Alcohol, Ester, Or Ether Patents (Class 585/639)
  • Patent number: 11097995
    Abstract: A method of making fuel including adding alcohol to a reactor with a zinc dihalide salt and heating the reactor to reflux, thereby forming a mixture. Water is removed from the mixture using azeotropic distillation. The mixture is distilled, thereby forming oligo(alkenes)n and residual alcohol. The oligo(alkenes)n are distilled using fractionation, thereby forming a first, a second, a third fraction, and removing the residual alcohol. The first fraction includes oligo(alkenes)n with n ranging from 2 to 4, the second fraction includes oligo(alkenes)n with n ranging from 4 to 8, and the third fraction includes oligo(alkenes)n with n ranging from 8 to 12. The first, second, and third fractions are hydrogenated, thereby forming oligo(alkanes)n. The first fraction includes oligo(alkanes)n with n ranging from 2 to 4, the second fraction includes oligo(alkanes)n with n ranging from 4 to 8, and the third fraction includes oligo(alkanes)n with n ranging from 8 to 12.
    Type: Grant
    Filed: May 18, 2020
    Date of Patent: August 24, 2021
    Assignee: The United States of America, as represented by the Secretary of the Navy
    Inventor: Matthew C. Davis
  • Patent number: 10661243
    Abstract: The present invention provides a process for the preparation of ethene by vapour phase chemical dehydration of ethanol using an adiabatic reactor, wherein the interior of the adiabatic reactor is separated into at least three reaction zones, comprising a first reaction zone, at least one intermediate reaction zone and a final reaction zone, and wherein each zone contains an ethanol dehydration catalyst; said process comprising the steps of; a) feeding a pre-heated reactant feed-stream into an inlet of the first reaction zone; b) extracting an effluent-stream from an outlet of the first reaction zone; c) feeding said effluent-stream into an inlet of a subsequent intermediate reaction zone; d) extracting an effluent-stream from an outlet of the intermediate reaction zone; e) repeating steps (c) and (d) for any subsequent intermediate reaction zones, if present; f) feeding, into an inlet of the final reaction zone, the effluent-stream from the preceding intermediate reaction zone; g) extracting a product stream
    Type: Grant
    Filed: December 8, 2015
    Date of Patent: May 26, 2020
    Assignee: Technip E&C Limited
    Inventor: Leslie William Bolton
  • Patent number: 10532349
    Abstract: A catalyst for selective catalytic reduction of NOx having one or more transition metals selected from Cr, Mn, Fe, Co, Ce, Ni, Cu, Zn, Ga, Mo, Ru, Rh, Pd, Ag, In, Sn, Re, Ir, Pt, and mixtures thereof supported on a support, wherein the support has a molecular sieve having at least one intergrowth phase having at least two different small-pore, three-dimensional framework structures.
    Type: Grant
    Filed: January 12, 2015
    Date of Patent: January 14, 2020
    Assignee: Johnson Matthey Public Limited Company
    Inventors: Paul J. Andersen, John Leonello Casci, Hai-Ying Chen, Joseph M. Fedeyko
  • Patent number: 10486147
    Abstract: A catalyst for converting dimethyl ether into light olefins, including ethylene and propylene. The catalyst comprises a mixture of two zeolites, ZSM-5 and ZSM-35, intimately mixed and kept in close proximity in a porous extruded binder system. The resulting combination of zeolites demonstrates a synergistic effect with respect to the conversion of the dimethyl ether and has improved resistance to deactivation due to carbon and coke formation than the individual zeolites alone when operating in this reaction. The catalyst is used to produce ethylene and propylene from a feed mixture containing methanol, dimethyl ether and water.
    Type: Grant
    Filed: August 8, 2019
    Date of Patent: November 26, 2019
    Assignee: Enerkem, Inc.
    Inventors: Stephane Marie-Rose, Ludovic Pinard, Jennifer Lorena Gil Coba
  • Patent number: 10472300
    Abstract: The present invention is a process for dehydrating an alcohol to prepare a corresponding olefin, comprising: (a) providing a composition (A) comprising at least an alcohol having at least 2 carbon atoms, optionally water, optionally an inert component, in a dehydration unit, (b) placing the composition (A) into contact with an acidic catalyst in a reaction zone of said dehydration unit at conditions effective to dehydrate at least a portion of the alcohol to make a corresponding olefin, (c) recovering from said dehydration unit an effluent (B) comprising: at least an olefin, water, undesired by-products including aldehydes and light products, optionally unconverted alcohol(s), optionally the inert component, wherein, said composition (A)—providing step (a) comprises adding an effective amount of one or more sulfur containing compound capable to reduce the undesired by-products by comparison with a non introduction of such sulfur containing compound.
    Type: Grant
    Filed: December 18, 2015
    Date of Patent: November 12, 2019
    Assignees: Total Research & Technology Feluy, IFP Energies Nouvelles
    Inventors: Delphine Minoux, Nikolai Nesterenko, Cindy Adam, Walter Vermeiren, Philip De Smedt, Jean-Pierre Dath, Vincent Coupard, Sylvie Maury, Nicolas Aribert
  • Patent number: 10464051
    Abstract: A process for the vapour phase chemical dehydration of ethanol in a reactor in the presence of a supported heteropolyacid catalyst, said process comprising a step of contacting the ethanol with the heteropolyacid catalyst, wherein the heteropolyacid catalyst comprises a partially neutralised silicotungstic acid salt, wherein the partially neutralised silicotungstic acid salt has from 30% to 70% of the hydrogen atoms replaced with cations selected from the group consisting of alkali metal cations, alkaline earth metal cations, transition metal cations, ammonium cations, and mixtures thereof; but with the proviso that the alkali metal cation is not lithium; and wherein, after attaining steady-state performance of the catalyst, said process is operated continuously with the same supported heteropolyacid catalyst for at least 150 hours, without any regeneration of the catalyst.
