Attachment To Side-chain, E.g., Telomerization, Etc. Patents (Class 585/452)
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Patent number: 11820743Abstract: The present disclosure belongs to the technical field of chemical separation and purification, and in particular relates to a purification method and device for continuous distillation and separation of an ibuprofen intermediate raw material. The purification method comprises the following steps: carrying out a primary distillation on synthetic liquid to obtain a primary material and recovered 4-methyl-1-pentene, then carrying out a second-stage distillation on the primary material to obtain a second-stage material and a recovered crude toluene product; and carrying out a third-stage distillation on the second-stage material to obtain isobutyl benzene and a recovered crude n-butylbenzene product. Embodiment results show that the purification method provided by the present disclosure is high in product recovery rate and high in product purity, the purity of isobutyl benzene is up to 99.99 wt %, the recovery rate is up to 99.9 wt %, the impurity content is not higher than 50 ppm.Type: GrantFiled: August 5, 2022Date of Patent: November 21, 2023Assignee: Qingdao University Science and TechnologyInventors: Peizhe Cui, Xin Li, Yinglong Wang, Zhaoyou Zhu, Kaiguang Wang, Jianguang Qi, Limei Zhong, Zhonghui Zheng, Wenhui Xu, Jianbo Jia, Deping Du
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Patent number: 11795132Abstract: Provided is an application of a metal hydride/palladium compound system in the preparation of a 1,3-dicarbonyl compound in a cascade reaction of an electron-deficient alkene compound, said reaction comprising the following steps: under the protection of nitrogen, a palladium compound and a metal hydride are suspended and stirred in a solvent, then an electron-deficient alkene compound is added; the mixture reacts at 0° C. to 100° C. for 0.3 to 10 hours; a saturated ammonium chloride aqueous solution is added to stop the reaction, and then extraction, drying by evaporation and purification by column chromatography are performed to obtain the product of 1,3-dicarbonyl compound. The hydride and palladium compound catalysts used in the method are reagents easily obtained in a laboratory; compared with the commonly used methods of hydrogenation with hydrogen gas, the method can be easily operated, and has high safety, mild conditions and high reaction yield.Type: GrantFiled: March 15, 2021Date of Patent: October 24, 2023Assignee: SOOCHOW UNIVERSITYInventors: Shilei Zhang, Yujian Mao
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Patent number: 9903810Abstract: Apparatus and method for the determination of weight fractions of hydrocarbons, water and acid in the acid catalyst phase of petroleum refinery alkylation catalyst streams by flowing the acid catalyst phase through a density detector and a spectrometer cell so that the determination can be made according to first principles. An alternative apparatus and method uses spectroscopy without the density detector.Type: GrantFiled: January 12, 2015Date of Patent: February 27, 2018Assignee: Yokogawa Corporation of AmericaInventor: William Marcus Trygstad
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Patent number: 8796497Abstract: 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: GrantFiled: November 6, 2013Date of Patent: August 5, 2014Assignee: Fina Technology, Inc.Inventors: Sivadinarayana Chinta, Joseph L. Thorman, James R. Butler, Joe Hunter, Taylor Rives
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Patent number: 8450546Abstract: 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: GrantFiled: June 29, 2009Date of Patent: May 28, 2013Assignee: Fina Technology, Inc.Inventors: Sivadinarayana Chinta, Joseph Thorman, James Butler, Joe Hunter, Taylor Rives
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Patent number: 8420876Abstract: This invention provides adducts, mixtures of adducts and oligomers, and/or mixtures of adducts, oligomers, and low molecular weight polymers formed from monovinylaromatic hydrocarbons.Type: GrantFiled: June 6, 2008Date of Patent: April 16, 2013Assignee: Albemarle CorporationInventors: William J. Layman, Jr., Arthur G. Mack, Charles H. Kolich
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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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Patent number: 8314282Abstract: A process for making ethylbenzene and/or styrene by reacting toluene with methane is disclosed. In one embodiment the process can include reacting toluene with methane to form a product stream comprising ethylbenzene and further processing the ethylbenzene to form styrene in an existing styrene production facility.Type: GrantFiled: November 7, 2011Date of Patent: November 20, 2012Assignee: Fina Technology, Inc.Inventors: James R. Butler, Joseph E. Pelati
