Having Plural Side-chains Patents (Class 585/321)
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Patent number: 11192834Abstract: A process for producing a para-xylene product from a hydrocarbon feed includes: hydrocracking the hydrocarbon feed in the presence of a catalyst to obtain a hydrocracking product; separating the hydrocracking product to obtain a gas stream and a liquid stream, the liquid stream comprising benzene, toluene, xylene, C9+ hydrocarbon, or a combination comprising at least one of the foregoing; separating the liquid stream to obtain a toluene stream, wherein toluene is present in the toluene stream in an amount equal to or greater than 70 wt %, preferably equal to or greater than 80 wt %, more preferably equal to or greater than 95 wt %, based on the total weight of the toluene stream; and reacting the toluene stream with methanol to obtain the para-xylene product.Type: GrantFiled: June 24, 2019Date of Patent: December 7, 2021Assignee: SABIC GLOBAL TECHNOLOGIES B.V.Inventor: Thomas Hubertus Maria Housmans
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Patent number: 11053176Abstract: Disclosed is a process for producing mixed xylenes and C9+ hydrocarbons in which an aromatic hydrocarbon feedstock comprising benzene and/or toluene is contacted with an alkylating agent comprising methanol and/or dimethyl ether under alkylation conditions in the presence of an alkylation catalyst to produce an alkylated aromatic product stream comprising the mixed xylenes and C9+ hydrocarbons. The mixed xylenes are subsequently converted to para-xylene, and the C9+ hydrocarbons and its components may be supplied as motor fuels blending components. The alkylation catalyst comprises a molecular sieve having a Constraint Index in the range from greater than zero up to about 3. The molar ratio of aromatic hydrocarbon to alkylating agent is in the range of greater than 1:1 to less than 4:1.Type: GrantFiled: March 15, 2019Date of Patent: July 6, 2021Assignee: ExxonMobil Chemical Patents Inc.Inventors: Tan-Jen Chen, Wenyih F. Lai, Anthony Go
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Patent number: 10843983Abstract: A method for producing para-xylene (PX) includes introducing a C8 aromatic-containing composition to a xylene rerun column to separate the C8 aromatic-containing composition into a xylene-containing effluent and a heavy effluent and passing the xylene-containing effluent to a PX processing loop that includes a PX recovery unit operable to separate a PX product from the xylene-containing effluent, a membrane isomerization unit operable to convert a portion of the MX, OX, or both from the xylene-containing effluent to PX, an EB dealkylation unit operable to dealkylate EB from the xylene-containing effluent to produce benzene, toluene, and other C7? compounds, and a membrane separation unit operable to produce a permeate that is PX-rich and a retentate that is PX-lean. The permeate is passed to the PX recovery unit for recovery of PX, which the retentate is bypassed around the PX recovery unit circulated through the xylene processing loop.Type: GrantFiled: February 22, 2019Date of Patent: November 24, 2020Assignee: Saudi Arabian Oil CompanyInventors: Zhonglin Zhang, Sohel K Shaikh, Veera Venkata R Tammana, Raed H. Abudawoud, Bruce Richard Beadle, Hisham Tawfiq Bassam, Rakan Sulaiman Bilaus
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Patent number: 10618855Abstract: Synthesis of aromatic hydrocarbons from synthesis gas in a fixed bed or a moving bed reactor loaded with a composite catalyst comprising Catalyst Component A and Catalyst Component B mixed via a mechanical mixing mode, wherein the active ingredient of the Catalyst Component A is active metal oxides; and the Catalyst Component B is one or both of ZSM-5 zeolite and metal modified ZSM-5; the pressure of the synthesis gas is 0.1-6 MPa; the reaction temperature is 300-600° C.; and the space velocity is 500-8000 h?1. The reaction process has a high product yield and selectivity, with the selectivity of aromatics reaching 50-85%, while the selectivity of the methane byproduct is less than 15%.Type: GrantFiled: July 12, 2016Date of Patent: April 14, 2020Assignee: DALIAN INSTITUTE OF CHEMICAL PHYSICS, CHINESE ACADEMY OF SCIENCESInventors: Xiulian Pan, Junhao Yang, Feng Jiao, Yifeng Zhu, Xinhe Bao
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Patent number: 10308571Abstract: The present invention relates to minimizing benzene, toluene, and an A9/A10 recycle loop in a zero benzene aromatics complex. More specifically, the present invention relates to a minimizing benzene, toluene, and an A9/A10 recycle loop in a zero benzene aromatics complex wherein the aromatic feed has a low methyl to phenyl ratio, and where the aromatic feed has a high methyl to phenyl ratio.Type: GrantFiled: October 11, 2017Date of Patent: June 4, 2019Assignee: UOP LLCInventors: Elizabeth A. Carter, Deng-Yang Jan, Timur V. Voskoboynikov
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Patent number: 10112191Abstract: A method of producing propylene and ethylene from a butene-containing hydrocarbon stream by cracking olefin compounds in the butene-containing hydrocarbon stream in the presence of a core-shell ZSM catalyst, wherein the core-shell ZSM catalyst comprises a ZSM-5 core and a silica shell disposed thereon. Various embodiments of the method of producing propylene and ethylene, and the method of making the core-shell ZSM catalyst are also provided.Type: GrantFiled: June 2, 2018Date of Patent: October 30, 2018Assignee: King Fahd University of Petroleum and MineralsInventors: Sulaiman Al-Khattaf, Palani Arudra, Amr Abdalla
