Including Alkylation To Produce Branched-chain Paraffin Patents (Class 585/331)
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Patent number: 11724972Abstract: Processes for the direct alkylation of ethylene with isobutane or isopentane using a highly active ionic liquid alkylation catalyst are described. Ethylene is sent to a high-temperature alkylation reactor loop, and C3, C4, and C5 olefins are routed to a low temperature alkylation reactor loop. In each reactor, the olefins are contacted with an excess of isobutane or isopentane in the presence of a highly active ionic liquid catalyst. Portions of the reactor effluent streams are fed to a common downstream catalyst separation and product fractionation sections. The remainder of the reactor effluent is recycled back to the respective alkylation reactor.Type: GrantFiled: September 28, 2022Date of Patent: August 15, 2023Assignee: UOP LLCInventors: Matthew C. Cole, Dominic P. Weber, Rajeswar R. Gattupalli, Hye Kyung Timken, Huping Luo, Bong Kyu Chang, Rebecca Mudrock
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Patent number: 11530172Abstract: Methods and systems for steam cracking a mixed butane containing feed stream are disclosed. The feed stream includes n-butane and isobutane. The disclosed methods and systems entail splitting the feed into an enriched n-butane fraction and an enriched isobutane fraction. The enriched n-butane fraction is provided to the cracking furnaces, which yield the olefin products and also yield C4 species. The C4 species are partially hydrogenated and provided as a reactant feed to an alkylation reaction. The enriched isobutane fraction is also provided to the alkylation reaction, whereby high value alkylate product is produced. The disclosed methods and systems have increase olefins (especially ethylene) yield because the feed to the cracking process is enriched in n-butane. The economics are also improved because high value alkylate product is produced from a portion of the isobutane.Type: GrantFiled: November 18, 2020Date of Patent: December 20, 2022Assignee: KELLOGG BROWN & ROOT LLCInventors: Rian Reyneke, Hendrik Wolterus Klavers
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Patent number: 11130914Abstract: The present invention provides methods, reactor systems and catalysts for converting biomass and biomass-derived feedstocks to C8+ hydrocarbons using heterogenous catalysts. The product stream may be separated and further processed for use in chemical applications, or as a neat fuel or a blending component in jet fuel and diesel fuel, or as heavy oils for lubricant and/or fuel oil applications.Type: GrantFiled: March 2, 2020Date of Patent: September 28, 2021Assignee: VIRENT, INC.Inventors: Paul G. Blommel, Brice Dally, Warren Lyman, Randy D. Cortright
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Patent number: 10737989Abstract: The present invention relates to the integration of an alkylation unit for use in a hydrocarbon conversion process. More specifically, the present invention relates to the integration of a dehydrogenation unit and an alkylation unit and the placement of different isomerization units located off the deisobutanizer and the debutanizer.Type: GrantFiled: April 18, 2019Date of Patent: August 11, 2020Assignee: UOP LLCInventors: Charles P. Luebke, Raul Zavala, Christopher D. DiGiulio
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Patent number: 10294173Abstract: The present invention relates to the integration of an alkylation unit for use in a hydrocarbon conversion process. More specifically, the present invention relates to the integration of a dehydrogenation unit and an alkylation unit and the placement of different isomerization units located off the deisobutanizer and the debutanizer.Type: GrantFiled: May 31, 2018Date of Patent: May 21, 2019Assignee: UOP LLCInventors: Charles P. Luebke, Raul Zavala, Christopher D. DiGiulio
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Patent number: 10179753Abstract: Methods of simultaneously converting butanes and methanol to olefins over Ti-containing zeolite catalysts are described. The exothermicity of the alcohols to olefins reaction is matched by endothermicity of dehydrogenation reaction of butane(s) to light olefins resulting in a thermo-neutral process. The Ti-containing zeolites provide excellent selectivity to light olefins as well as exceptionally high hydrothermal stability. The coupled reaction may advantageously be conducted in a staged reactor with methanol/DME conversion zones alternating with zones for butane(s) dehydrogenation. The resulting light olefins can then be reacted with iso-butane to produce high-octane alkylate. The net result is a highly efficient and low cost method for converting methanol and butanes to alkylate.Type: GrantFiled: October 21, 2016Date of Patent: January 15, 2019Assignee: Exelus, Inc.Inventors: Mitrajit Mukherjee, Vamsi M. Vadhri, Narendra Joshi
