Using Metal, Metal Oxide, Or Hydroxide Catalyst Patents (Class 585/467)
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Patent number: 6063976Abstract: The present invention provides a method comprising (a) contacting a first reaction mixture comprising an aromatic and a dilute stream comprising ethylene and propylene with a large pore microporous solid acid catalyst, preferably a large pore zeolite catalyst, which is effective to promote alkylation of the aromatic under first conditions effective to maintain a liquid phase comprising the aromatic and effective to cause the propylene to alkylate said aromatic but substantially ineffective to cause the ethylene to alkylate said aromatic, forming propylated aromatic and a second dilute stream comprising ethylene but substantially depleted of propylene, and (b) recovering the propylated aromatic.Type: GrantFiled: August 18, 1998Date of Patent: May 16, 2000Assignee: Exxon Chemical Patent Inc.Inventors: Dan E. Hendriksen, James R. Lattner, Jos P. Wristers
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Patent number: 6060632Abstract: A process for producing ethylated benzene by a reaction of benzene with ethylene in the presence of a catalyst containing a zeolite .beta. by using a fixed-bed ascending-flow type reactor, which comprisesa) carrying out the reaction under conditions under which ethylene bubbles are present at the inlet of a catalyst layer when ethylene is fed upward from under the catalyst layer,b) recovering reaction products as a liquid from the upper part of the reactor and at the same time taking out a distillate composed mainly of unreacted benzene therefrom as vapor, andc) adjusting the temperature of the catalyst layer at its inlet to a temperature at least 50.degree. C. lower than the maximum attained temperature of the catalyst layer.Type: GrantFiled: January 14, 1999Date of Patent: May 9, 2000Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Yoshikazu Takamatsu, Hiroshi Ishida, Yoshihito Itani
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Patent number: 6057485Abstract: Ethylbenzene is produced by alkylation over a split load of monoclinic silicalite alkylation catalysts having different silica/alumina ratios. A feedstock containing benzene and ethylene is applied to a multi-stage alkylation reaction zone having a plurality of series-connected catalyst beds. At least one catalyst bed contains a first monoclinic silicalite catalyst having a silica/alumina ratio of at least 275. At least one other catalyst bed contains a second monoclinic silicalite catalyst having a silica/alumina ratio of less than about 275. The alkylation reaction zone is operated at temperature and pressure conditions in which the benzene is in a gaseous phase to cause gas-phase alkylation of the aromatic substrate in the presence of the monoclinic silicalite catalysts to produce an alkylation product. The alkylation product is then withdrawn from the reaction zone for separation and recovery.Type: GrantFiled: November 17, 1998Date of Patent: May 2, 2000Assignee: Fina Technology, Inc.Inventors: James T. Merrill, James R. Butler, Ashim Kumar Ghosh
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Patent number: 6049018Abstract: This invention relates to a new synthetic porous crystalline material, designated MCM-68, a method and novel polycyclic organic cation for its preparation and its use in catalytic conversion of organic compounds. The new crystalline material exhibits a distinctive X-ray diffraction pattern and has a unique crystal structure which contains at least one channel system, in which each channel is defined by a 12-membered ring of tetrahedrally coordinated atoms, and at least two further, independent channel systems, in each of which each channel is defined by a 10-membered ring of tetrahedrally coordinated atoms, wherein the number of unique 10-membered ring channels is twice the number of 12-membered ring channels.Type: GrantFiled: January 21, 1999Date of Patent: April 11, 2000Assignee: Mobil CorporationInventors: David C. Calabro, Jane C. Cheng, Robert A. Crane, Jr., Charles T. Kresge, Sandeep S. Dhingra, Michael A. Steckel, David L. Stern, Simon C. Weston
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Patent number: 6043402Abstract: Reduction of the amount of 1,1-diphenylethane formed in the production of ethylbenzene by alkylation of benzene with ethylene and by transalkylation of benzene with polyethylbenzenes can be effected by reacting at a low concentration of ethylene. This invention allows operation at a low molar ratio of phenyl groups per ethyl group and leads to a product containing less than 1.0 wt-% 1,1-diphenylethane relative to ethylbenzene. This invention is applicable to processes for the production of a wide variety of other commercially important alkylated aromatics.Type: GrantFiled: June 3, 1998Date of Patent: March 28, 2000Assignee: UOP LLCInventor: Gregory J. Gajda
