With Hydrocarbon Recycle From Later To Earlier Synthesis Patents (Class 585/315)
  • Patent number: 5811608
    Abstract: A process for the production of saturated oligomers by the oligomerization of light olefins to heavier olefins and the saturation of the heavy olefins is improved by the recycle of the heavy paraffins to the oligomerization zone. The recycle of the heavy paraffins improves the selectivity of the oligomerization for C.sub.8 paraffin products and reduces catalyst fouling. The reduced catalyst fouling can be used to operate the oligomerization zone at lower pressure and facilitate its integration with a dehydrogenation zone for the production of the light olefin stream.
    Type: Grant
    Filed: December 15, 1995
    Date of Patent: September 22, 1998
    Assignee: UOP LLC
    Inventors: Laurence O. Stine, Brian S. Muldoon, Steven C. Gimre, Robert R. Frame
  • Patent number: 5763716
    Abstract: A process of converting a feed of hydrocarbon-containing gases into liquid hydrocarbon products including a first reaction of converting the feed into one to 2.5 parts of hydrogen to one part carbon monoxide in the presence of carbon dioxide and then secondly reacting the hydrogen and carbon monoxide in a Fischer-Tropsch synthesis reactor using a promoted iron oxide catalyst slurry to form liquid hydrocarbon products, wherein the carbon dioxide from the first and second reactions is separated from the product streams and at least a portion of the separated carbon dioxide is recycled into the first reaction feed and the hydrocarbon products are separated by distillation and a normally gaseous portion of the separated products are further reacted in another Fischer-Tropsch synthesis reactor to produce additional liquid hydrocarbon product.
    Type: Grant
    Filed: April 10, 1997
    Date of Patent: June 9, 1998
    Assignee: Rentech, Inc.
    Inventors: Charles B. Benham, Mark S. Bohn, Dennis L. Yakobson
  • Patent number: 5744670
    Abstract: A process for producing alkylnaphthalene from a feedstock comprising isomers of dialkylnaphthalene and naphthalene by contacting the feedstock with a catalyst composition, in which the process comprising transalkylation between isomers of dialkylnaphthalene and naphthalene to produce monoalkylnaphthalene, and isomerization of dialkylnaphthalene, wherein the catalyst composition comprising a synthetic zeolite characterized by an X-ray diffraction pattern including interplanar d-spacing as set forth in Table A of the specification.
    Type: Grant
    Filed: June 10, 1996
    Date of Patent: April 28, 1998
    Assignees: Kobe Steel, Ltd., Mobil Oil Corporation
    Inventors: Masahiro Motoyuki, Koji Yamamoto, John Paul McWilliams, Robert Glenn Bundens
  • Patent number: 5689015
    Abstract: A process for the production of ethers and alkylate from a paraffin feedstock. The process includes a novel arrangement of dehydrogenation, isomerization, separation, etherification and alkylation to provide such products.
    Type: Grant
    Filed: March 8, 1996
    Date of Patent: November 18, 1997
    Assignee: Phillips Petroleum Company
    Inventors: Harold R. Hunt, Mark D. Scharre, Warren M. Ewert
  • Patent number: 5602289
    Abstract: This invention relates to a process for converting alkoxy compounds into hydrocarbon compounds, mostly in the gasoline boiling range. This process proceeds with low heat exchange duty requirements for heating the alkoxy compounds and recycle streams used as feedstocks and for final cooling of reaction product gases for recovery of hydrocarbon product while at the same time offering an improved choice of operating conditions. As may be desired, steam may be added to obtain a desired final steam partial pressure in all catalyst contacts with the alkoxy compounds.
    Type: Grant
    Filed: November 9, 1994
    Date of Patent: February 11, 1997
    Assignee: Starchem, Inc.
    Inventor: Christiaan P. van Dijk
  • Patent number: 5563314
    Abstract: There is provided a process for the net catalytic oxidative dehydrogenation of alkanes to produce alkenes. The process involves simultaneous equilibrium dehydrogenation of alkanes to alkenes and combustion of the hydrogen formed to drive the equilibrium dehydrogenation reaction further to the product alkenes. In the present reaction, the alkane feed is dehydrogenated over an equilbrium dehydrogenation catalyst in a first reactor, and the effluent from the first reactor is then passed into a second reactor containing a reducible metal oxide which serves to selectively combust hydrogen in an oxidation/reduction (REDOX) reaction. This particular mode of operation is termed a separate reactor, REDOX mode.
    Type: Grant
    Filed: May 25, 1995
    Date of Patent: October 8, 1996
    Inventors: Pradyot A. Agaskar, Robert K. Grasselli, James N. Michaels, P. Thomas Reischman, David L. Stern, John G. Tsikoyiannis
  • Patent number: 5523502
    Abstract: A novel process having improved flexibility in olefins production is provided which integrates a deep catalytic cracking process with a steam cracking process, and optionally, also including steps of disproportionation and C.sub.4 hydrocarbon processing including methyl tertiary butyl ether synthesis.
