Plural Compounds Of Different Weight Become Midweight Compound, I.e., Averaging Patents (Class 585/474)
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Patent number: 11179714Abstract: Disclosed is an in-situ preparation method for a catalyst for Reaction I: methanol and/or dimethyl ether with toluene are used to prepare light olefins and co-produce para-xylene and/or Reaction II: methanol and/or dimethyl ether with benzene are used to prepare at least one of toluene, para-xylene and light olefins, comprising: contacting at least one of a phosphorus reagent, a silylation reagent and water vapor with a molecular sieve in a reactor to prepare, in situ, the catalyst for the Reaction I and/or the Reaction II, wherein the reactor is a reactor of the Reaction I and/or the Reaction II. By directly preparing a catalyst in a reaction system, the entire chemical production process is simplified, the catalyst preparation and transfer steps are saved, and the operation thereof is easy. The catalyst prepared in situ can be directly used for in situ reactions.Type: GrantFiled: April 27, 2017Date of Patent: November 23, 2021Assignee: DALIAN INSTITUTE OF CHEMICAL PHYSICS, CHINESE ACADEMY OF SCIENCESInventors: Zhongmin Liu, Zhengxi Yu, Shukui Zhu, Yue Yang
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Patent number: 10647932Abstract: Process and apparatuses for producing benzene and para-xylene from a reformate stream is provided. The process comprises separating the reformate stream to provide a first stream comprising C4 and lighter hydrocarbons and a second stream comprising aromatic hydrocarbons. The second steam is provided to a reformate splitter to provide a reformate bottoms stream comprising C8+ aromatic hydrocarbons and a reformate overhead stream comprising C7? aromatic hydrocarbons. The reformate overhead stream is passed to an aromatics extraction unit to provide an aromatics extract stream comprising benzene and toluene and a raffinate stream comprising non-aromatic hydrocarbons. The reformate bottoms stream and one of the first stream and the raffinate stream is passed to an olefin reduction zone, wherein the reformate bottoms stream and one of the first stream and the raffinate stream are contacted with an olefin saturation catalyst under olefin saturation conditions to produce an olefin-treated reformate stream.Type: GrantFiled: May 23, 2018Date of Patent: May 12, 2020Assignee: UOP LLCInventors: Jalesh Kalra, Robert J. L. Noe
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Patent number: 9079118Abstract: Two or three strippers are used to strip three hydroprocessed effluent streams, perhaps from a slurry hydrocracking reactor, separated by temperature instead of a single stripper to preserve separations previously made and conserving energy and reducing vessel size. A cold stripped stream may be taken as a diesel blending stock without further fractionation.Type: GrantFiled: March 15, 2013Date of Patent: July 14, 2015Assignee: UOP LLCInventors: Mark Van Wees, David M. Bowman, Xin X. Zhu
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Patent number: 8937205Abstract: A hydrocarbon upgrading process is described in which a hydrocarbon feed is treated in at least one of a steam cracker, catalytic cracker, coker, hydrocracker, and reformer under suitable conditions to produce a first stream comprising aliphatic and aromatic hydrocarbons. A second stream comprising C6-C9 aliphatic and aromatic hydrocarbons is recovered from the first stream and aliphatic hydrocarbons are removed from at least part of the second stream to produce an aliphatic hydrocarbon-depleted stream. The aliphatic hydrocarbon-depleted stream is then dealkylated and/or transalkylated and/or cracked (D/T/C) by contact with a catalyst under suitable reaction conditions to produce a third stream having an increased benzene and/or toluene content compared with said aliphatic hydrocarbon-depleted stream and a light paraffin by-product. Benzene and/or toluene from the third stream is then methylated with a methylating agent to produce a xylene-enriched stream.Type: GrantFiled: May 7, 2012Date of Patent: January 20, 2015Assignee: ExxonMobil Chemical Patents Inc.Inventors: Larry L. Iaccino, Glenn C. Wood, Jesus A. Ramos, Lane L. McMorris
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Publication number: 20140094633Abstract: A process for transalkylation of polyalkylated aromatic components can include providing a transalkylation reaction zone containing a transalkylation catalyst. A feedstock can be introduced into an inlet of the transalkylation reaction zone and into contact with the transalkylation catalyst. The feedstock can include a polyalkylated aromatic component derived from an aromatic substrate. The aromatic substrate can be supplied to the transalkylation reaction zone. The transalkylation reaction zone can be operated at temperature and pressure conditions sufficient to cause disproportionation of the polyalkylated aromatic component to produce a disproportionation product having a reduced polyalkylated aromatic content and an enhanced monoalkylated aromatic content. The disproportionation product can be withdrawn from the transalkylation reaction zone. Amounts of nitrogen containing compounds in the aromatic substrate can be monitored in a range of from 15 to 35 wppm by dry colorimetry.Type: ApplicationFiled: December 5, 2013Publication date: April 3, 2014Applicant: TOTAL PETROCHEMICALS FRANCEInventor: Jean-Bernard Cary