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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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Patent number: 8269053Abstract: 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: GrantFiled: November 1, 2011Date of Patent: September 18, 2012Assignee: Fina Technology, Inc.Inventor: James R. Butler
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Patent number: 8227652Abstract: 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 180° C. to about 220° C., adding the ethylene and conducting the synthesis reaction at about 130° C. to about 150° C.Type: GrantFiled: March 27, 2008Date of Patent: July 24, 2012Assignee: Albemarle CorporationInventors: Robert W. Nelson, Christopher A. Curtis, Stephen E. Belmont
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Patent number: 8076527Abstract: A process for making ethylbenzene and/or styrene by reacting toluene with methane is disclosed. In one embodiment the process can include reacting toluene with methane to form a product stream comprising ethylbenzene and further processing the ethylbenzene to form styrene in an existing styrene production facility.Type: GrantFiled: March 13, 2008Date of Patent: December 13, 2011Assignee: Fina Technology, Inc.Inventors: James R. Butler, Joseph E. Pelati
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Patent number: 8071836Abstract: 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: GrantFiled: March 13, 2008Date of Patent: December 6, 2011Assignee: Fina Technology, Inc.Inventor: James R. Butler
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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: 6984766Abstract: In a process for reducing the formation of polymers during side-chain alkylation or side-chain alkenylation of alkylaromatic compounds by reaction with olefins or diolefins in the presence of an alkali metal catalyst followed by distillation in order to isolate the alkylated or alkenylated compound, the alkali metal is present in the catalyst on an inorganic support, and the catalyst is mechanically separated from the reaction mixture after the reaction and before the distillation.Type: GrantFiled: August 10, 2001Date of Patent: January 10, 2006Assignee: BASF AktiengesellschaftInventors: Ulrich Steinbrenner, Ralf Böhling, Peter Zehner
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Publication number: 20040106834Abstract: In a process for reducing the formation of polymers during side-chain alkylation or side-chain alkenylation of alkylaromatic compounds by reaction with olefins or diolefins in the presence of an alkali metal catalyst followed by distillation in order to isolate the alkylated or alkenylated compound, the alkali metal is present in the catalyst on an inorganic support, and the catalyst is mechanically separated from the reaction mixture after the reaction and before the distillation.Type: ApplicationFiled: February 12, 2003Publication date: June 3, 2004Inventors: Ulrich Steinbrenner, Ralf Bhling, Peter Zehner
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Publication number: 20040059168Abstract: The invention relates to a process for the preparation of an alkali metal catalyst by mixing an alkali metal with pulverulent, solid potassium carbonate as support, wherein the potassium carbonate has a specific surface area of at least 0.3 m2/g, and to the use thereof for the side-chain alkylation of alkylbenzenes.Type: ApplicationFiled: June 11, 2003Publication date: March 25, 2004Inventor: Ulrich Steinbrenner
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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: 6355603Abstract: Thermal reaction products of maleic anhydride and oligoalkenes are obtainable by oligomerization of linear C8- to C12-1-alkenes, preferably in the presence of a titanium, zirconium or hafnium metallocene catalyst and of an activator based on organoaluminum, organoboron or carbocationic compounds and have a vinylidene double bond content of more than 30% and have a number average molecular weight from 1000 to 20,000. Derivatives thereof with amines or alcohols are used as fuel additives and lubricant additives.Type: GrantFiled: August 29, 2000Date of Patent: March 12, 2002Assignee: BASF AktiengesellschaftInventors: Hans Peter Rath, Helmut Mach
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Publication number: 20010044563Abstract: 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: ApplicationFiled: June 20, 2001Publication date: November 22, 2001Inventors: Ulrich Steinbrenner, Eugen Gehrer
