Preparing Esters By Esterification Or Carbonylation Patents (Class 560/204)
  • Patent number: 10465295
    Abstract: A jettable etchant composition includes 1 to 90 wt % active ingredient, and a remainder containing any combination of the following: 10 to 90 wt % solvent, 0 to 10 wt % reducing agents, <1 to 20 wt % pickling agent, 0 to 5 wt % surfactant, and 0 to 5 wt % antifoam agent. The composition can also include a soluble compound containing at least one element which when dissolved has a higher standard electrode potential than a metal to be etched or a soluble compound containing a group IA element, and a soluble platinum group metal. An ink composition can include a group VA compound or a group IIIA compound in a solvent system formulated to be jettable on a surface at a drop volume of about 5 to about 10 picoliters and to achieve a final sheet resistance of less than about 20 ?/? of the surface upon activation.
    Type: Grant
    Filed: May 19, 2015
    Date of Patent: November 5, 2019
    Assignee: Alpha Assembly Solutions Inc.
    Inventors: Steven Prokopiak, Ellen S. Tormey, Oscar Khaselev, Michael T. Marczi, Bawa Singh
  • Patent number: 10358457
    Abstract: The present invention relates to a metal oxalate hydrate body having a certain shape, a preparation method thereof, and a metal oxide/carbon composite body prepared by using the metal oxalate hydrate body. In the present invention, the metal oxalate body, whose shape is diversely controlled, and the metal oxide/carbon composite body therefrom are provided.
    Type: Grant
    Filed: August 28, 2015
    Date of Patent: July 23, 2019
    Assignee: Korea Institute of Energy Research
    Inventors: Ji Chan Park, Heon Jung, Ho Tae Lee, Jung Il Yang, Dong Hyun Chun, Sung Jun Hong, Seok Yong Hong
  • Patent number: 10119092
    Abstract: The presently claimed invention is directed to the novel use of polyester obtainable by reacting a mixture comprising adipic acid and an alcohol mixture comprising 1-nonanol, monomethyloctanols, dimethylheptanols and monoethylheptanols as lubricants and a lubricant composition comprising these polyesters.
    Type: Grant
    Filed: November 8, 2013
    Date of Patent: November 6, 2018
    Assignee: BASF SE
    Inventors: Markus Scherer, Boris Breitscheidel
  • Patent number: 9533925
    Abstract: A method for separating an alkyl aromatic hydrocarbon, the method having a step of adding a first diluent and an extractant having a superacid to a mixture comprising the alkyl aromatic hydrocarbon and one or more isomers thereof to carry out an acid-base extraction to thereby form a complex of the alkyl aromatic hydrocarbon with the superacid, and thereafter separating the complex from the mixture, and a step of adding an eliminating agent having a relative basicity in a range of 0.06 to 10 with respect to the alkyl aromatic hydrocarbon and a second diluent to the complex, and carrying out complex exchange of the alkyl aromatic hydrocarbon for the eliminating agent to thereby separate the alkyl aromatic hydrocarbon from the complex.
    Type: Grant
    Filed: June 25, 2013
    Date of Patent: January 3, 2017
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Junya Nishiuchi, Shinichi Nagao, Yoshitaka Tanaka, Mitsuharu Kitamura, Hiroaki Oka
  • Patent number: 9527796
    Abstract: A process for the production of dialkyl succinate from a bio-succinic acid feedstock commencing by feeding bio-succinic acid to a reaction distillation column to enable esterification of the succinic acid. The feedstock is passed co-currently with upflowing alkanol such that an esterification reaction occurs. An overhead vapor stream is removed from the reaction distillation column comprising di-ester, alkanol, water of esterification and organic components. The vapor stream is sent to an alkanol separation column where alkanol is separated from the water of esterification and organic components. A side draw is removed from the alkanol separation column comprising partially immiscible organic and aqueous phases. The side draw is passed to a phase separation apparatus where the partially immiscible organic and aqueous phases are separated. The organic phase is passed to a column where the dialkyl succinate is recovered from residual water and other organic components.
    Type: Grant
    Filed: December 2, 2014
    Date of Patent: December 27, 2016
    Assignee: Johnson Matthey Davy Technologies Limited
    Inventors: Martin Lucas Smidt, Ian Campbell, Graham Reed, Paul Gordon, Christopher Ferguson
  • Patent number: 9422226
    Abstract: The present invention describes a process for the preparation of dimethyl fumarate. The process involves the esterification of fumaric acid and methanol in the presence of sulfuric acid as an acid catalyst. The high purity dimethyl fumarate contains no more than trace amounts of dimethyl sulfate. The present invention also provides a process for the preparation of highly pure dimethyl fumarate with a particle size from 20 to 250???.
    Type: Grant
    Filed: June 8, 2012
    Date of Patent: August 23, 2016
    Assignee: Biogen MA Inc.