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Patent number: 8431758Abstract: Processes for increasing overall aromatics and xylenes yield in an aromatics complex are provided. A C8+ aromatics stream from an aromatics-rich reformate is separated into a C8 aromatics fraction and a C9+ aromatics fraction comprising higher alkyl group-substituted C9 and C10 aromatics. The C9+ aromatics fraction is separated into a lighter boiling, higher alkyl group-substituted C9 or C9/C10 aromatics fraction and a heavier boiling, C10+ or C11+ aromatics fraction. The lighter boiling, higher alkyl group-substituted C9 or C9/C10 aromatics fraction is isomerized to convert a portion of the higher alkyl group-substituted C9 or C9/C10 aromatics therein into methyl-enriched C9 aromatics or methyl-enriched C9/C10 aromatics. The methyl-enriched C9+ aromatics stream comprising the methyl-enriched C9+ aromatics stream or the methyl-enriched C9/C10 aromatics is transalkylated with a toluene-containing stream.Type: GrantFiled: September 16, 2010Date of Patent: April 30, 2013Assignee: UOP LLCInventors: Stanley J. Frey, Jason T. Corradi, Gregory Werba
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Publication number: 20120271084Abstract: Methods are disclosed for producing C8 aromatic hydrocarbons. Representative methods comprise fractionating a transalkylation effluent, exiting a transalkylation reaction zone and comprising C8 and C9 aromatic hydrocarbons, to provide a C8 aromatic hydrocarbon-enriched fraction and a C9 aromatic hydrocarbon-enriched fraction. The methods may further comprise (i) recycling the C9 aromatic hydrocarbon-enriched fraction to the transalkylation reaction zone and/or (ii) separating, in a xylene separation zone, isomers of C8 aromatic hydrocarbons in the C8 aromatic hydrocarbon-enriched fraction, into a para-xylene-enriched extract and a para-xylene-depleted raffinate. Performance in the transalkylation reaction zone is improved and/or downstream processing requirements in an aromatics complex are mitigated.Type: ApplicationFiled: April 22, 2011Publication date: October 25, 2012Applicant: UOP LLCInventors: ROBERT HAIZMANN, PAUL ALVIN SECHRIST
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Patent number: 8148592Abstract: The present invention relates to a method for performing catalytic transalkylation between long-chain dialkyl benzenes and benzene in order to obtain monoalkyl benzenes. As dialkyl benzene source, this method employs the by-products of a method for alkylation of benzene with linear C9-C16 monoolefins.Type: GrantFiled: May 8, 2006Date of Patent: April 3, 2012Assignee: Cepsa Quimica, S.A.Inventors: José Luis Goncalvez De Almeida, José Luis Berna Tejero
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Patent number: 7727490Abstract: One exemplary embodiment can include an aromatic production apparatus. The aromatic production apparatus can include a first fractionation zone, a second fractionation zone, and a third fractionation zone. Generally, the first fractionation zone can provide a stream rich in an aromatic C8? and a stream rich in an aromatic C9, the second fractionation zone can separate at least one of benzene and optionally toluene from a transalkylation zone effluent and provide a feed to the first fractionation zone, and the third fractionation zone can receive the stream rich in the aromatic C8? from the first fractionation zone. An effluent from the third fractionation zone can be directly comprised in a para-xylene-separation zone feed to a para-xylene-separation zone.Type: GrantFiled: August 17, 2007Date of Patent: June 1, 2010Assignee: UOP LLCInventor: Lubo Zhou
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Patent number: 7405335Abstract: Processes and apparatus are provided that provide high yields of xylenes per unit of aromatic-containing feed while enabling a high purity benzene co-product to be obtained without the need for an extraction or distillation to remove C6 naphthenes. The processes of this invention include a transalkylation section and a disproportionation section in the benzene and toluene-containing feed is directly provided to the transalkylation section and in which a benzene recycle loop in the transalkylation section isolates the disproportionation section from C6 naphthenes.Type: GrantFiled: June 28, 2006Date of Patent: July 29, 2008Assignee: UOP LLCInventors: Edward M. Casey, Patrick J. Silady, Antoine Negiz, Gregory R. Werba
