By Condensation Of Entire Molecules Or Entire Hydrocarbyl Moieties Thereof, E.g., Alkylation, Etc. Patents (Class 585/446)
  • Patent number: 10766834
    Abstract: Disclosed are selectivated transalkylation catalyst compositions and methods of making the same. The selectivated transalkylation catalyst compositions have a zeolite framework structure of MWW, FAU, BEA*, or MOR, or mixtures thereof, and are selectivated with a selectivating solution. The selectivating solution includes a dissolved ion of at least one element in Group 1, Group 2, Group 15, Group 16, or Group 17 of the Periodic Table. Also disclosed are processes of producing ethylbenzene and cumene using the selectivated transalkylation catalyst compositions.
    Type: Grant
    Filed: February 19, 2018
    Date of Patent: September 8, 2020
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Brett T. Loveless, Daniel J. Benedict, Kathleen M. Keville, Juan D. Henao, Matthew S. Ide
  • Patent number: 10173949
    Abstract: Alkylate is produced by supplying iso-C4+ hydrocarbon feed to an alkylation reactor, and by further selectively supplying to the alkylation reactor an olefin selected from the group consisting of refinery grade propylene (RGP) and polymer grade propylene (PGP), and combinations thereof. The olefin feed is controlled such that the proportion of PGP supplied through the olefin feed inlet exceeds that of RGP for a predetermined time interval, using a special purpose computer programmed to optimize the allocation of PGP between alkylation production and a commodity market in order to increase total net profit margin.
    Type: Grant
    Filed: July 20, 2018
    Date of Patent: January 8, 2019
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Ipokratis Polizopoulos, Ezra J. Czuba, Brian C. Mayo
  • Patent number: 9884798
    Abstract: The invention provides a process for the catalytic conversion of a saccharide-containing feedstock in a reactor, wherein saccharide-containing feedstock is provided to the reactor as a feed stream through a feed pipe and is contacted with a catalyst system in the reactor and a reaction product is continuously removed from the reactor and wherein the saccharide-containing feedstock is provided through the feed pipe as a pulsed flow and is alternated with a second feed stream comprising a solvent being provided through the same feed pipe.
    Type: Grant
    Filed: April 1, 2014
    Date of Patent: February 6, 2018
    Inventors: Evert Van Der Heide, Pieter Huizenga
  • Patent number: 9556084
    Abstract: Alkylation systems and methods of minimizing alkylation catalyst regeneration are described herein. The alkylation systems generally include a preliminary alkylation system adapted to receive an input stream including an alkyl aromatic hydrocarbon and contact the input stream with a preliminary alkylation catalyst disposed therein to form a first output stream. The preliminary alkylation catalyst generally includes a zeolite catalyst having a SiO2/Al2O3 ratio of less than about 25. The alkylation systems further include a first alkylation system adapted to receive the first output stream and contact the first output stream with a first alkylation catalyst disposed therein and an alkylating agent to form a second output stream.
    Type: Grant
    Filed: January 14, 2014
    Date of Patent: January 31, 2017
    Assignee: FINA TECHNOLOGY, INC.
    Inventors: James R. Butler, Xin Xiao, James T. Merrill
  • Patent number: 9556083
    Abstract: Alkylation systems and methods of minimizing alkylation catalyst regeneration are described herein. The alkylation systems generally include a preliminary alkylation system adapted to receive an input stream including an alkyl aromatic hydrocarbon and contact the input stream with a preliminary alkylation catalyst disposed therein to form a first output stream. The preliminary alkylation catalyst generally includes a zeolite catalyst having a SiO2/Al2O3 ratio of less than about 25. The alkylation systems further include a first alkylation system adapted to receive the first output stream and contact the first output stream with a first alkylation catalyst disposed therein and an alkylating agent to form a second output stream.
    Type: Grant
    Filed: August 18, 2011
    Date of Patent: January 31, 2017
    Assignee: FINA TECHNOLOGY, INC.
    Inventors: James Butler, Xin Xiao, Jim Merrill
  • Patent number: 9556093
    Abstract: A method for producing alkylphenol is provided. The method includes charging phenol and an olefinic compound into a reaction zone of a reactive distillation tower for a reaction; and separating a product stream containing alkylphenol from the reactive distillation tower, wherein the boiling point of the olefinic compound is lower than that of the phenol, and the phenol is charged into the reactive distillation tower at a charging position located above a position for charging the olefinic compound.
    Type: Grant
    Filed: January 20, 2016
    Date of Patent: January 31, 2017
    Assignee: Chang Chun Petrochemical Co., Ltd.
