Using Halogen-containing Catalyst Patents (Class 585/462)
  • Patent number: 8802908
    Abstract: Process and systems for alkane bromination and, in one or more embodiments, to separate, parallel methane and higher alkanes bromination in a bromine-based process. An embodiment discloses a bromine-based process for converting alkanes to liquid hydrocarbons that includes alkanes bromination, the process comprising: brominating a methane stream comprising methane and having less than about 2 mol % of ethane to form methane bromination products comprising brominated methane and a first fraction of hydrogen bromide; separately brominating a C2+ alkane stream comprising an alkane having 2 or more carbon atoms to form C2+ methane bromination products comprising brominated alkanes having 2 or more carbon atoms and a second fraction of hydrogen bromide; and catalytically reacting at least a portion of the brominated methane and the brominated alkanes to form higher molecular hydrocarbons.
    Type: Grant
    Filed: October 8, 2012
    Date of Patent: August 12, 2014
    Assignee: Marathon GTF Technology, Ltd.
    Inventors: John J. Waycullis, Sagar B. Gadewar, Raphael Thomas
  • Publication number: 20140100401
    Abstract: The present invention relates to catalyst composition prepared by a method wherein an aluminosilicate zeolite having its pores filled with templating agent with a specific organic silicon compound to deposit said organic silicon compound on the surface of the zeolite to provide an organosilicon treated catalyst precursor; and calcining the organosilicon treated catalyst precursor under conditions sufficient to remove the templating agent from the zeolite. Furthermore, the present invention relates to a method for preparing said catalyst composition and a process for alkylation of an aromatic hydrocarbon comprising contacting the catalyst composition of the present invention with a feed stream comprising said aromatic hydrocarbon and an alkylating agent under aromatic alkylation conditions.
    Type: Application
    Filed: May 3, 2012
    Publication date: April 10, 2014
    Applicant: Saudi Basic Industries Corporation
    Inventor: Debasish Das
  • Publication number: 20130324760
    Abstract: A method of crystallizing a crystalline molecular sieve having a pore size in the range of from about 2 to about 19 ?, said method comprising the steps of (a) providing a mixture comprising at least one source of ions of tetravalent element (Y), at least one hydroxide source (OH?), and water, said mixture having a solid-content in the range of from about 15 wt. % to about 50 wt. %; and (b) treating said mixture to form the desired crystalline molecular sieve with stirring at crystallization conditions sufficient to obtain a weight hourly throughput from about 0.005 to about 1 hr?1, wherein said crystallization conditions comprise a temperature in the range of from about 200° C. to about 500° C. and a crystallization time less than 100 hr.
    Type: Application
    Filed: August 7, 2013
    Publication date: December 5, 2013
    Inventors: Ivy D. Johnson, Wenyih Frank Lai
  • Patent number: 8492604
    Abstract: The present invention relates to a method and a reactor system for preparing linear alpha-olefins by oligomerization of ethylene in the presence of an organic solvent and an oligomerization catalyst, wherein a product fraction of C10+ alpha-olefins contaminated with aromatic C9+ compounds is separated from a product main stream and transferred into a conversion reactor, where C10+ alpha-olefins and aromatic C9+ components are reacted in the presence of a Friedel-Crafts alkylation catalyst to produce aromatic C19+ compound.
    Type: Grant
    Filed: January 31, 2007
    Date of Patent: July 23, 2013
    Assignee: Saudi Basic Industries Corporation
    Inventors: Peter M. Fritz, Wolfgang Müller, Florian Winkler, Heinz Bölt
  • Publication number: 20110178355
    Abstract: The present invention relates to a method and a reactor system for preparing linear alpha-olefins by oligomerization of ethylene in the presence of an organic solvent and an oligomerization catalyst, wherein a product fraction of C10+ alpha-olefins contaminated with aromatic C9+ compounds is separated from a product main stream and transferred into a conversion reactor, where C10+ alpha-olefins and aromatic C9+ components are reacted in the presence of a Friedel-Crafts alkylation catalyst to produce aromatic C19+ compounds.
