Resulting Side-chain Has Less Than Four C Atoms Patents (Class 585/453)
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Publication number: 20150105597Abstract: A process is disclosed for making styrene and/or ethylbenzene by reacting toluene with a C1 source over a catalyst in at least one radial reactor to form a product stream comprising styrene and/or ethylbenzene.Type: ApplicationFiled: May 14, 2012Publication date: April 16, 2015Inventors: Juan Mirabel Garza, Daniel Edward Gerwien, David Morris Hamilton, JR., Larry Lanier Marshall, Waleed Yousef Musallam, Anand Nilekar, Peter Tanev Tanev, Lizbeth Olivia Cisneros Trevino
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Publication number: 20140066677Abstract: A method for the oxidative coupling of hydrocarbons, such as the oxidative coupling of methane to toluene, includes providing an oxidative catalyst inside a reactor, and carrying out the oxidative coupling reaction under a set of reaction conditions. The oxidative catalyst includes (A) at least one element selected from the group consisting of the Lanthanoid group, Mg, Ca, and the elements of Group 4 of the periodic table (Ti, Zr, and Hf); (B) at least one element selected from the group consisting of the Group 1 elements of Li, Na, K, Rb, Cs, and the elements of Group 3 (including La and Ac) and Groups 5-15 of the periodic table; (C) at least one element selected from the group consisting of the Group 1 elements of Li, Na, K, Rb, Cs, and the elements Ca, Sr, and Ba; and (D) oxygen.Type: ApplicationFiled: November 6, 2013Publication date: March 6, 2014Applicant: FINA TECHNOLOGY, INC.Inventors: Sivadinarayana Chinta, Joseph L. Thorman, James R. Butler, Joe Hunter, Taylor Rives
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Patent number: 8399726Abstract: A method for the oxidative coupling of hydrocarbons includes providing an oxidative catalyst inside a reactor and carrying out the oxidative coupling reaction under a set of reaction conditions. The reactor surfaces that contact the reactants and products do not provide a significant detrimental catalyzing effect. In an embodiment the reactor contains an inert lining or a portion of the reactor inner surface is treated to reduce the detrimental catalytic effects. In an embodiment the reactor contains a lining that includes an oxidative catalyst.Type: GrantFiled: April 20, 2010Date of Patent: March 19, 2013Assignee: Fina Technology IncInventors: Sivadinarayana Chinta, Joseph Thorman
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Publication number: 20120296133Abstract: 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: ApplicationFiled: July 25, 2012Publication date: November 22, 2012Applicant: FINA TECHNOLOGY, INC.Inventor: James R. Butler
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Publication number: 20120296136Abstract: A process is disclosed for making styrene and/or ethylbenzene by reacting toluene with a C1 source over a catalyst in at least one radial reactor to form a product stream comprising styrene and/or ethylbenzene.Type: ApplicationFiled: April 27, 2012Publication date: November 22, 2012Applicant: FINA TECHNOLOGY, INC.Inventor: Sivadinarayana Chinta
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Publication number: 20120277509Abstract: A process is disclosed for making styrene and/or ethylbenzene by reacting toluene with a C1 source over a catalyst in one or more reactors to form a product stream comprising styrene and/or ethylbenzene where the catalyst time on stream prior to regeneration is less than 1 hour.Type: ApplicationFiled: July 12, 2012Publication date: November 1, 2012Applicant: FINA TECHNOLOGY, INC.Inventors: Joseph Thorman, James Butler, Sivadinarayana Chinta
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Publication number: 20120259148Abstract: The present invention relates to a process for the alkylation of an organic compound comprising: (a) providing a catalyst comprising one or more zeolitic materials having a BEA framework structure, wherein the BEA framework structure comprises YO2 and optionally comprises X2O3, wherein Y is a tetravalent element, and X is a trivalent element, (b) contacting the catalyst with one or more alkylatable organic compounds in the presence of one or more alkylating agents in one or more reactors for obtaining one or more alkylated organic compounds, wherein the one or more zeolitic materials is obtainable from a synthetic process which does not employ an organotemplate as structure directing agent.Type: ApplicationFiled: April 3, 2012Publication date: October 11, 2012Applicants: Tokyo Institute of Technology, BASF SEInventors: Bilge Yilmaz, Ulrich Müller, Faruk Özkirim, Dirk de Vos, Feng-Shou Xiao, Takashi Tatsumi, Xinhe Bao, Weiping Zhang, Hermann Gies, Hiroyuki Imai, Bart Tijsebaert