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Patent number: 6037513Abstract: There is described a process and a catalyst for the hydroalkylation of an aromatic hydrocarbon, particularly benzene, wherein the catalyst comprises a first metal having hydrogenation activity and a crystalline inorganic oxide material having a X-ray diffraction pattern including the following d-spacing maxima 12.4.+-.0.25, 6.9.+-.0.15, 3.57.+-.0.07 and 3.42.+-.0.07.Type: GrantFiled: July 9, 1998Date of Patent: March 14, 2000Assignee: Mobil Oil CorporationInventors: Clarence D. Chang, Jane C. Cheng, Terry E. Helton, Michael A. Steckel, Scott A. Stevenson
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Patent number: 6037512Abstract: The invention concerns the use of a catalyst for the dismutation of alkylaromatic hydrocarbons, and preferably for the dismutation of toluene to produce benzene and xylenes, and/or for the transalkylation of alkylaromatic hydrocarbons, preferably for the transalkylation of toluene and trimethylbenzenes to produce xylenes. The catalyst comprises a zeolite with structure type mazzite, comprising silicon and at least one element T selected from the group formed by gallium and aluminium, preferably aluminium, in which the number of extra-network T atoms is less than 15% of the global number of T atoms present in the zeolite, in which the global Si/T aromatic ratio is in the range 5 to 100, and its preparation by extraction of element T from the zeolitic framework, preferably by dealuminization of the framework by means of at least one hydrothermal treatment followed by at least one acid attack.Type: GrantFiled: November 5, 1998Date of Patent: March 14, 2000Assignee: Institut Francois du PetroleInventors: Eric Benazzi, Fabio Alario
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Patent number: 6034291Abstract: A catalytic composition is described for the alkylation and/or transalkylation of aromatic hydrocarbons consisting of beta zeolite, as such or modified by the isomorphous substitution of aluminum with boron, iron or gallium or by the introduction of alkaline and/or earth alkaline metals following an ion-exchange process, and an inorganic ligand, wherein the extrazeolite porosity, i.e. the porosity obtained by adding the mesoporosity and macroporosity fractions present in the catalytic composition itself, is such that a fraction of at least 25% is composed of pores with a radius higher than 100 .ANG., said composition being characterized by a total volume of extrazeolitic pores greater than or equal to 0.80 ml/g.Type: GrantFiled: December 10, 1997Date of Patent: March 7, 2000Assignee: Enichem S.p.A.Inventors: Gianni Girotti, Oscar Cappellazzo, Elena Bencini, Giannino Pazzuconi, Carlo Perego
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Patent number: 6027707Abstract: The invention concerns NU-88 zeolite, characterized by:i) a chemical composition with the following formula, expressed in terms of the mole ratios of the oxides for the anhydrous state:100 XO.sub.2, mY.sub.2 O.sub.3, pR.sub.2/n Owherem is 10 or less;p is 20 or less;R represents one or more cations with valency n;X represents silicon and/or germanium;Y represents one or more of the following elements: aluminium, iron, gallium, boron, titanium, vanadium, zirconium, molybdenum, arsenic, antimony, chromium and manganese; andii) an X ray diffraction diagram, in its as synthesized state, which comprises the results shown in Table 1 of the description.The invention also concerns the preparation of the zeolite, any catalyst containing the zeolite and any catalytic process using such a catalyst.Type: GrantFiled: August 22, 1997Date of Patent: February 22, 2000Assignee: Institut Francais du PetroleInventors: John Leonello Casci, Sheena Maberly, Eric Benazzi, Loic Rouleau, Roland Patrick Henney
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Patent number: 6018086Abstract: The present invention relates to a process of preparing dialkylnaphthylenes and polyalkylenenaphthyleneates.Type: GrantFiled: October 10, 1997Date of Patent: January 25, 2000Assignees: Kabushiki Kaisha Kobe Seiko Sho, Mobil Oil CorporationInventors: Masahiro Motoyuki, Koji Yamamoto, Ajit Vishwanath Sapre, John Paul Mc Williams, Susan Patricia Donnelly
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Patent number: 6013848Abstract: A process for the conversion of heavy bottoms from aromatic alkylation known as "flux oil" and containing heavier polyalkylaromatic compounds, in which the heavier polyalkylates are fed along with aromatic to a reactor containing an acidic zeolite catalyst for conversion to light mono-, and poly alkylaromatic compounds. The light polyalkylates may then be transalkylated with benzene to form additional monoalkylate.Type: GrantFiled: July 8, 1997Date of Patent: January 11, 2000Assignee: Catalytic Distillation TechnologiesInventors: Jamin Chen, Chuen Y. Yeh
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Patent number: 6010617Abstract: A process for reducing the mutagenicity of a coal-tar-based product containing polynuclear aromatic compounds. The process includes the step of contacting the coal-tar-based product in the presence of an alkylating agent with an acid catalyst under alkylation conditions sufficient to reduce the mutagenicity of the polynuclear aromatic containing coal-tar-based material to a level less than the initial mutagenicity index value. Also provided are non-carcinogenic coal-tar-derived products.Type: GrantFiled: June 6, 1994Date of Patent: January 4, 2000Assignee: Mobil Oil CorporationInventors: Carl R. Mackerer, Timothy A. Roy, Gary R. Blackburn
