Phenol Containing Reactant Patents (Class 568/362)
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Patent number: 10029971Abstract: A method of producing alpha-tocotrienol quinone or a stereoisomer thereof, the method comprising selective opening of alpha-tocotrienol chroman to alpha-tocotrienol quinone in the presence of non-alpha tocotrienol chromans by oxidizing alpha-tocotrienol with a metal salt oxidizing agent, wherein the stoichiometric ratio of metal salt oxidizing agent/alpha-tocotrienol is at least 4:1 and wherein said metal oxidizing agent is added in sequential additions, in order to reduce oxidation of any amounts of non-alpha tocotrienol chromans that might have been present in the starting alpha-tocotrienol chroman material. This process uses conditions favoring oxidation rates of the alpha tocotrienol chroman vs. the non-alpha tocotrienol chromans.Type: GrantFiled: January 20, 2017Date of Patent: July 24, 2018Assignee: BIOELECTRON TECHNOLOGY CORPORATIONInventor: Paul Mollard
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Patent number: 10023515Abstract: A method of preparing cyclohexanone by hydrogenating phenol is provided. The method includes a step of introducing an additional flammable gas to dilute hydrogen gas concentration, so as to increase the throughput and decrease energy consumption. Further, the discharged residual gases from the hydrogenation of phenol have a calorific value. Also provided is a system for generating cyclohexanone by hydrogenating phenol.Type: GrantFiled: May 10, 2017Date of Patent: July 17, 2018Assignee: China Petrochemical Development CorporationInventors: Chien-Hsien Li, Hung-Lung Chen, Ming-Syun Yang
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Patent number: 9567279Abstract: A method of producing alpha-tocotrienol quinone or a stereoisomer thereof, the method comprising selective opening of alpha-tocotrienol chroman to alpha-tocotrienol quinone in the presence of non-alpha tocotrienol chromans by oxidizing alpha-to-cotrienol with a metal salt oxidizing agent, wherein the stoichiometric ratio of metal salt oxidizing agent/alpha-tocotrienol is at least 4:1 and wherein said metal oxidizing agent is added in sequential additions, in order to reduce oxidation of any amounts of non-alpha tocotrienol chromans that might have been present in the starting alpha-tocotrienol chroman material. This process uses conditions favoring oxidation rates of the alpha tocotrienol chroman vs. the non-alpha tocotrienol chromans.Type: GrantFiled: September 10, 2015Date of Patent: February 14, 2017Assignee: Edison Pharmaceuticals, Inc.Inventor: Paul Mollard
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Patent number: 9388107Abstract: The present invention provides a process for continuously preparing a mixture of cyclohexanone and cyclohexanol comprising, a) hydrogenating phenol with gaseous hydrogen, in the presence of platinum or palladium, in a hydrogenation reactor, to produce a hydrogenation product stream comprising cyclohexanone, cyclohexanol, phenol and hydrogen; b) cooling the hydrogenation product stream to a temperature such that the fraction of phenol by mass in a first gas phase is lower than the fraction of phenol by mass in a first liquid phase; c) separating the first gas phase from the first liquid phase; d) returning at least part of the first gas phase to the hydrogenation reactor; e) heating the first liquid phase; f) purifying the first liquid phase by distillation; characterized in that heat is transferred from the hydrogenation product stream in step b) to another part of the process by means of in-process heat exchange; a mixture of cyclohexanone and cyclohexanol obtained by the process; and a chemical plant suitabType: GrantFiled: June 27, 2013Date of Patent: July 12, 2016Assignee: CAP III B.V.Inventors: Wilhelmus Rudolf Maria Martens, Robert Jan De Korte, Iris Verschuren, Corinne Daguenet, Johan Thomas Tinge, Roeland Wilhelmus Theodorus Maria Brands
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Patent number: 9109178Abstract: This invention relates to the petrochemical industry, in particular, to a method for improving the storage stability of biodiesel fuel via using an antioxidant additive. A method for improving the storage stability of biodiesel fuel, comprising addition of an alkylphenol-based antioxidant additive via providing an initial solution that contains 6 to 48 mass % of the alkylphenol-based composition comprised of, mass %: 2,6-di-tert-butyl-4-methylcyclohexanone—0.2-0.3; 2,6-di-tert-butylphenol—0.7-6.0; 2-sec-butyl-6-tert-butyl-p-cresol—1.5-5.0; 4,6-di-tert-butyl-o-cresol—3.0-8.0; 2,4-di-tert-butylphenol—0.3-0.5; 2,4-di-tort-butyl-6-dimethylaminomethylphenol—2.0-5.0; 4,4-methylene-bis(2,6-di-tert-butylphenol)—0.1-0.3; and 2,6-di-tert-butyl-4-methylphenol—to the balance, dissolved in biodiesel fuel; and adding the solution of the composition to the biodiesel fuel to reach a concentration of the composition of from 0.002 to 1.6 mass % based on the entire biodiesel fuel solution.Type: GrantFiled: March 7, 2013Date of Patent: August 18, 2015Assignee: Oktrytoe Aktsionernoe Obschestvo “Sterutamaxky Neftekhimichesky Zavod”Inventors: Roza Minizievna Salavatova, Nikolai Arkadievich Niyazov