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Publication number: 20120157739Abstract: Disclosed is a method for removing unsaturated aliphatic compounds from a hydrocarbon feed stream by contacting the hydrocarbon feed stream with an acidic molecular sieve to produce a hydrocarbon effluent stream having a lower unsaturated aliphatic content relative to the hydrocarbon feed stream. The hydrocarbon feed stream comprises an aromatic compound, a nitrogen compound, and an unsaturated aliphatic compound.Type: ApplicationFiled: December 8, 2011Publication date: June 21, 2012Applicant: UOP LLCInventors: Deng-Yang Jan, Michael A. Schultz, James A. Johnson
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Patent number: 8124035Abstract: Continuous processes for monoalkylating aromatic compound with an aliphatic feedstock comprising aliphatic olefin of 8 to 18 carbon atoms per molecule are effected using at least 3 reaction zones in series, each containing solid alkylation catalyst with effluent cooling between reaction zones, each of which reaction zones is supplied a portion of the fresh aliphatic feedstock, such that the Reaction Zone Delta T in each reaction zone is less than about 15° C. The overall aromatic compound to olefin molar ratio is less than about 20:1. The alkylation product has desirable linearity and low amounts of dimers, dealkylated compounds and diaryl compounds even though a low aromatic compound to olefin molar ratio is used.Type: GrantFiled: February 5, 2010Date of Patent: February 28, 2012Assignee: UOP LLCInventor: Mark G. Riley
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Publication number: 20100145121Abstract: Methods are provided for producing alkylbenzenes, such as propylbenzene, from aromatics, such as toluene, and alkenes, such as ethylene. Such methods comprise combining the toluene with about 100 ppm to about 350 ppm water and alkali metal catalyst, activating the catalyst at about 18O° C. to about 220° C., adding the ethylene and conducting the synthesis reaction at about 130° C. to about 15O° C.Type: ApplicationFiled: March 27, 2008Publication date: June 10, 2010Applicant: ALBEMARLEE CORPORATIONInventors: Stephen E. Belmont, Robert W. Nelson, Christopher A. Curtis
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Publication number: 20090036722Abstract: A process is described for producing an alkylaromatic compound, in which a first feed comprising an alkylatable aromatic compound and a second feed comprising an alkene are introduced into a first alkylation reaction zone comprising a first alkylation catalyst. The first alkylation reaction zone is operated under conditions effective to cause alkylation of the alkylatable aromatic compound by the alkene to produce said alkylaromatic compound, the conditions being such that the alkylatable aromatic compound is at least predominantly in the vapor phase. A first effluent comprising the alkylaromatic compound and unreacted alkylatable aromatic compound is withdrawn from the first alkylation reaction zone and at least part of the unreacted alkylatable aromatic compound is treated to remove catalyst poisons therefrom and produce a treated unreacted alkylatable aromatic stream.Type: ApplicationFiled: July 30, 2007Publication date: February 5, 2009Inventors: Michael C. Clark, Vijay Nanda, Maruti Bhandarkar, Joseph C. Peters, Chung-Ming Chi, Brian Maerz
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Patent number: 7030285Abstract: A side-chain of a substituted aromatic compound is alkylated by reacting the aromatic compound with an alkylating agent in the presence of a catalyst. The catalyst comprises a restructured smectite clay to which basic ions are incorporated by ion-exchange. The restructuring of the smectite clay is carried out by acid-treating the clay prior to ion-exchange.Type: GrantFiled: January 29, 2001Date of Patent: April 18, 2006Assignee: Optatech CorporationInventors: Adriana De Stefanis, Giorgio Perez, Anthony Tomlinson, Christer Bergst{umlaut over (r)}öm
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Patent number: 6414207Abstract: A catalyst comprising at least one alkali metal and at least one metallic or semimetallic promoter selected from the group consisting of Ca, Sr, Ba, Ag, Au, Zn, Cd, Hg, In, Tl, Sn, As, Sb and Bi, on a support which may be doped with one or more compounds of an alkali metal and/or alkaline earth metal, where the alkali metal/support ratio by weight is from 0.01 to 5, the promoter/alkali metal ratio by weight is from 0.0001 to 5 and, when a dopant is present, the dopant/support ratio by weight is from 0.01 to 5.Type: GrantFiled: June 20, 2001Date of Patent: July 2, 2002Assignee: BASF AktiengesellschaftInventors: Ulrich Steinbrenner, Eugen Gehrer
