Heavy Metal Containing Material Utilized Patents (Class 568/360)
  • Patent number: 5912388
    Abstract: A process for preparing an aldehyde or ketone comprising reacting a primary or secondary alcohol with oxygen in the presence of a base, a catalytic amount of a copper salt and a suitable lignad under anhydrous conditions.
    Type: Grant
    Filed: November 12, 1997
    Date of Patent: June 15, 1999
    Assignee: Zeneca Limited
    Inventors: Christopher John Urch, Istvan Ettienne Marko, Masao Tuskazaki, Paul Richard Giles, Stephen Martin Brown
  • Patent number: 5877354
    Abstract: The present invention is a process for the production of isophorone having improved color and color stability. Crude isophorone is selectively hydrogenated to remove color forming impurities. The product isophorone will have an APHA color of about 10 or less.
    Type: Grant
    Filed: December 3, 1997
    Date of Patent: March 2, 1999
    Assignee: Aristech Chemical Corporation
    Inventors: Chandrashekhar P. Kelkar, Alain A. Schutz
  • Patent number: 5767320
    Abstract: Cyclohexane is oxidized to a mixture of cyclohexanone and cyclohexanol by reaction with oxygen in the presence of a metal complex of phthalocyanine or porphyrin wherein some or all of the hydrogen atoms of the phthalocyanine or porphyrin have been replace by electron withdrawing groups.
    Type: Grant
    Filed: July 26, 1996
    Date of Patent: June 16, 1998
    Assignee: Council of Scientific & Industrial Research
    Inventors: Robert Raja, Paul Ratnasamy
  • Patent number: 5756852
    Abstract: Process for the catalytic oxidation of a saturated hydrocarbon to obtain a ketone which involves carrying out the oxidation simultaneously with the oxidation of H.sub.2 S to form elemental sulfur and the ketone.
    Type: Grant
    Filed: October 15, 1996
    Date of Patent: May 26, 1998
    Inventor: Derek H. R. Barton
  • Patent number: 5710342
    Abstract: 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: Grant
    Filed: December 6, 1995
    Date of Patent: January 20, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Laszlo Imre, Reinhard Schomacker, Judit Daun
  • Patent number: 5623090
    Abstract: 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: Grant
    Filed: October 25, 1995
    Date of Patent: April 22, 1997
    Assignee: Agency of Industrial Science & Technology, Ministry of International Trade & Industry
    Inventors: Masatake Haruta, Susumu Tsubota, Toshio Hayashi
  • Patent number: 5557014
    Abstract: 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: Grant
    Filed: November 16, 1995
    Date of Patent: September 17, 1996
    Assignee: Catalytica, Inc.
    Inventors: John H. Grate, David R. Hamm, Kenneth A. Klingman, Robert J. Saxton, Shannan J. Downey
  • Patent number: 5426237
    Abstract: The present invention provides a process for the oxidation of straight-chain, branched-chain or cyclic alkanes of 1-20 carbon atoms and benzene derivatives represented by the following formulas (1)-(2). The alcohols and ketones obtained by the oxidation of the alkanes mentioned above and those by the oxidation of the benzene derivatives mentioned above represented by the following formulas (3)-(6) are important as basic starting materials in producing various chemical products including resins, such as nylon and polyester, pharmaceuticals, agricultural chemicals, perfumes, dyes, etc.
    Type: Grant
    Filed: March 24, 1994
    Date of Patent: June 20, 1995
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Shun-Ichi Murahashi, Yoshiaki Oda
  • Patent number: 5414137
    Abstract: 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: Grant
    Filed: May 27, 1993
    Date of Patent: May 9, 1995
    Assignee: Idemitsu Kosan Company Limited
    Inventors: Hirotoshi Ishii, Masanori Tsuzuki, Yoshinori Saito
  • Patent number: 5250739
    Abstract: This invention is a process for catalytically oxidizing cycloolefins, particularly cyclohexenes, to form a variety of oxygenates. The catalyst used in the process is a covalently bonded iridium-heteropolyanion species. The process uses the catalyst in conjunction with a gaseous oxygen containing gas to form 2-cyclohexen-1-ol and also 2-cyclohexen-1-one.
