Including Alkylation To Produce Branched-chain Paraffin Patents (Class 585/331)
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Patent number: 7439410Abstract: An integrated isomerization-alkylation process is disclosed that uses a common distillation zone. The process can comprise halogen removal. The process is suitable for the production of motor fuels from isoparaffins and olefins using solid alkylation and isomerization catalysts.Type: GrantFiled: March 30, 2007Date of Patent: October 21, 2008Assignee: UOP LLCInventors: Lynn H. Rice, Dale J. Shields
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Publication number: 20080207971Abstract: A system and/or process for increasing the isobutane to olefin ratio in an alkylation process/system is disclosed. The system and/or process includes provisions for charging a portion of the settler effluent as a feed to at least one reaction zone downflow from the first reaction zone of a multi-zone alkylation reactor along with a portion of the olefin feed to the multi-zone alkylation reactor.Type: ApplicationFiled: April 8, 2008Publication date: August 28, 2008Inventors: Robert M. Gray, Keith W. Hovis
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Publication number: 20080146858Abstract: A process for producing alkylate comprising contacting a first hydrocarbon stream comprising at least one olefin having from 2 to 6 carbon atoms which contains 1-butene with an isomerization catalyst under conditions favoring the isomerization of 1-butene to 2-butene so the isomerized stream contains a greater concentration of 2-butene than the first hydrocarbon stream and contacting the isomerized stream and a second hydrocarbon stream comprising at least one isoparaffin having from 3 to 6 carbon atoms with an acidic ionic liquid catalyst under alkylation conditions to produce an alkylate stream is disclosed.Type: ApplicationFiled: December 14, 2006Publication date: June 19, 2008Inventors: Saleh Elomari, Hye-Kyung C. Timken
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Patent number: 7153432Abstract: A process for the production of highly purified water 38 from Fischer-Tropsch reaction water 12, includes at least the steps of a primary treatment stage comprising an equilibrium staged separation process 14 having at least one stage for removing at least a fraction of non-acid oxygenated hydrocarbons from the Fischer-Tropsch reaction water 12 to produce a primary water-enriched stream 16, a secondary treatment stage comprising at least one membrane separation process 28 for removing at least some suspended solids and acidic oxygenated hydrocarbons from at least a portion of the primary water-enriched stream 16 to produce a secondary water-enriched stream 34 and a tertiary treatment stage comprising a dissolved salt and organic removal stage 36 for removing at least some dissolved salts and organic constituents from at least a portion of the secondary water-enriched stream 34.Type: GrantFiled: December 16, 2004Date of Patent: December 26, 2006Assignee: Sasol Technology (Pty) Ltd.Inventors: Luis Pablo Fidel Dancuart Kohler, Gert Hendrik Du Plessis, Francois Jacobus Du Toit, Edward Ludovicus Koper, Trevor David Phillips, Janette Van Der Walt
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Patent number: 6919016Abstract: A process is disclosed for preparing a C4 stream for feeding to an alkylation process which reacts isobutane with butene to produce isooctane. The C4 stream is treated in a first distillation column reactor to remove dienes and mercaptans and separate out any C5's which might be present. The treated C4's are then fed to a second distillation column reactor that concurrently isomerizes 1-butene to 2-butene and splits the normal C4's from the iso C4's. The iso C4's are then fed to a third distillation column reactor where a portion of the isobutene is saturated to isobutane. The C4's from the isomerization/splitter are combined with the C4's from the hydrogenation unit and fed to a cold acid alkylation unit. The third distillation column may also oligomerize a portion of the isobutene to diisobutene in the upper end which is saturated in the bottom of the column to isooctane.Type: GrantFiled: August 5, 2004Date of Patent: July 19, 2005Assignee: Catalytic Distillation TechnologiesInventors: Gary G. Podrebarac, Mario J. Maraschino
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Patent number: 6897345Abstract: A process is described for the production of hydrocarbons with a high octane number starting from mixtures essentially consisting of n-butane and isobutane (such as for example field butanes) comprising a skeleton isomerization section, a dehydrogenation section of paraffins, a selective hydrogenation section of butadiene, two conversion sections of olefins, in which the isobutene is firstly selectively transformed by means of dimerization and/or etherification, followed by the linear butenes by means of alkylation, in order to obtain, by joining the products of the two conversion sections, a product having excellent motoristic properties (octane number, volatility and distillation curve).Type: GrantFiled: April 23, 2003Date of Patent: May 24, 2005Assignee: Snamprogetti S.p.A.Inventors: Mario Marchionna, Marco Di Girolamo, Domenico Sanfilippo, Alberto Paggini
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Patent number: 6872862Abstract: A method for making propylene from alpha olefins, internal linear olefins and isoolefins wherein the alpha olefins are subjected to a combination of hydrogenation and double bond isomerization to form additional internal linear olefins, the internal linear olefins are separated from the isoolefins and disproportionated with ethylene to form a propylene product, while the thus separated isoolefins are subjected to skeletal isomerization to form yet additional internal linear olefins to be converted into yet additional propylene product.Type: GrantFiled: June 25, 2003Date of Patent: March 29, 2005Assignee: Equistar Chemicals, LPInventors: Robert S. Bridges, Donald H. Powers, Steven T. Coleman