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Patent number: 7151199Abstract: Hydrocarbon or oxygenate conversion process in which a feedstock is contacted with a non zeolitic molecular sieve which has been treated to remove most, if not all, of the halogen contained in the catalyst. The halogen may be removed by one of several methods. One method includes heating the catalyst in a low moisture environment, followed by contacting the heated catalyst with air and/or steam. Another method includes steam-treating the catalyst at a temperature from 400° C. to 1000° C. The hydrocarbon or oxygenate conversion processes include the conversion of oxygenates to olefins, the conversion of oxygenates and ammonia to alkylamines, the conversion of oxygenates and aromatic compounds to alkylated aromatic compounds, cracking and dewaxing.Type: GrantFiled: June 10, 2002Date of Patent: December 19, 2006Assignee: ExxonMobil Chemical Patents Inc.Inventors: Luc Roger Marc Martens, Stephen N. Vaughn, Albert Edward Schweizer, John K. Pierce, Shun Chong Fung
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Patent number: 6573415Abstract: Process for the mono alkylation of a hydrocarbon substrate containing aromatic hydrocarbon compounds comprising contacting the aromatic substrate with an alkylating agent consisting of a mixture of olefinic compounds and poly-alkylated aromatic compounds in presence of a fluorinated sulphonic acid.Type: GrantFiled: August 20, 2001Date of Patent: June 3, 2003Assignee: Haldor Topsoe A/SInventors: Sven Ivar Hommeltoft, Karsten Laurents
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Patent number: 6207871Abstract: There is provided a process for producing high-purity meta-xylene by converting a hydrocarbon feedstream comprising at least about 5 wt % ethylbenzene and at least about 20 wt % meta-xylene, over a single molecular sieve catalyst under ethylbenzene conversion conditions sufficient to provide a primary product stream depleted of more than 50% of the ethylbenzene present in the feedstream. The process can further comprise stripping benzene and/or toluene by-products from the primary product stream to provide a secondary product stream comprising at least about 75 wt % mixed ortho-xylene and meta-xylene; and splitting the secondary product stream by removing substantially all of the ortho-xylene present therein to provide a tertiary product stream comprising at least about 95 wt % meta-xylene.Type: GrantFiled: December 19, 1997Date of Patent: March 27, 2001Assignee: Mobil Oil CorporationInventors: Stuart D. Hellring, David L. Stern
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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: 6008424Abstract: A process for the transalkylation of benzene, toluene and alkylaromatic hydrocarbons containing nine and ten carbon atoms form alkylaromatic hydrocarbons containing eight carbon atoms has been developed. The fixed bed reaction and adsorption zone contains a transalkylation catalyst and an adsorbent effective to selectively adsorb C.sub.9 and C.sub.10 alkylaromatic hydrocarbon reactants relative to the C.sub.8 alkylaromatic hydrocarbon products. Hydrogen and a desorbent are introduced to a first portion of the zone and an effluent containing at least one C.sub.8 alkylaromatic hydrocarbon product is withdrawn from a second portion of the zone. After a period of time, the desorbent is redirected to the second portion of the zone and concurrently the effluent containing at least one C.sub.8 alkylaromatic hydrocarbon product is withdrawn from the first portion of the zone.Type: GrantFiled: October 19, 1998Date of Patent: December 28, 1999Assignee: UOP LLCInventors: Herman A. Zinnen, Maureen L. Bricker, Charles P. McGonegal
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Patent number: 5952536Abstract: A gas phase, aromatics transalkylation process that comprises contacting a stream containing aromatic hydrocarbons with a catalyst comprising a zeolite selected from the group consisting of SSZ-26, Al-SSZ-33, CIT-1, SSZ-35, and SSZ-44 in the presence of added hydrogen and in the gas phase, to produce transalkylated product. The aromatics stream comprises one or more aromatic hydrocarbons, one of the hydrocarbons having at least one alkyl group attached thereto, the alkyl group comprising a C1, C2, C3 or C4 hydrocarbyl group. A preferred aromatics transalkylation process comprises contacting toluene or benzene or a mixture thereof with a stream containing trimethylbenzene in the presence of added hydrogen. The catalyst preferably contains a mild hydrogenation metal, such as nickel or palladium.Type: GrantFiled: April 2, 1998Date of Patent: September 14, 1999Assignee: Chevron Chemical Co. LLCInventors: Gerald J. Nacamuli, Roger F. Vogel, Stacey I. Zones
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Patent number: 5919995Abstract: The invention concerns the use of a catalyst for the dismutation of alkylaromatic hydrocarbons, 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 is a composite comprising at least one zeolite with structure type mazzite, at least partially in its acid form, at least one zeolite with structure type mordenite, at least partially in its acid form, at least one matrix and, optionally, at least one element selected from the group formed by groups IB and VIII of the periodic classification of the elements.Type: GrantFiled: February 7, 1997Date of Patent: July 6, 1999Assignee: Institut Fran.cedilla.ais du PetroleInventors: Fabio Alario, Eric Benazzi