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Patent number: 10112190Abstract: A method of producing propylene and ethylene from a butene-containing hydrocarbon stream by cracking olefin compounds in the butene-containing hydrocarbon stream in the presence of a core-shell ZSM catalyst, wherein the core-shell ZSM catalyst comprises a ZSM-5 core and a silica shell disposed thereon. Various embodiments of the method of producing propylene and ethylene, and the method of making the core-shell ZSM catalyst are also provided.Type: GrantFiled: June 2, 2018Date of Patent: October 30, 2018Assignee: King Fahd University of Petroleum and MineralsInventors: Sulaiman Al-Khattaf, Palani Arudra, Amr Abdalla
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Patent number: 9738573Abstract: In a process for producing para-xylene, a feed stream comprising C6+ aromatic hydrocarbons is separated into a toluene-containing stream, a C8 aromatic hydrocarbon-containing stream and a C9+ aromatic hydrocarbon-containing stream. The toluene-containing stream is contacted with a methylating agent to convert toluene to xylenes and produce a methylated effluent stream. Para-xylene is recovered from the C8 aromatic hydrocarbon-containing stream and the methylated effluent stream in a para-xylene recovery section to produce a para-xylene depleted stream, which is then contacted with a xylene isomerization catalyst under liquid phase conditions effective to isomerize xylenes in the para-xylene depleted stream and produce an isomerized stream. The C9+-containing stream with a transalkylation catalyst under conditions effective to convert C9+-aromatics to C8?-aromatics and produce a transalkylated stream, which is recycled together with the isomerized stream to the para-xylene recovery section.Type: GrantFiled: March 2, 2016Date of Patent: August 22, 2017Assignee: ExxonMobil Chemical Patents Inc.Inventors: Michel Molinier, Jeevan S. Abichandani, Jeffrey L. Andrews, Robert G. Tinger, Dennis J. Stanley, George J. Wagner
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Patent number: 9527007Abstract: A process and apparatus for the production of at least one xylene isomer is provided. The process includes passing a first stream to one side of a split shell fractionation column and a second stream to the other side of the column. The second stream has a higher ratio of ethylbenzene to total C8 aromatics than the first stream. A first overhead stream from the one side is separated and passed as a mixed xylene product and a second overhead stream from the other side is separated and passed as feed to a para-xylene separation zone.Type: GrantFiled: May 29, 2015Date of Patent: December 27, 2016Assignee: UOP LLCInventor: Patrick C. Whitchurch
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Patent number: 9382175Abstract: A method for removing tightly bound sodium from a zeolitic support comprising contacting the support with a sodium specific removal agent to produce a treated support. A method comprising providing an aromatization catalyst comprising a treated support, and contacting the aromatization catalyst with a hydrocarbon feed in a reaction zone under conditions suitable for the production of an aromatic product. A catalyst support comprising an L-zeolite having less than 0.35 wt. % sodium.Type: GrantFiled: August 28, 2014Date of Patent: July 5, 2016Assignee: Chevron Phillips Chemical Company LPInventor: Gyanesh P. Khare
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Patent number: 9249068Abstract: In a process for producing para-xylene, a feed stream comprising C6+ aromatic hydrocarbons is separated into a C7? aromatic hydrocarbon-containing stream, a C8 aromatic hydrocarbon-containing stream, and a C9+ aromatic hydrocarbon-containing stream. The C7? aromatic hydrocarbon-containing stream is contacted with a methylating agent to convert toluene to xylenes and produce a methylated effluent stream. Ethylbenzene is removed from the C8 aromatic hydrocarbon-containing stream, para-xylene is recovered from the ethylbenzene-depleted C8 aromatic hydrocarbon-containing stream and the methylated effluent stream in a para-xylene recovery section to produce a para-xylene depleted stream, which is then contacted with a xylene isomerization catalyst under liquid phase conditions effective to isomerize xylenes in the para-xylene depleted stream and produce an isomerized stream.Type: GrantFiled: June 10, 2015Date of Patent: February 2, 2016Assignee: ExxonMobil Chemical Patents Inc.Inventors: Robert G. Tinger, Jeffrey L. Andrews, Michel Molinier
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Patent number: 9221037Abstract: A transalkylation catalyst for the transalkylation of a heavy reformate is provided. The catalyst includes two solid acid zeolites having different physical and chemical properties, and at least three metals selected from the group 4 lanthanthides, and the elements found in groups 6 and 10 of the periodic table.Type: GrantFiled: March 12, 2013Date of Patent: December 29, 2015Assignees: SAUDI ARABIAN OIL COMPANY, KING FAHD UNIVERSITY OF PETROLEUM AND MINERALSInventors: Cemal Ercan, Yuguo Wang, Mohammed Ashraf Ali, Sulaiman Saleh Al-Khattaf, Syed Ahmed Ali, Abdullah Mohammed Aitani
