To Produce Aromatic Patents (Class 585/319)
  • Patent number: 6392109
    Abstract: An integrated process for producing alkylbenzenes, sulfonated alkylbenzenes and/or alkylcyclohexanes from syngas is disclosed. The process involves subjecting syngas to Fischer-Tropsch conditions. Fractions rich in C6-8 and C18-26 hydrocarbons are isolated from the resulting product stream. The C6-8 fraction is subjected to catalytic reforming conditions to form aromatics. The C18-26 fraction may include sufficient olefins for use in an alkylation reaction with the aromatics. Optionally, the fraction may be subjected to dehydrogenation conditions to provide additional olefins. The resulting olefins are reacted with the aromatics in an alkylation reaction to yield alkylbenzenes. Unconverted olefins, paraffins, and aromatics can be obtained from the product stream via fractional distillation and recycled to form additional products. The alkylbenzenes can be hydrogenated to yield alkylcyclohexanes, which are useful as synlubes or as components in lube oil compositions.
    Type: Grant
    Filed: February 29, 2000
    Date of Patent: May 21, 2002
    Assignee: Chevron U.S.A. Inc.
    Inventors: Dennis J. O'Rear, William L. Schinski
  • Patent number: 6380450
    Abstract: 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: Grant
    Filed: April 15, 2000
    Date of Patent: April 30, 2002
    Assignee: Nippon Petrochemicals Company, Limited
    Inventor: Yasuo Matsumura
  • Patent number: 6359184
    Abstract: 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: Grant
    Filed: January 19, 2000
    Date of Patent: March 19, 2002
    Assignee: Toray Industries, Inc.
    Inventors: Hajime Kato, Hitoshi Tanaka, Kazuyoshi Iwayama, Ryoji Ichioka
  • Patent number: 6350929
    Abstract: Process for isomerization of a feedstock that contains aromatic compounds with eight carbon atoms characterized in that it comprises at least one isomerization stage a) that is carried out in the presence of a catalyst that contains at least one metal of group VIII and that is activated according to an activation process that comprises at least one sulfurization stage and at least one stage for passivation with ammonia, and at least one dehydrogenation stage b).
    Type: Grant
    Filed: September 9, 1999
    Date of Patent: February 26, 2002
    Assignee: Institut Francais du Petrole
    Inventors: Julia Magne-Drisch, Vincent Coupard, Jean-François Joly, Fabio Alario, Elisabeth Merlen
  • Publication number: 20020016520
    Abstract: Integrated process for the preparation of cumene which comprises dehydrogenating a stream of propane to propylene in a dehydrogenation unit and sending the stream leaving the dehydrogenation unit, containing 25-40% by weight of propylene, to an alkylation unit together with a stream of benzene with a molar ratio benzene/propylene ranging from 8 to 10. The alkylation product is distilled in a first distillation column to recover a light fraction, essentially consisting of propane which is recycled to the dehydrogenation, and a heavy fraction which is distilled in a second distillation column to recover non-reacted benzene at the head, recycled to the alkylation unit, and cumene with a purity of over 99%, at the tail.
    Type: Application
    Filed: June 13, 2001
    Publication date: February 7, 2002
    Applicant: SNAMPROGETTI S.p.A.
    Inventors: Alberto Paggini, Domenico Sanfilippo, Elena Picciotto
  • Patent number: 6339179
    Abstract: A process for producing alkyl aromatics using a transalkylation reaction zone and an alkylation reaction zone is disclosed. One portion of the transalkylation reaction zone effluent passes to an alkylation reaction zone where an aromatic substrate is alkylated to the desired alkyl aromatic. At least a portion of the alkylation reaction zone effluent and another portion of the transalkylation reaction zone effluent pass to a product recovery zone. This process decreases the capital and operating costs of recycling aromatic substrate to the transalkylation and/or alkylation reaction zone while maintaining operational flexibility. This process is well suited for solid transalkylation and alkylation catalysts. Ethylbenzene and cumene may be produced by this process.
    Type: Grant
    Filed: July 25, 2000
    Date of Patent: January 15, 2002
    Assignee: UOP LLC
    Inventors: Russell C. Schulz, Gregory J. Gajda, Guy B. Woodle, Andrew S. Zarchy
  • Patent number: 6337427
    Abstract: A process for isomerising aromatic compounds containing eight carbon atoms is described in which the catalyst used contains at least one zeolite with structure type EUO and a group VIII element. In FIG. 1, the feed to be isomerised is introduced into reactor R via line 1. This fresh feed is enriched via lines 6 and 11 with a mixture containing at least one compound selected from the group formed by paraffins containing eight carbon atoms, benzene, toluene and naphthenes containing eight carbon atoms. Hydrogen is added via line 15.
