Alcohol, Ester, Or Ether Patents (Class 585/639)
  • 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: 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
  • 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
  • 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
  • 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
  • Patent number: 8975459
    Abstract: A process for making a bio-naphtha and optionally bio-propane from a complex mixture of natural occurring fats & oils, wherein said complex mixture is subjected to a refining treatment for removing the major part of non-triglyceride and non-fatty acid components, thereby obtaining refined fats & oils; said refined fats & oils are transformed into linear or substantially linear paraffin's as the bio-naphtha by an hydrodeoxygenation or from said refined fats & oils are obtained fatty acids that are transformed into linear or substantially linear paraffin's as the bio-naphtha by hydrodeoxygenation or decarboxylation of the free fatty acids or from said refined fats & oils are obtained fatty acids soaps that are transformed into linear or substantially linear paraffin's as the bio-naphtha by decarboxylation of the soaps.
    Type: Grant
    Filed: December 3, 2013
    Date of Patent: March 10, 2015
    Assignee: Total Research & Technology Feluy
    Inventors: Walter Vermeiren, Nicolas Van Gyseghem
  • 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: 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: 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: 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: 8957269
    Abstract: The invention relates to a method of producing olefinic monomers for the production of a polymer. The invention particularly relates to the production of tall oil-based biopolymers, such as polyolefins. In the stages of the method bio oil, with a content of over 50% of fatty acids of tall oil and no more than 25% of resin acids of tall oil, and hydrogen gas are fed into a catalyst bed (7); the oil is catalytically deoxygenated in the bed by hydrogen; the flow exiting the bed is cooled down and divided into a hydrocarbon-bearing liquid phase (10) and a gas phase; and the hydrocarbon-bearing liquid (13) is subjected to steam cracking (4) to provide a product containing polymerizing olefins. The deoxygenation in the bed can be followed by a catalytic cracking or, with a suitable catalyst, the deoxygenation and cracking can be simultaneous. The separated hydrogen-bearing gas phase can be circulated in the process.
    Type: Grant
    Filed: January 29, 2010
    Date of Patent: February 17, 2015
    Assignee: Stora Enso Oyj
    Inventors: Ali Harlin, Tapani Penttinen, Jari Räsänen, Olli Aaltonen
  • 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: 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
  • 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
  • Publication number: 20150044129
    Abstract: The invention relates to a method for processing coke oven gas, said coke oven gas containing hydrogen, wherein the coke oven gas is at least partially integrated into a method for producing dimethyl ether in conjunction with a gas containing carbon monoxide and/or carbon dioxide, whereby a DME-containing product gas is formed. At the outset of the method for the formation of dimethyl ether, a ratio of hydrogen to carbon monoxide, weighted with the carbon dioxide concentration (formula (I)), of 0.9 to 1.1 is set, wherein the DME-containing product gas is integrated into a method for converting dimethyl ether to olefins, whereby an olefin-containing product gas is formed, and wherein olefins, in particular ethylene and/or propylene, is/are separated from the olefin-containing product gas by means of separating methods.
    Type: Application
    Filed: August 7, 2012
    Publication date: February 12, 2015
    Applicant: LINDE AKTIENGESELLSCHAFT
    Inventors: Nicole Schodel, Ernst Haidegger, Holger Schmigalle, Volker Goke, Harald Schmaderer
  • Publication number: 20150045456
    Abstract: The invention relates to processes for production of dimethyl ether from methane or natural gas comprising: a dry-reforming step, wherein methane and carbon dioxide are converted into carbon monoxide and hydrogen, and a DME synthesis step, wherein the carbon monoxide and hydrogen formed in the dry-reforming step are converted into dimethyl ether, wherein the dry-reforming step and the synthesis step are carried out at identical pressures or at pressures, which do not differ more than 3 bar, preferably not more than 1 bar.