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Patent number: 9156746Abstract: Processes are described for improved utilization of the byproduct acetic acid universally produced in various oxidative processes for making acrylic acid and methacrylic acid, wherein at least a portion of the byproduct acetic acid is converted to isobutene and optionally to one or more further value-added products which may be prepared from isobutene.Type: GrantFiled: April 10, 2015Date of Patent: October 13, 2015Assignees: Washington State University, Archer Daniels Midland Co.Inventors: Junming Sun, Changjun Liu, Yong Wang, Kevin Martin, Padmesh Venkitasubramanian
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Publication number: 20150141700Abstract: A process for producing alkylated aromatic compounds includes pyrolyzing a coal feed to produce a coke stream and a coal tar stream. The coal tar stream is hydrotreated and the resulting hydrotreated coal tar stream is cracked. A portion of the cracked coal tar stream is separated to obtain a fraction having an initial boiling point in the range of about 60° C. to about 180° C., and an aromatics-rich hydrocarbon stream is extracted by contacting the fraction with one or more solvents. The aromatics-rich hydrocarbon stream is contacted with an alkylating agent to produce an alkylated aromatic stream, or the aromatics-rich hydrocarbon stream is reacted with an aliphatic compound or methanol in the presence of a catalyst to produce a methylated aromatic stream. The alkylated aromatic stream, the methylated aromatic stream, or both are separated into at least a benzene stream, a toluene stream, and a xylenes stream.Type: ApplicationFiled: August 22, 2014Publication date: May 21, 2015Inventors: James A. Johnson, Paul T. Barger, Maureen L. Bricker, John Q. Chen, Peter K. Coughlin, Stanley J. Frey, Joseph A. Kocal, Matthew Lippmann, Vasant P. Thakkar
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Publication number: 20150141715Abstract: A process for making a bio-naphtha and optionally bio-propane from a complex mixture of natural occurring fats & oils, wherein said complex mixture is subjected to a refining treatment for removing the major part of non-triglyceride and non-fatty acid components, thereby obtaining refined fats & oils; said refined fats & oils are transformed into linear or substantially linear paraffin's as the bio-naphtha by an hydrodeoxygenation or from said refined fats & oils are obtained fatty acids that are transformed into linear or substantially linear paraffin's as the bio-naphtha by hydrodeoxygenation or decarboxylation of the free fatty acids or from said refined fats & oils are obtained fatty acids soaps that are transformed into linear or substantially linear paraffin's as the bio-naphtha by decarboxylation of the soaps.Type: ApplicationFiled: January 28, 2015Publication date: May 21, 2015Inventors: Walter Vermeiren, Nicolas Van Gyseghem
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Publication number: 20150073187Abstract: A method of producing a purified mixed xylene comprising: introducing toluene and methanol to an alkylation reactor (32); reacting the toluene and the methanol in the alkylation reactor (32) to form a hydrocarbon stream (22) comprising a first mixed xylene, wherein the alkylation reactor (32) comprises an alkylation catalyst; separating the hydrocarbon stream (22) into a toluene stream (24) and a separated C8+ stream (14); introducing the toluene stream (24) to a transalkylation reactor (38) with a transalkylation catalyst to produce a transalkylated stream (17) comprising a second mixed xylene; adding the transalkylated stream (17) to the hydrocarbon stream (22); and separating a C8 product stream (19) comprising the purified mixed xylene from the separated C8+ stream (14).Type: ApplicationFiled: September 10, 2013Publication date: March 12, 2015Applicant: SAUDI BASIC INDUSTRIES CORPORATIONInventors: Ashim Kumar Ghosh, Mohamed Elbaccouch, Mohammad Shafiei, Murali Gopalakrishnan
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Publication number: 20150073131Abstract: The present invention is directed generally to a method of production of value-added, biobased chemicals from lignin sources, including waste lignin. A method of producing biobased aromatic chemicals, biobased aromatic fuels, and/or lignin residues from lignin is also described herein.Type: ApplicationFiled: March 11, 2013Publication date: March 12, 2015Inventors: John R. Peterson, Christopher M. Yost, Jian Wu
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Publication number: 20150031928Abstract: Processes and apparatuses for preparing aromatic compounds are provided herein. In an embodiment, a process for preparing aromatic compounds includes providing a first stream that includes an aromatic component, a non-aromatic component, and a sulfur-containing component. The aromatic component and the sulfur-containing component are separated from the non-aromatic component of the first stream to form a separated aromatic stream and a raffinate stream. The separated aromatic stream includes the aromatic component and the sulfur-containing component. The raffinate stream includes the non-aromatic component. The separated aromatic stream is concurrently transalkylated and desulfurized in the presence of a catalyst that includes acid function and metal function to produce a transalkylated aromatic stream and a sulfur-containing gas stream that is separate from the transalkylated aromatic stream.Type: ApplicationFiled: July 23, 2013Publication date: January 29, 2015Applicant: UOP LLCInventors: Jason L. Noe, Peter Kokayeff