    Type: Grant
    Filed: April 7, 1999
    Date of Patent: January 8, 2002
    Assignee: Institut Francais du Petrole
    Inventors: Fabio Alario, Jean-François Joly, Julia Magne-Drisch, Elisabeth Merlen, Eric Benazzi, Sylvie Lacombe
  • Publication number: 20010053867
    Abstract: Process for isomerization of a feedstock that contains aromatic compounds with eight carbon atoms characterized in that it comprises at least one isomerization stage a) that is carried out in the presence of a catalyst that contains at least one metal of group VIII and that is activated according to an activation process that comprises at least one sulfurization stage and at least one stage for passivation with ammonia, and at least one dehydrogenation stage b).
    Type: Application
    Filed: September 9, 1999
    Publication date: December 20, 2001
    Inventors: JULIA MAGNE-DRISCH, VINCENT COUPARD, JEAN-FRANCOIS JOLY, FABIO ALARIO, ELISABETH MERLEN
  • Publication number: 20010051754
    Abstract: A process for toluene disproportionation which obtains high xylene yields while minimizing ethylbenzene production employs a dual catalyst bed. The first bed employs an acid zeolite, e.g., ZSM-5 which disproportionates toluene and the downstream second bed uses an acid zeolite having hydrogenation-dehydrogenation activity, e.g., PtZSM-5, to selectively eliminate ethylbenzene.
    Type: Application
    Filed: August 3, 1999
    Publication date: December 13, 2001
    Inventors: DARIA N. LISSY, SANJAY B. SHARMA, DAVID S. SHIHABI
  • Patent number: 6313362
    Abstract: Akylation product is contacted with a purification medium in a liquid phase pre-reaction step to remove impurities and form a purified stream. The purified stream may then be further processed by liquid phase transalkylation to convert the polyalkylated aromatic compound to a monoalkylated aromatic compound. The process may use a large pore molecular sieve catalyst such as MCM-22 as the purification medium in the pre-reaction step because of its high reactivity for alkylation, strong retention of catalyst poisons and low reactivity for oligomerization under the pre-reactor conditions. Olefins, diolefins, styrene, oxygenated organic compounds, sulfur containing compounds, nitrogen containing compounds and oligomeric compounds are removed.
    Type: Grant
    Filed: December 17, 1998
    Date of Patent: November 6, 2001
    Assignee: ExxonMobil Corporation
    Inventors: John R. Green, Thomas F. Degnan, Yun-Yang Huang, Chaya R. Venkat, Ronald A. Weiss
  • Patent number: 6271429
    Abstract: A process for isomerising a feed comprising aromatic compounds containing 8 carbon atoms is carried out in two steps: an isomerisation step and a dehydrogenation step. In FIG. 1, the feed to be treated is introduced into isomerisation zone R1 via line 1. Substantially pure hydrogen is introduced into line 1 via line 12 and recycled hydrogen is introduced into line 1 via line 13. Hydrogen which circulates in line 13 is purged via line 15. The effluent from isomerisation zone R1 is sent to a separation zone S1 via line 2. In S1, hydrogen contained in the effluent is isolated and recycled to the inlet to isomerisation zone R1 via line 13, the remaining effluent being evacuated from this separation zone S1 via line 3. The fluid contained in line 3 is heated in an oven F1 then evacuated therefrom via line 4. The effluent leaving the oven is enriched in recycled hydrogen via line 14 then it is introduced into dehydrogenation zone R2. The effluent from zone R2 is sent via line 5 to separation zone S2.
    Type: Grant
    Filed: October 14, 1998
    Date of Patent: August 7, 2001
    Assignee: Institut Francais du Petrole
    Inventors: Jean-François Joly, Julia Magne-Drisch, Vincent Coupard, Fabio Alario, Gérard Miquel, Marc Reymond
  • Patent number: 6258989
    Abstract: A hydrocarbon feedstock containing C5 olefins, C5 diolefins, CPD, DCPD, and aromatics is processed by the steps of heating a hydrocarbon feedstock containing CPD, DCPD, C5 diolefins, benzene, toluene, and xylene in a heating zone, to dimerize CPD to DCPD, thereby forming a first effluent; separating the first effluent into a C6+ stream and a C5 diolefin stream; separating the C6+ stream into a C6-C9 stream and a C10+ stream; separating the C10+ stream into a fuel oil stream and a DCPD stream; and hydrotreating the C6-C9 stream to thereby form a BTX stream.
    Type: Grant
    Filed: September 30, 1999
    Date of Patent: July 10, 2001
    Assignee: Phillips Petroleum Company
    Inventors: Steven A. Owen, Marvin M. Johnson, Tin-Tack Peter Cheung, Mark E. Lashier
  • Patent number: 6248929
    Abstract: Disclosed is a rubber process oil in which the content of polycyclic aromatics (PCAs) as determined by the IP 346 method is less than 3% by mass and which is rich In aromatic hydrocarbons, and a method for producing the same. The aniline point of the rubber process oil is 80° C. or less, and the % CA value as determined by ring analysis according to the Kurtz method is from 20 to 50%. The rubber process oil is produced by using extraction of lube oil fraction with a solvent having a selective affinity for aromatics. The extraction conditions are determined so that the extraction yield is regulated to a predetermined requirement defined by the PCAs content of the lube oil fraction. Alternatively, the extract is cooled to further separate into the extract and the raffinate, and the second raffinate is used for the rubber process oil.
