Plural O-containing Organic Compounds Patents (Class 585/607)
  • Patent number: 11046623
    Abstract: Simple and economical conversion of aqueous ethanol feed streams into butenes by a single step method using transition metal oxides on a silica supports under preselected processing conditions. By directly producing a C4-rich olefin mixture from an ethanol containing stream various advantages are presented including, but not limited to, significant cost reduction in capital expenses and operational expenses.
    Type: Grant
    Filed: May 11, 2020
    Date of Patent: June 29, 2021
    Assignee: BATTELLE MEMORIAL INSTITUTE
    Inventors: Vanessa M. Dagle, Robert A. Dagle
  • Patent number: 10647625
    Abstract: A process for producing 1,3-butadiene (BD) from ethanol in a single step by s7passing a mixture containing ethanol in a gas phase over a multifunctional catalyst having a transition metal dispersion of at least 30% on a silica metal oxide support. In some examples the multifunctional catalyst comprises a silica metal oxide having a surface area of at least 200 m{circumflex over (?)}2/g. The multifunctional catalyst can include a transition metal oxide, a silica metal oxide made from a high purity silica gel, mesoporous silica and fumed silica, such as high purity SBA16, SBA15, or Davisil grade 646.
    Type: Grant
    Filed: December 11, 2017
    Date of Patent: May 12, 2020
    Assignee: BATTELLE MEMORIAL INSTITUTE
    Inventors: Vanessa Dagle, Robert A. Dagle
  • Patent number: 10647622
    Abstract: A simplified processes for producing desired chemicals such as butenes from feedstock mixtures containing ethanol. In one set of embodiments this is performed in a single step, wherein a feed containing ethanol in a gas phase is passed over an acidic metal oxide catalyst having a transition metal dispersion of at least 5% on a metal oxide support. The ethanol content of the feedstock mixture may vary from 10 to 100 percent of the feed and in those non-eat applications the ethanol feed may contain water.
    Type: Grant
    Filed: May 31, 2018
    Date of Patent: May 12, 2020
    Assignee: BATTELLE MEMORIAL INSTITUTE
    Inventors: Robert A. Dagle, Vanessa M. Dagle
  • Patent number: 10358396
    Abstract: A process for the production of butadiene from an ethanol feed having at least 80% by weight of ethanol, A) converting ethanol into acetaldehyde B) converting an ethanol/acetaldehyde mixture into butadiene, C1) hydrogen treatment, D1) butadiene extraction, a first butadiene purification D2), a subsequent butadiene purification D3), an effluent treatment E1), E2) eliminating impurities and brown oils and F) scrubbing with water.
    Type: Grant
    Filed: September 17, 2015
    Date of Patent: July 23, 2019
    Assignees: IFP Energies nouvelles, Compagnie Generale des Etablissements Michelin, MICHELIN RECHERCHE ET TECHNIQUE S.A.
    Inventors: Rejane Dastillung, Beatrice Fischer, Marc Jacquin, Raphael Huyghe
  • Patent number: 10300459
    Abstract: A process includes reacting a feed stream containing ethanol and optionally acetaldehyde in a dehydration reactor in the presence of a dehydration catalyst system having a Group 4 or Group 5 metal oxide and a support. The process includes obtaining a product stream containing butadiene from the dehydration reactor. Another process includes reacting a feed stream containing ethanol and optionally acetaldehyde in a dehydration reactor in the presence of a dehydration catalyst system containing a tungsten oxide supported on a zeolite or a tantalum oxide supported on a zeolite. The process includes obtaining a product stream containing butadiene from the dehydration reactor.
    Type: Grant
    Filed: December 10, 2018
    Date of Patent: May 28, 2019
    Assignee: FINA TECHNOLOGY, INC.