    Type: Grant
    Filed: March 20, 1992
    Date of Patent: October 5, 1993
    Assignee: Catalytica, Inc.
    Inventors: Noritaka Mizuno, David K. Lyon, Richard G. Finke
  • Patent number: 5237103
    Abstract: 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: Grant
    Filed: January 31, 1992
    Date of Patent: August 17, 1993
    Assignee: Kemitsu Kosan Company Limited
    Inventors: Yoshinori Saito, Masanori Tsuzuki, Hirotoshi Ishii
  • Patent number: 5235111
    Abstract: Process for oxidating paraffinic compounds into their corresponding alcoholic and/or ketonic derivatives, which process consists in causing said paraffins to react, at a temperature comprised within the range of from 0.degree. C. to 100.degree. C., preferably in an acidic medium, with a mixture of oxygen and hydrogen, in the presence of a catalyst on the basis of titanium-silicalite and of a noble metal and/or a derivative of such a metal.
    Type: Grant
    Filed: July 16, 1991
    Date of Patent: August 10, 1993
    Assignees: Eniricherche S.p.A., Shamprogetti S.p.A.
    Inventors: Mario G. Clerici, Giuseppe Bellussi
  • Patent number: 5233092
    Abstract: The invention relates to a new compound of the formular (1): ##STR1## wherein m.sub.1 =0, 1 or 2, m.sub.2 =0, 1 or 2, m.sub.1 and m.sub.2 are not to be simultaneously 0 or simultaneously 2; n.sub.1 =2-m.sub.1, n.sub.2 =2-m.sub.2 ; R=either H or alkyl with 1 to 8 carbon atoms, R'=alkyl with 1 through 18 carbon atoms, and X=H or OH.The invention also relates to the preparation thereof, the compositions containing them and the application in catalysis of oxidation of hydrocarbons, particularly in catalysis of oxidation of cyclohexane.
    Type: Grant
    Filed: January 17, 1992
    Date of Patent: August 3, 1993
    Inventor: Xiao Zaosheng
  • Patent number: 5149880
    Abstract: 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: Grant
    Filed: August 24, 1990
    Date of Patent: September 22, 1992
    Assignee: The Texas A & M University System
    Inventors: Donald T. Sawyer, Ceshing Sheu, Andrzej Sobkowiak, Hui-Chan Tung
  • Patent number: 5126490
    Abstract: 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: Grant
    Filed: November 28, 1990
    Date of Patent: June 30, 1992
    Assignee: Princeton University
    Inventors: Jeffrey Schwartz, H. Eric Fischer, Jeffrey W. McMillan
  • Patent number: 5118862
    Abstract: Disclosed is a process for producing an .alpha.,.beta.-unsaturated carbonyl compound represented by the formula [II]: ##STR1## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 each represents a hydrogen atom or a hydrocarbon residue and may be linear or may form a ring in optional combination thereof and total carbon atom number of R.sub.1, R.sub.2, R.sub.3 and R.sub.4 is 12 or less, which comprises contacting oxygen with an alkenyl compound represented by the formula [I]: ##STR2## wherein R.sub.1, R.sub.2, R.sub.3 and R.sub.4 are as defined above and X represents a trihydrocarbylsilyl group or an acyl group in the presence of a platinum group metal-supporting catalyst.
    Type: Grant
    Filed: August 27, 1990
    Date of Patent: June 2, 1992
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Toshihide Baba, Mitsuo Masai
  • Patent number: 5068464
    Abstract: A continuous process for the partial oxidation of hydrocarbons is disclosed wherein the oxidizing gas is partitioned into the hydrocarbon by means of countercurrent flow of an aqueous solution of oxygen prepared in a separate vessel, thus avoiding direct contact of hydrocarbon and oxidizing gas.
    Type: Grant
    Filed: May 26, 1988
    Date of Patent: November 26, 1991
    Assignee: BASF Corporation
    Inventor: David C. Hendrix
  • Patent number: 4959494
    Abstract: A method for oxidizing organic compounds by contacting organic compounds with molecular oxygen in the presence of a noble metal pyrochlore having the formula:A.sub.2+x B.sub.2-x O.sub.7-ywherein A is a pyrochlore structure metal cation, and B is one or more of Ru, Rh, Ir, Os, and Pt; x and y are greater than or equal to 0 and less than or equal to 1.0, at a temperature up to about 200.degree. C.