    Type: Grant
    Filed: December 18, 2015
    Date of Patent: November 5, 2019
    Assignee: TECHNIP E&C LIMITED
    Inventor: Stephen Roy Partington
  • Patent number: 10413889
    Abstract: The present invention relates to a fluid catalytic cracking additive composition for cracking of heavy hydrocarbon feed stocks and process for preparing the additive. The additive is suitable for enhancing yields of light olefins such as propylene, isobutylene, LPG and reduces the bottom yields. The invention specifically relates to a fluid catalytic cracking additive composition comprising a pentasil zeolite, zeolites having pore size in a range of 5.4-7.7 ?, alumina, colloidal silica, kaolin clay, and phosphate, wherein the zeolites having pore size in the range of 5.4-7.7 ? is present in an amount of 1 to 10 wt % with respect to the total amount of the pentasil zeolite and zeolite having the pore size in the range of 5.4-7.7 ?.
    Type: Grant
    Filed: August 15, 2016
    Date of Patent: September 17, 2019
    Assignee: Indian Oil Corporation Limited
    Inventors: Mahesh Kadgaonkar, Biswanath Sarkar, Alex Cheru Pulikottil, Velusamy Chidambaram, Arumugam Velayutham Karthikeyani, Mohan Prabhu Kuvettu, Shiba Prasad Choudhury, Jayaraj Christopher, Brijesh Kumar, Biswapriya Das
  • Patent number: 10246385
    Abstract: A method of making light olefins is described. The method involves producing an alkyne in a pyrolysis process. The alkyne is catalytically hydrogenated in a hydrogenation zone to produce a product stream containing a light olefin. A byproduct stream from the pyrolysis process comprises carbon oxide and hydrogen. The byproduct stream is treated to convert the carbon oxide and the hydrogen to an oxygenated product in a carbon oxide conversion zone, which can then be converted to an olefin in an oxygenate to olefin process.
    Type: Grant
    Filed: December 19, 2017
    Date of Patent: April 2, 2019
    Assignee: UOP LLC
    Inventors: Rajeswar R. Gattupalli, Andrea G. Bozzano, Laura E. Leonard, Gregory A. Funk
  • Patent number: 10213773
    Abstract: The present invention relates to a process for converting oxygenates to olefins, comprising (1) providing a gas stream comprising one or more ethers; (2) contacting the gas stream provided in (1) with a catalyst, the catalyst comprising a support substrate and a layer applied to the substrate, the layer comprising one or more zeolites of the MFI, MEL and/or MWW structure type.
    Type: Grant
    Filed: June 15, 2016
    Date of Patent: February 26, 2019
    Assignee: BASF SE
    Inventors: Kirsten Spannhoff, Florina Corina Patcas, Ekkehard Schwab, Alexander Weck, Kerem Bay
  • Patent number: 10214461
    Abstract: A process for producing olefins from oxygenates can include the following steps: (i) heterogeneously catalyzed conversion of at least one oxygenate to a product stream containing C2 olefins, C3 olefins, C4 olefins, C5/6 hydrocarbon compounds, and C7+ hydrocarbon compounds; and (ii) separation of a propylene stream consisting of C3 olefins for at least 95 wt-%, wherein at least 10 wt-% of the propylene stream are recirculated into process step (i).
    Type: Grant
    Filed: September 2, 2015
    Date of Patent: February 26, 2019
    Assignee: L'Air Liquide Societe Anonyme Pour L'Etude Et L'Exploitation Des Procedes Georges Claude
    Inventors: Martin Rothamel, Stephane Haag, Frank Castillo-Welter, Peter Trabold, Martin Gorny, Sven Pohl
  • Patent number: 10207259
    Abstract: Prepare a hybrid SAPO-34/ZSM-5 catalyst via sequential steps as follows: a) form a mixture consisting essentially of ZSM-5 as a sole source of silicon atoms, aluminum isopropoxide and a solution of orthophosphoric acid; b) combine the mixture with an aqueous solution of tetraethylammonium hydroxide to form a reaction mixture; and c) subject the reaction mixture to hydrothermal conditions for a period of time sufficient to convert the reaction mixture to a hybrid SAPO-34/ZSM-5 catalyst. Use the hybrid catalyst in converting an oxygenate (methanol and/or dimethyl ether) to an olefin.
    Type: Grant
    Filed: September 9, 2015
    Date of Patent: February 19, 2019
    Assignee: Dow Global Technologies LLC
    Inventors: Yu Liu, Andrzej Malek
  • Patent number: 10196327
    Abstract: The invention is concerned with the production of 1-hexene and octenes from ethene. 1-Butene is optionally also to be produced. The problem addressed by the present invention is that of developing a process for producing 1-hexene from ethene by MTHxE etherification to achieve better chemical utilization of the employed carbon atoms. This problem is solved by catalytic retrocleavage of MTHxE into the C6 olefins and the alcohol, reuse of the alcohol in the etherification and reaction of the obtained C6 olefins with ethene to afford C8 olefins. In this way the alcohol is not lost from the process but rather is internally recirculated as a derivatizing agent. The less attractive C6 olefins from the cleavage product are upgraded to octene with further ethene in order to provide a further commercial product.
