Having Plural Side-chains Patents (Class 585/321)
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Publication number: 20130237732Abstract: A method of making para-xylene or toluene is carried out by: (a) reacting a C5 or C6 linear monoene (itself, or formed from a C5 or C6 linear alkane) with a hydrogen acceptor in the presence of a hydrogen transfer catalyst to produce a C5 or C6 diene; (b) reacting the C5-C6 diene with ethylene to produce a cyclohexene having 1 or 2 methyl groups substituted thereon; and then (c) either (i) dehydrogenating the cyclohexene in the presence of a hydrogen acceptor with a hydrogen transfer catalyst to produce a compound selected from the group consisting of para-xylene and toluene, or (ii) dehydrogenating the cyclohexene in the absence of a hydrogen acceptor with a dehydrogenation catalyst, to produce para-xylene or toluene.Type: ApplicationFiled: May 2, 2013Publication date: September 12, 2013Applicant: The University of North Carolina at Chapel HillInventors: Maurice Brookhart, Michael Findlater, Damien Guironnet, Thomas Warren Lyons
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Publication number: 20130214207Abstract: 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: ApplicationFiled: October 24, 2011Publication date: August 22, 2013Inventor: Keki Hormusji Gharda
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Publication number: 20130217936Abstract: The invention concerns a method of making a catalyst adapted for isomerization of xylenes.Type: ApplicationFiled: January 25, 2013Publication date: August 22, 2013Applicant: ExxonMobil Chemical Patents Inc.Inventors: Jane C. Cheng, Doron Levin
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Publication number: 20130178650Abstract: A method of manufacturing aromatic hydrocarbons, which are suitable for the production of terephthalic acid, from tall oil-based raw material. According to the invention, the raw material that contains tall oil or its fraction is catalytically deoxygenated with hydrogen, and one or more aromatic hydrocarbons that can be converted into terephthalic acid are separated from the deoxygenated reaction yield. The deoxygenation catalyst is a NiMo catalyst and, in addition, a cracking catalyst can be used, such as an acidic zeolite catalyst. The separated hydrocarbon can be p-xylene, o-xylene or p-cymene. According to the invention, these can be converted by oxidation and, when needed, by a re-arrangement reaction into terephthalic acid that is suitable for the source material of the manufacture of bio-based polyethylene terephthalate.Type: ApplicationFiled: June 3, 2011Publication date: July 11, 2013Applicant: STORA ENSO OYJInventors: Ali Harlin, Jari Räsänen, Tapani Penttinen
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Publication number: 20130165709Abstract: A method of producing a hydrocarbon fuel from a hydrocarbon-containing gas is disclosed and described. A hydrocarbon-containing gas is produced (10) containing from about 25% to about 50% carbon dioxide and can be reformed (12) with a steam gas to form a mixture of hydrogen, carbon monoxide and carbon dioxide. The reforming can be a composite dry-wet reforming or a tri-reforming step. The mixture of hydrogen, carbon monoxide and carbon dioxide can be at least partially converted (14) to a methanol product. The methanol product can be converted to the hydrocarbon fuel (18), optionally via UME synthesis (16). The method allows for effective fuel production with low catalyst fouling rates and for operation in an unmanned, self-contained unit at the source of the hydrocarbon-producing gas.Type: ApplicationFiled: February 15, 2013Publication date: June 27, 2013Applicant: Oberon Fuels, Inc.Inventor: Oberon Fuels, Inc.