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Patent number: 6011190Abstract: 2,6-Dialkylnaphthalene is prepared from a feedstock comprising naphthalene and an alkylating agent, by a process comprising the steps:(I) transalkylating isomers of dialkylnaphthalene and naphthalene to produce monoalkylnaphthalene and isomers of dialkylnaphthalene;(II) separating the product obtained in step (I) into naphthalene, monoalkylnaphthalene, dialkylnaphthalene and other components;(III) alkylating the monoalkylnaphthalene fraction from step (II) with an alkylating agent to produce dialkylnaphthalene; and(IV) separating 2,6-dialkylnaphthalene from the dialkylnaphthalene fraction in step (II),wherein at least step (I) or step (III) is conducted in the presence of a catalyst having a composition comprising a synthetic zeolite having an X-ray diffraction pattern with an interplanar d-spacing (.ANG.)______________________________________ 12.36 .+-. 0.4 11.03 .+-. 0.2 8.83 .+-. 0.14 6.18 .+-. 0.12 6.00 .+-. 0.10 4.06 .+-. 0.07 3.91 .+-. 0.07 3.42 .+-. 0.06.Type: GrantFiled: July 2, 1997Date of Patent: January 4, 2000Assignees: Kabushiki Kaisha Kobe Seiko Sho, Mobil Oil CorporationInventors: Masahiro Motoyuki, Koji Yamamoto, Ajit Vishwanath Sapre, John Paul McWilliams
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Patent number: 6008422Abstract: A process for producing alkylaromatics using a multibed alkylation reaction zone is disclosed. The alkylation reaction zone effluent is divided into three portions, the first being recirculated to the inlet of the reaction zone, the second being cooled and recirculated to one or more other beds in the reaction zone, and the third being passed to a product recovery zone where the alkylaromatic is recovered. This process insures that all of the catalyst beds operate in an optimum temperature range. This in turn insures that byproduct formation is minimized and catalyst life is maximized. Ethylbenzene and cumene may be produced by this process.Type: GrantFiled: July 7, 1998Date of Patent: December 28, 1999Assignee: UOP LLCInventors: Russell C. Schulz, Perry K. Ho
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Patent number: 6005152Abstract: A process is described for preparing monoalkylated aromatic compounds which comprises subjecting an aromatic hydrocarbon to alkylation with an olefin containing from 2 to 4 carbon atoms, or to transalkylation with a polyalkylaromatic hydrocarbon, in the presence of ERS-10 zeolite.Type: GrantFiled: April 5, 1999Date of Patent: December 21, 1999Assignees: Enichem S.p.A., EniTechnologie S.p.A.Inventors: Stefano Amarilli, Luciano Carluccio, Carlo Perego, Giuseppe Bellussi
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Patent number: 6002057Abstract: A process for the alkylation of an aromatic compound with C.sub.2 to C.sub.4 olefin alkylating agent. A process to produce ethylbenzene by reaction of ethylene in stoichiometric or excess amount with benzene in the presence of a zeolite beta catalyst. This process is especially suitable for reaction of dilute ethylene with dilute benzene in a catalytic distillation column.Type: GrantFiled: September 5, 1997Date of Patent: December 14, 1999Assignee: Exxon Chemical Patents Inc.Inventors: Dan Eldon Hendriksen, James Richardson Lattner, Mechilium Johannes Gerardus Janssen
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Patent number: 5997730Abstract: A novel catalyst for the conversion of hydrocarbons comprising a material containing an acid treated zeolite, a boron component and a zinc component wherein the material is treated with a silylating agent. A method of making such novel catalyst and the use of the novel catalyst for converting paraffin hydrocarbons with a low rate of coke formation during such conversion are disclosed.Type: GrantFiled: February 2, 1998Date of Patent: December 7, 1999Assignee: Phillips Petroleum CompanyInventors: Charles A. Drake, An-hsiang Wu
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Patent number: 5998687Abstract: Benzene is catalytically alkylated with ethylene in a process which comprises at least two catalyst zones. Benzene and ethylene contact a catalyst comprising zeolite beta in a first catalyst zone. Ethylene and the effluent from the first catalyst zone contact a catalyst comprising zeolite Y to produce an alkylate containing ethylbenzene.Type: GrantFiled: July 29, 1998Date of Patent: December 7, 1999Assignee: UOP LLCInventors: Guy B. Woodle, Alan E. Cepla
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Patent number: 5998684Abstract: A separation arrangement for a cumene process that operates with a relatively wet feed to an alkylation zone and relatively dry feed to a transalkylation zone reduces utilities and capital expenses for the separation and recycle of distinct wet and dry components by using an arrangement that first separates effluent from the trans alkylation and alkylation reaction zone in a benzene column before performing light ends and drying in a downstream depropanizer column. The arrangement uses a portion of the net overhead stream from the benzene column as a wet recycle stream for return to the alkylation reaction zone and sends another portion of the benzene net overhead to the depropanizer to supply a dry benzene recycle for the trans alkylation reaction zone.Type: GrantFiled: November 10, 1997Date of Patent: December 7, 1999Assignee: UOP LLCInventors: Perry K. Ho, Russell C. Schulz