    Type: Grant
    Filed: June 15, 2017
    Date of Patent: February 5, 2019
    Assignee: Evonik Degussa GmbH
    Inventors: Guido Stochniol, Helene Reeker, Dietrich Maschmeyer, Stephan Peitz, Jörg Schallenberg
  • Patent number: 10144679
    Abstract: The present invention provides a process for the preparation of ethene by vapor phase chemical dehydration of a feed-stream comprising ethanol and optionally water and/or ethoxy ethane, said process comprising contacting a dried supported heteropolyacid catalyst in a reactor with the feed-stream having a feed temperature of at least 200° C.; wherein before the supported heteropolyacid catalyst is contacted with the feed-stream having a feed temperature of at least 200° C., the process is initiated by: (i) drying a supported heteropolyacid catalyst in a reactor under a stream of inert gas having a feed temperature of from above 100° C. to 200° C.; and (ii) contacting the dried supported heteropolyacid catalyst with an ethanol-containing vapor stream having a feed temperature of from above 100° C. to 160° C.
    Type: Grant
    Filed: November 19, 2015
    Date of Patent: December 4, 2018
    Assignee: Technip E&C Limited
    Inventors: Stephen Roy Partington, Stephen James Smith, Nakul Thakar
  • Patent number: 9975818
    Abstract: Processes are described for making biobased isoprene, wherein a biobased isobutene prepared from acetic acid in the presence of a catalyst is combined with a formaldehyde source to form a reaction mixture, and the reaction mixture is reacted to yield biobased isoprene. In certain embodiments, methyl-tert-butyl ether prepared by reacting the same biobased isobutene with methanol serves as a formaldehyde source, being oxidatively cracked to produce formaldehyde as well as isobutene for being converted to the biobased isoprene.
    Type: Grant
    Filed: April 10, 2015
    Date of Patent: May 22, 2018
    Assignees: Archer Daniels Midland Company, Washington State University
    Inventors: Junming Sun, Changjun Liu, Yong Wang, Kevin Martin, Padmesh Venkitasubramanian
  • Patent number: 9963477
    Abstract: The invention relates to a method for the isomerization of glucose into fructose in water in the presence of a solid base catalyst characterized by its reversibility of CO2 adsorption at a low temperature, the catalyst being a catalyst comprising at least one supported or non-supported lanthanide oxide or a molecular sieve based on silicon containing the organic template thereof. The invention also relates to a method for preparing HMF from glucose, comprising the isomerization of glucose into fructose.
    Type: Grant
    Filed: August 24, 2012
    Date of Patent: May 8, 2018
    Assignees: CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N.R.S.), UNIVERSITE CLAUDE BERNARD LYON I
    Inventors: Nadine Essayem, Rodrigo Lopes De Souza, Franck Rataboul, Cyril Feche, Dilson Cardoso, Demian Patrick Fabiano
  • Patent number: 9944861
    Abstract: A method for producing a hydrocarbon blendstock, the method comprising contacting at least one saturated acyclic alcohol having at least three and up to ten carbon atoms with a metal-loaded zeolite catalyst at a temperature of at least 100° C. and up to 550° C., wherein the metal is a positively-charged metal ion, and the metal-loaded zeolite catalyst is catalytically active for converting the alcohol to the hydrocarbon blendstock, wherein the method directly produces a hydrocarbon blendstock having less than 1 vol % ethylene and at least 35 vol % of hydrocarbon compounds containing at least eight carbon atoms.
    Type: Grant
    Filed: October 8, 2015
    Date of Patent: April 17, 2018
    Assignee: UT-BATTELLE, LLC
    Inventors: Chaitanya K. Narula, Brian H. Davison
  • Patent number: 9914672
    Abstract: A process for the production of jet and other heavy fuels from alcohols and mixture of alcohols is disclosed. The process may include contacting in a reaction zone at least one C2 to C11 alcohol with a solid catalyst having activity for the simultaneous dehydration of the alcohols to form olefins, isomerization of the olefins to form internal olefins, and oligomerization of the olefins produced in situ via the dehydration reaction to form an effluent comprising mono-olefinic hydrocarbons. Preferably, the alcohol feed is a mixture of alcohols, such as C2 to C7 alcohols or C4 and C6 alcohols, enabling the production of a mixture of branched hydrocarbons that may be used directly as a jet fuel without blending.
    Type: Grant
    Filed: October 14, 2013
    Date of Patent: March 13, 2018
    Assignee: Lummus Technology Inc.
    Inventors: Marvin I. Greene, Ruozhi Song, Arvids Judzis, Jr.
  • Patent number: 9902660
    Abstract: The invention provides a process for the preparation of an olefinic product, the process comprising the steps of: (a) reacting an oxygenate feedstock, comprising oxygenate, in an oxygenate reaction zone in the presence of a catalyst comprising a molecular sieve, at a temperature in the range of from 350 to 1000° C.
    Type: Grant
    Filed: December 13, 2013
    Date of Patent: February 27, 2018
    Assignee: SHELL OIL COMPANY
    Inventors: Antonius Gijsbertus Johannes Kloth, Sivakumar Sadasivan Vijayakumari, Jeroen Van Westrenen
  • Patent number: 9895671
    Abstract: A fluidized bed reactor is provided, comprising an inlet zone at a lower position, an outlet zone at an upper position, and a reaction zone between the inlet zone and the outlet zone. A guide plate with through holes is disposed in the reaction zone, comprising a dense channel region in an intermediate region thereof and a sparse channel region disposed on a periphery thereof and encompassing the dense channel region. Catalysts in said fluidized bed reactor can be homogeneously distributed in the reaction zone thereof, whereby the reaction efficiency can be improved. A reaction regeneration apparatus comprising said fluidized bed reactor, and a process for preparing olefins from oxygenates and a process for preparing aromatic hydrocarbons from oxygenates using the reaction regeneration apparatus.
