry.
    Type: Grant
    Filed: July 21, 1986
    Date of Patent: October 20, 1987
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventors: Michel DesBois, Louis Amiet
  • Patent number: 4695657
    Abstract: A process for the preparation of compounds containing a difluoromethylene group in a position .alpha. to an oxygen atom. An alcohol or a phenol is brought into contact with trifluoroacetic acid or a halide or anhydride thereof in anhydrous liquid hydrofluoric acid, in the presence of boron trifluoride, in a quantity such that the absolute pressure of boron trifluoride is at least about one bar. The compounds obtained according to the invention are used as synthesis intermediates in the pharmaceutical, plant-protection, and dye industries, as anesthetics and as additives for lubricating oils.
    Type: Grant
    Filed: December 17, 1985
    Date of Patent: September 22, 1987
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Michel Desbois
  • Patent number: 4659855
    Abstract: Certain novel aryl sulfonyl fluorides, their preparation, and their use in inhibiting serine proteases with chymotrypsin-like and elastase-like specificity.
    Type: Grant
    Filed: May 9, 1983
    Date of Patent: April 21, 1987
    Assignee: Georgia Tech Research Corporation
    Inventor: James C. Powers
  • Patent number: 4650913
    Abstract: Reaction of a perfluorinated iodide with an olefin initiated by a sulfinate salt to prepare fluorinated iodide and diiodide monomers and surface active agents.
    Type: Grant
    Filed: November 29, 1984
    Date of Patent: March 17, 1987
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Andrew E. Feiring
  • Patent number: 4647691
    Abstract: Ethyl and n-propyl esters of carboxylic acids are prepared in good yield from methanol, syngas and a carboxylic acid by contacting a mixture of the carboxylic acid, carbon monoxide, hydrogen and methanol with a catalyst composition comprising a ruthenium-containing compound, a cobalt-containing compound and a quaternary onium salt or base, and heating the resulting mixture at an elevated temperature and pressure for sufficient time to produce the desired ethyl and propyl esters, and then recovering the same from the reaction mixture.
    Type: Grant
    Filed: January 13, 1982
    Date of Patent: March 3, 1987
    Assignee: Texaco Inc.
    Inventors: Jiang-Jen Lin, John F. Knifton
  • Patent number: 4640802
    Abstract: Process for the co-production of carboxylic acids of the general formula R.sup.1 --COOH and R.sup.2 --COOH and carboxylic acid esters of the general formula R.sup.1 --COOCH.sub.2 R.sup.2 and R.sup.2 --COOCH.sub.2 R.sup.1 from carboxylic acid esters of the general formula R.sup.1 --COOR.sup.2 and/or ethers of the general formula R.sup.3 OR.sup.4 (R.sup.1, R.sup.2, R.sup.3, R.sup.4 representing (substituted) alkyl or (substituted) aryl, alkaryl or aralkyl, R.sup.1 also representing H), carbon monoxide and hydrogen at elevated temperature and pressure in the presence of a ruthenium compound, a further Group VIII metal compound, a phosphine oxide and a compound R.sup.5 Hal or R.sup.5 COHal where R.sup.5 has one of the meanings given for R.sup.2 and Hal is iodine or bromine, the reaction mixture being substantially free from other transition metal or Group II metal iodides or bromides, and containing a tertiary phosphine oxide.
    Type: Grant
    Filed: July 7, 1982
    Date of Patent: February 3, 1987
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4617140
    Abstract: Bicyclohexyl derivatives of formula IR.sup.1 --Cy--Cy--X--Y IwhereinX is --CO--O-- or --O--CO--,Y is alkyl or perfluoroalkyl in each case of 1-8 C atoms, --Cy--Cy--R.sup.2, --Cy--Ph--R.sup.2, --Ph--Cy--R.sup.2, --Ph--Ph--R.sup.2 or --Ph--Dio--R.sup.2,Cy is 1,4-cyclohexylene,Ph is 1,4-phenylene,Dio is 1,3-dioxane-2,5-diyl andR.sup.1 and R.sup.2 are each alkyl or alkoxy in each case of 1-8 C atoms,can be used as components of liquid crystal dielectrics.
