By Dealkylation Patents (Class 585/483)
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Patent number: 11192833Abstract: This present disclosure relates to processes and apparatuses for toluene and benzene methylation in an aromatics complex for producing paraxylene. More specifically, the present disclosure relates to processes and apparatuses for toluene and benzene methylation within an aromatics complex for producing paraxylene wherein an embodiment uses a reactor having a refractory comprising a low iron content refractory.Type: GrantFiled: April 8, 2019Date of Patent: December 7, 2021Assignee: UOP LLCInventors: Guanghui Zhu, Steven A. Bradley, Mitchell J. Kowalczyk, Gregory B. Kuzmanich, Joseph A. Montalbano
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Patent number: 10781382Abstract: The presently disclosed subject matter provides methods for producing olefins and/or aromatics from coker naphtha. In a non-limiting embodiment, a method for producing aromatics includes hydrogenating the coker naphtha stream in the presence of a first catalyst to remove diolefins and sulfur, if any, to obtain a hydrogenated stream and subjecting the hydrogenated stream to aromatization in the presence of a second catalyst to produce an aromatic-rich stream that includes benzene, toluene and xylene. In certain embodiments, a method for producing olefins includes hydrogenating the coker naphtha stream in the presence of a first catalyst to remove diolefins and sulfur, if any, to obtain a hydrogenated stream and subjecting the hydrogenated stream to catalytic cracking in the presence of a second catalyst to produce an olefin-rich stream that includes ethylene, propylene and aromatics.Type: GrantFiled: November 7, 2016Date of Patent: September 22, 2020Assignee: SABIC GLOBAL TECHNOLOGIES B.V.Inventors: Rajeshwer Dongara, Pankaj Mathure, Mohammad Basheer Ahmed, Venugopal Bv
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Patent number: 9687825Abstract: A process to make a Fischer-Tropsch catalyst with improved hydrothermal stability, comprising: a. contacting a crystalline oxide material with a solution of a tungsten and a phosphorus to make a tungsten-phosphorus modified support; b. calcining the tungsten-phosphorus modified support at a temperature less than or equal to 750° C. to make a calcined tungsten-phosphorus modified support that has the improved hydrothermal stability and that can be used to support a Co-loaded Fischer-Tropsch catalyst. A Co-loaded Fischer-Tropsch catalyst having improved hydrothermal stability and higher C5+ hydrocarbon productivity is also provided. A Fischer-Tropsch synthesis process is provided, comprising contacting a gaseous mixture comprising a carbon monoxide and a hydrogen with the Co-loaded Fischer-Tropsch catalyst having the improved hydrothermal stability and higher C5+ productivity, at a pressure of from 0.1 to 3 MPa and at a reaction temperature of from 180 to 260° C.Type: GrantFiled: June 27, 2016Date of Patent: June 27, 2017Assignee: Chevron U.S.A. Inc.Inventors: Kandaswamy Jothimurugesan, Mark Muraoka
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Patent number: 9233890Abstract: Provided is a process for producing cyclohexylbenzene, in which a benzene feed stream is subjected to each of the following treatment steps: treating the feed stream with at least one adsorbent and fractionating the feed stream to remove components having a different boiling point than benzene. The treatment steps are carried out in any order and produce a treated benzene feed stream. The treated benzene feed stream is then contacted with hydrogen in the presence of a hydroalkylation catalyst in a hydroalkylation unit under conditions effective to produce a reaction product containing cyclohexylbenzene.Type: GrantFiled: July 9, 2013Date of Patent: January 12, 2016Assignee: ExxonMobil Chemical Patents Inc.Inventors: Hari Nair, Christopher L. Becker, Ryan A. Sothen, Charles Morris Smith, Tan-Jen Chen
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Patent number: 8586809Abstract: A guard bed or absorber is placed upstream of a transalkylation reactor to avoid deposition of halide and/or halogen species on the catalysts in said reactor.Type: GrantFiled: July 14, 2011Date of Patent: November 19, 2013Assignee: ExxonMobil Chemical Patents Inc.Inventors: James H. Beech, Jr., Julia E. Steinheider, Doron Levin, Selma S. Lawrence
