Aldehyde Reacted With Ketone Patents (Class 568/345)
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Patent number: 9908833Abstract: The present technology discloses processes for producing carboxylic acid. In some embodiments, the processes include contacting methanol and carbon monoxide in the presence of a liquid reaction medium under carbonylation conditions sufficient to form a carbonylation product, including acetic acid and acetaldehyde. The liquid reaction medium may include a carbonylation catalyst selected from rhodium catalysts, iridium catalysts and palladium catalysts; and water in a water concentration in a range of 1 wt. % to 14 wt. % based on the total weight of the liquid reaction medium. In certain embodiments, the processes comprise contacting at least a portion of the carbonylation product or a derivative thereof with a micro-porous material such as a silicoaluminophosphate (SAPO) to selectively convert at least a portion of the acetaldehyde to crotonaldehyde.Type: GrantFiled: December 2, 2016Date of Patent: March 6, 2018Assignee: LyondellBasell Acetyls, LLCInventors: Noel C. Hallinan, David L. Ramage, Daniel F. White
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Patent number: 9687422Abstract: Methods of obtaining a carotenoid-containing composition were developed, in which degradation of carotenoids is suppressed even though extraction and purification are performed on a culture of microorganism that produces carotenoids including astaxanthin by simple steps using a lower alcohol which is a conventionally known solvent, and the compositions have high astaxanthin content and contain highly pure carotenoids and also have satisfactory crystal properties. Further addition of a simple step that promotes isomerization of astaxanthin successfully improved the carotenoid yield.Type: GrantFiled: October 2, 2013Date of Patent: June 27, 2017Assignees: JX NIPPON OIL & ENERGY CORPORATION, DAICEL CORPORATIONInventors: Kazuya Mitsuhashi, Takanori Someya, Motoko Hayashi, Manabu Yamada, Shotaro Uchizawa, Kazuaki Hirasawa, Yuki Kawashima
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Publication number: 20140275400Abstract: The present invention provides methylene beta-diketone monomers, methods for producing the same, and compositions and products formed therefrom. In the method for producing the methylene beta-diketones of the invention, a beta-diketone is reacted with a source of formaldehyde in a modified Knoevenagel reaction optionally in the presence of an acidic or basic catalyst, and optionally in the presence of an acidic or non-acidic solvent, to form reaction complex. The reaction complex may be an oligomeric complex. The reaction complex is subjected to further processing, which may be vaporization by contact with an energy transfer means in order to isolate the beta-diketone monomer. The present invention further compositions and products formed from methylene beta-diketone monomers of the invention, including monomer-based products (e.g., inks, adhesives, coatings, sealants or reactive molding) and polymer-based products (e.g., fibers, films, sheets, medical polymers, composite polymers and surfactants).Type: ApplicationFiled: October 18, 2012Publication date: September 18, 2014Inventors: Yangbin Chen, Adam G. Malofsky, Jeffrey M. Sullivan, Stanley C. Wojciak, Tanmoy Dey, Bernard M. Malofsky
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Patent number: 8519193Abstract: The present invention relates to a method for producing 4-isopropyl-3-methyl-phenol by alykylizing meta-cresol, distilling, and crystallizing.Type: GrantFiled: July 15, 2008Date of Patent: August 27, 2013Assignee: LANXESS Deutschland GmbHInventor: Lutz Heuer
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Publication number: 20120264820Abstract: A compound, pharmaceutical composition and method for the treatment of mammals wherein the active therapeutic agent is a compound having the structure: wherein: R1 is an electronegative substituent, R2 is R1 or alkyl, R3 is H or O-alkyl, R4 and R5 are the same or different and are alkyl and R6 is H or OH.Type: ApplicationFiled: December 31, 2007Publication date: October 18, 2012Inventors: Kinfe Redda, Chavonda Janeebra Mills, Nelly Maleeva
