Catalyst Utilized Patents (Class 568/881)
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Patent number: 6720439Abstract: trans-RuH(&eegr;1-BH4)[(S)-xylbinap][(S,S)-dpen] (0.00125 mmol), acetophenone (5.0 mmol), and 2-propanol (2.5 mL) were placed in an autoclave, and the resulting solution was repeatedly subject 5 times to a procedure of performing pressure reduction and argon introduction while stirring the solution for deaeration. A hydrogen tank was then connected to the autoclave, and after replacing the air inside an introduction tube with hydrogen, the pressure inside the autoclave was adjusted to 5 atmospheres and then hydrogen was released until the pressure dropped to 1 atmosphere. After repeating this procedure 10 times, the hydrogen pressure was adjusted to 8 atmospheres and stirring at 25° C. was performed for 12 hours. By concentrating the solution obtained by depressurization and subjecting the crude product to simple distillation, (R)-1-phenylethanol (yield: 95%) in the form of a colorless oily substance was obtained at an ee of 99%.Type: GrantFiled: November 12, 2002Date of Patent: April 13, 2004Assignee: Nagoya Industrial Science Research InstituteInventors: Takeshi Ohkuma, Masatoshi Koizumi, Kilian Muñiz, Ryoji Noyori
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Publication number: 20030204112Abstract: Process for enantioselectively hydrogenating prochiralen ketones to (S)-alcohols using platinum catalysts in the presence of cinchonines or quinidines as modifiers and in the presence of hydrogen, which is characterized in that the modifiers used are cinchonines unsubstituted in the 3-position, 3-ethylidenyl- or 9-methoxycinchonines or derivatives thereof in which the quinoline ring is replaced by other rings.Type: ApplicationFiled: April 11, 2003Publication date: October 30, 2003Inventors: Martin Studer, Stephan Burkhardt, Andreas Pfaltz, Christian Exner
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Publication number: 20030199713Abstract: Catalyst for the asymmetric (transfer) hydrogenation represented by the formula MLaXbSc, where M is a transition metal, to be chosen from rhodium and ruthenium, and X is a counter ion and S is a ligand, a ranges from 0.5 to 3 and b and c, each independently, range from 0 to 2, and L is a chiral ligand having the formula (1), where Cn together with the two 2 O-atoms and the P-atom forms a substituted or non-substituted ring with 2-4 C-atoms, R1 and R2 each independently represent H, an optionally substituted alkyl, aryl, alkaryl or aralkyl group or may form a (heterocyclic) ring together with the N-atom to which they are bound. And a process for the asymmetric (transfer) hydrogenation of an olefinically unsaturated compound, ketone, imine or oxime derivate in the presence of a hydrogen donor and of a catalyst, use being made of a catalyst represented by formula MLaXbSc, where M is a transition metal, to be chosen from rhodium, iridium and ruthenium, X is a counter ion, S is a ligand, a ranges from 0.Type: ApplicationFiled: January 7, 2003Publication date: October 23, 2003Inventors: Michel Berg Van Den, Ben Feringa, Adriaan Jacobus Minnaard, Johannes Gerardus Vries De
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Patent number: 6627782Abstract: A multi-stage synthesis is effective for preparing 1-olefins from aldehydes. The aldehyde is condensed with acetone to form an &agr;,&bgr;-unsaturated ketone. The unsaturated ketone is hydrogenated to yield a saturated alcohol. By dehydrating the saturated alcohol a 1-olefin is obtained. The olefin can be isolated in high yield and purified.Type: GrantFiled: February 8, 2002Date of Patent: September 30, 2003Assignee: Oxeno Olefinchemie GmbHInventors: Alfred Kaizik, Wilfried Bueschken, Klaus-Diether Wiese, Guido Protzmann
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Patent number: 6617064Abstract: The present invention features methods for preparing stabilized &agr;-AlH3 and &agr;′-AlH3, compositions containing these alane polymorphs, e.g., energetic compositions such as rocket propellants, and methods for using the novel polymorphs as chemical reducing agents, polymerization catalysts, and as a hydrogen source in fuel cells and batteries. The method produces stabilized alane by treating &agr;-AlH3 with an acidic solution that optionally contains a stabilizing agent such as an electron donor, an electron acceptor, or a compound which coordinates the Al3+ ion.Type: GrantFiled: March 29, 2001Date of Patent: September 9, 2003Assignee: SRI InternationalInventors: Mark A. Petrie, Jeffrey C. Bottaro, Robert J. Schmitt, Paul E. Penwell, David C. Bomberger
