Isomerization Patents (Class 568/341)
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Patent number: 10660351Abstract: The invention is related to a beverage having an improved flavor. More precisely, it is related to a beverage having an improved flavor, comprising an aqueous medium extract of a hop having been subjected to an oxidation treatment.Type: GrantFiled: June 20, 2013Date of Patent: May 26, 2020Assignee: Kirin Holdings Kabushiki KaishaInventors: Yuji Kaneko, Fumitoshi Manabe, Yoshimasa Taniguchi, Mikio Katayama
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Patent number: 9416082Abstract: The present invention concerns a process for the isomerization of an exo double bond toward an endo double bond being performed in the presence of a catalyst system comprising palladium (Pd) or platinum (Pt) and molecular hydrogen or a hydrogen source.Type: GrantFiled: February 7, 2014Date of Patent: August 16, 2016Assignee: Firmenich SAInventors: Ramez Boshra, Koenraad Vanhessche, Anatoly Alexander
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Patent number: 9364823Abstract: In a process for activating a hydroalkylation catalyst, a catalyst precursor comprising a solid acid component and a compound of a hydrogenation metal is heated at a heating rate of less than 50° C./hour in the presence of hydrogen to an activation temperature in a range from 100° C. to 260° C. and then the heated catalyst precursor is treated with hydrogen for a duration effective to reduce at least a portion of the metal compound to an elemental form.Type: GrantFiled: October 3, 2013Date of Patent: June 14, 2016Assignee: ExxonMobil Chemical Patents Inc.Inventors: Gabor Kiss, Christopher L. Becker, Tan-Jen Chen, Thomas E. Green
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Patent number: 9217122Abstract: The present invention relates to compounds of Formula (I), wherein one R group is a hydrogen atom and the other is a hydrogen atom or a C1-3 alkyl group; and each carbon-carbon double bond of said compound, independently from each other, can be in a configuration Z or E or a mixture thereof; which are useful perfuming ingredients.Type: GrantFiled: June 18, 2012Date of Patent: December 22, 2015Assignee: Firmenich SAInventor: Peter Fankhauser
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Patent number: 9000223Abstract: A process for preparing a ketone by conversion of a compound E which contains an epoxy group to the ketone in the presence of a mixture comprising at least one noble metal and at least one metal oxide as a catalyst system, wherein the metal oxide in the catalyst system is at least one of titanium dioxide and zirconium dioxide, and the process is conducted at 0 to 0.9 bar of hydrogen.Type: GrantFiled: February 27, 2014Date of Patent: April 7, 2015Assignee: Evonik Industries AGInventors: Kevin Micoine, Martin Roos, Peter Hannen, Harald Haeger, Klaus Bartosch
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Patent number: 8980953Abstract: According to the present invention, there are provided a food and a food additive obtained using an alkaline decomposition product of a hop extract, and an agent for suppressing fat accumulation or for suppressing weight gain comprising the same as an active ingredient.Type: GrantFiled: June 11, 2010Date of Patent: March 17, 2015Assignee: Kirin Holdings Kabushiki KaishaInventors: Yoshimasa Taniguchi, Fumitoshi Manabe, Yumie Kobayashi, Mikio Katayama
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Publication number: 20140249331Abstract: A process for preparing a ketone by conversion of a compound E which contains an epoxy group to the ketone in the presence of a mixture comprising at least one noble metal and at least one metal oxide as a catalyst system, wherein the metal oxide in the catalyst system is at least one of titanium dioxide and zirconium dioxide, and the process is conducted at 0 to 0.9 bar of hydrogen.Type: ApplicationFiled: February 27, 2014Publication date: September 4, 2014Applicant: Evonik Industries AGInventors: Kevin MICOINE, Martin Roos, Peter Hannen, Harald Haeger, Klaus Bartosch
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Patent number: 8766013Abstract: The invention relates to a process for the production of hexahydro-iso-alpha-acids starting from iso-alpha-acids (or tetrahydro-iso-alpha-acids) in which iso-alpha-acids (or tetrahydro-iso-alpha-acids) are mixed with a heterogeneous ruthenium containing catalyst, that catalyzes the hydrogenation from iso-alpha-acids or tetrahydro-iso-alpha-acids to hexahydro-iso-alpha-acids, either in solvent-free conditions, or in the presence of a solvent phase (e.g. carbon dioxide, water, ethanol or another organic solvent, or mixtures thereof), and in the absence or presence of other hop compounds (such as beta-acids).Type: GrantFiled: June 14, 2011Date of Patent: July 1, 2014Assignee: Katholieke Universiteit LeuvenInventors: Pascal Mertens, Dirk De Vos, Bart Steenackers
