Sulfuric Acid With Additional Nonhydrocarbon Agent Patents (Class 585/731)
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Patent number: 11958046Abstract: Methods and systems for alkylate production involving a multi-zone alkylation reactor. The multi-zone alkylation reactor includes a plurality of alkylation zones spaced vertically in a series configuration and a partition splitting the plurality of alkylation zones into at least two mechanically separated catalytic volumes.Type: GrantFiled: June 16, 2023Date of Patent: April 16, 2024Assignee: KELLOGG BROWN & ROOT LLCInventors: Rajeev Ranjan, Anubhav Kapil
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Patent number: 11639322Abstract: A process for sulfuric acid catalyzed alkylation involving the use of surfactants which form bi-continuous micro-emulsions with the sulfuric acid and the hydrocarbon is described. The bi-continuous phase facilitates and improves the sulfuric acid catalyzed alkylation reactions. The concentration of the surfactant is selected based on the type of olefin feed. Easy to alkylate feeds, such as 2-butene, use lower concentrations of surfactant, while feeds which are harder to alkylate, such as propene or isobutene, use higher concentrations of the surfactant. In addition, increasing the concentration of sulfuric acid when a surfactant is included resulted in higher calculated RON. The use of a surfactant and a high concentration of sulfuric acid can provide a calculated RON over 100 and close to theoretical yields.Type: GrantFiled: September 9, 2021Date of Patent: May 2, 2023Assignee: UOP LLCInventors: Christopher P. Nicholas, Susie C. Martins, David E. Mackowiak, Hayim Abrevaya, Joel T. Walenga
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Publication number: 20140323786Abstract: A continuous mixing reactor has an outer shell having a cylindrical portion with a central section and two opposite conical end sections; a circulation tube within the shell so that an annular passage forms between the shell and the circulation tube; an impeller within and positioned adjacent to one end of the circulation tube; and heat exchange means penetrating the outer shell and extending into the end of the circulation tube opposite the impeller. The outer shell has a hydraulic head forming one end of the shell, a heat exchange medium header at the opposite end of the shell. The circulation tube nearer the heat exchange medium header terminates at or downstream from a tangential plane extending through the shell at the intersection of the central section and the conical end section of the cylindrical portion of shell. The reactor is useful in an alkylation process.Type: ApplicationFiled: April 25, 2014Publication date: October 30, 2014Applicant: E I DU PONT DE NEMOURS AND COMPANYInventors: Mark Coleman Puett, Minye Liu
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Patent number: 8461408Abstract: A method for alkylating a hydrocarbon comprising at least one isoparaffin and at least one olefin that includes introducing a liquid catalyst and the hydrocarbon into a high shear device; processing the liquid catalyst and the hydrocarbon in the high shear device to form an emulsion comprising droplets of hydrocarbon dispersed in the liquid catalyst; introducing the emulsion into a vessel operating under suitable alkylation conditions whereby at least a portion of the isoparaffin is alkylated with the olefin to form alkylate, wherein suitable alkylation conditions comprise a bulk reaction temperature of from about 38° C. to about 90° C. and a bulk reaction pressure in the range of from about 1379 kPa to about 34 MPa; and removing a product stream comprising alkylate from the vessel.Type: GrantFiled: August 15, 2012Date of Patent: June 11, 2013Assignee: H R D CoporationInventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Patent number: 8269057Abstract: A method for alkylating a hydrocarbon comprising at least one isoparaffin and at least one olefin by introducing liquid acid catalyst and the hydrocarbon into a high shear reactor, forming an emulsion comprising droplets comprising hydrocarbon in a continuous acid phase, wherein the droplets have a mean diameter of less than about 5 ?m, introducing the emulsion into a vessel operating under suitable alkylation conditions whereby at least a portion of the isoparaffin is alkylated with the olefin to form alkylate, and removing a product stream comprising alkylate from the vessel. A system for carrying out the method is also disclosed.Type: GrantFiled: June 12, 2008Date of Patent: September 18, 2012Assignee: H R D CorporationInventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Patent number: 8084661Abstract: A process for the regeneration of spent sulfuric acid including contacting spent sulfuric acid containing acid soluble oils (ASO) with sulfur dioxide to extract at least a portion of the ASO from the spent sulfuric acid into the sulfur dioxide. The sulfuric acid phase having a reduced ASO content and a sulfur dioxide phase containing at least a portion of the ASO may be recovered. The resulting sulfuric acid and sulfur dioxide phases may be further separated to recover ASO, sulfur dioxide, and sulfuric acid.Type: GrantFiled: December 12, 2008Date of Patent: December 27, 2011Assignee: Catalytic Distillation TechnologiesInventor: William M. Cross, Jr.