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Publication number: 20030166978Abstract: The invention provides novel ruthenium complexes having an optically active diphosphine compound, which has asymmetry on carbon and is easy to synthesize, as the ligand and a process for preparing optically active alcoholic compounds using said complexes as the catalysts, wherein said process is the process for preparing optically active alcoholic compounds, which are excellent in terms of reactivity, enatioselectivity and the like in an asymmetric hydrogenation of carbonyl compounds compared with conventional ruthenium complex catalysts having an optically active diphosphine compound having the axial chirality or the asymmetry on carbon as the ligand.Type: ApplicationFiled: December 27, 2002Publication date: September 4, 2003Applicant: Kanto Kagaku Kabushiki KaishaInventors: Kunihiko Tsutsumi, Kunihiko Murata, Takeshi Ota, Takao Ikariya
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Patent number: 6613923Abstract: The present invention is a process for the catalytic hydrogenation of ketones and aldehydes to alcohols at low temperatures and pressures using organometallic molybdenum and tungsten complexes and the catalyst used in the process. The reactants include a functional group which is selected from groups represented by the formulas R*(C═O)R′ and R*(C═O)H, wherein R* and R′ are selected from hydrogen or any alkyl or aryl group. The process includes reacting the organic compound in the presence of hydrogen and a catalyst to form a reaction mixture. The catalyst is prepared by reacting Ph3C+A− with a metal hydride. A− represents an anion and can be BF4−, PF6−, CF3SO3− or Bar′4−, wherein Ar′=3,5-bis(trifluoromethyl)phenyl.Type: GrantFiled: April 19, 2000Date of Patent: September 2, 2003Assignee: Brookhaven Science Associates, LLCInventors: R. Morris Bullock, Barbara F. M. Kimmich, Paul J. Fagan, Elisabeth Hauptman
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Patent number: 6610894Abstract: A method of increasing enantioselectivity in a reduction reaction of a prochiral substrate with a borane reagent including a borohydride species (for example, a borohydride stabilized borane-tetrahydrofuran complex) catalyzed by a chiral catalyst includes the step of maintaining the concentration of borohydride species in the borane reagent below approximately 0.005 M during the reduction of the prochiral substrate. A method of increasing enantioselectivity in a reduction reaction of a prochiral substrate with a borane reagent including a borohydride species that is catalyzed by a chiral catalyst includes the step of reducing the detrimental effect the borohydride species has on enantioselectivity by adding a Lewis acid. For example, the prochiral substrate can be a ketone and the chiral catalyst can be a chiral oxazaborolidine.Type: GrantFiled: January 26, 2001Date of Patent: August 26, 2003Assignee: Mine Safety Appliances CompanyInventors: Karl Matos, Joseph A. Corella, II, Elizabeth R. Burkhardt, Shawn M. Nettles
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Publication number: 20030144537Abstract: The invention is directed to a process for carrying out a chemical reaction in a reactor, comprising passing a reaction mixture in liquid phase through at least one structured reactor element present in sad reactor, the internal surface of said reactor element that comes into contact with the reaction mixture being catalytically active, the improvement comprising passing said reaction mixture through the said at least one reactor element, said reaction mixture comprising at least one liquid and at least one gas in liquid phase.Type: ApplicationFiled: November 25, 2002Publication date: July 31, 2003Inventors: Bernard Hendrik Reesink, Marius Vaarkamp
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Patent number: 6600078Abstract: A heterogeneous liquid-phase process for the hydrogenation of aldehydes of Formula (I) and (III) to the corresponding alcohols of Formula (II) and (IV) which process comprises contacting alcoholic or aqueous-alcoholic solution of aldehydes and hydrogen gas with a catalyst comprising a reduced mixture of CuO and ZnO in presence of a metal of group IIIA of the Periodic Table, such as aluminium, as a promoter at a temperature of between about 110° and 180° C. and a pressure of between about 20 and 500 psig.Type: GrantFiled: August 12, 2002Date of Patent: July 29, 2003Assignee: Saudi Basic Industries CorporationInventors: Meftahuddin Mahmud, Ahmad Kamal Faizi, Vidyasagar Anchoori, Abdullah Al-Qahtani
