S-containing Patents (Class 585/730)
  • Patent number: 5958350
    Abstract: 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 porti
    Type: Grant
    Filed: January 28, 1999
    Date of Patent: September 28, 1999
    Assignee: Haldor Topsoe A/S
    Inventor: Sven Ivar Hommeltoft
  • Patent number: 5942654
    Abstract: 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 porti
    Type: Grant
    Filed: June 13, 1997
    Date of Patent: August 24, 1999
    Assignee: Haldor Topsoe A/S
    Inventor: Sven Ivar Hommeltoft
  • Patent number: 5925801
    Abstract: 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: Grant
    Filed: February 13, 1997
    Date of Patent: July 20, 1999
    Assignee: Institut Kataliza Imeni G.K. Boreskova Sibirskogo Otdelenia Rossiiskoi Akademii Nauk
    Inventors: Valery Kuzmich Duplyakin, Valentina Petrovna Finevich, Gleb Alexandrovich Urzhuntsev, Alexandr Ivanovich Lugovskoi
  • Patent number: 5906957
    Abstract: The invention concerns a catalyst comprising a porous organic or inorganic support and at least one active phase comprising at least one acid selected from acids with formula R--SO.sub.3 H, where R is fluorine or an alkyl group or a fluorinated alkyl group, and at least one weakly basic aprotic organic solvent, the support having been impregnated with the active phase, the catalyst being such that it is essentially constituted by particles with an average diameter in the range 0.1 .mu.m to 150 .mu.m, and being such that before impregnation with the active phase, the support has a total pore volume in the range 0.5 cm.sup.3 /g to 6 cm.sup.3 /g. The invention also concerns the use of the catalyst for aliphatic alkylation.
    Type: Grant
    Filed: September 10, 1996
    Date of Patent: May 25, 1999
    Assignee: Institut Francais du Petrole
    Inventors: Eric Benazzi, Jean-Francois Joly
  • Patent number: 5888920
    Abstract: 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: Grant
    Filed: January 15, 1997
    Date of Patent: March 30, 1999
    Inventors: Tse-Chuan Chou, Chao-Shan Chou, Yi-Lin Chen
  • 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: 5849978
    Abstract: The invention concerns the catalytic alkylation of at least one isoparaffin selected from the group formed by isobutane and isopentane in the presence of at least one olefin containing 3 to 6 carbon atoms per molecule, using a catalyst comprising 40% to 99% by weight of an acid selected from acids with formula R--SO.sub.3 H where R is fluorine or an alkyl group or a fluorinated alkyl group, R preferably being F or CF.sub.3, and more preferably CF.sub.3, and 1% to 60% by weight of a solvent selected from the group formed by sulpholane, dimethylsulphoxide and dioxanes, preferably sulpholane.
    Type: Grant
    Filed: July 19, 1996
    Date of Patent: December 15, 1998
    Assignee: Institut Francais du Petrole
    Inventors: Eric Benazzi, Jean-Francois Joly, Nathalie Ferrer, Bernard Torck
  • 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: 5817908
    Abstract: 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: Grant
    Filed: May 20, 1996
    Date of Patent: October 6, 1998
    Assignee: Amoco Corporation
    Inventor: Robert L. Mehlberg
  • Patent number: 5811627
    Abstract: 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: Grant
    Filed: September 13, 1996
    Date of Patent: September 22, 1998
    Inventor: Stanley M. Welsh
  • Patent number: 5792896
    Abstract: An alkylation process for reacting alkylatable hydrocarbons in the presence of a sulfolane and hydrofluoric acid catalyst within a natural circulation reaction and circulation system.
