Organic Hydroxy Containing Reactant Patents (Class 568/471)
  • Patent number: 9586884
    Abstract: The present invention provides the use of a metal-doped hydroxyapatite catalyst for highly selective conversion of an alcohol to an aldehyde at low temperatures. More specifically, the invention provides the use of a silver-doped hydroxyapatite catalyst for the highly selective oxidative dehydrogenation of ethanol to acetaldehyde. The present invention also provides the method for converting ethanol to acetaldehyde using a silver-doped hydroxyapatite catalyst.
    Type: Grant
    Filed: March 28, 2014
    Date of Patent: March 7, 2017
    Assignees: Agency for Science, Technology and Research, Nanyang Technological University
    Inventors: Kanaparthi Ramesh, Armando Borgna, Yi Ling Eileen Goh, Timothy John White
  • Patent number: 9422213
    Abstract: The present disclosure relates to a method and apparatus for producing dimethyl ether by catalytic dehydration of methanol and by distillation of the dehydration product. The method is characterized in that the catalytic dehydration takes place in at least two reaction stages which are connected in series and of which at least the first reaction stage is operated adiabatically, wherein a cooling of the reaction products takes place at least between the first and the second reaction stages.
    Type: Grant
    Filed: September 10, 2013
    Date of Patent: August 23, 2016
    Assignee: THYSSENKRUPP INDUSTRIAL SOLUTIONS AG
    Inventors: Melanie Bauer, Harald Kömpel, Alexander Schulz
  • Patent number: 9315439
    Abstract: Provided is an aldehyde production method that can provide target aldehydes with excellent aldehyde selectivity and a high conversion for a long period of time. The method includes bringing a mixed gas containing a vaporized primary alcohol and an inert gas into contact with a film-type dehydrogenation catalyst so as to dehydrogenate the primary alcohol in the mixed gas, thereby obtaining an aldehyde. The partial pressure of the primary alcohol in the mixed gas is 50 kPa or lower, and the film-type dehydrogenation catalyst is formed by providing a thin film catalyst layer on a support.
    Type: Grant
    Filed: June 11, 2013
    Date of Patent: April 19, 2016
    Assignee: Kao Corporation
    Inventors: Tsubasa Arai, Jun Kono, Takahiro Asada, Ryo Nishimura, Kunio Matsui, Satoshi Kodama
  • Patent number: 9206108
    Abstract: The invention relates to a process for production of at least one C4 oxidation product, comprising the steps: a) providing a feed composition comprising at least two feed compounds selected from tert-butyl alcohol, methyl tert-butyl ether and isobutylene; b) subjecting the feed composition to a catalytic reaction zone comprising at least one oxidation stage and obtaining a reaction phase comprising the C4 oxidation product, to a C4 oxidation product obtainable therefrom, to an apparatus for production of at least one C4 oxidation product, a process carried out in the apparatus, to a methacrylic acid, to a polymer comprising methacrylic acid and process for production thereof, to methyl methacrylate and a process for production thereof, to a methacrylate ester and a process for production thereof, to a polymer comprising at least one of methacrylic acid, methyl methacrylate and a methacrylate ester and a process for production thereof, to a composition comprising at least one of methacrylic acid, methyl methac
    Type: Grant
    Filed: February 25, 2008
    Date of Patent: December 8, 2015
    Assignee: EVONIK ROEHM GMBH
    Inventor: Torsten Balduf
  • Patent number: 9056304
    Abstract: The present invention refers to a catalyst for aldehyde production, in particular formaldehyde or acetaldehyde production, through selective oxidation of alkanol, especially methanol or ethanol, with oxygen, said catalyst having a spinel structure. The catalyst typically comprises a Fea+qVb+xMoc+y?zO4 spinel structure wherein ? is an optional cation vacancy and wherein z=3?q?x?y and q×a+x×b+y×c=8 in concentrations corresponding to 0.6<q<3, 0?x<1.5, 0?y?1 and 0?z<1.3 and 2?a?3, 3?b?5 and 3?c?6. The present invention further refers to a process for producing said catalyst and to the use of said catalyst for selective oxidation of alkanol, preferably methanol or ethanol, with oxygen to aldehyde, preferably formaldehyde or acetaldehyde.
    Type: Grant
    Filed: January 19, 2011
    Date of Patent: June 16, 2015
    Assignee: JOHNSON MATTHEY FORMOX A.B.
    Inventors: Arne Andersson, Robert Haggblad
  • Publication number: 20150126740
    Abstract: The present invention provides a method for producing farnesal that is useful as a production intermediate of pharmaceuticals, agricultural chemicals and perfumes. More specifically, the present invention provides a method for producing farnesal (3), comprising reacting (E)-nerolidol (1) with an oxidizing agent in the presence of a vanadium complex of the general formula (2): wherein R1 to R7 are the same as defined in the description and claims.