    Inventors: Tian-Yuan Lin, Shih-Bo Hung
  • Patent number: 9126184
    Abstract: A process is disclosed using a new catalyst for use in the alkylation of benzene with a substantially linear olefin. The catalyst allows for cation exchange with a rare earth element to increase the alkylation of benzene, while reducing the amount of isomerization of the alkyl group. This is important for increasing the quality of the alkylbenzene by increasing the linearity of the alkylbenzene.
    Type: Grant
    Filed: December 16, 2009
    Date of Patent: September 8, 2015
    Assignee: UOP LLC
    Inventors: Deng-Yang Jan, Mark G. Riley, Stephen W. Sohn, Jaime G. Moscoso, Raelynn M. Miller
  • Patent number: 9012696
    Abstract: Process for the alkylation of aromatic hydrocarbons by means of olefins containing from 2 to 8 carbon atoms, which comprises feeding the hydrocarbon, olefin, and possibly water, to the head of a fixed-bed reactor, operating with a “trickle flow” regime, containing at least one layer of a catalyst comprising a medium-or large-pore zeolite.
    Type: Grant
    Filed: June 21, 2012
    Date of Patent: April 21, 2015
    Assignee: Versalis S.p.A
    Inventors: Paolo Calaresu, Alessandro Del Seppia, Elena Bencini, Giovanni Antonio Fois, Alessandro Casalini
  • Patent number: 9006506
    Abstract: The invention relates to the production of paraxylene by an alkylation process that also produces oxygenates. The process is controlled to utilize recycle to minimize said oxygenates.
    Type: Grant
    Filed: September 14, 2012
    Date of Patent: April 14, 2015
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Xiaobo Zheng, John Di-Yi Ou, Mark P. Hagemeister, Jon E. R. Stanat
  • Patent number: 8946484
    Abstract: In a process for producing phenol and cyclohexanone a feed comprising cyclohexylbenzene hydroperoxide and water in an amount from 1 to 15,000 ppm, based upon total weight of feed, is contacted with a cleavage catalyst comprising an aluminosilicate of the FAU type under cleavage conditions effective to convert at least a portion of the cyclohexylbenzene hydroperoxide into phenol and cyclohexanone.
    Type: Grant
    Filed: December 15, 2011
    Date of Patent: February 3, 2015
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Kun Wang, Roberto Garcia
  • Patent number: 8937206
    Abstract: The process converts FCC olefins to heavier compounds. The heavier compounds are more easily separated from the unconverted paraffins. The heavier compounds can be recycled to an FCC unit or delivered to a separate FCC unit. Suitable conversion zones are oligomerization and aromatic alkylation zones.
    Type: Grant
    Filed: March 27, 2014
    Date of Patent: January 20, 2015
    Assignee: UOP LLC
    Inventors: Joao Jorge da Silva Ferreira Alves, James E. Rekoske, Christopher P. Nicholas
  • Patent number: 8937205
    Abstract: A hydrocarbon upgrading process is described in which a hydrocarbon feed is treated in at least one of a steam cracker, catalytic cracker, coker, hydrocracker, and reformer under suitable conditions to produce a first stream comprising aliphatic and aromatic hydrocarbons. A second stream comprising C6-C9 aliphatic and aromatic hydrocarbons is recovered from the first stream and aliphatic hydrocarbons are removed from at least part of the second stream to produce an aliphatic hydrocarbon-depleted stream. The aliphatic hydrocarbon-depleted stream is then dealkylated and/or transalkylated and/or cracked (D/T/C) by contact with a catalyst under suitable reaction conditions to produce a third stream having an increased benzene and/or toluene content compared with said aliphatic hydrocarbon-depleted stream and a light paraffin by-product. Benzene and/or toluene from the third stream is then methylated with a methylating agent to produce a xylene-enriched stream.
    Type: Grant
    Filed: May 7, 2012
    Date of Patent: January 20, 2015
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Larry L. Iaccino, Glenn C. Wood, Jesus A. Ramos, Lane L. McMorris
  • Patent number: 8921604
    Abstract: In a process for producing cyclohexylbenzene, benzene is reacted with cyclohexene in a first reaction zone under conditions effective to produce a reaction product comprising cyclohexylbenzene and at least one polycyclohexylbenzene. At least a portion of the reaction product and a stripping agent comprising at least one C1 to C11 hydrocarbon or hydrogen are then separately supplied to a separation device and separated into at least a first fraction rich in cyclohexylbenzene and a second fraction rich in the at least one polycyclohexylbenzene.
    Type: Grant
    Filed: November 21, 2011
    Date of Patent: December 30, 2014
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Christopher L. Becker, James R. Lattner, Charles Morris Smith, Kun Wang
  • Patent number: 8921636
    Abstract: Methods for converting an HF alkylation unit to an ionic liquid alkylation system configured for performing ionic liquid catalyzed alkylation processes may comprise connecting at least one component configured for ionic liquid catalyzed alkylation to at least one component of the HF alkylation unit, wherein the at least one component of the HF alkylation unit is retained, modified or adapted for use in the ionic liquid alkylation system. An ionic liquid alkylation system derived from an existing or prior HF alkylation unit is also disclosed.