    Inventors: Sivadinarayana Chinta, Kaushik Gandhi
  • Patent number: 9950969
    Abstract: The invention concerns a process for the production of butadiene from an ethanol feed comprising at least 80% by weight of ethanol, comprising a step for conversion of ethanol to acetaldehyde, a step for the extraction of butadiene, a step for scrubbing gaseous by-products with water, a step for eliminating impurities and brown oils, a step for treating effluents, a first butadiene purification step, and a subsequent butadiene purification step, said ethanol feed being supplied to said butadiene extraction step, the arrangement of the steps and recycles allowing the recycles to be maximized and allowing the water and energy consumption to be minimized.
    Type: Grant
    Filed: September 17, 2015
    Date of Patent: April 24, 2018
    Assignees: IFP Energies Nouvelles, Compagnie Generale des Etablissements Michelin, Michelin Recherche et Technique S.A.
    Inventors: Rejane Dastillung, Beatrice Fischer, Marc Jacquin, Raphael Huyghe
  • Patent number: 9878965
    Abstract: The present invention relates to a gas-phase process for the preparation of butadiene comprising (i) providing a gas stream G-1 comprising ethanol; (ii) contacting the gas stream G-1 comprising ethanol with a catalyst, thereby obtaining a gas stream G-2 comprising butadiene, wherein the catalyst comprises a zeolitic material having a framework structure comprising YO2, Y standing for one or more tetravalent elements, wherein at least a portion of Y comprised in the framework structure is isomorphously substituted by one or more elements X, as well as to a zeolitic material having a framework structure comprising YO2, Y standing for one or more tetravalent elements, wherein at least a portion of Y comprised in the framework structure is isomorphously substituted by one or more elements X, wherein the zeolitic material displays a specific X-ray powder diffraction pattern, and to its use.
    Type: Grant
    Filed: June 13, 2014
    Date of Patent: January 30, 2018
    Assignee: BASF SE
    Inventors: Kirsten Spannhoff, Andrei-Nicolae Parvulescu, Armin Lange de Oliveira, Stefan Marx, Mathias Feyen, Ulrich Müller, Ekkehard Schwab
  • Patent number: 8933285
    Abstract: Methods are provided for producing a jet fuel composition from a feedstock comprising a natural oil. The methods comprise reacting the feedstock with a low-weight olefin in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product. The methods further comprise hydrogenating the metathesized product under conditions sufficient to form a jet fuel composition.
    Type: Grant
    Filed: November 25, 2009
    Date of Patent: January 13, 2015
    Assignee: Elevance Renewable Sciences, Inc.
    Inventors: Melvin L. Luetkens, Jr., Steven A. Cohen, Chander Balakrishnan
  • Patent number: 8921635
    Abstract: This invention relates to gas-phase synthesis of butadiene from ethanol or ethanol and acetaldehyde mixture. The method of synthesis includes ethanol or ethanol and acetaldehyde mixture conversion in the presence of a catalyst, which differs from the known methods by the carrying out of the interaction in the presence of the solid catalyst, which contains metal, chosen from the group of silver, gold or copper, and metal oxide, chosen from the group of magnesium, titanium, zirconium, tantalum or niobium oxides. The method announced is used for condensation process under the conditions of continuous flow fixed bed reactor. The invention allows to reach high yield and selectivity to butadiene and high level of conversion of the feed.
    Type: Grant
    Filed: July 27, 2011
    Date of Patent: December 30, 2014
    Assignee: Obshchestvo S Ogranichennoy Otvetstvennostju “Unisit”
    Inventors: Vitaly Valerievich Ordomskiy, Vitaly Leonidovich Sushkevich, Irina Igorevna Ivanova
  • Publication number: 20130123554
    Abstract: This invention relates to gas-phase synthesis of butadiene from ethanol or ethanol and acetaldehyde mixture. The method of synthesis includes ethanol or ethanol and acetaldehyde mixture conversion in the presence of a catalyst, which differs from the known methods by the carrying out of the interaction in the presence of the solid catalyst, which contains metal, chosen from the group of silver, gold or copper, and metal oxide, chosen from the group of magnesium, titanium, zirconium, tantalum or niobium oxides. The method announced is used for condensation process under the conditions of continuous flow fixed bed reactor. The invention allows to reach high yield and selectivity to butadiene and high level of conversion of the feed.