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Method for isomerisation of hop alpha-acids using heterogeneous alkaline earth metal based catalysts
Patent number: 8710273Abstract: The invention relates to a process for the production of iso-alpha-acids starting from hop alpha-acids in which an hop alpha-acid containing feed is contacted with a heterogeneous alkaline earth metal based catalyst, that essentially does not dissolve in the alpha-acid containing feed or in the iso-alpha-acid product phase, either in solvent-free conditions or in the presence of water, carbon dioxide, or an organic solvent or a mixture thereof. The resulting mixture is subjected to a temperature of at least 293 K, preferably under an inert atmosphere, for a time sufficient to effect high conversion of the alpha-acid reactant into the iso-alpha-acid product. The molar ratio of alpha-acid to earth alkaline metal (Mg, Ca, Sr, Ba) varies preferably between 0.2 and 20. After the isomerization process, the heterogeneous alkaline earth metal based catalyst can be quantitatively separated from the iso-alpha-acid product phase by liquid-solid separation techniques.Type: GrantFiled: April 28, 2011Date of Patent: April 29, 2014Assignee: IFAST NVInventors: Luc De Cooman, Dirk De Vos, Pascal Mertens, Bart Steenackers -
Patent number: 8394994Abstract: The present invention relates to [1] a process for producing a 2-alkyl-2-cycloalken-1-one represented by the following general formula (2), which includes the step of subjecting a 2-(1-hydroxyalkyl)cycloalkan-1-one to dehydration and isomerization in the co-existence of an acid and a platinum group metal catalyst, and [2] a process for producing an alkyl(3-oxo-alkylcycloalkyl)acetate which is useful as a perfume material, using the 2-alkyl-2-cycloalken-1-one: wherein n is an integer of 1 or 2; and R1 and R2 are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms with the proviso that R1 and R2 may form a ring through a carbon atom adjacent thereto.Type: GrantFiled: April 2, 2009Date of Patent: March 12, 2013Assignee: Kao CorporationInventors: Makiko Muroi, Atsushi Nagasawa, Kunshi Matsumoto, Mariko Kagaya, Hirotsugu Nishimura, Yoshiharu Ataka
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METHOD FOR ISOMERISATION OF HOP ALPHA-ACIDS USING HETEROGENEOUS ALKALINE EARTH METAL BASED CATALYSTS
Publication number: 20130060066Abstract: The invention relates to a process for the production of iso-alpha-acids starting from hop alpha-acids in which an hop alpha-acid containing feed is contacted with a heterogeneous alkaline earth metal based catalyst, that essentially does not dissolve in the alpha-acid containing feed or in the iso-alpha-acid product phase, either in solvent-free conditions or in the presence of water, carbon dioxide, or an organic solvent or a mixture thereof. The resulting mixture is subjected to a temperature of at least 293 K, preferably under an inert atmosphere, for a time sufficient to effect high conversion of the alpha-acid reactant into the iso-alpha-acid product. The molar ratio of alpha-acid to earth alkaline metal (Mg, Ca, Sr, Ba) varies preferably between 0.2 and 20. After the isomerisation process, the heterogeneous alkaline earth metal based catalyst can be quantitatively separated from the iso-alpha-acid product phase by liquid-solid separation techniques.Type: ApplicationFiled: April 28, 2011Publication date: March 7, 2013Applicant: IFAST NVInventors: Luc De Cooman, Dirk De Vos, Pascal Mertens, Bart Steenackers -
Patent number: 8378147Abstract: The present invention relates to a process for producing a 2-alkyl-2-cycloalken-1-one represented by the following general formula (2), including the step of reacting a 2-alkylidene cycloalkanone in the presence of a palladium and/or platinum catalyst which is treated in the following steps (a) and (b); and a method for activating the palladium and/or platinum catalyst including the following steps (a) and (b): Step (a): activating the palladium and/or platinum catalyst in an atmosphere containing a hydrogen gas; and Step (b): replacing the hydrogen gas being present as the atmosphere for the catalyst in the step (a), with an inert gas to remove the hydrogen gas out of the reaction system, wherein m is 0 to 3; n is 1 or 2; R1 and R2 are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms; and R3 is an alkyl group having 1 to 5 carbon atoms. In accordance with the present invention, the 2-alkyl-2-cycloalken-1-one can be produced with a high purity and a high productivity.Type: GrantFiled: April 2, 2009Date of Patent: February 19, 2013Assignee: KAO CorporationInventors: Kunshi Matsumoto, Atsushi Nagasawa, Yoshiharu Ataka
