To Produce Unsaturate Patents (Class 585/324)
  • Patent number: 10577544
    Abstract: The present application discloses low temperature, low pressure methods (LTLP) for upgrading and/or stabilizing bio-oil or a bio-oil fraction. One method comprises providing a bio-oil or bio-oil fraction and hydrogen, which are reacted in the presence of a catalyst at a temperature of less than 150° C. and a pressure of less than 100 bar (absolute) to produce a hydrogenated liquid oil at a carbon yield of over 75%. Another method comprises providing a bio-oil or bio-oil fraction, providing oxygen reducing reaction conditions, and reacting the bio-oil or bio-oil fraction under the oxygen reducing reaction conditions at LTLP to produce an upgraded bio-oil product containing fewer carbonyls than the bio-oil or bio-oil fraction. Yet another method comprises providing a bio-oil or bio-oil fraction and a solution comprising one or more fermentation organisms and a sugar source. The solution and bio-oil or bio-oil fraction are combined to obtain a fermentation mixture, which is incubated at 15° C. to 30° C.
    Type: Grant
    Filed: April 15, 2015
    Date of Patent: March 3, 2020
    Assignee: Iowa State University Research Foundation, Inc.
    Inventors: Marjorie Rover, Robert C. Brown, Patrick H. Hall, Ryan G. Smith
  • Patent number: 10513476
    Abstract: The present invention relates to an integrated process to convert crude oil into petrochemical products comprising crude oil distillation, aromatic ring opening, and olefins synthesis, which process comprises subjecting a hydrocarbon feed to aromatic ring opening to produce LPG and subjecting the LPG produced in the integrated process to olefins synthesis. Furthermore, the present invention relates to a process installation to convert crude oil into petrochemical products comprising a crude distillation unit comprising an inlet for crude oil and at least one outlet for kerosene and/or gasoil; an aromatic ring opening unit comprising an inlet for a hydrocarbon feed to aromatic ring opening and an outlet for LPG; and a unit for the olefins synthesis comprising an inlet for LPG produced by the integrated petrochemical process installation and an outlet for olefins.
    Type: Grant
    Filed: October 5, 2018
    Date of Patent: December 24, 2019
    Assignees: SAUDI BASIC INDUSTRIES CORPORATION, SABIC GLOBAL TECHNOLOGIES B.V.
    Inventors: Andrew Mark Ward, Ravichander Narayanaswamy, Vijayanand Rajagopalan, Arno Johannes Maria Oprins, Egidius Jacoba Maria Schaerlaeckens, Raul Velasco Pelaez
  • Patent number: 10407356
    Abstract: The present invention relates to a process for producing ethene by the vapor phase dehydration of ethanol using a supported heteropolyacid catalyst. In particular, the present invention involves the use of a supported heteropolyacid catalyst, wherein the supported heteropolyacid catalyst is: i) a mixed oxide support comprising silica and a transition metal oxide, wherein silica is present in an amount of at least 50 wt. %, based on the weight of the mixed oxide support; or ii) a mixed oxide support comprising zirconia and a different transition metal oxide, wherein zirconia is present in an amount of at least 50 wt. %, based on the weight of the mixed oxide support. When used in a process for the preparation of ethene by vapor phase dehydration, and after attaining steady-state performance of the catalyst, the process may be 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: September 10, 2019
    Assignee: TECHNIP E&C LIMITED
    Inventor: Stephen Roy Partington
  • Patent number: 10407362
    Abstract: A method for producing diene comprises a step 1 of obtaining a straight chain internal olefin by removing a branched olefin from a raw material including at least the branched olefin and a straight chain olefin; and a step 2 of producing diene from the internal olefin by oxidative dehydrogenation using a first catalyst and a second catalyst, and the first catalyst has a complex oxide including bismuth, molybdenum and oxygen, and the second catalyst includes at least one selected from the group consisting of silica and alumina.
    Type: Grant
    Filed: February 16, 2016
    Date of Patent: September 10, 2019
    Assignee: JXTG NIPPON OIL & ENERGY CORPORATION
    Inventors: Nobuhiro Kimura, Junji Wakabayashi, Sosuke Higuchi
  • Patent number: 10322987
    Abstract: A method includes brominating a butanes feed stream including i-butane in a bromination reactor to form a bromination effluent stream including t-butyl bromide. The method includes dehydrobrominating the t-butyl bromide to form isobutylene. Another method includes brominating a mixed pentanes feed stream including i-pentane and n-pentane in a bromination reactor to form a bromination effluent stream including t-pentyl bromide. The method includes dehydrobrominating the t-pentyl bromide to form isoamylene and HBr.
    Type: Grant
    Filed: June 27, 2018
    Date of Patent: June 18, 2019
    Assignee: REACTION 35, LLC
    Inventors: Jeffrey H. Sherman, Peter K. Stoimenov
  • Patent number: 10300401
    Abstract: Separation of chlorosilane mixtures containing boron, arsenic, and/or phosphorus impurities is facilitated by a distillative separation using at least one divided column, with recycle streams to a first column being passed through an external absorbent for the impurities.