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Patent number: 8097761Abstract: A method for producing a composition containing carotenoid at a content of 80% or greater, characterized in performing extraction on a culture of a microorganism, a concentrate of the culture, or a dried substance thereof with at least one selected from the group consisting of lower alcohols, water-containing lower alcohols, lower dialkylketones and ethers; and then washing a precipitate, obtained by concentrating the extract solution, with at least one selected from the group consisting of lower alcohols, water-containing lower alcohols, hydrocarbon-based solvents and lower dialkylketones; and food, a pharmaceutical composition or a cosmetic substance comprising the carotenoid-containing composition.Type: GrantFiled: March 28, 2007Date of Patent: January 17, 2012Assignee: JX Nippon Oil & Energy CorporationInventors: Tomoyuki Ishizaki, Satoru Ishikawa, Akira Tsubokura, Kazuaki Hirasawa
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Publication number: 20110009673Abstract: The present invention relates to a process for producing a 2-(1-hydroxyalkyl)cycloalkanone which includes the steps of (i) continuously mixing a cycloalkanone and an alkyl aldehyde in the water and a base catalyst to form a reaction system and allow both the compounds to react with each other; (ii) continuously withdrawing a reaction mixture produced in the step (i) out of the reaction system while allowing the step (i) to proceed; and (iii) adding an additional amount of water containing the base catalyst to the reaction system to maintain a constant concentration of the base catalyst and/or a constant amount of water in the reaction system while allowing the step (ii) to proceed.Type: ApplicationFiled: December 22, 2008Publication date: January 13, 2011Applicant: KAO CORPORATIONInventors: Junko Ueda, Yoshiharu Ataka
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Patent number: 7858381Abstract: Improved process for preparing high-purity, halogen-free o-phthalaldehyde, in which a) tetrahalo-o-xylene is hydrolyzed at a temperature of 155-160° C. and a pressure of from 2 to 5 bar, where appropriate in the presence of a phase-transfer catalyst, to o-phthalaldehyde, which b) is converted in an acidic alcoholic solution at a temperature of from 0 to the reflux temperature into the corresponding dialkoxyphthalane and, subsequently, c) an acetal cleavage is effected by acid hydrolysis at a pH >1.5 to pH 7, resulting in high-purity, halogen-free o-phthalaldehyde.Type: GrantFiled: June 27, 2006Date of Patent: December 28, 2010Assignee: DSM Fine Chemicals Austria NFG GmbH & Co KGInventors: Karlheinz Giselbrecht, Klaus Reiter, Rudolf Hermanseder
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Patent number: 7842841Abstract: This invention relates to a novel process for the preparation of timberone useful for perfume or cosmetics.Type: GrantFiled: March 17, 2008Date of Patent: November 30, 2010Assignee: DSM IP Assets B.V.Inventors: Werner Bonrath, Jan Schuetz
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Publication number: 20100063325Abstract: This invention relates to a novel process for the preparation of timberone useful for perfume or cosmetics.Type: ApplicationFiled: March 17, 2008Publication date: March 11, 2010Inventors: Werner Bonrath, Jan Schuetz
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Patent number: 7563935Abstract: Mixtures of specific crystal forms of astaxanthin and the individual crystal forms designated crystal Form I and II and disclosed together with methods for preparing said crystal Forms. Methods for preparing nutritional dosage forms including the disclosed astaxanthin crystal forms for the life science industry are also disclosed.Type: GrantFiled: February 15, 2008Date of Patent: July 21, 2009Assignee: Phares Pharmaceutical Research N.V. et al.Inventors: Steve Leigh, Mathew Louis Steven Leigh, Peter Van Hoogevest
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Publication number: 20080234521Abstract: Mixtures of specific crystal forms of astaxanthin and the individual crystal forms designated crystal Form I and II and disclosed together with methods for preparing said crystal Forms. Methods for preparing nutritional dosage forms including the disclosed astaxanthin crystal forms for the life science industry are also disclosed.Type: ApplicationFiled: February 15, 2008Publication date: September 25, 2008Applicant: PHARES PHARMACEUTICAL RESEARCH N. V.Inventors: Steve LEIGH, Mathew Louis Steven Leigh, Peter Van Hoogevest