    Type: Grant
    Filed: November 10, 1993
    Date of Patent: June 4, 1996
    Assignee: Stone & Webster Engineering Corp.
    Inventor: Jacob N. Rubin
  • Patent number: 5523508
    Abstract: Linear alpha-olefin formation via oligomerization of ethylene using transition metal catalysis leads to a Schultz-Flory distribution of oligomers. At modest temperatures formation of heavy oligomers which are waxy solids only partly soluble in the LAO product mix causes reactor plugging and curtailing the time of continuous runs. Recycling a portion of a lighter oligomeric fraction obviates this problem and permits runs uninterrupted by solids formation.
    Type: Grant
    Filed: December 29, 1994
    Date of Patent: June 4, 1996
    Assignee: UOP
    Inventors: Mark A. Krawczyk, Richard E. Marinangeli, R. Joe Lawson
  • Patent number: 5475175
    Abstract: 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: Grant
    Filed: April 18, 1994
    Date of Patent: December 12, 1995
    Assignee: Mobil Oil Corporation
    Inventors: Altaf Husain, Albin Huss, Jr., Iraj I. Rahmim
  • Patent number: 5434325
    Abstract: The present invention provides an alkylation process which is highly selective towards the production of para-tertiarybutylethylbenzene in high yield and in high para isomer content, while minimizing the development of unwanted by-products and impurities during the alkylation reaction. In accordance with the process, a feed stream mixture comprising the olefin alkylating agent and a molar excess of an aromatic hydrocarbon substrate is introduced into the inlet of a reactor zone and through a bed of active zeolite alkylation catalyst under alkylation conditions such that substantially all of the olefin reacts with the aromatic substrate to produce a mixture comprising the alkylated product and unreacted aromatic compound. This mixture is continuously withdrawn from the reactor zone as reactor effluent, after which the effluent is split into a product stream and recycle stream.
    Type: Grant
    Filed: July 20, 1994
    Date of Patent: July 18, 1995
    Assignee: Deltech Corporation
    Inventors: Shiou-Shan Chen, Joseph C. Peters
  • Patent number: 5430209
    Abstract: There is provided a process for the net catalytic oxidative dehydrogenation of alkanes to produce alkenes. The process involves simultaneous equilibrium dehydrogenation of alkanes to alkenes and combustion of the hydrogen formed to drive the equilibrium dehydrogenation reaction further to the product alkenes. In the present reaction, the alkane feed is dehydrogenated over an equilbrium dehydrogenation catalyst in a first reactor, and the effluent from the first reactor is then passed into a second reactor containing a reducible metal oxide which serves to selectively combust hydrogen in an oxidation/reduction (REDOX) reaction. This particular mode of operation is termed a separate reactor, REDOX mode.
    Type: Grant
    Filed: August 27, 1993
    Date of Patent: July 4, 1995
    Assignee: Mobil Oil Corp.
    Inventors: Pradyot A. Agaskar, Robert K. Grasselli, James N. Michaels, P. Thomas Reischman, David L. Stern, John G. Tsikoyiannis
  • Patent number: 5430210
    Abstract: There is provided a process for the selective combustion of hydrogen using a membrane structure containing metal oxides, such as bismuth oxide, that can selectively oxidize hydrogen in the presence of hydrocarbons by virtue of their lattice oxygen. A hydrocarbon/hydrogen containing gas and an oxygen-containing gas, such as air, are passed on separate sides of the membrane. The lattice oxygen is continuously being replenished by air oxidation. The selective hydrogen combustion reactor can be used in dehydrogenation processes as an interstage heater and as a hydrogen scavenger for olefin yield maximization.
    Type: Grant
    Filed: July 8, 1994
    Date of Patent: July 4, 1995
    Assignee: Mobil Oil Corporation
    Inventors: Robert K. Grasselli, John G. Tsikoyiannis
  • Patent number: 5414183
    Abstract: An improved process is disclosed for the removal of nitrogen compounds from light hydrocarbon streams. Such nitrogen removal enhances the performance of catalytic processes which upgrade light hydrocarbons, especially light olefins, such as isomerization and etherification. The nitrogen-removal process can usefully be combined with steps for removal of sulfur compounds and highly unsaturated compounds in a process combination for upgrading the light hydrocarbons.
    Type: Grant
    Filed: December 24, 1992
    Date of Patent: May 9, 1995
    Assignee: UOP
    Inventors: Hayim Abrevaya, Suleyman M. Ozmen, Paul T. Barger, Christopher D. Gosling, Thomas A. Verachtert
  • Patent number: 5406011
    Abstract: An improved process for the catalytic dehydrogenation of paraffinic hydrocarbons is disclosed. Feed paraffinic hydrocarbons are dehydrogenated by means of contacting the dehydrogenatable hydrocarbon with a dehydrogenation catalyst in a first dehydrogenation zone wherein the endothermic dehydrogenation reaction reduces the temperature of the resulting hydrocarbon stream containing dehydrogenated hydrocarbon compounds. The resulting effluent from the first dehydrogenation zone is then contacted with a stream of gas comprising normally gaseous hydrocarbon compounds having a temperature greater than the hydrocarbon stream to increase the temperature of the hydrocarbon stream and then introducing the resulting heated stream into a second dehydrogenation zone to produce additional dehydrogenated hydrocarbon compounds.
