By Alkyl Or Aryl Transfer Between Molecules, E.g., Disproportionation, Etc. Patents (Class 585/470)
  • Patent number: 10781149
    Abstract: Disclosed is a transalkylation process for making an aromatic material between a light aromatic material and a heavier aromatic material in the presence of hydrogen and a transalkylation catalyst comprising a hydrogenation component and a transalkylation component. The process comprises conducting the transalkylation reaction under conditions conducive to reducing the amount of cyclic compounds in the transalkylation reaction mixture in the beginning phase of the operation that is different from the conditions after the beginning phase. The invention is useful, e.g., in transalkylation between toluene and C9+ aromatic feed materials to produce xylenes and/or benzene.
    Type: Grant
    Filed: November 16, 2015
    Date of Patent: September 22, 2020
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Michel Molinier, Jeffrey L. Andrews, Hari Nair
  • Patent number: 10392316
    Abstract: The present invention relates to minimizing benzene, toluene, and an A9/A10 recycle loop in a zero benzene aromatics complex. More specifically, the present invention relates to a minimizing benzene, toluene, and an A9/A10 recycle loop in a zero benzene aromatics complex wherein the aromatic feed has a low methyl to phenyl ratio, and where the aromatic feed has a high methyl to phenyl ratio.
    Type: Grant
    Filed: October 11, 2017
    Date of Patent: August 27, 2019
    Assignee: UOP LLC
    Inventors: Elizabeth A. Carter, Deng-Yang Jan, Timur V. Voskoboynikov
  • Patent number: 10239802
    Abstract: This present disclosure relates to processes and apparatuses for toluene methylation in an aromatics complex for producing paraxylene. More specifically, the present disclosure relates to processes and apparatuses wherein a toluene methylation zone is integrated within an aromatics complex for producing paraxylene thus allowing no benzene byproduct to be produced. This may be accomplished by incorporating a toluene methylation process into the aromatics complex and recycling the benzene to the transalkylation unit the aromatics complex.
    Type: Grant
    Filed: May 24, 2018
    Date of Patent: March 26, 2019
    Assignee: UOP LLC
    Inventors: David S. Krimsky, Robert B. Larson
  • Patent number: 10058854
    Abstract: Disclosed are a catalyst system and its use in a process for the conversion of a feedstock containing C8+ aromatic hydrocarbons to produce light aromatic products, comprising benzene, toluene and xylene.
    Type: Grant
    Filed: September 25, 2017
    Date of Patent: August 28, 2018
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Christine N. Elia, Shifang L. Luo, Hari Nair, Wenyih F. Lai, Robert G. Tinger
  • Patent number: 10017394
    Abstract: The present invention provides a mordenite zeolite having a mesopore surface area of greater than 30 m2/g and an average primary crystal size as measured by TEM of less than 80 nm, and methods of making the mordenite zeolite.
    Type: Grant
    Filed: January 21, 2016
    Date of Patent: July 10, 2018
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Wenyih F. Lai, Nicholas S. Rollman, Guang Cao
  • Patent number: 9174892
    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: October 30, 2013
    Date of Patent: November 3, 2015
    Assignee: UOP LLC
    Inventors: Antoine Negiz, Edwin P. Boldingh, Gregory J. Gajda, Dean E. Rende, James E. Rekoske, David E. Mackowiak, Paul T. Barger
  • Patent number: 9096484
    Abstract: The invention is directed to a bimetallic catalyst system adapted for the manufacture of xylenes, a process for making said catalyst system, and to the process of manufacture of xylenes using said catalyst system, providing, in embodiments, improved selectivity by at least one of higher ethylene saturation and low xylene loss, decreased susceptibility to poisoning from feedstream impurities, and ability to operate at less severe conditions.
    Type: Grant
    Filed: March 26, 2015
    Date of Patent: August 4, 2015
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: April D. Ross, Jane C. Cheng
  • Publication number: 20150126770
    Abstract: A process for increasing the production of monoalkylbenzenes is presented. The process includes utilizing a transalkylation process to convert dialkylbenzenes to monoalkylbenzenes. The feed to the transalkylation process has alkylated toluenes and alkylated ethylbenzenes and other alkylated aromatics having small alkyl groups with less than 8 carbons removed to improve the efficiency of the transalkylation process. The recycled dialkylbenzenes and a portion of the recycled benzene are converted to monoalkylbenzenes.