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Patent number: 6403852Abstract: There are provided a process for producing an alkenyl-substituted aromatic hydrocarbon by alkenylation of an alkyl-substituted aromatic hydrocarbon having a hydrogen atom at the &agr;-position of a side chain thereof with a conjugated diene, using a catalyst obtained by the action of an alkali metal compound and an alkali metal or an alkali metal hydroxide on an metal oxide selected from alumina or hydrotalcite by heating in a specific temperature range; and a process for producing an alkenyl-substituted aromatic hydrocarbon, characterized in that the reaction is carried out in the presence of an alkylaminopyridine of formula (1): wherein R1 is hydrogen or C1-C6 lower alkyl, and R1 is C1-C6 lower alkyl, using as a catalyst, Na metal, K metal, or an alloy thereof, or a catalyst carrying any of them on an inorganic compound support, or a catalyst obtained by the action of an alkali metal compound and alkali metal or an alkali metal hydride on a metal oxide selected from alumina, alkaline earthType: GrantFiled: June 25, 1999Date of Patent: June 11, 2002Assignee: Sumitomo Chemical Co., LimitedInventors: Michio Yamamoto, Gohfu Suzukamo
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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: 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: 6024897Abstract: There is disclosed a method of preparing benzyl metal compounds represented by general formula (2), comprising reacting a phenyl metal compound represented by general formula (1) with toluene, in the presence of a catalytic amount of amine. According to this method, benzyl metal compounds can be prepared at a high yield, and in an industrially advantageous manner. Further, there is also disclosed a method of preparing 4-phenyl-1-butenes, comprising reacting the benzyl metal compound obtained in the method, with an allyl halide. ##STR1## wherein M represents an alkali metal, ##STR2## wherein M has the same meaning as the above.Type: GrantFiled: January 30, 1998Date of Patent: February 15, 2000Assignee: K.sup..cndot. I Chemical Industry Co., Ltd.Inventors: Hidetoshi Tsumaki, Hidenori Matsuno
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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: 5659097Abstract: A process for producing a monoalkenyl aromatic hydrocarbon which comprises alkenylating a side chain of an aromatic hydrocarbon compound having at least one hydrogen atom at the .alpha.-position of a side chain (such as o-xylene) with a conjugated diene having 4 or 5 carbon atoms in the presence of a catalyst slurry prepared by adding an aromatic hydrocarbon compound to a catalyst comprising a alkali metal and an alkali metal compound. In the aforementioned process, it is particularly effective that the catalyst slurry is prepared by adding the aromatic hydrocarbon compound after the aromatic hydrocarbon compound has been deoxygenated and dehydrated by distillation, and the catalyst slurry thus prepared is supplied to the reaction system. According to the aforementioned process, an industrially useful monoalkenyl aromatic hydrocarbon compound, such as a monoalkenylbenzene, can be produced at a high selectivity, in a high yield, and with enhanced safety and stability for a long time.Type: GrantFiled: January 11, 1995Date of Patent: August 19, 1997Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Norio Fushimi, Makoto Takagawa
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Patent number: 5625102Abstract: A method of alkylating the side chain of alkyl-substituted aromatic hydrocarbons. The method comprises the steps of thermally treating an alumina by calcining in air and then degassing under vacuum to prepare an alumina carrier, loading an alkali metal on the alumina carrier by an impregnation method using the alkali metal dissolved in liquid ammonia, thermally treating the alkali metal loaded alumina carrier under vacuum to prepare a catalyst, then reacting an alkyl-substituted aromatic hydrocarbon with an aliphatic monoolefin, using the catalyst, under an atmosphere substantially free of oxygen, water and carbon dioxide gas to alkylate the side chain of the alkyl-substituted aromatic hydrocarbon.Type: GrantFiled: December 27, 1994Date of Patent: April 29, 1997Assignee: Mitsubishi Oil Co., Ltd.Inventors: Takaya Matsumoto, Yoshiichi Kumagai, Fumio Kumata