    Type: Grant
    Filed: April 6, 1994
    Date of Patent: April 11, 1995
    Assignee: UOP
    Inventors: William H. Radcliffe, Thomas R. Fritsch, Bipin V. Vora
  • Patent number: 5399787
    Abstract: In a process for producing tertiary alkyd ethers from an olefinic hydrocarbon feedstock, undesirable normal alkanes are removed from the process by passing at least a portion of a hydrocarbon process stream to an alkane isomerization zone to convert normal alkane to isoalkane and passing the alkane isomerization zone effluent to a separation zone to remove the isoalkane. Since no normal alkane is discharged from the process, the loss of valuable olefins, which have boiling points close to normal alkane, is prevented and olefins are retained in the process and converted to the appropriate tertiary alkyl ether. The result is an increase in the ether yield.
    Type: Grant
    Filed: September 20, 1993
    Date of Patent: March 21, 1995
    Assignee: UOP
    Inventors: Suleyman M. Ozmen, Paul J. Kuchar
  • Patent number: 5382731
    Abstract: There is provided a process for ring opening of aromatics or cycloaliphatics, as well as isomerization of aliphatics. The feedstream to this process comprises hydrocarbons having 6 carbon atoms. The process involves the use of a recycle stream containing a source of chlorine, such as carbon tetrachloride, and this process involves the use of at least two reactors connected in series. The first reactor comprises a ring opening catalyst and is operated under conditions which particularly promote ring opening. The catalyst in this first reactor may comprise zirconia modified with tungstate and platinum. A second, downstream reactor is operated under conditions to promote isomerization of aliphatics. The catalyst in the second reactor may comprise alumina, platinum and a chloride component. The catalysts in both the first and second reactors are chlorine resistant.
    Type: Grant
    Filed: July 22, 1993
    Date of Patent: January 17, 1995
    Assignee: Mobil Oil Corp.
    Inventors: Clarence D. Chang, Roy D. Bastian, Scott Han, Jose G. Santiesteban
  • Patent number: 5334792
    Abstract: There is provided a process for ring opening of aromatics and cycloaliphatics, as well as isomerization of aliphatics. The feedstream to this process comprises hydrocarbons having 6 carbon atoms. The process involves the use of at least two reactors connected in series. The first reactor contains a zeolite catalyst and is operated under conditions which particularly promote ring opening. The catalyst in this first reactor may comprise zeolite Beta and platinum. A downstream reactor is operated under conditions to promote isomerization of aliphatics. The catalyst in the second reactor may comprise alumina, platinum and a chloride component.
    Type: Grant
    Filed: October 9, 1992
    Date of Patent: August 2, 1994
    Assignee: Mobil Oil Corporation
    Inventors: Kenneth J. Del Rossi, David J. Dovedytis, David J. Esteves, Mohsen N. Harandi, Albin Huss, Jr.
  • Patent number: 5321177
    Abstract: Recently, as a process for manufacturing cyclopentadiene resin-shaped articles, an attention has been given to reaction injection molding (RIM). To conduct RIM, it is necessary to use high purity dicyclopentadiene (DCPD) as the raw material. Vapor-phase thermal cracking of DCPD is usually used as a step of process for manufacturing high purity DCPD. Hithertofore, when conducting thermal cracking of DCPD, coke formation within cracking tubes is the most serious and troublesome problem. A vapor-phase thermal cracking process for resolving the problem by a very simple procedure is described herein. Further, a process for manufacturing high purity DCPD suitable as a raw material for use in RIM utilizing the vapor-phase thermal cracking process just mentioned above is also described.
    Type: Grant
    Filed: April 16, 1992
    Date of Patent: June 14, 1994
    Assignee: Maruzen Petrochemical Co., Ltd.
    Inventors: Takao Nakamura, Masaru Kawakita, Katsumi Minomiya
  • Patent number: 5306854
    Abstract: The invention discloses a two step process for conversion of natural gas to liquid hydrocarbons of gasoline range comprising oxidation pyrolysis of natural gas olefins containing gaseous products in the first stage and conversion of the olefins, formed in the first step, without separating them from the gaseous product stream to liquid hydrocarbons of gasoline range in the second step. The process of the invention could be used in petrolium industries for producing gasoline liquid hydrocarbon fuels and aromatic hydrocarbons. The present invention is commercially viable and energy efficient.