    Inventors: John Guzowski, William Kiesman, Erwin Irdham
  • Patent number: 9365874
    Abstract: The invention provides a method of producing acrylic acid. The method includes contacting fumaric acid with a sufficient amount of ethylene in the presence of a cross-metathesis transformation catalyst to produce about two moles of acrylic acid per mole of fumaric acid. Also provided is an acrylate ester. The method includes contacting fumarate diester with a sufficient amount of ethylene in the presence of a cross-metathesis transformation catalyst to produce about two moles of acrylate ester per mole of fumarate diester. An integrated process for process for producing acrylic acid or acrylate ester is provided which couples bioproduction of fumaric acid with metathesis transformation. An acrylic acid and an acrylate ester production also is provided.
    Type: Grant
    Filed: May 3, 2013
    Date of Patent: June 14, 2016
    Assignee: Genomatica, Inc.
    Inventors: Mark J. Burk, Priti Pharkya, Stephen J. Van Dien, Anthony P. Burgard, Christophe H. Schilling
  • Patent number: 9267015
    Abstract: Compositions containing particular branched carboxylic acid diesters obtained from a mixture of branched dinitriles exhibit especially advantageous solvating properties and thus are useful substitutes for conventional solvents, in particular halogenated solvents.
    Type: Grant
    Filed: March 2, 2007
    Date of Patent: February 23, 2016
    Assignee: RHODIA OPERATIONS
    Inventors: Philippe Marion, Lise Trouillet-Fonti, Jean-Marie Bernard
  • Patent number: 9080110
    Abstract: Method of removing metals from hydrocarbon feedstock using esters of carboxylic acids, and additives for the same, are provided, wherein hydrocarbon stream including crude oil containing metals and salts thereof, wherein metal is calcium and its salt is calcium naphthenate, is mixed with an effective metal-removing-amount of an aqueous extraction-solution of non-precipitating and non-fouling additive comprising a chemical compound selected from a group consisting of methyl or ethyl or propyl or isopropyl mono- and/or di-esters of any one of the carboxylic acids selected from the groups consisting of maleic acid, maleic anhydride, and fumaric acid, or an appropriate combination of said esters, or an appropriate combination of any of said esters with any of said carboxylic acids to form a hydrocarbonous phase and an aqueous phase containing the metal ions; and separating aqueous phase.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: July 14, 2015
    Assignee: DORF KETAL CHEMICALS (I) PRIVATE LIMITED
    Inventor: Mahesh Subramaniyam
  • Patent number: 9056829
    Abstract: This invention relates to a process for the alkoxycarbonylation of carboxylic acid functionalized alkenes or esters thereof, said process comprising: (a) reacting (i) a carboxylic acid functionalized alkene or ester thereof; (ii) a catalyst system comprising a source of Pd and a ligand, (iii) a source of anions derived from an acid with a pKa<3, (iv) carbon monoxide, and (v) a hydroxylgroup comprising compound, under conditions wherein an ester carbonylation product is produced, whereby the process is carried out in the initial presence of an ester carbonylation product. The presence of the ester carbonylation product results in stabilization of the catalyst system and prevents the formation of Pd black.
    Type: Grant
    Filed: August 31, 2012
    Date of Patent: June 16, 2015
    Assignee: DSM IP ASSETS B.V.
    Inventors: Rudy Francois Maria Jozef Parton, Michèle Catherine Christianne Janssen
  • Publication number: 20150141693
    Abstract: Disclosed are methods for the continuous flow production of acrylic acid and derivatives thereof from an epoxide feedstock. In one embodiment, the method includes the steps of: contacting a process stream comprising ethylene oxide and an organic solvent with a carbonylation catalyst and carbon monoxide to provide a reaction stream containing beta propiolactone; applying the reaction stream containing the beta propiolactone to a nanofiltration membrane to produce a permeate stream containing beta lactone and a retentate stream containing carbonylation catalyst; and treating the permeate stream under conditions to convert the beta propiolactone into an acrylate ester. In some embodiments, the retentate stream is returned to the first step of the process where it is recharged with additional epoxide and passed through the sequence again.
    Type: Application
    Filed: July 2, 2013
    Publication date: May 21, 2015
    Inventors: Scott D. Allen, Geoffrey Coates
  • Publication number: 20150080599
    Abstract: Alkyl esters (butyl, hexyl, or other) of full composition palm fatty acids, palm fatty acid distillates (PFAD), and palm kernel fatty acid distillates (PKFAD) can be used to generate polyurethane and lubricant products. The alkyl esters of the present invention can be produced via ozonolysis. The improved method for producing alkyl esters includes reacting at least one substance having at least one carbon-to-carbon double bond with ozone in the presence of least one monoalcohol that azeotropes with water. In particular, the method may comprise reacting with at least one first mole of ozone and at least one second mole of ozone, and further comprises refluxing before addition of the second mole of ozone.
    Type: Application
    Filed: February 28, 2013
    Publication date: March 19, 2015
    Applicant: PETROLIAM NASIONAL BERHAD
    Inventors: Daniel B. Garbark, Herman Paul Benecke
  • Patent number: 8957242
    Abstract: Methods, processes, apparatus, equipment and systems are disclosed for converting carboxylic acids into esters by esterification with alcohol and a dual catalyst. The method combines a homogenous and heterogeneous catalyst in one or more reactors to increase the conversion of carboxylic acids compared to using a homogenous and/or heterogeneous catalyst independently. The invention converts free fatty acids into esters by esterification with alcohol and a dual catalyst such that the reaction mixture contains sufficiently low free fatty acids and the amount of free fatty acids in the product stream leaving the process remains stable over time.
