By Condensation Of Entire Molecules Or Entire Hydrocarbyl Moieties Thereof, E.g., Alkylation, Etc. Patents (Class 585/446)
  • 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: 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
  • 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
  • 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
  • Patent number: 8395006
    Abstract: A process for the alkylation of a benzene-containing refinery stream such as reformate with light refinery olefins which is capable of achieving high benzene conversion levels operates in a fixed bed of an MWW zeolite catalyst, preferably MCM-22, in single pass mode in the liquid phase at a relatively low to moderate temperatures with pressure maintained at a value adequate to ensure subcritical operation. High levels of benzene conversion with conversions of at least 90% and higher, e.g. 92% or 95% or even higher are achievable. A high octane product is produced, comprising mono-, di- and tri-alkylbenzenes with lesser levels of the tetra-substituted products. By operating with staged olefin injection, the end point of the alkylation product can be maintained at a low value while, at the same time, achieving high levels of benzene and olefin conversion.
    Type: Grant
    Filed: March 9, 2010
    Date of Patent: March 12, 2013
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Michael C. Clark, Benjamin S. Umansky, Elizabeth A. Nye, Mark J. Reichensperger, William C. Lewis
  • 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: 8344197
    Abstract: In a process for the production of para-xylene, methanol is preheated to a first temperature, an aromatic feedstock comprising toluene and/or benzene is preheated to a second temperature and the preheated methanol and aromatic feedstocks are fed to a reactor at a first methanol to aromatic feedstock molar ratio. The preheated aromatic feedstock is contacted with the preheated methanol under alkylation conditions in the reactor in the presence of a catalyst so that the methanol reacts with the aromatic feedstock to produce an effluent comprising para-xylene. During the reaction, a temperature is measured within the reactor and is compared with a predetermined optimal temperature. The methanol to aromatic feedstock molar ratio is then adjusted in a manner to reduce any difference between the measured and predetermined optimal temperatures in the reactor.
    Type: Grant
    Filed: September 30, 2010
    Date of Patent: January 1, 2013
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: James R. Lattner, Mark P. Hagemeister, Jon Edmond Randolph Stanat, John Di-Yi Ou, Xiaobo Zheng, Lu Han
  • Patent number: 8344200
    Abstract: A process for the purification of aromatic streams is provided that includes a new start up procedure that in embodiments significantly reduces impurities in an aromatics feedstock.
    Type: Grant
    Filed: April 8, 2010
    Date of Patent: January 1, 2013
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventor: Stephen H. Brown
  • Publication number: 20120316373
    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: Application
    Filed: June 9, 2011
    Publication date: December 13, 2012
    Applicant: UOP, LLC
    Inventors: Robert Haizmann, Laura E. Leonard, Paula L. Bogdan
  • Patent number: 8329969
    Abstract: A process for the conversion of biomass derived pyrolysis oil to liquid fuel components is presented. The process includes the production of diesel, aviation, and naphtha boiling point range fuels or fuel blending components by two-stage deoxygenation of the pyrolysis oil and separation of the products.
    Type: Grant
    Filed: April 6, 2009
    Date of Patent: December 11, 2012
    Assignee: UOP LLC
    Inventors: Michael J. McCall, Timothy A. Brandvold, Douglas C. Elliott
  • Patent number: 8329966
    Abstract: Synthetic base oil composition comprising dialkyl aromatic compound with alkyl side chain carbon number from C10 to C28, or preferably C11 to C24, or even more preferably, C12 to C18, wherein the branching characteristics of the alkyl side chain has a total methyl number (TMN) determined by C13 NMR spectroscopy to be from more than 2.1 to less than 3.5, or preferably from 2.15 to 3.25, or even more preferably from 2.2 to 3.0, or a branching index (BI) from more than 0.1 to less than 1.5, or more preferably, 0.15 to 1.25, or even more preferably, 0.2 to 1.0. The synthetic base oil composition has a combination of high viscometric index, low volatility, superior low temperature properties, and improved thermal/oxidation stability, and is particularly suitable to be used as a premium synthetic base stock, second base oil component, or additive for lubricant and additive package applications.
    Type: Grant
    Filed: October 10, 2007
    Date of Patent: December 11, 2012
    Assignee: Formosan Union Chemical Corp.