    Type: Application
    Filed: July 27, 2011
    Publication date: May 16, 2013
    Applicant: OBSHCHESTVO S OGRANICHENNOY OTVETSTVENNOSTJU "UNISIT"
    Inventors: Vitaly Valerievich Ordomskiy, Vitaly Leonidovich Sushkevich, Irina Igorevna Ivanova
  • Patent number: 7582777
    Abstract: The present invention is directed to unsaturated or derivatized long chain (C22-C50) polyunsaturated hydrocarbons and a method of preparing the long chain hydrocarbons via electrocoupling of C12-C26 fatty acids. It has been found that soapstock is an inexpensive source of starting materials for the present method. The present invention is also directed to compositions comprising the long chain polyunsaturated hydrocarbons, which can be used as reactive diluents and modifiers in latex, epoxy, alkyd and polymer compositions. In another aspect, the present invention is directed to derivitization or ozonolysis of the long chain polyunsaturated hydrocarbons. The present method is also useful for preparing C12-26 alkyl esters and C12-26 carbon chain compounds containing a terminal olefin.
    Type: Grant
    Filed: October 17, 2005
    Date of Patent: September 1, 2009
    Assignee: Archer-Daniels-Midland Company
    Inventor: Paul D. Bloom
  • Patent number: 7442844
    Abstract: A process for producing isoprene is provided, which includes continuously or intermittently supplying isobutylene and/or t-butanol, formaldehyde and water into an acidic aqueous solution, and reacting the reaction mixture while distilling away a mixture containing produced isoprene, water, unreacted starting materials and other low boiling point components from this reaction mixture to the outside of the reaction system, wherein the reaction is carried out while controlling the concentration of high boiling point byproducts, which is produced and accumulated in the reaction mixture, to fall within the range of 0.5-40 mass %.
    Type: Grant
    Filed: March 24, 2004
    Date of Patent: October 28, 2008
    Assignee: Kuraray Co., Ltd.
    Inventors: Osamu Yamada, Manabu Kusano, Nobuo Takayanagi, Hideki Arimoto
  • Patent number: 6667423
    Abstract: For the production of a diene a process in three stages comprises a stage a) for decomposition of at least one tertiary alkyl ether in a mixture that contains at least one tertiary olefin, at least one alcohol and at least one residual ether, in the presence of a catalyst that comprises at least one mineral solid that is grafted by at least one organic group such as alkyl sulfonic acid, sulfonic aryl and/or sulfonic alkylaryl, a stage b) for purification of the olefin that is obtained in stage a), and a stage c) for oxidizing dehydrogenation of the tertiary olefin that is obtained in stage b) in the presence of a catalyst under conditions for obtaining a diene.
    Type: Grant
    Filed: September 9, 1999
    Date of Patent: December 23, 2003
    Assignee: Institut Francais du Petrole
    Inventors: Claire Dumonteil, Alain Forestiere, Marie-Claire Marion
  • Publication number: 20030114725
    Abstract: For the production of a diene a process in three stages comprises
    Type: Application
    Filed: September 9, 1999
    Publication date: June 19, 2003
    Inventors: CLAIRE DUMONTEIL, ALAIN FORESTIERE, MARIE-CLAIRE MARION
  • Patent number: 5723708
    Abstract: A method for producing cyclopentadienes which comprises the step of cyclodehydration of an unsaturated carbonyl compound having a specific chemical structure in a vapor phase in the presence of a specific solid acid catalyst. The cyclopentadienes of the invention can be produced in a high yield from inexpensive starting materials through a simplified reaction process and are useful as intermediate compounds for organic synthesis.
