Reactant Contains -coo- Group Patents (Class 568/354)
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Patent number: 11840491Abstract: Systems for preparing butenes are provided. The systems can include a reactor inlet coupled to both a reactor and at least one reactant reservoir; at least one of the reactant reservoirs containing one or both of an aldehyde and/or ethanol; a catalyst within the reactor, the catalyst comprising a metal component and an acidic support material; and a reactor outlet operationally configured to convey a butene-rich reaction product to a product reservoir. Methods for preparing butenes are also provided. The methods can include exposing one or both of ethanol and/or an aldehyde to a catalyst comprising a metal component and an acidic support to form a butene-rich product that comprises one or both of 1-butene and/or 2-butene.Type: GrantFiled: June 22, 2022Date of Patent: December 12, 2023Assignee: Battelle Memorial InstituteInventors: Vanessa Dagle, Robert A. Dagle
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Patent number: 10011777Abstract: Systems and methods are provided for processing a feed derived from a biomass source that contains nitrogen in the form of fatty amides, e.g., derived from hydrothermal processing of a biomass source feed, while reducing/minimizing the amount of heteroatom removal performed during subsequent/concurrent hydroprocessing. Optionally, the feed can also contain free fatty acids. This is accomplished in part by first exposing the feed to a catalyst comprising a rare earth oxide, alkali oxide, and/or alkaline earth oxide, which can remove the nitrogen heteroatoms from the compounds within the feed or can convert the nitrogen to a form readily removed in subsequent hydroprocessing. The catalyst may also suitable for catalyzing coupling (such as condensation) or conversion reactions of amides, carboxylic acids, carboxylic acid derivatives, and/or other molecules in the feed suitable for participating in the coupling reaction.Type: GrantFiled: October 15, 2013Date of Patent: July 3, 2018Assignee: EXXONMOBIL RESEARCH AND ENGINEERING COMPANYInventors: Virginia M. Roberts, Michel Daage, Kun Wang
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Patent number: 9162956Abstract: A process for preparing cyclohexanol and cyclohexanone by cyclohexane oxidation includes steps of: non-catalyticly oxidizing cyclohexane with molecular oxygen in the air to obtain an oxidation mixture containing CHHP as a main product; performing a homogenous catalytic decomposition of the CHHP to obtain cyclohexanol and cyclohexanone; and rectifying to obtain products of the cyclohexanol and the cyclohexanone, wherein the step of performing the homogenous catalytic decomposition involves a homogeneous catalytic decomposition reaction and distillation vessel which removes water via azeotropic rectification to reduce a water content of a decomposition liquid to be below 100 ppm. A device therefor includes the homogeneous catalytic decomposition reaction and distillation vessel for performing the homogenous catalytic decomposition of the CHHP.Type: GrantFiled: May 17, 2012Date of Patent: October 20, 2015Inventor: Zaosheng Xiao
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Patent number: 9150481Abstract: A process for preparing cyclohexanol and cyclohexanone by cyclohexane oxidation, includes steps of: firstly processing uncatalyzed oxidation on cyclohexane by molecular oxygen, in such a manner that an oxidized mixture with cyclohexyl hydrogen peroxide serving as a primary product is generated; then decomposing the cyclohexyl hydrogen peroxide to produce cyclohexanol and cyclohexanone; and then distilling to obtain a cyclohexanol product and a cyclohexanone product, wherein the step decomposing the cyclohexyl hydrogen peroxide utilizes a three-step decomposition process including steps of: (1) performing the homogeneous catalytic decomposition by utilizing the bis(tert-butyl)chromate as a catalyst; (2) performing the heterogeneous catalytic decomposition of the sodium hydroxide alkaline aqueous solution under low alkalinity; and (3) performing the heterogeneous catalytic decomposition of the sodium hydroxide alkaline aqueous solution under high alkalinity.Type: GrantFiled: May 17, 2012Date of Patent: October 6, 2015Inventor: Zaosheng Xiao