    Type: Grant
    Filed: July 6, 1987
    Date of Patent: September 25, 1990
    Assignee: Monsanto Company
    Inventor: Timothy R. Felthouse
  • Patent number: 4943644
    Abstract: A method of oxidizing olefins or alkanes by contacting with oxygen and a catalyst composition of the formula:Ru.sub.3 O[OCO(CF.sub.2).sub.y CF.sub.3 ].sub.6 LWherein: Ru are reuthenium atoms having a formal oxidation state of +2 or +3,L is a neutral or anionic ligand,Y is an integer from 0 to 6, andx is an integer from 1 to 3; and an anion.
    Type: Grant
    Filed: November 23, 1988
    Date of Patent: July 24, 1990
    Assignee: The University of Florida
    Inventors: Russell S. Drago, Shannon Davis
  • Patent number: 4927974
    Abstract: The invention relates to a process for preparing cyclohexanol and/or cyclohexanone, in which cyclohexene in a feed stream containing cyclohexene, cyclohexane and benzene is hydrated into cyclohexanol and/or oxidized into cyclohexanone, the cyclohexanol and/or cyclohexanone formed is separated from the reaction mixture thus obtained and the remaining cyclohexane and benzene are recycled to a preconnected cyclohexene preparation section, part of the stream that is recycled to the cyclohexene preparation section being subjected to a dehydrogenation reaction and the remaining part to a hydrogenation reaction, and the reaction streams thus obtained being combined to form the feed stream to the hydration and/or oxidation step.
    Type: Grant
    Filed: April 6, 1989
    Date of Patent: May 22, 1990
    Assignee: Stamicarbon B.V.
    Inventors: Paul C. van Geem, Franciscus T. B. van den Brink
  • Patent number: 4918239
    Abstract: This invention provides a method for producing cyclohexanone from cyclohexanol using oxidative dehydrogenation. More particularly, this invention comprises adding a certain amount of a gaseous oxidant to the cyclohexanol feed stream; and, converting the cyclohexanol to cyclohexanone over a CuO-ZnO catalyst.
    Type: Grant
    Filed: December 27, 1988
    Date of Patent: April 17, 1990
    Assignee: National Science Council
    Inventors: Ikai Wang, Yu-Ming Lin
  • Patent number: 4877903
    Abstract: Mixtures containing cyclohexanol and cyclohexanone are produced by oxidizing cyclohexane with air, and then decomposing the cyclohexyl hydroperoxide in such reaction mixture, in the presence of the cyclohexane, to form cyclohexanol and cyclohexanone, such oxidation and/or decomposition being carried out in the presence of a manganese source, a Bronsted acid and a pyridine ligand.
    Type: Grant
    Filed: November 14, 1988
    Date of Patent: October 31, 1989
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Costantini, Francoise Igersheim
  • Patent number: 4847421
    Abstract: 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: Grant
    Filed: January 29, 1988
    Date of Patent: July 11, 1989
    Assignee: Catalytica, Associates
    Inventors: Janis Vasilevskis, Paul L. Ridgway, Eric R. Evitt
  • Patent number: 4820875
    Abstract: In a process for vapour-phase synthesis of carbonyl compounds from alcohols a mixture of the alcohol and air or oxygen is passed over a silver catalyst. The concentration of alcohol:air or alcohol:oxygen is below the explosive limits. The process is conducted as a temperature between 200.degree. and 450.degree. C. Previously the production of carbonyl compounds required a temperature of 450.degree.-700.degree. C. which necessitated the use of heat exchangers using fused salt baths. The silver catalyst may be supported.