    Type: Grant
    Filed: October 7, 2015
    Date of Patent: May 28, 2019
    Assignee: WACKER CHEMIE AG
    Inventors: Maximilian Aigner, Uwe Paetzold, Jan Prochaska
  • Patent number: 10272359
    Abstract: A process is presented for the removal or aromatics from a hydrocarbon stream. The hydrocarbon stream is generated by a dehydrogenation process that generates aromatics. The process includes a two contact cooler system with the first and second contact coolers using different coolants. The second coolant is a non-aromatic hydrocarbon coolant that will absorb aromatics.
    Type: Grant
    Filed: October 27, 2017
    Date of Patent: April 30, 2019
    Assignee: UOP LLC
    Inventors: Gregory J. Nedohin, Mike Banach, David N. Myers
  • Patent number: 10214466
    Abstract: According to one embodiment described in this disclosure, a process for producing propylene may comprise at least partially metathesizing a first stream comprising at least about 10 wt. % butene to form a metathesis-reaction product, at least partially cracking the metathesis-reaction product to form a cracking-reaction product comprising propylene, and at least partially separating propylene from the cracking-reaction product to form a product stream comprising at least about 80 wt. % propylene.
    Type: Grant
    Filed: July 24, 2018
    Date of Patent: February 26, 2019
    Assignee: Saudi Arabian Oil Company
    Inventors: Sohel Shaikh, Aqil Jamal, Zhonglin Zhang
  • Patent number: 10214464
    Abstract: A reactor comprising a thermal barrier surrounding a combustion zone. The reactor further comprises a cooling jacket inner wall and a binder disposed between the cooling jacket inner wall and the thermal barrier, and a cooling jacket outer wall, wherein the cooling jacket inner wall and the cooling jacket outer wall define a cooling channel. The reactor further comprises an outer reactor wall disposed over the cooling jacket outer wall, wherein the outer reactor wall is impermeable and is configured to contain high pressure gas within the reactor.
    Type: Grant
    Filed: May 4, 2017
    Date of Patent: February 26, 2019
    Assignee: UOP LLC
    Inventors: Antoine Negiz, Robert B. James, Carl J. Stevens, Donald L. Mittendorf
  • Patent number: 10208259
    Abstract: A naphtha cracking feed stream is taken, heated and passed to a cracking reactor. Hydrogen is added to the cracking reactor to mitigate catalyst deactivation. The aliphatic compounds are selectively cracked and at least a portion of the alkyl groups on the aromatic compounds are selectively dealkylated in the presence of a cracking catalyst to produce a cracked effluent stream comprising aromatic compounds and cracked olefins.
    Type: Grant
    Filed: October 13, 2017
    Date of Patent: February 19, 2019
    Assignee: UOP LLC
    Inventors: Avram M. Buchbinder, Stanley J. Frey, Hayim Abrevaya, Falaah Falih
  • Patent number: 10202319
    Abstract: The present invention relates to a process for obtaining an olefin by metathesis including the steps of i) feeding at least one stream with at least one olefin as starting material to at least one first reactor with at least one pre-bed having at least one compound selected from the group of alkaline earth oxides and ii) feeding the stream leaving the at least one first reactor to at least one second reactor downstream to the at least one first reactor including at least one main bed having a) at least one first catalyst component and b) at least one second catalyst component. The first and second catalyst are physically mixed with each other. The operational temperature of the at least one first reactor is lower than the operational temperature of the at least one second reactor.
    Type: Grant
    Filed: September 11, 2014
    Date of Patent: February 12, 2019
    Assignee: Borealis AG
    Inventors: Eberhard Ernst, Mariana Stoyanova, Evgeny Kondratenko, David Linke
  • Patent number: 10195574
    Abstract: Apparatus and methods are provided for converting methane in a feed stream to acetylene. A hydrocarbon stream is introduced into a supersonic reactor and pyrolyzed to convert at least a portion of the methane to acetylene. The reactor effluent stream may be treated to convert acetylene to another hydrocarbon process.
    Type: Grant
    Filed: June 9, 2017
    Date of Patent: February 5, 2019
    Assignee: UOP LLC
    Inventors: Robert L. Bedard, Christopher Naunheimer, Gavin P. Towler, Laura E. Leonard, Gregory O. Woodcock, Donald L. Mittendorf
  • Patent number: 10166524
    Abstract: Apparatus and methods are provided for converting methane in a feed stream to acetylene. A hydrocarbon stream is introduced into a supersonic reactor and pyrolyzed to convert at least a portion of the methane to acetylene. The reactor effluent stream may be treated to convert acetylene to another hydrocarbon process.