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Patent number: 5877373Abstract: A process for the transalkylation of benzene, toluene and alkylaromatic hydrocarbons containing 9 and 10 carbon atoms and at least one methyl or ethyl group to form alkylaromatic hydrocarbons containing 8 carbon atoms has been developed. The benzene, toluene, and alkylaromatic hydrocarbon reactants are introduced to a fixed bed reaction and adsorption zone operating under conditions effective for transalkylation and containing a catalyst effective to transalkylate the alkylaromatic hydrocarbons and benzene, and an adsorbent effective to selectively adsorb C.sub.9 and C.sub.10 alkylaromatic hydrocarbon reactants relative to the C.sub.8 alkylaromatic hydrocarbon products. Hydrogen and a desorbent capable of desorbing the C.sub.9 and C.sub.10 alkylaromatic hydrocarbons from the adsorbent is introduced to a first portion of the reaction and adsorption zone and an effluent containing at least one C.sub.8 alkylaromatic hydrocarbon product is withdrawn from a second portion of the reaction and adsorption zone.Type: GrantFiled: May 5, 1997Date of Patent: March 2, 1999Assignee: UOP LLCInventors: Herman A. Zinnen, Charles P. McGonegal
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Patent number: 5789641Abstract: The invention concerns the dismutation of alkylaromatic hydrocarbons, preferably the dismutation of toluene to produce benzene and xylenes, and/or the transalkylation of alkylaromatic hydrocarbons, preferably the transalkylation of toluene and trimethylbenzenes to produce xylenes, in a reaction zone comprising at least two catalytic beds each comprising a different catalyst, one of the catalysts containing at least one zeolite with mordenite type structure, at least partially in its acid form, and the other catalyst containing at least one zeolite with mazzite type structure, at least partially in its acid form, each catalyst containing at least one matrix and, optionally, at least one element selected from the group formed by groups IB and VIII of the periodic classification of the elements.Type: GrantFiled: February 6, 1997Date of Patent: August 4, 1998Assignee: Institut Francais du PetroleInventors: Fabio Alario, Eric Benazzi
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Patent number: 5773678Abstract: The invention concerns the use of a catalyst comprising at least one zeolite having a mazzite type structure in its acid form, the catalytic properties of the catalyst having been modified by depositing, on the external surface of the crystals, at least one metal selected from metals from group IIa of the periodic classification of the elements, such as Be, Mg, Ca, Sr or Ba, group IVb, such as Ti, Zr or Hf, group IIb such as Zn, Cd or Hg and group IVa such as Ge, Sn or Pb, said catalyst also comprising at least one matrix and, optionally at least one element selected from the group formed by IB and VIII of the periodic classification of the elements, for the dismutation of alkylaromatic hydrocarbons, 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.Type: GrantFiled: February 7, 1997Date of Patent: June 30, 1998Assignee: Institut Francais du PetroleInventors: Eric Benazzi, Fabio Alario
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Patent number: 5744673Abstract: The present invention relates to a zeolite beta catalyst characterized by critical limits of weak and strong acid species and exceptionally high catalytic activity. The catalyst is activated at a temperature effective to substantially reduce the concentration of strong acid species, i.e., hydronium cations, without substantially reducing the concentration of weak acid species, i.e., hydroxoaluminum cations, preferably following a calcining step wherein a synthesized zeolite beta catalyst containing a templating agent is calcined at a temperature in the range of from about 200.degree. to 1000.degree. C. in order to remove a substantial portion of the catalyst templating agent and an ion-exchanging step wherein the calcined catalyst is ion-exchanged with a salt solution containing at least one hydrogen forming cation selected from NH.sub.4.sup.+ and quaternary ammonium.Type: GrantFiled: December 20, 1996Date of Patent: April 28, 1998Assignee: UOPInventors: Gary W. Skeels, Edith M. Flanigen
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Patent number: 5670704Abstract: A method for the highly selective production of 2,6-dimethlynaphthalene by the transmethylation of naphthalene or 2-methylnaphthalene by the use of a specific acid catalyst and a highly regeospecific methylating agent.Type: GrantFiled: June 26, 1990Date of Patent: September 23, 1997Assignee: Amoco CorporationInventors: Gary P. Hagen, Deborah T. Hung
