With Specified Flow Rate Through Reactor Or Flow Procedure Within Or At Entrance To Reactor Patents (Class 585/447)
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Patent number: 10961168Abstract: A process for producing paraxylene by the catalytic alkylation of benzene and/or toluene with methanol, which produces a para-rich mixture of xylene isomers, together with water and some light organic by-products, particularly dimethyl ether and C4? olefins. The off-gas stream, containing the C4? olefins, may be recycled back to the reaction to be co-injected with methanol to reduce the methanol self-decomposition and the reaction of methanol to olefins or to fluidize catalyst particles recovered by a reactor cyclone. By using recycled off-gas rather than water or steam, the deleterious effects of water and/or steam on the catalyst aging and activity rates and the size of downstream equipment necessary to recover olefin by-products may be reduced.Type: GrantFiled: August 2, 2017Date of Patent: March 30, 2021Assignee: ExxonMobil Chemical Patents Inc.Inventors: Todd E. Detjen, Robert G. Tinger
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Patent number: 10722861Abstract: Reactor systems for use with ionic liquid catalyst. The reactor systems include one or more stages, which include a reactor and a heat exchanger, and a separation zone. The reactor and the heat exchanger may have a vertical orientation. Additionally, a separation vessel may also include a vertical orientation. The heat exchanger may allow for linear flow of process fluid to control residence time.Type: GrantFiled: May 23, 2018Date of Patent: July 28, 2020Assignee: UOP LLCInventors: Eric Leeton, Kurt Detrick, Christian D. Freet, David S. Lafyatis, Robert Mehlberg, Sean G. Mueller, Gregory J. Schrad, Zhanping Xu
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Patent number: 10570342Abstract: Systems and methods are provided for solvent deasphalting of steam cracker tar. The resulting deasphalted oil produced from the steam cracker tar can then be hydroprocessed, such as hydrotreated and/or hydrocracked in a fixed bed reactor. The solvent deasphalting can correspond to a mild or trim deasphalting or can correspond to solvent deasphalting at higher solvent to oil ratios. Performing a trim deasphalting can reduce or minimize the amount of deasphalting residue that is formed as a product from the deasphalting process.Type: GrantFiled: May 26, 2017Date of Patent: February 25, 2020Assignee: EXXONMOBIL RESEARCH AND ENGINEERING COMPANYInventors: Patrick L. Hanks, Anjaneya S. Kovvali, David T. Ferrughelli, Steven Pyl, Sumathy Raman
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Publication number: 20150119619Abstract: A method for producing isopropyl benzene includes the following steps. Step A: feeding a first stream containing benzene and a first stream containing propylene into a first reaction zone to contact a first catalyst for alkylation, and obtaining a first stream containing isopropyl benzene from the first reaction zone, dividing the first stream containing isopropyl benzene into a stream Ia and a stream IIa, the stream Ia circulating back into the first reaction zone and the stream IIa entering into a second reaction zone, having the stream entering the second reaction zone to contact a second catalyst for alkylation, and obtaining a second stream containing isopropyl benzene from the second reaction zone, and purifying at least a partial stream IIIa of the second stream containing isopropyl benzene, and obtaining a product isopropyl benzene.Type: ApplicationFiled: October 28, 2014Publication date: April 30, 2015Applicants: China Petroleum & Chemical Corporation, Shanghai Research Institute of Petrochemical Technology SINOPECInventors: Huanxin GAO, Hongyuan ZONG, Yilun WEI, Hui YAO, Ruifang GU, Hua FANG, Shufang JI
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Publication number: 20150119618Abstract: This invention relates to an alkylating process for alkyl benzenes, including the steps of: a) an alkyl benzene and a first stream of alkylating agent being fed into a first reaction zone, contacting with a catalyst A, to produce a process stream I; b) the process stream I and a second stream of alkylating agent being fed into at least one second reaction zone, contacting with a catalyst B, to produce a process stream II; and c) the process stream II being fed into at least one third reaction zone, contacting with a catalyst C, to produce a process stream III containing an alkylate. The present alkylating process can improve the utilization efficiency of the alkylating agent.Type: ApplicationFiled: July 4, 2013Publication date: April 30, 2015Inventors: Jian Jiang, Changxi Miao, Dongyu Jiang
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Patent number: 9012696Abstract: Process for the alkylation of aromatic hydrocarbons by means of olefins containing from 2 to 8 carbon atoms, which comprises feeding the hydrocarbon, olefin, and possibly water, to the head of a fixed-bed reactor, operating with a “trickle flow” regime, containing at least one layer of a catalyst comprising a medium-or large-pore zeolite.Type: GrantFiled: June 21, 2012Date of Patent: April 21, 2015Assignee: Versalis S.p.AInventors: Paolo Calaresu, Alessandro Del Seppia, Elena Bencini, Giovanni Antonio Fois, Alessandro Casalini