    Type: Grant
    Filed: April 19, 2017
    Date of Patent: January 1, 2019
    Assignee: UOP LLC
    Inventors: Robert L. Bedard, Christopher Naunheimer, Gavin P. Towler, Laura E. Leonard, Rodolphe Dudebout, Gregory O. Woodcock, Donald L. Mittendorf
  • Patent number: 10160697
    Abstract: Apparatus and methods are provided for converting methane in a feed stream to acetylene. A hydrocarbon stream is introduced into a supersonic reactor and pyrolyzed to convert at least a portion of the methane to acetylene. The reactor effluent stream may be treated to convert acetylene to another hydrocarbon process.
    Type: Grant
    Filed: June 22, 2017
    Date of Patent: December 25, 2018
    Assignee: UOP LLC
    Inventors: Robert L. Bedard, Christopher Naunheimer, Gavin P. Towler, Laura E. Leonard, Gregory O. Woodcock, Donald L. Mittendorf, Aziz Sattar, Christopher D. Gatto, Robert S. Murray
  • Patent number: 10137442
    Abstract: A novel catalyst blend for processing of feedstocks into monoaromatics in a single stage, comprising at least one cracking catalyst, one heterogeneous transition metal catalyst, and optionally at least one hydrogenation catalyst. The process occurs in one-step or single stage with substantially no solvents or external additives, or when the feedstock contains less than 15% oxygen, the process includes additional water or steam to enable sufficient amounts of H2 being produced in-situ.
    Type: Grant
    Filed: May 25, 2017
    Date of Patent: November 27, 2018
    Assignee: BASF CORPORATION
    Inventor: Robert McGuire
  • Patent number: 10131850
    Abstract: A naphtha and methanol mixed catalytic cracking reaction process involves a simultaneous cracking reaction of naphtha and methanol using a circulating fluidized-bed reactor comprising a reactor, a stripper, and a regenerator. The naphtha is supplied from the bottom part of the reactor at a position between 0%˜5% of the total length of the reactor, and the methanol is supplied from the bottom part of the reactor at a position between 10%˜80% of the total length of the reactor. The catalytic cracking reaction process uses the circulating fluidized-bed reactor and can crack naphtha and methanol simultaneously by having different introduction positions for the naphtha and methanol in the reactor, which is advantageous for heat neutralization, so that energy consumption can be minimized and also the yield of light olefins can be improved by suppressing the production of light saturated hydrocarbons such as methane, ethane and propane.
    Type: Grant
    Filed: July 30, 2015
    Date of Patent: November 20, 2018
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Na Young Kang, Yong Ki Park, Won Choon Choi, Dae Jin Kim, Hwi Min Seo, Sunyoung Park, Joo Hyeong Oh, Sin Cheol Kang
  • Patent number: 10076746
    Abstract: The invention concerns a process for the preparation of a catalyst starting from a pre-catalyst comprising at least one catalytic metal and a support, said pre-catalyst having undergone a heat treatment at at least 60° C. without calcining, in which process said pre-catalyst is impregnated with a basic solution having a pH of more than 7.5 and containing at least one molecule in the zwitterionic form, and the impregnated pre-catalyst is dried at a temperature of at most 240° C. without subsequent calcining. The molecule in the zeolite form is selected from the group formed by amino-alcohol acids containing secondary or tertiary amine groups and containing at least one carboxylic acid function (and preferably only one) and at least one alcohol function. It is bicine or tricine, for example. The invention also concerns the catalyst prepared using this process, and its use in hydrotreatment and/or hydroconversion.
    Type: Grant
    Filed: December 8, 2014
    Date of Patent: September 18, 2018
    Assignee: IFP Energies nouvelles
    Inventors: Magalie Roy-Auberger, Ali Jahel
  • Patent number: 10066031
    Abstract: Disclosed is a method of separating an ethylene oligomerization effluent, in which, during the separation and purification of a product obtained through ethylene oligomerization, the temperature of the reaction product is adjusted and used, thus improving energy efficiency.
    Type: Grant
    Filed: October 11, 2016
    Date of Patent: September 4, 2018
    Assignee: LG CHEM, LTD.
    Inventors: Eun-Kyo Kim, Jong-Ku Lee, Jeong-Seok Lee, Mi-Kyung Kim
  • Patent number: 10065906
    Abstract: According to one or more embodiments described herein, propylene may be produced by a process which may comprise one or more of at least partially metathesizing a first portion of a first stream to form a first metathesis-reaction product, at least partially cracking the first metathesis-reaction product to form a cracking-reaction product.
    Type: Grant
    Filed: October 31, 2017
    Date of Patent: September 4, 2018
    Assignee: Saudi Arabian Oil Company
    Inventors: Sohel Shaikh, Aqil Jamal, Zhonglin Zhang
  • Patent number: 10059645
    Abstract: According to one embodiment described in this disclosure, a process for producing propylene may comprise at least partially metathesizing a first stream comprising at least about 10 wt. % butene to form a metathesis-reaction product, at least partially cracking the metathesis-reaction product to form a cracking-reaction product comprising propylene, and at least partially separating propylene from the cracking-reaction product to form a product stream comprising at least about 80 wt. % propylene.
