Plural Alkylation Stages Patents (Class 585/449)
  • Patent number: 10099973
    Abstract: A method for preparing p-xylene and co-producing propylene with a high selectivity, comprising: a) bringing a raw material containing toluene and methanol and/or dimethyl ether into contact with a catalyst in a reaction system for reaction; returning an ethylene-enriched C2? component discharged from the reaction system to the reaction system, and continuing the reaction with the raw material on the catalyst to produce propylene; b) separating a C6+ component discharged from the reaction system to obtain a product p-xylene; and c) separating a C3 component discharged from the reaction system to obtain a product propylene.
    Type: Grant
    Filed: June 4, 2014
    Date of Patent: October 16, 2018
    Assignee: DALIAN INSTITUTE OF CHEMICAL PHYSICS, CHINESE ACADEMY OF SCIENCES
    Inventors: Lei Xu, Zhongmin Liu, Xinzhi Zhang
  • Patent number: 9751817
    Abstract: A process for producing alkylaromatic compounds is described. The process involves utilizing at least a portion of the aromatic compound used to regenerate the alkylation catalyst in a spent alkylation reaction zone as a reactant in the active alkylation reaction zone. The process further includes utilizing a portion of the process stream leaving the alkylation zone as a recycle stream to the alkylation zone.
    Type: Grant
    Filed: March 7, 2014
    Date of Patent: September 5, 2017
    Assignee: UOP LLC
    Inventors: Priyesh Jayendrakumar Jani, Soumendra Mohan Banerjee, Stephen Wayne Sohn
  • Patent number: 9375706
    Abstract: Alkylation systems and processes are described herein. The alkylation system generally includes a preliminary alkylation system containing a preliminary alkylation catalyst therein and adapted to contact an aromatic compound and an alkylating agent with the preliminary alkylation catalyst so as to alkylate the aromatic compound and form a preliminary output stream, wherein the preliminary alkylation system includes a first preliminary alkylation reactor and a second preliminary alkylation reactor connected in parallel to the first preliminary alkylation reactor and a primary alkylation system adapted to receive the preliminary output stream and contact the preliminary output stream and the alkylating agent with a primary alkylation catalyst disposed therein so as to form a primary output stream.
    Type: Grant
    Filed: February 16, 2011
    Date of Patent: June 28, 2016
    Assignee: FINA TECHNOLOGY, INC.
    Inventor: James Butler
  • Patent number: 9193642
    Abstract: A method of making dialkylaromatics as a primary product is described. The design involves a dual reaction zone system, both reaction zones containing alkylation catalysts. The olefin feed is split into two portions (or two feeds are used), the first portion being fed to a first alkylation reaction zone and reacted with a first olefin. The other portion of olefin is reacted in a second reaction zone with the linear alkylaromatics formed in the first reaction zone to form the dialkylaromatics.
    Type: Grant
    Filed: June 20, 2013
    Date of Patent: November 24, 2015
    Assignee: UOP LLC
    Inventors: Debarshi Majumder, Stephen W. Sohn
  • Publication number: 20150119618
    Abstract: This invention relates to an alkylating process for alkyl benzenes, including the steps of: a) an alkyl benzene and a first stream of alkylating agent being fed into a first reaction zone, contacting with a catalyst A, to produce a process stream I; b) the process stream I and a second stream of alkylating agent being fed into at least one second reaction zone, contacting with a catalyst B, to produce a process stream II; and c) the process stream II being fed into at least one third reaction zone, contacting with a catalyst C, to produce a process stream III containing an alkylate. The present alkylating process can improve the utilization efficiency of the alkylating agent.
    Type: Application
    Filed: July 4, 2013
    Publication date: April 30, 2015
    Inventors: Jian Jiang, Changxi Miao, Dongyu Jiang
  • Publication number: 20150119619
    Abstract: A method for producing isopropyl benzene includes the following steps. Step A: feeding a first stream containing benzene and a first stream containing propylene into a first reaction zone to contact a first catalyst for alkylation, and obtaining a first stream containing isopropyl benzene from the first reaction zone, dividing the first stream containing isopropyl benzene into a stream Ia and a stream IIa, the stream Ia circulating back into the first reaction zone and the stream IIa entering into a second reaction zone, having the stream entering the second reaction zone to contact a second catalyst for alkylation, and obtaining a second stream containing isopropyl benzene from the second reaction zone, and purifying at least a partial stream IIIa of the second stream containing isopropyl benzene, and obtaining a product isopropyl benzene.