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Patent number: 8034988Abstract: A process for alkylation of propylene, the process including: contacting a stream comprising propylene and propane with sulfuric acid in a first reaction zone under conditions to form propylene sulfate esters; contacting the propylene sulfate esters with isoparaffin and sulfuric acid in an alkylation reaction zone under conditions to react the propylene sulfate esters and the isoparaffin to form a reactor effluent comprising an acid phase and a hydrocarbon phase comprising unreacted isoparaffin and alkylate product; separating the hydrocarbon phase from the sulfuric acid; separating the hydrocarbon phase to form a fraction comprising unreacted isoparaffin and a fraction comprising the alkylate product.Type: GrantFiled: September 19, 2008Date of Patent: October 11, 2011Assignee: Catalytic Distillation TechnologiesInventors: Mitchell E. Loescher, William M. Cross, Jr., Lawrence A. Smith, Jr.
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Patent number: 7977525Abstract: A process for treating an alkylation feedstock comprising olefins, n-alkanes, and iso-alkanes, the process including: contacting at least a portion of the alkylation feedstock with sulfuric acid in a reaction zone under conditions to form sulfate esters of the olefins; separating the n-alkanes and the iso-alkanes from the sulfuric acid and the sulfate esters; recovering the n-alkanes and the iso-alkanes in a first product stream; and recovering the sulfate esters in a second product stream; wherein the sulfuric acid has a strength titrating as below 75 weight percent H2SO4/water mixtures.Type: GrantFiled: January 31, 2008Date of Patent: July 12, 2011Assignee: Catalytic Distillation TechnologiesInventors: Lawrence A. Smith, Jr., Abraham P. Gelbein, William M. Cross, Jr.
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Patent number: 7906700Abstract: A process for alkylating isobutene by introducing a feed containing isobutene and an isoparaffin, in the form of droplets, into an acid catalyst to produce an alkylation product, wherein the Sauter mean diameter of the droplets is greater than or equal to about 150 ?m and is less than or equal to about 500 ?m, is disclosed.Type: GrantFiled: June 1, 2006Date of Patent: March 15, 2011Assignee: UOP LLCInventors: Bruce B. Randolph, Keith W. Hovis, Kenneth C. Hoover
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Patent number: 7674945Abstract: 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: GrantFiled: January 19, 2005Date of Patent: March 9, 2010Assignee: China Petroleum & Chemical CorporationInventors: Yigong He, Zheng Man
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Patent number: 7652187Abstract: A process for the sulfuric acid catalyzed alkylation of C3-C5 olefins with isobutane is disclosed wherein the requisite mixing is accomplished by the use of eductors within the reactor. In addition the alkylate product is subjected to primary and secondary coalescers for removal of entrained sulfuric acid. The vaporized unreacted C4's are recovered as liquid by absorption and desorption in an absorber oil.Type: GrantFiled: February 23, 2009Date of Patent: January 26, 2010Inventor: Amarjit S. Bakshi
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Patent number: 7435864Abstract: Disclosed is a device for the production of alkylate(s) by sulfuric acid alkylation of at least one isoparaffin such as isobutane with at least one olefin, such as butylenes. The device includes a mixing chamber for preparing a mixture of the isoparaffin with recycled reaction products. It also includes an emulsion chamber for preparing a first hydrocarbons-in-sulfuric acid emulsion, where the mixture prepared in the mixing chamber is injected in multiple parallel jets into a sulfuric acid composition. The device further includes a pre-reaction chamber for preparing a second emulsion, where a given portion of the olefin is injected in jet streams into the first hydrocarbons-in-sulfuric acid emulsion coming from the emulsion chamber.Type: GrantFiled: June 1, 2001Date of Patent: October 14, 2008Assignee: Orgral International Technologies CorporationInventor: Semen Gershuni
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Patent number: 7256152Abstract: A composition defined: either as comprising at least one Broensted acid, designated HB, dissolved in a liquid medium with an ionic nature of general formula Q+A?, in which Q+ represents an organic cation and A? represents an anion that is different from B, or as resulting from dissolving at least one Broensted acid, designated HB, in a non-aqueous liquid medium with an ionic nature of general formula Q+A?, in which Q+ represents an organic cation and A? represents an anion that is identical to the anion B, can be used as a catalyst and solvent in acid catalysis processes, in particular in the alkylation of aromatic hydrocarbons, the oligomerization of olefins, the dimerization of isobutene, the alkylation of olefins by isoparaffins, the isomerization of n-paraffins into isoparaffins, the isomerization of n-olefins into iso-olefins, the isomerization of the double bond of an olefin and the purification of an olefin mixture that contains branched alpha olefins as impurities.Type: GrantFiled: September 3, 2002Date of Patent: August 14, 2007Assignee: Institut Francais du PetroleInventors: Helene Olivier-Bourbigou, Dominique Commereuc, Olivia Martin, Lionel Magna, Emmanuel Pellier
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Patent number: 7126038Abstract: An improvement in the alkylation of olefins with isoalkanes in the presence of sulfuric acid wherein the sulfuric acid is removed from the product by a mechanical coalescer means prior to fractionation. No water wash or caustic treatment is required. Any sulfonates or sulfonic esters are removed by hydrodesulfurization or decomposition catalyst in a separate reactor or in either the deisobutanizer (DIB) or debutanizer (DB) column.Type: GrantFiled: December 1, 2004Date of Patent: October 24, 2006Assignee: Catalytic Distillation TechnologiesInventor: Lawrence A. Smith, Jr.
