Using Metal, Metal Oxide, Or Hydroxide Catalyst Patents (Class 585/467)
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Patent number: 6479721Abstract: A process for the alkylation of aromatics with olefins using a solid catalyst is disclosed, wherein the olefin ratio and/or the maximum olefin concentration in the alkylation catalyst, bed is maintained less than an upper limit. Such operation can decrease the catalyst deactivation rate and the formation of diphenylalkanes. This invention is applicable to processes for the production of a wide variety of commercially important alkylated aromatics, including ethylbenzene and cumene.Type: GrantFiled: March 28, 2000Date of Patent: November 12, 2002Assignee: UOP LLCInventors: Gregory J. Gajda, James F. McGehee
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Publication number: 20020151758Abstract: A repeated “soak and dry” selectivation process for preparing a modified metallosilicate catalyst composite is disclosed comprising of a mixture of amorphous silica, alumina and a pore size controlled metallosilicate useful for alkylaromatic conversion. The process comprises (a) contacting an intermediate pore metallosilicate with an organosilicon compound in a solvent for a specific duration and then recovering the solvent, (b) combining the organosilicon compound treated metallosilicate with water and then drying the catalyst, (c), repeating the steps a) and b) above and (d) calcining the catalyst in an oxygen containing atmosphere sufficient to remove the organic material and deposit siliceous matter on the metallosilicate. In a another embodiment, when the organosilicon compound is water soluble, step (b) may be avoided.Type: ApplicationFiled: August 23, 2001Publication date: October 17, 2002Applicant: INDIAN PETROCHEMICALS CORPORATION LIMITEDInventors: Jagannath Das, Anand Bhimrao Halgeri
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Patent number: 6464857Abstract: Molecular sieves comprising (1) phosphorus oxide; (2) a first oxide comprising an oxide of silicon, germanium or mixtures thereof; and (3) a second oxide comprising an oxide of aluminum, boron or mixtures thereof, said molecular sieve having a mole ratio of the first oxide to the second oxide of greater than 1, containing at least about 10 weight percent phosphorus oxide in the crystal framework, and having pores greater than 5 Å in diameter are useful as catalysts in hydrocarbon conversion reactions.Type: GrantFiled: February 28, 2002Date of Patent: October 15, 2002Assignee: Chevron U.S.A. Inc.Inventor: Stephen J. Miller
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Patent number: 6459006Abstract: It has been discovered that para-xylene (PX) can be synthesized with improved selectivity by reacting an aromatic compound such as toluene and/or benzene with a reactant(s) from fuel syngas such as a combination of hydrogen and carbon monoxide and/or carbon dioxide and/or methanol,or methylating agents produced therefrom. The combination of the selective methylation technology and a source of fuel syngas creates several advantages including simplification of the selective methylation process and utilization of low cost feeds. The fuel syngas is used on a once-through basis.Type: GrantFiled: November 3, 1999Date of Patent: October 1, 2002Assignee: ExxonMobil Chemical Patents Inc.Inventors: John D. Y. Ou, Thomas J. Waddick
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Patent number: 6436866Abstract: Disclosed is a Lewis acid catalyst composition comprising a specific mixed medium and a Lewis acid catalyst (II), wherein the specific mixed medium is mixed medium (I) comprising a perfluorinated aliphatic hydrocarbon (A) and at least one non-fluorinated hydrocarbon or a mixed medium (I′) comprising a perfluorinated aliphatic hydrocarbon (A), a perfluorinated aromatic hydrocarbon (C) and water (D), and wherein the Lewis acid catalyst (II) is at least one compound selected from the group consisting of compounds respectively represented by the following formulae (1), (2) and (3): (RfSO3)nM (1), [(RfSO2)2N]nM (2), and [(RfSO2)3C]nM (3). Also disclosed is a Lewis acid catalyst represented by the above-mentioned formula (3).Type: GrantFiled: May 26, 2000Date of Patent: August 20, 2002Assignee: Asahi Kasei Kabushiki KaishaInventors: Joji Nishikido, Hitoshi Nakajima
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Publication number: 20020111522Abstract: An improved zeolite having a high number of strong acid sites wherein said zeolite has an AAI of at least 1.0. In a preferred embodiment, such zeolite is produced by controlling conditions after production of the crystalline structure such that loss of tetrahedral aluminum is minimized to thereby provide a zeolite with the above defined AAI.Type: ApplicationFiled: October 17, 2001Publication date: August 15, 2002Inventors: Rudolf Overbeek, Nelleke van der Puil, Chuen Y. Yeh, Lawrence L. Murrell, Yun-Feng Chang, Philip Jay Angevine, Johannes Hendrik Koegler