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Patent number: 6849773Abstract: A process is disclosed for preparing a C4 stream for feeding to an alkylation process which reacts isobutane with butene to produce isooctane. The C4 stream is treated in a first distillation column reactor to remove dienes and mercaptans and separate out any C5's which might be present. The treated C4's are then fed to a second distillation column reactor that concurrently isomerizes 1-butene to 2-butene and splits the normal C4's from the iso C4'S. The iso C4's are then fed to a third distillation column reactor where a portion of the isobutene is saturated to isobutane. The C4's from the isomerization/splitter are combined with the C4's from the hydrogenation unit and fed to a cold acid alkylation unit. The third distillation column may also oligomerize a portion of the isobutene to diisobutene in the upper end which is saturated in the bottom of the column to isooctane.Type: GrantFiled: January 23, 2002Date of Patent: February 1, 2005Assignee: Catalytic Distillation TechnologiesInventors: Gary G. Podrebarac, Mario J. Maraschino
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Patent number: 6784330Abstract: A process for treating methane-containing natural gas is provided which comprises: i) converting methane to methanol at or near a site of natural gas production; ii) transporting the methanol to a refinery remote from said site of production, said refinery producing ethylene and propylene and comprising an alkylation unit which can utilize a propylene feed; and iii) converting said methanol to gasoline boiling range fuel product and petrochemicals, including ethylene, propylene, butenes and xylenes.Type: GrantFiled: August 14, 2003Date of Patent: August 31, 2004Assignee: ExxonMobil Chemical Patents Inc.Inventors: Stephen H. Brown, William A. Weber, Reuel Shinnar
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Patent number: 6768035Abstract: A Fischer-Tropsch C3-C4 olefin stream is simultaneously dehydrated and isomerized to convert alcohols to olefins and 1-butenes to 2-butenes and thereby lower the oxygenate content. Another Fischer-Tropsch fraction is hydrotreated and hydrocracked to provide an isobutane stream. The treated C3-C4 olefin stream having an oxygenate content less than 4000 ppm, is reacted with the isobutane stream to provide a highly branched, high octane isoparaffinic alkylate. The alkylate is useful as a blending component in motor gasoline.Type: GrantFiled: January 31, 2002Date of Patent: July 27, 2004Assignee: Chevron U.S.A. Inc.Inventors: Dennis J. O'Rear, Steven S. Mathur, Thomas Van Harris, Curtis L. Munson, Cong-Yan Chan
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Publication number: 20040077910Abstract: A process is disclosed for preparing a C4 stream for feeding to an alkylation process which reacts isobutane with butene to produce isooctane. The C4 stream is treated in a first distillation column reactor to remove dienes and mercaptans and separate out any C5's which might be present. The treated C4's are then fed to a second distillation column reactor that concurrently isomerizes 1-butene to 2-butene and splits the normal C4's from the iso C4'S. The iso C4's are then fed to a third distillation column reactorwhere a portion of the isobutene is saturated to isobutane. The C4's from the isomerization/splitter are combined with the C4's from the hydrogenation unit and fed to a cold acid alkylation unit. The third distillation column may also oligomerize a portion of the isobutene to diisobutene in the upper end which is saturated in the bottom of the column to isooctane.Type: ApplicationFiled: January 23, 2002Publication date: April 22, 2004Applicant: CATALYTIC DISTILLATION TECHNOLOGIESInventors: Gary G. Podrebarac, Mario J. Maraschino
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Publication number: 20040054242Abstract: A process for treating methane-containing natural gas is provided which comprises: i) converting methane to methanol at or near a site of natural gas production; ii) transporting the methanol to a refinery remote from said site of production, said refinery producing ethylene and propylene and comprising an alkylation unit which can utilize a propylene feed; and iii) converting said methanol to gasoline boiling range fuel product and petrochemicals, including ethylene, propylene, butenes and xylenes.Type: ApplicationFiled: August 14, 2003Publication date: March 18, 2004Inventors: Stephen H. Brown, William A. Weber, Reuel Shinnar
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Publication number: 20040010171Abstract: A process is described for the production of hydrocarbons with a high octane number starting from mixtures essentially consisting of n-butane and isobutane (such as for example field butanes) comprising a skeleton isomerization section, a dehydrogenation section of paraffins, a selective hydrogenation section of butadiene, two conversion sections of olefins, in which the isobutene is firstly selectively transformed by means of dimerization and/or etherification, followed by the linear butenes by means of alkylation, in order to obtain, by joining the products of the two conversion sections, a product having excellent motoristic properties (octane number, volatility and distillation curve).Type: ApplicationFiled: April 23, 2003Publication date: January 15, 2004Applicant: SNAMPROGETTI S.p.A.Inventors: Mario Marchionna, Marco Di Girolamo, Domenico Sanfilippo, Alberto Paggini