    Type: Application
    Filed: October 28, 2014
    Publication date: April 30, 2015
    Applicants: China Petroleum & Chemical Corporation, Shanghai Research Institute of Petrochemical Technology SINOPEC
    Inventors: Huanxin GAO, Hongyuan ZONG, Yilun WEI, Hui YAO, Ruifang GU, Hua FANG, Shufang JI
  • Patent number: 8993820
    Abstract: The present invention provides an improved process for producing an alkylated aromatic compound from an at least partially untreated alkylatable aromatic compound having catalyst poisons, wherein said alkylatable aromatic compound stream is treated to reduce catalyst poisons with a treatment composition having a surface area/surface volume ratio of greater than or equal to 30 in?1 (12 cm?1) in a treatment zone separate from an alkylation reaction zone under treatment conditions including a temperature of from about 30° C. to about 300° C. to form an effluent comprising said treated alkylatable aromatic compound.
    Type: Grant
    Filed: April 15, 2011
    Date of Patent: March 31, 2015
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Matthew J. Vincent, Vijay Nanda, Terry E. Helton
  • Publication number: 20150025286
    Abstract: The present disclosure relates to a process for production of a monoalkyl aromatic compound by alkylation of alkylatable aromatic compounds with an alkylating agent in a reactor comprising at least a first and a second series-connected alkylation reaction zones and a cooler disposed between the first and the second series-connected alkylation reaction zones. The process comprising a step of cooling at least a portion of an effluent withdrawn from the first alkylation reaction zone before being introduced into the second alkylation reaction zone.
    Type: Application
    Filed: December 13, 2012
    Publication date: January 22, 2015
    Applicant: ExxonMobile Chemical Patents Inc.
    Inventors: Matthew J. Vincent, Vijay Nanda
  • Patent number: 8877996
    Abstract: Disclosed is a process for the production of alkylated aromatics by contacting a feed stream comprising an alkylatable aromatic, an alkylating agent and trace amounts of water and impurities in the presence of a first catalyst and an alkylation catalyst wherein such water and impurities are removed in order to improve the cycle length of such alkylation catalysts. Water and at least a portion of impurities are removed in a dehydration zone. A reaction zone having a first catalyst which, in some embodiments is a large pore molecular sieve, acts to remove another portion of impurities, such as nitrogenous and other species. An alkylation zone having an alkylation catalyst which, in some embodiments is a medium pore molecular sieve or a MCM-22 family material, acts to remove additional impurities, and to alkylate the alkylatable aromatic compound.
    Type: Grant
    Filed: November 8, 2013
    Date of Patent: November 4, 2014
    Assignees: ExxonMobil Chemical Patents Inc., Technip Process Technology, Inc.
    Inventors: Matthew J. Vincent, Vijay Nanda, Maruti Bhandarkar, Brian Maerz, Terry E. Helton
  • Patent number: 8865958
    Abstract: A method of producing an alkylaromatic by the alkylation of an aromatic with an alkylating agent, such as producing ethylbenzene by an alkylation reaction of benzene, is disclosed. The method includes using an H-beta catalyst to minimize process upsets due to alkylation catalyst deactivation and the resulting catalyst regeneration or replacement. The H-beta catalyst can be used in a preliminary alkylation reactor that is located upstream of the primary alkylation reactor. The H-beta catalyst used in a preliminary alkylation reactor can reduce the deactivation of the catalyst in the primary alkylation reactor.
    Type: Grant
    Filed: September 28, 2009
    Date of Patent: October 21, 2014
    Assignee: Fina Technology, Inc.
    Inventor: James R. Butler
  • Patent number: 8853481
    Abstract: A method for alkylation of a feedstock is described. The method includes contacting the feedstock comprising at least one alkylatable aromatic compound and an alkylating agent with a first alkylating catalyst composition under alkylating conditions, the first alkylating catalyst composition comprising UZM-8 zeolite and a binder, the first alkylating catalyst composition having less than 50 wt% UZM-8 zeolite; wherein a total alkylated selectivity at a temperature and a molar ratio of alkylatable aromatic compound to alkylating agent is greater than 99.0%.
    Type: Grant
    Filed: October 26, 2012
    Date of Patent: October 7, 2014
    Assignee: UOP LLC
    Inventors: Deng-Yang Jan, Robert J. Schmidt, Pelin Cox
  • Patent number: 8802911
    Abstract: A method of producing an alkylaromatic by the alkylation of an aromatic with an alkylating agent, such as producing ethylbenzene by an alkylation reaction of benzene, is disclosed. The method includes using an H-beta catalyst to minimize process upsets due to alkylation catalyst deactivation and the resulting catalyst regeneration or replacement. The H-beta catalyst can be used in a preliminary alkylation reactor that is located upstream of the primary alkylation reactor. The H-beta catalyst used in a preliminary alkylation reactor can reduce the deactivation of the catalyst in the primary alkylation reactor.
    Type: Grant
    Filed: April 23, 2013
    Date of Patent: August 12, 2014
    Assignee: Fina Technology, Inc.
