Gaseous Hydrogen Reactant Or Group Ia Or Iia Light Metal Containing Material Utilized Patents (Class 568/396)
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Publication number: 20150051425Abstract: In one embodiment, the invention is to a catalyst composition comprising lime and cement. Preferably, the catalyst composition comprises the lime and the cement in a weight ratio of at least 3.5:1 respectively.Type: ApplicationFiled: August 13, 2014Publication date: February 19, 2015Inventors: Gustavo Angel Robelo Grajales, Ricardo Alderete Delgadillo
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Publication number: 20150025277Abstract: Embodiments of the present invention describe systems and methods for production of methyl isobutyl ketone (MIBK) from acetone and hydrogen in a two-step process. In a first step, acetone is converted to a product stream containing mesityl oxide (MO) at a temperature in the range of about 0-120° C. and a pressure in the range of about 1-3 atm. The composition of the product stream from the first reaction step is adjusted so that the resulting stream can undergo a favorable liquid-liquid separation in a decanter, and an MO rich product stream can be recovered. The composition of the feed to the decanter is controlled by choosing the number of reactor stages for the first reaction step and their operating temperatures, and/or by recycling some MIBK to the decanter feed. The method does not require a substantially complete conversion of acetone in the first reaction step, nor does it require a removal of DAA from the product of the first reaction step by separation.Type: ApplicationFiled: May 28, 2014Publication date: January 22, 2015Applicant: ClearWaterBay Technology, Inc.Inventors: Vaibhav V. Kelkar, Drow Lionel O'Young, Christianto Wibowo, Madhura Kelkar, Hok Chung Chan
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Patent number: 8552223Abstract: A method of making a heterogeneous catalyst, the catalyst produced therefrom, and the use of the catalyst, comprising mixing a dried ion exchange resin with a solution of a ketone and a metal, swelling the ion exchange resin, distributing the metal in the resin, and transforming without reducing agents the metal to zero valent at a temperature below 120° C.Type: GrantFiled: June 24, 2011Date of Patent: October 8, 2013Assignee: Rohm and Haas CompanyInventors: James Tate, Jose Antonio Trejo-O'Reilly
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Patent number: 8492594Abstract: A polymeric catalyst, and methods of using the catalyst, comprising at least one of a monosulfonated ion exchange resin, monosulfonated gel, and macroreticular resin having a particle size of less than 560 ?m and metal impregnated within the resin, where the metal is palladium, platinum, iridium, rhodium, ruthenium, copper, gold, and/or silver.Type: GrantFiled: June 24, 2011Date of Patent: July 23, 2013Assignee: Rohm and Haas CompanyInventors: Daniel Martenak, James F. Tate, Jose Antonio Trejo-O'Reilly
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Patent number: 8471069Abstract: A mixed bed polymeric catalyst, and use of that catalyst, comprising 10-90% by weight of a first catalyst having ion exchange resin loaded with metal of palladium, platinum, iridium, rhodium, ruthenium, copper, gold, and/or silver and 10-90% by weight of a second catalyst having strong acidic ion exchange resin devoid of metal, where the metal is uniformly distributed throughout a mixed bed.Type: GrantFiled: June 29, 2011Date of Patent: June 25, 2013Assignee: Rohm and Haas CompanyInventors: John Kramer, Jose Antonio Trejo-O'Reilly
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Publication number: 20120296124Abstract: Efficient and recyclable heterogeneous nanocatalysts and methods of synthesizing and using the same are provided.Type: ApplicationFiled: February 14, 2012Publication date: November 22, 2012Inventors: Tewodros Asefa, Ankush V. Biradar, Yanfei Wang
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Publication number: 20120004468Abstract: A method of making a heterogeneous catalyst, the catalyst produced therefrom, and the use of the catalyst, comprising mixing a dried ion exchange resin with a solution of a ketone and a metal, swelling the ion exchange resin, distributing the metal in the resin, and transforming without reducing agents the metal to zero valent at a temperature below 120° C.Type: ApplicationFiled: June 24, 2011Publication date: January 5, 2012Inventors: James Tate, Jose Antonio Trejo-O'Reilly