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Patent number: 6593502Abstract: The invention relates to a process for the preparation of polyols having 3 or 4 hydroxyl groups, from an aldehyde and formaldehyde in the presence of water, followed by hydrogenation of the aldolisation product in the presence of a hydrogenation catalyst at an elevated temperature. The aledhyde is obtained by an aldolisation reaction of an aldehyde having at least two &agr;-hydrogen atoms and a formula according to R1CH2CHO, wherein R1 is selected from a group comprising hydrogen, alkyl groups having 1-7 carbon atoms which can have cycloalkyl substituents, cycloalkyl groups, aryl groups and aralkyl groups with 1-7 carbon atoms is the alkyl chain, with formaldehyde in the presence of water in an amount of 20-70 wt %, preferably 40-60 wt % and in the presence of an anion exchange resin. The hydrogenation is preferably carried out in the presence of water.Type: GrantFiled: January 2, 2002Date of Patent: July 15, 2003Assignee: Dynea Chemicals OyInventors: Tapio Salmi, Valentina Serra-Holm, Tiina-Kaisa Rantakylä, Päivi Mäki-Arvela, Lars-Peter Lindfors, Hannu Nousiainen
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Publication number: 20030130546Abstract: A process for the hydrogenation of acetone to prepare isopropanol is provided, wherein the hydrogenation reaction is carried out in a multi-tubular reactor.Type: ApplicationFiled: November 14, 2002Publication date: July 10, 2003Inventors: Leslie Andrew Chewter, Wilhelmus Cornelis Nicolaas Dekker, Stephane Jean Pierre Lecrivain, Andrew Neave Rogers
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Patent number: 6586636Abstract: Production of unsaturated aldehydes by the aldol condensation of straight chain aldehydes, e.g. butyraldehyde, by contacting the aldehyde in the vapour phase with a particulate catalyst comprising at least one basic alkali metal compound supported on an inert substrate at a temperature above 175° C.Type: GrantFiled: May 22, 2001Date of Patent: July 1, 2003Assignee: Imperial Chemical Industries PLCInventor: Gordon James Kelly
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Publication number: 20030120088Abstract: There are disclosed an optically active azetidincarboxamide-coordinated transition metal complex of formula (1): 1Type: ApplicationFiled: December 11, 2002Publication date: June 26, 2003Inventors: Taichi Senda, Kazunori Iwakura, Naoto Konya
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Publication number: 20030120122Abstract: Compounds of formula III, 1Type: ApplicationFiled: December 9, 2002Publication date: June 26, 2003Inventors: Benoit Pugin, Ivo Steiner, Rhony Niklaus Aufdenblatten, Antonio Togni
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Patent number: 6583312Abstract: The invention relates to a novel process for preparing optically active trimethyllactic acid and/or its esters by catalytic hydrogenation of trimethylpyruvic acid and/or its esters in the presence of noble metal complex catalysts containing phosphorus ligands.Type: GrantFiled: May 24, 2001Date of Patent: June 24, 2003Assignee: Bayer AktiengesellschaftInventors: Wolfram Sirges, Claus Dreisbach
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Patent number: 6583324Abstract: A process for producing an aldehyde, which comprises a reaction step of producing an aldehyde by reacting an olefinic compound with carbon monoxide and hydrogen in the presence of a rhodium complex catalyst comprising at least rhodium and an organic phosphite in a reaction zone, a separation step of obtaining a catalyst solution containing the rhodium complex catalyst by separating the aldehyde from a reaction solution taken from the reaction zone, and a recycling step of recycling the catalyst solution into the reaction zone, wherein the aldehyde is separated from the reaction solution in such a manner as to make an aldehyde concentration from 0.5 to 99 wt % in the catalyst solution.Type: GrantFiled: September 18, 2001Date of Patent: June 24, 2003Assignee: Mitsubishi Chemical CorporationInventors: Masaki Takai, Iwao Nakajima, Tooru Tsukahara, Yoshiyuki Tanaka, Hisao Urata, Akio Nakanishi
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Publication number: 20030114720Abstract: The invention relates to a process for the preparation of saturated C3-C20-alcohols in which a liquid hydrogenation feed comprising at least one C3-C20-aldehyde is passed over a bed of a hydrogenation catalyst in the presence of a hydrogen-containing gas, which comprises adding to the hydrogenation feed an amount, homogeneously soluble therein, of a salt-like base. The addition of base suppresses side reactions, such as acetalization, aldolization, Tischtschenko reaction or ether formation.Type: ApplicationFiled: November 14, 2002Publication date: June 19, 2003Inventors: Herwig Hoffmann, Michael Roper, Heinrich-Josef Blankertz, Max Strohmeyer, Helmut Walz, Helmut Zinke-Allmang