    Type: Grant
    Filed: July 10, 1992
    Date of Patent: April 26, 1994
    Assignee: Council of Scientific & Industrial Research
    Inventors: Vasant R. Choudhary, Subhash D. Sansare, Amarjeet M. Rajput
  • Patent number: 5276231
    Abstract: An improved process for the production of alkylated aromatic compounds by paraffin dehydrogenation and aromatic alkylation is disclosed. Aromatic by-products normally formed in paraffin dehydrogenation are selectively removed using at least one aromatics removal zone. Removal of these aromatic by-products significantly reduces the deactivation rate of solid alkylation catalysts. The improved process produces a detergent alkylate product that is significantly more linear than that produced by the prior art process.
    Type: Grant
    Filed: July 27, 1992
    Date of Patent: January 4, 1994
    Assignee: UOP
    Inventors: Joseph A. Kocal, Donald J. Korous
  • Patent number: 5254748
    Abstract: 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: Grant
    Filed: December 17, 1991
    Date of Patent: October 19, 1993
    Assignee: Phillips Petroleum Company
    Inventors: Harvey D. Hensley, Richard L. Anderson, Michael E. Olbrich
  • Patent number: 5243113
    Abstract: An economically advantageous process for preparing 2-methylnaphthalene is provided. The process comprises the steps of azeotropically distilling a 1-methylnaphthalene-containing oil with ethylene glycol to produce a denitrified oil; subjecting the denitrified oil to an isomerization to promote an isomerization from 1-methylnaphthalene to 2-methylnaphthalene and produce an isomerization product; and recovering 2-methylnaphthalene from the isomerization product. The process may further comprise the step of hydrodesulfurizing or hydrogenating a portion or all of the denitrified oil to produce a hydrodesulfurized or hydrogenated product so that the product alone or the product together with the non-hydrodesulfurized or hydrogenated oil can be subjected to the subsequent isomerization step. Catalytic life of the isomerization catalyst is markedly prolonged to enable a production of 2-methylnaphthalene at a high yield.
    Type: Grant
    Filed: August 10, 1992
    Date of Patent: September 7, 1993
    Assignee: Kawasaki Steel Corporation
    Inventors: Tatsuya Nobusawa, Yoshinori Takagi, Toshihide Suzuki, Tsugio Horita
  • Patent number: 5235120
    Abstract: A process combination is disclosed to selectively upgrade naphtha to obtain products suitable for further upgrading to reformulated fuels. A naphtha feedstock is hydrogenated to saturate aromatics, followed by selective isoparaffin synthesis to yield light and heavy naphtha and isobutane. The heavy naphtha may be processed by reforming, light naphtha may be isomerized, and isobutane may be upgraded by dehydrogenation, etherification and/or alkylation to yield gasoline components from the process combination suitable for production of reformulated gasoline.
    Type: Grant
    Filed: November 21, 1991
    Date of Patent: August 10, 1993
    Assignee: UOP
    Inventors: Paula L. Bogdan, R. Joe Lawson, J. W. Adriaan Sachtler
  • Patent number: 5210350
    Abstract: A method of preparing an alkylated aromatic product (12) by alkylation of an aromatic compound (1), the alkylation producing several alkylated aromatic products, this method being characterized by the following points:(a) the aromatic compound (1) is reacted with an alkylating agent (2) in the presence of an alkylation zeolite (4);(b) the alkylated aromatic product (12) is separated by crystallization from the products of the alkylation;(c) the uncrystallized part (13) of the alkylated aromatic products is subjected to a dealkylation in the presence of a dealkylation zeolite (15);(d) the regenerated aromatic compound (1.sub.b) is recycled in order to react it again with the alkylating agent (2) in the presence of the alkylation zeolite (4). Alkylated aromatic compounds (12) obtained by this method, in particular 2-6 dicyclohexyl naphthalene.
    Type: Grant
    Filed: March 11, 1991
    Date of Patent: May 11, 1993
    Assignee: Michelin Recherche et Technique
    Inventors: Jonis Solofo, Patrice Moreau, Patrick Geneste, Annie Finiels
  • Patent number: 5177114
    Abstract: This invention comprises a method for converting natural gas to a normally liquid carbon containing compound, such as methanol and/or dimethyl ether and/or to gasoline grade liquid hydrocarbons and/or olefins. The method of this invention eliminates the need for steam reforming and/or adiabatic reforming with essentially pure oxygen of the natural gas to a synthesis gas. In accordance with the process of this invention, a synthesis gas may be produced at an operating pressure suitable for conversion thereof to methanol and/or dimethyl ether without the need for synthesis gas recompression. Further, the vent or bleed gas from the overheads after conversion to the crude product methanol/DME and/or its conversion to gasoline grade liquid hydrocarbons, generally has a BTU capacity required to serve as a fuel gas for supplying the energy needed for operation of a gas turbine which powers the gas compression equipment requirements by which the process of this invention may be practiced.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: January 5, 1993
    Assignee: Starchem Inc.