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Patent number: 7279605Abstract: The invention relates to a process for the preparation, in a single step, of substituted 2-cyclopenten-1-ones by reacting a substituted enone with an aldehyde in the presence of a catalytic system. The catalytic system consists of a metal complex, such as a Ti(Cl)3(alkoxy), and a co-ingredient, such as a carboxylic acid anhydride or an anhydrous salt.Type: GrantFiled: April 19, 2007Date of Patent: October 9, 2007Assignee: Firmenich SAInventors: Denis Jacoby, Fabrice Keller
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Patent number: 7227044Abstract: The present invention relates to a cycloalkanone composition which contains cycloalkanone (1) in an amount of 70 wt % or more based on the composition, wherein the content of a dimer of a cycloalkanone represented by formula (2) is 0.055 or less in terms of weight ratio to the cycloalkanone (1), a process for producing the same, a process for producing a composition containing alkyl acetate (5) by using the cycloalkanone composition, and an alkyl acetate composition obtained by the process wherein n is an integer of 1 or 2, R1 and R2 each represent H, a C1 to C8 alkyl group etc., and R3 represents a C1 to C3 alkyl group.Type: GrantFiled: March 11, 2005Date of Patent: June 5, 2007Assignee: Kao CorporationInventor: Koji Mine
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Patent number: 6995289Abstract: A method for the synthesis of an ?,?-unsaturated ketone useful for making substituted 1,4-dihydropyridines is described by reacting an aldehyde with pyrrolidine and then adding a ketone followed by trifluoroacetic acid at low temperature. The synthesis is used in a process for making substituted 1,4-dihydropyridines wherein a vinylogous amide is prepared by reacting a 1,3-cyclohexanedione with a phenylethylamine. The ?,?-unsaturated ketone can be reacted with a vinylogous amide to form a 1,5-diketone which can be converted to a substituted 1,4-dihydropyridine.Type: GrantFiled: July 31, 2001Date of Patent: February 7, 2006Assignee: Astrazeneca ABInventors: Ian Patel, Philip Hopes
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Patent number: 6979751Abstract: Processes for producing higher molecular weight ketones are disclosed that include the steps of feeding an aldol catalyst solution, a lower molecular weight aldehyde, and a lower molecular weight ketone, through a reactor provided with a solid hydrogenation catalyst and hydrogen gas; recovering a liquid reactor effluent containing the higher molecular weight ketone as a reaction product; and recycling a portion of the recovered liquid reactor effluent back through the reactor.Type: GrantFiled: November 14, 2003Date of Patent: December 27, 2005Assignee: Eastman Chemical CompanyInventors: Jennifer Ellen McCusker-Orth, Brent Alan Tennant, James Charles Ciula
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Publication number: 20040171850Abstract: The present invention provides a process for producing 2-(1-hydroxyalkyl)cycloalkanone and/or 2-(1-hydroxyaryl)cycloalkanone in high yield and selectivity, as well as a process using the same to produce a cycloalkanone derivative useful as a perfume material and a physiologically active substance. Disclosed is a process for producing compound (3), which includes subjecting a cycloalkanone, and aldehyde (2) containing carboxylic acid (1), to aldol condensation in the presence of water and a basic catalyst, wherein the molar amount (referred to hereinafter as A) of the basic catalyst added is not less than the molar amount (referred to hereinafter as B) of the carboxylic acid (1) contained in the aldehyde (2) and the difference between A and B, that is, (A-B) is 0.06 mol or less per mol of the aldehyde (2), as well as a process for producing compounds (7) and (8) by using the compound (3) obtained by the above process.Type: ApplicationFiled: December 16, 2003Publication date: September 2, 2004Applicant: KAO CORPORATIONInventors: Koji Mine, Kimikazu Fukuda