    Type: Grant
    Filed: October 13, 2015
    Date of Patent: February 20, 2018
    Assignees: CHINA PETROLEUM & CHEMICAL CORPORATION, SHANGHAI RESEARCH INSTITUTE OF PETROCHEMICAL TECHNOLOGY SINOPEC
    Inventors: Weimin Yang, Xiaohong Li, Siqing Zhong, Guozhen Qi, Jun Xu, Zhinan Yu
  • Patent number: 9878962
    Abstract: A process for producing olefins from oxygenates comprises the following steps: (i) heterogeneously catalyzed conversion of at least one oxygenate to an entire stream containing liquid and gaseous organic compounds and water, and (ii) separating the entire stream in a first separating means into a fraction containing at least 90 vol-% of the gaseous organic compounds of the entire stream, into a fraction containing at least 90 wt-% of the liquid organic compounds of the entire stream, and into a fraction containing at least 90 wt-% of the water of the entire stream. Furthermore, the invention also comprises a plant for carrying out this process.
    Type: Grant
    Filed: December 3, 2013
    Date of Patent: January 30, 2018
    Assignee: L'AIR LIQUIDE SOCIÉTÉ ANONYME POUR L'ÉTUDE ET L'EXPLOITATION DES PROCEDES GEORGE CLAUDE
    Inventors: Bernd Ahlers, Martin Gorny, Hermann Bach
  • Patent number: 9725375
    Abstract: A method for improving the light olefin yield in the process of preparation of a light olefin using an oxygen-containing compound, more specifically, in which, a multi-stage dense phase fluidized bed comprising k secondary pre-carbon deposition zones (k?1) and n secondary reaction zones (n?1) is used as a reactor, and a multi-stage dense phase fluidized bed regenerator comprising in secondary regeneration zones (m?2) is used as a main equipment, and by re-refining hydrocarbons with four or more carbons obtained in the separation section, or adding naphtha, gasoline, condensate oil, light diesel oil, hydrogenation tail oil or kerosene in the reaction zone, the method primarily solves the problems in the prior art of the uniformity of carbon deposition amount and the carbon content of the catalyst being difficult to control, and the light olefin yield being low.
    Type: Grant
    Filed: December 3, 2013
    Date of Patent: August 8, 2017
    Assignee: DALIAN INSTITUTE OF CHEMICAL PHYSICS, CHINESE ACADEMY OF SCIENCES
    Inventors: Zhongmin Liu, Mao Ye, Tao Zhang, Changqing He, Xiangao Wang, Yinfeng Zhao
  • Patent number: 9718743
    Abstract: A method for preparing a light olefin using an oxygen-containing compound, and a device for use thereof, more specifically, taking methanol and/or dimethyl ether as main starting materials, using a multi-stage (n?2) dense phase fluidized bed reactor and a multi-stage (m?2) catalyst regenerator, which solves the problem in the prior art of the uniformity of catalyst carbon deposition and the carbon content being difficult to control and the light olefin selectivity being low.
    Type: Grant
    Filed: December 3, 2013
    Date of Patent: August 1, 2017
    Assignee: DALIAN INSTITUTE OF CHEMICAL PHYSICS, CHINESE ACADEMY OF SCIENCES
    Inventors: Zhongmin Liu, Mao Ye, Tao Zhang, Changqing He, Xiangao Wang, Yinfeng Zhao
  • Patent number: 9663414
    Abstract: A process for dehydration of an ethanol feedstock to ethylene by: a) preheating ethanol feedstock by heat exchange with effluent from e), b) pretreating the ethanol feedstock to produce pretreated ethanol feedstock, c) vaporizing a vaporization feedstock containing pretreated ethanol feedstock and at least a portion of the flow of treated water recycled in an exchanger to produce a vaporized feedstock, d) compressing said vaporized feedstock to produce a compressed feedstock, e) dehydrating said compressed feedstock in at least one adiabatic reactor, f) separating the effluent from the last adiabatic reactor of e) into an effluent containing ethylene and an effluent containing water, g) purifying at least a portion of the effluent containing water from 0 and separating at least one flow of treated water and at least one flow of unconverted ethanol, h) recycling at least a portion of the flow of treated water from g) upstream of c).
    Type: Grant
    Filed: November 18, 2013
    Date of Patent: May 30, 2017
    Assignees: TOTAL RESEARCH & TECHNOLOGY FELUY, IFP ENERGIES NOUVELLES
    Inventors: Vincent Coupard, Natacha Touchais, Thomas Plennevaux, Emilie Kobel, Stephanie Fleurier, Walter Vermeiren, Delphine Minoux, Philip De Smedt, Cindy Adam, Nikolai Nesterenko
  • Patent number: 9643898
    Abstract: Effect adiabatic, catalytic alkanol (alcohol) dehydration using two or more sequential dehydration catalyst beds each of which has disposed therein a different catalyst and, preferably, eliminating heating and heating apparatus disposed between each sequential pair of dehydration catalyst beds.