    Inventors: Christiaan P. Van Dijk, Lowell D. Fraley
  • Patent number: 5177279
    Abstract: An integrated process for the conversion of methanol feed to gasoline and distillate range liquid hydrocarbons comprising the steps of splitting the methanol feed into two portions, contacting the first portion of the methanol feed with a medium-pore shape selective zeolite catalyst in a first reaction zone at elevated temperature and moderate pressure to convert the first portion of the methanol feed to hydrocarbons comprising C.sub.2 + olefins; cooling and separating effluent from the first reaction zone to recover a C.sub.3 + olefin hydrocarbon stream and a C.sub.2 - light gas stream; pressurizing the C.sub.3 + olefin hydrocarbon stream and the second portion of the methanol feed and contacting the C.sub.3 + hydrocarbon stream and the methanol feed in a second reaction zone with a medium-pore shape selective oligomerization zeolite catalyst at substantially increased pressure and moderate temperature to convert at least a portion of the C.sub.
    Type: Grant
    Filed: October 1, 1991
    Date of Patent: January 5, 1993
    Assignee: Mobil Oil Corporation
    Inventor: Mohsen N. Harandi
  • Patent number: 5166455
    Abstract: A process has been discovered for the conversion of C.sub.5 -C.sub.7 olefinic hydrocarbons, such as those contained in FCC light naphtha, to iso-butene-rich and isoamylene-rich streams in an integrated process for the production of MTBE and TAME. The process involves the initial separation of the isoamylene-rich C.sub.5 -fraction of the feedstream which is converted to TAME. The C.sub.6 -C.sub.7 fraction plus unreacted C.sub.5 's are converted by olefin interconversion with medium pore zeolite catalyst into an isobutylene and isoamylene-rich stream which is then used as feedstream for etherification to MTBE and TAME.
    Type: Grant
    Filed: January 16, 1992
    Date of Patent: November 24, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Arthur A. Chin, Frederick J. Krambeck, Stephen S. Wong, Sergei Yurchak
  • Patent number: 5146032
    Abstract: An integrated process comprising the steps of pressurizing a C.sub.3.sup.+ olefin hydrocarbon stream and a methanol feed and contacting the C.sub.3.sup.+ hydrocarbon stream and methanol feed in a first reaction zone with a medium-pore shape selective oligomerization zeolite catalyst at elevated pressure and moderate temperature to convert at least a portion of the C.sub.3.sup.+ hydrocarbons and methanol feed to heavier liquid hydrocarbon product stream comprising olefinic gasoline and distillate range liquids. An ethene stream and a stream containing unreacted methanol and water are recovered from the first reaction zone effluent and the methanol is separated from the water.The ethene and the separated unreacted methanol are contacted with a medium-pore shape selective zeolite catalyst in a second reaction zone at elevated temperature and moderate pressure to convert the methanol feed to hydrocarbons comprising C.sub.3.sup.+ olefins and cooling effluent from the second reaction zone to recover a C.sub.3.sup.
    Type: Grant
    Filed: December 12, 1991
    Date of Patent: September 8, 1992
    Assignee: Mobil Oil Corporation
    Inventor: Mohsen N. Harandi
  • Patent number: 5110446
    Abstract: The present invention provides a process for decreasing the energy consumption of a catalytic cracking process product recovery section while improving gasoline yield by integrating multistage vapor compression and product recovery with deacidification and conversion of C.sub.2 -C.sub.4 aliphatics to C.sub.5 + normally liquid hydrocarbons.
    Type: Grant
    Filed: September 7, 1990
    Date of Patent: May 5, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Mohsen N. Harandi, Hartley Owen
  • Patent number: 5059744
    Abstract: An improved olefin upgrading technique and fixed-bed reactor system has been developed for increasing production of premium heavy hydrocarbons, such as distillate fuel, from lower olefinic feedstock. During recovery and recycle of intermediate range hydrocarbons products, a technique has been found for withdrawing a fraction rich in C.sub.5 -C.sub.9 gasoline range olefinic hydrocarbons from the oligomerization reactor effluent stream. By separating the reaction effluent in a multi-stage distillation system, fractionation feed can be separated into a heavier bottoms stream rich in C.sub.10 + hydrocarbons and a light hydrocarbon overhead, while withdrawing a liquid stream as an overflash fractionation stream rich in intermediate hydrocarbons. The overflash stream is combined to form a portion of the recycle stream to the reactor, thereby providing a more efficient and lower cost recovery process.
