Epoxidation At Site Of Ethylenic Unsaturation Patents (Class 549/523)
  • Patent number: 11952357
    Abstract: The present disclosure relates to the field of epoxide resin, and more particularly to an epoxide with a low total chlorine content and no heavy metal residues, and a preparation method thereof. Disclosed is an epoxide prepared from raw materials including an unsaturated cycloaliphatic compound containing a double bond, hydrogen peroxide, an organic acid compound, a solvent and an alkaline salt; wherein a molar ratio of the organic acid compound to the unsaturated cycloaliphatic compound containing a double bond is (1-1.5):1. The obtained epoxides obtained in the present disclosure have a high purity, a high yield, a low solvent content, low chroma, and a low chlorine and metal ion content; the reaction system is simple, environmentally friendly, safe and controllable, and the production cost is low, which can meet the technical and economic requirements and are suitable for large-scale industrial production.
    Type: Grant
    Filed: September 17, 2020
    Date of Patent: April 9, 2024
    Assignee: JIANGSU TETRA NEW MATERIAL TECHNOLOGY CO., LTD.
    Inventors: Jianwei Han, Quan Jia, Yangjun Chang, Xiangming Cao
  • Patent number: 11932615
    Abstract: Ethylene oxide purification by quenching and washing ethylene oxide reactor effluent prior to passing the gaseous ethylene oxide-containing stream to an ethylene oxide absorber to form a dilute aqueous ethylene oxide and carbon dioxide solution and thereafter stripping that solution in an EO stripper to produce a gaseous ethylene oxide and carbon dioxide-containing overhead vapor which is then passed to a reabsorber wherein the ethylene oxide and part of the carbon dioxide vapors are absorbed to form an aqueous reabsorbate solution from which carbon dioxide is removed to produce an ethylene oxide-containing solution is improved by passing an impurities-containing liquid bleed stream obtained from the quench wash to a second, small quench bleed stripper where steam and carbon dioxide are added and gaseous overhead from that quench bleed stripper is passed to the reabsorber for recovery of the EO and removal of formaldehyde and other impurities.
    Type: Grant
    Filed: May 14, 2019
    Date of Patent: March 19, 2024
    Inventor: Brian Ozero
  • Patent number: 11724976
    Abstract: An improved process for the recovery of high-purity ethylene-oxide water feed streams to EO purification and MEG reaction units when both are operating in EO plants that incorporate EO Stripper bypass technology, by installing a second lights stripper to exclusively degasify the diluted EO feed to the MEG reactor, thus permitting the use of additional bypassed (gasified) EO absorbate as the diluent and resulting in a substantial increase in the total amount of EO absorbate that can bypass the EO Stripper.
    Type: Grant
    Filed: November 30, 2022
    Date of Patent: August 15, 2023
    Assignees: Petron Scientech, Inc., Scientech Associates Inc.
    Inventor: Brian J. Ozero
  • Patent number: 11708341
    Abstract: The present invention provides new methods for preparing compound 5, and pharmaceutically acceptable salts thereof, of structure Compound 5, or a pharmaceutically acceptable salt thereof, is an important intermediate in the synthesis of carfilzomib. The invention further provides methods of making a useful manganese catalyst that may be used in the epoxidation step of the present invention.
    Type: Grant
    Filed: August 3, 2017
    Date of Patent: July 25, 2023
    Inventors: Matthew Beaver, Sheng Cui, Xiangqing Shi
  • Patent number: 11255604
    Abstract: A process for removing light components from an ethylene stream may include providing a dried ethylene stream containing ethylene, ethane, CO, CO2, H2, CH4, and C3+ hydrocarbons. The process may include sending the dried ethylene stream to a stripper to produce an overhead stream containing ethylene, CO, H2 and CH4, and a bottom stream containing ethylene, ethane, CO2, and C3+ hydrocarbons. The gaseous phase on top of the stripper may be condensed in a heat exchanger cooled by a refrigerant stream to get a first gaseous phase and a first liquid phase. The first gaseous phase may be condensed in a heat exchanger cooled by liquid ethane or liquid ethylene to get a second gaseous phase containing ethylene CO, H2 and CH4 and a second liquid phase. The first and second liquid phases may be the reflux of the stripper.
    Type: Grant
    Filed: August 21, 2018
    Date of Patent: February 22, 2022
    Assignee: Total Research & Technology Feluy
    Inventors: Walter Vermeiren, Catherine Boutrot, Manuela Arratia
  • Patent number: 11104686
    Abstract: The present invention discloses a composition comprising at least one or more stereoisomers of a compound represented by the following Formula (1), wherein, in a gas chromatogram obtained by analyzing the composition by gas chromatography, the ratio of the area of the maximum peak with respect to the total area of peaks derived from the stereoisomers is 90% or more. The present invention also discloses: a curable composition comprising the above described composition, and one selected from the group consisting of a thermal cationic polymerization initiator, an acid anhydride-based curing agent and a curing accelerator, and a photo-cationic polymerization initiator; as well as a cured product therefrom. The above described curable composition is useful in that it allows for the production of a cured product having a high heat resistance. (In the Formula (1), R1 to R18 are each independently selected from the group consisting of a hydrogen atom, an alkyl group and an alkoxy group.).
