Of Aldehyde Patents (Class 562/531)
  • Patent number: 10689320
    Abstract: The invention relates to a method for separating formic acid from a reaction mixture by means of extraction, wherein, in addition to the formic acid, the reaction mixture comprises a polyoxometalate ion of general formula [PMoxVyO40]n? as a catalyst and a solvent that dissolves the catalyst, wherein 6?x?11, 1?6, x+y=12 and 3<n<10, wherein n, x, and y are each a whole number, wherein the separation occurs via extraction by means of a polar organic extraction agent which extracts the formic acid and the catalyst and which is N-(n-hexadecyl)formamide, N-di-n-acetamide or an N,N-dialkylcarboxamide, wherein the N,N-dialkylcarboxamide forms a phase boundary between the solvent and the extraction agent during mixing with the solvent.
    Type: Grant
    Filed: July 17, 2017
    Date of Patent: June 23, 2020
    Assignee: OXFA GMBH
    Inventors: Hermann Wolf Jbach, Florian Kohler, Matthias Schmidt, Gunthard Scholz, Martin Dirauf
  • Patent number: 10661263
    Abstract: The invention relates to catalytically producing formic acid and regenerating the catalyst used in the process. A vanadyl ion, vandate ion, or polyoxometallate ion, which is used as the catalyst, of the general formula [PMoxVyO40]n? is brought into contact with an alpha hydroxyl aldehyde, an alpha hydroxy carboxylic acid, a carbohydrate, a glycoside, or a polymer, which contains a carbon chain and which comprises at least two OH groups bonded as substituents to the carbon chain as a substituent in a repeating manner and/or an O, N, or S atom contained in the carbon chain in a repeating manner, in a liquid solution (12) in a vessel (10) at a temperature above 70° C. and below 160° C., wherein 6?x?11, 1?y?6, 3<n<10, and x+y=12, where n, x, and y is each a whole number.
    Type: Grant
    Filed: July 17, 2017
    Date of Patent: May 26, 2020
    Assignee: OXFA GmbH
    Inventors: Hermann Wolf Jbach, Florian Kohler, Matthias Schmidt, Gunthard Scholz
  • Patent number: 10544079
    Abstract: Process for the direct conversion of diisobutene to a carboxylic acid.
    Type: Grant
    Filed: November 13, 2018
    Date of Patent: January 28, 2020
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Rui Sang, Peter Kucmierczyk, Kaiwu Dong, Ralf Jackstell, Matthias Beller, Robert Franke
  • Patent number: 10022890
    Abstract: In some examples, the disclosure describes a method including depositing a first layer including a resin and at least one of a carbon fiber or a carbon fiber precursor material on a work surface of a three-dimensional printing system, carbonizing at least the resin of the first layer using a carbonizer attached to the three-dimensional printer to form a first layer of carbon-carbon composite including carbon fibers and carbonized matrix material, depositing an additional layer including a resin and at least one of a carbon fiber or a carbon fiber precursor material of material on the first layer of carbon-carbon composite, and carbonizing at least the resin of the additional layer using the carbonizer to form an additional layer of carbon-carbon composite on the first layer of carbon-carbon composite.
    Type: Grant
    Filed: September 15, 2015
    Date of Patent: July 17, 2018
    Assignee: Honeywell International Inc.
    Inventors: Mark L. La Forest, Slawomir T. Fryska, David Flask, Jeffrey Troester
  • Patent number: 9975840
    Abstract: The oxidation of isobutyraldehyde produces isobutyric acid and byproducts, such as isopropyl formate. A process of reducing the isopropyl formate byproduct and other byproducts in the oxidation of isobutyraldehyde is described. The process uses a carbonyl compound, such as acetone, to reduce byproduct levels in the resulting product. Process for use of static mixers in oxidation reactions of aldehydes are also provided.
    Type: Grant
    Filed: July 20, 2016
    Date of Patent: May 22, 2018
    Assignee: Eastman Chemical Company
    Inventors: Damon Ray Billodeaux, Kenneth Wayne Hampton, Jr., Chad A. Johnson
  • Patent number: 9701652
    Abstract: The disclosure relates to a method for forming 2,5-furan dicarboxylic acid (FDCA) from aldaric acids. The aldaric acids are dehydrating and cyclizing via acid catalysis to form the FDCA product. Aldaric acids such as galactaric acid, gularic acid, mannaric acid, and glucaric acid can be used in the disclosed method, and the aldaric acids can be obtained from form renewable biomass sources which contain pectin, alginate, and/or other biomass carbohydrates. The FDCA can be used as a renewable feedstock for consumer product polymeric materials such as polyalkylene furoate polymers.