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Publication number: 20140121431Abstract: A method for alkylation of a feedstock is described. The method includes contacting the feedstock comprising at least one alkylatable aromatic compound and an alkylating agent with a first alkylating catalyst composition under alkylating conditions, the first alkylating catalyst composition comprising UZM-8 zeolite and a binder, the first alkylating catalyst composition having less than 50 wt % UZM-8 zeolite; wherein a total alkylated selectivity at a temperature and a molar ratio of alkylatable aromatic compound to alkylating agent is greater than 99.0%.Type: ApplicationFiled: October 26, 2012Publication date: May 1, 2014Applicant: UOP LLCInventors: Deng-Yang Jan, Robert J. Schmidt, Pelin Cox
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Publication number: 20130165724Abstract: The invention relates to a process of alkylating aromatic hydrocarbons, and more particularly a process of making paraxylene by alkylation of benzene and/or toluene with methanol and/or dimethyl ether, and to an apparatus for carrying out said process, the improvement comprising staged injection of one of the reactants, with the stages separated by structured packing so as to minimize at least one of gas phase back-mixing, by-pass phenomena, and gas bubble size.Type: ApplicationFiled: July 25, 2012Publication date: June 27, 2013Inventors: Lu Han, Rathna P. Davuluri, Christopher G. Smalley, Mark Hagemeister, Masaaki Sugita, Joseph S. Famolaro, Robert G. Tinger
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Patent number: 8455706Abstract: A method of producing a linear alkylbenzene that includes introducing an olefin into an aromatic stream to form a mixture; processing the mixture in a shear device at a shear rate greater than about 20,000 s?1 to form a dispersion; and reacting the dispersion in the presence of a catalyst in a reactor vessel to form a linear alkylbenzene product stream, wherein the reactor vessel is maintained at a bulk reaction temperature in the range of about 0° C. to about 60° C.Type: GrantFiled: August 1, 2012Date of Patent: June 4, 2013Assignee: H R D CorporationInventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Publication number: 20130137910Abstract: The present invention provides an improved process for the catalytic conversion of a feedstock comprising an alkylatable aromatic compound and an alkylating agent to form a conversion product comprising the desired alkylaromatic compound by contacting said feedstock in at least partial liquid phase under catalytic conversion conditions with a catalyst composition comprising a porous crystalline material having a structure type of FAU, BEA* or MWW, or a mixture thereof, wherein the porous crystalline material has a Relative Activity measured at 220° C. as an RA220 of at least 7.5 or measured at 180° C. as RA180 of at least 2.5, allowing operation at lower reaction pressures, e.g., a reaction pressure of about 450 psig (3102 kPa) or less, and lower alkylating agent feed supply pressure of 450 psig (3102 kPa) or less.Type: ApplicationFiled: January 22, 2013Publication date: May 30, 2013Applicant: ExxonMobil Chemical Patents Inc. and Stone & Webster Process Technology, Inc.Inventors: Matthew J. Vincent, Vijay Nanda, Brian Maerz, Maruti Bhandarkar
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Patent number: 8404914Abstract: The invention provides an efficient process for producing alkylated aromatic compounds such as cumene in a compact reactor. The invention also provides a process for producing phenol which includes a step of producing cumene by the above process. The process for producing alkylated aromatic compounds of the invention includes feeding raw materials including an aromatic compound and an alcohol in a gas-liquid downward concurrent flow mode to a fixed-bed reactor packed with a solid acid catalyst thereby to produce an alkylated aromatic compound, wherein the raw materials are fed to the reactor in a stream of a gas, and the reaction gas flow rate defined by the equation below is not less than 0.05 at an entrance of a solid acid catalyst layer: ?g·ug·[?air·?water/(?g·?l)]1/2(kgm?2s?1).Type: GrantFiled: June 3, 2009Date of Patent: March 26, 2013Assignee: Mitsui Chemicals, Inc.Inventors: Shinji Senoo, Kazuhiko Kato, Kenji Doi, Katsunari Higashi
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Patent number: 8395006Abstract: A process for the alkylation of a benzene-containing refinery stream such as reformate with light refinery olefins which is capable of achieving high benzene conversion levels operates in a fixed bed of an MWW zeolite catalyst, preferably MCM-22, in single pass mode in the liquid phase at a relatively low to moderate temperatures with pressure maintained at a value adequate to ensure subcritical operation. High levels of benzene conversion with conversions of at least 90% and higher, e.g. 92% or 95% or even higher are achievable. A high octane product is produced, comprising mono-, di- and tri-alkylbenzenes with lesser levels of the tetra-substituted products. By operating with staged olefin injection, the end point of the alkylation product can be maintained at a low value while, at the same time, achieving high levels of benzene and olefin conversion.Type: GrantFiled: March 9, 2010Date of Patent: March 12, 2013Assignee: ExxonMobil Research and Engineering CompanyInventors: Michael C. Clark, Benjamin S. Umansky, Elizabeth A. Nye, Mark J. Reichensperger, William C. Lewis