    Type: Grant
    Filed: January 21, 1999
    Date of Patent: June 19, 2001
    Assignee: Japan Energy Corporation
    Inventors: Takashi Kaimai, Kazumitsu Fujihara, Yoshiyuki Morishima
  • Publication number: 20010001448
    Abstract: The patent application discloses an integrated process for reformate upgrading. Such a process enables production of a high value product slate, by incorporating the step of reforming along with reaction/diffusion with a zeolite.
    Type: Application
    Filed: September 27, 1999
    Publication date: May 24, 2001
    Inventors: VINAYA A. KAPOOR, ROBERT A. CRANE, JEFFREY S. BECK, JOHN H. THURTELL, DAVID L. STERN
  • Patent number: 6187982
    Abstract: A process useful in steam cracking is disclosed for selectively converting a feed comprising C4+ dienes and oxygenate to a product comprising increased C2+ monoolefins and para-xylene levels by contacting said feed under diolefin conversion conditions with a catalyst comprising a porous crystalline material having a Diffusion Parameter for 2,2-dimethylbutane of about 0.1-100 sec−1 when measured at a temperature of 120° C. and a 2,2-dimethylbutane pressure of 60 torr (8 kPa), a temperature of 430° C. and 0.5 WHSV.
    Type: Grant
    Filed: October 15, 1999
    Date of Patent: February 13, 2001
    Assignee: Mobil Oil Corporation
    Inventors: Jeffrey S. Beck, Stephen H. Brown, William A. Weber
  • Patent number: 6147269
    Abstract: A C.sub.8 aromatic feedstock is isomerized by an isomerization stage conducted at 320-380.degree. C. with a catalyst containing at least one EUO-structure-type zeolite and at least one metal of group VIII, to obtain an effluent containing isomerized alkyl aromatics and about 10-30% by weight of naphthenes. The effluent is then subjected to a dehydrogenation stage so as to convert the naphthenes to additional alkyl aromatics.
    Type: Grant
    Filed: April 12, 1999
    Date of Patent: November 14, 2000
    Assignee: Institut Francais du Petrole
    Inventors: Jean-Fran.cedilla.ois Joly, Vincent Coupard, Julia Magne-Drisch, Fabio Alario, Elisabeth Merlen, Sylvie Lacombe, Eric Benazzi
  • Patent number: 6103808
    Abstract: The high aromatic oil provided in the present invention is characterized by that a glass transition point is -45 to -20.degree. C. and an aromatic component measured by Clay-Gel method accounts for 55 to 90% by weight and that a polycyclic aromatic compound measured by IP 346 method accounts for less than 3% by weight based on the whole components of hydrocarbons contained in the oil.This high aromatic oil can suitably be used for various rubber compositions such as tires, rubber vibration insulators and fenders, oil extended synthetic rubbers, printing inks and writing inks.
    Type: Grant
    Filed: September 30, 1997
    Date of Patent: August 15, 2000
    Assignee: Bridgestone Corporation
    Inventor: Takatsugu Hashimoto
  • Patent number: 6096935
    Abstract: A process for producing alkyl aromatics using a transalkylation reaction zone and an alkylation reaction zone is disclosed. The transalkylation reaction zone effluent passes to the alkylation reaction zone where aromatics in the transalkylation reaction zone effluent are alkylated to the desired alkyl aromatics. This process decreases the capital and operating costs of recycling the aromatics in the transalkylation reaction zone effluent. This process is well suited for solid transalkylation and alkylation catalysts. Ethylbenzene and cumene may be produced by this process.
    Type: Grant
    Filed: July 28, 1998
    Date of Patent: August 1, 2000
    Assignee: UOP LLC
    Inventors: Russell C. Schulz, Gregory J. Gajda
  • Patent number: 6005156
    Abstract: In a process for the separation of p-xylene from a feed to be treated containing a mixture of xylenes and olefinic impurities, at least a portion of the feed is circulated in an enrichment zone (14) to enrich a first fraction (15) in p-xylene and provide a second fraction (18) which is depleted in p-xylene. The second fraction is circulated in an isomerisation zone (19) and an isomerate (20) is recovered which is recycled to the enrichment zone. At least a portion of the feed to be treated, the isomerate, or a mixture thereof is circulated in at least one selective hydrogenation zone (3) to partially remove the olefinic impurities and thereafter in at least one clay tretment zone (8) to remove additional olefinic impurities. An effluent is recovered which is sent to the enrichment zone.
    Type: Grant
    Filed: January 27, 1998
    Date of Patent: December 21, 1999
    Assignee: Institut Francais du Petrole
    Inventors: Jean Fran.cedilla.ois Joly, Charles Cameron, Pierre Renard, Fran.cedilla.oise Montecot, Jean Cosyns, Gerard Leger
  • Patent number: 5998688
    Abstract: A method for minimizing the loss of xylenes in an ethylbenzene conversion/isomerization process by adding toluene to the feedstock. The concentration of toluene in the feedstock is increased by co-feeding toluene or by recycling toluene separated from the ethylbenzene conversion reactor effluent. The increased toluene concentration reduces the loss of xylenes during the ethylbenzene conversion reaction and under preferred operating conditions increases the amount of xylenes in the product.