    Type: Grant
    Filed: September 12, 2011
    Date of Patent: December 30, 2014
    Assignee: Chevron U.S.A. Inc.
    Inventors: Robert Fletcher Cleverdon, Christine Marie Phillips, Hye Kyung Cho Timken
  • Patent number: 8889937
    Abstract: One exemplary embodiment may be a process for producing one or more alkylated aromatics. Generally, the process includes providing a first stream including an effective amount of benzene for alkylating benzene from a fractionation zone, providing a second stream including an effective amount of ethene for alkylating benzene from a fluid catalytic cracking zone, providing at least a portion of the first and second streams to an alkylation zone; and passing at least a portion of an effluent including ethylbenzene from the alkylation zone downstream of a para-xylene separation zone.
    Type: Grant
    Filed: June 9, 2011
    Date of Patent: November 18, 2014
    Assignee: UOP LLC
    Inventors: Robert Haizmann, Laura E. Leonard, Paula L. Bogdan
  • Patent number: 8884065
    Abstract: In a process for producing a cycloalkylaromatic compound, an aromatic compound and a cyclic olefin are contacted with a first catalyst under conditions effective to produce a reaction product comprising the cycloalkylaromatic compound and at least one non-fused bicyclic by-product. The at least one non-fused bicyclic by-product is then contacted with a second catalyst under conditions effective to convert at least a portion of the at least one non-fused bicyclic by-product to a converted by-product.
    Type: Grant
    Filed: October 25, 2011
    Date of Patent: November 11, 2014
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Kun Wang, Jihad M. Dakka, Stephen Zushma, James R. Lattner, Christopher L. Becker, Tan-Jen Chen
  • Patent number: 8865956
    Abstract: Embodiments of methods for the production of linear alkylbenzene and optionally biofuel from a natural oil are provided. A method comprises the step of deoxygenating the natural oils to form paraffins. A first portion of the paraffins is hydrocracked to form a first stream of normal and lightly branched paraffins in the C9 to C14 range and a second stream of isoparaffins. The first stream is dehydrogenated to provide mono-olefins. Then, benzene is alkylated with the mono-olefins under alkylation conditions to provide an alkylation effluent comprising alkylbenzenes and benzene. Thereafter, the alkylbenzenes are isolated to provide the alkylbenzene product. Optionally a second portion of the paraffins and the isoparaffins are processed to form biofuel.
    Type: Grant
    Filed: July 30, 2013
    Date of Patent: October 21, 2014
    Assignee: UOP LLC
    Inventors: Amarendra Anumakonda, Srikantiah Raghuram, Joao Jorge da Sllva Ferreira Alves, Andrea G. Bozzano
  • Patent number: 8853479
    Abstract: Embodiments of methods for production of linear alkylbenzene and optionally biofuel from natural oil are provided. Natural oils are deoxygenated to form a stream comprising paraffins. A first portion of the paraffins are dehydrogenated to provide mono-olefins. Then, benzene is alkylated with the mono-olefins under alkylation conditions to provide an alkylation effluent comprising alkylbenzenes and benzene. Thereafter, the alkylbenzenes are isolated to provide the alkylbenzene product. Optionally, a second portion of the paraffins may be processed to form biofuel.
    Type: Grant
    Filed: July 30, 2013
    Date of Patent: October 7, 2014
    Assignee: UOP LLC
    Inventors: Andrea G. Bozzano, Matthew J. Griffiths, Amarendra Anumakonda
  • Publication number: 20140296598
    Abstract: The invention is directed to a process for the removal of olefin impurities from a feedstream comprising greater than equilibrium amounts of paraxylene by contact of the feedstream with a bed of solid acid catalyst to produce a product comprising reduced olefin impurities (when compared with said feedstream), said process comprising at least one of (i) reduced bed temperature on startup, and (ii) reduced flow rate on startup, wherein, in embodiments, there is a reduction in side reactions such as isomerization and/or transalkylation and/or disproportionation of paraxylene, when compared with conventional startup procedures.
    Type: Application
    Filed: February 21, 2014
    Publication date: October 2, 2014
    Inventors: Glenn A. Heeter, John D. Ou, Robert G. Tinger
  • Patent number: 8841500
    Abstract: Provided is a process for preparing alkyl aromatic compounds. The process comprises contacting an alkane under dehydrogenation conditions in the presence of a dehydrogenation catalyst, e.g., a pincer iridium catalyst, to form olefins, and then contacting the olefins generated with an aromatic compound under alkylation conditions. Both reactions are conducted in a single reactor, and occur simultaneously.