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Publication number: 20140249332Abstract: A method of producing alpha-tocotrienol quinone or a stereoisomer thereof, the method comprising selective opening of alpha-tocotrienol chroman to alpha-tocotrienol quinone in the presence of non-alpha tocotrienol chromans by oxidizing alpha-tocotrienol with a metal salt oxidizing agent, wherein the stoichiometric ratio of metal salt oxidizing agent/alpha-tocotrienol is at least 4:1 and wherein said metal oxidizing agent is added in sequential additions, in order to reduce oxidation of any amounts of non-alpha tocotrienol chromans that might have been present in the starting alpha-tocotrienol chroman material. This process uses conditions favoring oxidation rates of the alpha tocotrienol chroman vs the non-alpha tocotrienol chromans.Type: ApplicationFiled: July 19, 2012Publication date: September 4, 2014Inventor: Paul Mollard
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Patent number: 8802897Abstract: A method for hydrogenating optionally substituted phenols with one hydroxyl group to cyclohexanones over modified, palladium-comprising supported catalysts. This is possible surprisingly in selected alcoholic solvents with high selectivity. Here it is even possible to recycle the catalysts employed, which hitherto has only been possible with considerable loss of selectivity.Type: GrantFiled: December 12, 2012Date of Patent: August 12, 2014Assignee: Allessa GmbHInventors: Doris Neumann, Joachim Ritzer, Gunther Effenberger
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Patent number: 8772550Abstract: The invention relates to a method for hydrogenating an aromatic compound. The invention in particular relates to a method for preparing cyclohexanone, cyclohexanol or a mixture thereof in a continuous way by catalytically hydrogenating phenol fed into a reactor comprising a supported hydrogenation catalyst, comprising a dopant selected from the group of alkali metal hydroxides, alkaline earth metal hydroxides, alkaline earth metal oxides, carbonates of alkali metals and carbonates of alkaline earth metals, and in which process during the hydrogenation of phenol continuously or intermittently water is fed into the reactor, the weight to weight ratio of water fed into the reactor to phenol fed into the reactor on average being 0.1 or less.Type: GrantFiled: December 15, 2010Date of Patent: July 8, 2014Assignee: DSM IP Assets B.V.Inventors: Rudy Francois Maria Jozef Parton, Johan Thomas Tinge, Bert Hoeksema
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Patent number: 8679999Abstract: Titanosilicate catalyst is used in the oxidation reactions such as allylchloride epoxidation, phenol hydroxylation, Cyclohexanone ammoximation. During the reaction the catalyst is deactivated which further decrease in the efficiency of the oxidation reactions. The present invention provides a method for an efficient regeneration of catalyst titanosilicate catalyst at low temperature below 100° C. using a gaseous mixture containing ozone, without isolating the catalyst from the reactor system.Type: GrantFiled: January 31, 2013Date of Patent: March 25, 2014Assignee: Aditya Birla Science & Technology Co. Ltd.Inventors: Subbareddy Kanagasabapathy, Yogesh Laxman Borle, Bir Kapoor, Arati Verma
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Patent number: 8618334Abstract: Methods for continuously preparing cyclohexanone from phenol make use of a catalyst having at least one catalytically active metal selected from platinum and palladium. The process includes enriching phenol in a distillation fraction as compared to a subsequent fraction, wherein the subsequent fraction includes phenol and side-products having a higher boiling point than phenol. Distillation is carried out in a vacuum distillation column equipped with trays in the lower part of the column. In an upper part of the column, i.e., in the part above the feed inlet, packing material is present instead of trays in at least part thereof. The packing material has a comparable or improved separating efficiency, and provides a reduction of the pressure drop by at least 30%, preferably more than 50%, as compared to the case with trays in the upper part, under otherwise similar distillation conditions.Type: GrantFiled: December 16, 2008Date of Patent: December 31, 2013Assignee: DSM IP Assets B.V.Inventors: Marleen Horsels, Rudy Francols Marla Jozef Parton, Johan Thomas Tinge
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Publication number: 20130165697Abstract: A method for hydrogenating optionally substituted phenols with one hydroxyl group to cyclohexanones over modified, palladium-comprising supported catalysts. This is possible surprisingly in selected alcoholic solvents with high selectivity. Here it is even possible to recycle the catalysts employed, which hitherto has only been possible with considerable loss of selectivity.Type: ApplicationFiled: December 12, 2012Publication date: June 27, 2013Applicant: ALESSA GMBHInventor: ALESSA GMBH