    Type: Grant
    Filed: June 8, 2017
    Date of Patent: August 31, 2021
    Assignee: ENEOS Corporation
    Inventors: Shohei Takata, Ryuichi Ueno, Hisashi Sone, Atsushi Kameyama
  • Patent number: 10954205
    Abstract: In a process for the oxidation of a lower alkene, such as ethylene, over a catalyst containing Cu and one or more zeolite or zeotype materials, the oxidation is conducted in the presence of ammonia in the feed gas at a process temperature below 350° C. The oxidation can be performed in a continuous process.
    Type: Grant
    Filed: June 7, 2018
    Date of Patent: March 23, 2021
    Assignee: HALDOR TOPSØE A/S
    Inventors: Pablo Beato, Ton V. W. Janssens
  • Patent number: 10898887
    Abstract: In one example, a method for converting a first compound into a second compound is provided. The method includes providing the first compound in an entrance of a flow through reactor, wherein the entrance comprises a first catalyst and an oxidant, converting the first compound and the oxidant into the second compound as the first compound and the oxidant contact the first catalyst in the entrance of the flow through reactor while moving towards a tail end of the flow through reactor, and converting the first compound and the oxidant into the second compound via a solid catalyst comprising a white crystalline solid with a titanium content of about 0.5 to about 1.5 weight percent (wt %) in the tail end of the flow through reactor.
    Type: Grant
    Filed: August 22, 2017
    Date of Patent: January 26, 2021
    Assignee: THE REGENTS OF THE UNIVERSITY OF CALIFORNIA
    Inventors: Alexander Okrut, Alexander Katz
  • Patent number: 10781146
    Abstract: The object of the present invention is to provide a process for preparing a 5-alken-1-yne compound efficiently at low costs and a process for preparing (2E,6Z)-2,6-nonadienal by making use of the aforesaid process for preparing the 5-alken-1-yne compound. There is provided a process for preparing a 5-alken-1-yne compound of the following formula (4): Y—Z—CR1?CR2—(CH2)2—C?CH (4) in which Y in formula (4) represents a hydrogen atom or a hydroxyl group, the process comprising at least steps of: subjecting (i) an alkenylmagnesium halide compound prepared from a haloalkene compound of the following formula (1): Y—Z—CR1?CR2—(CH2)2—X1 (1) and (ii) an alkyne compound of the following formula (2): X2—C?C—Si(R3)(R4)(R5) (2) to a coupling reaction to form a silane compound of the following formula (3): Y—Z—CR1?CR2—(CH2)2—C?C—Si(R3)(R4)(R5) (3); and subjecting the silane compound (3) to a desilylation reaction to form the 5-alken-1-yne compound (4).
    Type: Grant
    Filed: August 6, 2019
    Date of Patent: September 22, 2020
    Assignee: Shin-Etsu Chemical Co., Ltd.
    Inventors: Tomohiro Watanabe, Takeshi Kinsho, Yuki Miyake
  • Patent number: 10549261
    Abstract: MOFs are disclosed that can efficiently adsorb oxygen from a gas stream, such as air. Systems and methods are also disclosed that utilize MOFs to separate oxygen from a gas stream. The separated oxygen may be used in a commercial process such as a combustion process.
    Type: Grant
    Filed: May 20, 2019
    Date of Patent: February 4, 2020
    Assignee: National Technology & Engineering Solutions of Sandia, LLC
    Inventors: Tina M. Nenoff, Dorina Florentina Sava Gallis, Marie Vernell Parkes, Jeffery Greathouse
  • Patent number: 10508032
    Abstract: Catalysts, catalytic systems and related synthetic methods for in situ production of H2O2 and use thereof in reaction with oxidizable substrates.
    Type: Grant
    Filed: March 18, 2016
    Date of Patent: December 17, 2019
    Assignee: Northwestern University
    Inventors: Kimberly A. Gray, Justin M. Notestein, Todd R. Eaton
  • Patent number: 10486111
    Abstract: A separation membrane structure includes a porous support, a first separation membrane and a second separation membrane. The first separation membrane is formed on the porous support and contains high silica zeolite having Si/Al atomic ratio of greater than or equal to 200. The second separation membrane is formed on the first separation membrane and contains cation.
    Type: Grant
    Filed: April 24, 2017
    Date of Patent: November 26, 2019
    Assignee: NGK Insulators, Ltd.
