Liquid Phase Oxidation Patents (Class 562/533)
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Patent number: 11597693Abstract: A process for production of malic acid includes obtaining a feed that includes one or more of crude maleic anhydride, pure maleic anhydride, crude maleic acid, crude fumaric acid, pure maleic acid, pure fumaric acid, vent gas scrubber solutions from production of maleic anhydride, and vent gas scrubber solutions from production of phthalic anhydride. The feed is passed in a tubular reactor assembly to obtain a first product stream, which includes unreacted feed and malic acid. The feed is made to undergo hydration reaction in the tubular reactor assembly for a first predetermined time period, and further hydration of the first product stream is caused in a stirred tank reactor assembly for a second predetermined time period to obtain a final product stream, which includes the malic acid.Type: GrantFiled: March 16, 2022Date of Patent: March 7, 2023Assignee: THIRUMALAI CHEMICALS LIMITEDInventor: Parthasarathy Rangaswamy
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Patent number: 10029975Abstract: The present invention relates to the manufacture of biobased acrylic acid from glycerol as starting material, the term “biobased acid” indicating that the acrylic acid is essentially based on a carbon source of natural origin.Type: GrantFiled: February 16, 2015Date of Patent: July 24, 2018Assignee: Arkema FranceInventors: Jean-Francois Devaux, Michel Fauconet, Sandeep Jain, Stephen Tlatlik
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Patent number: 8962881Abstract: The disclosed invention is a method for manufacturing an oxidized organic compound which includes a step of forming an oxidized organic compound, in use of a fixed-bed reactor having a reaction tube packed with an oxide catalyst, by supplying at least one type of organic compound as a reaction feedstock gas and using a molecular oxygen-containing gas to carry out a catalytic gas-phase oxidation reaction; and a step of stopping the catalytic gas-phase oxidation reaction. In the manufacturing method, when stopping the catalytic gas-phase oxidation reaction, the supply of the reaction feedstock gas is stopped, after which an inert gas is supplied to the reactor, then a molecular oxygen-containing gas is supplied, subsequent to which the supply of the molecular oxygen-containing gas to the reactor is stopped.Type: GrantFiled: March 9, 2009Date of Patent: February 24, 2015Assignee: Nippon Shokubai Co, LtdInventors: Michio Tanimoto, Nobuyuki Hakozaki
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Patent number: 8609895Abstract: A process for the oxidation of alcohol and/or aldehyde groups with a peroxo compound in the presence of a heterogeneous rhenium based catalyst, and a co-catalyst. The process of the invention may, for example, be applied to the manufacture of maleic acid which can be dehydrated to lead to maleic anhydride.Type: GrantFiled: July 16, 2009Date of Patent: December 17, 2013Assignee: Solvay SAInventors: Raffaele Saladino, Angela Farina
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Patent number: 8492584Abstract: The invention relates to a process for oxidizing at least one organic substance with oxygen, which comprises the following steps: (a) adding the at least one organic substance as a liquid and an oxygenous gas stream to a first reaction stage to form a reaction mixture, at least some of the oxygen reacting with the organic compound to form a reaction product, (b) adding the reaction mixture from the first reaction stage to an adiabatically operated reaction stage in which the unconverted organic substance reacts further at least partly to give the product. The invention further relates to an apparatus for performing the process.Type: GrantFiled: August 18, 2008Date of Patent: July 23, 2013Assignee: BASF SEInventors: Joaquim Henrique Teles, Steffen Oehlenschläger, Kai Gumlich, Martin Schäfer, Stephan Lamm, Stefan Berg, Michael Nilles, Hans-Peter Schildberg, Tilo John, Peter Zehner
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Patent number: 8426335Abstract: An object of the present invention is to provide: a catalyst for production of acrylic acid which is a catalyst usable for production of acrylic acid and is excellent in the catalytic performances such as catalytic activity and in the physical properties such as physical strength of the catalyst itself; and a process for production of acrylic acid using this catalyst. As a means of achieving this object, a catalyst for production of acrylic acid according to the present invention is a catalyst obtained by drying a mixed liquid of starting materials including molybdenum and vanadium as essential components to give a dried material, molding the dried material with a liquid binder, and calcining the resultant molding, with the catalyst being characterized in that an ignition loss ratio of the dried material is from 5 to 40% by mass.Type: GrantFiled: October 6, 2008Date of Patent: April 23, 2013Assignee: Nippon Shokubai Co., Ltd.Inventors: Hiromi Yunoki, Michio Tanimoto, Daisuke Nakamura
