Plural -coo- Groups In The Reactant Patents (Class 568/355)
  • Publication number: 20150099894
    Abstract: The present invention relates to an improved process for the production of 4-alkanoyloxy-2-methylbutanoic acid, as well as to the use of such compounds in organic syntheses, especially in processes forming intermediates (building blocks) for the synthesis of organic compounds comprising isoprene (isoterpene) units, such as ?-carotene or other carotenoids (e.g. canthaxanthin, zeaxanthin or astaxanthin) or as vitamin E or vitamin A as well as other structurally similar compounds.
    Type: Application
    Filed: June 5, 2013
    Publication date: April 9, 2015
    Inventors: Werner Bonrath, Jan Schütz, Bettina Wüstenberg, Thomas Netscher
  • Patent number: 8304581
    Abstract: The present invention relates to a method of enantioselective addition to enones, including: reacting R3(CH2)pCH?CR5C(?O)Y(CH2)qR4 with R6ZnR7 in the presence of a compound represented by the following formula (I) and a transition metal catalyst, in which Y, p, q, R1, R2, R3, R4, R5, R6 and R7 are defined the same as the specification. Accordingly, the present invention can perform asymmetric conjugate addition in high yields and enantioselectivity.
    Type: Grant
    Filed: July 19, 2010
    Date of Patent: November 6, 2012
    Assignee: National Tsing Hua University
    Inventors: Biing-Jiun Uang, Chih-Hao Tseng
  • Patent number: 7781619
    Abstract: A process for the production of a ketone having a carbon number between about 20 and about 40 comprising contacting fatty acids containing from about 10 to about 21 carbons atoms with a hydrotalcite catalyst under conditions effective to decarboxylate said acids. More particularly said decarboxylation conditions comprise: a temperature in the range between about 300° C. and about 400° C.; a pressure in the range between about 0.01 and about 5 bar; and a weight hourly space velocity (WHSV) of from about 0.1 to about 10 hr?1.
    Type: Grant
    Filed: March 14, 2007
    Date of Patent: August 24, 2010
    Assignee: Albemarle Netherlands B.V.
    Inventors: Eelko Brevoord, Stephan Janbroers, Francisco René Mas Cabre, Mark Hendrikus Harte
  • Publication number: 20080188689
    Abstract: A method for preparing a molecule bearing a trifluoromethyl group on a quaternary carbon atom, includes providing a reactant having a quaternary carbon atom bearing a carboxylic acid group and an electron withdrawing group; and reacting the reactant with SF4 in a solvent to substitute the carboxylic acid group with the trifluoromethyl group and provide a reaction product mixture including the molecule bearing the trifluoromethyl group on the quaternary carbon atom.
    Type: Application
    Filed: February 6, 2007
    Publication date: August 7, 2008
    Inventors: Gauri Sankar Lal, Michael Ulman, William Jack Casteel
  • Patent number: 7247753
    Abstract: The invention relates to a method for producing macrocyclic ketones of general formula (I) by direct cyclisation of compounds of general formula (II) in the gas phase on a heterogeneous catalyst. In general formula (I), X represents a monounsaturated or polyunsaturated or saturated C10–C17 alkyl radical which can be optionally substituted by a C1–C6 alkyl radical, and in general formula (II), R1, R2 can respectively be the same or different and represent hydrogen or C1–C6 alkyl, and has the above-mentioned designation.
    Type: Grant
    Filed: July 10, 2003
    Date of Patent: July 24, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Alexander Wartini, Klaus Ebel, Gisela Hieber, Hagen Weigl
  • Patent number: 6828464
    Abstract: The present invention provides a process for preparing 2-cyclopentenones of the general formula: where R1 to R4 are each hydrogen atoms or are alkyl or alkenyl radicals having from 1 to 12 carbon atoms, cycloalkyl or cycloalkenyl radicals having from 5 to 7 carbon atoms, aralkylene or aryl radicals, by converting hexenedioic acids and/or their esters of the general formulae where R1 to R4 are each as defined above and R5 and R6 are each hydrogen atoms or are alkyl radicals having from 1 to 12 carbon atoms, cycloalkyl radicals having 5 or 6 carbon atoms, aralkyl or aryl radicals, at temperatures of from 150 to 450° C., over solid, oxidic catalysts, wherein the catalysts on an oxidic support material comprise from 0.01 to 5% by weight of at least one alkali metal oxide.