    Type: Application
    Filed: January 31, 2007
    Publication date: July 21, 2011
    Applicants: LINDE AG, SAUDI BASIC INDUSTRIES CORPORATION
    Inventors: Peter M. Fritz, Wolfgang Müller, Florian Winnkler
  • Patent number: 7910783
    Abstract: A process for preparing a chelating ligand of the formula (II) from a chelating ligand of the formula (I) via an sp2-sp2 or sp2-sp3 coupling reaction with an organometallic compound of the formula (III).
    Type: Grant
    Filed: December 14, 2005
    Date of Patent: March 22, 2011
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Alexander Z. Voskoboynikov, Mikhail V. Nikulin, Alexey N. Ryabov, Alexander V. Lygin, Catalina L. Coker, Jo Ann M. Canich
  • Patent number: 7781599
    Abstract: A problem of the present invention is to provide an economical process with minimized toxicity for producing an aromatic compound having a variety of substituents such as various alkyl groups, and the problem is solved by a process for production of an aromatic compound represented by formula (1) below, which comprises reacting a compound represented by formula (2) below with an aromatic magnesium reagent represented by formula (3a) below in the presence of an iron catalyst and a diamine compound: wherein R is an optionally substituted hydrocarbon group or a C3-C10 saturated or unsaturated ring group; A is an optionally substituted C4-C20 aromatic group or an optionally substituted heteroaromatic group; X is a halogen atom or a sulfonic acid ester; and Y1 is bromine, iodine, chlorine or a carbanion ligand.
    Type: Grant
    Filed: February 10, 2005
    Date of Patent: August 24, 2010
    Assignee: Japan Science and Technology Agency
    Inventors: Masaharu Nakamura, Eiichi Nakamura, Keiko Matsuo, Shingo Ito
  • Publication number: 20100160703
    Abstract: A process for alkylating an aromatic compound containing no hydroxyl groups comprising reacting at least one non-hydroxyl containing aromatic compound with at least one olefinic oligomer in the presence of an acidic ionic liquid catalyst, wherein the olefinic oligomer has a carbon range of from about C12 to about C70 and is synthesized by oligomerizing at least one monoolefin monomer in the presence of an acidic ionic liquid catalyst.
    Type: Application
    Filed: February 19, 2010
    Publication date: June 24, 2010
    Applicant: Chevron Oronite Company LLC
    Inventors: Michael Driver, Curt B. Campbell, Thomas V. Harris
  • Patent number: 7732654
    Abstract: We provide a process for making a fuel or lubricant component, comprising: performing alkylation and oligomerization by contacting a stream comprising one or more olefins and one or more isoparaffins, wherein a molar ratio of the one or more olefins to the one or more isoparaffins in the stream is at least 0.8, an acidic chloroaluminate ionic liquid catalyst, and a halohalide; and recovering the fuel or lubricant component having a Bromine Number of less than 4. We provide a process comprising performing concurrent alkylation and oligomerization. We also provide a process for making a lubricant component having a kinematic viscosity at 100° C. of at least 6.9 mm2/s, a VI of at least 134, a cloud point less than or equal to ?28° C., and a Bromine Number of less than or equal to 6.1.
    Type: Grant
    Filed: June 9, 2009
    Date of Patent: June 8, 2010
    Assignee: Chevron U.S.A. Inc.
    Inventors: Saleh Elomari, Russell R. Krug
  • Patent number: 7723556
    Abstract: We provide a process for making a base oil, comprising: a) selecting an olefin feed produced by thermal cracking of a waxy feed; b) oligomerizing the olefin feed in an ionic liquid oligomerization zone at a set of oligomerization conditions to form an oligomer; and c) alkylating the oligomer in the presence of an isoparaffin, in an ionic liquid alkylation zone, at a set of alkylation conditions to form an alkylated oligomeric product having a kinematic viscosity at 100° C. of 6.9 mm2/s or greater, a VI of at least 134, and a Bromine Number of less than 4. We provide a process to make base oil from an olefin feed produced in a FCC unit. We also provide a process to make two or more viscosity grades of base oil from an olefin feed produced by thermal cracking of a waxy feed.
    Type: Grant
    Filed: July 6, 2009
    Date of Patent: May 25, 2010
    Assignee: Chevron U.S.A. Inc.