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Patent number: 9302951Abstract: A process for producing dimethylhexanes (DMH) is provided. The DMH can be used to produce p-xylene. The process involves the alkylation of isobutane and 1-butene using an ionic liquid to produce naphtha that is rich in DMH. The DMH is then converted in high selectivity to xylene, including p-xylene, by dehydrocyclization.Type: GrantFiled: January 30, 2014Date of Patent: April 5, 2016Assignee: UOP LLCInventors: Carl J. Stevens, Susie C. Martins, Paul T. Barger
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Patent number: 9233886Abstract: The present invention (in a first embodiment) relates to a process for the simultaneous dehydration and skeletal isomerization of isobutanol to make substantially corresponding olefins, having the same number of carbons and consisting essentially of a mixture of n-butenes and iso-butene, said process comprising: a) introducing in a reactor a stream (A) comprising isobutanol, optionally water, optionally an inert component, b) contacting said stream with a catalyst in said reactor at conditions effective to dehydrate and skeletal isomerize at least a portion of the isobutanol to make a mixture of n-butenes and iso-butene, c) recovering from said reactor a stream (B), removing water, the inert component if any and unconverted isobutanol if any to get a mixture of n-butenes and iso-butene, Wherein, the WHSV of the isobutanol is at least 1 h?1 or the temperature is from 200° C. to 600° C. and the catalyst is capable to make simultaneously the dehydration and skeletal isomerization of butene.Type: GrantFiled: March 15, 2011Date of Patent: January 12, 2016Assignee: Total Research & Technology FeluyInventors: Cindy Adam, Delphine Minoux, Nikolai Nesterenko, Sander Van Donk, Jean-Pierre Dath
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Patent number: 9193919Abstract: The invention relates to a process for hydrodeoxygenation (HDO) of pyrolysis oil and also to a process for upgrading of pyrolysis oil implementing said HDO process, and also to processing of the aqueous phase resulting from the HDO by steam pre-reforming and then steam reforming.Type: GrantFiled: November 21, 2011Date of Patent: November 24, 2015Assignee: TOTAL RAFFINAGE MARKETINGInventors: Vincent Mayeur, Alexandre Preau
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Publication number: 20150025285Abstract: Processes for eliminating oxygenates and water from a light hydrocarbon processing system, wherein oxygenates are removed from a light hydrocarbon stream by adsorption of the oxygenates on an oxygenate adsorption unit to provide a deoxygenated hydrocarbon stream, the oxygenate adsorption unit is regenerated via a regenerant stream to provide an oxygenated regenerant stream comprising the oxygenates, and the oxygenated regenerant stream is subjected to hydro-deoxygenation to convert the oxygenates into paraffins and water, wherein the water may also be permanently removed from the system.Type: ApplicationFiled: July 17, 2013Publication date: January 22, 2015Applicant: Chevron U.S.A. Inc.Inventors: Robert Fletcher Cleverdon, Clifford Michael Lowe, Hye Kyung Cho Timken
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Publication number: 20140357915Abstract: We provide a catalytic process to reduce an organic halide in a hydrocarbon, comprising: a. producing the hydrocarbon comprising the organic halide in a process unit; and b. contacting the hydrocarbon comprising the organic halide with a metal chloride under anhydrous conditions in a halide removal vessel to produce a contacted hydrocarbon having from 50-100 wt % of a total halide in the hydrocarbon removed. We also provide an apparatus for performing this process.Type: ApplicationFiled: May 30, 2013Publication date: December 4, 2014Applicant: Chevron U.S.A. Inc.Inventor: Howard Steven Lacheen
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Patent number: 8889932Abstract: Methods are provided for producing a jet fuel composition from a feedstock comprising a natural oil. The methods comprise reacting the feedstock with oxygen under conditions sufficient to form an oxygen-cleaved product. The methods further comprise hydrogenating the oxygen-cleaved product under conditions sufficient to form a jet fuel composition.Type: GrantFiled: November 25, 2009Date of Patent: November 18, 2014Assignee: Elevance Renewable Sciences, Inc.Inventors: Melvin L. Luetkens, Jr., Steven A. Cohen
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Publication number: 20140336430Abstract: A process for producing alkylated hydrocarbons includes the steps of: (a) combining a first feed stream comprising an olefin and an isoparaffin with an alkylation catalyst stream in a first alkylation reactor, (b) removing heat of reaction from the first alkylation reactor, (c) passing an effluent of the first alkylation reactor to a first reaction zone of a second alkylation reactor operating adiabatically to thereby form a first reaction zone effluent, (d) passing the first reaction zone effluent to a second reaction zone of the second alkylation reactor for mixture with a second feed stream comprising an olefin and an isoparaffin, and (e) passing an effluent of the second alkylation reactor to a settler for separation into a hydrocarbon stream and an alkylation catalyst effluent stream. An alkylation unit for carrying out the process is also disclosed.Type: ApplicationFiled: May 10, 2013Publication date: November 13, 2014Inventors: Mark L. Gravley, Martyn E. Pfile