    Type: Grant
    Filed: March 11, 2014
    Date of Patent: February 17, 2015
    Assignee: Renewable Energy Group, Inc.
    Inventors: David A. Slade, Cody J. Ellens, Jared N. Brown, Anthony J. S. Pollard, Bradley Neil Albin
  • Patent number: 8956851
    Abstract: The present invention provides for novel metabolic pathways to reduce or eliminate glycerol production and increase product formation. More specifically, the invention provides for a recombinant microorganism comprising a deletion of one or more native enzymes that function to produce glycerol and/or regulate glycerol synthesis and one or more native and/or heterologous enzymes that function in one or more engineered metabolic pathways to convert a carbohydrate source, such as lignocellulose, to a product, such as ethanol, wherein the one or more native and/or heterologous enzymes is activated, upregulated, or downregulated.
    Type: Grant
    Filed: April 5, 2012
    Date of Patent: February 17, 2015
    Assignee: Lallemand Hungary Liquidity Management, LLC
    Inventors: Aaron Argyros, William Ryan Sillers, Trisha Barrett, Nicky Caiazza, Arthur J. Shaw, IV
  • Patent number: 8940923
    Abstract: Disclosed herein a process for the synthesis of diacids or diesters of general formula ROOC—(CH2)x-COOR, in which n represents an integer between 5 and 14 and R is either H or an alkyl radical of 1 to 4 carbon atoms, starting from long-chain natural monounsaturated fatty acids or esters comprising at least 10 adjacent carbon atoms per molecule, of formula CH3—(CH2)n-CHR1—CH2—CH?CH—(CH2)p-COOR, in which R represents H or an alkyl radical comprising from 1 to 4 carbon atoms, R1 is either H or OH, and n and p, which are identical or different, are indices between 2 and 11.
    Type: Grant
    Filed: July 19, 2013
    Date of Patent: January 27, 2015
    Assignee: Arkema France
    Inventor: Jean-Luc Dubois
  • Publication number: 20150018260
    Abstract: Ester polyol esters are a unique class of lubricants that have adjustable molecular weights, viscosities, and pour points based on the character of their reaction materials and relative ratios. There is provided a method for preparing at least one ester polyol ester, the method comprising esterifying an ester polyol reaction mixture to produce ester polyol, the reaction mixture comprising an ozone acid mixture and at least one primary polyol, wherein the ozone acid mixture comprises at least one dicarboxylic acid and at least one monocarboxylic acid; and capping the ester polyol with at least one capping carboxylic acid to produce ester polyol ester.
    Type: Application
    Filed: February 28, 2013
    Publication date: January 15, 2015
    Inventors: Herman Paul Benecke, Daniel B. Garbark
  • Patent number: 8921592
    Abstract: A process of producing oxalate by CO gas phase method includes the following steps: a) introducing nitrite salt, water and an inorganic acid first into a reactor I to produce a NO containing effluent I; and separating the resultant effluent to obtain the effluent II of NO; b) introducing the effluent II of NO, a C1-C4 alkanol and oxygen into a reactor II to be subjected to the reaction, and separating the resultant effluent to obtain the effluent IV of C1-C4 alkyl nitrites; c) introducing the effluent IV of C1-C4 alkyl nitrites and a CO gas stream into a coupling reactor where they are reacted to produce a NO containing effluent VI. The reactor I and/or the reactor II are preferably rotating supergravity reactors. Therefore, the process is applicable to the industrial production of oxalate by CO gas phase method.
    Type: Grant
    Filed: June 9, 2011
    Date of Patent: December 30, 2014
    Assignees: China Petroleum & Chemical Corporation, Shanghai Research Institute of Petrochemical Technology, SINOPEC
    Inventors: Weimin Yang, Juntao Liu, Wanmin Wang, Lei Li
  • Patent number: 8889898
    Abstract: The invention relates to a process for preparing (2,3) disubstituted succinates that allows (2,3) disubstituted succinates to be obtained in good purity and with acceptable reaction yields. The (2) and (3) substitutions may be the same or different. The process comprises reacting a haloacetate with a malonic acid ester into a tricarboxylate, which is further reacted to a (2,3) disubstituted tricarboxylate, hydrolyzed, decarboxylated and optionally esterified. Esterified (2,3) disubstituted succinic esters may be used as internal donor in Ziegler-Natta type catalysts for the polymerization of olefins.
    Type: Grant
    Filed: August 23, 2012
    Date of Patent: November 18, 2014
    Assignee: Saudi Basic Industries Corporation
    Inventors: Jaiprakash Brijlal Sainani, Mahesh Davadra
  • Publication number: 20140336406
    Abstract: A process for preparing metal alkoxides starting with a metal chloride and esters of either succinic acid or glutaric acid to produce metal alkoxide, an acid anhydride and alkyl chloride. Esterification of the acid anhydride with alcohol regenerates the ester of organic acid. The first step is carried out under anhydrous conditions. By regenerating the organic acid esters in the process, the only byproduct is an alkyl chloride.