    Type: Application
    Filed: December 21, 2012
    Publication date: May 7, 2015
    Inventors: Munenori Inoue, Hiroshi Araki, Takeshi Tanaka
  • Publication number: 20140316149
    Abstract: 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: Application
    Filed: April 17, 2014
    Publication date: October 23, 2014
    Applicant: CALIFORNIA INSTITUTE OF TECHNOLOGY
    Inventors: ZACHARY K. WICKENS, BILL MORANDI, ROBERT H. GRUBBS, KACPER SKAKUJ, SARAH BRONNER
  • Patent number: 8796482
    Abstract: A process of oxidizing primary alcohols to their corresponding aldehydes is disclosed. The process is effected in the presence of noble metal polyoxometalate complexes. A novel process for preparing noble metal polyoxometalate complexes, and novel noble metal polyoxometalate complexes are also disclosed.
    Type: Grant
    Filed: September 19, 2010
    Date of Patent: August 5, 2014
    Assignee: Yeda Research and Development Co. Ltd.
    Inventors: Ronny Neumann, Delina Barats
  • Patent number: 8779213
    Abstract: The present invention relates to a bio-based glutaraldehyde compound and to the different non-fossil, natural raw material manufacture methods thereof. To prepare said compound, glycerol created by the methanolysis of vegetable oil or animal fat is used, leading after dehydration to acrolein that is caused to react with a vinyl/alkyl/ether as per a Diels-Alder cyclization reaction, followed by hydrolysis so as to obtain the bio-based glutaraldehyde of the invention. Sugars containing five carbon atoms, that is, pentoses created from for example hemicellulose, may also be used, leading after dehydration to furfural, which leads, after complete hydrogenation followed by selective oxidation, to the bio-based glutaraldehyde of the invention.
    Type: Grant
    Filed: October 19, 2010
    Date of Patent: July 15, 2014
    Assignee: Arkema France
    Inventors: Jean Luc Couturier, Jean Luc Dubois
  • Patent number: 8779212
    Abstract: The use of a supported noble metal catalyst obtainable by applying a sparingly soluble noble metal compound to a support from solution or suspension, and subsequently treating thermally, for preparing olefinically unsaturated carbonyl compounds.
    Type: Grant
    Filed: March 16, 2009
    Date of Patent: July 15, 2014
    Assignee: BASF SE
    Inventors: Torsten Mäurer, Georg Seeber, Radwan Abdallah, Thorsten Johann, Günter Wegner
  • Patent number: 8722940
    Abstract: A catalyst for the oxidation of an olefin to an unsaturated aldehyde comprising a mixed metal oxide having the formula (I): MoaWbMcM?dM?eZfOg??(I) where M represents trivalent metals, M? represents divalent metals, M? represents monovalent metals, Z represents elements in the form of an oxide, a, b, c, d, e, f and g are numbers, and where the catalyst has an anion to cation molar (ACM) ratio greater than 1.00 and less than 2.00 and an M? to M molar ratio between 1.95 and 2.15.
    Type: Grant
    Filed: March 1, 2012
    Date of Patent: May 13, 2014
    Assignee: Saudi Basic Industries Corporation
    Inventors: James W. Kauffman, David L. Sullivan, Joe D. Dostal
  • Patent number: 8680340
    Abstract: A method of production of a catalyst that has 0.05-0.25 wt. % of precious metal, preferably for the oxidative dehydrogenation of olefinically unsaturated alcohols, comprising the following steps a) producing a D.C. plasma, b) introducing the metal and support material into the plasma, c) evaporating the metal and support material or “shattering” the solid bodies of metal and support material in the plasma, and reaction of the particles, d) cooling, so that very small particles of composite material are obtained, e) applying the composite material on the catalyst support proper, the correspondingly produced catalyst and use thereof.
    Type: Grant
    Filed: April 27, 2012
    Date of Patent: March 25, 2014
    Assignee: BASF SE
    Inventors: Georg Seeber, Dirk Grossschmidt, Torsten Mäurer, Christian Baltes
  • Patent number: 8604252
    Abstract: Supported noble metal-comprising catalysts which can be obtained by a) application of colloidal noble metal in the form of a colloidal solution, optionally in admixture with additives acting as promoters, to a support material, b1) drying of the resulting product at from 150 to 350° C., or b2) drying of the resulting product at from 150 to 350° C. and subsequent calcination at from 350 to 550° C. for epoxidation or oxidative dehydrogenation, a process for producing it, its use and also the use of colloidal noble metal for producing supported catalysts.
