Ag, Au, Pd, Pt, Rh, Ir, Ru, Or Os Containing Catalyst Utilized Patents (Class 568/401)
-
Patent number: 11110443Abstract: A method comprising a) contacting a solvent, a carboxylic acid, and a peroxide-containing compound to form an acidic mixture wherein a weight ratio of solvent to carboxylic acid in the acidic mixture is from about 1:1 to about 100:1; b) contacting a titanium-containing compound and the acidic mixture to form a solubilized titanium mixture wherein an equivalent molar ratio of titanium-containing compound to carboxylic acid in the solubilized titanium mixture is from about 1:1 to about 1:4 and an equivalent molar ratio of titanium-containing compound to peroxide-containing compound in the solubilized titanium mixture is from about 1:1 to about 1:20; and c) contacting a chromium-silica support comprising from about 0.1 wt. % to about 20 wt. % water and the solubilized titanium mixture to form an addition product and drying the addition product by heating to a temperature in a range of from about 50° C. to about 150° C. and maintaining the temperature in the range of from about 50° C. to about 150° C.Type: GrantFiled: December 28, 2020Date of Patent: September 7, 2021Assignee: Chevron Phillips Chemical Company LPInventors: Max P. McDaniel, Kathy S. Clear, Jeremy M. Praetorius, Eric D. Schwerdtfeger, Mitchell D. Refvik, Mark L. Hlavinka
-
Patent number: 9120732Abstract: The disclosure provides a dual-catalysis system for direct conversion of olefins to alcohols. The cooperative catalytic system contains one oxidizing catalyst and one transfer-hydrogenation catalyst. A wide variety of olefins, including aromatic and aliphatic olefins, can be used as the reactant. The transformation proceeds with anti-Markovnikov selectivity, and in some aspects provides primary alcohols as major products. The disclosure further provides a system for oxidation of olefins with anti-Markovnikov selectivity.Type: GrantFiled: December 29, 2011Date of Patent: September 1, 2015Assignee: California Institute of TechnologyInventors: Guangbin Dong, Robert H. Grubbs, Peili Teo, Zach K. Wickens
-
Patent number: 8618346Abstract: The subject invention provides a potentially economically viable process for the destruction of small to large quantities of sulfur and nitrogen mustards and lewisite, their homologous/analogues, and similar chemical warfare agents at ambient conditions without producing any toxic by-products. The process uses the superoxide ion that is either electrochemically generated by the reduction of oxygen in ionic liquids or chemically by dissolving Group 1 (alkali metals) or Group 2 (alkaline earth metals) superoxides, e.g. potassium superoxide, in ionic liquids.Type: GrantFiled: March 26, 2008Date of Patent: December 31, 2013Assignee: King Saud UniversityInventors: Inas Muen Al Nashef, Saeed M. Al Zahrani
-
Patent number: 8507728Abstract: A method for manufacturing a ketone includes oxidizing an internal olefin or a cyclic olefin having one carbon-carbon double bond or more at a position other than terminals of a molecule thereof in an amide-based solvent in the presence of water, a palladium catalyst, and molecular oxygen, thereby bonding an oxo group to at least one of the carbon atoms constituting the carbon-carbon double bond, in which the amide-based solvent is represented by the formula in the formula (1), R1 represents an alkyl group having 1 to 4 carbon atoms, R2 and R3 each independently represent an alkyl group having 1 to 4 carbon atoms or an aryl group, and when R1 and R2 are alkyl groups, R1 and R2 may be bonded to each other to form a ring structure.Type: GrantFiled: November 24, 2009Date of Patent: August 13, 2013Assignee: JX Nippon Oil & Energy CorporationInventors: Kiyotomi Kaneda, Hisashi Sone
-