    Type: Grant
    Filed: March 4, 1997
    Date of Patent: August 11, 1998
    Assignee: Phillips Petroleum Company
    Inventors: Bruce B. Randolph, Richard L. Anderson, Harvey D. Hensley
  • Patent number: 5777189
    Abstract: Disclosed is a process for the alkylation of an olefin with an isoparaffin using sulphuric acid as a catalyst. In this process, a finely-dispersed emulsion of isoparaffin and sulphuric acid is prepared first, in a separate emulsion preparation zone. This preparation is carried out by injecting the isoparaffin into the acid through a set of nozzles, thereby allowing the isoparaffin to "scavenge" at high speed through the acid and thus to form an extremely homogeneous emulsion. This makes it possible to achieve proper mixing without need of impellers or other similar mixing devices that usually call for substantial maintenance and operating costs. Then, the emulsion that was so prepared and which forms an already "finished" phase per se, is fed into a reaction zone which is separate from the emulsion preparation zone and in which the olefin is injected preferably at a plurality of points and in directions perpendicular to the emulsion flow.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: July 7, 1998
    Assignee: Orgral International Technologies Corporation
    Inventors: Georgy G. Alexanyan, Nikolay B. Librovitch, Yuri A. Prochukhane
  • Patent number: 5767335
    Abstract: Disclosed is an alkylation process which utilizes a mixture of sulfone and hydrogen fluoride as an alkylation catalyst. The process provides for the removal of light ASO from the alkylation catalyst that accumulates therein as a result of the inability to remove the light ASO produced as a by-product of the alkylation reaction.
    Type: Grant
    Filed: December 18, 1995
    Date of Patent: June 16, 1998
    Assignee: Phillips Petroleum Company
    Inventors: Richard L. Anderson, Keith W. Hovis
  • Patent number: 5763728
    Abstract: An HF-agent complex, such as HF-pyridine complex where the complexing agent is pyridine, is recovered and recycled from a by-product containing stream in an alkylation process using the complex by (a) selectively removing a portion of the HF from the by-product stream to produce an HF-depleted stream having a molar ratio of HF per Lewis base site of the complexing agent of 3:1 to 5:1, (b) separating the resulting HF-depleted stream into a hydrocarbon phase enriched in ASO and an acid phase depleted in ASO and containing a substantial portion of the complex, and (c) recycling the acid phase to the hydrocarbon alkylation step.
    Type: Grant
    Filed: September 25, 1995
    Date of Patent: June 9, 1998
    Assignee: UOP
    Inventors: Joseph A. Kocal, Harold U. Hammershaimb, Robert J. Cornish, Terry L. Marker, James F. Himes
  • 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: 5731256
    Abstract: 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: Grant
    Filed: June 5, 1995
    Date of Patent: March 24, 1998
    Assignee: Institut Francais du Petrole
    Inventors: Eric Benazzi, Jean-Fran.cedilla.ois Joly, Christian Marcilly
  • Patent number: 5723715
    Abstract: 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: Grant
    Filed: May 30, 1995
    Date of Patent: March 3, 1998
    Inventors: Bruce B. Randolph, Ronald G. Abbott
  • Patent number: 5675053
    Abstract: Improved process for the supported liquid phase alkylation of an aliphatic hydrocarbon feedstock in the presence of a fluorinated sulphonic acid catalyst with an olefinic alkylating agent in a reactor containing a fixed bed of particular polar contact material, wherein a reaction zone with the fluorinated sulphonic acid catalyst is moveable established by absorbing the acid catalyst within a confined area of the contact material and passing a process stream of the aliphatic hydrocarbon feedstock and the olefinic alkylating agent through the reactor and the reaction zone, and withdrawing an alkylated product stream from the reactor, wherein the improvement comprises introduction of the fluorinated sulphonic acid alkylation catalyst into the reactor dissolved in a hydrocarbon solvent comprises C.sub.3 -C.sub.9 hydrocarbons and adsorption of the acid catalyst in the solution of the hydrocarbon solvent on the contact material at inlet end of the reactor.