    Type: Grant
    Filed: September 27, 1995
    Date of Patent: March 3, 1998
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Yasuo Matsumura, Kazuharu Suyama, Yoshihisa Inomata
  • Patent number: 5177290
    Abstract: The present invention is directed to a process for producing dienes which involves reacting a reaction mixture of tertiary alkyl ether and a source of oxygen over two functionally distinct catalysts under reaction conditions sufficient to produce high yields of the dienes with minimal recycle of the ether. The two functionally different catalysts are selected from a group of bifunctional catalysts having both oxidation sites and acidic sites and monofunctional acidic catalysts, such as bifunctional catalysts containing components selected from a group of oxides of vanadium, tungsten, molybdenum, copper, iron, chromium, and uranium and mixtures thereof; and monofuctional acid catalysts such as acid treated montmorillonite clays, and acid catalysts comprising an inorganic amorphous or substantially amorphous oxide material comprising the following components reacted therein:M.sup.1 /M.sup.2 /P/Owherein M.sup.1 is at least one Group IIIB element selected from the group consisting of Al, Ga, In and Tl; M.sup.
    Type: Grant
    Filed: January 10, 1991
    Date of Patent: January 5, 1993
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Ji-Yong Ryu, Robert C. Michaelson
  • Patent number: 4713458
    Abstract: Ketones and aldehydes are converted to ethenylidene-containing compounds by reaction thereof with dimethyl carbonate and a phosphine compound.
    Type: Grant
    Filed: August 21, 1984
    Date of Patent: December 15, 1987
    Assignee: The Dow Chemical Company
    Inventors: Kevin A. Frazier, James M. Renga
  • Patent number: 4593145
    Abstract: A process for producing isoprene in good yield is provided. The process is characterized in that an alkyl tertiary butyl ether and a formaldehyde source are fed, together with water, into a acidic aqueous solution continuously or intermittently while maintaining the reaction pressure in an adequate range and at the same time distilling off the product isoprene, unreacted starting materials, isobutene and tertiary butanol, together with water, from the reaction zone.
    Type: Grant
    Filed: March 4, 1985
    Date of Patent: June 3, 1986
    Assignee: Kuraray Company Limited
    Inventors: Yoichi Ninagawa, Osamu Yamada, Tsumoru Renge, Sunao Kyo, Takayoshi Osaki, Koichi Kushida
  • Patent number: 4527000
    Abstract: Novel diolefin insect pheromone mimics are used to disrupt the sexual communication between insects when applied to an agricultural area in behaviorally effective amounts as follows: (Z)-1,12-heptadecadiene used for Heliothis zea Boddie; (Z)-15-methyl-1,9-heptadecadiene used for Trogoderma variabile; (E)-15-methyl-1,9-heptadecadiene used for Trogoderma glabrum; and (Z,Z)-1,12,14-heptadecatriene used for Amyelois transitella.
    Type: Grant
    Filed: March 14, 1983
    Date of Patent: July 2, 1985
    Assignee: The United States of America as represented by the Secretary of Agriculture
    Inventors: David A. Carlson, John R. McLaughlin
  • Patent number: 4381416
    Abstract: A process for producing isoprene, which comprises decomposing a mixture of at least two compounds represented by the general formula ##STR1## wherein (i) W and Y each represent a hydrogen atom, and X and Z are identical or different and each represent the group OR, (ii) W and X together form a single bond, Y represents a hydrogen atom and Z represents the group OR, (iii) W represents a hydrogen atom, X and Y together form a single bond, and Z represents the group OR, or (iv) W represents a hydrogen atom, X represents the group OR, and Y and Z together form a single bond, in which R represents a hydrogen atom, a methyl group, a methoxymethyl group, a methylbutenyl group, a methylbutenyloxymethyl group, a 1,1-dimethyl-3-hydroxypropyl group, a 1,1-dimethyl-3-hydroxypropyloxymethyl group, a 3-methyl-3-hydroxybutyl group, a 3-methyl-3-hydroxybutyloxymethyl group, a 1,1-dimethyl-3-methoxypropyl group, a 1,1-dimethyl-3-methoxypropyloxymethyl group, a 3-methyl-3-methoxybutyl group or a 3-methyl-3-methoxybutyloxymethy
    Type: Grant
    Filed: December 1, 1980
    Date of Patent: April 26, 1983
    Assignee: Kuraray Co., Ltd.
    Inventors: Sunao Kyo, Tumoru Renge, Katsumi Omura