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Publication number: 20120184780Abstract: A process for preparing isohumulone compositions, which process provides an improvement over the extant art, and yields an isohumulone preparation derived from a hop extract of high yield and purity, which has excellent physical stability, and is essentially free from undesirable lupulones, fatty acids, hop oils and degradation compounds.Type: ApplicationFiled: September 22, 2010Publication date: July 19, 2012Applicant: KALAMAZOO HOLDINGS, INC.Inventors: Joshua James Tuinstra, Peter Collins Vanalstyne, Brian Patrick Buffin
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Patent number: 8222458Abstract: Disclosed is a process for the synthesis of (3R)-3-hydroxy-?-ionone and its (3S)-enantiomer in high optical purity from commercially available (rac)-?-ionone. The key intermediate for the synthesis of these hydroxyionones is 3-keto-?-ionone ketal that was prepared from (rac)-?-ionone after protection of this ketone as a 1,3-dioxolane. Reduction of 3-keto-?-ionone ketal followed by deprotection, lead to 3-hydroxy-?-ionone that was transformed into (rac)-3-hydrox-?-ionone by base-catalyzed double bond isomerization in 46% overall yield from (rac)-?-ionone. The racemic mixture of these hydroxyionones was then resolved by enzyme-mediated acylation in 96% ee. (3R)-3-Hydroxy-?-ionone and its (3S)-enantiomer were respectively transformed to (3R)-3-hydroxy-(?-ionylideneethyl)triphenylphosphonium chloride [(3R)-C15-Wittig salt] and its (3S)-enantiomer [(3S)-C15-Wittig salt] according to known procedures.Type: GrantFiled: June 15, 2009Date of Patent: July 17, 2012Assignee: University of Maryland, College ParkInventors: Frederick Khachik, An-Ni Chang
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Patent number: 8058479Abstract: A method for purifying a crude acetone raw material containing low molecular weight impurities using three columns in sequence is disclosed.Type: GrantFiled: December 8, 2009Date of Patent: November 15, 2011Assignee: Sabic Innovation Plastics IP B.V.Inventors: Mark Erik Nelson, Andrey Yurievich Sokolov, Ilya Yurievich Krupenko, Valery Yurievich Aristovich
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Publication number: 20110184198Abstract: The present invention concerns a process of isomerizing trans fused bicyclic derivatives into cis fused bicyclic derivatives and the preparation of vitamin D or analogs thereof comprising said isomerisation step.Type: ApplicationFiled: January 24, 2011Publication date: July 28, 2011Inventors: Jean-Luc MOUTOU, Florent Mouton, Gilles Pellegrino, Jean Lafay
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Publication number: 20110152575Abstract: The present disclosure describes processes for the epimerization of a cyclohexene comprising the steps of providing to a reactor a first isomer of a 1-(2-alkyl-3-cyclohexen-1-yl)-alkanone compound according to Formula I wherein R1 ad R2 are each independently C1-C4 alkyl, and R3, R4, R5, R6, R7, and R8 are each independently selected from the group consisting of H and C1-C4 alkyl; and epimerizing the first isomer of the 1-(2-alkyl-3-cyclohexen-1-yl)-alkanone with a metal alkoxide base to form a second isomer of the 1-(2-alkyl-3-cyclohexen-1-yl)-alkanone.Type: ApplicationFiled: December 18, 2009Publication date: June 23, 2011Inventors: Daniel Martin Bourgeois, Gregory Scot Miracle, Phillip John Porter, Eva Boros, Kenneth Richard Seddon, Harambage Quintus Nimal Gunaratne
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Patent number: 7902404Abstract: Provided that a method for inexpensively producing optically active ?-ionone with a high yield and a high asymmetric yield and with good workability in a short process, and a perfume composition comprising the optically active ?-ionone obtained by the aforementioned method. A method for producing optically active ?-ionone, comprising allowing ?-ionone as a mixture of optical isomers to react with an esterification agent, and hydrolyzing the obtained ?-ionone enol ester; a method for producing optically active ?-ionone comprising subjecting ?-ionone as a mixture of optical isomers to an asymmetric reduction, allowing the obtained optically active ?-ionol to react with an esterification agent to give an optically active ?-ionol ester, hydrolyzing the obtained optically active ?-ionol ester after purification as necessary, and then oxidizing the obtained optically active ?-ionol; and a perfume composition comprising thus obtained optically active ?-ionone.Type: GrantFiled: September 13, 2006Date of Patent: March 8, 2011Assignee: Takasago International CorporationInventors: Tetsuya Yamamoto, Kenji Yagi, Kenya Ishida