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Publication number: 20030114719Abstract: In a process for preparing alcohols by catalytic hydrogenation of carbonyl compounds over a catalyst comprising rhenium on activated carbon, the catalyst used comprises rhenium (calculated as metal) in a weight ratio to the activated carbon of from 0.0001 to 0.5, platinum (calculated as metal) in a weight ratio to the activated carbon of from 0.0001 to 0.5 and, if appropriate, at least one further metal selected from among Zn, Cu, Ag, Au, Ni, Fe, Ru, Mn, Cr, Mo, W and V in a weight ratio to the activated carbon of from 0 to 0.25, and the activated carbon has been nonoxidatively pretreated It is also possible to prepare ethers and lactones if the hydrogen pressure is not more than 25 bar. In this case, the activated carbon in the catalyst may also have been nonoxidatively pretreated.Type: ApplicationFiled: October 29, 2002Publication date: June 19, 2003Inventors: Rolf Hartmuth Fischer, Rolf Pinkos, Stephan Andreas Schunk, Joachim Wulff-Doring, Frank Stein, Thomas Nobel, Sylvia Huber
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Publication number: 20030109758Abstract: The present invention relates to a continuous process for the selective hydrogenation of olefinically unsaturated carbonyl compounds to give unsaturated alcohols in particular of citral to give a mixture of geraniol and nerol, in a reactor containing a liquid phase, in which at least one catalyst is suspended, and which can additionally contain a gas phase, wherein the liquid phase and, if present, the gas phase are passed through a device in the reactor having openings or channels.Type: ApplicationFiled: December 4, 2002Publication date: June 12, 2003Inventors: Hans-Georg Gobbel, Till Gerlach, Frank Funke, Klaus Ebel, Signe Unverricht, Gerd Kaibel
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Patent number: 6555715Abstract: A process has been developed for oxygenating linear C2 to C6 alkanes to ketones or aldehydes. The process involves reacting the alkanes with oxygen in the presence of a catalyst comprising an imide promoter and a metal co-catalyst. An example of the imide is N-hydroxyphthalimide and an example of the co-catalyst is Co (acetylacetonate). The process is preferably carried out using an inert solvent, an example of which is acetic acid. Optionally, the oxygenated product can be hydrogenated to give the corresponding alcohol which can optionally in turn be dehydrated to provide the corresponding olefin.Type: GrantFiled: October 11, 2001Date of Patent: April 29, 2003Assignee: UOP LLCInventors: Joseph A. Kocal, Robert R. Frame, Jeffery C. Bricker
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Patent number: 6555716Abstract: Aldehydes are prepared in a hydroformylation apparatus by the multiphase hydroformylation reaction of one or more olefins with hydrogen and carbon monoxide, where the continuous phase contains a solvent mixture and the hydroformylation catalyst is present in the continuous phase, at least one olefin is present in the dispersed phase, and the loading factor of the tube reactor is greater than or equal to 0.8.Type: GrantFiled: November 30, 2000Date of Patent: April 29, 2003Assignee: Oxeno Olefinchemie GmbHInventors: Guido Protzmann, Klaus-Diether Wiese, Wilfried Büschken, Dirk Röttger
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Patent number: 6534436Abstract: The invention relates to catalysts comprising cobalt supported on a solid silica support and, in particular, to a method for manufacturing such catalysts. The catalysts may be prepared by slurrying a silica powder or impregnating a silica particle with a solution of a cobalt compound, cobalt amine carbonate, and aging the resulting slurry or solid at elevated temperature; the cobalt amine carbonate is decomposed and precipitated as basic cobalt carbonate onto the silica support. Preferably, the catalysts have a cobalt surface area in the range of 25 to >100 m2 per gram total cobalt. The catalyst may be used in hydrogenation reactions, Fischer-Tropsch reactions and oxidation reactions.Type: GrantFiled: July 26, 2002Date of Patent: March 18, 2003Assignee: Imperial Chemical Industries PLCInventors: Cornelis M Lok, Stephen Bailey, Gavin Gray
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Patent number: 6534657Abstract: Ferrocene anchored chiral ligands and metal complexes based on such chiral ligands useful in asymmetric catalysis are disclosed. The metal complexes according to the present invention are useful as catalysts in asymmetric reactions, such as, hydrogenation, hydride transfer, allylic alkylation, hydrosilylation, hydroboration, hydrovinylation, hydroformylation, olefin metathesis, hydrocarboxylation, isomerization, cyclopropanation, Diels-Alder reaction, Heck reaction, isomerization, Aldol reaction, Michael addition; epoxidation, kinetic resolution and [m+n] cycloaddition. The new ligands are effective for asymmetric Pd-catalyzed allylic alkylation reactions and Ag-catalyzed [3+2] cyclization of azomethine ylides.Type: GrantFiled: February 9, 2001Date of Patent: March 18, 2003Assignee: The Penn State Research FoundationInventor: Xumu Zhang