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Patent number: 5994603Abstract: A process is provided for the production of paraxylene by the methylation of toluene in the presence of a zeolite bound zeolite catalyst. The catalyst comprises first zeolite crystals which are bound together by second zeolite crystals. When used to methylate toluene to para-xylene, the zeolite bound zeolite catalyst has a para-xylene selectivity greater than thermodynamic equilibrium. This selectivity can be enhanced by selectivating the catalyst.Type: GrantFiled: May 29, 1997Date of Patent: November 30, 1999Assignee: Exxon Chemical Patents Inc.Inventors: Gary D. Mohr, Robert Scott Smith
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Patent number: 5986155Abstract: Treating low reactivity alkylating agents in the vapor phase with catalysts converts the low reactivity alkylating agents to high reactivity alkylating agents. The alkylating agents are useful in synthesis of alkyl aromatics with Lewis acid catalysts.Type: GrantFiled: July 10, 1996Date of Patent: November 16, 1999Assignee: The Lubrizol CorporationInventors: James D. Burrington, Stuart L. Bartley, Douglas C. Rhubright, Paul A. Lewis, Marvin B. DeTar, Alicia L. Kliever, Frank A. Del Greco, Lawrence T. Novak
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Patent number: 5977424Abstract: A catalyst is disclosed which comprises a clay belonging to the family of smectites, containing multi-metal pillars, together with a process which uses such a catalyst for the alkylation of aromatic hydrocarbons by means of long chain linear olefins. The resulting alkyl-aromatic compounds are useful for preparing biodegradable synthetic detergents.Type: GrantFiled: April 23, 1998Date of Patent: November 2, 1999Assignee: Enichem Augusta S.p.A.Inventors: Giovanni Colombo, Stefano Amarilli, Imre Kiricsi, Carlo Perego
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Patent number: 5977426Abstract: A method for recovering crystalline 2,6-dimethylnaphthalene comprising crystallizing in a scraped-wall crystallizer apparatus at crystallization temperature T, a mixture of low melting components, LM, having melting points of 70.degree. F. and below, and high melting components (HM), including 2,6-dimethylnaphthalene, having melting points above 70.degree. F, such that: ##EQU1## where HM is the total weight percent of high melting components, including 2,6-dimethylnaphthalene, in the mixture, and LM is the total weight percent of low melting components in the mixture, and where T is the temperature of the crystallization in degrees Fahrenheit, and where A is at least 1.0.Type: GrantFiled: October 20, 1997Date of Patent: November 2, 1999Assignee: BP Amoco CorporationInventors: Thomas G. Smith, John M. Weis, Yenamandra Viswanath
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Patent number: 5972203Abstract: There is provided catalysts and conversion processes for converting hydrocarbons using the catalysts. The catalysts comprises a first alumino-phosphospho-molecular sieves and a binder comprising a second alumino-phopho-molecular sieves. Exemplary conversion processes include the conversion of oxygenates to olefins, dewaxing, reforming, dealkylation, dehydrogenation, transalkylation, alkylation, and isomerization.Type: GrantFiled: May 29, 1997Date of Patent: October 26, 1999Assignee: Exxon Chemical Patents Inc.Inventors: Robert Scott Smith, Gary D. Mohr
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Patent number: 5968343Abstract: A catalyst composition and a process for converting a hydrocarbon stream such as, for example, gasoline to olefins and C.sub.6 to C.sub.8 aromatic hydrocarbons such as toluene and xylenes are disclosed. The catalyst composition comprises a zeolite, a binder, and boron wherein the weight of boron is in the range of from about 0.01 to about 10 weight %. The process comprises contacting a hydrocarbon stream with the catalyst composition under a condition sufficient to effect the conversion of a hydrocarbon to an olefin and a C.sub.6 to C.sub.8 aromatic hydrocarbon. Also disclosed is a process for producing the catalyst composition which comprises: (1) combining a zeolite with a coke-reducing amount of a binder under a condition effective to produce a zeolite-binder mixture; (2) contacting said zeolite-binder mixture with coke-reducing amount of a boron compound under a condition effective to produce a boron-incorporated or -impregnated zeolite; and (3) calcining the boron-incorporated or -impregnated zeolite.Type: GrantFiled: May 5, 1997Date of Patent: October 19, 1999Assignee: Phillips Petroleum CompanyInventors: Charles A. Drake, An-hsiang Wu