    Type: Grant
    Filed: December 1, 1995
    Date of Patent: October 7, 1997
    Assignee: Haldor Topsoe A/S
    Inventor: Sven Ivar Hommeltoft
  • 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: 5659105
    Abstract: 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: Grant
    Filed: May 23, 1995
    Date of Patent: August 19, 1997
    Assignees: Eniricerche S.p.A., Agip Petroli S.p.A.
    Inventors: Mario Gabriele Clerici, Carlo Perego, Alberto de Angelis, Luciano Montanari
  • Patent number: 5654251
    Abstract: 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 and a sulfone. The novel alkylation catalyst is utilized in a novel process for alkylating olefin hydrocarbons with isoparaffin hydrocarbons.
    Type: Grant
    Filed: June 2, 1995
    Date of Patent: August 5, 1997
    Assignee: Phillips Petroleum Company
    Inventors: Ronald G. Abbott, Ralph P. Williams, Marvin M. Johnson, John W. Vanderveen
  • Patent number: 5646086
    Abstract: 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: Grant
    Filed: May 4, 1995
    Date of Patent: July 8, 1997
    Assignee: Institut Francais Du Petrole
    Inventors: Eric Benazzi, Jean-Fran.cedilla.ois Joly, Christian Marcilly
  • Patent number: 5639932
    Abstract: 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 blending components of gasoline motor fuel. The novel catalyst comprises a mixture of a hydrogen halide, a sulfone and water and has suitable corrosion properties which permit its utilization in alkylation process systems. The novel alkylation catalyst is utilized in a novel process for alkylating olefin hydrocarbons with isoparaffin hydrocarbons.
    Type: Grant
    Filed: May 26, 1995
    Date of Patent: June 17, 1997
    Assignee: Phillips Petroleum Company
    Inventors: Ronald G. Abbott, Bruce B. Randolph
  • Patent number: 5639930
    Abstract: Method of producing alkylates in which an isoparaffin, olefin, a diffusing agent and a solid, acid catalyst are combined to form a three phase reaction mixture; a hydrocarbon phase containing primarily isoparaffin, a diffusing agent phase containing the diffusing agent, olefin and diffuse isoparaffin and a solid, acid catalyst phase, the diffusing agent being a polar solvent in which the olefin and aromatics are soluble.
    Type: Grant
    Filed: January 4, 1995
    Date of Patent: June 17, 1997
    Inventor: Joe E. Penick
  • Patent number: 5625113
    Abstract: 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: Grant
    Filed: December 28, 1994
    Date of Patent: April 29, 1997
    Assignee: Mobil Oil Corporation
    Inventors: Mohsen N. Harandi, James H. Beech, Jr., Albin Huss, Jr., Robert A. Ware, Altaf Husain
  • Patent number: 5625114
    Abstract: 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: Grant
    Filed: May 25, 1995
    Date of Patent: April 29, 1997
    Assignee: Haldor Tops.o slashed.e A/S
    Inventor: Sven I. Hommeltoft
  • Patent number: 5574201
    Abstract: 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: Grant
    Filed: May 12, 1995
    Date of Patent: November 12, 1996
    Assignee: Phillips Petroleum Company
    Inventor: Lyle R. Kallenbach
  • Patent number: 5569807
    Abstract: 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 blending components of gasoline motor fuel. The novel catalyst comprises a mixture of a hydrogen halide, a sulfone and water and has suitable corrosion properties which permit its utilization in alkylation process systems. The novel alkylation catalyst is utilized in a novel process for alkylating olefin hydrocarbons with isoparaffin hydrocarbons.
    Type: Grant
    Filed: May 1, 1992
    Date of Patent: October 29, 1996
    Assignee: Phillips Petroleum Company
    Inventors: Ronald G. Abbott, Bruce B. Randolph
  • Patent number: 5547909
    Abstract: An improved process for the regeneration of an ASO-containing HF catalyst by the removal of ASO from said catalyst through the utilization of a separation column equipped with fixed valve fractionation trays. The separation column defines a separation zone having a top zone, an intermediate zone, and a bottom zone wherein contained within the bottom zone is a series of vertically spaced, fixed valve fractionation trays, wherein each of the fixed valve fractionation trays include a plate defining a plurality of apertures and wherein fixedly spaced above each of the apertures is a valve having a shape substantially the same as the apertures for directing the flow of gas passing upwardly through the apertures of the plate into the direction substantially parallel to the plate.
