Preparing Esters By Carbonylation Patents (Class 560/232)
  • Patent number: 10392336
    Abstract: This disclosure provides for routes of synthesis of acrylic acid and other ?,?-unsaturated carboxylic acids and their salts, including catalytic methods. For example, there is provided a process for producing an ?,?-unsaturated carboxylic acid or a salt thereof, the process comprising: (1) contacting in any order, a group 8-11 transition metal precursor, an olefin, carbon dioxide, a diluent, and a polyaromatic resin with associated metal cations to provide a reaction mixture; and (2) applying conditions to the reaction mixture suitable to produce the ?,?-unsaturated carboxylic acid or a salt thereof. Methods of regenerating the polyaromatic resin with associated metal cations are described.
    Type: Grant
    Filed: November 7, 2018
    Date of Patent: August 27, 2019
    Assignee: Chevron Phillips Chemical Company LP
    Inventors: Pasquale Iacono, Mark L. Hlavinka
  • Patent number: 10357763
    Abstract: A method for separating a homogeneous catalyst from a solution includes forming a host-guest compound between a first isomer of the catalyst and inclusion compound in the solution and isolating the host-guest compound from the solution. The catalyst may be released from the inclusion compound by converting the first isomer of the catalyst to a second isomer of the catalyst.
    Type: Grant
    Filed: August 22, 2017
    Date of Patent: July 23, 2019
    Assignee: Florida State University Research Foundation, Inc.
    Inventor: Hoyong Chung
  • Patent number: 10315980
    Abstract: The present disclosure relates to a catalyst used in the preparation of acrylic acid and acrylic acid preparation method using the same, and more specifically, discloses a catalyst capable of enhancing selectivity of acrylic acid and a production yield of acrylic acid when preparing acrylic acid from allyl alcohol using a heterogeneous catalyst including bimetallic alloy catalyst particles of gold and another metal, and an acrylic acid preparation method using the same.
    Type: Grant
    Filed: August 24, 2016
    Date of Patent: June 11, 2019
    Assignee: LG CHEM, LTD.
    Inventors: Dongsu Song, Daesung Kim, Wonjae Lee, Yongjin Choe, Hyunjoo Lee, Minsu Kim
  • Patent number: 10301250
    Abstract: A method of producing an ethylenically unsaturated carboxylic acid or ester, preferably an ?, ? ethylenically unsaturated carboxylic acid or ester. The method includes contacting formaldehyde or a suitable source thereof with a carboxylic acid or ester in the presence of a catalyst and optionally in the presence of an alcohol. The catalyst includes a nitrided metal oxide having at least two types of metal cations, M1 and M2, wherein M1 is selected from the metals of group 2, 3, 4, 13 (called also IIIA) or 14 (called also IVA) of the periodic table and M2 is selected from the metals of groups 5 or 15 (called also VA) of the periodic table.
    Type: Grant
    Filed: June 21, 2016
    Date of Patent: May 28, 2019
    Assignee: LUCITE INTERNATIONAL UK LIMITED
    Inventors: Ian Andrew York, Sabina Zieman
  • Patent number: 10300463
    Abstract: Provided is a catalyst for manufacturing an unsaturated aldehyde and/or an unsaturated carboxylic acid, which is prepared by a method in which a molybdenum component raw material is composed of only an ammonium molybdate, the weight of water for dissolution is 8.5 times or less relative to the weight of molybdenum contained in the ammonium molybdate; and a bismuth component raw material is composed of only bismuth nitrate, the weight of a nitric acid aqueous solution for dissolution is 2.3 times or more relative to the weight of bismuth contained in the bismuth nitrate, and a nitric acid concentration in the nitric acid aqueous solution for dissolving the bismuth nitrate is 10% by weight or more.
    Type: Grant
    Filed: February 25, 2016
    Date of Patent: May 28, 2019
    Assignee: NIPPON KAYAKU KABUSHIKI KAISHA
    Inventors: Tomoyuki Kawamura, Motohiko Sugiyama, Ryota Hiraoka
  • Patent number: 10227283
    Abstract: The present disclosure provides for a method for measuring the concentration of one or more components in a feed stream or reactor mixture of a process for producing acetic acid by both infrared and Raman spectroscopic analyses. In some embodiments, at least one feed stream comprising water is adjusted in response to the measured concentration of one or more components.
    Type: Grant
    Filed: June 28, 2018
    Date of Patent: March 12, 2019
    Assignee: LyondellBasell Acetyls, LLC
    Inventors: Noel C. Hallinan, John D. Hearn, Ryan J. Mathews, Brian A. Salisbury, Daniel F. White
  • Patent number: 10208008
    Abstract: A process is provided for converting mevalonic acid into various useful products and derivatives. More particularly, the process comprises reacting mevalonic acid, or a solution comprising mevalonic acid, in the presence of a solid catalyst at an elevated temperature and pressure to thereby form various biobased products. The process may also comprise: (a) providing a microbial organism that expresses a biosynthetic mevalonic acid pathway; (b) growing the microbial organism in fermentation medium comprising suitable carbon substrates, whereby biobased mevalonic acid is produced; and (c) reacting the biobased mevalonic acid in the presence of a solid catalyst at an elevated temperature and pressure to yield various biobased products.