    Inventors: Makoto Miyahara, Kenichi Noda, Makiko Ichikawa, Takeshi Hagio
  • Patent number: 10335772
    Abstract: A catalyst comprising gold and a porous support containing at least one refractory oxide, in which the gold content is in the range 0.01% to 5% by weight with respect to the total weight of catalyst, and in which the particles of gold are distributed homogeneously through said porous support and have a dimension, measured by transmission electron microscopy, in the range 0.5 to 5 nm.
    Type: Grant
    Filed: February 9, 2016
    Date of Patent: July 2, 2019
    Assignee: IFP Energies Nouvelles
    Inventors: Amandine Cabiac, Antoine Hugon
  • Patent number: 10232359
    Abstract: An abbreviated, energy efficient and manipulative process and recipe using a novel binder-combination, to custom-make shaped TS-1 product wherein, their physico-chemical attributes can be engineered, variegated or optimized independent of one another, according to specific stipulations for diverse catalytic reactions that employ them.
    Type: Grant
    Filed: March 25, 2014
    Date of Patent: March 19, 2019
    Assignee: SÜD-CHEMIE INDIA PVT LTD.
    Inventors: Arshia Altaf Lalljee, Rikeshchandra Sharadchandra Joshi, Rajeshkumar Manubhai Patel, Dhananjay Prabhakar Sabde
  • Patent number: 10221110
    Abstract: A process for dehydrating alkanes in which such feedstock mixtures may be used having a high proportion of olefins, i.e. approximately 1% by weight to 10% by weight. Specifically, alkenes having two to five carbon atoms are generated from alkanes having the same carbon length where the number of carbon atoms not change during by the dehydrogenation. The process is intended to be feasible on an industrial scale. A basic concept of the invention consists of hydrogenating alkenes present in the feedstock to the corresponding alkanes before they come in contact with the dehydrogenation catalyst. This avoids an undesired coke deposit. The hydrogenation is effected by minimal addition of hydrogen (80% to 120% of the stoichiometrically required amount). The hydrogenation is effected either over a dehydrogenation catalyst, or over the dehydrogenation catalyst itself.
    Type: Grant
    Filed: November 30, 2017
    Date of Patent: March 5, 2019
    Assignee: EVONIK DEGUSSA GMBH
    Inventors: Guido Stochniol, Robert Franke
  • Patent number: 10029240
    Abstract: Disclosed herein is a simple process for functionalization/grafting of carbon microspheres obtained from bagasse with various active functional groups onto it and use of the same as catalyst for various organic reactions, having very high selectivity and conversion rate.
    Type: Grant
    Filed: June 25, 2014
    Date of Patent: July 24, 2018
    Assignee: COUNCIL OF SCIENTIFIC AND INDUSTRIAL RESEARCH
    Inventors: Ankush Venkatrao Biradar, Shubhangi Bhalchandra Umbarkar, Mohan Keraba Dongare
  • Patent number: 9533282
    Abstract: A process for the separation of a gas from a gas stream using metal organic framework that is reversibly switchable between a first conformation that allows the first gas species to be captured in the metal organic framework, and a second conformation that allows the release of the captured first gas species, using light as the switching stimulus. The metal organic framework may comprise a metal and one or more ligands, in which the ligands contain an isomerizable group within the molecular chain that forms a link between adjacent metal atoms in the metal organic framework.
    Type: Grant
    Filed: July 26, 2013
    Date of Patent: January 3, 2017
    Assignee: Commonwealth Scientific and Industrial Research Organisation
    Inventors: Bradley Ladewig, Richelle Lyndon, Matthew Hill
  • Patent number: 9440939
    Abstract: A novel compound useful as a raw material for a resist material is described. A norbornene derivative having epoxy and a methylene-mediated reactive group in a norbornane skeleton is represented by the following formula. In the formula, R1 represents a hydrogen atom, acryloyl, methacryloyl or hydroxymethylacryloyl, and R2 represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms.
    Type: Grant
    Filed: November 28, 2013
    Date of Patent: September 13, 2016
    Assignees: JNC CORPORATION, JNC PETROCHEMICAL CORPORATION
    Inventors: Hirotsuna Yamada, Sakae Kawamura
  • Patent number: 9434683
    Abstract: The present invention provides a titanium-silicalite molecular sieve and a method for preparing the same. The method includes the steps of preparing a mixture of a titanium source, a silicon source, a metal source selected from IIA to IVA elements and a template agent; heating the mixture to form a gel mixture; heating the gel mixture in a water bath; and calcining the gel mixture after the gel mixture in the water bath to form the titanium-silicalite molecular sieve. The present invention further provides a method for preparing cyclohexanone oxime by using the titanium-silicalite molecular sieve as the catalyst which results in high conversion rate, high selectivity and high usage efficiency of hydrogen peroxide.
