P Compound On Solid Carrier, E.g., "solid Phosphoric Acid", Etc. Patents (Class 585/529)
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Patent number: 9522373Abstract: Disclosed is a process and apparatus for switching oligomerization feed between a first oligomerization zone that includes a uni-dimensional small pore zeolite to make more diesel and a second oligomerization zone that includes SPA catalyst for making more gasoline. The diesel can be recycled to make more propylene. The process and apparatus will provide refiners with flexibility to produce the most valuable product commensurate with fluctuating market conditions.Type: GrantFiled: November 8, 2013Date of Patent: December 20, 2016Assignee: UOP LLCInventors: Christopher P. Nicholas, Christian D. Freet, Steven L. Krupa, Kurt M. Vanden Bussche, Todd M. Kruse
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Patent number: 9403149Abstract: The present invention relates to solid phosphoric acid (SPA) catalysts, processes for making the catalysts, and processes for conversion of hydrocarbons using the catalysts, such as oligomerization of propylene. In an exemplary embodiment, the catalyst comprises a calcined extrudate of phosphoric acid, diatomaceous earth, and niobic acid. Methods for converting hydrocarbons to olefins comprise contacting a hydrocarbon feedstock with the catalyst at hydrocarbon conversion conditions.Type: GrantFiled: September 21, 2011Date of Patent: August 2, 2016Assignee: Clariant CorpoationInventors: Wayne Turbeville, Greg Korynta
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Patent number: 8933285Abstract: Methods are provided for producing a jet fuel composition from a feedstock comprising a natural oil. The methods comprise reacting the feedstock with a low-weight olefin in the presence of a metathesis catalyst under conditions sufficient to form a metathesized product. The methods further comprise hydrogenating the metathesized product under conditions sufficient to form a jet fuel composition.Type: GrantFiled: November 25, 2009Date of Patent: January 13, 2015Assignee: Elevance Renewable Sciences, Inc.Inventors: Melvin L. Luetkens, Jr., Steven A. Cohen, Chander Balakrishnan
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Patent number: 8865955Abstract: One exemplary embodiment is a process for oligomerizing one or more hydrocarbons. The process includes providing a feed including one or more C3 and C4 hydrocarbons to a separation zone, separating a first stream including an effective amount of C3 olefins for oligomerizing, separating a second stream including an effective amount of one or more C4 olefins for oligomerizing, providing at least a portion of the first stream to a first oligomerization zone for producing at least one of a C9 and a C12 hydrocarbon, and providing at least a portion of the second stream to a second oligomerization zone for producing at least one of a C8 and a C12 hydrocarbon.Type: GrantFiled: December 10, 2010Date of Patent: October 21, 2014Assignee: UOP LLCInventors: Steven Lee Krupa, Christian D. Freet, Mohamed Shakur
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Patent number: 8853483Abstract: A process for oligomerizing isoolefins, the process including: feeding an isoolefin to an oligomerization reaction zone; feeding an oxygen-containing reaction moderator to the oligomerization reaction zone; concurrently in the oligomerization reaction zone: contacting the isoolefin with an oligomerization catalyst to convert at least a portion of the isoolefin to oligomers comprising dimers and trimers of the isoolefin; reacting a portion of the moderator with a portion of at least one of the isoolefin and the oligomers to form an oxygenated oligomerization byproduct; recovering an effluent from the oligomerization reaction zone comprising the oligomers and the oxygenated oligomerization byproduct; fractionating at least a portion of the effluent to recover a fraction comprising the oxygenated oligomerization byproduct and the trimers and a fraction comprising the dimers.Type: GrantFiled: December 2, 2008Date of Patent: October 7, 2014Assignee: Catalytic Distillation TechnologiesInventors: Mitchell E. Loescher, Turi Odegard
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Publication number: 20140135543Abstract: Disclosed is a process and apparatus for switching oligomerization feed between a first oligomerization zone that includes a uni-dimensional small pore zeolite to make more diesel and a second oligomerization zone that includes SPA catalyst for making more gasoline. The diesel can be recycled to make more propylene. The process and apparatus will provide refiners with flexibility to produce the most valuable product commensurate with fluctuating market conditions.Type: ApplicationFiled: November 8, 2013Publication date: May 15, 2014Applicant: UOP LLCInventors: Christopher P. Nicholas, Christian D. Freet, Steven L. Krupa, Kurt M. Vanden Bussche, Todd M. Kruse
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Publication number: 20140135541Abstract: Oligomerizing C4 and C5 olefins over a SPA catalyst provides an oligomerate product stream comprising C6+ olefins that meets a gasoline T-90 specification of 380° F. The oligomerate product stream can be taken to the gasoline pool without further upgrading.Type: ApplicationFiled: November 8, 2013Publication date: May 15, 2014Applicant: UOP LLCInventors: Christopher P. Nicholas, Christian D. Freet, Steven L. Krupa, Kurt M. Vanden Bussche, Todd M. Kruse
