Plural Alkylation Stages Patents (Class 585/449)
-
Publication number: 20020198422Abstract: The present invention relates to a process for the catalytic alkylation of hydrocarbons comprising (i) reacting an alkylatable compound with an alkylation agent over a solid acid alkylation catalyst to form an alkylate, and (ii) regenerating said catalyst under mild regeneration conditions in the presence of hydrogen and hydrocarbon, wherein the hydrocarbon comprises at least a portion of the formed alkylate.Type: ApplicationFiled: June 5, 2002Publication date: December 26, 2002Inventors: Emanuel Hermanus Van Broekhoven, Johannes Wilhelmus Maria Sonnemans, Stephan Zuijdendorp
-
Patent number: 6486371Abstract: Vapor phase alkylation of an aromatic substrate in a multi-stage alkylation reaction zone having a plurality of series-connected catalyst beds providing mixing zones between adjacent catalyst beds. An aromatic substrate and a C2-C4 alkylating agent is supplied to an inlet side of a gas phase reaction zone causing vapor phase alkylation of the aromatic substrate as the aromatic substrate and the alkylating agent flow through the reaction zone from one catalyst bed to the next. A quench fluid comprising one or both of the aromatic substrate and the alkylating agent is supplied into the interior of the mixing zone through a plurality of flow paths. One portion of the flow paths is directed upwardly and another portion downwardly within the mixing zone. The quench fluid is supplied to the mixing zone through a plurality of dispersion channels spaced laterally from one another.Type: GrantFiled: November 28, 2000Date of Patent: November 26, 2002Assignee: Fina Technology, Inc.Inventors: James R. Butler, Denis Mignon
-
Publication number: 20020128529Abstract: A countercurrent process for the alkylation of aromatic materials with olefins which takes place in a multi-bed system. The aromatic material is in the liquid phase; the olefin in the gaseous phase; and the catalyst in the solid phase. The olefinic material is fed below the catalyst bed in the gaseous phase and aromatic is fed as a liquid phase above the catalyst bed under conditions of temperature and pressure to maintain the aromatic product in the liquid phase and the olefin in the vapor phase.Type: ApplicationFiled: March 13, 2002Publication date: September 12, 2002Applicant: CATALYTIC DISTILLATION TECHNOLOGIESInventor: Jamin Chen
-
Patent number: 6417420Abstract: A process for the production of alkylaromatic hydrocarbons by alkylating aromatic hydrocarbons with olefinic hydrocarbons is disclosed. The olefinic hydrocarbons are produced by dehydrogenating paraffinic hydrocarbons. Aromatic byproducts formed in dehydrogenation are removed using an aromatic byproducts removal zone and either a dividing wall distillation column or thermally coupled distillation columns. The process significantly decreases the cost of utilities in producing alkylaromatics, such as precursors for detergent manufacture.Type: GrantFiled: February 26, 2001Date of Patent: July 9, 2002Assignee: UOP LLCInventors: Douglas G. Stewart, Dennis E. O'Brien
-
Patent number: 6376729Abstract: A process for the production of ethylbenzene by the gas phase alkylation of benzene over a molecular sieve aromatic alkylation catalyst followed by liquid phase alkylation of the product of the gas phase alkylation. A feedstock containing benzene and ethylene is supplied to a first alkylation reaction zone containing a molecular sieve aromatic alkylation catalyst. The reaction zone is operated at temperature and pressure conditions to cause gas phase ethylation of the benzene with the production of an alkylation product comprising a mixture of ethylbenzene and polyalkylated aromatic components including diethylbenzene. The output from the first alkylation reaction zone is supplied, at least in part, to a second alkylation zone which is operated in the liquid phase or in the supercritical region followed by supply to an intermediate recovery zone for the separation and recovery of ethylbenzene and a polyalkylated aromatic compound component including diethylbenzene.Type: GrantFiled: December 4, 2000Date of Patent: April 23, 2002Assignee: Fina Technology, Inc.Inventors: James T. Merrill, James R. Butler
-
Patent number: 6350930Abstract: A method for producing an aromatic compound styrenic compound adduct comprising the steps of: (1) reacting an aromatic compound and a styrenic compound in a first reactor 1 of fixed-bed flow type in a liquid phase in the presence of a solid acid catalyst, (2) circulating a part of the reaction mixture from the above step to the first reactor 1, (3) feeding a reaction mixture flowing out from the first reactor to a second reactor 3, thereby reducing the content of unsaturated components with the aid of a solid acid catalyst, and (4) distilling the resultant reaction mixture, to thereby obtain a fraction having a reduced content of unsaturated components. The method can be used for producing an aromatic compound/styrenic compound adduct having a reduced content of unsaturated components in high yield and at a low cost.Type: GrantFiled: April 19, 2000Date of Patent: February 26, 2002Assignee: Nippon Petrochemicals Company, LimitedInventors: Hideyuki Dohi, Shozo Hayashi