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Patent number: 9126918Abstract: A process for preparing cyclohexanol and cyclohexanone from cyclohexane includes steps of: (1) non-catalyticly oxidizing cyclohexane with molecular oxygen to obtain an oxidized mixture liquid containing cyclohexyl hydroperoxide (CHHP) as a main product; (2) performing a homogenous catalytic decomposition with an oil-soluble transitional metal compound serving as a catalyst, and serving as a scale inhibitor by 1-hydroxy ethidene-1,1-diphosphonic acid (di)octyl ester, or a combination of 1-hydroxy ethidene-1,1-diphosphonic acid (di)octyl ester and phosphoric acid octyl ester, to decompose the CHHP in the oxidized mixture liquid into cyclohexanol and cyclohexanone; and (3) rectifying to obtain products of the cyclohexanol and the cyclohexanone.Type: GrantFiled: May 17, 2012Date of Patent: September 8, 2015Inventor: Zaosheng Xiao
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Patent number: 9096509Abstract: In a process for producing phenol, a mixture of cyclohexylbenzene with from 10 to 90 wt % of a solvent is contacted with oxygen in the presence of a catalyst and under conditions effective to oxidize at least a portion of the cyclohexylbenzene to cyclohexylbenzene hydroperoxide. The catalyst comprises a cyclic imide having an imide group of formula (I): wherein X represents an oxygen atom, a hydroxyl group, or an acyloxy group. At least a portion of the oxygen is dissolved in the mixture and the liquid phase molar ratio of cyclohexylbenzene to oxygen dissolved in the mixture is less than or equal to 20,000:1.Type: GrantFiled: December 3, 2012Date of Patent: August 4, 2015Assignee: ExxonMobil Chemical Patents Inc.Inventors: Bryan A. Patel, Jihad M. Dakka
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Patent number: 9067870Abstract: In a process for producing phenol, a feed comprising cyclohexylbenzene hydroperoxide is contacted with a cleavage catalyst comprising a fluorinated acidic resin under cleavage conditions effective to convert at least a portion of the cyclohexylbenzene hydroperoxide into phenol and cyclohexanone.Type: GrantFiled: August 10, 2012Date of Patent: June 30, 2015Assignee: ExxonMobil Chemical Patents Inc.Inventors: Kun Wang, Roberto Garcia, Francisco M. Benitez
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Publication number: 20110251399Abstract: The invention relates to a method for producing aldehydes and ketones from easily accessible primary and secondary alcohols by oxidation with atmospheric oxygen or pure oxygen using a catalyst system which consists of a derivative of a free nitroxyl radical.Type: ApplicationFiled: January 25, 2010Publication date: October 13, 2011Applicant: EVONIK DEGUSSA GMBHInventors: Uwe Dingerdissen, Jan Pfeffer, Thomas Tacke, Thomas Haas, Harald Schmidt, Florian Klasovsky, Roger Sheldon, Michiel Janssen, Michael Volland, Michael Rimbach, Stefanie Rinker
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Patent number: 7825277Abstract: A process for the ozonolysis of unsaturated starting materials, which is characterized in that the reaction is carried out in a structured reactor.Type: GrantFiled: May 9, 2007Date of Patent: November 2, 2010Assignee: Cognis IP Management GmbHInventors: Bernhard Gutsche, Stefan Franzen, Markus Kloeker
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Patent number: 7781619Abstract: 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: GrantFiled: March 14, 2007Date of Patent: August 24, 2010Assignee: Albemarle Netherlands B.V.Inventors: Eelko Brevoord, Stephan Janbroers, Francisco René Mas Cabre, Mark Hendrikus Harte
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Publication number: 20100137646Abstract: The invention describes the preparation and isolation of xanthophylls from plant sources. whereby a transesterification process is utilized without the necessity of an aqueous format.Type: ApplicationFiled: June 4, 2008Publication date: June 3, 2010Applicant: MULTI-TECH SPECIALTY CHEMICALS CO., LTD.Inventor: Jian DU