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Publication number: 20140135549Abstract: A process and apparatus that uses a debutanizer with a side stripper can recover a light stream, an intermediate stream and a liquid stream. One of the intermediate stream and the liquid stream can be recycled to oligomerization or to fluid catalytic cracking.Type: ApplicationFiled: November 7, 2013Publication date: May 15, 2014Applicant: UOP LLCInventors: Christian D. Freet, Charles P. Luebke, Clayton C. Sadler
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Patent number: 8598396Abstract: Olefin feeds with high olefin content and/or containing a substance that generates water when contacting the catalyst, are oligomerised over solid phosphoric acid catalyst in tubular reactors by introducing the olefin feed into the reactor and maintaining the reacting mixture under conditions whereby the peak temperature is controlled to be below 265° C. and preferably a single liquid or dense phase is maintained and the average temperature throughout the reactor is maintained in the range 190° C. to 260° C.Type: GrantFiled: June 9, 2006Date of Patent: December 3, 2013Assignee: ExxonMobil Chemical Patents Inc.Inventors: Stephen Wayne Beadle, John Stephen Godsmark, Robert L. Wolf
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Patent number: 8354566Abstract: An overbased salt of an oligomerized alkylhydroxyaromatic compound for use in a lubricating oil composition is disclosed, wherein the alkyl group of the alkylhydroxyaromatic compound is derived from an olefin mixture comprising propylene oligomers having an initial boiling point of at least about 195° C. and a final boiling point of greater than 325° C. and up to about 400° C. as measured by ASTM D86. Also disclosed is a propylene oligomer having an initial boiling point of at least about 195° C. and a final boiling point of greater than 325° C. and up to about 400° C. as measured by ASTM D8, wherein the propylene oligomer contains a distribution of carbon atoms that comprise at least about 50 weight percent of C14 to C20 carbon atoms.Type: GrantFiled: April 17, 2012Date of Patent: January 15, 2013Assignees: Chevron Oronite Company LLC, Chevron Oronite S.A.Inventors: Gilles P. Sinquin, Michael R. Adams
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Patent number: 8203025Abstract: The invention provides a solid phosphoric acid catalyst which has high activity and attains high dimer selectivity in olefin dimerization reactions and efficient methods of olefin dimerization. The solid phosphoric acid catalyst comprises a carrier and phosphoric acid supported thereon. When the solid phosphoric acid catalyst is heated at 250° C. for 20 minutes, heating loss of water is 50 mass % or more based on diphosphorus pentoxide (P2O5) derived from the phosphoric acid. A method of olefin dimerization comprises bringing an olefin-containing feed material containing water in an amount of 10-1000 mass ppm into contact with the catalyst to initiate the reaction.Type: GrantFiled: May 25, 2006Date of Patent: June 19, 2012Assignee: Nippon Oil CorporationInventors: Tatsuo Hamamatsu, Nobuhiro Kimura, Tsutomu Takashima, Takashi Morikita
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Patent number: 8178740Abstract: A process for the use in the oligomerization of olefins is presented. The process produces a gasoline boiling range product having a high research octane number and almost no aromatics content. The process utilizes a solid catalyst comprising a zeolite that is treated with a phosphorous containing reagent to generate a catalyst having phosphorous content between 0.5 and 15 wt %.Type: GrantFiled: December 9, 2008Date of Patent: May 15, 2012Assignee: UOP LLCInventors: Christopher P. Nicholas, Laszlo T. Nemeth, Deng-Yang Jan
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Publication number: 20120101321Abstract: The oligomerization of ethylene using a chromium catalyst having a bridged diphosphine ligand can produce a selective product distribution (to predominantly hexene or predominantly octene/hexene) when activated with an aluminoxane. The oligomerization reaction also produces polymer by product—particularly when the aluminoxane is provided in a non-aromatic solvent. The present invention mitigates this problem.Type: ApplicationFiled: September 22, 2011Publication date: April 26, 2012Inventors: Stephen John Brown, Charles Ashton Garret Carter, P. Scott Chisholm, Isam Jaber
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Patent number: 8153854Abstract: A process for producing an alkylate having a low Reid vapor pressure, the process including: contacting a C6+-containing hydrocarbon stream with a mixture of isopentane and isobutane in the presence of an acid catalyst in an alkylation reactor to form a dilute alkylate product, wherein the C6+-containing hydrocarbon stream includes at least one of oligomers of C3 to C5 olefins and a dilute alkylate produced by contacting an isoparaffin with at least one of C3 to C5 olefins and oligomers of C3 to C5 olefins; fractionating the dilute alkylate product to form an isobutane-rich fraction, a n-butane-rich fraction, a fraction containing isopentane, and an alkylate product having a Reid vapor pressure less than 0.35 bar (5 psi); recycling at least a portion of the fraction containing isopentane to the alkylation reactor.Type: GrantFiled: June 6, 2008Date of Patent: April 10, 2012Assignee: Catalytic Distillation TechnologiesInventors: Lawrence A. Smith, Jr., Abraham P. Gelbein, William M. Cross, Jr.