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Patent number: 6429345Abstract: The invention concerns a process for producing at least one compound selected from 2-, 3-, 4-, 5- and 6-phenylalkanes by alkylating benzene using at least one olefin containing at least 9 carbon atoms per molecule, in the presence of a catalyst comprising at least one zeolite with structure type EUO, at least partially in its acid form and at least one matrix, said zeolite comprising silicon and at least one element T selected from the group formed by aluminium, iron, gallium and boron (preferably aluminium and boron), with an Si/T atomic ratio of more than 5; said process being carried out at a temperature in the range 30° C. to 400° C., a pressure in the range 0.1 to 10 MPa, with an hourly space velocity of 0.50 to 200 h−1, and a benzene/olefins mole ratio in the range 1:1 to 50:1.Type: GrantFiled: June 22, 2000Date of Patent: August 6, 2002Assignee: Institut Francais du PetroleInventors: Jean-François Joly, Fabio Alario, Elisabeth Merlen, Julia Magne-Drisch
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Patent number: 6423879Abstract: There is provided a process for the selective production of para-xylene which comprises reacting toluene with methanol in the presence of a catalyst comprising a porous crystalline material having a Diffusion Parameter for 2,2 dimethylbutane of about 0.1-15 sec−1 when measured at a temperature of 120° C. and a 2,2 dimethylbutane pressure of 60 torr (8 kPa). The porous crystalline material is preferably a medium-pore zeolite, particularly ZSM-5, which has been severely steamed at a temperature of at least 950° C. The porous crystalline material is preferably combined with at least one oxide modifier, preferably including phosphorus, to control reduction of the micropore volume of the material during the steaming step.Type: GrantFiled: November 15, 1999Date of Patent: July 23, 2002Assignee: ExxonMobil Oil CorporationInventors: Stephen H. Brown, Mark F. Mathias, Robert A. Ware, David H. Olson
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Patent number: 6409986Abstract: The present invention relates to zeolithic materials having a characteristic X ray diffraction pattern, and its preparation method, characterized by the relatively low pH of the synthesis medium and the use of F− anions as mineralizing agent. The invention also claims the use of the obtained material in catalytic processes for the transformation of hydrocarbons and in oxidation process. The method comprises heating at 363-473° K a reaction mixture which contains a source of at least one tetravalent element T(IV), optionally a source of an element T(III), optionally H2O2, a structure director organic cation, a source of anions F− and water, the presence of alkaline cations is not necessary.Type: GrantFiled: June 19, 2000Date of Patent: June 25, 2002Assignee: Consejo Superior de Investigaciones Cientificas Universidad Politecnica de ValenciaInventors: Miguel-Angel Camblor Fernandez, Avelino Corma Canos, Susana Valencia Valencia
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Publication number: 20020062046Abstract: Method of performing alkylation or acylation reactions of aromatic substrates under supercritical or near-critical reaction conditions. In particular, a method of performing Friedel-Crafts alkylation or acylation reactions is disclosed under those conditions. Friedel-Crafts reactions may be effected using a heterogeneous catalyst in a continuous flow reactor containing a super-critical or near-critical reaction medium. Selectivity of product formation can be achieved by varying one or more of the temperature, pressure, catalyst, flow rates and also by varying the ratios of aromatic substrate to acylating or alkylating agent.Type: ApplicationFiled: August 24, 2001Publication date: May 23, 2002Inventors: Thomas M. Swan, Stephen K. Ross, Martyn Poliakoff, Martin G. Hitzler, Fiona R. Smail, Thomas Tacke, Stefan Wieland
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Patent number: 6392047Abstract: Biaryls, e,g,. biphenyls, phenylpyridines, phenylfurans, phenylpyrroles, phenylthiophenes, bipyridines, pyridylfurans or pyridylpyrroles are prepared in high yields by coupling aromatics with an aromatic boric acid or boric ester in the presence of a palladaphosphacyclobutane catalyst.Type: GrantFiled: July 13, 2000Date of Patent: May 21, 2002Assignee: Clariant GmbHInventors: Holger Geissler, Steffen Haber, Andreas Meudt, Frank Vollmueller, Stefan Scherer
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Patent number: 6388156Abstract: It has been discovered that para-xylene (PX) can be synthesized with improved selectivity by reacting an aromatic compound such as toluene and/or benzene with a reactant(s) such as a combination of hydrogen and carbon monoxide and/or carbon dioxide and/or methanol or methylating agents produced therefrom. Catalytic reaction systems are employed, such as crystalline or amorphous aluminosilicates having one-dimensional channel structure, para-alkyl selectivated crystalline or amorphous aluminosilicates, para-alkyl selectivated substituted aluminosilicates, crystalline or amorphous substituted silicates having one-dimensional channel structure, para-alkyl selectivated substituted silicates, crystalline or amorphous aluminophosphates, para-alkyl selectivated crystalline or amorphous aluminophosphates, para-alkyl selectivated zeolite-bound zeolite and para-alkyl selectivated substituted aluminophosphates, and mixtures thereof.Type: GrantFiled: May 14, 1999Date of Patent: May 14, 2002Assignee: ExxonMobil Chemical Patents Inc.Inventors: John D. Y. Ou, Gary F. Janda, Zongxuan Hong, Russell D. Sellen