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Patent number: 7119244Abstract: A process for the removal of organic sulfur compounds, primarily oxygenated organic compounds, such as sulfates and sulfonic esters from a hydrocarbon liquid is disclosed which comprises contacting the hydrocarbon liquid with a coalescer comprising a mesh material which has been wetted by sulfuric acid. The hydrocarbon liquid may be the product from a sulfuric acid catalyzed alkylation process and contain sufficient sulfuric acid to remove the sulfates and sulfonic esters. Sulfuric acid may be added to the coalescer vessel counter current to the hydrocarbon liquid to improve the efficiency of the contacting and removal.Type: GrantFiled: January 13, 2005Date of Patent: October 10, 2006Assignee: Catalytic Distillation TechnologiesInventor: Lawrence A. Smith, Jr.
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Patent number: 6852902Abstract: An improvement in the alkylation of olefins with isoalkanes in the presence of sulfuric acid wherein the sulfuric acid is removed from the product by a mechanical coalescer means prior to fractionation. No water wash or caustic treatment is required. Any sulfonates or sulfonic esters are removed by hydrodesulfurization or decomposition catalyst in a separate reactor or in either the deisobutanizer (DIB) or debutanizer (DB) column.Type: GrantFiled: October 11, 2002Date of Patent: February 8, 2005Assignee: Catalytic Distillation TechnologiesInventor: Lawrence A. Smith, Jr.
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Publication number: 20040204622Abstract: A method of operating a multi-phase downflow reactor so as to induce a pulsing flow regime is disclosed. The pulse may be induced by increasing the gas rate while maintaining the liquid rate until a pressure drop sufficient to induce the pulse flow is achieved. The method is particularly useful in the sulfuric acid catalyzed alkylation of olefins in a reactor packed with a stainless steel/polypropylene mesh.Type: ApplicationFiled: April 19, 2004Publication date: October 14, 2004Inventors: Lawrence A. Smith, William M. Cross
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Patent number: 6774275Abstract: A method of operating a multi-phase downflow reactor so as to induce a pulsing flow regime is disclosed. The pulse may be induced by increasing the gas rate while maintaining the liquid rate until a pressure drop sufficient to induce the pulse flow is achieved. The method is particularly useful in the sulfuric acid catalyzed alkylation of olefins in a reactor packed with a stainless steel/polypropylene mesh.Type: GrantFiled: August 19, 2002Date of Patent: August 10, 2004Assignee: Catalytic Distillation TechnologiesInventors: Lawrence A. Smith, Jr., William M. Cross, Jr.