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Patent number: 8063260Abstract: The present invention relates to a solid phosphoric acid catalyst and a process for conversion of hydrocarbons using a solid phosphoric acid catalyst. The solid phosphoric acid catalyst comprises silicon orthophosphate, and has a silicon orthophosphate to silicon pyrophosphate ratio of at least about 5:1. The total pore volume of the solid phosphoric acid catalyst is at least about 0.17 cm3 per gram of catalyst, of which at least about 0.15 cm3 per gram is contributed by pores with diameter of at least about 10,000 ?.Type: GrantFiled: July 7, 2009Date of Patent: November 22, 2011Assignee: Sud-Chemie Inc.Inventors: Ling Xu, Wayne Turbeville, Gregory A. Korynta, Jeffrey L. Braden
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Patent number: 7786337Abstract: In a process for oligomerizing an olefinic hydrocarbon feedstock, the feedstock is contacted under oligomerization conditions with (a) a first crystalline molecular sieve catalyst and (b) a second catalyst comprising a solid phosphoric acid. The first and second catalysts may be contained in separate reactors or as separate beds in a single reactor.Type: GrantFiled: May 26, 2005Date of Patent: August 31, 2010Assignee: ExxonMobil Chemical Patents Inc.Inventors: Stephen Harold Brown, John Stephen Godsmark, Georges Maria Karel Mathys
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Patent number: 7601309Abstract: Disclosed is a process for integrating a butene dimerization process with a metathesis process to remove isobutene from the feed stream to the metathesis reactor. The isobutene is preferentially dimerized in the dimerization process to leave n-butenes for metathesis with ethylene. An upstream selective hydrogenation process also isomerizes 1-butenes to 2-butenes which is the preferred butene reagent in the metathesis process. A common fractionator column for the dimerization and hydrogenation processes is also described.Type: GrantFiled: November 3, 2008Date of Patent: October 13, 2009Assignee: UOP LLCInventors: Steven L. Krupa, Jill M. Meister
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Publication number: 20090099400Abstract: A solid phosphoric acid catalyst which has high activity and attains high dimer selectivity in olefin dimerization reactions; and efficient methods of olefin dimerization reaction. The solid phosphoric acid catalyst comprises a carrier and phosphoric acid supported thereon. When the solid phosphoric acid catalyst is heated at 250° C. for 20 minutes, heating loss of water is 50 mass % or more based on diphosphorus pentaoxide (P2O5) derived from the phosphoric acid. One of the methods of olefin dimerization reaction comprises bringing an olefin-containing feed material containing water in an amount of 10-1000 mass ppm into contact with the catalyst to initiate the reaction.Type: ApplicationFiled: May 25, 2006Publication date: April 16, 2009Applicant: Nippon Oil CorporationInventors: Tatsuo Hamamatsu, Nobuhiro Kimura, Tsutomu Takashima, Takashi Morikita
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Patent number: 7485765Abstract: A process is described for obtaining a 1,3-butadiene homopolymer by the reaction of a catalytic system in the presence of 1,3-butadiene and one or more monoolefin(s) with 4 carbon atoms. This catalytic system is based on at least: a conjugated diene monomer, an organic phosphoric acid salt of one or more rare earth metals, said salt being in suspension in at least one inert, saturated and aliphatic or alicyclic hydrocarbon solvent, an alkylating agent of the formula AlR3 or HAlR2, where R is an alkyl group, and an alkylaluminum halide halogen donor.Type: GrantFiled: May 16, 2005Date of Patent: February 3, 2009Assignee: Michelin Recherche Et Technique S.A.Inventors: Fanny Barbotin, Jean-Philippe Rasigade
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Patent number: 7459593Abstract: Disclosed is a process for integrating a butene dimerization process with a metathesis process to remove isobutene from the feed stream to the metathesis reactor. The isobutene is preferentially dimerized in the dimerization process to leave n-butenes for metathesis with ethylene. An upstream selective hydrogenation process also isomerizes 1-butenes to 2-butenes which is the preferred butene reagent in the metathesis process. A common fractionator column for the dimerization and hydrogenation processes is also described.Type: GrantFiled: November 18, 2005Date of Patent: December 2, 2008Assignee: UOP LLCInventors: Steven L. Krupa, Jill M. Meister