    Type: Grant
    Filed: January 13, 2012
    Date of Patent: September 6, 2016
    Assignee: China Petrochemical Development Corporation
    Inventors: Ya-Ping Chen, Cheng-Fa Hsieh, Pin-To Yao, Chien-Chang Chiang
  • Patent number: 9353074
    Abstract: Process for dehydrating an ethanol feed to ethylene then oxidating the ethanol to ethylene oxide, comprising vaporizing the feed and a flow of diluting water comprising recycled ethanol to produce a vaporized feed, dehydrating a mixture of vaporized feed and a vaporized flow of diluting water comprising ethanol, separating the dehydration effluent into ethylene and water effluents, purifying at least a portion of the water effluent and separating a flow of treated water and a flow of diluting water comprising ethanol, recycling and vaporizing at least a portion of the separated diluting water by partial or complete vaporization in an exchanger using heat exchange with a quench flow obtained from the oxidation, said quench flow, cooled, then recycled to the oxidation reactor(s), and oxidation of the ethylene in the effluent comprising ethylene into ethylene oxide, this oxidation using a tubular oxidation reactor cooled by vaporization of said quench flow.
    Type: Grant
    Filed: February 6, 2014
    Date of Patent: May 31, 2016
    Assignee: IFP ENERGIES NOUVELLES
    Inventors: Vincent Coupard, Thomas Plennevaux
  • Patent number: 9346773
    Abstract: Dehydrating an ethanol feed to form ethylene then oxidation of the ethanol to ethylene oxide: vaporization of an ethanol feed and at least a portion of a flow of diluting water comprising recycled ethanol so as to produce a vaporized feed, compression in a compressor driven by a condensing turbine driven by the steam generated by an oxidation step, dehydration of a mixture of compressed vaporized feed, separation of effluent obtained from dehydration into ethylene and water, purification of at least a portion of effluent containing water and separation into at least a flow of treated water and a flow of diluting water containing ethanol, recycling the latter upstream of the vaporization, oxidation of ethylene containing in the effluent into ethylene oxide, in at least one tubular oxidation reactor cooled by vaporization of a quench flow, said vaporized quench flow being used to drive a condensing turbine.
    Type: Grant
    Filed: February 6, 2014
    Date of Patent: May 24, 2016
    Assignee: IFP ENERGIES NOUVELLES
    Inventors: Vincent Coupard, Thomas Plennevaux
  • Patent number: 9221774
    Abstract: A method for the epoxidation of an olefin comprising the steps of reacting a feed gas composition containing an olefin, oxygen, and a moderator having an optimal moderator concentration in the presence of an epoxidation catalyst at a first temperature and having a first selectivity; and increasing the optimal moderator concentration to a second moderator concentration and whereby the first selectivity is lowed to a second selectivity and the first temperature to a second temperature.
    Type: Grant
    Filed: October 18, 2012
    Date of Patent: December 29, 2015
    Assignee: Scientific Design Company, Inc.
    Inventors: Hassan Eisa Al-Ahmadi, Ashok S. Padia
  • Patent number: 9187442
    Abstract: A novel method for producing a stereoselective epoxyketone compound is provided. A method for producing an epoxyketone compound represented by the formula (1), as represented by the following scheme, whereby it is possible to obtain an epoxyketone derivative in good yield and at high selectivity and to provide an industrially useful production method and an intermediate thereof. wherein R1 is a hydrogen atom, a linear, branched or cyclic alkyl group, an aromatic group which may have a substituent, or a heterocyclic group which may have a substituent, and R2 is a protective group for an amino group. R is a hydrogen atom or a C1-10 alkyl group, and R's may be the same or different, provided that at least one R is a C1-10 alkyl group.
    Type: Grant
    Filed: June 27, 2013
    Date of Patent: November 17, 2015
    Assignee: Nissan Chemical Industies, Ltd.
    Inventors: Yukihiro Nishino, Kazuya Wakui, Shota Murase, Yoshifumi Sakai
  • Patent number: 9139544
    Abstract: The invention relates to a process for the production of ethylene oxide, comprising the steps of: producing ethylene resulting in a stream comprising ethylene and ethane; separating the stream comprising ethylene and ethane into a stream comprising ethylene and ethane in which stream the amount of ethylene is greater than the amount of ethane and a stream comprising ethane and ethylene in which stream the amount of ethane is greater than the amount of ethylene; producing ethylene oxide by subjecting ethylene and ethane from the stream comprising ethylene and ethane, in which stream the amount of ethylene is greater than the amount of ethane, to oxidation conditions resulting in a stream comprising ethylene oxide, unconverted ethylene and ethane; and recovering ethylene oxide from the stream comprising ethylene oxide, unconverted ethylene and ethane.