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Publication number: 20130131413Abstract: A reforming process using a medium pore zeolite under conditions to facilitate the conversion of C8 paraffinic compounds to para-xylene is provided. Para-xylene is produced at greater than thermodynamic equilibrium concentrations using the process.Type: ApplicationFiled: January 11, 2013Publication date: May 23, 2013Inventors: Cong-Yan Chen, Ann Jia-Bao Liang, Stephen Joseph Miller, James Nathan Ziemer
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Publication number: 20130060070Abstract: The invention relates to methods for producing fluid hydrocarbon products, and more specifically, to methods for producing fluid hydrocarbon product via catalytic pyrolysis. The reactants comprise solid hydrocarbonaceous materials, and hydrogen or a source of hydrogen (e.g., an alcohol). The products may include specific aromatic compounds (e.g., benzene, toluene, naphthalene, xylene, etc.).Type: ApplicationFiled: August 13, 2012Publication date: March 7, 2013Applicant: UNIVERSITY OF MASSACHUSETTSInventors: George W. Huber, Huiyan Zhang, Torren Carlson
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Publication number: 20130023706Abstract: This invention relates to compositions comprising fluid hydrocarbon products, and to methods for making fluid hydrocarbon products via catalytic pyrolysis. Some embodiments relate to methods for the production of specific aromatic products (e.g., benzene, toluene, naphthalene, xylene, etc.) via catalytic pyrolysis. Some such methods involve the use of a composition comprising a mixture of a solid hydrocarbonaceous material and a heterogeneous pyrolytic catalyst component. The methods described herein may also involve the use of specialized catalysts. For example, in some cases, zeolite catalysts may be used.Type: ApplicationFiled: August 30, 2012Publication date: January 24, 2013Applicant: University of MassachusettsInventors: George W. Huber, Yu-Ting Cheng, Torren Carlson, Tushar Vispute, Jungho Jae, Geoff Tompsett
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Publication number: 20120316373Abstract: One exemplary embodiment may be a process for producing one or more alkylated aromatics. Generally, the process includes providing a first stream including an effective amount of benzene for alkylating benzene from a fractionation zone, providing a second stream including an effective amount of ethene for alkylating benzene from a fluid catalytic cracking zone, providing at least a portion of the first and second streams to an alkylation zone; and passing at least a portion of an effluent including ethylbenzene from the alkylation zone downstream of a para-xylene separation zone.Type: ApplicationFiled: June 9, 2011Publication date: December 13, 2012Applicant: UOP, LLCInventors: Robert Haizmann, Laura E. Leonard, Paula L. Bogdan
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Publication number: 20120271082Abstract: The method of the present invention provides a high yield pathway to 2,5-dimethylhexadiene from renewable isobutanol, which enables economic production of renewable p-xylene (and subsequently, terephthalic acid, a key monomer in the production of PET) from isobutanol. In addition, the present invention provides methods for producing 2,5-dimethylhexadiene from a variety of feed stocks that can act as “equivalents” of isobutylene and/or isobutyraldehyde including isobutanol, isobutylene oxide, and isobutyl ethers and acetals. Catalysts employed in the present methods that produce 2,5-dimethylhexadiene can also catalyze alcohol dehydration, alcohol oxidation, epoxide rearrangement, and ether and acetal cleavage.Type: ApplicationFiled: April 19, 2012Publication date: October 25, 2012Applicant: Gevo, Inc.Inventors: Thomas Jackson Taylor, Joshua D. Taylor, Matthew W. Peters, David E. Henton
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Publication number: 20120203042Abstract: This invention relates to compositions and methods for fluid hydrocarbon product, and more specifically, to compositions and methods for fluid hydrocarbon product via catalytic pyrolysis. Some embodiments relate to methods for the production of specific aromatic products (e.g., benzene, toluene, naphthalene, xylene, etc.) via catalytic pyrolysis. Some such methods may involve the use of a composition comprising a mixture of a solid hydrocarbonaceous material and a heterogeneous pyrolytic catalyst component. In some embodiments, an olefin compound may be co-fed to the reactor and/or separated from a product stream and recycled to the reactor to improve yield and/or selectivity of certain products. The methods described herein may also involve the use of specialized catalysts. For example, in some cases, zeolite catalysts may be used. In some instances, the catalysts are characterized by particle sizes in certain identified ranges that can lead to improve yield and/or selectivity of certain products.Type: ApplicationFiled: September 9, 2010Publication date: August 9, 2012Applicants: ANELLOTECH, INC., UNIVERSITY OF MASSACHUSETTSInventors: George W. Huber, Anne Mae Gaffney, Jungho Jae, Yu-Ting Cheng