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Publication number: 20120330076Abstract: One exemplary embodiment can be a process for alkylating. The process can include providing a first effluent from a first alkylation zone, and providing a second effluent from a second alkylation zone. Generally, the first and second effluents are provided to an exchanger for reboiling a fractionation zone.Type: ApplicationFiled: June 27, 2011Publication date: December 27, 2012Applicant: UOP, LLCInventors: Michael Roy Smith, Russell Clarence Schulz, Phillip F. Daly, Paul Alvin Sechrist
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Publication number: 20120296144Abstract: A method of producing a linear alkylbenzene that includes introducing an olefin into an aromatic stream to form a mixture; processing the mixture in a shear device at a shear rate greater than about 20,000 s?1 to form a dispersion; and reacting the dispersion in the presence of a catalyst in a reactor vessel to form a linear alkylbenzene product stream, wherein the reactor vessel is maintained at a bulk reaction temperature in the range of about 0° C. to about 60° C.Type: ApplicationFiled: August 1, 2012Publication date: November 22, 2012Inventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Patent number: 8278494Abstract: Methods and systems for the production of linear alkylbenzenes are described herein. The methods and systems incorporate the novel use of a high shear device to promote dispersion and mixing of one or more olefins (e.g. propylene) with an aromatic. The high shear device may allow for lower reaction temperatures and pressures and may also reduce reaction time with existing catalysts.Type: GrantFiled: June 23, 2008Date of Patent: October 2, 2012Assignee: H R D CorporationInventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory Borsinger, Aziz Hassan
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Patent number: 8071829Abstract: A process is disclosed for the alkylation of aromatics by charging a hydrocarbon feed containing aromatic hydrocarbons and olefinic hydrocarbons to a distillation column for separation into at least one fraction; removing an aromatics/olefin stream containing at least a portion of the aromatic hydrocarbons and at least a portion of the olefinic hydrocarbons; charging the aromatics/olefin stream to an alkylation reactor, operated at a temperature in the range of from about 80° C. to about 220° C., for alkylation of at least a portion of the aromatic hydrocarbons with the olefinic hydrocarbons; recycling at least a portion of the resulting reactor effluent to the distillation column; and removing a product stream containing alkylated aromatics from the distillation column.Type: GrantFiled: February 20, 2009Date of Patent: December 6, 2011Assignee: ConocoPhillips CompanyInventors: Bradley M. Taylor, Barbara A. Todd
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Publication number: 20110087053Abstract: The invention provides an efficient process for producing alkylated aromatic compounds such as cumene in a compact reactor. The invention also provides a process for producing phenol which includes a step of producing cumene by the above process. The process for producing alkylated aromatic compounds of the invention includes feeding raw materials including an aromatic compound and an alcohol in a gas-liquid downward concurrent flow mode to a fixed-bed reactor packed with a solid acid catalyst thereby to produce an alkylated aromatic compound, wherein the raw materials are fed to the reactor in a stream of a gas, and the reaction gas flow rate defined by the equation below is not less than 0.05 at an entrance of a solid acid catalyst layer: ?g·ug·[?air·?water/(?g·?l)]1/2(kgm?2s?1).Type: ApplicationFiled: June 3, 2009Publication date: April 14, 2011Applicant: MITSUI CHEMICALS, INC.Inventors: Shinji Senoo, Kazuhiko Kato, Kenji Doi, Katsunari Higashi
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Patent number: 7923590Abstract: A process for producing a monoalkylation aromatic product, such as ethylbenzene and cumene, utilizing an alkylation reactor zone and a transalkylation zone in series or a combined alkylation and transalkylation reactor zone. This process requires significantly less total aromatics distillation and recycle as compared to the prior art.Type: GrantFiled: June 27, 2008Date of Patent: April 12, 2011Assignees: ExxonMobil Chemical Patents Inc, Stone & Webster, Inc.Inventors: Shiou-Shan Chen, Shyh-Yuan H. Hwang
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Patent number: 7683228Abstract: A process for producing an cumene product having a purity of at least 99.50 percent based on the weight of cumene present in the product by the propylation of the benzene present in non-extracted hydrocarbon composition feed, e.g., non-extracted reformate. The non-extracted hydrocarbon composition feed is substantially free of both C4? hydrocarbons and the C7+ aromatic hydrocarbons and contains benzene and benzene coboilers. The process is carried out in the liquid phase, in the presence of an acid-active catalyst containing MCM-22 family molecular sieve, and under specified conditions.Type: GrantFiled: February 12, 2007Date of Patent: March 23, 2010Assignee: Exxonmobil Chemical Patents Inc.Inventor: Stephen Harold Brown
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Patent number: 7652181Abstract: An improved alkylation reactor design is disclosed. The design uses reactor effluent recycle to reduce the difference in temperature across the reaction zone improving selectivity and insuring the maintenance of a liquid phase in the reactor.Type: GrantFiled: May 2, 2006Date of Patent: January 26, 2010Assignee: UOP LLCInventors: Robert J. Schmidt, Michael R. Smith, Elena Z. Maurukas, James A. Johnson, Laurence O. Stine
