Ag, Au, Pd, Pt, Rh, Ir, Ru, Or Os Containing Catalyst Utilized Patents (Class 568/478)
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Patent number: 11772080Abstract: A catalyst comprising molybdenum, bismuth, iron, and nickel, wherein a proportion of a surface concentration of the nickel to a bulk concentration of the nickel is 0.60 to 1.20.Type: GrantFiled: March 26, 2020Date of Patent: October 3, 2023Assignee: ASAHI KASEI KABUSHIKI KAISHAInventors: Shota Aiki, Akiyoshi Fukuzawa
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Patent number: 9586883Abstract: This disclosure is directed to methods of preparing organic aldehydes, each method comprising contacting a terminal olefin with an oxidizing mixture comprising: (a) a dichloro-palladium complex; (b) a copper complex; (c) a source of nitrite; under aerobic reaction conditions sufficient to convert at least a portion of the terminal olefin to an aldehyde.Type: GrantFiled: April 17, 2014Date of Patent: March 7, 2017Assignee: California Institute of TechnologyInventors: Zachary K. Wickens, Bill Morandi, Robert H. Grubbs, Kacper Skakuj, Sarah M. Bronner
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Publication number: 20140316149Abstract: This disclosure is directed to methods of preparing organic aldehydes, each method comprising contacting a terminal olefin with an oxidizing mixture comprising: (a) a dichloro-palladium complex; (b) a copper complex; (c) a source of nitrite; under aerobic reaction conditions sufficient to convert at least a portion of the terminal olefin to an aldehyde.Type: ApplicationFiled: April 17, 2014Publication date: October 23, 2014Applicant: CALIFORNIA INSTITUTE OF TECHNOLOGYInventors: ZACHARY K. WICKENS, BILL MORANDI, ROBERT H. GRUBBS, KACPER SKAKUJ, SARAH BRONNER
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Publication number: 20110295041Abstract: A method of preparing a catalyst for producing acrolein by oxidation of propylene at high space velocity, said catalyst is a Mo—Bi—Fe—Co based composite metal oxide. Producing unsaturated aldehyde via partial oxidation of lower unsaturated olefin at high space velocity using said catalyst is suitable for process with or without off-gas recirculating. Said catalyst is prepared by co-precipitation, the reaction conditions for using said catalyst to produce unsaturated aldehyde are, the space velocity of unsaturated lower olefin relative to catalyst being 120˜200 h-1(STP), reaction temperature being 300˜420° C. and absolute pressure being 0.1˜0.5 MPa; a single-stage unsaturated lower olefin conversion ratio of greater than 98.0% and carbon oxide yield of less than 3.3% with an overall yield of unsaturated lower aldehyde and acid of greater than 94.0% are obtained. The process to prepare the said catalyst is simple, easy to be repeated, and capable of industrial scale-up.Type: ApplicationFiled: May 26, 2011Publication date: December 1, 2011Applicant: Shanghai HuaYi Acrylic Acid Co. Ltd.Inventors: Jian Wang, Xuemei Li, Yan Zhuang, Kaimin Shi, Kun Jiao, Jianxue Ma, Xiaodong Chu, Jingming Shao
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Publication number: 20090156860Abstract: The object of the present invention is to provide a catalyst which can produce an ?,?-unsaturated carboxylic acid through liquid-phase oxidation of an olefin or an ?,?-unsaturated aldehyde in good reaction performance, a method for producing the catalyst, and a method for producing an ?,?-unsaturated carboxylic acid by using the catalyst. The present invention resides in a catalyst for producing an ?,?-unsaturated carboxylic acid, wherein a metal is supported on a carrier with a total pore volume of 0.40 to 1.50 cc/g as measured by nitrogen gas adsorption method, or wherein palladium with an average particle diameter in the range of 1 to 8 nm is supported on the carrier.Type: ApplicationFiled: February 19, 2009Publication date: June 18, 2009Applicant: Mitsubishi Rayon Co., Ltd.Inventors: Yuji Fujimori, Wataru Ninomiya, Akio Takeda, Mai Kojima