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Patent number: 6388157Abstract: A process for alkylation of aromatic compounds using a new family of related crystalline aluminosilicate zeolites has been developed. These zeolites are represented by the empirical formula: Mmn+Rrp+Al(1−x)ExSiyOz where M is an alkali or alkaline earth metal such as lithium and strontium, R is a nitrogen containing organic cation such as tetramethyl-ammonium and E is a framework element such as gallium.Type: GrantFiled: November 3, 2000Date of Patent: May 14, 2002Assignee: UOP LLCInventors: Deng-Yang Jan, Gregory J. Lewis, Jaime G. Moscoso, Mark A. Miller
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Publication number: 20020049359Abstract: A process for preparing alkyl substituted aromatic compounds by alkylating an aromatic compound with an alkylating agent in the presence of a porous crystalline zeolite in which the zeolite has been selectively deluminated to remove nonframework aluminum.Type: ApplicationFiled: March 20, 2001Publication date: April 25, 2002Inventors: Hye Kyung C. Timken, Arthur W. Chester, Susan Ardito, Mark P. Hagemeister
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Patent number: 6376729Abstract: A process for the production of ethylbenzene by the gas phase alkylation of benzene over a molecular sieve aromatic alkylation catalyst followed by liquid phase alkylation of the product of the gas phase alkylation. A feedstock containing benzene and ethylene is supplied to a first alkylation reaction zone containing a molecular sieve aromatic alkylation catalyst. The reaction zone is operated at temperature and pressure conditions to cause gas phase ethylation of the benzene with the production of an alkylation product comprising a mixture of ethylbenzene and polyalkylated aromatic components including diethylbenzene. The output from the first alkylation reaction zone is supplied, at least in part, to a second alkylation zone which is operated in the liquid phase or in the supercritical region followed by supply to an intermediate recovery zone for the separation and recovery of ethylbenzene and a polyalkylated aromatic compound component including diethylbenzene.Type: GrantFiled: December 4, 2000Date of Patent: April 23, 2002Assignee: Fina Technology, Inc.Inventors: James T. Merrill, James R. Butler
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Patent number: 6376730Abstract: A layered catalyst composition is disclosed where the composition is prepared by bonding an outer layer comprising a bound zeolite (e.g. zeolite beta) to an inner core material (e.g. cordierite). The use of an organic bonding agent in the catalyst preparation procedure provides a composition that is sufficiently resistant to mechanical attrition to be used commercially in aromatic alkylation processes (e.g. benzene alkylation to ethylbenzene). Advantages associated with the use of layered compositions include a significant reduction in the amount of zeolite used for a given reactor loading and improved selectivity to desired alkylated aromatic products. Further benefits are realized when the layered composition is formed into shapes having a sufficiently high void volume to reduce pressure drop across the alkylation catalyst bed. This is especially relevant for operation involving high recycle rates and consequently low alkylating agent concentrations in the reaction zone.Type: GrantFiled: June 26, 2000Date of Patent: April 23, 2002Assignee: UOP LLCInventors: Deng-Yang Jan, James F. Mc Gehee, Guy B. Woodle, Masao Takayama, Raelynn M. Miller
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Patent number: 6368496Abstract: Bromine reactive hydrocarbon contaminants are removed from aromatic streams by first providing an aromatic feedstream having a negligible diene level. The feedstream is contacted with an acid active catalyst composition under conditions sufficient to remove mono-olefins. An aromatic stream may be pretreated to remove dienes by contacting the stream with clay, hydrogenation or hydrotreating catalyst under conditions sufficient to substantially remove dienes but not mono-olefins.Type: GrantFiled: February 3, 1998Date of Patent: April 9, 2002Assignee: ExxonMobil Oil CorporationInventors: Stephen H. Brown, Terry E. Helton, Arthur P. Werner
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Publication number: 20020038775Abstract: There is provided macrostructures of porous inorganic material which can have controlled size, shape, and/or porosity and a process for preparing the macrostructures. The macrostructures comprise a three-dimension network of particles of porous inorganic materials. The process for preparing the macrostructures involves forming an admixture containing a porous organic ion exchanger and a synthesis mixture capable of forming a porous inorganic material and then converting the synthesis mixture to a solid porous inorganic material. After formation of the composite material, the porous organic ion exchanger can be removed from the composite material to obtain the macrostructures, either before or after the porous inorganic material is hydrothermally treated with a structure directing agent to convert at least a portion of such porous inorganic material to a crystalline molecular sieve composition. The resulting macrostructure is composed of particles of the crystalline molecular sieve composition.Type: ApplicationFiled: January 5, 2001Publication date: April 4, 2002Inventors: Per Johan Sterte, Lubomira Borislavova Tosheva-Jivkova