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Patent number: 8426663Abstract: A process for catalytically converting alkylaromatic compounds in a hydrocarbon feedstock, the process comprising passing a hydrocarbon feedstock including at least one alkylaromatic compound, wherein the alkyl group comprises at least two carbon atoms, through a reactor containing a crystalline silicate catalyst to produce an effluent including at least one aromatic compound and at least one light olefin selected from C2 and C3 olefins.Type: GrantFiled: July 13, 2007Date of Patent: April 23, 2013Assignee: Total Petrochemicals Research FeluyInventors: Jean-Pierre Dath, Walter Vermeiren
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Publication number: 20130066125Abstract: A method of extending the life of an aromatization catalyst comprising identifying a rapid deactivation threshold (RDT) of the catalyst, and oxidizing the catalyst prior to reaching the RDT. A method of aromatizing a hydrocarbon comprising identifying a rapid deactivation threshold (RDT) for an aromatization catalyst, and operating an aromatization reactor comprising the catalyst to extend the Time on Stream of the reactor prior to reaching the RDT. A method of extending the life of an aromatization catalyst comprising predicting a rapid deactivation threshold (RDT) for an aromatization reactor by employing the catalyst in a reactor system under an accelerated fouling condition to identify a test rapid deactivation threshold (t-RDT), predicting the RDT for the aromatization reactor based upon the t-RDT, and oxidizing the catalyst prior to the predicted RDT to extend the Time on Stream of the aromatization catalyst.Type: ApplicationFiled: September 13, 2012Publication date: March 14, 2013Applicant: CHEVRON PHILLIPS CHEMICAL COMPANY LPInventors: Scott H. BROWN, Tin-Tack Peter CHEUNG, Daniel P. HAGEWIESCHE, Baiyi ZHAO
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Publication number: 20120157728Abstract: 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: July 13, 2010Publication date: June 21, 2012Applicant: TOTAL PETROCHEMICALS RESEARCH FELUYInventors: Walter Vermeiren, Nicolas Van Gyseghem
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Patent number: 8084657Abstract: A process of making p-xylcne comprising processing a mixed feedstock containing benzene, toluene, C8 aromatic hydrocarbons, C9 and higher aromatic hydrocarbons, and non-aromatic hydrocarbons through a series of operations and various units, including a C9 and higher aromatic hydrocarbon dealkylation unit, a toluene selective disproportionate unit, an adsorption separation unit, an isomerization unit, and a crystallization separation unit.Type: GrantFiled: November 20, 2009Date of Patent: December 27, 2011Assignees: China Petroleum & Chemical Corporation, Shanghai Research Institute of Petrochemical Technology SinopecInventors: Dejin Kong, Hongli Guo, Luping Zhong, Weisheng Yang, Jian Xiao
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Patent number: 7897829Abstract: Aromatic by-products are sorbed from mono-olefin-containing feedstocks of olefins having from about 6 to 22 carbon atoms per molecule that contain aromatic by-products having from 7 to 22 carbon atoms per molecule. A benzene-containing regenerant displaces and desorbs the aromatic by-products from the sorbent and a regeneration effluent is provided. The regeneration effluent is treated in a regeneration effluent distillation system to provide a benzene-rich stream and an aromatic by-products-containing stream. The latter is subjected to benzene-forming conditions and recycled to the regeneration effluent distillation system where benzene is recovered.Type: GrantFiled: May 24, 2010Date of Patent: March 1, 2011Assignee: UOP LLCInventors: Bryan K. Glover, Andrea G. Bozzano, Antoine Negiz
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Publication number: 20080234527Abstract: The present invention provides a hydrogen production method capable of producing hydrogen with good efficiency while solving problems such as separation, lower-temperature reaction and heat supply in production of hydrogen by dehydrogenation reaction of raw material oil. Within a reaction tube of a double-tube structure comprising an inner tube composed of a hydrogen separating membrane, a metallic outer tube having a plurality of internal fins, and a metal oxide layer and further a catalyst supported on the fins, hydrocarbon having cyclohexane ring is dehydrogenated to produce hydrogen and aromatic hydrocarbon, and selective membrane separating operation of hydrogen is performed within the reaction system while conducting the dehydrogenation to remove mainly the hydrogen on a permeating side and obtain mainly the aromatic hydrocarbon on a non-permeating side.Type: ApplicationFiled: March 8, 2005Publication date: September 25, 2008Inventors: Takaya Matsumoto, Toshiyuki Enomoto, Yukinoro Kude, Yoshinori Kobori