-
Patent number: 6339179Abstract: A process for producing alkyl aromatics using a transalkylation reaction zone and an alkylation reaction zone is disclosed. One portion of the transalkylation reaction zone effluent passes to an alkylation reaction zone where an aromatic substrate is alkylated to the desired alkyl aromatic. At least a portion of the alkylation reaction zone effluent and another portion of the transalkylation reaction zone effluent pass to a product recovery zone. This process decreases the capital and operating costs of recycling aromatic substrate to the transalkylation and/or alkylation reaction zone while maintaining operational flexibility. This process is well suited for solid transalkylation and alkylation catalysts. Ethylbenzene and cumene may be produced by this process.Type: GrantFiled: July 25, 2000Date of Patent: January 15, 2002Assignee: UOP LLCInventors: Russell C. Schulz, Gregory J. Gajda, Guy B. Woodle, Andrew S. Zarchy
-
Patent number: 6281399Abstract: A process for producing isopropyl aromatics using a transalkylation reaction zone and an alkylation reaction zone is disclosed. Portions of the transalkylation reaction zone effluent pass to a multibed alkylation reaction zone where aromatics in the transalkylation reaction zone effluent are alkylated to the desired isopropyl aromatics. At least a portion of the transalkylation reaction zone effluent passes to an alkylation bed other than the first alkylation bed of the multibed alkylation reaction zone. This process decreases the capital and operating costs of recycling the aromatics in the transalkylation reaction zone effluent. This process is well suited for solid transalkylation and alkylation catalysts. Cumene may be produced by this process.Type: GrantFiled: February 23, 2000Date of Patent: August 28, 2001Assignee: UOP LLCInventors: Russell C. Schulz, Gregory J. Gajda, Guy B. Woodle
-
Patent number: 6268542Abstract: A process for the production of ethylbenzene by the alkylation of benzene over a molecular sieve aromatic alkylation catalyst followed by transalkylation of polyalkylated aromatic components and then liquid phase alkylation. A feedstock containing benzene and ethylene is supplied to a first alkylation reaction zone containing a molecular sieve aromatic alkylation catalyst. The reaction zone is operated at temperature and pressure conditions to cause gas phase ethylation of the benzene with the production of an alkylation product comprising a mixture of ethylbenzene and polyalkylated aromatic components including diethylbenzene with xylene present in only small amounts. The output from the alkylation reaction zone is supplied to an intermediate recovery zone for the separation and recovery of ethybenzene, a polyalkylated aromatic compound component including diethylbenzene.Type: GrantFiled: August 23, 1999Date of Patent: July 31, 2001Assignee: Fina Technology, Inc.Inventors: James T. Merrill, James R. Butler
-
Patent number: 6232515Abstract: A process for producing ethyl aromatics using a transalkylation reaction zone and an alkylation reaction zone is disclosed. Portions of the transalkylation reaction zone effluent pass to a multibed alkylation reaction zone where aromatics in the transalkylation reaction zone effluent are alkylated to the desired ethyl aromatics. At least a portion of the transalkylation reaction zone effluent passes to an alkylation bed other than the first alkylation bed of the multibed alkylation reaction zone. This process decreases the capital and operating costs of recycling the aromatics in the transalkylation reaction zone effluent. This process is well suited for solid transalkylation and alkylation catalysts. Ethylbenzene may be produced by this process.Type: GrantFiled: March 17, 2000Date of Patent: May 15, 2001Assignee: UOP LLCInventors: Russell C. Schulz, Gregory J. Gajda, Guy B. Woodle
-
Patent number: 6169219Abstract: Detergent-quality linear alkylaromatics are recovered from an alkylation reactor effluent containing polymeric byproducts, such as dimers and trimers of the olefinic feedstock. The effluent stream passes to another reactor operating at a higher temperature than the first reactor. Heavy alkylate is separated from the detergent-quality linear alkylaromatics by conventional separation methods such as distillation. This invention decreases the concentration of polymeric byproducts in the linear alkylaromatics. The benefits of this invention include a higher linearity and/or a lower bromine index in the detergent-quality linear alkylaromatic product, as well as a lower color after sulfonation of the linear alkylbenzene sulfonate.Type: GrantFiled: June 9, 1999Date of Patent: January 2, 2001Assignee: UOP LLCInventors: Masami Kojima, Thomas R. Fritsch, Kurt A. Detrick