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Publication number: 20030176755Abstract: A process for the alkylation of alkane with olefin or olefin precursor such as an oligomer of tertiary olefin comprising contacting a liquid system comprising acid catalyst, isoparaffin and olefin in concurrent downflow into contact in a reaction zone with a disperser mesh under conditions of temperature and pressure to react said isoparaffin and said olefin to produce an alkylate product is disclosed. Preferably, the liquid system is maintained at about its boiling point in the reaction zone. Unexpectedly, the olefin oligomers have been found to function as olefin precursors and not as olefins in the reaction. Thus, for example, a cold acid alkylation using an oligomer of isobutene (principally dimer and trimer) with isobutane produces isooctane with the isobutane reacting with the constituent isobutene units of the oligomers on a molar basis. The product isooctane is essentially the same as that produced in the conventional cold acid process.Type: ApplicationFiled: August 15, 2002Publication date: September 18, 2003Applicant: CATALYTIC DISTILLATION TECHNOLOGIESInventors: Lawrence A. Smith, Mitchell E. Loescher, John R. Adams, Abraham P. Gelbein
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Publication number: 20030158457Abstract: Disclosed is a device for the production of alkylate(s) by sulfuric acid alkylation of at least one isoparaffin such as isobutane with at least one olefin, such as butylenes. The device includes a mixing chamber for preparing a mixture of the isoparaffin with recycled reaction products. It also includes an emulsion chamber for preparing a first hydrocarbons-in-sulfuric acid emulsion, where the mixture prepared in the mixing chamber is injected in multiple parallel jets into a sulfuric acid composition. The device further includes a pre-reaction chamber for preparing a second emulsion, where a given portion of the olefin is injected in jet streams into the first hydrocarbons-in-sulfuric acid emulsion coming from the emulsion chamber.Type: ApplicationFiled: December 4, 2002Publication date: August 21, 2003Inventor: Seme Gershuni
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Patent number: 6296757Abstract: Diesel fuels or blending stocks having excellent lubricity, oxidative stability and high cetane number are produced from non-shifting Fischer-Tropsch processes by separating the Fischer-Tropsch product into a lighter and heavier fractions, e.g., at about 700° F., subjecting the 700° F.+fraction to hydro-treating, and combining the 700° F.− portion of the hydrotreated product with the lighter fraction that has not been hydrotreated.Type: GrantFiled: October 17, 1995Date of Patent: October 2, 2001Assignee: Exxon Research and Engineering CompanyInventors: Robert Jay Wittenbrink, Richard Frank Bauman, Paul Joseph Berlowitz, Bruce Randall Cook
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Patent number: 5986158Abstract: The invention pertains to a process for alkylating hydrocarbons in which an alkylatable organic compound is reacted with an alkylation agent to form an alkylate in the presence of a catalyst comprising a hydrogenating function and a solid acid constituent, with the catalyst being subjected intermittently to a regeneration step by being contacted with a feed containing a saturated hydrocarbon and hydrogen, said regeneration being carried out at 90% or less of the active cycle of the catalyst, with the active cycle of the catalyst being defined as the time from the start of the feeding of the alkylation agent to the moment when 20% of the alkylation agent leaves the catalyst-containing reactor section without being converted, not counting isomerization inside the molecule. The process according to the invention is especially attractive for the alkylation of isobutane with one or more butenes to form an alkylate with a high RON.Type: GrantFiled: November 20, 1997Date of Patent: November 16, 1999Assignee: Akzo Nobel NVInventors: Emanuel Hermanus Van Broekhoven, Francisco Rene Mas Cabre, Pieter Bogaard, Gijsbertus Klaver, Marco Vonhof
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Patent number: 5969206Abstract: The invention concerns a process for the alkylation of at least one isoaffin selected from the group formed by isobutane and isopentane by at least one olefin containing 2 to 6 carbon atoms per molecule in the presence of a liquid acid catalyst, the process comprising mixing a feed comprising the olefin to be converted with an effluent comprising a major portion of isoparaffin in a first mixing zone, and forming an emulsion of said catalyst in a hydrocarbon effluent comprising a major portion of isoparaffin in an emulsifying zone, said effluent constituting the continuous phase of the emulsion thus formed, then mixing a major portion of the emulsion of acid in hydrocarbon effluent with a major portion of the diluted feed comprising the olefin in a second mixing zone, followed by carrying out the majority of the reaction in a reaction zone which is supplied by the major portion of said mixture.Type: GrantFiled: January 17, 1997Date of Patent: October 19, 1999Assignee: Institut Francais du PetroleInventors: Jacques Alagy, Jean-Francois Joly, Eric Benazzi, Jean-Charles Viltard, Luis Borges, Alain Forestiere