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Patent number: 8766025Abstract: A process has been developed for producing fuel from renewable feedstocks such as plant and animal oils and greases. The process involves treating a first portion of a renewable feedstock by hydrogenating and deoxygenating in a first reaction zone and a second portion of a renewable feedstock by hydrogenating and deoxygenating in a second reaction zone to provide a diesel boiling point range fuel hydrocarbon product. If desired, the hydrocarbon product can be isomerized to improve cold flow properties. A portion of the hydrocarbon product is recycled to the first reaction zone to increase the hydrogen solubility of the reaction mixture.Type: GrantFiled: September 14, 2012Date of Patent: July 1, 2014Assignee: UOP LLCInventors: Charles P. Luebke, Stanley J. Frey
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Patent number: 8728301Abstract: Integrated isomerization and ionic liquid catalyzed alkylation processes may comprise integrating ionic liquid alkylation and n-butane isomerization using a common distillation unit for separating an n-butane containing fraction from at least one of an alkylation hydrocarbon phase from an ionic liquid alkylation reactor and an isomerization hydrocarbon stream from an isomerization unit. The n-butane containing fraction may undergo isomerization to provide an isomerization reactor effluent comprising the isomerization hydrocarbon stream. An isobutane containing fraction, separated from at least one of the alkylation hydrocarbon phase and the isomerization hydrocarbon stream, may be recycled from the distillation unit to the ionic liquid alkylation reactor.Type: GrantFiled: September 12, 2011Date of Patent: May 20, 2014Assignee: Chevron U.S.A. Inc.Inventor: Hye Kyung Cho Timken
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Patent number: 8658847Abstract: In the present invention, a biofuel composition and processes for the incorporation of biologically-derived ethanol into gasoline are disclosed. The present invention discloses ways to use biologically-derived ethanol in gasoline while simultaneously enabling the blending of products from saturation of benzene. In addition, the present invention also discloses ways to use this ethanol with other volatile compounds from petroleum such as isopentane.Type: GrantFiled: June 17, 2010Date of Patent: February 25, 2014Assignee: Chevron U.S.A. Inc.Inventors: Dennis J. O'Rear, Sven I. Hommeltoft, Hye-Kung Timken
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Publication number: 20140051872Abstract: The present invention provides catalysts, methods, and reactor systems for converting oxygenated hydrocarbons to oxygenated compounds. The invention includes methods for producing cyclic ethers, monooxygenates, dioxygenates, ketones, aldehydes, carboxylic acids, and alcohols from oxygenated hydrocarbons, such as carbohydrates, sugars, sugar alcohols, sugar degradation products, and the like, using catalysts containing palladium, molybdenum, tin, and tungsten. The oxygenated compounds produced are useful in the production of liquid fuels, chemicals, and other products.Type: ApplicationFiled: August 15, 2012Publication date: February 20, 2014Applicant: Virent, Inc.Inventors: Brian Blank, Randy Cortright, Taylor Beck, Elizabeth Woods, Mike Jehring
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Patent number: 8556999Abstract: The present invention provides non-petroleum high-octane fuel derived from biomass sources, and a method of producing same. The method of production involves reducing the biomass feedstocks to sugars, fermenting the sugars using microorganisms or mutagens thereof to produce ethanol or acetic acid, converting the acetic acid or ethanol to acetone, and converting the acetone to mesitylene and isopentane, the major components of the renewable engine fuel. Trimerization of acetone can be carried out in the presence of a catalyst containing at least one metal selected from the group consisting of niobium, iron and manganese. The ethanol can be converted to mesitylene in a dehydration reaction in the presence of a catalyst of zinc oxide/calcium oxide, and unreacted ethanol and water separated from mesitylene by distillation.Type: GrantFiled: March 4, 2010Date of Patent: October 15, 2013Assignee: Swift Fuels, LLCInventors: John J Rusek, Mary-Louise Rusek, Jonathon D Ziulkowski, Justin D Zink
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Patent number: 8524962Abstract: A process for producing a feedstock for gasolines having very little aromatic concentrations is disclosed. The present process uses by-product olefins and alkanes to produce an alkylate for use in gasoline blending.Type: GrantFiled: January 25, 2011Date of Patent: September 3, 2013Assignee: UOP LLCInventors: John J. Senetar, David A. Wegerer, Gavin P. Towler