    Type: Grant
    Filed: June 23, 2016
    Date of Patent: August 28, 2018
    Assignee: Saudi Arabian Oil Company
    Inventors: Sohel Shaikh, Aqil Jamal, Zhonglin Zhang
  • Patent number: 10035125
    Abstract: Producing C5 olefins from steam cracker C5 feeds may include reacting a mixed hydrocarbon stream comprising cyclopentadiene, C5 olefins, and C6+ hydrocarbons in a dimerization reactor where cyclopentadiene is dimerized to dicyclopentadiene. The dimerization reactor effluent may be separated into a fraction comprising the C6+ hydrocarbons and dicyclopentadiene and a second fraction comprising C5 olefins and C5 dienes. The second fraction, a saturated hydrocarbon diluent stream, and hydrogen may be fed to a catalytic distillation reactor system for concurrently separating linear C5 olefins from saturated hydrocarbon diluent, cyclic C5 olefins, and C5 dienes contained in the second fraction and selectively hydrogenating C5 dienes. An overhead distillate including the linear C5 olefins and a bottoms product including cyclic C5 olefins are recovered from the catalytic distillation reactor system.
    Type: Grant
    Filed: January 29, 2016
    Date of Patent: July 31, 2018
    Assignee: Lummus Technology Inc.
    Inventors: Yongqiang Xu, Peter Loezos, Willibrord A. Groten, Romain Lemoine
  • Patent number: 10029957
    Abstract: Apparatus and methods are provided for converting methane in a feed stream to acetylene. A hydrocarbon stream is introduced into a supersonic reactor and pyrolyzed to convert at least a portion of the methane to acetylene. The reactor effluent stream may be treated to convert acetylene to another hydrocarbon process.
    Type: Grant
    Filed: June 21, 2017
    Date of Patent: July 24, 2018
    Assignee: UOP LLC
    Inventors: Robert L. Bedard, Christopher Naunheimer, Gavin P. Towler, Laura E. Leonard, Rodolphe Dudebout, Gregory O. Woodcock, Donald L. Mittendorf, Aziz Sattar, Christopher D. Gatto, Robert S. Murray
  • Patent number: 9840676
    Abstract: A three step method for the conversion of ethanol into fuels that can be utilized as full-performance military jet or diesel fuels. Embodiments of the invention further describe methods for the selective conversion of ethanol to full performance saturated hydrocarbon fuels that are suitable for both jet and diesel propulsion.
    Type: Grant
    Filed: June 28, 2016
    Date of Patent: December 12, 2017
    Assignee: The Goverment of United States of America as Represented by to Secretary of the Navy
    Inventor: Benjamin G. Harvey
  • Patent number: 9834497
    Abstract: According to one or more embodiments described herein, a process for producing propylene, the process comprising at least partially metathesizing a first portion of a first stream to form a first metathesis-reaction product, at least partially cracking the first metathesis-reaction product to form a cracking-reaction product, the cracking reaction product comprising propylene and ethylene, at least partially separating ethylene from at least the cracking reaction product to form a first recycle stream, combining the first recycle stream with a second portion of the first stream to a form a mixed stream, and at least partially metathesizing the mixed stream to from a second metathesis-reaction product. In embodiments, the second metathesis-reaction product may comprise propylene, the first stream may comprise butene, and the first recycle stream may comprise ethylene.
    Type: Grant
    Filed: June 23, 2016
    Date of Patent: December 5, 2017
    Assignee: Saudi Arabian Oil Company
    Inventors: Sohel Shaikh, Aqil Jamal, Zhonglin Zhang
  • Patent number: 9790141
    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: Grant
    Filed: September 11, 2014
    Date of Patent: October 17, 2017
    Assignee: Total Research & Technology Feluy
    Inventors: Nikolai Nesterenko, Walter Vermeiren, Delphine Minoux, Sander Van Donk
  • Patent number: 9771307
    Abstract: A process may include contacting an oxygen-containing, halogenide-containing or sulphur-containing organic feedstock in an XTO reactor with a catalyst composite under conditions effective to convert the oxygen-containing, halogenide-containing or sulphur-containing organic feedstock to olefin products. The catalyst composite may include at least 10 weight percent of a modified molecular sieve. The modified molecular sieve may include at least 0.05 weight percent of an alkaline earth metal or a rare earth metal based on a weight of the modified molecular sieve. The modified molecular sieve may include at least 0.3 weight percent of P based on the weight of the modified molecular sieve.