    Type: Grant
    Filed: September 29, 1989
    Date of Patent: October 22, 1991
    Assignee: Mobil Oil Corporation
    Inventors: Moshen N. Harandi, Hartley Owen
  • Patent number: 5041690
    Abstract: Methanol or other alcohol is converted to high octane gasoline components by an integrated process wherein crude aqueous alcohol feedstock is extracted with a liquid extractant stream containing C.sub.4 +iso-olefin and reacted to form tertiary-alkyl ethers, such as MTBE. The aqueous raffinate is converted to olefinic hydrocarbons in a MTO catalytic reactor. Propene from the MTO reaction is reacted with water to produce di-isopropyl ether, which may be blended with MTBE and C.sub.6 +MTO hydrocarbons to produce high octane gasoline. Isobutylene and isoamylenes from the MTO reaction can be recovered and recycled as a liquid extractant stream.
    Type: Grant
    Filed: August 3, 1990
    Date of Patent: August 20, 1991
    Assignee: Mobil Oil Corporation
    Inventors: Mohsen N. Harandi, Hartley Owen
  • Patent number: 5026935
    Abstract: The present invention provides a process for the preparation of ethylene from C.sub.4 or higher feed by a combination of cracking and metathesis wherein higher hydrocarbon is cracked to form ethylene and propylene and at least a portion of the propylene is metathesized to ethylene.
    Type: Grant
    Filed: October 2, 1989
    Date of Patent: June 25, 1991
    Assignee: Arco Chemical Technology, Inc.
    Inventors: David W. Leyshon, John A. Sofranko, C. Andrew Jones
  • Patent number: 5026936
    Abstract: The present invention provides a process for the preparation of propylene from C.sub.4 or higher feed by a combination of cracking and metathesis wherein higher hydrocarbon is cracked to form ethylene and propylene and at least a portion of the ethylene is metathesized to propylene.
    Type: Grant
    Filed: October 2, 1989
    Date of Patent: June 25, 1991
    Assignee: Arco Chemical Technology, Inc.
    Inventors: David W. Leyshon, John A. Sofranko, C. Andrew Jones
  • Patent number: 5023389
    Abstract: 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: Grant
    Filed: February 10, 1989
    Date of Patent: June 11, 1991
    Assignee: Shell Oil Company
    Inventors: Pierre Grandvallet, Andras G. T. G. Kortbeek, Johannes P. Van Den Berg, Karl-Heinz Robschlager
  • Patent number: 5012021
    Abstract: An improved process for the production of alkylaromatic hydrocarbons is disclosed. Paraffinic hydrocarbons are dehydrogenated to yield an olefin-containing stream, which is later charged to an alkylation zone for reaction with an aromatic hydrocarbon in the presence of a solid alkylation catalyst. The olefin-containing stream is first passed through a selective hydrogenation zone in which diolefins are converted to monoolefins by contact with a selective catalyst. This increases the yield and the quality of the product alkylate by greatly reducing the production of biphenyl compounds and oligomers in the alkylation zone. Process efficiency is improved by passing unconverted paraffinic and monoolefinic hydrocarbons from the alkylation zone through another hydrogenation zone for the saturation of monoolefinic hydrocarbons and recycling the saturated stream to the dehydrogenation zone.
    Type: Grant
    Filed: September 18, 1990
    Date of Patent: April 30, 1991
    Assignee: UOP
    Inventors: Bipin V. Vora, Paul R. Cottrell
  • Patent number: 5008467
    Abstract: An integrated process of producing MTBE by the dehydrogenation of isobutane and the etherification of the resulting isobutene with methanol is simplified by directly charging the effluent of a dehydrogenation zone without prior separation to an etherification zone arranged to provide countercurrent contact of isobutene and the methanol reactants such that an MTBE product is recovered as a bottoms stream and a relatively isobutene-free overhead stream is recycled to the dehydrogenation zone. Overall separation facilities are simplified by only separating C.sub.3 hydrocarbons from the etherification zone product stream. This arrangement eliminates C.sub.3 separation facilities ahead of the etherification zone and reduces the quantity of C.sub.4 hydrocarbons that are received by the separation zone. The reaction zone may contain a series of beds arranged to further eliminate the carry over of isobutene to the separation facilities. This arrangement also allows a recovery of unreactive or unreacted C.sub.
    Type: Grant
    Filed: December 4, 1989
    Date of Patent: April 16, 1991
    Assignee: UOP
    Inventors: Bipin V. Vora, Norman H. Scott
  • Patent number: 4990712
    Abstract: Gasoline octane number and yield are improved while excess fuel gas production is decreased in a catalytic cracking process by integrating etherification and oxygenate/aliphatic upgrading processes into the catalytic cracking unit product fractionation section.
    Type: Grant
    Filed: May 18, 1990
    Date of Patent: February 5, 1991
    Assignee: Mobil Oil Corporation
    Inventors: Mohsen N. Harandi, Hartley Owen
  • Patent number: 4962249
    Abstract: Near linear higher olefinic hydrocarbons produced by the oligomerization of lower olefins using surface deactivated zeolite catalyst can be converted to a mixture comprising slightly branched and linear higher alpha olefins. These alpha olefins are oligomerized to lubricant grade hydrocarbons in contact with cationic, Ziegler or coordination catalyst. Oligomerization of the aforementioned alpha olefins using reduced valence state Group VIB metal oxide catalyst on porous support provides a hydrocarbon lubricant with a viscosity index of greater than 130 at 100.degree. C.