    Inventors: Saleh Elomari, Russell R. Krug, Stephen J. Miller
  • Patent number: 7674945
    Abstract: The present invention discloses a process for alkylation of an aromatic hydrocarbon or isoalkane with an olefin over the catalysis of a solid acid, comprising contacting a reaction material containing an aromatic hydrocarbon or C4-C6 isoalkane, C2-C18 monoolefin and a compound containing a strongly electronegative element as promoter with a solid acid catalyst to carry out the alkylation, characterized in that the solid acid catalyst is contacted with a compound having a strongly electronegative element prior to its contact with the reaction material. Said process not only greatly increases the selectivity of the target product of the alkylation but also improves stability of the solid acid catalyst.
    Type: Grant
    Filed: January 19, 2005
    Date of Patent: March 9, 2010
    Assignee: China Petroleum & Chemical Corporation
    Inventors: Yigong He, Zheng Man
  • Publication number: 20090163754
    Abstract: A process for alkylating an aromatic compound comprising reacting at least one aromatic compound with a mixture of olefins having from about 8 to about 100 carbon atoms, in the presence of a strong acid catalyst wherein the resulting product comprises at least about 60 weight percent of a 1, 2, 4 tri-alkylsubstituted aromatic compound.
    Type: Application
    Filed: December 21, 2007
    Publication date: June 25, 2009
    Inventors: Gilles P. Sinquin, Curt B. Campbell
  • Patent number: 7495140
    Abstract: A process for alkylating an aromatic compound comprising reacting (a) a first amount of at least one aromatic compound with a first amount of a mixture of olefins having from about 8 to about 100 carbon atoms, in the presence of a strong acid catalyst; and reacting the product of (a) with an additional amount of at least one aromatic compound and an additional amount of a strong acid catalyst, and optionally, with an additional amount of a mixture of olefins selected from olefins having from about 8 to about 100 carbon atoms, wherein the resulting product comprises at least about 80 weight percent of a 1,2,4 tri-alkylsubstituted aromatic compound.
    Type: Grant
    Filed: June 1, 2006
    Date of Patent: February 24, 2009
    Assignee: Chevron Cronite Company LLC
    Inventors: Curt B. Campbell, Gilles Sinquin
  • Patent number: 7297827
    Abstract: Disclosed is an alkylation reactor for preparing ethylbenzene. The reactor comprises a monolith catalyst system that includes a monolith support impregnated or co-formed with a catalyst suitable to catalyze the alkylation of benzene with ethylene. The catalyst may be selected from, for example, zeolites such as beta zeolite and MCM-22 zeolite, and fixed super acids. Also disclosed is a method of preparing ethylbenzene by alkylating a mixture of benzene and ethylene in an alkylation reactor comprising a monolith catalyst system, including a monolith support impregnated or co-formed with a suitable catalyst. In one embodiment the invention provides a convenient means of upgrading an existing reactor that has previously been used for conventional liquid phase alkylations such as those catalyzed by aluminum trichloride. The inventive alkylation method may be effectively and advantageously carried out under critical or near critical conditions, if desired.
    Type: Grant
    Filed: November 29, 2004
    Date of Patent: November 20, 2007
    Assignee: Fina Technology, Inc.
    Inventor: Kevin Kelly
  • Patent number: 7294420
    Abstract: A method of producing hydrogen for a fuel cell from a hydrocarbon fuel composition, by providing a hydrocarbon fuel composition, which is obtained by contacting a liquid hydrocarbon feed comprising an alkylating agent with an acidic catalyst, under conditions effective to alkylate at least a portion of the hydrocarbon feed; converting the hydrocarbon fuel composition into hydrogen; and optionally, introducing the hydrogen produced into a fuel cell. In a preferred embodiment the liquid hydrocarbon feed further comprises sulphur-containing impurities, at least a portion of which are alkylated during the alkylation step.
    Type: Grant
    Filed: August 28, 2002
    Date of Patent: November 13, 2007
    Assignee: BP P.L.C.