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Publication number: 20040122261Abstract: Processes for producing higher molecular weight ketones are disclosed that include the steps of feeding an aldol catalyst solution, a lower molecular weight aldehyde, and a lower molecular weight ketone, through a reactor provided with a solid hydrogenation catalyst and hydrogen gas; recovering a liquid reactor effluent containing the higher molecular weight ketone as a reaction product; and recycling a portion of the recovered liquid reactor effluent back through the reactor.Type: ApplicationFiled: November 14, 2003Publication date: June 24, 2004Inventors: Jennifer Ellen McCusker-Orth, Brent Alan Tennant, James Charles Ciula
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Publication number: 20040019239Abstract: 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: ApplicationFiled: May 30, 2003Publication date: January 29, 2004Inventors: Barry M. Trost, Hisanaka Ito
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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: 6603047Abstract: A process for conducting multiphase reactions, especially the preparation of &agr;,&bgr;-unsaturated ketones by condensation of aldehydes with ketones.Type: GrantFiled: February 11, 2002Date of Patent: August 5, 2003Assignee: Oxeno Olefinchemie GmbHInventors: Klaus-Diether Wiese, Wilfried Buschken, Guido Protzmann
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Patent number: 6590111Abstract: A process is provided for the preparation of cyclohexene derivatives of general formula I or II: in which the substituents R1 and R2 independently of one another are defined as follows: R2 is OH or a protective group convertible to a hydroxyl group by hydrolysis, R3 and R4 are hydrogen or C1-C4-alkyl, and R5 is hydrogen or C1-C4-acyl, by the reduction or alkyne compounds of general formula III or IV: wherein the reducing agent used is at least one salt of hyposulfurous acid or hydroxymethanesulfinic acid or a mixture of at least one salt of hyposulfurous acid and at least one salt of hydroxymethanesulfinic acid.Type: GrantFiled: August 14, 2002Date of Patent: July 8, 2003Assignee: BASF AktiengesellschaftInventors: Johannes Grimmer, Thomas Müller, Volker Bomm
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Publication number: 20030092942Abstract: The present invention relates to a novel process for the preparation of 2,3-pentanedione starting with hydroxyacetone and paraldehyde.Type: ApplicationFiled: November 7, 2002Publication date: May 15, 2003Inventors: Stefan Lambrecht, Oliver Franke, Klaus Zahlmann
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Patent number: 6541672Abstract: The invention deals with the derivatives of benzilidine having basic formula as follows (I): wherein X can be cyclohexanone, cyclopentanone, or acetone, while Y and Z can be either electron withdrawing, electron donating or steric group. Y may or may not be the same with Z. Methyl, ethyl, methoxy group or halogen were prefered in the experiment. The benzilidine cyclohexanone, benzilidine cyclopentanone, and benzilidine acetone derivates were found to be novel compounds showing anti-bacterial, antioxidant, and anti-inflammatory activities that enable them to be used for drug.Type: GrantFiled: February 20, 1998Date of Patent: April 1, 2003Assignee: Faculty of Pharmacy, The University of Gadjah MadaInventors: Sardjiman, Mochammad Samhoedi Reksohadiprodjo, Henk Timmerman
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Publication number: 20020161264Abstract: A process for conducting multiphase reactions, especially the preparation of &agr;,&bgr;-unsaturated ketones by condensation of aldehydes with ketones.Type: ApplicationFiled: February 11, 2002Publication date: October 31, 2002Applicant: DE GUSSA AGInventors: Klaus-Diether Wiese, Wilfried Buschken, Guido Protzmann
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Publication number: 20020147367Abstract: 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: ApplicationFiled: October 31, 2001Publication date: October 10, 2002Inventors: Barry M. Trost, Hisanaka Ito
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Patent number: 6437190Abstract: A process for preparing aldols by catalytic reaction of aldehydes and/or ketones comprises conducting said reaction in the channels of a microstructured reaction system.Type: GrantFiled: November 2, 2001Date of Patent: August 20, 2002Assignee: Siemens Axiva GmbH & Co. KGInventors: Inga Leipprand, Thorsten Lahrs