    Type: Grant
    Filed: August 25, 1998
    Date of Patent: December 7, 1999
    Assignee: Mobil Oil Corporation
    Inventors: Jeevan S. Abichandani, Jeffrey S. Beck, Stephen H. Brown, Ronald J. Cimini, Ivy D. Johnson, Selma Kwok, Dimitris K. Liguras, David L. Stern
  • Patent number: 5977420
    Abstract: A method for increasing the efficiency of xylene isomerization by using a two stage isomerization process. In the first stage of the process, a C.sub.9.sup.+ aromatics feedstock is subjected to ethylbenzene conversion and xylene isomerization. Non-C.sub.8 aromatics are removed from the effluent, which is then processed in a second stage of the process to remove para-xylene and isomerize the para-xylene depleted effluent. The effluent from the second stage isomerization unit is then recycled into the inlet of the second stage of the process and a slip stream from the para-xylene separator is recycled to the feedstock and to the effluent of the ethylbenzene conversion unit. In this way, the production of para-xylene is maximized. In a preferred embodiment, toluene is co-fed into the feedstock to minimize the loss of xylenes during the ethylbenzene conversion reaction.
    Type: Grant
    Filed: August 25, 1998
    Date of Patent: November 2, 1999
    Assignee: Mobil Oil Corporation
    Inventors: Jeevan S. Abichandani, Jeffrey S. Beck, Stephen H. Brown, Ronald J. Cimini, Ivy D. Johnson, Dimitris K. Liguras, David L. Stern
  • Patent number: 5959167
    Abstract: A process for converting lignin into high-quality reformulated hydrocarbon gasoline compositions in high yields is disclosed. The process is a two-stage, catalytic reaction process that produces a reformulated hydrocarbon gasoline product with a controlled amount of aromatics. In the first stage, a lignin material is subjected to a base-catalyzed depolymerization reaction in the presence of a supercritical alcohol as a reaction medium, to thereby produce a depolymerized lignin product. In the second stage, the depolymerized lignin product is subjected to a sequential two-step hydroprocessing reaction to produce a reformulated hydrocarbon gasoline product. In the first hydroprocessing step, the depolymerized lignin is contacted with a hydrodeoxygenation catalyst to produce a hydrodeoxygenated intermediate product.
    Type: Grant
    Filed: August 19, 1998
    Date of Patent: September 28, 1999
    Assignee: The University of Utah Research Foundation
    Inventors: Joseph S. Shabtai, Wlodzimierz W. Zmierczak, Esteban Chornet
  • Patent number: 5865986
    Abstract: This is a process for upgrading a petroleum naphtha fraction. The naphtha is subjected to reforming and the reformate is cascaded to a benzene and toluene synthesis zone over a benzene and toluene synthesis catalyst comprising a molecular sieve of low acid activity. The preferred molecular sieve is steamed ZSM-5. The benzene and toluene synthesis zone is operated under conditions compatible with the conditions of the reformer such as pressures of above about 50 psig (446 kPa) and temperatures above about 800.degree. F. (427.degree. C). In one aspect of the invention, the benzene and toluene synthesis catalyst includes a metal hydrogenation component such as cobalt, nickel, platinum or palladium. In one mode of operation, the benzene and toluene synthesis catalyst replaces at least a portion of the catalyst of the reformer. The process produces a product containing an increased proportion of benzene and toluene, and a reduced proportion of C8 aromatics, particularly ethylbenzenes, as compared to the reformate.
    Type: Grant
    Filed: November 3, 1995
    Date of Patent: February 2, 1999
    Assignee: Mobil Oil Corporation
    Inventors: John Scott Buchanan, Jane C. Cheng, David G. Freyman, Werner Otto Haag, Mohsen N. Harandi, Dominick N. Mazzone, Roger A. Morrison, Norman J. Rouleau, Charles M. Sorensen, Hye Kyung C. Timken, Robert Adams Ware
  • Patent number: 5792899
    Abstract: A process for the management of polynuclear aromatic compounds produced in a hydrocarbon dehydrogenation zone wherein the effluent from the hydrocarbon dehydrogenation zone is contacted with an adsorbent to reduce the concentration of polynuclear aromatic compounds. The resulting dehydrogenated hydrocarbon having a reduced concentration of polynuclear aromatic compounds is reacted with methanol to produce an ether. A portion of the ether is contacted with a spent bed of adsorbent to recover at least a portion of the polynuclear aromatic compounds adsorbed thereon to thereby regenerate the adsorbent.