    Type: Grant
    Filed: February 24, 1994
    Date of Patent: August 20, 1996
    Assignee: Phillips Petroleum Company
    Inventor: LeRoy W. Carlson
  • Patent number: 5534657
    Abstract: 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 blending components of gasoline motor fuel. The novel catalyst comprises a mixture of a hydrogen halide, a sulfone and water and has suitable corrosion properties which permit its utilization in alkylation process systems. The novel alkylation catalyst is utilized in a novel process for alkylating olefin hydrocarbons with isoparaffin hydrocarbons.
    Type: Grant
    Filed: January 20, 1995
    Date of Patent: July 9, 1996
    Assignee: Phillips Petroleum Company
    Inventors: Bruce B. Randolph, Ronald G. Abbott, Jonathan E. Child, Kenneth J. Del Rossi
  • Patent number: 5527980
    Abstract: An improved process for the regeneration of an ASO-containing HF catalyst by the removal of ASO from said catalyst through the utilization of a separation column equipped with fixed valve fractionation trays. The separation column defines a separation zone having a top zone, an intermediate zone, and a bottom zone wherein contained within the bottom zone is a series of vertically spaced, fixed valve fractionation trays, wherein each of the fixed valve fractionation trays includes a plate defining a plurality of apertures and wherein fixedly spaced above each of the apertures is a valve having a shape substantially the same as the apertures for directing the flow of gas passing upwardly through the apertures of the plate into the direction substantially parallel to the plate.
    Type: Grant
    Filed: August 30, 1994
    Date of Patent: June 18, 1996
    Assignee: Phillips Petroleum Company
    Inventor: LeRoy W. Carlson
  • Patent number: 5498818
    Abstract: 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 blending components of gasoline motor fuel. The novel catalyst comprises a mixture of a hydrogen halide, a sulfone and water and has suitable corrosion properties which permit its utilization in alkylation process systems. The novel alkylation catalyst is utilized in a novel process for alkylating olefin hydrocarbons with isoparaffin hydrocarbons. Also, described is a method for suppressing the rate of evaporation of hydrogen fluoride from a mixture of hydrogen fluoride and sulfolane that has been exposed to the atmosphere.
    Type: Grant
    Filed: April 28, 1994
    Date of Patent: March 12, 1996
    Assignee: Phillips Petroleum Company
    Inventors: Bruce B. Randolph, Ronald G. Abbott
  • 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: 5493067
    Abstract: 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: Grant
    Filed: November 12, 1993
    Date of Patent: February 20, 1996
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Howard P. Angstadt, Elmer J. Hollstein, Chao-Yang Hsu
  • Patent number: 5491278
    Abstract: 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: Grant
    Filed: November 12, 1993
    Date of Patent: February 13, 1996
    Assignee: Sun Company, Inc. (R&M)
    Inventors: Howard P. Angstadt, Elmer J. Hollstein, Chao-Yang Hsu
  • Patent number: 5489730
    Abstract: 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: Grant
    Filed: September 12, 1994
    Date of Patent: February 6, 1996
    Assignee: Institut Francais du Petrole
    Inventors: Jean Francois Joly, Christian Marcilly, Eric Benazzi, Frederic Chaigne, Jean Yves Bernhard
  • Patent number: 5489728