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Patent number: 6673977Abstract: A procedure for the alkylation of isobutane by olefinic hydrocarbons, in which a first hydrocarbon charge (3) rich in isobutane is put in contact with a second hydrocarbon charge rich in light olefins (2), under conditions that will provoke the alkylation of the isobutane by the light olefins, the effluents that emanate from the reaction area in a fractionation column (6) are treated in order to extract therefrom at least a first cut rich in alkylate (7), a second cut rich in normal butane (8) and a third cut rich in isobutane (9), said third cut (9) is then recycled at the entry of the alkylation reaction area. The second cut (8) rich in normal butane is purified (12) so as to lower its content in compounds with 5 or more carbon atoms to a value that is less than or equal to 5% by weight, the cut thus purified (14) is treated in an isomerization reactor (16) of normal butane to isobutane, this cut is then recycled (21) at the entry of the alkylation effluents fractionation column (6).Type: GrantFiled: December 20, 2000Date of Patent: January 6, 2004Assignee: Total Raffinage Distribution S.A.Inventors: Jean-Louis Mauleon, Pedro Nascimento
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Patent number: 6632971Abstract: A process for treating methane-containing natural gas is provided which comprises: i) converting methane to methanol at or near a site of natural gas production; ii) transporting the methanol to a refinery remote from said site of production, said refinery producing ethylene and propylene and comprising an alkylation unit which can utilize a propylene feed; and iii) converting said methanol to gasoline boiling range fuel product and petrochemicals, including ethylene, propylene, butenes and xylenes.Type: GrantFiled: August 30, 2001Date of Patent: October 14, 2003Assignee: ExxonMobil Chemical Patents Inc.Inventors: Stephen H. Brown, William A. Weber, Reuel Shinnar
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Publication number: 20030166982Abstract: A Fischer-Tropsch C3-C4 olefin stream is treated to lower the oxygenate content to below 4000 ppm. Another Fischer-Tropsch fraction is hydrotreated and hydrocracked to provide an isobutane-containing stream. The treated C3-C4 olefin stream is reacted with the isobutane stream in an alkylation reactor to provide a highly branched, high octane isoparaffinic alkylate. The alkylate is useful as a blending component in motor gasoline.Type: ApplicationFiled: January 31, 2002Publication date: September 4, 2003Inventors: Dennis J. O' Rear, Steven S. Mathur, Thomas Van Harris, Curtis L. Munson, Cong-Yan Chen
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Publication number: 20030158456Abstract: A Fischer-Tropsch C3-C4 olefin stream is simultaneously dehydrated and isomerized to convert alcohols to olefins and 1-butenes to 2-butenes and thereby lower the oxygenate content. Another Fischer-Tropsch fraction is hydrotreated and hydrocracked to provide an isobutane stream. The treated C3-C4 olefin stream having an oxygenate content less than 4000 ppm, is reacted with the isobutane stream to provide a highly branched, high octane isoparaffinic alkylate. The alkylate is useful as a blending component in motor gasoline.Type: ApplicationFiled: January 31, 2002Publication date: August 21, 2003Inventors: Dennis J. O'Rear, Steven S. Mathur, Thomas Van Harris, Curtis Munson, Cong-Yan Chen
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Patent number: 6566569Abstract: A process for preparing a C4- product stream and a C6+ product stream is disclosed. The process involves contacting a C5 containing paraffinic feedstock with a catalyst that includes a hydrogenation/dehydrogenation catalyst and an olefin metathesis catalyst under conditions which dehydrogenate the paraffins to olefins. The olefins are then metathesized and rehydrogenated to provide a product stream. A C4- fraction and a C6+ fraction can each be isolated from the product stream. The C4- fraction can be used, for example, in an alkylation reaction to provide compounds useful in gasoline compositions. Unconverted C5 paraffins can be recycled. The C6+ fraction can be used, for example, as solvents. Alternatively, they can be isomerized to form gasoline additives, or can be converted to aromatic compounds via reforming, for example, using conventional reforming techniques, preferably using the AROMAX™ process or traditional rheniforming conditions.Type: GrantFiled: June 23, 2000Date of Patent: May 20, 2003Assignee: Chevron U.S.A. Inc.Inventors: Cong-Yan Chen, Dennis J. O'Rear, Scott R. Brundage
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Publication number: 20030073875Abstract: An integrated process for upgrading a mixed C4 or mixed C5 alkane/isoalkane stream first separates the iso from the normal alkane by distillation. Then a portion of the normal alkane is dehydrogenated to the corresponding alkene. The isoalkane and normal alkene are then fed to an alkylation unit where they are reacted together to form a branched chain alkane having a desirable octane number. If desired a portion of the separated normal alkane may be skeletally isomerized to additional isoalkane.Type: ApplicationFiled: February 8, 2002Publication date: April 17, 2003Applicant: CATALYTIC DISTILLATION TECHNOLOGIESInventors: J. Yong Ryu, Lawrence A. Smith, Abraham P. Gelbein, Frits Dautzenberg