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Publication number: 20110040127Abstract: The present invention relates to a process for producing a 2-alkyl-2-cycloalken-1-one represented by the following general formula (2), including the step of reacting a 2-alkylidene cycloalkanone in the presence of a palladium and/or platinum catalyst which is treated in the following steps (a) and (b); and a method for activating the palladium and/or platinum catalyst including the following steps (a) and (b): Step (a): activating the palladium and/or platinum catalyst in an atmosphere containing a hydrogen gas; and Step (b): replacing the hydrogen gas being present as the atmosphere for the catalyst in the step (a), with an inert gas to remove the hydrogen gas out of the reaction system, wherein m is 0 to 3; n is 1 or 2; R1 and R2 are each independently a hydrogen atom or an alkyl group having 1 to 8 carbon atoms; and R3 is an alkyl group having 1 to 5 carbon atoms. In accordance with the present invention, the 2-alkyl-2-cycloalken-1-one can be produced with a high purity and a high productivity.Type: ApplicationFiled: April 2, 2009Publication date: February 17, 2011Applicant: KAO CORPORATIONInventors: Kunshi Matsumoto, Atsushi Nagasawa, Yoshiharu Ataka
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Patent number: 7674765Abstract: The invention relates to a method for producing cyclohexadecanone by hydrogenating cyclohexadecenone, to mixtures of aromatic substances, and to products containing the inventive cyclohexadecanone.Type: GrantFiled: May 22, 2003Date of Patent: March 9, 2010Assignee: Symrise GmbH & Co., KGInventors: Ingo Wöhrle, Walter Kuhn, Hans-Ulrich Funk, Alfred Körber
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Patent number: 7622614Abstract: The present invention is directed to novel methods for production of 5-epi-?-vetivone, 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-2,6-dien-8-one and 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-1,6-dien-8-one, which are useful for their fragrant qualities. In one embodiment the present invention describes a method for production of 5-epi-?-vetivone by the use of premnaspirodiene as starting material. In another embodiment the present invention describes a method for production of 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-2,6-dien-8-one and 2-isopropyl-6,10-dimethyl-spiro[4.5]deca-1,6-dien-8-one by the use of premnaspirodiene as starting material. In yet another embodiment the present invention describes a novel method for production of premnaspirodiene from a terpene substrate.Type: GrantFiled: March 20, 2008Date of Patent: November 24, 2009Assignee: Allylix, Inc.Inventors: Bryan N. Julien, David M. Wallace
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Publication number: 20090216039Abstract: Provided that a method for inexpensively producing optically active ?-ionone with a high yield and a high asymmetric yield and with good workability in a short process, and a perfume composition comprising the optically active ?-ionone obtained by the aforementioned method. A method for producing optically active ?-ionone, comprising allowing ?-ionone as a mixture of optical isomers to react with an esterification agent, and hydrolyzing the obtained ?-ionone enol ester; a method for producing optically active ?-ionone comprising subjecting ?-ionone as a mixture of optical isomers to an asymmetric reduction, allowing the obtained optically active ?-ionol to react with an esterification agent to give an optically active ?-ionol ester, hydrolyzing the obtained optically active ?-ionol ester after purification as necessary, and then oxidizing the obtained optically active ?-ionol; and a perfume composition comprising thus obtained optically active ?-ionone.Type: ApplicationFiled: September 13, 2006Publication date: August 27, 2009Applicant: Takasago International CorporationInventors: Tetsuya Yamamoto, Kenji Yagi, Kenya Ishida
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Patent number: 7569732Abstract: A process of preparation of cis-2-acetyl-1,2,3,4,5,6,7,8-octahydro-1,2,8,8-tetramethylnaphthalene (“?-Georgywood”) from cis-1-[1,2-dimethyl-4(4-methyl-pent-3-enyl)-cyclohex-3-enyl]-ethanone (“?-Georgywood”), comprising the reaction of ?-Georgywood with more than one molar equivalent of a Lewis acid. The method allows the preparation of isomeric mixtures that contain a much higher proportion of the olfactorily-desirable ?-Georgywood than was previously possible.Type: GrantFiled: February 16, 2006Date of Patent: August 4, 2009Assignee: Givaudan SAInventor: Fridtjof Schröder
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Patent number: 7414158Abstract: Processes for producing intermediate materials used for perfumery, specifically, epimerized cyclohexenyl ketones, are disclosed. Processes for employing the epimerising reaction in an Aldol condensation reaction are also disclosed.Type: GrantFiled: July 23, 2007Date of Patent: August 19, 2008Assignee: The Procter & Gamble CompanyInventors: Yousef Georges Aouad, Daniel Martin Bourgeois, Gregory Scot Miracle, Jean Wevers, Harambage Quintas Nimal Gunaratne, Kenneth Richard Seddon, Eva Boros, Suhas Prabhaker Katdore, Tayeb Belhocine