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Patent number: 8940950Abstract: The process relates to the use of any naphtha-range stream containing a portion of C8+ aromatics combined with benzene, toluene, and other non-aromatics in the same boiling range to produce toluene. By feeding the A8+ containing stream to a dealkylation/transalkylation/cracking reactor to increase the concentration of toluene in the stream, a more suitable feedstock for the methylation reaction can be produced. This stream can be obtained from a variety of sources, including the pygas stream from a steam cracker, “cat naphtha” from a fluid catalytic cracker, or the heavier portion of reformate.Type: GrantFiled: November 23, 2011Date of Patent: January 27, 2015Assignee: ExxonMobil Chemical Patents Inc.Inventors: Justin M. Ellrich, Robert D. Strack, John W. Rebeck, Allen S. Gawlik, Larry L. Iaccino, Glenn C. Wood, Stephen H. Brown, Timothy Paul Bender
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Publication number: 20150025283Abstract: The invention is directed to a multimetallic catalyst and its use in a reactor system in a C9+ aromatics conversion process in order to reduce the saturation of aromatic species, reduce the production of C6+ non-aromatics byproducts, and achieve higher benzene purity. The multimetallic catalyst exhibits improved selectivity towards aromatic hydrocarbons in comparison to a traditional Pt/ZSM-5 catalyst and comprises ZSM-5, a Group 6-10 metal, and an additional metal not in Group 6-10. The C9+ aromatics conversion reactor system comprises a top bed containing the multimetallic catalyst for dealkylation of ethyl and propyl side chains, a second bed containing a catalyst comprising a hydrogenation component for transalkylation, and an optional third bed containing a catalyst without a hydrogenation component to convert non-aromatic hydrocarbons to gas products.Type: ApplicationFiled: June 23, 2014Publication date: January 22, 2015Inventors: Jane C. Cheng, Christopher G. Oliveri
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Patent number: 8937205Abstract: A hydrocarbon upgrading process is described in which a hydrocarbon feed is treated in at least one of a steam cracker, catalytic cracker, coker, hydrocracker, and reformer under suitable conditions to produce a first stream comprising aliphatic and aromatic hydrocarbons. A second stream comprising C6-C9 aliphatic and aromatic hydrocarbons is recovered from the first stream and aliphatic hydrocarbons are removed from at least part of the second stream to produce an aliphatic hydrocarbon-depleted stream. The aliphatic hydrocarbon-depleted stream is then dealkylated and/or transalkylated and/or cracked (D/T/C) by contact with a catalyst under suitable reaction conditions to produce a third stream having an increased benzene and/or toluene content compared with said aliphatic hydrocarbon-depleted stream and a light paraffin by-product. Benzene and/or toluene from the third stream is then methylated with a methylating agent to produce a xylene-enriched stream.Type: GrantFiled: May 7, 2012Date of Patent: January 20, 2015Assignee: ExxonMobil Chemical Patents Inc.Inventors: Larry L. Iaccino, Glenn C. Wood, Jesus A. Ramos, Lane L. McMorris
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Patent number: 8921633Abstract: In a hydrocarbon upgrading process, a hydrocarbon feed is treated in at least one of a steam cracker, catalytic cracker, coker, hydrocracker, and reformer under suitable conditions to produce a first stream comprising olefinic and aromatic hydrocarbons. A second stream composed mainly of C4 to C12+ olefinic and aromatic hydrocarbons is recovered from the first stream and blended said second stream with a residual fraction from a steam cracker or an atmospheric or vacuum distillation unit to produce a third stream. The third stream is then catalytically pyrolyzed in a reactor under conditions effective to produce a fourth stream having an increased benzene and/or toluene content compared with said second stream and a C3-olefin by-product. The C3-olefin by-product is recovered and benzene and/or toluene are recovered from the fourth stream.Type: GrantFiled: May 7, 2012Date of Patent: December 30, 2014Assignee: ExxonMobil Chemical Patents Inc.Inventors: Larry L. Iaccino, Stephen M. Davis, Steven E. Silverberg
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Publication number: 20140378723Abstract: A method of making dialkylaromatics as a primary product is described. The design involves a dual reaction zone system, both reaction zones containing alkylation catalysts. The olefin feed is split into two portions (or two feeds are used), the first portion being fed to a first alkylation reaction zone and reacted with a first olefin. The other portion of olefin is reacted in a second reaction zone with the linear alkylaromatics formed in the first reaction zone to form the dialkylaromatics.Type: ApplicationFiled: June 20, 2013Publication date: December 25, 2014Inventors: DEBARSHI MAJUMDER, STEPHEN W. SOHN
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Publication number: 20140378710Abstract: Disclosed is a method for producing p-xylene and/or p-tolualdehyde with high yield through a short process using biomass resource-derived substances as raw materials. The method for producing p-xylene and/or p-tolualdehyde of the present invention comprises: a cyclization step of producing 4-methyl-3-cyclohexenecarboxaldehyde from isoprene and acrolein; and an aromatization step of producing p-xylene and/or p-tolualdehyde from 4-methyl-3-cyclohexenecarboxaldehyde by gas-phase flow reaction using a catalyst(s).Type: ApplicationFiled: January 23, 2013Publication date: December 25, 2014Applicant: TORAY INDUSTRIES, INC.Inventors: Satoshi Sakami, Daijiro Tsukamoto, Katsushige Yamada