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Patent number: 7652183Abstract: In a process for the preparation of alkylaromatic compounds by reacting C3-30-olefins, or alcohols from which C3-30-olefins are formed under the reaction conditions, with an aromatic hydrocarbon in the presence of an alkylation catalyst, the reaction is carried out in a reactor cascade of at least two reactors, where each of the reactors comprises the alkylation catalyst, at least 80% of the aromatic hydrocarbon are fed into the first reactor of the reactor cascade, and at least 40% of the olefins are intermediately fed in after the first reactor.Type: GrantFiled: April 14, 2004Date of Patent: January 26, 2010Assignee: BASF AktiengesellschaftInventors: Ulrich Steinbrenner, Thomas Narbeshuber, Joerg Unger, Peter Zehner, Soeren Zimdahl, Regina Benfer
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Patent number: 7566429Abstract: The present invention relates to an atmospheric pressure, reactive separation column packed with a solid acid zeolite catalyst for producing cumene from the reaction of benzene with propylene. Use of this un-pressurized column, where simultaneous reaction and partial separation occur during cumene production, allow separation of un-reacted, excess benzene from other products as they form. This high-yielding, energy-efficient system allows for one-step processing of cumene, with reduced need for product purification. Reacting propylene and benzene in the presence of beta zeolite catalysts generated a selectivity greater than 85% for catalytic separation reactions at a reaction temperature of 115 degrees C and at ambient pressure. Simultaneously, up to 76% of un-reacted benzene was separated from the product; which could be recycled back to the reactor for re-use.Type: GrantFiled: June 14, 2005Date of Patent: July 28, 2009Assignee: Sandia CorporationInventors: Genoveva Buelna, Tina M. Nenoff
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Publication number: 20080319242Abstract: The present invention provides an improved process for conversion of feedstock comprising an alkylatable aromatic compound and an alkylating agent to desired alkylaromatic conversion product under at least partial liquid phase conversion conditions in the presence of specific catalyst comprising a porous crystalline material, e.g. a crystalline aluminosilicate, and binder in the ratio of crystal/binder of from about 20/80 to about 60/40. The porous crystalline material of the catalyst may comprise a crystalline molecular sieve having the structure of Beta, an MCM-22 family material, e.g. MCM-49, or a mixture thereof.Type: ApplicationFiled: June 21, 2007Publication date: December 25, 2008Inventors: Michael C. Clark, Frederick Y. Lo, Christine N. Elia, Matthew J. Vincent
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Publication number: 20080194890Abstract: A process for producing an cumene product having a purity of at least 99.50 percent based on the weight of cumene present in the product by the propylation of the benzene present in non-extracted hydrocarbon composition feed, e.g., non-extracted reformate. The non-extracted hydrocarbon composition feed is substantially free of both C4? hydrocarbons and the C7+ aromatic hydrocarbons and contains benzene and benzene coboilers. The process is carried out in the liquid phase, in the presence of an acid-active catalyst containing MCM-22 family molecular sieve, and under specified conditions.Type: ApplicationFiled: February 12, 2007Publication date: August 14, 2008Inventor: Stephen Harold Brown
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Patent number: 7393988Abstract: An improvement in a process for the production of ethylbenzene from a dilute ethylene stream wherein an ethylene-containing stream derived from a cracking process is directed to an ethylene fractionator for separation of ethylene and ethane. The improvement includes providing the dilute ethylene stream by liquefying and separating out a portion of the ethylene-containing stream prior to directing the remainder of the ethylene-containing stream to the ethylene fractionator and/or by drawing off a side stream from the ethylene fractionator; and, directing the dilute ethylene stream as a feed to an alkylator for alkylation with benzene to produce ethylbenzene.Type: GrantFiled: July 6, 2007Date of Patent: July 1, 2008Assignee: Lummus Technology Inc.Inventors: James M. Hildreth, Kerman Nariman Dukandar, Ronald M. Venner
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Patent number: 7282616Abstract: A process for converting an olefin feed to hydrocarbons suitable for fuel components or their feedstock. According to the process, an olefin feed, possibly together with another hydrocarbon feed, is contacted in a reactor with a catalyst in order to produce a hydrocarbon having at least one alkyl side chain. In the invention, the olefin feed is contacted with a particle-form fluidized catalyst in a circulating-bed reactor, wherein the catalyst forms the circulating bed of the reactor. When the operation is carried out in a circulating-bed reactor, the retention time of the feedstock is short. In this case, iso-olefins are formed quite selectively from n-olefins in isomerization. Since the useful life of the catalyst lengthens while the catalytic activity of the bed remains high for a long time, the conversion level also remains high. A long useful life of the catalyst is an economically highly significant advantage.Type: GrantFiled: December 19, 2001Date of Patent: October 16, 2007Assignee: Fortum OyjInventors: Jouko Nikkonen, Jyrki Hiltunen, Jaana Makkonen, Marja Tiitta, Isto Eilos, Pasi Hagelberg