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Patent number: 6433230Abstract: &agr;,&bgr;-Unsaturated keto compounds are prepared by base-catalyzed aldol condensation of aldehydes and/or ketones having from 1 to 15 carbon atoms, comprising: reacting the aldehydes and/or ketones with an aqueous catalyst solution under adiabatic reaction conditions; and separating the reaction mixture obtained by rapid distillation into a top product comprising water, aldehyde and/or ketone and a bottom product comprising &agr;,&bgr;-unsaturated keto compounds and aqueous catalyst phase.Type: GrantFiled: November 22, 2000Date of Patent: August 13, 2002Assignee: Oxeno Olefinchemie GmbHInventors: Wilfried Bueschken, Klaus-Diether Wiese, Guido Protzmann
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Publication number: 20020055655Abstract: A process for preparing aldols by catalytic reaction of aldehydes and/or ketones comprises conducting said reaction in the channels of a microstructured reaction system.Type: ApplicationFiled: November 2, 2001Publication date: May 9, 2002Inventors: Inga Leipprand, Thorsten Lahrs
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Patent number: 6339159Abstract: An aldehyde compound is reacted with an amino compound and hydrogen cyanate in the presence of a chiral zirconium catalyst obtained by mixing a zirconium alkoxide with an optically active binaphthol compound.Type: GrantFiled: July 13, 2001Date of Patent: January 15, 2002Assignee: Japan Science and Technology CorporationInventors: Shu Kobayashi, Haruro Ishitani
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Patent number: 6303823Abstract: A process for preparing ketones by so-called “crossed aldol condensation” of a ketone with an aldehyde in the presence of a catalyst system consisting of approximately equimolar amounts of a secondary amine and of a carboxylic acid containing at least 2 C atoms, to form an &agr;,&bgr;-unsaturated ketone, and, where appropriate, subsequent catalytic hydrogenation. The process is used in particular for preparing 6-methyl-3-hepten-2-one by reacting acetone with isovaleraldehyde, and for preparing its hydrogenation product, 6-methylheptan-2-one, which is an important precursor for numerous active substances, in particular for preparing lipid-soluble vitamins such as vitamin E.Type: GrantFiled: December 5, 2000Date of Patent: October 16, 2001Assignee: BASF AktiengesellschaftInventors: Andreas Kramer, Christian Knoll, Johann-Peter Melder, Wolfgang Siegel, Gerd Kaibel
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Publication number: 20010003784Abstract: A process for preparing ketones by so-called “crossed aldol condensation” of a ketone with an aldehyde in the presence of a catalyst system consisting of approximately equimolar amounts of a secondary amine and of a carboxylic acid containing at least 2 C atoms, to form an &agr;,&bgr;-unsaturated ketone, and, where appropriate, subsequent catalytic hydrogenation.Type: ApplicationFiled: December 5, 2000Publication date: June 14, 2001Inventors: Andreas Kramer, Christian Knoll, Johann-Peter Melder, Wolfgang Siegel, Gerd Kaibel
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Patent number: 6150561Abstract: A widely applicable process for the manufacture of carotenoids by a Wittig reaction comprises carrying out the Wittig reaction in a polar reaction medium in a manner such that neither the reactants nor the thus-manufactured carotenoid are significantly dissolved in the reaction medium. An especially suitable reaction medium is a polar, toxicologically harmless solvent which remains monophasic on the addition of water in an amount up to about 30 vol. % and which permits the triarylphosphine oxide which is formed to dissolve well. Lower alcohols and acetone, as sole solvents or as mixtures with one another and/or with water, are especially suitable as the polar reaction medium. This process permits the use of much more concentrated reaction mixtures, simplifies the regeneration of the solvent and generally the reaction procedure, and avoids toxicologically objectionable solvents such as halogenated hydrocarbons.Type: GrantFiled: September 4, 1998Date of Patent: November 21, 2000Assignee: Roche Vitamins Inc.Inventors: Paul Kreienbuhl, Peter Rudin, Werner Rudolph