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Publication number: 20140371500Abstract: A method for removing tightly bound sodium from a zeolitic support comprising contacting the support with a sodium specific removal agent to produce a treated support. A method comprising providing an aromatization catalyst comprising a treated support, and contacting the aromatization catalyst with a hydrocarbon feed in a reaction zone under conditions suitable for the production of an aromatic product. A catalyst support comprising an L-zeolite having less than 0.35 wt. % sodium.Type: ApplicationFiled: August 28, 2014Publication date: December 18, 2014Inventor: Gyanesh P. Khare
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Publication number: 20140350316Abstract: The process concerns ethylbenzene conversion and xylene isomerization with a catalyst pretreated by sulfiding.Type: ApplicationFiled: August 11, 2014Publication date: November 27, 2014Inventors: Chunshe Cao, Jeffrey L. Andrews, Michel Molinier
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Publication number: 20140350315Abstract: A method of converting hydrocarbons requires contacting a hydrocarbon stream containing alkylated aromatic hydrocarbons with a catalyst of a phosphorus-containing pentasil zeolite in a reactor. The phosphorus-containing pentasil zeolite having a phosphorus content of 7.5% or less by weight of zeolite, a pore volume of at least 0.2 ml/g, and a 27Al MAS NMR spectrum characterized by a peak at or near 50 ppm that is greater than any other peak in said spectrum. A benzene-enriched output stream is recovered from the reactor.Type: ApplicationFiled: May 23, 2013Publication date: November 27, 2014Inventors: Ashim Kumar Ghosh, Pamela Harvey, Neeta Kulkarni, Manuel Castelan
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Publication number: 20140349361Abstract: The present invention provides methods, reactor systems, and catalysts for increasing the yield of aromatic hydrocarbons produced while converting biomass to hydrocarbons. The invention includes methods of using catalysts to increase the yield of benzene, toluene, and mixed xylenes in the hydrocarbon product.Type: ApplicationFiled: May 22, 2014Publication date: November 27, 2014Applicant: Virent, Inc.Inventors: Paul Blommel, Andrew Held, Ralph Goodwin, Randy Cortright
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Publication number: 20140316174Abstract: Methods are provided for the treatment of a feed stream containing C9 aromatic components to produce mesitylene-containing products. The methods include hydrodealkylating the feed stream to remove C2 and higher alkyl groups from the aromatic components and transalkylating the feed stream to rearrange the distribution of methyl groups among the aromatic components. Disclosed methods also include the treatment of a hydrocarbon feedstock by hydrodealkylation and/or transalkylation in order to produce a hydrocarbon product having an increased mass percentage of mesitylene.Type: ApplicationFiled: April 18, 2014Publication date: October 23, 2014Inventors: Chris D'Acosta, Jeffery Miller, Robert Hoch
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Publication number: 20140296589Abstract: A process is presented for the purification of 1,3 butadiene. The process is for treating a butadiene stream from an oxidative dehydrogenation unit, where a butane stream is dehydrogenated, generating a butadiene rich stream. The butadiene rich stream is fractionated and passed through a butadiene recovery unit. Additional C4 compounds recovered from the fractionation bottoms stream are further processed for increasing yields of butadiene.Type: ApplicationFiled: March 28, 2013Publication date: October 2, 2014Applicant: UOP LLCInventor: Steven L. Krupa
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Publication number: 20140296595Abstract: A method for converting coal into BTX in which feed coal is converted to a 600-700° F.? product stream by direct liquefaction. This product stream is hydrocracked and hydroprocessed to produce a 350° F.? stream which in turn is fractionated to produce a 160° F.? stream and a 160/350° F. stream that contains 85-90% naphthenes. The 160/350° F. stream is catalytically reformed to produce an aromatic stream and a 160° F.? paraffinic stream. The aromatics stream can be separated into benzene toluene and xylene streams by distillation.Type: ApplicationFiled: March 29, 2014Publication date: October 2, 2014Applicant: ACCELERGY CORPORATIONInventors: Richard F. Bauman, Kenneth Lee Trachte
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Publication number: 20140275571Abstract: Methods, catalysts, and reactor systems for producing in high yield aromatic chemicals and liquid fuels from a mixture of oxygenates comprising di- and polyoxygenates are disclosed. Also disclosed are methods, catalysts, and reactor systems for producing aromatic chemicals and liquid fuels from oxygenated hydrocarbons such as carbohydrates, sugars, sugar alcohols, sugar degradation products, and the like; and methods, catalysts, and reactor systems for producing the mixture of oxygenates from oxygenated hydrocarbons such as carbohydrates, sugars, sugar alcohols, sugar degradation products, and the like. The disclosed catalysts for preparing the mixture of oxygenates comprise a Group VIII metal and a crystalline alumina support.Type: ApplicationFiled: March 14, 2014Publication date: September 18, 2014Applicant: Virent, Inc.Inventors: Taylor Beck, Brian Blank, Casey Jones, Elizabeth Woods, Randy Cortright