    Type: Application
    Filed: November 1, 2013
    Publication date: May 7, 2015
    Applicant: UOP LLC
    Inventors: Stephen W. Sohn, Mark G. Riley, Michael A. Moore
  • Publication number: 20150119620
    Abstract: In a process for the synthesis of a crystalline molecular sieve material having the EUO framework type, a synthesis mixture is provided suitable for the formation of an EUO framework type molecular sieve and comprising N,N,N,N?,N?,N?-hexamethylhexanediammonium, Q, cations and a colloidal suspension of seed crystals of an EUO framework type molecular sieve. The synthesis mixture is crystallized and an EUO framework type molecular sieve in the form individual crystals and/or aggregates of crystals having an average size, d50, as measured by laser scattering, of less than 15 ?m is recovered from the synthesis mixture.
    Type: Application
    Filed: June 7, 2013
    Publication date: April 30, 2015
    Inventor: Machteld M. W. Mertens
  • Patent number: 9000247
    Abstract: A method of forming mixed xylenes from a heavy reformate using a dealkylation-transalkylation system includes the step of introducing both a heavy reformate containing methyl ethyl benzenes and tri-methyl benzenes and that is sufficiently free of toluene and a hydrogen-containing material into the dealkylation stage such that the heavy reformate and the hydrogen-containing material intermingle and contact the hydrodealkylation catalyst. The dealkylation-transalkylation system includes dealkylation, non-aromatic product gas separations and transalkylation stages. Toluene forms from the reaction of methyl ethyl benzenes and hydrogen in the presence of the hydrodealkylation catalyst. The method also includes the step of introducing a dealkylated heavy reformate into the transalkylation stage such that the dealkylated heavy reformate contacts a transalkylation catalyst, forming a transalkylation stage product mixture includes mixed xylenes.
    Type: Grant
    Filed: April 19, 2013
    Date of Patent: April 7, 2015
    Assignee: Saudi Arabian Oil Company
    Inventor: Raed Abudawoud
  • Publication number: 20150094508
    Abstract: Methods and systems are provided for separating a selected xylene isomer. The method includes separating a feed stream including a plurality of aromatic hydrocarbons into a first stream including toluene and isomers of xylene, and a second stream including isomers of xylene. The method further includes separating the first stream into a third stream including toluene and a fourth stream including isomers of xylene. The method further includes combining the second stream and the third stream in an adsorptive separation unit including an adsorbent configured to adsorb the selected xylene isomer from the second stream. The third stream desorbs the selected xylene isomer to produce a fifth stream including the selected xylene isomer and toluene and a sixth stream including non-selected xylene isomers and toluene. Still further, the method includes separating the sixth stream into a seventh stream including the non-selected xylene isomers and the third stream including toluene.
    Type: Application
    Filed: September 27, 2013
    Publication date: April 2, 2015
    Applicant: UOP LLC
    Inventors: Jason T. Corradi, Gregory Werba, Rajeswar Gattupalli
  • Publication number: 20150094507
    Abstract: Apparatuses and methods are provided for isolating C8 aromatics from hydrocarbon streams. In one embodiment, a method for separating C8 aromatics from a hydrocarbon stream includes introducing the hydrocarbon stream to a fractionation column at a feed point. Further, the method includes fractionating the hydrocarbon stream in the fractionation column. Also, the method includes withdrawing a sidedraw fraction from the fractionation column at a draw point located above the feed point, wherein the sidedraw fraction includes C8 aromatics.
    Type: Application
    Filed: September 27, 2013
    Publication date: April 2, 2015
    Applicant: UOP LLC
    Inventors: Rajeswar Gattupalli, Jason T. Corradi, Patrick Whitchurch, Gregory Werba
  • Publication number: 20150038755
    Abstract: A process and system for the production of at least one xylene isomer is provided. The process includes passing a first stream to one side of a split shell fractionation column and a second stream to the other side of the column. The first stream has a higher ratio of methyl to C2+ alkyl-substituted C9 aromatic compounds than the second stream. A bottoms stream from the one side is separated and passed as feed to a transalkylation zone.
    Type: Application
    Filed: June 11, 2014
    Publication date: February 5, 2015
    Inventors: Jason T. Corradi, Leonid Bresler
  • 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
  • Publication number: 20140357916
    Abstract: A group V metal/rhenium-modified molecular sieve catalyst can be used in hydrocarbon conversion reactions. Embodiments can provide a toluene conversion of at least 30 wt % with selectivity to benzene above 40 wt % and to xylenes above 40 wt % and non-aromatics selectivity of less than 2.0 wt %.