    Type: Grant
    Filed: November 24, 2015
    Date of Patent: February 19, 2019
    Assignee: Visolis, Inc.
    Inventors: Deepak Dugar, Brian Neltner
  • Patent number: 10189768
    Abstract: The present invention relates to a method for hydrogenolysis of alpha-hydroxy esters or acids, comprising reacting the alpha-hydroxy ester or acid in the presence of a heterogeneous catalyst. The present invention also relates to a method for producing propionic acid ester, and the use of any of the methods for the production of propionic acid esters, such as alkyl propionate.
    Type: Grant
    Filed: June 23, 2016
    Date of Patent: January 29, 2019
    Assignee: Danmarks Tekniske Universitet
    Inventors: Shunmugavel Saravanamurugan, Santosh Govind Khokarale, Anders Riisager
  • Patent number: 10183906
    Abstract: Process for the hydrolysis of a methyl acetate with at least one of water and methanol in the presence of at least one Brønsted acid catalyst to produce acetic acid. The process employs a methyl acetate feed in which the total amount of acetaldehyde and 1,1 dimethoxyethane impurities is maintained at 100 pm wt or less calculated as mass equivalents of acetaldehyde.
    Type: Grant
    Filed: June 12, 2015
    Date of Patent: January 22, 2019
    Assignee: BP CHEMICALS LIMITED
    Inventors: Berian John Daniel, John Glenn Sunley, Russell Alan Taylor, Gareth Gerald Armitage
  • Patent number: 10160712
    Abstract: A method of catalytic oxidation of a lignite using oxygen as an oxidant at atmospheric pressure is provided. The method includes the following steps, pulverizing the lignite to 200-mesh or less; drying the pulverized lignite at a temperature of 80° C. in vacuum for 10 h; weighing 0.5 g of the dried lignite and sequentially adding 10 ml of acetic acid, 0.5 mmol of a catalyst and 0.15-0.25 mmol of a cocatalyst into a round-bottom flask filled with the oxygen, keeping oxygen pressure at 0.1 MPa, reacting at a temperature of 80-120° C. for 4-12 h; using oxygen as the oxidant to catalytically oxidize the reacted lignite at an atmospheric pressure of 0.1 MPa; filtering after the reaction is finished; decompressing the filtrate to remove the acetic acid, adding a small amount of ethyl acetate to dissolve, and using an excess CH2N2/ether solution to esterify for 10 h at room temperature; and analyzing the esterified product through a gas chromatography-mass spectrometer.
    Type: Grant
    Filed: December 7, 2016
    Date of Patent: December 25, 2018
    Assignee: CHINA UNIVERSITY OF MINING AND TECHNOLOGY
    Inventors: Jing Liang, Huihui Yang, Xianyong Wei, Zhimin Zong
  • Patent number: 10160711
    Abstract: This disclosure provides for routes of synthesis of acrylic acid and other ?,?-unsaturated carboxylic acids and their salts, including catalytic methods. For example, there is provided a process for producing an ?,?-unsaturated carboxylic acid or a salt thereof, the process comprising: (1) contacting in any order, a group 8-11 transition metal precursor, an olefin, carbon dioxide, a diluent, and a polyaromatic resin with associated metal cations to provide a reaction mixture; and (2) applying conditions to the reaction mixture suitable to produce the ?,?-unsaturated carboxylic acid or a salt thereof. Methods of regenerating the polyaromatic resin with associated metal cations are described.
    Type: Grant
    Filed: December 13, 2016
    Date of Patent: December 25, 2018
    Assignee: Chevron Phillips Chemical Company LP
    Inventors: Pasquale Iacono, Mark L. Hlavinka
  • Patent number: 10160830
    Abstract: An alkylene oxide mixture containing greater than 50% by weight ethylene oxide is continuously polymerized in the presence of a double metal cyanide polymerization catalyst and certain magnesium, Group 3-Group 15 metal or lanthanide series metal compounds. The presence of the magnesium, Group 3-Group 15 metal or lanthanide series metal compound permits the polymerization to be performed continuously without premature deactivation of the double metal cyanide catalyst.
    Type: Grant
    Filed: June 15, 2016
    Date of Patent: December 25, 2018
    Assignee: Dow Global Technologies LLC
    Inventors: David A. Babb, Jean-Paul Masy, Mattias Schaefer, William A. Koonce, Donald Cameron
  • Patent number: 10144693
    Abstract: Carboxylic acids are prepared by a one-step gas phase process comprising the step of contacting under halogen-free hydroxycarbonylation conditions an alkene, carbon monoxide, water, and a solid sulfide-containing catalyst.
    Type: Grant
    Filed: October 6, 2015
    Date of Patent: December 4, 2018
    Assignee: Dow Global Technologies LLC
    Inventors: David G. Barton, Gerolamo Budroni, Steven L. F. Corthals
  • Patent number: 10138196
    Abstract: A catalytic process for preparing an ?,?-ethylenically unsaturated carboxylic acid salt from an alkene, carbon dioxide and an alkoxide having a secondary or tertiary carbon atom directly bound to a [O?] group is described. The alcohol byproduct is distilled off after an intermediate phase separation. This provides pure ?,?-ethylenically unsaturated carboxylic acid salt at minimum effort.