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Patent number: 6433235Abstract: An improved process for the conversion of normally gaseous methane-containing hydrocarbon mixtures, such as natural gas, to a normally liquid hydrocarbon product comprises separating the methane component of the gaseous mixture from the heavier hydrocarbon component, cracking the separated heavier: hydrocarbon component at a relatively low temperature and optionally cracking the methane component at a relatively high temperature. The low temperature cracking product and any high temperature cracking product are separated into a light product of principally hydrogen and a heavy product comprising unsaturated hydrocarbons. This heavy product is reacted with methane in the presence of an acidic alkalization catalyst. The resulting product mixture is separated into a light product, a portion of which is recycled, and the normally liquid hydrocarbon product.Type: GrantFiled: June 9, 2000Date of Patent: August 13, 2002Assignee: Bryan Research & Engineering, Inc.Inventor: Joel G. Cantrell
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Publication number: 20020087040Abstract: A process is described for the production of hydrocarbons with a high octane number starting from mixtures essentially consisting of n-butane and isobutane (such as for example field butanes) comprising a skeleton isomerization section, a dehydrogenation section of paraffins, a selective hydrogenation section of butadiene, two conversion sections of olefins, in which the isobutene is firstly selectively transformed by means of dimerization and/or etherification, followed by the linear butenes by means of alkylation, in order to obtain, by joining the products of the two conversion sections, a product having excellent motoristic properties (octane number, volatility and distillation curve).Type: ApplicationFiled: November 9, 2001Publication date: July 4, 2002Applicant: SNAMPROGETTI S.p.A.Inventors: Mario Marchionna, Marco Di Girolamo, Domenico Sanfilippo, Alberto Paggini
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Patent number: 6333442Abstract: An aliphatic alkylate with a high octane number is prepared from a C4 catalytic cracking or steam-cracking fraction that contains mainly isobutane, isobutene, butene-1 and butenes-2 by: (a) hydro-isomerizing said C4 fraction, obtaining a mixture that contains for the most part butenes-2, isobutene and isobutane; (b) separating, by distillation of the hydro-isomerized fraction, of a butene-2-rich effluent that is collected at the bottom and an isobutane- and isobutene-rich effluent that is collected at the top; (c) sending said isobutene- and isobutane-rich effluent into a hydrogenation zone that produces an effluent that for the most part contains isobutane; (d) sending of said butenes-2-rich effluent that is derived from (b) and of said effluent that for the most part contains the isobutane that is derived from (c) into an alkylation zone producing, by addition of isobutane to butenes-2, an isooctane mixture that contains excess isobutane; (e) separating by distillation of excess isobutane, which comesType: GrantFiled: February 24, 1999Date of Patent: December 25, 2001Assignee: Institut Francais du PetroleInventors: Jean Cosyns, Blaise Didillon, Lionel Quicke
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Patent number: 6194625Abstract: Disclosed are various embodiments for alkylating olefins and isoparaffins in the presence of an acid to reduce and/or control acid consumption or maximize and/or control the octane number of the produced alkylate product. One embodiment includes alkylation by controlling the C3/iso-C5 olefin ratio to reduce acid consumption. Another embodiment includes alkylation of C3 and C5 olefins in separate alkylation zones to maximize alkylate octane number. Even another embodiment includes propylene alkylation followed by C4 and/or C5 olefin alkylation, with the spent propylene acid used in the C4 and/or C5 olefin alkylation. Still another embodiment includes alkylation of C3, C4 and C5 olefins in separate alkylation zones, with the spent propylene acid used in the C4 alkylation, and the spent butylene acid used in the C5 alkylation. Yet another embodiment includes alkylation by controlling the C3/C4 olefin ratio to maximize the octane number of the produced alkylate.Type: GrantFiled: September 22, 1998Date of Patent: February 27, 2001Assignee: Stratco, Inc.Inventors: David C. Graves, Ken Edward Kranz, James Kevin Millard, Lyle Frederick Albright
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Patent number: 5907072Abstract: A multi-stage process for treating n-paraffin feed is provided, including the steps of: (a) providing an n-paraffin feed; (b) contacting the n-paraffin feed with a dehydroisomerization catalyst under dehydroisomerization conditions so as to provide a dehydroisomerization product stream comprising n-paraffin, iso-paraffin, olefin and iso-olefin fractions; (c) mixing at least the iso-olefin fraction from the dehydroisomerization product stream with an alkyl alcohol to provide an etherification reaction feed; (d) contacting the etherification reaction feed with an etherification catalyst under etherification conditions so as to provide an etherification product stream comprising alkyl tert alkyl ether, n-paraffin, iso-paraffin and olefin fractions.Type: GrantFiled: December 2, 1997Date of Patent: May 25, 1999Assignee: Intevep, S.A.Inventor: Maria Magdalena Ramirez de Agudelo
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Patent number: 5877371Abstract: A solid state insoluble salt catalyst system for the carbocationic polymerization of olefin monomer in the presence of a polar or non-polar reaction medium, which comprises (a) solid state catalyst component comprising at least one salt of a strong acid and a carbocationically active transition metal selected from Groups III A, IV A, V A and VI A of the Periodic Table of Elements, wherein said salt is insoluble in the reaction medium; and (b) cocatalyst component effective for promoting the carbocationic polymerization.Type: GrantFiled: June 25, 1998Date of Patent: March 2, 1999Assignee: Exxon Chemical Patents Inc.Inventors: Frank Joung-Yei Chen, Herve Cheradame, Jon Edmond Stanat, Gerard Rissoan