    Type: Grant
    Filed: March 25, 2013
    Date of Patent: September 22, 2015
    Assignee: Shell Oil Company
    Inventors: Jovan Jovanovic, Timothy Michael Nisbet, Timothe Johannes Olthof, Michael Johannes Franciscus Maria Verhaak
  • Patent number: 9115037
    Abstract: The present invention relates to a process for removing dimethylether from an olefin stream comprising dimethylether, comprising: (a) providing to an oxygenate recovery zone the olefin stream comprising dimethylether and a methanol-comprising solvent, treating the olefin stream comprising dimethylether with the methanol comprising solvent, and retrieving at least a dimethylether-depleted, methanol-comprising olefin stream; and (b) providing to the oxygenate recovery zone a non-aqueous C2 to C4 alcohol solvent and treating the dimethylether-depleted, methanol-comprising olefin stream with the non-aqueous C2 to C4 alcohol solvent, and retrieving from the oxygenate recovery zone at least an olefinic product that is depleted in dimethylether and methanol and a spent solvent comprising at least one C2 to C4 alcohol and methanol.
    Type: Grant
    Filed: December 20, 2013
    Date of Patent: August 25, 2015
    Assignee: Shell Oil Company
    Inventor: Jeroen Van Westrenen
  • Patent number: 9115103
    Abstract: The present invention relates to a process for producing an olefinic product, comprising (a) preparing a reaction product by converting an oxygenate-comprising feedstock in an oxygenate to olefin process, the reaction product comprising at least C2+ olefins and DME, (b) separating at least part of the reaction product by means of extractive distillation using a butanol solvent into: (i) a first fraction comprising C3? olefins and butanol; and (ii) a second fraction comprising C4+ olefins, DME and butanol; (c) separating the first fraction into: (iii)a C3? olefinic product; and (iv) a third fraction comprising butanol; (d) separating the second fraction into: (v) a DME-comprising C4-C5 olefinic product; and (vi) a fourth fraction comprising butanol and C6+ olefins, wherein at least part of the third and/or fourth fraction are recycled to step (b) together with or as part of the butanol solvent.
    Type: Grant
    Filed: December 20, 2013
    Date of Patent: August 25, 2015
    Assignee: Shell Oil Company
    Inventor: Jeroen Van Westrenen
  • Patent number: 9085544
    Abstract: The present invention provides an efficient method of synthesizing and purifying dianhydrohexitols such as dianhydrogalactitol. In general, as applied to dianhydrogalactitol, the method comprises: (1) reacting dulcitol with a concentrated solution of hydrobromic acid at a temperature of about 80° C. to produce dibromogalactitol; (2) reacting the dibromogalactitol with potassium carbonate in t-butanol to produce dianhydrogalactitol; and (3) purifying the dianhydrogalactitol using a slurry of ethyl ether to produce purified dianhydrogalactitol. Another method produces dianhydrogalactitol from dulcitol; this method comprises: (1) reacting dulcitol with a reactant to convert the 1,6-hydroxy groups of dulcitol to an effective leaving group to generate an intermediate; and (2) reacting the intermediate with an inorganic weak base to produce dianhydrogalactitol through an intramolecular SN2 reaction. Other methods for the synthesis of dianhydrogalactitol from dulcitol are described.
    Type: Grant
    Filed: November 5, 2013
    Date of Patent: July 21, 2015
    Assignee: DEL MAR PHARMACEUTICALS
    Inventors: Dennis M. Brown, Mike Tso-Ping Li
  • Patent number: 9073883
    Abstract: A process for the production of HFPO includes introducing a feedstock comprising HFP and molecular oxygen into a heated reaction zone of a reactor. The reaction zone is at a reaction temperature Tr, where 180° C.?Tr?230° C. The feedstock is allowed to react, by epoxidation of the HFP, to produce HFPO. The HFPO is withdrawn from the reaction zone. The introduction of the feedstock into the reaction zone and the withdrawal of the product from the reaction zone is continuous.
    Type: Grant
    Filed: March 15, 2013
    Date of Patent: July 7, 2015
    Assignee: UNIVERSITY OF KWAZULU-NATAL
    Inventors: David Lokhat, Maciej Starzak, Deresh Ramjugernath
  • Patent number: 9073034
    Abstract: At least one method to efficiently produce alkylene oxide from partial oxidation of hydrocarbons using a high efficiency heterogeneous catalyst in a fixed bed enclosed within a reaction vessel, and a reaction vessel constructed to facilitate the same.
    Type: Grant
    Filed: March 17, 2011
    Date of Patent: July 7, 2015
    Assignee: DOW TECHNOLOGY INVESTMENTS LLC
    Inventors: Max M. Tirtowidjojo, Subrata Sen, Christina Zarth, Pramod D. Patil
  • Patent number: 9067901
    Abstract: The invention relates to a process for the production of ethylene oxide, comprising the steps of: producing ethylene by converting a stream comprising an oxygenate into a stream comprising ethylene and ethane; producing ethylene oxide by subjecting ethylene and ethane from the stream comprising ethylene and ethane to oxidation conditions resulting in a stream comprising ethylene oxide, unconverted ethylene and ethane; and recovering ethylene oxide from the stream comprising ethylene oxide, unconverted ethylene and ethane.