    Type: Grant
    Filed: November 23, 2016
    Date of Patent: July 11, 2017
    Assignee: BOARD OF TRUSTEES OF MICHIGAN STATE UNIVERSITY
    Inventors: Dennis J. Miller, Lars Peereboom, Evan Wegener, Matthew Gattinger
  • Patent number: 9428435
    Abstract: The oxidation of isobutyraldehyde produces isobutyric acid and byproducts, such as isopropyl formate. A process of reducing the isopropyl formate byproduct and other byproducts in the oxidation of isobutyraldehyde is described. The process uses a carbonyl compound, such as acetone, to reduce byproduct levels in the resulting product. Process for use of static mixers in oxidation reactions of aldehydes are also provided.
    Type: Grant
    Filed: December 12, 2014
    Date of Patent: August 30, 2016
    Assignee: Eastman Chemical Company
    Inventors: Damon Ray Billodeaux, Kenneth Wayne Hampton, Jr., Chad A. Johnson
  • Patent number: 9399208
    Abstract: This application discloses catalysts and methods of making the catalysts. In one embodiment, a catalyst comprising: a reduced precious group metal in an amount greater than about 30 wt % based on the total precious group metal weight in the catalyst, wherein the catalyst oxidizes volatile organic compounds and/or carbon monoxide at a temperature of about 150° C. or lower, is disclosed. In another embodiment, a catalyst for oxidation of formaldehyde, methanol, formic acid, and/or carbon monoxide to form carbon dioxide at a temperature of from about 20° C. to about 45° C. and at about atmospheric pressure, the catalyst comprising: a reduced precious group metal dispersed on a support selected from the group consisting of CeO2, TiO2, ZrO2, Al2O3, SiO2, and combinations thereof, is disclosed.
    Type: Grant
    Filed: August 21, 2014
    Date of Patent: July 26, 2016
    Assignee: BASF Corporation
    Inventors: Xiaolin Yang, Pascaline Tran, Qingyuan Hu
  • Patent number: 9227904
    Abstract: The present disclosure relates to a method for producing glucaric acid, and more particularly, to a method for producing glucaric acid including the steps of: (1) inputting aldohexose and potassium hydroxide to an aqueous solution; and (2) deriving a catalytic oxidation reaction after adding a supported noble metal catalyst to the aqueous solution under the presence of oxygen gas.
    Type: Grant
    Filed: December 9, 2014
    Date of Patent: January 5, 2016
    Assignees: HYUNDAI MOTOR COMPANY, SNU R&DB FOUNDATION
    Inventors: Chae Hwan Hong, Si Hwan Kim, Young Gyu Kim, Na Ra Shin
  • Patent number: 9187398
    Abstract: A process utilizing nitric acid and oxygen as co-oxidants to oxidize aldehydes, alcohols, polyols, preferably carbohydrates, specifically reducing sugars to produce the corresponding carboxylic acids.
    Type: Grant
    Filed: March 12, 2014
    Date of Patent: November 17, 2015
    Assignee: Rivertop Renewables, Inc.
    Inventors: Steven Donen, Kirk Hash, Tyler Smith, Keith Jensen
  • Patent number: 9162959
    Abstract: A controlled nitric acid process employing oxygen and nitric acid as co-oxidants is used to oxidize organic compounds subject to nitric acid oxidation, to their corresponding carboxylic acids. Oxidation of some carbohydrates by this process can produce one or more of their corresponding acid forms. The process is carried out at moderate temperatures, typically in the range of 20° C. to 45° C. in a closed reactor, with oxygen gas being introduced into the reaction chamber as needed in order to sustain the reaction. Computer controlled reactors allow for careful and reproducible control of reaction parameters. Nitric acid can be recovered by a distillation/evaporation process, or by diffusion dialysis, the aqueous solution made basic with inorganic hydroxide, and the residual inorganic nitrate removed using a filtration (nanofiltration) device.
    Type: Grant
    Filed: January 8, 2014
    Date of Patent: October 20, 2015
    Assignee: The University of Montana
    Inventors: Donald E. Kiely, Kirk R. Hash, Sr.
  • Patent number: 9072754
    Abstract: The present disclosure relates to a process for pre-treating raw propolis comprising at least one allergenic activity substance, which comprises reacting propolis with a probiotic microorganism containing one or more cinnamoyl-esterase activity enzymes to obtain a semisolid propolis derivative substantially without or impoverished of allergenic substances. The present invention also relates to a method of purifying semisolid propolis derivative to obtain a hydroalcoholic hydrodispersible propolis derivative.
    Type: Grant
    Filed: March 15, 2011
    Date of Patent: July 7, 2015
    Assignee: MR. GIUSEPPE MARIA RICCHIUTO
    Inventors: Giuseppe Maria Ricchiuto, Claudio Sebastiano Gardana, Simone Domenico Guglielmetti
  • Patent number: 9029597
    Abstract: A reactive rectification column suitable for the production of 2-hydroxy-4-methylmercaptobutyric acid and/or methionine contains a weir having a height of 100 mm or more.