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Patent number: 5841014Abstract: Disclosed are various embodiments for alkylating olefins and isoparaffins in the presence of an acid to reduce and/or control acid consumption or maximize and/or control the octane number of the produced alkylate product. One embodiment includes alkylation by controlling the C.sub.3 /C.sub.5 olefin ratio to reduce acid consumption. Another embodiment includes alkylation of C.sub.3 and C.sub.5 olefins in separate alkylation zones to maximize alkylate octane number. Even another embodiment includes propylene alkylation followed by C.sub.4 and/or C.sub.5 olefin alkylation, with the spent propylene acid used in the C.sub.4 and/or C.sub.5 olefin alkylation. Still another embodiment includes alkylation of C.sub.3, C.sub.4 and C.sub.5 olefins in separate alkylation zones, with the spent propylene acid used in the C.sub.4 alkylation, and the spent butylene acid used in the C.sub.5 alkylation. Yet another embodiment includes alkylation by controlling the C.sub.3 /C.sub.Type: GrantFiled: August 15, 1997Date of Patent: November 24, 1998Assignee: Stratco, Inc.Inventors: David Campbell Graves, Ken Edward Kranz, James Kevin Millard, Lyle Frederick Albright
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Patent number: 5672795Abstract: An etherification process combines an alkylation zone with a skeletal olefin isomerization zone in an arrangement that rejects isoalkanes and normal alkanes with only minor loss of valuable olefin isomers. The invention also provides a balanced feed to an alkylation zone for the production of high octane gasoline components. This invention can be used to provide ethers and gasoline boiling range alkylates from either C.sub.4 or C.sub.5 feedstocks. The invention fully utilizes all olefin isomers improve octane and vapor pressure charactristics of the gasoline components.Type: GrantFiled: September 25, 1995Date of Patent: September 30, 1997Assignee: UOPInventors: Bipin V. Vora, Tamotsu Imai, Peter R. Pujado
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Patent number: 5648586Abstract: A process is provided to react a feedstock comprising isobutane with pentenes in the presence of sulfuric acid catalyst to produce a high octane alkylate as well as a higher octane isopentane gasoline blending component. A method to reduce sulfuric acid consumption during alkylation is provided wherein a diolefinic contaminant of a pentene system feed is selectively hydrogenated before alkylation. An alkylation method is provided wherein the alkylation feed is separated into a fraction comprising substantially C.sub.4 and lower olefins and a fraction comprising substantially C.sub.5 olefins and the stream comprising C.sub.5 olefins is alkylated in a different reactor than the fraction comprising substantially C.sub.4 and lower olefins.Type: GrantFiled: September 5, 1995Date of Patent: July 15, 1997Assignee: Atlantic Richfield CompanyInventor: Vijay R. Sampath
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Patent number: 5649281Abstract: A process is provided to react a feedstock comprising isobutane with pentenes in the presence of sulfuric acid catalyst to produce a high octane alkylate as well as a higher octane isopentane gasoline blending component. A method to reduce sulfuric acid consumption during alkylation is provided wherein a diolefinic contaminant of a pentene system feed is selectively hydrogenated before alkylation. An alkylation method is provided wherein the alkylation feed is separated into a fraction comprising substantially C.sub.4 and lower olefins and a fraction comprising substantially C.sub.5 olefins and the stream comprising C.sub.5 olefins is alkylated in a different reactor than the fraction comprising substantially C.sub.4 and lower olefins.Type: GrantFiled: July 17, 1995Date of Patent: July 15, 1997Assignee: Atlantic Richfield CompanyInventor: Vijay R. Sampath
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Patent number: 5583275Abstract: Disclosed is an alkylation process in which C.sub.3 to C.sub.5 olefins are reacted with an isoparaffin mixture of isobutane and isopentane in the presence of a catalyst. Varying the amount of isopentane present in the mixture can control and/or eliminate the amount of isopentane produced in the alkylation reaction. The disclosed reaction has an improved alkylation yield, and also produces an alkylate having a lowered Reid Vapor Pressure and results in lowered olefin content for reformulated gasoline.Type: GrantFiled: August 19, 1994Date of Patent: December 10, 1996Assignee: Stratco, Inc.Inventors: Ken E. Kranz, James K. Millard
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Patent number: 5569788Abstract: A process is directed to the removal of impurities such as sulfur compounds, oxygenates, and/or olefins from a light paraffin hydrocarbon feedstock such as a C.sub.4 -C.sub.6 fraction, which may be used subsequently in an isomerization process in an integrated complex for the production of ethers such as MTBE and TAME. The hydrocarbon feedstream is passed to a removal zone wherein the hydrocarbon feedstream is contacted with a selective solvent for the removal of the impurities comprising at least one of sulfur compounds, oxygenates and olefins to provide a rich solvent stream and a treated hydrocarbon stream. The rich solvent comprising the trace impurities is contacted with a stripping medium stream to regenerate the selective solvent in a stripping zone. The removal zone may be a liquid-liquid extraction zone or a gas absorption zone.Type: GrantFiled: March 20, 1995Date of Patent: October 29, 1996Assignee: UOPInventors: Paulino Forte, Stanley J. Frey