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Patent number: 7396966Abstract: Aromatic by-products are sorbed from mono-olefin-containing feedstocks of olefins having from about 6 to 22 carbon atoms per molecule that contain aromatic by-products having from 7 to 22 carbon atoms per molecule. A benzene-containing regenerant displaces and desorbs the aromatic by-products from the sorbent and a regeneration effluent is provided. The regeneration effluent is treated in a regeneration effluent distillation system to provide a benzene-rich stream and an aromatic by-products-containing stream. The latter is subjected to benzene-forming conditions and recycled to the regeneration effluent distillation system where benzene is recovered.Type: GrantFiled: December 20, 2005Date of Patent: July 8, 2008Assignee: UOP LLCInventors: Bryan K. Glover, Andrea G. Bozzano, Antoine Negiz
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Patent number: 7169730Abstract: Compositions including modified carbide-containing nanorods and/or modified oxycarbide-containing nanorods and/or modified carbon nanotubes bearing carbides and oxycarbides and methods of making the same are provided. Rigid porous structures including modified oxycarbide-containing nanorods and/or modified carbide containing nanorods and/or modified carbon nanotubes bearing modified carbides and oxycarbides and methods of making the same are also provided. The compositions and rigid porous structures of the invention can be used either as catalyst and/or catalyst supports in fluid phase catalytic chemical reactions. Processes for making supported catalyst for selected fluid phase catalytic reactions are also provided.Type: GrantFiled: June 22, 2004Date of Patent: January 30, 2007Assignee: Hyperion Catalysis International, Inc.Inventors: Jun Ma, David Moy
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Patent number: 7151199Abstract: Hydrocarbon or oxygenate conversion process in which a feedstock is contacted with a non zeolitic molecular sieve which has been treated to remove most, if not all, of the halogen contained in the catalyst. The halogen may be removed by one of several methods. One method includes heating the catalyst in a low moisture environment, followed by contacting the heated catalyst with air and/or steam. Another method includes steam-treating the catalyst at a temperature from 400° C. to 1000° C. The hydrocarbon or oxygenate conversion processes include the conversion of oxygenates to olefins, the conversion of oxygenates and ammonia to alkylamines, the conversion of oxygenates and aromatic compounds to alkylated aromatic compounds, cracking and dewaxing.Type: GrantFiled: June 10, 2002Date of Patent: December 19, 2006Assignee: ExxonMobil Chemical Patents Inc.Inventors: Luc Roger Marc Martens, Stephen N. Vaughn, Albert Edward Schweizer, John K. Pierce, Shun Chong Fung
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Patent number: 6900365Abstract: A catalytic hydrodealkylation/reforming process which comprises contacting a heavy hydrocarbon feedstream under catalytic hydrodealkylation/reforming conditions with a composition comprising borosilicate molecular sieves having a pore size greater than about 5.0 Angstroms and a Constraint Index smaller than about 1.0; further containing a hydrogenation/dehydrogenation component; wherein at least a portion of the heavy hydrocarbon feedstream is converted to a product comprising benzene, toluene, xylenes and ethylbenzene.Type: GrantFiled: December 11, 2001Date of Patent: May 31, 2005Assignee: Chevron Phillips Chemical Company LPInventors: Cong-Yan Chen, Stacey I. Zones, Andrew Rainis, Dennis J. O'Rear
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Supported noble metal nanometer catalyst particles containing controlled (111) crystal face exposure
Patent number: 6746597Abstract: A noble metal nanometer-sized catalyst composition is described along with the method for preparation of the composition. The crystal face of the catalyst contains a preponderance of (111) type crystal phase exposure. The crystal phase exposure is controlled by sequestering the noble metal cation before deposition on a catalyst support. Controlled catalyst face exposition combined with the nanometer scale of the catalyst increases the catalyst selectivity and activity, particularly for hydrogenation and dehydrogenation reactions.Type: GrantFiled: January 31, 2002Date of Patent: June 8, 2004Assignee: Hydrocarbon Technologies, Inc.Inventors: Bing Zhou, Michael Rueter -