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Publication number: 20140257002Abstract: Provided are processes for producing a lube basestock or wax from a feedstock of biological origin, the method including: providing a fatty acid originated from the feedstock of biological origin and an aromatic acid in a solvent comprising a base; and electrically coupling the fatty acid and the aromatic acid to produce a hydrocarbon, wherein the molar concentration of the fatty acid is greater than the molar concentration of the aromatic acid.Type: ApplicationFiled: March 7, 2013Publication date: September 11, 2014Applicant: EXXONMOBIL RESEARCH AND ENGINEERING COMPANYInventors: Kun Wang, Liena Tan
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Patent number: 8802905Abstract: A unique, integrated non-obvious pathway to convert biomass to biofuels using integration of chemical processes is described herein. The present invention is simple, direct, and provides for the shortest or minimum path between biomass and transportation fuels with alcohols as intermediates, while avoiding hydrogen use during processing. Furthermore, the present invention allows the manufacture of “drop-in” substitutable fuels to be used as-is without modifications instead of conventional petroleum based fuels. The processing described herein is done under mild conditions, under relatively low pressures and temperatures, and under non-corrosive conditions obviating use of special equipment or materials.Type: GrantFiled: June 18, 2010Date of Patent: August 12, 2014Assignees: The Texas A&M University System, Byogy Renewables, Inc.Inventors: Mahmoud M. El-Halwagi, Kenneth R. Hall, Harold Dennis Spriggs
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Publication number: 20140221714Abstract: A method for producing xylene from feedstock oil includes a cracking/reforming reaction step of bringing the feedstock oil into contact with a catalyst to produce monocyclic aromatic hydrocarbons; a separation/recovery step of separating and recovering, from a product obtained by the cracking/reforming reaction step, a fraction A containing monocyclic aromatic hydrocarbons having a 10 vol % distillation temperature of 75° C. or higher and a 90 vol % distillation temperature of 140° C. or lower, a xylene fraction containing xylene, and a fraction B containing monocyclic aromatic hydrocarbons having a 10 vol % distillation temperature of 145° C. or higher and a 90 vol % distillation temperature of 215° C. or lower; and a xylene conversion step of bringing a mixed fraction obtained by mixing the fractions A and B with each other into contact with a catalyst containing a solid acid to convert the mixed fraction into xylene.Type: ApplicationFiled: May 24, 2012Publication date: August 7, 2014Applicants: CHIYODA CORPORATION, JX NIPPON OIL & ENERGY CORPORATIONInventors: Shinichiro Yanagawa, Yuichiro Fujiyama, Yasuyuki Iwasa, Ryoji Ida, Susumu Yasui, Yoshishige Sugi, Atsushi Fukui, Akira Utatsu
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Publication number: 20140200378Abstract: Method for producing monocyclic aromatic hydrocarbons includes a cracking and reforming reaction step of obtaining products containing monocyclic aromatic hydrocarbons having 6 to 8 carbon atoms and a heavy fraction having 9 or more carbon atoms by bringing the feedstock oil into contact with a catalyst for producing monocyclic aromatic hydrocarbons containing crystalline aluminosilicate to cause a reaction, a catalyst separation step of separating and removing the catalyst for producing monocyclic aromatic hydrocarbons together with tricyclic aromatic hydrocarbons contained in the products from a mixture of the products and a small amount of the catalyst for producing monocyclic aromatic hydrocarbons carried by the products, both of which are derived in the cracking and reforming reaction step, and a purification and recovery step of purifying and recovering the monocyclic aromatic hydrocarbons having 6 to 8 carbon atoms which are separated from the products formed in the cracking and reforming reaction stepType: ApplicationFiled: May 24, 2012Publication date: July 17, 2014Applicants: CHIYODA CORPORATION, JX NIPPON OIL & ENERGY CORPORATIONInventors: Shinichiro Yanagawa, Yuichiro Fujiyama, Yasuyuki Iwasa, Ryoji Ida, Masahide Kobayashi, Susumu Yasui, Yoshishige Sugi, Atsushi Fukui, Atsuro Nagumo
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Publication number: 20140163277Abstract: A method of making one or more 2,5-dimethylhexenes is described. The method includes reacting isobutene with isobutanol in the presence of a platinum group metal catalyst to form one or more 2,5-dimethylhexenes. A method of making p-xylene using one or more 2,5-dimethylhexenes is also described. The p-xylene can be made from totally renewable sources, if desired.Type: ApplicationFiled: December 11, 2013Publication date: June 12, 2014Applicant: UOP LLCInventors: Christopher P. Nicholas, Stuart E. Smith, Alakananda Bhattacharyya
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Publication number: 20140163276Abstract: A new family of coherently grown composites of TUN and IMF zeotypes has been synthesized and shown to be effective catalysts for dehydrocyclodimerization reactions. These zeolites are represented by the empirical formula. NanMmn+RrQqAl1-xExSiyOz where M represents zinc or a metal or metals from Group 1, Group 2, Group 3 or the lanthanide series of the periodic table, R is an A,?-dihalosubstituted paraffin such as 1,4-dibromobutane, Q is a neutral amine containing 5 or fewer carbon atoms such as 1-methylpyrrolidine and E is a framework element such as gallium. The process involves contacting at least one aliphatic hydrocarbon having from 2 to about 6 carbon atoms per molecule with the coherently grown composites of TUN and IMF zeotypes to produce at least one aromatic hydrocarbon.Type: ApplicationFiled: December 11, 2013Publication date: June 12, 2014Applicant: UOP LLCInventors: Christopher P. Nicholas, Mark A. Miller
