Preparing By Oxidation Patents (Class 568/836)
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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
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Patent number: 6143927Abstract: This invention relates to methods for controlling the oxidation of hydrocarbons to intermediate oxidation products, such as adipic acid for example, by removing the catalyst from the reaction mixture, outside the reaction zone, after the oxidation has taken place at least partially. The catalyst is at least partially precipitated by reducing the water level in the reaction mixture and subjecting the reaction mixture to a temperature, at which or over which catalyst precipitates.Type: GrantFiled: March 12, 1999Date of Patent: November 7, 2000Assignee: RPC Inc.Inventors: Mark W. Dassel, Ader M. Rostami, David C. DeCoster, Eustathios Vassiliou
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Patent number: 6075169Abstract: In a process for preparing oxidation products of cyclohexane by catalytic oxidation with oxygen-containing gases in the liquid phase, where the gases are brought into contact essentially uniformly with the liquid cyclohexane in a reaction zone, liquid cyclohexane and the oxygen-containing gases are passed in countercurrent through the reaction zone.Type: GrantFiled: April 14, 1999Date of Patent: June 13, 2000Assignee: BASF AktiengesellshcaftInventors: Alwin Rehfinger, Martin Gann, Robert Markl, Rudiger Schmitt
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Patent number: 6075170Abstract: This invention relates to a process for preparing cyclohexanol and cyclohexanone, in particular, to a process for preparing cyclohexanol and cyclohexanone by selectively oxidizing cyclohexane with Fe/Pd catalyst in a flow of hydrogen and oxygen gases in the mixture of acetone and acetic acid.Type: GrantFiled: September 1, 1998Date of Patent: June 13, 2000Assignee: Korea Research Institute of Chemical TechnologyInventors: Ki Won Jun, Sang Bum Kim, Seong Bo Kim, Kyu Wan Lee
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Patent number: 6037491Abstract: This invention relates to methods and devices of preparing acids, such as adipic acid for example, by oxidizing a hydrocarbon, such as cyclohexane for example, with a gas containing an oxidant, preferably oxygen. A respective hydrocarbon is reacted, preferably at a steady state, with a gaseous oxidant to form an acid in a liquid mixture which preferably contains a solvent, a catalyst, water, and an initiator. The ratio of solvent to hydrocarbon may be controlled in a manner to maintain in the reaction zone maximum reaction rate and/or reactivity, or reaction rate and/or reactivity within a desired range, or reaction rate and/or reactivity directed toward a desired range. In addition, the ratio of solvent to hydrocarbon is controlled in a manner to maintain in the reaction zone substantially maximum selectivity and/or yield, or selectivity and/or yield within a desired range, or selectivity and/or yield directed toward a desired range.Type: GrantFiled: July 25, 1997Date of Patent: March 14, 2000Assignee: RPC Inc.Inventors: Eustathios Vassiliou, Mark W. Dassel, Sharon M. Aldrich, Ader M. Rostami, David C. DeCoster
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Patent number: 6008415Abstract: Cyclohexane is catalytically oxidized to produce cyclohexanol and cyclohexanone and precursors of these products. The oxidation is carried out in a liquid oxidation reactor at high oxygen concentrations (greater than 30% and preferably greater than 90% oxygen concentration) and at relatively low temperatures (less than 160.degree. C.). The use of the liquid oxidation reactor permits the use of these high oxygen concentrations without forming dangerously high levels of oxygen in the overhead gas phase. The result is an increased yield and selectivity of the desired products.Type: GrantFiled: July 10, 1998Date of Patent: December 28, 1999Assignee: ABB Lummus Global Inc.Inventors: Marvin I. Greene, Charles Summer, Robert J. Gartside
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Patent number: 6002026Abstract: The present invention relates to novel oxidative processes for substrates such as olefins, alkanes, aromatics and alcohols using metallic porphyrin or salen catalytic complexes which have been specifically designed to maximize catalytic activity, thereby enhancing efficiency, selectively and speed of oxidation of these substrates. The choice of the substituents in the metallic complexes may be varied, but must be chosen to prevent specific ligand set arrangements known to be stable and therefore less catalytically efficient. Coordination complexes, particularly porphyrins and salens having nitrosyl axial ligands and electron-withdrawing peripheral substituents are preferred. Ruthenium coordination metals are the preferred metal center, with the highly reactive catalytic species found to be Ru.sup.III.Type: GrantFiled: December 5, 1996Date of Patent: December 14, 1999Assignee: The Trustees of Princeton UniversityInventors: John T. Groves, Tommaso Carofiglio, Marcella Bonchio, Anthony Sauve
