Fluorine In Acid Moiety Patents (Class 560/227)
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Patent number: 5072030Abstract: 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: GrantFiled: February 12, 1990Date of Patent: December 10, 1991Assignee: Bayer AktiengesellschaftInventors: Dietmar Bielefeldt, Karl-Rudolf Gassen, Walter Lange
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Patent number: 5068397Abstract: 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: GrantFiled: August 15, 1990Date of Patent: November 26, 1991Assignee: Ciba-Geigy CorporationInventors: Robert A. Falk, Kirkland P. Clark, Michael Jacobson, Athanasios Karydas, Juliana Rodgers
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Patent number: 5068390Abstract: 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: GrantFiled: July 31, 1990Date of Patent: November 26, 1991Assignee: American Cyanamid CompanyInventors: David G. Kuhn, Kenneth A. M. Kremer
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Patent number: 5030792Abstract: 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: GrantFiled: June 22, 1987Date of Patent: July 9, 1991Assignee: Shell Oil CompanyInventor: Lynn H. Slaugh
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Patent number: 5026898Abstract: 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: GrantFiled: January 31, 1990Date of Patent: June 25, 1991Assignee: E. I. Du Pont de Nemours and CompanyInventors: Frank W. Hobbs, James L. Meek
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Patent number: 5025003Abstract: 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: GrantFiled: September 18, 1989Date of Patent: June 18, 1991Assignee: E. R. Squibb & Sons, Inc.Inventor: Scott A. Biller
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Patent number: 5021453Abstract: Compounds of formula (I) and (II): ##STR1## are HMG-CoA reductase inhibitors.Type: GrantFiled: June 6, 1990Date of Patent: June 4, 1991Assignee: Merck & Co., Inc.Inventors: Henry Joshua, Kenneth E. Wilson, Michael S. Schwartz, Ta J. Lee, Gerald E. Stokker
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Patent number: 5017718Abstract: A process for preparing a perfluoroalkyl-substituted compound is disclosed. The process comprises reacting a halopolyfluoroalkane having 1 to 20 carbon atoms with a compound selected from the group consisting of (1) a substituted or unsubstituted ethylene, (2) a substituted or unsubstituted acetylene and (3) a substituted or unsubstituted allylsilane, in the presence of a metal-carbonyl complex of the metal of the Group VIII of the Periodic Table. Alternatively, the reaction between the halopolyfluoroalkane and the substituted or unsubstituted allylsilane is effected under radical generating condition.Type: GrantFiled: January 26, 1984Date of Patent: May 21, 1991Assignee: Sagami Chemical Research CenterInventors: Iwao Ojima, Takamasa Fuchikami
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Patent number: 5013475Abstract: 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: GrantFiled: October 27, 1989Date of Patent: May 7, 1991Assignee: Adeka Argus Chemical Co., Ltd.Inventors: Toshihiro Shibata, Masaki Kimura, Norio Kurosawa
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Patent number: 5004569Abstract: 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: GrantFiled: December 6, 1988Date of Patent: April 2, 1991Assignee: Bayer AktiengesellschaftInventors: Helmut-Martin Meier, Klaus Kircher, Klaus Berg
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Patent number: 4983747Abstract: 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: GrantFiled: March 15, 1990Date of Patent: January 8, 1991Assignee: Tokuyama Soda Kabushiki KaishaInventors: Masakatsu Nishimura, Naoya Okada, Yasuo Murata, Yasuhiko Hirai
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Patent number: 4980501Abstract: A process for the production of secondary-butyl perfluoroester is provided by reacting ethylene with a perfluorocarboxylic acid in the presence of oxygen.Type: GrantFiled: March 19, 1990Date of Patent: December 25, 1990Assignee: National Distillers and Chemical CorporationInventor: John A. Scheben
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Patent number: 4973426Abstract: 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: GrantFiled: February 25, 1988Date of Patent: November 27, 1990Assignee: Chisso CorporationInventors: Kouji Ohno, Shinichi Saito, Hiromichi Inoue, Kazutoshi Miyazawa, Makoto Ushioda
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Patent number: 4956123Abstract: 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: GrantFiled: September 14, 1988Date of Patent: September 11, 1990Assignee: Nippon Oils & Fats Company, Ltd.Inventors: Hideo Sawada, Michio Kobayashi, Masato Yoshida
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Patent number: 4952580Abstract: 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: GrantFiled: November 9, 1988Date of Patent: August 28, 1990Assignee: FMC CorporationInventors: Anthony J. Martinez, Thomas G. Cullen