    Type: Grant
    Filed: September 12, 2012
    Date of Patent: September 23, 2014
    Assignees: Chevron U.S.A. Inc., Rutgers, The State University of New Jersey
    Inventors: Alan Stuart Goldman, Long Van Dinh, William L. Schinski
  • Patent number: 8704021
    Abstract: The process converts FCC olefins to heavier compounds. The heavier compounds are more easily separated from the unconverted paraffins. The heavier compounds can be recycled to an FCC unit or delivered to a separate FCC unit. Suitable conversion zones are oligomerization and aromatic alkylation zones.
    Type: Grant
    Filed: May 23, 2013
    Date of Patent: April 22, 2014
    Assignee: UOP LLC
    Inventors: Joao Jorge da Silva Ferreira Alves, James E. Rekoske, Christopher P. Nicholas
  • Publication number: 20140100402
    Abstract: A process for producing para-xylene, by (a) contacting toluene with methanol in the presence of an alkylation catalyst under conditions effective to produce an alkylation effluent comprising xylenes and a by-product mixture comprising water, dimethyl ether and C4? hydrocarbons; (b) separating the alkylation effluent into a first fraction containing xylenes and a second fraction containing the by-product mixture; (c) removing water from the second fraction to produce a dried by-product mixture; (d) fractionating the dried by-product mixture to separate the mixture into a bottoms stream containing dimethyl ether and an overhead stream containing at least some of the C4- hydrocarbons; and (e) recovering ethylene and propylene from the overhead stream.
    Type: Application
    Filed: September 24, 2013
    Publication date: April 10, 2014
    Inventors: Allen S. Gawlik, Indulis J. Eilands, Terrance C. Osby
  • Publication number: 20140100401
    Abstract: The present invention relates to catalyst composition prepared by a method wherein an aluminosilicate zeolite having its pores filled with templating agent with a specific organic silicon compound to deposit said organic silicon compound on the surface of the zeolite to provide an organosilicon treated catalyst precursor; and calcining the organosilicon treated catalyst precursor under conditions sufficient to remove the templating agent from the zeolite. Furthermore, the present invention relates to a method for preparing said catalyst composition and a process for alkylation of an aromatic hydrocarbon comprising contacting the catalyst composition of the present invention with a feed stream comprising said aromatic hydrocarbon and an alkylating agent under aromatic alkylation conditions.
    Type: Application
    Filed: May 3, 2012
    Publication date: April 10, 2014
    Applicant: Saudi Basic Industries Corporation
    Inventor: Debasish Das
  • Publication number: 20140066678
    Abstract: We provide processes, and process units for practicing the processes, comprising a. regenerating a used catalyst comprising an ionic liquid catalyst and a chloride, from an alkylation reactor, in a hydrogenation reactor to produce a regenerated catalyst effluent; b. separating at least a portion of the regenerated catalyst effluent into a gas fraction comprising a hydrogen gas and into a light hydrocarbon fraction comprising a hydrogen chloride; c. recycling at least a part of the gas fraction comprising the hydrogen gas to the hydrogenation reactor; and d. recovering at least an amount of the light hydrocarbon fraction comprising the hydrogen chloride and recycling the at least the amount of the light hydrocarbon fraction to the alkylation reactor. The alkylation process units comprise a hydrogenation reactor, a fractionation unit, and connections for transmitting the gas fraction to the hydrogenation reactor and for transmitting the light hydrocarbon fraction to the alkylation reactor.
    Type: Application
    Filed: July 31, 2012
    Publication date: March 6, 2014
    Applicant: Chevron U.S.A. Inc.
    Inventors: Hye Kyung Cho Timken, Bong-Kyu Chang
  • Patent number: 8652321
    Abstract: Production of gasolines with low sulfur contents from a starting gasoline containing sulfur-containing compounds comprising a stage a) for selective hydrogenation of non-aromatic polyunsaturated compounds present in the starting gasoline, a stage b) for increasing the molecular weight of the light sulfur-containing products that are initially present in the gasoline that enters this stage, a stage c) for alkylation of at least a portion of the sulfur-containing compounds present in the product that originates from stage b), a stage d) for fractionation of the gasoline that originates from stage c) into at least two fractions, one fraction virtually lacking in sulfur-containing compounds, whereby the other contains a larger proportion of sulfur-containing compounds (heavy gasoline), a stage e) for catalytic treatment of the heavy gasoline for transformation of sulfur-containing compounds under conditions for the at least partial decomposition of hydrogenation of these sulfur-containing compounds.