-
Patent number: 6166281Abstract: This invention is directed to a fluorine-containing mordenite catalyst and use thereof in the manufacture of linear alkylbenzene (LAB) by alkylation of benzene with an olefin. The paraffin may have from about 10 to 14 carbons. The fluorine-containing mordenite is prepared typically by treatment with an aqueous hydrogen fluoride solution. The benzene alkylation may be conducted using reactive distillation. This invention is also directed to a process for production of LAB having a high 2-phenyl isomer content by combining LAB product from the fluorine-containing mordenite product from a conventional LAB alkylation catalyst such as hydrogen fluoride.Type: GrantFiled: October 19, 1998Date of Patent: December 26, 2000Assignee: Huntsman Petrochemical CorporationInventor: Prakasa Rao Anantaneni
-
Patent number: 6156949Abstract: There is provided a process for shape selective xylene methylation that involves contacting a feedstream which includes xylene and methanol under alkylation conditions, with a low activity catalyst. Xylene conversions of at least 15% at methanol utilization levels of 25% or greater are achieved by sequential injection of methanol The xylene methylation process has a selectivity for pseudocumene of over 85% and up to 99%, with a pseudocumene:durene ratio of up to 20 or more.Type: GrantFiled: December 28, 1998Date of Patent: December 5, 2000Assignee: Mobil Oil CorporationInventors: Stephen H. Brown, Mark F. Mathias
-
Patent number: 6150578Abstract: A separation arrangement for a cumene process that operates with a relatively wet feed to an alkylation zone and relatively dry feed to a transalkylation zone reduces utilities and capital expenses for the separation and recycle of distinct wet and dry components by using an arrangement that first separates effluent from the trans alkylation and alkylation reaction zone in a benzene column before performing light ends and drying in a downstream depropanizer column. The arrangement uses a portion of the net overhead stream from the benzene column as a wet recycle stream for return to the alkylation reaction zone and sends another portion of the benzene net overhead to the depropanizer to supply a dry benzene recycle for the trans alkylation reaction zone.Type: GrantFiled: December 7, 1999Date of Patent: November 21, 2000Assignee: UOP LLCInventors: Perry K. Ho, Russell C. Schulz
-
Patent number: 6133492Abstract: This invention is directed to a fluorine-containing mordenite catalyst and use thereof in the manufacture of linear alkylbenzene (LAB) by alkylation of benzene with an olefin. The olefin may have from about 10 to 14 carbons. The fluorine-containing mordenite is prepared typically by treatment with an aqueous hydrogen fluoride solution. The benzene alkylation may be conducted using reactive distillation. This invention is also directed to a process for production of LAB having a high 2-phenyl isomer content by use of the fluorine-containing mordenite in conjunction with a conventional solid LAB alkylation catalyst. The two catalysts may be used in a mixed catalyst bed or may be packed in series, with the relative proportions being adjusted to provide a desired 2-phenyl isomer content of in the final product.Type: GrantFiled: October 19, 1998Date of Patent: October 17, 2000Assignee: Huntsman Petrochemical CorporationInventor: Prakasa Rao Anantaneni
-
Patent number: 6121501Abstract: A process for producing 2,6-dialkylnaphthalene from a hydrocarbon feedstock that contains at least one component selected from the group consisting of dialkylnaphthalene isomers, monoalkylnaphthalene isomers, polyalkylnaphthalenes, and naphthalene, is provided that includes the following steps:I. separating the hydrocarbon feedstock and/or a dealkylation product fed from step III into a naphthalene fraction, a monoalkylnaphthalene fraction, a dialkylnaphthalene fraction and a remaining products fraction;II. separating and purifying 2,6-dialkylnaphthalene from the dialkylnaphthalene fraction of step I;III. dealkylating the hydrocarbon feedstock and/or the remaining products fraction of step I and feeding the dealkylation product to step I; andIV. alkylating the naphthalene and monoalkylnaphthalene fractions of step I;wherein the hydrocarbon feedstock is fed to step I or step III.Type: GrantFiled: April 9, 1999Date of Patent: September 19, 2000Assignees: Kabushiki Kaisha Kobe Seiko Sho, Mobil Oil CorporationInventors: Masahiro Motoyuki, Koji Yamamoto, Ajit Vishwanath Sapre, John Paul Mc Williams, Susan Patricia Donnelly
