From Nonhydrocarbon Feed Patents (Class 585/638)
  • Patent number: 10640582
    Abstract: The present invention relates to an olefin polymerization process comprising polymerization of at least one olefin monomer in one or more polymerization reactors. In addition, the present invention relates to a system for vapor phase polymerization of at least one polymerizable monomer.
    Type: Grant
    Filed: November 29, 2016
    Date of Patent: May 5, 2020
    Assignee: SABIC GLOBAL TECHNOLOGIES B.V.
    Inventors: Petrus Johannes Hubertus Bronsaer, Arjen van Miltenburg
  • Patent number: 10550046
    Abstract: Provided are: a catalyst for dehydration, with which isobutylene is able to be produced with high conversion and high selectivity through a dehydration reaction of isobutanol; and a method for producing isobutylene. This catalyst has a BET specific surface area within the range of from 210 m2/g to 350 m2/g (inclusive) as calculated from N2 adsorption/desorption isotherms. It is preferable that this catalyst is formed of at least one substance selected from among alumina, silica alumina, zeolite, and solid phosphoric acid. It is more preferable that this catalyst contains alumina, and it is especially preferable that this catalyst is formed of alumina. In this method for producing isobutylene, the isobutanol concentration in the starting material gas is preferably 20% by volume or more, more preferably 40% by volume or more, and especially preferably 60% by volume or more. In addition, the temperature of a catalyst layer is preferably from 230° C. to 370° C. (inclusive), and more preferably from 240° C.
    Type: Grant
    Filed: April 20, 2016
    Date of Patent: February 4, 2020
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Tatsuya Suzuki, Akio Takeda, Toshiya Yasukawa, Wataru Ninomiya, Ken Ooyachi
  • Patent number: 10384986
    Abstract: A process is presented for the production of light olefins. The process utilizes a SAPO-18 catalyst and is operated at an elevated pressure. The process generates higher concentrations of heavier olefins which can then be processed to generate light olefins. The processing of the heavier olefins can include metathesis reactions and olefin cracking processes.
    Type: Grant
    Filed: June 7, 2019
    Date of Patent: August 20, 2019
    Assignee: UOP LLC
    Inventors: Thulasidas Chellppannair, Nicholas J. Schoenfeldt, Andrea G. Bozzano, Wolfgang A. Spieker, Christopher D. DiGiulio, Gregory A. Funk, Jaime G. Moscoso
  • Patent number: 10131588
    Abstract: Carbon monoxide and molecular hydrogen are converted to an alcohol mixture, which is separated into a first methanol-containing stream and a second C2+ alcohol-containing stream. The first stream's methanol is converted into a propylene-rich product, and the second stream's C2+ alcohol is converted to ethylene and additional propylene.
    Type: Grant
    Filed: November 17, 2014
    Date of Patent: November 20, 2018
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Nikolaos Soultanidis, James H. Beech, Jr., Steven E. Silverberg
  • Patent number: 10093593
    Abstract: A process is presented for generating light olefins with the methanol to olefins process from a combination of catalysts. The process controls the product distribution for ethylene, propylene and butylenes, to enable shifting of the product distribution. The process includes passing a second catalyst to a reactor while the process is on-going.
    Type: Grant
    Filed: June 8, 2017
    Date of Patent: October 9, 2018
    Assignee: UOP LLC
    Inventors: Gregory A. Funk, Andrea G. Bozzano, Nicholas J. Schoenfeldt, Thulasidas Chellppannair, Wolfgang A. Spieker, Bipin V. Vora
  • Patent number: 10059638
    Abstract: Processes are provided for conversion of oxygenated hydrocarbon, such as methanol and/or dimethyl ether, to aromatics, such as a para-xylene, and olefins, such as ethylene and propylene. The processes entail using a reactor having multiple reaction zones where each zone is prepared to promote desired reactions.
    Type: Grant
    Filed: December 7, 2015
    Date of Patent: August 28, 2018
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Nikolaos Soultanidis, Jeevan S. Abichandani, Mayank Shekhar
  • Patent number: 9938205
    Abstract: Apparatuses and processes for converting an oxygenate feedstock, such as methanol and dimethyl ether, in a fluidized bed containing a catalyst to hydrocarbons, such as gasoline boiling components, olefins and aromatics are provided herein.