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Publication number: 20120149958Abstract: 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: ApplicationFiled: November 23, 2011Publication date: June 14, 2012Inventors: Justin M. Ellrich, Robert D. Strack, John W. Rebeck, Allen S. Gawlik, Larry L. Iaccino, Glenn C. Wood, Stephen H. Brown
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Publication number: 20120095272Abstract: 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: ApplicationFiled: June 18, 2010Publication date: April 19, 2012Applicant: THE TEXAS A&M UNIVERSITY SYSTEMInventors: Mahmoud M. El-Halwagi, Kenneth R. Hall, Harold Dennis Spriggs
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Publication number: 20120036889Abstract: A process for converting a gaseous hydrocarbon feed comprising methane to an aromatic hydrocarbon is integrated with liquefied natural gas (LNG) and/or pipeline gas production. In the integrated process, the gaseous hydrocarbon feed is supplied to a conversion zone comprising at least one dehydroaromatization catalyst and is contacted with the catalyst under conversion conditions to produce a gaseous effluent stream comprising at least one aromatic compound, unreacted methane and H2. The gaseous effluent stream is then separated into a first product stream comprising said at least one aromatic compound and a second product stream comprising unreacted methane and H2. The second product stream is further separated into a methane-rich stream and a hydrogen-rich stream and at least part of the methane-rich stream is passed to LNG and/or pipeline gas production.Type: ApplicationFiled: July 18, 2011Publication date: February 16, 2012Inventors: Larry L. Iaccino, Robert D. Denton, Garth M. Norman, James R. Lattner
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Publication number: 20110245543Abstract: Processes and reactor systems are provided for the conversion of oxygenated hydrocarbons to hydrocarbons, ketones and alcohols useful as liquid fuels, such as gasoline, jet fuel or diesel fuel, and industrial chemicals. The process involves the conversion of mono-oxygenated hydrocarbons, such as alcohols, ketones, aldehydes, furans, carboxylic acids, diols, triols, and/or other polyols, to C4+ hydrocarbons, alcohols and/or ketones, by condensation. The oxygenated hydrocarbons may originate from any source, but are preferably derived from biomass.Type: ApplicationFiled: June 17, 2011Publication date: October 6, 2011Applicant: Virent Energy Systems, Inc.Inventors: Randy D. Cortright, Paul G. Blommel
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Publication number: 20110130603Abstract: This disclosure relates to a catalyst system adapted for processing aromatic feedstreams comprising C9+ aromatic feedstock to produce at least one xylene.Type: ApplicationFiled: October 14, 2010Publication date: June 2, 2011Inventor: Doron Levin
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Publication number: 20110009682Abstract: This invention relates to a method of efficiently producing a high-purity para-substituted aromatic hydrocarbon while suppressing caulking without requiring isomerization-adsorption separation steps, and more particularly to a method of producing a para-substituted aromatic hydrocarbon, characterized in that a methylating agent and an aromatic hydrocarbon are reacted in the presence of a catalyst formed by coating MFI type zeolite having a particle size of not more than 100 ?m with a crystalline silicate.Type: ApplicationFiled: March 26, 2009Publication date: January 13, 2011Applicant: JX NIPPON OIL & ENERGY CORPORATIONInventors: Koichi Matsushita, Chikanori Nakaoka, Naoharu Igarashi, Makoto Oyamada
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Publication number: 20100228066Abstract: The present invention provides an integrated process for the production of p-xylene, comprising the steps of A) separating a mixed feedstock containing benzene, toluene, C8 aromatic hydrocarbons, C9 and higher aromatic hydrocarbons, and non-aromatic hydrocarbons from a reforming unit, to obtain a first benzene stream, a first toluene stream, a first C8 aromatic hydrocarbon stream, a stream of C9 and higher aromatic hydrocarbons, and a stream of non-aromatic hydrocarbons; B) feeding the stream of C9 and higher aromatic hydrocarbons from step A) to a C9 and higher aromatic hydrocarbon dealkylation unit, where dealkylation reaction occurs in the presence of hydrogen, and separating the reaction effluent to obtain a second benzene stream, a second toluene stream, and a second C8 aromatic hydrocarbon stream; C) feeding both the first toluene stream and the second toluene stream to a toluene selective disproportionation unit, where toluene selective disproportionation reaction occurs in the presence of hydrogen toType: ApplicationFiled: November 