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Patent number: 5523503Abstract: Hydrocarbons such as isobutane and benzenes are alkylated using a solid catalyst in a process which simulates the cocurrent movement of the catalyst bed versus the reactants. This has been found to greatly reduce the rate of catalyst deactivation compared to simulated countercurrent flow. The process may be performed using five or more beds of catalyst, with two undergoing regeneration at any one time. One bed is subjected to a short term liquid-phase regeneration while the other is subjected to long term vapor-phase regeneration. The catalyst preferably contains a metal hydrogenation function effective to selectively hydrogenate C.sub.6 -plus materials trapped on the used catalyst.Type: GrantFiled: July 13, 1994Date of Patent: June 4, 1996Assignee: UOPInventors: Gregory A. Funk, Simon H. Hobbs, Anil R. Oroskar, Stanley A. Gembicki, Joseph A. Kocal
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Patent number: 5481057Abstract: A process for catalytic cracking and C3/C4 olefin alkylation with phosphorus stabilized faujasite catalyst is disclosed. Catalytic cracking produces C3 and C4 olefins, which are alkylated using phosphorus stabilized and water activated cracking catalyst. Spent alkylation catalyst may be discharged into the FCC unit.Type: GrantFiled: March 25, 1994Date of Patent: January 2, 1996Assignee: Mobil Oil CorporationInventors: Weldon K. Bell, Tracy J. Huang, Rudolph M. Lago, Ying-Yen P. Tsao, D. Duayne Whitehurst
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Patent number: 5475175Abstract: This invention provides a process for upgrading hydrocarbon feedstock comprising the steps of:(i) recovering a C.sub.4 -rich aliphatic stream from a catalytic cracking process;(ii contacting said C.sub.4 -rich aliphatic stream with an isomerization catalyst comprising a zeolite sorbing 30 to 55 mg n-hexane at 90.degree. C., 83 torr, and 15 to 40 mg 3-methylpentane at 90.degree. C., 90 torr, per g dry zeolite in the hydrogen form in a first reaction stage to selectively isomerize C.sub.4 n-olefins to C.sub.4 isoolefins; and(iii) contacting the product stream from said first reaction stage with a solid acid alkylation catalyst selected from the group consisting of MCM-36 and MCM-49, as described herein and zeolites having a Constraint Index of less than or equal to about 2, to produce isoparaffinic alkylate gasoline.Type: GrantFiled: April 18, 1994Date of Patent: December 12, 1995Assignee: Mobil Oil CorporationInventors: Altaf Husain, Albin Huss, Jr., Iraj I. Rahmim
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Patent number: 5258560Abstract: Ethers suitable for use as high octane oxygenate additives for motor fuels are produced by a catalytic distillation process wherein a mixture of C.sub.4 -plus isoolefin(s) and an alcohol are recovered from a catalytic distillation zone as an overhead stream and charged to a packed liquid-phase reaction zone containing an etherification catalyst before being recycled to one or more portions of the overall catalytic distillation zone. The process is useful in the coprocessing of a mixture of isobutylene and isoamylene and in other hydrocarbon conversion processes such as hydration and alkylation.Type: GrantFiled: June 22, 1992Date of Patent: November 2, 1993Assignee: UOPInventor: Terry L. Marker
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Patent number: 5254748Abstract: A method for integrating several petroleum refining processes so as to efficiently produce tertiary alkyl ether compounds from a feed stream containing both saturated and unsaturated hydrocarbons is disclosed. An important step for forming isoolefins in the integrated process involves simultaneous catalytic conversion of an isoparaffin to an isoolefin and an n-olefin to an n-paraffin in a combination hydrogenation/dehydrogenation reactor. The thus produced isoolefin is reacted with a primary alcohol to form the desired tertiary alkyl ether compound in an ether forming process. Other conversion process included in the overall integration are an isomerization process to convert n-paraffins to isoparaffins and optionally an alkylation process to convert isoparaffins and olefins to an alkylate product.Type: GrantFiled: December 17, 1991Date of Patent: October 19, 1993Assignee: Phillips Petroleum CompanyInventors: Harvey D. Hensley, Richard L. Anderson, Michael E. Olbrich
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Patent number: 5254790Abstract: An integrated process for converting C.sub.4 /C.sub.5 hydrocarbons contained in a gasoline feedstock to more valuable motor fuel components includes various distillation steps, a hydroisomerization step, an etherification step (for producing t-amyl methyl ether), and an alkylation step. In a preferred embodiment, this process additionally includes a dehydrogenation step and a step of using formed debydrogenated hydrocarbons in the etherification step.Type: GrantFiled: July 1, 1992Date of Patent: October 19, 1993Assignee: Phillips Petroleum CompanyInventors: Gregory D. Thomas, Vernon A. Cawi
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Patent number: 5237115Abstract: A novel integrated olefin processing scheme is provided where olefins and paraffins are processed to produce high octane gasoline blending components. The integrated process involves the dehydrogenation of paraffin compounds to olefin compounds and the processing of olefins by hydroisomerization to produce hydroisomerate streams which are subsequently etherified. Those olefin compounds which are not etherified pass to an alkylation process where they are alkylated with branched chain paraffin compounds to produce an alkylate product.Type: GrantFiled: June 16, 1992Date of Patent: August 17, 1993Assignee: Phillips Petroleum CompanyInventors: Donald J. Makovec, Robert O. Dunn, Martyn E. Pfile, Gary R. Patton, Larry E. Lew