    Type: Application
    Filed: August 14, 2014
    Publication date: December 4, 2014
    Inventors: James Butler, Olga Khabashesku, Darek Wachowicz, Callum Bailey
  • Patent number: 8884087
    Abstract: The present invention provides compositions of crystalline coordination copolymers wherein multiple organic molecules are assembled to produce porous framework materials with layered or core-shell structures. These materials are synthesized by sequential growth techniques such as the seed growth technique. In addition, the invention provides a simple procedure for controlling functionality.
    Type: Grant
    Filed: June 4, 2009
    Date of Patent: November 11, 2014
    Assignees: UOP LLC, The Regents of the University of Michigan
    Inventors: Kyoung Moo Koh, Antek G. Wong-Foy, Adam J. Matzger, Annabelle I. Benin, Richard R. Willis
  • Publication number: 20140316174
    Abstract: Methods are provided for the treatment of a feed stream containing C9 aromatic components to produce mesitylene-containing products. The methods include hydrodealkylating the feed stream to remove C2 and higher alkyl groups from the aromatic components and transalkylating the feed stream to rearrange the distribution of methyl groups among the aromatic components. Disclosed methods also include the treatment of a hydrocarbon feedstock by hydrodealkylation and/or transalkylation in order to produce a hydrocarbon product having an increased mass percentage of mesitylene.
    Type: Application
    Filed: April 18, 2014
    Publication date: October 23, 2014
    Inventors: Chris D'Acosta, Jeffery Miller, Robert Hoch
  • 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
  • Publication number: 20140288342
    Abstract: Described herein an apparatus and methods used to remove unwanted by-products of metathesis reactions.
    Type: Application
    Filed: March 19, 2014
    Publication date: September 25, 2014
    Applicant: Apeiron Catalysts Sp. zo.o.
    Inventor: Krzysztof Skowerski
  • Patent number: 8822747
    Abstract: The xylene isomerization process unit and the transalkylation process units are combined in the present invention. A fractionation column can be shared by the two units, reducing the capital cost of the complex. In some embodiments, a split shell fractionation column and a split separator can be used.
    Type: Grant
    Filed: September 25, 2012
    Date of Patent: September 2, 2014
    Assignee: UOP LLC
    Inventors: Jason T. Corradi, David W. Ablin, David W. Liu
  • Patent number: 8772564
    Abstract: This invention relates to a method wherein a high-purity paraxylene can be produced efficiently by using a catalyst having a molecular sieving action (or shape selectivity) and being excellent in the catalytic activity without isomerization and adsorption-separation steps. More particularly, it relates to a method of producing a high-purity paraxylene, characterized in that MFI type zeolite having a primary particle size of not more than 100 ?m, a structure defining agent and silica material having an average particle size of not less than 10 nm but less than 1.0 ?m are used as a starting material, and a synthetic zeolite catalyst produced by subjecting the MFI type zeolite to a coating treatment with an aqueous solution obtained by mixing so as to satisfy X×Y<0.05 (wherein X is a concentration of the silica material (mol %) and Y is a concentration of the structure defining agent (mol %)) is used in the alkylation or disproportionation of at least one of benzene and toluene as a starting material.
    Type: Grant
    Filed: September 29, 2009
    Date of Patent: July 8, 2014
    Assignee: JX Nippon Oil & Energy Corporation
    Inventors: Koichi Matsushita, Chikanori Nakaoka, Norikazu Nishiyama
  • Patent number: 8754247
    Abstract: A catalyst is described which comprises at least one IZM-2 zeolite and at least one matrix, said zeolite having a chemical composition expressed as the anhydrous base in terms of moles of oxides by the following general formula: XO2: aY2O3: bMnO, in which X represents at least one tetravalent element, Y represents at least one trivalent element and M is at least one alkali metal and/or alkaline-earth metal, a and b respectively representing the number of moles of Y2O3 and MnO; and a is in the range 0.001 to 0.5, b is in the range 0 to 1 and n is in the range 1 to 2. Said catalyst is used in various processes for the transformation of hydrocarbon feeds.
    Type: Grant
    Filed: July 21, 2009
    Date of Patent: June 17, 2014
    Assignee: IFP Energies nouvelles
    Inventors: Amandine Cabiac, Nicolas Cadran, Emmanuelle Guillon, Vincent Lecocq, Sylvie Maury
  • Patent number: 8742191
    Abstract: A process for transalkylation of polyalkylated aromatic components can include providing a transalkylation reaction zone containing a transalkylation catalyst. A feedstock can be introduced into an inlet of the transalkylation reaction zone and into contact with the transalkylation catalyst. The feedstock can include a polyalkylated aromatic component derived from an aromatic substrate. The aromatic substrate can be supplied to the transalkylation reaction zone. The transalkylation reaction zone can be operated at temperature and pressure conditions sufficient to cause disproportionation of the polyalkylated aromatic component to produce a disproportionation product having a reduced polyalkylated aromatic content and an enhanced monoalkylated aromatic content. The disproportionation product can be withdrawn from the transalkylation reaction zone. Amounts of nitrogen containing compounds in the aromatic substrate can be monitored in a range of from 15 to 35 wppm by dry colorimetry.