    Inventor: Michael Graham Hodges
  • Patent number: 7151199
    Abstract: 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: Grant
    Filed: June 10, 2002
    Date of Patent: December 19, 2006
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Luc Roger Marc Martens, Stephen N. Vaughn, Albert Edward Schweizer, John K. Pierce, Shun Chong Fung
  • Patent number: 7148388
    Abstract: In a process for preparing an olefinic hydrocarbon mixture comprising at least 5% by weight of mono-olefin oligomers of the empirical formula: CnH2n where n is greater than or equal to 6, a feedstock comprising n-butene and propylene in a molar ratio of about 1:0.01 to about 1:0.49 is contacted under oligomerization conditions with surface deactivated ZSM-23. The resultant mono-olefin oligomers comprise at least 20 percent by weight of olefins having at least 12 carbon atoms, wherein said olefins having at least 12 carbon atoms have an average of from about 0.8 to about 2.0 C1–C3 alkyl branches per carbon chain.
    Type: Grant
    Filed: March 28, 2003
    Date of Patent: December 12, 2006
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Stephen W. Beadle, Cesar M. Cheng-Guajardo, Carolyn B. Duncan, David Wayne Turner, Ramzi Y. Saleh
  • Patent number: 7105713
    Abstract: A method of modifying a ZSM-5-type zeolite catalyst to increase selectivity of the catalyst for para-isomers in aromatic alkylation reactions is provided. The method includes contacting a ZSM-5-type zeolite catalyst with a fluoride-containing compound. The fluoride-containing zeolite catalyst can be used in aromatic alkylation to provide di-alkyl aromatic products. A method of preparing a xylene product is also accomplished by providing a fluoride-treated ZSM-5-type zeolite catalyst within a reactor. The fluoride-treated ZSM-5 zeolite catalyst is contacted with a toluene/methanol feed under reaction conditions conditions suitable for toluene methylation to form a xylene product containing at least 50% para-xylene by total mixed xylenes.
    Type: Grant
    Filed: June 8, 2005
    Date of Patent: September 12, 2006
    Assignee: Saudi Basic Industries Corporation
    Inventors: Ashim Kumar Ghosh, Pamela Harvey
  • Patent number: 7038099
    Abstract: A method of alkylating aliphatic or aromatic hydrocarbons with olefins using solid hydrogen fluoride-equivalent catalysts is described. Preferred catalysts comprise solid polymeric onium polyhydrogen fluoride complexes.
    Type: Grant
    Filed: November 26, 2003
    Date of Patent: May 2, 2006
    Inventor: George A Olah
  • Patent number: 6605566
    Abstract: A novel supported bimetallic catalyst comprises a group VIII metal such as platinum, and tin, at least a portion of which interacts strongly with the group VIII metal in the catalyst in the reduced state. In the partially oxidized state, the catalyst of the invention contains at least 10% of tin in the form of a reduced tin species with oxidation state 0, said species having an isomer shift in the range 0.80 to 2.60 mm/s and a quadrupolar splitting in the range 0.65 to 2.00 mm/s. The invention also concerns the preparation of said catalyst, and processes using said catalyst for transforming hydrocarbons into aromatic compounds, such as gasoline reforming processes and aromatic production processes.
    Type: Grant
    Filed: August 23, 2001
    Date of Patent: August 12, 2003
    Assignee: Institut Francais du Petrole
    Inventors: Fabienne Le Peltier, Blaise Didillon, Jean-Claude Jumas, Josette Olivier-Fourcade
  • Patent number: 6573415
    Abstract: 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: Grant
    Filed: August 20, 2001
    Date of Patent: June 3, 2003
    Assignee: Haldor Topsoe A/S
    Inventors: Sven Ivar Hommeltoft, Karsten Laurents
  • Publication number: 20030097033
    Abstract: The present invention relates to a process for the preparation of an alkali metal catalyst by mixing a melt of the alkali metal with a pulverulent, solid inorganic material at above the melting point of the alkali metal, wherein the pulverulent, solid inorganic material comprises a mixture of potassium carbonate and at least one alkali metal chloride selected from sodium chloride and potassium chloride.
    Type: Application
    Filed: October 29, 2002
    Publication date: May 22, 2003
    Inventor: Ulrich Steinbrenner
  • Patent number: 6534690
    Abstract: A process for the preparation of at least one spherically shaped porous microcomposite is provided which microcomposite comprises a perfluorinated ion-exchange polymer containing pendant sulfonic and/or carboxylic acid groups entrapped within and highly dispersed throughout a network of inorganic oxide, wherein the weight percentage of the perfluorinated ion-exchange polymer in the microcomposite is from about 0.1 to about 90 percent, and wherein the size of the pores in the microcomposite is about 0.