    Type: Grant
    Filed: December 23, 1987
    Date of Patent: April 11, 1989
    Assignee: Johnson Matthey Public Limited Company
    Inventors: Dennis E. Webster, Phillip J. Player
  • Patent number: 4816606
    Abstract: Aldehydes and ketones of the general formula I ##STR1## where R.sup.1 is hydrogen or an organic radical of 1 to n carbon atoms and R.sup.2 is a non-aromatic organic radical of 1 to m carbon atoms, (m+n) ranging from 2 to 24 and R.sup.1 and R.sup.2 being combinable to form a 4- to 12-membered ring, are prepared in a continuous manner by oxidizing an alcohol of the general formula II ##STR2## with oxygen or an oxygen-containing gas at elevated temperatures in the gas phase in the presence of a catalyst, by effecting the oxidation by means of a supported catalyst composed of an inert carrier having a smooth surface and from 0.1 to 20% by weight, based on the amount of carrier, of an active layer of copper, silver and/or gold in a tubular reactor or tube bundle reactor where the internal diameter D of the tube or tubes ranges from 10 to 50 mm and the largest diameter d of the coated supported catalysts is subject to the relationship d=from 0.1 to 0.2 D.
    Type: Grant
    Filed: September 30, 1987
    Date of Patent: March 28, 1989
    Assignee: Basf Aktiengesellschaft
    Inventors: Karl Brenner, Manfred Eggersdorfer, Wilhelm Ruppel, Harald Schultheiss, Hans-Ulrich Scholz
  • Patent number: 4806692
    Abstract: 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: Grant
    Filed: January 21, 1986
    Date of Patent: February 21, 1989
    Assignee: Babcock-Hitachi Kabushiki Kaisha
    Inventors: Mutsuo Yamada, Taiji Kamiguchi, Hirotoshi Tanimoto, Yoshijiro Arikawa, Hiroyuki Kaku, Shigehito Takamoto
  • Patent number: 4723041
    Abstract: 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: Grant
    Filed: March 31, 1986
    Date of Patent: February 2, 1988
    Assignee: Catalytica Associates
    Inventors: Janis Vasilevskis, Jacques C. De Deken, Robert J. Saxton, Paul R. Wentrcek, Jere D. Fellmann, Lyubov S. Kipnis
  • Patent number: 4675450
    Abstract: Production of cyclohexyl hydroperoxide during the cobalt catalyzed oxidation of cyclohexane is enhanced by conducting the oxidation in the presence of a phosphate ester.
    Type: Grant
    Filed: November 12, 1985
    Date of Patent: June 23, 1987
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: John B. Lyon, Gerald T. Stowe
  • Patent number: 4659829
    Abstract: The invention concerns peroxide complexes of metals complying with the general formula LnMXpY, wherein M is a metal selected from groups VIII, IB and VIIB, particularly cobalt, X is an anionic group, for example carboxylate, R is an alkyl, cycloalkyl or arylalkyl group, n=1 or 2, p=0 or 1 and n+p=2.L is a tridentated ligand from the group of 1,3 bis (2-pyridylimino) isoindolines.These complexes are obtained by reaction of a hydroperoxide ROOH with a complex of formula LnMXp. They can be used in oxidizing hydrocarbons to a mixture of alcohols and ketones, either as reactants or as catalysts.They are particularly useful to prepare tert-butanol by oxidation of isobutane in liquid phase, by means of an oxygen-containing gas such as air.
    Type: Grant
    Filed: January 31, 1985
    Date of Patent: April 21, 1987
    Assignee: Institut Francais du Petrole
    Inventors: Lucien Saussine, Alain Robine, Hubert Mimoun
  • Patent number: 4658056
    Abstract: A process for the catalytic oxidation of liquid cycloparaffins to oxidation products thereof is disclosed. In the process, partial oxidation products are formed by oxidizing the cycloparaffin with molecular oxygen-containing gas in the presence of an oxidation catalyst comprising two heavy metal compounds. The first heavy metal compound is a cobalt compound having ligands selected from dialkyl phosphate, dicycloalkylphosphate and alkylcycloalkylphosphate, optionally additionally combined with pyridine. The second heavy metal compound is a chromium alkanoate. A preferred catalyst is cobalt bis[di(2-ethylhexyl)phosphate] combined with chromium naphthenate.
    Type: Grant
    Filed: April 22, 1982
    Date of Patent: April 14, 1987
    Assignee: Du Pont Canada Inc.