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Patent number: 5981420Abstract: A substrate (e.g., a cycloalkane, a polycyclic hydrocarbon, an aromatic compound having a methyl group) is oxidized with oxygen in the presence of an oxidation catalytic system comprising an imide compound of the following formula (1) (e.g., N-hydroxyphthalimide) and a co-catalyst containing a element selected from Group 3 to 12 elements (in particular, Group 4 to 11 elements) of the Periodic Table of Elements. The co-catalyst comprises a compound containing plural elements (except heteropolyacid and a combination of Group 7 and 8 elements of the Periodic Table of Elements), and is useful for the formation of an oxide (e.g., a ketone, an alcohol, a carboxylic acid): ##STR1## wherein R.sup.1 and R.sup.2 represent a substituent such as a hydrogen atom or a halogen atom, or R.sup.1 and R.sup.2 may together form a double bond or an aromatic or nonaromatic 5- to 12-membered ring, X is O or OH, and n is 1 to 3.Type: GrantFiled: February 17, 1998Date of Patent: November 9, 1999Assignees: Daicel Chemical Industries, Ltd., Yasutaka IshiiInventors: Tatsuya Nakano, Yasutaka Ishii
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Patent number: 5892122Abstract: An improved method for making cyclohexanone and cyclohexanol from oxidation of cyclohexane in which a polyprotic acid is used to neutralize caustic to prevent oligomerization of cyclohexanone during fractional distillation.Type: GrantFiled: August 25, 1997Date of Patent: April 6, 1999Assignee: E. I. du Pont de Nemours and CompanyInventors: John Joseph Ostermaier, George Crumbaugh Russell, III
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Patent number: 5817868Abstract: Methods and devices for controlling the oxidation of a hydrocarbon to an acid by regulating the temperature, hold-up time, and conversion in consecutive reaction zones. The temperature in the consecutive reaction zones progressively decreases, while the hold-up time increases. Preferably, the conversion also increases. One of the major advantages of the methods and devices of the present invention is that an outstanding balance between productivity and selectivity/yield of the desired acid may be achieved. In this respect high yields and selectivities may be obtained without sacrificing productivity.Type: GrantFiled: May 21, 1997Date of Patent: October 6, 1998Assignee: Twenty-First Century Research CorporationInventors: Ader M. Rostami, Mark W. Dassel, Eustathios Vassiliou, David C. DeCoster
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Patent number: 5811599Abstract: A process for the oxidation of hydrocarbons and their derivatives having the general formula RX, wherein R is from n-alkyl, iso-alkyl, benzyl, cyclohexyl, mono, di or tricyclic aryl, or alkenic groups and X is selected from H, OH or Cl to compounds having formula R.sup.1 XY wherein R.sup.1 =(R--H), X has the meaning defined as above and Y=OH; which comprises of reacting the appropriate hydrocarbon or it's derivative of the formula RX where R and X have the meaning given above, with a solution of aqueous hydrogen peroxide at a temperature in the range of 10.degree.-100.degree. C. in the presence of an amorphous titanium-silicate catalyst having molar chemical composition in terms of the anhydrous oxides of TiO.sub.2 : (5-400) SiO.sub.2, having an average micropore radius between 10 and 40 .ANG., an absorption band around 220 nm in the ultraviolet region, a band around 960 cm.sup.-1 in the infrared region, interatomic vectors around 1.6-1.7, 2.7-2.8, 4.1-4.2 and 5.0-5.2 .ANG.Type: GrantFiled: August 2, 1995Date of Patent: September 22, 1998Inventors: Keshavaraja Alive, Ramaswamy Arumugamangalam Venkataraman, Ratnasamy Paul
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Patent number: 5801282Abstract: Methods of making intermediate oxidation products by atomizing a first liquid (in the form of droplets) containing a reactant into a gas containing an oxidant in a manner to form an intermediate oxidation product different than carbon monoxide and/or carbon dioxide. The oxidation is controlled by monitoring the pre-coalescing temperature (temperature of the droplets just before they coalesce into a mass of liquid), or transient temperature difference (difference between the pre-coalescing temperature and the temperature of the droplets just before atomized), or transient conversion (conversion taking place in the time interval between the formation of the droplets and their coalescence into a mass of liquid) or a combination thereof.Type: GrantFiled: June 7, 1995Date of Patent: September 1, 1998Assignee: Twenty-First Century Research CorporationInventors: Mark William Dassel, Eustathios Vassiliou