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Patent number: 5625103Abstract: There is provided a continuous toluene disproportionation process to selectively produce para-xylene. The process includes a steady-state of operation, wherein the conversion of toluene and selectivity to para-xylene is maintained at essentially constant target levels. Prior to such a steady-state of operation, the reaction is conducted under a relatively high temperature.Type: GrantFiled: May 15, 1995Date of Patent: April 29, 1997Assignee: Mobil Oil CorporationInventors: Jeevan S. Abichandani, Jeffrey S. Beck, Ronald H. Fischer, Ivy D. Johnson, David L. Stern
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Patent number: 5522984Abstract: This invention relates to a novel zeolite which has the crystal structure of zeolite beta. The novel zeolite SN-beta has a unique infrared absorbance spectrum, shows enhanced activity for transalkylation of di-isopropyl-benzene and shows less deactivation for cumene synthesis. The zeolite beta is prepared by taking an as-synthesized zeolite beta, steam treating it and then ammonium ion treating it to give a zeolite SN-beta with enhanced catalytic properties.Type: GrantFiled: May 30, 1995Date of Patent: June 4, 1996Assignee: UOPInventors: Gregory J. Gajda, Richard T. Gajek
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Patent number: 5227556Abstract: A process for turbulently flowing together reactants in uniform proportions in a reactor vessel. A process for producing ethylbenzene by reacting ethylene and benzene in the presence of a catalyst in a reactor vessel from which useful heat generated by the reaction is transferred to a heat transfer medium flowing through the reactor and in which the reaction occurs in a relatively short time period. In one embodiment, polyethylbenzenes produced in the reactor vessel are not recycled into the vessel. A reactor for a reaction of reactant materials that are uniformly and turbulently mixed together.Type: GrantFiled: April 17, 1990Date of Patent: July 13, 1993Assignee: The Dow Chemical CompanyInventors: James H. Benton, John B. Ivy, Jack Broodo, Kirk A. Leissner, Ellroy G. Fox
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Patent number: 5210355Abstract: A method for the highly selective production of 2,6-methylethylnaphthalene involving the use of a specific acid catalyst and a highly regeospecific ethylating agent.Type: GrantFiled: June 26, 1990Date of Patent: May 11, 1993Assignee: Amoco CorporationInventors: Gary P. Hagen, Thomas G. Smith
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Patent number: 5177286Abstract: A method for the highly selective production of a p-alkyltoluene or 4,4'-alkylmethylbiphenyl involving the use of a specific Lewis acid catalyst and a highly regeospecific methylating agent.Type: GrantFiled: June 26, 1990Date of Patent: January 5, 1993Assignee: Amoco CorporationInventors: Gary P. Hagen, Deborah T. Hung
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Patent number: 5171917Abstract: A method for the highly selective production of a p-alkylethylbenzene or 4,4'-alkylethylbiphenyl involving the use of a Lewis acid or Bronsted acid alkylation catalyst and a highly regiospecific ethylating agent.Type: GrantFiled: June 26, 1990Date of Patent: December 15, 1992Assignee: Amoco CorporationInventors: Gary P. Hagen, Deborah T. Hung
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Patent number: 5110778Abstract: Boron, aluminum and gallium C.sub.1 -C.sub.18 perfluoroalkane-sulfonates (CF.sub.3 (CF.sub.2).sub.n SO.sub.3).sub.3 M (M=B, A1, Ga; n=0-17) as well as perfluororesin sulfonates such as Nafionates are new, highly effective Friedel-Crafts catalysts. In contrast to volatile aluminum and boron trihalides, the Group III-B perfluoroalkanesulfonates are generally of low or no volatility and, except for boron triflate and some of its homologs, only sparingly soluble incommon organic solvents. This allows their use as solid or supported Friedel-Crafts catalysts of wide utility and scope in continuous heterogenous catalytic processes. At the same time, boron triflate and related lower perfluoroalkanesulfonates are particularly efficient soluble catalysts in solution reactions.Type: GrantFiled: October 23, 1987Date of Patent: May 5, 1992Inventor: George A. Olah
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Patent number: 5087783Abstract: An improved process for the alkylation of benzene in the presence of an alkylation catalyst. The catalyst bed may be caused to move in a direction countercurrent to the movement of the benzene and olefin, or a portion of the catalyst bed is periodically removed and replaced. A regeneration step, whereby the catalyst is heated in a controlled oxygen atmosphere in order to reactivate the catalyst, is also described.Type: GrantFiled: November 9, 1990Date of Patent: February 11, 1992Assignee: Lummus Crest, Inc.Inventors: Roger C. Johnson, Daniel McCarthy, Andrei Rhoe