Patent number: 8258348Abstract: A process for producing a carbonyl compound corresponding to an olefin, the process comprising reacting the olefin with molecular oxygen in a water-containing liquid phase comprising a palladium catalyst, a vanadium compound, and a heteropoly acid having a heteropoly anion represented by the Formula: [XaMbM?cOd]n? wherein X is any of elements selected from P, Si, and S; a represents an integer of 1 or 2; M and M? represent any of elements selected from Mo, W, V, Ta, and Nb; b and c represent an integer of 0 or more; d represents an integer of 1 or more; and n represents an integer of 1 or more.Type: GrantFiled: March 18, 2009Date of Patent: September 4, 2012Assignee: Sumitomo Chemical Company, LimitedInventors: Junichi Nishimoto, Masayoshi Murakami
-
Publication number: 20120197036Abstract: A method for manufacturing a ketone, includes oxidizing an internal olefin or a cyclic olefin having a functional group containing a hetero atom and one carbon-carbon double bond or more at a position other than terminals of a molecule thereof in an amide-based solvent in the presence of water, a palladium catalyst, and molecular oxygen, without oxidizing the functional group, thereby bonding an oxo group to at least one of the carbon atoms constituting the carbon-carbon double bond. The amide-based solvent is represented by formula (1): wherein R1 represents an alkyl group having 1 to 4 carbon atoms; R2 and R3 each independently represent an alkyl group having 1 to 4 carbon atoms or an aryl group; and when R1 and R2 are alkyl groups, R1 and R2 may be bonded to each other to form a ring structure.Type: ApplicationFiled: October 8, 2010Publication date: August 2, 2012Applicants: Osaka University, JX NIPPON OIL & ENERGY CORPORATIONInventors: Kiyotomi Kaneda, Hisashi Sone
-
Publication number: 20110288340Abstract: A method for manufacturing a ketone includes oxidizing an internal olefin or a cyclic olefin having one carbon-carbon double bond or more at a position other than terminals of a molecule thereof in an amide-based solvent in the presence of water, a palladium catalyst, and molecular oxygen, thereby bonding an oxo group to at least one of the carbon atoms constituting the carbon-carbon double bond, in which the amide-based solvent is represented by the formula in the formula (1), R1 represents an alkyl group having 1 to 4 carbon atoms, R2 and R3 each independently represent an alkyl group having 1 to 4 carbon atoms or an aryl group, and when R1 and R2 are alkyl groups, R1 and R2 may be bonded to each other to form a ring structure.Type: ApplicationFiled: November 24, 2009Publication date: November 24, 2011Applicant: JX NIPPON OIL & ENERGY CORPORATIONInventors: Kiyotomi Kaneda, Hisashl Sone
-
Publication number: 20110172448Abstract: A cost effective process is presented for carrying out catalytic, in particular also exothermic, endothermic or autothermal reactions with optimum yield and selectivity. The system used is a wall-flow monolith which forces a flow from the inlet channel through the porous wall into the outlet channel by reciprocal closure of the gas channels. This is operated such that mass transfer and heat transport are determined virtually exclusively by convection, and diffusion-related thermal conduction phenomena can be neglected.Type: ApplicationFiled: June 24, 2009Publication date: July 14, 2011Inventors: Martin Votsmeier, Susanne Ungermann, Juergen Gieshoff, Thomas Kreuzer
-
Patent number: 7820854Abstract: The present invention relates to an improved process for the conversion of alkanes to unsaturated carboxylic acids.Type: GrantFiled: March 19, 2008Date of Patent: October 26, 2010Assignee: Rohm and Haas CompanyInventors: Andrew Michael Lemonds, Eric Gustave Lundquist, Donald Lee Zolotorofe
-
Patent number: 7569734Abstract: In accordance with aspects of the invention methods of using rhodium hydroquinone catalysts for the conjugate addition of boronic acids are disclosed.Type: GrantFiled: June 15, 2006Date of Patent: August 4, 2009Assignee: Brown UniversityInventors: William C. Trenkle, Julia L. Barkin, Seung Uk Son, Dwight A. Sweigart, Marcus D. Faust, Jr.