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Patent number: 5801273Abstract: Methods and devices for controlling the reaction rate of a hydrocarbon to an acid or other intermediate oxidation product by pressure drop rate adjustments. The pressure drop rate measurements are conducted at predetermined time intervals, after stopping the feeding and exiting of gases. The pressure drop at a predetermined time interval is measured or the time it takes for the pressure to drop by a certain degree. Adjustments are then made in one or more temperature, feeding rates of hydrocarbon, solvent, catalyst, promoter, and the like until the pressure drop rate and the reaction rate fall within desirable predetermined limits.Type: GrantFiled: May 21, 1997Date of Patent: September 1, 1998Assignee: Twenty-First Century Research CorporationInventors: Eustathios Vassiliou, Mark W. Dassel, David C. DeCoster, Ader M. Rostami, Sharon M. Aldrich
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Patent number: 5780683Abstract: Cyclohexane is catalytically oxidized to produce cyclohexanol and cyclohexanone and precursors of these products. The product is then catalytically hydrogenated while the product is still at reaction temperature to produce additional cyclohexanol and cyclohexanone from the precursors. The oxidation is carried out in a liquid oxidation reactor at high oxygen concentrations (greater than 30% and preferably greater than 90% oxygen concentration) and at relatively low temperatures (less than 160.degree. C.). The use of the liquid oxidation reactor permits the use of these high oxygen concentrations without forming dangerously high levels of oxygen in the overhead gas phase. The result is an increased yield and selectivity of the desired products. The hydrogenation is carried out in a reactor using a catalyst of palladium supported on carbon.Type: GrantFiled: September 11, 1996Date of Patent: July 14, 1998Assignee: ABB Lummus Global Inc.Inventors: Marvin I. Greene, Charles Sumner, Robert J. Gartside
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Patent number: 5767320Abstract: 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: GrantFiled: July 26, 1996Date of Patent: June 16, 1998Assignee: Council of Scientific & Industrial ResearchInventors: Robert Raja, Paul Ratnasamy
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Patent number: 5654475Abstract: Methods of making intermediate oxidation products by atomizing a first liquid (in the form of droplets) containing a reactant into a gas containing an oxidant in a manner to form an intermediate oxidation product different than carbon monoxide and/or carbon dioxide. The oxidation rate is controlled by monitoring and adjusting the temperatures and/or conversions at critical points of the process.Type: GrantFiled: March 25, 1996Date of Patent: August 5, 1997Assignee: Twenty-First Century Research CorporationInventors: Eustathios Vassiliou, Mark William Dassel
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Patent number: 5512543Abstract: The chiral isomers of 3,3-dimethyl-5-(2,2,3-trimethyl-3-cyclopenten-1-yl)-4-penten-2-ol and, more particularly, the (-)-(1'R,2S,E)-3,3-dimethyl-5-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4- penten-2-ol and (+)-(1'S,2S,E)-3,3-dimethyl-5-(2',2',3'-trimethyl-3'-cyclopenten-1'-yl)-4- penten-2-ol, are useful as perfuming ingredients to impart sandalwood type odor notes to the perfuming compositions and perfumed articles into which they are incorporated.Type: GrantFiled: August 2, 1994Date of Patent: April 30, 1996Assignee: Firmenich S.A.Inventors: Christian Chapuis, Antoine Gautier, Pierre-Alain Blanc
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Patent number: 5502245Abstract: Methods of making intermediate oxidation products by atomizing a first liquid containing a reactant into a gas containing an oxidant in a manner to form an intermediate oxidation product different than carbon monoxide and/or carbon dioxide. The oxidation is controlled by monitoring the transient conversion (conversion taking place in the time interval between the formation of the droplets and their coalescence into a mass of liquid) of first reactant to oxidation product just before the droplets coalesce into a mass of a second liquid.Type: GrantFiled: June 7, 1995Date of Patent: March 26, 1996Assignee: Twenty-First Century Research CorporationInventors: Mark W. Dassel, Eustathios Vassiliou