    Inventor: James R. Butler
  • Publication number: 20140194660
    Abstract: A process is described for alkylating benzene contained in a refinery gasoline stream, in which the refinery gasoline stream is contacted with an alkylating agent comprising one or more C2 to C5 olefins in an alkylation reaction zone under alkylation conditions to produce an alkylated effluent. The alkylation reaction zone comprises at least a first alkylation reaction stage and a second alkylation reaction stage and a portion of said alkylating agent is fed to each of said first and second alkylation reaction stages so that, although the molar ratio of alkylatable aromatic to alkylating agent in the total feed to the alkylation reaction zone is less than 1, the molar ratio of alkylatable aromatic to alkylating agent at the inlet of each of the first and second alkylation reaction stages is at least 1.0.
    Type: Application
    Filed: November 30, 2011
    Publication date: July 10, 2014
    Applicant: BADGER LICENSING LLC
    Inventors: Shyh-Yuan H. Hwang, Ronald Birkhoff, Richard F. Guarino, J. Erik Moy, Geeta Pherwani
  • Publication number: 20140128651
    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: Application
    Filed: January 14, 2014
    Publication date: May 8, 2014
    Applicant: FINA TECHNOLOGY, INC.
    Inventors: James R. Butler, Xin Xiao, James T. Merrill
  • Patent number: 8680354
    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 29, 2013
    Date of Patent: March 25, 2014
    Assignee: Fina Technology, Inc.
    Inventors: James R. Butler, Xin Xiao, James T. Merrill
  • Patent number: 8637720
    Abstract: Alkylation systems and methods of minimizing alkylation catalyst regeneration are discussed 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 first preliminary alkylation catalyst disposed therein to form a first output stream. The first preliminary alkylation catalyst generally includes a Y zeolite. The 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: March 19, 2013
    Date of Patent: January 28, 2014
    Assignee: Fina Technology, Inc.
    Inventors: James T. Merrill, Marcus Ledoux
  • Patent number: 8633342
    Abstract: In a process for alkylation of an alkylatable aromatic compound to produce a monoalkylated aromatic compound, a first feed stream comprising fresh alkylatable aromatic compound is passed to a first reaction zone which comprises a transalkylation catalyst and which also receives a second feed stream comprising polyalkylated aromatic compounds. The first and second feed streams are contacted with the transalkylation catalyst in the first reaction zone under conditions to transalkylate the polyalkylated aromatic compounds with the alkylatable aromatic compound to produce the desired monoalkylated aromatic compound. A first effluent stream comprising unreacted alkylatable aromatic compound and the monoalkylated aromatic compound is removed from the first reaction zone and passed to a fractionation system to separate the first effluent stream into a first light fraction comprising the unreacted alkylatable aromatic compound and a first heavy fraction comprising the monoalkylated aromatic compound.
    Type: Grant
    Filed: September 24, 2009
    Date of Patent: January 21, 2014
    Assignee: Badger Licensing LLC
    Inventors: Matthew J. Vincent, Charles Morris Smith
  • Patent number: 8629311
    Abstract: Disclosed is a process for the production of alkylated aromatics by contacting a feed stream comprising an alkylatable aromatic, an alkylating agent and trace amounts of water and impurities in the presence of first and second alkylation catalysts wherein the water and impurities are removed in order to improve the cycle length of such alkylation catalysts. Water and a portion of impurities are removed in a dehydration zone. A first alkylation zone having a first alkylation catalyst which, in some embodiments is a large pore molecular sieve, acts to remove a larger portion of impurities, such as nitrogenous and other species, and to alkylate a smaller portion of the alkylatable aromatic compound. A second alkylation zone, which in some embodiments is a medium pore molecular sieve, acts to remove a smaller portion of impurities, and to alkylate a larger portion of the alkylatable aromatic compound.
    Type: Grant
    Filed: March 10, 2010
    Date of Patent: January 14, 2014
    Assignees: Stone & Webster, Inc., ExxonMobil Chemical Patents Inc.
    Inventors: Matthew J. Vincent, Vijay Nanda, Maruti Bhandarkar, Brian Maerz, Terry E. Helton
  • Patent number: 8609915
    Abstract: Processes for preparing alkylation aromatic compounds are provided herein. In an embodiment, a process for preparing alkylated aromatic compounds includes reacting an aromatic compound and an olefin in a first alkylation reaction in the presence of a first alkylation catalyst to produce a first effluent that includes an alkylated aromatic compound and unreacted aromatic compound. Unreacted aromatic compound from the first effluent and additional olefin are reacted in at least one downstream alkylation reaction in the presence of a second alkylation catalyst to produce a second effluent including the alkylated aromatic compound. A recycle stream including the alkylated aromatic compound is recycled from the second effluent to the at least one downstream alkylation reaction and, optionally, the first alkylation reaction. A ratio of the recycle stream to a total mass flow is greater in the at least one downstream alkylation reaction than in the first alkylation reaction.