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Patent number: 8497404Abstract: Processes for upgrading Fischer-Tropsch condensate olefins by alkylation of hydrocrackate involves providing an olefin enriched condensate stream and further providing a Fischer-Tropsch derived hydrocarbon stream comprising wax, hydrocracking the latter Fischer-Tropsch hydrocarbon stream to provide a distillate enriched hydrocracked product comprising isoparaffins, and alkylating the olefins with the isoparaffins in an alkylation zone to provide an alkylate product. The alkylate product is fed to a distillation unit together with the hydrocracked product, while a naphtha containing fraction from the distillation unit is fed to the alkylation zone together with the olefin enriched hydrocarbon stream.Type: GrantFiled: February 12, 2013Date of Patent: July 30, 2013Assignee: Chevron U.S.A. Inc.Inventors: Sven Ivar Hommeltoft, Bi-Zeng Zhan
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Publication number: 20130165720Abstract: A new family of coherently grown composites of TUN and IMF zeotypes have been synthesized. These zeolites are represented by the empirical formula. NanMmk+TtAl1-xExSiyOz where “n” is the mole ratio of Na to (Al+E), M represents a metal or metals from zinc, Group 1, Group 2, Group 3 and or the lanthanide series of the periodic table, “m” is the mole ratio of M to (Al+E), “k” is the average charge of the metal or metals M, T is the organic structure directing agent or agents, and E is a framework element such as gallium. These zeolites are similar to TNU-9 and IM-5 but are characterized by unique compositions and synthesis procedures and have catalytic properties for carrying out various hydrocarbon conversion processes and separation properties for carrying out various separations.Type: ApplicationFiled: December 14, 2012Publication date: June 27, 2013Applicant: UOP LLCInventor: UOP LLC
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Patent number: 8471084Abstract: The process converts FCC olefins to heavier compounds. The heavier compounds are more easily separated from the unconverted paraffins. The heavier compounds can be recycled to an FCC unit or delivered to a separate FCC unit. Suitable conversion zones are oligomerization and aromatic alkylation zones.Type: GrantFiled: March 31, 2010Date of Patent: June 25, 2013Assignee: UOP LLCInventors: Joao Jorge da Silva Ferreira Alves, James E. Rekoske, Christopher P. Nicholas
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Patent number: 8436221Abstract: Processes for upgrading Fischer-Tropsch condensate olefins by alkylation of hydrocrackate may involve providing an olefin enriched condensate stream and further providing a Fischer-Tropsch derived hydrocarbon stream comprising wax, hydrocracking the latter Fischer-Tropsch hydrocarbon stream to provide a distillate enriched hydrocracked product comprising isoparaffins, and alkylating the olefins with the isoparaffins in an alkylation zone to provide an alkylate product. The alkylate product may be fed to a distillation unit together with the hydrocracked product, while a naphtha containing fraction from the distillation unit may be fed to the alkylation zone together with the olefin enriched hydrocarbon stream.Type: GrantFiled: December 22, 2010Date of Patent: May 7, 2013Assignee: Chevron U.S.A. Inc.Inventors: Sven Ivar Hommeltoft, Bi-Zeng Zhan
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Patent number: 8350108Abstract: Processes and reactor systems are provided for the conversion of oxygenated hydrocarbons to paraffins useful as liquid fuels. The process involves the conversion of water soluble oxygenated hydrocarbons to oxygenates, such as alcohols, furans, ketones, aldehydes, carboxylic acids, diols, triols, and/or other polyols, followed by the subsequent conversion of the oxygenates to paraffins by dehydration and alkylation. The oxygenated hydrocarbons may originate from any source, but are preferably derived from biomass.Type: GrantFiled: August 27, 2009Date of Patent: January 8, 2013Assignee: Virent, Inc.Inventors: Randy D. Cortright, Paul G. Blommel, Michael J. Werner, Matthew R. Vanstraten
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Patent number: 8319000Abstract: A process for reacting an iso-pentane, comprising: alkylating the iso-pentane with a converted olefinic feedstock comprising at least 5 wt % C5 olefins, wherein the C5 olefins in the converted olefinic feedstock are predominantly 2-pentene, to make a naphtha and a middle distillate, and wherein a formation of iso-butane during the alkylating is less than 35 wt % of an amount of olefins in the converted olefinic feedstock.Type: GrantFiled: June 29, 2012Date of Patent: November 27, 2012Assignee: Chevron U.S.A. Inc.Inventor: Sven Hommeltoft
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Patent number: 8319001Abstract: A process for reacting an iso-pentane, comprising: a) partially converting an olefinic feedstock comprising at least 15 wt % iso-pentene to make a converted olefinic feedstock, wherein the iso-pentene is reduced and an amount of 2-pentene is retained; and b) alkylating the iso-pentane with the converted olefinic feedstock to make a naphtha and a middle distillate.Type: GrantFiled: June 29, 2012Date of Patent: November 27, 2012Assignee: Chevron U.S.A. Inc.Inventor: Sven Hommeltoft