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Patent number: 5608132Abstract: A method of alkylating a side chain of alkyl-substituted aromatic hydrocarbons. The method involves the steps of loading an alkali metal on a thermally treated hydrotalcite carrier represented by formula (I) by an impregnation method using the alkali metal dissolved in liquid ammonia, thermally treating the alkali metal loaded hydrotalcite carrier under vacuum to prepare a catalyst, then reacting an alkyl-substituted aromatic hydrocarbon with an aliphatic monoolefin using the catalyst under an atmosphere substantially free of oxygen, water and carbon dioxide gas to alkylate a side chain of the alkyl-substituted aromatic hydrocarbon:[M.sup.2+.sub.(1-x) .multidot.M.sup.3+.sub.x (OH).sub.2 ].sup.x+ .multidot.[A.sup.n-.sub.x/n ].sup.x- .multidot.yH.sub.2 O (I)wherein M.sup.2+ represents a divalent metallic cation, M.sup.3+ represents a trivalent metallic cation, A.sup.n- represents an n-valent anion, n=0.1 to 0.5, x=0.1 to 0.5, and y=0 to 8.Type: GrantFiled: April 6, 1995Date of Patent: March 4, 1997Assignee: Mitsubishi Oil Co., Ltd.Inventors: Takaya Matsumoto, Shinji Nishikawa, Fumio Kumata
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Patent number: 5600048Abstract: There is provided a process for preparing ethylbenzene using liquid phase alkylation and vapor phase transalkylation. The liquid phase alkylation reaction may be catalyzed by an acidic solid oxide, such as MCM-22, MCM-49 and MCM-56. The vapor phase transalkylation may be catalyzed by a medium-pore size zeolite such as ZSM-5. The process may be run continuously with the continuous introduction of fresh benzene feed containing at least 500 ppm of nonbenzene hydrocarbon impurities. The combined ethylbenzene product of these alkylation and transalkylation reactions has very low levels of impurities including xylene, hydrocarbons having 7 or less carbon atoms and hydrocarbons having 9 or more carbon atoms.Type: GrantFiled: December 27, 1994Date of Patent: February 4, 1997Assignee: Mobil Oil CorporationInventors: Jane C. Cheng, C. Morris Smith, Chaya R. Venkat, Dennis E. Walsh
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Patent number: 5557024Abstract: Relatively short chain alkyl aromatic compounds are prepared by alkylating an alkylatable aromatic compound with a relatively short chain alkylating agent under sufficient reaction conditions in the presence of a catalyst comprising zeolite MCM-56. The liquid phase syntheses of ethylbenzene and cumene are particular examples of such MCM-56 catalyzed reactions.Type: GrantFiled: May 30, 1995Date of Patent: September 17, 1996Assignee: Mobil Oil CorporationInventors: Jane C. Cheng, Anthony D. Fung, Donald J. Klocke, Stephen L. Lawton, Daria N. Lissy, Wieslaw J. Roth, C. Morris Smith, Dennis E. Walsh
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Patent number: 5545788Abstract: The present invention relates to a process for alkylating a reformate feedstream containing benzene, toluene, xylenes, and ethylbenzene, said process comprising:1) contacting said reformate feedstream with a hydrocarbon stream comprising C.sub.2 -C.sub.5 olefins in the presence of a catalyst comprising an active form of synthetic porous crystalline MCM-49 under benzene alkylation conditions whereby an effluent stream is produced having a benzene content at least 50 wt % less than that of said feedstream, an octane rating no less than that of said feedstream, and a total liquid product greater than that of said feedstream; and2) collecting the gasoline boiling range fraction of said effluent stream.Type: GrantFiled: December 6, 1994Date of Patent: August 13, 1996Assignee: Mobil Oil CorporationInventors: Jane C. Cheng, Tracy J. Huang
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Patent number: 5453554Abstract: Relatively short chain alkyl aromatic compounds are prepared by alkylating an alkylatable aromatic compound with a relatively short chain alkylating agent under sufficient reaction conditions in the presence of a catalyst comprising zeolite MCM-56. The liquid phase syntheses of ethylbenzene and cumene are particular examples of such MCM-56 catalyzed reactions.Type: GrantFiled: May 26, 1994Date of Patent: September 26, 1995Assignee: Mobil Oil Corp.Inventors: Jane C. Cheng, Anthony S. Fung, Donald J. Klocke, Stephen L. Lawton, Daria N. Lissy, Wieslaw J. Roth, C. Morris Smith, Dennis E. Walsh
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Patent number: 5444172Abstract: There is disclosed a process for producing a monoalkenylbenzene which comprises alkenylating a side chain of an aromatic hydrocarbon compound having at least one hydrogen atom bonded at .alpha.-position of the side chain (such as xylene) with a conjugated diene having 4 or 5 carbon atoms (such as butadiene) in the presence of a catalyst produced by calcining the mixture of a basic potassium compound and alumina and then heat treating the calcined product together with metallic sodium in an atmosphere of an inert gas. According to the aforesaid process, an industrially useful monoalkenylbenzene can be produced in high yield at a low cost with enhanced safety.Type: GrantFiled: December 20, 1993Date of Patent: August 22, 1995Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Makoto Takagawa, Kenji Inamasa, Norio Fushimi, Akio Hashimoto, Takayo Sasaki