    Type: Grant
    Filed: November 17, 2014
    Date of Patent: May 9, 2017
    Assignee: Dow Global Technologies LLC
    Inventors: Derrick W. Flick, Mark W. Stewart
  • Patent number: 9604888
    Abstract: Method of producing ethylene and, optionally, propylene by subjecting a feedstock to steam cracking to produce a first olefin containing stream; heating an ethanol containing stream with heat from a steam cracker; passing the heated ethanol containing stream over a dehydration catalyst at a temperature between 200 C to 500 C preferably 250 C to 450 C to produce a second olefin containing stream; and combining the first and second olefin containing streams to give an initial product stream containing ethylene and optionally propylene. The initial product stream is subjected to purification including at least i) water content reduction ii) hydrogen content reduction iii) reduction of content of molecules containing 4 or more carbon atoms and iv) ethane content reduction.
    Type: Grant
    Filed: June 26, 2012
    Date of Patent: March 28, 2017
    Assignee: INEOS EUROPE AG
    Inventors: Laurent Caranoni, Bernard Descales, Neil Turnbull, Vaughn Clifford Williams
  • Patent number: 9598326
    Abstract: The present invention relates to a process for the conversion of oxygenates to olefins comprising (i) providing a gas stream comprising one or more oxygenates; and (ii) contacting the gas stream with a catalyst; wherein the catalyst comprises a zeolitic material having an MFI, MEL, and/or MWW-type framework structure comprising YO2 and X2O3, wherein Y is a tetravalent element, and X is a trivalent element, said zeolitic material being obtainable and/or obtained according to a method comprising (1) preparing a mixture comprising one or more sources for YO2, one or more sources for X2O3, and one or more solvents; and (2) crystallizing the mixture obtained in step (1) to obtain a zeolitic material having an MFI, MEL and/or MWW-type framework structure; wherein the mixture crystallized in step (2) contains 3 wt.-% or less of the one or more elements M based on 100 wt.-% of YO2, wherein M stands for sodium.
    Type: Grant
    Filed: November 11, 2013
    Date of Patent: March 21, 2017
    Assignee: BASF SE
    Inventors: Manuela Gaab, Ulrich Müller, Milan Kostur, Kirsten Spannhoff, Kerem Bay, Andrei-Nicolae Parvulescu
  • Patent number: 9586878
    Abstract: A method for synthesizing a sugar alcohol comprising the step of hydrolyzing a polysaccharide in the presence of hydrogen ions (H+), an alcoholic reducing agent and a hydrogen transfer catalyst to form the sugar alcohol.
    Type: Grant
    Filed: April 5, 2013
    Date of Patent: March 7, 2017
    Assignee: Agency for Science, Technology and Research
    Inventors: Guangshun Yi, Yugen Zhang
  • Patent number: 9580365
    Abstract: A process is disclosed for converting acetic acid to propylene and isobutene as the principal hydrocarbon products made, in the presence of a catalyst and in the further presence of hydrogen. In certain embodiments, a ZnxZryOz mixed oxide catalyst is used for carrying out a gas phase process, and propylene is produced preferentially to isobutene by using at least a certain amount of hydrogen in the process. In some embodiments, a ZnxZryOz mixed oxide catalyst made by an incipient wetness impregnation method is used and is indicated to be very stable for carrying out the conversion.
    Type: Grant
    Filed: April 10, 2015
    Date of Patent: February 28, 2017
    Assignee: Archer-Daniels-Midland-Company
    Inventors: Junming Sun, Changjun Liu, Yong Wang, Kevin Martin, Padmesh Venkitasubramanian
  • Patent number: 9505673
    Abstract: A process for the dehydration of an alcohol having at least 2 carbon atoms to make a corresponding olefin may include introducing in a reactor a stream (A) containing the alcohol, optionally water, and optionally an inert component. The stream (A) may be contacted with a catalyst in the reactor at conditions effective to dehydrate at least a portion of the alcohol to make the corresponding olefin. The process includes recovering from the reactor an olefin containing stream (B). The catalyst may be a crystalline silicate, dealuminated crystalline silicate, or phosphorus modified crystalline silicate, each of the group FER, MWW, EUO, MFS, ZSM-48, MTT or TON having Si/Al ranging from 25 to 90. The weight hourly space velocity (WHSV) of the alcohol may be at least 4 h?1. The temperature may range from 280° C. to 600° C., or from 320° C. to 600° C.
    Type: Grant
    Filed: July 23, 2015
    Date of Patent: November 29, 2016
    Assignee: Total Research & Technology Feluy
    Inventors: Delphine Minoux, Nikolai Nesterenko, Cindy Adam, Sander Van Donk, Walter Vermeiren
  • Patent number: 9447346
    Abstract: A two-step process for the oligomerization and hydration of a mixed butenes feed is provided and is implemented in a two-stage system. The two-step process yields a product consisting of diisobutenes (DIBs) and mixed butanols. The DIBs are produced via the selective oligomerization of isobutene in a first stage and the mixed butanols are produced via the hydration, in a second stage, of mixed butenes that remain unreacted in the first stage.
    Type: Grant
    Filed: December 11, 2013
    Date of Patent: September 20, 2016
    Assignee: SAUDI ARABIAN OIL COMPANY
    Inventors: Kareemuddin M. Shaik, Wei Xu, Thamer Mohammed, Hassan Babiker, Gautam Tavanappa Kalghatgi
  • Patent number: 9422205
    Abstract: Process for the production of high-purity isobutene starting from a stream prevalently containing MTBE (Methyl-Tert Butyl Ether) or ETBE (Ethyl-Tert Butyl Ether) which essentially comprises the following areas in sequence: • a fractionation area for obtaining a stream of high-purity MTBE or ETBE; • a cracking area of said stream of MTBE or ETBE for obtaining an outgoing stream prevalently containing isobutene and the relative alcohol, methanol or ethanol; • a washing area with water of the stream leaving the cracking area for the recovery of the relative alcohol, in order to obtain a stream containing isobutene, the ether fed and light compounds and a stream substantially consisting of water and relative alcohol, with a relevant fractionation section for separating the washing water to be recycled to the same washing area from the relative alcohol; • a fractionation area of the stream containing isobutene, the ether fed and light compounds for separating a stream of high-purity isobutene.