    Type: Grant
    Filed: March 12, 2012
    Date of Patent: December 17, 2013
    Assignee: UOP LLC
    Inventors: Debarshi Majumder, Carl John Stevens, Robert James Schmidt
  • Patent number: 8609916
    Abstract: Processes for preparing alkylation aromatic compounds are provided. One process for preparing alkylated aromatic compounds includes reacting an aromatic compound and an olefin in at least one primary alkylation reaction in the presence of a first alkylation catalyst to produce a first effluent. The first effluent is split into a first product-rich stream and a first recycle stream, and the first recycle stream is recycled to the at least one primary alkylation reaction. Unreacted aromatic compound from the first product-rich stream and an additional olefin are reacted in at least one downstream alkylation reaction in the presence of a second alkylation catalyst to produce a second effluent. The second effluent is split into a second product-rich stream and a second recycle stream, and the second recycle stream is recycled to the at least one primary alkylation reaction and, optionally, to the at least one downstream alkylation reaction.
    Type: Grant
    Filed: March 12, 2012
    Date of Patent: December 17, 2013
    Assignee: UOP LLC
    Inventors: Debarshi Majumder, Carl John Stevens, Robert James Schmidt
  • 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
  • Patent number: 8552238
    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: April 16, 2013
    Date of Patent: October 8, 2013
    Assignee: Fina Technology, Inc.
    Inventors: James R. Butler, Xin Xiao, James T. Merrill
  • 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: 8524964
    Abstract: This disclosure relates to a process for hydrocarbon conversion comprising contacting, under conversion conditions, a feedstock suitable for hydrocarbon conversion with a catalyst comprising an EMM-10 family molecular sieve.
    Type: Grant
    Filed: February 14, 2011
    Date of Patent: September 3, 2013
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Wieslaw J. Roth, Jane C. Cheng, Mohan Kalyanaraman, Michael C. Kerby, Terry E. Helton
  • Patent number: 8481794
    Abstract: Embodiments of methods and apparatuses for producing ethylbenzene are provided. The method comprises the steps of introducing a first feed mixture comprising benzene and ethylene to UZM-8 zeolite-based catalyst at a first predetermined inlet temperature to form a first intermediate outlet stream comprising ethylbenzene and benzene. Ethylene is added to the first intermediate outlet stream to form a second intermediate feed mixture. The second intermediate feed mixture is introduced to beta zeolite-based catalyst at a second predetermined inlet temperature to form ethylbenzene.
    Type: Grant
    Filed: May 9, 2011
    Date of Patent: July 9, 2013
    Assignee: UOP LLC
    Inventors: Wugeng Liang, Deng-Yang Jan
  • Publication number: 20130131415
    Abstract: A method of producing an alkylaromatic by the alkylation of an aromatic with ethanol, such as producing ethylbenzene by an alkylation reaction of benzene, is disclosed.
    Type: Application
    Filed: November 22, 2011
    Publication date: May 23, 2013
    Applicant: FINA TECHNOLOGY, INC.
    Inventors: James R. Butler, Aspen Texada, William Sheets
  • Patent number: 8426662
    Abstract: Alkylation systems and methods of minimizing alkylation catalyst regeneration are discussed 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 first preliminary alkylation catalyst disposed therein to form a first output stream. The first preliminary alkylation catalyst generally includes a Y zeolite. The 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 5, 2012
    Date of Patent: April 23, 2013
    Assignee: Fina Technology, Inc.
    Inventors: James T. Merrill, Marcus Ledoux
  • Patent number: 8420877
    Abstract: A method of producing an alkylaromatic by the alkylation of an aromatic with an alkylating agent, such as producing ethylbenzene by an alkylation reaction of benzene, is disclosed. The method includes using an H-beta catalyst in a preliminary alkylation reactor that is located upstream of the primary alkylation reactor. The H-beta catalyst used in a preliminary alkylation reactor can be regenerated and the regenerated H-beta zeolite catalyst can have a deactivation rate that is no more than 120% of the deactivation rate of a fresh H-beta zeolite catalyst.
    Type: Grant
    Filed: May 2, 2011
    Date of Patent: April 16, 2013
    Assignee: Fina Technology, Inc.