    Type: Grant
    Filed: September 27, 1996
    Date of Patent: August 11, 1998
    Assignee: UOP LLC
    Inventor: Paul R. Cottrell
  • Patent number: 5750814
    Abstract: A improved process is provided for the alkylation of aromatic compounds under at least partial liquid phase conditions, and in the presence of a zeolite-type alkylation/transalkylation catalyst. In accordance with the present process, a diluted aromatic hydrocarbon feedstock containing C.sub.5 -C.sub.7 olefins is brought into contact with a diluted olefinic feedstream in the presence of the alkylation/transalkylation catalyst. Prior to contact with the olefinic feedstream, C.sub.5 -C.sub.7 olefins present in the aromatic hydrocarbon feedstock are selectively hydrogenated.
    Type: Grant
    Filed: June 6, 1995
    Date of Patent: May 12, 1998
    Assignee: Fina Research, S.A.
    Inventors: Jacques F. Grootjans, Pierre-Frederic J. Belloir, Eric J.G.M. Romers
  • Patent number: 5489724
    Abstract: Aliphatic feeds are converted to olefins and/or aromatics in a multi pressure reactor system. A high pressure first stage reactor generates much or all of the hydrogen needed to reduce catalyst coking in lower pressure downstream reactors. High pressure operation protects catalyst stability in the first reactor, while produced hydrogen helps protect downstream catalyst. Low pressure downstream operation improves yields.
    Type: Grant
    Filed: December 13, 1994
    Date of Patent: February 6, 1996
    Assignee: Mobil Oil Corporation
    Inventor: Mohsen N. Harandi
  • Patent number: 5409595
    Abstract: Catalytically cracked naphthas containing C.sub.9 + hydrocarbons are hydrocracked over a crystalline zeolite, typically, mildly steamed zeolite beta then subjected to reforming to achieve a gasoline product of reduced end boiling range and higher octane than the feed. A hydrogen stream from the reformer which contains a catalytic promoter, such as chlorine, is separated into a first stream and a second stream. The first stream is treated over a solid sorbent to remove the promoter and recycled promoter to the hydrocracking step while the untreated second hydrogen stream which contains promoter is recycled to the reformer.
    Type: Grant
    Filed: April 4, 1994
    Date of Patent: April 25, 1995
    Assignee: Mobil Oil Corporation
    Inventors: Mohsen N. Harandi, Roger A. Morrison, Gerald J. Teitman
  • Patent number: 5300715
    Abstract: An improved process for the production of linear olefinic hydrocarbons by paraffin dehydrogenation and adsorptive separation is disclosed. Aromatic by-products normally formed in paraffin dehydrogenation are selectively removed using at least one aromatics removal zone. Removal of these aromatic by-products significantly increases the purity of the olefinic hydrocarbon product and increases the capacity of the adsorptive separation zone. The improved process is believed to increase the life of the adsorbent in the adsorptive separation zone and the life of the catalyst in the dehydrogenation zone.
    Type: Grant
    Filed: October 9, 1992
    Date of Patent: April 5, 1994
    Assignee: UOP
    Inventor: Bipin V. Vora
  • Patent number: 5288390
    Abstract: A process for the processing or upgrading of heavy oil fractions containing polynuclear aromatics is disclosed. The process comprises selectively oxidizing a feedstock under low severity conditions in a multi-phase system, wherein one phase is an aqueous and contains water-soluble catalyst, deoxygenating that product followed by hydroprocessing to yield a substantially mononuclear product.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: February 22, 1994
    Assignee: Sun Company, Inc. (R&M)
    Inventor: Vincent A. Durante
  • Patent number: 5278344
    Abstract: 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: Grant
    Filed: December 14, 1992
    Date of Patent: January 11, 1994
    Assignee: UOP
    Inventors: Christopher D. Gosling, John D. Swift
  • Patent number: 5276231
    Abstract: An improved process for the production of alkylated aromatic compounds by paraffin dehydrogenation and aromatic alkylation is disclosed. Aromatic by-products normally formed in paraffin dehydrogenation are selectively removed using at least one aromatics removal zone. Removal of these aromatic by-products significantly reduces the deactivation rate of solid alkylation catalysts. The improved process produces a detergent alkylate product that is significantly more linear than that produced by the prior art process.
    Type: Grant
    Filed: July 27, 1992
    Date of Patent: January 4, 1994
    Assignee: UOP
    Inventors: Joseph A. Kocal, Donald J. Korous
  • Patent number: 5258563
    Abstract: A process is disclosed for the conversion of light aliphatic hydrocarbons such as propane into aromatic hydrocarbons and especially high purity benzene. The feed hydrocarbon is converted to aromatic hydrocarbons in a dehydrocyclodimerization zone. The product stream from the dehydrocyclodimerization zone which contains benzene, toluene, xylenes and C.sub.6 -C.sub.10 non-aromatics are separated into an overhead stream which contains the non-aromatic hydrocarbons and a small fraction of the benzene and a bottoms stream which contains the remainder of the benzene and other aromatic components. The overhead stream is then flowed to a conversion zone where the C.sub.6 -C.sub.7 non-aromatic hydrocarbons are cracked and the benzene is combined with the bottoms stream and further separated to give a high purity benzene product stream and a toluene, xylenes and C.sub.9 + product stream. The toluene, xylenes and C.sub.9 + product stream may further be separated into a toluene and xylenes product and a C.sub.