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Publication number: 20020038067Abstract: The present invention provides a process for regenerating a spent aromatics alkylation or transalkylation catalyst comprising a molecular sieve by contacting the spent catalyst with an oxygen-containing gas at a temperature of about 120 to about 600° C. and then contacting the catalyst with an aqueous medium, such as an ammonium nitrate solution, an ammonium carbonate solution or an acetic acid solution.Type: ApplicationFiled: July 11, 2001Publication date: March 28, 2002Inventors: Ajit B. Dandekar, Michael Hryniszak, David Lawrence Stern, Jeffrey Scott Beck
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Patent number: 6355851Abstract: A zeolite-catalyzed cumene synthesis process in which benzene and propylene feedstocks are pre-treated to remove catalyst poisons. The benzene feedstock is pre-treated under pressure by contact with a “hot” clay bed at a temperature of about 200 to 500° C., followed by distillation of the benzene feedstock to separate the benzene from the higher molecular weight materials formed from olefinic poisons during the hot clay treatment. The benzene feed is also subjected to a “cold” clay treatment wherein the benzene distillate is contacted with an ambient-temperature clay. The propylene feedstock is pre-treated by contact with an alumina to remove trace sodium compounds and moisture, a molecular sieve to remove moisture, and two modified aluminas to remove catalyst poisons. The pre-treated propylene and benzene feedstocks are then reacted in the presence of a zeolite catalyst to form cumene without causing rapid degradation of the catalyst's activity.Type: GrantFiled: November 13, 2000Date of Patent: March 12, 2002Assignee: Sunoco, Inc. (R&M)Inventors: Albert H. Wu, James T. Wei
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Patent number: 6339179Abstract: A process for producing alkyl aromatics using a transalkylation reaction zone and an alkylation reaction zone is disclosed. One portion of the transalkylation reaction zone effluent passes to an alkylation reaction zone where an aromatic substrate is alkylated to the desired alkyl aromatic. At least a portion of the alkylation reaction zone effluent and another portion of the transalkylation reaction zone effluent pass to a product recovery zone. This process decreases the capital and operating costs of recycling aromatic substrate to the transalkylation and/or alkylation reaction zone while maintaining operational flexibility. This process is well suited for solid transalkylation and alkylation catalysts. Ethylbenzene and cumene may be produced by this process.Type: GrantFiled: July 25, 2000Date of Patent: January 15, 2002Assignee: UOP LLCInventors: Russell C. Schulz, Gregory J. Gajda, Guy B. Woodle, Andrew S. Zarchy
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Patent number: 6316675Abstract: A process for the synthesis of olefins having aromatic substituents is described in which olefins are reacted with aryl halides in the presence of catalysts consisting of palladium compounds and tetraaryl phosphonium salts.Type: GrantFiled: September 23, 1999Date of Patent: November 13, 2001Assignee: Studiengesellschaft Kohle mbHInventors: Manfred T. Reetz, Gunther Lohmer, Renate Lohmer
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Patent number: 6303840Abstract: A process for the alkylation of aromatic substrates under supercritical or near-critical reaction conditions is described. In particular, a method for performing Friedel-Crafts alkylation reactions is disclosed under those conditions. Friedel-Crafts reactions may be effected using a heterogeneous catalyst in a continuous flow reactor containing a supercritical or near-critical reaction medium. Selectivity of product formation can be achieved by varying one or more of temperature, pressure, catalyst, flow rates and also by varying the ratios of aromatic substrate to alkylating agent.Type: GrantFiled: June 18, 1999Date of Patent: October 16, 2001Assignee: Thomas Swan & Co., LimitedInventors: Martyn Poliakoff, Thomas M. Swan, Thomas Tacke, Martin G. Hitzler, Stephen K. Ross, Stefan Wieland, Fiona Ruth Smail
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Patent number: 6297417Abstract: A process of preparing an alkylated benzene or mixture of alkylated benzenes involving contacting a benzene feedstock with a solid acid, such as an acidic clay or acid zeolite, in a pretreatment zone at a temperature greater than about 130° C. but less than about 300° C. to form a pretreated benzene feedstock, and thereafter contacting the pretreated benzene feedstock with (a) an alkylating agent in an alkylation zone or (b) a transalkylating agent in a transalkylation zone, in the presence of an alkylation/transalkylation catalyst so as to prepare the alkylated benzene or mixture of alkylated benzenes. The pretreatment step improves the lifetime of the alkylation/transalkylation catalyst. Preferred products are ethylbenzene and cumene.Type: GrantFiled: February 18, 1999Date of Patent: October 2, 2001Assignee: The Dow Chemical CompanyInventors: Mohammed S. U. Samson, Matheus J. M. Van der Aalst, Garmt R. Meima, Guo-shuh John Lee, Juan M. Graces