    Type: Grant
    Filed: November 24, 2003
    Date of Patent: December 7, 2004
    Assignee: BASF Aktiengesellschaft
    Inventors: Shelue Liang, Rolf-Hartmuth Fischer, Sylvia Huber-Dirr, Andrea Haunert
  • Patent number: 6762327
    Abstract: A safe and effective process for the oxidation of a primary or secondary alcohol to the corresponding aldehyde or ketone via the reaction of said alcohol with an anhydride solution of a 1,1,1-tri(C2-C4 alkanoyloxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one, and a composition useful in this process.
    Type: Grant
    Filed: April 3, 2003
    Date of Patent: July 13, 2004
    Assignee: Wyeth
    Inventors: Ugo Chiacchio, Antonio Rescifina, Giuseppe Miraglia, Mariangela Magnano, Paola Di Raimondo
  • Publication number: 20040102655
    Abstract: The present invention provides a process for preparing 2-cyclopentenones of the general formula: 1
    Type: Application
    Filed: November 24, 2003
    Publication date: May 27, 2004
    Inventors: Shelue Liang, Rolf-Hartmuth Fischer, Sylvia Huber-Dirr, Andrea Haunert
  • Publication number: 20030078455
    Abstract: Disclosed are a process of subjecting a diester of a long-chain dicarboxylic acid having 18 to 21 carbon atoms to intramolecular condensation in the presence of titanium tetrachloride or zirconium tetrachloride and a trialkylamine to form an &agr;-alkoxycarbonylated macrocyclic ketone, and a process for producing a macrocyclic ketone by hydrolyzing an &agr;-alkoxycarbonylated macrocyclic ketone obtained by the process and then subjecting the hydrolyzate to decarboxylation. The invention provides a process for producing a macrocyclic ketone efficiently, which permits high concentration synthesis.
    Type: Application
    Filed: September 19, 2002
    Publication date: April 24, 2003
    Inventors: Yoo Tanabe, Atsushi Makita
  • Patent number: 6500990
    Abstract: A process for efficiently producing a 2-alkyl-2-cyclopentenone comprising reacting an amine and a hydrogen halide, which are present in a ratio ranging from 1.1:1 to 5:1, with a 2-alkylidene cyclopentanone to carry out an isomerization reaction. A process for producing a jasmonate derivative comprising reacting a 2-alkyl-2-cyclopentenone with a malonic acid diester.
    Type: Grant
    Filed: March 13, 2001
    Date of Patent: December 31, 2002
    Assignee: Kao Corporation
    Inventors: Takahiro Asada, Yoshiharu Ataka, Junji Koshino
  • Patent number: 6429339
    Abstract: A process for preparing cyclopentanone by reacting adipic esters of the formula R1OOC—(CH2)4—COOR2  I where R1 and R2 are each alkyl having from 1 to 12 carbon atoms, cycloalkyl having 5 or 6 carbon atoms, aralkyl or aryl and R2 may additionally be hydrogen, in the presence of oxidic catalysts comprises reacting adipic esters of the formula I having less than 5% by weight of by-products other than adipic esters in the gas phase in the presence of water, a carrier gas and a) from 0.01 to 10% by weight of at least one metal oxide selected from the first or second main group of the periodic table or from the group of the rare earth metals on titanium dioxide or zirconium dioxide as catalyst support, or b) from 0.01 to 50% by weight of at least one metal oxide selected from the second main group of the periodic table on zink oxide as catalyst support.
    Type: Grant
    Filed: November 15, 2000
    Date of Patent: August 6, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Shelue Liang, Rolf Fischer, Frank Stein, Joachim Wulff-Döring
  • Patent number: 6369276
    Abstract: A catalyst structure and method of making and using the same in a ketone production process. The catalyst structure includes a substantial theoretical monolayer of catalyst on a catalyst support to optimize ketone yield and weight hourly space velocities.
    Type: Grant
    Filed: September 2, 1999
    Date of Patent: April 9, 2002
    Assignee: EagleView Technologies, Inc.
    Inventor: Jack S. Warren
  • Patent number: 5856581
    Abstract: Cyclic ketones, notably cyclopentanone and 2,2-dimethylcyclopentanone, are simply, economically and efficiently prepared, even on an industrial scale, by decarboxylating/cyclizing a dicarboxylic acid, in liquid phase, in the presence of a catalytically effective amount of a metal or compound thereof selected from among boron, aluminum, gallium, indium, thallium, tin, antimony, bismuth, molybdenum, rubidium, cesium and vanadium.