    Type: Grant
    Filed: June 11, 1992
    Date of Patent: November 2, 1993
    Assignee: UOP
    Inventors: Christopher D. Gosling, David A. Hamm
  • Patent number: 5100534
    Abstract: An improved process for upgrading paraffinic naphtha to high octane fuel by contacting a naphtha feedstock, such as virgin naphtha feedstock stream containing predominantly C.sub.7 -C.sub.12 alkanes and naphthenes, with solid medium pore acid zeolite cracking catalyst under low pressure selective cracking conditions effective to produce at least 10 wt % selectivity C.sub.4 -C.sub.5 isoalkene. Cracking effluent is separated to obtain a light olefinic fraction rich in C.sub.4 -C.sub.5 isoalkene and a C.sub.6 + liquid fraction of enhanced octane value containing less than 50 wt % aromatic hydrocarbons. In a multistage operation enhanced octane products are obtained by etherifying the isoalkene fraction and by contacting the C.sub.6 + normally liquid fraction with reforming catalyst under moderate reforming conditions at elevated temperature to obtain a reformate product of enhanced octane value.
    Type: Grant
    Filed: November 6, 1990
    Date of Patent: March 31, 1992
    Assignee: Mobil Oil Corporation
    Inventors: Quang N. Le, Paul H. Schipper, Hartley Owen
  • Patent number: 5043500
    Abstract: A dehydrogenation process, where a hydrocarbon feed is dehydrogenated in a dehydrogenation zone and then oxidatively reheated by the combustion of hydrogen in an oxidation zone containing an oxidation catalyst, is improved by using a stream of dilution steam as an educing fluid to draw oxygen into contact with the effluent from the dehydrogenation zone ahead of the oxidation zone. A stream of dilution steam is often combined with the dehydrogenation zone effluent in order to control the oxygen concentration ahead of the oxidation zone and to lower the hydrogen partial pressure. Educing the oxygen-containing gas for the oxidation zone into the process by using the dilution steam an an educing fluid eliminates the need for compression of the oxygen-containing gas and prevents oxygen from contacting the dehydrogenation zone effluent before the dilution steam is admixed therewith. This process is particularly beneficial in the dehydrogenation of ethylbenzene to produce styrene.
    Type: Grant
    Filed: December 20, 1989
    Date of Patent: August 27, 1991
    Assignee: UOP
    Inventor: Constante P. Tagamolila
  • Patent number: 5001291
    Abstract: This invention relates to a process for (a) catalytically dehydrogenating a saturated hydrocarbon to the corresponding unsaturated hydrocarbon and hydrogen, (b) removing hydrogen from the products of step (a) over a catalyst supported on tin oxide and (c) dehydrogenating the products from step (b) under conditions of step (a). The process is effective for the production of e.g. styrene from ethylbenzene.
    Type: Grant
    Filed: March 28, 1989
    Date of Patent: March 19, 1991
    Assignee: BP Chemicals Limited
    Inventors: Andrew Holt, Paul C. J. Smith
  • Patent number: 4997991
    Abstract: The invention provides an inexpensive synthesis process for preparation of diethynylbenzene monomers that are useful in the preparation of polyacetylenes. This process provides for the preparation of thermally sensitive monomers in a one-pot reaction using readily available materials at low temperatures in an environment capable of absorbing large amounts of energy. Divinylbenzene is first brominated and then dehydrobrominated with sodium hydroxide or potassium hydroxide preferably in the presence of a phase transfer agent followed by distillation to recover the diethylnylbenzene product.
    Type: Grant
    Filed: March 26, 1990
    Date of Patent: March 5, 1991
    Assignee: Hercules Incorporated
    Inventors: Lawrence E. Carosino, David C. Herak
  • Patent number: 4982029
    Abstract: A method for the direct preparation of olefins from ketones and Grignard reagents without isolation of the intermediate alcohol and in the absence of acidic dehydration catalysts. Ketones are reacted with a Grignard reagent in the presence of a low boiling solvent for the Grignard reagent to form a Grignard reaction mixture. An active hydrogen-containing compound is added to the Grignard reaction mixture to form a reaction mixture comprising an alcohol and Grignard salts. The alcohol is dehydrated in the presence of the Grignard salts and a solvent which has a higher boiling point than solvents typically emloyed during the Grignard condensation. The higher boiling solvent can be an active hydrogen-containing compound such as n-octanol and otherwise can be added at any time, including the initial condensation step.
    Type: Grant
    Filed: December 16, 1988
    Date of Patent: January 1, 1991
    Assignee: The Dow Chemical Company
    Inventor: Kuo-Yuan Chang, deceased
  • Patent number: 4886925
    Abstract: An integrated process is disclosed for the conversion of C.sub.2 + normal olefins into methyl tertiaryalkyl ethers and high octane gasoline. The process combines olefins interconversion with etherification and conversion of unreacted methanol and olefins in contact with acidic, shape selective metallosilicate zeolite catalyst.