-
Publication number: 20070161812Abstract: A process for oxidizing a hydrocarbon, which comprises subjecting the hydrocarbon to a liquid phase catalytic oxidation reaction in the presence of at least one oxidation catalyst to form an oxidized product.Type: ApplicationFiled: December 28, 2006Publication date: July 12, 2007Inventors: Andrew Michael Lemonds, Donald Lee Zolotorofe
-
Patent number: 6911563Abstract: A method for carrying out a reaction of one substance capable of being activated by a catalyst with another substance capable of reacting with said one substance activated, characterized in that the substance capable of being activated is activated by passing the substance through a diaphragm type catalyst and the reaction is thus performed in one reaction step; a method for producing an aromatic alcohol utilizing the above method; and a reaction apparatus suitable for these reactions. In the method, one substance is activated by passing through a diaphragm type catalyst and an objective reaction is carried out by using the activated substance, and the reaction can be performed in one reaction step and with safety. Moreover, the contact of the above activated substance with a compound to be reacted therewith can be freely controlled, and therefore, over-reaction can be prevented and an objective product can be produced in high yield.Type: GrantFiled: December 27, 2001Date of Patent: June 28, 2005Assignees: National Institute of Advanced Industrial Science, NOK CorporationInventors: Fujio Mizukami, Shuichi Niwa, Makoto Toba, Naotsugu Itoh, Tomonari Saito, Takemi Nanba, Hiroshi Shoji, Kazuhiko Haba
-
Publication number: 20040138506Abstract: Aliphatic or alicyclic monoketones or alicyclic diketones of formula (I): R1—C(═O)—R2, wherein R1 is a linear or branched C1-10-alkyl group and R2 is a linear or branched C1-10-alkyl group or a phenyl group, or R1 and R2 together are —(CH2)m—[C(═O)]n—(CH2)p—, wherein m and p independently are integers from 1 to 4 and n is 0 or 1, thus forming an alicyclic ring together with the carbonyl group of (I), are produced by oxidizing an alcohol of formula (II): R1′—CHOH—R2′, in which R1′ and R2′ either have the same meaning as R1 and R2 above or, if R1 and R2 together are —(CH2)m—[C(═O]n—(CH2)p—, are together —(CH2)m—(CHOH)n—(CH2)p— wherein m, n and p are as defined above, with a peroxy compound in the presence of a carboxylic acid and a manganese(IV) complex of 1,4,7-trimethyl-1,4,7-triazacyclononane.Type: ApplicationFiled: October 27, 2003Publication date: July 15, 2004Inventors: Georg Sss-Fink, Georgiy B Shul'Pin, Lidia S Shul'Pina
-
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
-
Patent number: 6723882Abstract: Dialkyl ketones are prepared by reductive carbonylation of &agr;-olefins by means of carbon monoxide and hydrogen in the presence of a catalyst system comprising (a) palladium or a palladium compound; (b) a phosphine; (c) a protic acid having a pKa of ≦4.5, measured in aqueous solution at 25° C.; and (d) a solubilizable carboxamide.Type: GrantFiled: July 18, 2002Date of Patent: April 20, 2004Assignee: BASF AktiengesellschaftInventors: Michael Slany, Martin Schäfer, Michael Röper
-
Patent number: 6703528Abstract: There are disclosed are a method for producing at least one compound selected from a carbonyl compound and a hydroxy adduct compound by an oxidative cleavage or addition reaction of an olefinic double bond of an olefin compound, which contains reacting an olefin compound with hydrogen peroxide, utilizing as a catalyst, at least one member selected from (a) tungsten, (b) molybdenum, or (c) a tungsten or molybdenum metal compound containing (ia) tungsten or (ib) molybdenum and (ii) an element of Group IIIb, IVb, Vb or VIb excluding oxygen, and a catalyst composition.Type: GrantFiled: August 10, 2001Date of Patent: March 9, 2004Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Hagiya, Naoyuki Takano, Akio Kurihara
-
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
-
Patent number: 6479707Abstract: The present invention provides a process for producing 2-butanone and 2-butanol under comparatively mild conditions with a decreased number of steps by direct oxidization of a hydrocarbon, which is cheaper than butenes, as a raw material using molecular oxygen such as air. The process for producing 2-butanone and 2-butanol comprises directly oxidizing n-butane using molecular oxygen in the presence of aluminum phosphate containing transition metal atoms and a selectivity-improving agent, as required.Type: GrantFiled: December 12, 2001Date of Patent: November 12, 2002Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Hideki Omori, Kazuhiko Haba
-