    Type: Grant
    Filed: August 29, 2012
    Date of Patent: May 12, 2015
    Assignee: Evonik Degussa GmbH
    Inventors: Martin Steffan, Hans Joachim Hasselbach, Martin Koerfer, Harald Jakob, Jignesh Gangadwala
  • Publication number: 20150065749
    Abstract: Disclosed is the oxidation of uronic acids, such as galacturonic acid, to the corresponding aldaric acids (characterized by the formula HOOC—(CHOH)n-COOH, with n being an integer of from 1 to 5) such as galactaric acids. The starting material comprising the uronic acid is subjected to oxygen under the influence of a supported gold catalyst and in the presence of a base. The oxidation occurs in good selectivity and yield, under unexpectedly mild conditions. A source of galacturonic acids is pectin, such as that derived from sugar beet pulp.
    Type: Application
    Filed: March 28, 2013
    Publication date: March 5, 2015
    Inventors: Daniël Stephan Van Es, Jacobus van Haveren, Henricus Wilhelmus Carolina Raaijmakers, Frits van der Klis, Gerardus Petrus Franciscus Maria van Engelen, Augustinus Emmanuël Frissen
  • Publication number: 20150018576
    Abstract: The invention relates to a method for producing a product mixture (2) by means of the technical hydroformylation of a hydrocarbon stream (1) that contains isobutene, and for separating the product mixture (2) that is obtained, as well as to a device for the claimed method and to the use of a claimed device. The problem addressed thereby is that of providing a method and an associated device that allow the amount of high-boiling substances in the product mixture (2) to be kept as low as possible and thus the yield of the reaction to be increased. The problem is solved by the use of a nano-filtration device (M) for separating the catalyst from the product mixture (2), said device having especially high permeability to 3-methylbutanoic acid.
    Type: Application
    Filed: February 11, 2013
    Publication date: January 15, 2015
    Applicant: Evonik Degussa GmbH
    Inventors: Goetz Baumgarten, Michael Grass, Alfred Kaizik, Markus Winterberg, Hans-Gerd Lueken, Bart Hamers, Markus Priske, Dirk Fridag, Robert Franke, Dieter Hess
  • Publication number: 20150005526
    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 19, 2014
    Publication date: January 1, 2015
    Applicants: ARKEMA FRANCE, NIPPON KAYAKU KABUSHIKI KAISHA
    Inventors: Yasuhiro MAGATANI, Kimito OKUMURA, Jean-Luc DUBOIS, Jean-Francois DEVAUX
  • Publication number: 20140275621
    Abstract: A process utilizing nitric acid and oxygen as co-oxidants to oxidize aldehydes, alcohols, polyols, preferably carbohydrates, specifically reducing sugars to produce the corresponding carboxylic acids.
    Type: Application
    Filed: March 12, 2014
    Publication date: September 18, 2014
    Inventors: Steven Donen, Kirk Hash, Tyler Smith
  • Publication number: 20140275622
    Abstract: A process utilizing nitric acid and oxygen as co-oxidants to oxidize aldehydes, alcohols, polyols, preferably carbohydrates, specifically reducing sugars to produce the corresponding carboxylic acids.
    Type: Application
    Filed: March 12, 2014
    Publication date: September 18, 2014
    Inventors: Steven Donen, Keith Jensen
  • Publication number: 20140275623
    Abstract: A process utilizing nitric acid and oxygen as co-oxidants to oxidize aldehydes, alcohols, polyols, preferably carbohydrates, specifically reducing sugars to produce the corresponding carboxylic acids.
    Type: Application
    Filed: March 12, 2014
    Publication date: September 18, 2014
    Inventors: Steven Donen, Kirk Hash, Tyler Smith, Keith Jensen
  • Publication number: 20140171676
    Abstract: A method of preparing acrolein from glycerol or glycerine is disclosed. The method includes dehydrating glycerol or glycerine in the presence of a catalyst consisting of at least (a) a mixed oxide of zirconium and at least one metal, said metal being selected from niobium, tantalum and vanadium, or (b) a zirconium oxide and at least one metal oxide, the metal being selected from niobium, tantalum and vanadium, or (c) a silicon oxide and a mixed oxide of zirconium and at least one metal, the metal being selected from tungsten, cerium, manganese, niobium, tantalum, titanium, vanadium and silicon, or (d) a titanium oxide and a mixed oxide of zirconium and at least one metal, said metal being selected from tungsten, cerium, manganese, niobium, tantalum, titanium, vanadium and silicon.