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Patent number: 5965104Abstract: The present invention relates to new crystalline zeolite SSZ-43 prepared using a substituted piperidinium or decahydroquinolinium cation templating agent.Type: GrantFiled: December 17, 1997Date of Patent: October 12, 1999Assignee: Chevron U.S.A. Inc.Inventors: Gregory S. Lee, Yumi Nakagawa, Richard Norman Reynolds
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Patent number: 5962760Abstract: A process for the alkylation of aromatic compounds with an olefin or alkyl halide having from 1 to 24 carbon atoms utilizes a novel catalyst comprising: a) a refractory inorganic oxide, b) the reaction product of a first metal halide and bound surface hydroxyl groups of the refractory inorganic oxide, c) a second metal cation, and d) optionally a zerovalent third metal. The refractory inorganic oxide is selected from the group consisting of alumina, titania, zirconia, chromia, silica, boria, silica-alumina, and combinations thereof and the first metal halide is a fluoride, chloride, or bromide of aluminum, gallium, zirconium, or boron. The second metal cation is selected from the group consisting of: monovalent metal cations in an amount from 0.0026 up to about 0.20 gram atoms per 100 grams refractory inorganic oxide for lithium, potassium, cerium, rubidium, silver, and copper, and from 0.012 to about 0.20 gram atoms for sodium; and alkaline earth metal cations in an amount from about 0.0013 up to about 0.Type: GrantFiled: August 4, 1997Date of Patent: October 5, 1999Assignee: UOP LLCInventors: Joseph A. Kocal, Anil R. Oroskar
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Patent number: 5962759Abstract: Reduction of the amount of 1,1-diphenylethane and heavier polyalkylated benzenes produced in the formation of ethylbenzene by alkylation of benzene with ethylene can be effected by treating a non-templated zeolite beta at thermal oxidation conditions. The precursor zeolite beta contains at least 0.5% carbon which represents a combination of coke and high molecular organic compounds which are not removed by an extended benzene wash at about 200-250.degree. C. The improvement leads to a product containing less than 0.3 weight percent 1,1-diphenylethane relative to ethylbenzene.Type: GrantFiled: April 8, 1997Date of Patent: October 5, 1999Assignee: UOP LLCInventor: Gregory J. Gajda
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Patent number: 5959168Abstract: A zeolite-based ethylbenzene process which is suitable for retrofitting aluminum chloride-based ethylbenzene plants. The process involves alkylating benzene with ethylene in an alkylation zone in the presence of zeolite beta or Y or an MCM zeolite so as to produce an alkylation product mixture containing benzene, ethylbenzene, and polyethylbenzenes which can be separated in the aromatics recovery (distillation) stage of an aluminum chloride-based plant. The polyethylbenzenes are subsequently contacted with benzene in a transalkylation zone using zeolite beta or mordenite or Y so as to produce a transalkylation product mixture which is also separable in the aromatics recovery stage of an aluminum chloride-based plant.Type: GrantFiled: February 17, 1998Date of Patent: September 28, 1999Assignee: The Dow Chemical CompanyInventors: Matheus J. M. van der Aalst, Mohammed S. U. Samson, Garmt R. Meima, Michael Q. de Steenwinkel
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Patent number: 5955642Abstract: An alkylation/transalkylation process involving vapor phase alkylation of a benzene feedstock in a multi-stage alkylation zone having a plurality of series connected catalyst beds containing a pentasil aromatic alkylation catalyst, such as silicalite, coupled with intermediate separation and recirculation steps and liquid phase transalkylation over a transalkylation catalyst comprising a molecular sieve having a pore size greater than the pore size of the silicalite. The benzene containing feedstock is supplied to the multi-stage alkylation reaction zone along with a C.sub.2 -C.sub.4 alkylating agent operated under temperature and pressure conditions to maintain the benzene in the gas phase. Alkylated product is recovered from the alkylation zone and supplied to a benzene recovery zone for the separation of the benzene from the alkylation product. Benzene from the benzene recovery zone is recycled to the reaction zone.Type: GrantFiled: October 30, 1996Date of Patent: September 21, 1999Assignee: Fina Technology, Inc.Inventors: James T. Merrill, James R. Butler
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Patent number: 5955641Abstract: The method of the invention includes making dimethyinaphthalenes by first contacting, in an alkylation zone, at alkylation conditions, a toluene-containing stream with a pentene-containing stream in the presence of an acid alkylation catalyst. At least a portion of the toluene and pentenes react to form pentyltoluenes. At least a portion of the pentyltoluenes is then contacting in a reforming zone with reforming catalyst, at reforming conditions. At least a portion of the pentyltoluenes is converted to dimethylnaphthalenes.Type: GrantFiled: May 28, 1998Date of Patent: September 21, 1999Assignee: Chevron Chemical Company LLCInventors: Cong-Yan Chen, William L. Schinski, Dennis J. O'Rear, Thomas V. Harris