    Type: Application
    Filed: May 8, 2013
    Publication date: November 13, 2014
    Inventor: John E. STAUFFER
  • Patent number: 8871968
    Abstract: The present invention relates to a process of producing oxalate by CO gas phase method for chiefly solving the technical problem of the low utilization efficiency of nitrogen oxides or nitrous acid esters in the prior art.
    Type: Grant
    Filed: April 13, 2011
    Date of Patent: October 28, 2014
    Assignees: China Petroleum & Chemical Corporation, Shanghai Research Institute of Petrochemical Technology Sinopec
    Inventors: Juntao Liu, Fengxia Sun, Jun Kuai
  • Publication number: 20140309435
    Abstract: The invention provides a process for preparing esters from formates and olefinically unsaturated compounds with catalysts based on palladium compounds. In addition, the invention discloses a polyphasic reaction mixture and nonyl methyl ester mixtures prepared by the process according to the invention.
    Type: Application
    Filed: December 17, 2012
    Publication date: October 16, 2014
    Applicant: EVONIK INDUSTRIES AG
    Inventors: Robert Franke, Dieter Hess, Matthias Beller, Ralf Jackstell, Daniela Cozzula, Ivana Fleischer, Reiko Jennerjahn
  • Publication number: 20140310827
    Abstract: A novel microalgal strain whose lipid production has been enhanced compared to the wild type. The lipid content produced by the microalgae is particularly rich in neutral lipids. The use of the microalgal strain and the lipids are also described.
    Type: Application
    Filed: August 16, 2012
    Publication date: October 16, 2014
    Applicant: INSTITUT FRANCAIS DE RECHERCHE POUR L'EXPLOITATION DE LA MER (IFREMER)
    Inventors: Nolween Dubois, Jean-Paul Cadoret, Gael Bougaran, Catherine Rouxel, Sophie Doulin
  • Publication number: 20140296564
    Abstract: The invention belongs to the technical field of preparing oxalate in coal to ethylene glycol, aiming at providing a preparation process for nanocatalysts with (111) crystal facet exposed and a process for vapour-phase CO oxidative coupling to oxalate. The nanocatalysts with (111) crystal facet exposed comprise carrier, active component and promoter on the carrier, wherein, in term of the weight of the carrier, the active component accounts for 0.05-2% of the weight of the carrier, the weight percentage of metal elements in the promoter is 20% or less. The nanocatalysts with (111) crystal facet exposed are prepared by the nanometals in situ supporting process. The preparation process is simple in procedure, has low energy consumption and can precisely control the size and exposed crystal facet of the active component nanoparticles. The obtained nanocatalysts with (111) crystal facet exposed are highly active for vapour-phase CO oxidative coupling to oxalate at a lower loading of noble metal.
    Type: Application
    Filed: June 10, 2014
    Publication date: October 2, 2014
    Inventors: Zhongning Xu, Guocong Guo, Mingsheng Wang, Yuangen Yao
  • Publication number: 20140275612
    Abstract: Methods, processes, apparatus, equipment and systems are disclosed for converting carboxylic acids into esters by esterification with alcohol and a dual catalyst. The method combines a homogenous and heterogeneous catalyst in one or more reactors to increase the conversion of carboxylic acids compared to using a homogenous and/or heterogeneous catalyst independently. The invention converts free fatty acids into esters by esterification with alcohol and a dual catalyst such that the reaction mixture contains sufficiently low free fatty acids and the amount of free fatty acids in the product stream leaving the process remains stable over time.
    Type: Application
    Filed: March 11, 2014
    Publication date: September 18, 2014
    Applicant: Renewable Energy Group, Inc.
    Inventors: David A. Slade, Cody J. Ellens, Jared N. Brown, Anthony J.S. Pollard, Bradley Neil Albin
  • Publication number: 20140206896
    Abstract: The present disclosure is a method and system for production of oxalic acid and oxalic acid reduction products. The production of oxalic acid and oxalic acid reduction products may include the electrochemical conversion of CO2 to oxalate and oxalic acid. The method and system for production of oxalic acid and oxalic acid reduction products may further include the acidification of oxalate to oxalic acid, the purification of oxalic acid and the hydrogenation of oxalic acid to produce oxalic acid reduction products.
    Type: Application
    Filed: March 20, 2014
    Publication date: July 24, 2014
    Applicant: Liquid Light, Inc.