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Patent number: 5227534Abstract: A process for upgrading olefin feedstock containing a mixture of diene, iso-olefin and linear olefin to produce tertiary-alkyl ether and high octane gasoline components comprising iso-olefin. Product recovery is integrated between primary and secondary reaction stages.In a preferred embodiment, a two stage etherification process employs a secondary solid acid regenerable catalyst bed to etherify and/or oligomerize unconverted diene, and optionally, iso-butene in the debutanizer overhead stream of a conventional MTBE primary reactor stage. Both stages can utilize a regenerable acid catalyst such as ZSM-5 or Zeolite Beta for etherification and to upgrade unconverted alkenes and methanol from the primary stage.Type: GrantFiled: January 6, 1992Date of Patent: July 13, 1993Assignee: Mobil Oil CorporationInventor: Mohsen N. Harandi
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Patent number: 5023389Abstract: The invention relates to a process for preparing normally liquid hydrocarbon products such as middle distillates and methyl-t-butylether from a hydrocarbon feed containing linear and branched olefins (e.g. propane and butenes in light ends) comprising at least the following steps:i) selectively converting branched olefins in the feed in the presence of a catalyst into a normally liquid hydrocarbonaceous product (e.g. MTBE);ii) separating linear olefins from product obtained in step (i), andiii) catalytically oligomerizing linear olefins obtained from step (ii) into liquid hydrocarbons such as middle distillates.Type: GrantFiled: February 10, 1989Date of Patent: June 11, 1991Assignee: Shell Oil CompanyInventors: Pierre Grandvallet, Andras G. T. G. Kortbeek, Johannes P. Van Den Berg, Karl-Heinz Robschlager
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Patent number: 4918255Abstract: An improved process for alkylation of isoparaffins with olefins to yield a product which includes a high proportion of highly branched paraffins for making gasoline having improved octane is taught. The improved process comprises isomerizing the olefins and then contacting effluent and isoparaffins with a composite catalyst comprising a Lewis acid and a large pore zeolite and/or a non-zeolitic inorganic oxide. The beneficial effects of low temperature operation and the use of water in the process are also noted. The process results in reduced catalyst aging and obviates environmental problems associated with prior art processes.Type: GrantFiled: July 15, 1988Date of Patent: April 17, 1990Assignee: Mobil Oil Corp.Inventors: Tai-Sheng Chou, Albin Huss, Jr., Clinton R. Kennedy, Robert S. Kurtas
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Patent number: 4910357Abstract: A process selective for converting dimethylhexanes to aromatic analogs is described. Application of the exhibited selectivity of the process allows upgrading alkylate dimethylhexane(s) of low RON to produce higher RON analogs without affecting changes in other components of the alkylate. The catalysts preferred comprise platinum and non-acidic supports such as [Sn]ZSM-5 and [In]ZSM-5.Type: GrantFiled: June 24, 1988Date of Patent: March 20, 1990Assignee: Mobil Oil CorporationInventors: Ralph M. Dessau, Paul G. Rodewald
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Patent number: 4886925Abstract: An integrated process is disclosed for the conversion of C.sub.2 + normal olefins into methyl tertiaryalkyl ethers and high octane gasoline. The process combines olefins interconversion with etherification and conversion of unreacted methanol and olefins in contact with acidic, shape selective metallosilicate zeolite catalyst.Type: GrantFiled: May 2, 1988Date of Patent: December 12, 1989Inventor: Mohsen N. Harandi
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Patent number: 4868342Abstract: A process for the production of propylene and high octane blending components from C.sub.3 and C.sub.4 hydrocarbons that provides the dual benefit of flexibility between alkylate and propylene products while allowing the processing of large amounts of normal butane. The process includes the steps of passing a combined feed of C.sub.3 and C.sub.4 hydrocarbons to a dehydrogenation zone, contacting the feed stream with a dehydrogenation catalyst, and recovering an effluent containing C.sub.3 and C.sub.4 olefins and admixing the effluent with another feed comprising paraffins and olefins having from 3-4 carbon atoms and recovering an intermediate stream. The intermediate stream enters a separation zone, which removes C.sub.2 hydrocarbons and lower boiling materials from the process, recovers a first propylene product stream, produces an alkylation zone feed stream containing C.sub.3 and C.sub.4 hydrocarbons, and produces a recycle stream.Type: GrantFiled: March 4, 1988Date of Patent: September 19, 1989Assignee: UOPInventor: Ronald L. Verson
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Patent number: 4816607Abstract: A multistep hydrocarbon conversion process for the production of ethers including methyl tertiary butyl ether (MTBE) from light paraffins and alcohols is disclosed. A mixture of C.sub.4 isoparaffins, normal paraffins, an etherification recycle and butane isomerization effluent enter a deisobutanizer column. Normal paraffins withdrawn from the fractionator are isomerized and returned to the fractionator, and isoparaffins are withdrawn from the fractionator and dehydrogenated. The resulting olefins enter an etherification zone for reaction of isobutene with a C.sub.2 -C.sub.5 alcohol. Unreacted paraffins and olefins comprise a portion of the etherification effluent entering the deisobutanizer. After separation for recovery of the ether product, unreacted paraffins and olefins are passed through a dehydrogenation zone for saturation of the olefins and then returned to the deisobutanizer column. Normal butanes are withdrawn as a sidecut from the deisobutanizer.Type: GrantFiled: June 24, 1988Date of Patent: March 28, 1989Assignee: UOP Inc.Inventors: Bipin V. Vora, Peter R. Pujado, Richard E. Conser