    Type: Grant
    Filed: June 1, 2010
    Date of Patent: February 18, 2014
    Assignee: IFP Energies nouvelles
    Inventors: Quentin Debuisschert, Denis Uzio, Jean-Luc Nocca, Florent Picard
  • Patent number: 8609917
    Abstract: One exemplary embodiment can be a process for increasing a mole ratio of methyl to phenyl of one or more aromatic compounds in a feed. The process can include reacting an effective amount of one or more aromatic compounds and an effective amount of one or more non-aromatic compounds to convert about 90%, by weight, of one or more C6+ non-aromatic compounds.
    Type: Grant
    Filed: January 19, 2010
    Date of Patent: December 17, 2013
    Assignee: UOP LLC
    Inventors: Antoine Negiz, Edwin Paul Boldingh, Gregory J. Gajda, Dean E. Rende, James E. Rekoske, David E. Mackowiak, Paul Barger
  • Publication number: 20130331626
    Abstract: In a process for alkylating benzene contained in a benzene-containing refinery gasoline stream, the benzene-containing refinery gasoline stream is contacted with an alkylating agent selected from one or more C2 to C5 olefins in at least one alkylation reaction zone under alkylation conditions to produce an alkylated effluent which has reduced benzene content as compared with said refinery gasoline stream and is essentially free of said alkylating agent. An aliquot of the alkylated effluent is then recycled to the one at least one alkylation reaction zone such that the molar ratio of alkylatable aromatic compounds to said alkylating agent in the combined refinery gasoline and recycle streams introduced into the at least one alkylation reaction zone is at least 1.0:1.
    Type: Application
    Filed: November 30, 2011
    Publication date: December 12, 2013
    Applicant: BADGER LICENSING LLC
    Inventors: Shyh-Yuan H. Hwang, Ronald Birkhoff, Richard F. Guarino, J. Erik Moy, Joseph C. Peters
  • Publication number: 20130331627
    Abstract: A process for reducing the benzene content of gasoline stream, such as a reformate or light naphtha, comprises alkylating the gasoline stream in a reaction zone with an olefin alkylating agent. A paraffinic stream comprising C5 to ClO paraffins is fed to the inlet of the alkylation reaction zone.
    Type: Application
    Filed: February 7, 2011
    Publication date: December 12, 2013
    Applicant: BADGER LICENSING LLC
    Inventors: Shyh-Yuan H. Hwang, Ronald Birkhoff, Richard F. Guarino, J. Erik Moy, Geeta Pherwani
  • Publication number: 20130324780
    Abstract: The invention is directed to purification of an aromatic hydrocarbon stream including selective removal of phenol from a process stream comprising aromatic hydrocarbon mixtures, especially aromatic hydrocarbon mixtures that contain higher-than-equilibrium paraxylene, by contact with suitable adsorbents, to provide a product stream having lower concentration of phenol than said process stream.
    Type: Application
    Filed: May 2, 2013
    Publication date: December 5, 2013
    Inventors: John Di-Yi Ou, Glenn A. Heeter, Shifang L. Luo, Indulis J. Eilands, Jeevan S. Abichandani, Allen Scott Gawlik, Mark W. Nash, Terrance C. Osby, Robert G. Tinger
  • Publication number: 20130324779
    Abstract: The invention relates to removal of styrene from hydrocarbon mixtures, and more particularly, removal of styrene from hydrocarbon mixtures containing higher than equilibrium paraxylene concentrations.
    Type: Application
    Filed: May 2, 2013
    Publication date: December 5, 2013
    Inventors: Glenn A. Heeter, John Di-Yi Ou, Allen Scott Gawlik, Terrance C. Osby, Jeevan S. Abichandani, Robert G. Tinger, Indulis J. Eilands, Shifang L. Luo
  • Patent number: 8598395
    Abstract: One exemplary embodiment can be a process for increasing a mole ratio of methyl to phenyl of one or more aromatic compounds in a feed. The process can include reacting an effective amount of one or more aromatic compounds and an effective amount of one or more aromatic methylating agents to form a product having a mole ratio of methyl to phenyl of at least about 0.1:1 greater than the feed.
    Type: Grant
    Filed: January 19, 2010
    Date of Patent: December 3, 2013
    Assignee: UOP LLC
    Inventors: Antoine Negiz, Edwin Paul Boldingh, Gregory J. Gajda, Dean E. Rende, James E. Rekoske, David E. Mackowiak, Paul Barger
  • Patent number: 8586496
    Abstract: A method is described for preparing a molecular sieve-containing catalyst for use in a catalytic process conducted in a stirred tank reactor. The method comprises providing a mixture comprising a molecular sieve crystal and forming the mixture into catalyst particles having an average cross-sectional dimension of between about 0.01 mm and about 3.0 mm. The mixture may include a binder and the catalyst particles are then calcined to remove water therefrom and, after calcination and prior to loading the catalyst particles into a reactor for conducting the catalytic process, the catalyst particles are coated with a paraffin inert to the conditions employed in the catalytic process.