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Patent number: 5942654Abstract: A process for the removal of corrosive compounds from a fluid stream, comprising the steps of: in an extraction column with an outer steel tube and an inner tube of corrosion resistant material having an open inlet end and an open outlet end and being arranged coaxially with and spaced apart within at least top portion of the outer tube, introducing at elevated temperature at the inlet end of the inner tube the fluid stream and an extraction agent and effecting in the mixed stream of the fluid and extraction agent extraction of the corrosive compounds; introducing into an annular space between the walls of the outer and the inner tube a shell stream of a non-corrosive fluid, thereby absorbing in the shell stream amounts of the corrosive compounds diffusing through the wall of the inner tube; passing the shell stream to the bottom portion of the outer tube; cooling the mixed stream at the outlet end of the inner tube by introducing into the stream a cooling stream; passing the cooled stream to the bottom portiType: GrantFiled: June 13, 1997Date of Patent: August 24, 1999Assignee: Haldor Topsoe A/SInventor: Sven Ivar Hommeltoft
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Patent number: 5925801Abstract: A process for preparing high-octane gasoline components consists in that a feed stock, composed of isobutane and olefins, preferably butylenes, in a molar ratio between 1 and 40, is contacted at temperatures of from about 50 to about 160.degree. C. and at pressures of from about 1 to about 40 atm. with a heterogeneous acid catalyst, whose active component is a metal-complex or metaloxopolymeric compound of the general formula H.sub.k (Me.sup.1); (Me.sup.2).sub.m O.sub.n X.sub.p wherein k=1-6; j=1-3; m=1-5; n=1-10, p=2-10, dispersed in a porous organic or inorganic matrix, followed by the extraction regeneration of the deactivated catalyst with an organic or inorganic solvent.Type: GrantFiled: February 13, 1997Date of Patent: July 20, 1999Assignee: Institut Kataliza Imeni G.K. Boreskova Sibirskogo Otdelenia Rossiiskoi Akademii NaukInventors: Valery Kuzmich Duplyakin, Valentina Petrovna Finevich, Gleb Alexandrovich Urzhuntsev, Alexandr Ivanovich Lugovskoi
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Patent number: 5888920Abstract: This invention discloses an integrated process of alkylation of olefins and regeneration of spent sulfuric acid. The alkylation of olefins may be replaced by nitration of toluene or by chlor-alkali process. The sulfuric acid is used as a catalyst or a absorbent, and the spent sulfuric acid is regenerated in situ and is recycled in the alkylation of olefins, nitration of toluene or chlor-alkali processes.Type: GrantFiled: January 15, 1997Date of Patent: March 30, 1999Inventors: Tse-Chuan Chou, Chao-Shan Chou, Yi-Lin Chen
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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.
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Patent number: 5817908Abstract: A staged alkylation process in the presence of an acid catalyst in a fixed bed of particulate contact material in an alkylation reactor is disclosed.Type: GrantFiled: May 20, 1996Date of Patent: October 6, 1998Assignee: Amoco CorporationInventor: Robert L. Mehlberg
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Patent number: 5811627Abstract: Improved acid catalyzed alkylation reactions occur for the addition of a hydrocarbyl reactant to an alkene, by the optimized addition of an oxidizing agent, such as a peroxide, molecular oxygen, ozone, peracid, and one or more of the peroxide, molecular oxygen, ozone, or peracid mixed with at least one material selected from the group consisting of the hydrocarbyl reactant, and the alkene. The hydrocarbyl reactant contains at least one tertiary carbon atom attached to hydrogen, such as isobutane. The alkene is preferably an alkene of at least 2 carbon atoms. Suitable peroxides are found in the group consisting of: tert-butyl peroxyneopentanoate ((CH.sub.3).sub.3 C--O--OCO--C(CH.sub.3).sub.3); acetyl peroxide (CH.sub.3 CO--O--OCOCH.sub.3); di-tert-butyl peroxide ((CH.sub.3).sub.3 C--O--O--C(CH.sub.3).sub.3); hydrogen peroxide (H.sub.2 O.sub.2) and peracids of carboxylic acid having up to 10 carbon atoms, and a general chemical formula C.sub.n H.sub.2n O.sub.3, where n has values in the range 2-10.Type: GrantFiled: September 13, 1996Date of Patent: September 22, 1998Inventor: Stanley M. Welsh