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Publication number: 20120004469Abstract: A polymeric catalyst, and methods of using the catalyst, comprising at least one of a monosulfonated ion exchange resin, monosulfonated gel, and macroreticular resin having a particle size of less than 560 ?m and metal impregnated within the resin, where the metal is palladium, platinum, iridium, rhodium, ruthenium, copper, gold, and/or silver.Type: ApplicationFiled: June 24, 2011Publication date: January 5, 2012Inventors: Daniel Martenak, James F. Tate, Jose Antonio Trejo-O'Reilly
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Publication number: 20110237837Abstract: A low-pressure one-step gas-phase process for the production and recovery of methyl isobutyl ketone (MIBK) is disclosed. One-step gas-phase synthesis of MIBK from acetone and hydrogen over nano-Pd/nano-ZnCr2O4 catalyst at atmospheric pressure is used as an example. The said process is designed to recover the additional heat associated with the reactor effluent via heating acetone feed and recycle (mixed acetone) before entering the reactor. A compressor is introduced to the gas-phase process to increase slightly the reactor effluent pressure before this effluent is cooled and fed to a flash drum. The compressed reactor effluent is used to preheat hydrogen feed and recycle (mixed hydrogen) before entering the reactor. The separation scheme of low-pressure one-step gas-phase process comprises of several distillation columns used for MIBK separation and purification.Type: ApplicationFiled: June 7, 2011Publication date: September 29, 2011Applicant: King Abdulaziz City for Science and Technology (KACST)Inventors: Abdulrahman A. Al-Rabiah, Vagif Malik Akhmedov, Abdulaziz A. Bagabas
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Patent number: 7973198Abstract: The present invention relates to a process for preparing optically active carbonyl compounds by asymmetrically hydrogenating ?,?-unsaturated carbonyl compounds in the presence of optically active transition metal catalysts which are soluble in the reaction mixture and have at least one carbon monoxide ligand, the optically active catalyst which has at least one carbon monoxide ligand and is to be used in each case being prepared by pretreating a catalyst precursor with a gas mixture comprising carbon monoxide and hydrogen and the asymmetric hydrogenation being performed in the presence of carbon monoxide supplied additionally to the reaction mixture.Type: GrantFiled: April 17, 2008Date of Patent: July 5, 2011Assignee: BASF SEInventors: Joachim Schmidt-Leithoff, Christoph Jäkel, Rocco Paciello
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Patent number: 7935849Abstract: Saturated aliphatic ketones, e.g. hexahydropseudoionone, may be prepared by hydrogenating an olefinically unsaturated ketone, e.g. pseudoionone in a continuous fixed-bed mode in the absence of a solvent in the presence of a catalyst comprising a noble metal deposited on a carrier.Type: GrantFiled: September 14, 2005Date of Patent: May 3, 2011Assignee: DSM IP Assets B.V.Inventors: Werner Bonrath, Thomas Kircher, Rolf Kuenzi, Johannes Tschumi
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Patent number: 7767863Abstract: An improved method for the manufacture of MIBK and DIBK from DMK and/or IPA, by reacting, in the presence of an aldol condensation catalyst, a gaseous mixture comprising hydrogen and DMK and/or IPA. The improvement is the use of a reaction pressure greater than 207 kPa (30 psig) to increase the ratio of MIBK to DIBK. In addition a method for the manufacture of MIBK and DIBK by reacting, in the presence of an aldol condensation catalyst, a gaseous mixture consisting essentially of DMK and/or IPA and optionally water.Type: GrantFiled: September 26, 2006Date of Patent: August 3, 2010Inventors: Jeffrey S. Sawrey, Richard W. Wegman
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Patent number: 7071361Abstract: Continuous single-step processes for producing higher molecular weight ketones are disclosed that involve a liquid-phase crossed condensation of an aldehyde with a ketone in the presence of a hydrogenation catalyst and a small amount of a catalyst comprising a concentrated hydroxide or alkoxide of an alkali-metal (from Group 1 or Group IA of the Periodic Table of the Elements) or alkali-earth metal (from Group 2, or Group IIA of the Periodic Table of the Elements), wherein the amount of water provided to the reaction mixture, or reaction zone, is relatively low, with respect to the total initial weight of the reaction mixture. The reaction may be carried out in the absence of solubilizing agents or phase transfer agents. The product mixture is largely free of by-products resulting from further condensation reactions of the desired ketone product or intermediates, and free of the self-condensation products of the reactant aldehyde, that are afterward difficult to remove from the reaction mixture.Type: GrantFiled: June 25, 2004Date of Patent: July 4, 2006Assignee: Fastman Chemical CompanyInventors: Scott Donald Barnicki, Jennifer Ellen McCusker-Orth, Joseph Franklin Knight, Jerry Lynn Miller