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Patent number: 5436381Abstract: There is disclosed a process for producing a monoalkenylbenzene which comprises alkenylating a side chain of an aromatic hydrocarbon compound having at least one hydrogen atom bonded at .alpha.-position of the side chain (such as xylene) with a conjugated diene having 4 or 5 carbon atoms (such as butadiene) in the presence of a catalyst produced by calcining the mixture of potassium hydroxide and aluminum hydroxide and then heat treating the calcined product together with metallic sodium in an atmosphere of an inert gas. According to the aforesaid process, an industrially useful monoalkenylbenzene can be produced in high yield at a low cost with enhanced safety.Type: GrantFiled: December 20, 1993Date of Patent: July 25, 1995Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Makoto Takagawa, Kinji Kato, Norio Fushimi, Ko Kedo
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Patent number: 5371310Abstract: Relatively short chain alkyl aromatic compounds are prepared by alkylating or transalkylating an alkylatable aromatic compound with a relatively short chain alkylating or transalkylating agent under sufficient reaction conditions in the presence of catalyst comprising zeolite MCM-49.Type: GrantFiled: June 16, 1993Date of Patent: December 6, 1994Assignee: Mobil Oil Corp.Inventors: J. Michael Bennett, Clarence D. Chang, Jane C. Cheng, Stephen L. Lawton, Michael E. Leonowicz, Daria N. Lissy, Mae K. Rubin, C. Morris Smith, Dennis E. Walsh
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Patent number: 5347062Abstract: An alkyl-substituted hydrocarbon is prepared by alkylating an aromatic hydrocarbon having at least one hydrogen atom at an alpha-position in a side chain with an olefin in the presence of a solid base which is obtainable by heating an alumina, an alkali metal hydroxide and an alkali metal or an alumina containing at least 1.3% by weight of water and an alkali metal in an inert gas atmosphere at a specific temperature as a catalyst.Type: GrantFiled: February 24, 1993Date of Patent: September 13, 1994Assignee: Sumitomo Chemical Co., Ltd.Inventors: Masami Fukao, Takuo Hibi, Kazuo Kimura, Masahiro Usui, Gohfu Suzukamo
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Patent number: 5344806Abstract: There is disclosed a process for producing a monoalkenyl aromatic hydrocarbon compound which comprises alkenylating a side chain of an aromatic hydrocarbon compound having at least one hydrogen atom bonded at .alpha.-position of the side chain (such as xylene) with a conjugated diene having 4 or 5 carbon atoms (such as butadiene) in the presence of a catalyst comprising the mixture obtained by heat treating metallic sodium together with an alkaline earth metal oxide containing a potassium compound in the atmosphere of an inert gas. According to the aforesaid process, a monoalkenyl aromatic hydrocarbon compound such as industrially useful monoalkenylbenzene can be produced in high yield at a low cost with enhanced safety from a specific aromatic hydrocarbon compound and a specific conjugated diene compound.Type: GrantFiled: January 29, 1993Date of Patent: September 6, 1994Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Norio Fushimi, Kenji Inamasa, Makoto Takagawa
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Patent number: 5334795Abstract: Ethylbenzene is produced by the alkylation of benzene with ethylene in the presence of an alkylation catalyst having a particular structure defined by its X-ray diffraction pattern. A preferred catalyst is the zeolite MCM-22. The process is typically carried out at a temperature of 300.degree. to 1000.degree. F. but the catalyst provides sufficient activity for the reaction to be carried out at temperatures below 700.degree. F. Liquid phase operation is preferred, giving a lower yield of polyethylated products. The use of the selected catalyst also results in a reduction of the xylene impurity level to values below 500 ppm in the product.Type: GrantFiled: October 27, 1992Date of Patent: August 2, 1994Assignee: Mobil Oil Corp.Inventors: Pochen Chu, Michael E. Landis, Quang N. Le