    Type: Grant
    Filed: December 5, 2013
    Date of Patent: June 3, 2014
    Assignee: Total Petrochemicals France
    Inventor: Jean-Bernard Cary
  • Publication number: 20140094633
    Abstract: A process for transalkylation of polyalkylated aromatic components can include providing a transalkylation reaction zone containing a transalkylation catalyst. A feedstock can be introduced into an inlet of the transalkylation reaction zone and into contact with the transalkylation catalyst. The feedstock can include a polyalkylated aromatic component derived from an aromatic substrate. The aromatic substrate can be supplied to the transalkylation reaction zone. The transalkylation reaction zone can be operated at temperature and pressure conditions sufficient to cause disproportionation of the polyalkylated aromatic component to produce a disproportionation product having a reduced polyalkylated aromatic content and an enhanced monoalkylated aromatic content. The disproportionation product can be withdrawn from the transalkylation reaction zone. Amounts of nitrogen containing compounds in the aromatic substrate can be monitored in a range of from 15 to 35 wppm by dry colorimetry.
    Type: Application
    Filed: December 5, 2013
    Publication date: April 3, 2014
    Applicant: TOTAL PETROCHEMICALS FRANCE
    Inventor: Jean-Bernard Cary
  • Patent number: 8636976
    Abstract: This invention relates to a crystalline molecular sieve having, in its as-synthesized form, an X-ray diffraction pattern including d-spacing maxima at 13.18±0.25 and 12.33±0.23 Angstroms, wherein the peak intensity of the d-spacing maximum at 13.18±0.25 Angstroms is at least as great as 90% of the peak intensity of the d-spacing maximum at 12.33±0.23 Angstroms. This invention also relates to a method of making thereof.
    Type: Grant
    Filed: June 28, 2012
    Date of Patent: January 28, 2014
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Wieslaw J. Roth, Thomas Yorke, Michael C. Kerby, Simon C. Weston
  • Publication number: 20130324760
    Abstract: A method of crystallizing a crystalline molecular sieve having a pore size in the range of from about 2 to about 19 ?, said method comprising the steps of (a) providing a mixture comprising at least one source of ions of tetravalent element (Y), at least one hydroxide source (OH?), and water, said mixture having a solid-content in the range of from about 15 wt. % to about 50 wt. %; and (b) treating said mixture to form the desired crystalline molecular sieve with stirring at crystallization conditions sufficient to obtain a weight hourly throughput from about 0.005 to about 1 hr?1, wherein said crystallization conditions comprise a temperature in the range of from about 200° C. to about 500° C. and a crystallization time less than 100 hr.
    Type: Application
    Filed: August 7, 2013
    Publication date: December 5, 2013
    Inventors: Ivy D. Johnson, Wenyih Frank Lai
  • Patent number: 8586809
    Abstract: A guard bed or absorber is placed upstream of a transalkylation reactor to avoid deposition of halide and/or halogen species on the catalysts in said reactor.
    Type: Grant
    Filed: July 14, 2011
    Date of Patent: November 19, 2013
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: James H. Beech, Jr., Julia E. Steinheider, Doron Levin, Selma S. Lawrence
  • Patent number: 8580702
    Abstract: The present invention discloses a catalyst for toluene shape selective disproportionation, comprising: a) 45 to 95 wt % of ZSM-5 molecular sieve having an average particle size of from 0.3 to 6 ?m and a molar ratio of SiO2 to Al2O3 of from 20 to 120; b) 0.01 to 30 wt % of at least one metal selected from the group consisting of Group IIB metals, Group IIIB metals, rare earth elements and Group VIII metals other than nickel, or oxide(s) thereof; c) 0 to 20 wt % of at least one metal selected from the group consisting of Group VA metals, Group VIB metals and alkaline earth metals, or oxide(s) thereof; d) 1 to 25 wt % of a silica inert surface coating derived from an organopolysiloxane; and e) 1 to 50 wt % of a binder. The present invention further discloses a process for shape selectively disproportionating toluene into p-xylene, comprising contacting a reaction stream containing toluene with the catalyst for toluene shape selective disproportionation under toluene disproportionation conditions.