    Inventor: James R. Butler
  • Patent number: 8373014
    Abstract: Systems and processes for the alkylation of a hydrocarbon are provided that utilize a plurality of moving bed radial flow reactors. An olefin injection point can be provided prior to each reactor by providing a mixer that mixes olefin with a hydrocarbon feed, or with the effluent stream from an upstream reactor, to produce a reactor feed stream. Catalyst can be provided from the reaction zone of one reactor to the reaction zone of a downstream reactor through catalyst transfer pipes, and can be regenerated after passing through the reaction zones of the reactors. The moving bed radial flow reactors can be stacked in one or more reactor stacks.
    Type: Grant
    Filed: December 2, 2010
    Date of Patent: February 12, 2013
    Assignee: UOP LLC
    Inventors: Clayton C. Sadler, Mary Jo Wier, Laurence O. Stine, Christopher Naunheimer
  • Patent number: 8357830
    Abstract: A process for producing a monoalkylated aromatic compound in an alkylation reaction zone, comprising providing upstream of said alkylation reaction zone a reactive guard bed having a catalyst of *BEA, MWW, or FAU framework structure and an alkylation feed wherein at least a portion of any reactive impurities are removed from the alkylation feed to form an effluent; and providing the effluent and a first catalytic particulate material which comprises MCM-56 and an alumina binder sized 50-60 mesh and having a ratio of surface area over volume ratio in the range of 241 to 2867 cm-1 and optionally additional alkylating agent to said alkylation reaction zone; and contacting said alkylatable aromatic compound and said alkylating agent with said catalytic particulate material in said alkylation reaction zone maintained under alkylation conditions, to form a product comprised of said monoalkylated aromatic compound.
    Type: Grant
    Filed: June 29, 2012
    Date of Patent: January 22, 2013
    Assignee: Exxonmobil Chemical Patents Inc.
    Inventors: Michael C. Clark, Christine N. Elia, Frederick Y. Lo, Yun-Feng Chang
  • Publication number: 20120289677
    Abstract: One exemplary embodiment can be a process for alkylating benzene. The process can include obtaining at least a portion of a stream from a transalkylation zone, combining the at least the portion of the stream from the transalkylation zone with a fuel gas stream, and providing at least a portion of the combined stream to a benzene methylation zone. Typically, the fuel gas stream includes an effective amount of one or more alkanes for alkylating at least partially from a hydrogen purification process tail gas.
    Type: Application
    Filed: May 11, 2011
    Publication date: November 15, 2012
    Applicant: UOP, LLC
    Inventors: Laura E. Leonard, Robert Haizmann
  • Patent number: 8258360
    Abstract: A process for producing a monoalkylated aromatic product in a reactor by reacting a mixed phase mixture of an alkylatable aromatic compound feedstock with another feedstock comprising alkene component in a reaction zone containing an alkylation catalyst. An effluent comprising the monoalkylated aromatic product and polyalkylated aromatic compounds exits from the reaction zone in liquid phase. The polyalkylated aromatic compounds can be separated as feed stream for transalkylation reaction in a transalkylation reaction zone.
    Type: Grant
    Filed: March 1, 2006
    Date of Patent: September 4, 2012
    Assignees: ExxonMobil Chemical Patents Inc., Stone & Webster, Inc.
    Inventors: Michael C. Clark, Vijay Nanda, Brian Maerz
  • Patent number: 8237001
    Abstract: The present invention refers to a procedure for obtaining a linear monoalkylaromatic compound, with adjustable 2-phenyl isomer content and an extremely low sulphonation color, in which a catalytic system is used based on highly stable and active solid catalysts and with a high selectivity for linear monoalkylaromatic compounds.
    Type: Grant
    Filed: December 4, 2007
    Date of Patent: August 7, 2012
    Assignee: Cepsa Quimica, S.A.
    Inventors: José Luis Berna Tejero, José Luis Goncalvez De Almeida
  • Patent number: 8124035
    Abstract: Continuous processes for monoalkylating aromatic compound with an aliphatic feedstock comprising aliphatic olefin of 8 to 18 carbon atoms per molecule are effected using at least 3 reaction zones in series, each containing solid alkylation catalyst with effluent cooling between reaction zones, each of which reaction zones is supplied a portion of the fresh aliphatic feedstock, such that the Reaction Zone Delta T in each reaction zone is less than about 15° C. The overall aromatic compound to olefin molar ratio is less than about 20:1. The alkylation product has desirable linearity and low amounts of dimers, dealkylated compounds and diaryl compounds even though a low aromatic compound to olefin molar ratio is used.