    Type: Grant
    Filed: June 7, 2010
    Date of Patent: December 10, 2013
    Assignee: BASF SE
    Inventors: Georg Seeber, Peter Löchner, Stefan Bauer, Tobias Rosendahl, Torsten Mäurer, Günter Wegner, Martin Kamasz
  • Publication number: 20130310604
    Abstract: There is provided a process for producing aerolein, acrylic acid, methacrolein, methacrylic acid in a safe and steady manner and in high yields, which avoids a phenomenon of occurrence of an abnormal reaction attributable to the fact that the temperature at a raw material gas outlet side becomes considerably higher than the temperature at a raw material gas inlet side, with regard to the temperature of a catalyst packed in a reaction tube at vapor-phase catalytic oxidation of propylene, isobutylene, or the like.
    Type: Application
    Filed: January 16, 2012
    Publication date: November 21, 2013
    Applicant: NIPPONKAYAKU KABUSHIKIKAISHA
    Inventors: Tatsuhiko Kurakami, Susumu Matsumoto, Atsushi Sudo, Kazuo Shiraishi, Masashi Hashiba
  • Patent number: 8507736
    Abstract: A method of producing short chain alcohols from glycerol generated as a byproduct of biodiesel production is provided.
    Type: Grant
    Filed: May 15, 2008
    Date of Patent: August 13, 2013
    Assignee: BioFuel-Solution i Malmo AB
    Inventors: Christian Hulteberg, Jan Brandin, Richard R. Woods, Brook Porter
  • Patent number: 8481790
    Abstract: 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: Grant
    Filed: May 26, 2011
    Date of Patent: July 9, 2013
    Assignee: Shanghai Huayi Acrylic Acid Co., Ltd.
    Inventors: Jian Wang, Xuemei Li, Yan Zhuang, Kaimin Shi, Kun Jiao, Jianxue Ma, Xiaodong Chu, Jingming Shao
  • Patent number: 8410315
    Abstract: A process for preparing olefinically unsaturated carbonyl compounds by oxidative dehydrogenation in an oxygenous atmosphere over a supported catalyst which comprises gold and optionally further noble metals at temperatures in the range from 50 to 240° C.
    Type: Grant
    Filed: February 27, 2009
    Date of Patent: April 2, 2013
    Assignee: BASF SE
    Inventors: Michael Limbach, Joaquim Henrique Teles, Radwan Abdallah, Torsten Mäurer, Thorsten Johann
  • Publication number: 20130053595
    Abstract: A catalyst composition comprising at least an heteropolyacid deposited on a porous titania carrier. A catalyst composition comprising at least an heteropolyacid in which protons in the heteropolyacid may be partially exchanged by at least one cation selected from elements belonging to Group 1 to Group 16 of the Periodic Table of Elements that have been deposited on a porous titania carrier. A method for preparing the catalyst composition, comprising impregnating a titania carrier with a solution of at least one metal selected from elements belonging to the Group 1 to Group 16 of the Periodic Table of Elements or onium, drying and firing the resulting solid mixture, secondly impregnating the resulting solid mixture with a solution of heteropolyacid, drying, and firing the resulting solid mixture. A process for preparing acrolein and acrylic acid by dehydration of glycerin, carried out in the presence of the catalyst.
    Type: Application
    Filed: September 18, 2009
    Publication date: February 28, 2013
    Applicants: ARKEMA FRANCE, NIPPON KAYAKU KABUSHIKI KAISHA
    Inventors: Yasuhiro Magatani, Kimito Okumura, Jean-Luc Dubois, Jean-Francois Devaux
  • Publication number: 20130006019
    Abstract: The present invention refers to a catalyst for aldehyde production, in particular formaldehyde or acetaldehyde production, through selective oxidation of alkanol, especially methanol or ethanol, with oxygen, said catalyst having a spinel structure. The catalyst typically comprises a Feaq+Vb+Moc+y+?zO4 spinel structure wherein ? is an optional cation vacancy and wherein wherein z=3?q?x?y and q×a+x×b+y×c=8 in concentrations corresponding to 0.6<q<3, 0<x<1.5, 0<y<1 and 0<z<1.3 and 2<a<3, 3<b<5 and 3<c<6. The present invention further refers to a process for producing said catalyst and to the use of said catalyst for selective oxidation of alkanol, preferably methanol or ethanol, with oxygen to aldehyde, preferably formaldehyde or acetaldehyde.
    Type: Application
    Filed: January 19, 2011
    Publication date: January 3, 2013
    Inventors: Arne Andersson, Robert Haggblad
  • Publication number: 20120277475
    Abstract: The present invention relates to a bio-based glutaraldehyde compound and to the different non-fossil, natural raw material manufacture methods thereof. To prepare said compound, glycerol created by the methanolysis of vegetable oil or animal fat is used, leading after dehydration to acrolein that is caused to react with a vinyl/alkyl/ether as per a Diels-Alder cyclization reaction, followed by hydrolysis so as to obtain the bio-based glutaraldehyde of the invention. Sugars containing five carbon atoms, that is, pentoses created from for example hemicellulose, may also be used, leading after dehydration to furfural, which leads, after complete hydrogenation followed by selective oxidation, to the bio-based glutaraldehyde of the invention.