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Publication number: 20120323042Abstract: The invention relates to a method for hydrogenating an aromatic compound. The invention in particular relates to a method for preparing cyclohexanone, cyclohexanol or a mixture thereof in a continuous way by catalytically hydrogenating phenol fed into a reactor comprising a supported hydrogenation catalyst, comprising a dopant selected from the group of alkali metal hydroxides, alkaline earth metal hydroxides, alkaline earth metal oxides, carbonates of alkali metals and carbonates of alkaline earth metals, and in which process during the hydrogenation of phenol continuously or intermittently water is fed into the reactor, the weight to weight ratio of water fed into the reactor to phenol fed into the reactor on average being 0.1 or less.Type: ApplicationFiled: December 15, 2010Publication date: December 20, 2012Inventors: Rudy Francois Maria Jozef Parton, Johan Thomas Tinge, Bert Hoeksema
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Patent number: 8247614Abstract: Fluorinated copolymers are prepared via copolycondensation polymerization in a process comprising reacting A) a telechelic fluoroazido compound of formula N3(Y)p—(CH2)n—R—(CH2)m—(Y)pN3, wherein Y is SO, SO2, C6H4, or CO, p=0 or 1, n and m are independently 1 to 4, and R is selected from the group consisting of i) a C3-C10 fluoroalkylene group, ii) a C3-C10 fluoroalkoxylene group, iii) a substituted aryl group, iv) an oligomer comprising copolymerized units of vinylidene fluoride and perfluoro(methyl vinyl ether), v) an oligomer comprising copolymerized units of vinylidene fluoride and hexafluoropropylene, vi) an oligomer comprising copolymerized units of tetrafluoroethylene and perfluoro(methyl vinyl ether), and vii) an oligomer comprising copolymerized units of tetrafluoroethylene and a hydrocarbon olefin with B) a telechelic diyne or dinitrile compound in the presence of copper halide catalyst.Type: GrantFiled: June 17, 2009Date of Patent: August 21, 2012Assignees: E I du Pont de Nemours and CompanyInventors: Ming-Hong Hung, Bruno Ameduri, Bernard Boutevin, Aurelien Soules
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Publication number: 20110054142Abstract: The present invention relates to a method for continuously preparing cyclohexanone from phenol making use of a catalyst comprising at least one catalytically active metal selected from platinum and palladium comprising a) hydrogenating phenol to form a product stream comprising cyclohexanone and unreacted phenol; b) separating at least part of the product stream, or at least part of the product stream from which one or more components having a lower boiling point than cyclohexanone have been removed, into a first fraction comprising cyclohexanone and a second fraction comprising phenol and cyclohexanol, using distillation; c) separating the second fraction into a third fraction, rich in cyclohexanol, and a fourth fraction, rich in phenol and, using distillation; d) subjecting at least part of the fourth fraction to a further distillation step, thereby forming a fifth fraction and a sixth fraction, wherein the fifth fraction is enriched in phenol compared to the sixth fraction, and wherein the sixth fraction cType: ApplicationFiled: December 16, 2008Publication date: March 3, 2011Inventors: Marleen Horsels, Rudy Francols Maria Jozef Parton, Johan Thomas Tinge
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Publication number: 20110028675Abstract: The present invention relates to a method for continuously preparing cyclohexanone from phenol making use of a catalyst comprising at least one catalytically active metal selected from platinum and palladium comprising hydrogenating phenol to form a product stream comprising cyclohexanone and unreacted phenol; separating at least part of the product stream, or at least part of the product stream from which one or more components having a lower boiling point than cyclohexanone have been removed, into a first fraction comprising cyclohexanone and a second fraction comprising phenol and cyclohexanol, using distillation; separating the second fraction into a third fraction, rich in cyclohexanol, and a fourth fraction, rich in phenol, using distillation;—subjecting at least part of the fourth fraction to a further distillation step, thereby forming a fifth fraction and a sixth fraction, wherein the fifth fraction is enriched in phenol compared to the sixth fraction, and wherein the sixth fraction comprises side-prType: ApplicationFiled: December 16, 2008Publication date: February 3, 2011Inventors: Godefridus Maria Van Dortmont, Marleen Horsels, Rudy Francois Maria Josef Parton, Johan Thomas Tinge