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Patent number: 8313540Abstract: The present invention provides non-petroleum high-octane fuel derived from biomass sources, and a method of producing same. The method of production involves reducing the biomass feedstocks to sugars, fermenting the sugars using microorganisms or mutagens thereof to produce ethanol or acetic acid, converting the acetic acid or ethanol to acetone, and converting the acetone to mesitylene and isopentane, the major components of the renewable engine fuel. Trimerization of acetone can be carried out in the presence of a catalyst containing at least one metal selected from the group consisting of niobium, iron and manganese. The ethanol can be converted to mesitylene in a dehydration reaction in the presence of a catalyst of zinc oxide/calcium oxide, and unreacted ethanol and water separated from mesitylene by distillation.Type: GrantFiled: March 4, 2010Date of Patent: November 20, 2012Assignee: Swift Fuels, LLCInventors: John J Rusek, Mary-Louise Rusek, Jonathon D Ziulkowski, Justin D Zink
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Publication number: 20120283493Abstract: An integrated method for production of fuels, fuel additives, or chemicals in a biorefinery by the conversion of cellulosic materials is disclosed herein. The method is based on converting a source of C6 sugar into a mixture of hydrotreated compounds. Embodiments of the method can be highly integrated, with reagents for particular steps being provided by other steps of the process.Type: ApplicationFiled: March 7, 2012Publication date: November 8, 2012Inventors: Edwin S. Olson, Carsten Heide
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Patent number: 8304592Abstract: A process has been developed for producing fuel from renewable feedstocks such as plant and animal oils and greases. The process involves treating a first portion of a renewable feedstock by hydrogenating and deoxygenating in a first reaction zone and a second portion of a renewable feedstock by hydrogenating and deoxygenating in a second reaction zone to provide a diesel boiling point range fuel hydrocarbon product. If desired, the hydrocarbon product can be isomerized to improve cold flow properties. A portion of the hydrocarbon product is recycled to the first reaction zone to increase the hydrogen solubility of the reaction mixture.Type: GrantFiled: May 20, 2009Date of Patent: November 6, 2012Assignee: UOP LLCInventor: Charles P. Luebke
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Patent number: 8299311Abstract: A process for reacting an iso-pentane with an olefinic feedstock, comprising: a) partially converting one or more olefins in the olefinic feedstock with an ionic liquid catalyst to make a converted olefinic feedstock, wherein linear internal olefins remain unconverted; and b) alkylating the converted olefinic feedstock with the iso-pentane. A process, comprising: alkylating an iso-pentane with a converted olefinic feedstock comprising at least 5 wt % C5 olefins, wherein the C5 olefins in the converted olefinic feedstock are predominantly 2-pentene, to make a naphtha and a middle distillate, and wherein a formation of iso-butane during the alkylating is low. Also a process, comprising: a) partially converting an olefinic feedstock comprising at least 15 wt % iso-pentene to make a converted olefinic feedstock, wherein the iso-pentene is reduced and an amount of 2-pentene is retained; and b) alkylating the iso-pentane with the converted olefinic feedstock to make a naphtha and a middle distillate.Type: GrantFiled: November 30, 2009Date of Patent: October 30, 2012Assignee: Chevron U.S.A. Inc.Inventor: Sven Ivar Hommeltoft
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Patent number: 8288601Abstract: A process for reacting an iso-alkane, comprising: a) partially converting one or more olefins in an olefinic feedstock to make a converted olefinic feedstock, wherein the converting is different from isomerization; b) isolating from the converted olefinic feedstock: i. an enriched feed that has linear internal olefins, and ii. products having a boiling point of 150° C. or higher; and c) alkylating the iso-alkane with the enriched feed to make an alkylate gasoline blending component.Type: GrantFiled: May 14, 2012Date of Patent: October 16, 2012Assignee: Chevron U.S.A. Inc.Inventors: Sven Ivar Hommeltoft, Hye Kyung Cho Timken, Steve Sarup Mathur
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Patent number: 8247628Abstract: A process for reacting an iso-alkane, comprising: a) partially converting one or more olefins in an olefinic feedstock with an ionic liquid catalyst to make a converted olefinic feedstock; and b) alkylating the iso-alkane with the converted olefinic feedstock, wherein a reaction heat that is evolved during the alkylating is at least 20% less than if the alkylating step is done with the iso-alkane and the olefinic feedstock without the partially converting step. Also, a process for reacting an iso-alkane, comprising: a) partially converting one or more olefins in an olefinic feedstock to make a converted olefinic feedstock, wherein the converting is different from isomerization; b) isolating from the converted olefinic feedstock: i. an enriched feed that has linear internal olefins, and ii. products having a boiling point of 150° C. or higher; and c) alkylating the iso-alkane with the enriched feed to make an alkylate gasoline blending component.Type: GrantFiled: November 30, 2009Date of Patent: August 21, 2012Assignee: Chevron U.S.A. Inc.Inventors: Sven Ivar Hommeltoft, Hye-Kyung C. Timken, Steve S. Mathur