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Patent number: 8389760Abstract: Disclosed is a palladium-containing catalyst which enables to produce an ?,?-unsaturated carboxylic acid in high selectivity from an olefin or an ?,?-unsaturated aldehyde. Also disclosed are a method for producing such a catalyst and a method for producing an ?,?-unsaturated carboxylic acid using such a catalyst. Specifically disclosed is a palladium-containing catalyst containing 0.001 to 0.25 mole of antimony element to 1 mole of palladium element or a palladium-containing catalyst containing palladium element which composes a metal, tellurium element, and bismuth element.Type: GrantFiled: November 8, 2011Date of Patent: March 5, 2013Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Toshiya Yasukawa, Toshiki Matsui, Ken Ooyachi, Yoshiyuki Himeno, Wataru Ninomiya
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Patent number: 8378136Abstract: The subject of the present invention is a process for preparing acrolein by dehydration of glycerol in the presence of a catalyst system comprising oxygen, phosphorus and at least one metal chosen from vanadium, boron or aluminium. The process is preferably carried out in the gas phase in the presence of oxygen starting from aqueous solutions of glycerol.Type: GrantFiled: October 5, 2009Date of Patent: February 19, 2013Assignee: Arkema FranceInventor: Jean-Luc Dubois
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Patent number: 8362296Abstract: The present invention relates to a process for preparing 4-pentenoic acid, at least comprising the oxidation of a mixture (G) comprising 4-pentenal, 3-methyl-2-butanone and cyclopentene oxide, and to the use of a mixture (G) comprising 4-pentenal, 3-methyl-2-butanone and cyclopentene oxide for preparing 4-pentenoic acid. In the context of the present invention, the mixture (G) is preferably obtained as a by-product of the oxidation of cyclopentene to cyclopentanone by means of dinitrogen monoxide.Type: GrantFiled: August 19, 2010Date of Patent: January 29, 2013Assignee: BASF SEInventors: Joaquim Henrique Teles, Michael Schelper, Kai Gumlich, Mathieu Chabanas, Christian Müller, Anton Meier
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Publication number: 20120330058Abstract: The present invention relates to the manufacture of bioresourced acrolein and bioresourced acrylic acid from glycerol as starting material and more particularly comes within the scope of a process for the manufacture of acrolein and acrylic acid according to which the reaction for the dehydration of glycerol to give acrolein is carried out and the organic compounds which are heavier than water liable to be present in the various streams of the process arc removed, so as to obtain a stream which can be recycled to the dehydration stage without accumulation of heavy impurities, while minimizing the consumption of water and the discharge of polluted aqueous streams.Type: ApplicationFiled: December 10, 2010Publication date: December 27, 2012Inventors: Jean-Francois Devaux, Andre Lozowski, Nabil Tlili
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Patent number: 8173838Abstract: Disclosed is a method for producing at least one of an ?,?-unsaturated aldehyde and an ?,?-unsaturated carboxylic acid from an alcohol in a liquid phase through a simple process. Namely, at least one of an ?,?-unsaturated aldehyde and an ?,?-unsaturated carboxylic acid is produced by dehydrating and oxidizing an alcohol in a liquid phase at 110 to 250° C. in the presence of molecular oxygen and a noble metal-containing catalyst. Alternatively, at least one of an ?,?-unsaturated aldehyde and an ?,?-unsaturated carboxylic acid is produced by dehydrating and oxidizing an alcohol in a liquid phase in the presence of molecular oxygen, a noble metal-containing catalyst, and an acidic substance.Type: GrantFiled: October 3, 2006Date of Patent: May 8, 2012Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Akio Takeda, Yuji Fujimori, Seiichi Kawato
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Publication number: 20120046433Abstract: A process for producing (meth)acrylic acid, comprising a crystallizing step of supplying a cooling medium from a refrigerator to a crystallizer and returning the cooling medium from the crystallizer to the refrigerator, thereby obtaining a (meth)acrylic acid crystal from a (meth)acrylic acid-containing solution; and a melting step of supplying a heating medium from a refrigerator to the crystallizer and returning the heating medium from the crystallizer to the refrigerator, thereby melting the (meth)acrylic acid crystal; wherein the crystallizing step and the melting step are respectively performed at least once, thereby producing purified (meth)acrylic acid from a crude (meth)acrylic acid solution; temperature of the cooling medium discharged from the refrigerator is maintained constant at temperature T1; temperature of the cooling medium to be returned to the refrigerator is maintained constant at temperature T2; the temperature T2 is adjusted depending on a production amount of the purified (meth)acrylic aType: ApplicationFiled: May 7, 2010Publication date: February 23, 2012Inventor: Satoshi Nakagawa