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Patent number: 5073653Abstract: Process 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 conditions and under pressure 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 temperature and pressure conditions effective to cause 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.Type: GrantFiled: June 23, 1989Date of Patent: December 17, 1991Assignee: Fina Technology, Inc.Inventor: James R. Butler
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Patent number: 5030784Abstract: The instant invention relates to a process for converting methyl- and/or ethyl-substituted benzene or naphthalene and butadiene to 4-aryl-1-butene or 4-aryl-1-pentene and propylene by:a) reacting a methyl- and/or ethyl-substituted benzene or naphthalene and 1,3-butadiene in the presence of an alkali metal catalyst,b) reacting the butenylated reaction product of step a) with ethylene in the presence of of a disproportionation catalyst, andc) separating from the reaction product of step b) product 4-aryl-1-butene or 4-aryl-1-pentene and propylene.Type: GrantFiled: February 26, 1990Date of Patent: July 9, 1991Assignee: Shell Oil CompanyInventor: Lynn H. Slaugh
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Patent number: 5008480Abstract: The instant invention relates to a process for converting toluene and butadiene to styrene and 1-pentene by:(a) reacting touene and 1,3-butadiene in the presence of an alkali metal catalyst,(b) contacting the butenylated reaction product of step (a) with a double bond isomerization catalyst at a temperature sufficient to cause double isomerization,(c) reacting the isomerized product of step (b) with ethylene in the presence of a disproportionation catalyst, and(d) separating from the reaction product of step (c) product styrene and 1-pentene.Type: GrantFiled: February 26, 1990Date of Patent: April 16, 1991Assignee: Shell Oil CompanyInventor: Lynn H. Slaugh
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Patent number: 4992608Abstract: Cumene is prepared by alkylation of benzene with propylene, or by transalkylation of diisopropylbenzenes in the presence of benzene, on a silica and alumina gel catalyst which is amorphous to X-rays and has an SiO.sub.2 /Al.sub.2 O.sub.3 ratio of between 50/1 and 300/1, a surface area of between 500 and 1000 m.sup.2 /g, an overall pore volume of between 0.3 and 0.6 ml/g and mean pore diameter of the order of 10 .ANG., and which is free or substantially free of pores having a diameter exceeding 30 .ANG..Type: GrantFiled: April 24, 1989Date of Patent: February 12, 1991Assignees: Enichem Synthesis SpA, Eniricerche SpAInventors: Fabrizio Cavani, Virginio Arrigoni
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Patent number: 4983274Abstract: The catalytic properties of a metal-containing shape selective crystalline silicate zeolite are significantly improved by converting said metal to an intermetallic compound. Thus, for example, zeolite beta containing the intermetallic component platinum zeolite demonstrates improved catalytic properties for dewaxing a hydrocarbon feedstock compared to zeolite beta containing platinum metal alone.Type: GrantFiled: October 6, 1988Date of Patent: January 8, 1991Assignee: Mobil Oil Corp.Inventors: Nai Y. Chen, Thomas F. Degnan, Paul B. Weisz
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Patent number: 4956511Abstract: Process for the disproportionation of toluene over a nickel modified mordenite catalyst in which catalyst activity and aging quality are enhanced for carrying out the disproportionation reaction under relatively low temperature conditions with small increases of temperature as the process continues. The catalyst is loaded into a catalytic reaction zone. A preflush gas such as hydrogen is passed into the reaction zone while withdrawing the gas from the reaction zone and progressively increasing the temperature of the reaction zone to a desired level. A toluene feedstock is then passed into the reaction zone. Hydrogen is supplied with the toluene to the reaction zone, normally at a hydrogen/toluene mole ratio of 4 or less. At the conclusion of the initial transient conditions accompanying the initiation of toluene feed to the reaction zone, initial steady state conditions for disproportionation of toluene to benzene and xylene in the presence of the catalyst are established.Type: GrantFiled: January 4, 1989Date of Patent: September 11, 1990Assignee: Fina Technology, Inc.Inventors: James R. Butler, J. Randall Curtis