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Patent number: 5324877Abstract: A composition useful for catalyzing alkylation and transalkylation reactions comprises a molecular sieve having alkylation and/or transalkylation activity, an inorganic refractory oxide component and greater than 3.5 weight percent water. Such a catalyst has been found to maintain a long life when used to produce ethylbenzene in an integrated process in which benzene is alkylated with ethylene and transalkylated with diethylbenzene. The catalyst can also be used to produce cumene via an integrated process in which benzene is alkylated with propylene and transalkylated with diisopropylbenzene.Type: GrantFiled: April 22, 1993Date of Patent: June 28, 1994Assignee: Union Oil Company of CaliforniaInventors: Martin West, Suheil F. Abdo
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Patent number: 5321181Abstract: Aromatic compounds are alkylated in a catalytic distillation, wherein the catalyst structure also serves as a distillation component by contacting the aromatic compound with a C.sub.2 to C.sub.10 olefin in the catalyst bed under 0.25 to 50 atmospheres of pressure and at temperatures in the range of 80.degree. C. to 500.degree. C., using as the catalyst a mole sieve characterized as acidic or an acidic cation exchange resin. For example, ethyl benzene is produced by feeding ethylene below the catalyst bed while benzene is conveniently added through the reflux in molar excess to that required to react with ethylene, thereby reacting substantially all of the ethylene and recovering benzene as the principal overhead and ethyl benzene in the bottoms.Type: GrantFiled: May 17, 1993Date of Patent: June 14, 1994Assignee: Chemical Research & Licensing CompanyInventors: Lawrence A. Smith, Jr., Robert P. Arganbright, Dennis Hearn
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Patent number: 5227559Abstract: An alkyl-substituted hydrocarbon is prepared by alkylating an aromatic hydrocarbon having at least one hydrogen atom at an alpha-position in a side chain with an olefin in the presence of a solid base which is obtainable by heating an alumina, an alkali metal hydroxide and an alkali metal or an alumina containing at least 1.3% by weight of water and an alkali metal in an inert gas atmosphere at a specific temperature as a catalyst.Type: GrantFiled: January 7, 1992Date of Patent: July 13, 1993Assignee: Sumitomo Chemical Company, Ltd.Inventors: Masami Fukao, Takuo Hibi, Kazuo Kimura, Masahiro Usui, Gohfu Suzukamo
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Patent number: 5202515Abstract: An alkyl-substituted hydrocarbon is prepared by alkylating an alkyl aromatic hydrocarbon having at least one hydrogen atom at an alpha-position in a side chain with an olefin in the presence of a solid base which is obtainable by heating and reacting an alumina with at least one carbonate of an alkali metal and at least one material selected from the group consisting of potassium and alkali metal hydrides at a temperature of from 180.degree. to 800.degree. C. in an inert gas atmosphere, as a catalyst.Type: GrantFiled: May 14, 1991Date of Patent: April 13, 1993Assignee: Sumitomo Chemical Company, LimitedInventors: Masami Fukao, Takuo Hibi, Kiyoshi Ikimi, Gohfu Suzukamo
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Patent number: 5196623Abstract: A process is provided for the alkylation of aromatic substrates with a C.sub.2 -C.sub.4 alkylating agent over an alkylation catalyst comprising zeolite omega at moderate temperature and pressure conditions to provide liquid phase conditions.The liquid phase alkylation process is carried out using a plurality of series connected reaction stages operated at an average temperature of no more than 300.degree. C. with the interstage injection of the C.sub.2 -C.sub.4 alkylating agent in a manner to maintain at least 2 mole percent of alkylating agent solubilized in the aromatic substrate.The reaction stages of a multistage system are operated at a pressure above the vapor pressure of the aromatic substrate and below the vapor pressure of the alkylating agent at the alkylation reaction conditions. The aromatic substrate and the alkylating agent are supplied to a first of the reaction stages in relative amouns to provide a first mole ratio of aromatic substrate to alkylating agent.Type: GrantFiled: December 16, 1991Date of Patent: March 23, 1993Assignee: Fina Technology, Inc.Inventor: James R. Butler
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Patent number: 5157186Abstract: A process of using a catalyst composition having enhanced effectiveness in coupling an alkene with an aromatic hydrocarbon having an active hydrogen on a saturated .alpha.-carbon is accomplished with a catalyst obtained by treating an alkali metal with an alkali metal carbonate.Type: GrantFiled: January 13, 1992Date of Patent: October 20, 1992Assignee: Ethyl CorporationInventors: James S. Staton, Michael D. Standiford, David A. Rockstraw