    Type: Grant
    Filed: November 2, 2007
    Date of Patent: November 12, 2013
    Assignees: China Petroleum & Chemical Corporation, Shanghai Research Institute of Petrochemical Technology Sinopec
    Inventors: Zaiku Xie, Dejin Kong, Zhirong Zhu, Wei Li, Qingling Chen, Rong Zhang
  • Patent number: 8529752
    Abstract: This invention relates to a process for hydrocarbon conversion comprising contacting a hydrocarbon feedstock with a crystalline molecular sieve, in its ammonium exchanged form or in its calcined form, under conversion conditions to form a conversion product, said crystalline molecular sieve comprising unit cells with MWW topology and is characterized by diffraction streaking from the unit cell arrangement in the c direction as evidenced by the arced hk0 patterns of electron diffraction pattern.
    Type: Grant
    Filed: December 15, 2011
    Date of Patent: September 10, 2013
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Wieslaw J. Roth, Thomas Yorke, Douglas Lewis Dorset, Mohan Kalyanaraman, Michael Charles Kerby, Simon Christopher Weston
  • Publication number: 20130197178
    Abstract: The present invention provides novel and stable crystalline 1H-1,2,3 triazolium carbenes and metal complexes of 1H-1,2,3 triazolium carbenes. The present invention also provides methods of making 1H-1,2,3 triazolium carbenes and metal complexes of 1H-1,2,3 triazolium carbenes. The present invention also provides methods of using 1H-1,2,3 triazolium carbenes and metal complexes of 1H-1,2,3 triazolium carbenes in catalytic reactions.
    Type: Application
    Filed: April 26, 2011
    Publication date: August 1, 2013
    Applicant: The Regents of the University of California
    Inventors: Guy Bertrand, Gregorio Gulsado-Barrios, Jean Bouffard, Bruno Donnadieu
  • Publication number: 20130190546
    Abstract: A process for making an alkylated aromatic is described. The alkylating agent is introduced into the reactor in at least two positions. This decreases the propane/benzene ratio at each injection point, improving the methylation reagent selectivity.
    Type: Application
    Filed: January 24, 2012
    Publication date: July 25, 2013
    Applicant: UOP LLC
    Inventors: Feng Xu, John Bauer
  • Publication number: 20130130345
    Abstract: The invention provides a process for producing a variety renewable aromatic compounds such as benzene, toluene, xylenes, and cumene, as well as compounds derived from these including, for example, aniline, benzoic acid, cresol, cyclohexane, cyclohexanone, phenol and bisphenol A, toluene di-isocyanate, isophthalic acid, phthalic anhydride, terephthalic acid and dimethyl terephthalate. The invention also provides for renewable forms of these aromatic compounds.
    Type: Application
    Filed: June 28, 2011
    Publication date: May 23, 2013
    Applicant: JNF BIOCHEMICALS, LLC
    Inventors: Wendy Thai, David A. Sikkenga, Will Schroeder
  • Patent number: 8431759
    Abstract: A process for increasing the production of monoalkylbenzenes is presented. The process includes utilizing a transalkylation process to convert dialkylbenzenes to monoalkylbenzenes. The transalkylation process recycles a portion of the effluent stream from the transalkylation reactor back to the feed of the transalkylation reactor. The recycled dialkylbenzenes and a portion of the recycled benzene are converted to monoalkylbenzenes.
    Type: Grant
    Filed: November 30, 2012
    Date of Patent: April 30, 2013
    Assignee: UOP LLC
    Inventors: Stephen W. Sohn, Mark G. Riley
  • Patent number: 8431758
    Abstract: Processes for increasing overall aromatics and xylenes yield in an aromatics complex are provided. A C8+ aromatics stream from an aromatics-rich reformate is separated into a C8 aromatics fraction and a C9+ aromatics fraction comprising higher alkyl group-substituted C9 and C10 aromatics. The C9+ aromatics fraction is separated into a lighter boiling, higher alkyl group-substituted C9 or C9/C10 aromatics fraction and a heavier boiling, C10+ or C11+ aromatics fraction. The lighter boiling, higher alkyl group-substituted C9 or C9/C10 aromatics fraction is isomerized to convert a portion of the higher alkyl group-substituted C9 or C9/C10 aromatics therein into methyl-enriched C9 aromatics or methyl-enriched C9/C10 aromatics. The methyl-enriched C9+ aromatics stream comprising the methyl-enriched C9+ aromatics stream or the methyl-enriched C9/C10 aromatics is transalkylated with a toluene-containing stream.