    Type: Application
    Filed: August 27, 2013
    Publication date: June 19, 2014
    Applicants: Centre National De La Recherche Scientifique, Adisseo France S.A.S
    Inventors: Virginie BELLIERE-BACA, STEPHANE LORIDANT, JEAN-MARC MILLET, PASCALINE LAURIOL-GARBEY
  • Patent number: 8754255
    Abstract: The invention relates to a method for preparing an aqueous solution of glyoxylic acid by oxidation of an aqueous solution of glyoxal with oxygen or a gas containing oxygen, in the presence of a catalytic quantity of nitric acid and/or at least one nitrogen oxide, a strong acid not oxidizing glyoxal, and by maintaining conditions satisfying the equation KLa/Q>10, where KLa is the total volumetric mass transfer coefficient and Q is the heat load liberated by the reaction per mole of glyoxal.
    Type: Grant
    Filed: January 21, 2009
    Date of Patent: June 17, 2014
    Assignee: Clariant Specialty Fine Chemicals (France)
    Inventors: François Bleger, Olivier Simon, Alain Schouteeten
  • Patent number: 8673245
    Abstract: A fixed-bed reactor containing a first catalyst layer filled with a first catalyst for producing acrolein from propylene; a second catalyst layer filled with a second catalyst for producing acrylic acid from acrolein; and an inert substance layer provided between the first catalyst layer and the second catalyst layer, and filled with an inert substance of a cylindrical shape having a surrounding wall in which an opening is formed. A process for producing acrylic acid containing the step of producing acrylic acid from propylene by using the aforementioned fixed-bed reactor.
    Type: Grant
    Filed: September 9, 2009
    Date of Patent: March 18, 2014
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Michio Tanimoto, Nobuyuki Hakozaki
  • Patent number: 8664434
    Abstract: A process for preparing aliphatic carboxylic acids having 3 to 10 carbon atoms by oxidizing the corresponding aldehydes with oxygen or oxygen-containing gases, characterized in that (i) the oxidation is performed in a microreactor at elevated pressure and with an oxygen excess based on the stoichiometrically required amount of oxygen, and (ii) in that the reaction mixture removed from the microreactor is passed through at least one postreactor without further addition of oxygen, and (iii) wherein the oxidation reaction in the microreactor is performed under such conditions that aldehyde and corresponding peracid formed are present in the reaction mixture removed in a molar ratio within a range of 1:(0.9 to 1.1), preferably of 1:(0.95 to 1.05).
    Type: Grant
    Filed: March 3, 2010
    Date of Patent: March 4, 2014
    Assignee: Oxea GmbH
    Inventors: Tonia Weber, Alexander Kaufmann, Oliver Borgmeier, Thorsten Kreickmann, Heinz Strutz, Diana Utz, Elias Klemm, Claudia Liebold
  • Publication number: 20130345473
    Abstract: The present disclosure relates to processes for the separation of at least one di-carboxylic acid compound and/or at least one mono-carboxylic acid compound from a mixture. The separation processes involve contacting the mixture with an ion exchange medium to cause at least one of the mono- and/or di-carboxylic acid compounds to be retained by the medium, eluting at least one of the mono-carboxylic acid compound or the di-carboxylic acid compound using an eluent to form an eluate, wherein the eluate is enriched in at least one of the mono-carboxylic acid compound or di-carboxylic acid relative to the concentration of such eluted acid in the mixture having contacted the medium and wherein the eluent comprises an organic acid. The process has particular utility in the production of di-carboxylic acid compounds from glucose.
    Type: Application
    Filed: November 30, 2012
    Publication date: December 26, 2013
    Applicant: Rennovia, Inc.
    Inventors: Raymond ARCHER, Gary M. DIAMOND, Eric L. DIAS, Vincent J. MURPHY, Miroslav PETRO, John D. SUPER
  • Publication number: 20130331605
    Abstract: Disclosed is a process for the production and purification of glycolic acid or glycolic acid derivatives by the carbonylation of aqueous formaldehyde. The water in the hydrocarboxylation zone is reduced via reaction with the ester bonds in a recycle stream comprising glycolic acid oligomers and/or methyl glycolate oligomers.
    Type: Application
    Filed: June 8, 2012
    Publication date: December 12, 2013
    Applicant: EASTMAN CHEMICAL COMPANY
    Inventors: Mesfin Ejerssa Janka, Scott Donald Barnicki, Robert Thomas Hembre, Kelley Margaret Moran, Stephen Neal Falling
  • Patent number: 8586499
    Abstract: A method for producing a catalyst for the preparation of methacrylic acid comprising a heteropolyacid compound containing phosphorus, molybdenum and an element X selected from the group consisting of potassium, rubidium, cesium and thallium and having an atomic ratio of the element X to molybdenum of 0.5:12 to 2:12, which method comprises the steps of mixing aqueous slurry A containing starting compounds of the heteropolyacid compound in which an atomic ratio of the element X to molybdenum is from 2:12 to 4:12, and aqueous slurry B containing starting compounds of the heteropolyacid compound in which an atomic ratio of the element X to molybdenum is from 0:12 to 0.5:12 to form a slurry mixture; heat-treating the slurry mixture at a temperature of 100° C. or higher; drying the slurry mixture; and calcining the dried mixture.