Publication number: 20040059169Abstract: The invention relates to a method for producing hydrocarbons having a modified carbon skeleton by reacting aliphatic hydrocarbons a) with themselves, b) with another aliphatic hydrocarbon or c) with aromatic alkyl substituted hydrocarbons, in the presence of a metal organic catalyst or the hybrid thereof, at a temperature of between 20-400° C. and a pressure of between 0.2-100 bars, wherein the reaction takes place in the presence of hydrogen.Type: ApplicationFiled: June 25, 2003Publication date: March 25, 2004Inventors: Dominic Vanoppen, Ekkehard Schwab, Jean-Marie Basset, Jean Thivolle-Cazat, Mostapha Taoufik, Michael Schulz, Arthur Hohn
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Patent number: 6677496Abstract: A process for the coproduction of purified benzene and ethylene is provided. The method comprises providing a first mixture comprising benzene, toluene, and one or more C6 to C7 non-aromatics and separating the majority of the benzene and the one or more C6 to C7 non-aromatics from the majority of the toluene to form a second mixture containing benzene and at least a portion of the one or more C6 to C7 non-aromatics. Thereafter at least about 80% of the C6 to C7 non-aromatics in the second mixture are cracked while maintaining essentially no cracking of benzene to produce a cracked product containing ethylene, propylene and pyrolysis gasoline comprising olefins, di-olefins and benzene. The pyrolysis gasoline is preferably hydrotreated and then fractionated to form a purified benzene product comprising at least about 80 wt % benzene. The purified benzene can be used as a feed to a liquid phase or mixed phase alkylation and/or to produce ethylbenzene or cumene.Type: GrantFiled: October 23, 2001Date of Patent: January 13, 2004Inventor: David Netzer
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Publication number: 20030125593Abstract: A catalyst composition and a process for hydrodealkylating a C9+ aromatic compound such as, for example, 1,2,4-trimethylbenzene to a C6 to C8 aromatic hydrocarbon such as a xylene are disclosed. The composition comprises an alumina, a metal oxide, a phosphorus oxide and optionally, an acid site modifier selected from the group consisting of silicon oxides, sulfur oxides, boron oxides, magnesium oxides, tin oxides, titanium oxides, zirconium oxides, molybdenum oxides, germanium oxides, indium oxides, lanthanum oxides, cesium oxides, and combinations of any two or more thereof. The process comprises contacting a fluid which comprises a C9+ aromatic compound with the catalyst composition under a condition sufficient to effect the conversion of a C9+ aromatic compound to a C6 to C8 aromatic hydrocarbon.Type: ApplicationFiled: January 9, 2003Publication date: July 3, 2003Applicant: Phillips Petroleum CompanyInventors: An-Hsiang Wu, Charles A. Drake
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Publication number: 20020077517Abstract: The system and method for optimizing para-xylene production from a feed stream containing para-xylene, ortho-xylene, meta-xylene, ethylbenzene and non-aromatics propose directing the feed stream into an isomerization unit of the system rather than to a separator of the system to avoid causing a bottleneck at the separator and to initially remove ethylbenzene and non-aromatics from the feed stream. This system and method may further provide a reactor in the feed stream used in a pretreatment step, the reactor containing an isomerization catalyst in an amount sufficient to convert substantially all the ethylbenzene in the feed stream to benzene, which is immediately removed and to convert and remove non-aromatics therefrom to optimize equilibrium isomer concentration in the isomerization unit and substantially eliminate coking therein.Type: ApplicationFiled: July 10, 2001Publication date: June 20, 2002Inventors: Goerge R. Winter, Zvi Merchav
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Publication number: 20020016258Abstract: A catalyst composition and a process for hydrodealkylating a C9+ aromatic compound such as, for example, 1,2,4-trimethylbenzene to a C6 to C8 aromatic hydrocarbon such as a xylene are disclosed. The composition comprises an alumina, a metal oxide, and a coke suppressor selected from the group consisting of silicon oxides, phosphorus oxides, boron oxides, magnesium oxides, tin oxides, titanium oxides, zirconium oxides, molybdenum oxides, germanium oxides, indium oxides, lanthanum oxides, cesium oxides, and combinations of any two or more thereof. The process comprises contacting a fluid which comprises a C9+ aromatic compound with the catalyst composition under a condition sufficient to effect the conversion of a C9+ aromatic compound to a C6 to C8 aromatic hydrocarbon.Type: ApplicationFiled: February 23, 1999Publication date: February 7, 2002Applicant: Phillips Petroleum CompanyInventors: AN-HSIANG WU, CHARLES A. DRAKE