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Patent number: 6100437Abstract: An alkylbenzene is alkylated with an alkene, in the presence of a sodium/potassium alloy catalyst, on a saturated carbon atom which is alpha to the ring at temperatures which are lower than the temperatures used in a current commercial process. In a pre-alkylation reaction, the catalyst is reacted with a compound which has a saturated carbon atom alpha to a double bond in order to form a catalytic species. Higher amounts of catalyst are used in the pre-alkylation reaction than in the analogous reaction of the current commercial process. Following alkylation, the phase which contains the alkylation product is separated from the phase which contains the catalytic species. The process produces less isomeric and other soluble byproducts, and enables the efficacious production of longer chain alkylbenzenes without the formation of insoluble tars characteristic of the current commercial process.Type: GrantFiled: July 10, 1998Date of Patent: August 8, 2000Assignee: Albemarle CorporationInventors: David J. Koehl, Edward A. Burt, Patrick T. Ward
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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: 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: 5789639Abstract: A process for manufacturing an alkenyl compound which comprises reacting an alkylbenzene and 1,3-butadiene in the presence of metallic sodium or a combination of metallic sodium and an oxide, a hydroxide, or a salt of potassium, rubidium or an alkaline earth metal, or a mixture of these under a pressure of 1 kPa (gauge) to 30 MPa (gauge). The process can produce alkenyl compound which is an industrially valuable compound as a raw material for the manufacture of naphthalenedicarboxylic acid, a highly useful raw material of polymers, at a high yield using a small amount of metallic sodium.Type: GrantFiled: July 14, 1995Date of Patent: August 4, 1998Assignees: Cosmo Oil Co., Ltd., Petroleum Energy CenterInventor: Takashi Itoh
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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: 5527977Abstract: Their is disclosed a process for producing a monoalkenyl aromatic hydrocarbon compound (e.g. 5-(o-tolyl)-2-pentene) which comprises the steps of alkenylating a side chain of an aromatic hydrocarbon compound having at lease one hydrogen atom bonded to .alpha.-position of the side chain (e.g. alkylbenzene) by the use of a conjugated diene having 4 to 5 carbon atoms (e.g. 1-3 butadiene) in the presence an alkali metal-based catalyst supported on a carrier; removing at least part of the catalyst from the resultant reaction product by separating the same; inactivating and optionally removing the catalyst contained in the reaction product; and thereafter distilling the reaction produce in liquid form to separate and recover the objective monoalkenyl aromatic hydrocarbon compound.Type: GrantFiled: June 27, 1994Date of Patent: June 18, 1996Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Makoto Takagawa, Kenichi Nakamura, Kinji Kato, Akio Hashimoto, Takayo Sasaki
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Patent number: 5523504Abstract: A process for manufacturing an alkenyl aromatic compound which is an industrially valuable compound as a raw material for the manufacture of naphthalenedicarboxylic acid, a highly useful raw material of polymers. The process comprises reacting an alkylbenzene and 1,3-butadiene in the presence of (a) metallic sodium, (b) at least one compound selected from the group consisting of salts of potassium, salts of rubidium, and salts of an alkaline earth metal, and (c) an aromatic compound capable of producing a charge-transfer complex together with metallic sodium. High purity alkenyl aromatic compound can be manufactured at a high yield using a simple procedure.Type: GrantFiled: September 15, 1994Date of Patent: June 4, 1996Assignees: Cosmo Oil Co., Ltd., Petroleum Energy CenterInventor: Takashi Itoh
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Patent number: 5510563Abstract: 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: December 29, 1993Date of Patent: April 23, 1996Assignee: Amoco CorporationInventors: Thomas G. Smith, John M. Weis, Yenamandra Viswanath
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Patent number: 5488194Abstract: A process is provided for selective catalytic conversion of certain hydrocarbon feedstocks to product rich in para-dialkyl substituted benzenes. The catalyst required in the process comprises a crystalline material having the structure of PSH-3, MCM-22 or MCM-49, or a mixture of said crystalline materials, said crystalline material having been treated with one or more monomeric or polymeric siloxane compounds which decompose to oxide or non-oxide ceramic or solid-state carbon species.Type: GrantFiled: May 16, 1994Date of Patent: January 30, 1996Assignee: Mobil Oil Corp.Inventors: Jeffrey S. Beck, Ralph M. Dessau
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Patent number: 5475177Abstract: Process for the synthesis of alkylated aromatic hydrocarbons containing a saturated alkyl chain comprising at least four carbon atoms, according to which an aromatic hydrocarbon substituted by a saturated short-chain alkyl group comprising one to three carbon atoms is reacted with an olefin in the presence of a catalyst which comprises at least one alkali metal or one alkali metal hydride impregnated on an alumina support and the catalyst is prepared in the reaction medium in the presence of the aromatic hydrocarbon containing a short alkyl chain by mixing anhydrous alumina with the alkali metal hydride or with the alkali metal, the ratio by weight of the alkali metal or of the alkali metal hydride to the alumina support being between 0.6 and 1.8. Use of the process for the synthesis of tert-amylbenzene by alkylation of cumene with ethylene.Type: GrantFiled: May 19, 1994Date of Patent: December 12, 1995Assignee: Solvay Interox (Societe Anonyme)Inventor: Jean-Pierre Ganhy