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Patent number: 7259282Abstract: An improvement in a process for the production of ethylbenzene from a dilute ethylene stream wherein an ethylene-containing stream derived from a cracking process is directed to an ethylene fractionator for separation of ethylene and ethane. The improvement includes providing the dilute ethylene stream by liquefying and separating out a portion of the ethylene-containing stream prior to directing the remainder of the ethylene-containing stream to the ethylene fractionator and/or by drawing off a side stream from the ethylene fractionator; and, directing the dilute ethylene stream as a feed to an alkylator for alkylation with benzene to produce ethylbenzene.Type: GrantFiled: September 8, 2003Date of Patent: August 21, 2007Assignee: ABB Lummus Global Inc.Inventors: James M. Hildreth, Kerman Nariman Dukandar, Ronald M. Venner
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Publication number: 20040188324Abstract: The present invention relates to new crystalline molecular sieve SSZ-65 prepared using 1-[1-(4-chlorophenyl)-cyclopropylmethyl]-1-ethyl-pyrrolidinium or 1-ethyl-1-(1-phenyl-cyclopropylmethyl)-pyrrolidinium cation as a structure-directing agent, methods for synthesizing SSZ-65 and processes employing SSZ-65 in a catalyst.Type: ApplicationFiled: March 26, 2003Publication date: September 30, 2004Inventor: Saleh Elomari
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Publication number: 20030149320Abstract: A process for the alkylation of aromatics with olefins using a solid catalyst is disclosed, wherein the olefin ratio and/or the maximum olefin concentration in the alkylation catalyst bed is maintained less than an upper limit. Such operation can decrease the catalyst deactivation rate and the formation of diphenylalkanes. This invention is applicable to processes for the production of a wide variety of commercially important alkylated aromatics, including ethylbenzene and cumene.Type: ApplicationFiled: November 4, 2002Publication date: August 7, 2003Inventors: Gregory J. Gajda, James F. McGehee
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Patent number: 6555722Abstract: A countercurrent process for the alkylation of aromatic materials with olefins which takes place in a multi-bed system. The aromatic material is in the liquid phase; the olefin in the gaseous phase; and the catalyst in the solid phase. The olefinic material is fed below the catalyst bed in the gaseous phase and aromatic is fed as a liquid phase above the catalyst bed under conditions of temperature and pressure to maintain the aromatic product in the liquid phase and the olefin in the vapor phase.Type: GrantFiled: March 13, 2002Date of Patent: April 29, 2003Assignee: Catalytic Distillation TechnologiesInventor: Jamin Chen
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Patent number: 6544408Abstract: Process for the production of aromatic compounds, such as reforming, that uses at least one fixed catalyst bed with a base of platinum and 0.08% rhenium. In said process, before moving onto the bed, the feedstock undergoes a heat exchange with the effluent that is obtained from the process, whereby the exchange is carried out with a pressure drop that is less than 1 bar and a temperature difference that is less than 70° C. The beds are preferably radial and those that are located at the top of the reactor are covered by a cloth layer. The process preferably uses at least two fixed catalyst beds, whereby the first bed (in the direction of circulation of the feedstock) has an Re/Pt ratio by weight that is greater than that of the second bed, and whereby the second catalyst preferably contains at least 0.08% of Re.Type: GrantFiled: March 13, 2000Date of Patent: April 8, 2003Assignee: Institut Francais du PetroleInventor: Jean de Bonneville
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Patent number: 6479721Abstract: A process for the alkylation of aromatics with olefins using a solid catalyst is disclosed, wherein the olefin ratio and/or the maximum olefin concentration in the alkylation catalyst, bed is maintained less than an upper limit. Such operation can decrease the catalyst deactivation rate and the formation of diphenylalkanes. This invention is applicable to processes for the production of a wide variety of commercially important alkylated aromatics, including ethylbenzene and cumene.Type: GrantFiled: March 28, 2000Date of Patent: November 12, 2002Assignee: UOP LLCInventors: Gregory J. Gajda, James F. McGehee
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Publication number: 20020128529Abstract: A countercurrent process for the alkylation of aromatic materials with olefins which takes place in a multi-bed system. The aromatic material is in the liquid phase; the olefin in the gaseous phase; and the catalyst in the solid phase. The olefinic material is fed below the catalyst bed in the gaseous phase and aromatic is fed as a liquid phase above the catalyst bed under conditions of temperature and pressure to maintain the aromatic product in the liquid phase and the olefin in the vapor phase.Type: ApplicationFiled: March 13, 2002Publication date: September 12, 2002Applicant: CATALYTIC DISTILLATION TECHNOLOGIESInventor: Jamin Chen