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Patent number: 5489716Abstract: The invention provides novel methods for the oxidation of hydrocarbons with oxygen-containing gas to form hydroxy-group containing compounds and for the decomposition of hydroperoxides to form hydroxygroup containing compounds. The catalysts used in the methods of the invention comprise transition metal complexes of a porphyrin ring having 1 to 12 halogen substituents on the porphyrin ring, at least one of said halogens being in a meso position and/or the catalyst containing no aryl group in a meso position. The catalyst compositions are prepared by halogenating a transition metal complex of a porphyrin.Type: GrantFiled: September 7, 1994Date of Patent: February 6, 1996Assignee: Sun Company, Inc. (R&M)Inventors: Paul E. Ellis, Jr., James E. Lyons
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Patent number: 5463082Abstract: Stoichiometric and catalytic chemical transformations may be carried out in solution using novel fluorous multiphase systems (FMS). The term "fluorous" is defined as a carbon-fluorine bond rich organic molecule. The FMS consists of a fluorous phase containing a fluorous solvent, typically a fluorocarbon or a fluorohydrocarbon and a reagent or a catalyst containing a sufficient number of fluorous moieties to render it preferentially soluble in the fluorous solvent without impairing the ability of the catalyst or reagent to be effective in the reaction and while maintaining the reaction in a liquid or fluid phase. The nonfluorous solvent may be any suitable organic or nonorganic solvent(s) with limited or no solubility in the fluorous solvent that is effective for dissolving the reactant(s) and most desirably, for separating the resulting product(s). Typically, such solvents have a Hildebrand solubility parameter of at least about 18.0 MPa1/2.Type: GrantFiled: July 8, 1993Date of Patent: October 31, 1995Assignee: Exxon Research and Engineering CompanyInventors: Istvan T. Horvath, Jozsef Rabai
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Patent number: 5426237Abstract: 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: GrantFiled: March 24, 1994Date of Patent: June 20, 1995Assignee: Sumitomo Chemical Co., Ltd.Inventors: Shun-Ichi Murahashi, Yoshiaki Oda
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Patent number: 5414157Abstract: Process and apparatus are provided for oxidation of oxidation of organic compounds in which a reaction zone is provided, containing an open space and a bed of solid granular catalyst, an organic feedstock and oxygen are passed in gas phase through the open space and then into contact with the catalyst bed, and reaction products are removed from the open space after relatively less contact with the catalyst, and from at least one other location after relatively greater contact with the catalyst. Greater yield of desired product may be obtained in such operation than in operation where all of the reaction products are removed after the greater contact with the catalyst.Type: GrantFiled: July 20, 1992Date of Patent: May 9, 1995Assignee: Sun Company, Inc. (R&M)Inventors: Vincent A. Durante, Darrell W. Walker, Steven M. Gussow, James E. Lyons, Robert C. Hayes
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Patent number: 5406002Abstract: An organophosphine-treated titanium-containing zeolite is a catalyst for hydrocarbon oxidation.Type: GrantFiled: February 25, 1994Date of Patent: April 11, 1995Assignee: Exxon-Chemical Patents Inc.Inventors: Luc R. M. Martens, Georges M. K. Mathys
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Patent number: 5406001Abstract: The present invention relates to a method for the continuous preparation of a mixture of a cycloalkanone, a cycloalkanol and a cycloalkylhydroperoxide. In the method, a cycloalkane, corresponding to the cycloalkenone, cycloalkenol and cycloalkylhydroperoxide, is oxidized in a continuous process, with the aid of an oxygen-containing gas, in the absence of a metal catalyst, at a temperature of between 130.degree. C. and 200.degree. C. The oxidation is at least partly carried out in the presence of between 0.002 and 2 mmol of a phenolic compound per kg of reaction mixture (mmol/kg).Type: GrantFiled: December 15, 1993Date of Patent: April 11, 1995Assignee: DSM N.V.Inventors: Johannes G. H. M. Housmans, Ubaldus F. Kragten
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Patent number: 5233099Abstract: A process for producing an alcohol by continuously passing a fatty acid ester, a fatty acid triglyceride or a fatty acid through a hydrogenation catalyst to thereby produce the aimed alcohol through catalytic reduction is disclosed, wherein the employed reactor is a fixed bed reactor in which the liquid phase and the gas phase are continuously passed together in descending parallel flows through the hydrogenation catalyst fixed in the reactor; and at least one cooling mean for cooling the reaction system is provided at a position in the vertical direction of the reactor. According to the process of the present invention with the use of a fixed bed reactor, an alcohol, which has extremely high qualities and a high purity and is contaminated with little hydrocarbon and aldehyde by-products, can be produced. The process of the present invention further makes it possible to omit the post-treatment for eliminating the by-products.Type: GrantFiled: December 24, 1991Date of Patent: August 3, 1993Assignee: Kao CorporationInventors: Osamu Tabata, Kunizo Hashiba, Takahiro Kawakami