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Patent number: 7348304Abstract: The invention provides a novel fragrance material comprising a compound having the structure (IUPAC name (1R,2S,7R,8R,9S)-2,6,6,9-tetramethyltricyclo-[5.4.0.02,8]undecan-10-one). The novel fragrance material has a strong, pleasant cedar wood fragrance and is useful for imparting, strengthening, or improving the odor of perfumes and perfumed products. Methods for preparing the novel fragrance material are described.Type: GrantFiled: December 20, 2004Date of Patent: March 25, 2008Inventor: Laurence G. Cool
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Patent number: 7332633Abstract: The present invention relates to a process for the preparation of an optically active 5-substituted cyclohexenone (II) by treating an achiral macrocyclic 3-substituted-1,5-diketone (I) in the presence of an optically active sodium, potassium or cesium alkoxide.Type: GrantFiled: July 10, 2006Date of Patent: February 19, 2008Assignee: Firmenich SAInventor: Oliver Knopff
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Patent number: 7262329Abstract: A two-step aldol condensation process is disclosed. ?-Campholenic aldehyde (ACA) and methyl ethyl ketone (MEK) react in the presence of a base under conditions effective to produce a mixture comprising a high yield of ketol condensation products. Dehydration of the ketols in the presence of an organic sulfonic acid provides unsaturated ketones that are valuable intermediates for fragrance components for synthetic sandalwood products. Compared with the usual one-step, base-catalyzed approach, the two-step process increases the yield of all condensation products and maximizes production of the most valuable ketone isomers.Type: GrantFiled: November 27, 2006Date of Patent: August 28, 2007Assignee: Millennium Specialty Chemicals, Inc.Inventors: Gennadiy G. Kolomeyer, Jacob Oyloe, Douglas A. Ferone
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Patent number: 7250536Abstract: The present invention relates to a process for the carbon-carbon double bond isomerisation of a 2-alkyl-cyclohex-3-enyl alkyl or alkenyl ketone into a mixture comprising the corresponding 2-alkyl-cyclohex-2-enyl ketones and the corresponding 2-alkylene-cyclohexyl ketones, using as catalyst a ruthenium complex obtainable by the reaction of an appropriate ruthenium organometallic precursor and an acid.Type: GrantFiled: May 22, 2006Date of Patent: July 31, 2007Assignee: Firmenich SAInventors: Denis Jacoby, Bessaa Neffah, Christian Chapuis
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Patent number: 7241551Abstract: A positive-working resist composition comprising (A) a resin that increases solubility in an alkali developing solution by the action of an acid, (B) a compound which generates an acid upon irradiation of an actinic ray or radiation, (C) a nonionic cyclic compound having at least one partial structure represented by the following formula (I) or (II) and at least having either a melting point of 35° C. or more or a boiling point of 100° C./10 mmHg or more: and (D) a solvent.Type: GrantFiled: June 9, 2004Date of Patent: July 10, 2007Assignee: Fujifilm CorporationInventors: Hyou Takahashi, Tsukasa Yamanaka, Toru Fujimori
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Patent number: 7057077Abstract: A method for producing 2-(alkyl)cycloalkenone and a method for producing alkyl(3-oxo-2-alkylcycloalkyl) acetate and 5-alkyl-5-alkanolide which are useful as flavoring materials and physiologically active substances using the same are provided. A method for producing Compound (2) including the steps of: dehydrating Compound (1) using an acid catalyst until the conversion ratio of dehydration reaction reaches 20 to 90% based on Compound (1), thereby obtaining a mixture containing Compound (1) and Compound (3); and isomerizing Compound (3) while dehydrating the remaining Compound (1), and a method for producing Compound (5) or (6) using obtained Compound (2). (wherein n represents 1 or 2, R1 and R2 each represent H, C1-8 alkyl groups and the like and R3 represents C1-3 alkyl groups).Type: GrantFiled: December 11, 2003Date of Patent: June 6, 2006Assignee: Kao CorporationInventors: Hirotsugu Nishimura, Koji Mine
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Patent number: 6958421Abstract: A salt-free process for preparing cyclobutanone, including isomerizing cyclopropylmethanol, preferably in aqueous solution, in the presence of an acidic heterogeneous catalyst to form cyclobutanol and, preferably after extraction and removal of the extractant, dehydrogenating the cyclobutanol over a heterogeneous catalyst.Type: GrantFiled: June 13, 2003Date of Patent: October 25, 2005Assignee: Degussa AGInventors: Kerstin Bodmann, Manuela Imig, Günther Köhler, Karl-Heinz Brühl