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Patent number: 6987203Abstract: A process for the preparation of a novel intermediate compound useful in the preparation of phytone and vitamin E.Type: GrantFiled: January 13, 2003Date of Patent: January 17, 2006Assignee: Adisseo France S.A.S.Inventor: Jean-Erick Ancel
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Patent number: 6984761Abstract: A process is disclosed for producing ?-methylstyrene, acetone, and phenol wherein the amount of ?-methylstyrene produced may be controlled by selectively converting a portion of the cumene hydroperoxide to dimethyl phenyl carbinol, the hydrated form of ?-methylstyrene. The dimethyl phenyl carbinol thus produced will lead to increased production of ?-methylstyrene upon dehydration in the acid cleavage unit of the phenol plant. By controlling the fraction of the cumene hydroperoxide reduced to dimethyl phenyl carbinol, the amount of ?-methylstyrene produced in the plant can be continuously set to meet the demand of the market for ?-methylstyrene. Also disclosed is a non-acidic catalyst for reduction of cumene hydroperoxide.Type: GrantFiled: December 16, 2002Date of Patent: January 10, 2006Assignee: ExxonMobil Chemical Patents Inc.Inventors: Doron Levin, C. Morris Smith, Jose Guadalupe Santiesteban, James C. Vartuli
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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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Patent number: 6977314Abstract: A method for preparing ketones in greater yield and selectivity compared to previous catalyzed reactions by acid-catalyzed condensation reaction using a metal-doped polysulfonated ion exchange resin catalyst is disclosed. For example, use of polysulfonated ion exchange resins having at least 5.0 milliequivalents sulfonic acid groups/gram catalyst and loaded with metal, such as palladium, provides enhanced yields of methyl isobutyl ketone from the condensation reaction of acetone compared to use of conventional monosulfonated ion exchange resin catalysts.Type: GrantFiled: December 3, 2002Date of Patent: December 20, 2005Assignee: Rohm and Haas CompanyInventors: Mark Thornton Vandersall, Rudolf Alfred Weinand
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Patent number: 6960694Abstract: Processes for producing ?-hydroxy-ketones and ?,?-unsaturated ketones are disclosed which comprise the crossed condensation of an aldehyde with a ketone in the presence of a hydroxide or alkoxide of alkali metal or an alkaline earth metal as catalyst. The products of the process, ?-hydroxy-ketones and ?,?-unsaturated ketones, are useful for the preparation of many commercially important products in the chemical process industries including solvents, drug intermediates, flavors and fragrances, other specialty chemical intermediates.Type: GrantFiled: July 1, 2003Date of Patent: November 1, 2005Assignee: Eastman Chemical CompanyInventors: Scott Donald Barnicki, Jennifer Ellen McCusker-Orth, Jerry Lynn Miller
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Patent number: 6762328Abstract: A process for producing methyl isobutyl ketone includes introducing acetone into a catalytic distillation. Some of the acetone is converted to mesityl oxide (‘MSO’), water and, optionally, diacetone alcohol (‘DAA’) and/or other by-products. A product stream comprising MSO, water, and, optionally, DAA, other by-products and/or unreacted acetone is withdrawn from the catalytic distillation zone. When the product stream includes DAA, other by-products and/or unreacted acetone, it is treated in a treatment zone to remove at least some of the DAA, other by-products and/or the unreacted acetone therefrom. The product stream and hydrogen are fed into a reaction zone in which MSO present in the product stream and hydrogen react to form methyl isobutyl ketone (‘MIBK’). A MIBK rich product stream is withdrawn from this reaction zone. Both a markup and clean copy of the substitute Abstract are attached to this amendment.Type: GrantFiled: November 7, 2002Date of Patent: July 13, 2004Assignee: Catalytic Distillation TechnologiesInventors: Nelis Saayman, Grand James Lund, Sybrandus Kindermans
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Patent number: 6706928Abstract: Production of unsaturated ketones by the aldol condensation of ketones such as acetone or methyl ethyl ketone by contacting the ketone in the vapor phase with a particulate catalyst comprising at least one basic alkali metal compound supported on an inert substrate at a temperature above 175° C. The produce ketones may be hydrogenated to form saturated ketones or alcohols.Type: GrantFiled: November 18, 2002Date of Patent: March 16, 2004Assignee: Johnson Matthey PLCInventor: Gordon J Kelly