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Patent number: 7790929Abstract: The invention relates to chiral phenols, preferably of formula (I), the different parameters having the meaning indicated in the description, liquid crystal media which contain said compounds as chiral doping agents and/or stabilizers, and the use thereof in electro-optical displays.Type: GrantFiled: September 18, 2003Date of Patent: September 7, 2010Assignee: Merck Patent GmbHInventors: Volker Reiffenrath, Michael Heckmeier
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Patent number: 7601877Abstract: A process for the preparation of ubihydroquinones and ubiquinones by condensation of a prenol or isoprenol with a hydroquinone or derivative thereof in the presence of 0.005-1.0 mol % of a catalyst which is a Broensted-acid, a Lewis-acid from the group consisting of a derivative of Bi or In or an element of group 3 of the periodic table of the elements, a heteropolyacid, an NH— or a CH-acidic compound, and optionally oxidizing the ubihydroquinone obtained.Type: GrantFiled: August 2, 2006Date of Patent: October 13, 2009Assignee: DSM IP Assets B.V.Inventors: Fabrice Aquino, Werner Bonrath, Patrick Bohrer, Max Hugentobler, Thomas Netscher, Alexander Radspieler
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Publication number: 20080275275Abstract: A process for the preparation of ubihydroquinones and ubiquinones by condensation of a prenol or isoprenol with a hydroquinone or derivative thereof in the presence of 0.005-1.0 mol % of a catalyst which is a Broensted-acid, a Lewis-acid from the group consisting of a derivative of Bi or In or an element of group 3 of the periodic table of the elements, a heteropolyacid, an NH- or a CH-acidic compound, and optionally oxidizing the ubihydroquinone obtained.Type: ApplicationFiled: August 2, 2006Publication date: November 6, 2008Inventors: Fabrice Aquino, Werner Bonrath, Patrick Bohrer, Max Hugentobler, Thomas Netscher, Alexander Radspieler
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Publication number: 20080200702Abstract: The present invention relates to an improved process for the preparation of Coenzyme Q. Coenzyme Q10 or CoQ10 has the chemical name 2-[(all-trans)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl]-5,6-dimethoxy-3-methyl-1,4-benzoquinone and has the formula I. The invention also provides new intermediates useful for the preparation of CoQ10 and processes for their preparation.Type: ApplicationFiled: June 21, 2006Publication date: August 21, 2008Applicant: NICHOLAS PIRAMAL INDIA LIMITEDInventors: Palanivelu Gurumurthy, Suneel Manohar Babu Chennamsettyl, Vaithyanathan Visweswaran
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Patent number: 7250537Abstract: The present invention provides a novel method of hydrogenating a phenol for hydrogenating a phenol industrially advantageously. The present invention relates, in the case of phenol hydrogenation in which carbon dioxide is made to participate in the reaction, to a method of hydrogenating a phenol characterized by using a supported rhodium and/or ruthenium catalyst, whereby the phenol is hydrogenated efficiently at a lower reaction temperature than with prior art; such a method characterized in that carbon dioxide having a temperature of 20 to 250° C. and a pressure of 0.1 to 50 MPa is used as the carbon dioxide; and such a method characterized in that hydrogen under conditions of a temperature of 20 to 250° C. and a pressure of 0.1 to 50 MPa is used. An environmentally friendly phenol hydrogenation process that uses no harmful organic solvents can be realized.Type: GrantFiled: March 30, 2004Date of Patent: July 31, 2007Assignee: National Institute of Advanced Industrial Science and TechnologyInventors: Masayuki Shirai, Chandrashekhar Vasant Rode, Uday Dattopant Joshi, Kazuo Torii, Takafumi Sato
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Patent number: 7183119Abstract: The present invention relates to a method of detecting biological analytes comprising suspending a target analyte in a suspending solution containing polymeric particles marked with a probe, wherein the probe has an affinity for said target analyte; adding recognition unit-peroxidase conjugate marker to the suspending solution; forming a complex of the target analyte, the polymeric particles marked with a probe, and the recognition unit-peroxidase conjugate marker; contacting a gelatin surface with the suspending solution; adding developer to the suspending solution in contact with the gelatin surface in the presence of phenol to attach the complex to the gelatin surface; washing the gelatin surface; and detecting the complex attached to the gelatin surface.Type: GrantFiled: November 15, 2004Date of Patent: February 27, 2007Assignee: Eastman Kodak CompanyInventors: Tiecheng A. Qiao, Brian J. Kelley