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Publication number: 20140121430Abstract: A process is described for making renewable para-xylene, comprising converting acetic acid to isobutene in the presence of a catalyst then converting the acetic acid-derived isobutene to a product composition including para-xylene. The catalyst can be a ZnxZryOz mixed oxide catalyst.Type: ApplicationFiled: October 22, 2013Publication date: May 1, 2014Applicants: ARCHER DANIELS MIDLAND COMPANY, WASHINGTON STATE UNIVERSITYInventors: Junming Sun, Changjun Liu, Yong Wang, Colin Smith, Kevin Martin, Padmesh Venkitasubramanian
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Publication number: 20140114105Abstract: A process can include making a bio-diesel, a bio-naphtha, and optionally bio-propane from a complex mixture of natural occurring fats & oils. The complex mixture can be subjected to a refining treatment for removing a major part of non-triglyceride and non-fatty acid components to obtain refined oils. The refined oils can be subjected to a fractionation step to obtain a substantially unsaturated liquid triglyceride part (phase L), and a substantially saturated solid triglyceride part (phase S). The phase L can transformed into alkyl-esters as bio-diesel by a transesterification. The phase S can be transformed into substantially linear paraffin's as the bio-naphtha by an hydrodeoxygenation. Fatty acids can be obtained from the phase S and transformed into substantially linear paraffin's as the bio-naphtha by hydrodeoxygenation or decarboxylation. Fatty acids soaps can be obtained from the phase S that are transformed into substantially linear paraffin's as the bio-naphtha by decarboxylation.Type: ApplicationFiled: November 5, 2013Publication date: April 24, 2014Applicant: TOTAL PETROCHEMICALS RESEARCH FELUYInventors: Walter Vermeiren, Francois Bouvart, Nicolas Dubut
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Patent number: 8696937Abstract: A process for obtaining petrochemical products from a carbonaceous feedstock is provided. The carbonaceous feedstock may be coal, coke, lignite, biomass, bitumen and the like. The carbonaceous feedstock is pulverized and fed to a pyrolysis reactor where the feedstock is pyrolyzed at 700-1000° C. at a pressure of 2-25 bar for 2-10 seconds, wherein the feedstock is entrained in hot syngas during the pyrolysis process.Type: GrantFiled: October 24, 2011Date of Patent: April 15, 2014Inventor: Keki Hormusji Gharda
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Publication number: 20140066675Abstract: The invention concerns a xylenes isomerization process for the production of equilibrium or near-equilibrium xylenes from a feedstream comprising phenol and/or styrene.Type: ApplicationFiled: August 7, 2013Publication date: March 6, 2014Inventors: John Di-Yi Ou, Shifang Luke Luo, Surbhi Jain
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Publication number: 20140031598Abstract: A process comprising feeding bromine into a first reactor; feeding low molecular weight alkanes into the first reactor; and withdrawing alkyl bromides from the first reactor wherein the bromine and low molecular weight alkanes are fed through an apparatus that rapidly mixes the bromine and low molecular weight alkanes. A process is disclosed further comprising reacting the alkyl bromides to form aromatic hydrocarbons.Type: ApplicationFiled: November 21, 2011Publication date: January 30, 2014Inventors: Sujata Degaleesan, Glenn Charles Komplin, Vishwanath Subramaniam, Kuochen Tsai
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Publication number: 20140018587Abstract: This invention relates to fuel compositions for use in combustion engines, such as for motor vehicle and aircraft usage. The fuel composition contains at least 99.5% of aromatic hydrocarbons and paraffinic hydrocarbons. The composition also preferably contains no lead, no multi-ring compound (only single ring compounds are present), less than about 15 ppm sulfur, and/or less than about 5 ppm nitrogen species. The resulting fuel is a drop-in fuel that provides clean burning with little to no engine deposit, high lubricity, high stability, and low corrosion.Type: ApplicationFiled: July 12, 2013Publication date: January 16, 2014Applicant: Primus Green Energy Inc.Inventors: Howard L. FANG, Meifang QIN, Moshe BEN-REUVEN
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Publication number: 20130324772Abstract: The invention relates to a method for producing a fluid hydrocarbon product, and more specifically, to a method for producing a fluid hydrocarbon product via catalytic pyrolysis. The reactants comprise hydrocarbonaceous materials (e.g., biomass). The catalyst comprises a zeolite catalyst treated with a silicone compound. The product comprises p-xylene.Type: ApplicationFiled: September 27, 2012Publication date: December 5, 2013Applicant: UNIVERSITY OF MASSACHUSETTSInventors: George W. Huber, Yu-Ting Cheng, Zhuopeng Wang, Wei Fan