    Type: Grant
    Filed: September 16, 2010
    Date of Patent: April 30, 2013
    Assignee: UOP LLC
    Inventors: Stanley J. Frey, Jason T. Corradi, Gregory Werba
  • Patent number: 8350112
    Abstract: A process for transalkylating aromatic hydrocarbon compounds, the process comprising introducing an aromatic hydrocarbon feed stream and a water source to a transalkylation zone. The feed stream contacts a catalyst in the transalkylation zone in the presence of water, and produces a reaction product stream comprising benzene and xylene. The invention includes methods to control the transalkylation process.
    Type: Grant
    Filed: July 10, 2012
    Date of Patent: January 8, 2013
    Assignee: UOP LLC
    Inventors: Edwin P. Boldingh, Antoine Negiz
  • Patent number: 8350110
    Abstract: A process for increasing the production of monoalkylbenzenes is presented. The process includes utilizing a transalkylation process to convert dialkylbenzenes to monoalkylbenzenes. The transalkylation process recycles a portion of the effluent stream from the transalkylation reactor back to the feed of the transalkylation reactor. The recycled dialkylbenzenes and a portion of the recycled benzene are converted to monoalkylbenzenes.
    Type: Grant
    Filed: November 2, 2010
    Date of Patent: January 8, 2013
    Assignee: UOP LLC
    Inventors: Stephen W. Sohn, Mark G. Riley
  • Patent number: 8350113
    Abstract: A process for transalkylating aromatic hydrocarbon compounds, the process comprising introducing an aromatic hydrocarbon feed stream and a sulfur source to a transalkylation zone. The feed stream contacts a catalyst in the transalkylation zone in the presence of sulfur, and produces a reaction product stream comprising benzene and xylene. The invention includes methods to control the transalkylation process.
    Type: Grant
    Filed: July 10, 2012
    Date of Patent: January 8, 2013
    Assignee: UOP LLC
    Inventor: Edwin P. Boldingh
  • Patent number: 8314045
    Abstract: A porous solid acid catalyst having high concentration of acidic sites and a large surface area includes a porous silica support and a sulfonated carbon layer disposed within the pores of the silica support. The catalyst, in certain embodiments, has a concentration of —SO3H groups of at least about 0.5 mmol/g and a predominant pore size of at least about 300 ?. The catalyst is used to catalyze a variety of acid-catalyzed reactions, including but not limited to alkylation, acylation, etherification, olefin hydration and alcohol dehydration, dimerization of olefin and bicyclic compounds, esterification and transesterification. For example, the catalyst can be used to catalyze esterification of free fatty acids (FFAs) and, in certain embodiments, to catalyze transesterification of triglycerides in fats and oils.
    Type: Grant
    Filed: October 27, 2010
    Date of Patent: November 20, 2012
    Assignee: Entreprises Sinoncelli S.A.R.L.
    Inventors: Jacques Sinoncelli, Sergey V. Gurevich
  • Publication number: 20120271084
    Abstract: Methods are disclosed for producing C8 aromatic hydrocarbons. Representative methods comprise fractionating a transalkylation effluent, exiting a transalkylation reaction zone and comprising C8 and C9 aromatic hydrocarbons, to provide a C8 aromatic hydrocarbon-enriched fraction and a C9 aromatic hydrocarbon-enriched fraction. The methods may further comprise (i) recycling the C9 aromatic hydrocarbon-enriched fraction to the transalkylation reaction zone and/or (ii) separating, in a xylene separation zone, isomers of C8 aromatic hydrocarbons in the C8 aromatic hydrocarbon-enriched fraction, into a para-xylene-enriched extract and a para-xylene-depleted raffinate. Performance in the transalkylation reaction zone is improved and/or downstream processing requirements in an aromatics complex are mitigated.
    Type: Application
    Filed: April 22, 2011
    Publication date: October 25, 2012
    Applicant: UOP LLC
    Inventors: ROBERT HAIZMANN, PAUL ALVIN SECHRIST
  • Patent number: 8207388
    Abstract: A catalytic composition is described for the transalkylation of aromatic hydrocarbons comprising a zeolite and an inorganic binder, characterized by an extra-zeolitic porosity, i.e. the porosity obtained by adding the mesoporosity and the macroporosity fractions present in the catalytic composition, higher than or equal to 0.7 cc/g, which is such as to consist for a fraction of at least 30% of pores having a diameter greater than 100 nanometers. These catalytic compositions have a crushing strength not lower than 1.7 kg/mm and an apparent density not higher than 0.5 g/cc. A process is also described for the transalkylation of polyalkylated aromatic hydrocarbons which uses these catalytic compositions.
    Type: Grant
    Filed: December 15, 2003
    Date of Patent: June 26, 2012
    Assignee: Polimeri Europa S.p.A.