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Patent number: 5233100Abstract: A process for producing an alcohol from a fatty acid ester, a fatty acid triglyceride or a fatty acid by continuously catalytically reducing the starting material in the presence of a hydrogenation catalyst is disclosed. In the process of the present invention, two reactors (i.e., the main reactor located upstream and the after reactor located downstream) being located in series are employed. In the process of the present invention, two reactors are employed and the temperatures thereof are individually controlled, whereby the conversion ratio is elevated while suppressing the formation of hydrocarbon and aldehyde by-products. Thus, an alcohol of extremely high quality and high purity can be produced. Further, the process of the present invention makes it possible to omit any post-treatment for eliminating the by-products. Furthermore, the active life of the hydrogenation catalyst can be remarkably prolonged by using three reactors (i.e., the guard reactor, the main reactor and the after reactor).Type: GrantFiled: December 27, 1991Date of Patent: August 3, 1993Assignee: Kao CorporationInventors: Osamu Tabata, Atsuhito Mori, Takahiro Kawakami, Kunizo Hashiba, Kiyoshi Tsukada
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Patent number: 5233092Abstract: 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: GrantFiled: January 17, 1992Date of Patent: August 3, 1993Inventor: Xiao Zaosheng
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Patent number: 5208392Abstract: The present invention provides a novel Fe-Pd catalyst prepared by impregnating, either together or respectively, an iron source compound and a palladium source compound onto a carrier selected from the group consisting of silica, alumina and silica-alumina, and drying and calcining said Fe-Pd impregnated carrier in a flow of air or H.sub.2 /N.sub.2 ; and a method for preparing a mixture of cyclohexanol and cyclohexanone by selectively oxidizing cyclohexane in a reaction medium provided with hydrogen and oxygen gases in the presence of said Fe-Pd catalyst.Type: GrantFiled: April 27, 1992Date of Patent: May 4, 1993Assignee: Korea Research Institute of Chemical TechnologyInventors: Kyu-Wan Lee, Ki-Won Jun, Eun-Kyung Shim
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Patent number: 5175316Abstract: The preparation of cyclohexene oxide, cyclohexanol and cyclohexanone involvesa) oxidizing cyclohexane using a gas containing molecular oxygen to form cyclohexyl hydroperoxide, cyclohexanol and cyclohexanone,b) jointly separating the mixture from a) and c) by distillation, andc) reaction of the cyclohexyl hydroperoxide fraction from b) with cyclohexene in the presence of a transition-metal compound from group 4 to 6, forming cyclohexene oxide, and separating the product mixture in b).Type: GrantFiled: February 10, 1992Date of Patent: December 29, 1992Assignee: BASF AktiengesellschaftInventors: David Agar, Paul-Michael Bever, Hans H. Schuster, Gerald Neubauer
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Patent number: 5168983Abstract: A process for separating cyclohexanol and other impurities from a mixture containing cyclohexanone and cyclohexanol is disclosed.Type: GrantFiled: March 22, 1991Date of Patent: December 8, 1992Assignee: Mitsubishi Kasei CorporationInventors: Kazuo Tan, Kazuhiro Fujii, Michio Nakamura, Kazunao Hanada
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Patent number: 5132472Abstract: Process is provided for oxidation of organic compounds in which a reaction zone is provided, containing an open space and a bed of solid granular catalyst, an organic feedstock and oxygen are passed in gas phase through the open space and then into contact with the catalyst bed, and reaction products are removed from the open space after relatively less contact with the catalyst, and from at least one other location after relatively greater contact with the catalyst. Greater yield of desired product may be obtained in such operation than in operation where all of the reaction products are removed after the greater contact with the catalyst.Type: GrantFiled: October 17, 1990Date of Patent: July 21, 1992Assignee: Sun Refining and Marketing CompanyInventors: Vincent A. Durante, Darrell W. Walker, Steven M. Gussow, James E. Lyons, Robert C. Hayes