    Type: Grant
    Filed: October 1, 2015
    Date of Patent: April 10, 2018
    Assignee: EXXONMOBIL RESEARCH AND ENGINEERING COMPANY
    Inventors: Bing Du, Samuel A. Tabak, Mitch L. Hindman, Eric B. Shen, David L. Johnson, Mohsen N. Harandi, Clay R. Sutton, Lu Han, Michael F. Raterman, Zhongcheng Wang, Rohit Vijay, Stephen J. McCarthy
  • Patent number: 9902663
    Abstract: Production of a mixture of ethylene and propylene from a mixture containing ethanol and isopropanol and having a water content between 30 and 75 wt. % is obtained by a process comprising: a) contacting the mixture in a dehydration unit with a dehydration catalyst chosen from: an alumina (A) having a BET specific surface area between 200 and 350 m2/g, a mean mesopore diameter between 5 and 15 nm, a sodium content of less than 50 ppm by weight, and a sulphur content of less than 40 ppm by weight; and an alumina (B) having a BET specific surface area between 130 and 180 m2/g, a mean mesopore diameter between 14 and 20 nm, a sodium content between 300 and 600 ppm by weight, and a sulphur content between 800 and 1300 ppm by weight; b) withdrawing an effluent containing ethylene and propylene from the dehydration unit.
    Type: Grant
    Filed: October 8, 2014
    Date of Patent: February 27, 2018
    Assignees: IFP Energies nouvelles, TOTAL RESEARCH & TECHNOLOGY FELUY
    Inventors: Nicolas Aribert, Laure Brandhorst, Vincent Coupard, Sylvie Maury, Tom Vivien
  • Patent number: 9878963
    Abstract: The invention relates to process for the preparation of an olefinic product comprising ethylene and/or propylene from an oxygenate, the process comprising the following steps: a) an oxygenate conversion step wherein a gaseous effluent comprising olefins and a water-soluble oxygenate is obtained; b) separation of water from the effluent; c) compression of the effluent; d) acid gas removal from the compressed gaseous effluent obtained in step c), wherein the compressed gaseous effluent is treated with a caustic solution in a caustic tower; and e) separating the olefinic product from the gaseous effluent treated in step d), wherein, in a final stage in the caustic tower, water-depleted compressed gaseous effluent is treated with a water stream that is essentially free of water-soluble oxygenate and a spent water stream comprising caustic and water-soluble oxygenate is obtained, which spent water stream is withdrawn from the process.
    Type: Grant
    Filed: December 24, 2013
    Date of Patent: January 30, 2018
    Inventors: Antonius Gijsbertus Johannes Kloth, Sivakumar Sadasivan Vijayakumari, Jeroen Van Westrenen
  • Patent number: 9873655
    Abstract: Processes for producing carboxylic acid are included herein. The processes include contacting methanol and carbon monoxide in the presence of a liquid reaction medium under carbonylation conditions sufficient to form a carbonylation product including acetic acid and one or more components selected from acetaldehyde, formic acid and combinations thereof, wherein the liquid reaction medium includes: a carbonylation catalyst selected from rhodium catalysts, iridium catalysts and palladium catalysts; and water in a water concentration in a range of 1 wt. % to 14 wt. % based on the total weight of the liquid reaction medium; and contacting at least a portion of the carbonylation product or a derivative thereof with an adsorbent at adsorption conditions sufficient to selectively reduce a concentration of one or more components present in the carbonylation product, wherein the adsorbent includes a silicoaluminophosphate (SAPO).
    Type: Grant
    Filed: December 2, 2016
    Date of Patent: January 23, 2018
    Assignee: LyondellBasell Acetyls, LLC
    Inventors: Noel C. Hallinan, David L. Ramage, Daniel F. White, Brian A. Salisbury, John D. Hearn
  • Patent number: 9840670
    Abstract: Carbon dioxide is hydrogenated by water at elevated temperature in an inorganic sulfate fortified sulfuric acid medium, in the presence of a transition metal catalyst and the absence of a sacrificial metal or hydrogen gas. The reaction sequence forms formaldehyde, immediately forming glycolaldehyde then concatenating to longer hydrocarbon chains possessing at least one alcohol group to maintain solubility in the reaction medium. As products of sufficient molecular weight are attained the alcohol group becomes hydrogenated and the hydrocarbons vaporize. Water's hydrogen is sacrificed as the byproduct oxygen reacts with sulfuric acid forming monoperoxysulfuric acid (Caro's acid) that decomposes at elevated temperatures. Products are removed under partial vacuum to preclude partial oxidation of the hydrocarbon fuels facilitating a continuous process.
    Type: Grant
    Filed: May 12, 2016
    Date of Patent: December 12, 2017
    Inventor: M. K. Carter
  • Patent number: 9834488
    Abstract: The invention provides a process for the preparation of an olefinic product, the comprising: (a) reacting an oxygenate to produce an effluent stream, comprising at least oxygenate, olefin, water and acidic by-products; (b) cooling the effluent stream by means of an indirect heat exchange to a temperature greater than the dew point temperature of effluent stream; (c) further rapidly cooling the effluent stream to a temperature at or lower than the dew point temperature of the reaction effluent stream by direct injection of a first aqueous liquid into the effluent stream, to form a quench effluent stream; (d) separating the first quench effluent stream into a liquid quench stream and a gaseous quench stream; and passing the gaseous quench stream into a quench tower and contacting the gaseous quench stream with a second aqueous liquid, to produce a quench tower gaseous stream comprising the olefinic product.