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Patent number: 7176335Abstract: A process prepares methacrolein from isobutane by subjecting isobutane to a partial catalytic dehydrogenation in the gas phase and using the isobutenic product gas mixture to charge an oxidation zone in which the isobutene is oxidized to methacrolein in the gas phase with heterogeneous catalysis using molecular oxygen accompanied by molecular nitrogen as the oxygen source.Type: GrantFiled: June 28, 2002Date of Patent: February 13, 2007Assignee: BASF AktiengesellschaftInventors: Silke Berndt, Klaus Joachim Mueller-Engel, Goetz-Peter Schindler, Frank Rosowski, Jochen Petzoldt
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Patent number: 7161044Abstract: An object of the present invention is to provide a catalytic gas phase oxidation reaction in which: even under reaction conditions of a higher gas pressure, a higher concentration of the raw material gas and a larger space velocity of a reaction gas, the thermal accumulation at the hot spot portion can be sufficiently suppressed with ease and at low costs, so that the reaction can be continued for a long time while a high yield is maintained.Type: GrantFiled: October 4, 2004Date of Patent: January 9, 2007Assignee: Nippon Shokubai Co., Ltd.Inventors: Daisuke Nakamura, Michio Tanimoto
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Patent number: 7102034Abstract: A process for preparing sulfonated arylphosphines by reaction of arylphosphines with oleum, wherein, after reaction of the arylphosphines with oleum, the sulfonation mixture is firstly diluted with water, an inert gas stream is then passed through the diluted sulfonation mixture until SO2 is no longer liberated from the diluted sulfonation mixture and the latter is then worked up further in a customary manner and its use.Type: GrantFiled: December 8, 2004Date of Patent: September 5, 2006Assignee: Celanese Chemicals Europe GmbHInventors: Michael Riedel, Ernst Wiebus, Carl D Frohning, Wilfried Fenske, Florian Rampf, Jurgen Herwig, Helmut Bahrmann, Klaus Bergrath, Wolfgang Zgorzel-Ski, Robert Eckl, Hans Bohnen, Richard Fischer, Kurt Schalapski, Wolfgang Greb
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Patent number: 6901334Abstract: Methods of analyzing processes for making catalysts and/or certain properties of catalysts using a plurality of reaction zones are provided. The methods of the present invention have the capability to define and execute, in rapid succession, a plurality of experiments under disparate reaction conditions. An operator may define and execute a plurality of experiments on user-defined quantities of disparate catalysts, using user-defined input feeds, residence times, and temperature profiles.Type: GrantFiled: December 2, 2002Date of Patent: May 31, 2005Assignee: Rohm and Haas CompanyInventors: Michael William Linsen, Edward Albert Schmitt, Mark Richard Schure
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Patent number: 6864391Abstract: A process for preparing hydroformylation products of propylene and for preparing acrylic acid and/or acrolein comprises a) feeding a propylene-containing feed in which from 2 to 40% by weight of propane is present and also carbon monoxide and hydrogen into a reaction zone and reacting this mixture in the presence of a hydroformylation catalyst to form hydroformylation products of propane, b) separating a stream consisting essentially of unreacted propylene and propane from the output from the reaction zone, and c) subjecting the stream consisting essentially of propylene and propane to a catalytic gas-phase oxidation in the presence of molecular oxygen to form acrylic acid and/or acrolein.Type: GrantFiled: June 27, 2001Date of Patent: March 8, 2005Assignee: BASF AktiengesellschaftInventors: Roland Krokoszinski, Ulrich Hammon, Kevin Todd
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Patent number: 6812366Abstract: A catalyst useful for oxidation reactions is disclosed. The catalyst is useful for the gas phase oxidation of alkanes, propylene, acrolein, or isopropanol to unsaturated aldehydes or carboxylic acids.Type: GrantFiled: September 2, 2003Date of Patent: November 2, 2004Assignee: Rohm and Haas CompanyInventor: Manhua Lin