    Type: Grant
    Filed: March 26, 2015
    Date of Patent: September 26, 2017
    Assignee: TOTAL RESEARCH & TECHNOLOGY FELUY
    Inventors: Nikolai Nesterenko, Walter Vermeiren, Sander Van Donk, Delphine Minoux
  • Patent number: 9771521
    Abstract: A method of reforming a heavy hydrocarbon distillate, which includes treating a heavy hydrocarbon distillate and a lignocellulosic biomass with a solvent, is provided. The method can be useful in maximizing conversion of the heavy hydrocarbon distillate into higher value-added distillate, for example, naphtha and a middle distillate, and allowing a sulfur compound produced by the decomposition of a heavy hydrocarbon distillate to catalyze pretreatment of the lignocellulosic biomass. Also, oxygen, hydroxymethylfurfural (HMF), levulinic acid, formic acid, and sulfuric acid produced by decomposition of the lignocellulosic biomass can catalyze decomposition of a heavy hydrocarbon distillate and lignocellulosic biomass, thereby activating decomposition of a heavy hydrocarbon distillate.
    Type: Grant
    Filed: December 28, 2012
    Date of Patent: September 26, 2017
    Assignee: Industry-Academic Cooperation Foundation, Yonsei University
    Inventors: Chang Ha Lee, Jae Hyuk Lee, Tran Tan Viet, Ik Sung Ahn, Doo Wook Kim
  • Patent number: 9751816
    Abstract: The present invention relates to a process of producing partly renewable light unsaturated hydrocarbons, in which at least one pyrolysis furnace of a unit for producing light unsaturated hydrocarbons from hydrocarbons is replaced by at least one reactor for conversion of ethanol to light unsaturated hydrocarbons.
    Type: Grant
    Filed: December 17, 2013
    Date of Patent: September 5, 2017
    Assignee: Braskem S.A.
    Inventors: Maria Ignez Broglio, Augusto Teruo Morita, Roberto Werneck do Carmo, Luis Felipe de Souza Tavares, Bruno Maia Moreira
  • Patent number: 9701913
    Abstract: A process for catalytic cracking includes the steps of: (a) contacting a hydrocarbon feed with a catalyst at catalytic cracking conditions; (b) adsorbing hydrogen on the catalyst during cracking; and (c) producing a cracked product, preferably propylene, wherein the catalyst comprises (i) a matrix, (ii) a catalytically active material, and (iii) a hydrogen adsorption material. Another process for catalytic cracking includes the steps of: (a) contacting a hydrocarbon feed with a catalyst at catalytic cracking conditions; (b) contacting the hydrocarbon feed with a hydrogen adsorption material; (c) adsorbing hydrogen on the hydrogen adsorption material during cracking; and (d) producing a cracked product, wherein the catalyst comprises (i) a matrix and (ii) a catalytically active material.
    Type: Grant
    Filed: December 17, 2013
    Date of Patent: July 11, 2017
    Assignee: UOP LLC
    Inventors: Matthew Lippmann, Alex A. Rio, Keith A. Couch
  • Patent number: 9687829
    Abstract: A novel catalyst blend for processing of feedstocks into monoaromatics in a single stage, comprising at least one cracking catalyst, one heterogeneous transition metal catalyst, and optionally at least one hydrogenation catalyst. The process occurs in one-step or single stage with substantially no solvents or external additives, or when the feedstock contains less than 15% oxygen, the process includes additional water or steam to enable sufficient amounts of H2 being produced in-situ.
    Type: Grant
    Filed: February 6, 2015
    Date of Patent: June 27, 2017
    Assignee: BASF CORPORATION
    Inventor: Robert McGuire
  • Patent number: 9677014
    Abstract: An apparatus and process are provided for processing hydrocarbon feeds. The process enhances the conversion of hydrocarbon feeds into conversion products, such as ethylene and propylene. In particular, the present techniques utilize two high-severity pyrolysis reactors integrated with another reactor type to convert hydrocarbons to other petrochemical products. The pyrolysis reactors recycle a portion of one of the reactor products to at least one of the pyrolysis reactors to further enhance the process.
    Type: Grant
    Filed: December 20, 2011
    Date of Patent: June 13, 2017
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Paul F. Keusenkothen, Frank Hershkowitz
  • Patent number: 9611193
    Abstract: A process for the production of C4 olefins, which may include: contacting a hydrocarbon mixture comprising alpha-pentenes with an isomerization catalyst to form an isomerization product comprising beta-pentenes; contacting ethylene and the beta-pentenes with a first metathesis catalyst to form a first metathesis product comprising butenes and propylene, as well as any unreacted ethylene and C5 olefins; and fractionating the first metathesis product to for an ethylene fraction, a propylene fraction, a butene fraction, and a C5 fraction.
    Type: Grant
    Filed: October 5, 2015
    Date of Patent: April 4, 2017
    Assignee: Lummus Technology Inc.