    Type: Grant
    Filed: July 29, 1985
    Date of Patent: October 14, 1986
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Rudolf Eidenschink, Joachim Krause
  • Patent number: 4602105
    Abstract: A process for the preparation of alpha-haloalkylesters, wherein an acylhalide having the general formula ##STR1## in which R.sup.1 represents a substituted or unsubstituted hydrocarbyl group and Hal represents chlorine or bromine is contacted with hydrogen at elevated temperature and pressure in the presence of a catalytic system comprising at least one Group VIII element.
    Type: Grant
    Filed: March 26, 1984
    Date of Patent: July 22, 1986
    Assignee: Shell Oil Company
    Inventor: Eit Drent
  • Patent number: 4596828
    Abstract: [(2-Hydroxy-5-alkoxyphenyl)methylthio]phenylmethanol and derivatives thereof were prepared from an appropriate 2-hydroxy-5-alkoxybenzaldehyde with a hydroxymethylthiophenol. These compounds were found to be potent anti-inflammatory agents.
    Type: Grant
    Filed: March 28, 1985
    Date of Patent: June 24, 1986
    Assignee: Merck & Co., Inc.
    Inventors: Milton L. Hammond, Robert A. Zambias
  • Patent number: 4582924
    Abstract: An .alpha.-fluoroalkyl carboxylic acid ester of the general formula ##STR1## wherein A is R.sup.1 R.sup.2 COR.sup.3 -- or R.sup.4 CO--, wherein R.sup.1 and R.sup.2 are independently hydrogen, alkyl, alkoxyl or phenyl, with or without the formation of a common ring therebetween, R.sup.3 is hydrogen or alkyl, R.sup.4 and R are independently alkyl, and R.sub.f is fluoroalkyl. The .alpha.-fluoroalkyl carboxylic acid ester is prepared by reacting a fluoroalkyl silyl ketene acetal of the formula ##STR2## wherein R' is alkyl and R.sub.f and R are the same as defined above, with the corresponding acetal, ketone or acyl halide.
    Type: Grant
    Filed: March 7, 1984
    Date of Patent: April 15, 1986
    Assignee: Daikin Kogyo Co., Ltd.
    Inventors: Nobuo Ishikawa, Takeshi Nakai
  • Patent number: 4570018
    Abstract: A novel chemical, fluorochlorocyclopropane (I) of the following formula: ##STR1## is prepared by the addition of fluorochlorocarbene to the corresponding olefin (II) of the following formula:CH.sub.2 .dbd.CR.sup.1 -R.sup.2The compound is a useful intermediate for synthesizing some chemicals, e.g., some cephalosporins.(wherein R.sup.1 is hydrogen, halogen, 1 to 8C alkylamino, alkoxy, or alkylthio andR.sup.2 is halogen, 1 to 8C alkylamino, alkoxy, or alkylthio).
    Type: Grant
    Filed: May 16, 1984
    Date of Patent: February 11, 1986
    Assignee: Shionogi & Co., Ltd.
    Inventors: Tsutomu Aoki, Hiromi Takahashi, Toshiro Konoike, Teruji Tsuji, Wataru Nagata
  • Patent number: 4568478
    Abstract: There is disclosed a solution of at least one fluoroxy compound, wherein said solution has a fluoroxy compound concentration of at least 0.5 meq/liter; said concentration containing about 35 to 100% of an acyl hypofluorite, based on the total number of equivalents of fluoroxy compounds present. The acyl hypofluorite has the formula X(CF.sub.2).sub.n COOF wherein X is H or F and n is 5 to 16. The solution is prepared by treating a suspension of a corresponding specified alkali salt with excess F.sub.2, and is useful as a selective fluorinating agent.
    Type: Grant
    Filed: April 18, 1984
    Date of Patent: February 4, 1986
    Assignee: E. I. Dupont de Nemours and Company
    Inventors: William J. Middleton, Shlomo Rozen
  • Patent number: 4567296
    Abstract: 1-Fluoro-1,1,5-trinitro-3-oxa-5-azahexane which is prepared by reacting one mole of 2-fluoro-2,2-dinitroethanol with one mole of an acetate of the formula ##STR1## wherein R is --CF.sub.3 or CH.sub.3.
    Type: Grant
    Filed: June 29, 1984
    Date of Patent: January 28, 1986
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Theodore C. Adams, Jr., Horst G. Adolph
  • Patent number: 4546200
    Abstract: 2,2-Dinitrobutane-1,4-diol and 4-monoesters thereof.