    Type: Application
    Filed: January 15, 2013
    Publication date: February 12, 2015
    Applicant: LINDE AKTIENGESELLSCHAFT
    Inventors: Nicole Schoedel, Ernst Haidegger, Holger Schmigalle, Axel Behens, Volker Goeke, Christian Thaller, Harald Schmaderer
  • 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: 8940953
    Abstract: The invention relates to a process for converting a feed stream consisting of reactive components and an optional feed diluent to a product stream comprising aromatic hydrocarbons and C2-C3 olefins, wherein the reactive components comprise at least 90 vol % of an aliphatic ether selected from the group consisting of methyl tertiary butyl ether and ethyl tertiary butyl ether, the process comprising the step of contacting the feed stream with a catalyst composition comprising a zeolite catalyst, wherein the zeolite catalyst is a zeolite modified by Ga and an element M1 selected from the group consisting of Zn, Cd and Cu.
    Type: Grant
    Filed: May 9, 2013
    Date of Patent: January 27, 2015
    Assignee: Saudi Basic Industries Corporation
    Inventors: Aghaddin Kh. Mammadov, Ali Said Al-Khuraimi
  • 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: 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
  • Publication number: 20150025288
    Abstract: A method and apparatus for dehydrating bio-1-alcohols to bio-1-alkenes with high selectivity. The bio-1-alkenes are useful in preparing high flashpoint diesel and jet biofuels which are useful to civilian and military applications. Furthermore, the bio-1-alkenes may be converted to biolubricants useful in the transporation sector and other areas requiring high purity/thermally stable lubricants.
    Type: Application
    Filed: September 8, 2014
    Publication date: January 22, 2015
    Inventor: Michael E. Wright
  • Publication number: 20150018592
    Abstract: The invention relates to a process for production of DME (17) comprising the steps of: generating a syngas (12) containing CO and H2 in a device (11) for syngas generation, passing the syngas (12) into a DME reactor (13) for direct synthesis of DME by catalysed conversion of the syngas (12) by means of a catalyst to form a product stream (14) containing DME, CO2, H2O, CH3OH and unconverted syngas (12). The invention provides that the direct synthesis is carried out at or close to the chemical equilibrium.
    Type: Application
    Filed: January 15, 2013
    Publication date: January 15, 2015
    Applicant: LINDE AKTIENGESELLSCHAFT
    Inventors: Nicole Schodel, Ernst Haidegger, Holger Schmigalle, Volker Goke, Christian Thaller, Harald Schmaderer
  • Publication number: 20150018591
    Abstract: A method of converting an oxygenate comprising feedstock to olefins comprising: feeding an oxygenate comprising feedstock into a reactor containing an oxygenate to olefins conversion catalyst; contacting the feedstock with the catalyst at oxygenate conversion conditions to produce olefins; removing an effluent comprising the olefins from the reactor; passing the effluent through a compression section to form a compressed effluent; and adding methane to the compression section.
    Type: Application
    Filed: June 30, 2014
    Publication date: January 15, 2015
    Inventors: Saravana BHAVAN, Jeroen VAN WESTRENEN, Jeroen Gerard MARSMAN, Lesllie Andrew CHEWTER
  • 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
  • Publication number: 20150011801
    Abstract: Renewable resources comprising bagasse, corn stover, wood sawdust and switch grass are subject to direct catalytic conversion or bio-fermentation producing ethanol leaving complex lignin compounds for disposal. Chemical conversion of lignin compounds (recoverable from digested lignin) to substituted phenols followed by a carbon steel catalyzed pulsed flow hydrogenation produces cresol and substituted creosol compounds. The pulsed flow process produced close to 100 percent reduction of the reactants compared to 25 percent with continuous flow and is applicable to aliphatic carboxylic acid compounds such as natural oils producing valued liquid hydrocarbons.
    Type: Application
    Filed: July 8, 2013
    Publication date: January 8, 2015
    Applicant: Carter Technologies Corporation
    Inventor: M. K. Carter
  • Patent number: 8921629
    Abstract: Biofuels can be produced via an organic phase hydrocatalytic treatment of biomass using an organic solvent that is partially miscible with water. An organic hydrocarbon-rich phase from the hydrocatalytically treated products can be recycled to form at least a portion of the organic phase.
    Type: Grant
    Filed: October 29, 2012
    Date of Patent: December 30, 2014
    Assignee: Shell Oil Company
    Inventors: Joseph Broun Powell, Kimberly Ann Johnson
  • Patent number: 8921632
    Abstract: 1-butene is recovered as a purified product from an MTO synthesis and especially from an integrated MTO synthesis and hydrocarbon pyrolysis system in which the MTO system and its complementary olefin cracking reactor are combined with a hydrocarbon pyrolysis reactor in a way that facilitates the flexible production and recovery of olefins and other petrochemical products, particularly butene-1 and MTBE.