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Patent number: 5475176Abstract: The present invention relates to a process for preparing vinyl-substituted aromatic compounds of the formula (I) Ar--CH.dbd.CH.sub.2, where Ar is a phenyl group that may bear 1 to 5 substituents, naphthyl or anthryl or a naphthyl radical bearing 1 to 7 substituents or an anthryl radical bearing 1 to 8 substituents, or a mononuclear five-, six- or seven-membered heterocyclic aromatic group which contains an oxygen atom and/or one or two nitrogen atoms in the ring and may bear 1 to 5 substituents, wherein an arylamine of the formula (II) Ar--NH.sub.2, where Ar has the aforementioned meaning, is reacted in an organic acid with an organic nitrite of the formula (III) R--ONO, where R is an alkyl group having 1 to 18 carbon atoms, a phenyl radical which may bear 1 to 3 alkyl groups each having 1 to 4 carbon atoms, or is an alkylcarbonyl group having 2 to 5 carbon atoms, and ethylene in an organic solvent in the presence of a palladium(0) of palladium(II) compound at temperatures of 0.degree. to 35.degree. C.Type: GrantFiled: April 4, 1994Date of Patent: December 12, 1995Assignee: Hoechst AktiengesellschaftInventors: Matthias Beller, Heinz Strutz
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Patent number: 5461180Abstract: A process is disclosed for the catalytic norbornylation of aromatics comprising the steps of contacting norborene and an aromatic hydrocarbon with a solid catalyst comprising a porous crystalline material having a Constraint Index of from about 0.1 to about 12 under norbornylation conditions to evolve a product containing norbornylated aromatics.Type: GrantFiled: May 5, 1994Date of Patent: October 24, 1995Assignee: Mobil Oil CorporationInventors: Costandi A. Audeh, James R. Boulton, Ross A. Kremer, Yusheng Xiong
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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: 5436361Abstract: A process for synthesizing enediynes is provided. Specifically, the formed enediynes contain a hex-3-ene-1,5-diynyl group. Production of the enediynes involves adding a base to a propargylic halide in the presence of a chelating agent, which causes a carbenoid coupling-elimination sequence of the propargylic halides. A carbenoid destabilizing agent can also be added to the reaction mixture in order to enhance yield. Acyclic and cyclic enediynes can be synthesized according to this process. The enediynes are useful compounds that can be used in a variety of applications including use in the production of anti-tumor agents.Type: GrantFiled: April 22, 1994Date of Patent: July 25, 1995Assignee: Clemson UniversityInventors: Graham B. Jones, Robert S. Huber
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Patent number: 5414174Abstract: There is disclosed a side-chain alkylation reaction wherein an alkyl aromatic compound having a benzyl hydrogen is reacted with unsaturated hydrocarbons to produce a desired target product with excellent selectivity. The reaction is conducted in the presence of an alkyl ether and an alkaline metal catalyst. In comparison with conventional methods, it was observed that target selectivity was improved remarkably when equimolar addition of the reactants was employed, that very little catalyst was needed, and that the catalyst could be treated as a linear or uniform system, allowing the reaction to be easily scaled to meet industrial requirements.Type: GrantFiled: June 7, 1993Date of Patent: May 9, 1995Assignee: Sumikin Chemical Co., Ltd.Inventors: Toshio Sato, Ikuo Ito, Hiromichi Yamaguchi, Kyoichi Takeda
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Patent number: 5367098Abstract: 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 an .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 a mixture obtained by heat treating metallic sodium together with a mixture of an aluminum oxide and a potassium compound in an inert gas atmosphere. The process produces a commercially useful monoalkenyl aromatic hydrocarbon compounds in a high yields and at a low cost with enhanced safety.Type: GrantFiled: April 15, 1993Date of Patent: November 22, 1994Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Norio Fushimi, Ko Kedo, Kenji Inamasa, Makoto Takagawa