    Type: Grant
    Filed: May 9, 2016
    Date of Patent: November 27, 2018
    Assignee: BASF SE
    Inventors: Thomas Schaub, Nuria Huguet Subiela, Rocco Paciello, Donata Maria Fries, Simone Manzini
  • Patent number: 10138197
    Abstract: This disclosure describes a new route to acrylate esters via direct catalytic partial oxidation of allyl ether using heterogeneous manganese oxide catalysts. The method involves forming allyl acrylate by contacting allyl ether, where the allyl ether is in solution with a solvent, with one or more oxidants in the presence of a mesoporous manganese oxide (MnOx) catalyst. Oxygen or peroxide can be used as the oxidant. The yield of and selectivity for acrylate ester can be very high, and process efficiency is improved over current processes.
    Type: Grant
    Filed: February 26, 2018
    Date of Patent: November 27, 2018
    Assignee: EXXONMOBIL RESEARCH AND ENGINEERING COMPANY
    Inventors: Partha Nandi, Steven L. Suib, Timothy D. Shaffer
  • Patent number: 10124321
    Abstract: A carbon nitride heterogeneous catalyst containing rhodium, a method for preparing the catalyst, and a method for preparing acetic acid using the catalyst is disclosed. The heterogeneous catalyst is characterized in that the rhodium metal is contained in carbon nitride which is a support insoluble in a liquid solvent, such as water or alcohol. Thus, the catalyst can easily be separated from a resulting product even by a simple process such as filtration. Accordingly, the carbon nitride heterogeneous catalyst exhibits excellent long-term stability and activity by being capable of overcoming the disadvantages of the method using a conventional homogeneous catalyst and minimizing the phenomenon of rhodium leaching, compared to the results of the conventional homogeneous catalytic reactions. The catalyst can thus be effectively used for the preparation of acetic acid by a carbonylation reaction between methanol and carbon monoxide.
    Type: Grant
    Filed: January 26, 2018
    Date of Patent: November 13, 2018
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Jong Wook Bae, Tae Sun Chang, Beom Sik Kim, Jae Hyun Park, Ji Soo Nam
  • Patent number: 10125081
    Abstract: Provided is a production method whereby corresponding carboxylic acid anhydrides and carboxylic acid esters can be obtained at high yield from various carboxylic acids even without a solvent and near room temperature. A method for producing a carboxylic acid anhydride represented by formula (II), the method comprising reacting a compound represented by formula (I) and a carboxylic acid in the presence of a Group II metal compound having an ionic ligand containing an oxygen atom. A method for producing a carboxylic acid ester, the method comprising reacting a carboxylic acid anhydride produced by the aforementioned method and an alcohol. In formula (I), R1 represents a C1-20 hydrocarbon group. In formula (II), R2 represents a C1-20 hydrocarbon group.
    Type: Grant
    Filed: June 4, 2015
    Date of Patent: November 13, 2018
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Akihiro Goto, Yoshihiro Kamon
  • Patent number: 10106487
    Abstract: The present invention relates to a simple one step oxidative dehydrogenation process for the synthesis of alkyl pyruvate with 100% selectivity towards alkyl pyruvate comprising reacting an alkyl lactate in the presence of catalyst at the temperature ranging from 25-100° C. for the time period ranging from 5 to 40 hours in an organic solvent and hydrogen peroxide to afford alkyl pyruvate.
    Type: Grant
    Filed: June 10, 2016
    Date of Patent: October 23, 2018
    Assignee: COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH
    Inventors: Shubhangi Bhalchandra Umbarkar, Mohan Keraba Dongare, Swati Laxmikantrao Pandhare, Sonali Balasaheb Khomane, Dhananjay Shahauraj Doke
  • Patent number: 10100007
    Abstract: A continuous flow process for the preparation of one or more esters of lactic acid and 2-hydroxy-3-butenoic acid or ?-hydroxy methionine analogs from a sugar in the presence of a solid Lewis acid catalyst and a solvent comprising an organic solvent and water. The invention provides a means for stabilizing a Lewis acid catalyst for use in a continuous reaction process wherein the water is present in an amount of up to or equal to 10 vol. % of the organic solvent.
    Type: Grant
    Filed: November 12, 2015
    Date of Patent: October 16, 2018
    Assignee: Haldor Topsoe A/S
    Inventors: Irantzu Sadaba Zubiri, Esben Taarning
  • Patent number: 10067113
    Abstract: Processes for producing acetic acid and determining corrosion therein are described herein. The processes generally include contacting methanol and carbon monoxide in the presence of a liquid reaction medium under carbonylation conditions sufficient to form acetic acid, wherein the liquid reaction medium includes: a carbonylation catalyst selected from rhodium catalysts, iridium catalysts and palladium catalysts; from 1 wt. % to 14 wt. % water; and one or more, in-situ generated derivatives of the one or more additives and combinations thereof; wherein the one or more additives are independently selected from non-benzoyl containing pentavalent phosphine oxides, compound mixtures of at least four phosphine oxides and pentavalent aryl or alkaryl phosphine oxides including one or more benzoyl groups; and recovering acetic acid from the process.