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Patent number: 8088945Abstract: Disclosed is a palladium-containing catalyst which enables to produce an ?,?-unsaturated carboxylic acid in high selectivity from an olefin or an ?,?-unsaturated aldehyde. Also disclosed are a method for producing such a catalyst and a method for producing an ?,?-unsaturated carboxylic acid using such a catalyst. Specifically disclosed is a palladium-containing catalyst containing 0.001 to 0.25 mole of antimony element to 1 mole of palladium element or a palladium-containing catalyst containing palladium element which composes a metal, tellurium element, and bismuth element.Type: GrantFiled: December 10, 2010Date of Patent: January 3, 2012Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Toshiya Yasukawa, Toshiki Matsui, Ken Ooyachi, Yoshiyuki Himeno, Wataru Ninomiya
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Patent number: 8088946Abstract: The present invention provides: a palladium-containing supported catalyst which is used for producing an ?,?-unsaturated carboxylic acid from an olefin or an ?,?-unsaturated aldehyde in high selectivity; a method for manufacturing the catalyst; and a method for producing an ?,?-unsaturated carboxylic acid in high selectivity. In particular, the present invention resides in a method for manufacturing a palladium-containing supported catalyst for producing an ?,?-unsaturated carboxylic acid from an olefin or an ?,?-unsaturated aldehyde, comprising the step of reducing palladium oxide contained in a catalyst precursor wherein at least the palladium oxide is supported on a carrier. By using such a palladium-containing supported catalyst, an ?,?-unsaturated carboxylic acid is produced through liquid-phase oxidation of an olefin or an ?,?-unsaturated aldehyde with molecular oxygen.Type: GrantFiled: November 14, 2005Date of Patent: January 3, 2012Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Yoshiyuki Himeno, Wataru Ninomiya, Ken Ooyachi
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Patent number: 8058473Abstract: Disclosed is a method for producing an ?, ?-unsaturated carboxylic acid from an olefin or an ?, ?-unsaturated aldehyde, while suppressing dissolution of a silica carrier, which is a carrier for a silica-supported noble metal-containing catalyst, in a water-containing solvent. Specifically disclosed is a method for producing an ?, ?-unsaturated carboxylic acid through oxidation of an olefin or an ?, ?-unsaturated aldehyde in a water-containing solvent in the presence of a silica-supported noble metal-containing catalyst in a reactor, in which at least one of silicic acid and ions thereof is supplied into the reactor.Type: GrantFiled: December 26, 2007Date of Patent: November 15, 2011Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Toshiki Matsui, Yoshiyuki Himeno, Kazunori Matake
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Patent number: 7999133Abstract: Methods for making unsaturated acids using catalysts for oxidation of unsaturated and/or saturated aldehyde to unsaturated acids is disclosed where the catalyst including at least molybdenum (Mo) and phosphorus (P), where the catalyst has a pore size distribution including at least 50% medium pores and if bismuth is present, a nitric acid to molybdenum mole ratio of at least 0.5:1 or at least 6.0:1 moles of HNO3 per mole of Mo12.Type: GrantFiled: May 31, 2010Date of Patent: August 16, 2011Assignee: Sabic Basic Industries CorporationInventors: Scott A. Stevenson, Wugeng Liang, James W. Kauffman, Lixia Cai, Angie McGuffey, Joseph R. Linzer
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Patent number: 7994091Abstract: Disclosed is a palladium-containing catalyst for producing an ?, ?-unsaturated carboxylic acid from an olefin or an ?, ?-unsaturated aldehyde in high productivity. Also disclosed are a method for producing such a catalyst, and a method for producing an ?, ?-unsaturated carboxylic acid in high productivity. Specifically, a palladium-containing catalyst is produced by a method containing a step in which palladium in an oxidation state is reduced by a compound (A) which is represented by the following formula (1).Type: GrantFiled: December 26, 2006Date of Patent: August 9, 2011Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Yoshiyuki Himeno, Ken Ooyachi, Toshiya Yasukawa
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Patent number: 7880033Abstract: A benzyl vinyl ether represented by the following formula is hydrolyzed in the presence of a catalyst selected among Arrhenius acids and Lewis acids to obtain 3,3,3-trifluoropropionaldehyde. Subsequently, the 3,3,3-trifluoropropionaldehyde is oxidized with an oxidizing agent. Thus, 3,3,3-trifluoropropionic acid can be more advantageously produced than in conventional techniques from an inexpensive starting material.Type: GrantFiled: October 24, 2006Date of Patent: February 1, 2011Assignee: Central Glass Company, LimitedInventors: Takeo Komata, Kenji Hosoi, Shinya Akiba