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Patent number: 7090817Abstract: The invention relates to a process for the preparation of hydroxylammonium, said process comprising the steps of: a) feeding gaseous hydrogen to a reaction mixture, said reaction mixture comprising an aqueous reaction medium and a gaseous phase; b) catalytically reducing, in said reaction mixture, nitrate or nitrogen oxide with hydrogen to form the hydroxylammonium; c) withdrawing a gas mixture from the reaction mixture, said gas mixture comprising gaseous hydrogen and gaseous non-hydrogen compounds; d) separating at least part of the gaseous non-hydrogen compounds from the gas mixture to obtain a hydrogen-enriched gas; and e) passing the hydrogen-enriched gas to a hydrogenation zone.Type: GrantFiled: July 11, 2002Date of Patent: August 15, 2006Assignee: DSM IP Assets B.V.Inventors: Arno Herald Benneker, Johannes A. L. Brouwers, Godefridus M. Van Dortmont
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Patent number: 7078570Abstract: The present invention relates to substituted cyclohexenes, to their use as well as to their preparation method. These compounds have powerful long lasting natural fruity grapefruit notes with minty and fresh green tonalities.Type: GrantFiled: December 3, 2001Date of Patent: July 18, 2006Assignee: Givaudan SAInventor: Andreas Goeke
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Patent number: 7074622Abstract: The present invention relates to a method of particle separation comprising preparing a suspension of particles containing at least one recognizable target particle in a suspending solution, labeling the target particle with a conjugate marker, wherein the conjugate marker comprises at least one recognition unit for the recognizable target particle and at least one peroxidase enzyme, contacting a gelatin surface with the suspending solution, adding developer to the suspending solution in contact with the gelatin surface and in the presence of phenol to attach the target particle to the gelatin surface, and washing the gelatin surface to remove unattached particles. The method may also include detecting the presence of the target particle on the gelatin surface as well as detaching and recovering the attached particles after removal of the non-target particles.Type: GrantFiled: November 15, 2004Date of Patent: July 11, 2006Assignee: Eastman Kodak CompanyInventors: Tiecheng A. Qiao, Yun C. Chang, Eric R. Schmittou, Thomas I. Penner
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Patent number: 7030279Abstract: An alcohol can be oxidized by a process in which a primary or secondary alcohol are reacted with an oxygen-containing gas in the presence of a catalyst composition containing (i) a stable free nitroxyl radical derivative, (ii) a nitrate source, (iii) a bromide source, and (iiii) a carboxylic acid, thereby obtaining an aldehyde or a ketone.Type: GrantFiled: December 23, 2004Date of Patent: April 18, 2006Assignee: Degussa AGInventors: Setrak Tanielyan, Robert Augustine, Oliver Meyer, Michael Korell
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Publication number: 20040127750Abstract: A highly pure 2,4,4,6-tetrabromo-2,5-cyclohexadienone has been prepared in a single pot, eco-friendly procedure in yields of 91-94% from phenol. In this method, a mixture of alkali/alkaline earth metal bromide and alkali/alkaline earth metal bromate was employed as brominating agent in place of corrosive liquid bromine. The reaction between phenol and the brominating reagent was initiated by the action of a mineral acid or moderately strong organic acid. The crude product was further characterized by standard analytical and spectroscopic methods.Type: ApplicationFiled: December 31, 2002Publication date: July 1, 2004Applicant: Council of Scientific and Industrial ResearchInventors: Ashutosh Vasant Bedekar, Ramachandraiah Gadde, Pushhpito Kumar Ghosh
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Patent number: 6740785Abstract: Improved oxidation methods are provided wherein a reaction mixture comprising a substrate to be oxidized (e.g., phenols, alkenes) and an oxidation catalyst (typically dispersed in an organic solvent system) is supplemented with a compressed gas which expands the reaction mixture, thus accelerating the oxidation reaction. In preferred practice pressurized subcritical or supercritical carbon dioxide is used as the expanding gas, which is introduced into the reaction mixture together with an oxidizing agent. The inventive methods improve the substrate conversion and product selectivity by increasing the solubility of the oxidizing agent in the reaction mixture.Type: GrantFiled: July 26, 2002Date of Patent: May 25, 2004Assignee: The University of KansasInventors: Bala Subramaniam, Daryle H. Busch, Ghezai T. Musie, Ming Wei
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Patent number: 6703527Abstract: Allyl alcohols are converted into corresponding aldehydes or ketones in a high yield under a mild condition by using an inexpensive aluminum alkoxide as an Oppenauer oxidation catalyst and a hydride acceptor. Thus, there is provided an industrially useful method for converting allyl alcohols to corresponding aldehydes or ketones.Type: GrantFiled: May 21, 2002Date of Patent: March 9, 2004Assignee: Nikken Chemicals Co., Ltd.Inventors: Shin Tanikawa, Sou Matsubayashi, Michika Tanikawa, Toshiya Komatsu