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Patent number: 7208440Abstract: The invention relates to a method for pretreatment of a solid catalyst that is obtained by a reaction between an inorganic binder and phosphoric acid, whereby said method comprises a stage in which said catalyst is brought into contact with a mixture of hydrocarbons under swelling conditions of the catalyst up to a predetermined volume increase, with no significant volume constraint on said catalyst. The invention also relates to an operating process of said catalyst in an alkylation or oligomerization reactor.Type: GrantFiled: October 13, 2004Date of Patent: April 24, 2007Assignee: Institut Francais du PetroleInventors: Florent Picard, Julia Magne-Drisch, Alain Forestiere, Aurélien Hainault
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Patent number: 6875900Abstract: An oligomerization process for the production of higher aliphatic olefins is disclosed. In the process, a liquid oligomerization feed stream comprising lighter aliphatic olefins is passed to a reactor vessel. The liquid oligomerization feed stream is transported upwardly in the reactor vessel against gravity through a fixed bed of solid oligomerization catalyst under oligomerization conditions. The catalyst has a Hammett acidity value of ?4 or less. A liquid oligomerization effluent stream is recovered comprising product higher aliphatic olefins.Type: GrantFiled: April 30, 2002Date of Patent: April 5, 2005Assignee: UOP LLCInventor: William J. Koves
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Patent number: 6787577Abstract: Process for increasing the branching in products from a slurry-type Fischer-Tropsch unit by use of potassium promoted iron-based catalyst, an integrated process for increasing the yield of lubricating base oils, and an iron-based Fischer-Tropsch catalyst composition having a high atomic ratio of potassium promoter.Type: GrantFiled: March 25, 2003Date of Patent: September 7, 2004Assignee: Chevron U.S.A. Inc.Inventors: Burtron H. Davis, Stephen J. Miller
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Patent number: 6689927Abstract: A process for the production of C8 alkenes with high selectivities to 2,4,4-trimethylpentene by the oligomerization of isobutene and/or n-butene at lower temperatures is disclosed. Higher proportions of heavy paraffins mixed with the butene feed in the oligomerization zone improve the selectivity to 2,4,4-trimethylpentene along with better selectivity to octene and lower selectivity to dodecene. Additionally, we have found that n-butene codimerizes with isobutene selectively to 2,4,4-trimethylpentene.Type: GrantFiled: May 7, 2001Date of Patent: February 10, 2004Assignee: UOP LCCInventors: Robert R. Frame, Laurence O. Stine, Hayim Abrevaya
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Publication number: 20040015028Abstract: This invention is to a method of oligomerizing an olefin feed stream. The olefin feed stream contains at least one C2 to C12 olefin to obtain an olefin feed stream and has from about 1,000 ppm to about 10 percent by weight oxygenated hydrocarbon. The olefin is oligomerized by contacting with an acid based oligomerization catalyst.Type: ApplicationFiled: July 22, 2002Publication date: January 22, 2004Inventors: Stephen Harold Brown, Georges M.K. Mathys
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Patent number: 6602922Abstract: A process for increasing the yield of olefinic products from a Fischer-Tropsch unit and increasing the yield of products within the lube and diesel boiling range by use of a potassium promoted iron-based catalyst.Type: GrantFiled: February 19, 2002Date of Patent: August 5, 2003Assignee: Chevron U.S.A. Inc.Inventors: Burtron H. Davis, Stephen J. Miller
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Patent number: 6501001Abstract: In order to carry out selective dimerization of propylene principally into branched dimers, a catalytic composition resulting from at least partly dissolving a nickel compound mixed or complexed with a tertiary phosphine carrying a functional group is used in a medium resulting from mixing at least one quaternary ammonium halide and/or at least one quaternary phosphonium halide, at least one aluminum halide and optionally at least one organometallic aluminum compound.Type: GrantFiled: February 5, 2001Date of Patent: December 31, 2002Assignee: Institut Francais du PetroleInventors: Dominique Commereuc, Dominique Le Pennec, Hélène Olivier-Bourbigou