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Patent number: 6951964Abstract: The present invention relates to a novel thermo-isomerization method for rapidly and simply producing macrocyclic ketones of the formula Ia or Ib. The macrocyclic ketones are prepared in the gas phase at temperatures above 500° C. rapidly and in a simple manner from alcohols of the formula IIa and IIb directly with a high yield. In the formulae Ia, Ib, IIa and IIb, R1-R5, and n have the meanings given in the description.Type: GrantFiled: February 15, 2002Date of Patent: October 4, 2005Assignee: Givaudan SAInventors: Georg Frater, Matthias Nagel
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Patent number: 6884913Abstract: A process for the manufacture of an alpha, beta-unsaturated cyclic ketone, such as carvone, comprises the dehydrogenation of a secondary allylic cyclic alcohol, such as carveol, in the presence of at least one metal carboxylate. The process can be performed in a batchwise or continuous mode. Examples of suitable metal carboxylates include magnesium stearate, calcium 2-ethylhexanoate, and zinc 2-ethylhexanoate.Type: GrantFiled: May 30, 2003Date of Patent: April 26, 2005Assignee: Millennium Specialty ChemicalsInventors: Gennadiy G. Kolomeyer, Jacob S. Oyloe
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Patent number: 6861563Abstract: In the process for producing a cyclododecanone by isomerizing an epoxycyclododecane-containing starting material in the presence of an isomerization reaction catalyst containing lithium bromide and/or lithium iodide, in order to perform the reaction with high efficiency (high reaction rate) and high selectivity and stably produce a high-purity cyclododecanone in industry while maintaining a high-level reaction rate, the epoxycyclododecane-containing starting material is produced by contacting an epoxycyclododecadiene with hydrogen in the presence of a hydrogen-reduction catalyst and has a content of the hydroxyl group-containing cyclododecane compounds contained in the epoxycyclododecane-containing starting material controlled to 5 mol % or less.Type: GrantFiled: August 9, 2002Date of Patent: March 1, 2005Assignees: Ube Industries, Ltd., EMS-Chemie AGInventors: Ryoji Sugise, Shuji Tanaka, Takashi Doi, Masayuki Nishio, Sadao Niida, Tsunao Matsuura
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Patent number: 6833481Abstract: Industrially advantageous processes for producing a 2-alkyl-2-cyclopentenone in high yields starting from a 2-(1-hydroxyalkyl)cyclopentanone or a 2-alkylidenecyclopentanone, which are obtainable from a cyclopentanone and a carbonyl compound. A 2-(1-hydroxyalkyl)cyclopentanone represented by the following general formula (1): (wherein R1, R2, R3, R4, R5, R6 and R7 each independently represents hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may have one or more substituents or an aromatic group which may have one or more substituents, and each of (1) R6 or R7 with R3 and (2) R6 or R7 with R4 or R5 may be together combined to form a ring which may have a double bond) is subjected to dehydrative isomerization in the presence of a bromine compound and/or an iodine compound.Type: GrantFiled: November 29, 2002Date of Patent: December 21, 2004Assignee: Takasago International CorporationInventors: Takeshi Yamamoto, Kenichiro Adachi, Shinya Watanabe, Hideo Ujihara, Toshimitsu Hagiwara
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Patent number: 6822121Abstract: An economical process for producing (2- and/or 1-)cyclohexenyl methyl ketones which are intermediates for the synthesis of &agr;- or &bgr;-damascone. In the presence of a catalyst, a 3-cyclohexenyl methyl ketone represented by the following formula (1a): wherein, R1, R2 and R3 each independently represents a hydrogen atom or a methyl group and at least two of R1, R2 and R3 are methyl groups, is isomerized.Type: GrantFiled: June 7, 2001Date of Patent: November 23, 2004Assignee: Takasago International CorporationInventors: Shinya Watanabe, Hideo Ujihara, Takeshi Yamamoto, Toshimitsu Hagiwara
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Patent number: 6815413Abstract: Lower alkyl- and lower alkylidene-substituted, saturated or unsaturated cyclohexadecanones are grand fragrances with muscone note with which perfumes with new odor notes can be prepared.Type: GrantFiled: August 2, 2001Date of Patent: November 9, 2004Assignee: Symrise GmbH & Co. KGInventors: Marcus Eh, Ingo Wöhrle
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Publication number: 20040181096Abstract: In the process for producing a cyclododecanone by isomerizing an epoxycyclododecane-containing starting material in the presence of an isomerization reaction catalyst containing lithium bromide and/or lithium iodide, in order to perform the reaction with high efficiency (high reaction rate) and high selectivity and stably produce a high-purity cyclododecanone in industry while maintaining a high-level reaction rate, the epoxycyclododecane-containing starting material is produced by contacting an epoxycyclododecadiene with hydrogen in the presence of a hydrogen-reduction catalyst and has a content of the hydroxyl group-containing cyclododecane compounds contained in the epoxycyclododecane-containing starting material controlled to 5 mol % or less.Type: ApplicationFiled: February 13, 2004Publication date: September 16, 2004Inventors: Ryoji Sugise, Shuji Tanaka, Takashi Doi, Masayuki Nishio, Sadao Niida, Tsunao Matsuura