    Type: Grant
    Filed: May 31, 1994
    Date of Patent: January 5, 1999
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Alas, Michel Crochemore
  • Patent number: 5856582
    Abstract: A process for the manufacture of 2-hydroxy-3-methylcyclopent-2-ene-1-one, in which an ester of alpha-methyl glutaric acid and an ester of oxalic acid react in a polar aprotic solvent in the presence of an alkali metal alkoxide to form an intermediate compound which, after removal of said polar aprotic solvent and alcohols formed in the reaction, is hydrolyzed and decarboxylated to form said 2-hydroxy-3-methycyclopent-2-ene-1-one.
    Type: Grant
    Filed: September 26, 1997
    Date of Patent: January 5, 1999
    Inventor: Glen Francis Crum
  • Patent number: 5824820
    Abstract: The present invention relates to a novel process for the preparation of citraconic anhydride. More precisely, the invention relates to a process for the preparation of citraconic anhydride from a starting material comprising itaconic acid.The process for the preparation of citraconic anhydride may be performed continuously starting from itaconic acid, or continuously or in a batchwise manner starting directly from a fermentation broth of itaconic acid or of by-products from the manufacture of itaconic acid.
    Type: Grant
    Filed: June 19, 1996
    Date of Patent: October 20, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventor: Michel Alas
  • Patent number: 5672763
    Abstract: 2-Substituted cyclopentanones are prepared by reacting adipic ester with an alkoxide in the presence of an inert solvent, thus obtaining a salt of the cyclopentanone-2-carboxylic ester, alkylating this without isolation, thus obtaining a 2-alkyl-cyclopentanone-2-carboxylic ester and, without isolation, hydrolysing and decarboxylating this by treatment with an acid and heating.
    Type: Grant
    Filed: June 21, 1996
    Date of Patent: September 30, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Nikolaus Muller, Thomas Essert
  • Patent number: 5600013
    Abstract: Cyclic ketones, notably cyclopentanone and 2,2-dimethylcyclopentanone, are simply, economically and efficiently prepared, even on an industrial scale, by decarboxylating/cyclizing a dicarboxylic acid, in liquid phase, in the presence of a catalytically effective amount of a condensed or uncondensed neutral phosphate.
    Type: Grant
    Filed: October 4, 1995
    Date of Patent: February 4, 1997
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Alas, Michel Crochemore
  • Patent number: 5567851
    Abstract: The present invention relates to optically active cyclohexene diol derivatives and optically active cyclohexenone derivatives, and a process for production of these compounds in which a special cyclohexene diol of a starting material is reacted by selectively positioning transesterification in the presence of lipase to obtain an optically active cyclohexene diol derivative and then an optically active cyclohexenone derivative represented by the following formula: ##STR1## According to the present invention, optically active cyclohexene diol derivatives and optically-active cyclohexenone derivatives, which are intermediates for synthesizing physiologically active materials, can be obtained efficiently.
    Type: Grant
    Filed: May 24, 1995
    Date of Patent: October 22, 1996
    Assignee: Chisso Corporation
    Inventors: Seiichi Takano, Kunio Ogasawara
  • Patent number: 5426235
    Abstract: Cyclic ketones of the general formula I ##STR1## where n is an integer from 4 to 6, are prepared by reacting aliphatic dicarbonitriles of the general formula IINC--(CH.sub.2).sub.n --CN (II),where n has the abovementioned meaning, in the gas phase in the presence of water at from 250.degree. to 500.degree. C. on solid oxide catalysts.
    Type: Grant
    Filed: June 1, 1994
    Date of Patent: June 20, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Juergen Schroeder, Klaus Ebel, Charles Schommer
  • Patent number: 5399775
    Abstract: The present invention relates to a process for the preparation of substituted cyclobutanes and their use as intermediates for the preparation of anti-viral nucleoside analogs.
    Type: Grant
    Filed: June 14, 1993
    Date of Patent: March 21, 1995
    Assignee: Bristol-Myers Squibb Co.
    Inventors: Richard J. Pariza, Steven M. Hannick, Thomas J. Sowin, Elizabeth M. Doherty
  • Patent number: 5386039
    Abstract: Perhydro-5,5-8a-trimethyl-2-naphthalenone is prepared by acid cyclization of carboxylic esters of formula ##STR1## having a double bond in one of the positions indicated by the dotted lines and wherein symbol R designates a C.sub.1 -C.sub.6 alkyl radical, X stands for a monovalent radical of formula P(O)(OR.sup.1).sub.2 or C(O)R.sup.2, R.sup.1 represents a C.sub.1 -C.sub.6 alkyl group and R.sup.2 is either a linear or branched alkyl group or a substituted or unsubstituted phenyl radical, and wherein the wavy line represents a C--C bond of cis or trans configuration, or of formula ##STR2## wherein the wavy lines and symbol R are defined as above, and R.sup.0 represents a C.sub.3 -C.sub.6 alkyl radical, preferably branched, followed by basic decarboxylation of the obtained product.