    Type: Application
    Filed: October 19, 2010
    Publication date: November 1, 2012
    Applicant: ARKEMA FRANCE
    Inventors: Jean Luc Couturier, Jean Luc Dubois
  • Publication number: 20120232279
    Abstract: The invention concerns processes for oxidizing an alcohol to produce a carbonyl compound. The processes comprise contacting the alcohol with (i) a gaseous mixture comprising oxygen; and (ii) an amine compound in the presence of a catalyst, having the formula: where each of R1-R12 are independently H, alkyl, aryl, CF3, halogen, OR13, SO3R14, C(O)R15, CONR16R17 or CO2R18; each of R13-R18 is independently alkyl or aryl; and Z is alkl or aryl.
    Type: Application
    Filed: March 8, 2012
    Publication date: September 13, 2012
    Applicant: LOS ALAMOS NATIONAL SECURITY, LLC
    Inventors: Susan Kloek Hanson, Louis A. Silks, Ruilian Wu
  • Publication number: 20120220792
    Abstract: Provided is a process for producing aldehydes or ketones by oxidizing alcohols with oxygen, which comprises oxidizing alcohols to aldehydes or ketones in an organic solvent at room temperature with oxygen or air as an oxidant, wherein ferric nitrate (Fe(NO3)3.9H2O), 2,2,6,6-tetramethylpiperidine N-oxyl (TEMPO) and an inorganic chloride are used as catalysts, the reaction time is 1-24 hours, and the molar ratio of said alcohols, 2,2,6,6-tetramethylpiperidine N-oxyl and the inorganic chloride is 100:1˜10:1˜10:1˜10. The present process has the advantages of high yield, mild reaction conditions, simple operation, convenient separation and purification, recoverable solvents, substrates used therefor being various and no pollution, and therefore it is adaptable to industrialization.
    Type: Application
    Filed: July 30, 2010
    Publication date: August 30, 2012
    Inventors: Shengming Ma, Jinxian Liu, Jinqiang Kuang, Yu Liu, Yuli Wang, Qiong Yu, Weiming Yuan, Suhua Li, Bo Chen, Jiajia Cheng, Baoqiang Wan, Juntao Ye, Shichao Yu
  • Publication number: 20120197033
    Abstract: A process of oxidizing primary alcohols to their corresponding aldehydes is disclosed. The process is effected in the presence of noble metal polyoxometalate complexes. A novel process for preparing noble metal polyoxometalate complexes, and novel noble metal polyoxometalate complexes are also disclosed.
    Type: Application
    Filed: September 19, 2010
    Publication date: August 2, 2012
    Applicant: Yeda Research and Development Co., Ltd.
    Inventors: Ronny Neumann, Delina Barats
  • Publication number: 20110295041
    Abstract: 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: Application
    Filed: May 26, 2011
    Publication date: December 1, 2011
    Applicant: Shanghai HuaYi Acrylic Acid Co. Ltd.
    Inventors: Jian Wang, Xuemei Li, Yan Zhuang, Kaimin Shi, Kun Jiao, Jianxue Ma, Xiaodong Chu, Jingming Shao
  • Publication number: 20110251399
    Abstract: The invention relates to a method for producing aldehydes and ketones from easily accessible primary and secondary alcohols by oxidation with atmospheric oxygen or pure oxygen using a catalyst system which consists of a derivative of a free nitroxyl radical.
    Type: Application
    Filed: January 25, 2010
    Publication date: October 13, 2011
    Applicant: EVONIK DEGUSSA GMBH
    Inventors: Uwe Dingerdissen, Jan Pfeffer, Thomas Tacke, Thomas Haas, Harald Schmidt, Florian Klasovsky, Roger Sheldon, Michiel Janssen, Michael Volland, Michael Rimbach, Stefanie Rinker
  • Publication number: 20110123423
    Abstract: The invention relates to the realization of synthesis of organic compounds or abatement of volatile organic compounds (VOCs) in gas-solid fluidised bed photocatalytic reactor with improved illumination efficiency. The photoreactor consists of a two-dimensional fluidized bed catalytic reactor with two walls transparent to ultraviolet radiation, by an illumination system bases on a matrix of LEDs positioned near its external walls, and heated for Joule effect inside the catalytic bed to monitor the reaction temperature. Surprisingly, through the choice of a suitable catalyst and fluidized bed photoreactor operating conditions both total and partial oxidation reactions can be achieved with high activity and selectivity. Even more surprisingly, the value of the illuminated catalyst surface area per unit irradiated volume reaches values in the order of 106 m?1, significantly higher than those of microreactors, amounting to 250,000 m?1 and slurry reactors with values in 8500-170000 m?1.