    Type: Grant
    Filed: April 26, 2001
    Date of Patent: March 18, 2003
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Qun Sun
  • Publication number: 20020173684
    Abstract: A method of alkylating aliphatic or aromatic hydrocarbons with olefins using solid hydrogen fluoride-equivalent catalysts is described. Preferred catalysts comprise solid polymeric onium polyhydrogen fluoride complexes.
    Type: Application
    Filed: May 17, 2001
    Publication date: November 21, 2002
    Inventor: George A. Olah
  • Patent number: 6436866
    Abstract: Disclosed is a Lewis acid catalyst composition comprising a specific mixed medium and a Lewis acid catalyst (II), wherein the specific mixed medium is mixed medium (I) comprising a perfluorinated aliphatic hydrocarbon (A) and at least one non-fluorinated hydrocarbon or a mixed medium (I′) comprising a perfluorinated aliphatic hydrocarbon (A), a perfluorinated aromatic hydrocarbon (C) and water (D), and wherein the Lewis acid catalyst (II) is at least one compound selected from the group consisting of compounds respectively represented by the following formulae (1), (2) and (3): (RfSO3)nM  (1), [(RfSO2)2N]nM  (2), and [(RfSO2)3C]nM  (3). Also disclosed is a Lewis acid catalyst represented by the above-mentioned formula (3).
    Type: Grant
    Filed: May 26, 2000
    Date of Patent: August 20, 2002
    Assignee: Asahi Kasei Kabushiki Kaisha
    Inventors: Joji Nishikido, Hitoshi Nakajima
  • Patent number: 6399835
    Abstract: Processes for the electrophilic substitution of aromatic compounds, such as alkylation, with a desired substituent are disclosed. The processes include contacting the aromatic compound, a precursor of the desired substituent and an aqueous reagent containing zinc halide at elevated temperatures such as above 50° C.
    Type: Grant
    Filed: April 6, 2000
    Date of Patent: June 4, 2002
    Assignee: Bromine Compounds Ltd.
    Inventors: Ariel Ewenson, David Itzhak, Miriam Freiberg Bergstein, Asher Shushan, Bertha Croitoru, David Beneish, Naim Faza
  • Publication number: 20020045788
    Abstract: 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: Application
    Filed: August 20, 2001
    Publication date: April 18, 2002
    Applicant: Haldor Topsoe A/S
    Inventors: Sven I. Hommeltoft, Karsten Laurents
  • Publication number: 20010037045
    Abstract: A process for the preparation of at least one spherically shaped porous microcomposite is provided which microcomposite comprises a perfluorinated ion-exchange polymer containing pendant sulfonic and/or carboxylic acid groups entrapped within and highly dispersed throughout a network of inorganic oxide, wherein the weight percentage of the perfluorinated ion-exchange polymer in the microcomposite is from about 0.1 to about 90 percent, and wherein the size of the pores in the microcomposite is about 0.
    Type: Application
    Filed: April 26, 2001
    Publication date: November 1, 2001
    Inventors: Mark Andrew Harmer, Qun Sun
  • Patent number: 6281400
    Abstract: The present invention relates to a process for preparing a microcomposite comprising a highly fluorinated ion-exchange polymer containing pendant sulfonate functional groups, said polymer existing as aggregated particles entrapped within and dispersed throughout a network of silica. Due to their high surface area and acid functionality, these microcomposites possess wide utility as improved solid acid catalysts, particularly in the substitution of aromatic compounds, in the decomposition of hydroperoxides, and in the isomerization of olefins.
    Type: Grant
    Filed: January 14, 2000
    Date of Patent: August 28, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Qun Sun
  • Patent number: 6248930
    Abstract: This invention concerns fluorine-modified perfluorinated ion-exchange microcomposites, comprising a perfluorinated ion-exchange polymer containing pendant sulphonic acid groups and/or carboxylic acid groups, entrapped within and highly dispersed throughout a network of inorganic oxide, said network having a plurality of fluoride groups bonded thereto; processes for their preparation and their use as catalysts in chemical processes such as alkylation of aromatic compounds.