-
Patent number: 6096935Abstract: A process for producing alkyl aromatics using a transalkylation reaction zone and an alkylation reaction zone is disclosed. The transalkylation reaction zone effluent passes to the alkylation reaction zone where aromatics in the transalkylation reaction zone effluent are alkylated to the desired alkyl aromatics. This process decreases the capital and operating costs of recycling the aromatics in the transalkylation reaction zone effluent. This process is well suited for solid transalkylation and alkylation catalysts. Ethylbenzene and cumene may be produced by this process.Type: GrantFiled: July 28, 1998Date of Patent: August 1, 2000Assignee: UOP LLCInventors: Russell C. Schulz, Gregory J. Gajda
-
Patent number: 6090991Abstract: Ethylbenzene is produced by alkylation over monoclinic silicalite catalysts having a weak acid site concentration of less than 50 micromoles per gram. A feedstock containing benzene and ethylene is applied to an alkylation reaction zone having at least one catalyst bed containing a monoclinic silicalite catalyst having a weak acid site concentration of less than 50 micromoles per gram. The alkylation reaction zone is operated at temperature and pressure conditions in which the benzene is in a gaseous phase to cause gas-phase alkylation of the aromatic substrate in the presence of the silicalite catalysts to produce an alkylation product. The alkylation product is then withdrawn from the reaction zone for separation and recovery.Type: GrantFiled: February 27, 1999Date of Patent: July 18, 2000Assignee: Fina Technology, Inc.Inventors: James R. Butler, Ashim Kumar Ghosh
-
Patent number: 6069285Abstract: An integrated alkylaromatic process using a solid alkylation catalyst and an aromatic rectifier is disclosed for alkylating aromatics with olefins and for regenerating the solid alkylation catalyst. The aromatic rectifier produces a relatively low-purity aromatic-containing overhead stream that is used in producing alkylaromatics, and an aromatic column produces a relatively high-purity aromatic-containing overhead stream that is used in regenerating the solid alkylation catalyst. In another embodiment, this process is further integrated with a paraffin dehydrogenation zone and an aromatic by-products removal zone. This invention produces the benzene-containing streams that are necessary for alkylating and for regenerating in a more economical manner than prior art processes.Type: GrantFiled: June 9, 1999Date of Patent: May 30, 2000Assignee: UOP LLCInventors: Thomas R. Fritsch, Steven F. Eshelman, Dennis E. O'Brien
-
Patent number: 6063976Abstract: The present invention provides a method comprising (a) contacting a first reaction mixture comprising an aromatic and a dilute stream comprising ethylene and propylene with a large pore microporous solid acid catalyst, preferably a large pore zeolite catalyst, which is effective to promote alkylation of the aromatic under first conditions effective to maintain a liquid phase comprising the aromatic and effective to cause the propylene to alkylate said aromatic but substantially ineffective to cause the ethylene to alkylate said aromatic, forming propylated aromatic and a second dilute stream comprising ethylene but substantially depleted of propylene, and (b) recovering the propylated aromatic.Type: GrantFiled: August 18, 1998Date of Patent: May 16, 2000Assignee: Exxon Chemical Patent Inc.Inventors: Dan E. Hendriksen, James R. Lattner, Jos P. Wristers
-
Patent number: 6057485Abstract: Ethylbenzene is produced by alkylation over a split load of monoclinic silicalite alkylation catalysts having different silica/alumina ratios. A feedstock containing benzene and ethylene is applied to a multi-stage alkylation reaction zone having a plurality of series-connected catalyst beds. At least one catalyst bed contains a first monoclinic silicalite catalyst having a silica/alumina ratio of at least 275. At least one other catalyst bed contains a second monoclinic silicalite catalyst having a silica/alumina ratio of less than about 275. The alkylation reaction zone is operated at temperature and pressure conditions in which the benzene is in a gaseous phase to cause gas-phase alkylation of the aromatic substrate in the presence of the monoclinic silicalite catalysts to produce an alkylation product. The alkylation product is then withdrawn from the reaction zone for separation and recovery.Type: GrantFiled: November 17, 1998Date of Patent: May 2, 2000Assignee: Fina Technology, Inc.Inventors: James T. Merrill, James R. Butler, Ashim Kumar Ghosh
-