    Type: Grant
    Filed: July 20, 1993
    Date of Patent: January 31, 1995
    Assignee: Firmenich SA
    Inventors: Roger L. Snowden, Cyril Mahaim, Dana P. Simmons
  • Patent number: 5360819
    Abstract: A release tag reagent suitable for use in the chemical analysis of a substance to be detected, which substance contains reactive groups, such as for, but not limited to gas phase detection groups, which reagent comprises three covalently bonded groups: a signal group which on release provides a ketone signal compound to be detected, a release group which may be cleaved to release the ketone signal group, which release group contains, for example, a vic glycol or an olefin group and a reactivity group which is reactive with a reactive group of the substance to be detected.
    Type: Grant
    Filed: March 11, 1985
    Date of Patent: November 1, 1994
    Assignee: Northeastern University
    Inventor: Roger W. Giese
  • Patent number: 5262552
    Abstract: An optically active (S)- or (R)-pentane compound of the general formula (11): ##STR1## wherein R.sub.11, R.sub.12 and R.sub.13 independently represent a hydrogen atom or a lower alkyl group having 1 to 4 carbon atoms, R.sub.14 represents a hydroxy, protected hydroxy or oxo group, if R.sub.14 is an oxo group, the ring denoting benzene in the above formula (11) is benzoquinone, R.sub.15 represents a hydrogen atom, hydroxy or acyloxy group, R.sub.16 represents a hydroxy or acyloxy group, and the chiral central carbon marked with a symbol * in said formula (11) alternatively has one of an R-configuration and an S-configuration, is disclosed. Further, intermediate products of the compound of the formula (11) are also disclosed. Still further, a process for manufacturing the above compounds is disclosed. The compound of the formula (11) is easily synthesized from an easily available optically active starting material.
    Type: Grant
    Filed: February 20, 1991
    Date of Patent: November 16, 1993
    Assignee: Asahi Denka Kogyo K.K.
    Inventors: Seiichi Takano, Kunio Ogasawara
  • Patent number: 5210272
    Abstract: The preparation of magnesium benzyl fluoromalonate and other equivalent materials, the synthetic equivalents of the --CH.sub.2 F moiety, is described. Reaction between these reagents and the in situ-formed imidazolides of various carboxylic acids gives beta-keto-alpha-fluoroesters, which upon hydrogenation and spontaneous decarboxylation yields fluoromethyl ketones in excellent yields. The overall transformation from RCOOH to RCOCH.sub.2 F is thus illustrated.
    Type: Grant
    Filed: August 14, 1991
    Date of Patent: May 11, 1993
    Assignee: Prototek, Inc.
    Inventor: James T. Palmer
  • Patent number: 4983774
    Abstract: The preparation of ketones by reacting an acylating agent with an organo-manganous compound is catalyzed by a copper compound.
    Type: Grant
    Filed: December 16, 1988
    Date of Patent: January 8, 1991
    Assignee: Societe Nationale Elf Aquitaine
    Inventors: Gerard Cahiez, Blandine Laboue, Pierre Tozzolino
  • Patent number: 4895985
    Abstract: The invention relates to a process for the preparation of cyclopentanone from adipic acid wherein adipic acid vapor in an inert gas at a temperature of from 250.degree. C. to 450.degree. C., possibly accompanied by water vapor, is passed over an oxygenous acidic or basic catalyst.
    Type: Grant
    Filed: August 25, 1988
    Date of Patent: January 23, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Martin Decker, Harro Wache, Wolfgang Franzischka
  • Patent number: 4827044
    Abstract: Process of preparation of ketones by the reaction of an organo-metallic compound with a compound carrying a carbonyl, within a solvent, in the presence of a manganous salt as catalyst. The manganous salt is in the form of a double salt of Mn and an alkali metal cation.