    Inventors: Chi-Hsing Tsai, Chien-Hsun Tsai
  • Publication number: 20120296143
    Abstract: The proposed process uses crystallization technology to purify paraxylene simultaneously of large concentrations of C8 aromatics and also small concentrations of oxygenated species.
    Type: Application
    Filed: July 26, 2012
    Publication date: November 22, 2012
    Inventors: Mark P. Hagemeister, David Lee Johnson, John Joseph Monson
  • 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: 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: 8309780
    Abstract: Provided is a process for oligomerizing n-olefins. The process has the step of reacting (oligomerizing) an amount of one or more n-olefins in the presence of a catalytically effective amount of a two or more metal oxides at a temperature effective to effect oligomerization. The two or more metal oxides are represented by the formula MOn/M?On?. M and M?, are, independently, selected from the group consisting of Al, Ce, Fe, P, W, Zr, and combinations thereof. M and M? are different metals or combinations of metals. “n” and “n?” are positive numbers and vary stoichiometrically depending on the valency of M and M?, respectively. Provided is also a process for alkylation of an alkylatable aromatic compound. The process has the step of contacting an amount of one or more n-olefins with an amount of aromatic compound in the presence of a catalytically effective amount of the two or more metal oxides at a temperature effective to effect alkylation of the aromatic compound.
    Type: Grant
    Filed: December 21, 2007
    Date of Patent: November 13, 2012
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Jihad Mohammed Dakka, Jeffrey T. Elks, James C. Vartuli
  • Patent number: 8288602
    Abstract: The present invention describes a cost-efficient method for preparing di-substituted fluorenes in high yield.
    Type: Grant
    Filed: March 28, 2007
    Date of Patent: October 16, 2012
    Assignee: Total Petrochemicals Research Feluy
    Inventors: Alexander Z. Voskoboynikov, Artyom Y. Le Bedev, Andrey F. Asachenko, Abbas Razavi
  • Patent number: 8288604
    Abstract: A method of rapid methylation of an aromatic compound or an alkenyl compound, which is capable of obtaining an aromatic compound or an alkenyl compound labeled with a methyl group or a fluoromethyl group under a mild condition rapidly in high yield using an organic boron compound whose toxicity is not so high as a substrate. A kit for preparing a PET tracer and a method of producing a PET tracer can be practiced using the rapid methylation method. In an aprotic polar solvent, methyl iodide or X—CH2F (wherein X is a functional group which can be easily released as an anion), and an organic boron compound in which an aromatic ring or an alkenyl group is attached to boron are subjected to cross-coupling in the presence of a palladium(0) complex, a phosphine ligand, and a base.
    Type: Grant
    Filed: August 24, 2007
    Date of Patent: October 16, 2012
    Assignees: Gifu University, Riken, Hamamatsu Photonics K.K.
    Inventors: Masaaki Suzuki, Hisashi Doi, Hideo Tsukada
  • Patent number: 8269053
    Abstract: A process for making ethylbenzene and/or styrene by reacting toluene with methane in one or more microreactors is disclosed. In one embodiment a method of revamping an existing styrene production facility by adding one or more microreactors capable of reacting toluene with methane to produce a product stream comprising ethylbenzene and/or styrene is disclosed.
    Type: Grant
    Filed: November 1, 2011
    Date of Patent: September 18, 2012
    Assignee: Fina Technology, Inc.
    Inventor: James R. Butler
  • Patent number: 8247627
    Abstract: In a process for producing phenol and/or cyclohexanone, benzene and hydrogen are contacted with a first catalyst in a hydroalkylation step to produce a first effluent stream comprising cyclohexylbenzene, cyclohexane, and unreacted benzene. At least part of the first effluent stream is supplied to a first separation system to divide the first effluent stream part into a cyclohexylbenzene-rich stream and a C6 product stream comprising unreacted benzene and cyclohexane.