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Publication number: 20010018545Abstract: A new process for the preparation of ethylbenzene by alkylation of benzene with dilute ethylene contained in dry gas by catalytic distillation and the apparatus used therefor are disclosed. The new process includes the pretreatment of raw refinery dry gas, the gas-liquid-solid three phases alkylation of benzene with the ethylene over a solid catalyst in a catalytic distillation tower, and concurring course of distillation separation of product mixture. The performance, type, and loading way of catalyst and distillation packing should satisfy the given requirements. The invention has many advantages such as simple apparatus structure and ease in operation, moderate operation conditions, large catalyst capacity, high product quality, long catalyst lifetime, etc.Type: ApplicationFiled: December 11, 2000Publication date: August 30, 2001Inventors: Jirui Zhang, Dongfeng Li, Jiquan Fu, Gang Cao
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Patent number: 6281399Abstract: A process for producing isopropyl aromatics using a transalkylation reaction zone and an alkylation reaction zone is disclosed. Portions of the transalkylation reaction zone effluent pass to a multibed alkylation reaction zone where aromatics in the transalkylation reaction zone effluent are alkylated to the desired isopropyl aromatics. At least a portion of the transalkylation reaction zone effluent passes to an alkylation bed other than the first alkylation bed of the multibed alkylation reaction zone. This process decreases the capital and operating costs of recycling the aromatics in the transalkylation reaction zone effluent. This process is well suited for solid transalkylation and alkylation catalysts. Cumene may be produced by this process.Type: GrantFiled: February 23, 2000Date of Patent: August 28, 2001Assignee: UOP LLCInventors: Russell C. Schulz, Gregory J. Gajda, Guy B. Woodle
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Patent number: 6262325Abstract: The catalyst comprises at least one alkali metal on a support which has the general formula (I) An′Tim′Zrp′Hfq′On′+2(m′+p′+q′) (I) where A is a divalent metal, 20·(m′+p′+q′)>n′>0.05·(m′+p′+q′), and which may be doped with at least one compound of an alkali metal and/or alkaline earth metal, where the alkali metal/support ratio by weight is 0.01-5:1 and, when a dopant is present, the dopant/support ratio by weight is 0.01-5:1, and where the proportion of support phase corresponding to the ZrO2 structure or an alkaline earth metal oxide structure or consisting of ZrO2 or alkaline earth metal oxide is less than 10% by weight.Type: GrantFiled: October 6, 1999Date of Patent: July 17, 2001Assignee: BASF AktiengessellschaftInventors: Thomas Narbeshuber, Ulrich Steinbrenner
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Patent number: 6252126Abstract: An ethylbenzene production system comprises a reactor vessel, a vapor phase ethylene feed stream, a benzene feed stream entering the reactor vessel, and a product stream containing ethylbenzene exiting the reactor vessel. The reactor vessel has an ethylation section and a benzene stripping section, whereby fluid communication via integrated vapor and liquid traffic is maintained between the ethylation section and stripping section. The vapor phase ethylene feed stream contains 3 to 50 mol % ethylene and at least 20 mol % methane entering the reactor vessel.Type: GrantFiled: December 22, 1998Date of Patent: June 26, 2001Inventor: David Netzer
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Publication number: 20010002426Abstract: There is provided a process for converting hydrocarbons which utilizes a zeolite bound zeolite catalyst that has enhanced performance when utilized in hydrocarbon conversion processes, e.g., catalytic cracking, alkylation, disproportionation of toluene, isomerization, and transalkylation reactions. The catalyst comprises a first zeolite having particles of greater than about 0.1 micron average particle size and a binder comprising second zeolite particles having an average particle size less than said first particles.Type: ApplicationFiled: January 8, 2001Publication date: May 31, 2001Inventors: Gary David Mohr, Marcel Johannes Gerardus Janssen
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Patent number: 6232515Abstract: A process for producing ethyl aromatics using a transalkylation reaction zone and an alkylation reaction zone is disclosed. Portions of the transalkylation reaction zone effluent pass to a multibed alkylation reaction zone where aromatics in the transalkylation reaction zone effluent are alkylated to the desired ethyl aromatics. At least a portion of the transalkylation reaction zone effluent passes to an alkylation bed other than the first alkylation bed of the multibed alkylation reaction zone. This process decreases the capital and operating costs of recycling the aromatics in the transalkylation reaction zone effluent. This process is well suited for solid transalkylation and alkylation catalysts. Ethylbenzene may be produced by this process.Type: GrantFiled: March 17, 2000Date of Patent: May 15, 2001Assignee: UOP LLCInventors: Russell C. Schulz, Gregory J. Gajda, Guy B. Woodle