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Patent number: 7649118Abstract: There are provided a novel norbornene derivative which is a material for a chemically amplifying type photoresist for F2 laser, possesses excellent transparency and improved dry etching resistivity and has a fluorine-containing ketone unit or fluorine-containing tertiary alcohol unit directly bonded to the norbornene backbone; a fluorine-containing polymer obtained by using the norbornene derivative as a copolymerizable monomer; and a chemically amplifying type photoresist composition comprising the fluorine-containing polymer, a photoacid generator and a solvent.Type: GrantFiled: January 4, 2007Date of Patent: January 19, 2010Assignee: Daikin Industries, Ltd.Inventors: Takayuki Araki, Takuji Ishikawa, Takuji Kume, Akinori Yamamoto
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Publication number: 20090221832Abstract: A process for preparing ketones of the general formula (III) where R is an optionally substituted carbocyclic aromatic radical having 6 to 24 carbon atoms or an optionally substituted alkyl radical or an optionally substituted heteroaromatic radical having 5 to 24 carbon atoms, and R1 is an optionally substituted carbocyclic aromatic radical having 6 to 24 carbon atoms or an optionally substituted heteroaromatic radical having 5 to 24 carbon atoms, by reacting alpha-oxo carboxylates of the general formula (I) wherein n and m is a number in the range from 1 to 6, M(m+) is a cation, and R has the meaning indicated for formula (III), with aryl bromides of the general formula (II) R1—Br ??(II) where R1 has the meaning indicated for formula (III), in the presence of two transition metals or compounds thereof as catalyst, is described.Type: ApplicationFiled: February 19, 2009Publication date: September 3, 2009Applicant: SALTIGO GMBHInventors: Alain Cotte, Matthias Gotta, Lukas Goossen, Felix Rudolphi, Christoph Oppel, Nuria Rodriguez Garrido
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Patent number: 7396961Abstract: The present invention relates to a process for decomposing organic hydroperoxides in the presence of a catalyst. It provides a process for decomposing organic hydroperoxides in the presence of a catalyst into a mixture of alcohols and ketones, in which the catalyst comprises at least one ruthenium-based catalytically active metallic element incorporated into a solid support chosen from the group comprising metal oxides and carbon blacks, such as the carbon blacks obtained by the pyrolysis of organic compounds. The process of the invention is especially useful in the decomposition of important chemical intermediates such as cyclohexyl hydroperoxide.Type: GrantFiled: January 20, 2006Date of Patent: July 8, 2008Assignee: Rhodia Polyamide IntermediatesInventors: Didier Bonnet, Eric Fache, Aline Seigneurin
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Patent number: 7268258Abstract: The present invention provides a process for producing a muscone represented by (1) by subjecting a citronellic acid derivative and an undecenoate to a Claisen condensation reaction to produce a keto ester compound represented by (2) decarboxylating the keto ester compound to produce 2,6-dimethyl-8-oxy-2,17-heptadecadiene, cyclizing the heptadecadiene using a metathesis catalyst to produce a 6-dehydromuscone represented by (3) and then hydrogenating the double bond.Type: GrantFiled: December 1, 2005Date of Patent: September 11, 2007Assignee: Takasago International CorporationInventors: Yoo Tanabe, Tomonori Misaki, Ryohei Nagase, Kunshi Matsumoto
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Patent number: 7081552Abstract: A cyclic ketone/alcohol mixture is prepared by catalytic oxidation of the corresponding cycloalkane or catalytic decomposition of the corresponding cycloalkyl hydroperoxide. Gold supported on a porous crystalline silicate containing less than about 2 wt. % aluminum or a crystalline phosphate is used as a catalyst. The support material optionally contains one or more heteroatoms.Type: GrantFiled: August 17, 2004Date of Patent: July 25, 2006Assignee: Solutia Inc.Inventors: Larisa V. Pirutko, Alexander S. Kharitonov, Mikhail I. Khramov, Anthony K. Uriarte