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Patent number: 6620973Abstract: A catalyst composition for the production of unsaturated aldehydes by the oxidation of the corresponding olefins, and methods of making and using such catalyst compositions. The catalysts of the present invention include compositions of the formula: MoaPdbBicFedX1eX2fX3gOz, wherein X1 is an element selected from Co, Ni, V, Pt, Rh, or mixtures thereof; X2 is an element selected from Al, Ga, Ge, Mn, Nb, Zn, Ag, P, Si, W, or mixtures thereof; X3 is an element selected from K, Mg, Rb, Ca, Sr, Ba, Na, In, or mixtures thereof; a is 1; b is 0<b<0.3; c is 0<c<0.9; d is 0<d<0.9; e is 0<e<0.9; f is 0<f<0.9; g is 0<g<0.3; and z is an integer representing the number of oxygen atoms required to satisfy the valency of Mo, Pd, Bi, Fe, X1, X2, and X3 in the catalyst composition. Using the methods of the present invention, one may effectively oxidize the desired starting materials at relatively high levels of conversion, selectivity, and productivity, and with minimal side products.Type: GrantFiled: October 19, 2001Date of Patent: September 16, 2003Assignee: Saudi Basic Industries CorporationInventors: Khalid Karim, Yajnavalkya Subrai Bhat, Syed Irshad Zaheer, Asad Ahmad Khan
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Patent number: 6545178Abstract: In the production of acrolein and acrylic acid by the catalytic gas phase oxidation of propylene with a molecular oxygen-containing gas, a method is provided which enables acrolein and acrylic acid to be stably produced with a high yield for a long time from propylene by effectively repressing such secondary reactions as are responsible for the formation of organic acids, high boiling compounds, and tarry compounds, the deposition of carbonized materials, and the deterioration of the quality of products. The content of unsaturated hydrocarbons (excluding propylene) of 2-5 carbon atoms in the raw material for propylene is kept below 500 ppm (by weight). Particularly, it is proper to use a raw material for propylene which has a content of unsaturated hydrocarbons (excluding propylene) of 2-5 carbon atoms of not more than 200 ppm (by weight) and a total content of diene and acetylenic compounds of 2-5 carbon atoms of not more than 200 ppm (by weight).Type: GrantFiled: May 18, 1999Date of Patent: April 8, 2003Assignee: Nippon Shokubai Co., Ltd.Inventors: Michio Tanimoto, Daisuke Nakamura, Tatsuya Kawajiri
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Patent number: 6506944Abstract: C6 compounds of the formula (I) E—CH2—CH═CH—CH2—E1 (I) are prepared by self metathesis or cross metathesis of compounds of the formulae (II) and/or (III) R—CH═CH—CH2—E (II) R1—CH═CH—CH2—E1 (III) where E, E1 are independently —CHO, —COOH, —COOR2, —C(O)NR3R4, —CN, R, R1 are independently H, C1-12-alkyl, C6-12-aryl or C7-13-alkylaryl and R2, R3, R4 are independently H, C1-12-alkyl, C7-13-aralkyl, in the presence of a homogeneous catalyst comprising ruthenium compounds or ruthenium complexes.Type: GrantFiled: February 17, 2000Date of Patent: January 14, 2003Assignee: BASF AktiengesellschaftInventors: Peter Schwab, Michael Schulz
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Patent number: 6410785Abstract: In a process for the preparation of acrolein by gas-phase partial oxidation under heterogeneous catalysis, a reaction gas starting mixture which contains propene and molecular oxygen in a molar C3H6:O2 ratio of >1 is reacted in reaction zones connected in series, at elevated temperatures, over solid-state catalysts, further molecular oxygen being added to the reaction gas mixture in the course of the partial oxidation.Type: GrantFiled: July 18, 2001Date of Patent: June 25, 2002Assignee: BASF AktiengesellschaftInventors: Peter Zehner, Otto Machhammer, Heiko Arnold, Klaus Joachim Müller-Engel
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Patent number: 6346646Abstract: A process for producing methacrolein and methacrylic acid by catalytically oxidizing isobutylene or tertiary butanol in the presence of a catalyst comprising a compound oxide containing molybdenum, bismuth and iron as the essential components, wherein a catalytic oxidation reaction is started at a temperature of (T−3)° C. or lower wherein T° C. is defined as the boundary temperature of activation energy of a reaction for obtaining methacrolein and methacrylic acid from isobutylene using said catalyst, the reaction is continued while the reaction temperature is increased as the activity of the catalyst decreases, and an activation treatment is conducted for the catalyst at least once before the reaction temperature exceeds the boundary temperature of activation energy.Type: GrantFiled: January 27, 2000Date of Patent: February 12, 2002Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Seigo Watanabe, Motomu Oh-Kita