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Patent number: 5994589Abstract: A process for preparing 2,5,6-trimethyl-2-cyclohexen-1-one by reacting diethyl ketone with crotonaldehyde or a compound which is converted under the chosen reaction conditions into crotonaldehyde, in the presence of basic agents at elevated temperature, which comprisesa) simultaneously pumping one mole of crotonaldehyde or one mole of a compound which is converted under the reaction conditions into crotonaldehyde, about 5 to 30 moles of diethyl ketone and the aqueous solution or suspension of a strong base, through separate lines or at least partly in the form of a suitable mixture, continuously into a pressure vessel, which is heated where appropriate and which ensures vigorous mixing, in such a way thatb) the reaction temperature is between 150.degree. C. and 350.degree. C., and the average residence time in the pressure vessel is only about 0.1 second to 20 minutes.Type: GrantFiled: March 10, 1999Date of Patent: November 30, 1999Assignee: BASF AktiengesellschaftInventors: Detlef Ruff, Wolfram Burst, Wulf Kaiser, Manfred Stroezel
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Patent number: 5654488Abstract: Improved process for the preparation of astaxanthin by Wittig reaction of 2 mol of 3-methyl-5-(2,6,6-trimethyl-3-oxo-4-hydroxy-1-cyclohexenyl)-2,4-pentadieny ltriarylphosphonium salts with one mol of 2,7-dimethyl-2,4,6-octatrienedial avoiding the use of halohydrocarbons as solvents.Type: GrantFiled: March 15, 1996Date of Patent: August 5, 1997Assignee: BASF AktiengesellschaftInventors: Wolfgang Krause, Klaus Henrich, Joachim Paust, Hansgeorg Ernst
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Patent number: 5637774Abstract: Disclosed is a very economical way to produce vinyl carbonyls such as ethyl vinyl ketone. Disclosed also is a purification process of separating vinyl carbonyls and coreactants. The catalyst and reaction conditions give useful yields of vinyl carbonyls, the thermodynamically unfavorable product along with coreactants that are more thermodynamically favored. Disclosed also is the separation of reactants that takes place at low distillation temperatures and pressures in the presence of antioxidant.Type: GrantFiled: September 29, 1995Date of Patent: June 10, 1997Assignee: Eastman Chemical CompanyInventor: William A. Beavers
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Patent number: 5625099Abstract: Abstract of the Disclosure: Compounds of the formula I ##STR1## where R.sup.1 is H or C.sub.1 -C.sub.4 -alkyl, R.sup.2 is C.sub.1 -C.sub.4 -alkyl and R.sup.3 is an ether, silyl ether or acetal protective group which can be converted into a hydroxyl group by hydrolysis, in particular one of the radicals ##STR2## and a process for preparing these compounds by reacting an alkenyne of the formula II ##STR3## in an inert solvent in the presence of lithium amide with a cyclohexenone of the formula III ##STR4## and the use of the compounds of the formula I for preparing astaxanthin, are described.Type: GrantFiled: May 23, 1995Date of Patent: April 29, 1997Inventors: Hansgeorg Ernst, Walter Dobler, Joachim Paust, Udo Rheude
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Patent number: 5496709Abstract: A process for production of canthaxanthin comprising the steps of culturing a microorganism capable of producing canthaxanthin and belonging to the genus Corynebacterium, such as Corynebacterium sp. SQH 348 (FERM BP-4284), and recovering canthaxanthin from the culture.Type: GrantFiled: June 10, 1994Date of Patent: March 5, 1996Assignee: Nippon Oil Co., Ltd.Inventors: Akira Tsubokura, Hisashi Yoneda, Mikihiro Takai, Takashi Kiyota
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Patent number: 5300654Abstract: .beta.-hydroxyketones are prepared by reacting an aldehyde with acetone in the presence of perhydroisoindole or pyrrolidine and water. The resulting .beta.-hydroxyketone is further reacted in the presence of a solvent mixture to produce .alpha.-.beta.-unsaturated ketones.Type: GrantFiled: July 15, 1991Date of Patent: April 5, 1994Assignee: Nippon Soda Co., Ltd.Inventors: Masashi Nakajima, Tadashi Kyotani, Mikio Sawaki