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Patent number: 6399843Abstract: An oligomerization process for the production of higher aliphatic olefins is disclosed. In the process, a liquid oligomerization feed stream comprising lighter aliphatic olefins is passed to a reactor vessel. The liquid oligomerization feed stream is transported upwardly in the reactor vessel against gravity through a fixed bed of solid oligomerization catalyst under oligomerization conditions. The catalyst has a Hammett acidity value of −4 or less. A liquid saturate stream comprising paraffins is passed into contact with the feed stream and the catalyst. A liquid oligomerization effluent stream is recovered comprising the paraffins and product higher aliphatic olefins.Type: GrantFiled: October 12, 2000Date of Patent: June 4, 2002Assignee: UOP LLCInventor: William J. Koves
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Patent number: 6184428Abstract: A catalyst and a process are provided for oligomerizing ethylene. A heterogeneous catalyst system comprises: (1) a chelating ligand, preferably 2-diphenyl phosphino benzoic acid (DPPBA); (2) a nickel precursor, preferably nickel chloride hexahydrate (NiCl2.6H2O); (3) a catalyst activator, preferably sodium tetraphenylborate (NaBPh4); and (4) silica. A 1:1:1 molar ratio of Ni:DPPBA:BPh4 catalyst components are fixed on a silica support using low-temperature fixation. The catalyst components are dispersed in a diluent, preferably ethanol, and silica is added. The ethanol is evaporated using freeze-drying equipment to form a silica-supported catalyst system. The silica-supported catalyst is slurried in ethanol in a reactor, and ethylene is added. The reactor pressure and temperature are maintained at about 725 psig and 100° C., respectively, for about two hours.Type: GrantFiled: February 17, 1999Date of Patent: February 6, 2001Assignee: Saudi Basic Industries CorporationInventors: Mohammad Akhtar Zahoor, Fahad Al-Sherehy, Olagoke Olabisi, Mohammed M. Abdillahi, Mian Rahat Saeed
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Patent number: 6127301Abstract: The present invention provides a novel catalyst system which can be preferably used in the trimerization, oligomerization reaction or polymerization reaction of an olefin, and a method for the trimerization, oligomerization or polymerization reaction of an olefin, which comprises using the catalyst system. A catalyst system obtained by contacting the following components (A) to (C):(A) a chromium compound,(B) an imine compound, and(C) a metal alkyl compound, and a method for the trimerization, oligomerization or polymerization reaction of an olefin, which comprises using the catalyst system are disclosed.Type: GrantFiled: June 27, 1997Date of Patent: October 3, 2000Assignee: Sumitomo Chemical Company, LimitedInventors: Kiyoshi Iwanaga, Mitsuhisa Tamura
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Patent number: 6111159Abstract: A method is provided for putting a fresh bed of solid phosphoric acid catalyst into service to catalyze a hydrocarbon conversion process. The method involves establishing hydrocarbon conversion conditions of temperature and pressure in the catalyst bed while it is immersed in a hydrocarbon liquid which is substantially free of water and compounds which can yield water upon contact with the catalyst. Thereafter, the catalyst bed is used to catalyze the conversion of a hydrocarbon feedstock which contains a minor amount of a hydrating agent which is effective to provide a desired level of catalyst hydration. The method permits the catalyst to be rapidly brought to an optimum level of activity for the specific hydrocarbon conversion process.Type: GrantFiled: December 1, 1998Date of Patent: August 29, 2000Assignee: BP Amoco CorporationInventors: George A. Huff, Anthony M. Valente, Robert L. Mehlberg, David B. Johnson
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Patent number: 6043401Abstract: Catalysts and processes are described to make low molecular weight, essentially terminally-unsaturated, viscous poly(1-olefin) or copoly(1-olefin) having a high terminal vinylidine content from a feed stock containing one or more 1-olefin and other volatile hydrocarbon liquids using a Ziegler catalyst made from a Group IVb metallocene and an aluminoxane cocatalyst, particularly bis(cyclopentadienyl) and bis(indenyl) titanium(IV), zirconium(IV) or hafnium(IV) compounds and methylaluminoxane. A particularly useful feed stock is a refinery stream containing 1-olefins and isobutylene which is used to make polyisobutylene.Type: GrantFiled: January 15, 1998Date of Patent: March 28, 2000Assignee: BP Amoco CorporationInventors: Vahid Bagheri, Bruce Edward Firth, Frank Calabrese, Robert Scott Hensey