    Inventor: Peter A. Sipos
  • Patent number: 4568769
    Abstract: Disclosed in a method for producing a mixture containing cycloalkanone and/or cycloalkanol which comprises oxidizing a cycloalkane with molecular oxygen to a cycloalkyl hydroperoxide represented by the formula (1): ##STR1## (wherein m represents an integer of 4.ltoreq.m.ltoreq.11) and decomposing the cycloalkyl hydroperoxide to obtain a mixture containing cycloalkanone and/or cycloalkanol, wherein the oxidation of the cycloalkane with molecular oxygen and/or the decomposition of the cycloalkyl hydroperoxide are carried out in the presence of a catalyst composition comprising at least one metallic salt represented by the formula (2):MX.sub.n (2)(wherein M represent Co, Mn, Cr or Fe, X represents an anionic ligand and n represents 2 or 3) and at least one compound represented by the formula (3): ##STR2## (wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.
    Type: Grant
    Filed: June 20, 1984
    Date of Patent: February 4, 1986
    Assignee: Sumitomo Chemical Company
    Inventors: Akira Yashima, Teruo Matsuda, Tadao Sato, Mitsuaki Takahashi, Kiyomi Sakai
  • Patent number: 4568770
    Abstract: 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: Grant
    Filed: September 28, 1983
    Date of Patent: February 4, 1986
    Assignee: The British Petroleum Company p.l.c.
    Inventors: Howard Alper, Krzysztof R. Januszkiewicz, David J. H. Smith
  • Patent number: 4560804
    Abstract: 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: Grant
    Filed: July 25, 1983
    Date of Patent: December 24, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Chuen Y. Yeh, Charles Savini
  • Patent number: 4560803
    Abstract: 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: Grant
    Filed: July 25, 1983
    Date of Patent: December 24, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Chuen Y. Yeh, Charles Savini
  • Patent number: 4551555
    Abstract: 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: Grant
    Filed: June 1, 1984
    Date of Patent: November 5, 1985
    Assignee: Idemitsu Kosan Company Limited
    Inventors: Yoshio Hironaka, Takashi Kumazawa
  • Patent number: 4532347
    Abstract: The instant invention relates to a membrane solvent extraction and reaction system. More particularly it pertains to an improvement in the membrane solvent extraction system wherein a solute is extracted through a polymeric membrane from one solvent liquid phase to an extracting solvent liquid without direct contact between the liquid phases which are separated by the membrane and in which the extracting solvent has no greater solubility and usually substantially less solubility for the solute than the feed solvent. The impovement comprises converting the solute permeating across the membrane to a different chemical compound, whereby a high concentration gradient for the solute across the membrane is maintained to improve the separation of the solute from the feed solvent liquid phase.
    Type: Grant
    Filed: January 21, 1980
    Date of Patent: July 30, 1985
    Assignee: Varen Technology
    Inventor: Ronald J. Vaughan
  • Patent number: 4532362
    Abstract: The use of fluorocarbons during the multiphase oxidation of olefins to ketones with Wacker-type catalysts improves reaction efficiency.
    Type: Grant
    Filed: February 17, 1984
    Date of Patent: July 30, 1985
    Assignee: Phillips Petroleum Company
    Inventors: Simon G. Kukes, Tod K. Shioyama
  • Patent number: 4528401
    Abstract: An improved process is provided for forming ketones from the corresponding olefins in the vapor phase in the presence of water vapor employing a heterogeneous catalyst comprising a molybdenum disulfide catalyst formed by the thermal decomposition of a thiomolybdate compound. 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: Grant
    Filed: July 25, 1983
    Date of Patent: July 9, 1985
    Assignee: Exxon Research & Engineering Co.
    Inventors: Chuen Y. Yeh, Charles Savini
  • Patent number: 4507507
    Abstract: A Pd/heteropolyacid/surfactant catalyst system, when used with proper diluents, improves the oxidation of olefins to ketones, while reducing corrosive effects.
    Type: Grant
    Filed: October 12, 1983
    Date of Patent: March 26, 1985
    Assignee: Phillips Petroleum Company
    Inventor: Timothy P. Murtha
  • Patent number: 4419525
    Abstract: Wacker-type oxidation catalysts can be recovered and rejuvenated for further use by separating catalyst solids from the reaction mixture and, optionally, adjusting pH.