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Patent number: 6179996Abstract: Processes and apparatus for providing improved contaminant removal and hydrogen recovery in hydrogenation reactors, particularly in refineries and petrochemical plants. The improved contaminant removal is achieved by selective purging, by passing gases in the hydrogenation reactor recycle loop or purge stream across membranes selective in favor of the contaminant over hydrogen.Type: GrantFiled: May 21, 1999Date of Patent: January 30, 2001Assignee: Membrane Technology and Research, Inc.Inventors: Richard W. Baker, Kaaeid A. Lokhandwala
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Patent number: 6096938Abstract: An improved zeolite catalyst having enhanced dealkylation activity is provided. The catalyst is prepared by incorporating fluorine into the zeolite structure. In another embodiment, a transition element such as nickel is additionally incorporated into the zeolite structure. The process for producing the catalyst also includes ion-exchange and calcining steps. A mordenite type catalyst has been found to be particularly effective. The catalyst of the present invention demonstrates improved activity for the dealkylation of polyalkylaromatic compounds found in residue from the alkylation process and in heavy reformate streams from refineries. A dealkylation process using the catalyst of the present invention is provided. The dealkylation process shows good selectivity for benzene and monoalkylated aromatic products, and catalyst stability, particularly at high reaction temperatures.Type: GrantFiled: November 10, 1999Date of Patent: August 1, 2000Assignee: Fina Technology, Inc.Inventor: Ashim Kumar Ghosh
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Patent number: 6040490Abstract: Aromatic hydrocarbons are efficiently converted by bringing feedstock containing from 5 to 50% by weight of an aromatic hydrocarbon having an ethyl group and a C.sub.9 alkyl aromatic hydrocarbon into contact with a catalyst capable of disproportionation, trans-alkylation and dealkylation, a secondary particle diameter of a zeolite in the catalyst being 10 .mu.m or less.Type: GrantFiled: August 12, 1998Date of Patent: March 21, 2000Assignee: Toray Industries, Inc.Inventors: Ryoji Ichioka, Shinobu Yamakawa, Hirohito Okino, Hajime Kato, Kazuyoshi Iwayama, Hiroshi Konta, Akira Kitamura
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Patent number: 6018086Abstract: The present invention relates to a process of preparing dialkylnaphthylenes and polyalkylenenaphthyleneates.Type: GrantFiled: October 10, 1997Date of Patent: January 25, 2000Assignees: Kabushiki Kaisha Kobe Seiko Sho, Mobil Oil CorporationInventors: Masahiro Motoyuki, Koji Yamamoto, Ajit Vishwanath Sapre, John Paul Mc Williams, Susan Patricia Donnelly
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Patent number: 5962758Abstract: Ethylbenzene is produced from benzene and ethylene in an alkylation reactor wherein the feedstocks also contain propylbenzenes and/or components that produce propylbenzene. Polyethylbenzenes are also produced in the process. The ethylbenzene product and unreacted benzene are separated and then the propylbenzenes are separated from the polyethylbenzenes by distillation. The propylbenzenes are destroyed in a vapor-phase reactor and the polyethylbenzenes are transalkylated with benzene in a liquid or partial liquid phase at a lower temperature.Type: GrantFiled: April 9, 1998Date of Patent: October 5, 1999Assignee: ABB Lummus Global Inc.Inventors: Angel S. Sy, Richard J. Wilcox
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Patent number: 5866743Abstract: Carburization and metal-dusting while hydrodealkylating a hydrodealkylatable hydrocarbon are reduced even in the substantial absence of added sulfur.Type: GrantFiled: January 11, 1996Date of Patent: February 2, 1999Assignee: Chevron Chemical CompanyInventors: John V. Heyse, Bernard F. Mulaskey, Robert A. Innes, Daniel P. Hagewiesche, William J. Cannella, David C. Kramer
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Patent number: 5856608Abstract: A catalyst composition and a process for converting a C.sub.9 + aromatic compound such as, for example, 1,2,4-trimethylbenzene to a C.sub.6 to C.sub.8 aromatic hydrocarbon such as a xylene are disclosed. The composition comprises a zeolite, a metal oxide, and optionally a selectivity modifier selected from the group consisting of silicon, sulfur, phosphorus, boron, magnesium, tin, titanium, zirconium, germanium, indium, lanthanum, cesium, oxides thereof and combinations of any two or more thereof. The process comprises contacting a fluid which comprises a C.sub.9 + aromatic compound with the catalyst composition under a condition sufficient to effect the conversion of a C.sub.9 + aromatic compound to a C.sub.6 to C.sub.8 aromatic hydrocarbon.Type: GrantFiled: February 21, 1997Date of Patent: January 5, 1999Assignee: Phillips Petroleum CompanyInventors: An-hsiang Wu, Charles A. Drake