    Type: Grant
    Filed: October 29, 2013
    Date of Patent: December 5, 2017
    Assignee: SHELL OIL COMPANY
    Inventors: Antonius Gijsberius Johannes Kloth, Sivakumar Sadasivan Vijayakumari, Jeroen Van Westrenen
  • Patent number: 9828306
    Abstract: The invention provides a process for preparing an olefin, comprising: (a) reacting an oxygenate, in a reaction zone in the presence of a molecular sieve catalyst, at a temperature from 350 to 1000° C., to produce a effluent stream, comprising at least oxygenate, olefin, water and acidic by-products; (b) cooling the reaction effluent stream by an indirect heat exchange to a temperature greater than the dew point temperature of effluent stream; (c) further rapidly cooling the effluent stream to a temperature lower than the dew point temperature of the effluent stream by direct injection of an aqueous liquid into the effluent stream, to form a quench effluent stream; and (d) passing the quench effluent stream into a quench tower and contacting the quench effluent stream with a second aqueous liquid in the presence of at least one set of internals, to produce a quench tower gaseous stream comprising the olefin.
    Type: Grant
    Filed: October 29, 2013
    Date of Patent: November 28, 2017
    Assignee: SHELL OIL COMPANY
    Inventors: Antonius Gijsbertus Johannes Kloth, Sivakumar Sadasivan Vijayakumari, Jeroen Van Westrenen
  • Patent number: 9714200
    Abstract: The invention relates to a process for the continuous production of one or more olefins from an aqueous solution of corresponding alcohol(s) including: Providing a solid-free aqueous solution of the alcohol(s); putting the solution through a reactor, which is filled with a fixed-bed catalyst such that the solution comes into contact with the catalyst when flowing through the reactor at a temperature of at least 300° C. and a pressure of at least 220 bar in such a temperature/pressure combination that the alcohol(s) are reacted under supercritical conditions; and transferring a resulting two-stage mixture to a separator, in which the mixture is separated in a raw olefin gas phase and an aqueous liquid phase; wherein the catalyst is selected from among metal oxides having the properties of a Bronstedt acid, insoluble metallic or semi-metallic phosphates as well as porous materials selected from among pumice and carbon, the surface area of which is coated with inorganic acid groups.
    Type: Grant
    Filed: January 24, 2013
    Date of Patent: July 25, 2017
    Assignee: Fraunhofer-Gesellschaft zur Foerderung der angewandten Forschung e.V.
    Inventors: Gerd Unkelbach, Rainer Schweppe, Thomas Hirth
  • Patent number: 9682915
    Abstract: Production of methacrylic acid ester comprising a step of having acetone undergo a dehydration reaction in the presence of a dehydration reaction catalyst to obtain a reaction mixture; a step of separating a mixture containing propyne and propadiene as main components from the obtained reaction mixture; a step of separating the separated mixture containing propyne and propadiene as main components into a liquid, gas, or gas-liquid mixture containing propyne as a main component, and a liquid, gas, or gas-liquid mixture containing propadiene as a main component; and a step of bringing the obtained liquid, gas, or gas-liquid mixture containing propyne as a main component into contact with carbon monoxide and an alcohol having 1 to 3 carbon atoms in the presence of a catalyst containing at least one selected from the group consisting of Group 8 metal elements, Group 9 metal elements, and Group 10 metal elements.
    Type: Grant
    Filed: March 19, 2014
    Date of Patent: June 20, 2017
    Assignee: SUMITOMO CHEMICAL COMPANY, LIMITED
    Inventors: Kohei Seki, Tetsuya Suzuta, Naoki Miura
  • Patent number: 9567266
    Abstract: The invention has objects of providing an olefin production method which can produce an olefin with high efficiency by the dehydration reaction of an alcohol even in the presence of a ketone without the occurrence of side reactions such as the Aldol condensation of the ketone, as well as providing an olefin production method which can produce an olefin with high activity and high selectivity in a single reaction step by directly reacting a corresponding ketone and hydrogen.
    Type: Grant
    Filed: December 20, 2012
    Date of Patent: February 14, 2017
    Assignee: MITSUI CHEMICALS, INC.
    Inventors: Masayasu Ishibashi, Tsuneyuki Ohkubo
  • Patent number: 9550178
    Abstract: Disclosed is a method for converting an alkyl halide to an olefin. The method includes contacting a silicoaluminophosphate (SAPO) catalyst with a feed that includes an alkyl halide under reaction conditions sufficient to produce an olefin hydrocarbon product that includes C2 to C4 olefins. The SAPO catalyst has bimodal acidity designated as weak acid sites and strong acid sites. The weak acid concentration is less than 0.55 mmol/g-cat and the total acid concentration is less than 1.5 mmol/g-cat.