    Type: Grant
    Filed: June 19, 2009
    Date of Patent: November 19, 2013
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Carolyn B. Duncan, Jon E. R. Stanat, Daria N. Lissy, Jane C. Cheng
  • Patent number: 8575413
    Abstract: The invention relates to a process for the alkylation of benzene with isopropanol (IPA) as alkylating agent, or blends of isopropanol and propylene, which comprises effecting said reaction completely in gaseous phase and in the presence of a catalytic system containing a zeolite belonging to the MTW family.
    Type: Grant
    Filed: September 7, 2009
    Date of Patent: November 5, 2013
    Assignee: Polimeri Europa S.p.A.
    Inventors: Loreno Lorenzoni, Paolo Calaresu, Pier Gianni Cabras
  • Patent number: 8563795
    Abstract: One exemplary embodiment can be a process using an aromatic methylating agent. Generally, the process includes reacting an effective amount of the aromatic methylating agent having at least one of an alkane, a cycloalkane, an alkane radical, and a cycloalkane radical with one or more aromatic compounds. As such, at least one of the one or more aromatic compounds may be converted to one or more higher methyl substituted aromatic compounds to provide a product having a greater mole ratio of methyl to phenyl than a feed.
    Type: Grant
    Filed: January 19, 2010
    Date of Patent: October 22, 2013
    Assignee: UOP LLC
    Inventors: Antoine Negiz, Edwin P. Boldingh, Gregory J. Gajda, Dean E. Rende, James E. Rekoske, David E. Mackowiak, Paul Barger
  • Patent number: 8558046
    Abstract: The present invention is for a process for the alkylation of aromatic compounds, with a shape-selective zeolite catalyst. The process has reactors in series with C8+ aromatics being separated from the product stream effluents from each reactor before passing the reactor effluent to the next reactor with an additional input of methanol. The C8+ aromatics are separated into para-xylene and other C8+ aromatics. This process is applicable for toluene methylation having a molar excess of toluene:methanol. i.e., greater than 1:1, with a shape-selective catalyst of an aluminosilicate zeolite, such as ZSM-5 which has been modified with phosphorus, to produce para-xylene (p-xylene).
    Type: Grant
    Filed: May 28, 2009
    Date of Patent: October 15, 2013
    Assignee: Saudi Basic Industries Corporation
    Inventors: Frederick Merrill Galloway, Jr., Ashim Kumar Ghosh, Mohammad Shafiei, Peter N. Loezos
  • Publication number: 20130267748
    Abstract: This disclosure relates to a process for regenerating a catalyst composition to improve the aging rate in subsequent cycles.
    Type: Application
    Filed: July 20, 2011
    Publication date: October 10, 2013
    Applicant: ExxonMobil Chemical Patents Inc.
    Inventors: James H. Beech, JR., Julia E. Steinheider, Doron Levin, Selma S. Lawrence
  • Publication number: 20130261359
    Abstract: The process converts FCC olefins to heavier compounds. The heavier compounds are more easily separated from the unconverted paraffins. The heavier compounds can be recycled to an FCC unit or delivered to a separate FCC unit. Suitable conversion zones are oligomerization and aromatic alkylation zones.
    Type: Application
    Filed: May 23, 2013
    Publication date: October 3, 2013
    Applicant: UOP LLC
    Inventors: Joao Jorge da Silva Ferreira Alves, James E. Rekoske, Christopher P. Nicholas
  • Patent number: 8546629
    Abstract: Embodiments of methods for co-production of linear alkylbenzene and biofuel from a natural oil are provided. A method comprises the step of deoxygenating the natural oils to form a stream comprising paraffins. A first portion of the paraffins are dehydrogenated to provide mono-olefins. Then, benzene is alkylated with the mono-olefins under alkylation conditions to provide an alkylation effluent comprising alkylbenzenes and benzene. Thereafter, the alkylbenzenes are isolated to provide the alkylbenzene product. A second portion of the paraffins is processed to form biofuel.
    Type: Grant
    Filed: September 23, 2011
    Date of Patent: October 1, 2013
    Assignee: UOP LLC
    Inventors: Andrea G. Bozzano, Matthew James Griffiths, Amarendra Anumakonda
  • Patent number: 8546633
    Abstract: A method for producing an alkylated aromatic compound includes a step (i) of producing a reaction product (a1) containing the alkylated aromatic compound and water by the reaction of an aromatic compound, a ketone, and hydrogen using a metal component containing at least one metallic element of copper, nickel, cobalt, and rhenium and a solid acid substance; a step (ii) of forming a dehydrated product (a2) from at least a portion of the reaction product (a1) by removing at least a portion of the water in the reaction product (a1); and a step (iii) of producing a reaction product (a3) containing the alkylated aromatic compound by bringing at least a portion of the dehydrated product (a2) into contact with a solid acid substance.