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Patent number: 6222084Abstract: Process for the production of ethylbenzene by alkylation over a silicalite alkylation catalyst with subsequent transalkylation of diethylbenzene with the alkylation catalyst and conditions selected to retard xylene production and also heavies production. Benzene and ethylene are applied to a multi-stage alkylation reaction zone having a plurality of series-connected catalyst beds containing silicalite of a predominantly monoclinic symmetry having a silica/alumina ratio of at least 275. Gas-phase ethylation of benzene is at a flow rate to provide a space velocity of benzene over the catalyst to produce a xylene concentration of about 600 ppm or less of the ethylbenzene content. Periodically the space velocity may be increased to a value which is greater than the space velocity associated with a minimum concentration of diethylbenzene in the alkylation product such that diethylbenzene production is enhanced while minimizing any attendant transalkylation reactions within the alkylation reaction zone.Type: GrantFiled: April 9, 1999Date of Patent: April 24, 2001Assignee: Fina Technology, Inc.Inventors: Ashim Kumar Ghosh, James T. Merrill, James R. Butler
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Patent number: 6215035Abstract: The invention relates to a process for the preparation of aralkylated aromatic compound with both small and large size aralkylating agents; wherein the catalyst used is heterogeneous solid catalyst removable from the reaction products by simple filtration, thus allowing the separated catalyst to be reused in the process. The catalyst is selected from micro or mesoporous gallosilicates and galloaluminosilicates, having structure similar to that of zeolites known in the prior art.Type: GrantFiled: January 11, 1999Date of Patent: April 10, 2001Assignee: Council of Scientific and Industrial ResearchInventors: Vasant Ramchandra Choudhary, Suman Kumar Jana, B-Phani Kiran
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Patent number: 6204423Abstract: A description follows of a catalytic composition comprising a mixture of Y zeolite and pillared clay and a process which uses this catalytic composition for the alkylation of aromatic hydrocarbons by means of long-chain linear olefins. The aromatic alkyl compounds thus obtained are useful for the preparation of biodegradable synthetic detergents.Type: GrantFiled: December 15, 1997Date of Patent: March 20, 2001Assignee: Enichem Augusta Industriale S.r.l.Inventors: Stefano Amarilli, Carlo Perego, Giuseppe Bellussi, Giovanni Colombo
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Patent number: 6172274Abstract: A solid catalyst alkylation process that wets catalyst particles with the alkylation substrate prior to introducing the catalyst particles to a liquid phase alkylation reactor is disclosed. A vapor stream from the wetting step that comprises the alkylation substrate and a reactor effluent stream comprising product alkylate and excess alkylation substrate are both passed to the product recovery zone, which recovers the alkylate product and recycles the alkylation substrate. Routing the vapor stream and the reactor effluent stream together to the product recovery zone minimizes pressure imbalances, ensures steady catalyst flow, and minimizes equipment costs. This process is applicable to alkylation processes that produce motor fuels.Type: GrantFiled: December 16, 1998Date of Patent: January 9, 2001Assignee: UOP LLCInventor: Christopher D. Gosling
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Patent number: 6166281Abstract: This invention is directed to a fluorine-containing mordenite catalyst and use thereof in the manufacture of linear alkylbenzene (LAB) by alkylation of benzene with an olefin. The paraffin may have from about 10 to 14 carbons. The fluorine-containing mordenite is prepared typically by treatment with an aqueous hydrogen fluoride solution. The benzene alkylation may be conducted using reactive distillation. This invention is also directed to a process for production of LAB having a high 2-phenyl isomer content by combining LAB product from the fluorine-containing mordenite product from a conventional LAB alkylation catalyst such as hydrogen fluoride.Type: GrantFiled: October 19, 1998Date of Patent: December 26, 2000Assignee: Huntsman Petrochemical CorporationInventor: Prakasa Rao Anantaneni
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Patent number: 6160190Abstract: Porous microcomposites have been prepared from perfluorinated ion-exchange polymer and metal oxides such as silica using the sol-gel process. Such microcomposites possess high surface area and exhibit extremely high catalytic activity. The microcomposites catalyze, among others, the reaction between organic aromatic compounds and olefins.Type: GrantFiled: June 3, 1999Date of Patent: December 12, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: Mark Andrew Harmer, Qun Sun