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Patent number: 4950824Abstract: A process for the production of 2,6-diisopropylnaphthalene is disclosed wherein an isopropylation reaction mixture containing isopropylated naphthalenes is subjected to transalkylation with a triisopropylnaphthalene-containing mixture to obtain a mixture containing mono-, di- and tri-isopropylnaphthalenes which is then separated into a first fraction containing monisopropylnaphthalenes, a second fraction containing diisopropylnaphthalenes and a third fraction containing triisopropylnaphthalenes. The first and third fractions are recycled to the above system, while the second fraction is subjected to separation treatments for the recovery of 2,6-diisopropylnaphthalene. The second fraction from which 2,6-diisopropylnaphthalene has been removed is subjected to transalkylation with naphthalene to obtain a monoisopropylnaphthalene-rich mixture which is to be fed to the isopropylation step.Type: GrantFiled: August 2, 1989Date of Patent: August 21, 1990Assignees: Chiyoda Corporation, NKK CorporationInventors: Yoshimi Shiroto, Mitsunori Shimura, Kenji Shimokawa, Yoshio Fukui, Sachio Asaoka, Hiroto Tajima, Kazuaki Ueda, Yakudo Tachibana, Kazuhiko Tate, Hiroaki Taniguchi
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Patent number: 4943553Abstract: This invention relates to a method of making ethylbiphenyls by the reaction of biphenyl with polyethylbenzenes or with ethylene and polyethylbenzenes in the presence of a solid acid catalyst and offers advantages of industrial significance such as absence of acidic waste water, no need of costly materials for equipment, catalyst reuse, and adaptability to a fixed-bed flow reaction system suitable for large-scale production.Type: GrantFiled: November 2, 1989Date of Patent: July 24, 1990Assignee: Nippon Steel Chemical Co., Ltd.Inventors: Kathuhiko Sakura, Genki Takeuchi, Naoko Takeshita
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Patent number: 4899009Abstract: A method for producing m-benzyltoluene with a high yield and excellent selectivity without producing undesirable heavier by-products. The method is characterized in that toluene and diphenylmethane are allowed to react at a reaction temperature in the range of 170.degree. to 400.degree. C. in the presence of a crystalline synthetic zeolite catalyst in which the molar ratio of SiO.sub.2 /Al.sub.2 O.sub.3 is 20 or higher and the openings of main pores are formed by ten-membered oxygen rings.Type: GrantFiled: June 9, 1989Date of Patent: February 6, 1990Assignee: Nippon Petrochemicals Co. Ltd.Inventors: Shigenobu Kawakami, Keiji Endo, Hideyuki Dohi, Atsushi Sato
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Patent number: 4891458Abstract: 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: December 17, 1987Date of Patent: January 2, 1990Inventors: Robert A. Innes, Stacey I. Zones, Gerald J. Nacamuli
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Patent number: 4885426Abstract: A process is provided for transalkylation of polyalkylaromatics over a catalyst comprising a molecular sieve having a high lattice aluminum content whereby its silica/alumina mole ratio is less than 40 and an alpha value of at least about 140.Type: GrantFiled: March 23, 1989Date of Patent: December 5, 1989Assignee: Mobil Oil CorporationInventors: Yung F. Chu, David O. Marler, John P. McWilliams
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Patent number: 4873386Abstract: A method for the highly selective production of 2,6-diethylnaphthalene involving the use of a specific Lewis acid catalyst and a highly regiospecific ethylating agent.Type: GrantFiled: June 28, 1988Date of Patent: October 10, 1989Assignee: Amoco CorporationInventors: Gary P. Hagen, Thomas E. Nemo
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Patent number: 4870222Abstract: A process for the production of a monoalkylated aromatic compound which minimizes the production of undesirable alkylating agent oligomers, while producing monoalkylaromatics in high yields. The process entails the combination of an alkylation reaction zone, a separations zone, and a transalkylation reaction zone wherein the alkylation catalyst and transalkylation catalyst are dissimilar and where the alkylation catalyst is comprised of noncrystaline silica-alumina material and the transalkylation catalyst is comprised of an acid-modified crystalline aluminosilicate material that is characterized as having a surface area of at least 580 m.sup.2 /g following acid washing after catalyst particle formulation.Type: GrantFiled: November 2, 1988Date of Patent: September 26, 1989Assignee: UOPInventors: Steve T. Bakas, Paul T. Barger
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Patent number: 4861935Abstract: Superior aromatic alkylation and transalkylation performance is obtained with a novel catalytic composition comprising a hydrogen form mordenite incorporated with alumina. The superior performance is a direct result of the catalyst composition having a surface area of at least 580 m.sup.2 /g. A novel method of preparing a catalyst having a surface area of at least 580 m.sup.2 /g is characterized by contacting a formed catalytic composite with an acidic aqueous solution.Type: GrantFiled: November 3, 1988Date of Patent: August 29, 1989Assignee: UOPInventors: Steve T. Bakas, Paul T. Barger