    Type: Grant
    Filed: October 26, 2010
    Date of Patent: November 19, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Toshiaki Miyatake, Junji Shibata, Eiichi Shiraishi
  • Patent number: 8575379
    Abstract: The invention relates to a process for the oxidation of organic compounds by means of oxygen, in which, in a first step, the organic compound and at least part of the oxygen required for the oxidation are introduced into a first reaction zone which is operated isothermally and with backmixing and, in a second step, the reaction mixture from the first reaction zone is introduced into a second reaction zone which is operated adiabatically. The invention further relates to a reactor for carrying out the process, which comprises at least one isothermal reaction zone (3, 5) and an adiabatic reaction zone (7) which are arranged in a reactor shell (8), with each isothermal reaction zone (3, 5) being configured in the form of a jet loop reactor and the adiabatic reaction zone (7) being configured as a bubble column.
    Type: Grant
    Filed: August 1, 2008
    Date of Patent: November 5, 2013
    Assignee: BASF SE
    Inventors: Joaquim Henrique Teles, Kai Gumlich, Jochen Schäfer, Steffen Oehlenschläger, Stephan Lamm, Roland Merten, Martin Schäfer, Rüdiger Grob, Uwe Emnet
  • Publication number: 20130245318
    Abstract: A reactive rectification column suitable for the production of 2-hydroxy-4-methylmercaptobutyric acid and/or methionine contains a weir having a height of 100 mm or more.
    Type: Application
    Filed: August 29, 2012
    Publication date: September 19, 2013
    Applicant: Evonik Degussa GmbH
    Inventors: Martin Steffan, Hans Joachim Hasselbach, Martin Koerfer, Harald Jakob, Jignesh Gangadwala
  • Publication number: 20130245319
    Abstract: The invention relates to a method for catalytically producing formic acid. A polyoxometallate ion, which is used as a catalyst, of the general formula [PMoxVyO40]5? is brought into contact with an alpha-hydroxyaldehyde, an alpha-hydroxycarboxylic acid, a carbohydrate, or a glycoside in a liquid solution at a temperature below 120° C., wherein 6<x<11, 1<y<6, x+y=12, and x and y are each a whole number.
    Type: Application
    Filed: August 26, 2011
    Publication date: September 19, 2013
    Applicant: JBACH GmbH
    Inventors: Andreas Bösmann, René Wölfel, Peter Wasserscheid, Nicola Taccardi, Jakob Albert
  • Publication number: 20130204036
    Abstract: An alternative method for efficiently producing lactic acids from a carbohydrate-containing raw material such as cellulose is provided. The method for producing lactic acid and/or lactic acid ester comprises performing heat treatment on a carbohydrate-containing raw material in a solvent containing a catalyst, wherein the catalyst is at least one type of compound selected from the group consisting of a tin compound, an indium compound, and a rhenium compound, and the solvent contains water and/or alcohol.
    Type: Application
    Filed: March 31, 2011
    Publication date: August 8, 2013
    Applicants: National Institute of Advanced Industrial Science and Technology, Nippon Shokubai Co. Ltd.
    Inventors: Kenichi Tominaga, Atsushi Mori, Kazuhiko Satoh, Shigeru Shimada, Hideaki Tsuneki, Yoshiaki Hirano
  • Patent number: 8492584
    Abstract: 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: Grant
    Filed: August 18, 2008
    Date of Patent: July 23, 2013
    Assignee: BASF SE
    Inventors: Joaquim Henrique Teles, Steffen Oehlenschläger, Kai Gumlich, Martin Schäfer, Stephan Lamm, Stefan Berg, Michael Nilles, Hans-Peter Schildberg, Tilo John, Peter Zehner
  • Patent number: 8481448
    Abstract: The invention is a heteropoly acid compound catalyst composition, a method of making the catalyst composition and a process for the oxidation of saturated and/or unsaturated aldehydes to unsaturated carboxylic acids using the catalyst composition. The catalyst composition is a heteropoly acid compound containing molybdenum, vanadium, phosphorus, cesium, bismuth, copper and antimony. Thermal stability is achieved with higher cesium content (up to less than 3.0) but antimony, copper and bismuth must be present to maintain good activity. The catalyst is made by dissolving compounds of the components of each of the heteropoly acid compounds in a solution, precipitating the heteropoly acid compounds, obtaining a catalyst precursor and calcining the catalyst precursor to form a heteropoly acid compound catalyst. Unsaturated aldehydes, such as methacrolein, may be oxidized in the presence of the heteropoly acid compound catalyst to produce an unsaturated carboxylic acid, such as methacrylic acid.