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Patent number: 6395947Abstract: A method for preparing diarylethane is disclosed. Alkylation is carried out in a continuous type process at 100-300° C. under a pressure of 1-45 kg/cm2 G in the presence of a solid acid catalyst while a reactant mixture comprising alpha-methylbenzylalcohol and at least one aromatic hydrocarbon at a volume ratio of 1:1-10, is fed at a weight hourly space velocity of 0.1-10 h−1. The alpha-methylbenzylalcohol acts as an ailylating agent. Diarylethane can be prepared at a low cost, but a high production yield by the method.Type: GrantFiled: July 11, 2000Date of Patent: May 28, 2002Assignee: SK CorporationInventors: Byong Sung Kwak, Seung Gweon Hong, Tae Jin Kim
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Patent number: 6255549Abstract: A fraction of low bromine number mainly containing a styrenic compound/aromatic compound adduct can be attained, by feeding reaction materials of a styrenic compound and an aromatic compound to a fixed-bed flow reactor packed with a solid acid catalyst in a liquid phase at a temperature in the range of 40 to 350° C. to form a styrenic compound/aromatic compound adduct, in which (1) the feed of reaction materials is stopped when the bromine number of the above fraction is increased up to a predetermined value, (2) a saturated aromatic hydrocarbon having a mean value of the proportion of aromatic ring carbons in a molecule of 55% or more is fed to the reactor in a liquid phase at a temperature higher by 5 to 150° C. than that of the reaction mixture just before the above stopping, and (3) the feed of reaction materials is then restarted to obtain the fraction.Type: GrantFiled: April 19, 2000Date of Patent: July 3, 2001Assignee: Nippon Petrochemicals Company, LimitedInventors: Hideyuki Dohi, Shozo Hayashi
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Patent number: 6156949Abstract: There is provided a process for shape selective xylene methylation that involves contacting a feedstream which includes xylene and methanol under alkylation conditions, with a low activity catalyst. Xylene conversions of at least 15% at methanol utilization levels of 25% or greater are achieved by sequential injection of methanol The xylene methylation process has a selectivity for pseudocumene of over 85% and up to 99%, with a pseudocumene:durene ratio of up to 20 or more.Type: GrantFiled: December 28, 1998Date of Patent: December 5, 2000Assignee: Mobil Oil CorporationInventors: Stephen H. Brown, Mark F. Mathias
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Patent number: 6123836Abstract: Process for the removal of acid compounds contained in a hydrocarbon process stream by passing the process stream through a fixed bed of an adsorption material at conditions where the acid compounds adsorb on the material and withdrawing a purified hydrocarbon process stream, wherein water has been adsorbed on the material prior to contact with the hydrocarbon process stream.Type: GrantFiled: July 2, 1998Date of Patent: September 26, 2000Assignee: Haldor Topsoe A/SInventors: Sven Ivar Hommeltoft, Karsten Laurents
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Patent number: 5939597Abstract: Para-xylene is produced by toluene methylation by charging toluene and a methylating agent to a fluidized bed of catalyst at a rate sufficient to maintain the fluidized bed in a turbulent sub-transport flow regime, reacting the toluene with the methylating agent, and recovering para-xylene from the fluidized bed. The fluidizable catalyst is a microporous material having a Constraint Index of about 1 to about 12. The relative concentration of the catalyst particles having a major dimension of less than 40 microns is controlled at between about 5 and 35 weight percent. The catalyst particles have an apparent particle density of about 0.9 to 1.6 grams per cubic centimeter, a size range of about 1 to 150 microns, and average particle size of about 20 to 100 microns.Type: GrantFiled: October 21, 1997Date of Patent: August 17, 1999Assignee: Mobil Oil CorporationInventors: Ralph M. Dessau, David H. Olson, Robert A. Ware, Sadi Mizrahi
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Patent number: 5856606Abstract: Paraffins or other hydrocarbons are alkylated in a process featuring a reaction zone containing a pool of liquid maintained at its boiling point and containing a suspended solid catalyst, which allows the heat of reaction to vaporize a portion of the liquid phase feed hydrocarbon. The vapor phase withdrawn from the top of the reaction zone is at least partially recycled to the reaction zone either as vapor or liquid. The feed hydrocarbons are introduced to the bottom of the reaction zone as a vapor phase stream, which may contain hydrogen. The catalyst is suspended within the liquid in the reaction zone.Type: GrantFiled: September 27, 1996Date of Patent: January 5, 1999Assignee: UOP LLCInventor: Anil R. Oroskar
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Patent number: 5847254Abstract: This invention is directed to a fluorine-containing mordenite catalyst and use thereof in the manufacture of linear alkylbenzene (LAB) by alkylation of benzene with an olefin. The olefin may have from about 10 to 14 carbons. The fluorine-containing mordenite is prepared typically by treatment with an aqueous hydrogen fluoride solution. The benzene alkylation may be conducted using reactive distillation.Type: GrantFiled: February 8, 1996Date of Patent: December 8, 1998Assignee: Huntsman Petrochemical CorporationInventors: John F. Knifton, Prakasa Rao Anantaneni, P. Eugene Dai