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Patent number: 5118896Abstract: An aromatic alkylation process comprising the steps of contacting a hydrocarbon feed comprising an aromatic hydrocarbon with an alkylating agent under liquid phase alkylation condition in the presence of a silica-containing molecular sieve wherein said said catalyst possesses a pore volume of about 0.25-0.50 cc/g in pores having a radius greater than 450 Angstroms and a catalyst particle diameter of not more than about 1/32 of an inch.Type: GrantFiled: October 31, 1990Date of Patent: June 2, 1992Assignee: Amoco CorporationInventors: Edward F. Steigelmann, Terry L. Marker
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Patent number: 5097088Abstract: An alkyl-substituted hydrocarbon is prepared by alkylating an alkylaromatic hydrocarbon having at least one hydrogen atom on an alpha-carbon in a side chain with an olefin in the presence of a solid base which is obtainable by treating an alumina with at least one compound of an alkaline earth metal at a temperature of from 200.degree. to 800.degree. C. and then with at least one compound selected from the group consisting of an alkali metal and an alkali metal hydride in an inert gas at a temperature of from 200.degree. to 800.degree. C.Type: GrantFiled: September 21, 1990Date of Patent: March 17, 1992Assignee: Sumitomo Chemical Company, LimitedInventors: Masami Fukao, Takuo Hibi, Kiyoshi Ikimi, Gohfu Suzukamo
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Patent number: 5087784Abstract: An aromatic alkylation process comprising continuously feeding catalyst particles through at least one substantially vertically-positioned permeable tube disposed in a vessel surrounding said permeable tube, contacting said catalyst particles with at least one aromatic hydrocarbon and at least one alkylating agent under liquid phase alkylation conditions, continuously removing said catalyst particles from a lower end of said tube, and recovering said alkyl-substituted aromatic.Type: GrantFiled: October 31, 1990Date of Patent: February 11, 1992Assignee: Amoco CorporationInventors: Harold S. Primack, Ronald L. Cutshall
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Patent number: 5081323Abstract: A process for the alkylation or transalkylation of an aromatic hydrocarbon which comprises contacting the aromatic hydrocarbon with a C.sub.2 to C.sub.4 olefin alkylating agent or a polyalkyl aromatic hydrocarbon transalkylating agent, under at least partial liquid phase conditions, and in the presence of a catalyst comprising zeolite beta.Type: GrantFiled: November 22, 1989Date of Patent: January 14, 1992Assignee: Chevron Research and Technology CompanyInventors: Robert A. Innes, Stacey I. Zones, Gerald J. Nacamuli
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Patent number: 5043507Abstract: An alkyl-substituted hydrocarbon is prepared by alkylating an alkyl aromatic hydrocarbon having at least one hydrogen atom at an alpha-position in a side chain with an olefin in the presence of a solid base which is obtainable by reacting an alumina with an alkali metal carbonate and/or aluminate and an alkali metal amd/or its hydride in an inert gas atmosphere at a temperature of 180.degree. to 800.degree. C. as a catalyst.Type: GrantFiled: August 29, 1989Date of Patent: August 27, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Masami Fukao, Takuo Hibi, Kiyoshi Ikimi, Gohfu Suzukamo
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Patent number: 5015796Abstract: This invention relates to a process for the alkylation of methylbenzene to produce ethylbenzene and styrene. In this process methylbenzene and methanol are contacted with a catalyst formed from a zeolite and an alkali(ne earth) metal compound wherein said compound is selected from alkaline earth metal compound and a mixture of alkaline earth metal compound and alkali metal compound and wherein the sum of the amount of the alkali(ne earth) metal in the compound plus any metal cation exchanged into the zeolite is in excess of that required to provide a fully metal cation-exchanged zeolite.Type: GrantFiled: December 14, 1989Date of Patent: May 14, 1991Assignee: Shell Oil CompanyInventors: Lynn H. Slaugh, Thomas F. Brownscombe