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Patent number: 6610889Abstract: Methods and compositions are provided for the direct catalytic asymmetric aldol reaction of aldehydes with donor molecules selected from ketones and nitroalkyl compounds. The reactions employ as catalyst a Group 2A or Group 2B metal complex of a ligand of formula I, as defined further herein.Type: GrantFiled: October 31, 2001Date of Patent: August 26, 2003Assignee: The Board of Trustees of the Leland Stanford Junior UniversityInventors: Barry M. Trost, Hisanaka Ito
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Patent number: 6448454Abstract: Improved oxidation methods are provided wherein a reaction mixture comprising a substrate to be oxidized (e.g., phenols, alkenes) and an oxidation catalyst (typically dispersed in an organic solvent system) is supplemented with a compressed gas which expands the reaction mixture, thus accelerating the oxidation reaction. In preferred practice pressurized subcritical or supercritical carbon dioxide is used as the expanding gas, which is introduced into the reaction mixture together with an oxidizing agent. The inventive methods improve the substrate conversion and product selectivity by increasing the solubility of the oxidizing agent in the reaction mixture.Type: GrantFiled: April 7, 2000Date of Patent: September 10, 2002Assignee: The University of KansasInventors: Bala Subramaniam, Daryle H. Busch, Ghezai T. Musie, Ming Wei
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Patent number: 6376717Abstract: The present invention provides a method for preparing astaxanthin from zeaxanthin. Specifically, the present invention provides a method for said conversion using a halogenating agent with the salt of chloric or bromic acid in an inert solvent.Type: GrantFiled: March 19, 2001Date of Patent: April 23, 2002Assignee: Prodemex, S.A. de C.V.Inventors: George C. Schloemer, Jeffery L. Davis
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Patent number: 6372946Abstract: A method of preparing &bgr;-carotene derivatives such as canthaxanthin and astaxanthin is described. The method employs an in situ system to generate hypobromous acid as the oxidizing agent using a salt of sulfite, hydrogen sulfite or bisulfite in combination with a bromate salt. Astaxanthin and canthaxanthin are obtained in good yield with a significantly reduced reaction time.Type: GrantFiled: September 13, 2001Date of Patent: April 16, 2002Assignee: Prodemex, S.A. DE C.V.Inventors: George C. Schloemer, Danuta A. Schloemer, Jeffery L. Davis
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Patent number: 6313351Abstract: The process for producing alicyclic monoketones (hydroxyphenylcyclohexanone derivatives) according to the present invention comprises hydrogenating substituted bisphenols such as bisphenol A in a solvent in the presence of a palladium/alkali metal catalyst in which palladium and an alkali metal are both supported on a carrier to obtain alicyclic monoketones such as 2-(4-oxocyclohexyl)-2-(4-hydroxyphenyl)propane. The process for producing alicyclic diketones according to the present invention comprises hydrogenating substituted bisphenols such as bisphenol A in a solvent in the presence of a palladium/alkali metal catalyst in which palladium and an alkali metal are both supported on a carrier to obtain alicyclic diketones such as 2,2-bis(4-oxocyclohexyl)propane and 4,4′-bicyclohexanone.Type: GrantFiled: September 2, 1999Date of Patent: November 6, 2001Assignee: Honshu Chemical Industry Co., Ltd.Inventors: Norimoto Kiya, Shinsaku Kawasaki, Kenji Ekawa, Kenji Sugiyama, Toyokazu Kitaura
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Patent number: 6215028Abstract: The invention relates to a process for the preparation of cyclohexanones from the corresponding phenols by partial hydrogenation, characterized in that the reaction mixture obtained by means of the hydrogenation is treated with sulfonating agents before the isolation of the cyclohexanone.Type: GrantFiled: November 2, 1998Date of Patent: April 10, 2001Assignee: Merck Patent Gesellschaft mitInventors: Bernd Oster, Peter Mackert, Detlef Pauluth, Markus Wydra
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Patent number: 6046365Abstract: Unsubstituted or substituted cyclohexanones are advantageously prepared by hydrogenation of the corresponding phenols in the presence of a palladium-on-carbon catalyst at from 100 to 250.degree. C. and from 1 to 20 bar of hydrogen pressure if the catalyst is mixed with a base component and from 20 to 200% by weight of water (based on the base component) and this mixture is used in the hydrogenation. For identical batches, this gives virtually identical hydrogenation times and virtually equally good yields of cyclohexanones.Type: GrantFiled: June 29, 1998Date of Patent: April 4, 2000Assignee: Bayer AktiengesellschaftInventor: Wolfgang Kiel