Patent number: 6031144Abstract: The residual olefin content of the alkylation reaction product of a single-ring aromatic hydrocarbon with an olefin is reduced by removing at least a portion of the non-alkylated single-ring aromatic hydrocarbon, then reacting the remaining alkylation reaction product at about atmospheric pressure and at a temperature of about from 100.degree. to 250.degree. C. in the presence of an acidic catalyst. The olefin has at least sixteen carbon atoms. The acidic catalyst can be a molecular sieve (such as a natural or synthetic zeolite) or clay.Type: GrantFiled: August 6, 1997Date of Patent: February 29, 2000Assignee: Chevron Chemical Company LLCInventors: Curt B. Campbell, Thomas V. Harris
-
Patent number: 6018086Abstract: The present invention relates to a process of preparing dialkylnaphthylenes and polyalkylenenaphthyleneates.Type: GrantFiled: October 10, 1997Date of Patent: January 25, 2000Assignees: Kabushiki Kaisha Kobe Seiko Sho, Mobil Oil CorporationInventors: Masahiro Motoyuki, Koji Yamamoto, Ajit Vishwanath Sapre, John Paul Mc Williams, Susan Patricia Donnelly
-
Patent number: 6013848Abstract: A process for the conversion of heavy bottoms from aromatic alkylation known as "flux oil" and containing heavier polyalkylaromatic compounds, in which the heavier polyalkylates are fed along with aromatic to a reactor containing an acidic zeolite catalyst for conversion to light mono-, and poly alkylaromatic compounds. The light polyalkylates may then be transalkylated with benzene to form additional monoalkylate.Type: GrantFiled: July 8, 1997Date of Patent: January 11, 2000Assignee: Catalytic Distillation TechnologiesInventors: Jamin Chen, Chuen Y. Yeh
-
Patent number: 6011190Abstract: 2,6-Dialkylnaphthalene is prepared from a feedstock comprising naphthalene and an alkylating agent, by a process comprising the steps:(I) transalkylating isomers of dialkylnaphthalene and naphthalene to produce monoalkylnaphthalene and isomers of dialkylnaphthalene;(II) separating the product obtained in step (I) into naphthalene, monoalkylnaphthalene, dialkylnaphthalene and other components;(III) alkylating the monoalkylnaphthalene fraction from step (II) with an alkylating agent to produce dialkylnaphthalene; and(IV) separating 2,6-dialkylnaphthalene from the dialkylnaphthalene fraction in step (II),wherein at least step (I) or step (III) is conducted in the presence of a catalyst having a composition comprising a synthetic zeolite having an X-ray diffraction pattern with an interplanar d-spacing (.ANG.)______________________________________ 12.36 .+-. 0.4 11.03 .+-. 0.2 8.83 .+-. 0.14 6.18 .+-. 0.12 6.00 .+-. 0.10 4.06 .+-. 0.07 3.91 .+-. 0.07 3.42 .+-. 0.06.Type: GrantFiled: July 2, 1997Date of Patent: January 4, 2000Assignees: Kabushiki Kaisha Kobe Seiko Sho, Mobil Oil CorporationInventors: Masahiro Motoyuki, Koji Yamamoto, Ajit Vishwanath Sapre, John Paul McWilliams
-
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
-
Patent number: 6005152Abstract: A process is described for preparing monoalkylated aromatic compounds which comprises subjecting an aromatic hydrocarbon to alkylation with an olefin containing from 2 to 4 carbon atoms, or to transalkylation with a polyalkylaromatic hydrocarbon, in the presence of ERS-10 zeolite.Type: GrantFiled: April 5, 1999Date of Patent: December 21, 1999Assignees: Enichem S.p.A., EniTechnologie S.p.A.Inventors: Stefano Amarilli, Luciano Carluccio, Carlo Perego, Giuseppe Bellussi
-
Patent number: 5998684Abstract: A separation arrangement for a cumene process that operates with a relatively wet feed to an alkylation zone and relatively dry feed to a transalkylation zone reduces utilities and capital expenses for the separation and recycle of distinct wet and dry components by using an arrangement that first separates effluent from the trans alkylation and alkylation reaction zone in a benzene column before performing light ends and drying in a downstream depropanizer column. The arrangement uses a portion of the net overhead stream from the benzene column as a wet recycle stream for return to the alkylation reaction zone and sends another portion of the benzene net overhead to the depropanizer to supply a dry benzene recycle for the trans alkylation reaction zone.Type: GrantFiled: November 10, 1997Date of Patent: December 7, 1999Assignee: UOP LLCInventors: Perry K. Ho, Russell C. Schulz
-
Patent number: 5998687Abstract: Benzene is catalytically alkylated with ethylene in a process which comprises at least two catalyst zones. Benzene and ethylene contact a catalyst comprising zeolite beta in a first catalyst zone. Ethylene and the effluent from the first catalyst zone contact a catalyst comprising zeolite Y to produce an alkylate containing ethylbenzene.Type: GrantFiled: July 29, 1998Date of Patent: December 7, 1999Assignee: UOP LLCInventors: Guy B. Woodle, Alan E. Cepla
-