    Type: Grant
    Filed: February 5, 2010
    Date of Patent: February 28, 2012
    Assignee: UOP LLC
    Inventor: Mark G. Riley
  • Patent number: 8110161
    Abstract: The invention relates to a process for the production of alkylated aromatic compounds comprising introducing olefin and aromatic compounds into at least first and second vertically spaced catalytic reaction zones in an alkylation unit under alkylation reaction conditions to provide an alkylated product, wherein the second catalytic reaction zone is positioned above the first catalytic reaction zone; wherein aromatic compound from each of the at least first and second catalytic reaction zones are contacted with a cooling means for re-condensing at least a portion of the aromatic compounds vaporized from the exothermic heat of reaction of the alkylation process; and wherein the olefin is introduced into the at least first and second catalytic reaction zones via respective first and second olefin feed streams at respective olefin feed rates such as to maintain olefin partial pressures at inlets to at least first and second catalytic reaction zones which vary by less than about ten percent.
    Type: Grant
    Filed: December 11, 2009
    Date of Patent: February 7, 2012
    Assignee: Lummus Technology Inc.
    Inventor: Kevin John Schwint
  • Patent number: 8071829
    Abstract: A process is disclosed for the alkylation of aromatics by charging a hydrocarbon feed containing aromatic hydrocarbons and olefinic hydrocarbons to a distillation column for separation into at least one fraction; removing an aromatics/olefin stream containing at least a portion of the aromatic hydrocarbons and at least a portion of the olefinic hydrocarbons; charging the aromatics/olefin stream to an alkylation reactor, operated at a temperature in the range of from about 80° C. to about 220° C., for alkylation of at least a portion of the aromatic hydrocarbons with the olefinic hydrocarbons; recycling at least a portion of the resulting reactor effluent to the distillation column; and removing a product stream containing alkylated aromatics from the distillation column.
    Type: Grant
    Filed: February 20, 2009
    Date of Patent: December 6, 2011
    Assignee: ConocoPhillips Company
    Inventors: Bradley M. Taylor, Barbara A. Todd
  • Patent number: 8058494
    Abstract: A process for the production of phenylalkanes comprising at least two catalytic alkylation reactors placed in parallel among which are present in reaction zones that each contain at least one acidic solid catalyst, whereby n is greater than or equal to 2, is described. One of the reactors carries out the alkylation of at least one aromatic compound by at least one olefin that has 9 to 16 atoms. An olefin fraction is introduced at the inlet of each of the reaction zones of the reactor that operates in alkylation mode. While one of the reactors carries out the alkylation, the other reactor carries out the reactivation of each catalyst, partially deactivated, that it contains. The functions of each reactor are switched regularly so as to limit the deactivation of catalysts in each of the reactors. The phenylalkanes that are obtained by the process according to the invention are particularly suitable for the production of detergents.
    Type: Grant
    Filed: October 4, 2005
    Date of Patent: November 15, 2011
    Assignee: IFP Energies Nouvelles
    Inventors: Emmanuelle Guillon, Eric Sanchez
  • Patent number: 7923589
    Abstract: A process for producing an alkylated aromatic product in a reactor by reacting an alkylatable aromatic compound feedstock with another feedstock comprising alkene component and alkane component in a reaction zone containing an alkylation catalyst. The reaction zone is operated in predominantly liquid phase without inter-zone alkane removal. The polyalkylated aromatic compounds can be separated as feed stream for transalkylation reaction in a transalkylation reaction zone.
    Type: Grant
    Filed: March 1, 2006
    Date of Patent: April 12, 2011
    Assignees: ExxonMobil Chemical Patents Inc., Stone & Webster, Inc.
    Inventors: Michael C. Clark, Brian Maerz
  • Patent number: 7868218
    Abstract: A process is described for producing an alkylaromatic compound in a multistage reaction system comprising at least first and second series-connected alkylation reaction zones each containing an alkylation catalyst. A first feed comprising an alkylatable aromatic compound and a second feed comprising an alkene and one or more alkanes are introduced into said first alkylation reaction zone, having operating conditions, e.g., temperature and pressure, which are controlled effective to cause the alkylatable aromatic compound to be partly in the vapor phase and partly in the liquid phase with the ratio of liquid volume to vapor volume of the feed in each zone to be from about 0.5 to about 10.
    Type: Grant
    Filed: June 9, 2010
    Date of Patent: January 11, 2011
    Assignees: ExxonMobil Chemical Patents Inc., Badger Licensing, LLC
    Inventors: Michael C. Clark, Brian Maerz
  • Publication number: 20100305378
    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: Application
    Filed: May 28, 2009
    Publication date: December 2, 2010
    Applicant: Saudi Basic Industries Corporation
    Inventors: Frederick Merrill Galloway, JR., Ashim Kumar Ghosh, Mohammad Shafiei, Peter N. Loezos
  • Publication number: 20100249472
    Abstract: A process is described for producing an alkylaromatic compound in a multistage reaction system comprising at least first and second series-connected alkylation reaction zones each containing an alkylation catalyst. A first feed comprising an alkylatable aromatic compound and a second feed comprising an alkene and one or more alkanes are introduced into said first alkylation reaction zone, having operating conditions, e.g., temperature and pressure, which are controlled effective to cause the alkylatable aromatic compound to be partly in the vapor phase and partly in the liquid phase with the ratio of liquid volume to vapor volume of the feed in each zone to be from about 0.5 to about 10.