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Patent number: 6337424Abstract: The present invention provides a catalyst composition for the production of unsaturated aldehydes by the oxidation of the corresponding olefins, and methods of making and using such catalyst compositions. The catalysts of the present invention include compositions of the formula: MoaPdbBicFedX1eX2fX3gOz, wherein X1 is an element selected from Co, Ni, V, Pt, Rh, or mixtures thereof; X2 is an element selected from Al, Ga, Ge, Mn, Nb, Zn, Ag, P, Si, W, or mixtures thereof; X3 is an element selected from K, Mg, Rb, Ca, Sr, Ba, Na, In, or mixtures thereof; a is 1; b is 0<b<0.3;c is 0<c<0.9; d is 0<d<0.9; e is 0<e<0.9; f is 0<f<0.9; g is 0<g<0.3; and z is an integer representing the number of oxygen atoms required to satisfy the valency of Mo, Pd, Bi, Fe, X1, X2, and X3 in the catalyst composition.Type: GrantFiled: April 28, 2000Date of Patent: January 8, 2002Assignee: Saudi Basic Industries CorporationInventors: Khalid Karim, Yajnavalkya Subrai Bhat, Syed Irshad Zaheer, Asad Ahmad Khan
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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
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Patent number: 5449821Abstract: A process for the gas phase catalytic oxidation of a C.sub.3-6 alkane, alkanol, alkene or alkenal using as a catalyst multimetal oxide compositions of the formula I, [X.sup.1.sub.a X.sup.2.sub.b O.sub.x ].sub.p [X.sup.3.sub.c X.sup.4.sub.d X.sup.5.sub.e X.sup.6.sub.f X.sup.7.sub.g X.sup.2.sub.h O.sub.y ].sub.q, where X.sup.1 is bismuth, tellurium, antimony, tin and/or copper, X.sup.2 is molybdenum and/or tungsten, X.sup.3 is an alkali metal, thallium and/or samarium, X.sup.4 is an alkaline earth metal, nickel, cobalt, copper, manganose, zinc, tin, cadmium and/or mercury, X.sup.6 is iron, chromium, cerium and/or vanadium, X.sup.6 is phosphorus, arsenic, boron and/or antimony, X.sup.7 is a rare-earth metal, titanium, zirconium, niobium, tantalum, rhenium, ruthenium, rhodium, silver, gold, aluminum, gallium, indium, silicon, geranium, lead, thorium and/or uranium, a is from 0.01 to 8, b is from 0.Type: GrantFiled: June 30, 1994Date of Patent: September 12, 1995Assignee: BASF AktiengesellschaftInventors: Hans-Peter Neumann, Hans Martan, Hermann Petersen, Walter Doerflinger
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Patent number: 5144090Abstract: A method for preparing acrolein or methacrolein comprises subjecting propylene, secondary propanol, isobutylene or tertiary butanol to gas phase catalytic oxidation with molecular oxygen in the presence of a catalyst represented by the following general formula (I):Mo.sub.a Bi.sub.b Fe.sub.c X.sub.d Y.sub.O Z.sub.f O.sub.g (I)wherein X represents at least one element selected from the group consisting of Ni and Co; Y represents at least one element selected from the group consisting of K, Rb, Cs and Tl; and Z represents at least one element selected from the group consisting of Be, Mg, Ca, Sr, Ba, Ce, Ti, Zr, Nb, Cr, W, Mn, Cu, Ag, Zn, Cd, B, Al, Si, Ge, Sn, Pb, P, As, Sb, S, Se and Te; a, b, c, d, e, f and g each represents an atomic ratio of the corresponding element and when a is assumed to be 12, b=0.1.about.10, c=0.1.about.20, d=2.about.20, e=0.01.about.2, f=0.about.Type: GrantFiled: June 6, 1991Date of Patent: September 1, 1992Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Tadatoshi Honda, Tokio Nagayama, Nobuhiko Horiuchi, Jun Kitagawa, Kazunori Kawahara, Masami Murakami