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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: 6518462Abstract: A process for producing methyl isobutyl ketone includes introducing acetone into a catalytic distillation. Some of the acetone is converted to mesityl oxide (‘MSO’), water and, optionally, diacetone alcohol (‘DAA’) and/or other by-products. A product stream comprising MSO, water, and, optionally, DAA, other by-products and/or unreacted acetone is withdrawn from the catalytic distillation zone. When the product stream includes DAA, other by-products and/or unreacted acetone, it is treated in a treatment zone to remove at least some of the DAA, other by-products and/or the unreacted acetone therefrom. The product stream and hydrogen are fed into a reaction zone in which MSO present in the product stream and hydrogen react to form methyl isobutyl ketone (‘MIBK’). A MIBK rich product stream is withdrawn from this reaction zone.Type: GrantFiled: September 11, 2001Date of Patent: February 11, 2003Assignee: Catalytic Distillation TechnologiesInventors: Nelis Saayman, Grant James Lund, Sybrandus Kindermans
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Publication number: 20020165415Abstract: Commercially feasible methods for synthesizing various epothilones precursors needed for the preparation of final epothilones are provided, including techniques for the synthesis of epothilone segment C using a stereoselective Noyori-type reduction, and the coupling of epothilone segments B and C using an aldol condensation reaction. The synthesis methods may be used to prepare naturally occurring segments as well as a large number of related analogs and homologs thereof. Final epothilones in accordance with the invention may also be of the naturally occurring variety (16-membered macrolides), while the homologs and analogs thereof are preferably up to 20-membered macrolides.Type: ApplicationFiled: March 2, 2001Publication date: November 7, 2002Inventors: Gunda I. Georg, Sajiv K. Nair, Emily Reiff, Ashok Rao Tunoori, John T. Henri
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Patent number: 6417406Abstract: The present invention provides a process for producing 6-methyl heptanone and corresponding methyl ketones, in particular phytone and tetrahydrogeranyl acetone, by aldolization of aldehydes with acetone in the presence of an aldolization catalyst and a heterogeneous hydrogenation catalyst containing a polyhydric alcohol.Type: GrantFiled: September 10, 2001Date of Patent: July 9, 2002Assignee: Degussa AGInventors: Steffen Krill, Klaus Huthmacher
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Patent number: 6369277Abstract: An &agr;,&bgr;-unsaturated carbonyl compound of formula (I) where R1 is saturated C1-40-hydrocarbyl or a substituted or unsubstituted aromatic radical containing moiety, and R2, R3 and R4, independently of one another, are hydrogen or a C1- to C4-alkyl group, is selectively hydrogenated in the liquid phase to a saturated carbonyl compound of formula (II) with hydrogen in the presence of a pulverulent palladium and/or rhodium catalyst and in the presence of an organic base, by conducting the hydrogenation in a packed bubble column reactor in which product is recycled and hydrogen gas is recirculated.Type: GrantFiled: August 25, 2000Date of Patent: April 9, 2002Assignee: BASF AktiengesellschaftInventors: Franz Josef Broecker, Gerd Kaibel, Werner Aquila, Hartwig Fuchs, Guenter Wegner, Manfred Stroezel
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Patent number: 6288281Abstract: A process for the carbonylation of saturated hydrocarbons to give an oxygenated saturated hydrocarbon is disclosed and claimed. The process involves using an acidic ionic liquid catalyst to catalyze the carbon monoxide addition to the saturated hydrocarbon at reaction conditions to form an oxygenate. The acidic ionic liquid comprises a Lewis or Bronsted acid in combination with a quaternary nitrogen-containing compound. A specific example is a mixture of aluminum chloride and n-butylpyridinium chloride.Type: GrantFiled: November 16, 2000Date of Patent: September 11, 2001Assignee: UOP LLCInventors: Laszlo T. Nemeth, Jeffery C. Bricker, Jennifer S. Holmgren, Lyle E. Monson
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Patent number: 6248928Abstract: A method of manufacturing a strontium &bgr;-diketonate precursor suitable for MOCVD techniques comprises the step of reacting strontium with a sterically hindered alcohol to produce strontium alkoxide, subsequently reacting the strontium alkoxide with a &bgr;-diketone to form a strontium &bgr;-diketonate alcohol adduct and removing the alcohol from the adduct.Type: GrantFiled: July 21, 2000Date of Patent: June 19, 2001Assignee: Inorgtech LimitedInventor: Anthony Copeland Jones