    Inventors: Narayanappa Sivasankar, Robert Farrauto, Robert Augustine, Setrak Tanielyan, Mohanreddy Kasireddy, Emily Barton Cole, Kate A. Keets, Rishi Parajuli, Jerry J. Kaczur, Yizu Zhu, Farah Dhun, Kyle Teamey, Alexander Bauer, Theodore J. Kramer, Paul Majsztrik, George Leonard
  • Publication number: 20140206893
    Abstract: This invention relates to a process for the alkoxycarbonylation of carboxylic acid functionalized alkenes or esters thereof, said process comprising: (a) reacting (i) a carboxylic acid functionalized alkene or ester thereof; (ii) a catalyst system comprising a source of Pd and a ligand, (iii) a source of anions derived from an acid with a pKa<3, (iv) carbon monoxide, and (v) a hydroxylgroup comprising compound, under conditions wherein an ester carbonylation product is produced, whereby the process is carried out in the initial presence of an ester carbonylation product. The presence of the ester carbonylation product results in stabilization of the catalyst system and prevents the formation of Pd black.
    Type: Application
    Filed: August 31, 2012
    Publication date: July 24, 2014
    Applicant: DSM IP ASSETS B.V.
    Inventors: Rudy Francois Maria Jozef Parton, Michèle Catherine Christianne Janssen
  • Publication number: 20140206895
    Abstract: The present disclosure is a method and system for production of oxalic acid and oxalic acid reduction products. The production of oxalic acid and oxalic acid reduction products may include the electrochemical conversion of CO2 to oxalate and oxalic acid. The method and system for production of oxalic acid and oxalic acid reduction products may further include the acidification of oxalate to oxalic acid, the purification of oxalic acid and the hydrogenation of oxalic acid to produce oxalic acid reduction products.
    Type: Application
    Filed: March 20, 2014
    Publication date: July 24, 2014
    Applicant: Liquid Light, Inc.
    Inventors: Zbigniew Twardowski, Emily Barton Cole, Jerry J. Kaczur, Kyle Teamey, Kate A. Keets, Rishi Parajuli, Alexander Bauer, Narayanappa Sivasankar, George Leonard, Theodore J. Kramer, Paul Majsztrik, Yizu Zhu
  • Publication number: 20140206894
    Abstract: The present disclosure is a method and system for production of oxalic acid and oxalic acid reduction products. The production of oxalic acid and oxalic acid reduction products may include the electrochemical conversion of CO2 to oxalate and oxalic acid. The method and system for production of oxalic acid and oxalic acid reduction products may further include the acidification of oxalate to oxalic acid, the purification of oxalic acid and the hydrogenation of oxalic acid to produce oxalic acid reduction products.
    Type: Application
    Filed: March 20, 2014
    Publication date: July 24, 2014
    Applicant: Liquid Light, Inc.
    Inventors: Emily Barton Cole, Jerry J. Kaczur, Kyle Teamey, Kate A. Keets, Rishi Parajuli, Alexander Bauer, Narayanappa Sivasankar, George Leonard, Theodore J. Kramer, Paul Majsztrik, Yizu Zhu, Robert Farrauto, Robert Augustine, Setrak Tanielyan, Mohanreddy Kasireddy
  • Publication number: 20140200363
    Abstract: The present invention describes a process for the preparation of dimethyl fumarate. The process involves the esterification of fumaric acid and methanol in the presence of sulfuric acid as an acid catalyst. The high purity dimethyl fumarate contains no more than trace amounts of dimethyl sulfate. The present invention also provides a process for the preparation of highly pure dimethyl fumarate with a particle size from 20 to 250???.
    Type: Application
    Filed: June 8, 2012
    Publication date: July 17, 2014
    Applicant: Biogen IDEC MA Inc.
    Inventors: John Guzowski, William Kiesman, Erwin Irdam
  • Publication number: 20140194647
    Abstract: The invention relates to a process for preparing (2,3) disubstituted succinates that allows (2,3) disubstituted succinates to be obtained in good purity and with acceptable reaction yields. The (2) and (3) substitutions may be the same or different. The process comprises reacting a haloacetate with a malonic acid ester into a tricarboxylate, which is further reacted to a (2,3) disubstituted tricarboxylate, hydrolysed, decarboxylated and optionally esterified. Esterified (2,3) disubstituted succinic esters may be used as internal donor in Ziegler-Natta type catalysts for the polymerisation of olefins.
    Type: Application
    Filed: August 23, 2012
    Publication date: July 10, 2014
    Applicant: Saudi Basic Industries Corporation
    Inventors: Jaiprakash Brijlal Sainani, Mahesh Davadra
  • Patent number: 8772532
    Abstract: Provided are processes for the production of (meth)acrylic esters of polyols, in which for 80 mol % or more of the esters, all of the OH groups of the polyols are esterified. Certain processes relate to reaction of polyols with acrylic acid and/or methacrylic acid in the presence of acidic esterification catalysts and in the presence of polymerization inhibitors, operating with reaction mixtures which are liquid at reaction temperature and are free from nonreacting solvents and/or azeotropic entrainers, the resultant water of condensation being stripped from the gas phase of the reaction space, and the (meth)acrylic acid is metered in three or more portions.
    Type: Grant
    Filed: August 2, 2012
    Date of Patent: July 8, 2014
    Assignee: Cognis IP Management GmbH
    Inventors: Juergen Baro, Jean-Marc Ballin
  • Patent number: 8729295
    Abstract: The present invention provides methods of using a novel sulfonated resin catalyst, showing improved performance. The catalyst has reduced or partial functionalization, throughout the sulfonated region of the polymer, leading to reduced by-product formation and other desirable features. This catalyst has particular usefulness in reactions or processes sensitive to high acidity, e.g., esterification-transesterification.