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Patent number: 6025534Abstract: A method is provided for regenerating a fixed bed of olefin polymerization catalyst which can be performed without taking the catalyst bed out of service. The method involves the use of two different olefin-containing feedstocks, wherein the first feedstock is a conventional olefin-containing feedstock which contains little if any content of aromatic compounds. The second feedstock contains a significant concentration of aromatic compounds. In the practice of the invention, the second feedstock is substituted for the first feedstock whenever catalyst regeneration is deemed appropriate, and the flow of the second feedstock to the catalyst bed is continued for a period of time which is effective to at least partially regenerate the catalyst.Type: GrantFiled: April 7, 1998Date of Patent: February 15, 2000Assignee: BP Amoco CorporationInventors: Anthony M. Valente, David B. Johnson, George A. Huff, Jr., Robert L. Mehlberg
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Patent number: 6011191Abstract: A process is described for the production of hydrocarbons with a high octane number starting from hydrocarbon cuts containing isobutene by selective dimerization with acid catalysts characterized in that the dimerization reaction is carried out in the presence of primary alcohols and alkyl others in such a quantity as to have in the feeding a molar ratio primary alcohols+alkyl ethers/isobutene of more than 0.1 and a molar ratio primary alcohols/isobutene of less than 0.2, operating, preferably, at a reaction temperature of between 30 and 120.degree. C., at a pressure of less than 5 MPa and feeding space velocities of less than 30 h.sup.-1.Type: GrantFiled: May 15, 1998Date of Patent: January 4, 2000Assignee: Snamprogetti S.p.A.Inventors: Marco Di Girolamo, Lorenzo Tagliabue
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Patent number: 5932778Abstract: A method is provided which can be used to quickly and easily take a fixed-bed of solid acid olefin polymerization catalyst out of service without causing any significant catalyst deactivation. The method involves substituting a substantially olefin-free hydrocarbon fluid for at least a portion of the olefin-containing feedstock to the polymerization process, wherein the substantially olefin-free hydrocarbon fluid boils within the range from about 20.degree. to about 250.degree. C. and contains at least about 5 vol. % aromatics.Type: GrantFiled: September 30, 1997Date of Patent: August 3, 1999Assignee: BP Amoco CorporationInventors: Anthony M. Valente, David B. Johnson, George A. Huff, Jr.
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Patent number: 5898090Abstract: This invention is drawn to a process for isomerizing a non-equilibrium mixture of xylenes and ethylbenzene using a silicoaluminophosphate molecular sieve which is enriched in framework silicon at the surface, resulting in a greater yield of para-xylene compared to prior-art processes.Type: GrantFiled: December 17, 1997Date of Patent: April 27, 1999Assignee: UOP LLCInventors: John Ivor Hammerman, Edith Marie Flanigen, Gregory J. Gajda, Jennifer S. Holmgren, David A. Lesch, Robert Lyle Patton, Thomas Matthew Reynolds, Cara Moy Roeseler
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Patent number: 5811608Abstract: A process for the production of saturated oligomers by the oligomerization of light olefins to heavier olefins and the saturation of the heavy olefins is improved by the recycle of the heavy paraffins to the oligomerization zone. The recycle of the heavy paraffins improves the selectivity of the oligomerization for C.sub.8 paraffin products and reduces catalyst fouling. The reduced catalyst fouling can be used to operate the oligomerization zone at lower pressure and facilitate its integration with a dehydrogenation zone for the production of the light olefin stream.Type: GrantFiled: December 15, 1995Date of Patent: September 22, 1998Assignee: UOP LLCInventors: Laurence O. Stine, Brian S. Muldoon, Steven C. Gimre, Robert R. Frame
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Patent number: 5792894Abstract: A process is disclosed for alkylating a volatile aromatic compound with a light aliphatic mono-olefinic alkylating agent and concurrently condensing the alkylating agent in the presence of a solid alkylation- and condensation-promoting catalyst and at a temperature of at least the critical temperature of the reactant mixture and at a total pressure that is above the critical pressure of the reactant mixture.Type: GrantFiled: September 7, 1997Date of Patent: August 11, 1998Assignee: Amoco CorporationInventors: George A. Huff, Jr., Robert L. Mehlberg, Peter M. Train