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Patent number: 6150564Abstract: The invention relates to a process for the selective liquid-phase hydrogenation of .alpha.,.beta.-unsaturated carbonyl compounds of the formula I, ##STR1## where R.sub.1 is hydrogen or an organic radical, and R.sub.2, R.sub.3 and R.sub.4, independently of one another, are hydrogen or a C.sub.1 -- to C.sub.4 --alkyl group, to saturated carbonyl compounds of the formula II ##STR2## using hydrogen in the presence of a pulverulent palladium and/or rhodium catalyst and in the presence of an organic base. The process is carried out in a packed bubble column reactor (1, 2) with product recycling (11, 17) and circulating hydrogen gas (4, 15, 16). It is particularly suitable for the selective hydrogenation of citral to citronellal.Type: GrantFiled: March 25, 1999Date of Patent: November 21, 2000Assignee: BASF AktiengesellschaftInventors: Franz Josef Brocker, Gerd Kaibel, Werner Aquila, Hartwig Fuchs, Gunter Wegner, Manfred Stroezel
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Patent number: 6008416Abstract: A process for the production of methyl isobutyl ketone from acetone and hydrogen utilizing a catalytic distillation column reactor. The reactions take place in a reaction zone with the reaction products being removed from the reaction zone and unreacted acetone being refluxed. The equilibrium is thus continuously disturbed allowing for greater than equilibrium conversion of acetone.Type: GrantFiled: June 16, 1998Date of Patent: December 28, 1999Assignee: Catalytic Distillation TechnologiesInventors: Keith Henry Lawson, Bongani Nkosi
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Patent number: 6002047Abstract: The present invention is concerned with a process for the catalytic hydrogenation of organic compounds on a catalyst of amorphous metal alloys and in a solvent, with the hydrogenation being carried out under near-critical or supercritical conditions of the solvent. The amorphous metal alloys can be produced by the shock cooling of alloy melts having eutectic solidification points. By hydrogenation at hydrogen partial pressures between 5 and 400 bar there is obtained outstanding space-time yields with high long-term stability of the catalytic activity.Type: GrantFiled: October 28, 1997Date of Patent: December 14, 1999Assignee: Roche Vitamins Inc.Inventors: Michael Jansen, Claus Rehren
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Patent number: 5684207Abstract: A one-step process for selective production of methyl isobutyl ketone includes reacting in the vapor/liquid phase acetone and hydrogen at a temperature of about 100.degree. to 300.degree. C. and a pressure of about 100 to 1000 psig, in the presence of a modified ZSM-5 catalyst having a molar ratio of SiO.sub.2 /Al.sub.2 O.sub.3 from about 20:1 to 680:1, the catalyst being prepared by treating a ZSM-5 zeolite with an organic acid having a pKa of 2 to 5, ion-exchanging or impregnating the ZSM-5 zeolite with a cation selected from the group consisting of palladium cation, platinum cation, copper cation and nickel cation, and activating the resultant catalyst in a reducing atmosphere.Type: GrantFiled: July 19, 1996Date of Patent: November 4, 1997Assignee: Industrial Technology Research InstituteInventors: Po-Yu Chen, Shiao-Jung Chu, Kuo-Ching Wu, Wen-Chyi Lin
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Patent number: 5600015Abstract: There is described a process for the manufacture of isoprene derivatives of the general formula ##STR1## wherein the asymmetric centres can each individually have the (R)- or (S)-configuration, R represents a residue of the formulae ##STR2## R.sup.1 signifies lower alkyl or both R.sup.1 's together signify ethylene or propylene and n stands for the number 0, 1 or 2,in which a compound, which is present in the (E)- or (Z)-form, of the general formula ##STR3## wherein R, n and an optionally present asymmetric centre have the above significance,is asymmetrically hydrogenated with a ruthenium complex of an optically active atropisomeric diphosphine.Type: GrantFiled: May 19, 1995Date of Patent: February 4, 1997Assignee: Hoffmann-La Roche Inc.Inventors: Emil A. Broger, Robert K. M uller
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Patent number: 5583263Abstract: A multistep process for producing amyl ketones is provided. In the process, a methyl ketone is reacted with butyraldehyde to form a C.sub.7 aldol condensation product which is then dehydrated to form an olefinic ketone and hydrogenated to form an amyl ketone. The process is suitable for coproduction along with the production of MIBK and yields products with a high selectivity.Type: GrantFiled: August 30, 1995Date of Patent: December 10, 1996Assignee: Shell Oil CompanyInventors: Duraisamy Muthusamy, Chia-Chung Wang, Richard D. Swain, David B. Litzen, William R. Pledger