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Patent number: 8198494Abstract: 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 4 to 6 carbon atoms with an acidic ionic liquid catalyst under alkylation conditions to produce an alkylate stream, wherein the alkylate stream has a RON that is increased from 5 to 32 numbers compared to a comparison alkylate stream made from the first hydrocarbon stream without the step of contacting with the isomerization catalyst.Type: GrantFiled: February 21, 2011Date of Patent: June 12, 2012Assignee: Chevron U.S.A. Inc.Inventors: Saleh Elomari, Hye Kyung C. Tlmken
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Patent number: 8143469Abstract: The invention relates to a process for producing saturated C5-C28 hydrocarbons, suitable as diesel fuels, kerosenes and gasolines, comprising the steps where feedstock derived from starting material of biological origin, is subjected to a condensation step and subsequently subjected to a combined hydrodefunctionalization and isomerization step.Type: GrantFiled: June 10, 2008Date of Patent: March 27, 2012Assignee: Neste Oil OyjInventors: Eija Koivusalmi, Rami Piilola, Pekka Aalto
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Patent number: 8124819Abstract: A process for oligomerization of isobutene, the process including: feeding a hydrocarbon stream comprising n-butane, 1-butene, 2-butene, isobutane, and isobutene to a catalytic distillation reactor system comprising a hydroisomerization catalyst; feeding hydrogen to the catalytic distillation reactor system; concurrently in the catalytic distillation reactor system: contacting the 1-butene with the hydrogen in the presence of the hydroisomerization catalyst to convert at least a portion of the 1-butene to 2-butene; separating the isobutane and the isobutene from the n-butane and the 2-butene; recovering the isobutane and the isobutene from the catalytic distillation reactor system as an overheads fraction; recovering the n-butane and the 2-butene from the catalytic distillation reactor system as a bottoms fraction; contacting the overheads fraction in an oligomerization reaction system with an oligomerization catalyst to convert a portion of the isobutene to oligomers.Type: GrantFiled: January 8, 2009Date of Patent: February 28, 2012Assignee: Catalytic Distillation TechnologiesInventor: Mitchell E. Loescher
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Patent number: 8110161Abstract: The invention relates to a process for the production of alkylated aromatic compounds comprising introducing olefin and aromatic compounds into at least first and second vertically spaced catalytic reaction zones in an alkylation unit under alkylation reaction conditions to provide an alkylated product, wherein the second catalytic reaction zone is positioned above the first catalytic reaction zone; wherein aromatic compound from each of the at least first and second catalytic reaction zones are contacted with a cooling means for re-condensing at least a portion of the aromatic compounds vaporized from the exothermic heat of reaction of the alkylation process; and wherein the olefin is introduced into the at least first and second catalytic reaction zones via respective first and second olefin feed streams at respective olefin feed rates such as to maintain olefin partial pressures at inlets to at least first and second catalytic reaction zones which vary by less than about ten percent.Type: GrantFiled: December 11, 2009Date of Patent: February 7, 2012Assignee: Lummus Technology Inc.Inventor: Kevin John Schwint
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Patent number: 8034988Abstract: A process for alkylation of propylene, the process including: contacting a stream comprising propylene and propane with sulfuric acid in a first reaction zone under conditions to form propylene sulfate esters; contacting the propylene sulfate esters with isoparaffin and sulfuric acid in an alkylation reaction zone under conditions to react the propylene sulfate esters and the isoparaffin to form a reactor effluent comprising an acid phase and a hydrocarbon phase comprising unreacted isoparaffin and alkylate product; separating the hydrocarbon phase from the sulfuric acid; separating the hydrocarbon phase to form a fraction comprising unreacted isoparaffin and a fraction comprising the alkylate product.Type: GrantFiled: September 19, 2008Date of Patent: October 11, 2011Assignee: Catalytic Distillation TechnologiesInventors: Mitchell E. Loescher, William M. Cross, Jr., Lawrence A. Smith, Jr.