    Type: Application
    Filed: May 29, 2009
    Publication date: May 26, 2011
    Inventors: Paolo Ciambelli, Diana Sannino, Vincenzo Palma, Vincenzo Vaiano
  • Patent number: 7906689
    Abstract: A catalyst composition for use in manufacturing methacrolein by reacting with one of isobutene and t-butanol, the catalyst composition being represented by the formula of: x (Mo12BiaFebCocAdBeOf)/y Z. Mo12BiaFebCocAdBeOf is an oxide compound. Z is a catalyst carrier is one of graphite, boron, silicon, germanium powder, and a mixture thereof. Mo, Bi, Fe, Co, and O are chemical symbols of molybdenum, bismuth, iron, cobalt, and oxygen respectively. A is one of W, V, Ti, Zr, Nb, Ni, and Re. B is one of K, Rb, Cs, Sr, and Ba. The catalyst is adapted to not only enhance the production of methacrolein with high activeness and high selectivity but also effectively control the heat point of the catalyst during the methacrolein manufacturing process to prolong the catalyst life.
    Type: Grant
    Filed: November 7, 2007
    Date of Patent: March 15, 2011
    Inventors: Yan Zhuang, Chunlei Zhang, Xin Wen, Jun Li, Jingming Shao, Peizhang Zhang
  • Patent number: 7880038
    Abstract: A metal catalyst obtained by contacting (A) at least one metal or metal compound selected from i) tungsten compounds composed of tungsten and an element of group IIIb, IVb, Vb, or VIb, ii) molybdenum compounds composed of molybdenum and an element of group IIIb, IVb, Vb, or VIb, and iii) tungsten metal and molybdenum metal; (B) at least one compound selected from tertiary amine compounds, tertiary amine oxide compounds, nitrogen-containing aromatic compounds and nitrogen-containing aromatic N-oxide compounds; (C) hydrogen peroxide; and (D) a phosphate compound, is provided.
    Type: Grant
    Filed: April 14, 2004
    Date of Patent: February 1, 2011
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masaji Hirota, Koji Hagiya
  • Publication number: 20110004025
    Abstract: A process for preparing olefinically unsaturated carbonyl compounds by oxidative dehydrogenation in an oxygenous atmosphere over a supported catalyst which comprises gold and optionally further noble metals at temperatures in the range from 50 to 240° C.
    Type: Application
    Filed: February 27, 2009
    Publication date: January 6, 2011
    Applicant: BASF SE
    Inventors: Michael Limbach, Joaquim Henrique Teles, Radwan Abdallah, Torsten Mäurer, Thorsten Johann
  • Patent number: 7803972
    Abstract: The invention relates to a coated catalyst, especially for oxidation of methanol to formaldehyde, which, on an inert, preferably essentially nonporous, support body, has at least one coating which comprises, before the removal of the organic fractions of components b) and c): (a) oxides, or precursor compounds convertible to the corresponding oxides, of molybdenum and iron, where the molar ratio of Mo:Fe is between 1:1 and 5:1, and optionally further metallic components or metal oxide components or precursor compounds convertible to the corresponding oxides, (b) at least one organic binder, preferably an aqueous dispersion of copolymers, especially selected from vinyl acetate/vinyl laurate, vinyl acetate/ethylene, vinyl acetate/acrylate, vinyl acetate/maleate, styrene/acrylate or mixtures thereof, and (c) at least one further component selected from the group consisting of SiO2 sol or precursors thereof, Al2O3 sol or precursors thereof, ZrO2 sol or precursors thereof, TiO2 sol or precursors thereof, waterglas
    Type: Grant
    Filed: November 23, 2006
    Date of Patent: September 28, 2010
    Assignee: Süd-Chemie AG
    Inventors: Christian Gückel, Klaus Wanninger, Marvin Estenfelder, Claudia Fischer, Uwe Dürr
  • Patent number: 7772442
    Abstract: Disclosed is a shell-and-tube reactor that may be used for fixed-bed catalytic partial oxidation, the reactor being characterized by including at least one reaction zone of a first-step reaction zone for mainly producing unsaturated aldehydes and a second-step reaction zone for mainly producing unsaturated acids, wherein at least one reaction zone of the above reaction zones comprises two or more catalytic layers; each of the catalytic layers is packed with a formed product of catalyst that is different in pore density and/or pore size in a catalytically active component; and the pore density and/or pore size is controlled in such a manner that specific surface area of the catalytically active component increases from the inlet of the reactor to the outlet of the reactor. A method for producing unsaturated aldehydes and/or unsaturated fatty acids from olefins using the same reactor is also disclosed.
    Type: Grant
    Filed: March 31, 2009
    Date of Patent: August 10, 2010
    Assignee: LG Chem, Ltd.