    Type: Grant
    Filed: May 2, 1988
    Date of Patent: December 12, 1989
    Inventor: Mohsen N. Harandi
  • Patent number: 4855518
    Abstract: 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: Grant
    Filed: July 19, 1988
    Date of Patent: August 8, 1989
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Isoo Shimizu, Yuuichi Tokumoto
  • Patent number: 4855519
    Abstract: 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: Grant
    Filed: November 14, 1988
    Date of Patent: August 8, 1989
    Assignee: Nippon Petrochemicals Company
    Inventors: Isoo Shimizu, Hitoshi Mitsuyuki, Kazumichi Uchida, Yuuichi Tokumoto
  • Patent number: 4827046
    Abstract: An improved process for reacting crude aqueous methanol feedstock with tertiary-olefinic hydrocarbons to produce C.sub.5.sup.+ methyl tertiary-alkyl ethers, which comprises: contacting the aqueous methanol feedstock with a liquid hydrocarbon extractant rich in C.sub.4.sup.+ isoalkylene under liquid extraction conditions; recovering an organic extract phase comprising the hydrocarbon extractant and a major amount of methanol introduced in the feedstock; reacting the extracted methanol and C.sub.4.sup.+ isoalkene in contact with an acid etherification catalyst under catalytic reaction conditions to produce ether product; separating ether product from unreacted methanol and olefin; recovering an aqueous methanol raffinate phase containing the major amount of water introduced with the feedstock and a minor amount of feedstock methanol; and converting methanol from the aqueous raffinate phase concurrently with unreacted methanol and olefin from etherification effluent separation to produce hydrocarbons.
    Type: Grant
    Filed: April 11, 1988
    Date of Patent: May 2, 1989
    Assignee: Mobil Oil Corporation
    Inventors: Mohsen N. Harandi, Hartley Owen
  • Patent number: 4827066
    Abstract: A process for the catalytic dehydrogenation of a dehydrogenatable C.sub.2 -plus feed hydrocarbon which comprises the steps of: (a) passing a feed stream comprising the C.sub.2 -plus feed hydrocarbon into an isothermal dehydrogenation zone and through at least one bed of dehydrogenation catalyst maintained at isothermal dehydrogenation conditions selected to convert at least about 50 weight percent of the dehydrogenatable C.sub.2 -plus feed hydrocarbon and producing an isothermal dehydrogenation zone effluent stream comprising hydrogen, unconverted C.sub.2 -plus feed hydrocarbon and C.sub.
    Type: Grant
    Filed: May 23, 1988
    Date of Patent: May 2, 1989
    Assignee: UOP Inc.
    Inventors: Raymond R. Herber, Gregory J. Thompson
  • Patent number: 4827065
    Abstract: A method for producing p-isobutylstyrene which is characterized in that starting materials are inexpensive, processes are easy to be done and products are highly pure. The method comprises the step of catalytically cracking 1,1-bis(p-isobutylphenyl)ethane at temperatures in the range of 200.degree. to 650.degree. C. in the presence of a protonic acid catalyst and/or a solid acid catalyst to produce p-isobutylstyrene and isobutylbenzene, and at least a portion of said isobutylbenzene is recycled to produce said 1,1-bis(p-isobutylphenyl)ethane by reaction with acetaldehyde in the presence of sulfuric acid.
    Type: Grant
    Filed: July 10, 1985
    Date of Patent: May 2, 1989
    Assignee: Nippon Petrochemicals Company, Limited
    Inventors: Isoo Shimizu, Ryotaro Hirano, Yasuo Matsumura, Hideki Nomura, Kazumichi Uchida, Atsushi Sato
  • Patent number: 4822937
    Abstract: A process for the production of isobutylbenzenes in particular, isobutylbenzene itself, is provided. The process is in two stages and comprises (1) reacting a vinylcyclohexane with an isoolefin of formula (R)(R.sup.1)C.dbd.C(CH.sub.3).sub.2 in the presence of a dismutation catalyst to produce an isobutenylcyclohexene and (2) contacting the isobutenylcyclohexene with a dehydroisomerisation catalyst to produce an isobutylbenzene. Examples of vinylcyclohexenes which can be used include 4-vinylcyclohexene and styrene.
    Type: Grant
    Filed: May 24, 1988
    Date of Patent: April 18, 1989
    Assignee: BP Chemicals Limited
    Inventors: Derek K. MacAlpine, Malcolm J. Lawrenson
  • Patent number: 4822938
    Abstract: There is provided a process for converting methane to higher molecular weight hydrocarbons. In a first step, methane is contacted with elemental sulfur under conditions sufficient to produce carbon disulfide. Carbon disulfide from this step is then contacted with methane and hydrogen under conditions sufficient to convert methane and to produce CH.sub.3 SH. This CH.sub.3 SH is then contacted with a sufficient catalyst, such as a zeolite, especially ZSM-5, under conditions sufficient to produce hydrocarbons having two or more carbon atoms.