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Patent number: 4857666Abstract: An alkylation-transalkylation process for the production of a monoalkylated aromatic compound is disclosed which maximizes the production of desirable monoalkylaromatic compounds, while limiting transalkylation catalyst deactivation. The process entails the combination of an alkylation reaction zone, a first seperation zone, a second separation zone, and a transalkylation reaction zone wherein the alkylation catalyst and transalkylation catalyst are dissimilar and where the alkylation catalyst is comprised of phosphoric acid material and the transalkylation catalyst is comprised of a crystalline aluminosilicate material. The transalkylation catalyst deactivation is reduced by transalkylating only dialkylated aromatic compounds. Additionally, the transalkylation catalyst is regenerable utilizing a hot liquid hydrocarbon wash.Type: GrantFiled: September 21, 1988Date of Patent: August 15, 1989Assignee: UOPInventors: Paul T. Barger, Gregory J. Thompson, Raymond R. Herber, Tamotsu Imai
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Patent number: 4835337Abstract: A method for producing efficiently a highly pure 1-(m-ethylphenyl)-1-phenylethane or m-ethylphenylphenylmethane which are used as the starting materials for preparing medicines and other organic compounds. The method comprises the step of reacting a diaryl compound with benzene or alkylbenzene in the presence of an acid catalyst selected from the group consisting of AlCl.sub.3, AlBr.sub.3, HF.BF.sub.3 complex and Y-type zeolites.Type: GrantFiled: March 9, 1988Date of Patent: May 30, 1989Assignee: Nippon Petrochemicals Company, LimitedInventors: Isoo Shimizu, Yasuo Matsumura, Kazumichi Uchida
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Patent number: 4774377Abstract: An alkylation-transalkylation process for the production of a monoalkylated aromatic compound is disclosed which maximizes the production of desirable monoalkylaromatic compounds, while limiting transalkylation catalyst deactivation. The process entails the combination of an alkylation reaction zone, a first separation zone, a second separation zone, and a transalkylation reaction zone wherein the alkylation catalyst and transalkylation catalyst are dissimilar and where the alkylation catalyst is comprised of phosphoric acid material and the transalkylation catalyst is comprised of a crystalline aluminosilicate material. The transalkylation catalyst deactivation is reduced by transalkylating only dialkylated aromatic compounds.Type: GrantFiled: September 11, 1987Date of Patent: September 27, 1988Assignee: UOP Inc.Inventors: Paul T. Barger, Gregory J. Thompson, Raymond R. Herber, Tamotsu Imai
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Patent number: 4723048Abstract: The invention concerns an improved process for dismutation and transalkylation of alkylaromatic hydrocarbons in the presence of a catalyst consisting essentially of acid mordenite having a total SiO.sub.2 /Al.sub.2 O.sub.3 molar ratio from 9 to 80 and a sodium content lower than 1% by weight, said catalyst containing at least one metal selected from group M formed of nickel, palladium and metals from group I.sub.B of the periodic classification of elements and containing at least one metal of group IV.sub.A of said classification.The catalyst preferably contains from 30 to 99.9 % by weight of mordenite, from 0.005 to 25% by weight of a group M metal, from 0.05 to 10% by weight of a group IV.sub.A metal and optionally up to 50% by weight of a binding agent.The invention is particularly useful for dismutation of toluene or transalkylation of toluene and of alkylaromatic hydrocarbons having at least 9 carbon atoms per molecule.Type: GrantFiled: August 28, 1986Date of Patent: February 2, 1988Assignee: Institut Francais du PetroleInventors: Pierre Dufresne, Christian Marcilly, Francis Raatz
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Patent number: 4677240Abstract: A catalytic process is provided for upgrading a hydrocarbon feed stream containing pseudocumene together with a fraction of close boiling hydrocarbon compounds having a normal boiling point in a temperature range of about 320.degree. F. to about 365.degree. F. comprising contacting such hydrocarbon feed steam in the presence of hydrogen with a catalyst comprising AMS-1B crystalline borosilicate molecular sieve whereby such close boiling hydrocarbon compounds are converted to compounds having a normal boiling point below a temperature of about 300.degree. F., and fractionating the effluent product stream.Type: GrantFiled: January 10, 1986Date of Patent: June 30, 1987Assignee: Amoco CorporationInventors: Ronald E. Carlson, Stephen R. Ely, Allen I. Feinstein, Ibrahim Ghanayem
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Patent number: 4665253Abstract: Feedstock comprising aromatic compounds is converted by isomerization, alkylation, disproportionation or transalkylation to product comprising aromatic compounds which differs from the feedstock over catalyst having been prepared by reacting a high-silica zeolite with an acidic inorganic oxide in the presence of water.Type: GrantFiled: October 29, 1985Date of Patent: May 12, 1987Assignee: Mobil Oil CorporationInventors: Pochen Chu, William E. Garwood