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Patent number: 7015358Abstract: A process for the production of aliphatic or alicyclic monoketones or alicyclic diketones of the formula R1—C(?O)—R2 in which R1 is a linear or branched C1-10-alkyl group and R2 is a linear or branched C1-10-alkyl group or a phenyl group, or R1 or R2 together are —(CH2)m—[C(?O)]n—(CH2)p—, wherein m and p independently are integers from 1 to 4 and n is 0 or 1, thus forming an alicyclic ring together with the carbonyl group of R1—C(?O)—R2 by oxidizing a secondary alcohol of formula R1?—CHOH—R2? in which R1? and R2? either have the same meaning as R1 and R2 above or, if R1 and R2 together are —(CH2)m—[C(?O)]n—(CH2)p—, are together —(CH2)m—(CHOH)n—(CH2)p— wherein m, n and p are as defined above, with a peroxy compound in the presence of a carboxylic acid and a manganese(IV) complex of 1,4,7-trimethyl-1,4,7-triazacyclononane.Type: GrantFiled: April 23, 2002Date of Patent: March 21, 2006Assignee: Lonza AGInventors: Georg Süss-Fink, Georgiy B Shul′Pin, Lidia S. Shul′Pina
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Patent number: 6969776Abstract: The present invention provides a process whereby fluorinated ketones of various structures can be produced by short process steps and which is useful as an industrial production process.Type: GrantFiled: June 17, 2004Date of Patent: November 29, 2005Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu, Hirokazu Takagi
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Patent number: 6861551Abstract: 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 ?-alkoxycarbonylated macrocyclic ketone, and a process for producing a macrocyclic ketone by hydrolyzing an ?-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: GrantFiled: March 28, 2001Date of Patent: March 1, 2005Assignee: Japan Energy CorporationInventors: Yoo Tanabe, Atsushi Makita
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Patent number: 6803488Abstract: The present invention provides a process whereby fluorinated ketones of various structures can be produced by short process steps and which is useful as an industrial production process.Type: GrantFiled: February 26, 2003Date of Patent: October 12, 2004Assignee: Asahi Glass Company, LimitedInventors: Takashi Okazoe, Kunio Watanabe, Masahiro Ito, Daisuke Shirakawa, Shin Tatematsu, Hirokazu Takagi
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Patent number: 6762327Abstract: 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: GrantFiled: April 3, 2003Date of Patent: July 13, 2004Assignee: WyethInventors: Ugo Chiacchio, Antonio Rescifina, Giuseppe Miraglia, Mariangela Magnano, Paola Di Raimondo
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Patent number: 6677490Abstract: The invention relates to a method for producing a mixture of alcohols/ketones by decomposing an alkyl hydroperoxide, particularly to a method for producing a cyclohexanol/cyclohexanone by decomposing cyclohexyl hydroperoxide in the presence of a heterogeneous catalyst. According to the invention, the reaction is carried out in the presence of a heterogeneous catalyst containing an organometallic segment fixed on the surface of a porous solid compound such as silicon. The organometallic segment can be formula (I).Type: GrantFiled: October 15, 2002Date of Patent: January 13, 2004Assignee: Rhodia Polyamide IntermediatesInventors: James Clark, Eric Fache, Ducan Macquarrie, Peter Price, John Rafelt
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Patent number: 6545185Abstract: A method and apparatus for the production of ketones via a one-step synthesis from aldehydes. In the method of the invention, an aldehyde, a carboxylic acid, and a source of oxygen, such as water, are allowed to react in the vapor phase in a catalytic tube reactor. Asymmetrical ketones, such as methyl cyclopropyl ketone, are particularly desirable reaction products.Type: GrantFiled: October 17, 2001Date of Patent: April 8, 2003Assignee: EagleView Technologies, Inc.Inventors: Jack S. Warren, David R. Westphal, Steve J. Zoubek
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Publication number: 20020193638Abstract: A method and apparatus for continuously producing a ketone in a tube reactor at elevated weight hourly space velocities and in the presence of a catalyst from feed material comprised of a first carboxylic acid or aldehyde or their derivatives and a second carboxylic acid and a method for using the ketone production method to produce herbicidal or other agricultural compounds.Type: ApplicationFiled: May 10, 2002Publication date: December 19, 2002Applicant: EagleView Technologies, Inc.Inventor: Jack S. Warren