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Patent number: 5847255Abstract: Process for the production of ethylbenzene by alkylation over a silicalite alkylation catalyst with the subsequent transalkylation of diethylbenzene with the alkylation catalyst and conditions selected to retard xylene production and also heavies production. A feedstock containing benzene and ethylene is applied to a multi-stage alkylation reaction zone having a plurality of series-connected catalyst beds containing a pentasil molecular sieve alkylation catalyst which is silicalite of a predominantly monoclinic symmetry having a silica/alumina ratio of at least 275. The feedstock is supplied to the alkylation reaction zone to cause gas-phase ethylation of benzene at a flow rate to provide a space velocity of benzene over the catalyst to produce a xylene concentration in the product of about 600 ppm or less based upon the ethylbenzene content.Type: GrantFiled: May 21, 1997Date of Patent: December 8, 1998Assignee: Fina Technology, Inc.Inventors: Ashim Kumar Ghosh, James T. Merrill, James R. Butler
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Patent number: 5789640Abstract: Disclosed is a process for continuous alkylation of aromatics or their derivatives in the presence of a solid acid catalyst in a liquid-solid circulating fluidized bed system, said system comprising a liquid-solid cocurrent upflow reactor, a sedimentation washing tower for the used catalyst, a liquid-solid cocurrent upflow regenerator, a sedimentation washing tower for the regenerated catalyst, and two vortical liquid-solid separators. By regeneration of the used catalyst, continuous alkylation process is achieved in this system.Type: GrantFiled: April 29, 1996Date of Patent: August 4, 1998Assignees: China Petro-Chemical Corporation, Tsinghua University, Research Institute of Petroleum Processing SinopecInventors: Yong Jin, Wugeng Liang, Zhanwen Wang, Zhiging Yu, Enze Min, Mingyuan He, Zhijian Da
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Patent number: 5777187Abstract: This invention is directed to a fluorine-containing mordenite catalyst and use thereof in the manufacture of linear alkylbenzene (LAB) by alkylation of benzene with an olefin. The olefin may have from about 10 to 14 carbons. The fluorine-containing mordenite is prepared typically by treatment with an aqueous hydrogen fluoride solution. The benzene alkylation may be conducted using reactive distillation. Yield and bromine index of the LAB may be improved by further alkylation using a fluorine containing clay catalyst such as montmorillonite clay.Type: GrantFiled: June 12, 1996Date of Patent: July 7, 1998Assignee: Huntsman Petrochemical CorporationInventors: John F. Knifton, Prakasa Rao Anantaneni
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Patent number: 5648579Abstract: A novel continuous process for the preparation of alkylated benzenes effected by solid catalysts which become deactivated under alkylation conditions uses a single catalyst zone for both reaction and catalyst flushing to prevent deactivation. The process utilizes a pulsed flow of the linear monoolefins into the catalyst zone during a reaction cycle with benzene acting as a desorbent for catalyst deactivating agents to prevent significant catalyst deactivation. The process can be generalized to encompass many types of reactions.Type: GrantFiled: February 21, 1995Date of Patent: July 15, 1997Assignee: UOPInventors: Santi Kulprathipanja, Joseph A. Kocal, Stanley A. Gembicki
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Patent number: 5395513Abstract: A continuous process for upgrading reformate feedstock or the like to reduce benzene content and increase octane fuel rating. The improved process comprises maintaining a fluidized bed of regenerable acid solid medium pore zeolite catalyst particles in a turbulent regime reaction zone, preferably maintained with a superficial gas velocity of 0.1 to 1 meter/sec. with reformate feedstock being introduced at a bottom portion of the reaction zone at a weight hourly space velocity (WHSV) of 0.1 to 5, based on active catalyst solids; reaction zone total pressure being less than 2000 kPa. The preferred catalyst particles have an average particle size of 20 to 100 microns (.mu.), with about 10 to 25% of the catalyst particles comprising fine particles having a particle size less than 30 microns; and the preferred zeolite catalyst comprises shape selective medium pore aluminosilicate zeolite having a constraint index of 1 to 12. The benzene is reacted by contacting reformate feedstock, such as C.sub.Type: GrantFiled: August 16, 1993Date of Patent: March 7, 1995Assignee: Mobil Oil CorporationInventors: Arthur A. Chin, Mohsen N. Harandi, Karen M. Millane, Robert A. Ware, James S. Warwick
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Patent number: 5262576Abstract: A method and apparatus for conducting a catalytic distillation process is provided which allows for maintaining a liquid level in selected portions of the catalyst bed. Three particular processes disclosed are the production of methyl tertiary butyl ether, tertiary butyl alcohol and cumene.Type: GrantFiled: February 19, 1992Date of Patent: November 16, 1993Assignee: Chemical Research & Licensing CompanyInventor: Lawrence A. Smith, Jr.