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Patent number: 5939597Abstract: Para-xylene is produced by toluene methylation by charging toluene and a methylating agent to a fluidized bed of catalyst at a rate sufficient to maintain the fluidized bed in a turbulent sub-transport flow regime, reacting the toluene with the methylating agent, and recovering para-xylene from the fluidized bed. The fluidizable catalyst is a microporous material having a Constraint Index of about 1 to about 12. The relative concentration of the catalyst particles having a major dimension of less than 40 microns is controlled at between about 5 and 35 weight percent. The catalyst particles have an apparent particle density of about 0.9 to 1.6 grams per cubic centimeter, a size range of about 1 to 150 microns, and average particle size of about 20 to 100 microns.Type: GrantFiled: October 21, 1997Date of Patent: August 17, 1999Assignee: Mobil Oil CorporationInventors: Ralph M. Dessau, David H. Olson, Robert A. Ware, Sadi Mizrahi
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Patent number: 5932777Abstract: A hydrocarbon conversion process comprises: (1) contacting a hydrocarbon feed such as, for example, gasoline, with a catalyst under a sufficient condition to effect the conversion of the hydrocarbon to a product stream comprising aromatic hydrocarbons and olefins; (2) separating the product stream into a lights fraction comprising primarily hydrocarbons less than 6 carbon atoms per molecule, a middle fraction comprising C.sub.6 -C.sub.8 aromatic hydrocarbons and non-aromatic hydrocarbons, and a C.sub.9 + fraction comprising aromatic compounds; (3) separating the C.sub.6 -C.sub.8 aromatic hydrocarbons from the middle fraction; and (4) separating hydrocarbons containing 5 or more carbons per molecule (C.sub.5 + hydrocarbons) from the lights fraction. The C.sub.5 + hydrocarbons can be combined with the hydrocarbon feed. The non-aromatic hydrocarbons can also be converted to olefins by a thermal cracking process. Furthermore, the middle fraction can also be obtained by reforming naphtha.Type: GrantFiled: July 23, 1997Date of Patent: August 3, 1999Assignee: Phillips Petroleum CompanyInventors: Edward L. Sughrue, II, Charles A. Drake, Scott D. Love
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Patent number: 5922922Abstract: An alkylated aromatic hydrocarbon is produced having the following properties: (a) less than 40 wt. % of the alkylated aromatic hydrocarbon is 2-aryl; and (b) at least 20 wt. % of the alkylated aromatic hydrocarbon is a monoalkylate. That alkylated aromatic hydrocarbon is produced by isomerizing a normal alpha-olefin having from 20 to 28 carbon atoms in the presence of a first acidic catalyst to produce a partially-branched, isomerized olefin, then either benzene or toluene is alkylated with the partially-branched, isomerized olefin in the presence of a second solid, acidic catalyst. The first acidic catalyst can be a molecular sieve with a one-dimensional pore system. The second acidic catalyst can be a zeolite Y having a silica to alumina ratio of at least 40:1.Type: GrantFiled: July 17, 1997Date of Patent: July 13, 1999Assignee: Chevron Chemical CompanyInventors: Thomas V. Harris, Curt B. Campbell, Mohammed M. Habib
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Patent number: 5910299Abstract: A porous, crystalline material, designated ERS-10 zeolite, having in its calcined and anhydrous form a molecular composition of oxides corresponding to the formula (I):mM.sub.2/n O.zX.sub.2 O.sub.3.YO.sub.2 (1)wherein m, n, M, z, X and Y are as defined herein, the crystalline material having an X-ray diffraction spectrum shown in Table 1 herein.Type: GrantFiled: March 5, 1997Date of Patent: June 8, 1999Assignee: Eniricerche S.p.A.Inventors: Luciano Carluccio, Roberto Millini, Giuseppe Bellussi
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Patent number: 5907073Abstract: A process for the alkylation of an aromatic substrate over a molecular sieve zeolite catalyst involving supplying an aromatic substrate to a reaction zone containing the catalyst. The molecular sieve catalyst is an effective aromatic alkylation catalyst and comprises a modified zeolite beta alkylation catalyst having an intergrowth of a ZSM-12 crystalline framework within the crystalline framework of zeolite beta. An alkylating agent is also supplied to the reaction zone which is operated under temperature and pressure conditions effective to cause alkylation of the aromatic substrate by the alkylating agent. An alkylated substrate is recovered from the reaction zone.Type: GrantFiled: February 24, 1998Date of Patent: May 25, 1999Assignee: Fina Technology, Inc.Inventor: Ashim Kumar Ghosh
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Patent number: 5902917Abstract: There is provided a process for producing alkylaromatics, especially ethylbenzene and cumene, wherein a feedstock is first fed to a transalkylation zone and the entire effluent from the transalkylation zone is then cascaded directly into an alkylation zone along with an olefin alkylating agent, especially ethylene or propylene.Type: GrantFiled: November 26, 1997Date of Patent: May 11, 1999Assignee: Mobil Oil CorporationInventors: Nick A. Collins, Dominick N. Mazzone, Chaya R. Venkat