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Patent number: 6770618Abstract: Trans-2,2,6-trimethylcyclohexyl methyl ketone, including (1S,6R)-2,2,6-trimethylcyclohexyl methyl ketone represented by the formula (1a): and (1R,6S)-2,2,6-trimethylcyclohexyl methyl ketone represented by the formula (1b): are useful components in a perfume composition. A process for producing the same is also described. A unique eucalyptus, mint-like and white floral perfume material is provided using the ketone compounds disclosed in the present invention. The process of the present invention produces the optically active ketone compounds having optical purity up to at least 98.0 % e.e.Type: GrantFiled: June 7, 2001Date of Patent: August 3, 2004Assignee: Takasago International Corp.Inventors: Hideo Ujihara, Shinya Watanabe, Takeshi Yamamoto, Toshimitsu Hagiwara
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Publication number: 20040082816Abstract: The present invention relates to a novel thermo-isomerization method for rapidly and simply producing macrocyclic ketones of the formula Ia or Ib.Type: ApplicationFiled: August 22, 2003Publication date: April 29, 2004Inventors: Georg Frater, Matthias Nagel
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Patent number: 6583322Abstract: This invention describes heretofore unknown forms of dihydro (DHIA) and hexahydro (HHIA) isoalpha acids having a high ratio of trans to cis isomers and a process for their production. Also, non-precipitating clear 5, 10, 20% and higher aqueous solutions thereof, since they are soluble at room temperature in soft water. This is due to the high ratio of trans to cis isomers. Unlike prior art essentially all cis isomer products, they remain haze free both at a neutral pH in water and at 1% to 2% and higher concentrations. This invention has the advantage over the prior art in that DHIA and HHIA can be provided as stable, non-separating liquids, at practical concentrations in the range of 5% to about 40%, which do not require heating to about 50° to 90° C. and above with stirring to effect dissolution of precipitates. The high trans products described herein can be admixed with isoalpha- and tetrahydro-isoalpha acids.Type: GrantFiled: February 25, 2000Date of Patent: June 24, 2003Assignee: Kalamazoo Holdings, Inc.Inventors: Khalil Shahlai, Randall H. Mennett, Paul H. Todd, James A. Guzinski
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Patent number: 6548711Abstract: A process for producing 2-vinylcyclododecanone, the process comprising isomerizing 2-ethylidenecyclododecanone represented by the following formula (1): wherein the wavy line signifies that the double bond is a Z-isomer, an E-isomer or a mixture of an E-isomer and a Z-isomer; in the presence of a catalyst and separating 2-vinylcyclododecanone represented by the following formula (2) from the reaction product by fractionation:Type: GrantFiled: June 8, 2001Date of Patent: April 15, 2003Assignee: Takasago International CorporationInventors: Kenichi Yamamoto, Misao Yagi, Toshimitsu Hagiwara
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Patent number: 6521796Abstract: This invention describes heretofore unknown forms of dihydro (DHIA) and hexahydro (HHIA) isoalpha acids having a high ratio of trans to cis isomers and a process for their production. Also, non-precipitating clear 5, 10, 20% and higher aqueous solutions thereof, since they are soluble at room temperature in soft water. This is due to the high ratio of trans to cis isomers. Unlike prior art essentially all cis isomer products, they remain haze free both at a neutral pH in water and at 1% to 2% and higher concentrations. This invention has the advantage over the prior art in that DHIA and HHIA can be provided as stable, non-separating liquids, at practical concentrations in the range of 5% to about 40%, which do not require heating to about 50° to 90° C. and above with stirring to effect dissolution of precipitates. The high trans products described herein can be admixed with isoalpha- and tetrahydro-isoalpha acids.Type: GrantFiled: July 23, 2001Date of Patent: February 18, 2003Assignee: Kalamazoo Holdings, Inc.Inventors: Khalil Shahlai, Randall H. Mennett, Paul H. Todd, James A. Guzinski
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Patent number: 6500990Abstract: A process for efficiently producing a 2-alkyl-2-cyclopentenone comprising reacting an amine and a hydrogen halide, which are present in a ratio ranging from 1.1:1 to 5:1, with a 2-alkylidene cyclopentanone to carry out an isomerization reaction. A process for producing a jasmonate derivative comprising reacting a 2-alkyl-2-cyclopentenone with a malonic acid diester.Type: GrantFiled: March 13, 2001Date of Patent: December 31, 2002Assignee: Kao CorporationInventors: Takahiro Asada, Yoshiharu Ataka, Junji Koshino