    Inventors: Yeon Shick Yoo, Hyun Jong Shin, Byung Yul Choi, Young Hyun Choi, Young Jin Cho, Duk Ki Kim, Joo Yeon Park, Kwang Ho Park
  • Publication number: 20090287018
    Abstract: A catalyst for use in the production of an unsaturated aldehyde and/or an unsaturated carboxylic acid, the catalyst comparing (or, preferably, being composed of) a mixed oxide containing molybdenum, bismuth and iron, which has improved mechanical strength, is produced by a method including the steps of (1) drying an aqueous solution or an aqueous slurry containing raw materials of the catalyst and then firstly calcining a dried product in a molecular oxygen-containing gas atmosphere to obtain a calcined product; (2) heating the calcined product obtained in Step (1) in the presence of a reducing material to obtain a reduced product having a mass loss of 0.05 to 6%; and (3) secondly calcining the reduced product obtained in Step (2) in a molecular oxygen-containing gas atmosphere.
    Type: Application
    Filed: May 15, 2009
    Publication date: November 19, 2009
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Naoki MIURA, Eiichi Shiraishi, Koichi Nagai
  • Publication number: 20090171117
    Abstract: A catalyst suitable for the gas-phase oxidation of organic compounds to ?,?-unsaturated aldehydes and/or carboxylic acids and having an active phase comprising a multimetal oxide material is prepared by a process in which a particulate catalyst precursor which contains oxides and/or compounds of the elements other than oxygen which constitute the multimetal oxide material, which compounds can be converted into oxides, is prepared and said catalyst precursor is converted by calcination into a catalytically active form, wherein a stream of the particulate catalyst precursor is passed at substantially constant speed through at least one calcination zone at constant temperature for calcination.
    Type: Application
    Filed: March 2, 2009
    Publication date: July 2, 2009
    Applicant: BASF Aktiengesellschaft
    Inventors: Heiko Arnold, Signe Unverricht, Raimund Felder, Klaus Harth, Klaus Joachim Muller-Engel
  • Publication number: 20090069605
    Abstract: A catalyst composition for use in manufacturing methacrolein by reacting with one of isobutene and t-butanol, the catalyst composition being represented by the formula of: x (Mo12Bi8FebCocAdBeOf)/y Z. Mo12BiaFebCocAdBeOf is an oxide compound. Z is a catalyst carrier is one of graphite, boron, silicon, germanium powder, and a mixture thereof Mo, Bi, Fe, Co, and O are chemical symbols of molybdenum, bismuth, iron, cobalt, and oxygen respectively. A is one of W, V, Ti, Zr, Nb, Ni, and Re. B is one of K, Rb, Cs, Sr, and Ba. The catalyst is adapted to not only enhance the production of methacrolein with high activeness and high selectivity but also effectively control the heat point of the catalyst during the methacrolein manufacturing process to prolong the catalyst life.
    Type: Application
    Filed: November 7, 2007
    Publication date: March 12, 2009
    Inventors: Yan Zhuang, Chunlei Zhang, Xin Wen, Jun Li, Jingming Shao, Peizhang Zhang
  • Patent number: 7491852
    Abstract: The present invention discloses a novel use of a catalyst with core-porous shell structure, which includes carrying out an oxidation of an alcohol in vapor phase and in the presence of the catalyst with core-porous shell structure to form an aldehyde or ketone, wherein the catalyst with core-porous shell structure is constituted of a core material and a porous shell material. The core material is a metal having a catalytic activity, and the shell material is a porous inorganic oxide.
    Type: Grant
    Filed: February 28, 2008
    Date of Patent: February 17, 2009
    Assignee: National Tsing Hua University
    Inventors: Kan-Sen Chou, Chen-Chih Chen
  • Patent number: 7423184
    Abstract: A method of making a carbonyl compound comprises contacting a compound comprising a secondary hydroxyl group with a basic metal oxide catalyst at a temperature sufficient to maintain the compound comprising a secondary hydroxyl group in a vapor phase.
    Type: Grant
    Filed: August 29, 2005
    Date of Patent: September 9, 2008
    Assignee: Sabic Innovative Plastics IP B.V.
    Inventors: Hugo Ingelbrecht, Arun Kumar, Ashok Ramakrishnan Menon, Pradeep Nadkarni, Rupesh Pawar
  • Publication number: 20080004173
    Abstract: A process for regenerating a catalyst consisting of a mixed oxide having molybdenum, bismuth and iron used for preparing an unsaturated aldehyde and/or an unsaturated carboxylic acid by catalytically oxidizing propylene, isobutylene and/or tert.-butanol with molecular oxygen in a gas phase, in which the catalyst is regenerated by thermally treating the deteriorated catalyst in an atmosphere of a gas containing molecular oxygen at a temperature of 200 to 500° C., and then thermally treating the catalyst in the presence of a reducing compound at a temperature of 200 to 500° C.