    Type: Grant
    Filed: October 24, 2008
    Date of Patent: May 20, 2014
    Assignee: The Purolite Company
    Inventors: James A. Dale, Luc Froment, Satish Bapat
  • Publication number: 20140128631
    Abstract: The invention relates to a carbonylation process for the preparation of an alkanoic acid ester comprising reacting: (a) an alkene; (b) a source of Pd; (c) a bidentate phosphine ligand of formula I; R1R2P—R3—R—R4—PR5R6??(I) wherein P represents a phosphorus atom; R1, R2, R5 and R6 can independently represent the same or different optionally substituted organic groups containing a tertiary carbon atom through which the group is linked to the phosphorus atom; R3 and R4 independently represent optionally substituted lower alkylene groups and R represents an optionally substituted aromatic group; (d) a source of anions derived from an acid with a pKa<3; (e) carbon monoxide; and (f) an alkanol; characterized in that the process is performed in the presence of between 0.1 and 3 wt water.
    Type: Application
    Filed: March 30, 2012
    Publication date: May 8, 2014
    Applicant: DSM IP ASSETS B.V.
    Inventors: Johannes Gerardus De Vries, Natascha Sereinig, Elisabeth Wilhelmina Maria Van De Vondervoort, Michele Catherine Christianne Janssen
  • Publication number: 20140031490
    Abstract: The invention relates to a mixture of glycerol, mono-, di- and triacetylglycerolester in which the amount of tri-ester is less than 15 mol %, the amount of glycerol is less than 25 mol %, the amount of monoester is about 20 mol % or more, more preferred about 30 mol % or more and the amount of diester is about 20 mol % or more preferred about 40 mol % or more. The invention further relates to methods to prepare such glycerolacetylester mixtures, and to the use thereof in the preparation of unsaturated polyesters. Polyesters comprising said glycerolacetylester mixtures are made from a higher amount of raw materials than obtainable from renewable resources.
    Type: Application
    Filed: April 4, 2012
    Publication date: January 30, 2014
    Applicants: WAIKATOLINK LIMITED, NUPLEX RESINS B.V.
    Inventors: Kim Pickering, Carmen Viljoen, Casparus Johannes Reinhard Verbeek, Christopher Brian King
  • Patent number: 8598303
    Abstract: The invention provides a process for the preparation of valerolactone, said process comprising reacting levulinic acid with hydrogen by using a solid Ru catalyst, characterized in that the process is carried out in the presence of at least 0.08% (w/w) water relative to the amount of levulinic acid. Said process may be faster and more selective. This process advantageously allows the production of valerolactone from renewable sources. The valerolactone may be used in the preparation of methylpentenoate, adipic acid dimethylester, adipic acid, hexamethylenediamine, and polyamide 6,6 (all claimed).
    Type: Grant
    Filed: June 20, 2012
    Date of Patent: December 3, 2013
    Assignee: DSM IP Assets B.V.
    Inventors: Anna Maria Cornelia Francisca Castelijns, Michele Catherine Christianne Janssen, Henricus Wilhemus Leonardus Marie Vaessen
  • Patent number: 8586519
    Abstract: The present invention is generally directed to the present invention provides for multi-grade engine oil formulations comprising a diester component, wherein the diester component comprises vicinal diester species, and wherein at least a portion of said diester component is bio-derived. Many such formulations of the present invention are expected to favorably compete with similar, existing formulations comprising synthetic esters, but such formulations are generally expected to meet or exceed such existing formulations in a number of areas including, but not limited to, economics, biodegradability, and/or toxicity.
    Type: Grant
    Filed: August 26, 2009
    Date of Patent: November 19, 2013
    Assignee: Chevron U.S.A. Inc.
    Inventors: Stephen Joseph Miller, Saleh A. Elomari, Zhen Zhou
  • Publication number: 20130303796
    Abstract: A method for continuously preparing a carboxylic acid ester is disclosed. In the method of the present invention, a vertical reactor is filled with a solid catalyst, a carboxylic acid and an alcohol are introduced into a lower part of the vertical reactor, esterification is performed to form an esterized mixture, the esterized mixture is output from an upper part of the vertical reactor, and distillation is performed to isolate the carboxylic acid ester. The method of the present invention is simple, easily controlled and environmental friendly, and has significantly high conversion rate and selectivity.
    Type: Application
    Filed: October 15, 2012
    Publication date: November 14, 2013
    Applicant: China Petrochemical Development Corporation, Taipei (Taiwan)
    Inventors: Jih-Dar Hwang, Yung-Shun Kung, Yao-Ching Tsai
  • Publication number: 20130289278
    Abstract: Disclosed embodiments relate to improved methods for the synthesis of activated fumarate intermediates and their use in chemical synthesis. Disclosed embodiments describe the synthesis of activated fumarate esters including those derived from activating groups including: 4-nitrophenyl, diphenylphosphoryl azide, pivaloyl chloride, chlorosulfonyl isocyanate, p-nitrophenol, MEF, trifluoroacetyl and chlorine, for example, ethyl fumaroyl chloride and the subsequent use of the activated ester in situ. Further embodiments describe the improved synthesis of substituted aminoalkyl-diketopiperazines from unisolated and unpurified intermediates allowing for improved yields and reactor throughput.