20, 2009Publication date: September 9, 2010Applicants: 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: 7727490Abstract: One exemplary embodiment can include an aromatic production apparatus. The aromatic production apparatus can include a first fractionation zone, a second fractionation zone, and a third fractionation zone. Generally, the first fractionation zone can provide a stream rich in an aromatic C8? and a stream rich in an aromatic C9, the second fractionation zone can separate at least one of benzene and optionally toluene from a transalkylation zone effluent and provide a feed to the first fractionation zone, and the third fractionation zone can receive the stream rich in the aromatic C8? from the first fractionation zone. An effluent from the third fractionation zone can be directly comprised in a para-xylene-separation zone feed to a para-xylene-separation zone.Type: GrantFiled: August 17, 2007Date of Patent: June 1, 2010Assignee: UOP LLCInventor: Lubo Zhou
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Publication number: 20100094068Abstract: This disclosure relates to a catalyst system adapted for transalkylation a C9+ aromatic feedstock with a C6-C7 aromatic feedstock, comprising: (a) a first catalyst comprising a first molecular sieve having a Constraint Index in the range of 3-12 and 0.01 to 5 wt. % of at least one source of a first metal element of Groups 6-10; and (b) a second catalyst comprising a second molecular sieve having a Constraint Index less than 3 and 0 to 5 wt. % of at least one source of a second metal element of Groups 6-10, wherein the weight ratio of the first catalyst over the second catalyst is in the range of 5:95 to 75:25 and wherein the first catalyst is located in front of the second catalyst when they are brought into contacting with the C9+ aromatic feedstock and the C6-C7 aromatic feedstock in the present of hydrogen.Type: ApplicationFiled: December 17, 2009Publication date: April 15, 2010Inventor: Doron Levin
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Patent number: 7411101Abstract: 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 transkylation reactor zone.Type: GrantFiled: February 6, 2002Date of Patent: August 12, 2008Assignee: ExxonMobil Chemical Patents Inc.Inventors: Shiou-Shan Chen, Henry Hwang
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Patent number: 7381858Abstract: Processes are disclosed for production of purified products from a fluid mixtures of C8 aromatics by means of integration of perm-selective separations with purified product recovery operations. The perm-selective separations of the invention comprise of one or more devices using polymeric perm-selective membrane devices to separate a meta-xylene enriched stream from fluid mixtures of C8 aromatics thereby producing a fluid comprising the remaining aromatic compounds which advantageously includes para-xylene. Processes of the invention are particularly useful for recovery of very pure meta-xylene and para-xylene co-products from liquid mixtures even containing ethylbenzene as well as the three xylene isomers.Type: GrantFiled: January 30, 2004Date of Patent: June 3, 2008Assignee: BP Corporation North America Inc.Inventors: George A. Huff, Jr., Bo Chen, Craig W. Colling, Jeffrey T. Miller
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Patent number: 7358414Abstract: Processes and apparatus are disclosed for recovery of purified products from a fluid mixture by means of integrated perm-selective separations with purified product recovery operations. More particularly, integrated processes of the invention comprise separations by means of one or more devices using polymeric membranes coupled with recovery of purified products by means of fractional crystallization and/or selective sorption. Processes of the invention are particularly useful for recovery of a very pure aromatic isomer when processing aromatic starting materials, for example, a pure para-xylene product from liquid mixtures even containing ethylbenzene as well as the three xylene isomers.Type: GrantFiled: January 30, 2004Date of Patent: April 15, 2008Inventors: Jeffrey T. Miller, Bo Chen, Craig W. Colling, George A. Huff, Jr., Marvin L. Cadwell
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Publication number: 20030125591Abstract: In a process for the selective production of meta-diisopropylbenzene, a C9+ aromatic hydrocarbon feedstock containing meta- and ortho-diisopropylbenzene is contacted with benzene under conversion conditions with a catalyst comprising a molecular sieve selected from the group consisting of zeolite beta, mordenite and a porous crystalline inorganic oxide material having an X-ray diffraction pattern including the d-spacing maxima at 12.4±0.25, 6.9±0.15, 3.57±0.07 and 3.42±0.07 Angstrom. The contacting step selectively converts ortho-diisopropylbenzene in the feedstock to produce an effluent in which the ratio of meta-diispropylbenzene to ortho-diispropylbenzene is greater than that of the feedstock. The effluent is the fed to a separation zone for recovery of a product rich in meta-diisopropylbenzene.Type: ApplicationFiled: December 13, 2002Publication date: July 3, 2003Inventors: William A. Weber, Charles Morris Smith, Francis S. Bryan, Stephen H. Brown, Jane C. Cheng