    Type: Grant
    Filed: March 11, 1982
    Date of Patent: December 6, 1983
    Assignee: Phillips Petroleum Company
    Inventors: Tod K. Shioyama, Jim J. Straw
  • Patent number: 4400544
    Abstract: The invention provides an efficient method for the preparation of cycloheone by the liquid-phase oxidation of cyclohexene in the presence of a catalyst system. The rate of conversion of the cyclohexene and the yield of cyclohexanone are unexpectedly increased when the reaction mixture brought into contact with oxygen or air contains a limited amount of an aliphatic alcohol having 2-10 carbon atoms in a molecule such as ethyl alcohol with the catalyst system composed of a palladium compound, e.g. PdCl.sub.2, and at least one co-catalytic ingredient which is a copper compound or iron compound such as CuCl.sub.2 or FeCl.sub.3. The influence of benzene or cyclohexane admixed in the reaction mixture was studied to indicate no adverse effects or even better results in the reaction giving further advantages of the process in which the starting cyclohexene need not be purified and can be used as prepared by the partial hydrogenation of benzene or partial dehydrogenation of cyclohexane.
    Type: Grant
    Filed: January 22, 1982
    Date of Patent: August 23, 1983
    Assignee: Director-General of the Agency of Industrial Science and Technology
    Inventors: Katsuomi Takehira, Toshio Ishikawa, Takashi Hayakawa, Juichi Imamura
  • Patent number: 4393244
    Abstract: Cyclic terpenes containing at least one unsubstituted methylene group adjacent to a double bond are converted into cyclic mono- and/or diketones by oxidation with oxygen in the presence of a transition metal catalyst.
    Type: Grant
    Filed: August 26, 1981
    Date of Patent: July 12, 1983
    Assignee: Indian Explosives Limited
    Inventors: Sumit Bhaduri, Madan M. Mahandru
  • Patent number: 4393243
    Abstract: A process for synthesizing 3,5,5-trimethyl-4-[(E)-3-oxo-1-butenyl]-2-cyclohexen-1-one which is a known intermediate in a process for preparing a carotenoid.
    Type: Grant
    Filed: March 17, 1981
    Date of Patent: July 12, 1983
    Assignee: Hoffmann-La Roche Inc.
    Inventor: Bruno Lohri
  • Patent number: 4341907
    Abstract: A process is disclosed for the catalytic oxidation of a cycloparaffin, e.g., cyclohexane, to partial oxidation products thereof, especially for the production of mixtures of cycloalkanols and cycloalkanones. In the process, molecular oxygen, usually in the presence of an inert gas, is introduced into the cycloparaffin at elevated pressure and a temperature of 130.degree.-180.degree. C., in the presence of an oxidation catalyst comprising a heavy metal compound along with an N-heterocyclic compound. The heavy metal of the heavy metal compound may be cobalt, vanadium, manganese, copper, iron or nickel. The heavy metal compound may have ligands of alkanoate, dialkylphosphate, dicycloalkylphosphate or alkylcycloalkylphosphate. The N-heterocyclic compound may be dipyridyl, pyrimidine, pyrazine, pyridine and pyridine substituted with --CN, --R, and/or --OR where R is alkyl. A preferred catalyst is cobalt bis[di(2-ethylhexyl)phosphate] in combination with pyridine.
    Type: Grant
    Filed: January 30, 1981
    Date of Patent: July 27, 1982
    Assignee: Du Pont Canada Inc.
    Inventor: Ronald A. Zelonka
  • Patent number: 4339604
    Abstract: An improved method for the preparation of cyclohexanol and/or cyclohexanone from benzene. Cyclohexanol and/or cyclohexanone is prepared by the steps of hydrogenating benzene to form a hydrogenation reaction mixture containing cyclohexene, unreacted benzene, and by-product cyclohexane, hydrating cyclohexene thus obtained to form a hydration reaction mixture containing cyclohexanol, unreacted benzene and by-product cyclohexane and/or oxidating this cyclohexene to form an oxidation reaction mixture containing cyclohexanone, unreacted benzene and by-product cyclohexane, recovering from said hydration reaction mixture the cyclohexanol product and/or from said oxidation reaction mixture the cyclohexanone product, and an organic phase containing unreacted benzene and by-product cyclohexane, and recycling unconverted benzene to the benzene hydrogenation step.