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Patent number: 7820856Abstract: Disclosed is a method for enhancing a yield of an ?,?-unsaturated carboxylic acid obtained by liquid-phase oxidation reaction of an olefin or an ?,?-unsaturated aldehyde. In particular, there is provided a method for producing an ?,?-unsaturated carboxylic acid, wherein the method includes the step of carrying out oxidation reaction of an olefin or an ?,?-unsaturated aldehyde in a liquid phase to obtain a reaction mixture containing an ?,?-unsaturated carboxylic acid and an ?,?-unsaturated carboxylic acid anhydride and the step of bringing the ?,?-unsaturated carboxylic acid anhydride into contact with an alcohol or water to obtain an ?,?-unsaturated carboxylic acid resulting from decomposition of the ?,?-unsaturated carboxylic acid anhydride.Type: GrantFiled: February 8, 2006Date of Patent: October 26, 2010Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Atsushi Koizumi, Kazunori Matake, Toshihiko Fukuda, Yuji Fujimori
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Publication number: 20100234639Abstract: Disclosed is a palladium-containing catalyst for producing an ?,?-unsaturated carboxylic acid from an olefin or an ?,?-unsaturated aldehyde in high productivity. Also disclosed are a method for producing such a catalyst, and a method for producing an ?,?-unsaturated carboxylic acid in high productivity. Specifically, a palladium-containing catalyst is produced by a method containing a step in which palladium in an oxidation state is reduced by a compound (A) which is represented by the following formula (1).Type: ApplicationFiled: December 26, 2006Publication date: September 16, 2010Applicant: Mitsubishi Rayon Co., Ltd.Inventors: Yoshiyuki Himeno, Ken Ooyachi, Toshiya Yasukawa
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Publication number: 20100137638Abstract: Disclosed is a method for producing an ?, ?-unsaturated carboxylic acid from an olefin or an ?, ?-unsaturated aldehyde, while suppressing dissolution of a silica carrier, which is a carrier for a silica-supported noble metal-containing catalyst, in a water-containing solvent. Specifically disclosed is a method for producing an ?, ?-unsaturated carboxylic acid through oxidation of an olefin or an ?, ?-unsaturated aldehyde in a water-containing solvent in the presence of a silica-supported noble metal-containing catalyst in a reactor, in which at least one of silicic acid and ions thereof is supplied into the reactor.Type: ApplicationFiled: December 26, 2007Publication date: June 3, 2010Inventors: Toshiki Matsui, Yoshiyuki Himeno, Kazunori Matake
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Patent number: 7649111Abstract: A heteropolyacid catalyst for oxidation of isobutyraldehyde, methacrolein or mixtures or combinations thereof to methacrylic acid is disclosed where the heteropolyacid catalyst includes at least molybdenum (Mo), phosphorus (P), vanadium (V), and a first component including bismuth (Bi) and/or boron (B). The heteropolyacid catalyst can also optionally include a second component including potassium (K), rubidium (Rb), cesium (Cs), and/or thallium (Tl) and optionally a third component including antimony (Sb), cerium (Ce), niobium (Nb), indium (In), iron (Fe), chromium (Cr), cobalt (Co), nickel (Ni), manganese (Mn), arsenic (As), silver (Ag), zinc (Zn), germanium (Ge), gallium (Ga), zirconium (Zr), magnesium (Mg), barium (Ba), lead (Pb), tin (Sn), titanium (Ti), aluminum (Al), silicon (Si), tantalum (Ta), tungsten (W), and/or lanthanum (La). The heteropolyacid catalyst can also include an ammonium-containing compound designed to increase a value of medium pores in the final heteropolyacid catalyst.Type: GrantFiled: July 25, 2005Date of Patent: January 19, 2010Assignee: Saudi Basic Industries CorporationInventors: Wugeng Liang, Scott A. Stevenson, Angie McGuffey, Joseph R. Linzer
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Patent number: 7635786Abstract: Disclosed are a Mo—Bi—Nb—Te based composite metal oxide; and a process for producing (meth)acrylic acid from at least one reaction material selected from the group consisting of propylene, propane, isobutylene, t-butyl alcohol and methyl-t-butyl ether, wherein the Mo—Bi—Nb—Te based composite metal oxide is used as a catalyst. Also, disclosed is a process for producing (meth)acrylic acid comprising a first step of producing (meth)acrolein as a main product from at least one reaction material selected from the group consisting of propylene, propane, isobutylene, t-butyl alcohol and methyl-t-butyl ether, and a second step of producing (meth)acrylic acid from the (meth)acrolein, wherein yield of (meth)acrylic acid in the product of the first step is 20 mole % or higher.Type: GrantFiled: October 16, 2008Date of Patent: December 22, 2009Assignee: LG Chem, Ltd.Inventors: Hyun Jong Shin, Byung Yul Choi, Yeon Shick Yoo, Young Hyun Choe, Young Jin Cho, Duk Ki Kim, Kwang Ho Park, Joo Yeon Park