    Type: Grant
    Filed: February 15, 1990
    Date of Patent: October 9, 1990
    Assignee: Mobil Oil Corporation
    Inventors: Catherine S. H. Chen, Margaret M. S. Wu
  • Patent number: 4935568
    Abstract: A continuous multistage process for preparing gasoline and/or distillate range hydrocarbons from lower molecular weight oxygenate feedstock wherein hydrocarbon yield is increased by recovering a vapor stream rich in ethene from an oxygenates conversion stage and reacting the ethene in a high severity reaction zone containing high activity zeolite catalyst.
    Type: Grant
    Filed: December 5, 1988
    Date of Patent: June 19, 1990
    Assignee: Mobil Oil Corporation
    Inventors: Mohsen N. Harandi, Hartley Owen
  • Patent number: 4906788
    Abstract: A combined process for the dehydrogenation of C.sub.4 -C.sub.5 paraffins in a first zone and the etherification of olefins in a second zone improves efficiency by directly charging all but the lightest components of the dehydrogenation zone effluent to the etherification zone. This process is particularly suited for the production of gasoline boiling range ethers where an isoparaffin is dehydrogenated in a first zone to produce isoolefins. After separation of hydrogen and methane, the dehydrogenation zone effluent is charged along with methanol to an etherification zone for the production of MTBE. The etherification zone effluent is separated into at least three component streams comprising light ends, isoparaffins, and the ether product. Isoparaffins, separated from the etherification zone effluent, are recycled and combined with the feed to dehydrogenation zone.
    Type: Grant
    Filed: October 26, 1988
    Date of Patent: March 6, 1990
    Assignee: UOP
    Inventors: Norman H. Scott, Bipin V. Vora
  • Patent number: 4891457
    Abstract: A staged reactor technique for converting ethene-rich olefinic feedstock to heavier hydrocarbons, particularly gasoline and distillate range products. By employing low temperature and high temperature separators, an economic recycle is provided for each stage.
    Type: Grant
    Filed: September 13, 1985
    Date of Patent: January 2, 1990
    Inventors: Hartley Owen, Bernard S. Wright
  • Patent number: 4879428
    Abstract: An improved olefin upgrading technique has been developed for increasing production of premium heavy hydrocarbons, such as distillate fuel, from lower olefinic feedstock. During recovery and recycle of intermediate range hydrocarbons products, a process has been found for withdrawing a fraction rich in C.sub.5 -C.sub.9 gasoline range olefinic hydrocarbons from the oligomerization reactor effluent stream. By separating the reaction effluent in a multistage distillation system, fractionation feed can be separated into a heavier bottoms stream rich in C.sub.10+ hydrocarbons and a light hydrocarbon overhead, while withdrawing a liquid stream as an overflash fractionation stream rich in intermediate hydrocarbons. The overflash stream is combined to form a portion of the recycle stream to the reactor, thereby providing a more efficient and lower cost recovery process.
    Type: Grant
    Filed: March 3, 1988
    Date of Patent: November 7, 1989
    Inventors: Mohsen N. Harandi, Hartley Owen
  • Patent number: 4849562
    Abstract: The oxychlorination process for producing ethylene dichloride is carried out by reacting ethylene with hydrogen chloride and oxygen in an oxychlorination reactor. Thereby, ethyl chloride and perhaps vinyl chloride are produced as by-products. The effluent from the reactor is at least fractionated into an ethylene dichloride-rich fraction (I) and an ethyl chloride-rich fraction (II) so that fraction (I) contains less than 50 percent of the total weight of ethyl chloride produced in step (a) and the sum of the weight of ethylene dichloride and vinyl chloride in fraction (II) is less than 30 percent of the weight of ethyl chloride in fraction (II). The ethyl chloride-rich fraction (II) is subjected to a cracking reaction in the presence or absence of an inert diluent wherein ethyl chloride is converted into ethylene and hydrogen chloride in the presence of a catalyst.
    Type: Grant
    Filed: August 26, 1988
    Date of Patent: July 18, 1989
    Assignee: The Dow Chemical Company
    Inventors: Christoph Buhs, Eberhard Dreher, Garnet E. McConchie
  • Patent number: 4832919
    Abstract: A heat balanced system for converting an olefinic feedstock comprising ethylene and C.sub.3.sup.+ olefins to heavier liquid hydrocarbon product in a catalytic exothermic process. Means are provided for prefractionating the olefinic feedstock to obtain a gaseous stream rich in ethylene and a liquid stream containing C.sub.3.sup.+ olefin, and a reactor for contacting an olefinic feedstock stream from the prefractionating step with ZSM-5 type oligomerization catalyst in a series of exothermic catalytic reactors to provide a heavier hydrocarbon effluent stream comprising distillate, gasoline and lighter hydrocarbons. In a preferred embodiment a catalytic system is provided for making gasoline or diesel fuel from an olefinic feedstock containing ethylene and C.sub.3.sup.+ lower olefins comprising a prefractionation system for separating and recovering ethylene and a liquid stream rich in C.sub.3.sup.