    Type: Grant
    Filed: July 29, 2011
    Date of Patent: December 30, 2014
    Assignee: UOP LLC
    Inventors: Joseph A. Montalbano, Steven Lee Krupa, John Joseph Senetar, Joseph H. Gregor, Andrea G. Bozzano, Gary S. Sandhu
  • Publication number: 20140378730
    Abstract: Olefms may be produced by the non-reductive dehydroxylation of vicinal polyols and/or their respective esters, in a liquid reaction medium, under a substantially non- reductive atmosphere, in the presence of a halogen-based, preferably iodine-based, catalyst. The reaction medium may be aqueous, non- aqueous, or a combination thereof, and may in some embodiments include a solubility enhancing agent.
    Type: Application
    Filed: December 5, 2012
    Publication date: December 25, 2014
    Inventors: Raj Deshpande, Paul Davis, Vandana Pandey, Nitin Kore
  • Publication number: 20140378729
    Abstract: Olefins may be produced by the reductive dehydroxylation of vicinal polyols and/or their respective esters, in an aqueous reaction medium, under a hydrogen atmosphere, under suitable conditions, and in the presence of a halogen-based, preferably iodine-based, catalyst, wherein a solubility enhancing agent is employed to increase the solubility of the iodine-based catalyst in the aqueous reaction medium.
    Type: Application
    Filed: December 5, 2012
    Publication date: December 25, 2014
    Applicant: DOW GLOBAL TECHNOLOGIES LLC
    Inventors: Raj Deshpande, Paul Davis, Vandana Pandey, Nitin Kore
  • Publication number: 20140371502
    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: Application
    Filed: December 20, 2012
    Publication date: December 18, 2014
    Inventors: Masayasu Ishibashi, Tsuneyuki Ohkubo
  • Patent number: 8912373
    Abstract: A method and apparatus for dehydrating bio-1-alcohols to bio-1-alkenes with high selectivity. The bio-1-alkenes are useful in preparing high flashpoint diesel and jet biofuels which are useful to civilian and military applications. Furthermore, the bio-1-alkenes may be converted to biolubricants useful in the transportation sector and other areas requiring high purity/thermally stable lubricants.
    Type: Grant
    Filed: March 29, 2012
    Date of Patent: December 16, 2014
    Assignee: The United States of America as Represented by the Secretary of the Navy
    Inventor: Michael E. Wright
  • Patent number: 8912379
    Abstract: Disclosed is a method of preparing an alkene compound including introducing an acidic catalyst and a solvent into a reactor, increasing a temperature the reactor, and continuously removing water from the reactor while continuously supplying an alcohol into the reactor and continuously collecting an alkene compound.
    Type: Grant
    Filed: May 31, 2010
    Date of Patent: December 16, 2014
    Assignee: Songwon Industrial Co., Ltd.
    Inventors: Dong-Kyung Park, Chang-Heon Shon, Duk-Suk Jung, Young-Tae Song
  • Publication number: 20140357921
    Abstract: Crude alcohol streams are converted to olefins under reductive or non-reductive dehydroxylation conditions, in the presence of a halogen-based catalyst. The process includes autogenous gas pressure or a gas pressure from 1 psig (˜6.89 KPa) to 2000 psig (˜13.79 MPa), a temperature from 50° C. to 250° C., a liquid reaction medium, and a molar ratio of alcohol to halogen from 1:10 to 100:1.
    Type: Application
    Filed: December 5, 2012
    Publication date: December 4, 2014
    Inventors: Raj Deshpande, Paul Davis, Vandana Pandey, Nitin Kore
  • Publication number: 20140357920
    Abstract: Olefins are produced by the reductive dehydroxylation of vicinal polyols or esters thereof, or a combination thereof, in a liquid reaction medium, under a hydrogen atmosphere, at a temperature from 50° C. to 250° C., in the presence of a halogen-based, preferably iodine-based, catalyst. Examples of the catalyst, which may be included independently or generated in situ, are iodine (I2), hydroiodic acid (HI), iodic acid (HIO3), lithium iodide (LiI), and combinations thereof.