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Patent number: 7935320Abstract: A system and/or process for decreasing the level of at least one organic fluoride present in a hydrocarbon phase contained in an alkylation settler by contacting the hydrocarbon phase with an HF containing stream, containing greater than about 80 wt. % and less than about 94 wt. % HF, in the intermediate portion of the settler which contains at least one tray system, with each tray system comprising a perforated tray defining a plurality of perforations and a layer of packing below the perforated tray, are disclosed.Type: GrantFiled: October 9, 2008Date of Patent: May 3, 2011Assignee: UOP LLCInventors: Keith W. Hovis, Bruce B. Randolph
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Patent number: 7915468Abstract: 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: GrantFiled: April 3, 2009Date of Patent: March 29, 2011Assignee: Chevron U.S.A. Inc.Inventors: Hye-Kyung C. Timken, Saleh Elomari
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Patent number: 7902412Abstract: A process for producing a feedstock for gasolines having very little aromatic concentrations is disclosed. The present process uses by-product olefins and alkanes to produce an alkylate for use in gasoline blending.Type: GrantFiled: July 23, 2007Date of Patent: March 8, 2011Assignee: UOP LLCInventors: John J. Senetar, David A. Wegerer, Gavin P. Towler
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Publication number: 20100174121Abstract: The present invention relates to the production of butenes and derivatives thereof from dry ethanol, optionally obtained from a fermentation broth. The butenes thus produced find use as intermediates for the production of polyethylenes and other materials.Type: ApplicationFiled: November 30, 2007Publication date: July 8, 2010Applicant: E.I DU PONT DE NEMOURS AND COMPANYInventors: Leo Ernest Manzer, Michael B. D'Amore, Edward S. Miller, JR.
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Patent number: 7744742Abstract: The process as described herein produces a moderately aromatic isoparaffinic base oil from a distillate range product. This process comprises: (a) providing a distillate range paraffin feed comprising paraffins and cycloparaffins; (b) mildly reforming the distillate range paraffin feed to convert at least a portion of the cycloparaffins to alkylaromatics and provide a mildly reformed distillate range stream; (c) treating a stream comprising the mildly reformed distillate range stream in a molecular redistribution reactor to provide a distributed stream; (d) dewaxing at least a portion of the distributed stream to provide a dewaxed stream; (e) combining at least a portion of the dewaxed stream with the stream to be processed in the molecular redistribution reactor to provide the distributed stream; and (f) isolating a moderately aromatic isoparaffinic base oil from the dewaxed stream.Type: GrantFiled: November 28, 2007Date of Patent: June 29, 2010Assignee: Chevron U.S.A. Inc.Inventor: Dennis J. O'Rear
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Patent number: 7728185Abstract: A process for increasing the propylene yields for hydrocarbon cracking processes. The process includes adding using alkylation of the C4s coming from the hydrocarbon cracker, and passing larger olefins to an olefin cracking unit.Type: GrantFiled: July 23, 2007Date of Patent: June 1, 2010Assignee: UOP LLCInventors: John J. Senetar, Bryan K. Glover
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Publication number: 20100081854Abstract: A process for treating an alkylation feedstock comprising olefins, n-alkanes, iso-alkanes, and impurities including one or more of butadiene, oxygenates, nitrogen-containing compounds, and sulfur-containing compounds, the process including: contacting an alkylation feedstock containing at least one of oxygenates and nitrogen-containing compounds with water to produce a hydrocarbon fraction having a reduced concentration of the at least one of oxygenates and nitrogen-containing compounds and an aqueous fraction comprising at least a portion of the at least one of oxygenates and nitrogen-containing compounds; separating water from the hydrocarbon fraction having a reduced concentration to produce a hydrocarbon fraction having a reduced water content; contacting the hydrocarbon fraction having a reduced water content with an oligomerization catalyst in a first oligomerization reaction zone under oligomerization conditions to react at least a portion of the olefins to form a reactor effluent comprising olefin oliType: ApplicationFiled: October 1, 2008Publication date: April 1, 2010Applicant: CATALYTIC DISTILLATION TECHNOLOGIESInventors: William M. Cross, JR., Lawrence A. Smith, JR., Gary G. Podrebarac