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Patent number: 5426246Abstract: Disclosed are a catalyst for directly reducing a carboxylic acid, the catalyst comprising a tin compound and a ruthenium compound supported on a carrier, the catalyst being prepared by the steps of calcining the tin compound in the presence of oxygen after deposition of the tin compound alone on the carrier, and activating the obtained product after deposition of the ruthenium compound on said carrier, a process for preparing the catalyst, and a process for preparing an alcohol compound using the catalyst.Type: GrantFiled: July 26, 1994Date of Patent: June 20, 1995Assignee: Arakawa Chemical Industries, Ltd.Inventors: Eiji Nagahara, Yasushi Itoi
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Patent number: 5360938Abstract: This invention relates to asymmetric syntheses in which a prochiral or chiral compound is contacted in the presence of an optically active metal-ligand complex catalyst to produce an optically active product.Type: GrantFiled: July 16, 1992Date of Patent: November 1, 1994Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: James E. Babin, Gregory T. Whiteker
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Patent number: 5349107Abstract: Disclosed herein is a process for producing a .gamma.-hydroxyketone (2), which comprises asymmetrically hydrogenating a .gamma.-diketone (1) in the presence of a ruthenium-optically active phosphine complex as a catalyst ##STR1## wherein R.sup.1 and R.sup.2 mean individually an alkyl or phenyl group which may have a substituent group. According to the invention, optically active .gamma.-hydroxyketones useful in synthesizing optically active moiety in, biodegradable polymers, perfumes, intermediates for synthesizing medicines and the like can be efficiently prepared.Type: GrantFiled: October 1, 1993Date of Patent: September 20, 1994Assignee: Takasago International CorporationInventors: Seiji Watanabe, Shigeru Mitsuhashi, Hidenori Kumobayashi
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Patent number: 5274136Abstract: An improved method for the decarbalkoxylation of alkylated .beta.-keto esters to obtain high yields of ketones. In accordance with the method, decarbalkoxylation of alkylated .beta.-keto esters is accomplished by heating the esters in the presence of dilute aqueous alkali and an effective amount of a phase-transfer agent. The method produces commercially practical yields of ketone in a manner which is facile, economical and environmentally safe. Novel methylene-linked pyrethroid ketones produced from the improved method exhibit insecticidal activity against various agricultural pests.Type: GrantFiled: July 1, 1992Date of Patent: December 28, 1993Assignee: The United States of America as represented by the Secretary of AgricultureInventors: Frank D. Mills, Richard T. Brown, Giles D. Mills, Jr.
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Patent number: 5162586Abstract: The conjugate addition of hydrocarbon equivalents to alpha,beta-unsaturated carbonyl compounds using a series of novel catalysts is described. The catalysts comprise copper(I) complexes with ligand systems comprising either tropocoronand macrocycles or N,N'-dialkylsubstituted aminotroponeimines.Type: GrantFiled: May 9, 1989Date of Patent: November 10, 1992Assignee: Massachusetts Institute of TechnologyInventors: Gilberto M. Villacorta, Kwang-Hyun Ahn, Stephen J. Lippard
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Patent number: 5149881Abstract: A method for producing methyl isobutyl ketone, which comprises contacting acetone and hydrogen in the presence of palladium and a metal oxide and/or metal hydroxide treated with an organosilicon compound of the formula (I):R.sub.a.sup.1 (OR.sup.2).sub.b X.sub.c Si (I)wherein each of R.sup.1 and R.sup.2 is a group selected from the group consisting of hydrogen, and alkyl, vinyl and aryl groups having a total carbon number of at most 30, which may have substituents, and R.sup.1 and R.sup.2 may be the same or different from each other, X is an element selected from the group consisting of hydrogen, fluorine, chlorine, bromine and iodine, and a, b and c are 0.ltoreq.a<4, 0.ltoreq.b.ltoreq.4 and 0.ltoreq.c.ltoreq.4, respectively, and a+b+c=4.Type: GrantFiled: May 20, 1991Date of Patent: September 22, 1992Assignee: Mitsubishi Kasei CorporationInventors: Takashi Ushikubo, Yumiko Kakuno, Hisako Tsujiura