    Type: Grant
    Filed: February 24, 2015
    Date of Patent: September 4, 2018
    Assignee: LyondellBasell Acetyis, LLC
    Inventors: Noel C. Hallinan, Brian A. Salisbury, Daniel F. White, David L. Ramage
  • Patent number: 10059594
    Abstract: In an embodiment, a method of producing phosgene in a tube reactor comprises introducing a feed comprising carbon monoxide and chlorine to a tube of the reactor, the tube having a particulate catalyst disposed therein, wherein a thermally conductive material separate from the tube contacts at least a portion of the particulate catalyst; to produce a product composition comprising phosgene, and carbon tetrachloride in an amount of 0 to 10 ppm by volume based on the volume of the phosgene.
    Type: Grant
    Filed: July 25, 2014
    Date of Patent: August 28, 2018
    Assignee: SABIC GLOBAL TECHNOLOGIES B.V.
    Inventors: Pankaj Singh Gautam, William E. Hollar, Jr.
  • Patent number: 10011551
    Abstract: Catalytic process for preparing an ?,?-ethylenically unsaturated carboxylic acid salt, comprising reacting an alkene and carbon dioxide in the presence of a carboxylation catalyst and releasing the ?,?-ethylenically unsaturated carboxylic acid salt with a base, the carboxylation catalyst being a transition metal complex, which comprises a structurally constrained bidentate P,X ligand, wherein X is selected from the group consisting of P, N, O, and carbene, the P and X atom are separated by 2 to 4 bridging atoms, and wherein the bridging atoms are part of at least one 5- to 7-membered cyclic substructure. A further catalytic processes for preparing ?,?ethylenically unsaturated carboxylic acid derivatives from CO2 and an alkene is provided.
    Type: Grant
    Filed: May 13, 2015
    Date of Patent: July 3, 2018
    Assignee: BASF SE
    Inventors: Michael Limbach, Ivana Jevtovikj, Nuria Huguet Subiela, Alvaro Gordillo, Sabine Chantal Eileen Stieber, Ronald Lindner, Miriam Bru Roig, Michael Lejkowski, Takeharu Kageyama, Stephan A. Schunk
  • Patent number: 9988268
    Abstract: The present invention relates to novel anthraquinone derivatives, 2,6-diisohexylanthracene-9,10-dione and 2,7-diisohexyl-anthracene-9,10-dione, preferably to be used for the preparation of hydrogen peroxide, and to a process for the preparation of these anthraquinone derivatives.
    Type: Grant
    Filed: May 28, 2015
    Date of Patent: June 5, 2018
    Assignee: BASF SE
    Inventors: Dominic Riedel, Joaquim Henrique Teles, Thomas Wurm
  • Patent number: 9981903
    Abstract: The invention relates to a method for preparing di- or tricarboxylic esters by alkoxycarbonylation of dienes having conjugated double bonds. The method includes the steps of initially charging a diene having two conjugated double bonds, adding a phosphine ligand according to formula (I) and a catalyst precursor, adding an alcohol, feeding in CO, and heating the reaction mixture with conversion of the diene to a di- or tricarboxylic ester.
    Type: Grant
    Filed: July 17, 2017
    Date of Patent: May 29, 2018
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Kaiwu Dong, Ralf Jackstell, Matthias Beller, Dirk Fridag, Dieter Hess, Katrin Marie Dyballa, Frank Geilen, Robert Franke
  • Patent number: 9950984
    Abstract: An object of the present invention is to provide a process for producing ?-fluoroacrylic acid esters at a high starting material conversion and a high yield. The present invention provides, as a means to achieve the object, a process for producing a compound represented by formula (1): wherein R1 and R2 are the same or different and each represent alkyl, fluoroalkyl, aryl optionally substituted with at least one substituent, halogen, or hydrogen; and R3 represents alkyl, fluoroalkyl, or aryl optionally substituted with at least one substituent, the process comprising step A of reacting a compound represented by formula (2): wherein the symbols are as defined above, with carbon monoxide and an alcohol represented by formula (3): R3—OH??(3) wherein the symbol is as defined above, in the presence of a transition metal complex catalyst containing at least one bidentate phosphine ligand and a base to thereby obtain the compound represented by formula (1).
    Type: Grant
    Filed: June 6, 2017
    Date of Patent: April 24, 2018
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Akihiro Gotou, Manaho Miyazaki, Sumi Ishihara, Takashi Namikawa, Tatsuya Ohtsuka, Yosuke Kishikawa
  • Patent number: 9944587
    Abstract: A process for vapor-phase carbonylation of methanol to methyl formate, whereby a feed gas containing methanol, carbon monoxide, hydrogen and oxygen is passed through a reactor loaded with a supported nano-scaled platinum group metal heterogeneous catalyst to produce methyl formate by a vapor-phase carbonylation reaction, under reaction conditions with a space velocity of 500-5000 h?1, a temperature of 50-150° C. and a pressure of 0.01-2 MPa. Supported nano-scaled platinum group metal heterogeneous catalysts are prepared via ultrasonic dispersion and calcination. Methyl formate is produced and isolated under relatively mild conditions.