    Type: Grant
    Filed: September 1, 1999
    Date of Patent: June 19, 2001
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Qun Sun
  • Patent number: 6160190
    Abstract: Porous microcomposites have been prepared from perfluorinated ion-exchange polymer and metal oxides such as silica using the sol-gel process. Such microcomposites possess high surface area and exhibit extremely high catalytic activity. The microcomposites catalyze, among others, the reaction between organic aromatic compounds and olefins.
    Type: Grant
    Filed: June 3, 1999
    Date of Patent: December 12, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Qun Sun
  • Patent number: 6133493
    Abstract: This invention concerns a modified porous microcomposite comprising a perfluorinated ion-exchange polymer entrapped within and highly dispersed throughout a network of inorganic oxide wherein the network and optionally the pendant groups of the polymer have been modified with a Lewis acid. These modified microcomposites can be used in catalyst compositions for various chemical processes, such as in the alkylation or acylation of aromatics.
    Type: Grant
    Filed: May 6, 1999
    Date of Patent: October 17, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Mark Andrew Harmer, Qun Sun
  • Patent number: 6005151
    Abstract: The invention relates to a process for preparing monofunctional, bifunctional or polyfunctional aromatic olefins of the formula (I) ##STR1## wherein a palladium compound of the formula (IV) ##STR2## is used as a catalyst in the preparation of the compounds of the formula (I).
    Type: Grant
    Filed: January 30, 1996
    Date of Patent: December 21, 1999
    Assignee: Aventis
    Inventors: Wolfgang Anton Herrmann, Matthias Beller, Ahmed Tafesh
  • Patent number: 5994602
    Abstract: This invention relates to a process for the alkylation of aromatics by reacting an aromatic hydrocarbon with an olefin in the presence of an ionic liquid comprising (a) a compound of the formula R.sub.n MX.sub.3-n wherein R is a C1-C6 alkyl radical, M is aluminium or gallium, X is a halogen atom and n is 0, 1 or 2 and, (b) a hydrocarbyl substituted imidazolium halide or a hydrocarbyl substituted pyridinium halide wherein at least one of the said hydrocarbyl substituents in the imidazolium halide is an alkyl group having 1-18 carbon atoms. The process allows ready separation of reaction products from the ionic liquid and improves selectivity to alkylated products.
    Type: Grant
    Filed: July 29, 1997
    Date of Patent: November 30, 1999
    Assignee: BP Chemicals Limited
    Inventors: Ala'a K Abdul-Sada, Martin Philip Atkins, Brian Ellis, Philip Kenneth Gordon Hodgson, Mark Louis Michael Morgan, Kenneth Richard Seddon
  • Patent number: 5986155
    Abstract: 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: Grant
    Filed: July 10, 1996
    Date of Patent: November 16, 1999
    Assignee: The Lubrizol Corporation
    Inventors: 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: 5977422
    Abstract: This invention relates to an improved catalytic process for the alkylation of benzene or substituted benzene with alkyl halides for the continuous production of diarylalkanes or substituted derivatives thereof using ethylaluminum dichloride or methylaluminum dichloride as an organoaluminum dichloride catalyst. A process and apparatus are provided for reacting either benzene (or a substituted benzene compound) together with either an alkyl halide or an aromatic halide.
    Type: Grant
    Filed: June 9, 1997
    Date of Patent: November 2, 1999
    Assignee: The Dow Chemical Company
    Inventors: Steven A. Costello, Douglas L. Potts, Randall F. Pogue
  • Patent number: 5959169
    Abstract: Process for the selective removal of aromatic compounds from a hydrocarbon mixture by contacting the mixture in presence of an olefinic alkylating agent with an alkylation catalyst selected from the group of fluorinated alkyl sulphonic acids movably adsorbed on a silica comprising carrier material.