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Patent number: 5077394Abstract: Disclosed are tetraphenyl porphyrins which are beta-substituted by fluoro or chloro and/or bear electronegative substituents on the phenyl including one or two water solubilizing substituents. The new porphorins are particularly suitable as catalysts in a variety of oxidative reactions and methods.Type: GrantFiled: December 21, 1989Date of Patent: December 31, 1991Assignee: Sandoz Ltd.Inventors: David H. Dolphin, Taku Nakano, Thomas K. Kirk, Tilak P. Wijesekera, Roberta L. Farrell, Theodore E. Maione
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Patent number: 5068464Abstract: 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: GrantFiled: May 26, 1988Date of Patent: November 26, 1991Assignee: BASF CorporationInventor: David C. Hendrix
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Patent number: 5021607Abstract: Saturated hydrocarbon chains are oxidized using a titanium containing silicalite catalyst having an infra red absorption band around 950 cm.sup.-1 preferably in solutions, the chains may be alkanes or alkyl groups of alkyl cyclic compounds.Type: GrantFiled: September 10, 1990Date of Patent: June 4, 1991Assignee: Exxon Chemical Patents Inc.Inventor: Diana R. Huybrechts
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Patent number: 4943644Abstract: 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: GrantFiled: November 23, 1988Date of Patent: July 24, 1990Assignee: The University of FloridaInventors: Russell S. Drago, Shannon Davis
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Patent number: 4927974Abstract: 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: GrantFiled: April 6, 1989Date of Patent: May 22, 1990Assignee: Stamicarbon B.V.Inventors: Paul C. van Geem, Franciscus T. B. van den Brink
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Patent number: 4877903Abstract: 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: GrantFiled: November 14, 1988Date of Patent: October 31, 1989Assignee: Rhone-Poulenc ChimieInventors: Michel Costantini, Francoise Igersheim
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Patent number: 4735741Abstract: Solutions of molecular oxygen in liquid hydrocarbons are prepared by bringing a liquid hydrocarbon into contact with molecular oxygen under superatmospheric pressure in a vertical absorption zone, by a process in which(a) a layer of water is maintained at the lower end of the absorption zone,(b) molecular oxygen is passed into the layer of water,(c) a liquid hydrocarbon is fed in above the layer of water,(d) the finely divided molecular oxygen rising from the layer of water is passed upward together with the liquid hydrocarbon at from 0.degree. to 50.degree. C., with thorough mixing in the absorption zone, with the proviso that no cohesive gas phase is formed, and(e) the solution of molecular oxygen in the liquid hydrocarbon is discharged in the upper part of the absorption zone.Type: GrantFiled: April 23, 1986Date of Patent: April 5, 1988Assignee: BASF AktiengesellschaftInventors: Otto-Alfred Grosskinsky, Guenter Herrmann, Ulrich Loeffler, Rolf Schnabel, Dieter Stuetzer
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Patent number: 4720592Abstract: The reaction mixture obtained by oxidation of cyclohexane using a cobalt catalyst is extracted with water to remove undesirable oxidation products such as diacids, hydroxy acids, and cobalt catalyst. The resulting mixture is then hydrogenated using a fixed bed hydrogenation catalyst to convert cyclohexyl hydroperoxide to cyclohexanol and cyclohexanone.Type: GrantFiled: September 5, 1986Date of Patent: January 19, 1988Assignee: E. I. Du Pont de Nemours and CompanyInventors: Usamah N. Besmar, John B. Lyon, Francis J. Miller, Michael T. Musser
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Patent number: 4691053Abstract: A novel process for producing oxygen-containing organic compounds with high selectivity and good yield by oxidizing organic compounds under mild conditions is provided, which process comprises using as a catalyst for the oxidation, a complex (M.sub.m X.sub.n.L.sub.l) consisting of a transition metal compound (M.sub.m X.sub.n) and an organic phosphorous compound (L) as a ligand, wherein M represents a transition metal belonging to group I, group IV.about.VII or iron group in group VIII of the periodic table; X represents an anion such as a halogen; ligand L represents an organic phosphorous compound; and m and n mean a number of the atomic valence of said transition metal (ion) M and said anion X, respectively, and l means a number of said ligand.Type: GrantFiled: June 4, 1984Date of Patent: September 1, 1987Assignee: Babcock-Hitachi Kabushiki KaishaInventors: Mutsuo Yamada, Yasuyuki Nishimura, Yoshijiro Arikawa, Takanori Kuwahara, Taiji Kamiguchi, Hirotoshi Tanimoto