    Type: Grant
    Filed: May 6, 1983
    Date of Patent: October 8, 1985
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Michael E. Sitzmann, Horst G. Adolph
  • Patent number: 4540810
    Abstract: This invention concerns the improved preparation of alkanol and glycol esters, such as ethylene glycol diesters, by reaction of carbon monoxide and hydrogen in the presence of a catalyst system comprising ruthenium and a quaternary aryl or alkaryl phosphonium salt and a liquid phase medium containing a carboxylic acid co-reactant.
    Type: Grant
    Filed: September 20, 1979
    Date of Patent: September 10, 1985
    Assignee: Texaco Development Corporation
    Inventor: John F. Knifton
  • Patent number: 4539130
    Abstract: This invention relates to peroxygen bleaching activator compounds and bleaching compositions. The peroxygen bleach activator compounds, used in combination with peroxygen bleach compounds which yield hydrogen peroxide in an aqueous solution, provide effective and efficient bleaching of textiles over a wide range of temperatures. In a highly preferred embodiment the bleaching compositions of the invention are detergent compositions.
    Type: Grant
    Filed: October 30, 1984
    Date of Patent: September 3, 1985
    Assignee: The Procter & Gamble Company
    Inventors: James E. Thompson, Charles D. Broaddus
  • Patent number: 4486327
    Abstract: The invention relates to bodies containing bleach activators. The bodies comprise specific peroxygen bleach activators and select binder or enrobing materials. When formulated in such bodies the peroxygen bleach activators have excellent storage stability and maintain excellent dispersibility in wash water.
    Type: Grant
    Filed: December 22, 1983
    Date of Patent: December 4, 1984
    Assignee: The Procter & Gamble Company
    Inventors: Alan P. Murphy, Ali Kassamali, John D. Curry
  • Patent number: 4483778
    Abstract: This invention relates to peroxygen bleaching activator compounds and bleaching compositions. The peroxygen bleach activator compounds, used in combination with peroxygen bleach compounds which yield hydrogen peroxide in an aqueous solution, provide effective and efficient bleaching of textiles over a wide range of temperatures. In a highly preferred embodiment the bleaching compositions of the invention are detergent compositions.
    Type: Grant
    Filed: December 22, 1983
    Date of Patent: November 20, 1984
    Assignee: The Procter & Gamble Company
    Inventors: James E. Thompson, Charles D. Broaddus
  • Patent number: 4479966
    Abstract: Prostaglandin I.sub.2 analogues of the formula: ##STR1## [wherein the symbol between the carbon atoms in positions 5 and 6 represents a single or double bond, Y represents ethylene or trans-vinylene, R.sup.1 represents hydrogen, alkyl of 1 to 12 carbon atoms, aralkyl of 7 to 12 carbon atoms, cycloalkyl of 4 to 7 carbon atoms optionally substituted by alkyl of 1 to 4 carbon atoms, phenyl optionally substituted by chlorine, trifluoromethyl, alkyl of 1 to 4 carbon atoms or phenyl, a --C.sub.m H.sub.2m COOR.sup.7 group (wherein m represents an integer of from 1 to 12 and R.sup.7 represents alkyl of 1 to 4 carbon atoms), a --C.sub.n H.sub.2n OR.sup.8 group (wherein n represents an integer of from 2 to 12 and R.sup.8 represents hydrogen or alkyl of 1 to 4 carbon atoms) or a ##STR2## group (wherein R.sup.9 and R.sup.10 each represent alkyl of 1 to 4 carbon atoms and n is as hereinbefore defined), R.sup.2 represents hydrogen or a hydroxy-protecting group, R.sup.
    Type: Grant
    Filed: January 21, 1980
    Date of Patent: October 30, 1984
    Assignee: Ono Pharmaceutical Company, Ltd.
    Inventors: Masaki Hayashi, Yoshitaka Konishi, Yoshinobu Arai
  • Patent number: 4478760
    Abstract: The process for making a fluorinated product comprising reacting a perfluoroalkyl iodide and an olefin in the presence of a finely divided zinc and an acidic solvent.
    Type: Grant
    Filed: March 30, 1981
    Date of Patent: October 23, 1984
    Assignee: Produits Chimiques Ugine Kuhlmann
    Inventors: Hubert Blancou, Auguste Commeyras, Robert Teissedre