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Patent number: 5849969Abstract: Carburization and metal-dusting while hydrodealkylating a hydrodealkylatable hydrocarbon are reduced even in the substantial absence of sulfur.Type: GrantFiled: June 7, 1995Date of Patent: December 15, 1998Assignee: Chevron Chemical CompanyInventors: John V. Heyse, Bernard F. Mulaskey, Robert A. Innes, Daniel P. Hagewiesche, William J. Cannella, David C. Kramer
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Patent number: 5817903Abstract: A catalyst composition and a process for converting a C.sub.9 + aromatic compound to C.sub.6 to C.sub.8 aromatic hydrocarbons such as xylenes are disclosed. The catalyst composition comprises a zeolite and a metal. The process comprises contacting a fluid stream containing a C.sub.9 + aromatic compound with the catalyst composition under a condition sufficient to effect the production of C.sub.6 to C.sub.8 aromatic hydrocarbon. Also disclosed is a process for producing the catalyst composition which can comprise: (1) impregnating a zeolite with an effective and coke-reducing amount of a metal compound under a condition sufficient to effect the production of a metal-promoted zeolite and (2) calcining the metal-promoted zeolite.Type: GrantFiled: April 4, 1997Date of Patent: October 6, 1998Assignee: Phillips Petroleum CompanyInventors: An-hsiang Wu, Charles A. Drake
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Patent number: 5811615Abstract: A catalyst composition and a process for hydrodealkylating a C.sub.9 + aromatic compound to a C.sub.6 to C.sub.8 aromatic hydrocarbon such as a xylene are disclosed. The composition comprises an alumina and hexavalent chromium oxide. The process comprises contacting a fluid which comprises a C.sub.9 + aromatic compound with the catalyst composition under a condition sufficient to effect the conversion of a C.sub.9 + aromatic compound to a C.sub.6 to C.sub.8 aromatic hydrocarbon.Type: GrantFiled: October 30, 1996Date of Patent: September 22, 1998Assignee: Phillips Petroleum CompanyInventors: An-hsiang Wu, Charles A. Drake
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Patent number: 5714659Abstract: A catalyst composition and a process for hydrodealkylating a C.sub.9 + aromatic compound such as, for example, 1,2,4-trimethylbenzene to a C.sub.6 to C.sub.8 aromatic hydrocarbon such as a xylene are disclosed. The composition comprises an alumina, a metal oxide, and a acid site modifier selected from the group consisting of silicon oxides, boron oxides magnesium oxides, tin oxides, titanium oxides, zirconium oxides, molybdenum oxides, germanium oxides, indium oxides, lanthanum oxides, cesium oxides, and combinations of any two or more thereof. The process comprises contacting a fluid which comprises a C.sub.9 + aromatic compound with the catalyst composition under a condition sufficient to effect the conversion of a C.sub.9 + aromatic compound to a C.sub.6 to C.sub.8 aromatic hydrocarbon.Type: GrantFiled: August 29, 1996Date of Patent: February 3, 1998Assignee: Phillips Petroleum CompanyInventors: An-hsiang Wu, Charles A. Drake
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Patent number: 5714660Abstract: A catalyst composition and a process for hydrodealkylating a C.sub.9 + aromatic compound such as, for example, 1,2,4-trimethylbenzene to a C.sub.6 to C.sub.8 aromatic hydrocarbon such as a xylene are disclosed. The composition comprises an alumina, a metal oxide, and an acid site modifier selected from the group consisting of silicon oxides, phosphorus oxides, boron oxides, magnesium oxides, tin oxides, titanium oxides, zirconium oxides, molybdenum oxides, germanium oxides, indium oxides, lanthanum oxides, cesium oxides, and combinations of any two or more thereof. The process comprises contacting a fluid which comprises a C.sub.9 + aromatic compound with the catalyst composition under a condition sufficient to effect the conversion of a C.sub.9 + aromatic compound to a C.sub.6 to C.sub.8 aromatic hydrocarbon.Type: GrantFiled: August 29, 1996Date of Patent: February 3, 1998Assignee: Phillips Petroleum CompanyInventors: An-hsiang Wu, Charles A. Drake, Ralph J. Melton
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Patent number: 5689026Abstract: A process for hydrodealkylating C.sub.9 -C.sub.12 alkyl-substituted benzenes (preferably trimethylbenzenes) to C.sub.6 -C.sub.8 aromatic hydrocarbons (in particular, toluene and xylenes) and C.sub.1 -C.sub.5 alkanes employs a catalyst containing zeolite Beta, nickel, molybdenum and sulfur (preferably as sulfides of nickel and of molybdenum).Type: GrantFiled: April 24, 1996Date of Patent: November 18, 1997Assignee: Phillips Petroleum CompanyInventors: An-hsiang Wu, Charles A. Drake, Ralph J. Melton