    Inventors: Sukwon Choi, Bala Ramachandran
  • Patent number: 9567269
    Abstract: The present disclosure provides oxidative coupling of methane (OCM) systems for small scale and world scale production of olefins. An OCM system may comprise an OCM subsystem that generates a product stream comprising C2+ compounds and non-C2+ impurities from methane and an oxidizing agent. At least one separations subsystem downstream of, and fluidically coupled to, the OCM subsystem can be used to separate the non-C2+ impurities from the C2+ compounds. A methanation subsystem downstream and fluidically coupled to the OCM subsystem can be used to react H2 with CO and/or CO2 in the non-C2+ impurities to generate methane, which can be recycled to the OCM subsystem. The OCM system can be integrated in a non-OCM system, such as a natural gas liquids system or an existing ethylene cracker.
    Type: Grant
    Filed: March 21, 2016
    Date of Patent: February 14, 2017
    Assignee: SILURIA TECHNOLOGIES, INC.
    Inventors: Guido Radaelli, Humera A. Rafique, Srinivas Vuddagiri, Erik C. Scher, Jarod McCormick, Joel Cizeron, Bipinkumar Patel, Satish Lakhapatri
  • Patent number: 9517447
    Abstract: A process for the providing a regenerant gas stream for a regenerable adsorbent used to remove water and hydrogen sulfide from a reactor effluent in a catalytic dehydrogenation process is described. The reactor effluent is compressed in a compressor to provide a compressed effluent. The compressed effluent may be treated to remove chlorides, and then passed to a dryer zone having a regenerable adsorbent. A regenerant gas stream is used to desorb the water and hydrogen sulfide and the spent regenerant stream may be passed to a cleaning zone having a sorbent configured to remove hydrogen sulfide from the spent regenerant stream. The cleaned regenerant gas stream may be recycled to the dryer zone to desorb and/or regenerate the regenerable adsorbent.
    Type: Grant
    Filed: June 1, 2015
    Date of Patent: December 13, 2016
  • Patent number: 9512047
    Abstract: Integrated systems are provided for the production of higher hydrocarbon compositions, for example liquid hydrocarbon compositions, from methane using an oxidative coupling of methane system to convert methane to ethylene, followed by conversion of ethylene to selectable higher hydrocarbon products. Integrated systems and processes are provided that process methane through to these higher hydrocarbon products.
    Type: Grant
    Filed: March 21, 2016
    Date of Patent: December 6, 2016
    Assignee: SILURIA TECHNOLOGIES, INC.
    Inventors: Greg Nyce, Peter Czerpak, Carlos Faz, Jarod McCormick, William Michalak, Bipinkumar Patel, Guido Radaelli, Tim A. Rappold, Ron Runnebaum, Erik C. Scher, Aihua Zhang, Joel Cizeron
  • Patent number: 9499458
    Abstract: Mixed pentenes may be converted to propylene by feeding an alcohol, linear pentenes, and isopentenes to an etherification reactor. The alcohol and isopentenes may be reacted in the etherification reactor to convert isopentenes to tertiary amyl alkyl ether, which may be separated from the linear pentenes, recovered as a linear pentene fraction. The tertiary amyl alkyl ether may be fed to a decomposition reactor to convert at least a portion of the tertiary amyl alkyl ether to alcohol and isopentenes. The alcohol and isopentenes may then be separated to recover an isopentene fraction and an alcohol fraction. The isopentene fraction is then fed to a skeletal isomerization reactor to convert at least a portion of the isopentenes to linear pentenes, the effluent from which may be recycled to the etherification reactor. Ethylene and the linear pentene fraction may then be to a metathesis reactor to produce propylene.
    Type: Grant
    Filed: November 1, 2013
    Date of Patent: November 22, 2016
    Assignee: Lummus Technology Inc.
    Inventors: Bala Ramachandran, Sukwon Choi
  • Patent number: 9452422
    Abstract: Hydrotreating catalysts and processes useful for the conversion of methoxylated aromatic compounds to simple aromatic compounds are provided. The catalysts comprise transition metal selected from the group consisting of Group 8 metals, Group 9 metals, Group 10 metals, Group 11 metals, and mixtures thereof, and catalyst support selected from the group consisting of shape-selective zeolite, silica, titania, zirconia, and mixtures thereof.
    Type: Grant
    Filed: March 12, 2013
    Date of Patent: September 27, 2016
    Assignee: The Procter & Gamble Company
    Inventors: Patti Jean Kellett, Dimitris Ioannis Collias
  • Patent number: 9334204
    Abstract: The present disclosure provides oxidative coupling of methane (OCM) systems for small scale and world scale production of olefins. An OCM system may comprise an OCM subsystem that generates a product stream comprising C2+ compounds and non-C2+ impurities from methane and an oxidizing agent. At least one separations subsystem downstream of, and fluidically coupled to, the OCM subsystem can be used to separate the non-C2+ impurities from the C2+ compounds. A methanation subsystem downstream and fluidically coupled to the OCM subsystem can be used to react H2 with CO and/or CO2 in the non-C2+ impurities to generate methane, which can be recycled to the OCM subsystem. The OCM system can be integrated in a non-OCM system, such as a natural gas liquids system or an existing ethylene cracker.