    Type: Grant
    Filed: July 28, 2015
    Date of Patent: January 24, 2017
    Assignee: SABIC Global Technologies B.V.
    Inventors: Ashim Kumar Ghosh, Alla Khanmamedova, Mike Mier, Jonathan Banke
  • Patent number: 9546116
    Abstract: A catalyst composite may include a molecular sieve having pores of 10- or more-membered rings and a metal silicate different from the molecular sieve. The metal silicate may include at least one alkaline earth metal and one or more of the following metals: Ga, Al, Ce, In, Cs, Sc, Sn, Li, Zn, Co, Mo, Mn, Ni, Fe, Cu, Cr, Ti and V. The catalyst composite may include at least 0.1 wt % of silicate. The catalyst composite may be used in an XTO reactor or for catalytic cracking.
    Type: Grant
    Filed: December 29, 2015
    Date of Patent: January 17, 2017
    Assignee: TOTAL RESEARCH & TECHNOLOGY FELUY
    Inventors: Nikolai Nesterenko, Walter Vermeiren, Sander Van Donk
  • Patent number: 9505669
    Abstract: The invention provides a process for the preparation of an olefinic product comprising ethylene and/or propylene comprising: a) steam cracking a paraffinic feedstock to obtain an effluent comprising olefins; b) converting an oxygenate to obtain a gaseous effluent comprising olefins; c) subjecting both effluents to water removal and compression steps, wherein the effluents are combined before the water removal step, between the water removal and the compression steps or after the compression step to obtain a combined gaseous effluent; d) removing acid gas from the combined gaseous effluent obtained in step c), wherein the combined gaseous effluent is treated with a caustic solution in a caustic tower and a non-aqueous liquid stream comprising one or more aromatic C7+ hydrocarbons is added to the caustic solution to control the formation of red oil, to obtain a treated gaseous effluent; and e) separating the olefinic product from the treated gaseous effluent.
    Type: Grant
    Filed: December 24, 2013
    Date of Patent: November 29, 2016
    Assignee: Shell Oil Company
    Inventors: Jeroen Van Westrenen, Sivakumar Sadasivan Vijayakumari
  • Patent number: 9505670
    Abstract: The invention relates to a process for the preparation of an olefinic product comprising ethylene and/or propylene from an oxygenate comprising: a) an oxygenate conversion step wherein a gaseous effluent comprising olefins is obtained; b) separation of water from the effluent; c) compression of the effluent; d) acid gas removal from the effluent wherein the water-depleted compressed gaseous effluent is treated with a caustic solution in a caustic tower and a non-aqueous liquid stream comprising one or more aromatic C7+ hydrocarbons is added to the caustic solution to control the formation of red oil; and e) separating the olefinic product from the gaseous effluent treated in step d).
    Type: Grant
    Filed: December 24, 2013
    Date of Patent: November 29, 2016
    Assignee: Shell Oil Company
    Inventors: Sivakumar Sadasivan Vijayakumari, Jeroen Van Westrenen
  • Patent number: 9399603
    Abstract: A process is presented for increasing the conversion efficiency of oxygenates to olefins. The conversion of oxygenates recycles unconverted oxygenates and oxygenate by-products to a second reactor unit. The present of oxygenate by-products decreases the efficiency of the methanol to olefins reaction, and passing recycled oxygenates to a second reactor unit maintains the methanol to olefins conversion efficiency while converting the by-products in a secondary zone.
    Type: Grant
    Filed: November 25, 2013
    Date of Patent: July 26, 2016
    Assignee: UOP LLC
    Inventors: John J. Senetar, Daniel A. Kauff, Andrea G. Bozzano
  • Patent number: 9249065
    Abstract: A process may include selecting a zeolite, introducing phosphorus (P) to the zeolite, calcining the zeolite and obtaining a P modified zeolite. The process may include contacting an oxygen-containing, halogenide-containing or sulphur-containing organic feedstock in a first reactor with a first catalyst that includes the P-modified zeolite at conditions effective to convert at least a portion of the feedstock to form a first reactor effluent that includes light olefins and a heavy hydrocarbon fraction. The process may include separating the light olefins from the heavy hydrocarbon fraction, and contacting the heavy hydrocarbon fraction in a second reactor with a second catalyst that includes the P-modified zeolite at conditions effective to convert at least a portion of the heavy hydrocarbon fraction to light olefins. The first catalyst and the second catalyst may be the same or different.
    Type: Grant
    Filed: April 7, 2015
    Date of Patent: February 2, 2016
    Assignee: Fina Technology, Inc.