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Patent number: 6476274Abstract: The invention relates to a process for preparing cyclobutanone by oxidizing cyclobutanol with an alkali metal hypochlorite or alkaline earth metal hypochlorite in the presence of an acid.Type: GrantFiled: September 6, 2001Date of Patent: November 5, 2002Assignee: Bayer AktiengesellschaftInventors: Hans-Joachim Knops, Bernd Gallenkamp, Lubbertus Mulder, Stefan Antons
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Patent number: 6392099Abstract: A method for continuously producing a ketone in a tube reactor at elevated weight hourly space velocities and in the presence of a catalyst from feed material comprised of a first carboxylic acid or aldehyde or their derivatives and a second carboxylic acid and a method for using the ketone production method to produce herbicidal or other agricultural compounds.Type: GrantFiled: September 13, 1999Date of Patent: May 21, 2002Assignee: EagleView Technologies, Inc.Inventor: Jack S. Warren
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Patent number: 6369276Abstract: 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: GrantFiled: September 2, 1999Date of Patent: April 9, 2002Assignee: EagleView Technologies, Inc.Inventor: Jack S. Warren
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Patent number: 6316659Abstract: A process for preparing cyclopentanone and cyclopentene-1-carboxylic acid or an ester thereof of the formula I where R is hydrogen or an aliphatic radical having 1-6 carbon atoms or a cycloaliphatic, araliphatic or aromatic radical having 6-12 carbon atoms comprises heating a compound of the formula II X—(CH2)4—COOR II where X is formyl or hydroxymethyl and R is defined as above, and/or a compound which is converted into a compound of the formula II by reaction with water or alcohols ROH under the reaction conditions to from 200 to 450° C. in the gas or liquid phase in the presence of a heterogeneous oxidic catalyst.Type: GrantFiled: March 7, 2000Date of Patent: November 13, 2001Assignee: BASF AktiengesellschaftInventors: Rolf Fischer, Shelue Liang, Rolf Pinkos, Frank Stein
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Patent number: 6262313Abstract: This invention provides a method for thermally converting volatile fatty acid (VFA) salts to ketones by mixing dry calcium salts of VFAs with hot heat transfer agent in an evacuated container, thereby causing thermal decomposition of the calcium salts of VFAs to form ketone-containing vapor and calcium carbonate; and separating the ketone-containing vapor from the calcium carbonate and heat transfer agent by condensing a mixture of ketones from the ketone-containing vapor. This invention also provides a process for conversion of VFA salts, produced by anaerobic fermentation of cellulosic biomass, into liquid fuels, volatile fatty acids, aldehydes, alcohols, and lactic acid.Type: GrantFiled: December 22, 1999Date of Patent: July 17, 2001Assignee: Texas A&M University SystemInventors: Mark T. Holtzapple, Richard R. Davison
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Patent number: 6200786Abstract: A method of producing nootkatone by laccase catalyzed oxidation of valencene. Valencene and a composition having laccase activity are reacted in the presence of an oxygen source, at a valencene concentration greater than 0.1%, to form valencene hydroperoxide. Optionally, a mediator and/or a solvent at a concentration that maintains laccase activity may also be included. The valencene hydroperoxide is degraded to form nootkatone, and nootkatone is then recovered. The method produces nootkatone in commercially viable yields.Type: GrantFiled: September 8, 1999Date of Patent: March 13, 2001Assignee: Givaudan S.A.Inventors: Rongmin Huang, Philip A. Christenson, Ivica M. Labuda
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Patent number: 6025527Abstract: Described are trimethylcyclohexenylcyclopropyl ketones having the structure: ##STR1## wherein one of the dashed lines is a carbon--carbon double bond and the other of the dashed lines is a carbon--carbon single bond, uses thereof in augmenting, enhancing or imparting aromas in or to perfume compositions, colognes and perfumed articles, and mixtures of same with 3-methyl-1-phenylpentanol-5 and/or butanoylcyclohexane derivatives and/or acetic or propionic acid esters of o-methylphenyl isopropanol.Type: GrantFiled: June 18, 1999Date of Patent: February 15, 2000Assignee: International Flavors & Fragrances Inc.Inventors: Richard M. Boden, Marie R. Hanna