    Type: Grant
    Filed: July 1, 2015
    Date of Patent: May 10, 2016
    Assignee: Siluria Technologies, Inc.
    Inventors: Guido Radaelli, Humera A. Rafique, Srinivas Vuddagiri, Erik C. Scher, Jarod McCormick, Joel Cizeron, Bipinkumar Patel, Satish Lakhapatri
  • Patent number: 9309168
    Abstract: Processes for forming propylene are described herein.
    Type: Grant
    Filed: January 10, 2013
    Date of Patent: April 12, 2016
    Assignees: Equistar Chemicals, LP, Lyondell Chemical Technology, L.P.
    Inventors: Allen David Hood, Jr., Robert S. Bridges
  • Patent number: 9279088
    Abstract: Steam pyrolysis and hydroprocessing are integrated including hydrogen redistribution to permit direct processing of crude oil feedstocks to produce petrochemicals including olefins and aromatics. A feed is initially split into a light portion and a heavy portion, and the heavy portion is hydroprocessed. A hydroprocessed effluent is charged, along with steam, to a convection section of a steam pyrolysis zone. The mixture is heated and passed to a vapor-liquid separation section. A residual portion is removed and light components are charged to a pyrolysis section of the steam pyrolysis zone. A mixed product stream is recovered from the steam pyrolysis zone and it is separated into product including olefins and aromatics.
    Type: Grant
    Filed: April 17, 2013
    Date of Patent: March 8, 2016
    Assignee: Saudi Arabian Oil Company
    Inventors: Raheel Shafi, Abdennour Bourane, Esam Sayed, Ibrahim A Abba, Abdul Rahman Zafer Akhras
  • Patent number: 9120736
    Abstract: The invention relates to a method for producing compositions containing unsaturated compounds, wherein (A) one or more unsaturated monocarboxylic acids having 10 to 24 C-atoms or esters of said monocarboxylic acids and optionally (B) one or more compounds having at least one C?C double bond (wherein the compounds (B) are different from the compounds (A)) are subjected to a tandem isomerization/metathesis reaction sequence in the presence of a palladium catalyst and a ruthenium catalyst, providing that the palladium catalysts used are compounds that contain at least one structural element Pd—P(R1R2R3), wherein the radicals R1 to R3, independently of one another, each comprise 2 to 10 C-atoms, which may be aliphatic, alicyclic, aromatic or heterocyclic respectively, providing that at least one of the radicals R1 to R3 contains a beta-hydrogen, wherein the palladium catalyst is used as such or is produced in situ, providing that the method is carried out in the absence of substances that have a pKa value of 3 or
    Type: Grant
    Filed: February 25, 2012
    Date of Patent: September 1, 2015
    Assignee: Cognis IP Management GmbH
    Inventors: Lukas J. Gooβen, Dominik Ohlmann, Markus Dierker
  • Patent number: 9051519
    Abstract: Methods are provided for refining natural oil feedstocks and partially hydrogenating polyunsaturated olefins and polyunsaturated esters. 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 polyunsaturated olefins from the polyunsaturated esters in the metathesized product. In certain embodiments, the methods further comprise partially hydrogenating the polyunsaturated olefins in the presence of a hydrogenation catalyst, wherein at least a portion of the polyunsaturated olefins are converted to monounsaturated olefins. In other embodiments, the methods further comprise partially hydrogenating the polyunsaturated esters in the presence of a hydrogenation catalyst, wherein at least a portion of the polyunsaturated esters are converted to monounsaturated esters.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: June 9, 2015
    Assignee: Elevance Renewable Sciences, Inc.
    Inventors: Linda A. Kunz, Tessa M. Pals, Steven A. Cohen, Melvin L. Luetkens, Jr., Chander Balakrishnan, Robert B. Snyder
  • Publication number: 20150148575
    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: Application
    Filed: November 25, 2013
    Publication date: May 28, 2015
    Applicant: UOP LLC
    Inventors: John J. Senetar, Daniel A. Kauff, Andrea G. Bozzano
  • Patent number: 9040762
    Abstract: Metal oxide catalysts comprising various dopants are provided. The catalysts are useful as heterogenous catalysts in a variety of catalytic reactions, for example, the oxidative coupling of methane to C2 hydrocarbons such as ethane and ethylene. Related methods for use and manufacture of the same are also disclosed.
    Type: Grant
    Filed: October 17, 2014
    Date of Patent: May 26, 2015
    Assignee: Siluria Technologies, Inc.