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Publication number: 20020065444Abstract: A process and a system for increasing para-xylene production from a C8 aromatic feedstream by coupling at least one xylene isomerization reactor with at least one pressure swing adsorption unit or temperature swing absorption unit to produce a product having a super-equilibrium para-xylene concentration. This product is then subjected to para-xylene separation and purification.Type: ApplicationFiled: February 22, 2001Publication date: May 30, 2002Inventors: Harry W. Deckman, Ronald Richard Chance, John Di-Yi Ou, James Alexander McHenry, Juan Joes Reinoso
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Patent number: 6392112Abstract: Polyacetylene compounds and process for the preparation thereof from a chiral dihydroxy amide are described. The compounds preferably have diacyl groups attached to the amide. The compounds are useful for making films which are electrically conductive, near infrared absorbing, polarizing, and have the optical characteristic and other properties of polyacetylenes.Type: GrantFiled: August 23, 2000Date of Patent: May 21, 2002Assignee: Board of Trustees of Michigan State UniversityInventors: Rawle I. Hollingsworth, Guijun Wang
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Patent number: 6380450Abstract: Tetrahydroindene is dehydrogenated in a vapor phase in the presence of a metallic catalyst, e.g., a nickel-molybdenum catalyst, to produce indene, which is industrially useful in high yield while inhibiting the catalyst from suffering a decrease in activity. In particular, a higher yield can be attained by a method in which tetrahydroindene is dehydrogenated to first convert it into indane, which is further dehydrogenated to obtain indene.Type: GrantFiled: April 15, 2000Date of Patent: April 30, 2002Assignee: Nippon Petrochemicals Company, LimitedInventor: Yasuo Matsumura
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Patent number: 6376733Abstract: This invention relates to a process and a chemical plant for the production primarily of paraxylene. In particular the process and chemical plant utilise zeolite membranes for enhanced paraxylene production.Type: GrantFiled: January 25, 1996Date of Patent: April 23, 2002Assignee: ExxonMobil Chemical Patents Inc.Inventors: John Michael Ferraro, Robert Michael Osman, John Di-Yi Ou, Graeme Ian Cox, James Richardson Lattner, Kenneth Ray Clem
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Patent number: 6359184Abstract: Disclosed herein is a catalyst composition for transalkylation of alkylaromatic hydrocarbons which exhibits the percent conversion of ethyltoluene higher than 50 wt %, is composed of mordenite (100 pbw), inorganic oxide and/or clay (25-150 pbw), and at least one metal component of rhenium, platinum, and nickel, and contains mordenite such that the maximum diameter of secondary particles of mordenite is smaller than 10 &mgr;m. Disclosed also herein is a process for producing xylene by the aid of said catalyst from alkylaromatic hydrocarbons containing C9 alkylaromatic hydrocarbons containing more than 5 wt % ethyltoluene and less than 0.5 wt % naphthalene, in the presence of hydrogen.Type: GrantFiled: January 19, 2000Date of Patent: March 19, 2002Assignee: Toray Industries, Inc.Inventors: Hajime Kato, Hitoshi Tanaka, Kazuyoshi Iwayama, Ryoji Ichioka
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Patent number: 6204422Abstract: A rational technical process for producing dialkylnaphthalenes from petroleum-derived starting materials which exist in abundance is established.Type: GrantFiled: November 4, 1998Date of Patent: March 20, 2001Assignee: Fuji Oil Company, Ltd.Inventors: Toshio Tsutsui, Takumi Sasaki, Yoshitaka Satou, Osamu Kubota, Shinichi Okada, Masaki Fujii
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Patent number: 6143166Abstract: This process relates to reforming a full-boiling range hydrocarbon feed in two parallel stages while maximizing the catalyst life of the heavy cut reformer and/or reducing the complexity of the plant by preferentially sending the higher purity Aromax.RTM. hydrogen to the heavy cut reformer.Type: GrantFiled: August 16, 1999Date of Patent: November 7, 2000Assignee: Chevron Chemical Co. LLCInventor: Gerald J. Nacamuli
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Patent number: 6015930Abstract: The invention discloses a method of making 2,6-dimethylnaphthalene from any DMN with one methyl on each ring in a two-step hydroisomerization/dehydrogenation process. The catalyst used in the hydroisomerization step is an acidic catalyst such as a silica aluminum catalyst with a hydrogenation/dehydrogenation metal. The catalyst used in the dehydrogenation step is a reforming type catalyst.Type: GrantFiled: July 14, 1997Date of Patent: January 18, 2000Assignee: Chevron Chemical CompanyInventors: Donald S. Santilli, Cong-Yan Chen