Patent number: 6395904Abstract: The subject invention provides a binuclear metal complex having structure (I) wherein M1, and M2 are independently selected from the group consisting of Fe, Co, Mn and Ru; wherein m and n are independently +2 or +3; wherein R1, R2, R3, R4, R5 and R6 are independently a linear C1-C6 alkyl, C5-C6 cycloalkyl, phenyl, etc.; wherein (i) R1 and R2, (ii) R3 and R4, or (iii) R5 and R6 independently and optionally are linked covalently and together with the respective adjoining C atom comprise a spirocyclic ring; wherein i, j and k are integers such that 2≦i+j+k≦4; wherein p is 1 or 2, and q is 0, 1 or 2 such that m+n−4=p×q; wherein (i) R1 or R2 and R3 or R4, (ii) R3 or R4 and R4 or R5, or (iii) R1 or R2 and R5 or R6 independently and optionally are linked covalently and together with the respective adjoining C atoms comprise a fused ring; wherein Ar is 1,2-phenylene, 1,2- or 2,3-naphthylene, etc.Type: GrantFiled: June 6, 2000Date of Patent: May 28, 2002Assignee: Yale UniversityInventors: John P. Caradonna, Subhasish Mukerjee, Adonis Stassinopoulos
-
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
-
Patent number: 6160183Abstract: A catalytic process is disclosed for oxidizing cycloalkanes directly to form, in a single step, a mixture containing the corresponding alcohol and ketone. In particular, the invention relates to oxidizing a cycloalkane by contacting it with a source of oxygen and a catalytic amount of a heterogeneous catalyst. The catalysts of the invention include gold (including gold sol-gel compounds) and sol-gel compounds containing particular combinations of Cr, Co, Zr, Ta, Si, Mg, Nb, Al and Ti, wherein certain of those metals have been combined with an oxide, such as an inorganic matrix of hydroxides or oxides, or combinations thereof. The catalysts may also optionally be supported on a suitable support member.Type: GrantFiled: February 8, 1999Date of Patent: December 12, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Joe Douglas Druliner, Norman Herron, Kostantinos Kourtakis
-
Patent number: 6140544Abstract: A process for oxidizing a reaction gas in the presence of a catalyst solution comprisinga) oxidizing the reaction gas in a reactor in the presence of the catalyst solution, a reaction mixture being formed comprising droplets of the catalyst solution,b) passing the reaction gas into a first separator wherein the droplets of the catalyst solution are removed from the reaction mixture,c) passing the remaining reaction mixture from the first separator into a scrubbing apparatus wherein the oxidation product is removed from the reaction mixture, andd) passing the reaction mixture from the first separator through a second separator downstream of the first separator and upstream of a scrubbing apparatus wherein residual catalyst solution from the reaction mixture is removed.Type: GrantFiled: April 19, 1999Date of Patent: October 31, 2000Assignee: Celanese GmbHInventors: Bernd Rinne, Erhard Franken-Stellamans
-
Patent number: 6124505Abstract: The invention provides a catalyst for partial oxidation of hydrocarbon in the presence of a reducing compound, the catalyst comprising ultra-fine gold particles immobilized on a titanium-containing oxide, and a process for preparing an oxygen-containing organic compound, the process comprising the step of oxidizing hydrocarbon with oxygen in the presence of the above catalyst and a reducing compound.Type: GrantFiled: October 29, 1998Date of Patent: September 26, 2000Assignees: Agency of Industrial Science and Technology, Nippon Shokubai Co., Ltd.Inventors: Masatake Haruta, Yuri Angelov Kalvachev, Susumu Tsubota, Toshio Hayashi, Masahiro Wada
-
Patent number: 6121498Abstract: A method of producing acetaldehyde hydrogenates acetic acid in the presence of an iron oxide catalyst containing between 2.5 and 90 wt % Pd, more preferably 10 and 80 wt % Pd and most preferably 20 and 60 wt % Pd. The catalyst has a specific surface area of less than 150 m.sup.2 /g. Hydrogen and acetic acid are fed to a reactor in a hydrogen to acetic acid ratio of 2:1 to 25:1, more preferably in a hydrogen to acetic acid ratio of 3:1 to 15:1 and most preferably in a hydrogen to acetic acid ratio of 4:1 to 12:1. The hydrogenation is performed at a temperature of about 250.degree. C. to 400.degree. C., more preferably about 270.degree. C. to 350.degree. C. and most preferably about 280.degree. C. to 325.degree. C. The hydrogenation of acetic acid produces a partially gaseous product, and acetaldehyde is absorbed from the partially gaseous product with a solvent containing acetic acid. The gas remaining after the absorption step contains hydrogen, and this gas is recycled for the hydrogenation of acetic acid.Type: GrantFiled: April 30, 1998Date of Patent: September 19, 2000Assignee: Eastman Chemical CompanyInventors: Gerald C. Tustin, Leslie S. Depew, Nick A. Collins