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Patent number: 5811626Abstract: Disclosed is a process for the alkylation of an isoparaffin by an olefin in the presence of a catalyst. In the process, a portion of the isoparaffin recovered after extraction from the reaction zone (R) is recycled to the reaction zone and the feed is periodcally injected into the reaction zone while the recycled isoparafin fraction is continuously injected into the reaction zone.Type: GrantFiled: March 22, 1996Date of Patent: September 22, 1998Assignee: Institut Francais du PetroleInventors: Jean-Fran.cedilla.ois Joly, Alain Forestiere, Jean-Luc Duplan, Eric Benazzi
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Patent number: 5750818Abstract: 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: GrantFiled: June 20, 1996Date of Patent: May 12, 1998Assignee: Amoco CorporationInventors: Robert L. Mehlberg, James B. Young
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Patent number: 5731256Abstract: The present invention concerns a catalyst comprising a porous organic or mineral support, preferably silica, and an acidic phase containing B(OSO.sub.2 CF.sub.3).sub.3 and at least one acid selected from the group formed by sulphuric acid (H.sub.2 SO.sub.4) and trifluoromethane sulphonic acid (CF.sub.3 SO.sub.3 H), the support having been impregnated by said acidic phase, said catalyst being such that it is constituted essentially by particles with an average diameter of between 0.1 and 150 .mu.m, such that the support, prior to its impregnation with said acidic phase, has a total pore volume of between 0.5 and 6 cm.sup.3 per gram and said catalyst being characterized in that said acidic phase contains:between 0.1 and 70% by weight of B(OSO.sub.2 CF.sub.3).sub.3 ;between 0 and 90% by weight of H.sub.2 SO.sub.4 ;between 0 and 90% by weight of CF.sub.3 SO.sub.3 H.Type: GrantFiled: June 5, 1995Date of Patent: March 24, 1998Assignee: Institut Francais du PetroleInventors: Eric Benazzi, Jean-Fran.cedilla.ois Joly, Christian Marcilly
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Patent number: 5723715Abstract: A novel alkylation catalyst is described which is used in processes for alkylating olefin hydrocarbons with isoparaffin hydrocarbons to produce high octane alkylate products suitable for use as a blending component of gasoline motor fuel. The novel catalyst comprises a mixture of a hydrogen halide, a sulfone and a promoter. The novel alkylation catalyst is utilized in a novel process for alkylating olefin hydrocarbons with isoparaffin hydrocarbons.Type: GrantFiled: May 30, 1995Date of Patent: March 3, 1998Inventors: Bruce B. Randolph, Ronald G. Abbott
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Patent number: 5689030Abstract: A method for prolonging the life of a defluorinator material contained within an alkylation process product stream defluorination zone used to remove organic fluorides from a product stream produced by an alkylation process that utilizes an alkylation catalyst containing HF and sulfone. The life of the defluorinator material is extended by reducing the amount of organic fluorides produced in the alkylation process through the addition of trifluoromethanesulfonic acid to the HF/sulfone alkylation catalyst.Type: GrantFiled: March 6, 1996Date of Patent: November 18, 1997Assignee: Phillips Petroleum CompanyInventor: Bruce B. Randolph
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Patent number: 5663474Abstract: 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: GrantFiled: March 7, 1996Date of Patent: September 2, 1997Assignee: 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
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Patent number: 5659105Abstract: A process for the alkylation of aliphatic hydrocarbons with olefins catalyzed by a silica-based material, characterised in that the surface Si--OH groups of said silica are esterified with a fluoroalkylsulphonic acid of formula CF.sub.3 (CF.sub.2).sub.n SO.sub.3 H, where n is a whole number between 0 and 11, said material having a Hammett acidity Ho.ltoreq.-11.4.Type: GrantFiled: May 23, 1995Date of Patent: August 19, 1997Assignees: Eniricerche S.p.A., Agip Petroli S.p.A.Inventors: Mario Gabriele Clerici, Carlo Perego, Alberto de Angelis, Luciano Montanari
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Patent number: 5646086Abstract: A catalyst comprising a porous organic or mineral support, preferably silica, and an acidic phase containing B(OSO.sub.2 CF.sub.3).sub.3 and at least one acid selected from the group formed by sulphuric acid (H.sub.2 SO.sub.4) and trifluoromethane sulphonic acid (CF.sub.3 SO.sub.3 H), said support having been impregnated with said acidic phase and said support prior to impregnation having a total pore volume of 0.1-0.6 cm.sup.3 /g, said catalyst being essentially constituted by particles with an average diameter of between 0.1 and 30 .mu.m, said catalyst being characterized in that said acidic phase contains:between 0.1 and 70% by weight of B(OSO.sub.2 CF.sub.3).sub.3 ;between 0 and 90% by weight of H.sub.2 SO.sub.4 ;between 0 and 90% by weight of CF.sub.3 SO.sub.3 H.is suitable for the catalytic alkylation of isobutane and/or isopentane in the presence of at least one olefin containing 2 to 6 carbon atoms per molecule, preferably 3 to 6 carbon atoms per molecule.Type: GrantFiled: May 4, 1995Date of Patent: July 8, 1997Assignee: Institut Francais Du PetroleInventors: Eric Benazzi, Jean-Fran.cedilla.ois Joly, Christian Marcilly