    Type: Grant
    Filed: June 12, 2014
    Date of Patent: April 17, 2018
    Assignee: FUJIAN INSTITUTE OF RESEARCH ON THE STRUCTURE OF MATTER, CHINESE ACADEMY OF SCIENCES
    Inventors: Zhongning Xu, Guocong Guo, Siyan Peng, Zhiqiao Wang, Qingsong Chen, Mingsheng Wang, Yuangen Yao
  • Patent number: 9938226
    Abstract: Alkyl alkanoates, e.g., methyl propionate, are made by a gas phase process comprising the step of contacting under carbonylation conditions an alkene (e.g., ethylene), carbon monoxide, an alkanol (e.g., methanol), and a solid sulfide-based metal catalyst (e.g., iron sulfide). The alkyl alkanoate can be converted in a second step to an alkyl ester of an aliphatic carboxylic acid, e.g., methyl methacrylate, through condensation with an aldehyde, e.g., formaldehyde.
    Type: Grant
    Filed: September 11, 2014
    Date of Patent: April 10, 2018
    Assignee: Dow Global Technologies LLC
    Inventors: David G. Barton, Gerolamo Budroni, Steven L. F. Corthals
  • Patent number: 9873654
    Abstract: A mixture of polyfluoroalkene carboxylic acids or salts thereof represented by the general formulas: CnF2n+1CH?CF(CF2CF2)mCF2COOM and Cn?1F2n?1CF?CHCF2(CF2CF2)mCF2COOM wherein M is a hydrogen atom, an ammonium salt, an organic amine salt or an alkali metal, n is an integer of 1 to 6 and m is an integer of 0 to 2. The mixture of polyfluoroalkene carboxylic acids or salts thereof is produced by subjecting a polyfluoroalkane carboxylic acids represented by the general formula: CnF2n+1(CH2CF2)(CF2CF2)mCF2COOH to a dehydrofluorination reaction in the presence of a nitrogen-containing heterocyclic compound catalyst, and has a lower critical micelle concentration and less surface tension at that time, therefore, the mixture of polyfluoroalkene carboxylic acids or salts thereof can be effectively used as a surfactant in the polymerization of fluorine-containing monomers.
    Type: Grant
    Filed: July 28, 2015
    Date of Patent: January 23, 2018
    Assignee: Unimatec Co., Ltd.
    Inventors: Yuichiro Oda, Ryota Negishi
  • Patent number: 9809692
    Abstract: Provided is a plurality of resin beads, wherein the resin beads comprise polymerized units of monovinyl aromatic monomer and polymerized units of multivinyl aromatic monomer, and wherein the resin beads have BET surface area of 15 to 38 m2/g and volume capacity of 0.7 or higher. Also provided is a method of making a product of the chemical reaction of one or more reactants, where the method comprises reacting the reactants with each other in the presence of such resin beads.
    Type: Grant
    Filed: April 9, 2015
    Date of Patent: November 7, 2017
    Assignee: Rohm and Haas Company
    Inventors: Jose Antonio Trejo O'Reilly, Takashi Masudo, Daika Kouzaki
  • Patent number: 9809611
    Abstract: Novel bidentate ligands of general formula (I) are described. In formula (I), A and B each independently represent a linking group; and R represents a hydrocarbyl aromatic structure. The substituent(s) Yi on the aromatic structure together have a total number ?ti of atoms other than hydrogen such that ?ti is greater than or equal to 4, wherein ti represents the number of atoms other than hydrogen on a particular substituent Yi. i ranges from 1 to n; and n is the total number of substituent(s) Yi. The groups X1, X2, X3 and X4 are joined via tertiary carbon atoms to the respective atom Q2 or Q1. Q1 and Q2 each independently represent phosphorus, arsenic, or antimony. A catalyst system and a process for the carbonylation of ethylenically unsaturated compounds utilizing the catalyst system are also described.
    Type: Grant
    Filed: November 27, 2007
    Date of Patent: November 7, 2017
    Assignee: LUCITE INTERNATIONAL UK LIMITED
    Inventors: Graham Ronald Eastham, Ian Butler
  • Patent number: 9809528
    Abstract: The present disclosure is directed to methods and composition used in the preparation of alpha-hydroxy carboxylic acids and esters from higher sugars using a tandem catalyst system comprising retro-aldol catalysts and Lewis acid catalysts. In some embodiments, these alpha-hydroxy carboxylic acids may be prepared from pentoses and hexoses. The retro-aldol and Lewis catalysts may be characterized by their respective ability to catalyze a 1,2-carbon shift reaction and a 1,2-hydride shift reaction on an aldose or ketose substrate.