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Patent number: 5969189Abstract: This invention provides a method for thermally converting volatile fatty acid (VFA) salts to ketones by mixing dry calcium salts of VFAs with hot heat transfer agent in an evacuated container, thereby causing thermal decomposition of the calcium salts of VFAs to form ketone-containing vapor and calcium carbonate; and separating the ketone-containing vapor from the calcium carbonate and heat transfer agent by condensing a mixture of ketones from the ketone-containing vapor.Type: GrantFiled: June 30, 1997Date of Patent: October 19, 1999Assignee: The Texas A&M University SystemInventors: Mark T. Holtzapple, Richard R. Davison
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Patent number: 5750795Abstract: The present invention provides a process for producing a ketone represented by a general formula RCOR' (wherein R is a C.sub.1 -C.sub.17 alkyl group, a C.sub.7 -C.sub.12 aralkyl group, a C.sub.7 -C.sub.12 aryl group or a C.sub.5 -C.sub.8 cycloalkyl group; R' is a C.sub.1 -C.sub.17 alkyl group, a C.sub.7 -C.sub.12 aralkyl group, a C.sub.7 -C.sub.12 aryl group or a C.sub.5 -C.sub.8 cycloalkyl group; R and R' may the same), which process comprises reacting a carboxylic acid represented by a general formula RCOOH (wherein R has the same definition as given above) with a carboxylic acid represented by a general formula R'COOH (wherein R' has the same definition as given above) in a gas phase in the presence of a catalyst containing at least either of MgO and CaO.The process allows for production of an intended ketone at a high yield at high productivity.Type: GrantFiled: January 26, 1996Date of Patent: May 12, 1998Assignee: Nippon Shokubai, Ltd.Inventor: Noboru Saito
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Patent number: 5567851Abstract: 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: GrantFiled: May 24, 1995Date of Patent: October 22, 1996Assignee: Chisso CorporationInventors: Seiichi Takano, Kunio Ogasawara
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Patent number: 5498799Abstract: An optically active 5-methylenedioxolan-4-one derivative is subjected to Diels-Alder reaction with cyclopentadiene, and the resulting Diels-Alder reaction product is hydrolyzed to convert it into an optically active 2-hydroxynorbornene-2-carboxylic acid, which is then subjected to catalytic hydrogenation to form an optically active 2-hydroxynorbornane-2-carboxylic acid. The hydroxycarboxylic acid is subjected to oxidative decarboxylation to obtain an optically active 2-norbornanone.Type: GrantFiled: August 19, 1994Date of Patent: March 12, 1996Assignee: Kuraray Co., Ltd.Inventors: Masahiro Torihara, Yoshin Tamai
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Patent number: 5466877Abstract: A process for converting perfluorinated carboxylic acid esters to perfluorinated acyl fluorides and/or perfluorinated ketones comprises the step of combining at least one perfluorinated carboxylic acid ester with at least one initiating reagent selected from the group consisting of gaseous, non-hydroxylic nucleophiles; liquid, non-hydroxylic nucleophiles; and mixtures of at least one non-hydroxylic nucleophile (gaseous, liquid, or solid) and at least one solvent which is inert to acylating agents. The process enables the dissociation of even high molecular weight, perfluorinated esters.Type: GrantFiled: March 15, 1994Date of Patent: November 14, 1995Assignee: Minnesota Mining and Manufacturing CompanyInventor: George G. I. Moore
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Patent number: 5430193Abstract: The invention provides a method for converting a lactone of a diamondoid compound to the hydroxyketone of the diamondoid compound wherein the hydroxyl group and the carbonyl group are separated by at least one bridgehead carbon comprising reacting an anhydride containing from about 2 to about 20 carbon atoms with the lactone of the diamondoid compound in the presence of acid.Type: GrantFiled: April 22, 1994Date of Patent: July 4, 1995Assignee: Mobil Oil CorporationInventor: Dong-Ming Shen