    Type: Grant
    Filed: March 26, 1984
    Date of Patent: May 23, 1989
    Assignee: Mobil Oil Corporation
    Inventors: Bernard S. Wright, Hartley Owen, Chung H. Hsia
  • Patent number: 4808764
    Abstract: A process for introducing a exothermic reactant vapor stream to an adiabatic catalyst zone comprising the steps of: preheating a volatile liquid exothermic reactant stream below its autogenous temperature under process pressure; contacting the preheated liquid reactant stream in a saturator unit with a hot diluent gas to vaporize the reactant stream in gaseous mixture with the diluent stream; directing the gaseous mixture from the saturator unit to the catalyst zone for exothermic conversion of the reactant under substantially adiabatic reaction conditions in the presence of diluent gas; recovering reaction products and diluent gas from the catalyst zone; separating diluent gas from the products, compressing and recycling the diluent gas to the saturator unit.
    Type: Grant
    Filed: April 13, 1983
    Date of Patent: February 28, 1989
    Assignee: Mobil Oil Corporation
    Inventors: Dietmar R. A. Fremuth, Alan E. Rogers, John C. Zahner
  • Patent number: 4788366
    Abstract: A multi-stage catalytic olefin upgrading technique for converting lower olefinic feedstock to heavier liquid hydrocarbon product.
    Type: Grant
    Filed: December 28, 1987
    Date of Patent: November 29, 1988
    Assignee: Mobil Oil Corporation
    Inventors: Mohsen N. Harandi, Hartley Owen, Samuel A. Tabak
  • Patent number: 4788365
    Abstract: An integrated process for the conversion of methanol to high octane gasoline and distillate. Methanol is converted to olefins in the presence of zeolite type catalyst. C.sub.4 and C.sub.5 olefin fraction is converted to MTBE and TAME in the presence of excess methanol and acid etherification catalyst. Unreacted methanol and hydrocarbons are passed to an olefins to gasoline and distillate oligomerization unit in conjunction with C.sub.3, C.sub.6 and C.sub.7 olefins from the methanol to olefins unit whereby distillate and LPG products are produced. Gasoline products from the oligomerization unit are passed to the etherification unit whereby an ether-rich gasoline fraction is separated.
    Type: Grant
    Filed: December 8, 1987
    Date of Patent: November 29, 1988
    Assignee: Mobil Oil Corporation
    Inventors: Mohsen N. Harandi, Hartley Owen
  • Patent number: 4774376
    Abstract: This invention relates to a process for producing liquid products e.g. gasoline blending components by conversion of a mixed paraffin/olefin gaseous feedstock over two types of catalysts. In a first stage, the mixed feedstock is brought into contact with a partially deactivated catalyst which converts olefins in the feed into liquid products. Gaseous products now rich in paraffins are separated and brought into contact in a second stage with another catalyst which is more active than that used in the first stage. The liquid products emerging from the second stage are thereafter separated and recovered. The catalyst is preferably a gallium oxide loaded MFI type zeolite.
    Type: Grant
    Filed: May 3, 1985
    Date of Patent: September 27, 1988
    Assignee: The British Petroleum Company, p.l.c
    Inventor: Antony H. P. Hall
  • Patent number: 4755627
    Abstract: Diisopropenylbenzene is a monomer that can be used in the preparation of many useful polymers and is also a chemical intermediate that can be employed in a number of chemical processes. Diisopropenylbenzene is normally synthesized by the dehydrogenation of diisopropylbenzene. Unfortunately in this dehydrogenation process a number of olefinic impurities are produced as by-products. This invention discloses a process for the separation of diisopropenylbenzene from these impurities and for recycling some of the impurities.
    Type: Grant
    Filed: November 24, 1986
    Date of Patent: July 5, 1988
    Assignee: The Goodyear Tire & Rubber Company
    Inventors: Howard A. Colvin, Ronald D. Fiedler, Joel Muse, Jr., Donald E. Smith
  • Patent number: 4754092
    Abstract: A process for reducing methane formation and increasing liquid (C.sub.5.sup.+) yields in Fischer-Tropsch hydrocarbon synthesis processes of CO and H.sub.2 comprising adding one or more olefins to the reactor bed at a point below 10% of the distance from the top to the bottom of the reactor bed and above a point 10% above the bottom of the reactor bed to the top of the reactor bed in an amount sufficient to reduce said methane formation.
    Type: Grant
    Filed: December 22, 1986
    Date of Patent: June 28, 1988
    Assignee: Exxon Research and Engineering Company
    Inventors: Enrique Iglesia, Rostam Madon