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Patent number: 5132464Abstract: There is disclosed a catalytic hydrogenation process resulting in compounds of the formula ##STR1## wherein the dotted line represents a facultative bond, by hydrogenating the compound of the formula ##STR2## in the presence of a platinum or a nickel catalyst.Type: GrantFiled: January 23, 1990Date of Patent: July 21, 1992Assignee: Hoffmann-La Roche, Inc.Inventors: Bryant E. Rossiter, Francois Montavon, Felix Roessler
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Patent number: 5059724Abstract: Process for selective synthesis of methyl isobutyl ketone by reacting in vapor phase or vapor/liquid phase acetone and hydrogen, e.g. in 0.5-3:1 molar ratio at 150.degree.-300.degree. C. and 1-30 atm., in the presence of a modified palladium-containing ZSM-5 zeolite catalyst, e.g. of 0.05-5% Pd content, as porous crystalline aluminosilicate catalyst having a 15-700:1 silica to alumina ratio, e.g. at a weight hourly space velocity of 0.5-8 hr.sup.-1, the catalyst being prepared by treating a completely acidic ZSM-5 zeolite sequentially with alkali metal cations and palladium ions and then activating the resultant zeolite in a reducing atmosphere.Type: GrantFiled: May 31, 1990Date of Patent: October 22, 1991Assignee: Industrial Technology Research InstituteInventors: Po Y. Chen, Shiao J. Chu, Cha C. Chen, Nan S. Chang, Wen C. Lin, T. K. Chuang
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Patent number: 4940819Abstract: The catalytic hydrogenation of .alpha.,.beta.-unsaturated ketones of the formulaR.sup.1 --CH.dbd.CH--CO--R.sup.2,in whichR.sup.1 and R.sup.2 independently of one another represent straight-chain or branched alkyl, hydroxy-alkyl, alkenyl, cycloalkyl, cycloalkenyl, aralkyl or aryl, where at least one of the radicals R.sup.1 and R.sup.2 is monosubstituted to trisubstituted by halogen,can be carried out on a Ni-containing catalyst and in the presence of an organic sulphur compound of the formulaR.sup.3 --S(.dbd.O).sub.n --R.sup.4in whichR.sup.3 and R.sup.4 independently of one another denote straight-chain or branched alkyl, hydroxy-alkyl, carboxyalkyl or phenyl, and furthermoreR.sup.3 and R.sup.4 may together represent --CH.dbd.CH--CH.dbd.CH--, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 --, --(CH.sub.2).sub.2 --S--(CH.sub.2).sub.2 -- or --(CH.sub.2).sub.2 --O--(CH.sub.2).sub.2 --,R.sup.4 may additionally denote hydrogen or CO--C.sub.1 -C.sub.12 -alkyl and n assumes the value 0 or 1.Type: GrantFiled: July 5, 1989Date of Patent: July 10, 1990Assignee: Bayer AktiengesellschaftInventors: Wolfgang Kiel, Heinz Ziemann
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Patent number: 4866210Abstract: Ketones of the formula ##STR1## where R.sup.1 to R.sup.3 are each hydrogen and R.sup.1 to R.sup.4 are each alkyl of 1 to 12 carbon atoms, cycloalkyl of 4 to 8 carbon atoms, aryl, aralkyl or alkylaryl, which each in turn may be substituted, or R.sup.1 and R.sup.2 and R.sup.3 together with the carbon atoms to which they are bonded form a cycloalkane, are prepared by reacting ketones of the formula ##STR2## where one of R.sup.1, R.sup.2, R.sup.3 and R.sup.5 is hydroxyl, alkoxy or carboxyl while the remaining R.sup.1 to R.sup.4 have the abovementioned meanings, with hydrogen in the presence of acid catalysts supporting one or more hydrogenation components, zeolites of the pentasil type being particularly suitable.Type: GrantFiled: January 15, 1988Date of Patent: September 12, 1989Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Leopold Hupfer, Kurt Schneider
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Patent number: 4739122Abstract: A process to produce Methyl Amyl Ketone heterogeneously via the cross-aldol condensation reaction between a C.sub.3 (isopropanol or acetone feed) and a C.sub.4 (butanol or butyraldehyde feed). The catalyst, hydrogen reduced copper oxide on gamma alumina, produces both high reactivity and long catalyst lifetimes. The catalyst is successfully regenerated. Efficiencies to MAK range from 50 to 80 wt. % and efficiencies to useful products range from 75 to 95 wt. % depending on the composition of the feed and temperature. Temperatures range from 200.degree. to 262.degree. C.In general, this catalyst readily catalyzes the cross-aldol condensation reaction between aldehydes (or primary alcohols) and ketones (or secondary alcohols) to produce higher molecular weight ketones; likewise, this catalyst catalyzes the aldol condensation reaction between the same or different ketones to again produce higher molecular weight ketones.Type: GrantFiled: October 18, 1985Date of Patent: April 19, 1988Assignee: Union Carbide CorporationInventor: John B. Letts