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Patent number: 5136105Abstract: A process for the oxidation of a compound having a terminal carbon-carbon double bond to produce the corresponding aldehyde is disclosed. In one embodiment, the process comprises contacting the compound with molecular oxygen in the presence of a Group VIII metal component initially substantially free of NO ligands and NO.sub.2 ligands in an amount effective to promote the oxidation of the compound, a reoxidation component in an amount effective to reoxidize a reduced Group VIII metal component to the Group VIII metal component and at least one alcohol selected from secondary alcohols, tertiary alcohols and mixture thereof in an amount effective to increase the aldehyde selectivity of the oxidation. The contacting occurs at conditions effective to oxidize the compound and the form the corresponding aldehyde.Type: GrantFiled: March 28, 1991Date of Patent: August 4, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Timothy T. Wenzel
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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
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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
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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
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Patent number: 4746753Abstract: Bismuth cerium molybdate catalysts promoted with alkali metal and other optional ingredients provide high yields of acrylonitrile in the ammoxidation of propylene.Type: GrantFiled: July 1, 1986Date of Patent: May 24, 1988Assignee: The Standard Oil CompanyInventors: James F. Brazdil, Jr., Dev D. Suresh, Robert K. Grasselli
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Patent number: 4709070Abstract: A process for improving the activity of tellurium containing metal oxide catalysts useful as catalysts for oxidation, ammoxidation or oxidative dehydrogenation of organic compounds by heating the catalysts together with an activity-improving agent to a temperature up to about 900.degree. C. in a gaseous atmosphere. The process can be effectively applied to deteriorated or spent catalysts, the activity of which has been deteriorated due to use for a long period of time.Type: GrantFiled: November 9, 1984Date of Patent: November 24, 1987Assignee: Nitto Chemical Industry Co., Ltd.Inventors: Yutaka Sasaki, Yutaka Kiyomiya, Toshio Nakamura
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Patent number: 4564703Abstract: In a process for preparing methacrylic acid by the vapor-phase catalytic oxidation of methacrolein or a methacrolein-containing mixture with molecular oxygen in the presence of an oxidation catalyst; the improvement wherein said process comprisesa first-stage oxidation step of oxidizing methacrolein or a methacrolein-containing mixture as a starting material,a first-stage separating step of separating the resulting methacrylic acid from the reaction product obtained in the first-stage oxidation step,a second-stage oxidation step of oxidizing the mixture containing the unreacted methacrolein and obtained in the first-stage separating step, anda second-stage separating step of separating the resulting methacrylic acid from the reaction product obtained in the second-stage oxidation step, andwith or without at least one additional oxidation step and separating step subsequent to the second-stage separating step,and wherein the conversion of methacrolein in the first-stage oxidation step is adjusted to 30-85 moleType: GrantFiled: April 16, 1979Date of Patent: January 14, 1986Assignee: Nippon Zeon Co., Ltd.Inventors: Haruhisa Yamamoto, Shinichi Akiyama
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Patent number: 4556731Abstract: Iron-bismuth-molybdate catalysts further containing specific promoter elements have been found to exhibit excellent redox stability even under high stress conditions in the catalytic oxidation of olefins to unsaturated aldehydes and acids.Type: GrantFiled: April 19, 1982Date of Patent: December 3, 1985Assignee: The Standard Oil CompanyInventors: Andrew T. Guttmann, Robert K. Grasselli