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Publication number: 20100076233Abstract: Processes and reactor systems are provided for the conversion of oxygenated hydrocarbons to paraffins useful as liquid fuels. The process involves the conversion of water soluble oxygenated hydrocarbons to oxygenates, such as alcohols, furans, ketones, aldehydes, carboxylic acids, diols, triols, and/or other polyols, followed by the subsequent conversion of the oxygenates to paraffins by dehydration and alkylation. The oxygenated hydrocarbons may originate from any source, but are preferably derived from biomass.Type: ApplicationFiled: August 27, 2009Publication date: March 25, 2010Inventors: Randy D. Cortright, Paul G. Blommel, Michael J. Werner, Matthew R. Vanstraten
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Publication number: 20100036173Abstract: The present invention relates to the production of butenes and derivatives thereof from aqueous ethanol, optionally obtained from a fermentation broth. The butenes thus produced find use as intermediates for the production of polyethylenes and for the production of other known, useful materials.Type: ApplicationFiled: November 30, 2007Publication date: February 11, 2010Applicant: E.I. DU PONT DE NEMOURS AND COMPANYInventors: Leo Ernest Manzer, Michael B. D'amore, Edwark S. MIller, JR.
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Patent number: 7601879Abstract: A process for paraffin alkylation of isoalkane with isoolefins in which an olefin component comprising oligomerized propylene, oligomerized isoolefin or mixtures thereof is fed to a paraffin alkylation unit wherein the dissociated olefin components forming the oligomers react with isoalkane to produce a reaction mixture containing an alkylate and unreacted isoalkane The reaction mixture is fractionally distilled to recover unreacted isoalkane as overheads and alkylate as bottoms. The stoichiometry of isoolefins to isoalkane in the alkylation unit is maintained by adjustment of the feed to the oligomerization, for example, by adding fresh isoalkane to the recovered, unreacted isoalkane from the alkylation unit being recycled to the oligomerization. Alternatively, a portion of the recovered unreacted isoalkane is dehydrogenation to an isoolefin which is added to the oligomerization.Type: GrantFiled: August 16, 2006Date of Patent: October 13, 2009Assignee: Catalytic Distillation TechnologiesInventors: William M. Cross, Jr., Lawrence A. Smith, Jr.
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Patent number: 7572944Abstract: A process for making and a composition of a superior lubricant or lubricant component by the oligomerization of a mixture comprising olefins and isoparaffins to produce an alkylated (“capped”) olefin oligomer having a very high VI and a low cloud point. The process preferably uses an acidic chloroaluminate ionic liquid catalyst system. Preferably the ionic liquid catalyst system comprises a Brönsted acid.Type: GrantFiled: December 20, 2005Date of Patent: August 11, 2009Assignee: Chevron U.S.A. Inc.Inventors: Saleh Elomari, Russell Krug
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Patent number: 7572943Abstract: A process and method for making a superior lubricant or distillate fuel component by the oligomerization of a mixture comprising olefins to form an oligomer and the alkylation of the oligomer with isoparaffins to produce an alkylated (“capped”) olefin oligomer preferably using an acidic chloroaluminate ionic liquid catalyst system. Preferably the ionic liquid catalyst system comprises a Brönsted acid.Type: GrantFiled: December 20, 2005Date of Patent: August 11, 2009Assignee: Chevron U.S.A. Inc.Inventors: Saleh Elomari, Russell Krug, Thomas V. Harris, Michael S. Driver
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Patent number: 7553999Abstract: 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: GrantFiled: December 14, 2006Date of Patent: June 30, 2009Assignee: Chevron U.S.A. Inc.Inventors: Saleh Elomari, Hye-Kyung Timken