    Type: Application
    Filed: June 27, 2007
    Publication date: January 3, 2008
    Inventors: Naoki Miura, Koichi Nagai, Noriaki Suyasu
  • Publication number: 20070167647
    Abstract: Disclosed is a shell-and-tube reactor or heat exchanger comprising: first tubes, through the inside of which a first object for heat transfer with a heat transfer medium is passed, some of the first tubes being provided in a zone in which a flow of the heat transfer medium (parallel flow) parallel to the axis of the tubes is present; and a second tube, through the inside of which the first object is not passed, the second tube being provided in said zone such that it is parallel to the axis of the first tubes. Also disclosed is a method for producing an oxide, comprising using said shell-and-tube reactor or heat exchanger, and causing a catalytic vapor-phase oxidation reaction in first tubes, through the inside of which the first object for heat transfer with the heat transfer medium is passed.
    Type: Application
    Filed: January 18, 2007
    Publication date: July 19, 2007
    Inventors: Sang Baek Shin, Sang Phil Han, Ye Hoon Im, Young Bae Kim, Jung Hoon Chang, Sang Oeb Na, Won Am Lee
  • Patent number: 7235701
    Abstract: The invention provides a film-type dehydrogenation reaction catalyst for aldehyde production, which is used in producing an aldehyde from an alcohol as a starting material, as well as a process for producing an aldehyde, which includes reacting an alcohol in the presence of the film-type dehydrogenation reaction catalyst.
    Type: Grant
    Filed: June 6, 2005
    Date of Patent: June 26, 2007
    Assignee: Kao Corporation
    Inventors: Shoji Hasegawa, Toru Nishimura, Osamu Tabata
  • Patent number: 7208634
    Abstract: A method for preparing an aldehyde or ketone by oxidizing a primary or secondary alcohol in the presence of a nitroxyl radical compound and a co-oxidant in an organic solvent, which process is characterized in using an organic N-bromoamide compound or a combination of N-chlorosuccinimide and a compound having bromide ion as the co-oxidant.
    Type: Grant
    Filed: December 1, 2005
    Date of Patent: April 24, 2007
    Assignee: Daiso Co., Ltd.
    Inventors: Kimitaka Igi, Makoto Hirata, Masafumi Mikami
  • Patent number: 7169954
    Abstract: A ruthenium-carrying alumina, which is prepared by suspending alumina in a solution containing trivalent ruthenium and adding a base to the suspension, is provided. This ruthenium-carrying alumina is useful as a catalyst for oxidizing alcohols by contacting the alcohols with molecular oxygen, and can be used for oxidizing the alcohols at a high conversion to produce ketones, aldehydes, carboxylic acids, etc. with good productivity.
    Type: Grant
    Filed: April 25, 2003
    Date of Patent: January 30, 2007
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Noritaka Mizuno, Kazuya Yamaguchi, Hajime Ishida
  • Patent number: 7118920
    Abstract: Multiphasic reactions, especially those reactions using a phase transfer catalyst, are conducted in microchannel apparatus. Advantageously, these reactions can be conducted with two, planar microlayers of reactants in adjacent laminar flow streams. Microchannel apparatus and methods for conducting unit operations such as reactions and separations in microchannel apparatus is also described. Microchannel apparatus can provide advantages for controlling reactions and separating products, solvents or reactants in multiphase reactions.
    Type: Grant
    Filed: October 22, 2002
    Date of Patent: October 10, 2006
    Assignee: Battelle Memorial Institute
    Inventors: John H. Brophy, Bruce F. Monzyk
  • Patent number: 7034170
    Abstract: Manganese(IV) complex salts of formula [LMn(?-O)3MnL]n[XM12O40]m, (I), wherein L is 1,4,7-trimethyl-1,4,7-triazacyclononane, X is P or Si, M is Mo or W, n is 2 or 3, and m is 1 or 2, with the provisos that (i) if X is Si, then n=2 and m=1 and (ii) if X is P, then n=3 and m=2. These compounds are active catalysts in the partial oxidation of various organic compounds with peroxy compounds, e.g., the preparation of ketones from secondary alcohols or the epoxidation of olefins.
    Type: Grant
    Filed: January 13, 2003
    Date of Patent: April 25, 2006
    Assignee: Lonza AG
    Inventors: Marco Bosch, Dario Veghini
  • Patent number: 7030279
    Abstract: An alcohol can be oxidized by a process in which a primary or secondary alcohol are reacted with an oxygen-containing gas in the presence of a catalyst composition containing (i) a stable free nitroxyl radical derivative, (ii) a nitrate source, (iii) a bromide source, and (iiii) a carboxylic acid, thereby obtaining an aldehyde or a ketone.