    Type: Grant
    Filed: March 16, 2009
    Date of Patent: August 21, 2012
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Jihad M. Dakka, J. Scott Buchanan, Jane C. Cheng, Tan-Jen Chen, Lorenzo C. DeCaul, Terry E. Helton, Jon E. Stanat, Francisco M. Benitez
  • Patent number: 8237002
    Abstract: A method for producing an unsaturated organic compound represented by the formula (3): (Y1)m-1—R1—R2—(Y2)n-1??(3) wherein Y1 represents R2 or X1, and Y2 represents R1 or B(X2)2, which comprises reacting a compound represented by the formula (1): R1(X1)m??(1) wherein R1 represents an aromatic group or the like, X1 represents a leaving group and m represents 1 or 2, with a compound represented by the formula (2): R2{B(X2)2}n??(2) wherein R2 represents an aromatic group or the like, X2 represents a hydroxyl group or the like, and n represents 1 or 2, in the presence of (a) a nickel compound selected from a nickel carboxylate, nickel nitrate and a nickel halide, (b) a phosphine compound such as 1,4-bis(dicyclohexylphosphino) butane, (c) an amine selected from a primary amine and a diamine such as N,N,N?,N?-tetramethyl-1,2-ethanediamine, and (d) an inorganic base.
    Type: Grant
    Filed: April 28, 2009
    Date of Patent: August 7, 2012
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Taku Asaumi, Takashi Kamikawa
  • Patent number: 8211820
    Abstract: The invention provides a catalyst composition for use in a cross-coupling reaction containing an iron or cobalt fluoride and a nitrogen-containing heterocyclic ring compound represented by General Formula (1A) or (1B), wherein R1 and R2 are same or different, and represent substituted or unsubstituted aryl group etc.; and R3 and R4 are same or different, and represent hydrogen etc., ?represents a single bond or a double bond, and X? represents a monovalent anion. The invention also provides a method for producing a cross-coupling compound by reacting an organic magnesium compound with an organic halogen compound in the presence of the catalyst composition.
    Type: Grant
    Filed: March 3, 2008
    Date of Patent: July 3, 2012
    Assignees: Kyoto University, Tosoh Finechem Corporation
    Inventors: Masaharu Nakamura, Takuji Hatakeyama
  • Patent number: 8207380
    Abstract: An alkylated hydroxyaromatic compound prepared by reacting at least one hydroxyaromatic compound with a branched olefinic oligomer having from about 20 to about 80 carbon atoms in the presence of a acid catalyst. 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: April 27, 2007
    Date of Patent: June 26, 2012
    Assignee: Chevron Oronite LLC
    Inventors: Curt B. Campbell, James J. Harrison
  • Patent number: 8183420
    Abstract: An alkylaromatic hydrocarbon composition prepared by the process which comprises oligomerizing an olefin selected from the group consisting of propylene, n-butene and mixtures thereof over an oligomerization catalyst, to form a oligomerization product comprising at least 95% by weight of mono-olefin oligomers of the empirical formula: CnH2n wherein n is greater than or equal to 10, the mono-olefin oligomers comprise at least 20% by weight of olefins having at least 12 carbon atoms, and the olefins having at least 12 carbon atoms having an average of from 0.8 to 2.0 C1-C3 alkyl branches per carbon chain. Sulfonation of the alkylaromatic hydrocarbon product produces an alkylaryl sulfonate mixture that exhibits advantageous properties, such as biodegradability and hard and cold water performance.
    Type: Grant
    Filed: October 8, 2009
    Date of Patent: May 22, 2012
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Carolyn B. Duncan, David Wayne Turner, Jane C. Cheng, Charles M. Yarbrough, Raphael Frans Caers, Ramzi Y. Saleh, James L. Propp
  • Publication number: 20120095276
    Abstract: Disclosed are a novel NU-85 molecular sieve having a specific surface area ranging from about 405 m2/g to about 470 m2/g and a pore volume ranging from about 0.27 cm3/g to about 0.35 cm3/g, and processes for preparing the NU-85 molecular sieve.
    Type: Application
    Filed: October 11, 2011
    Publication date: April 19, 2012
    Inventors: Zhizhi ZHANG, Xiwen Zhang, Bo Qin
  • Publication number: 20120088937
    Abstract: One exemplary embodiment can be a method for processing polyisopropylbenzene for producing cumene. The method can include passing a transalkylation feed stream to a transalkylation zone, and passing a reaction product to a separation zone. Typically, the separation zone produces a stream including di-isopropylbenzene, tri-isopropylbenzene, and one or more heavy compounds. Moreover, the stream may include at least about 0.7%, by weight, of the one or more heavy compounds based on the weight of the di-isopropylbenzene, tri-isopropylbenzene, and the one or more heavy compounds in the stream, and at least a portion of the stream is recycled to the transalkylation zone.