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Patent number: 5659096Abstract: In a process for alkylating C.sub.4 -C.sub.18 alkenes in the presence of an acid catalyst, propylene is separated from the alkenes feed, the propylene is oligomerized to oligomers containing maily propylene tetramers, and the propylene oligomers are then combined with the remainder of the alkene feed before the alkylation reaction is carried out.Type: GrantFiled: June 5, 1995Date of Patent: August 19, 1997Assignee: Phillips Petroleum CompanyInventors: Bruce B. Randolph, Marvin M. Johnson
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Patent number: 5650548Abstract: Alpha-olefin oligomer is prepared by contacting an alpha-olefin monomer which contains from about 6 to about 20 carbon atoms with a catalyst system comprising boron trifluoride, a protic promoter, and an organic sulfone, sulfoxide, carbonate, thiocarbonate, or sulfonate. Oligomer containing as much as 50% or more of dimer can be produced at high conversions, at modest reaction temperatures, and in acceptably short reaction periods.Type: GrantFiled: June 16, 1995Date of Patent: July 22, 1997Assignee: Amoco CorporationInventors: Kevin J. Theriot, Robert G. Irwin
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Patent number: 5633420Abstract: Alpha-olefin oligomers are prepared by a process which comprises contacting an oligomerizable olefin monomer with a catalyst system comprising a catalytic amount of boron trifluoride, a protic promoter, and an organic modifier selected from the group consisting of phosphate, thiophosphate, phosphine oxide, and phosphine sulfide. The oligomerizable olefin monomer is a C.sub.6 to C.sub.20 linear olefin comprising at least 50 mole % alpha olefin.Type: GrantFiled: September 22, 1995Date of Patent: May 27, 1997Assignee: Amoco CorporationInventors: Kevin J. Theriot, Robert G. Irwin
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Patent number: 5620935Abstract: Zeolites containing titanium atoms used as catalyst for the preparation of epoxides from olefins and hydrogen peroxide are regenerated by treating the spent catalyst with hydrogen peroxide in the absence of olefins and the regenerated catalyst is again used for the epoxidation.Type: GrantFiled: June 14, 1996Date of Patent: April 15, 1997Assignee: Degussa AktiengesellschaftInventor: Georg Thiele
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Patent number: 5557027Abstract: The present invention relates to a catalyst suitable for oligomerization of olefins which is prepared by a process which comprises reacting a catalyst precursor ligand having a formula ##STR1## wherein R.sub.1 and R.sub.2 each independently is an alkyl, alkoxy, aryl, or aryloxy group having from about 1 to about 20 carbon atoms, with the proviso that R.sub.1 and R.sub.2 are not both aryl, or R.sub.1 and R.sub.2 together form a divalent hydrocarbon moiety, and X is 1,2-arylene, O-CH.sub.2, S-CH.sub.2, or Se-CH.sub.2 with a deprotonation source, a transition metal compound and a catalyst activator. The invention further relates to an oligomerization process utilizing this catalyst.Type: GrantFiled: January 13, 1995Date of Patent: September 17, 1996Assignee: Shell Oil CompanyInventor: Richard A. Kemp
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Patent number: 5059737Abstract: A hydrocarbon conversion process which utilizes a solid phosphoric acid catalyst having a total X-ray intensity of at least 40 percent relative to alpha-alumina. The solid phosphoric acid catalyst is produced by crystallizing an amorphous mixture of an acid oxide of phosphorus and a siliceous material at a temperature of from 350.degree. to 450.degree. C. and in the presence of from 10 to 50 mole percent water vapor based upon the total vapor rate to the crystallizing means. Embodiments of the new hydrocarbon conversion process include alkylation, oligomerization, and hydration, of hydrocarbons and oxygenated hydrocarbons.Type: GrantFiled: July 2, 1990Date of Patent: October 22, 1991Assignee: UOPInventors: Tai-Hsiang Chao, Fiona P. Wilcher, Mark R. Ford, Andrzej Z. Ringwelski