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Publication number: 20030018224Abstract: A first invention group is characterized by 1,3-butylene glycol which, at a period of three months after production, exhibits potassium permanganate color-fading time of at least five minutes as measured according to JIS K1351 3.10.Type: ApplicationFiled: January 2, 2002Publication date: January 23, 2003Inventors: Yasuo Tsuji, Hiroaki Uenakai, Hiroshi Koyama
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Patent number: 6509472Abstract: Prochiral ketones are enantioselectively reduced to chiral secondary alcohols with a compound having the formula I: where, the two R2 groups are identical and are each a substituted or unsubstituted, aryl, alkyl, cycloalkyl or aralkyl group; and R3 is a hydrogen atom or a substituted or unsubstituted, alkyl, aryl, aralkyl or alkoxy group; wherein the substituents on the R2 and R3 groups are substantially non-reactive.Type: GrantFiled: August 30, 2001Date of Patent: January 21, 2003Assignee: Schering CorporationInventor: Richard W. Draper
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Patent number: 6500957Abstract: A platinum complex is described to include a platinum(IV) metal center so positioned and oriented in the complex so as to complex in cis orientations with two hydride groups and with an alkyl group.Type: GrantFiled: May 16, 2002Date of Patent: December 31, 2002Assignee: Technion Research and Development Foundation Ltd.Inventors: Ehud Keinan, Ariel Haskel
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Patent number: 6486366Abstract: A method for preparation of alcohols by catalytic hydrogenation of carbonyl compounds with hydrogen or hydrogen-containing gases in the presence of a hydrogenation catalyst of Raney type, where the catalyst is used in the form of hollow bodies, Preferred as catalytically active components are nickel, cobalt, copper, iron, platinum, palladium or ruthenium.Type: GrantFiled: December 21, 2001Date of Patent: November 26, 2002Assignee: Degussa AGInventors: Daniel Ostgard, Monika Berweiler, Stefan Röder
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Patent number: 6476278Abstract: Alcohols are produced in a practical and advantageous method, by the hydrogenation of a carbonyl compound under mild conditions, by reacting the carbonyl compounds with hydrogen in the presence of a bipyridyl derivative, a group VIII transition metal complex, and a base, or by reducing a carbonyl compound in the presence of a bipyridyl derivative, a group VIII transition metal complex, a base, and an alcoholic solvent.Type: GrantFiled: October 25, 2001Date of Patent: November 5, 2002Assignees: Japan Science and Technology Corporation, Takasago International CorporationInventors: Hideyuki Ikehira, Kunihiko Murata, Eiji Katayama, Masami Kozawa, Toru Yokozawa, Takeshi Ohkuma, Takao Ikariya, Ryoji Noyori
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Patent number: 6462206Abstract: Ketones and aldehydes are hydrogenated to the corresponding alcohol or alkyl group, using H2 gas as the stoichiometric reductant, and organometallic ruthenium complexes as the catalysts.Type: GrantFiled: June 20, 2001Date of Patent: October 8, 2002Assignees: E. I. du Pont de Nemours and Company, Brookhaven Science AssociatesInventors: R. Morris Bullock, Marcel Schlaf, Elisabeth M. Hauptman
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Patent number: 6455743Abstract: A process for producing alcohols, which comprises subjecting a mixture comprising an aldehyde having from 2 to 5 carbon atoms and a polycondensate of the aldehyde at a weight ratio of from 95:5 to 5:95 to a mixing hydrogenation reaction in the presence of a catalyst to produce alcohols corresponding to the aldehydes at the same time wherein substantially no by-product is produced.Type: GrantFiled: November 26, 1999Date of Patent: September 24, 2002Assignee: Mitsubishi Chemical CorporationInventors: Akio Ueda, Yuichi Fujita, Atsuhiro Adachi, Hiroki Emoto
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Patent number: 6444863Abstract: A process for producing alcohols, to obtain a straight-chain alcohol having a carbon number of n (where n=3 to 6), a branched chain alcohol having a carbon number of n (where n=3 to 6) and a branched chain alcohol having a carbon number of 2n (where n=3 to 6) from a mixed aldehyde comprising a straight-chain aldehyde having a carbon number of n (where n=3 to 6) and a branched chain aldehyde having a carbon number of n (where n=3 to 6) in an optional proportion, which comprises supplying the mixed aldehyde to a distillation column, withdrawing from the bottom of the column an aldehyde rich in the straight-chain aldehyde, dimerizing the straight-chain aldehyde, followed by hydrogenation to obtain the branched chain alcohol having a carbon number of 2n, while obtaining, as a fraction from the top of the column, an aldehyde rich in the branched chain aldehyde and having a straight-chain aldehyde concentration in the fraction of at least 30 wt %, subjecting the fraction to hydrogType: GrantFiled: May 20, 1999Date of Patent: September 3, 2002Assignee: Mitsubishi Chemical CorporationInventors: Akio Ueda, Atsuhiro Adachi