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Patent number: 5243081Abstract: The present invention provides an aldol condensation dehydration catalyst, a process for preparing the same comprising reacting an aluminium salt with at least one magnesium compound selected from the group consisting of magnesium oxide and magnesium hydroxide to support thereon an aluminium compound and heating said supported product at a temperature in the range from 350.degree. to 700.degree. C., and a process for preparing an aldol condensation dehydrate by using the process.Type: GrantFiled: May 15, 1992Date of Patent: September 7, 1993Assignee: Sumitomo Chemical Company, LimitedInventors: Masaru Ishino, Masami Fukao, Kazuaki Sasaki, Gohfu Suzukamo, Masao Sasaki
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Patent number: 5210314Abstract: A process for preparing canthaxanthin (Ia) and astaxanthin (Ib) of the formula I ##STR1##where R is H (a) or OH (b), comprises reacting a tertiary alcohol of the formula II ##STR2##where R is H (a) or OH (b), with trifluoroacetic acid, reacting the resulting novel trifluoroacetate of the formula III ##STR3##with triphenylphosphine, and reacting the resulting novel triphenylphosphonium trifluoroacetate of the formula IV ##STR4##with 2,7-dimethyl-2,4,6-octatriene-1,8-dial under the conditions of a Wittig synthesis. The present invention also relates to the novel trifluoroacetates of the formula III and the corresponding triphenylphosphonium trifluoroacetates of the formula IV.Type: GrantFiled: April 29, 1991Date of Patent: May 11, 1993Assignee: BASF AktiengesellschaftInventors: Hansgeorg Ernst, Joachim Paust, Werner Hoffmann
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Patent number: 5124486Abstract: The invention provides a process for the preparation of cyclic ketones of the general formula ##STR1## in which R represents an optionally substituted alkyl or cycloalkyl group and R.sup.1 and R.sup.2 independently represent an optionally substituted alkyl, cycloalkyl or aryl group, which comprises heating a compound of the general formula ##STR2## in which X represents a chlorine or bromine atom and R is as defined above, with a compound of the general formula ##STR3## in which R.sup.1 and R.sup.2 are as defined above, in the presence of an organic acid.Certain cyclic ketones of formula (I) are useful as intermediates in the preparation of certain fungicidally active cyclopentane derivatives.Type: GrantFiled: April 19, 1991Date of Patent: June 23, 1992Assignee: Shell Research LimitedInventor: Paul H. Briner
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Patent number: 5081309Abstract: Cyclopentanones monoalkylated in the 2-position and of the general formula I ##STR1## where R.sup.1 is a branched or straight-chain aliphatic group of 2 to 12 carbon atoms and R.sup.2 to R.sup.7 may be identical or different and are each hydrogen or alkyl of 1 to 5 carbon atoms, are prepared by a process in which a cyclopentanone of the general formula II ##STR2## or a corresponding cyclopentenone, is reacted with an aldehyde of the general formula III ##STR3## at from 80.degree. to 280.degree. C. in the presence of hydrogen in an autoclave, over a catalyst which contains, as active components, on the one hand an oxide or a phosphate of magnesium, aluminum, titanium or zinc or of one of the rare earth metals, and on the other hand a noble metal of group VIII of the periodic table, preferably palladium.Type: GrantFiled: June 22, 1987Date of Patent: January 14, 1992Assignee: BASF AktiengesellschaftInventors: Walter Gramlich, Wolfgang Lengsfeld
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Patent number: 5026919Abstract: Basic intermediate or large pore zeolites having a Constraint Index less than 12 are useful as catalysts in the dehydrogenation-aromatization of cyclie dienes, in the isomerization of olefins and in the aldol condensation, and particularly in the cyclization of acetonylacetone to 3-methyl-2-cyclopenten-1-one.Type: GrantFiled: December 20, 1985Date of Patent: June 25, 1991Assignee: Mobil Oil CorporationInventor: Ralph M. Dessau
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Patent number: 5004839Abstract: Unsaturated ketones are produced from ketones and paraformadehyde under mild reaction conditions utilizing a catalyst comprising a halogen acid salt of a secondary amine and a nonsoluble solid oxide of an element selected from groups IB, IIIA, IVA, IVB, VA, VB, VIB and VIII of the periodic table. Temperatures of 120-150 and pressures of 700-1200 kpa are preferred; by-products may include di-unsaturated ketones such as divinyl ketone. Unsaturated ketones such as methyl vinyl ketone are useful in imparting ultraviolet sensitivity to plastics which enhances degradability.Type: GrantFiled: April 13, 1990Date of Patent: April 2, 1991Assignee: Aristech Chemical CorporationInventors: Joseph Pugach, Jeffrey S. Salek