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Patent number: 4521631Abstract: A process for producing acetaldehyde from ethylene under mild reaction conditions, selectively and with high yield is provided, which process comprises preparing a composite catalyst comprising a complex of a transition metal capable of forming an oxygen complex by coordination of oxygen molecule with the metal ion of the transition metal, and a complex of a transition metal capable of forming an ethylene complex by coordination of ethylene with the metal ion of the transition metal, and oxidizing ethylene activated by forming the ethylene complex with the combined oxygen in the oxygen complex, activated by forming the oxygen complex.Type: GrantFiled: June 13, 1984Date of Patent: June 4, 1985Assignee: Babcock-Hitachi Kabushiki KaishaInventors: Yasuyuki Nishimura, Mutsuo Yamada, Yoshijiro Arikawa, Taiji Kamiguchi, Takanori Kuwahara, Hirotoshi Tanimoto
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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
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Patent number: 4499301Abstract: Vapor phase process for the preparation of unsaturated aldehydes, carboxylic acids and mixtures thereof which comprises contacting a gaseous mixture of an open-chain olefin of from 3 to 8 carbon atoms, water and oxygen at an elevated temperature up to about 250.degree. with a solid catalyst comprising a catalytically effective amount of noble metal promoted by a solid acid consisting of mixed metal oxides.Type: GrantFiled: May 14, 1982Date of Patent: February 12, 1985Assignee: National Distillers and Chemical CorporationInventor: Jawad H. Murib
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Patent number: 4474997Abstract: An oxidation catalyst comprising boron phosphate impregnated with from 5 to 20 weight percent silver and its use to oxidize propylene, butene-1, butadiene-1,3 and methanol is disclosed. The oxidation takes place at from 200.degree. to 700.degree. C. Preferably water vapor is present.Type: GrantFiled: September 19, 1983Date of Patent: October 2, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventor: Velliyur N. M. Rao
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Patent number: 4447648Abstract: Saturated aliphatic aldehydes are prepared by contacting acetals or ketals with synthesis gas and a Group VIII compound, preferably a cobalt compound.Type: GrantFiled: August 31, 1982Date of Patent: May 8, 1984Assignee: Union Carbide CorporationInventor: Richard W. Wegman
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Patent number: 4446328Abstract: A process for producing methacrolein by oxidizing isobutylene or tertiary butanol with molecular oxygen, characterized by contacting a gaseous mixture of isobutylene or tertiary butanol, air or oxygen and optionally steam and an inert gas with a catalyst having the general composition:Mo.sub.12 Fe.sub.a Ni.sub.b Te.sub.c X.sub.d Z.sub.f Y.sub.g O.sub.hwherein a, b, c, d, f and g represent the numbers of atoms of the respective elements per 12 molybdenum atoms; X is Tl, Rb or Cs; Z is In or Ti; Y represents at least one element selected from the group consisting of Cu, Nd, Sm and Pb; a is a value of 0.2-6; b is a value of 0.2-6; a+b is a value of 1-10; c is a value of 0.1-4; d is a value of 0.1-3; f is a value of 0.1-3; g is a value of 0-5; and h is the number of oxygen atoms for satisfying the valencies of the existing elements. The use of this catalyst enables the selectivity for methacrolein to be improved to 90 or more and the yield based on the starting material to be increased to 89-91%.Type: GrantFiled: May 14, 1981Date of Patent: May 1, 1984Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Atsushi Aoshima, Ryoichi Mitsui
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Patent number: 4435598Abstract: An improved process for the catalytic oxidation of propylene to acrylic acid the improvement comprising conducting the process in the presence of an effective amount of hydroquinone. The improved process is particularly applicable to the aqueous liquid phase reaction of propylene with molecular oxygen using a supported palladium catalyst.Type: GrantFiled: October 28, 1977Date of Patent: March 6, 1984Assignee: National Distillers and Chemical CorporationInventor: James A. Hinnenkamp
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Patent number: 4419525Abstract: 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: GrantFiled: March 11, 1982Date of Patent: December 6, 1983Assignee: Phillips Petroleum CompanyInventors: Tod K. Shioyama, Jim J. Straw