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Patent number: 4948912Abstract: 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: GrantFiled: September 8, 1986Date of Patent: August 14, 1990Assignee: Southwest Research InstituteInventors: Robert E. Lyle, Jr., Donald J. Mangold, Nollie F. Swynnerton
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Patent number: 4946992Abstract: 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: GrantFiled: April 14, 1989Date of Patent: August 7, 1990Assignee: Ciba-Geigy CorporationInventors: Robert A. Falk, Kirtland P. Clark, Athanasios Karydas, Michael Jacobson
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Patent number: 4927954Abstract: 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: GrantFiled: April 19, 1989Date of Patent: May 22, 1990Assignee: Union Carbide Chemicals and Plastics Company, Inc.Inventors: Robert J. Knopf, Louis F. Theiling Jr., Leroy P. Berti
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Patent number: 4916256Abstract: 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: GrantFiled: August 18, 1988Date of Patent: April 10, 1990Assignee: Ausimont, S.p.A.Inventors: Saverio Grego, Adriano Checchin, Giorgio Guglielmo
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Patent number: 4879407Abstract: 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: GrantFiled: October 16, 1987Date of Patent: November 7, 1989Assignee: Rhone-Poulenc ChimieInventor: Louis Amiet
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Patent number: 4866189Abstract: 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: GrantFiled: September 16, 1988Date of Patent: September 12, 1989Assignee: Bristol-Myers CompanyInventors: Dolatrai M. Vyas, Paul M. Skonezny
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Patent number: 4855487Abstract: 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: GrantFiled: July 10, 1987Date of Patent: August 8, 1989Assignee: Sagami Chemical Research CenterInventors: Takamasa Fuchikami, Hisao Urata, Yoshimitsu Ishii, Yoshiko Obata
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Patent number: 4836958Abstract: 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: GrantFiled: July 31, 1986Date of Patent: June 6, 1989Assignee: Ciba-Geigy CorporationInventor: Athanasios Karydas
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Patent number: 4835305Abstract: 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: GrantFiled: April 13, 1988Date of Patent: May 30, 1989Assignee: Hoechst AktiengelselschaftInventors: Peter Blickle, Klaus Hintzer, Werner Schwertfeger, Dieter Ulmschneider
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Patent number: 4778915Abstract: 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: GrantFiled: October 16, 1986Date of Patent: October 18, 1988Assignee: AtochemInventors: Marie-Jose Lina, Andre Dessaint
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Patent number: 4766238Abstract: 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: GrantFiled: September 3, 1987Date of Patent: August 23, 1988Assignee: Daikin Industries, Ltd.Inventors: Yasuhisa Furutaka, Masayuki Yamana, Tsunetoshi Honda
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Patent number: 4730082Abstract: 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: GrantFiled: June 12, 1986Date of Patent: March 8, 1988Assignee: Rhone-Poulenc Specialties ChimiquesInventor: Louis Amiet
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Patent number: 4727199Abstract: 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: GrantFiled: July 10, 1985Date of Patent: February 23, 1988Assignee: Union Carbide CorporationInventor: Stephen W. King
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Patent number: 4719052Abstract: 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: GrantFiled: December 20, 1984Date of Patent: January 12, 1988Assignee: Daikin Industries Ltd.Inventors: Yohnosuke Ohsaka, Takashi Tohzuka, Shoji Takaki, Yoshio Negishi, Satoru Kohno
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Patent number: 4713469Abstract: 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: GrantFiled: March 27, 1986Date of Patent: December 15, 1987Assignee: Daikin Industries, Ltd.Inventors: Yoshio Takeuchi, Toru Koizumi, Kozo Hori
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Patent number: 4701551Abstract: 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: GrantFiled: July 21, 1986Date of Patent: October 20, 1987Assignee: Rhone-Poulenc Specialites ChimiquesInventors: Michel DesBois, Louis Amiet
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Patent number: 4695657Abstract: 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: GrantFiled: December 17, 1985Date of Patent: September 22, 1987Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Michel Desbois