    Type: Grant
    Filed: July 12, 2016
    Date of Patent: November 7, 2017
    Assignee: California Institute of Technology
    Inventors: Marat Orazov, Mark E. Davis
  • Patent number: 9802185
    Abstract: The present invention provides a catalyst system capable of catalyzing the carbonylation of an ethylenically unsaturated compound, which system is obtainable by combining: a) a metal of Group VIB or Group VIIIB or a compound thereof, b) a bidentate phosphine, arsine or stibine ligand, and c) an acid, wherein the ligand is present in at least a 2:1 molar excess compared to the metal or the metal in the metal compound, and that the acid is present in at least a 2:1 molar excess compared to the ligand, a process for the carbonylation of an ethylenically unsaturated compound, a reaction medium, and use of the system.
    Type: Grant
    Filed: April 9, 2015
    Date of Patent: October 31, 2017
    Assignee: LUCITE INTERNATIONAL UK LIMITED
    Inventors: Graham Eastham, Neil Tindale
  • Patent number: 9776947
    Abstract: In a process for the production of dialkyl succinate from a feedstock comprising maleic anhydride, feed in the liquid phase is provided to a reactor operated at a temperature of at least about 150° C. The feed is contacted with hydrogen at a pressure of at least about 300 psig in the presence of an acid tolerant catalyst and an alkanol wherein at least some of the carbon carbon double bonds of the maleic anhydride are hydrogenated to form succinic acid and that the heat generated promotes esterification to dialkyl succinate in situ. A stream of dialkyl succinate is recovered from the reactor.
    Type: Grant
    Filed: October 13, 2014
    Date of Patent: October 3, 2017
    Assignee: JOHNSON MATTHEY DAVY TECHNOLOGIES LIMITED
    Inventors: Graham Reed, Andrew George Hiles, Rikard Umberto Andersson, Simon Nicholas Tilley, Paul Gordon
  • Patent number: 9776179
    Abstract: In one aspect, the invention provides a method for synthesizing a fatty olefin derivative. The method includes: a) contacting an olefin according to Formula I with a metathesis reaction partner according to Formula IIb in the presence of a metathesis catalyst under conditions sufficient to form a metathesis product according to Formula IIIb: and b) converting the metathesis product to the fatty olefin derivative. Each R1 is independently selected from H, C1-18 alkyl, and C2-18 alkenyl; R2b is C1-8 alkyl; subscript y is an integer ranging from 0 to 17; and subscript z is an integer ranging from 0 to 17. In certain embodiments, the metathesis catalyst is a tungsten catalyst or a molybdenum catalyst. In various embodiments, the fatty olefin derivative is a pheromone. Pheromone compositions and methods of using them are also described.
    Type: Grant
    Filed: November 17, 2016
    Date of Patent: October 3, 2017
    Assignee: PROVIVI, INC.
    Inventors: Keith M Wampler, Peter Meinhold, Pedro Coelho, Vu Bui, Levente Ondi, Hasan Mehdi
  • Patent number: 9771312
    Abstract: Process for the co-production of acetic acid and dimethyl ether with reduced formic acid content by distilling a mixture containing dimethyl ether, methanol and methyl formate, separating methyl formate from the mixture to recover dimethyl ether and methanol, and catalytically reacting the methanol and methyl acetate to produce a reaction product of acetic acid an dimethyl ether.
    Type: Grant
    Filed: June 12, 2015
    Date of Patent: September 26, 2017
    Assignee: BP CHEMICALS LIMITED
    Inventors: Mareike Beckers, Timothy Crispin Bristow
  • Patent number: 9771315
    Abstract: Provided is a method that can produce phenyl(meth)acrylate inexpensively and at high yields. The phenyl(meth)acrylate production method of the present invention reacts (meth)acrylic acid with carbonic acid diphenyl. Further, the phenyl(meth)acyrlate composition of the present invention contains 90-99.999 wt % phenyl(meth)acrylate and 0.001-10% carbonic acid diphenyl. Or, the phenyl(meth)acrylate composition of the present invention contains 90-99.999 wt % phenyl(meth)acrylate and 0.001-10 wt % of a specified compound.
    Type: Grant
    Filed: October 24, 2014
    Date of Patent: September 26, 2017
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Ryo Aizawa, Takeshi Matsuo, Naoshi Murata, Hiroyuki Mori
  • Patent number: 9738583
    Abstract: A process for preparing acrylic acid from formaldehyde and acetic acid, is performed by (i) providing a gaseous stream S1 comprising formaldehyde, acetic acid, oxygen and water, where the formaldehyde content of stream S1 is in the range from 8% to 18% by volume, based on the total volume of stream S1, the ratio of the volumes of acetic acid to formaldehyde is in the range from 0.6:1 to 1.1:1, and the molar ratio of oxygen to the total amount of organic carbon is in the range from 0.02:1 to 0.15:1; and (ii) contacting stream S1 with an aldol condensation catalyst in a reaction zone to obtain a gaseous stream S2 containing acrylic acid.