    Type: Application
    Filed: December 5, 2012
    Publication date: December 4, 2014
    Inventors: Raj Deshpande, Paul Davis, Vandana Pandey, Nitin Kore, John R. Briggs
  • Publication number: 20140343340
    Abstract: Polyether polyols, derivatives and combinations thereof are converted to olefins under reductive or non-reductive dehydroxylation conditions, in the presence of a halogen-based catalyst. Derivatives include polyether polyols incorporated in polyurethanes. The process includes gas pressure from 1 psig (˜6.89 KPa) to 2000 psig (˜13.79 MPa), a temperature from 50° C. to 250° C., a liquid reaction medium, and a molar ratio of the starting material to halogen atoms from 1:10 to 100:1.
    Type: Application
    Filed: December 5, 2012
    Publication date: November 20, 2014
    Inventors: Raj Deshpande, Paul Davis, Vandana Pandey, Nitin Kore, John R. Briggs
  • Publication number: 20140343339
    Abstract: The invention relates to a method for processing furnace gas (4) from a steel and/or iron works, wherein said furnace gas (4) contains carbon dioxide and/or carbon monoxide and is at least partially integrated into a method (7) for the formation of dimethyl ether in conjunction with a hydrogen-containing gas (2), whereby a DME-containing product gas (8) is formed. At the outset of the method (7) for forming dimethyl ether, a ratio of hydrogen to carbon monoxide, weighted with the carbon dioxide concentration (formula (I)), of 0.9 to 1.1 is set and dimethyl ether is formed. The DME-containing product gas (8) is integrated into a method (9) for converting dimethyl ether to olefins, whereby an olefin-containing product gas (10) is formed, and wherein olefins (12), in particular ethylene and/or propylene, is/are separated from the olefin-containing product gas (10) by means of separating methods (11).
    Type: Application
    Filed: August 7, 2012
    Publication date: November 20, 2014
    Applicant: LINDE AKTIENGESELLSCHAFT
    Inventors: Nicole Schodel, Ernst Haidegger, Holger Schmigalle, Volker Goke, Harald Schmaderer
  • Patent number: 8889941
    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 obtain a stream enriched in unsaturated C4 hydrocarbons comprising isobutene and n-butenes, and a stream enriched in saturated C4 hydrocarbons; converting the isobutene in the stream enriched in unsaturated C4 hydrocarbons into an alkyl tertiary butyl ether to obtain an isobutene-depleted unsaturated C4 hydrocarbon stream and alkyl tertiary-butyl ether; and recycling at least part of the isobutene-depleted unsaturated C4 hydrocarbon stream and/or at least part of the alkyl tertiary-butyl ether, optionally after conversion into tertiary butanol and/or isobutene, to the oxygenate-to-olefins conversion step.
    Type: Grant
    Filed: December 27, 2012
    Date of Patent: November 18, 2014
    Assignee: Shell Oil Company
    Inventors: Leslie Andrew Chewter, Rajaram Ramesh, Jeroen Van Westrenen
  • Patent number: 8884090
    Abstract: An olefin is prepared from an alkyl alcohol in a process which comprises the steps: a) converting the alkyl alcohol into a dialkylether over a first catalyst, to yield a hot dialkylether product stream containing alkyl alcohol, dialkylether and water; b) cooling the hot dialkylether product stream at least partly by indirect heat exchange with a cold dialkylether product stream to below the dew point of water at the prevailing conditions to obtain a gas-liquid mixture; c) separating the obtained mixture into a liquid water-containing stream and a vaporous dialkylether-rich stream; d) subjecting at least part of the vaporous dialkylether-rich stream, as the cold dialkylether product stream in step b), to heat exchange with the hot dialkylether product stream, to yield a heated dialkylether-rich feed; and e) converting the heated dialkylether-rich feed to an olefin over a second catalyst.
    Type: Grant
    Filed: November 19, 2008
    Date of Patent: November 11, 2014
    Assignee: shell Oil Company
    Inventors: Jeroen Van Westrenen, Leslie Andrew Chewter, Ferry Winter
  • Patent number: 8884089
    Abstract: The present invention provides a process for producing olefins, comprising: a. cracking an ethane-comprising feed in a cracking zone under cracking conditions to obtain at least olefins and hydrogen; b. converting an oxygenate feedstock in an oxygenate-to-olefin zone to obtain at least olefins; wherein at least part of the oxygenate feedstock is obtained by providing hydrogen obtained in step a) and a feed containing carbon monoxide and/or carbon dioxide to an oxygenate synthesis zone and synthesizing oxygenates. In another aspect the invention provides an integrated system for producing olefins.