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Publication number: 20090182170Abstract: Disclosed is a method for enhancing a yield of an ?,?-unsaturated carboxylic acid obtained by liquid-phase oxidation reaction of an olefin or an ?,?-unsaturated aldehyde. In particular, there is provided a method for producing an ?,?-unsaturated carboxylic acid, wherein the method includes the step of carrying out oxidation reaction of an olefin or an ?,?-unsaturated aldehyde in a liquid phase to obtain a reaction mixture containing an ?,?-unsaturated carboxylic acid and an ?,?-unsaturated carboxylic acid anhydride and the step of bringing the ?,?-unsaturated carboxylic acid anhydride into contact with an alcohol or water to obtain an ?,?-unsaturated carboxylic acid resulting from decomposition of the ?,?-unsaturated carboxylic acid anhydride.Type: ApplicationFiled: February 8, 2006Publication date: July 16, 2009Applicant: Mitsubishi Rayon Co., Ltd.Inventors: Atsushi Koizumi, Kazunori Matake, Toshihiko Fukuda, Yuji Fujimori
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Patent number: 7498462Abstract: The object of the present invention is to provide a method for producing an ?,?-unsaturated carboxylic acid in higher selectivity. The present invention resides in a method for producing an ?,?-unsaturated carboxylic acid from an olefin or an ?,?-unsaturated aldehyde in liquid phase by using a noble metal-containing catalyst and by causing a compound (A) having an acid dissociation exponent (pKa) of less than 4 to be present in the liquid phase.Type: GrantFiled: February 7, 2005Date of Patent: March 3, 2009Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Yoshiyuki Himeno, Akio Takeda, Seiichi Kawato, Wataru Ninomiya
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Patent number: 7351849Abstract: The present invention is to provide a method for producing the desired optically active ?-amino acid derivatives of high optical purities in high yields, without requiring a step of deprotection. More particularly, the present invention relates to a method for producing an optically active ?-amino acid derivative or a salt thereof represented by the formula (2): which comprises reacting an ?,?-unsaturated carboxylic acid derivative or a salt thereof represented by the formula (1): with an amines or a salt thereof in the presence of a chiral catalyst and in the presence or absence of an acid.Type: GrantFiled: August 18, 2004Date of Patent: April 1, 2008Assignee: Takasago International CorporationInventors: Mikiko Sodeoka, Yoshitaka Hamashima
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Patent number: 7304179Abstract: The present invention provides a method for producing methacrylic acid through gas-phase catalytic oxidation of methacrolein or a methacrolein-containing gas with molecular oxygen or a gas containing molecular oxygen by the use of a fixed-bed multitubular reactor comprising a plurality of reaction tubes each having a catalyst layer therein, wherein the above catalyst layer is divided in the direction of the tube axis of a reaction tube into two or more layers, to thereby provide a plurality of reaction zones, and the catalyst is caused to be present in the catalyst layer in such a way that a reaction load ratio CRc(i) per unit mass of the catalyst in each reaction zone becomes 0.8 to 1.0.Type: GrantFiled: August 27, 2004Date of Patent: December 4, 2007Assignee: Mitsubishi Rayon Co., Ltd.Inventors: Tomomichi Hino, Akira Ogawa
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Patent number: 6706916Abstract: In producing optically-active amino acid benzyl esters by reacting optically-active amino acids with benzyl alcohols, hydrazines are present in the reaction system, or the compounds are reacted in the absence of oxygen, or the compounds are reacted in the absence of oxygen while hydrazines are present in the reaction system. The processes are simple and give optically-active amino acid benzyl esters of high optical purity.Type: GrantFiled: August 17, 2001Date of Patent: March 16, 2004Assignee: Toray Fine Chemicals Co., Ltd.Inventors: Haruyo Sato, Takae Ohno, Shiho Iwata
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Publication number: 20030100793Abstract: The invention relates to a method for producing aliphatic carboxylic acids from aldehydes by means of oxidation with oxygen or gases containing oxygen. This novel process is carried out in at least two stages at different temperatures, preferably in the absence of catalysts.Type: ApplicationFiled: September 10, 2002Publication date: May 29, 2003Inventors: Helmut Springer, Peter Heymanns