    Type: Application
    Filed: June 9, 2010
    Publication date: September 30, 2010
    Inventors: Michael C. Clark, Brian Maerz
  • Patent number: 7795483
    Abstract: The present invention is a process for producing phenyl-alkanes by paraffin adsorptive separation followed by paraffin dehydrogenation and then by alkylation of a phenyl compound by a lightly branched olefin. The adsorptive separation step employs a silicalite adsorbent and, as the desorbent, a C5-C8 linear paraffin, a C5-C8 cycloparaffin, a branched paraffin such as isooctane, or mixtures thereof. The effluent of the alkylation zone comprises paraffins that are recycled to the adsorptive separation step or to the dehydrogenation step. This invention is also a process that that sulfonates phenyl-alkanes having lightly branched aliphatic alkyl groups that to produce modified alkylbenzene sulfonates. In addition, this invention is the compositions produced by these processes, which can be used as detergents having improved cleaning effectiveness in hard and/or cold water while also having biodegradability comparable to that of linear alkylbenzene sulfonates, as lubricants, and as lubricant additives.
    Type: Grant
    Filed: September 9, 2003
    Date of Patent: September 14, 2010
    Assignee: UOP LLC
    Inventors: Santi Kulprathipanja, Richard E. Marinangeli, Stephen W. Sohn, Thomas R. Fritsch, R. Joe Lawson
  • Patent number: 7790939
    Abstract: A process for alkylation or transalkylation of an alkylatable aromatic compound having reactive impurities with an alkylating agent to produce a monoalkylated aromatic compound, comprising the steps of contacting at least a portion of said alkylatable aromatic compounds and said alkylating agent with a first molecular sieve catalyst in a guard bed under suitable conditions to remove said reactive impurities and form a first effluent comprising monoalkylated aromatic compound, unreacted alkylatable aromatic compounds and unreacted alkylating agent; contacting said first effluent with a second molecular sieve catalyst different from said first molecular sieve catalyst in said reaction zone under suitable alkylation or transalkylation conditions to produce additional said monoalkylated aromatic compounds; and maintaining said water content from about 1 wppm to about 10 wt.
    Type: Grant
    Filed: December 2, 2009
    Date of Patent: September 7, 2010
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Michael C. Clark, Vijay Nanda
  • Patent number: 7777087
    Abstract: A process is disclosed for producing an alkylaromatic compound in a multistage reaction system comprising at least first and second series-connected alkylation reaction zones, each containing an alkylation catalyst. A first feed comprising an alkylatable aromatic compound and a second feed comprising an alkene are introduced into the first alkylation reaction zone. The first and second alkylation reaction zones are operated under conditions of temperature and pressure effective to cause alkylation of the aromatic compound with the alkene in the presence of the alkylation catalyst, the temperature and pressure being such that the aromatic compound is at least partly in the liquid phase. The alkylation catalyst in the first alkylation reaction zone, which may be a reactor guard bed, has more acid sites per unit volume of catalyst than the alkylation catalyst in the second reaction zone.
    Type: Grant
    Filed: November 23, 2009
    Date of Patent: August 17, 2010
    Assignees: ExxonMobil Chemical Patents Inc., Stone & Webster, Inc.
    Inventors: Michael C. Clark, Vijay Nanda, Chung-Ming Chi, Maruti Bhandarkar, Brian Maerz, Matthew J. Vincent
  • Patent number: 7772448
    Abstract: A process is described for producing an alkylaromatic compound in a multistage reaction system comprising at least first and second series-connected alkylation reaction zones each containing an alkylation catalyst. A first feed comprising an alkylatable aromatic compound and a second feed comprising an alkene and one or more alkanes are introduced into said first alkylation reaction zone. The operating conditions, e.g. temperature and pressure, of the first alkylation reaction zone are controlled effective to cause the alkylatable aromatic compound to be partly in the vapor phase and partly in the liquid phase, and the ratio of the volume of liquid to the volume of vapor of the feed in each zone to be from about 0.1 to about 10. The aromatic compound and the alkene of the feed are reacted in the presence of the alkylation catalyst to form an effluent comprising the alkylaromatic compound, unreacted alkylatable aromatic compound, any unreacted alkene and the alkane.
    Type: Grant
    Filed: January 28, 2009
    Date of Patent: August 10, 2010
    Assignees: Badger Licensing LLC, ExxonMobil Chemical Patents Inc.