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Patent number: 6441255Abstract: Carrier-bound ruthenium catalysts are used to produce alcohols by the catalytic hydrogenation of aldehydes and ketones. The problem of deactivation of the catalyst is solved by the use of a ruthenium catalyst on an oxide carrier of the series TiO2, SiO2, ZrO2, MgO, mixed oxides thereof and silicates thereof. In particular, Ru on TiO2 or SiO2 results in a long service life of the catalyst.Type: GrantFiled: September 27, 1999Date of Patent: August 27, 2002Assignee: Degussa -Huls AGInventors: Thomas Haas, Bernd Jaeger, Jörg Sauer, Rudolf Vanheertum
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Patent number: 6420613Abstract: A method of preparing a reduced product by efficiently reducing an unsaturated organic compound by using, as a reducing agent, a trichlorosilane which is industrially cheaply available and is easy to handle, and a reducing agent therefor. A reduced product of an unsaturated organic compound is obtained by mixing the unsaturated organic compound and a trichlorosilane together to reduce the unsaturated organic compound in the presence of a compound that forms a silicon complex having five coordinations upon acting on the trichlorosilane such as an N-formylated product of a secondary amine having not less than 3 carbon atoms. The invention further provides a reducing agent comprising a particular silicon complex.Type: GrantFiled: December 11, 2000Date of Patent: July 16, 2002Assignee: Tokuyama CorporationInventors: Fumiaki Iwasaki, Yoshihiro Matsumura, Osamu Onomura, Kenji Tanaka
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Publication number: 20020082457Abstract: The present invention relates to a process for the preparation of 1-(2,2,6-trimethylcyclohexyl)-3-alkanols with a content of at least 15% of trans isomers, based on the total amount of the 1-(2,2,6-trimethylcyclohexyl)-3-alkanol, by catalytic hydrogenation, where a) 1-(2,6,6-trimethyl-1 or 2-cyclohexen-1-yl)-1-alken-3-ones are reacted in the presence of ruthenium-containing catalysts or catalyst mixtures, or b) 1 -(2,6,6-trimethyl-1 or 2-cyclohexen-1-yl)-1-alken-3-ols are reacted in the presence of catalysts which contain 1 or more elements of groups Ib, VIb and VIII of the Periodic Table of the Elements.Type: ApplicationFiled: December 12, 2001Publication date: June 27, 2002Inventors: Walter Kuhn, Horst Surburg
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Patent number: 6403836Abstract: The present invention is a process for preparing C4-25 aldehydes by hydroformylating the corresponding C3-24 olefins in the presence of a cobalt hydroformylation catalyst, and catalytically decomposing the formic acid formed in the hydroformylation reaction or in the subsequent catalyst work-up. The aldehydes so produced may be hydrogenated to form alcohols.Type: GrantFiled: February 22, 2001Date of Patent: June 11, 2002Assignee: Oxeno Olefinchemie GmbHInventors: Alfred Kaizik, Walter Toetsch, Wilfried Bueschken, Felix Gosmann
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Patent number: 6392103Abstract: A process for the enantioselective reduction of prochiral ketones to chiral alcohols by (a) the reaction of a prochiral ketone with a silane agent, which is present in a stoichiometric quantity, in the presence of a catalyst derived from a Zn, Co or Cd precursor compound and from a chiral amine, imine, alcohol or amino alcohol ligand; (b) the hydrolysis of the siloxane obtained using an appropriate agent; and (c) the separation and purification of the optically active alcohol formed. Polymethylhydrosiloxane (PMHS) is a preferred silane agent, zinc is a preferred metal, and the precursor compound is produced by reacting a salt or complex of the respective metal with the reducing agent. In another embodiment, an appropriate salt of the chosen metal is used directly in the reaction with the chiral ligand to produce the catalytic form after reaction with the ligand. The process enables high enantiomeric excesses (ee) to be obtained in chiral alcohols.Type: GrantFiled: February 9, 2000Date of Patent: May 21, 2002Assignee: Firmenich SAInventor: Hubert Mimoun
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Publication number: 20020035159Abstract: Unsaturated coconut and/or palm nut fatty alcohols having an iodine number in the range from 65 to 85, which essentially comprise unsaturated fatty alcohols and mixtures of saturated fatty alcohols of the formula (I):Type: ApplicationFiled: June 5, 2001Publication date: March 21, 2002Inventors: Stephan Heck, Norbert Klein, Horst-Dieter Komp, Christiane Boehr, Norbert Huebner, Alfred Westfechtel