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Patent number: 5210348Abstract: A substantially benzene-free product suitable for gasoline blending is formed from a benzene-containing refinery stream. At least about 30% of the benzene initially present in the stream is catalytically alkylated with C.sub.2 -C.sub.4 olefins to form alkylated products. Most preferably, the alkylation zone is present in the distillation column and the alkylated products drop to the lower portion of the column and are recovered with the heavy fraction. Alternatively, the alkylation zone is downstream of the distillation column and a secondary distillation column removes the heavier alkylated products. The remaining light fraction is hydrogenated to convert substantially all of the remaining non-alkylated benzene to cyclohexane and is isomerized to boost the octane of C.sub.5 -C.sub.7 paraffins, preferably in a single reactor.Type: GrantFiled: May 23, 1991Date of Patent: May 11, 1993Assignee: Chevron Research and Technology CompanyInventors: C. Richard Hsieh, Richard C. Robinson
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Patent number: 5113031Abstract: A process for the catalytic distillation production of alkylated aromatic compounds is provided wherein the vapor pressure of the olefin may be increased while maintaining the same olefin feed rate and aromatic to olefin ratio. In one embodiment a side stream from the vapor from the second column below the catalyst and olefin feed is condensed and rerouted to the aromatic make up stream from the reflux drum. The vapor pressure of the olefin in the lower end of the first column in the catalyst bed is thus increased which increases the equilibrium concentration of the olefin in the liquid phase. In another embodiment of the invention the effective driving force for the reaction is increased by injecting the olefin at different heights within the catalyst bed. If additional olefin is injected more catalyst bed height would be required, but the additional catalyst is more that offset by the increased throughput at the same overall olefin conversion.Type: GrantFiled: November 9, 1990Date of Patent: May 12, 1992Inventor: Angel Sy
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Patent number: 4950831Abstract: An alkene is coupled with an aromatic hydrocarbon having an active hydrogen on a saturated alpha-carbon in the presence of an unsupported alkali metal as a catalyst under high shear agitation conditions. In preferred embodiments of the invention, the alkene is an alkene of 2-20 carbons, such as ethene or propene; the active hydrogen-containing aromatic hydrocarbon is an alkyl-benzene, such as toluene; the alkali metal is potassium or a potassium alloy; and the high shear agitation conditions are attained by operating a turbine-type impeller at a tip speed of at least about 5 m/sec.Type: GrantFiled: September 28, 1989Date of Patent: August 21, 1990Assignee: Ethyl CorporationInventors: James S. Staton, Ronald A. Turnblad, Jr., Robert B. Agee
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Patent number: 4292457Abstract: A new crystalline borosilicate comprises a molecular sieve material having the following composition in terms of mole ratios of oxides:0.9.+-.0.2 M.sub.2/n O:B.sub.2 O.sub.3 :YSiO.sub.2 :ZH.sub.2 O,wherein M is at least one cation, n is the valence of the cation, Y is a value within the range of 4 to about 600, and Z is a value within the range of 0 to about 5/8, and providing a specific X-ray diffraction pattern.The borosilicate is used to catalyze various processes, such as isomerization, disproportionation, alkylation, transalkylation, and conversion of alcohols into gasoline-boiling-range products, olefins, and/or aromatics.Type: GrantFiled: August 29, 1980Date of Patent: September 29, 1981Assignee: Standard Oil Company (Indiana)Inventor: Marvin R. Klotz