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Publication number: 20030100781Abstract: The invention relates to a non-catalysed method for the synthesis of straight-chain aliphatic carboxylic acids by oxidation of straight-chain aldehydes with oxygen-containing gas mixtures. The invention is characterised in that during the novel process of oxidation branched aldehydes are present in the reaction mixture.Type: ApplicationFiled: September 5, 2002Publication date: May 29, 2003Inventor: Helmut Springer
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Patent number: 6414183Abstract: The present invention provides a method for stabilizing waste oil which is taken of each chemical apparatus of the manufacturing line of (meth)acryl acid and/or ester thereof, and treating the waste oil such as draining it out of the production apparatus, for example, a distillation tower from its bottom, sending and transporting it by a pump through a pipeline, and storing it in a storage tank in a simple manner while keeping the waste oil in a stable state. The waste oil can be stabilized by coexisting with solvent. The solvent used in the present invention is typically at least one selected from the group consisting of water, alcohol, ether, carboxylic acid, ketone, aromatic hydrocarbons, and aliphatic hydrocarbons.Type: GrantFiled: April 5, 2000Date of Patent: July 2, 2002Assignee: Nippon Shokubai Co., Ltd.Inventors: Kazuhiko Sakamoto, Sei Nakahara, Masatoshi Ueoka
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Patent number: 6384275Abstract: A method of producing acrylic acid using a catalyst for acrolein oxidation reaction. Metallic salt components of the catalyst including molybdate, vanadate and tungstate are dissolved in water. An additional metallic salt component of the catalyst is added to the aqueous solution of the salts to form a suspension of the catalyst. In the suspension, the total weight of water is about 0.8 to about 5 times of the total weight of the metallic salts in the catalyst. This method of preparing suspension minimizes the amount of water required to dissolve the metallic salts, which reduces the amount of time and energy to be used in evaporating water from the suspension in the following step of obtaining catalyst. Additionally, in obtaining catalyst from the suspension prepared by this method, it is possible to avoid the deterioration of the catalytic performance since less heat is required to evaporate the water. Disclosed also is a method of producing a carrier-retained catalyst.Type: GrantFiled: December 22, 2000Date of Patent: May 7, 2002Assignee: LG Chem, Ltd.Inventors: Won-Ho Lee, Kyung-Hwa Kang, Dong-Hyun Ko, Young-Chang Byun
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Publication number: 20020010364Abstract: This invention relates to a process for producing one or more organic acids in high purity which process comprises (i) oxidizing in a liquid oxidation reactor one or more organic liquids with essentially pure oxygen or oxygen-enriched air containing at least about 50% oxygen, at a temperature sufficiently stable to prevent cycling of reaction rate, to produce a crude reaction product fluid, and (ii) refining said crude reaction product fluid to give said one or more organic acids in high purity. The oxidation temperature is preferably controlled to within about ±3° C. of a target temperature. The organic acids described herein is useful in a variety of applications, such as intermediates in the manufacture of chemical compounds, pharmaceutical manufacture and the like.Type: ApplicationFiled: April 21, 1998Publication date: January 24, 2002Inventors: JOHN BRAITHWAITE, DAVID ROBERT BRYANT, DAVID JAMES MILLER, JOHN EARL LOGSDON
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Publication number: 20010005762Abstract: The present invention provides a method of producing easily and in a high yield a threo-2-hydroxy-3-nitrobutanoic acid compound or a mixture of a threo- and an erythro-2-hydroxy-3-nitrobutanoic acid compounds, this mixture having an erythro compound:threo compound ratio of about 1:1, which method includes reacting, in a solvent, a 2-hydroxy-3-nitrobutanoic acid compound having the formula (I) 1Type: ApplicationFiled: December 27, 2000Publication date: June 28, 2001Inventors: Tetsuya Shintaku, Masahide Tanaka, Nobushige Itaya
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Patent number: 6111084Abstract: Bioactive fucopeptides and libraries of fucopeptides having advanced activities against P-selectin as sialyl Lewis X mimetics with IC.sub.50 values in the low mM range are synthesized by solid phase synthesis using para-acyloxymethylenzlidene acetal (p-AMBA) as an anchoring group. A rapid parallel synthesis is employed which proceeds with a bi-directional functionalization of glycosylated amino acid derivatives.Type: GrantFiled: June 1, 1998Date of Patent: August 29, 2000Assignee: The Scripps Research InstituteInventors: Chi-Huey Wong, Thomas F. J. Lampe