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Patent number: 6015927Abstract: Substituted or unsubstituted cyclohexanones are advantageously prepared by hydrogenation of the corresponding phenols in the presence of a palladium-on-carbon catalyst at from 100 to 250.degree. C. and from 1 to 20 bar of hydrogen pressure if the reaction is carried out in the presence of straight-chain, branched or cyclic alkanes having a boiling point at atmospheric pressure of over 70.degree. C. as solvents. This makes it possible to obtain substituted or unsubstituted cyclohexanones in short hydrogenation times and in high yields using low-toxicity, physically problem-free solvents which are easy to handle from a safety point of view.Type: GrantFiled: June 29, 1998Date of Patent: January 18, 2000Assignee: Bayer AktiengesellschaftInventor: Wolfgang Kiel
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Patent number: 5932753Abstract: A process for producing 2-methyl-1,4-benzoquinone at a high conversion, a high selectivity and at a low cost by oxidizing m-cresol with oxygen at a low partial pressure in the presence of at least one copper (I) halide catalyst and a mixed solvent of ketone and acetonitrile. The 2-methyl-1,4-benzoquinone is useful as an intermediate compound to produce vitamin K.Type: GrantFiled: February 9, 1998Date of Patent: August 3, 1999Assignee: Chuo Chemical Co., Inc.Inventors: Kenji Onodera, Eiko Nakatu, Masayuki Kobayashi
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Patent number: 5880301Abstract: The present invention provides a novel optically active bidentate phosphine ligand palladium complex of formula (I) or (II) which can be used for the preparation of optically active .beta.-hydroxyketones: ##STR1## ?wherein Y.sup.- represents an anion pair which may form salt; X represents ##STR2## {wherein R.sup.1 represents hydrogen atom, C.sub.1-6 alkyl group, C.sub.1-6 alkoxyl group, cyano group, nitro group, halogen atom or phenyl group, etc.; m represents 1 or 2; when m is 2, two R.sup.1 s may be same or different}; andA and B each independently represents phenyl group or cyclohexyl group {said phenyl group and cyclohexyl group each is unsubstituted or substituted by R.sup.2 (R.sup.2 has the same meaning as defined in R.sup.1)}).Type: GrantFiled: September 16, 1997Date of Patent: March 9, 1999Assignee: Nissan Chemical Industries, Ltd.Inventors: Masakatsu Shibasaki, Mikiko Sodeoka, Kazuhiko Ohrai
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Patent number: 5744648Abstract: A new process for the manufacture of 1,3-cyclohexanedione is disclosed wherein a selected resorcinol is reduced with a hydrogen donor in the presence of a metal catalyst to produce a product which is then neutralized with an acid.Type: GrantFiled: August 1, 1996Date of Patent: April 28, 1998Assignee: Hoechst Celanese CorporationInventors: Varadaraj Elango, Rajagopal Sakamuri
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Patent number: 5712416Abstract: Process for preparing benzoquinones by oxidation of phenols in the presence of a diluent and of an oxygen-transferring catalyst which contains a heavy metal ion bound in a complex, wherein oxygen, hydrogen peroxide, a compound which liberates hydrogen peroxide, an organic hydroperoxide, a percarboxylic acid or peroxomonosulfuric acid or salts thereof are used as oxidizing agent, and wherein the oxygen-transferring catalyst is from the class of iron, manganese or chromium tetraaza?14!annulenes.Type: GrantFiled: November 27, 1995Date of Patent: January 27, 1998Assignee: BASF AktiengesellschaftInventor: Thomas Gessner
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Patent number: 5395976Abstract: In the hydrogenation of phenol with H.sub.2 over Pd supported catalysts, the ratio of the products formed, cyclohexanone and cyclohexanol, can be predetermined by specific treatment of the catalysts during the initial activation and regeneration by O.sub.2 pretreatment and H.sub.2 treatment, the following time/temperature conditions being used:a) Cyclohexanone:cyclohexanol=85:15 to 98:2a1) for initial activation, no O.sub.2 pretreatment and H.sub.2 treatment for 50-10 hours at 300.degree.-500.degree. C.;a2) for regeneration, O.sub.2 pretreatment for 30-0.5 hours at 220.degree.-380.degree. C. and H.sub.2 treatment for 2-6 hours at 150.degree.-250.degree. C.;b) Cyclohexanone:cyclohexanol=30:70 to below 85:15b1) for initial activation, O.sub.2 pretreatment for 40-3 hours at 250.degree.-500.degree. C. and H.sub.2 treatment for 2-6 hours at 150.degree.-250.degree. C.;b2) for regeneration, O.sub.2 pretreatment for 30-0.5 hours at 380.degree.-600.degree. C. and H.sub.2 treatment for 2-6 hours at 150.degree.-250.Type: GrantFiled: December 10, 1993Date of Patent: March 7, 1995Assignee: Bayer AktiengesellschaftInventors: Jurgen Scharschmidt, Christine Mendoza-Frohn, Hans-Josef Buysch, Rainer Klotzbucher