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Patent number: 5958217Abstract: A hydrocarbon feed is reformed to enhance para-xylene yield and to minimize ethylbenzene production. The hydrocarbon feed is subjected to catalytic aromatization at elevated temperatures in the presence of hydrogen, using a non-acidic catalyst having at least one Group VIII metal on a non-acidic zeolite support, to produce a reformate stream containing ethylbenzene and xylenes in which the para-xylene content of the xylene fraction is less than equilibrium. Then, at least some of the reformate is reacted at elevated temperatures in the presence of hydrogen, using an intermediate pore size zeolitic catalyst having a modifier in the absence of a Group VIII metal, to isomerize the non-equilibrium xylene fraction. The modifier can be magnesium, calcium, barium, or phosphorus. At least 20 wt. % of the ethylbenzene in the reformate is converted by hydrodealkylation.Type: GrantFiled: November 15, 1995Date of Patent: September 28, 1999Assignee: Chevron Chemical Company LLCInventors: Gerald J. Nacamuli, Roger F. Vogel
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Patent number: 5436402Abstract: A method for preparing a high-purity p-isobutylstyrene is here disclosed which comprises the first step of reacting o- and/or m-isobutylethylbenzene, if necessary, together with isobutylbenzene, in the presence of an acid catalyst in a liquid phase at a reaction temperature of -10.degree. to 600.degree. C. so that the production of sec-butylethylbenzene in butylethylbenzene may not exceed 20% by weight, in order to form a mixture of p-isobutylethylbenzene and sec-butylethylbenzene; and the second step of bringing the mixture of p-isobutylethylbenzene and sec-butylethylbenzene recovered from the first step into contact with a dehydrogenation metal catalyst containing at least one metal selected from the groups Ib, IIb, VIa, VIIa and VIII of the periodic table at a reaction temperature of 300.degree. to 650.degree. C. under a reaction pressure of 50 kg/cm.sup.2 or less in a gaseous phase.Type: GrantFiled: October 17, 1994Date of Patent: July 25, 1995Assignee: Nippon Petrochemicals Co., Ltd.Inventors: Isoo Shimizu, Yasuo Matsumura, Yuichi Tokumoto, Kazumichi Uchida
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Patent number: 5300717Abstract: In a multi-step process, dixylylpropane is obtained inter alia via the hitherto unknown 1,2-dimethyl-4-(.alpha.-chloroisopropyl)benzene, the readily accessible compounds o-xylene and propene being employed as starting compounds. The process yields the desired compound in high yield and isomer purity and is distinguished by a small amount of by-products. It is therefore particularly suitable for further processing without problems. The process involves the sequence of (a) Friedel-Crafts alkylation of ortho-xylene with propylene, (b) dehydrogenation of the isoproplyxlene into isopropenylxylene, (c) which is then hydrochlorinated into chloroisopropylxylene, (d) and then alkylated with a second ortho-xylene modecule to obtain the final product dixylylpropane.Type: GrantFiled: April 8, 1993Date of Patent: April 5, 1994Assignee: Hoechst AktiengesellschaftInventor: Freimund Rohrscheid
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Patent number: 5008479Abstract: A process for production of 2,6-dimethylnaphthalene is disclosed, comprising the steps: (1) an acylation step where p-tolyl sec-butyl ketone is produced from toluene, n-butene and carbon monoxide: (2) a hydrogenation step where the carbonyl group of the p-tolyl sec-butyl ketone is hydrogenated: and (3) a dehydrogenation and cyclization step where the hydrogenated product obtained above is subjected to dehydrogenation and cyclization to produce the desired 2,6-dimethylnaphthalene. The process enables efficiently producing a high quality or high purity 2,6-dimethylnaphthalene.Type: GrantFiled: July 5, 1989Date of Patent: April 16, 1991Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takafumi Abe, Seiji Uchiyama, Takahiro Ojima, Koichi Kida
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Patent number: 4899004Abstract: Trimethylbenzene is selectively prepared by contacting a C.sub.1 to C.sub.4 alkane with magnesium under reaction conditions to produce a reaction product. The reaction product thus produced, is contacted with water or a lower alcohol to promote a protonolysis reaction. The reaction mixture or a fraction thereof from the protonolysis reaction is contacted with a metal containing Y zeolite catalyst under reaction conditions to produce trimethylbenzene.Type: GrantFiled: September 9, 1988Date of Patent: February 6, 1990Assignee: Conoco Inc.Inventors: Joe D. Allison, Richard M. Tillman