    Inventors: Nikolai Nesterenko, Walter Vermeiren, Delphine Minoux, Sander Van Donk
  • Patent number: 9205415
    Abstract: Disclosed is a propylene production catalyst for producing propylene from one or more selected from a group consisting of methanol, dimethyl ether and olefins having from 4 to 8 carbon atoms. The catalyst comprises a binderless crystalline aluminosilicate shaped body having a silicon/aluminum atomic ratio of from 500 to 10000, in which the crystalline aluminosilicate contains an MFI-type crystal structure and/or an MEL-type crystal structure. The catalyst reduces the production amount of ethylene, paraffin components such as propane, and aromatic components, and increases the propylene yield and the propylene/propane ratio, and the catalyst life is long.
    Type: Grant
    Filed: March 2, 2011
    Date of Patent: December 8, 2015
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Katsumi Higuchi, Saori Kakuta
  • Patent number: 9180430
    Abstract: Catalytic composition for production of olefins and methods of using same to decrease production of oxygenate byproducts. The catalytic composition includes an admixture of an alumina dehydration catalyst and at least one additional metal oxide.
    Type: Grant
    Filed: February 25, 2011
    Date of Patent: November 10, 2015
    Assignee: Dow Global Technologies LLC
    Inventors: Yu Liu, Andrzej M. Malek, Duncan Coffey, Eric E. Stangland, Albert E. Schweizer
  • Patent number: 9162937
    Abstract: The present invention is a process for making an olefin product from an oxygen-containing organic feedstock comprising: providing a mixture of said oxygen-containing feedstock, an hydrocarbon and optionally an inert diluent, contacting said mixture in a reaction zone having an inner surface (the MTO reactor) with a zeolitic catalyst at conditions effective to convert at least a part of the oxygen-containing organic feedstock to olefin products (the MTO reactor effluent), recovering a reactor effluent comprising light olefins, a heavy hydrocarbon fraction and undesired by-products, wherein: at least a part of the inner surface is passivated such that the undesired by-products are reduced by comparison with a non passivated inner surface and/or one or more sulphur compound is co-injected with the said oxygen-containing feedstock and the hydrocarbon and said sulphur compound is capable to reduce the undesired by-products by comparison with a non injection of sulphur compound.
    Type: Grant
    Filed: July 3, 2009
    Date of Patent: October 20, 2015
    Assignee: TOTAL RESEARCH & TECHNOLOGY FELUY
    Inventors: Giacomo Grasso, Nikolai Nesterenko, Sander Van Donk, Jean-Pierre Dath, Eric Duchesne
  • 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
  • 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
  • Patent number: 8987539
    Abstract: Acyclic monterpene alcohols, like linalool, to be converted through a series of highly efficient catalytic reactions a biogasoline blending component, and a drop-in biodiesel fuel.
    Type: Grant
    Filed: September 10, 2012
    Date of Patent: March 24, 2015
    Assignee: The United States of America as Represented by the Secretary of the Navy
    Inventors: Michael E. Wright, Roxanne L. Quintana
  • Publication number: 20150080623
    Abstract: A catalytic process is provided which produces in a single reaction branched, cyclic and aromatic hydrocarbons, or cracked straight-chain hydrocarbons, from fatty acids in which the fatty acids are reacted over a multifunctional catalyst and undergo both decarboxylation and a further transformation (isomerization, cyclization, aromatization, or cracking) to form reaction products useful as fuels and for other applications that require a source of energy, or as feedstock for hydrocarbon-based commercial products such as surfactants, solvents and lubricants.
    Type: Application
    Filed: September 18, 2014
    Publication date: March 19, 2015
    Inventors: Paul Ratnasamy, Moises A. Carron, Masoudeh Ahmadi
  • Patent number: 8981172
    Abstract: A ternary V—Ti—P mixed oxide is shown to catalytically dehydrate 2-methyl-tetrahydrofuran in high conversion to give piperylene, in good yield. Volatile products collected from this reaction contain piperylene in concentrations as high as 80 percent by weight. Dehydration of glycerol to acrolein in high conversion and moderate selectivity is also demonstrated. The catalyst is also shown to dehydrate other alcohols and ether substrates. The catalyst is resistant to deactivation and maintains activity between runs.
    Type: Grant
    Filed: September 16, 2011
    Date of Patent: March 17, 2015
    Assignee: Eastman Chemical Company
    Inventor: David William Norman
  • Patent number: 8981173
    Abstract: The present invention is the use of a catalyst in a MTO process to convert an alcohol or an ether into light olefins wherein said catalyst comprises a phosphorus modified zeolite and is made by a method comprising the following steps in this order, a) the essential portion of the phosphorus is introduced into a zeolite comprising at least one ten members ring in the structure, b) the phosphorus modified zeolite of step a) is mixed with at least a component selected among one or more binders, salts of alkali-earth metals, salts of rare-earth metals, clays and shaping additives, b)* making a catalyst body from mixture b), c) an optional drying step or an optional drying step followed by a washing step, d) a calcination step, d*) an optional washing step followed by drying, e) optionally a small portion of phosphorus is introduced in the course of step b) or b)* or at end of step b) or b)*.