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Patent number: 5043509Abstract: Catalyst particles which are employed in reactions involving the conversion of organic compounds should possess a desired configuration in order to maintain a desired voidage which will permit passage of the feedstock through the catalyst bed during the conversion reaction. Solid phosphoric acid catalysts which comprise an admixture of an acid of phosphorus and a solid binder such as a siliceous material may be formed into polylobular, tubular, ridged, fluted, or channeled cylindrical particles which will permit a sufficient amount of voidage in the catalyst bed to be maintained even though the catalyst particles will swell during the reaction due to the formation of coke on the surface thereof.Type: GrantFiled: August 18, 1989Date of Patent: August 27, 1991Assignee: UOPInventors: Tamotsu Imai, Paul T. Barger, Harold U. Hammershaimb
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Patent number: 4946815Abstract: A solid phosphoric acid catalyst having a total X-ray intensity of at least 30 percent relative to alpha-alumina. The solid phosphoric acid catalyst is produced by crystallizing an amorphous mixture of an acid oxide of phosphorus and a siliceous material at a temperature of from 250.degree. to 450.degree. C. and in the presence of from 3 to 50 mole percent water vapor based upon the total vapor rate to the crystallizing means.Type: GrantFiled: December 23, 1988Date of Patent: August 7, 1990Assignee: UOPInventors: Tai-Hsiang Chao, Fiona P. Wilcher, Mark R. Ford, Andrzej Z. Ringwelski
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Patent number: 4880520Abstract: Crystalline molecular sieves having three-dimensional microporous framework structures of TiO.sub.2, AlO.sub.2, SiO.sub.2 and PO.sub.2 tetrahedral units are disclosed. These molecular sieves have an empirical chemical composition on an anhydrous basis expressed by the formula:mR: (Ti.sub.w Al.sub.x P.sub.y Si.sub.z)O.sub.2wherein "R" represents at least one organic templating agent present in the intracrystalline pore system; "m" represents the molar amount of "R" present per mole of (Ti.sub.w Al.sub.x P.sub.y Si.sub.z)O.sub.2 ; and "w", "x", "y" and "z" represent the mole fractions of titanium, aluminum, phosphorus and silicon, respectively, present as tetrahedral oxides. Their use as adsorbents, catalysts, etc. is also disclosed.Type: GrantFiled: October 21, 1988Date of Patent: November 14, 1989Assignee: UOPInventors: Brent M. T. Lok, Bonita K. Marcus, Edith M. Flanigen
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Patent number: 4749675Abstract: The present invention relates to a catalyst for the selective dimerization of ethylene or of propylene into monoolefines of the type based on nickel on a silica support whose active sites are complexes of the Ni.sup.+ ion. This catalyst is characterized in that practically the whole of the nickel is present in the form of Ni.sup.+ complexes co-ordinated with the oxygen of the surface of the silica support and whose co-ordination sphere comprises one or two trialkylphosphine ligands. The invention also relates to a process for the preparation of these catalysts and to a process of dimerization employing them.Type: GrantFiled: June 27, 1986Date of Patent: June 7, 1988Assignee: Centre National de la Recherche Scientifique (CNRS)Inventors: Daniele Olivier, Feng X. Cai, Christine Lepetit, Maggy Kermarec
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Patent number: 4742032Abstract: Spent solid phosphoric acid catalyst is neutralized prior to removal from a reactor vessel to avoid generation of toxic dust or acidic washings during catalyst removal.Type: GrantFiled: October 3, 1986Date of Patent: May 3, 1988Assignee: Conoco Inc.Inventor: Norman M. Whitton
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Patent number: 4675463Abstract: An improved process for oligomerizing olefins is provided in which olefin feed is contacted with phosphoric acid catalyst to form an olefin oligomerization product containing phosphorous-containing foulant precursors. The olefin oligomerization product is then contacted with a foulant adsorbent comprising at least one member selected from the group consisting of alumina, activated alumina and magnesium oxide in an amount and under conditions sufficient to effect removal of at least a portion of said foulant precursors. The treated olefin oligomerization product stream can then be passed to downstream recovery and process equipment with minimized fouling.Type: GrantFiled: February 5, 1986Date of Patent: June 23, 1987Assignee: Exxon Chemical Patents Inc.Inventors: Alexandr P. Glivicky, Donald J. Norris