    Type: Grant
    Filed: November 9, 2010
    Date of Patent: November 11, 2014
    Assignee: Shell Oil Company
    Inventors: Leslie Andrew Chewter, Jeroen Van Westrenen
  • Patent number: 8877997
    Abstract: A process and apparatus is presented for the removal of solid particles from a gas stream. The process and apparatus includes adding a second stream of liquid that is sprayed over the openings in trays in a quench tower. The second spray stream provides for a veil of liquid to wash out solid particles from the vapor stream.
    Type: Grant
    Filed: December 13, 2011
    Date of Patent: November 4, 2014
    Assignee: UOP LLC
    Inventors: Joseph A. Montalbano, John J. Senetar, Daniel A. Kauff, Gurjit S. Sandhu
  • Patent number: 8859837
    Abstract: The present invention relates to a process for producing lower olefinic hydrocarbons by oxidative dehydrogenation of paraffinic lower hydrocarbons. More particularly the present invention provides a process for converting a feedstream comprising a paraffinic lower hydrocarbon and carbon dioxide to a product stream comprising an olefinic lower hydrocarbon and synthesis gas in the presence of the catalyst composition La—Mn/inert support, wherein said catalyst composition comprises 1-10 mass % lanthanum and 1-10 mass % manganese and optionally 0.3-3 mass % alkali metal.
    Type: Grant
    Filed: November 23, 2009
    Date of Patent: October 14, 2014
    Assignee: Saudi Basic Industries Corporation
    Inventors: Aggadin Kh. Mamedov, Ali S. Al-Khuraimi
  • Patent number: 8846997
    Abstract: The present invention is a process for removing oxygenated contaminants and water from an hydrocarbon stream comprising: introducing the contaminated hydrocarbon stream in a gaseous phase in an absorption zone, contacting said hydrocarbon stream in said absorption zone at a pressure of at least 5 bars, advantageously in the range 5 to 40 bars with an alcohol capable to absorb water and oxygenated contaminants at conditions effective to produce an overhead hydrocarbon stream having a reduced oxygenated contaminants and water content and an absorbent bottoms stream comprising the alcohol, hydrocarbons and having an enhanced oxygenated contaminants and water content, sending the overhead of the absorption zone to a wash column (referred to as the high pressure water wash column) at a pressure of at least 5 bars, advantageously in the range 5 to 40 bars, essentially washed with water at conditions effective to produce an overhead hydrocarbon stream having a reduced oxygenated contaminants and an aqueous bott
    Type: Grant
    Filed: December 20, 2010
    Date of Patent: September 30, 2014
    Assignee: Total Research & Technology Feluy
    Inventors: Laurent Avaullee, Jean-Pierre Thoret Bauchet
  • Patent number: 8841497
    Abstract: The present invention relates to a process of formulating and preparing supported multi-metal catalysts based on metal oxides and inorganic salts of metals. The impregnation technique is employed by two methods: the slurry method and the modified-pH variation method, which are used in two steps for obtaining the catalyst. The present invention also relates to a process called Glycerol to Propene (GTP) process, corresponding to the transformation of glycerol or glycerin to propene. The reaction involved in the process of the present invention is the selective hydrogenation of glycerin, which takes place by contact of the charge of glycerin carried by hydrogen in a continuous stream system on the catalytic bed containing multi-metal catalysts, specifically prepared for this purpose.
    Type: Grant
    Filed: June 24, 2009
    Date of Patent: September 23, 2014
    Assignees: Quattor Petroquimica S.A., Universidade Federal do Rio de Janeiro—UFRJ
    Inventors: José´ Carlos Sousa Fadigas, Rossano Gambetta, Cláudio José´ de Araújo Mota, Valter Luiz da Conceição Gonçalves
  • Publication number: 20140275592
    Abstract: Disclosed is the use of a metal catalyst or catalyst precursor that catalyzes the isomerization of an unsaturated fatty acid, unsaturated fatty acid derivative, or an unsaturated triglyceride. Also disclosed is the use of a metal catalyst or catalyst precursor that catalyzes the decarboxylation of an unsaturated organic compound. Also disclosed is the use of a catalyst or catalyst precursor for the dual function isomerization and decarboxylation of an unsaturated fatty acid to an unsaturated organic compound.