    Inventors: Elena Bencini, Gianni Girotti
  • Patent number: 8168843
    Abstract: A process for reducing benzene content in a reformate stream, including: fractionating a full range reformate comprising benzene, C7 to C9 monoalkyl aromatics, and C10+ polyalkyl aromatics into at least three fractions including a light reformate fraction comprising the benzene; a medium reformate fraction comprising the C7 to C9 monoalkyl aromatics; and a heavy reformate fraction comprising the C10+ polyalkyl aromatics; feeding the light reformate fraction, the heavy reformate fraction and a transalkylation catalyst to a transalkylation reaction zone; contacting the light fraction and the heavy fraction in presence of the transalkylation catalyst in the transalkylation reaction zone to react at least a portion of the benzene with C10+ polyalkyl aromatics to form monoalkyl aromatics; separating an effluent from the transalkylation reaction zone to form a catalyst fraction and a liquid fraction comprising the monoalkyl aromatics.
    Type: Grant
    Filed: August 20, 2008
    Date of Patent: May 1, 2012
    Assignee: Catalytic Distillation Technologies
    Inventors: Kerry L. Rock, Christopher C. Boyer, Lawrence A. Smith, Jr.
  • Publication number: 20120083639
    Abstract: Processes for maximizing high-value aromatics production utilizing stabilized crude benzene withdrawal are provided. Aromatic reactor effluent comprising a C5? fraction and a C6 to C10 fraction is separated into a benzene-rich stream and liquid and vapor streams depleted in benzene, one of the liquid streams depleted in benzene being a benzene-depleted C6? fraction. At least a portion of the C5? fraction from the benzene-rich stream is removed.
    Type: Application
    Filed: October 1, 2010
    Publication date: April 5, 2012
    Applicant: UOP LLC
    Inventors: Michael R. Smith, Gavin P. Towler
  • Patent number: 8138384
    Abstract: In a process for converting methane to alkylated aromatic hydrocarbons, a feed containing methane is contacted with a dehydrocyclization catalyst under conditions effective to convert said methane to aromatic hydrocarbons and produce a first effluent stream comprising aromatic hydrocarbons and hydrogen. At least a portion of said aromatic hydrocarbon from said first effluent stream is then contacted with an alkylating agent under conditions effective to alkylate said aromatic hydrocarbon and produce an alkylated aromatic hydrocarbon having more alkyl side chains than said aromatic hydrocarbon prior to the alkylating.
    Type: Grant
    Filed: December 2, 2005
    Date of Patent: March 20, 2012
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Larry L. Iaccino, Elizabeth L. Stavens, Gary D. Mohr, Matthew J. Vincent
  • Publication number: 20120022279
    Abstract: A catalyst is described which comprises at least one IZM-2 zeolite and at least one matrix, said zeolite having a chemical composition expressed as the anhydrous base in terms of moles of oxides by the following general formula: XO2: aY2O3: bMnO, in which X represents at least one tetravalent element, Y represents at least one trivalent element and M is at least one alkali metal and/or alkaline-earth metal, a and b respectively representing the number of moles of Y2O3 and MnO; and a is in the range 0.001 to 0.5, b is in the range 0 to 1 and n is in the range 1 to 2. Said catalyst is used in various processes for the transformation of hydrocarbon feeds.
    Type: Application
    Filed: July 21, 2009
    Publication date: January 26, 2012
    Applicant: IFP Energies nouvelles
    Inventors: Amandine Cabiac, Nicolas Cadran, Emmanuelle Guillon, Vincent Lecocq, Sylvie Maury
  • Patent number: 8084657
    Abstract: A process of making p-xylcne comprising processing a mixed feedstock containing benzene, toluene, C8 aromatic hydrocarbons, C9 and higher aromatic hydrocarbons, and non-aromatic hydrocarbons through a series of operations and various units, including a C9 and higher aromatic hydrocarbon dealkylation unit, a toluene selective disproportionate unit, an adsorption separation unit, an isomerization unit, and a crystallization separation unit.
    Type: Grant
    Filed: November 20, 2009
    Date of Patent: December 27, 2011
    Assignees: China Petroleum & Chemical Corporation, Shanghai Research Institute of Petrochemical Technology Sinopec
    Inventors: Dejin Kong, Hongli Guo, Luping Zhong, Weisheng Yang, Jian Xiao
  • Patent number: 8052938
    Abstract: The present invention provides a reactor system having: (1) a first reactor receiving an oxygenate component and a hydrocarbon component and capable of converting the oxygenate component into a light olefin and the hydrocarbon component into alkyl aromatic compounds; (2) a separator system for providing a first product stream containing a C3 olefin, a second stream containing a C7 aromatic, and a third stream containing C8 aromatic compounds; (3) a first line connecting the separator to the inlet of the first reactor for conveying the second stream to the first reactor; (4) a second line in fluid communication with the separator system for conveying the C3 olefin to a propylene recovery unit, and (4) a third line in fluid communication with the separator system for conveying the C8 aromatic compounds to a xylene recovery unit.