-
Patent number: 5710342Abstract: Carbonyl compounds can be prepared by catalytic oxidation of olefins with oxygen or oxygen-containing gases in a microemulsion (ME) as reaction medium and catalyst support. The catalysts present in ME and used for this purpose are characterized by a content of 0.0001-10% by weight of a Pd compound and by a content of 0.0005-20% by weight of a subgroup metal compound or a quinone, based on the total weight of the catalysts present in the ME.Type: GrantFiled: December 6, 1995Date of Patent: January 20, 1998Assignee: Bayer AktiengesellschaftInventors: Laszlo Imre, Reinhard Schomacker, Judit Daun
-
Patent number: 5623090Abstract: An alcohol or a ketone or a mixture thereof is produced from a saturated hydrocarbon or an epoxide is produced from an unsaturated hydrocarbon by passing a mixture comprising of molecular hydrogen, the saturated or unsaturated hydrocarbon and oxygen through a bed of a catalyst comprising a titanium dioxide carrier and ultrafine gold particles deposited on the carrier, thereby effecting the oxidation of the hydrocarbon with oxygen.Type: GrantFiled: October 25, 1995Date of Patent: April 22, 1997Assignee: Agency of Industrial Science & Technology, Ministry of International Trade & IndustryInventors: Masatake Haruta, Susumu Tsubota, Toshio Hayashi
-
Patent number: 5557014Abstract: The present invention provides aqueous catalyst solutions useful for oxidation of olefins to carbonyl products, comprising a palladium catalyst and a polyoxoacid or polyoxoanion oxidant comprising vanadium. It also provides processes for oxidation of olefins to carbonyl products, comprising contacting olefin with the aqueous catalyst solutions of the present invention. It also provides processes for oxidation of olefins to carbonyl products by dioxygen, comprising contacting olefin with the aqueous catalyst solutions of the present invention, and further comprising contacting dioxygen with the aqueous catalyst solutions. In certain aqueous catalyst solutions and related processes of the present invention, the solution has a hydrogen ion concentration greater than 0.10 mole per liter when essentially all of the oxidant is in its oxidized state. In other aqueous catalyst solution and related processes of the present invention, the solution is essentially free of sulfuric acid and sulfate ions.Type: GrantFiled: November 16, 1995Date of Patent: September 17, 1996Assignee: Catalytica, Inc.Inventors: John H. Grate, David R. Hamm, Kenneth A. Klingman, Robert J. Saxton, Shannan J. Downey
-
Patent number: 5506363Abstract: The present invention provides aqueous catalyst solutions useful for oxidation of olefins to carbonyl products, comprising a palladium catalyst, a polyoxoacid or polyoxoanion oxidant comprising vanadium, and chloride ions. It also provides processes for oxidation of olefins to carbonyl products, comprising contacting olefin with the aqueous catalyst solutions of the present invention. It also provides processes for oxidation of olefins to carbonyl products by dioxygen, comprising contacting olefin with the aqueous catalyst solutions of the present invention, and further comprising contacting dioxygen with the aqueous catalyst solutions. The present invention also provides a process for the oxidation of palladium(0) to palladium(II) comprising contacting the palladium(0) with an aqueous solution comprising chloride ions and a polyoxoacid or polyoxoanion oxidant comprising vanadium.Type: GrantFiled: September 4, 1992Date of Patent: April 9, 1996Assignee: Catalytica, Inc.Inventors: John H. Grate, David R. Hamm, Robert J. Saxton, Mark T. Muraoka
-
Patent number: 5414137Abstract: An improved process for preparing carbonyl compounds by oxidizing olefins is disclosed. The process comprises oxidizing an olefin with oxygen or an oxygen containing gas in the presence of a palladium compound or metallic palladium, a polyoxoanion compound and an organic phosphorus compound in a solvent selected from oxygen-containing organic compounds, sulfur-containing organic compounds and nitrogen-containing organic compounds. In this process, precipitating of the palladium component is prevented and the high, reaction rate is well maintained through the prolonged reaction period and thus carbonyl compounds can be produced with high efficiency and productivity.Type: GrantFiled: May 27, 1993Date of Patent: May 9, 1995Assignee: Idemitsu Kosan Company LimitedInventors: Hirotoshi Ishii, Masanori Tsuzuki, Yoshinori Saito
-