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Patent number: 4855518Abstract: A method for producing p-alkylstyrene which is characterized in that side reaction scarcely occurs, catalyst and unreacted material are easily recovered for the reuse, the p-position selectivity is excellent and yield of aimed product is high. In the method, monoalkylbenzene having an alkyl group with 3 or more carbon atoms is reacted with acetaldehyde in the presence of hydrogen fluoride catalyst under the conditions of a temperature of 0.degree. C. or lower, a molar ratio of 2 to 100 in "alkylbenzene/acetaldehyde", the other molar ratio of 1.7 to 300 in "hydrogen fluoride/acetaldehyde", the proportion of hydrogen fluoride to the sum of hydrogen fluoride and water in the reaction system of 65% by weight or higher, and the concentration of acetaldehyde in the reaction system of 1.0% by weight or lower to obtain 1,1-bis(p-alkylphenyl)ethane, and then subjecting it to catalytic cracking at a temperature in the range of 200.degree. to 650.degree. C. in the presence of an acid catalyst.Type: GrantFiled: July 19, 1988Date of Patent: August 8, 1989Assignee: Nippon Petrochemicals Company, LimitedInventors: Isoo Shimizu, Yuuichi Tokumoto
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Patent number: 4855519Abstract: A method for producing arylethylene comprising four steps of: (I) bringing 1,1-diarylethane into contact with an acid catalyst in the presence of an inert gas to crack said compound into arylethylenes and alkylbenzenes; (II) separating the reaction mixture obtained in the above cracking step (I) into at least a fraction mainly containing 1,1-diarylethane; (III) bringing said fraction mainly containing 1,1-diarylethane into contact with hydrogen gas in the presence of a hydrogenation catalyst; and (IV) re-cracking hydrogenated fraction obtained in the preceding hydrogenation step (III) by bringing it into said cracking step (I).Particularly, this method is useful for producing p-isobutylstyrene which is a starting material for preparing a valuable medicine of ibuprofen.Type: GrantFiled: November 14, 1988Date of Patent: August 8, 1989Assignee: Nippon Petrochemicals CompanyInventors: Isoo Shimizu, Hitoshi Mitsuyuki, Kazumichi Uchida, Yuuichi Tokumoto
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Patent number: 4755627Abstract: Diisopropenylbenzene is a monomer that can be used in the preparation of many useful polymers and is also a chemical intermediate that can be employed in a number of chemical processes. Diisopropenylbenzene is normally synthesized by the dehydrogenation of diisopropylbenzene. Unfortunately in this dehydrogenation process a number of olefinic impurities are produced as by-products. This invention discloses a process for the separation of diisopropenylbenzene from these impurities and for recycling some of the impurities.Type: GrantFiled: November 24, 1986Date of Patent: July 5, 1988Assignee: The Goodyear Tire & Rubber CompanyInventors: Howard A. Colvin, Ronald D. Fiedler, Joel Muse, Jr., Donald E. Smith
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Patent number: 4665246Abstract: The process of producing ethynyl aromatic compounds which are useful as intermediates in the preparation of 3-dimensional carbon-carbon structures for aerospace and military applications and as starting materials in the preparation of organic semi-conductors. The ethynyl aromatic compounds may be any of the classes illustrated in FIGS. 1, 2 and 3 of the drawing. Starting compounds for the process may by any compound from the classes illustrated in FIGS. 4, 5 and 6. The starting compound is reacted in the presence of a Friedel-Crafts catalyst in a suitable solvent with an acyl compound from the class illustrated in FIG. 7 to yield a compound within the classes illustrated in FIGS. 8, 9 and 10. The carbonyl groups in this compound are reduced to yield a corresponding alcohol. Each hydroxy group in the alcohol is converted to an easily eliminatable group, e.g., by reacting it with methane sulfonyl chloride, when subjected to basic conditions.Type: GrantFiled: March 9, 1984Date of Patent: May 12, 1987Assignee: Chem Biochem Research, Inc.Inventor: Chris Anderson
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Patent number: 4528413Abstract: Diisopropenylbenzene is a monomer that can be used in the preparation of many useful polymers and is also a chemical intermediate that can be employed in a number of chemical processes. Diisopropenylbenzene is normally synthesized by the dehydrogenation of diisopropylbenzene. Unfortunately in this dehydrogenation process a number of olefinic impurities are produced as by-products. This invention discloses a process for the separation of diisopropenylbenzene from these impurities and for recycling some of the impurities.Type: GrantFiled: March 5, 1984Date of Patent: July 9, 1985Assignee: The Goodyear Tire & Rubber CompanyInventors: Howard A. Colvin, Ronald D. Fiedler, Joel Muse, Jr., Donald E. Smith