    Type: Grant
    Filed: July 19, 2010
    Date of Patent: July 9, 2013
    Assignee: Saudi Basic Industries Corporation
    Inventors: Wugeng Liang, David Sullivan, James W. Kauffman, Clark Rea, Joe Linzer, Shahid Shaikh
  • Publication number: 20130158283
    Abstract: Novel synthetic routes, which are highly applicable for industrial preparation of therapeutically beneficial oxidized phospholipids are disclosed. Particularly, novel methods for efficiently preparing compounds having a glycerolic backbone and one or more oxidized moieties attached to the glycerolic backbone, which are devoid of column chromatography are disclosed. Further disclosed are novel methods of introducing phosphorous-containing moieties such as phosphate moieties to compounds having glycerolic backbone and intermediates formed thereby.
    Type: Application
    Filed: December 10, 2012
    Publication date: June 20, 2013
    Applicant: Vascular Biogenics Ltd.
    Inventor: Vascular Biogenics Ltd.
  • Publication number: 20130109884
    Abstract: The present invention relates to a process for producing an ?-ketocarboxylic acid, comprising a step of oxidizing an ?-ketoaldehyde by mixing a base, carbon dioxide, the ?-ketoaldehyde and a compound represented by formula (2-1).
    Type: Application
    Filed: June 21, 2011
    Publication date: May 2, 2013
    Applicant: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventor: Koji Hagiya
  • Patent number: 8404887
    Abstract: A process for producing acrylic acid of the present invention comprises the step of conducting gas-phase oxidative dehydrogenation of a composition containing propionaldehyde using a solid catalyst containing molybdenum and vanadium as essential components, thereby obtaining acrylic acid. The obtained acrylic acid is preferably purified by crystallization, and a monomeric component containing the purified acrylic acid is polymerized to thereby give a hydrophilic resin such as an absorbent resin and a water-soluble resin.
    Type: Grant
    Filed: December 24, 2009
    Date of Patent: March 26, 2013
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Toshimitsu Moriguchi, Yoshitaka Arita
  • Publication number: 20120330049
    Abstract: The invention relates to a method for preparing acrolein from glycerol or glycerin, according to which dehydration of glycerol or glycerin is carried out in the presence of a catalyst which consists in at least one silica modified with zirconium dioxide, titanium dioxide or tungsten trioxide or any combination of these oxides, and a heteropolyacid. This method may be used for making 3-(methylthio)propionic aldehyde (MMP), 2-hydroxy-4-methylthiobutyronitrile (HMBTN), methionine or its analogs, from acrolein.
    Type: Application
    Filed: December 21, 2010
    Publication date: December 27, 2012
    Applicants: ADISSEO FRANCE S.A.S., UNIVERSITE LILLE 1 - SCIENCES ET TECHNOLOGIES, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE
    Inventors: Sebastien Paul, Benjamin Katryniok, Franck Dumeignil, Mickael Capron
  • Patent number: 8299281
    Abstract: Provided are processes for making, and processes for using triglycerides as plasticizers. Mixed triglyceride plasticizers can be produced by recovery of linear or branched C4 to C13 aldehydes from a hydroformylation product, oxidation to the acid with oxygen and/or air, recovery of the resulting acid, and esterification with a crude glycerol, wherein the total carbon number of the triester groups is from 20 to 25 for greater than or equal to 45 wt % of the plasticizer. The product selectivity obtained from esterifying with crude glycerol is comparable to that of esterifying with pure glycerol. Such plasticizers can be phthalate-free and provide outstanding properties including a suitable melting or glass transition or pour point, low volatility, increased compatibility, and excellent low temperature properties in a range of polymeric resins.
    Type: Grant
    Filed: March 16, 2010
    Date of Patent: October 30, 2012
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Jihad Mohammed Dakka, Edmund J Mozeleski, Lisa Saunders Baugh
  • Publication number: 20120130108
    Abstract: Novel synthetic routes, which are highly applicable for industrial preparation of therapeutically beneficial oxidized phospholipids are disclosed. Particularly, novel methods for efficiently preparing compounds having a glycerolic backbone and one or more oxidized moieties attached to the glycerolic backbone, which are devoid of column chromatography are disclosed. Further disclosed are novel methods of introducing phosphorous-containing moieties such as phosphate moieties to compounds having glycerolic backbone and intermediates formed thereby.
    Type: Application
    Filed: January 26, 2012
    Publication date: May 24, 2012
    Applicant: Vascular Biogenics Ltd.