    Type: Grant
    Filed: January 25, 2011
    Date of Patent: March 17, 2015
    Assignee: Total Research & Technology Feluy
    Inventors: Nikolai Nesterenko, Sander Van Donk, Delphine Minoux, Jean-Pierre Dath
  • Publication number: 20150068110
    Abstract: Techniques, systems and material are disclosed for transport of energy and/or materials. In one aspect, a method includes generating gaseous fuel (e.g., from biomass dissociation) at a first location of a low elevation. The gaseous fuel can be self-transported in a pipeline to a second location at a higher elevation than the first location by traveling from the first location to the second location without adding energy of pressure. A liquid fuel can be generated at the second location of higher elevation by reacting the gaseous fuel with at least one of a carbon donor, a nitrogen donor, and an oxygen donor harvested from industrial waste. The liquid fuel can be delivered to a third location of a lower elevation than the second location while providing pressure or kinetic energy.
    Type: Application
    Filed: August 13, 2014
    Publication date: March 12, 2015
    Inventor: Roy Edward McAlister
  • Patent number: 8975457
    Abstract: Described herein are methods for producing fuels and solvents from fatty acid resources. In general, the pyrolysis products of fatty acids are extracted in order to remove residual fatty acids and produce very pure hydrocarbon compositions composed of alkanes and alkenes. The fatty acids removed from the extraction step can be further pyrolyzed to produce additional hydrocarbons or, in the alternative, the fatty acids can be isolated and used in other applications. Also disclosed herein are fuels and solvents produced by the methods described herein.
    Type: Grant
    Filed: February 24, 2011
    Date of Patent: March 10, 2015
    Assignee: The Governors of the University of Alberta
    Inventor: David Bressler
  • Patent number: 8969635
    Abstract: A method of: providing a mixture of fecal waste and a bacterium; incubating the mixture to produce a fatty acid enriched mixture; removing water from the fatty acid enriched mixture to produce a dried mixture; and pyrolyzing the dried mixture in an inert atmosphere to produce an alkane from the C5-C32 fatty acid. The bacterium is a type that produces a C5-C32 fatty acid in the presence of any microbes in the fecal waste.
    Type: Grant
    Filed: October 27, 2010
    Date of Patent: March 3, 2015
    Assignee: The United States of America, as represented by the Secretary of the Navy
    Inventors: Justin C. Biffinger, Lisa A. Fitzgerald, Cherie Ziemer, Kurt Henry, Bradley R Ringeisen
  • Patent number: 8968670
    Abstract: A process and system for separating and upgrading bio-oil into renewable fuels is provided. The process comprises separating bio-oil into a light fraction and heavy fraction based on their boiling points. The heavy fraction is then subjected to hydrotreatment, while the light fraction is not subjected to hydrotreatment. At least a portion of the un-hydrotreated light fraction and at least a portion of the hydrotreated heavy fraction are blended with petroleum-derived gasoline to thereby provide a renewable gasoline, and at least a portion of the hydrotreated heavy fraction is blended with petroleum-derived diesel to thereby provide a renewable diesel.
    Type: Grant
    Filed: December 27, 2013
    Date of Patent: March 3, 2015
    Assignee: KiOR, Inc.
    Inventors: Maria Magdalena Ramirez Corredores, Vicente Sanchez Iglesias
  • Patent number: 8962904
    Abstract: Catalytic composition for producing an alpha-olefin and methods of making same. The catalytic composition includes a gamma-alumina substrate dopes with at least one element consisting of bismuth, copper, gallium, phosphorus, tin, and zinc, an amount of each element being within a range of from 150 parts per million to 1000 parts per million relative to a total doped weight of the gamma-alumina substrate. Additionally, at least one element is combined with at least one element consisting of cesium, lithium, and magnesium, an amount of each element being within the range of from 150 parts per million to 1000 parts per million relative to the total doped weight of the gamma-alumina substrate.
    Type: Grant
    Filed: December 14, 2010
    Date of Patent: February 24, 2015
    Assignee: Dow Global Technologies LLC
    Inventors: Daniela Ferrari, Alberto Martinez Joaristi, Billy B. Bardin, Garmt R. Meima
  • Patent number: 8962905
    Abstract: Process for the continuous hydrogenation of triglyceride containing raw materials in a fixed bed reactor system having several catalyst beds arranged in series and comprising at least one hydrogenation catalyst comprising an active phase constituted by a nickel and molybdenum element. The raw material feed, hydrogen containing gas and diluting agent are passed together through the catalyst beds at hydrogenation conditions. The raw material feed stream as well as the stream of hydrogen containing gas are divided into an equal number of different partial streams. These are each passed to one catalyst bed in such a manner that the weight ratio of diluting agent to raw material feed is essentially the same at the entrance of all catalyst beds and does not exceed 4:1. The claimed process is preferably conducted at low temperatures and allows the utilization of existing units due to the low recycle ratio.