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Patent number: 5410092Abstract: The invention provides a method for converting a lactone of a diamondoid compound to the hydroxyketone of the diamondoid compound wherein the hydroxyl group and the carbonyl group are separated by at least one bridgehead carbon comprising reacting an anhydride containing from about 2 to about 20 carbon atoms with the lactone of the diamondoid compound in the presence of acid.Type: GrantFiled: December 9, 1993Date of Patent: April 25, 1995Assignee: Mobil Oil CorporationInventor: Dong-Ming Shen
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Patent number: 5336809Abstract: A new process for the preparation of 1-fluorocyclopropyl methyl ketone of the formula ##STR1## which process comprises a) in a first step, reacting 2-acetyl-2-chloro-4-butanolide of the formula ##STR2## with an addition product of triethylamine and hydrogen fluoride of the formula(C.sub.2 H.sub.5).sub.3 N.multidot.n HFin whichn represents the numbers 1, 2 or 3,in the presence of a diluent at a temperature between 20.degree. C. and 120.degree. C. andb) in a second step, reacting the resulting 2-acetyl-2-fluoro-4-butanolide of the formula ##STR3## with a nucleophilic agent in the presence of a diluent at a temperature between 50.degree. C. and 200.degree. C.New halogenoketones of the formula ##STR4## in which Hal represents chlorine or bromine.Type: GrantFiled: March 2, 1993Date of Patent: August 9, 1994Assignee: Bayer AktiengesellschaftInventors: Stefan Bohm, Albrecht Marhold
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Patent number: 5266728Abstract: The present invention provides a method for producing optically active 3-substituted-2-norbornanones which are useful as starting materials for several kinds of physiologically active materials, and to their intermediates, optically active 2-hydroxy-2-norbornanecarboxylic acid and to a method for producing these intermediates.Type: GrantFiled: August 19, 1992Date of Patent: November 30, 1993Assignee: Chisso CorporationInventors: Naoyuki Yoshida, Teruyo Sugiura, Kazutoshi Miyazawa, Yasuyuki Koizumi
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Patent number: 5151411Abstract: A compound of the formula ##STR1## wherein the dotted line signifies an optional bond, as racemates or individual enantiomers, odorant compositions containing the same, and a process for the manufacture of the compounds of formula I which comprises rearranging sclareolide, episclareolide or isosclareolide at an elevated temperature in acidic medium with dehydration and, if desired, reducing the carbon-carbon double bond present in the reaction product.Type: GrantFiled: August 20, 1991Date of Patent: September 29, 1992Assignee: Givaudan CorporationInventors: Georg Frater, Daniel Helmlinger
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Patent number: 5144070Abstract: Disclosed is a process for the preparation of .alpha.-iodocarbonyl compounds such as .alpha.-iodocarboxylic acid anhydrides and .alpha.-iodoketones by the reaction of a carboxylic anhydride with molecular iodine. Hydrolysis of the .alpha.-iodocarboxylic acid anhydrides gives the corresponding .alpha.-iodocarboxylic acids.Type: GrantFiled: August 30, 1989Date of Patent: September 1, 1992Assignee: Eastman Kodak CompanyInventors: Joseph R. Zoeller, Michael R. Cushman, Regina M. Moncier
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Patent number: 5136100Abstract: A process for producing 3-methyl-2-pentylcyclopent-2-en-1-one by cyclodehydration of .gamma.-methyl-.gamma.-decalatone, which comprises heating .gamma.-methyl-.gamma.-decalactone at a temperature effective for said cyclodehydration in the presence of an effective amount of phosphoric acid as a catalyst, and a mineral oil having a boiling point which is higher than that of said starting material and said product, and removing said product from the reaction mixture.Type: GrantFiled: November 15, 1989Date of Patent: August 4, 1992Assignee: Huls AktiengesellschaftInventor: Harald Claus
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Patent number: 4983774Abstract: The preparation of ketones by reacting an acylating agent with an organo-manganous compound is catalyzed by a copper compound.Type: GrantFiled: December 16, 1988Date of Patent: January 8, 1991Assignee: Societe Nationale Elf AquitaineInventors: Gerard Cahiez, Blandine Laboue, Pierre Tozzolino