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Patent number: 5900520Abstract: Alkyl aromatic compounds are prepared by alkylating an alkylatable aromatic compound with a paraffin alkylating agent under alkylation reaction conditions in the presence of catalyst comprising synthetic porous crystalline material characterized by an X-ray diffraction pattern including interplanar d-spacings at 12.36.+-.0.4, 11.03.+-.0.2, 8.83.+-.0.14, 6.18.+-.0.12, 6.00.+-.0.10, 4.06.+-.0.07, 3.91.+-.0.07, and 3.42.+-.0.06 Angstroms.Type: GrantFiled: January 23, 1995Date of Patent: May 4, 1999Assignee: Mobil Oil CorporationInventors: Dominick N. Mazzone, David O. Marler, Kathleen M. Keville, Larry A. Green
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Patent number: 5900519Abstract: A catalytic process is described for the selective alkylation of a polycyclic aromatic compound comprising reacting the polycyclic aromatic compound with an alkylating agent in the presence of a catalyst to thereby yield the desired alkyl substituted polycyclic aromatic compound with improved selectivity and improved yield. The process is particularly suitable for the selective dialkylation of polycyclic aromatic compounds in the para-, respectively beta-positions. The catalyst is a protonic form of a mordenite having an atomic Si/Al ratio of at least 5:1, comprising additional metal species in a molar ratio metal (in the metal species)/aluminium of at least 0.10 and having a biphenyl sorption of at least 0.05 g biphenyl per g of catalyst.Type: GrantFiled: October 28, 1996Date of Patent: May 4, 1999Assignee: Solutia Inc.Inventors: Patrick Pierre Bernard Notte, Georges Marie Joseph Luc Poncelet, Marc Joseph Henri Remy, Pierre Fernand Marcel Ghislain Lapdinois, Marina Jeanne Madeleine Van Hoecke
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Patent number: 5900518Abstract: The present invention addresses heat integration in an alkylation/transalkylation process involving alkylation of an aromatic substrate with a C.sub.2 -C.sub.4 alklating agent coupled with separation to recover a monoalkylated aromatic product and liquid phase transalkylation of a polyalkylated product. Aromatic feedstock and a C.sub.2 -C.sub.4 alkylating agent are supplied to an alkylation reaction zone which is operated to produce an alkylated product. The output from the alkylation reaction zone initially travels through an arrangement of heat exchangers. From there, the alkylation effluent passes into the first separation zone which is operated to produce a lower boiling fraction comprising the aromatic substrate, which may be recycled to the alkylation reaction zone, and a higher boiling fraction comprising a mixture of monoalkylated and polyalkylated aromatics.Type: GrantFiled: October 30, 1996Date of Patent: May 4, 1999Assignee: Fina Technology, Inc.Inventors: James T. Merrill, Joseph Honn Tudor
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Patent number: 5880322Abstract: A method for producing diarylalkanes at a high yield using an aromatic hydrocarbon and inexpensive formalin in the presence of an easily usable solid acid catalyst, and in the method, a mixture of an aromatic hydrocarbon and formalin, said mixture containing 1.5 to 12% by weight of water, is reacted at a temperature of 170 to 450.degree. C. under an elevated pressure in the presence of a zeolitic catalyst.Type: GrantFiled: December 11, 1997Date of Patent: March 9, 1999Assignee: Nippen Petrochemicals Company, LimitedInventors: Hideyuki Dohi, Syozo Hayashi
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Patent number: 5880321Abstract: In a process for preparing unsubstituted or substituted 1,1-diphenylethanes by catalytic reaction of benzene and styrene in the presence of a zeolite catalyst, it being possible for benzene and styrene each independently to have 1 to 5 substituents selected from halogen, C.sub.1-10 -alkyl, C.sub.1-10 -alkoxy, C.sub.1-10 -acyl, C.sub.1-10 -acyloxy or cyano, the zeolite catalyst is of the EMT or ZSM-20 type.Type: GrantFiled: March 24, 1998Date of Patent: March 9, 1999Assignee: BASF AktiengesellschaftInventors: Eugen Gehrer, Karsten Eller, Gunther Effler
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Patent number: 5877371Abstract: A solid state insoluble salt catalyst system for the carbocationic polymerization of olefin monomer in the presence of a polar or non-polar reaction medium, which comprises (a) solid state catalyst component comprising at least one salt of a strong acid and a carbocationically active transition metal selected from Groups III A, IV A, V A and VI A of the Periodic Table of Elements, wherein said salt is insoluble in the reaction medium; and (b) cocatalyst component effective for promoting the carbocationic polymerization.Type: GrantFiled: June 25, 1998Date of Patent: March 2, 1999Assignee: Exxon Chemical Patents Inc.Inventors: Frank Joung-Yei Chen, Herve Cheradame, Jon Edmond Stanat, Gerard Rissoan