    Type: Grant
    Filed: October 22, 2009
    Date of Patent: October 1, 2013
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Kenji Fujiwara, Tsuneyuki Ohkubo, Terunori Fujita, Shinobu Aoki, Masayasu Ishibashi, Masao Imai, Kozo Yasuda
  • Patent number: 8536394
    Abstract: According to a process of the invention, a ketone, an aromatic compound and hydrogen as starting materials are reacted together in a single reaction step to produce an alkylaromatic compound in high yield. A process for producing phenols in the invention includes a step of performing the above alkylation process and does not increase the number of steps compared to the conventional cumene process. The process for producing alkylated aromatic compounds includes reacting an aromatic compound such as benzene, a ketone such as acetone and hydrogen in the presence of a solid acid substance, preferably a zeolite, and a silver-containing catalyst.
    Type: Grant
    Filed: March 12, 2010
    Date of Patent: September 17, 2013
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Tsuneyuki Ohkubo, Shinobu Aoki, Masayasu Ishibashi, Masao Imai, Terunori Fujita, Kenji Fujiwara
  • Patent number: 8536395
    Abstract: A solid catalyst, such as a molecular sieve catalyst or solid acid catalyst, is supported by a binder, such as amorphous silica or alumina, wherein the binder is charged with metal ions to form an ion-modified binder. The ion-modified binder is capable of attachment to polar contaminants and inhibit their contact with the catalyst. The catalyst can be a zeolite and can be the catalyst for an alkylation reaction, such as the alkylation of benzene with ethylene.
    Type: Grant
    Filed: December 22, 2011
    Date of Patent: September 17, 2013
    Assignee: Fina Technology, Inc.
    Inventors: Joseph E. Pelati, Taylor Rives
  • Patent number: 8519194
    Abstract: In a process for producing cyclohexylbenzene, benzene and hydrogen are fed to at least one reaction zone comprising a catalyst system which comprises a molecular sieve and at least one hydrogenation metal. The MCM-22 family molecular sieve having an X-ray diffraction pattern including d-spacing maxima at 12.4±0.25, 6.9±0.15, 3.57±0.07 and 3.42±0.07 Angstrom, and the hydrogenation metal is selected from the group consisting of palladium, ruthenium, nickel, zinc, tin, cobalt, and combinations of any two or more thereof. Hydroalkylation conditions of temperature and pressure are selected to produce a hydroalkylation conversion in a range of from about 15% to about 75% The benzene and hydrogen are then contacted in the at least one reaction zone under said selected hydroalkylation condition to produce an effluent containing cyclohexylbenzene.
    Type: Grant
    Filed: November 24, 2009
    Date of Patent: August 27, 2013
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Tan-Jen Chen, Francisco M. Benitez, John S. Buchanan, Jane C. Cheng, Jon E. Stanat
  • Patent number: 8507741
    Abstract: Embodiments of methods for co-production of linear alkylbenzene and biofuel from a natural oil are provided. A method comprises the step of deoxygenating the natural oils to form paraffins. A first portion of the paraffins is hydrocracked to form a first stream of normal and lightly branched paraffins in the C9 to C14 range and a second stream of isoparaffins. The first stream is dehydrogenated to provide mono-olefins. Then, benzene is alkylated with the mono-olefins under alkylation conditions to provide an alkylation effluent comprising alkylbenzenes and benzene. Thereafter, the alkylbenzenes are isolated to provide the alkylbenzene product. A second portion of the paraffins and the isoparaffins are processed to form biofuel.
    Type: Grant
    Filed: September 23, 2011
    Date of Patent: August 13, 2013
    Assignee: UOP LLC
    Inventors: Amarendra Anumakonda, Srikantiah Raghuram, Joao Jorge da Silva Ferreira Alves, Andrea G. Bozzano
  • Patent number: 8502005
    Abstract: A method for producing a linear paraffin product from natural oil and kerosene includes providing a first feed stream comprising kerosene, pre-fractionating the first feed stream to produce a heart cut paraffin stream comprising paraffins in a heart cut range, and combining the heart cut paraffin stream with a second feed stream comprising natural oil to form a combined stream. The method further includes deoxygenating the natural oil and fractionating the combined stream to remove paraffins that are heavier than the heart cut range.