    Type: Grant
    Filed: October 4, 2013
    Date of Patent: August 23, 2016
    Assignee: Saipem S.P.A.
    Inventors: Maura Brianti, Massimo Conte
  • Patent number: 9388052
    Abstract: A silicoaluminophosphate molecular sieve being represented by the compositional formula (SiaAlbPcMd)O2 where M is magnesium, a is 0.05 to 0.17, b is 0.45 to 0.55, c is 0.33 to 0.45, d is 0.001 to 0.030, and a+b+c+d=1, and an average primary particle size of 60 nm or less. A method of producing the silicoaluminophosphate molecular sieve includes carrying out a hydrothermal treatment on a mixture that contains a silicon source, an aluminum source, a phosphorus source, a structure-directing agent, and at least one of an inorganic magnesium salt or an organic magnesium salt or an inorganic manganese salt or an organic manganese salt at 0.001 to 0.1 mole per mole of the aluminum source.
    Type: Grant
    Filed: August 20, 2012
    Date of Patent: July 12, 2016
    Assignee: TOYOTA JIDOSHA KABUSHIKI KAISHA
    Inventor: Kanji Takaoka
  • Patent number: 9295963
    Abstract: A process for producing light olefins is provided. A feedstock enters a pre-reaction zone and contacts a catalyst comprising at least one silicon-aluminophosphate molecular sieve and produces a gas-phase stream; the gas-phase stream and the catalyst enter at least one riser, and the gas-phase stream and the catalyst pass from an outlet of the at least one riser and enter a gas-solid rapid separation zone; the separated gas-phase stream enters a separation section; a first portion of the separated catalyst returns to the pre-reaction zone, and a second portion is regenerated in a regenerator; wherein an inlet of the at least one riser extends into the pre-reaction zone, about 60% to about 90% of the height of the at least one riser passes through a heat exchange zone, and the outlet extends into the gas-solid rapid separation zone.
    Type: Grant
    Filed: March 5, 2014
    Date of Patent: March 29, 2016
    Assignees: China Petroleum & Chemical Corporation, Shanghai Research Institute of Petrochemical Technology, Sinopec
    Inventors: Guozhen Qi, Siqing Zhong, Wei Chen, Zhinan Yu
  • Patent number: 9233350
    Abstract: The invention provides a start-up method for a reaction-regeneration unit for preparing light olefins from methanol, which comprises: (a) heating a regenerator with an auxiliary combustion chamber and a reactor with a start-up furnace; (b) charging a catalyst into the regenerator and reactor; (c) closing a spent catalyst slide valve and a regenerated catalyst slide valve after the reactor reaches about 350° C. or more; (d) feeding methanol to the reactor after the dense phase stage of the regenerator reaches about 350° C. or more; (e) opening the spent catalyst slide valve and introducing a carbon deposited catalyst from the reactor to the regenerator after the dense phase stage reaches about 400° C. or more and the average amount of carbon deposits on the catalyst in the reactor reaches about 2.5% or more; (f) raising the regenerator to above about 580° C.; and (g) stopping the start-up furnace and auxiliary combustion chamber.
    Type: Grant
    Filed: January 8, 2013
    Date of Patent: January 12, 2016
    Assignees: CHINA PETROLEUM & CHEMICAL CORPORATION, SHANGHAI RESEARCH INSTITUTE OF PETROCHEMICAL TECHNOLOGY, SINOPEC
    Inventors: Guozhen Qi, Siqing Zhong, Zhinan Yu, Yongming Jin
  • Patent number: 9233885
    Abstract: A process and apparatus is presented for the improved selectivity of oxygenate conversion to olefins. The process includes passing a process stream through a two stage reactor, wherein the process stream is separated from the catalyst in the first stage before passing the process stream to the second stage. The catalyst is continuously passed through the two stages, and cycles through a regeneration unit to control the carbon content on the catalyst.
    Type: Grant
    Filed: June 3, 2010
    Date of Patent: January 12, 2016
    Assignee: UOP LLC
    Inventors: Carl J. Stevens, Paul A. Sechrist, Richard A. Johnson, II
  • Patent number: 9227885
    Abstract: A process for the conversion of an alcohol mixture may include introducing into a reactor a stream including the alcohol mixture mixed with a stream including olefins having 4 carbon atoms or more. The process may include contacting the stream with a single catalyst at a temperature above 500° C. in the reactor at conditions effective to dehydrate isobutanol, forming C4+ olefins, and to catalytically crack the C4+ olefins. The single catalyst may be an acid catalyst adapted to cause both the dehydration and catalytic cracking. The process may include recovering an effluent including ethylene, propylene, and water, and fractionating the effluent.
    Type: Grant
    Filed: August 20, 2015
    Date of Patent: January 5, 2016
    Assignee: TOTAL RESEARCH & TECHNOLOGY FELUY
    Inventors: Cindy Adam, Delphine Minoux, Nikolai Nesterenko, Sander Van Donk, Jean-Pierre Dath
  • Patent number: 9206099
    Abstract: Provided is a method for efficiently producing high-purity hydrogenated biphenol based on a simple method that can be industrially utilized using easily-available biphenol as a starting material. The method for producing hydrogenated biphenol according to the present invention is a method for producing hydrogenated biphenol by hydrogenating biphenol represented by the following formula (1): to obtain hydrogenated biphenol represented by the following formula (2): the method including: a reaction step of hydrogenating the biphenol represented by formula (1); and a purification step of washing or crystallizing a reaction product obtained from the reaction step using an aromatic hydrocarbon.