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Publication number: 20130296624Abstract: A hydrocarbon upgrading process is described in which a hydrocarbon feed is treated in at least one of a steam cracker, catalytic cracker, coker, hydrocracker, and reformer under suitable conditions to produce a first stream comprising aliphatic and aromatic hydrocarbons. A second stream comprising C6-C9 aliphatic and aromatic hydrocarbons is recovered from the first stream and aliphatic hydrocarbons are removed from at least part of the second stream to produce an aliphatic hydrocarbon-depleted stream. The aliphatic hydrocarbon-depleted stream is then dealkylated and/or transalkylated and/or cracked (D/T/C) by contact with a catalyst under suitable reaction conditions to produce a third stream having an increased benzene and/or toluene content compared with said aliphatic hydrocarbon-depleted stream and a light paraffin by-product. Benzene and/or toluene from the third stream is then methylated with a methylating agent to produce a xylene-enriched stream.Type: ApplicationFiled: May 7, 2012Publication date: November 7, 2013Inventors: Larry L. Iaccino, Glenn C. Wood, Jesus A. Ramos, Lane L. McMorris
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Publication number: 20130296622Abstract: In a hydrocarbon upgrading process, a hydrocarbon feed is treated in at least one of a steam cracker, catalytic cracker, coker, hydrocracker, and reformer under suitable conditions to produce a first stream comprising olefinic and aromatic hydrocarbons. A second stream composed mainly of C4+ olefinic and aromatic hydrocarbons is recovered from the first stream and is fed together with a methylating agent to a reaction zone containing a catalyst under reaction conditions including a temperature of about 450° C. to about 700° C., such that aromatics components in the second stream undergo dealkylation, transalkylation and/or methylation and aliphatic components undergo cracking and aromatization to produce a third stream having an increased xylene content compared with said second stream and a C3? olefin by-product. The C3? olefin by-product is recovered and para-xylene is removed from at least part of said third stream.Type: ApplicationFiled: May 7, 2012Publication date: November 7, 2013Inventors: LARRY L. IACCINO, S. MARK DAVIS, JOHN D.Y. OU, XIAOBO ZHENG
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Publication number: 20130296623Abstract: In a hydrocarbon upgrading process, a hydrocarbon feed is treated in at least one of a steam cracker, catalytic cracker, coker, hydrocracker, and reformer under suitable conditions to produce a first stream comprising olefinic and aromatic hydrocarbons. A second stream composed mainly of C4 to C12+ olefinic and aromatic hydrocarbons is recovered from the first stream and blended said second stream with a residual fraction from a steam cracker or an atmospheric or vacuum distillation unit to produce a third stream. The third stream is then catalytically pyrolyzed in a reactor under conditions effective to produce a fourth stream having an increased benzene and/or toluene content compared with said second stream and a C3-olefin by-product. The C3-olefin by-product is recovered and benzene and/or toluene are recovered from the fourth stream.Type: ApplicationFiled: May 7, 2012Publication date: November 7, 2013Inventors: Larry L. Iaccino, Stephen M. Davis, Steven E. Silverberg
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Publication number: 20130296621Abstract: In a hydrocarbon upgrading process, a hydrocarbon feed is treated in at least one of a steam cracker, catalytic cracker, coker, hydrocracker, and reformer under suitable conditions to produce a first stream comprising olefinic and aromatic hydrocarbons. A second stream composed mainly of C4 to C12 olefinic and aromatic hydrocarbons is recovered from the first stream and at least part of the second stream is contacted with a catalyst in the absence of added hydrogen under reaction conditions including a temperature of about 450° C. to about 70° C. effective to dealkylate, transalkylate, crack and aromatize components of the second stream to produce a third stream having an increased benzene and/or toluene content compared with the second stream and a C3? olefin by-product. The C3? olefin by-product and a fourth stream comprising toluene are then recovered from the third stream.Type: ApplicationFiled: May 7, 2012Publication date: November 7, 2013Inventors: LARRY L. IACCINO, JAMES R. LATTNER, GLENN C. WOOD, SURBHI JAIN, STEPHEN M. DAVIS
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Publication number: 20130281750Abstract: A method of forming mixed xylenes from a heavy reformate using a dealkylation-transalkylation system includes the step of introducing both a heavy reformate containing methyl ethyl benzenes and tri-methyl benzenes and that is sufficiently free of toluene and a hydrogen-containing material into the dealkylation stage such that the heavy reformate and the hydrogen-containing material intermingle and contact the hydrodealkylation catalyst. The dealkylation-transalkylation system includes dealkylation, non-aromatic product gas separations and transalkylation stages. Toluene forms from the reaction of methyl ethyl benzenes and hydrogen in the presence of the hydrodealkylation catalyst. The method also includes the step of introducing a dealkylated heavy reformate into the transalkylation stage such that the dealkylated heavy reformate contacts a transalkylation catalyst, forming a transalkylation stage product mixture includes mixed xylenes.Type: ApplicationFiled: April 19, 2013Publication date: October 24, 2013Applicant: Saudi Arabian Oil CompanyInventor: RAED ABUDAWOUD