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Patent number: 4659855Abstract: Certain novel aryl sulfonyl fluorides, their preparation, and their use in inhibiting serine proteases with chymotrypsin-like and elastase-like specificity.Type: GrantFiled: May 9, 1983Date of Patent: April 21, 1987Assignee: Georgia Tech Research CorporationInventor: James C. Powers
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Patent number: 4650913Abstract: 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: GrantFiled: November 29, 1984Date of Patent: March 17, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventor: Andrew E. Feiring
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Patent number: 4647691Abstract: 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: GrantFiled: January 13, 1982Date of Patent: March 3, 1987Assignee: Texaco Inc.Inventors: Jiang-Jen Lin, John F. Knifton
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Patent number: 4640802Abstract: 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: GrantFiled: July 7, 1982Date of Patent: February 3, 1987Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4617140Abstract: 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: GrantFiled: July 29, 1985Date of Patent: October 14, 1986Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Rudolf Eidenschink, Joachim Krause
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Patent number: 4602105Abstract: 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: GrantFiled: March 26, 1984Date of Patent: July 22, 1986Assignee: Shell Oil CompanyInventor: Eit Drent
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Patent number: 4596828Abstract: [(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: GrantFiled: March 28, 1985Date of Patent: June 24, 1986Assignee: Merck & Co., Inc.Inventors: Milton L. Hammond, Robert A. Zambias
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Patent number: 4582924Abstract: 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: GrantFiled: March 7, 1984Date of Patent: April 15, 1986Assignee: Daikin Kogyo Co., Ltd.Inventors: Nobuo Ishikawa, Takeshi Nakai
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Patent number: 4570018Abstract: 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: GrantFiled: May 16, 1984Date of Patent: February 11, 1986Assignee: Shionogi & Co., Ltd.Inventors: Tsutomu Aoki, Hiromi Takahashi, Toshiro Konoike, Teruji Tsuji, Wataru Nagata
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Patent number: 4568478Abstract: 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: GrantFiled: April 18, 1984Date of Patent: February 4, 1986Assignee: E. I. Dupont de Nemours and CompanyInventors: William J. Middleton, Shlomo Rozen
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Patent number: 4567296Abstract: 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: GrantFiled: June 29, 1984Date of Patent: January 28, 1986Assignee: The United States of America as represented by the Secretary of the NavyInventors: Theodore C. Adams, Jr., Horst G. Adolph
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Patent number: 4546200Abstract: 2,2-Dinitrobutane-1,4-diol and 4-monoesters thereof.Type: GrantFiled: May 6, 1983Date of Patent: October 8, 1985Assignee: The United States of America as represented by the Secretary of the NavyInventors: Michael E. Sitzmann, Horst G. Adolph
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Patent number: 4540810Abstract: 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: GrantFiled: September 20, 1979Date of Patent: September 10, 1985Assignee: Texaco Development CorporationInventor: John F. Knifton
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Patent number: 4539130Abstract: 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: GrantFiled: October 30, 1984Date of Patent: September 3, 1985Assignee: The Procter & Gamble CompanyInventors: James E. Thompson, Charles D. Broaddus
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Patent number: 4486327Abstract: 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: GrantFiled: December 22, 1983Date of Patent: December 4, 1984Assignee: The Procter & Gamble CompanyInventors: Alan P. Murphy, Ali Kassamali, John D. Curry
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Patent number: 4483778Abstract: 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: GrantFiled: December 22, 1983Date of Patent: November 20, 1984Assignee: The Procter & Gamble CompanyInventors: James E. Thompson, Charles D. Broaddus
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Patent number: 4479966Abstract: 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: GrantFiled: January 21, 1980Date of Patent: October 30, 1984Assignee: Ono Pharmaceutical Company, Ltd.Inventors: Masaki Hayashi, Yoshitaka Konishi, Yoshinobu Arai
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Patent number: 4478760Abstract: 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: GrantFiled: March 30, 1981Date of Patent: October 23, 1984Assignee: Produits Chimiques Ugine KuhlmannInventors: Hubert Blancou, Auguste Commeyras, Robert Teissedre