    Inventors: Gideon Halperin, Eti Kovalevski-Ishai
  • Publication number: 20120035393
    Abstract: A process for preparing aliphatic carboxylic acids having 3 to 10 carbon atoms by oxidizing the corresponding aldehydes with oxygen or oxygen-containing gases, characterized in that (i) the oxidation is performed in a microreactor at elevated pressure and with an oxygen excess based on the stoichiometrically required amount of oxygen, and (ii) in that the reaction mixture removed from the microreactor is passed through at least one postreactor without further addition of oxygen, and (iii) wherein the oxidation reaction in the microreactor is performed under such conditions that aldehyde and corresponding peracid formed are present in the reaction mixture removed in a molar ratio within a range of 1:(0.9 to 1.1), preferably of 1:(0.95 to 1.05).
    Type: Application
    Filed: March 3, 2010
    Publication date: February 9, 2012
    Inventors: Tonia Weber, Alexander Kaufmann, Oliver Borgmeier, Thorsten Kreickmann, Heinz Strutz, Diana Utz, Elias Klemm, Claudia Liebold
  • Publication number: 20120016159
    Abstract: The invention is a heteropoly acid compound catalyst composition, a method of making the catalyst composition and a process for the oxidation of saturated and/or unsaturated aldehydes to unsaturated carboxylic acids using the catalyst composition. The catalyst composition is a heteropoly acid compound containing molybdenum, vanadium, phosphorus, cesium, bismuth, copper and antimony. Thermal stability is achieved with higher cesium content (up to less than 3.0) but antimony, copper and bismuth must be present to maintain good activity. The catalyst is made by dissolving compounds of the components of each of the heteropoly acid compounds in a solution, precipitating the heteropoly acid compounds, obtaining a catalyst precursor and calcining the catalyst precursor to form a heteropoly acid compound catalyst. Unsaturated aldehydes, such as methacrolein, may be oxidized in the presence of the heteropoly acid compound catalyst to produce an unsaturated carboxylic acid, such as methacrylic acid.
    Type: Application
    Filed: July 19, 2010
    Publication date: January 19, 2012
    Applicant: Saudi Basic Industries Corporation
    Inventors: Wugeng Liang, David Sullivan, James W. Kauffman, Clark Rea, Joe Linzer, Shahid Shaikh
  • Publication number: 20110306790
    Abstract: Disclosed are catalysts comprised of platinum and gold. The catalysts are generally useful for the selective oxidation of compositions comprised of a primary alcohol group and at least one secondary alcohol group wherein at least the primary alcohol group is converted to a carboxyl group. More particularly, the catalysts are supported catalysts including particles comprising gold and particles comprising platinum, wherein the molar ratio of platinum to gold is in the range of about 100:1 to about 1:4, the platinum is essentially present as Pt(0) and the platinum-containing particles are of a size in the range of about 2 to about 50 nm. Also disclosed are methods for the oxidative chemocatalytic conversion of carbohydrates to carboxylic acids or derivatives thereof. Additionally, methods are disclosed for the selective oxidation of glucose to glucaric acid or derivatives thereof using catalysts comprising platinum and gold. Further, methods are disclosed for the production of such catalysts.
    Type: Application
    Filed: December 13, 2010
    Publication date: December 15, 2011
    Applicant: RENNOVIA, INC.
    Inventors: Vincent J. Murphy, James Shoemaker, Guang Zhu, Raymond Archer, George Frederick Salem, Eric L. Dias
  • Publication number: 20110288323
    Abstract: The invention relates to a method for preparing acrolein from glycerol or glycerine, comprising dehydrating glycerol or glycerine in the presence of a catalyst consisting of at least a) a mixed oxide of zirconium and at least one metal, said metal being selected from niobium, tantalum and vanadium, b) a zirconium oxide and at least one metal oxide, the metal being selected from niobium, tantalum and vanadium, c) a silicon oxide and a mixed oxide of zirconium and at least one metal, the metal being selected from tungsten, cerium, manganese, niobium, tantalum, titanium, vanadium and silicon, d) a silicon oxide and a mixed oxide of zirconium and at least one metal, the metal being selected from tungsten, cerium, manganese, niobium, tantalum, vanadium and titanium, e) a titanium oxide and a mixed oxide of zirconium and at least one metal, said metal being selected from tungsten, cerium, manganese, niobium, tantalum, titanium, vanadium and silicon, f) a titanium oxide and a mixed oxide or zirconium and at least on
    Type: Application
    Filed: December 16, 2009
    Publication date: November 24, 2011
    Applicants: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE, ADISSEO FRANCE S.A.S
    Inventors: Virginie Belliere-Baca, Stephane Loridant, Jean-Marc Millet, Pascaline Lauriol-Garbey
  • Patent number: 7999133
    Abstract: 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: Grant
    Filed: May 31, 2010
    Date of Patent: August 16, 2011
    Assignee: Sabic Basic Industries Corporation
    Inventors: Scott A. Stevenson, Wugeng Liang, James W. Kauffman, Lixia Cai, Angie McGuffey, Joseph R. Linzer
  • Publication number: 20110144388
    Abstract: A process for producing glycolic acid from carbon monoxide and formaldehyde, optionally in a solvent, using a catalyst comprising an acidic polyoxometalate compound insoluble in formaldehyde, glycolic acid and the optional solvent, wherein the insoluble acidic polyoxometalate compound has a concentration of acid sites of greater than 60 ?mol g?1 on the external surface and/or has a Hammett Acidity value of less than ?12.8.