    Type: Grant
    Filed: March 22, 2012
    Date of Patent: August 6, 2013
    Assignee: UOP LLC
    Inventors: Andrea G. Bozzano, Stephen Wayne Sohn
  • Patent number: 8486877
    Abstract: An alkylated hydroxyaromatic compound is disclosed which is prepared by reacting at least one hydroxyaromatic compound with at least one branched olefinic propylene oligomer having from about 20 to about 80 carbon atoms in the presence of an acid catalyst, wherein the at least one branched olefinic propylene oligomer is substantially free of any vinylidene content. The alkylated hydroxyaromatic compound has been determined to be substantially free of endocrine disruptive chemicals when the effects were quantified on pubertal development and thyroid function in the intact juvenile female rat.
    Type: Grant
    Filed: November 18, 2009
    Date of Patent: July 16, 2013
    Assignee: Chevron Oronite Company LLC
    Inventors: Curtis Bay Campbell, James J. Harrison
  • Publication number: 20130150608
    Abstract: This invention is directed to an improvement in the process for the production of alkylaromatic compounds that results in lower levels of residual unreacted materials in the final product. This invention comprises: 1) alkylation of an aromatic compound with an alkylating agent and a catalyst to produce an effluent stream comprising an alkylaromatic compound and unreacted materials; 2) heating the effluent stream; 3) stripping the effluent stream in a stripping device in the presence of steam; 4) separating a stripping stream from the stripping device, the stripping stream rich in unreacted materials; and 5) separating a product stream from the stripping device, the product stream rich in alkylated aromatic compound.
    Type: Application
    Filed: December 13, 2011
    Publication date: June 13, 2013
    Inventors: Beth A. Winsett, James I. Arnett, II, Kenwyn M. Leger, Brady A. Compton
  • Publication number: 20130150607
    Abstract: This invention is directed to a new process for making an alkylaromatic compound. In an embodiment of this invention, the process is directed to selective synthesizing an alkylaromatic compound comprising a high amount of dialkylate product. In general, this process involves contacting at least one alkylatable aromatic compound with an alkylating agent and a catalyst under suitable reaction conditions such that the resulting reactor effluent prior to any stripping step may be characterized by a dialkylate product content of at least 44 wt % and a trialkylate and higher polyalkylate product content of no more than 20 wt %. The alkylaromatic compounds produced have excellent thermal and oxidative stabilities, good additive solvency, and improved seal compatibility while maintaining good VI and low temperature properties. They are useful as lubricant basestocks and lubricant additives.
    Type: Application
    Filed: December 7, 2011
    Publication date: June 13, 2013
    Inventor: Beth A. WINSETT
  • Patent number: 8445738
    Abstract: A process is described for producing cumene comprising contacting a feed stream comprising benzene and a further feed stream comprising isopropanol or a mixture of isopropanol and propylene in the presence of an alkylation catalyst comprising at least a molecular sieve of the MCM-22, family in an alkylation zone under alkylation conditions of at least partial liquid phase and with a water concentration in the liquid phase of at least 50 ppm to react at least part of said isopropanol and benzene to produce an effluent stream containing cumene.
    Type: Grant
    Filed: September 23, 2009
    Date of Patent: May 21, 2013
    Assignee: Badger Licensing LLC
    Inventors: Shyh-Yuan Hwang, Dana E. Johnson, Joseph C. Peters, Chung-Ming Chi, Kevin J. Fallon, Francis A. Demers
  • Patent number: 8426613
    Abstract: This invention relates to the synthesis of substituted tetrahydroindenyls and the use of the synthesized complexes in the homo- and co-polymerization of ethylene and alpha-olefins.
    Type: Grant
    Filed: December 15, 2009
    Date of Patent: April 23, 2013
    Assignee: Total Petrochemicals Research Feluy
    Inventors: Alexander Z. Voskoboynikov, Vyatcheslav V. Izmer, Dmitry S. Kononovich, Abbas Razavi
  • Patent number: 8404914
    Abstract: The invention provides an efficient process for producing alkylated aromatic compounds such as cumene in a compact reactor. The invention also provides a process for producing phenol which includes a step of producing cumene by the above process. The process for producing alkylated aromatic compounds of the invention includes feeding raw materials including an aromatic compound and an alcohol in a gas-liquid downward concurrent flow mode to a fixed-bed reactor packed with a solid acid catalyst thereby to produce an alkylated aromatic compound, wherein the raw materials are fed to the reactor in a stream of a gas, and the reaction gas flow rate defined by the equation below is not less than 0.05 at an entrance of a solid acid catalyst layer: ?g·ug·[?air·?water/(?g·?l)]1/2(kgm?2s?1).
    Type: Grant
    Filed: June 3, 2009
    Date of Patent: March 26, 2013
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Shinji Senoo, Kazuhiko Kato, Kenji Doi, Katsunari Higashi