    Type: Grant
    Filed: March 8, 1988
    Date of Patent: May 2, 1989
    Assignee: Societe Nationale Elf Aquitaine
    Inventors: Pierre Tozzolino, Gerard Cahiez
  • Patent number: 4822920
    Abstract: Cyclopentanone is prepared from adipic esters by reacting adipic esters of the formulaR.sup.1 OOC--(CH.sub.2).sub.4 --COOR.sup.2where R.sup.1 and R.sup.2 are alkyl of 1 to 12 carbon atoms, cycloalkyl of 5 or 6 carbon atoms, aralkyl or aryl and R.sup.2 can additionally be hydrogen, in the gas or liquid phase at from 150.degree. C. to 450.degree. C. in the presence of zeolitic catalysts and/or phosphate catalysts, preferably zeolites of the pentasil type.
    Type: Grant
    Filed: November 5, 1987
    Date of Patent: April 18, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Helmut Lermer, Wolfgang Hoelderich, Matthias Schwarzmann
  • Patent number: 4788343
    Abstract: Cycloheptanone (suberone) is prepared by first evaporating suberic-acid esters which are reacted in alcoholic and/or aqueous dilution in the gas phase on aluminum oxide support catalyst doped with zinc oxide and/or cerium oxide at temperatures between 300.degree. and 600.degree. C.
    Type: Grant
    Filed: August 14, 1987
    Date of Patent: November 29, 1988
    Assignee: Huls Aktiengesellschaft
    Inventor: Walter Kleine-Homann
  • Patent number: 4764641
    Abstract: A process is described for preparing optically active alpha-halogenated carbonyl compounds.This process consists of transforming the carbonyl compound into the corresponding acetal with tartaric acid or a derivative thereof, halogenating this acetal and releasing the carbonyl compound.
    Type: Grant
    Filed: October 6, 1986
    Date of Patent: August 16, 1988
    Assignee: Zambon SpA
    Inventors: Graziano Castaldi, Silvia Cavicchioli, Claudio Giordano, Carlo Restelli
  • Patent number: 4499307
    Abstract: Described is a process for preparing 4,4A,5,6-tetrahydro-7-methyl-2-(3H)-naphthalenone having the structure: ##STR1## and intermediates useful in such process defined according to the structure: ##STR2## wherein one of R.sub.3 or R.sub.4 is hydrogen and the other of R.sub.3 or R.sub.4 is acetyl; and one of R.sub.1 or R.sub.2 is methyl and the other of R.sub.1 or R.sub.2 is acetoxy, said compound defined according to the structure: ##STR3## being useful in augmenting or enhancing the aroma or taste of consumable materials including foodstuffs, chewing gums, medicinal products, chewing tobaccos, toothpastes, smoking tobaccos, smoking tobacco articles, perfumes, colognes and perfumed articles including solid or liquid anionic, cationic, nonionic or zwitterionic detergents, fabric softeners, fabric softener articles and perfumed polymers.
    Type: Grant
    Filed: February 23, 1984
    Date of Patent: February 12, 1985
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan O. Pittet, Ranya Muralidhara, Myrna L. Hagedorn
  • Patent number: 4440740
    Abstract: A method and drug form enhancing the absorption of a rectally or orally administered drug from the rectal compartment into the blood stream of a warm blooded animal. The method includes the steps of preparing a drug form capable of being rectally and orally administered. The drug form comprises a therapeutically effective unit dosage amount of a selected drug of the type which is capable of being absorbed into the blood stream from the gastrointestinal area and an .alpha.-keto aldehyde or salts thereof being present in the drug form in a sufficient amount to be effective in enhancing the drug absorption rate, when administering the drug form to warm blooded animals.
    Type: Grant
    Filed: April 26, 1982
    Date of Patent: April 3, 1984
    Assignee: Merck & Co., Inc.
    Inventors: Joseph A. Fix, Stefano A. Pogany
  • Patent number: 4407757
    Abstract: Novel compounds of the formulae ##STR1## wherein R represents lower alkyl or lower alkoxy, A represents --CH.sub.2 --, --CO-- or ##STR2## n represents an integer of 1 to 8, X represents hydrogen or hydroxyl which may be protected and Y represents hydroxyl which may be protected, and their esters show an excellent action on the lysosomal membranes of cells, and exhibit excellent pharmacological activities such as physiologic host defense control activity, especially immuno-potentiating activity.
    Type: Grant
    Filed: December 31, 1980
    Date of Patent: October 4, 1983
    Assignee: Takeda Chemical Industries, Ltd.
    Inventors: Hiroshi Morimoto, Isuke Imada, Masazumi Watanabe, Mitsuru Kawada