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Patent number: 6084124Abstract: The present invention is a method to produce an unsaturated carboxylic acid which includes the steps of: providing an epoxy compound; contacting the epoxy compound with carbon monoxide in the presence of a catalytically effective amount of a catalyst system comprising tin and cobalt under conditions effective for carbonylation of the epoxy; and recovering a .alpha.-.beta. unsaturated carboxylic acid product. The preferred epoxy is ethylene oxide which is reacted to acrylic acid by the method of the present invention.Type: GrantFiled: February 4, 1999Date of Patent: July 4, 2000Assignee: Shell Oil CompanyInventors: Lynn Henry Slaugh, Thomas Clayton Forschner
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Patent number: 5907056Abstract: An oxide catalyst comprising the elements Mo, V and Nb with small amounts of phosphorus, boron, hafnium, Te and/or As. The modified catalyst provides both higher selectivity and yield of acetic acid in the low temperature oxidation of ethane with molecular oxygen-containing gas. A process for the higher selective production of acetic acid by the catalytic oxidation of ethane with oxygen, in the presence of the improved catalyst.Type: GrantFiled: May 27, 1998Date of Patent: May 25, 1999Assignee: Saudi Basic Industries Corp.Inventors: Khalid Karim, Mohammed H. Al-Hazmi, Edouard Mamedov
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Patent number: 5304549Abstract: Compounds of the formula ##STR1## wherein A is the group ##STR2## R.sup.1 is hydrogen, amino, protected amino, acylamino or lower alkyl optionally substituted by aryl, hydroxy, protected hydroxy, amino, protected amino, acylamino, maleimido, succinimido, naphthalimido, 2,3-dihydro-1,3-dioxo-1H-benz[d,e]isoquinol-2-yl, carboxy, protected carboxy, carbamoyl, mono(lower alkyl)carbamoyl, di(lower alkyl)carbamoyl, di(lower alkyl)amino, carboxy-lower alkanoylamino, pyrrolidino or morpholino; R.sup.2 is hydrogen or lower alkyl optionally substituted by aryl, amino, protected amino, di(lower alkyl)- amino, guanidino, carboxyl, protected carboxyl, carbamoyl, mono(lower alkyl) carbamoyl, di(lower alkyl)carbamoyl, di(lower alkoxy)phosphinyl, dihydroxyphosphinyl, pyrrolidino, piperidino or morpholino; R.sup.3 is hydrogen or lower alkyl optionally substituted by hydroxy, protected hydroxy, amino or protected amino; R.sup.4 is hydrogen, hydroxy, lower alkoxy or benzyloxy; and R.sup.Type: GrantFiled: January 21, 1992Date of Patent: April 19, 1994Assignee: Hoffmann-La Roche Inc.Inventors: Michael J. Broadhurst, Paul A. Brown, William H. Johnson, Geoffrey Lawton
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Patent number: 5208258Abstract: A method of preparing compactin and mevinolin, ketoacid, enone, and glutarate analogs thereof, and related compounds. The compounds are prepared in substantially enantiomerically pure form using a structurally convergent synthesis. Total syntheses of (+)-compactin, (+)-mevinolin and related compounds are provided. Novel compounds are identified, several of which show significant anti-hypercholesterolemic activity.Type: GrantFiled: April 17, 1990Date of Patent: May 4, 1993Assignee: The Regents of the University of CaliforniaInventors: Clayton H. Heathcock, Terry J. Rosen
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Patent number: 5095143Abstract: A method to oxidize an oxidizable component in a liquid phase with an oxygen-containing gas is disclosed. The method comprises mixing the liquid phase and gas phase in a reactor with a rotating agitator element operated at constant power.Type: GrantFiled: June 13, 1990Date of Patent: March 10, 1992Assignee: Amoco CorporationInventors: Daniel L. Heberer, Paul R. Schiller, Virginia R. Seemann, Michael J. Yerkes
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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: 4549025Abstract: Carboxylic acids having the general formula:R--COOHwherein R is selected from the group consisting of aryl, aralkyl, aralkenyl, aralkynyl, heteroaryl, heteroarylalkyl, heteroarylalkenyl, heteroarylalkynyl, alkyl, alkenyl and alkynyl, optionally substituted by inert or non-reactive substituents under the reaction conditions, are obtained by oxidation of the corresponding aldehydes with an alkali metal or alkaline-earth metal chlorite in the presence of hydrogen peroxide and in an aqueous-organic solvent. The resulting carboxylic acids are utilizable as intermediates for preparing fine chemicals in known ways.Type: GrantFiled: December 12, 1984Date of Patent: October 22, 1985Assignee: Montedison S.p.A.Inventors: Enrico Dalcanale, Giorgio Bottaccio, Stefano Campolmi, Fernando Montanari
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Patent number: 4353832Abstract: A process for the production of carboxyl compounds such as caprolactones, in which the corresponding carbonyl compounds are oxidized with hydrogen peroxide in the presence of a catalyst in a substantially anhydrous liquid medium. The water formed by the reaction and any water introduced into the reaction mixture are removed from the reaction mixture.Type: GrantFiled: June 5, 1980Date of Patent: October 12, 1982Assignee: INTEROX (Societe Anonyme)Inventors: Andre Lecloux, Claude Declerck, Franz Legrand