    Type: Grant
    Filed: September 7, 2011
    Date of Patent: February 24, 2015
    Assignee: IFP Energies Nouvelles
    Inventors: Thierry Chapus, Nathalie Dupassieux, Antoine Daudin
  • Patent number: 8957274
    Abstract: The present invention relates to a process to make light olefins and aromatics, in a combined XTO-OC process, from an oxygen-containing, halogenide-containing or sulphur-containing organic feedstock comprising: a0) providing a first portion and a second portion of said oxygen-containing, halogenide-containing or sulphur-containing organic feedstock, a) providing a catalyst comprising zeolitic molecular sieves containing at least 10 membered ring pore openings or larger in their microporous structure, b) providing an XTO reaction zone, an OC reaction zone and a catalyst regeneration zone, said catalyst circulating in the three zones, such that at least a portion of the regenerated catalyst is passed to the OC reaction zone, at least a portion of the catalyst in the OC reaction zone is passed to the XTO reaction zone and at least a portion of the catalyst in the XTO reaction zone is passed to the regeneration zone; c) contacting the first portion of said oxygen-containing, halogenide-containing or sulphur-cont
    Type: Grant
    Filed: June 24, 2009
    Date of Patent: February 17, 2015
    Assignee: Total Research & Technology Feluy
    Inventors: Nikolai Nesterenko, Walter Vermeiren, Giacomo Grasso, Sander Van Donk, Wolfgang Garcia
  • Patent number: 8957268
    Abstract: Methods are provided for refining natural oil feedstocks. The methods comprise reacting the feedstock in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product comprising olefins and esters. In certain embodiments, the methods further comprise separating the olefins from the esters in the metathesized product. In certain embodiments, the methods further comprise hydrogenating the olefins under conditions sufficient to form a fuel composition. In certain embodiments, the methods further comprise transesterifying the esters in the presence of an alcohol to form a transesterified product.
    Type: Grant
    Filed: October 11, 2010
    Date of Patent: February 17, 2015
    Assignee: Elevance Renewable Sciences, Inc.
    Inventors: Steven A. Cohen, Melvin L. Luetkens, Jr., Chander Balakrishnan, Robert Snyder
  • Patent number: 8957272
    Abstract: The present invention relates to a process to make light olefins, in a combined XTO-OC process, from an oxygen-containing, halogenide-containing or sulphur-containing organic feedstock comprising: a0) providing a first portion and a second portion of said oxygen-containing, halogenide-containing or sulphur-containing organic feedstock, a) providing a catalyst comprising zeolitic molecular sieves containing at least 10 membered ring pore openings or larger in their microporous structure, b) providing an XTO reaction zone, an OC reaction zone and a catalyst regeneration zone, said catalyst circulating in the three zones, such that at least a portion of the regenerated catalyst is passed to the OC reaction zone, at least a portion of the catalyst in the OC reaction zone is passed to the XTO reaction zone and at least a portion of the catalyst in the XTO reaction zone is passed to the regeneration zone; c) contacting the first portion of said oxygen-containing, halogenide-containing or sulphur-containing organic
    Type: Grant
    Filed: June 24, 2009
    Date of Patent: February 17, 2015
    Assignee: Total Research & Technology Feluy
    Inventors: Nikolai Nesterenko, Walter Vermeiren, Giacomo Grasso, Sander Van Donk, Wolfgang Garcia
  • Patent number: 8957273
    Abstract: The present invention relates to a process to make light olefins, in a combined XTO-OC process, from an oxygen-containing, halogenide-containing or sulphur-containing organic feedstock comprising: a0) providing a first portion and a second portion of said oxygen-containing, halogenide-containing or sulphur-containing organic feedstock, a) providing a catalyst comprising zeolitic molecular sieves containing at least 10 membered ring pore openings or larger in their microporous structure, b) providing an XTO reaction zone, an OC reaction zone and a catalyst regeneration zone, said catalyst circulating in the three zones, such that at least a portion of the regenerated catalyst is passed to the OC reaction zone, optionally at least a portion of the catalyst in the OC reaction zone is passed to the XTO reaction zone and at least a portion of the catalyst in the XTO reaction zone is passed to the regeneration zone; c) contacting the first portion of said oxygen-containing, halogenide-containing or sulphur-contain
    Type: Grant
    Filed: June 24, 2009
    Date of Patent: February 17, 2015
    Assignee: Total Research & Technology Feluy
    Inventors: Nikolai Nesterenko, Walter Vermeiren, Giacomo Grasso, Sander Van Donk, Wolfgang Garcia
  • Patent number: 8957271