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Patent number: 6359179Abstract: A process for the direct carbonylation of saturated hydrocarbons has been developed. The process involves contacting the saturated hydrocarbons, which contain at least one primary, secondary or tertiary carbon atom, with carbon monoxide in the presence of a solid strong acid catalyst to produce an oxygenated saturated hydrocarbon. In a specific embodiment isobutane is reacted with carbon monoxide using sulfated zirconia as the catalyst to produce methylisopropyl ketone. The oxygenated hydrocarbon can subsequently be hydrogenated to give a reduced oxygenated saturated hydrocarbon. The hydrogenation can also be done simultaneously with the carbonylation, i.e., reductive carbonylation.Type: GrantFiled: December 22, 1999Date of Patent: March 19, 2002Assignee: UOP LLCInventors: Laszlo T. Nemeth, Jeffrey C. Bricker, Jules Rabo, Ralph D. Gillespie
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Patent number: 6355848Abstract: The invention relates to a process for the preparation of optically active alcohols from optically active carboxylic acids by reducing an optically active carboxylic acid with hydrogen in the presence of a catalyst comprising ruthenium and at least one further metal or transition metal having an atomic number in the range of from 23 to 82.Type: GrantFiled: July 25, 2000Date of Patent: March 12, 2002Assignee: Bayer AktiengesellschaftInventors: Stefan Antons, Andreas Schulze Tilling, Erich Wolters
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Publication number: 20020019574Abstract: A process for producing alcohols, to obtain a straight-chain alcohol having a carbon number of n (where n=3 to 6), a branched chain alcohol having a carbon number of n (where n=3 to 6) and a branched chain alcohol having a carbon number of 2n (where n=3 to 6) from a mixed aldehyde comprising a straight-chain aldehyde having a carbon number of n (where n=3 to 6) and a branched chain aldehyde having a carbon number of n (where n=3 to 6) in an optional proportion, which comprises supplying the mixed aldehyde to a distillation column, withdrawing from the bottom of the column an aldehyde rich in the straight-chain aldehyde, dimerizing the straight-chain aldehyde, followed by hydrogenation to obtain the branched chain alcohol having a carbon number of 2n, while obtaining, as a fraction from the top of the column, an aldehyde rich in the branched chain aldehyde and having a straight-chain aldehyde concentration in the fraction of at least 30 wt %, subjecting the fraction to hydrogType: ApplicationFiled: May 20, 1999Publication date: February 14, 2002Inventors: AKIO UEDA, ATSUHIRO ADACHI
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Patent number: 6340778Abstract: The invention relates to a process for the catalytic aldol condensation of aldehydes by means of a multiphase reaction in a tube reactor, wherein the catalyst is present in the continuous phase and at least one aldehyde is present in a dispersed phase and the loading factor B of the tube reactor is equal to or greater than 0.8; the aldol condensation products obtained in this way can be used for preparing alcohols or carboxylic acids.Type: GrantFiled: October 24, 2000Date of Patent: January 22, 2002Assignee: Oxeno Olefinchemie GmbHInventors: Wilfried Bueschken, Klaus-Diether Wiese, Guido Protzmann, Juergen Koch
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Patent number: 6333441Abstract: A cis-olefin of the formula: R1—CH═CH—R2 is prepared by reducing an alkyne of the formula: R1—C≡C—R2 with formic acid in the presence of a palladium catalyst. R1 and R2 are independently selected from the group consisting of a hydrogen atom, ester group, substituted silyl group, carboxyl group, cyano group, aliphatic C1-C20 hydrocarbon group, and phenyl group. The cis-olefin which is a useful intermediate for the synthesis of fine chemicals is selectively produced in high yields.Type: GrantFiled: March 4, 1993Date of Patent: December 25, 2001Assignees: Nissan Chemical Industries, Ltd.Inventors: Fumie Sato, Katsuaki Miyaji, Takehiro Amano
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Publication number: 20010053800Abstract: A mixture of monounsaturated alcohols with 14 to 24 linear carbons in the linear chain is represented by jojoba alcohol, which remains an oily liquid at moderate ambient temperature. Jojoba alcohol is prepared by chemical hydrogenolysis of jojoba oil using a metal hydride reducing agent. A similar mixture of long chain monounsaturated alcohols can be prepared by hydrogenolysis of sperm whale oil. Mixtures of long chain monounsaturated alcohols penetrate epidermal layers of the skin to the vascular cells underneath where herpes viral infection, pain and other disorders occur.Type: ApplicationFiled: February 21, 2001Publication date: December 20, 2001Inventor: Anthony J. Verbiscar