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Patent number: 4727196Abstract: Higher carbonyl compounds are prepared from C.sub.1 to C.sub.8 cyclic or acyclic alcohols containing at least one active hydrogen atom bonded to the beta carbon atom or readily convertible thereto under the reaction conditions by reacting the alcohol in the presence as catalyst of ruthenium metal or an oxide thereof supported on a solid support.Type: GrantFiled: August 22, 1986Date of Patent: February 23, 1988Assignee: BP Chemicals LimitedInventors: Derek K. MacApline, Bruce L. Williams, Peter S. Williams
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Patent number: 4704480Abstract: A novel process is described for the production of aliphatic ketones and an optional consequetive production of the corresponding carbinols. The starting reactants comprise ketones or aldehydes or compounds capable of converting to these in situ, such as alcohols. The reaction takes place in the presence of hydrogen in a selective temperature range, utilizing a catalyst comprising copper oxide.Type: GrantFiled: August 4, 1986Date of Patent: November 3, 1987Assignee: Allied CorporationInventors: Fred J. Gefri, Divakaran Masilamani, Andiappan K. S. Murthy
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Patent number: 4701562Abstract: Aldehydes can be condensed with ketones or aldehydes to produce higher aldehydes or ketones by contacting the materials to be condensed with a nonzeolitic molecular sieve. The condensation may be carried out in the presence of hydrogen to give as product a saturated aldehyde or ketone. The ketone and/or aldehyde may be generated in situ by dehydrogenation of an alcohol, and the hydrogen thus liberated used to effect hydrogenation of the immediate unsaturated product of the condensation, thereby producing as the final product a saturated aldehyde or ketone. The non-zeolitic molecular sieves can achieve improved conversion rates and selectivities as compared with conventional catalysts for the reaction.Type: GrantFiled: June 25, 1986Date of Patent: October 20, 1987Assignee: Union Carbide CorporationInventor: Kurt D. Olson
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Patent number: 4567004Abstract: Monomethyl-substituted methylene compounds are obtained by reacting methylene compounds of the formula ##STR1## in which R.sup.1 and R.sup.2 independently of one another represent --CN, --CO--R.sup.3, --SO.sub.2 --R.sup.3 or --NO.sub.2 andR.sup.1 can additionally denote -aryl(R.sup.1).sub.n,whereinR.sup.3 denotes --OH, alkyl, aralkyl, aryl, alkoxy, aralkoxy or aryloxy, or amino which is substituted by alkyl and/or aralkyl and/or aryl, and furthermoretwo radicals R.sup.3 together can be an alkylene group, the radical of an aliphatic diol or of an aliphatic diamine or the group --NH--CO--NH-- and n represents 1, 2 or 3,with formaldehyde and with hydrogen in the presence of a condensation catalyst and a hydrogenation catalyst at elevated temperature, the methylene compound being introduced into the liquid phase of the mixture of reactants in the course of the reaction.Type: GrantFiled: July 18, 1984Date of Patent: January 28, 1986Assignee: Bayer AktiengesellschaftInventors: Heinz U. Blank, Erich Wolters
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Patent number: 4343953Abstract: The present invention relates to a novel method for producing cyclopentenolone of the formula (I), ##STR1## which is a useful intermediate for producing agricultural chemicals, which comprises reacting an acetonedicarboxylic ester of the formula (VII), ##STR2## wherein R is a C.sub.1 -C.sub.6 alkyl group, with 2-propynyl chloride in the presence of magnesium alkoxide and in the presence of alkali iodide to obtain novel mono-(2-propynyl)-substituted acetonedicarboxylic ester of the formula (VI), ##STR3## wherein R is as defined above; hydrolyzing the mono-(2-propynyl)-substituted acetonedicarboxylic ester of the formula (VI) under alkaline conditions with an alkali and then reacting the hydrolyzed product with methylglyoxal of the formula, ##STR4## to obtain novel .gamma.-diketone of the formula (V), ##STR5## and ring-closing the .gamma.-diketone of the formula (V) under alkaline condition.Type: GrantFiled: June 16, 1980Date of Patent: August 10, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Noritada Matsuo, Nobushige Itaya, Kohichi Aketa, Osamu Magara, Toshio Nishioka
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Patent number: 4339606Abstract: Ketones are converted in one step to saturated dimeric ketones by passing them over a zeolite having a silica to alumina ratio of at least 12 and a Constraint Index of from 1 to 12 and containing a Group VIII metal.Type: GrantFiled: February 6, 1981Date of Patent: July 13, 1982Assignee: Mobil Oil CorporationInventors: Tracy J. Huang, Werner O. Haag