Patent number: 5237103Abstract: The process for preparing the carbonyl compound involves oxidizing the olefins in the presence of the catalyst composed of the palladium compound and the polyoxoanion compound in a mixture of water with a cyclic ether having at least a dioxane ring or a dioxolan ring or in the presence of the catalyst composed of the palladium compound, the polyoxoanion compound and the quinone and/or the aromatic diol in a solvent. This process yields carbonyl compounds, such as ketones and aldehydes, useful as solvents, raw chemicals and so on, with a high production rate per unit time and unit palladium quantity.Type: GrantFiled: January 31, 1992Date of Patent: August 17, 1993Assignee: Kemitsu Kosan Company LimitedInventors: Yoshinori Saito, Masanori Tsuzuki, Hirotoshi Ishii
-
Patent number: 5149880Abstract: Nitrogen-containing aromatic heterocyclic ligand-metal complexes and their use for the activation of hydrogen peroxide and dioxgen are disclosed. Processes whereby activated hydrogen peroxide or dioxygen are used to transform various organic substrates are also disclosed. In particular, processes for the conversion of methylenic carbons to carbonyls, for the dioxygenation of aryl olefins, acetylenes and aryl-.alpha.-diols, for the oxidation of alcohols and aldehydes and for the removal of mercaptans from gaseous streams and for the removal of hydrogen sulfide and/or mercaptans from liquid streams are disclosed.Type: GrantFiled: August 24, 1990Date of Patent: September 22, 1992Assignee: The Texas A & M University SystemInventors: Donald T. Sawyer, Ceshing Sheu, Andrzej Sobkowiak, Hui-Chan Tung
-
Patent number: 5126490Abstract: A process is disclosed for the catalytic oxydation of olefins to carbonyl compounds with molecular oxygen at elevated temperatures in the presence of rhodium oxide on a support. The process is applicable to a broad variety of olefins and is not limited to special olefins and forms especially ketones in a high selectivity.Type: GrantFiled: November 28, 1990Date of Patent: June 30, 1992Assignee: Princeton UniversityInventors: Jeffrey Schwartz, H. Eric Fischer, Jeffrey W. McMillan
-
Patent number: 5103064Abstract: A carbonyl compound is produced efficiently, stably and with good productivity by oxidizing a chain olefin in an alcoholic solvent in the presence of a catalyst system comprising palladium and a polyoxoanion as active components.Type: GrantFiled: September 4, 1990Date of Patent: April 7, 1992Assignee: Idemitsu Kosan Company LimitedInventors: Yoshinori Saito, Masanori Tsuzuki
-
Patent number: 4885399Abstract: Tischtschenko condensation of aldehydes is used to remove aldehydes from dry ketone-containing streams. The tischtschenko condensation is used to condense the aldehydes into esters whose boiling points are significantly different than the ketones, greatly simplifying the separation of the esters from the ketones. An organic extraction step is used to obtain a substantially dry ketone containing stream. One particularly preferred class of extraction solvents is selected from the group consisting of butane, pentane, hexane, heptane, octane, nonane, decane and mixtures thereof. In particularly preferred embodiments, the Tischtschenko reaction is used in the context of aqueous-phase catalyzed olefin oxidation to ketones. The aldehyde to ester condensation permits easy and efficient removal of the aldehyde analogs of the desired ketones.Type: GrantFiled: July 13, 1988Date of Patent: December 5, 1989Assignee: Catalytica, Inc.Inventors: Stanley F. Newman, Jacques C. De Deken, Michael L. Cook
-
Patent number: 4885377Abstract: Ruthenium trifluoroalkyl carboxylates are disclosed.Type: GrantFiled: January 22, 1988Date of Patent: December 5, 1989Assignee: University of FloridaInventors: Russell S. Drago, Shannon Davis
-
Patent number: 4847421Abstract: A substantially chloride-free palladium oxidation system, comprising a palladium component, a copper component, and a ligand is described. The Wacker system, consisting of palladium and copper chlorides is also improved by the addition of a ligand. The palladium and copper counterion are independently selected from BF.sub.4.sup.--, CF.sub.3 COO.sup.--, CH.sub.3 COO.sup.--, SO.sub.4.sup..dbd., and NO.sub.3.sup.--. The ligand is preferably a nitrile-containing compound.Type: GrantFiled: January 29, 1988Date of Patent: July 11, 1989Assignee: Catalytica, AssociatesInventors: Janis Vasilevskis, Paul L. Ridgway, Eric R. Evitt
-