    Type: Grant
    Filed: March 28, 2013
    Date of Patent: December 8, 2015
    Assignee: DAICEL CORPORATION
    Inventors: Mitsuru Ohno, Tomohiro Hashizume
  • Patent number: 9199845
    Abstract: Process for producing alkene(s) from an oxygenate feedstock in a reactor by dehydration in the presence of a supported heteropolyacid catalyst. The pore volume of the supported heteropolyacid catalyst satisfies the following formula: PV>0.6?0.3[HPAloading/Surface Area of Dried Catalyst]where; PV is the Pore Volume of the dried supported heteropolyacid catalyst (measured in ml/g catalyst); HPA loading is the amount of heteropolyacid present in the dried supported heteropolyacid catalyst (measure in micro moles/g); and Surface Area of Dried Catalyst is the surface area of the dried supported heteropolyacid catalyst (measured in m2/g).
    Type: Grant
    Filed: November 8, 2007
    Date of Patent: December 1, 2015
    Assignee: BP CHEMICALS LIMITED
    Inventors: Benjamin Patrick Gracey, Gordon John Haining, Stephen Roy Partington
  • Patent number: 9162950
    Abstract: Provided is a method for efficiently producing high-purity hydrogenated biphenol based on a simple method that can be industrially utilized using easily-available biphenol as a starting material. The method for producing hydrogenated biphenol according to the present invention is a method for producing hydrogenated biphenol by hydrogenating biphenol represented by the following formula (1): to obtain hydrogenated biphenol represented by the following formula (2): the method including: a reaction step of hydrogenating the biphenol represented by formula (1); and a purification step of washing or crystallizing a reaction product obtained from the reaction step using an aromatic hydrocarbon.
    Type: Grant
    Filed: March 28, 2013
    Date of Patent: October 20, 2015
    Assignee: DAICEL CORPORATION
    Inventors: Mitsuru Ohno, Tomohiro Hashizume
  • Patent number: 9120069
    Abstract: A process and a reactor system for the preparation of an olefinic product by reacting an oxygenate feedstock in the presence of an oxygenate conversion catalyst within a reactor system under oxygenate-to-olefin conversion conditions, to obtain the olefinic product, wherein the reactor system has a contact surface coming in contact with oxygenates and wherein at least part of the contact surface is an material of the formula MX wherein: M is a metal and X is C, or M is a metal or Si and X is N.
    Type: Grant
    Filed: December 21, 2009
    Date of Patent: September 1, 2015
    Assignee: Shell Oil Company
    Inventors: Leslie Andrew Chewter, Jeroen Van Westrenen, Ferry Winter
  • Patent number: 9102532
    Abstract: Method for producing synthesis gas for methanol production The present invention relates to a method for producing synthesis gas from a hydrocarbon containing feed, which synthesis gas is particularly suitable for subsequent use in methanol production. In this method, a feed (100) is divided into two streams, wherein one stream is subjected to catalytic partial oxidation (CPO) (2) and the other stream is subjected to steam reforming (5) followed by a water gas shift reaction (51). The two streams are then recombined and can be used further in methanol synthesis (6). The recombined stream preferably has an R ratio, being a molar ratio (H2?C02)/(CO+C02), in the range of 1.9-2.2 and preferably about 2. The invention further relates to a method for producing methanol from a hydrocarbon containing feed, wherein first synthesis gas is obtained according to the method of the invention, which synthesis gas is further used to produce methanol.
    Type: Grant
    Filed: October 26, 2012
    Date of Patent: August 11, 2015
    Assignee: STAMICARBON B.V.
    Inventors: Gaetano Iaquaniello, Elena Antonetti, Palma Contaldo
  • Patent number: 9085500
    Abstract: A process for producing a product containing C3H6 and C2H4 includes simultaneous conversion of MeOH and EtOH in an adiabatic sequentially operated reactor containing a plurality of reaction stages. Each of the plurality of reaction stages of the reactor is provided with a fixed bed of a form-selective catalyst. A gaseous feed stream including MeOH, DME and H2O is charged to at least a first of the reaction stages of the reactor with a temperature in a range of 300 to 600° C. at a pressure in a range of 0.1 to 20 bar[a]. EtOH is fed into at least, one of the reaction stages of the reactor.
    Type: Grant
    Filed: November 25, 2009
    Date of Patent: July 21, 2015
    Assignee: AIR LIQUIDE GLOBAL E&C SOLUTIONS GERMANY GMBH
    Inventors: Henning Buchold, Harald Koempel, Sven Pohl, Martin Rothaemel, Ulrich Wagner
  • Patent number: 9067860
    Abstract: The invention relates to a process for converting an alkyl tert-alkyl ether into an alkanol and an iso-alkane wherein the alkyl tert-alkyl ether is contacted with a hydrocracking catalyst in the presence of hydrogen under hydrocracking process conditions.