    Type: Grant
    Filed: January 23, 2012
    Date of Patent: June 30, 2015
    Assignee: Shell Oil Company
    Inventors: Michael Johannes Franciscus Maria Verhaak, Jeroen Van Westrenen
  • Publication number: 20150141675
    Abstract: The present invention provides a method for producing an alicyclic diepoxy compound at a higher yield by carrying out epoxidation of an alicyclic olefin compound at a higher reaction rate. The method is a method for producing an alicyclic diepoxy compound represented by formula (1) below by reacting an alicyclic olefin compound represented by formula (2) below with hydrogen peroxide in the coexistence of the alicyclic olefin compound represented by formula (2) below, a hydrogen peroxide solution, a powdered solid catalyst support and a powdered solid catalyst all together: wherein R1 to R12 are each hydrogen, halogen, an alkyl group optionally having halogen or an alkoxy group optionally having a substituent.
    Type: Application
    Filed: April 26, 2013
    Publication date: May 21, 2015
    Inventors: Junko Ichihara, Shunro Yamaguchi, Atsushi Kameyama, Takashi Suzuki, Takashi Morikita
  • Publication number: 20150141676
    Abstract: In order to produce an epoxy compound with a less chlorine content at a higher reaction rate and yield, the present invention provides a method for producing an epoxy compound by reacting a compound having a carbon-carbon double bond with hydrogen peroxide in the coexistence of the compound having a carbon-carbon double bond, the hydrogen peroxide solution, a powdered solid catalyst support and a powdered solid catalyst all together, the solid catalyst comprising isopolyacids produced from (a) tungstic acid or a salt thereof and (b) a quaternary ammonium salt compound and/or a pyridinium salt, selected from halogen-free compounds.
    Type: Application
    Filed: April 26, 2013
    Publication date: May 21, 2015
    Inventors: Junko Ichihara, Shunro Yamaguchi, Atsushi Kameyama, Takashi Suzuki, Takashi Morikita
  • Publication number: 20150141677
    Abstract: A method is provided for carrying out epoxidation of an olefin compound with good productivity. The method produces an epoxy compound by reacting a compound having a carbon-carbon double bond with hydrogen peroxide by carrying out repeatedly or continuously the following steps: (1) reacting a compound having a carbon-carbon double bond with hydrogen peroxide in the coexistence of (a) the compound having a carbon-carbon double bond, (b) a hydrogen peroxide solution, (c) a powdered solid catalyst support, and (d) a powdered solid catalyst, and optionally further (e) an organic solvent to produce an epoxy compound; (2) separating the epoxy compound reaction product from the reaction mixture produced in (1); and (3) adding (d) and also adding (a), (b), (c), and optionally further (e) to the mixture of the powdered solid catalyst support and powdered solid catalyst after separating the reaction product in (2).
    Type: Application
    Filed: April 26, 2013
    Publication date: May 21, 2015
    Applicant: OSAKA UNIVERSITY
    Inventors: Junko Ichihara, Shunro Yamaguchi, Atsushi Kameyama, Takashi Suzuki, Takashi Morikita
  • Patent number: 9035078
    Abstract: The invention relates to novel nitrile compounds according to formula I and II: (I) Formula I wherein: X=—CH3 or —C?N, (II) Formula II wherein: X=—CH3 or —C?N, each Y is independently chosen from —OH or RC(0)0-, each R is independently chosen from a C1-21 alkyl group. The invention also relates to processes for the preparation of nitrile compounds according to formula I and II and to uses of the nitrile compounds.
    Type: Grant
    Filed: July 6, 2012
    Date of Patent: May 19, 2015
    Assignee: DSM IP ASSETS B.V.
    Inventors: Paulus Lambertus Alsters, Edwin Gerard Ijpeij
  • Publication number: 20150133629
    Abstract: There is provided a diepoxy compound that can be polymerized to form a cured product having thermal stability that has excellent heat resistance, and can maintain excellent mechanical properties even if exposed to a high temperature environment. The saturated diepoxy compound of the present invention is represented by the following formula (1) and can be produced by hydrogenating the unsaturated bond of an unsaturated diepoxy compound represented by the following formula (2). In the following formulas, R1 to R20 are each an independent group and identically or differently represent a hydrogen atom, a methyl group, or an ethyl group.
    Type: Application
    Filed: April 2, 2013
    Publication date: May 14, 2015
    Applicant: DAICEL CORPORATION
    Inventors: Kyuhei Kitao, Hideyuki Takai, Michihiro Sugahara
  • Publication number: 20150126756
    Abstract: In a process for producing propylene oxide, cyclohexylbenzene is contacted with an oxygen-containing compound under oxidation conditions with or without a suitable catalyst to produce an oxidation reaction effluent comprising cyclohexylbenzene hydroperoxide. At least a portion of the cyclohexylbenzene hydroperoxide is then reacted with propylene in the presence of an epoxidation catalyst under conditions effective to produce an epoxidation reaction effluent comprising phenylcyclohexanol and propylene oxide.