Patent number: 4806692Abstract: A process for producing an oxygen-containing organic compound by oxidizing olefins under milder conditions is provided, which process comprises oxidizing an olefin activated by its complex formation, in the presence of a platinum group metal complex capable of forming an olefin complex through coordination of the platinum group metal with said olefin, and also in the presence of water, and further oxidizing and regenerating the resulting reduced platinum group metal complex with oxygen coordinated with a transition metal and activated thereby.Type: GrantFiled: January 21, 1986Date of Patent: February 21, 1989Assignee: Babcock-Hitachi Kabushiki KaishaInventors: Mutsuo Yamada, Taiji Kamiguchi, Hirotoshi Tanimoto, Yoshijiro Arikawa, Hiroyuki Kaku, Shigehito Takamoto
-
Patent number: 4769464Abstract: The invention relates to a process for the preparation of monocarbonyl or biscarbonyl compounds by reacting organic carbon compounds having one or more olefinic or aromatic double bonds in the molecule with the equivalent amount of ozone and by subsequently catalytically hydrogenating the ozonization products, wherein the peroxide-containing ozonization solution is fed continuously into a suspension of the hydrogenation catalyst in a lower aliphatic alcohol, while a peroxide content of not more than 0.1 mole/l is maintained, and the ozonization products are continuously cleaved reductively to give the corresponding carbonyl compounds.Type: GrantFiled: December 17, 1984Date of Patent: September 6, 1988Assignee: Chemie Linz Gesellschaft m.b.H.Inventor: Alexander Sajtos
-
Patent number: 4738943Abstract: A substantially chloride-free palladium oxidation system, comprising a palladium component, a copper component, and a ligand is described. The Wacker system, consisting of palladium and copper chlorides is also improved by the addition of a ligand. The palladium and copper counterion are independently selected from BF.sub.4.sup.-, CF.sub.3 COO.sup.-, SO.sub.4.sup.=, and NO.sub.3.sup.-. The ligand is preferably a nitrile-containing compound.Type: GrantFiled: August 21, 1987Date of Patent: April 19, 1988Assignee: Catalytica AssociatesInventors: Janis Vasilevskis, Paul L. Ridgway, Eric R. Evitt
-
Patent number: 4723041Abstract: The addition of redox-active metal components and ligands, alternatively or simultaneously, results in increased conversion and selectivity in the palladium-catalyzed oxidation of olefins to carbonyl products in the presence of polyoxoanions. In preferred modes, heteropolyoxoanions and isopolyoxoanions containing tungsten, molybdenum and vanadium, individually or in combination, are described. The use of copper as the redox-active metal component shows reduced allylic reactivity. The elimination of chloride from the catalyst system provides substantial engineering advantages over the prior art, particularly, the reduction of corrosion and chloro-organic by-product formation. The use of redox-active metal components and/or ligands makes the palladium-polyoxoanion catalyst system industrially practicable.Type: GrantFiled: March 31, 1986Date of Patent: February 2, 1988Assignee: Catalytica AssociatesInventors: Janis Vasilevskis, Jacques C. De Deken, Robert J. Saxton, Paul R. Wentrcek, Jere D. Fellmann, Lyubov S. Kipnis
-
Patent number: 4620038Abstract: A process for producing methyl ethyl ketone selectively and with a high yield by oxygen-oxidizing 1-butene under mild conditions is provided, which process is characterized by using a composite catalyst containing a complex (MmXn.Ll) capable of forming an oxygen complex by coordination of the complex with oxygen and a complex catalyst (M'm'Xn'.L'l') capable of forming a 1-butene complex by coordination of the complex with 1-butene, wherein M represents a specified transition metal such as Cu; X, an anion; L, an organic phosphorus compound as ligand; M', a specified transition metal such as palladium; L', a nitrile, organic fluorine or phosphorus compound as ligand; m, m', n and n', each a number determined by the valences of the transition metals and the anion; l and l', each the number of ligands.Type: GrantFiled: February 27, 1985Date of Patent: October 28, 1986Assignee: Babcock-Hitachi Kabushiki KaishaInventors: Hirotoshi Tanimoto, Mutsuo Yamada, Yoshijiro Arikawa, Taiji Kamiguchi, Yasuyuki Nishimura, Hiroyuki Kaku
-
Patent number: 4605776Abstract: A process for producing acetone selectively and with a high yield by oxidizing propylene by means of the combined oxygen in an oxygen complex under milder conditions and at a single stage is provided wherein a composite catalyst comprising as catalyst components, a transition metal complex with the metal ion of which oxygen molecule can coordinate to form an oxygen complex, and another kind transition metal complex with the metal ion of which propylene can coordinate to form a propylene complex is employed, and propylene activated by the complex formation is oxidized by the combined oxygen activated by the complex formation to thereby obtain acetone.Type: GrantFiled: January 23, 1985Date of Patent: August 12, 1986Assignee: Babcock-Hitachi Kabushiki KaishaInventors: Taiji Kamiguchi, Mutsuo Yamada, Yoshijiro Arikawa, Takanori Kuwahara, Hirotoshi Tanimoto, Yasuyuki Nishimura, Hiroyuki Kaku