    Type: Application
    Filed: March 15, 2013
    Publication date: October 31, 2013
    Applicant: MANNKIND CORP
    Inventors: Kelly Sullivan Kraft, John J. Freeman, Paul Serwinski, Vinnie Pavia, Otto Phanstiel, IV, Navneet Kaur
  • Publication number: 20130289301
    Abstract: Mixture of triglycerides obtained from vegetable oils comprising one or more of the following oligomeric structures: R4—[O—C(O)—R1—C(O)—O—CH2—CH(OR2)—CH2]n—O—R3 wherein R1 is selected from C2-C22 alkylenes, R2 is selected from one or more of the following groups consisting of C6-C24 dicarboxylic acid residues and C6-C24 monocarboxylic acid residues, R3 is selected from one or more of the following groups consisting of H, C6-C24 dicarboxylic acid residues and C6-C24 monocarboxylic acid residues, R4 is an alkyl group, n is an integer greater than or equal to 2, said C6-C24 dicarboxylic acid residues of R2 and R3 being esterified with monoalcohols and said mixture of triglycerides having a Numerical Average Molecular Weight (Mn) of between 800 and 10.000 Da.
    Type: Application
    Filed: December 20, 2011
    Publication date: October 31, 2013
    Applicant: NOVAMONT S.p.A.
    Inventors: Catia Bastioli, Luigi Capuzzi, Paolo Magistrali, Sebastia Gesti' Garcia
  • Patent number: 8552080
    Abstract: Polyurethane foams are prepared from polyester polyols obtained by reaction of diols with a mixture of diacids derived from a mixture of dinitrile compounds obtained as by-products in the manufacture of adiponitrile by hydrocyanation of butadiene.
    Type: Grant
    Filed: January 22, 2009
    Date of Patent: October 8, 2013
    Assignee: Rhodia Operations
    Inventors: Jean-Claude Masteau, Edson Leme Rodrigues
  • Publication number: 20130197265
    Abstract: The present invention relates to a process of producing oxalate by CO gas phase method for chiefly solving the technical problem of the low utilization efficiency of nitrogen oxides or nitrous acid esters in the prior art.
    Type: Application
    Filed: April 13, 2011
    Publication date: August 1, 2013
    Applicants: SHANGHAI RESEARCH INSTITUTE OF PETROCHEMICAL TECHNOLOGY SINOPEC, CHINA PETROLEUM & CHEMICAL CORPORATION
    Inventors: Juntao Liu, Fengxia Sun, Jun Kuai
  • Publication number: 20130190217
    Abstract: According to a first aspect, an ester oil, in particular for producing a hydraulic fluid and/or a lubricant, containing an esterification product from the esterification of at least one monoalcohol with at least one polycarboxylic acid, is characterized in that the monoalcohol and/or the polycarboxylic acid originates from renewable raw materials. According to a second aspect, an ester oil, in particular for producing a hydraulic fluid and/or a lubricant, containing an esterification product from the esterificati-on of at least one monocarboxylic acid with at least one dialcohol, is characterized in that the dialcohol and/or the monocarboxylic acid originates from renewable raw materials.
    Type: Application
    Filed: August 25, 2011
    Publication date: July 25, 2013
    Applicant: PANOLIN Holding AG
    Inventors: Patrick Lämmle, Bernardo Walterspiel, Mathias Woydt
  • Publication number: 20130172598
    Abstract: The present invention relates to a process for preparing ethylene glycol dimethacrylate, which comprises transesterification of ethylene glycol with an ester of methacrylic acid in the presence of catalysts, wherein a combination comprising lithium amide (LiNH2) and lithium chloride (LiCl) is used as catalyst. The process of the invention makes it possible to prepare ethylene glycol dimethacrylate particularly inexpensively and in a very high purity.
    Type: Application
    Filed: May 8, 2008
    Publication date: July 4, 2013
    Applicant: Evonik Roehm GmbH
    Inventors: Joachim Knebel, Thorben Schuetz, Guido Protzmann, Harald Trauthwein, Guenther Lauster, Thomas Kehr, Gerhard Koelbl, Guenter Westhaeuser
  • Publication number: 20130158286
    Abstract: This invention relates to a process for the preparation of alkenoic acid esters comprising contacting a lactone with an alcohol and an acidic heterogeneous catalyst, characterised in that the process is carried out in the presence of at least 20 ppm of an acid having a pKa of 5 or less, relative to the amount of the lactone. The presence of at least 20 ppm of an acid having a pKa of 5 or less may stabilise the catalyst during the reaction and may also be used for reactivating an acidic heterogeneous catalyst. The improved yield advantageously allows energy conservation.