    Type: Grant
    Filed: October 12, 2010
    Date of Patent: November 8, 2011
    Assignee: UOP LLC
    Inventors: Andrea G. Bozzano, Timur V. Voskoboynikov, Tom N. Kalnes, Paul T. Barger, Gavin P. Towler, Bryan K. Glover
  • Patent number: 8030533
    Abstract: A process for the combined production of para-xylene and benzene comprises: separating a first feed, by adsorption in a simulated moving bed SMB, to produce an extract E rich in para-xylene and at least one raffinate R which is depleted in para-xylene; converting a secondary feed of toluene by selective disproportionation to produce benzene and xylenes; a) at the start of the cycle, producing a supplemental quantity of para-xylene in a crystallization unit supplied with the xylenes from the disproportionation; b) at the end of the cycle, when the adsorbant has aged: dividing the distilled extract E into a first fraction Ea and a complementary second fraction Eb; replacing the feed to the initial crystallization by the stream Ea; and recycling the xylenes from the disproportionation to the SMB. The invention enables para-xylene and benzene production to be maintained despite ageing of the SMB absorbent.
    Type: Grant
    Filed: March 14, 2006
    Date of Patent: October 4, 2011
    Assignee: IFP Energies Nouvelles
    Inventors: Gerard Hotier, Kim Seo Il
  • Patent number: 8030238
    Abstract: The present invention relates to a new zeolite having a beta-type crystalline structure, characterized by a distribution of the Lewis acid sites and Brønsted acid sites corresponding to a molar ratio [Lewis sites] [Brønsted sites] equal to or higher than 1.5. This new zeolite is useful in preparation processes of alkylated aromatic hydrocarbons through the alkylation and/or transalkylation of aromatic compounds. The preparation method of the new zeolite is also object of the present invention.
    Type: Grant
    Filed: June 21, 2005
    Date of Patent: October 4, 2011
    Assignees: Polimeri Europa S.p.A., Eni S.p.A.
    Inventors: Guido Spano′, Stefano Ramello, Gianni Girotti, Franco Rivetti, Angela Carati
  • Patent number: 8022261
    Abstract: A catalyst composition comprises a crystalline MCM-22 family molecular sieve and a binder, wherein the catalyst composition is characterized by an extra-molecular sieve porosity greater than or equal to 0.122 ml/g for pores having a pore diameter ranging from about 2 nm to about 8 nm, wherein the porosity is measured by N2 porosimetry. The catalyst composition may be used for the process of alkylation or transalkylation of an alkylatable aromatic compound with an alkylating agent. The molecular sieve may have a Constraint Index of less than 12, e.g., less than 2. Examples of molecular sieve useful for this disclosure are a MCM-22 family molecular sieve, zeolite Y, and zeolite Beta.
    Type: Grant
    Filed: October 18, 2010
    Date of Patent: September 20, 2011
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Mohan Kalyanaraman, Christine N. Elia, Darryl D. Lacy, Jean W. Beeckman, Michael C. Clark
  • Publication number: 20110201863
    Abstract: This invention relates to a method wherein a high-purity paraxylene can be produced efficiently by using a catalyst having a molecular sieving action (or shape selectivity) and being excellent in the catalytic activity without isomerization and adsorption-separation steps. More particularly, it relates to a method of producing a high-purity paraxylene, characterized in that MFI type zeolite having a primary particle size of not more than 100 ?m, a structure defining agent and silica material having an average particle size of not less than 10 nm but less than 1.0 ?m are used as a starting material, and a synthetic zeolite catalyst produced by subjecting the MFI type zeolite to a coating treatment with an aqueous solution obtained by mixing so as to satisfy X×Y<0.05 (wherein X is a concentration of the silica material (mol %) and Y is a concentration of the structure defining agent (mol %)) is used in the alkylation or disproportionation of at least one of benzene and toluene as a starting material.
    Type: Application
    Filed: September 29, 2009
    Publication date: August 18, 2011
    Applicant: JX NIPPON OIL & ENERGY CORPORATION
    Inventors: Koichi Matsushita, Chikanori Nakaoka, Norikazu Nishiyama