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Patent number: 5625114Abstract: A process for the recovery of a sulphonic acid catalyst from an aqueous extract of an alkylation effluent stream comprising the steps ofevaporating the extract to obtain a hydrate of the sulphonic acid catalyst;reacting the hydrate with an olefin containing hydrocarbon stream to its corresponding sulphonic acid ester; andintroducing the acid ester to a process for the alkylation of a hydrocarbon feedstock with an olefinic alkylation agent at alkylation conditions, thereby decomposing the sulphonic acid ester to its acid form being catalytic active in the alkylation process.Type: GrantFiled: May 25, 1995Date of Patent: April 29, 1997Assignee: Haldor Tops.o slashed.e A/SInventor: Sven I. Hommeltoft
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Patent number: 5625113Abstract: A process is disclosed for alkylating an isoparaffin with an olefin comprising the steps of:(a) reacting an isoparaffin having from 4 to 8 carbon atoms with an olefin having from 2 to 12 carbon atoms in a first alkylation reaction stage at temperature from about -40.degree. C. to about 500.degree. C. and overall isoparaffin:olefin feed weight ratio of from about 1:1 to about 250:1 with a solid alkylation catalyst comprising a synthetic porous crystalline material characterized by an X-ray diffraction pattern including values substantially as set forth in Table I of the specification and having a composition comprising the molar relationshipX.sub.2 O.sub.3 :(n)YO.sub.Type: GrantFiled: December 28, 1994Date of Patent: April 29, 1997Assignee: Mobil Oil CorporationInventors: Mohsen N. Harandi, James H. Beech, Jr., Albin Huss, Jr., Robert A. Ware, Altaf Husain
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Patent number: 5574201Abstract: The alkylation of C.sub.2 -C.sub.12 alkanes (preferably isobutane) with C.sub.2 -C.sub.12 alkenes (preferably butene-2), in the presence of trifluoromethanesulfonic acid on a solid inorganic material as catalyst, is carried out with dicyclopentadiene and/or tetrahydrodicyclopentadiene as additional alkylating agent(s).Type: GrantFiled: May 12, 1995Date of Patent: November 12, 1996Assignee: Phillips Petroleum CompanyInventor: Lyle R. Kallenbach
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Patent number: 5493067Abstract: Isoparaffins and olefins are alkylated by contact with a solid superacid such as sulfated zirconia optionally containing added metals, and containing added heteropolyacids (HPA's) or polyoxoanions (POA's). The presence of HPA's or POA's in the solid superacid catalyst results in higher yields of desired high-octane components in the product mixture than are obtained in the absence of HPA's or POA's.Type: GrantFiled: November 12, 1993Date of Patent: February 20, 1996Assignee: Sun Company, Inc. (R&M)Inventors: Howard P. Angstadt, Elmer J. Hollstein, Chao-Yang Hsu
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Patent number: 5491278Abstract: Isoparaffins and olefins are alkylated in the liquid phase by contact with a solid superacid such as sulfated zirconia containing heteropolyacids or polyoxoanions. High octane number blending components for motor fuel and other valuable products are obtained, with important advantages over processes using liquid acid catalysts, and over vapor phase alkylation with solid superacid catalysts.Type: GrantFiled: November 12, 1993Date of Patent: February 13, 1996Assignee: Sun Company, Inc. (R&M)Inventors: Howard P. Angstadt, Elmer J. Hollstein, Chao-Yang Hsu
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Patent number: 5489729Abstract: The present invention relates to a catalyst comprising silica and an acid phase comprising sulphuric acid and the compound HB(HSO.sub.4).sub.4, the silica having been impregnated by said acid phase, said catalyst being such that is consists essentially of particles of an average diameter of between 0.1 and 150 .mu.m, its content by weight of acid phase is greater than 40%, the silica, prior to its impregnation with said acid phase, has a total porous volume of between 0.5 and 6 cm.sup.3 per gram and said acid phase contains between 0.4% and 68.8% by weight of the compound HB(HSO.sub.4).sub.4, said acid phase containing neither sulphuric anhydride nor boric acid.The invention also relates to the preparation and use of said catalyst in catalytic alkylation of isobutane and/or isopentane in the presence of at least one olefin containing 3 to 6 carbon atoms per molecule.Type: GrantFiled: September 12, 1994Date of Patent: February 6, 1996Assignee: Institut Francais du PetroleInventors: Eric Benazzi, Jean Francois Joly, Frederic Chaigne, Jean Yves Bernhard, Christian Marcilly