    Type: Grant
    Filed: April 2, 1998
    Date of Patent: September 28, 1999
    Assignee: Haldor Topsoe A/S
    Inventor: Sven Ivar Hommeltoft
  • Patent number: 5877383
    Abstract: A process for the manufacture of a hydrocarbon mixture being rich in middle distillate products with the boiling part range of 175.degree.-360.degree. C. by alkylation of a hydrocarbon feed stock with an olefinic alkylating agent, comprises the steps of contacting a hydrocarbon feedstock and an olefinic alkylating agent with a catalyst composition containing an acid selected from the group of fluorinated alkane sulphonic acids having the general formula: ##STR1## wherein R'=F, Cl, Br, I, H, an alkyl or perfluoro alkyl group,R"=H, alkyl, aryl or a perfluoro alkoxy group, andrecovering a product stream of alkylated hydrocarbons and optionally recycling to the reactor lower isoalkanes being formed during the alkylation.
    Type: Grant
    Filed: November 5, 1997
    Date of Patent: March 2, 1999
    Assignee: Haldor Topsoe A/S
    Inventors: Sven Ivar Hommeltoft, Annemarie Bauer
  • Patent number: 5849965
    Abstract: 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: Grant
    Filed: May 22, 1997
    Date of Patent: December 15, 1998
    Assignee: Amoco Corporation
    Inventors: Robert L. Mehlberg, George A. Huff, Jr.
  • Patent number: 5824832
    Abstract: A low temperature molten ionic liquid composition comprising a mixture of a metal halide and an alkyl-containing amine hydrohalide salt can be used in linear alkylbenzene formation. The metal halide is a covalently bonded metal halide which can contain a metal selected from the group comprised of aluminum, gallium, iron, copper, zinc, and indium, and is most preferably aluminum trichloride. The alkyl-containing amine hydrohalide salt may contain up to three alkyl groups, which are preferably lower alkyl, such as methyl and ethyl.
    Type: Grant
    Filed: March 27, 1997
    Date of Patent: October 20, 1998
    Assignee: Akzo Nobel NV
    Inventors: Fawzy G. Sherif, Lieh-Jiun Shyu, Carl C. Greco
  • Patent number: 5750818
    Abstract: A process for cooling unreacted hydrocarbon substrate that is recycled to an alkylation reactor and for minimizing the concentration of lower boiling hydrocarbons in such recycle.
    Type: Grant
    Filed: June 20, 1996
    Date of Patent: May 12, 1998
    Assignee: Amoco Corporation
    Inventors: Robert L. Mehlberg, James B. Young
  • Patent number: 5663474
    Abstract: This invention relates to catalysts for alkylation reactions and their preparation. More particularly, the invention relates to an alkylation process using a hydrogen fluoride-containing alkylation catalyst, which catalyst may be safely and easily handled, transported, and stored.
    Type: Grant
    Filed: March 7, 1996
    Date of Patent: September 2, 1997
    Assignee: AlliedSignal Inc.
    Inventors: Hang Thanh Pham, Robert Pratt, Charles Lewis Redmon, John James Thompson, Michael Van Der Puy, Rajiv Ratna Singh, William James Hague, Harold John Kieta, Matthew Hermes Luly, Jeffrey Warren McKown
  • Patent number: 5648580
    Abstract: A supported Lewis acid catalyst system for catalyzing hydrocarbon conversion reactions including cationic polymerization, alkylation, isomerization and cracking reactions is disclosed, wherein the catalyst system comprises an inorganic oxide support having immobilized thereon at least one relatively strong Lewis acid and at least one relatively weak Lewis acid.
    Type: Grant
    Filed: September 4, 1996
    Date of Patent: July 15, 1997
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Frank Joung-yei Chen, Christophe Le Deore, Roger Spitz, Alan Guyot
  • Patent number: 5600050
    Abstract: Disclosed is a modified zeolite catalyst for the liquid phase alkylation and transalkylation of benzene comprising 30 to 70% by weight of H-beta zeolite with a silicon to aluminium ratio of 20 to 40; 0.5 to 10% by weight of halogen; and .gamma.-Al.sub.2 O.sub.3 of the balance. Also disclosed a method for preparing the said catalyst comprising adding a halogen-containing compound to a mixture of H-beta zeolite and a precursor of .gamma.-Al.sub.2 O.sub.3, forming followed by calcining.