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Patent number: 5015786Abstract: In a first form, a process is provided for preparing phenol by converting acetone by-produced by the cumene process into isopropanol, and alkylating benzene with the isopropanol and optional propylene, thereby forming phenol without acetone by-product. And cumene is prepared by alkylating benzene in the presence of a zeolite catalyst using isopropanol or a mixture of isopropanol and propylene as an alkylating agent. Further provided is the continuous alkylation of benzene with isopropanol wherein a reaction mixture is divided into first and second portions, with the first portion being recycled to the reactor and the second portion being taken out as a reaction product.Type: GrantFiled: November 27, 1989Date of Patent: May 14, 1991Assignee: Mitsui Petrochemical Industries Inc.Inventors: Shintaro Araki, Fujihisa Matsunaga, Hiroshi Fukuhara
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Patent number: 4846945Abstract: Oxidation of alcohols to ketones using bromine suffers from a side reaction of comparable speed in which a bromide substituted product is formed. Additionally, the use of bromine as reagent is relatively unpleasant and it creates a major waste disposal problem.The latter problem can be solved by generating bromine in situ by reaction between hydrogen peroxide and bromide ions or hydrogen bromide, but this inevitably increases the exposure of the alcohol to HBr/Br.sup.-. The selectivity of the process towards non-substituted oxidation depending upon the inherent deactivation or reactivity of the alcohol can be improved by irradiating the reactants with light of suitable frequency to generate bromine radicals in the mixture, and/or by controlling the rate of introduction of the hydrogen peroxide and controlling the extent to which mole ratio of HBr:alcohol is substoichiometric.Type: GrantFiled: September 2, 1987Date of Patent: July 11, 1989Assignee: Interox Chemicals LimitedInventors: Philip J. Turner, Vincent I. Routledge, Martin Jeff
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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: 4612401Abstract: 4-Hydroxy-2,4,6-trimethyl-2,5-cyclohexadienone is made by chlorinating 2,4,6-trimethylphenol with chlorine in an organic solvent in the absence of base while the hydrogen chloride formed is removed as it is formed by physical means and hydrolyzing the reaction mixture with water optionally in the presence of an inorganic base.Type: GrantFiled: March 19, 1985Date of Patent: September 16, 1986Assignee: Rhone-Poulenc SanteInventors: Michel Costantini, Francoise Igersheim, Leon Krumenacker
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Patent number: 4565895Abstract: 4-Hydroxy-2,4,6-trimethyl-2,5-cyclohexadienone is prepared by oxidation of 2,4,6-trimethylphenol with a manganese derivative of valency greater than 2 in an aqueous acidic medium.Type: GrantFiled: September 21, 1984Date of Patent: January 21, 1986Assignee: Rhone-Poulenc SanteInventors: Michel Costantini, Francoise Igersheim, Leon Krumenacker
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Patent number: 4562294Abstract: Spiro[5.5]undeca-1,4,8-trien-3-ones are prepared by heating a reaction mixture consisting essentially of a 4-aminomethylphenol, a conjugated diene, and an inert solvent at a temperature of at least about 190.degree. C.Type: GrantFiled: October 15, 1984Date of Patent: December 31, 1985Assignee: Ethyl CorporationInventor: Jerry M. Roper
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Patent number: 4560801Abstract: 4-Hydroxy-2,4,6-trimethyl-2,5-cyclohexadienone is prepared by treatment of 2,4,6-trimethylphenol with a halogenation agent and water in the presence of an organic solvent which is inert to the halogenation agent.Type: GrantFiled: July 10, 1984Date of Patent: December 24, 1985Assignee: Rhone-Poulenc SanteInventors: Michel Costantini, Francoise Igersheim, Leon Krumenacker
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Patent number: 4480133Abstract: Novel 2,4-dihydrocarbylspiro[5.5]undeca-1,4,8-trien-3-one compounds are prepared by reacting an N,N-dihydrocarbyl,2,6-dihydrocarbyl-4-aminomethylphenol with a conjugated diene and an alkyl halide in a liquid solvent medium.Type: GrantFiled: March 4, 1983Date of Patent: October 30, 1984Assignee: Ethyl CorporationInventor: Jerry M. Roper
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Patent number: 4477682Abstract: A process for the preparation of 4-hydroxy-2,4,6-trimethylcyclohexa-2,5-diene-1-one from 2,4,6-trimethylphenol is disclosed, comprising reacting 2,4,6-trimethylphenol with an aqueous solution or suspension of hypohalogenous acid or salt thereof in an aqueous medium or mixed medium of water and specific organic solvents. This process enables to prepare 4-hydroxy-2,4,6-trimethylcyclohexa-2,5-diene-1-one, which is a precursor for 2,3,5-trimethylhydroquinone, a starting material for the preparation of vitamin E, by a simplified operation, safely and at high yields.Type: GrantFiled: December 21, 1982Date of Patent: October 16, 1984Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tetsuo Tomita, Masahiro Jono, Toshiaki Takata