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Patent number: 5877370Abstract: Reduction of the amount of 1,1-diphenylethane formed in the production of ethylbenzene by alkylation of benzene with ethylene can be effected by alkylating at a low concentration of ethylene. This invention allows operation at a low molar ratio of phenyl groups per ethyl group and leads to a product containing less than 1.0 wt-% 1,1-diphenylethane relative to ethylbenzene. This invention is applicable to processes for the production of a wide variety of other commercially important alkylated aromatics.Type: GrantFiled: June 16, 1997Date of Patent: March 2, 1999Assignee: UOP LLCInventor: Gregory J. Gajda
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Patent number: 5866736Abstract: The benzene content of light reformate is reduced by selectively alkylating the toluene contained therein with olefins by contacting the light reformate with the olefins in a catalyst bed. The catalyst structure in the catalyst bed acts as both a catalyst for the alkylation reaction and as distillation structure thus immediately separating the reaction product from the reaction zone to prevent reverse reactions and increase the overall reaction rate. The alkylated toluene is then used to transalkylate benzene to reduce the amount of benzene in the gasoline.Type: GrantFiled: October 14, 1997Date of Patent: February 2, 1999Assignee: Catalytic Distillation TechnologiesInventor: Jamin Chen
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Patent number: 5866739Abstract: The present invention relates to a catalyst composition, its methods of preparation and its use in aromatic alkylation processes. The composition comprises a heteropoly compound selected from the group consisting of heteropoly salts and heteropolyacid salts deposited in the interior of a porous support selected from the group consisting of silica, titania, and zirconia, wherein said salt of said heteropoly salt and said heteropolyacid salt is selected from the group consisting of ammonium, cesium, potassium, and rubidium salts and mixtures thereof, and wherein said heteropoly salt and said heteropolyacid salt are formed with a heteropolyacid selected from the group consisting of 12-tungstophosphoric, 12-tungstosilicic, 12-molybdophosphoric, and 12-molybdosilicic acid.Type: GrantFiled: July 29, 1997Date of Patent: February 2, 1999Assignee: Exxon Research and Engineering CompanyInventors: Stuart Leon Soled, Jose Augusto da Costa Paes, Antonio Gutierrez, Sabato Miseo, William E. Gates, Kenneth L. Riley
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Patent number: 5856607Abstract: The present invention relates to a process for the production of ethylbenzene from dilute ethylene streams, especially from mixtures of ethane and ethylene where such mixture is the offgas from a refinery operation, such as a fluid catalytic cracking (FCC) operation and wherein the unreacted ethane from the alkylation reactor is dehydrogenated to produce ethylene which is recycled into the original dilute ethylene stream.Type: GrantFiled: May 2, 1997Date of Patent: January 5, 1999Assignee: Amoco CorporationInventor: Dae K. Kim
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Patent number: 5856608Abstract: A catalyst composition and a process for converting a C.sub.9 + aromatic compound such as, for example, 1,2,4-trimethylbenzene to a C.sub.6 to C.sub.8 aromatic hydrocarbon such as a xylene are disclosed. The composition comprises a zeolite, a metal oxide, and optionally a selectivity modifier selected from the group consisting of silicon, sulfur, phosphorus, boron, magnesium, tin, titanium, zirconium, germanium, indium, lanthanum, cesium, oxides thereof and combinations of any two or more thereof. The process comprises contacting a fluid which comprises a C.sub.9 + aromatic compound with the catalyst composition under a condition sufficient to effect the conversion of a C.sub.9 + aromatic compound to a C.sub.6 to C.sub.8 aromatic hydrocarbon.Type: GrantFiled: February 21, 1997Date of Patent: January 5, 1999Assignee: Phillips Petroleum CompanyInventors: An-hsiang Wu, Charles A. Drake
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Patent number: 5856606Abstract: Paraffins or other hydrocarbons are alkylated in a process featuring a reaction zone containing a pool of liquid maintained at its boiling point and containing a suspended solid catalyst, which allows the heat of reaction to vaporize a portion of the liquid phase feed hydrocarbon. The vapor phase withdrawn from the top of the reaction zone is at least partially recycled to the reaction zone either as vapor or liquid. The feed hydrocarbons are introduced to the bottom of the reaction zone as a vapor phase stream, which may contain hydrogen. The catalyst is suspended within the liquid in the reaction zone.Type: GrantFiled: September 27, 1996Date of Patent: January 5, 1999Assignee: UOP LLCInventor: Anil R. Oroskar
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Hydrocarbon conversion process with alkaline earth metal ion exchanged selectivated zeolite catalyst
Patent number: 5849968Abstract: There is provided a zeolite catalyst, which is first selectivated with a siliceous material and then treated with an aqueous solution comprising alkaline earth metal ions under ion exchange conditions.Type: GrantFiled: July 28, 1997Date of Patent: December 15, 1998Assignee: Mobil Oil CorporationInventors: Jeffrey S. Beck, David L. Stern