    Type: Grant
    Filed: October 30, 1980
    Date of Patent: July 13, 1982
    Assignee: Stamicarbon, B.V.
    Inventors: Paul C. van Geem, Theodorus F. M. de Graaf, Dirk Knol, Otto G. Plantema
  • Patent number: 4326084
    Abstract: There is disclosed an improved process for oxidizing cyclohexane to produce a reaction mixture containing cyclohexyl hydroperoxide and decomposing the cyclohexyl hydroperoxide to form a mixture containing cyclohexanone and cyclohexanol comprising using in the oxidation step and/or the decomposition step as a catalyst a transitional metal complex of certain 1,3-bis(pyridylimino)isoindolines.
    Type: Grant
    Filed: September 16, 1980
    Date of Patent: April 20, 1982
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Joe D. Druliner, Steven D. Ittel, Paul J. Krusic, Chadwick A. Tolman
  • Patent number: 4322562
    Abstract: An oxidation process in which a metal nitro complex transfers an oxygen atom from the nitro ligand to a substrate; especially such process conducted cyclically or catalytically using molecular oxygen as the oxygen source. Metal nitrosyl complex is formed as a coproduct together with an oxidation product of the substrate. In a cyclic process, nitrosyl ligand of the metal nitrosyl coproduct is reoxidized by molecular oxygen in presence of a monodentate base such as pyridine to nitro ligand; and the nitro complex, thus regenerated, can be used again to oxidize the substrate. In a catalytic process, using an activator such as a Lewis acid with alcohols or divalent palladium with olefins, elemental oxygen maintains a concentration of nitro ligand in the reaction mixture. In particular the metal is a Group VIII metal, especially cobalt and the ligand is saloph or tetraphenylporphyrin.
    Type: Grant
    Filed: December 19, 1980
    Date of Patent: March 30, 1982
    Assignee: Allied Corporation
    Inventors: Benjamin S. Tovrog, S. Elliot Diamond, Frank Mares
  • Patent number: 4271320
    Abstract: An industrially suitable process for producing a higher carbonyl compound by the oxidation of an olefinic compound having at least six carbon atoms is provided. Said improved process comprises oxidizing the olefinic compound in aqueous medium containing palladium or salt thereof and a copper salt in the presence of a specific water-soluble polyoxyalkylene compound in an amount of from about 1/4 to about 3 parts by weight per 1 part by weight of water contained in the reaction mixture. The improvement is demonstrated in terms of yield, selectivity, separation of the product, and recycle of the catalyst.
    Type: Grant
    Filed: August 31, 1979
    Date of Patent: June 2, 1981
    Assignee: Kuraray Co., Ltd.
    Inventors: Yasuo Tokitoh, Noriaki Yoshimura, Masuhiko Tamura
  • Patent number: 4250121
    Abstract: Carbonyl compounds are manufactured by oxidizing alcohols or polyalcohols with molecular oxygen in the presence of a catalyst which comprises ruthenium salts or complexes associated with copper or iron salts or complexes.
    Type: Grant
    Filed: May 24, 1979
    Date of Patent: February 10, 1981
    Assignee: Institut Francais du Petrole
    Inventor: Hubert Mimoun
  • Patent number: 4250118
    Abstract: An improved process for the preparation of cyclohexanone from benzene. Benzene is hydrogenated in a gaseous phase in a hydrogenation zone to form cyclohexane; cyclohexane is oxidized in a liquid phase to form a mixture containing cyclohexanol and cyclohexanone; and cyclohexanone is separated from this mixture and is catalytically dehydrogenated to form cyclohexanone and a hydrogen containing gas. The resulting hydrogen containing gas is introduced into a washing zone wherein it is washed with cyclohexane or benzene and the hydrogen gas thus purified is fed into the hydrogenation zone.
    Type: Grant
    Filed: April 20, 1979
    Date of Patent: February 10, 1981
    Assignee: Stamicarbon, B.V.
    Inventors: Theodorus J. van de Mond, Hubertus J. A. Delahaye