    Inventors: Michael C. Clark, Brian Maerz
  • Patent number: 7745674
    Abstract: A process for alkylation of benzene, including: feeding benzene, a polyalkylate, and a catalyst to a reactor comprising a first and a second reaction zone; reacting the benzene and the polyalkylate in the first reaction zone under transalkylation conditions to form a monoalkylate product; feeding a C2-C4 olefin to the reactor intermediate the first and second reaction zones; reacting benzene and the C2-C4 olefin in the second reaction zone under alkylation conditions to form additional monoalkylate product; recovering an effluent from the reactor, wherein the effluent comprises benzene, the monoalkylate product, any unreacted C2-C4 olefins, heavy hydrocarbons, and the catalyst; separating the catalyst from the effluent; separating the benzene from the monoalkylate product and the heavy hydrocarbons within the liquid effluent; separating the monoalkylate product from the heavy hydrocarbons within the liquid effluent; and recovering the monoalkylate product.
    Type: Grant
    Filed: August 20, 2008
    Date of Patent: June 29, 2010
    Assignee: Catalytic Distillation Technologies
    Inventors: Christopher C. Boyer, Lawrence A. Smith, Jr.
  • Patent number: 7745676
    Abstract: A process is described for producing an alkylaromatic compound, in which a first feed comprising an alkylatable aromatic compound and a second feed comprising an alkene are introduced into a first alkylation reaction zone comprising a first alkylation catalyst. The first alkylation reaction zone is operated under conditions effective to cause alkylation of the alkylatable aromatic compound by the alkene to produce said alkylaromatic compound, the conditions being such that the alkylatable aromatic compound is at least predominantly in the vapor phase. A first effluent comprising the alkylaromatic compound and unreacted alkylatable aromatic compound is withdrawn from the first alkylation reaction zone and at least part of the unreacted alkylatable aromatic compound is treated to remove catalyst poisons therefrom and produce a treated unreacted alkylatable aromatic stream.
    Type: Grant
    Filed: July 30, 2007
    Date of Patent: June 29, 2010
    Assignees: ExxonMobil Chemical Patents Inc., Stone & Webster, Inc.
    Inventors: Michael C. Clark, Vijay Nanda, Maruti Bhandarkar, Joseph C. Peters, Chung-Ming Chi, Brian Maerz
  • Patent number: 7692054
    Abstract: Continuous processes for monoalkylating aromatic compound with an aliphatic feedstock comprising aliphatic olefin of 8 to 18 carbon atoms per molecule are effected using at least 3 reaction zones in series, each containing solid alkylation catalyst with effluent cooling between reaction zones, each of which reaction zones is supplied a portion of the fresh aliphatic feedstock, such that the Reaction Zone Delta T in each reaction zone is less than about 15° C. The overall aromatic compound to olefin molar ratio is less than about 20:1. The alkylation product has desirable linearity and low amounts of dimers, dealkylated compounds and diaryl compounds even though a low aromatic compound to olefin molar ratio is used.
    Type: Grant
    Filed: October 16, 2007
    Date of Patent: April 6, 2010
    Assignee: UOP LLC
    Inventor: Mark G. Riley
  • Publication number: 20100048966
    Abstract: A process for alkylation of benzene, including: feeding benzene, a polyalkylate, and a catalyst to a reactor comprising a first and a second reaction zone; reacting the benzene and the polyalkylate in the first reaction zone under transalkylation conditions to form a monoalkylate product; feeding a C2-C4 olefin to the reactor intermediate the first and second reaction zones; reacting benzene and the C2-C4 olefin in the second reaction zone under alkylation conditions to form additional monoalkylate product; recovering an effluent from the reactor, wherein the effluent comprises benzene, the monoalkylate product, any unreacted C2-C4 olefins, heavy hydrocarbons, and the catalyst; separating the catalyst from the effluent; separating the benzene from the monoalkylate product and the heavy hydrocarbons within the liquid effluent; separating the monoalkylate product from the heavy hydrocarbons within the liquid effluent; and recovering the monoalkylate product.
    Type: Application
    Filed: August 20, 2008
    Publication date: February 25, 2010
    Applicant: CATALYTIC DISTILLATION TECHNOLOGIES
    Inventors: Christopher C. Boyer, Lawrence A. Smith, JR.
  • Patent number: RE41136
    Abstract: The present invention relates to a process of preparing dialkylnaphthylenes and polyalkylenenaphthyleneates dialkylnaphthalenes and polyalkylenenaphthalates.
    Type: Grant
    Filed: January 24, 2002
    Date of Patent: February 16, 2010
    Assignees: Kobe Steel, Ltd, ExxonMobil Chemical Patents, Inc.
    Inventors: Masahiro Motoyuki, Koji Yamamoto, Ajit Vishwanath Sapre, John Paul McWilliams, Susan Patricia Donnelly