    Type: Grant
    Filed: November 10, 2016
    Date of Patent: August 22, 2017
    Assignee: BASF SE
    Inventors: Marco Hartmann, Lukas Schulz, Nicolai Tonio Woerz, Yong Liu, Till Christian Brueggemann, Michael Lejkowski, Johannes Lieberknecht
  • Patent number: 9732027
    Abstract: An object of the present invention is to provide a process for producing ?-fluoroacrylic acid esters at a high starting material conversion and a high yield. The present invention provides, as a means to achieve the object, a process for producing a compound represented by formula (1): wherein R1 and R2 are the same or different and each represent alkyl, fluoroalkyl, aryl optionally substituted with at least one substituent, halogen, or hydrogen; and R3 represents alkyl, fluoroalkyl, or aryl optionally substituted with at least one substituent, the process comprising step A of reacting a compound represented by formula (2): wherein the symbols are as defined above, with carbon monoxide and an alcohol represented by formula (3): R3—OH??(3) wherein the symbol is as defined above, in the presence of a transition metal complex catalyst containing at least one bidentate phosphine ligand and a base to thereby obtain the compound represented by formula (1).
    Type: Grant
    Filed: December 26, 2014
    Date of Patent: August 15, 2017
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Akihiro Gotou, Manaho Miyazaki, Sumi Ishihara, Takashi Namikawa, Tatsuya Ohtsuka, Yosuke Kishikawa
  • Patent number: 9701614
    Abstract: An object of the present invention is to provide a process for producing ?-fluoroacrylic acid esters at a high starting material conversion and a high yield. The present invention provides, as a means to achieve the object, a process for producing a compound represented by formula (1): wherein R1 and R2 are the same or different and each represent alkyl, fluoroalkyl, aryl optionally substituted with at least one substituent, halogen, or hydrogen; and R3 represents alkyl, fluoroalkyl, or aryl optionally substituted with at least one substituent, the process comprising step A of reacting a compound represented by formula (2): wherein the symbols are as defined above, with carbon monoxide and an alcohol represented by formula (3): R3—OH??(3) wherein the symbol is as defined above, in the presence of a transition metal complex catalyst containing at least one bidentate phosphine ligand and a base to thereby obtain the compound represented by formula (1).
    Type: Grant
    Filed: December 26, 2014
    Date of Patent: July 11, 2017
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Akihiro Gotou, Manaho Miyazaki, Sumi Ishihara, Takashi Namikawa, Tatsuya Ohtsuka, Yosuke Kishikawa
  • Patent number: 9695099
    Abstract: The present invention relates to a process for preparing acrylic acid from acetic acid and formaldehyde, which comprises (a) provision of a stream S1 comprising acetic acid and formaldehyde, where the molar ratio of acetic acid to formaldehyde in the stream S1 is in the range from 0.5:1 to 2:1; (b) contacting of the stream S1 with an aldol condensation catalyst comprising vanadium, phosphorus and oxygen to give a stream S2 comprising acrylic acid, where, in (b), the space velocity WHSV is in the range from 0.35 to 7.0 kg/kg/h.
    Type: Grant
    Filed: December 2, 2015
    Date of Patent: July 4, 2017
    Assignee: BASF SE
    Inventors: Yong Liu, Martin Dieterle, Nicolai Tonio Woerz, Andrei-Nicolae Parvulescu, Michael Lejkowski, Johannes Lieberknecht, Christian Walsdorff, Kazuhiko Amakawa
  • Patent number: 9695106
    Abstract: In an embodiment, a method of producing a carbonate comprises reacting carbon monoxide and chlorine in a phosgene reactor in the presence of a catalyst to produce a first product comprising phosgene; wherein carbon tetrachloride is present in the first product in an amount of 0 to 10 ppm by volume based on the total volume of phosgene; and reacting a monohydroxy compound with the phosgene to produce the carbonate; wherein the phosgene reactor comprises a tube, a shell, and a space located between the tube and the shell; wherein the tube comprises one or more of a mini-tube section and a second tube section; a first concentric tube concentrically located in the shell; a twisted tube; an internal scaffold; and an external scaffold.
    Type: Grant
    Filed: February 4, 2015
    Date of Patent: July 4, 2017
    Assignee: SABIC GLOBAL TECHNOLOGIES B.V.
    Inventors: Pankaj Singh Gautam, William E. Hollar, Jr., Sergio Ferrer Nadal, John Joseph Anderson
  • Patent number: 9656950
    Abstract: Provided is a method for efficiently producing an oxime, which is a method for producing an oxime by oxidizing, an amine, the method comprising a first contact step and a second contact step, wherein the second contact step is performed by bringing an additional amine into contact with oxygen in the presence of at least a part of an oxidation product obtained in the first contact step.
    Type: Grant
    Filed: March 17, 2014
    Date of Patent: May 23, 2017
    Assignee: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Masahiro Hoshino, Yuta Kikuchi
  • Patent number: 9656248
    Abstract: Provided is a catalyst having high activity and yield of a target product for producing an unsaturated aldehyde and/or an unsaturated carboxylic acid and further having high mechanical strength. The catalyst is a catalyst prepared by a method in which a catalyst formulation satisfies specified atomic ratios; and in the preparation thereof, a molybdenum component raw material is an ammonium molybdate, a solvent for dissolving the ammonium molybdate is water, a bismuth component raw material is bismuth nitrate, and a solvent for dissolving bismuth nitrate is a nitric acid aqueous solution, and the weight of water for dissolving the ammonium molybdate, the weight of the nitric acid aqueous solution for dissolving the bismuth nitrate, and the acid concentration of the nitric acid aqueous solution are satisfied with specified ranges, respectively.