    Type: Application
    Filed: March 11, 2014
    Publication date: September 18, 2014
    Applicant: The United States of America, as represented by the Secretary of Agriculture
    Inventors: Rex E. Murray, Kenneth M. Doll, Zengshe Liu
  • Patent number: 8835703
    Abstract: The present invention describes a method for the production of one or more olefins from the residue of at least one renewable natural raw material. The present invention is advantageously related to a method that is integrated with a processing method for processing renewable natural agricultural raw materials for the production of propylene, and optionally of ethylene and butylene, mainly from the residues of the processed renewable natural agricultural raw material. The propylene is obtained from the gasification reaction of the lignocellulosic materials and of other organic products contained in the raw material residues, followed by the formation of methanol and its subsequent transformation into propylene, where this route may further generate ethylene and/or butylene as by-products.
    Type: Grant
    Filed: November 30, 2007
    Date of Patent: September 16, 2014
    Assignee: Braskem S.A.
    Inventor: Antonio Luiz Ribeiro De Castro Morschbacker
  • Patent number: 8829259
    Abstract: An integrated MTO synthesis and hydrocarbon pyrolysis system is described in which the MTO system and its complementary olefin cracking reactor are combined with a hydrocarbon pyrolysis reactor in a way that facilitates the flexible production of olefins and other petrochemical products, such as butene-1 and MTBE.
    Type: Grant
    Filed: July 29, 2011
    Date of Patent: September 9, 2014
    Assignee: UOP LLC
    Inventors: Andrea G. Bozzano, Joseph H. Gregor, John J. Senetar
  • Patent number: 8829260
    Abstract: A process for the production of olefins from at least one of an alcohol and ether, the process including: contacting at least one alcohol or ether with a hydrofluoric acid-treated amorphous synthetic alumina-silica catalyst under decomposition conditions to produce an olefin.
    Type: Grant
    Filed: April 19, 2012
    Date of Patent: September 9, 2014
    Assignee: Catalytic Distillation Technologies
    Inventor: J. Yong Ryu
  • Patent number: 8822748
    Abstract: Process for the production of ethene by the vapor phased chemical dehydration of a feed containing ethanol, water and ethoxyethane in a reactor at elevated temperature and pressure in the presence of a bed of catalyst comprising a supported heteropolytungstic acid, by maintaining or configuring the reactor so that it operates in a regime which satisfies the following parameters: 0.05<(Pwater/Pethanol+Pethoxyethane))/(8×10?5×GHSV+0.75)??(1) and ?20<Treaction?Tdew point?40×Ptotal feed+40×Pinerts<+80??(2) wherein Pwater, Pethanol and Pethoxyethane, GHSV, Treaction, Tdew point, Ptotal feed and Pinerts are as defined in the specification.
    Type: Grant
    Filed: October 8, 2008
    Date of Patent: September 2, 2014
    Assignee: BP P.L.C.
    Inventors: Benjamin Patrick Gracey, Stephen Roy Partington
  • Patent number: 8822749
    Abstract: Process for the preparation of an olefinic product, which process comprises reacting an oxygenate feedstock and an olefinic co-feed in a reactor in the presence of an oxygenate conversion catalyst comprising a molecular sieve having one-dimensional 10-membered ring channels, and a further molecular sieve having more-dimensional channels, wherein the weight ratio between the one-dimensional molecular sieve and the further molecular sieve is in the range of from 1:1 to 100:1, to prepare an olefinic reaction effluent; separating the olefinic reaction effluent into at least a first olefinic fraction and a second olefinic fraction; recycling at least part of the second olefinic fraction; and recovering at least part of the first olefinic fraction as olefinic product.
    Type: Grant
    Filed: November 19, 2008
    Date of Patent: September 2, 2014
    Assignee: Shell Oil Company
    Inventors: Jeroen Van Westrenen, Leslie Andrew Chewter, Ferry Winter