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Patent number: 4405513Abstract: Compounds useful as fluorescers in aqueous chemiluminescent mixtures, have the formula ##STR1## wherein X and Y represent hydrogen, or a quaternary ammonium group ##STR2## wherein m is 0 or 1n is an integer from one to fiveR.sub.1, R.sub.2, R.sub.3 represent C.sub.1 -C.sub.8 alkyl, or two of them form ring with N to make piperidinium, morpholinium or pyrrolidinium, andZ is an ion,the compound having at least one such quaternary group.Type: GrantFiled: June 16, 1982Date of Patent: September 20, 1983Assignee: American Cyanamid CompanyInventor: Victor M. Kamhi
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Patent number: 4401585Abstract: Bis(p-alkylphenylethynyl)anthracenes are described for use as fluorescer components in chemiluminescent reaction mixtures and in precursor solutions or solid mixtures. Chemiluminescent mixtures comprising these fluorescers are shown to generate higher light capacity and higher quantum yields than those made with similar prior art fluorescers.Type: GrantFiled: January 21, 1982Date of Patent: August 30, 1983Assignee: American Cyanamid CompanyInventors: Frank J. Arthen, Jr., Robert J. Manfre
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Patent number: 4211886Abstract: Benzene, toluene and xylene are produced in high yield from aromatic naphtha by a processing technique which combines (1) high temperature isomerization of eight carbon atom aromatics over a catalyst having relatively low activity and constrained access to the internal pore surface and (2) processing of heavy single ring aromatics of nine or more carbon atoms together with toluene under dealkylation/transalkylation conditions. The effluents of the two reactions are blended for processing through separation and recovery equipment. The unique chemistry of the isomerization stage results in splitting off alkyl side chains of two or more carbon atoms while retaining methyl groups attached to aromatic rings. Because of these reaction characteristics, full range reformate is advantageously added to the isomerizer charge for conversion to methyl benzene and redistribution of methyl groups to the thermodynamic equilibrium values.Type: GrantFiled: September 25, 1978Date of Patent: July 8, 1980Assignee: Mobil Oil CorporationInventors: Samuel A. Tabak, Roger A. Morrison
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Patent number: 4169865Abstract: A process for the dimerization and cyclization of isobutene to form, as preferred product, paraxylene in which the whole of the product of isobutene dimerization (including unreacted feedstock) is contacted with a catalyst for the cyclization of the isobutene dimer. The process is operable in a single dimerization/cyclization stage or in separate dimerization and cyclization stages with no intermediate separation of products. Optionally, the isobutene feedstock is provided by dehydrogenation of isobutane, unreacted isobutane in the resulting feedstock being carried through the dimerization/cyclization and eventually recycled.Type: GrantFiled: June 13, 1978Date of Patent: October 2, 1979Assignee: Imperial Chemical Industries LimitedInventors: John R. Bamforth, Raymond Higgins
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Patent number: 4158025Abstract: Selected aromatic hydrocarbon concentrates -- benzene, mixed xylenes -- are produced by way of a combination process which involves catalytic reforming followed by dealkylation. Although the process affords flexibility respecting the precise aromatic concentrate produced, it is particularly directed toward the maximization of benzene.Type: GrantFiled: March 13, 1978Date of Patent: June 12, 1979Assignee: UOP Inc.Inventor: George E. Addison
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Patent number: 4158026Abstract: Selected aromatic hydrocarbon concentrates -- benzene, mixed xylenes, etc. -- are produced by way of a combination process which involves catalytic reforming followed by hot flash separation of a portion of the reformed product and dealkylation of the resulting hot flash liquid phase in admixture with a second portion of the reformed product. Although the process affords flexibility respecting the precise aromatic concentrate produced, it is particularly directed toward the maximization of benzene from normally liquid naphtha hydrocarbons boiling up to about 425.degree. F. (218.degree. C.).Type: GrantFiled: March 13, 1978Date of Patent: June 12, 1979Assignee: UOP Inc.Inventor: George E. Addison
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Patent number: 4157355Abstract: Selected aromatic hydrocarbon concentrates--benzene, mixed xylenes, etc.--are produced by way of a combination process which involves catalytic reforming followed by hot flash separation and dealkylation of the separated hot flash liquid phase. Although the process affords flexibility respecting the precise aromatic concentrate produced, it is particularly directed toward the maximization of benzene.Type: GrantFiled: March 13, 1978Date of Patent: June 5, 1979Assignee: UOP Inc.Inventor: George E. Addison