    Type: Application
    Filed: October 12, 2010
    Publication date: April 12, 2012
    Applicant: UOP, LLC
    Inventors: Deng-Yang Jan, Christopher Lepine Standing, James Albert Johnson, Margo W. Steward, Mathias P. Koljack
  • Patent number: 8153853
    Abstract: A method for the separation of hydrocarbon compounds utilizing a dividing wall distillation column is described. The dividing wall distillation column enables one or more side draw stream to be removed from the dividing wall distillation column in addition to an overhead stream and a bottoms stream.
    Type: Grant
    Filed: April 27, 2011
    Date of Patent: April 10, 2012
    Assignee: Fina Technology, Inc.
    Inventor: James R. Butler
  • 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
  • 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: 8101810
    Abstract: A process for reformate benzene reduction, the process including: feeding a light reformate fraction, an olefin feed, and an alkylation catalyst to an alkylation reaction zone; contacting the light reformate fraction and the olefin feed in the presence of the alkylation catalyst in the alkylation reaction zone to convert at least a portion of the benzene and the olefin to a monoalkylate; recovering a catalyst fraction from an alkylation reaction zone effluent; and recovering a light reformate product having a reduced benzene content.
    Type: Grant
    Filed: August 20, 2008
    Date of Patent: January 24, 2012
    Assignee: Catalytic Distillation Technologies
    Inventors: Christopher C. Boyer, Lawrence A. Smith, Jr., Arvids Judzis, Jr., John R. Adams
  • Publication number: 20120004484
    Abstract: A new family of crystalline aluminosilicate zeolites has been synthesized designated UZM-7. These zeolites are represented by the empirical formula. Mmn+Rrp+Al(1-x)ExSiyOz where M is an alkali, alkaline earth, or rare earth metal such as lithium, potassium and barium, R is an organoammonium cation such as the choline or the diethyldimethylammonium cation and E is a framework element such as gallium. These zeolites are characterized by unique x-ray diffraction patterns and compositions and have catalytic properties for carrying out various hydrocarbon conversion processes.
    Type: Application
    Filed: June 29, 2011
    Publication date: January 5, 2012
    Applicant: UOP LLC
    Inventors: Gregory J. Lewis, Mark A. Miller, Lisa M. Knight
  • Publication number: 20110306813
    Abstract: Methods of forming ethylbenzene are described herein. In one embodiment, the method includes contacting dilute ethylene with benzene in the presence of an alkylation catalyst to form ethylbenzene, wherein such contact occurs in a reaction zone containing a gaseous phase and recovering ethylbenzene from the reaction zone.
    Type: Application
    Filed: July 7, 2011
    Publication date: December 15, 2011
    Applicant: Fina Technology, Inc.
    Inventor: James R. Butler
  • 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: 20110201861
    Abstract: The present invention relates to a process for making a crystalline metallosilicate composition and comprising crystallites having an inner part (the core) and an outer part (the outer layer or shell) such that: the ratio Si/Metal is higher in the outer part than in the inner part, the crystallites have a continuous distribution of metal and silicon over the crystalline cross-section, said process comprising: a) providing an aqueous medium comprising OH? anions and a metal source, b) providing an aqueous medium comprising an inorganic source of silicon and optionally a templating agent, c) optionally providing a non aqueous liquid medium comprising optionally an organic source of silica, d) mixing the medium a), b) and the optional c) at conditions effective to partly crystallize the desired metallosilicate, e) cooling down the reaction mixture a)+b)+c) to about room temperature, f) decreasing the pH of the reaction mixture by at least 0.1 preferably by 0.3 to 4, more preferably by 0.