-
Patent number: 4568770Abstract: Terminal carbon-carbon double bonds of olefinic hydrocarbons are converted to carbonyl groups by reacting the olefin with oxygen in the presence of (a) a catalyst comprising (i) one or more of the metals palladium, rhodium, ruthenium or iridium, and (ii) copper, (b) a diluent comprising two liquid phases, and (c) a surfactant, provided that when the metal is palladium no alkali or alkaline earth metal is present and the surfactant is dodecyltrimethylammonium or cetyltrimethylammonium chloride or bromide.Type: GrantFiled: September 28, 1983Date of Patent: February 4, 1986Assignee: The British Petroleum Company p.l.c.Inventors: Howard Alper, Krzysztof R. Januszkiewicz, David J. H. Smith
-
Patent number: 4560803Abstract: An improved process is provided for forming ketones from the corresponding olefins by vapor phase oxidation of the olefin in the presence of molecular oxygen and water vapor employing a heterogeneous catalyst comprising rhenium compounds and complexes, optionally containing at least one metal compound or complex selected from the group consisting of Group VIB metals and Group VIII noble metals, and mixtures thereof. It has been surprisingly found that these catalysts effect the formation of ketones in high selectivities with minimal selectivities to the undesirable carbon dioxide and carbon monoxide by-products.Type: GrantFiled: July 25, 1983Date of Patent: December 24, 1985Assignee: Exxon Research & Engineering Co.Inventors: Chuen Y. Yeh, Charles Savini
-
Patent number: 4560804Abstract: An improved process is provided for forming ketones from the corresponding olefins by vapor phase oxidation of the olefin in the presence of water vapor, and optionally in the additional presence of molecular oxygen employing a heterogeneous catalyst comprising at least one member selected from the group consisting of Ce, Nd and La and compounds and complexes thereof, optionally containing at least one metal compound or complex selected from the group consisting of Group VIB metals and Group VIII noble metals, and mixtures thereof. It has been surprisingly found that these catalysts effect the formation of ketones in high selectivities with minimal selectivities to the undesirable carbon dioxide and carbon monoxide by-products.Type: GrantFiled: July 25, 1983Date of Patent: December 24, 1985Assignee: Exxon Research & Engineering Co.Inventors: Chuen Y. Yeh, Charles Savini
-
Patent number: 4551555Abstract: In the process for producing a carbonyl compound by contacting olefin and oxygen or oxygen-containing gas with a catalyst in the presence of water, a catalyst comprising a carrier and (a) rhodium, (b) manganese and (c) at least one of the Group IIIA elements (excluding an actinium series elements) is used. Also, the catalyst further containing zinc compounds as the component (d) is used.According to this invention, the selectivity and the conversion of carbonyl compound such as methyl ethyl ketone are highly improved, and halogenated compounds are not produced.Type: GrantFiled: June 1, 1984Date of Patent: November 5, 1985Assignee: Idemitsu Kosan Company LimitedInventors: Yoshio Hironaka, Takashi Kumazawa
-
Patent number: 4550212Abstract: A Pd/heteropolyacid/boric acid catalyst system, when used with proper diluents, improves the oxidation of olefins to ketones, while reducing scum and deposits on reactor surfaces.Type: GrantFiled: March 9, 1982Date of Patent: October 29, 1985Assignee: Phillips Petroleum CompanyInventor: Tod K. Shioyama
-
Patent number: 4532362Abstract: The use of fluorocarbons during the multiphase oxidation of olefins to ketones with Wacker-type catalysts improves reaction efficiency.Type: GrantFiled: February 17, 1984Date of Patent: July 30, 1985Assignee: Phillips Petroleum CompanyInventors: Simon G. Kukes, Tod K. Shioyama
-
Patent number: 4507507Abstract: A Pd/heteropolyacid/surfactant catalyst system, when used with proper diluents, improves the oxidation of olefins to ketones, while reducing corrosive effects.Type: GrantFiled: October 12, 1983Date of Patent: March 26, 1985Assignee: Phillips Petroleum CompanyInventor: Timothy P. Murtha
-
Patent number: 4507506Abstract: The conversion of long-chain alpha-olefins to methyl ketones can be efficiently carried out using reaction systems containing palladium, a co-catalyst, and an aqueous solvent system.Type: GrantFiled: April 21, 1983Date of Patent: March 26, 1985Assignee: Phillips Petroleum CompanyInventor: Tod K. Shioyama