    Type: Grant
    Filed: October 16, 2012
    Date of Patent: June 30, 2015
    Assignee: Shell Oil Company
    Inventors: Leslie Andrew Chewter, Hervé Henry, Pieter Oldenhove, Rajaram Ramesh, Jeroen Van Westrenen
  • Patent number: 9035120
    Abstract: A method of making light olefins in a combined XTO (organics to olefins) and OCP (olefins cracking) process, from an oxygen-containing, halogenide-containing, or sulphur-containing organic feedstock contacted with a catalyst in a first reactor to convert the feedstock into a reactor effluent comprising light olefins and a heavy hydrocarbon fraction; separating the light olefins from the heavy hydrocarbon fraction, then contacting the heavy hydrocarbon fraction in a second reactor with a catalyst to convert a portion of the heavy hydrocarbons into light olefins; wherein the catalyst is a zeolite selected among a H+ or NH4+—form of MFI, MEL, FER, MOR, or clinoptilolite; modifying the zeolite by adding from 0.05 to 7 wt % of phosphorous to the zeolite, and an optional washing and/or drying in either order, then calcination. In an embodiment, the initial zeolite Si:Al atomic ratio of at least one catalyst is 100 or less.
    Type: Grant
    Filed: July 28, 2008
    Date of Patent: May 19, 2015
    Assignee: TOTAL RESEARCH & TECHNOLOGY FELUY
    Inventors: Nikolai Nesterenko, Walter Vermeiren, Delphine Minoux, Sander Van Donk
  • Patent number: 9029619
    Abstract: The present invention relates to a process to make alpha olefins comprising: dehydrating ethanol to recover an ethylene stream, introducing said ethylene stream into an oligomerization zone containing an oligomerization catalyst and into contact with said oligomerization catalyst, operating said oligomerization zone at conditions effective to produce an effluent consisting essentially of 1-butene, 1-hexene, optionally heavier alpha olefins and unconverted ethylene if any, introducing the above effluent into a fractionation zone to recover a stream consisting essentially of 1-butene, a stream consisting essentially of 1-hexene, optionally a stream consisting essentially of heavier alpha olefins and an optional ethylene stream. In an advantageous embodiment the 1-hexene or at least one heavier alpha olefins, if any, are isomerized to an internal olefin and subsequently transformed by metathesis with the aid of additional ethylene into different alpha-olefins with even or odd number of carbons.
    Type: Grant
    Filed: December 10, 2009
    Date of Patent: May 12, 2015
    Assignee: Total Research & Technology Feluy
    Inventor: Walter Vermeiren
  • Patent number: 9024103
    Abstract: The present invention provides a method for producing an olefin from a carboxylic acid having a ?-hydrogen atom or an anhydride thereof in the presene of a catalyst containing at least one metal element selected from metals of Group 8, Group 9 and Group 10 and bromine element at a reaction temperature of 120° C. to 270° C.
    Type: Grant
    Filed: November 10, 2010
    Date of Patent: May 5, 2015
    Assignee: Kao Corporation
    Inventors: Daisuke Ishihara, Nobuyoshi Suzuki, Hideo Tahara, Hiroshi Danjo
  • Publication number: 20150119616
    Abstract: A method for converting oxygenates to olefins comprising: a) feeding an oxygenate containing stream to a reactor; b) contacting the oxygenate containing stream with a molecular sieve catalyst under oxygenate-to-olefin conversion conditions to form products wherein the catalyst becomes deactivated due to the formation of coke on the catalyst; c) removing the products from the reactor; d) removing at least a portion of the catalyst from the reactor and sending the catalyst to a catalyst regenerator; e) contacting the catalyst with a regeneration medium and a fuel to combust at least a portion of the coke and to heat the catalyst; and f) returning at least a portion of the heated catalyst to the reactor wherein the fuel is a light hydrocarbon gas that has been at least partially diluted with nitrogen and/or air.
    Type: Application
    Filed: October 29, 2014
    Publication date: April 30, 2015
    Inventors: Richard Addison SANBORN, Sivakumar SADASIVAN VIJAYAKUMARI, Leslie Andrew CHEWTER, Ye-Mon CHEN
  • Patent number: 9000246
    Abstract: Methods are provided for refining natural oil feedstocks and producing dibasic esters and/or dibasic acids. The methods comprise reacting a terminal olefin with an internal olefin in the presence of a metathesis catalyst to form a dibasic ester and/or dibasic acid. In certain embodiments, the olefin esters are formed by reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters, separating the olefins from the esters in the metathesized product, and transesterifying the esters in the presence of an alcohol to form a transesterified product having olefin esters.
    Type: Grant
    Filed: October 9, 2012
    Date of Patent: April 7, 2015
    Assignee: Elevance Renewable Sciences, Inc.
    Inventors: Thomas E. Snead, Steven A. Cohen, Demond L. Gildon
  • Patent number: 9000248
    Abstract: The present invention relates to a process for producing an olefin, including the step of subjecting an aliphatic primary alcohol having 12 to 24 carbon atoms to liquid phase dehydration reaction in the presence of a solid acid catalyst, wherein among a total acid content of the solid acid catalyst as measured by an ammonia temperature-programmed desorption (NH3-TPD) method, an acid content of the solid acid catalyst as calculated from an amount of ammonia desorbed at a temperature not higher than 300° C. in the method is 70% or larger of the total acid content.
    Type: Grant
    Filed: October 29, 2010
    Date of Patent: April 7, 2015
    Assignee: KAO Corporation
    Inventor: Shingo Takada
  • Publication number: 20150087866
    Abstract: The present invention relates to the process of production of olefins by means of the dehydration of light alcohols using ionic liquids as an acidic medium. Furthermore, the present invention relates to the use of such olefins, for example, for the production of polymers and ethylene glycol.
    Type: Application
    Filed: August 30, 2012
    Publication date: March 26, 2015
    Applicants: UNIVERSIDADE FEDERAL DO RIO GRANDE DO SUL-UFRGS, BRASKEM S.A.
    Inventor: Michèle Oberson De Souza