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Patent number: 6156949Abstract: There is provided a process for shape selective xylene methylation that involves contacting a feedstream which includes xylene and methanol under alkylation conditions, with a low activity catalyst. Xylene conversions of at least 15% at methanol utilization levels of 25% or greater are achieved by sequential injection of methanol The xylene methylation process has a selectivity for pseudocumene of over 85% and up to 99%, with a pseudocumene:durene ratio of up to 20 or more.Type: GrantFiled: December 28, 1998Date of Patent: December 5, 2000Assignee: Mobil Oil CorporationInventors: Stephen H. Brown, Mark F. Mathias
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Patent number: 6153806Abstract: 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 reducing the number of hydride transfer active sites on a zeolite beta. One way of producing this "site-modified" beta is to take a parent or precursor zeolite beta that has at least 0.5% carbon on it and treat it under oxidation conditions at a temperature of about 450.degree. C. to about 750.degree. C. The use of such a catalyst gives a product containing less than 0.3 wt. % 1,1-diphenylethane relative to ethylbenzene.Type: GrantFiled: June 21, 1999Date of Patent: November 28, 2000Assignee: UOP LLCInventor: Gregory J. Gajda
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Patent number: 6137020Abstract: A process for reducing the amount of undesirable byproducts, for example multi-ring compounds known as heavy residue in a process for the alkylation of an aromatic hydrocarbon with an olefin using a silicalite catalyst is disclosed. The process comprises supplying a feedstock containing benzene to a reaction zone with an alkylating agent in a molar ratio of benzene to alkylating agent of from about 2:1 to about 20:1 and into contact with an aluminosilicate alkylation catalyst having an average crystallite size of less than about 0.50 .mu.m and wherein the size of about 90% of the crystallites is less than 0.70 .mu.m. The catalyst is characterized by an Si/Al atomic ratio in the range from between 50 and 150 and a maximum pore size in the range from about 1000 to 1800 .ANG.. The catalyst has a sodium content of less than about 50 ppm and the reaction is carried out under conversion conditions including a temperature of from about 250.degree. C. to about 550.degree. C.Type: GrantFiled: July 31, 1998Date of Patent: October 24, 2000Assignee: Fina Technology, Inc.Inventors: James R. Butler, Mark E. Kuchenmeister
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Patent number: 6133492Abstract: This invention is directed to a fluorine-containing mordenite catalyst and use thereof in the manufacture of linear alkylbenzene (LAB) by alkylation of benzene with an olefin. The olefin may have from about 10 to 14 carbons. The fluorine-containing mordenite is prepared typically by treatment with an aqueous hydrogen fluoride solution. The benzene alkylation may be conducted using reactive distillation. This invention is also directed to a process for production of LAB having a high 2-phenyl isomer content by use of the fluorine-containing mordenite in conjunction with a conventional solid LAB alkylation catalyst. The two catalysts may be used in a mixed catalyst bed or may be packed in series, with the relative proportions being adjusted to provide a desired 2-phenyl isomer content of in the final product.Type: GrantFiled: October 19, 1998Date of Patent: October 17, 2000Assignee: Huntsman Petrochemical CorporationInventor: Prakasa Rao Anantaneni
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Patent number: 6121501Abstract: A process for producing 2,6-dialkylnaphthalene from a hydrocarbon feedstock that contains at least one component selected from the group consisting of dialkylnaphthalene isomers, monoalkylnaphthalene isomers, polyalkylnaphthalenes, and naphthalene, is provided that includes the following steps:I. separating the hydrocarbon feedstock and/or a dealkylation product fed from step III into a naphthalene fraction, a monoalkylnaphthalene fraction, a dialkylnaphthalene fraction and a remaining products fraction;II. separating and purifying 2,6-dialkylnaphthalene from the dialkylnaphthalene fraction of step I;III. dealkylating the hydrocarbon feedstock and/or the remaining products fraction of step I and feeding the dealkylation product to step I; andIV. alkylating the naphthalene and monoalkylnaphthalene fractions of step I;wherein the hydrocarbon feedstock is fed to step I or step III.Type: GrantFiled: April 9, 1999Date of Patent: September 19, 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: 6111158Abstract: The present invention is a process for producing phenyl-alkanes at alkylation conditions in the presence of a zeolite having an NES zeolite structure type, such as NU-87. This invention produces phenyl-alkanes having lightly branched aliphatic alkyl groups which are used to produce modified alkylbenzene sulfonates that have improved cleaning effectiveness in hard and/or cold water while also having biodegradability comparable to that of linear alkylbenzene sulfonates.Type: GrantFiled: March 4, 1999Date of Patent: August 29, 2000Assignee: UOP LLCInventors: Richard E. Marinangeli, Michael G. Gatter, R. Joe Lawson, Thomas R. Fritsch