    Type: Application
    Filed: February 24, 2009
    Publication date: August 18, 2011
    Applicant: TOTAL PETROCHEMICALS RESEARCH FELUY
    Inventors: Metin Bulut, Pierre Jacobs, Delphine Minoux, Nikolai Nesterenko, Jean-Pierre Dath, Sander Van Donk
  • Publication number: 20110178353
    Abstract: The present invention provides an improved process for conversion of feedstock comprising an alkylatable aromatic compound and an alkylating agent to desired alkylaromatic conversion product under at least partial liquid phase conversion conditions in the presence of specific catalyst comprising a porous crystalline material, e.g., a crystalline aluminosilicate, and binder in the ratio of crystal/binder of from about 20/80 to about 60/40. The porous crystalline material of the catalyst may comprise a crystalline molecular sieve having the structure of Beta, an MCM-22 family material, e.g., MCM-49, or a mixture thereof.
    Type: Application
    Filed: March 31, 2011
    Publication date: July 21, 2011
    Inventors: Michael C. Clark, Frederick Y. Lo, Christine N. Elia, Matthew J. Vincent
  • Publication number: 20110178352
    Abstract: Disclosed are ethylbenzene processes in which a series-arranged or combined vapor phase alkylation/transalkylation reaction zone is retrofitted to have a vapor phase alkylation reactor and a liquid phase transalkylation reactor, and in which a parallel-arranged vapor phase alkylation reactor and vapor phase transalkylation reactor is retrofitted to have a vapor phase alkylation reactor and liquid phase transalkylation reactor, wherein the xylenes content of the ethylbenzene product is less than 700 wppm.
    Type: Application
    Filed: March 31, 2011
    Publication date: July 21, 2011
    Inventors: Michael C. Clark, Vijay Nanda, Carlos N. Lopez, Brian Maerz, Maruti Bhandarkar
  • Publication number: 20110178354
    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: Application
    Filed: January 19, 2010
    Publication date: July 21, 2011
    Inventors: Antoine Negiz, Edwin Paul Boldingh, Gregory J. Gajda, Dean E. Rende, James E. Rekoske, David E. Mackowiak, Paul Barger, Paula L. Bogdan
  • Publication number: 20110178351
    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: Application
    Filed: February 14, 2011
    Publication date: July 21, 2011
    Inventors: Wieslaw J. Roth, Jane C. Cheng, Mohan Kalyanaraman, Michael C. Kerby, Terry E. Helton
  • Publication number: 20110178342
    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: Application
    Filed: September 23, 2009
    Publication date: July 21, 2011
    Applicant: BADGER LICENSING LLC
    Inventors: Shyh-Yuan Henry Hwang, Dana E. Johnson, Joseph C. Peters, Chung-Ming Chi, Kevin J. Fallon, Francis A. Demers
  • Publication number: 20110130608
    Abstract: The present invention is a process for the alkylation of an aromatic substrate comprising: (a) providing an alkylation reaction zone containing an alkylation catalyst; (b) introducing a feedstock comprising an aromatic substrate and an alkylating agent into the inlet of said alkylation reaction zone and into contact with said alkylation catalyst; (c) operating said alkylation reaction zone at temperature and pressure conditions to cause alkylation of said aromatic substrate in the presence of said alkylation catalyst to produce an alkylation product comprising a mixture of said aromatic substrate and monoalkylated and polyalkylated aromatic components; (d) withdrawing the alkylation product from said alkylation reaction zone; wherein the nitrogen containing compounds impurities in the aromatic substrate or in the alkylating agent or both in the aromatic substrate and in the alkylating agent are monitored in a range 15 wppb-35 wppm by dry colorimetry.
    Type: Application
    Filed: April 3, 2009
    Publication date: June 2, 2011
    Applicant: TOTAL PETROCHEMICALS FRANCE
    Inventor: Jean-Bernard Cary
  • Patent number: 7939693
    Abstract: A process for producing sec-butylbenzene comprises feeding reactants comprising benzene and a C4 olefin to a distillation column reactor having a first reaction zone containing an alkylation catalyst and a second distillation zone, which is located below said first reaction zone and which is substantially free of alkylation catalyst, wherein the ratio of the number of distillation stages in said first reaction zone to the number of distillation stages in said second distillation zone is less than 1:1. Concurrently in the distillation reactor, the reactants are contacted with the alkylation catalyst in the first reaction zone under conditions such that the C4 olefin reacts with the benzene to produce sec-butylbenzene and the sec-butylbenzene is fractioned from the unreacted C4 olefin. The sec-butylbenzene thereby passes as a liquid phase stream from the first reaction zone to the second distillation zone and the liquid phase steam is withdrawn from the distillation column reactor as bottoms.