    Type: Grant
    Filed: May 8, 2014
    Date of Patent: May 23, 2017
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Yuuta Nakazawa, Yoshiko Shoya, Masaki Nakahara, Eiji Nishimura, Kazuo Shiraishi, Tatsuhiko Kurakami, Ryota Hiraoka
  • Patent number: 9546120
    Abstract: Integrated process for the production of methyl acetate and methanol by carbonylating dimethyl ether with synthesis gas, recovering a methyl acetate stream and an unreached synthesis gas stream containing methyl acetate, and scrubbing the synthesis gas to remove methyl acetate. The scrubbed synthesis gas is passed for methanol synthesis.
    Type: Grant
    Filed: December 19, 2013
    Date of Patent: January 17, 2017
    Assignee: BP CHEMICALS LIMITED
    Inventor: Timothy Crispin Bristow
  • Patent number: 9512061
    Abstract: Process for the preparation of racemic ?-amino acids or of glycine, wherein the corresponding ?-hydroxycarboxylic acid, selected from hydroxyacetic acid, lactic acid, malic acid, ?-hydroxyglutamic acid, isocitric acid, tartronic acid and tartaric acid, or at least one salt of the corresponding ?-hydroxycarboxylic acid is reacted in the presence of at least one heterogeneous catalyst which comprises at least one transition metal, in the presence of hydrogen with at least one nitrogen compound (c), where the nitrogen compound (c) is selected from primary and secondary amines and ammonia.
    Type: Grant
    Filed: December 19, 2012
    Date of Patent: December 6, 2016
    Assignee: BASF SE
    Inventors: Roland Bou Chedid, Alfred Oftring, Wolfgang Staffel, Markus Christian Biel, Johann-Peter Melder, Christian Gruenanger
  • Patent number: 9505702
    Abstract: Integrated process for the production of methyl acetate and methanol. The process is carried out by carbonylating dimethyl ether with synthesis gas and recovering methanol and unreacted synthesis gas. The recovered synthesis gas is utilized as the sole fresh synthesis gas for methanol synthesis.
    Type: Grant
    Filed: December 19, 2013
    Date of Patent: November 29, 2016
    Assignee: BP CHEMICALS LIMITED
    Inventors: Edo Johann Becker, Timothy Crispin Bristow
  • Patent number: 9505703
    Abstract: Process for the production of methyl acetate by carbonylating dimethyl ether with carbon monoxide in the presence of hydrogen and a zeolite catalyst. The process is carried out with a molar ratio of hydrogen to carbon monoxide of at least 1 and the catalyst has been calcined at a temperature of from about 375° C. to about 475° C.
    Type: Grant
    Filed: March 6, 2014
    Date of Patent: November 29, 2016
    Assignee: BP CHEMICALS LIMITED
    Inventors: Evert Jan Ditzel, Bogdan Costin Gagea, Nicholas John Hazel, John Glenn Sunley, Gordon John Haining
  • Patent number: 9493608
    Abstract: This invention relates to a novel process for preparing an aliphatic hybrid ester/ether polyol. This process simultaneously transesterifies and alkoxylates a mixture of at least one ester group containing compound which is free of ether groups, and at least one or more hydroxyl group containing compound which is free of ester groups; with the proviso that the mixture has an overall hydroxyl number of less than or equal to 350; with at least one alkylene oxide; in the presence of a mixture of catalysts. The catalyst mixture comprises at least one DMC catalyst, and at least one non-alkaline transesterification catalyst.
    Type: Grant
    Filed: December 21, 2015
    Date of Patent: November 15, 2016
    Assignee: Covestro LLC
    Inventors: Kenneth G. McDaniel, Rick L. Adkins, Don S. Wardius
  • Patent number: 9492814
    Abstract: In accordance with the invention, there is provided a novel catalyst composition comprising MoVGaPdNbXY, wherein X comprises La, Te, Ge, Zn, In, or W; and Y comprises Al or Si; wherein Mo, V, Ga, Pd, Nb, La, Te, Ge, Zn, In, W, Al, or Si are optionally present in combination with oxygen; wherein the catalyst does not comprise an additional element that acts as a catalyst in the conversion of a propylene to the product. Also, disclosed is a method for the conversion of a propylene to a carboxylic acid moiety by contacting the propylene with the disclosed catalyst.
    Type: Grant
    Filed: April 7, 2014
    Date of Patent: November 15, 2016
    Assignee: SAUDI BASIC INDUSTRIES CORPORATION
    Inventors: Zaheer Irshad, Khalid Karim
  • Patent number: 9469591
    Abstract: Integrated process for the production of methyl acetate and methanol. The process is carried out by carbonylating dimethyl ether with synthesis gas, recovering methyl acetate and unreacted synthesis gas and supplying unreacted synthesis gas and fresh synthesis gas for methanol synthesis.
    Type: Grant
    Filed: December 19, 2013
    Date of Patent: October 18, 2016
    Assignee: BP CHEMICALS LIMITED
    Inventor: Timothy Crispin Bristow