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Patent number: 6111157Abstract: A process is provided for the alkylation, transalkylation, or isomerization of aromatic hydrocarbons. The processes comprises contacting aromatic hydrocarbons under conversion conditions with a zeolite bound zeolite catalyst. The zeolite bound zeolite catalyst comprises first crystals of a first large pore zeolite which are bound together by second crystals of a second zeolite.Type: GrantFiled: May 29, 1997Date of Patent: August 29, 2000Assignee: Exxon Chemical Patents, Inc.Inventors: Dan Eldon Hendriksen, Gary David Mohr, Johannes Petrus Verduijn, Robert Scott Smith
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Patent number: 6107534Abstract: An improved zeolite catalyst containing an acid-treated zeolite, a boron component and a zinc component manufactured by a novel method having certain process steps necessary for providing the improved zeolite catalyst. The process steps include a first steam treatment of an acid-treated zeolite, followed by incorporation of such zeolite with a boron component and a zinc component, followed by a second steam treatment. Processes are also disclosed for using the improved zeolite catalyst in the conversion of hydrocarbons, preferably non-aromatic hydrocarbons, to lower olefins (such as ethylene and propylene) and aromatic hydrocarbons (such as benzene, toluene, and xylene).Type: GrantFiled: August 25, 1999Date of Patent: August 22, 2000Assignee: Phillips Petroleum CompanyInventors: Charles A. Drake, An-hsiang Wu
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Patent number: 6096935Abstract: A process for producing alkyl aromatics using a transalkylation reaction zone and an alkylation reaction zone is disclosed. The transalkylation reaction zone effluent passes to the alkylation reaction zone where aromatics in the transalkylation reaction zone effluent are alkylated to the desired alkyl aromatics. This process decreases the capital and operating costs of recycling the aromatics in the transalkylation reaction zone effluent. This process is well suited for solid transalkylation and alkylation catalysts. Ethylbenzene and cumene may be produced by this process.Type: GrantFiled: July 28, 1998Date of Patent: August 1, 2000Assignee: UOP LLCInventors: Russell C. Schulz, Gregory J. Gajda
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Patent number: 6093866Abstract: An alkylation catalyst comprises from 50 to 70 wt % of hydrogen type ZSM-SM-11 co-crystaline zeolite containing rare earth element and the rest amount of porous inorganic oxide matrix material. The zeolite has particular chemical composition and X-ray diffraction lines. This catalyst has higher activity, selectivity and stability in alkylation process than that of the prior art. With this catalyst the process for preparing ethyl benzene by alkylation of benzene with ethylene has higher ethylene conversion and ethyl benzene selectivity.Type: GrantFiled: June 23, 1997Date of Patent: July 25, 2000Assignees: China Petro-Chemical Corporation, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Fushun Petrochemical Company of SinopecInventors: Qingxia Wang, Shurong Zhang, Guangyu Cai, Feng Li, Longya Xu, Zuxian Huang, Yuying Li
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Patent number: 6090991Abstract: Ethylbenzene is produced by alkylation over monoclinic silicalite catalysts having a weak acid site concentration of less than 50 micromoles per gram. A feedstock containing benzene and ethylene is applied to an alkylation reaction zone having at least one catalyst bed containing a monoclinic silicalite catalyst having a weak acid site concentration of less than 50 micromoles per gram. 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 silicalite catalysts to produce an alkylation product. The alkylation product is then withdrawn from the reaction zone for separation and recovery.Type: GrantFiled: February 27, 1999Date of Patent: July 18, 2000Assignee: Fina Technology, Inc.Inventors: James R. Butler, Ashim Kumar Ghosh
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Patent number: 6084143Abstract: A catalytic composition is described for the alkylation or transalkylation of aromatic compounds consisting of zeolite Beta, as such or modified by the isomorphic substitution of aluminium with boron, iron or gallium or by the introduction of alkaline/earth-alkaline metals following ion exchange processes, and of 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 as to be composed for a fraction of at least 25% of pores with a radius higher than 100 .ANG..Type: GrantFiled: July 15, 1998Date of Patent: July 4, 2000Assignee: Enichem Synthesis S.p.A.Inventors: Gianni Girotti, Oscar Cappellazzo
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Patent number: 6080382Abstract: The present invention relates to new crystalline zeolite SSZ-48 prepared using a decahydroquinolinium cation templating agent.Type: GrantFiled: December 17, 1997Date of Patent: June 27, 2000Assignee: Chevron U. S. A. Inc.Inventors: Gregory S. Lee, Stacey I. Zones
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Patent number: 6071864Abstract: Novel methods for the preparation of modified poly .alpha.-olefins, and compositions prepared by the novel methods are disclosed. The modified poly alpha-olefins of the present invention are useful as base fluids or additives in synthetic lubricants.Type: GrantFiled: July 17, 1998Date of Patent: June 6, 2000Assignee: Mobil Oil CorporationInventors: Suzzy Chen Hsi Ho, Margaret May-Som Wu