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Patent number: 4777323Abstract: A continuous process for alkylating an alkylatable hydrocarbon in the presence of a acid-type catalyst. The reaction product is separated in a first separation zone into an alkylate product phase, located in the upper portion and a catalyst phase located in the lower portion. The catalyst phase is separated into a first portion and second portion, the first portion is cooled and recycled for use in the alkylation reaction zone, and the second portion is passed into a second separation zone, wherein the second portion catalyst phase is further separated into a hot rerun catalyst stream and an acid soluble oil stream. The rerun catalyst stream is passed into the alkylate product phase of the first separation zone. In order to prevent excessive pressure in the first separation zone as a result of the hot rerun catalyst stream, two liquid hydrocarbon drawoffs from the first separation zone are employed.Type: GrantFiled: July 19, 1985Date of Patent: October 11, 1988Assignee: Phillips Petroleum CompanyInventors: Paul D. Hann, Joe Van Pool
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Patent number: 4774375Abstract: A process using selective hydrogenation and HF alkylation in combination that employs a multifunction alkylation stripper for removal of light ends from the selective hydrogenation and a alkylation operations. The process combines the effluent from the selective hydrogenation operation, an isobutane feed stream and a bottoms stream from the HF stripper in the alkylation feed stripper. The feed stripper provides a C.sub.4 -plus bottoms stream that serves as the feed to the alkylation zone and a C.sub.3 -minus overhead that can be recovered as fuel gas. Significant benefit is obtained from this process when processing a mixed olefin feed of C.sub.3 /C.sub.4 hydrocarbons and recovering a high purity C.sub.3 product stream ahead of the selective hydrogenation zone. Another variation of this process allows a C.sub.3 product stream to be withdrawn from the alkylation feed stripper either directly as a sidecut or downstream of an overhead condensor.Type: GrantFiled: December 11, 1987Date of Patent: September 27, 1988Assignee: UOP Inc.Inventors: Harold U. Hammershaimb, Joel B. Spinner
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Patent number: 4767604Abstract: Alkylate is produced by catalytically converting oxygenate feedstock, such as methanol, to lower olefins comprising C.sub.2 -C.sub.4 olefins. Ethene is separated by interstage sorption of C.sub.3 + components and an isoparaffin is alkylated with C.sub.3 -C.sub.4 olefins derived from sorbate. The system comprises means for fractionating an olefinic feedstream containing ethene and C.sub.3 + olefinic components by contacting the olefinic feedstream in a sorption zone with a liquid hydrocarbon sorbent to selectively sorb C.sub.3.sup.+ components; means for reacting C.sub.3.sup.+ olefins with excess isoparaffin in a catalytic alkylation reactor to produce C.sub.7 + alkylate hydrocarbons; fractionating the alkylation reactor effluent to provide a liquid hydrocarbon fraction rich in C.sub.7.sup.+ alkylate. Liquid recycle or C.sub.5.sup.+ liquid coproduced with the lower olefin may be passed to the sorption zone as lean sorbent. C.sub.7.sup.+ alkylate product and C.sub.5.sup.Type: GrantFiled: October 15, 1986Date of Patent: August 30, 1988Assignee: Mobil Oil CorporationInventors: Hartley Owen, Samuel A. Tabak, Bernard S. Wright
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Patent number: 4761504Abstract: A process is disclosed for the simultaneous alkylation of light hydrocarbons to produce gasoline blending components and the etherification of an isoolefin to produce an ether. The etherification zone effluent stream contains normal olefins and isoparaffins consumed in an acid-catalyzed alkylation zone. The etherification zone effluent stream is separated in a fractionation column in a manner which provides a small amount of ether in the hydrocarbon-rich overhead stream. The presence of the ether in the acid-catalyst is beneficial to the alkylation reaction by providing a higher octane number product.Type: GrantFiled: December 29, 1986Date of Patent: August 2, 1988Assignee: UOP Inc.Inventor: Peter R. Pujado
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Patent number: 4754078Abstract: A multistep hydrocarbon conversion process for the production of ethers including methyl tertiary butyl ether (MTBE) from light paraffins and alcohols is disclosed. A mixture of C.sub.4 isoparaffins, normal paraffins, an etherification recycle and butane isomerization effluent enter a deisobutanizer column. Normal paraffins withdrawn from the fractionator are isomerized and returned to the fractionator, and isoparaffins are withdrawn from the fractionator and dehyrogenated. The resulting olefins enter an etherification zone for reaction of isobutene with a C.sub.2 -C.sub.5 alcohol. Unreacted paraffins and olefins comprise the etherification effluent entering the deisobutanizer. Normal butanes and olefins are withdrawn as a sidecut from the deisobutanizer. Hydrogenation of the sidecut saturates any olefins contained therein which would interfere with the isomerization of normal butanes.Type: GrantFiled: March 2, 1987Date of Patent: June 28, 1988Assignee: UOP Inc.Inventors: Bipin V. Vora, Peter R. Pujado, Richard E. Conser