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Patent number: 4992577Abstract: A process for preparing a compound of the formula ##STR1## in which Y is halogen, alkyl or cycloalkyl optionally substituted by halogen or C.sub.1-4 -alkoxy, alkenyl optionally substituted by halogen, aryl, heteroaryl or alkoxycarbonyl,X is hydrogen, halogen or optionally halogen-substituted alkyl, orX and Y, together with the adjacent C atom, form a saturated cycloalkphatic ring having up to 6 C atoms, andR is hydrogen or C.sub.1 -C.sub.4 -alkyl, comprising reacting an aldehyde of the formula ##STR2## with 2-methylbutan-3-one of the formula ##STR3## in the presence of a hydrohalic acid thereby to form a 4,4-dimethyl-3-halogeno-1-hexen-5-one of the formula ##STR4## in which Hal is halogen, halogenating said compound to produce a compound of the formula ##STR5## and reacting said compound with a base of the formulaR--OM (VI)in whichM is one equivalent of an alkali or alkaline earth metal ion.Compounds IV and V are new. By suitable conditions the trans isomer is selectively produced.Type: GrantFiled: May 22, 1989Date of Patent: February 12, 1991Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Dieter Arlt, Manfred Jautelat
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Patent number: 4945184Abstract: Unsaturated ketones are produced from ketones and paraformaldehyde under mild reaction conditions utilizing a catalyst comprising a halogen acid salt of a secondary amine and a small amount of a carboxylic acid.Temperatures of 120.degree.-150.degree. C. and pressures of 775-1135 kilopascals are preferred. Di-unsaturated ketones such as divinyl ketone may also be produced; if the starting ketone already has an unsaturated group, a second unsaturated group will be produced.Type: GrantFiled: June 19, 1989Date of Patent: July 31, 1990Assignee: Aristech Chemical CorporationInventors: Joseph Pugach, Jeffrey S. Salek
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Patent number: 4877904Abstract: Novel odorant and/or flavoring substances are described. These are the compounds of the formula ##STR1## wherein: R.sup.1 represents methyl or ethyl,R.sup.2 represents hydrogen or methyl,the dotted line represents an optional carbon-carbon bond,n is 0 or 1, and,when n is O, R.sup.3 is hydrogen and R.sup.4 represents acetyl or propronyl, and,when n is 1, R.sup.3 represents methyl or ethyl and R.sup.4 represents hydrogen or methyl,with the exception of 1,4,4,7a-tetramethyl-3a,4,5,7a-tetrahydro-7(6H)-ind-1-enone.The compounds of formula I possess organoleptic properties which make them particularly suitable for use as odorant and/or flavoring substances.Type: GrantFiled: September 9, 1987Date of Patent: October 31, 1989Assignee: Givaudan CorporationInventor: Peter Naegeli
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Patent number: 4874900Abstract: A process is provided for the preparation of pseudoionones by the condensation reaction of citral with a ketone in the presence of lithium hydroxide catalyst.Type: GrantFiled: June 16, 1987Date of Patent: October 17, 1989Assignee: Union Camp CorporationInventor: Peter W. D. Mitchell
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Patent number: 4820874Abstract: The yield of 2,5,6-trimethyl-cyclohex-2-en-1-one is increased by reacting diethyl ketyone, in the presence of an alkali, with crotonaldehyde or a compound which is converted to crotonaldehyde under the reaction conditions chose, and working up the reaction mixture by distillation, by a method in which the distillation residue obtained is either(a) heated at from 120.degree. to 250.degree. C. in particular from 120.degree. to 200.degree. C., with the addition of a catalytic amount of an alkali, or(b) heated at from 150.degree. to 250.degree. C. without the addition of such a substance,and the mixture of 2,5,6-trimethylcyclohex-2-en-1-one and diethyl ketone which is formed from the distillation residue as a result of the heat treatment is separated by distillation.Type: GrantFiled: October 23, 1987Date of Patent: April 11, 1989Assignee: BASF AktiengesellschaftInventors: Peter Tavs, Harald Laas, Horst Schauer, Lothar Arnold