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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: 5334794Abstract: 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 an .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 a mixture obtained by heat treating metallic sodium together with a mixture of a zirconium oxide and a potassium compound in an inert gas atmosphere. An industrially useful monoalkenyl aromatic hydrocarbon compound is produced in a high yield at a low cost with enhanced safety from a specific aromatic hydrocarbon compound and a specific conjugated diene compound.Type: GrantFiled: April 15, 1993Date of Patent: August 2, 1994Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Norio Fushimi, Ko Kedo, Kenji Inamasa, Makoto Takagawa
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Patent number: 5334796Abstract: An improved process for alkylating an alkylaromatic having at least one benzylic hydrogen atom with an olefinic compound comprising contacting the alkylaromatic under liquid phase conditions with an olefinic compound in the presence of at least one alkali metal activated by amine compound.Type: GrantFiled: February 19, 1993Date of Patent: August 2, 1994Assignee: Amoco CorporationInventors: Lawrence D. Lillwitz, Anne M. Karachewski
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Patent number: 5329058Abstract: In a process for producing an alkenylbenzene by the reaction of an alkylbenzene having 8 or more carbon atoms and a conjugated diolefin, the improvement in which the reaction is performed in the presence of a catalyst obtained by dispersing (a) an alkali metal and (b) potassium carbonate and/or potassium hydroxide in the presence of (c) an aromatic hydrocarbon having at least a substituent with a double bond.Type: GrantFiled: October 23, 1992Date of Patent: July 12, 1994Assignee: Teijin LimiedInventors: Keizo Shimada, Koji Sumitani, Seiji Itoh, Kazuhiro Sato
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Patent number: 5288936Abstract: Process for the synthesis of aromatic alkylated hydrocarbons with a saturated alkyl chain including at least four carbon atoms, according to which an aromatic hydrocarbon, replaced by an alkyl group with a short saturated chain comprising one to three carbon atoms, is made to react with an olefin in the presence of a catalyst made up of at least one alkaline metal or a alkaline metal hydride impregnated on an alumina support. The process is characterised by the fact that the catalyst is prepared in the reaction medium in the presence of the aromatic hydrocarbon with a short alkyl chain by mixing anhydrous alumina with the alkaline metal hydride or with the alkaline metal, and then the olefin is introduced in order to start the reaction.Type: GrantFiled: January 24, 1992Date of Patent: February 22, 1994Assignee: Interox (Societe Anonyme)Inventors: Jean-Pierre Ganhy, Pierre Jacobs, Marleen Baes, Johan Martens
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Patent number: 5276227Abstract: Liquid hydrocarbon lubricant viscosity index improver compositions are disclosed having high shear stability. The compositions comprise the homopolymer or copolymer product of the oligomerization of C.sub.3 to C.sub.5 alpha-olefin or mixtures thereof, with or without ethylene as co-monomer. The process is carried out under oligomerization conditions in contact with a reduced valence state Group VIB metal catalyst on porous support. The viscosity index improver of the invention has a regio-irregularity of at least 20%, weight average molecular weight between 6,000 and 30,000 and molecular weight distribution between 2 and 5.Type: GrantFiled: February 3, 1992Date of Patent: January 4, 1994Assignee: Mobil Oil CorporationInventors: Margaret M. Wu, Alice S. Chu
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Patent number: 5243116Abstract: Alkylated benzenes such as ethylbenzene and cumene are produced by alkylation and/or transalkylation in the presence of an acidic mordenite zeolite catalyst having a silica/alumina molar ratio of at least 30:1 and a crystalline structure which is determined by X-ray diffraction to be a matrix of Cmcm symmetry having dispersed therein domains of Cmmm symmetry.Type: GrantFiled: December 22, 1989Date of Patent: September 7, 1993Assignee: The Dow Chemical CompanyInventors: Guo-shuh J. Lee, Juan M. Garces, Garmt R. Meima, Matheus J. M. van der Aalst
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Patent number: RE34706Abstract: The title compounds can be prepared by reaction of a styrene derivative with ethylene in the presence of a nickel catalyst which carries a phosphorus-oxygen chelate ligand, at a temperature of 20.degree. to 160.degree. C. and an ethylene pressure of 1 to 200 bar. Styrene derivatives extended with ethylene, of the formula ##STR1## in which R.sup.19 denotes hydrogen, C.sub.1 -C.sub.4 -alkyl, vinyl or chlorine and R.sup.38 denotes C.sub.1 -C.sub.4 -alkenyl, C.sub.2 -C.sub.7 -acyl, flourine, chlorine or bromine andm assumes values of 4-104,with the exception of compounds wherein R.sup.19 denotes hydrogen and R.sup.38 denotes i-butyl or benzoyl, and m assumes the value 4, are new.Type: GrantFiled: June 29, 1993Date of Patent: August 23, 1994Assignee: Bayer AktiengesellschaftInventor: Karl-Heinz A. O. Starzewski