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Patent number: 4415757Abstract: A process for the production of a saturated carbonyl compound which comprises bringing into reaction at an elevated temperature in the gas phase an alkane with molecular oxygen and a hydrogen halide in the presence of a solid particulate catalyst composition comprising (1) metallic silver and/or a compound thereof and (2) one or more compounds of at least one other metal having a variable valency.Useful for the production of acetaldehyde from ethane.Type: GrantFiled: March 15, 1982Date of Patent: November 15, 1983Assignee: Imperial Chemical Industries PLCInventors: David R. Pyke, Robert Reid
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Patent number: 4404397Abstract: A stabilized heteropoly molybdate catalyst precursor in calcined form and containing anionic molybdenum in defect state is surface impregnated with certain metal cations. The stabilized precursor is one obtained by incorporating into the reaction product of a molybdate and a soluble phosphate, silicate or arsenate, an aqueous chloride ion and a compound of phosphotungstate, silicotungstate, vanadium arsenate, silico-arsenate, phosphovanadate, or silicovanadate, followed by drying and calcining. During the chloride ion stabilization step other metals may be optionally incorporated in forming the stabilized precursor.The obtained precursor is catalytically active in the conversion of the unsaturated aldehydes to the corresponding unsaturated carboxylic acids with or without incorporation of the metal cation during the chloride ion stabilization step.Type: GrantFiled: December 29, 1980Date of Patent: September 13, 1983Assignee: Air Products and Chemicals, Inc.Inventor: Chelliah Daniel
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Patent number: 4340765Abstract: 4-Phenoxy-2-butene derivatives are disclosed as inhibitors of cytokinin plant growth regulatory activity and as possessing seed germination regulatory properties and senescence delaying activity when applied to plants. 4-Phenoxy-2-butene derivatives can also be useful as plant dwarfing agents, agents to retard seedling development or as herbicides.Type: GrantFiled: August 14, 1980Date of Patent: July 20, 1982Inventors: Gary M. Gray, George Schwartzkopf, Jr., J. T. Baker Chemical Co.
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Patent number: 4335264Abstract: The catalytic vapor phase oxidation of an olefin of 3 to 5 carbon atoms to .alpha.,.beta.-unsaturated aldehydes with the formation of substantially no .alpha.,.beta.-unsaturated acids is achieved by contacting the olefin, oxygen, an inert gas or moderator and optionally water with a catalyst at a temperature of from 300.degree. C. to 500.degree. C. for a period of time sufficient to achieve from 25 to 80% conversion of said olefin to said aldehyde, separating unreacted olefin and byproduct inert gas from the product stream and recycling the unreacted olefin and byproduct inert gas together with additional olefin and oxygen if required to react with said catalyst.Type: GrantFiled: July 7, 1976Date of Patent: June 15, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventor: Paul C. Yates
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Patent number: 4323520Abstract: The present invention relates to a process for the conversion of tertiary-butyl-containing compounds to methacrylic derivatives, and more particularly to a process for the conversion of tertiary-butyl-containing compounds selected from the group consisting of alkyl tertiary-butyl ethers, tertiary-butyl alcohol, isobutylene dimer (2,2,4-trimethylpentene) and isobutylene trimer, to methacrolein, methacrylic acid or methacrylonitrile.Type: GrantFiled: May 9, 1977Date of Patent: April 6, 1982Assignee: The Standard Oil Co.Inventors: Harley F. Hardman, James L. Callahan, Robert K. Grasselli