    Type: Application
    Filed: August 30, 2012
    Publication date: May 7, 2015
    Applicant: ExxonMobil Chemical Patents Inc.
    Inventors: Hari Nair, Charles Morris Smith, James R. Lattner, Krystle J. Chavez, James C. Vartuli
  • Patent number: 8993791
    Abstract: To provide an efficient method of producing an epoxy compound comprising reacting hydrogen peroxide and acetonitrile with the carbon-carbon double bond of an organic compound having a carbon-carbon double bond. A method of producing an epoxy compound comprising epoxidizing the carbon-carbon double bond of an organic compound having a carbon-carbon double bond in the presence of acetonitrile by using hydrogen peroxide as an oxidizing agent, wherein the reaction proceeds while controlling the acetonitrile concentration in the reaction system in the range of 0.6-5 mol/L by using a solvent containing an alcohol.
    Type: Grant
    Filed: December 17, 2010
    Date of Patent: March 31, 2015
    Assignee: Showa Denko K.K.
    Inventors: Hiroshi Uchida, Takamitsu Kobayashi, Naoya Fukumoto
  • Publication number: 20150073160
    Abstract: A process for the production of HFPO includes introducing a feedstock comprising HFP and molecular oxygen into a heated reaction zone of a reactor. The reaction zone is at a reaction temperature Tr, where 180° C.?Tr<230° C. The feedstock is allowed to react, by epoxidation of the HFP, to produce HFPO. The HFPO is withdrawn from the reaction zone. The introduction of the feedstock into the reaction zone and the withdrawal of the product from the reaction zone is continuous.
    Type: Application
    Filed: March 15, 2013
    Publication date: March 12, 2015
    Inventors: David Lokhat, Maciej Starzak, Deresh Ramjugernath
  • Patent number: 8969602
    Abstract: The invention relates to a process for the production of ethylene oxide, comprising the steps of producing ethylene resulting in a stream comprising ethylene and ethane; producing ethylene oxide by subjecting ethylene and ethane from the stream comprising ethylene and ethane to oxidation conditions resulting in a stream comprising ethylene oxide, unconverted ethylene and ethane; and recovering ethylene oxide from the stream comprising ethylene oxide, unconverted ethylene and ethane.
    Type: Grant
    Filed: January 23, 2012
    Date of Patent: March 3, 2015
    Assignee: Shell Oil Company
    Inventor: Michael Johannes Franciscus Maria Verhaak
  • Patent number: 8962872
    Abstract: A method for preparing an epoxide is disclosed. The method for preparing an epoxide includes the step of performing a reaction of an alkene and oxidant in the presence of a Ti—Si molecular sieve as a catalyst, and increases the conversion rate of hydrogen peroxide and the yield of the epoxide.
    Type: Grant
    Filed: September 13, 2012
    Date of Patent: February 24, 2015
    Assignee: China Petrochemical Development Corporation
    Inventors: Yu-Chuan Hsu, Cheng-Fa Hsieh, I-Hui Lin
  • Publication number: 20150018515
    Abstract: A method of producing an epoxy compound, which comprises reacting hydrogen peroxide with a compound having a carbon-carbon double bond, in the presence of at least one of a tungsten compound and a molybdenum compound; and an onium salt comprising 20 or more carbon atoms and one or more of substituents convertible to a functional group containing an active hydrogen or a salt thereof.
    Type: Application
    Filed: September 30, 2014
    Publication date: January 15, 2015
    Applicant: MITSUBISHI CHEMICAL CORPORATION
    Inventors: Akemi HOSOKAWA, Haruhiko KUSAKA
  • Patent number: 8932980
    Abstract: The invention discloses three-dimensional, ordered, mesoporous titanosilicates wherein the Ti is in a tetrahedral geometry and exclusively substituted for Si in the silica framework. Such titanosilicates find use as catalysts for epoxidation, hydroxylation, C—H bond oxidation, oxidation of sulfides, aminolysis of epoxide and amoximation, with approx. 100% selectivity towards the products.
    Type: Grant
    Filed: July 20, 2011
    Date of Patent: January 13, 2015
    Assignee: Council of Scientific & Industrial Research
    Inventors: Srinivas Darbha, Anuj Kumar
  • Publication number: 20150011782
    Abstract: Disclosed herein is a novel route of synthesis of syn azide epoxide of formula 5, which is used as a common intermediate for asymmetric synthesis of HIV protease inhibitors such as Amprenavir, Fosamprenavir, Saquinavir and formal synthesis of Darunavir and Palinavir obtained by Cobalt-catalyzed hydrolytic kinetic resolution of racemic anti-(2SR,3SR)-3-azido-4-phenyl-1,2-epoxybutane (azido-epoxide).