Patent number: 5986155Abstract: Treating low reactivity alkylating agents in the vapor phase with catalysts converts the low reactivity alkylating agents to high reactivity alkylating agents. The alkylating agents are useful in synthesis of alkyl aromatics with Lewis acid catalysts.Type: GrantFiled: July 10, 1996Date of Patent: November 16, 1999Assignee: The Lubrizol CorporationInventors: James D. Burrington, Stuart L. Bartley, Douglas C. Rhubright, Paul A. Lewis, Marvin B. DeTar, Alicia L. Kliever, Frank A. Del Greco, Lawrence T. Novak
-
Patent number: 5962758Abstract: Ethylbenzene is produced from benzene and ethylene in an alkylation reactor wherein the feedstocks also contain propylbenzenes and/or components that produce propylbenzene. Polyethylbenzenes are also produced in the process. The ethylbenzene product and unreacted benzene are separated and then the propylbenzenes are separated from the polyethylbenzenes by distillation. The propylbenzenes are destroyed in a vapor-phase reactor and the polyethylbenzenes are transalkylated with benzene in a liquid or partial liquid phase at a lower temperature.Type: GrantFiled: April 9, 1998Date of Patent: October 5, 1999Assignee: ABB Lummus Global Inc.Inventors: Angel S. Sy, Richard J. Wilcox
-
Patent number: 5955642Abstract: An alkylation/transalkylation process involving vapor phase alkylation of a benzene feedstock in a multi-stage alkylation zone having a plurality of series connected catalyst beds containing a pentasil aromatic alkylation catalyst, such as silicalite, coupled with intermediate separation and recirculation steps and liquid phase transalkylation over a transalkylation catalyst comprising a molecular sieve having a pore size greater than the pore size of the silicalite. The benzene containing feedstock is supplied to the multi-stage alkylation reaction zone along with a C.sub.2 -C.sub.4 alkylating agent operated under temperature and pressure conditions to maintain the benzene in the gas phase. Alkylated product is recovered from the alkylation zone and supplied to a benzene recovery zone for the separation of the benzene from the alkylation product. Benzene from the benzene recovery zone is recycled to the reaction zone.Type: GrantFiled: October 30, 1996Date of Patent: September 21, 1999Assignee: Fina Technology, Inc.Inventors: James T. Merrill, James R. Butler
-
Patent number: 5902917Abstract: There is provided a process for producing alkylaromatics, especially ethylbenzene and cumene, wherein a feedstock is first fed to a transalkylation zone and the entire effluent from the transalkylation zone is then cascaded directly into an alkylation zone along with an olefin alkylating agent, especially ethylene or propylene.Type: GrantFiled: November 26, 1997Date of Patent: May 11, 1999Assignee: Mobil Oil CorporationInventors: Nick A. Collins, Dominick N. Mazzone, Chaya R. Venkat
-
Patent number: 5900518Abstract: The present invention addresses heat integration in an alkylation/transalkylation process involving alkylation of an aromatic substrate with a C.sub.2 -C.sub.4 alklating agent coupled with separation to recover a monoalkylated aromatic product and liquid phase transalkylation of a polyalkylated product. Aromatic feedstock and a C.sub.2 -C.sub.4 alkylating agent are supplied to an alkylation reaction zone which is operated to produce an alkylated product. The output from the alkylation reaction zone initially travels through an arrangement of heat exchangers. From there, the alkylation effluent passes into the first separation zone which is operated to produce a lower boiling fraction comprising the aromatic substrate, which may be recycled to the alkylation reaction zone, and a higher boiling fraction comprising a mixture of monoalkylated and polyalkylated aromatics.Type: GrantFiled: October 30, 1996Date of Patent: May 4, 1999Assignee: Fina Technology, Inc.Inventors: James T. Merrill, Joseph Honn Tudor
-
Patent number: 5877384Abstract: An apparatus and process for separating propane and benzene from alkylation reaction products in cumene production. An integrated fractionation tower combines the functions of propane separation, recycle benzene recovery as well as system dewatering to eliminate the need for separate depropanizer and dehydration columns and thus save capital and operating expenses.Type: GrantFiled: February 12, 1996Date of Patent: March 2, 1999Assignee: The M. W. Kellogg CompanyInventors: Harold Edward Gimpel, Eric Wing-Tak Wong, Kourosh Faiz Ghassemi
-
Patent number: 5849965Abstract: In a multistage process, a relatively unreactive paraffinic substrate is alkylated in a primary stage while a more reactive aromatic substrate is alkylated in a secondary stage wherein at least a portion of the effluent from the primary stage is used as a diluent in the secondary stage. The alkylation reaction in each stage is catalyzed by an acid catalyst which is adsorbed on a particulate solid support.Type: GrantFiled: May 22, 1997Date of Patent: December 15, 1998Assignee: Amoco CorporationInventors: Robert L. Mehlberg, George A. Huff, Jr.