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Patent number: 4311563Abstract: The invention relates to a process for the isolation of chloroacetaldehyde which is obtained as a by-product during the synthesis of acetaldehyde from ethylene and air in an aqueous palladium/cupric chloride solution by the 2-stage process. The mixture to be worked-up to chloroacetaldehyde is taken from the acetaldehyde distillation column and transferred to a distillation and extraction system, where it is fractionally condensed. The chloroacetaldehyde-containing fraction is extracted with water and the aqueous extract is subjected to purification distillation.Type: GrantFiled: March 31, 1981Date of Patent: January 19, 1982Assignee: Wacker-Chemie GmbHInventors: Werner Opavsky, Josef Reisner, Alois Maier
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Patent number: 4306090Abstract: Methacrolein is produced by the catalytic vapor phase oxidation of isobutylene (including compounds converted to isobutylene). The catalyst has the following formula: Mo.sub.a P.sub.b Fe.sub.c Co.sub.d Ni.sub.e Bi.sub.f Te.sub.g Sb.sub.h Cs.sub.i Zr.sub.j X.sub.k O.sub.x wherein a-k represent the number of atoms of the particular element depicted, X is another element and x is the number of oxygens present.Type: GrantFiled: August 29, 1980Date of Patent: December 15, 1981Assignee: Rohm and Haas CompanyInventors: Lawrence S. Kirch, William J. Kennelly
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Patent number: 4263448Abstract: An oxidizable hydrocarbon is oxidized in a reaction zone at elevated temperature in the presence of a liquid reaction medium by introducing the hydrocarbon and a feed stream containing molecular oxygen to the reaction zone under conditions sufficient to oxidize at least a portion of the hydrocarbon; withdrawing at least a portion of the liquid reaction medium from the reaction zone; passing at least a portion of the withdrawn liquid reaction medium to an oxygen injection zone located external to the reaction zone; contacting the liquid in said oxygen-injection zone with a gas stream containing molecular oxygen under conditions sufficient to form a two-phase gas/liquid mixture; and passing said two-phase gas/liquid mixture to the reaction zone as the feed of molecular oxygen thereto.Type: GrantFiled: March 30, 1979Date of Patent: April 21, 1981Assignee: Halcon Research and Development Corp.Inventor: James Leacock
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Patent number: 4226798Abstract: A method is disclosed for using a pendulum viscometer having damped torsional oscillations, in a laboratory catalytic fluid-bed reactor, to monitor a propensity to stick which is exhibited by certain supported catalysts. A fluid-bed of such catalysts has been found to become suddenly more sticky just before a point at which a change in pressure drop across the fluid-bed can be measured due to a process "upset". At this point ("the inversion point"), the upset is usually irremediable. The method includes correlating data on catalyst stickiness from a laboratory reactor operating at atmospheric pressure, with an expected level of catalyst stickiness in a commercial reactor operating at elevated pressure.A pendulum viscometer and related auxiliary apparatus is disclosed for magnetically and electrically measuring and recording the rate at which the pendulum's torsional oscillations are damped.Type: GrantFiled: October 6, 1978Date of Patent: October 7, 1980Assignee: The B. F. Goodrich CompanyInventors: Joseph A. Cowfer, Dane E. Jablonski, Ronald M. Kovach, Angelo J. Magistro
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Patent number: 4217309Abstract: Methacrolein is produced in a high yield by catalytically oxidizing isobutylene at a temperature of from 250.degree. to 500.degree. C. by using a catalyst represented by the formula:Mo.sub.a Co.sub.b Fe.sub.c Bi.sub.d Cs.sub.e X.sub.f Y.sub.g O.sub.hwherein X is either both vanadium and palladium, Y is at least one member selected from titanium, nickel, tin and zirconium, a=12, b=2-12, c=0.5-7, d=0.1-5, e=0.0005-0.5, f=0.01-2, g=0-5 and h is a positive number proportional to the number of oxygen atoms satisfying the average valency of the metal atoms stated in the formula, which catalyst has a high resistance to compression and abrasion and exhibits a high catalytic efficiency, mechanical strength and durability.Type: GrantFiled: February 28, 1979Date of Patent: August 12, 1980Assignee: Ube Industries, Ltd.Inventors: Sumio Umemura, Kyoji Ohdan, Kenichi Suzuki, Yasuo Bando, Terumi Hisayuki