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Patent number: 5004841Abstract: Aromatic compounds, such as benzene or biphenyl, are alkylated with an alkylating agent having from one to eight carbons atoms, such as propylene, in the presence of an acidic mordenite zeolite catalyst under conditions sufficient to produce a mixture of substituted aromatic compounds enriched in the linear alkylated isomers, such as p-diisopropylbenzene or p,p'-di(isopropyl)biphenyl, respectively. The novel acidic mordenite catalyst is characterized by its silica/alumina molar ratio, its porosity, and a Symmetry Index. The p,p'-disubstituted isomers of aromatic compounds are useful as monomers in the preparation of thermotropic, liquid crystal polymers.Type: GrantFiled: March 14, 1989Date of Patent: April 2, 1991Assignee: The Dow Chemical CompanyInventors: Guo-shuh J. Lee, Juan M. Garces, Joseph J. Maj, Stephen C. Rocke
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Patent number: 4982035Abstract: An alkene selected from ethene, propene, and mixtures thereof is coupled with an aromatic hydrocarbon having an active hydrogen on a saturated alpha-carbon in the presence of a supported potassium or potassium alloy as a catalyst and cesium oxide as a co-catalyst. In a preferred embodiment of the invention, the active hydrogen-containing aromatic hydrocarbon is an alkylbenzene, such as toluene.Type: GrantFiled: June 27, 1989Date of Patent: January 1, 1991Assignee: Ethyl CorporationInventor: R. Scott Smith
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Patent number: 4962254Abstract: An alkyl-substituted hydrocarbon is prepared by alkylating an alkyl aromatic hydrocarbon having at least one hydrogen atom at an alpha-position in a side chain with an olefin in the presence of a solid base which is obtainable by heating an alumina, an alkali metal hydroxide and an alkali metal hydride or an alumina containing at least 1.3% by weight of water and an alkali metal hydride in an inert gas atmosphere at a temperature of 200.degree. to 800.degree. C. as a catalyst.Type: GrantFiled: August 9, 1989Date of Patent: October 9, 1990Assignee: Sumitomo Chemical Company, LimitedInventors: Masami Fukao, Takuo Hibi, Kiyoshi Ikimi, Gohfu Suzukamo
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Patent number: 4950831Abstract: An alkene is coupled with an aromatic hydrocarbon having an active hydrogen on a saturated alpha-carbon in the presence of an unsupported alkali metal as a catalyst under high shear agitation conditions. In preferred embodiments of the invention, the alkene is an alkene of 2-20 carbons, such as ethene or propene; the active hydrogen-containing aromatic hydrocarbon is an alkyl-benzene, such as toluene; the alkali metal is potassium or a potassium alloy; and the high shear agitation conditions are attained by operating a turbine-type impeller at a tip speed of at least about 5 m/sec.Type: GrantFiled: September 28, 1989Date of Patent: August 21, 1990Assignee: Ethyl CorporationInventors: James S. Staton, Ronald A. Turnblad, Jr., Robert B. Agee
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Patent number: 4929783Abstract: An alkene selected from ethene, propene, and mixtures thereof is coupled with an aromatic hydrocarbon having an active hydrogen on a saturated alpha-carbon in the presence of a supported potassium or potassium alloy as a catalyst and an alkaline earth metal oxide as a co-catalyst. In a preferred embodiment of the invention, the active hydrogen-containing aromatic hydrocarbon is an alkylbenzene, such as toluene.Type: GrantFiled: June 27, 1989Date of Patent: May 29, 1990Assignee: Ethyl CorporationInventor: R. Scott Smith
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Patent number: 4922054Abstract: An alkene selected from ethene, propene, and mixtures thereof is coupled with an aromatic hydrocarbon having an active hydrogen on a saturated alpha-carbon in the presence of a supported potassium or potassium alloy as a catalyst and sodium oxide, potassium oxide, rubidium oxide, or a mixture of any two or all three thereof as a co-catalyst. In preferred embodiments of the invention, the active hydrogen-containing aromatic hydrocarbon is an alkylbenzene, such as toluene; and the co-catalyst is sodium oxide.Type: GrantFiled: May 24, 1989Date of Patent: May 1, 1990Assignee: Ethyl CorporationInventor: R. Scott Smith
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Patent number: 4914250Abstract: An alkene selected from ethene, propene, and mixtures thereof is coupled with an aromatic hydrocarbon having an active hydrogen on a saturated alpha-carbon in the presence of a supported potassium or potassium alloy as a catalyst and sodium hydroxide, potassium hydroxide, or a mixture thereof as a co-catalyst. In preferred embodiments of the invention, the active hydrogen-containing aromatic hydrocarbon is an alkylbenzene, such as toluene; and the co-catalyst is a hydroxide or hydroxide mixture formed in situ by adding water to the potassium or potassium alloy.Type: GrantFiled: May 24, 1989Date of Patent: April 3, 1990Assignee: Ethyl CorporationInventor: R. Scott Smith