    Abstract: 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: Grant
    Filed: September 12, 1994
    Date of Patent: February 6, 1996
    Assignee: Institut Francais du Petrole
    Inventors: Eric Benazzi, Jean Francois Joly, Christian Marcilly, Frederic Chaigne, Jean Yves Bernhard
  • Patent number: 5489729
    Abstract: 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: Grant
    Filed: September 12, 1994
    Date of Patent: February 6, 1996
    Assignee: Institut Francais du Petrole
    Inventors: Eric Benazzi, Jean Francois Joly, Frederic Chaigne, Jean Yves Bernhard, Christian Marcilly
  • Patent number: 5489560
    Abstract: 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: Grant
    Filed: January 6, 1995
    Date of Patent: February 6, 1996
    Assignee: Institut Francais du Petrole
    Inventors: Jean-Francois Joly, Eric Benazzi, Frederic Chaigne, Jean-Yves Bernhard, Jean-Charles Viltard
  • Patent number: 5476983
    Abstract: The present invention provides a method for reclaiming HF and producing valuable gasoline blending components from the conjunct polymeric byproducts (acid soluble oil or ASO) formed as a byproduct of acid-catalyzed isoparaffin-olefin alkylation comprising the steps of:(a) reacting isoparaffin and olefin in the presence of a liquid acid alkylation catalyst to form alkylate and ASO byproduct;(b) separating alkylate, unreacted isoparaffin, and a majority of said liquid acid alkylation catalyst from said ASO;(c) reacting said separated ASO of step (b) under conditions of elevated temperature and pressure to convert the hydrocarbon portion of said ASO to gasoline boiling range hydrocarbons and to liberate HF.In a preferred embodiment, the ASO is pre-mixed with hydrogen or a hydrogen donor before reaction at elevated temperature and pressure. In a particularly preferred embodiment, the elevated temperature reaction is carried out in the presence of a catalyst such as activated carbon.
    Type: Grant
    Filed: August 4, 1994
    Date of Patent: December 19, 1995
    Assignee: Mobil Oil Corporation
    Inventor: Tsoung Y. Yan
  • Patent number: 5475184
    Abstract: 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: Grant
    Filed: April 20, 1994
    Date of Patent: December 12, 1995
    Assignee: Institut Francais Du Petrole
    Inventors: Jean-Francois Joly, Nathalie Ferrer, Jean-Yves Bernhard, Eric Benazzi
  • Patent number: 5461183
    Abstract: A method for separating conjunct polymers which are formed as byproducts of acid catalyzed isoparaffin-olefin alkylation and sulfolane from a mixture containing conjunct polymers, sulfolane, and hydrofluoric acid comprising stripping HF from the spent catalyst, treating the stripped, spent catalyst with hydrogen to provide a stripped hydrotreated catalyst stream, and gravitationally separating the stripped hydrotreated catalyst stream to remove conjunct polymeric byproducts.
    Type: Grant
    Filed: July 15, 1994
    Date of Patent: October 24, 1995
    Assignee: Mobil Oil Corporation
    Inventors: Kenneth J. Del Rossi, Tomas R. Melli
  • Patent number: 5457258
    Abstract: A method of recovery of acid catalyst from acid soluble oil being formed in a process for alkylation of hydrocarbons and containing valuable amounts of spent acid catalyst which method comprises,treating the acid soluble oil with hydrogen in the presence of a catalyst comprising one or more metals from Group VIII of the Periodic Table supported on an acid resistant carrier; andrecycling the hydrotreated acid soluble oil to the alkylation process.