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Patent number: 4675450Abstract: 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: GrantFiled: November 12, 1985Date of Patent: June 23, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventors: John B. Lyon, Gerald T. Stowe
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Patent number: 4659829Abstract: 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: GrantFiled: January 31, 1985Date of Patent: April 21, 1987Assignee: Institut Francais du PetroleInventors: Lucien Saussine, Alain Robine, Hubert Mimoun
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Patent number: 4658056Abstract: 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: GrantFiled: April 22, 1982Date of Patent: April 14, 1987Assignee: Du Pont Canada Inc.Inventor: Peter A. Sipos
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Patent number: 4609763Abstract: A process for the oxidation of alkanes or alkenes is described. The process uses a hydrocarbyl hydroperoxide as an oxidizing agent in combination with a ruthenium catalyst and optionally a hydrogen bromide or hydrobromide acid promoter. The products of the oxidation are alcohols, ketones or a mixture of both.Type: GrantFiled: September 3, 1985Date of Patent: September 2, 1986Assignee: The British Petroleum Company P.L.C.Inventors: Colin G. Griggs, Anthony R. Middleton
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Patent number: 4587363Abstract: Oxygen-containing compounds are prepared by oxidizing a hydrocarbon in the liquid phase with a gas containing molecular oxygen, at elevated temperatures and under superatmospheric pressure, by a continuous process in which the said gas is fed into the liquid reaction mixture, in a downward direction, at several points along the reaction zone via nozzle apertures, so that it emerges at each nozzle aperture with a velocity of from 0.01 to 1 m/sec in an amount of from 0.001 to 10 liters per second per nozzle aperture, and the said reaction mixture is brought into substantially uniform contact with the gas containing molecular oxygen, over the volume of the reaction zone.Type: GrantFiled: August 10, 1984Date of Patent: May 6, 1986Assignee: BASF AktiengesellschaftInventors: Jurgen Hartig, Gunter Schuch, Armin Stoessel, Guenter Herrmann, Arthur Brunner, Peter Zehner, Otto-Alfred Grosskinsky
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Patent number: 4568769Abstract: 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: GrantFiled: June 20, 1984Date of Patent: February 4, 1986Assignee: Sumitomo Chemical CompanyInventors: Akira Yashima, Teruo Matsuda, Tadao Sato, Mitsuaki Takahashi, Kiyomi Sakai
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Patent number: 4532347Abstract: 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: GrantFiled: January 21, 1980Date of Patent: July 30, 1985Assignee: Varen TechnologyInventor: Ronald J. Vaughan
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Patent number: 4491674Abstract: A process for the safe supply of molecular oxygen or gas containing molecular oxygen to an oxidation of hydrocarbons in the liquid phase, wherein, immediately before the point of entry into the liquid hydrocarbon, the oxygen, or gas containing oxygen, to be supplied is at least 20.degree. C. colder than the hydrocarbon, and wherein, as soon as the oxygen, or gas containing oxygen, which is to be supplied exceeds the predetermined temperature at the supply orifice, the supply ceases.Type: GrantFiled: December 8, 1980Date of Patent: January 1, 1985Assignee: BASF AktiengesellschaftInventors: Norbert Rieber, Hans Hellbach, Gerhard Hunziker, Guenter Mueller
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Patent number: 4459427Abstract: A mixture of the alcohol and ketone derivatives of alkanes is produced by reacting the alkane with a hydrocarbyl hydroperoxide, eg t-butyl hydroperoxide, at ambient or elevated temperature and pressure in the presence as catalyst of an iron or manganese square planar complex having heterocyclic nitrogen-donor ligands, e.g. a porphyrin or phthalocyanine complex, which complex has either no axial ligands, eg the lower valency or cationic complex, or an axial ligand which is non-coordinating or weakly-coordinating.Type: GrantFiled: October 26, 1982Date of Patent: July 10, 1984Assignee: The British Petroleum Company p.l.c.Inventors: Anthony R. Middleton, David J. H. Smith
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Patent number: 4341907Abstract: 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: GrantFiled: January 30, 1981Date of Patent: July 27, 1982Assignee: Du Pont Canada Inc.Inventor: Ronald A. Zelonka