    Type: Grant
    Filed: July 11, 2008
    Date of Patent: May 10, 2011
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Jane C. Cheng, Jihad M. Dakka, Travis A. Reine, Jon E. Stanat
  • Publication number: 20110092756
    Abstract: In a process for the production of para-xylene, an aromatic feedstock comprising toluene and/or benzene is reacted with methanol under alkylation conditions in a reactor in the presence of a fluidized bed of solid catalyst particles to produce a vapor phase effluent comprising para-xylene, water, unreacted toluene and/or benzene and solid catalyst fines. The vapor phase effluent is contacted with a liquid hydrocarbon quench stream under conditions to condense a minor portion of the vapor phase effluent and produce a condensate which contains at least some of the catalyst fines and which is substantially free of an aqueous phase. The condensate containing said catalyst fines is then separated from the remainder of the vapor phase effluent.
    Type: Application
    Filed: October 6, 2010
    Publication date: April 21, 2011
    Inventors: James R. Lattner, Mark P. Hagemeister, Christopher Gordon Smalley, Jon Edmond Randolph Stanat, Timothy Paul Bender, Masaaki Sugita, Rathna P. Davuluri, Lu Han
  • Patent number: 7910778
    Abstract: In a process for producing cyclohexylbenzene, benzene and hydrogen are contacted with a catalyst under hydroalkylation conditions to produce an effluent containing cyclohexylbenzene. The catalyst comprises a composite of a molecular sieve, an inorganic oxide different from said molecular sieve and at least one hydrogenation metal, wherein at least 50 wt % of said hydrogenation metal is supported on the inorganic oxide.
    Type: Grant
    Filed: July 11, 2008
    Date of Patent: March 22, 2011
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Tan-Jen Chen, John Scott Buchanan, Jane Chi-ya Cheng, Terry E. Helton
  • Patent number: 7910779
    Abstract: In a process for producing cyclohexylbenzene, benzene and hydrogen are fed to at least one reaction zone. The benzene and hydrogen are then contacted in the at least one reaction zone under hydroalkylation conditions with a catalyst system comprising a 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 at least one hydrogenation metal to produce an effluent containing cyclohexylbenzene. The catalyst system has an acid-to-metal molar ratio of from about 75 to about 750.
    Type: Grant
    Filed: October 14, 2010
    Date of Patent: March 22, 2011
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Tan-Jen Chen, Jane C. Cheng, Terry E. Helton, John Scott Buchanan
  • Patent number: 7906685
    Abstract: In a process for producing cyclohexylbenzene, benzene and hydrogen are fed to at least one reaction zone. The benzene and hydrogen are then contacted in the at least one reaction zone under hydroalkylation conditions with a catalyst system comprising a 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 at least one hydrogenation metal to produce an effluent containing cyclohexylbenzene. The ratio of the total number of moles of hydrogen fed to said at least one reaction zone to the number of moles of benzene fed to said at least one reaction zone is between 0.4 and 0.9:1.
    Type: Grant
    Filed: August 12, 2008
    Date of Patent: March 15, 2011
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Tan-Jen Chen, Francisco M. Benitez, Jane C. Cheng, Jon E. Stanat, John Scott Buchanan
  • Patent number: 7902414
    Abstract: A catalytic process for the selective production of para-xylene comprises the step of reacting an aromatic hydrocarbon selected from the group consisting of toluene, benzene and mixtures thereof with a feed comprising carbon monoxide and hydrogen in the presence of a selectivated catalyst. The process includes a catalyst selectivation phase and a para-xylene production phase. In the catalyst selectivation phase, the aromatic hydrocarbon and the feed are contacted with the catalyst under a first set of conditions effective to increase the para-selectivity of said catalyst. In the para-xylene production phase, the aromatic hydrocarbon and said feed are contacted with the catalyst under a second set of conditions different from the first set of conditions effective to selectively produce para-xylene.
    Type: Grant
    Filed: October 3, 2007
    Date of Patent: March 8, 2011
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: John D. Y. Ou, Zongxuan Hong, Songsheng Tan, Timothy E. McMinn