    Type: Application
    Filed: March 16, 2009
    Publication date: June 16, 2011
    Inventors: Ying Sun, Hua Wang, Zhongmin Liu, Martin Philip Atkins
  • Publication number: 20110137077
    Abstract: 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: Application
    Filed: August 18, 2008
    Publication date: June 9, 2011
    Applicant: BASF SE
    Inventors: Joaquim H. Teles, Steffen Oehlenschläger, Kai Gumlich, Martin Schäfer, Stephan Lamm, Stefan Berg, Michael Nilles, Hans-Peter Schildberg, Tilo John, Peter Zehner
  • Publication number: 20110087038
    Abstract: The invention relates to a process for the oxidation of organic compounds by means of oxygen, in which, in a first step, the organic compound and at least part of the oxygen required for the oxidation are introduced into a first reaction zone which is operated isothermally and with backmixing and, in a second step, the reaction mixture from the first reaction zone is introduced into a second reaction zone which is operated adiabatically. The invention further relates to a reactor for carrying out the process, which comprises at least one isothermal reaction zone (3, 5) and an adiabatic reaction zone (7) which are arranged in a reactor shell (8), with each isothermal reaction zone (3, 5) being configured in the form of a jet loop reactor and the adiabatic reaction zone (7) being configured as a bubble column.
    Type: Application
    Filed: August 1, 2008
    Publication date: April 14, 2011
    Applicant: BASF SE
    Inventors: Joaquim H Teles, Kai Gumlich, Jochen Schäfer, Steffen Oehlenschläger, Stephan Lamm, Roland Merten, Martin Schäfer, Rüdiger Grob, Uwe Emnet
  • Patent number: 7880033
    Abstract: 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: Grant
    Filed: October 24, 2006
    Date of Patent: February 1, 2011
    Assignee: Central Glass Company, Limited
    Inventors: Takeo Komata, Kenji Hosoi, Shinya Akiba
  • Patent number: 7868201
    Abstract: A process for the oxidation of hydrocarbons comprises contacting the hydrocarbon with an oxygen-containing gas in the presence of a catalyst comprising a microporous solid support, preferably a zeolite, having from 8- to 12-ring open windows and comprising non-framework metal cations selected from manganese, iron, cobalt, vanadium, chromium, copper, nickel, and ruthenium, and mixtures thereof, providing that the oxygen-containing gas does not contain significant amounts of added hydrogen. The catalyst is novel and forms part of the invention. The process may be used for oxidation of alkanes, cycloalkanes, benzene and alkylbenzenes, and is suitable for use in regioselective terminal oxidation of straight chain alkanes and for selective oxidation/separation of p-dialkylbenzenes from an alkylbenzene mixture, for example, p-xylene from an isomeric mixture of xylenes.
    Type: Grant
    Filed: July 1, 2005
    Date of Patent: January 11, 2011
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Bi-Zeng Zhan, Bjorn Moden, Jihad Dakka, Jose Santiesteban, Sebastian C. Reyes, Enrique Iglesia
  • Publication number: 20100312011
    Abstract: The invention relates to a process for separating glyoxylic acid starting from an aqueous reaction medium containing glyoxylic acid and hydrochloric acid, comprising a step of countercurrent steam stripping of the reaction medium in order to obtain, on the one hand, a gas phase containing the volatile hydrochloric acid and, on the other hand, a liquid phase containing the purified glyoxylic acid.
    Type: Application
    Filed: January 21, 2009
    Publication date: December 9, 2010
    Applicant: CLARIANT SPECIALTY FINE CHEMICALS (FRANCE)
    Inventor: Olivier Simon
  • Patent number: 7820858
    Abstract: The present invention provides a method for the synthesis of ?2-amino acids. The method also provides methods yielding ?-substituted ?-amino aldehydes and ?-substituted ?-amino alcohols. The present method according to this invention allows for increased yield and easier purification using minimal chromatography or crystallization. The methods described herein are based on an aldehyde aminomethylation which involves a Mannich reaction between an aldehyde and a formaldehyde-derived N,O-acetal (iminium precursor) and a catalyst, such as, for example, L-proline or a pyrrolidine. The invention allows for large scale, commercial preparation of ?2-amino acids.
    Type: Grant
    Filed: March 26, 2007
    Date of Patent: October 26, 2010
    Assignee: Wisconsin Alumni Research Foundation
    Inventors: Yonggui Chi, Samuel H. Gellman, William C. Pomerantz, William S. Horne, Li Guo, Emily P. English