    Type: Grant
    Filed: December 23, 2004
    Date of Patent: April 18, 2006
    Assignee: Degussa AG
    Inventors: Setrak Tanielyan, Robert Augustine, Oliver Meyer, Michael Korell
  • Patent number: 7000382
    Abstract: A method of partially oxidizing an alcohol to an aldehyde or ketone comprises contacting a gas containing the alcohol with a solid catalyst containing molybdenum, preferably in a +6 oxidation state, and having a surface area of 10 m2/g or higher, preferably 100 m2/g or higher. The molybdenum is supported on a high surface area carrier. The alcohol is a primary or secondary alcohol and preferably contains from 1 to 6 carbon atoms. In a preferred embodiment, the alcohol is ethanol. NOx emissions from an internal combustion engine can be lowered by combining the product of partial oxidation with the exhaust stream before passing the exhaust mixture through a lean NOx catalyst.
    Type: Grant
    Filed: July 2, 2003
    Date of Patent: February 21, 2006
    Assignee: General Motors Corporation
    Inventors: Jong-Hwan Lee, Steven J. Schmieg, Se H. Oh
  • Patent number: 6995291
    Abstract: The present invention relates to the field of organic synthesis and more precisely to a process for the synthesis of an unsaturated aldehyde or ketone by oxidation of the corresponding alcohol. The oxidation is performed by a hypochlorite salt and a catalytic amount of a N-(2,2,6,6-tetraalkyl-4-piperidinyl-N-oxyl)-2-amino-1,3,5-triazine compound, preferably a N-oxyl derivative of one of the polymers known under the trademark Chimassorb® 944 or 2020.
    Type: Grant
    Filed: September 22, 2003
    Date of Patent: February 7, 2006
    Assignee: Firmenich SA
    Inventor: Eric Walther
  • Patent number: 6897342
    Abstract: A process for making aldehydes involving: (a) providing a fatty alcohol; (b) providing an oxidic copper/zinc catalyst; and (c) continuously dehydrogenating the fatty alcohol, in the presence of the oxidic copper/zinc catalyst, at a temperature of from about 200 to 280° C. and a pressure of from about 10 mbar to 1 bar.
    Type: Grant
    Filed: June 19, 2001
    Date of Patent: May 24, 2005
    Assignee: Cognis Deutschland GmbH & Co. KG
    Inventors: Albrecht Schwerin, Gerrit Pelzer, Lothar Friesenhagen, Bernhard Gutsche
  • Patent number: 6878847
    Abstract: A catalyst useful for catalytic vapor-phase oxidation of isobutylene, t-butanol or propylene to produce respectively corresponding unsaturated aldehyde and unsaturated carboxylic acid is provided. The catalyst consists of ring-formed shaped bodies composed of (i) a catalyst composition containing at least molybdenum and bismuth as the active ingredients and (ii) inorganic fibers. The catalyst excels in mechanical strength, can give the object products at high yield and shows little activity degradation with time.
    Type: Grant
    Filed: April 20, 2004
    Date of Patent: April 12, 2005
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Hiroto Kasuga, Eiichi Shiraishi
  • Patent number: 6825384
    Abstract: The present invention relates to a process of oxidation of alcohols selectively to aldehydes or ketones with NaOCl using a TEMPO—borate catalyst system. It is shown that the oxidation can be efficiently carried out without KBr additives under solvent free conditions. Aldehydes such as 3,3-dimethylbutyraldehyde can be produced efficiently using the present invention.
    Type: Grant
    Filed: January 29, 2004
    Date of Patent: November 30, 2004
    Assignee: The NutraSweet Company
    Inventors: Indra Prakash, Setrak K. Tanielyan, Robert L. Augustine, Kenneth E. Furlong, Robert C. Scherm, Handley E. Jackson
  • Patent number: 6768013
    Abstract: A novel process for the direct oxidation of hydrogen and hydrocarbons is disclosed, where the explosion risks inherent in gas phase oxidations are substantially eliminated. Gaseous oxidation reactants are soluble in a first reaction solvent phase such as a perfluorocarbon (e.g. C8F18) and the oxidation product is preferentially soluble in a second product solvent phase such as water or a dilute acid. A solid catalyst such as palladium on alumina is then contacted with the dissolved reactants. The oxidation product such as hydrogen peroxide may be separated from the reaction solvent phase by extraction into the immiscible product solvent phase and then separated from it by distillation, thereby allowing re-use of the aqueous phase. The present invention may be carried out using a two-phase reaction system whereby both the reaction solvent and product solvent are contained within a reaction vessel into which the solid catalyst is slurried and mechanically agitated to promote the reaction.
    Type: Grant
    Filed: June 15, 2001
    Date of Patent: July 27, 2004
    Assignee: UOP LLC
    Inventor: Peter R. Pujado