    Inventors: Joel M. Cizeron, Erik C. Scher, Fabio R. Zurcher, Wayne P. Schammel, Greg Nyce, Anja Rumplecker, Jarod McCormick, Marian Alcid, Joel Gamoras, Daniel Rosenberg, Erik-Jan Ras
  • Patent number: 9040757
    Abstract: In one embodiment, the present application discloses methods to selectively synthesize higher alcohols and hydrocarbons useful as fuels and industrial chemicals from syngas and biomass. Ketene and ketonization chemistry along with hydrogenation reactions are used to synthesize fuels and chemicals. In another embodiment, ketene used to form fuels and chemicals may be manufactured from acetic acid which in turn can be synthesized from synthesis gas which is produced from coal, biomass, natural gas, etc.
    Type: Grant
    Filed: March 8, 2013
    Date of Patent: May 26, 2015
    Assignee: PIONEER ENERGY
    Inventors: John Henri, Jan Zygmunt, Mark Bergren, Robert Zubrin
  • Publication number: 20150139895
    Abstract: A process for converting polycyclic aromatic compounds to monocyclic aromatic compounds includes pyrolyzing a coal feed to produce a coke stream and a coal tar stream. The coal tar stream is cracked, and the cracked coal tar stream is fractionated to produce an aromatic fraction comprising the polycyclic aromatic compounds. The process further includes hydrocracking the aromatic fraction to partially hydrogenate at least a first portion of the aromatic fraction, and to open at least one ring of a second portion of the aromatic fraction to form the monocyclic aromatic compounds from the polycyclic compounds, and recycling the first portion of the aromatic fraction.
    Type: Application
    Filed: August 28, 2014
    Publication date: May 21, 2015
    Inventors: James A. Johnson, John Q. Chen, Peter K. Coughlin, Stanley J. Frey, Vasant P. Thakkar
  • Publication number: 20150141726
    Abstract: A process for producing olefins from a coal feed includes providing a coal tar stream and fractionating the coal tar stream to provide a hydrocarbon stream that includes hydrocarbons having an initial boiling point of about 250° C. or greater. The hydrocarbon stream is hydrotreated to reduce a concentration of one or more of nitrogen, sulfur, and oxygen in the hydrocarbon stream, and the hydrotreated hydrocarbon stream is cracked in a fluidized catalytic cracking zone to produce an olefin stream.
    Type: Application
    Filed: August 25, 2014
    Publication date: May 21, 2015
    Inventors: Vasant P. Thakkar, Paul T. Barger, Maureen L. Bricker, John Q. Chen, Peter K. Coughlin, Stanley J. Frey, James A. Johnson, Joseph A. Kocal, Matthew Lippmann, Kurt M. Vanden Bussche
  • Publication number: 20150137043
    Abstract: A method of processing a coal feed to produce aromatic hydrocarbon compounds includes providing a coal tar stream and converting the coal tar stream to a conversion product comprising at least olefins, paraffins, and aromatics. The process further includes separating the olefins and C5? paraffins from the conversion product, and contacting the separated olefins and the C5? paraffins with a catalyst to dehydrogenize, oligomerize, and cyclize the olefins and the C5? paraffins, to form aromatic hydrocarbon compounds.
    Type: Application
    Filed: August 26, 2014
    Publication date: May 21, 2015
    Inventors: John Q. Chen, Peter K. Coughlin, Stanley J. Frey, James A. Johnson, Vasant P. Thakkar
  • Publication number: 20150141720
    Abstract: A process for the double-bond isomerization of olefins is disclosed. The process may include contacting a hydrocarbon stream including olefins with a ?-alumina-titania isomerization catalyst to convert at least a portion of the olefin to its positional isomer. The ?-alumina-titania isomerization catalysts disclosed herein may also have the activity to convert alcohol into additional olefins, while having increased resistance to oxygenate poisons.
    Type: Application
    Filed: November 20, 2014
    Publication date: May 21, 2015
    Applicant: LUMMUS TECHNOLOGY INC.
    Inventors: Bala Ramachandran, Sukwon Choi, Robert J. Gartside
  • Publication number: 20150141721
    Abstract: Processes for the production of olefins are disclosed, which may include: contacting a hydrocarbon mixture comprising linear butenes with an isomerization catalyst to form an isomerization product comprising 2-butenes and 1-butenes; contacting the isomerization product with a first metathesis catalyst to form a first metathesis product comprising 2-pentene and propylene, as well as any unreacted C4 olefins, and byproducts ethylene and 3-hexene; and fractionating the first metathesis product to form a C3? fraction and a C5 fraction comprising 2-pentene. The 2-pentene may then be advantageously used to produce high purity 1-butene, 3-hexene, 1-hexene, propylene, or other desired products.
    Type: Application
    Filed: November 20, 2014
    Publication date: May 21, 2015
    Applicant: LUMMUS TECHNOLOGY INC.
    Inventors: Sukwon Choi, Bala Ramachandran