-
Patent number: 5847255Abstract: Process for the production of ethylbenzene by alkylation over a silicalite alkylation catalyst with the subsequent transalkylation of diethylbenzene with the alkylation catalyst and conditions selected to retard xylene production and also heavies production. A feedstock containing benzene and ethylene is applied to a multi-stage alkylation reaction zone having a plurality of series-connected catalyst beds containing a pentasil molecular sieve alkylation catalyst which is silicalite of a predominantly monoclinic symmetry having a silica/alumina ratio of at least 275. The feedstock is supplied to the alkylation reaction zone to cause gas-phase ethylation of benzene at a flow rate to provide a space velocity of benzene over the catalyst to produce a xylene concentration in the product of about 600 ppm or less based upon the ethylbenzene content.Type: GrantFiled: May 21, 1997Date of Patent: December 8, 1998Assignee: Fina Technology, Inc.Inventors: Ashim Kumar Ghosh, James T. Merrill, James R. Butler
-
Patent number: 5777187Abstract: This invention is directed to a fluorine-containing mordenite catalyst and use thereof in the manufacture of linear alkylbenzene (LAB) by alkylation of benzene with an olefin. The olefin may have from about 10 to 14 carbons. The fluorine-containing mordenite is prepared typically by treatment with an aqueous hydrogen fluoride solution. The benzene alkylation may be conducted using reactive distillation. Yield and bromine index of the LAB may be improved by further alkylation using a fluorine containing clay catalyst such as montmorillonite clay.Type: GrantFiled: June 12, 1996Date of Patent: July 7, 1998Assignee: Huntsman Petrochemical CorporationInventors: John F. Knifton, Prakasa Rao Anantaneni
-
Patent number: 5756872Abstract: A process wherein an FCCU off gas is treated by first subjecting the off gas to an alkylation with a heavy reformat to remove the propylene and contaminants after which the gas is separated from the reformat and alkylated products by distillation to produce an ethylene feed suitable for the reaction with benzene to produce ethyl benzene.Type: GrantFiled: January 27, 1997Date of Patent: May 26, 1998Assignee: Catalytic Distillation TechnologiesInventors: Lawrence A. Smith, Jr., John R. Adams
-
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
-
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
-
Patent number: 5489732Abstract: Hydrocarbons are alkylated in a fluidized riser-reactor using a solid catalyst which is regenerated within the process by contact with hydrogen. The alkylation and regeneration steps are separated to prevent the admixture of hydrogen and any olefins present in the process. Two separate modes of regeneration are performed simultaneously: a mild liquid-phase washing and a vapor-phase hot hydrogen stripping operation.Type: GrantFiled: October 14, 1994Date of Patent: February 6, 1996Assignee: UOPInventors: Scott Y. Zhang, Christopher D. Gosling, Paul A. Sechrist, Gregory A. Funk
-
Patent number: 5446223Abstract: The aging rate of the catalyst in a process for the concurrent alkylation of aromatic with olefin and distillation of reaction components (reactants and products) in a distillation column reactor in a catalyst bed wherein the catalyst also serves as the distillation structure, is retarded by limiting the conversion of olefin in the catalyst bed to about 90 percent. A portion up to and including the entire unreacted aromatic and olefin in the overhead from the distillation column reactor are condensed and fed to a fixed bed alkylation reactor to substantially finish the conversion with a portion of the effluent from the fixed bed reactor recycled thereto to control the olefin content in the fixed bed reactor inlet to less than one volume percent, preferably less than 0.50 volume percent and thereby reduce the aging in that catalyst. A fixed bed transalkylation reactor is used to convert the polysubstituted alkylated aromatic products to mono-substituted alkylated aromatic products.Type: GrantFiled: May 23, 1994Date of Patent: August 29, 1995Assignee: Chemical Research & Licensing CompanyInventor: Lawrence A. Smith, Jr.