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Patent number: 5489560Abstract: The invention concerns a process for regenerating an impure catalyst comprising sulphuric acid deposited on silica.It is characterized in that the catalyst is calcined at least once to eliminate organic hydrocarbon substances contained in the catalyst, in particular as a result of its use in aliphatic alkylation reactions.Type: GrantFiled: January 6, 1995Date of Patent: February 6, 1996Assignee: Institut Francais du PetroleInventors: Jean-Francois Joly, Eric Benazzi, Frederic Chaigne, Jean-Yves Bernhard, Jean-Charles Viltard
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Patent number: 5489730Abstract: The present invention relates to a catalyst comprising silica and sulphuric acid which impregnates said silica, and the use of said catalyst in catalytic alkylation of isobutane and/or isopentane in the presence of at least one olefin containing 3 to 6 carbon atoms per molecule, said catalyst being characterized in that the silica, prior to its impregnation with sulphuric acid, has a total porous volume greater than 1.5 cm.sup.3 per gram and in that said catalyst consists essentially of particles of an average diameter of between 0.1 and 150 .mu.m.Type: GrantFiled: September 12, 1994Date of Patent: February 6, 1996Assignee: Institut Francais du PetroleInventors: Jean Francois Joly, Christian Marcilly, Eric Benazzi, Frederic Chaigne, Jean Yves Bernhard
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Patent number: 5489728Abstract: The present invention relates to a catalyst comprising silica and an acid phase comprising sulphuric acid and the compound HB(HSO.sub.4).sub.4, the silica having been impregnated by said acid phase, said catalyst being such that is consists essentially of particles of an average diameter of between 0.1 and 30 .mu.m, prior to its impregnation with said acid phase, has a total porous volume of between 0.1 and 6 cm.sup.3 per gram and said acid phase contains between 0.4% and 68.8% by weight of the compound HB(HSO.sub.4).sub.4, and between 31.2% and 99.6% by weight of the compound containing neither sulphuric anhydride nor boric acid.The invention also relates to the preparation and use of said catalyst in catalytic alkylation of isobutane and/or isopentane in the presence of at least one olefin containing 3 to 6 carbon atoms per molecule.Type: GrantFiled: September 12, 1994Date of Patent: February 6, 1996Assignee: Institut Francais du PetroleInventors: Eric Benazzi, Jean Francois Joly, Christian Marcilly, Frederic Chaigne, Jean Yves Bernhard
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Patent number: 5475184Abstract: Catalyst comprising a porous mineral or organic support and a mixture constituted by sulphuric acid, trifluoromethanesulphonic acid and, optionally, water. The invention also relates to a method for the preparation of the catalyst and its use in catalytic alkylation of isobutane and/or isopentane in the presence of at least one olefin comprising 3 to 6 carbon atoms per molecule.Type: GrantFiled: April 20, 1994Date of Patent: December 12, 1995Assignee: Institut Francais Du PetroleInventors: Jean-Francois Joly, Nathalie Ferrer, Jean-Yves Bernhard, Eric Benazzi
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Patent number: 5444175Abstract: The invention relates to an alkylation process, in which a charge incorporating at least one isoparaffin and at least one olefin containing 2 to 6 carbon atoms per molecule, is treated in the presence of a solid alkylation catalyst. In the process, catalyst present in a reaction R is contacted with the charge, recycled liquid effluent discharged from reaction zone R and liquid effluent discharged from an isobutane/n-butane/alkylate separation zone S. The process uses a specific catalyst, e.g., sulfuric acid impregnated on a porous support.Type: GrantFiled: August 20, 1993Date of Patent: August 22, 1995Assignee: Institut Francais Du PetroleInventors: Jean-Francois Joly, Eric Benazzi, Christian Marcilly, Renaud Pontier, Jean-Francois Le Page
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Patent number: 5420093Abstract: Catalyst based on silica and sulfuric acid and its use in the catalytic alkylation of isobutane and/or isopentane in the presence of at least one olefin having 3 to 6 carbon atoms per molecule. The catalyst may contain an additive, e.g., B(OH).sub.3, HBF.sub.4, H.sub.3 PO.sub.4, FSO.sub.3 H, CF.sub.3 SO.sub.3 H, SbF.sub.5, CF.sub.3 COOH and SO.sub.3.Type: GrantFiled: February 25, 1994Date of Patent: May 30, 1995Assignee: Institut Francais du PetroleInventors: Jean-Francois Joly, Christian Marcilly, Eric Benazzi
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Patent number: 5336833Abstract: Impregnated catalyst based on silica and a solid state sulfuric acid and its use in the catalytic alkylation of isobutene and/or isopentane in the presence of at least one olefin having 3-6 carbon atoms per molecule. The catalyst may contain an additive, e.g., B(OH).sub.3, HBF.sub.4, H.sub.3 PO.sub.4, FSO.sub.3 H, CF.sub.3 SO.sub.3 H, SbF.sub.5, CF.sub.3 COOH, and SO.sub.3.Type: GrantFiled: October 26, 1992Date of Patent: August 9, 1994Assignee: Institut Francais du PetroleInventors: Jean-Francois Joly, Christian Marcilly, Eric Benazzi