    Type: Application
    Filed: December 20, 2012
    Publication date: June 20, 2013
    Applicant: DSM IP ASSETS B.V.
    Inventor: DSM IP ASSETS B.V.
  • Publication number: 20130125907
    Abstract: A method for producing triethyl citrate from one or more plants of genus Nicotiana is provided. The triethyl citrate can be derived inter alia from Nicotiana species biomass or from seed. In certain embodiments, the triethyl citrate is produced by condensation of ethanol, generated by fermentation of starting material derived from tobacco biomass or seed, and citric acid, also derived from tobacco biomass or seed. The invention also provides articles and compositions including tobacco articles and tobacco compositions that include triethyl citrate produced from one or more plants of genus Nicotiana.
    Type: Application
    Filed: November 17, 2011
    Publication date: May 23, 2013
    Inventors: Michael Francis Dube, William Coleman
  • Publication number: 20130131247
    Abstract: The present invention relates to a thermoplastic composition comprising a) at least one thermoplastic polymer, b) at least one lubricant, and c) optionally further additives, the lubricant being a reaction mixture which is obtainable by the reaction of a component comprising saturated triglycerides with a primary alcohol. The present invention also relates to a process for preparing a thermoplastic composition, to the thermoplastic composition obtainable by this process, to a process for producing a moulding based on a thermoplastic composition, to a moulding obtainable by this process, and to the use of a reaction mixture.
    Type: Application
    Filed: August 1, 2011
    Publication date: May 23, 2013
    Applicant: EMERY OLEOCHEMICALS GMBH
    Inventors: Peter Daute, Thomas Schweichler
  • Patent number: 8440072
    Abstract: Method of removing metals from hydrocarbon feedstock using esters of carboxylic acids, and additives for the same, are provided, wherein hydrocarbon stream including crude oil containing metals and salts thereof, wherein metal is calcium and its salt is calcium naphthenate, is mixed with an effective metal-removing-amount of an aqueous extraction-solution of non-precipitating and non-fouling additive comprising a chemical compound selected from a group consisting of methyl or ethyl or propyl or isopropyl mono- and/or di-esters of any one of the carboxylic acids selected from the groups consisting of maleic acid, maleic anhydride, and fumaric acid, or an appropriate combination of said esters, or an appropriate combination of any of said esters with any of said carboxylic acids to form a hydrocarbonous phase and an aqueous phase containing the metal ions; and separating aqueous phase.
    Type: Grant
    Filed: July 24, 2009
    Date of Patent: May 14, 2013
    Assignee: Dorf Ketal Chemicals (I) Private Limited
    Inventor: Mahesh Subramaniyam
  • Patent number: 8425628
    Abstract: Reacting an alkylene carbonate, such as ethylene carbonate, with dimer acid in the presence of a catalyst, such as a tertiary amine catalyst, gives a dimer acid diester having essentially no sulfur, and thus may be added to ultra-low sulfur diesel fuel downstream of a refinery. The diester enhances the lubricity properties of hydrocarbon fuels, increases their service life and fuel efficiency. The manufacturing process time may be decreased significantly compared with a process using ethylene glycol instead of ethylene carbonate, and much less ethylene glycol by-product results.
    Type: Grant
    Filed: August 29, 2012
    Date of Patent: April 23, 2013
    Assignee: Baker Hughes Incorporated
    Inventors: Viet Q. Hoang, Philip L. Leung, Gordon T. Rivers
  • Publication number: 20130079549
    Abstract: A process of producing oxalate by CO gas phase method includes the following steps: a) introducing nitrite salt, water and an inorganic acid first into a reactor I to produce a NO containing effluent I; and separating the resultant effluent to obtain the effluent II of NO; b) introducing the effluent II of NO, a C1-C4 alkanol and oxygen into a reactor II to be subjected to the reaction, and separating the resultant effluent to obtain the effluent IV of C1-C4 alkyl nitrites; c) introducing the effluent IV of C1-C4 alkyl nitrites and a CO gas stream into a coupling reactor where they are reacted to produce a NO containing effluent VI. The reactor I and/or the reactor II are preferably rotating supergravity reactors. Therefore, the process is applicable to the industrial production of oxalate by CO gas phase method.
    Type: Application
    Filed: June 9, 2011
    Publication date: March 28, 2013
    Applicants: Shanghai Research Institute of Petrochemical Technology, Sinopec, China Petroleum & Chemical Corporation
    Inventors: Weimin Yang, Juntao Liu, Wanmin Wang, Lei Li
  • Publication number: 20130079548
    Abstract: This invention relates to a process for the preparation of alkenoic acid esters comprising contacting a lactone with an alcohol and an acidic catalyst in the gas phase, characterised in that the process is carried out in the presence of at least 0.26 wt. % water, relative to the amount of the lactone. The process may result in a good production yield and selectivity with respect to the production of alkenoic acid esters and may also result in less formation of dialkylethers. The improved yield advantageously allows energy conservation.
    Type: Application
    Filed: September 21, 2012
    Publication date: March 28, 2013
    Applicant: DSM IP ASSETS B.V.
    Inventor: DSM IP ASSETS B.V.