    Abstract: The present invention relates to a process to make light olefins, in a combined XTO-OC process, from an oxygen-containing, halogenide-containing or sulphur-containing organic feedstock comprising: a) providing a catalyst comprising zeolitic molecular sieves containing 10 member and larger channels in their microporous structure, b) providing an XTO reaction zone, an OC reaction zone and a catalyst regeneration zone, said catalyst circulating in the three zones, such that at least a portion of the regenerated catalyst is passed to the OC reaction zone, at least a portion of the catalyst in the OC reaction zone is passed to the XTO reaction zone and at least a portion of the catalyst in the XTO reaction zone is passed to the regeneration zone; c) contacting said oxygen-containing, halogenide-containing or sulphur-containing organic feedstock in the XTO reactor with the catalyst at conditions effective to convert at least a portion of the feedstock to form a XTO reactor effluent comprising light olefins and a h
    Type: Grant
    Filed: June 24, 2009
    Date of Patent: February 17, 2015
    Assignee: Total Research & Technology Feluy
    Inventors: Nikolai Nesterenko, Walter Vermeiren, Giacomo Grasso, Sander Van Donk, Wolfgang Garcia
  • Publication number: 20150038754
    Abstract: A phosphorous modified zeolite (A) can be made by a process that includes selecting a zeolite, steaming the zeolite, leaching the zeolite, separating solids from liquid, and calcining. An olefin product can be made from an oxygen-containing, halogenide-containing or sulphur-containing organic feedstock by contacting the feedstock with the phosphorous modified zeolite (A) in an XTO reactor under conditions effective to convert at least a portion of the feedstock to olefin products. The XTO reactor effluent can include light olefins and a heavy hydrocarbon fraction. The light olefins can be separated from the heavy hydrocarbon fraction. The heavy hydrocarbon fraction can be contacted in an OCP reactor at conditions effective to convert at least a portion of the heavy hydrocarbon fraction to light olefins.
    Type: Application
    Filed: September 11, 2014
    Publication date: February 5, 2015
    Inventors: Nikolai Nesterenko, Walter Vermeiren, Delphine Minoux, Sander Van Donk
  • Patent number: 8946496
    Abstract: The invention relates to a process for preparing lower olefins from an oxygenate, the process comprising: subjecting C4 hydrocarbons obtained in an oxygenate-to-olefins conversion step to extractive distillation to an etherification step to convert isobutene into an alkyl tertiary butyl ether to obtain an isobutene-depleted C4 hydrocarbon stream and alkyl tertiary-butyl ether; subjecting the isobutene-depleted C4 hydrocarbon stream to extractive distillation to obtain a stream enriched in unsaturated C4 hydrocarbons and a stream enriched in saturated C4 hydrocarbons; and recycling at least part of the stream enriched in unsaturated C4 hydrocarbons and/or at least part of the alkyl tertiary-butyl ether to the oxygenate-to-olefins conversion step.
    Type: Grant
    Filed: December 27, 2012
    Date of Patent: February 3, 2015
    Assignee: Shell Oil Company
    Inventors: Leslie Andrew Chewter, Rajaram Ramesh, Jeroen Van Westrenen
  • Patent number: 8940949
    Abstract: A process for the conversion of biomass to hydrocarbon products such as transportation fuels, kerosene, diesel oil, fuel oil, chemical and refinery plant feeds. The instant process uses a hydrocarbon or synthesis gas co-feed and hot pressurized water to convert the biomass in a manner commonly referred to as hydrothermal liquefaction.
    Type: Grant
    Filed: September 24, 2012
    Date of Patent: January 27, 2015
    Inventor: Gary Peyton Miller
  • Patent number: 8940951
    Abstract: A process for preparing isobutene by dissociation of MTBE, including: a) reaction of isobutene-containing hydrocarbon mixtures, with methanol, present in one or more methanol-containing streams, over acidic ion exchangers to give a stream, containing MTBE and TBA; b) separation of a stream containing MTBE and TBA, from a stream by distillation; c) dissociation of a stream in the gas phase over a heterogeneous catalyst to give a stream containing at least isobutene, methanol, MTBE and water and possibly TBA, d) separation of a stream by distillation to give a stream containing in each case more than 50% by mass of the amounts of methanol, TBA and water present in another stream and a stream containing isobutene, e) separation of water from stream to below 1% by mass by distillation to give a stream, f) total or partial recirculation of the methanol-containing stream.
    Type: Grant
    Filed: June 16, 2010
    Date of Patent: January 27, 2015
    Assignee: Evonik Degussa GmbH
    Inventors: Markus Winterberg, Dirk Roettger, Armin Rix, Reiner Bukohl, Walter Luh, Holger Wiederhold, Gunnar Schilling, Christian Boeing
  • 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