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Patent number: 6331657Abstract: A process for preparing higher oxo alcohols from mixtures of isomeric olefins having from 5 to 24 carbon atoms by two-stage hydroformylation in the presence of a cobalt catalyst or rhodium catalyst at elevated temperature and at elevated pressure, which comprises selectively hydrogenating the first hydroformylation stage reaction mixture, separating the hydrogenation mixture in a distillation into crude alcohol and low-boilers predominantly consisting of olefins, passing these low-boilers to the second hydroformylation stage, again selectively hydrogenating the second hydroformylation stage reaction mixture, separating the hydrogenation mixture in one distillation into crude alcohol and low-boilers, working up the crude alcohol by distillation to pure alcohol and taking off at least some of the low-boilers to discharge saturated hydrocarbons.Type: GrantFiled: September 15, 1999Date of Patent: December 18, 2001Assignee: Oxeno Olefinchemie GmbHInventors: Alfred Kaizik, Bernhard Scholz, Walter Toetsch, Wilfried Bueschken, Franz Nierlich
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Patent number: 6326512Abstract: Disclosed is a method of producing an optically active &bgr;-hydroxy sulfonic acid compound comprising hydrogenating a &bgr;-keto sulfonic acid compound represented by formula 1: where R1 represents an alkyl or a phenyl group, which may be substituted, and R2 represents sodium or an alkyl group, in an acidic solvent, in the presence of an asymmetric catalyst comprising a complex of bivalent Ru, having 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl as a ligand, to produce a compound represented by formula 2: where R1 and R2 are as defined above, and * designates an asymmetric carbon atom.Type: GrantFiled: June 1, 2000Date of Patent: December 4, 2001Assignee: President of Nagoya UniversityInventors: Masato Kitamura, Masahiro Yoshimura, Naoki Kanda, Ryoji Noyori
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Publication number: 20010047116Abstract: A method of increasing enantioselectivity in a reduction reaction of a prochiral substrate with a borane reagent including a borohydride species (for example, a borohydride stabilized borane-tetrahydrofuran complex) catalyzed by a chiral catalyst includes the step of maintaining the concentration of borohydride species in the borane reagent below approximately 0.005 M during the reduction of the prochiral substrate. A method of increasing enantioselectivity in a reduction reaction of a prochiral substrate with a borane reagent including a borohydride species that is catalyzed by a chiral catalyst includes the step of reducing the detrimental effect the borohydride species has on enantioselectivity by adding a Lewis acid. For example, the prochiral substrate can be a ketone and the chiral catalyst can be a chiral oxazaborolidine.Type: ApplicationFiled: January 26, 2001Publication date: November 29, 2001Applicant: Mine Safety Appliances CompanyInventors: Karl Matos, Joseph A. Corella, Elizabeth R. Burkhardt, Shawn M. Nettles
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Publication number: 20010034464Abstract: A reductive system including a silane, preferably PMHS, and an active zinc compound, which is monomeric and not a hydride, wherein a reduction of a carbonyl substrate to a corresponding alcohol is achievable.Type: ApplicationFiled: April 6, 2001Publication date: October 25, 2001Applicant: FIRMENICH SAInventor: Hubert Mimoun
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Patent number: 6306359Abstract: Hydrogenation catalysts based on palladium, platinum or rhodium comprising at least one other metal M which are deposited on zirconium oxide and silicon oxide supports. Process for the manufacture of these catalysts by successive impregnation of the support using palladium, platinum or rhodium and using another metal M. Use of these catalysts in hydrogenation reactions and in particular in preparing hydrogen peroxide.Type: GrantFiled: June 22, 1999Date of Patent: October 23, 2001Assignee: Solvay Interox (Societe Anon.)Inventors: Véronique Mathieu, Pascal Pennetreau, Noel Vanlautem
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Patent number: 6297409Abstract: The invention relates to a continuous process for the preparation of a high-purity hydrogenated ose by catalytic hydrogenation of the corresponding ose in falling film reactors, wherein the hydrogenation is carried out in a series of fixed beds of ruthenium catalyst comprising: a) a first hydrogenation zone consisting of at least one fixed bed of ruthenium catalyst, and b) a second hydrogenation zone consisting of at least one fixed bed of ruthenium catalyst containing a promoter.Type: GrantFiled: February 17, 2000Date of Patent: October 2, 2001Assignee: Roquette FreresInventors: Jean-Christophe Choque, Guy Fleche