    Type: Grant
    Filed: December 14, 1994
    Date of Patent: February 4, 1997
    Assignees: ChinaPetro-Chemical Corp., Research Institute of Petroleum Processing
    Inventors: Zhiyuan Huang, Suxian Tian, Yali Xu, Bin Zhu, Weidong Wang, Fengmei Zhang, Xie Wang
  • Patent number: 5498820
    Abstract: Process for the alkylation of a hydrocarbon feedstock with an olefinic alkylating agent comprising the steps of contacting the hydrocarbon feedstock and the olefinic alkylating agent with a fluorinated alkoxy alkane sulphonic acid catalyst for a sufficient time and recovering a product stream of alkylated hydrocarbons.
    Type: Grant
    Filed: August 9, 1994
    Date of Patent: March 12, 1996
    Assignee: Haldor Topsoe A/S
    Inventor: Sven I. Hommeltoft
  • Patent number: 5488193
    Abstract: A process for reducing the mutagenicity of a polynuclear aromatic containing material containing from three to seven fused aromatic rings, especially a hydrocarbon refinery stream. The process reduces the initial mutagenicity index to a lower value by alkylating the compound with an alkylating agent which introduces an alkyl substituent having from three to five carbon atoms into the aromatic compound in the presence of an acid catalyst under alkylation conditions.
    Type: Grant
    Filed: January 25, 1995
    Date of Patent: January 30, 1996
    Assignee: Mobil Oil Corporation
    Inventors: Carl R. Mackerer, Timothy A. Roy, Gary R. Blackburn
  • Patent number: 5386072
    Abstract: Process for the preparation of linear alkylbenzenes, wherein the benzene is reacted, in the presence of aluminum chloride or aluminum in powder form, with a mixture composed of C.sub.7 -C.sub.20 n-olefins and C.sub.7 -C.sub.20 chloroparaffins, with a molar ratio n-olefins/chloroparaffins between 70:30 and 99:1.
    Type: Grant
    Filed: January 29, 1993
    Date of Patent: January 31, 1995
    Assignee: Enichem Augusta S.p.A.
    Inventors: Pierluigi Cozzi, Giuseppe Giuffrida, Tullio Pellizzon, Pierino Radici
  • Patent number: 5344997
    Abstract: A fluorided silica-alumina catalyst, particularly one with a silica:alumina ratio in the range of 1:1-9:1 containing from 1 to 6 weight percent fluoride, is particularly effective in the liquid phase alkylation of benzene by linear olefins to produce linear alkyl benzenes at temperatures no greater than 140.degree. C. These catalysts also are effective in the liquid phase alkylation of alkylatable aromatics generally with a variety of alkylating agents, including olefins, alcohols, and alkyl halides.
    Type: Grant
    Filed: December 14, 1992
    Date of Patent: September 6, 1994
    Assignee: UOP
    Inventor: Joseph A. Kocal
  • Patent number: 5324695
    Abstract: A process for regenerating deactivated metal oxide catalysts comprising at least one of the elements antimony, iron, bismuth, molybdenum, vanadium, tungsten and/or uranium and a peptizable carrier, comprises the steps of:a) grinding the metal oxide catalyst in the presence of water to a particle size of from 10 nm to 10 .mu.m,b) heating the aqueous suspension of the metal oxide catalyst of stage a) to 30-100.degree. C. and adding an acid which peptizes the carrier,c) spray drying the acidic suspension of the metal oxide catalyst,d) heating the fluidizable metal oxide catalyst particles of stage c) to 500.degree.-850.degree. C.
    Type: Grant
    Filed: January 8, 1993
    Date of Patent: June 28, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Lothar Karrer, Klaus Herzog, Heinrich Aichinger, Hans-Dieter Eichhorn, Guenter Herrmann
  • Patent number: 5324877
    Abstract: A composition useful for catalyzing alkylation and transalkylation reactions comprises a molecular sieve having alkylation and/or transalkylation activity, an inorganic refractory oxide component and greater than 3.5 weight percent water. Such a catalyst has been found to maintain a long life when used to produce ethylbenzene in an integrated process in which benzene is alkylated with ethylene and transalkylated with diethylbenzene. The catalyst can also be used to produce cumene via an integrated process in which benzene is alkylated with propylene and transalkylated with diisopropylbenzene.
    Type: Grant
    Filed: April 22, 1993
    Date of Patent: June 28, 1994
    Assignee: Union Oil Company of California
    Inventors: Martin West, Suheil F. Abdo