    Type: Grant
    Filed: July 6, 1994
    Date of Patent: October 10, 1995
    Assignee: Haldor Topoe A/S
    Inventors: Sven I. Hommeltoft, Claus J. H. Jacobsen
  • Patent number: 5420093
    Abstract: 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: Grant
    Filed: February 25, 1994
    Date of Patent: May 30, 1995
    Assignee: Institut Francais du Petrole
    Inventors: Jean-Francois Joly, Christian Marcilly, Eric Benazzi
  • Patent number: 5414187
    Abstract: The present invention provides a process for the conversion of a reactant into a reaction product in the presence of a novel acid catalyst complex comprising an organosulfonic acid having the formula[(R.sup.2 O).sub.2 P(O)].sub.y R(SO.sub.r R.sup.1).sub.xwherein R is an organo radical having at least one covalent carbon-fluorine bond, R.sup.1 is hydrogen, R.sup.1 is a hydrocarbyl radical having up to 20 carbon atoms or hydrogen, r is 2 or 3, x is an integer from 1 to 3, y is an integer of from 1 to 3 with the proviso that the phosphorus and the sulfur are covalently bonded to a carbon atom and which organosulfonic acid has been contacted with a Lewis Acid to produce a catalyst complex containing said Lewis Acid. In the elected claims, a process for providing a high octane alkylate stream by converting a mixture comprising isoparaffins and olefins into said alkylate in the presence of said acid catalyst complex, is described.
    Type: Grant
    Filed: October 30, 1992
    Date of Patent: May 9, 1995
    Assignee: Catalytica, Inc.
    Inventors: David L. King, Michael D. Cooper, William A. Sanderson
  • Patent number: 5349116
    Abstract: A composition of matter comprises trifluorometbanesulfonic acid and a solid inorganic material which contains aluminum borate and aluminum oxide, This composition is used as a catalyst for alkylating at least one C.sub.2 -C.sub.10 alkane (preferably isobutane and/or an isooctane) with at least one C.sub.2 -C.sub.10 alkene (preferably pentene-1 and/or hexene-1).
    Type: Grant
    Filed: June 25, 1993
    Date of Patent: September 20, 1994
    Assignee: Phillips Petroleum Company
    Inventors: Lyle R. Kallenbach, Marvin M. Johnson
  • Patent number: 5347067
    Abstract: Described is a novel acid-soluble oil composition produced as a by-product from an alkylation reaction catalyzed by a sulfone-containing catalyst. Also described is a novel process for regenerating an alkylation catalyst which contains a sulfone component. The regeneration process utilizes alumina adsorbent to remove a substantial portion of the hydrogen halide from the spent catalyst, thereby producing a neutralized stream, which is then treated with carbon to remove a substantial portion of the reaction by-product to produce a sulfone stream substantially free of reaction by-product and hydrogen halide.
    Type: Grant
    Filed: August 24, 1993
    Date of Patent: September 13, 1994
    Assignee: Phillips Petroleum Company
    Inventors: Alan D. Eastman, Ronald G. Abbott
  • Patent number: 5347066
    Abstract: A process for producing an alkylate product having an improved octane value from an olefin stream having a reduced concentration of the butene isomer of isobutylene. The olefin feed stream to the process system is substantially free of isobutylene and can have undergone prior processing to remove isobutylene therefrom. The olefin feed is subjected to an alkylation reaction catalyzed by a mixture of hydrogen fluoride and sulfone.
    Type: Grant
    Filed: May 6, 1993
    Date of Patent: September 13, 1994
    Assignee: Phillips Petroleum Company
    Inventor: Bruce B. Randolph
  • Patent number: 5345028
    Abstract: Disclosed is an alkylation catalyst to form adducts or alkylates of a C.sub.3 -C.sub.9 olefin with a C.sub.4 to C.sub.9 isoparaffin comprising a sulfated mixed oxide of titanium and nickel, wherein the percent by weight of titanium is at least 80%; of nickel is in the range 1-4%; and of sulfur in the range 1-10%. Also disclosed are the appropriate ratios of olefin to isoparaffin and the use of adamantane to increase yields.
    Type: Grant
    Filed: March 10, 1993
    Date of Patent: September 6, 1994
    Assignee: Ashland Oil, Inc.
    Inventor: Saeed Alerasool
  • Patent number: 5336833
    Abstract: 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: Grant
    Filed: October 26, 1992
    Date of Patent: August 9, 1994
    Assignee: Institut Francais du Petrole
    Inventors: Jean-Francois Joly, Christian Marcilly, Eric Benazzi