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Patent number: 4950763Abstract: Ketones of the general formula (I) ##STR1## where R.sup.1 and R.sup.2 independently of one another are each alkyl, cycyloalkyl, arylalkyl, aryl or hetaryl, and one or more of the radicals R.sup.1 and R.sup.2 carry one or more hydrogen atoms on the .alpha.-carbon atom, are prepared by reacting two carboxylic acids of the general formulae (IIa/IIb), R.sup.1 --COOH (IIa) and R.sup.2 --COOH (IIb) or by reacting a carboxylic acid R.sup.1 --COOH (IIa) and a ketone ##STR2## or by reacting a mixture of IIa, IIb and Ib, in the gas phase in the presence of a catalyst, by a process in which a catalyst is used whose active material contains at least 50% by weight of titanium dioxide having a specific surface area greater than 10 m.sup.2 /g.0.Type: GrantFiled: July 18, 1989Date of Patent: August 21, 1990Assignee: BASF AktiengesellschaftInventors: Charles Schommer, Klaus Ebel, Toni Dockner, Matthias Irgang, Wolfgang Hoelderich, Harald Rust
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Patent number: 4900870Abstract: Process for the preparation of cycloaliphatic ketones of formula ##STR1## wherein index m designates integer 0, 1 or 2, n stands for 0 or 1 and the dotted lines represent an optional supplemental bond, which process consists in the deprotonation of an ester of formula ##STR2## having either an isolated double bond in position 1 or 2 (exocyclic), or two conjugated double bonds in position 1 and 3 or 2 (exocyclic) and 3 as indicated by the dotted lines, and wherein symbol R' represents a linear or branched alkyl radical, preferably a C.sub.1 -C.sub.6 alkyl radical, or a substituted or unsubstituted phenyl, and Y designates an oxygen or a sulphur atom, the deprotonation being followed by the addition of an organo-metallic compound of formula ##STR3## wherein m and n have the meaning defined above and Z represents a MgX radical or an alkali metal, preferably lithium, X defining a halogen and the dotted lines an optional supplemental bond, and finally a hydrolysis.Type: GrantFiled: September 1, 1987Date of Patent: February 13, 1990Assignee: Firmenich S.A.Inventors: Charles Fehr, Jose Galindo
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Patent number: 4855460Abstract: A process for the preparation of perfluoroalkylated ketones and/or perfluoroalkylated alcohols, comprising the step of contacting a perfluoroalkyl iodide or perfluoroalkyl bromide with an acid anhydride, in the presence of a metal chosen from zinc and cadmium.Type: GrantFiled: July 11, 1988Date of Patent: August 8, 1989Assignee: Rhone-Poulenc ChimieInventors: Marc Tordeux, Claude Wakselman, Catherine Francese
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Patent number: 4827044Abstract: 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: GrantFiled: March 8, 1988Date of Patent: May 2, 1989Assignee: Societe Nationale Elf AquitaineInventors: Pierre Tozzolino, Gerard Cahiez
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Patent number: 4663487Abstract: The invention provides a process for the preparation of 4,4-disubstituted cyclohexadienones of which at least one of the substituents is fluorine, which comprises reacting a compound of formula ##STR1## wheren X represents a hydrogen or halogen atom or an alkyl group, each R independently represents a halogen atom or an alkyl, alkoxy, or cyano or optionally substituted amino group, Z represents a hydrogen atom or an alkyl, acyl or aryloxycarbonyl group, and n is 0 to 4, with hydrogen fluoride and a Pb(IV) compound, in the presence of a compound which acts as a base towards HF.Type: GrantFiled: January 14, 1986Date of Patent: May 5, 1987Assignee: Shell Oil CompanyInventors: Jan H. H. Meurs, David W. Sopher
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Patent number: 4571436Abstract: Optically active cyclopentenolones, which are useful as an intermediate of pyrethroid insecticides, are produced from racemic cyclopentenolones according to the following procedures; (1) asymmetric hydrolysis of racemic carboxylate esters of the cyclopentenolones, (2) nitrate- or sulfonate-esterification of the asymmetrical hydrolysis products, and (3) hydrolysis of the esterification products.Type: GrantFiled: May 21, 1984Date of Patent: February 18, 1986Assignee: Sumitomo Chemical Company, LimitedInventors: Takeaki Umemura, Ayumu Inoue, Satoshi Mitsuda