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Patent number: 6469215Abstract: A process for the production of an intermediate mixture of &bgr;-isophorone epoxide and its isomer 4-hydroxyisophorone (HIP), comprising reacting &bgr;-isophorone with an organic percarboxylic acid, in the form of its non-aqueous solution, in an inert solvent.Type: GrantFiled: February 28, 2002Date of Patent: October 22, 2002Assignee: Degussa AGInventors: Steffen Krill, Klaus Huthmacher, Sylvain Perrin
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Patent number: 6444841Abstract: A highly pure hydroquinone dietser derivative can be produced from the reaction product of ketoisophorone with an acylating agent in a high yield by a simple and easy operation. In the presence of an acid catalyst, a cyclohex-2-ene-1,4-dione derivative shown by the following formula (3) was allowed to react with an acylating agent (e.g., acetic anhydride), and the reaction product was purified by crystallization to obtain a hydroquinone diester derivative shown by the following formula (1). The compound (1) contains about 0 to 4% by weight of a catechol diester derivative represented by the following formula (2), being highly pure. As a solvent for crystallization, a mixed solvent of an organic carboxylic acid (e.g., acetic acid) corresponding to the acylating agent and water may be used. In the formulae, R1 and R2 each represents an alkyl group, a cycloalkyl group, an aryl group or a heterocyclic group.Type: GrantFiled: October 30, 1998Date of Patent: September 3, 2002Assignee: Daicel Chemical Industries, Ltd.Inventors: Ikuo Takahashi, Hikaru Shibata
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Publication number: 20020099242Abstract: A cyclododecanone compound is continuously produced by feeding a liquid feed containing a corresponding epoxycyclododecane compound and LiBr and/or LiI into a frontmost reaction region of a plurality of reaction regions connected to each other in series; successively passing the liquid feed through the series of reaction regions to catalytically isomerize the epoxycyclododecane compound into a corresponding cyclododecanone compound; and collecting the resultant reaction mixture containing the target cyclododecanone compound from a rearmost reaction region of the series of reaction regions.Type: ApplicationFiled: June 13, 2001Publication date: July 25, 2002Applicant: Ube Industries, LtdInventors: Ryoji Sugise, Shuji Tanaka, Takashi Doi, Masayuki Nishio, Sadao Niida, Tsunao Matsuura
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Patent number: 6423874Abstract: A process for obtaining Ketone of formula 1a,b, which includes contacting a Ketone represented by formula 2a,b with a first catalyst under conditions and for a time sufficient to obtain an intermediate mixture, which intermediate mixture contains a Ketone represented by formula 4a,b; and contacting the intermediate mixture, or a fraction thereof, with a second catalyst under conditions effective to provide a product containing a Ketone of formula 1a,b. Moreover, the first catalyst preferably differs from the second catalyst with the first catalyst preferably being an isomerization catalyst and the second catalyst being a cyclization catalyst. The process is capable of providing unexpectedly incresased yields of both Ketone 4 and Ketone 1.Type: GrantFiled: February 18, 2000Date of Patent: July 23, 2002Assignee: Millennium Speciality Chemicals, Inc.Inventors: Mark B. Erman, Melissa J. Williams, Carlos G. Cárdenas
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Patent number: 6420609Abstract: Process for the production of 2,2,6-trimethylcyclohexane-1,4-dione by epoxidation of &bgr;-isophorone with organic percarboxylic acids at a water content below 5 wt.-% and subsequent isomerization of the mixture of &bgr;-isophorone epoxide and hydroxyisophorone.Type: GrantFiled: May 8, 2001Date of Patent: July 16, 2002Assignee: Degussa AGInventors: Steffen Krill, Klaus Huthmacher, Sylvain Perrin
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Publication number: 20020077509Abstract: A cyclododecanone compound is continuously produced by an isomerization reaction of a corresponding epoxycyclododecane compound in the presence of a catalyst including lithium bromide and/or lithium iodide, the isomerization reaction being carried out by passing a reaction mixture containing the epoxycyclododecane compound and the catalyst through a continuous reaction apparatus including at least one tubular reactor preferably at a temperature of 100 to 350° C.Type: ApplicationFiled: October 19, 2001Publication date: June 20, 2002Applicant: Ube Industries, Ltd.Inventors: Ryoji Sugise, Shuji Tanaka, Takashi Doi, Masayuki Nishio, Sadao Niida, Tsunao Matsuura