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Patent number: 5457255Abstract: A catalyst for hydrogenolytic dealkylation comprising rhodium on a crystalline metallo-silicate carrier and a process for hydrogenolytically dealkylating a hydrocarbon mixture mainly comprising alkyl aromatic hydrocarbons in the presence of such a catalyst are disclosed. The catalyst exhibits catalytic activity at low temperatures and high reaction selectivity and has a prolonged duration.Type: GrantFiled: May 24, 1994Date of Patent: October 10, 1995Assignee: Mitsubishi Oil Co., Ltd.Inventors: Fumio Kumata, Toshihiko Masuda, Iwao Ueda
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Patent number: 5278344Abstract: The present invention is an integrated catalytic reforming/hydrodealkylation process that maximizes benzene recovery by incorporating refrigeration and pressure swing adsorption separation units. In the refrigeration separation unit, liquid reformate is used as a sponge oil to recover benzene from a hydrodealkylation purge gas stream, which in the past has been vented. The pressure swing adsorption unit remove impurities from a hydrogen-rich gas stream prior to use in the hydrodealkylation unit.Type: GrantFiled: December 14, 1992Date of Patent: January 11, 1994Assignee: UOPInventors: Christopher D. Gosling, John D. Swift
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Patent number: 5210350Abstract: 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: GrantFiled: March 11, 1991Date of Patent: May 11, 1993Assignee: Michelin Recherche et TechniqueInventors: Jonis Solofo, Patrice Moreau, Patrick Geneste, Annie Finiels
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Patent number: 5160500Abstract: There is provided a method for preparing a zeolite other than ZSM-5 from a reaction mixture comprising a mixed organic directing agent which is a combination of (a) an organic nitrogen containing compound such as an amine or a quaternary ammonium compound and (b) an alcohol and/or diol. Particular zeolites synthesized by this method include ZSM-22 and ZSM-23. The use of an alcohol or a diol may inhibit the coformation of ZSM-5. Especially when used to prepare ZSM-23, this method enables the preparation of more catalytically active ZSM-23 of reduced crystallite size and also enables the use of lower crystallization temperatures. Particular mixed organic directing agents for the preparation of ZSM-23 are combinations of (a) pyrrolidine and (b) ethanol or ethylene glycol.Type: GrantFiled: October 30, 1991Date of Patent: November 3, 1992Assignee: Mobil Oil CorporationInventors: Pochen Chu, Donald J. Klocke, David O. Marler, John P. McWilliams, James C. Vartuli
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Patent number: 4806700Abstract: A process is disclosed for the conversion of a light aliphatic hydrocarbon, such as propane, into benzene and optionally also naphthalene. The feed hydrocarbon is converted to aromatic hydrocarbons in a dehydrocyclodimerization zone. The aromatics, and other cyclic hydrocarbons, are passed into a hydrodealkylation zone which is preferably supplied with hydrogen produced in the dehydrocyclodimerization zone. Benzene may be separated from the effluent of the dehydrocyclodimerization zone prior to passage of the aromatics into the hydrodealkylation zone.Type: GrantFiled: October 22, 1986Date of Patent: February 21, 1989Assignee: UOP Inc.Inventor: David C. Martindale
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Patent number: 4670615Abstract: A process is provided for converting feedstock comprising aromatic hydrocarbon compounds to product comprising aromatic hydrocarbon compounds which differs from the feedstock over a catalyst composition comprising a crystalline layered silicate material.Type: GrantFiled: February 5, 1986Date of Patent: June 2, 1987Assignee: Mobil Oil CorporationInventor: Ernest W. Valyocsik
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Patent number: 4577049Abstract: A process is disclosed for dealkylating durene under elevated temperatures and pressures with a polynuclear aromatic compound. The dealkylation is carried out in the presence of a carbon-containing molecular sieve.Type: GrantFiled: April 24, 1985Date of Patent: March 18, 1986Assignee: Mobil Oil CorporationInventor: Leslie R. Rudnick