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Patent number: 4338462Abstract: In the process for oxidizing methacrolein to a methacrylic acid salt with an oxidizing gas in a strongly alkaline medium at a temperature of 0 to 100.degree. C. and in the presence of a finely divided silver catalyst and recovering methacrylic acid by acidification, the improvement which comprises carrying out said oxidation in the presence of a small amount of dissolved alkali metal carbonate.Type: GrantFiled: June 9, 1980Date of Patent: July 6, 1982Assignee: Atlantic Richfield CompanyInventor: Gregory A. Wheaton
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Patent number: 4225694Abstract: Primary and secondary unsaturated alcohols are converted to their corresponding aldehydes and/or carboxylic acids and ketones respectively with alkali metal (per) halate, preferably sodium periodate, in the presence of ruthenium catalyst. The process is particularly useful in the oxidation of chrysanthemyl alcohol. Any unconverted intermediate aldehyde formed may be converted to the acid by recycling or by a separate oxidation step.Type: GrantFiled: September 6, 1977Date of Patent: September 30, 1980Assignee: Air Products and Chemicals, Inc.Inventors: Augustine I. Dalton, Jr., Henry J. Doran, Robert D. H. Murray
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Patent number: 4147884Abstract: Process for the liquid phase oxidation of an unsaturated lower aliphatic aldehyde to the corresponding carboxylic acid wherein the oxidation is carried out by passage of an oxygen-containing gas through a liquid medium containing the unsaturated aldehyde and a fluorine-containing organic compound.Type: GrantFiled: April 26, 1976Date of Patent: April 3, 1979Assignee: Atlantic Richfield CompanyInventors: Ming N. Sheng, Jar-Lin Kao
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Patent number: 4138417Abstract: A process for producing a perfluorocarboxylic acid comprises reacting a perfluoroalkyl olefin with ozone to produce a perfluoroalkyl ozonide and a perfluoroalkyl aldehyde and converting said perfluoroalkyl ozonide and perfluoroalkyl aldehyde to perfluorocarboxylic acid with an oxidizing agent.Type: GrantFiled: May 3, 1977Date of Patent: February 6, 1979Assignee: Asahi Glass Company, Ltd.Inventors: Hiroshi Ukihashi, Takao Hayashi, Yukio Takasaki
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Patent number: 4127603Abstract: A method of preparing methacrylic acid, which comprises liquid-phase oxidation of alpha-methylacrolein with an oxygen-containing gas in a medium of an organic solvent at a temperature ranging from 50.degree. to 100.degree. C and under a pressure of from 1 to 50 atm in the presence of a heterogeneous catalyst such as borides, carbides or nitrides of elements pertaining to Groups IVB-VB of the periodic system, or aluminum boride, carbide or nitride and in the presence of a polymerization inhibitor, whereafter the desired product is separated from the resulting reaction mixture. The method according to the present invention makes it possible to produce methacrylic acid with a high selectivity (up to 86% as calculated for the reacted alpha-methylacrolein). Conversion degree of the starting aldehyde is as high as 55%. There is no formation of polymeric products during the oxidation process.Type: GrantFiled: February 16, 1977Date of Patent: November 28, 1978Inventors: Erna A. Bljumberg, Gennady F. Vytnov, Oleg V. Isaev, Oleg V. Krylov, Sergei A. Maslov, Lia Y. Margolis, Alexandr P. Sineokov, Evgeny S. Smirnov, Levon A. Tavadian, Nikolai M. Emanuel, Kapitalina I. Grobova, Valentina V. Krylova
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Patent number: 4124633Abstract: A process for the preparation of acrylic acid or methacrylic acid which comprises catalytically decomposing or converting in the presence of tellurium the peroxide (peroxy) compounds contained in the oxidate solution derived from the autoxidation of acrolein or methacrolein, particularly, the conversion of permethacrylic acid and methacrolein monopermethacrylate to methacrylic acid.Type: GrantFiled: August 1, 1977Date of Patent: November 7, 1978Assignee: Atlantic Richfield CompanyInventors: John J. Leonard, Jar-lin Kao
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Patent number: 4124635Abstract: A process for the liquid phase oxidation of .alpha.,.beta.-unsaturated aliphatic aldehydes, such as methacrolein and the in situ decomposition or conversion of unsaturated peroxy (peroxide) compounds formed during the oxidation to the corresponding .alpha.,.beta.-unsaturated aliphatic carboxylic acids which comprises passing oxygen or an oxygen-containing gas such as air through an inert solvent solution of the unsaturated aldehyde at a suitable temperature and pressure in the presence of an organic or inorganic zinc salt catalyst.Type: GrantFiled: March 7, 1977Date of Patent: November 7, 1978Assignee: Atlantic Richfield CompanyInventors: Jar-lin Kao, John J. Leonard