    Type: Grant
    Filed: May 3, 1988
    Date of Patent: April 18, 1989
    Assignee: Mobil Oil Corporation
    Inventors: Costandi A. Audeh, Weldon K. Bell, Scott Han, Robert E. Palermo
  • Patent number: 4778941
    Abstract: More efficient mixing, more complete hydrogen consumption, and more thorough cooling of a dehydrogenation zone effluent is obtained by educting a portion of the dehydrogenation effluent from the reaction and externally cooling the withdrawn effluent in a heat exchanger and externally admixing the withdrawn effluent with an oxygen-containing stream. Eduction of the hydrogenation effluent by the oxygen-containing stream provides the necessary pressure drop for passing the dehydrogenation effluent through the heat exchanger and then admixing the effluent and oxygen-containing stream.
    Type: Grant
    Filed: January 19, 1988
    Date of Patent: October 18, 1988
    Assignee: UOP Inc.
    Inventor: Constante P. Tagamolila
  • Patent number: 4749820
    Abstract: Disclosed is a method and apparatus for producing gasoline and distillate grade products which employs integrating catalytic (or thermal) dehydrogenation of paraffins with MOGD to minimize interstage compression and gas plant separation cost. The process cascades the product from a low temperature propane or butane dehydrogenation zone into a first catalytic reactor zone which operates at low pressure and contains zeolite oligomerization catalysts, where the low molecular weight olefins are reacted to primarily gasoline range materials. These gasoline range materials can then be pressurized to the pressure required for reacting to distillate in a second catalytic reactor zone operating at high pressure and containing zeolite oligomerization catalyst. The first catalytic reactor zone also acts to remove the olefins from the dehydrogenation reactor effluent to allow recycle of the unreacted paraffins.
    Type: Grant
    Filed: September 14, 1984
    Date of Patent: June 7, 1988
    Assignee: Mobil Oil Corporation
    Inventors: James C. Kuo, Samuel A. Tabak
  • Patent number: 4717779
    Abstract: Dehydrogenatable hydrocarbons may be subjected to a dehydrogenation reaction in which the hydrocarbons are treated with a dehydrogenation catalyst comprising a modified iron catalyst in the presence of steam in a multicatalyst bed system. The reaction mixture containing unconverted hydrocarbons, dehydrogenated hydrocarbons, hydrogen and steam is then contacted with an oxidation catalyst whereby hydrogen is selectively oxidized. The selective oxidation catalyst which is used will comprise a noble metal of Group VIII of the Periodic Table, a metal of Group IVA and, if so desired, a metal of Group IA or IIA composited on a porous inorganic support. The inorganic support will comprise an alumina precursor which possesses and ABD less than about 0.6 g/cc, a pore volume greater than about 0.5 cc/g, and a pore distribution such that between 10% and 70% of the pore volume is present as pores whose diameters are greater than about 300 Angstroms. After peptizing and calcination at a temperature of about 900.degree.
    Type: Grant
    Filed: August 6, 1986
    Date of Patent: January 5, 1988
    Assignee: UOP Inc.
    Inventors: Jeffery C. Bricker, Tamotsu Imai, David E. Mackowiak
  • Patent number: 4691071
    Abstract: Dehydrogenatable hydrocarbons may be subjected to a dehydrogenation reaction by treating the hydrocarbons in the presence of a dehydrogenation catalyst comprising an alkaline metal-promoted iron compound. The effluent is then subjected to a selective oxidation step in which the hydrogenation produced from the first reaction is oxidized in preference to the dehydrogenated and unconverted hydrocarbons. The catalyst which is used to effect this selective oxidation comprises a Group VIII noble metal, a Group IVA metal and a Group IA or IIA metal composited on a metal oxide support. The present invention is concerned with the use of a cerium-containing alumina as a support for this selective oxidation catalyst.
    Type: Grant
    Filed: December 11, 1986
    Date of Patent: September 1, 1987
    Assignee: UOP Inc.
    Inventor: Jeffery C. Bricker
  • Patent number: 4675461
    Abstract: Disclosed is a method and apparatus for conversion of LPG hydrocarbons into distillate fuels by integrating LPG dehydrogenation with catalytic oligomerization and recovering the distillates produced. The described method and apparatus may comprise an H.sub.2 separation zone, wherein a lean oil stream contacts a dehydrogenation effluent stream to produce a C.sub.3.sup.+ rich liquid stream to feed oligomerization. An energy efficient separation zone comprising dual debutanizers is disclosed. In addition, a method and apparatus is disclosed for a fluid bed dehydrogenation reactor zone using an FCC catalyst contaminated with a metal, such as nickel and/or vanadium.
    Type: Grant
    Filed: March 5, 1986
    Date of Patent: June 23, 1987
    Assignee: Mobil Oil Corporation
    Inventors: Hartley Owen, John C. Zahner