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Patent number: 4551235Abstract: There is disclosed a system for measuring and controlling the concentration of hydrogen in hydrogen recycle processes used in oil refineries and petrochemical plants. The system is intended to reduce the amount of hydrogen and hydrocarbon vapor circulating in such systems, thus reducing the quantity of utilities needed to operate such systems. Specifically, there is a savings of compressor power and fuel required for heating. The system is dependent on the recognition that a decrease in cooling medium temperature results in an increase in hydrogen flow, which can be decreased to the minimum permissible without endangering catalyst activity and stability and product yield if hydrogen concentration is monitored, and that partial pressure is the key parameter.Type: GrantFiled: June 28, 1984Date of Patent: November 5, 1985Assignee: UOP Inc.Inventor: Don B. Carson
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Patent number: 4536276Abstract: There is disclosed a system for measuring and controlling the concentration of hydrogen in hydrogen recycle processes used in oil refineries and petrochemical plants. The system is intended to permit reduction in hydrogen use in hydrogen-consuming hydrogen recycle processes. The system is dependent on the recognition that a decrease in cooling medium temperature results in an increase in vent gas flow, which can be decreased to the minimum permissible without endangering catalyst activity and stability and product yield if hydrogen concentration is monitored, and that partial pressure is the key parameter.Type: GrantFiled: June 28, 1984Date of Patent: August 20, 1985Assignee: UOP Inc.Inventor: Don B. Carson
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Patent number: 4469909Abstract: This invention provides a catalytic process for converting to BTX a C.sub.9 + monocyclic aromatic hydrocarbon feed having a prescribed content of alkyl groups with more than one carbon atom. It further provides a process wherein said conversion is coupled with a catalytic xylene isomerization unit. The catalyst used in the process is a steamed composite comprising platinum and a crystalline zeolite such as ZSM-5.Type: GrantFiled: September 1, 1983Date of Patent: September 4, 1984Assignee: Mobil Oil CorporationInventors: Arthur W. Chester, Yung-Feng Chu
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Patent number: 4463206Abstract: A stabilized hydrocarbon fraction comprising toluene, xylene, sulfur and olefinic hydrocarbons is converted to benzene by (a) catalytic hydrodesulfuration, (b) hydrodealkylation and (c) catalytic hydrogenation.Type: GrantFiled: January 7, 1983Date of Patent: July 31, 1984Assignee: Institut Francais du PetroleInventors: Michel Derrien, Jean Cosyns
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Patent number: 4387261Abstract: A process is disclosed for the dealkylation of durene resulting from a methanol to gasoline conversion by contacting a durene-containing fraction with zeolite ZSM-12 at elevated temperatures and pressures.Type: GrantFiled: April 9, 1982Date of Patent: June 7, 1983Assignee: Mobil Oil CorporationInventors: Arthur W. Chester, Yung F. Chu
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Patent number: 4347398Abstract: Charge hydrocarbon stream containing diisopropyl toluene isomers is catalytically treated to recover product stream containing increased proportions of 1-methyl-3,5-diisopropyl benzene.Type: GrantFiled: July 13, 1980Date of Patent: August 31, 1982Assignee: Texaco Inc.Inventors: John M. Crone, Jr., Robert M. Suggitt
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Patent number: 4314091Abstract: Charge hydrocarbon stream containing diisopropyl toluene isomers is catalytically treated to recover product stream containing increased proportions of 1-methyl-3,5-diisopropyl benzene.Type: GrantFiled: March 31, 1980Date of Patent: February 2, 1982Assignee: Texaco Inc.Inventors: John M. Crone, Jr., Robert M. Suggitt
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Patent number: RE38532Abstract: Carburization and metal-dusting while hydrodealkylating a hydrodealkylatable hydrocarbon are reduced even in the substantial absence of added sulfur.Type: GrantFiled: December 6, 1999Date of Patent: June 8, 2004Assignee: Chevron Phillips Chemical Company LPInventors: John V. Heyse, Bernard F. Mulaskey, Robert A. Innes, Daniel P. Hagewiesche, William J. Cannella, David C. Kramer
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Patent number: RE41136Abstract: The present invention relates to a process of preparing dialkylnaphthylenes and polyalkylenenaphthyleneates dialkylnaphthalenes and polyalkylenenaphthalates.Type: GrantFiled: January 24, 2002Date of Patent: February 16, 2010Assignees: Kobe Steel, Ltd, ExxonMobil Chemical Patents, Inc.Inventors: Masahiro Motoyuki, Koji Yamamoto, Ajit Vishwanath Sapre, John Paul McWilliams, Susan Patricia Donnelly