    Type: Application
    Filed: January 10, 2013
    Publication date: January 8, 2015
    Inventors: Sunita Khanderao Gadakh, Reddy Santhosh Rekula, Arumugam Sudalai
  • Patent number: 8916495
    Abstract: The present invention relates to an improved carrier for an ethylene epoxidation catalyst, the carrier comprising alumina in combination with a stability-enhancing amount of mullite. The invention is also directed to an improved catalyst containing the improved carrier, as well as an improved process for the epoxidation of ethylene using the catalyst of the invention.
    Type: Grant
    Filed: December 27, 2012
    Date of Patent: December 23, 2014
    Assignee: Scientific Design Company, Inc.
    Inventors: Serguei Pak, Andrzej Rokicki, Shuji Kawabata
  • Publication number: 20140356280
    Abstract: Provided is a surfactant-free, single-step synthesis of delaminated aluminosilicate zeolites. The process comprises the step of heating a borosilicate zeolite precursor in a metal salt solution, e.g., an aluminum nitrate solution, zinc nitrate solution or manganese nitrate solution. The delaminated aluminosilicate zeolite product is then recovered from the solution.
    Type: Application
    Filed: May 30, 2014
    Publication date: December 4, 2014
    Applicants: CHEVRON U.S.A. INC., THE REGENTS OF THE UNIVERSITY OF CALIFORNIA
    Inventors: Xiaoying OUYANG, Alexander KATZ, Stacey Ian ZONES
  • Publication number: 20140350274
    Abstract: Embodiments of the present disclosure relate to asymmetric epoxidation of olefinic alcohols, using a chiral alcohol chelated titanium catalyst and an organic peroxide performed in a microreactor flow reactor system that can comprise multiple microreactor modules. Molecular sieves can be used to remove any adventitious water in the reagent feed solutions and ensure an anhydrous reaction solution. The use of a microreactor flow reactor allows for the epoxidation reaction to be run at elevated temperatures of at least 20, 30, or even 50° C., which dramatically accelerates the reaction, but without a large drop in enantioselectivity. The reaction can therefore be performed with short reaction times resulting in a high throughput.
    Type: Application
    Filed: November 6, 2012
    Publication date: November 27, 2014
    Applicant: Corning Incorporated
    Inventor: Patrick Rosaire Bazinet
  • Patent number: 8895763
    Abstract: An integrated process for preparing alkylene oxides and alkylene glycols is described. For this purpose, an alkylene oxide plant and an alkylene glycol plant are combined with one another and the water originating from the alkylene oxide plant and also other constituents of the reaction mixture are introduced into the alkylene glycol plant. In this way, alkylene glycols which have been produced in the alkylene oxide plant can be recovered as materials of value and the water circulation into the alkylene glycol plant can be eliminated or drastically reduced. In addition, the energy-intensive treatment of the process water from the alkylene oxide plant can be dispensed with. The integration of the two processes leads overall to better energy efficiency and conservation of resources in the work-up of residues from the process.
    Type: Grant
    Filed: August 12, 2010
    Date of Patent: November 25, 2014
    Assignee: Thyssenkrupp UHDE GmbH
    Inventor: Ferdinand Rudolf Reif
  • Patent number: 8889892
    Abstract: A process for producing an olefin oxide which comprises reacting an olefin with oxygen in the presence of a catalyst comprising (a) ruthenium metal or a ruthenium oxide, (b) manganese oxide and (c) alkaline metal component or alkaline earth metal component.
    Type: Grant
    Filed: May 26, 2011
    Date of Patent: November 18, 2014
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yoshihiko Ohishi, Anusorn Seubsai, Selim Senkan
  • Patent number: 8871519
    Abstract: The present invention relates to methods for qualifying material for using in the cleaning of alkylene oxide equipment. Qualified material is not expected to contribute to the formation of determinable amounts of alkylene oxide by-products. Methods of cleaning alkylene oxide equipment, and alkylene oxide processes incorporating these methods are also provided.
    Type: Grant
    Filed: May 10, 2012
    Date of Patent: October 28, 2014
    Assignee: Dow Technology Investments LLC
    Inventor: Paul Victor Hinman
  • Patent number: 8822709
    Abstract: The invention relates to an integrated process for preparing an epoxide from an oxygenate, wherein the oxygenate is converted into a lower olefin and the lower olefin is subsequently epoxidised, and wherein isobutane obtained after hydrogenation and subsequent normal/iso separation of C4 hydrocarbons obtained as by-product of the oxygenate conversion, is converted into a hydroperoxide that is used for the conversion of the lower olefin into the corresponding epoxide.
    Type: Grant
    Filed: October 16, 2012
    Date of Patent: September 2, 2014
    Assignee: Shell Oil Company
    Inventors: Leslie Andrew Chewter, Hervé Henry, Pieter Oldenhove, Rajaram Ramesh, Jeroen Van Westrenen