-
Patent number: 5434325Abstract: The present invention provides an alkylation process which is highly selective towards the production of para-tertiarybutylethylbenzene in high yield and in high para isomer content, while minimizing the development of unwanted by-products and impurities during the alkylation reaction. In accordance with the process, a feed stream mixture comprising the olefin alkylating agent and a molar excess of an aromatic hydrocarbon substrate is introduced into the inlet of a reactor zone and through a bed of active zeolite alkylation catalyst under alkylation conditions such that substantially all of the olefin reacts with the aromatic substrate to produce a mixture comprising the alkylated product and unreacted aromatic compound. This mixture is continuously withdrawn from the reactor zone as reactor effluent, after which the effluent is split into a product stream and recycle stream.Type: GrantFiled: July 20, 1994Date of Patent: July 18, 1995Assignee: Deltech CorporationInventors: Shiou-Shan Chen, Joseph C. Peters
-
Patent number: 5336821Abstract: A process for the alkylation of aromatic hydrocarbons such as cumene and ethylbenzene is disclosed. A portion of the effluent stream from an alkylation reactor passes through an indirect heat exchanger to transfer heat to a flashed stream containing the product aromatic hydrocarbons. The heat exchanger recovers the exothermic heat of reaction from the effluent stream for use elsewhere in the process. This method of heat exchange is especially useful in alkylation processes where the temperature of the effluent stream is relatively low, such as where the alkylation reactor contains a zeolite catalyst.Type: GrantFiled: May 6, 1993Date of Patent: August 9, 1994Assignee: UOPInventors: Richard R. DeGraff, Peter J. Van Opdorp, Russell C. Schulz
-
Patent number: 5336820Abstract: A process is disclosed for enhancing the alkylation conversion rate of a benzene-rich gasoline boiling range hydrocarbon feedstream alkylated with C.sub.2 -C.sub.5 olefins. The process comprises contacting the benzene-rich stream and olefins sequentially in decreasing order of olefin oligomerization activity comprising a first contact with C.sub.3 -C.sub.5 olefins followed by contact with C.sub.2 olefin, preferably at different points of an alkylation zone containing solid, shape selective aluminosilicate catalyst particles under benzene alkylation conditions. Gasoline is produced having a reduced benzene content.Type: GrantFiled: August 11, 1993Date of Patent: August 9, 1994Assignee: Mobil Oil CorporationInventors: Hartley Owen, Mohsen N. Harandi
-
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
-
Patent number: 5198595Abstract: Monoalkylated benzene such as ethylbenzene and cumene or monoalkylated substituted benzene are produced by alkylation in the presence of an acidic mordenite zeolite catalyst having a silica/alumina molar ratio of at least 40:1, preferably 160:1. In a subsequent, optional process, the polyalkylated benzene or polyalkylated substituted benzene produced in the alkylation is transalkylated in the presence of an acidic mordenite zeolite catalyst.Type: GrantFiled: June 21, 1991Date of Patent: March 30, 1993Assignee: The Dow Chemical CompanyInventors: Guo-shuh J. Lee, Juan M. Garces, Garmt R. Meima, Matheus J. M. van der Aalst
-
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
-
Patent number: 5185487Abstract: An improved method and apparatus for the safe handling of alkylation catalyst. The method and apparatus comprises a process vessel which serves a dual function of storing alkylation catalyst and of recontacting alkylation hydrocarbon product with alkylation catalyst. Alkylate product is passed through an eductor-mixer device which intimately mixes alkylate with catalyst. This mixture flows into the dual function recontacting vessel where a phase separation of the catalyst and alkylation hydrocarbon product takes place. Conduits are provided to connect the process reactor, cooling heat exchanger, settler, and interconnecting piping so as to allow the quick release of pressure from the combination storage-recontacting vessel and subsequent draining of catalyst into the vessel by use of gravitational force.Type: GrantFiled: November 7, 1991Date of Patent: February 9, 1993Assignee: Phillips Petroleum CompanyInventors: Scott D. Love, Stone P. Washer