Transition Metal-containing Catalyst Patents (Class 585/489)
  • 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: 6207871
    Abstract: There is provided a process for producing high-purity meta-xylene by converting a hydrocarbon feedstream comprising at least about 5 wt % ethylbenzene and at least about 20 wt % meta-xylene, over a single molecular sieve catalyst under ethylbenzene conversion conditions sufficient to provide a primary product stream depleted of more than 50% of the ethylbenzene present in the feedstream. The process can further comprise stripping benzene and/or toluene by-products from the primary product stream to provide a secondary product stream comprising at least about 75 wt % mixed ortho-xylene and meta-xylene; and splitting the secondary product stream by removing substantially all of the ortho-xylene present therein to provide a tertiary product stream comprising at least about 95 wt % meta-xylene.
    Type: Grant
    Filed: December 19, 1997
    Date of Patent: March 27, 2001
    Assignee: Mobil Oil Corporation
    Inventors: Stuart D. Hellring, David L. Stern
  • Patent number: 6133494
    Abstract: A catalyst composition and a process for hydrodealkylating C.sub.9 + aromatic compounds such as, for example, trimethylbenzenes, to C.sub.6 to C.sub.8 aromatic hydrocarbons such as toluene and xylenes are disclosed. The composition comprises an alumina and a silica wherein the weight ratio of aluminum to silicon is in the range of from about 0.005:1 to about 0.25:1. The process comprises contacting, in the presence of the catalyst composition, a fluid which comprises a C.sub.9 + aromatic compound with a hydrogen-containing fluid under a condition sufficient to effect the conversion of a C.sub.9 + aromatic compound to a C.sub.6 to C.sub.8 aromatic hydrocarbon; and the C.sub.9 + aromatic compound contains at least 9 carbon atoms.
    Type: Grant
    Filed: May 21, 1999
    Date of Patent: October 17, 2000
    Assignee: Phillips Petroleum Company
    Inventors: An-hsiang Wu, Charles A. Drake
  • Patent number: 6121501
    Abstract: A process for producing 2,6-dialkylnaphthalene from a hydrocarbon feedstock that contains at least one component selected from the group consisting of dialkylnaphthalene isomers, monoalkylnaphthalene isomers, polyalkylnaphthalenes, and naphthalene, is provided that includes the following steps:I. separating the hydrocarbon feedstock and/or a dealkylation product fed from step III into a naphthalene fraction, a monoalkylnaphthalene fraction, a dialkylnaphthalene fraction and a remaining products fraction;II. separating and purifying 2,6-dialkylnaphthalene from the dialkylnaphthalene fraction of step I;III. dealkylating the hydrocarbon feedstock and/or the remaining products fraction of step I and feeding the dealkylation product to step I; andIV. alkylating the naphthalene and monoalkylnaphthalene fractions of step I;wherein the hydrocarbon feedstock is fed to step I or step III.
    Type: Grant
    Filed: April 9, 1999
    Date of Patent: September 19, 2000
    Assignees: Kabushiki Kaisha Kobe Seiko Sho, Mobil Oil Corporation
    Inventors: Masahiro Motoyuki, Koji Yamamoto, Ajit Vishwanath Sapre, John Paul Mc Williams, Susan Patricia Donnelly
  • Patent number: 6077984
    Abstract: A novel zeolite catalyst composition comprising a mixture of a zeolite, a binder, and a zinc borate compound wherein such mixture is calcined or treated with steam. Preferably, the zeolite has not been treated with an acid. Also provided is a process of making such composition, a product by such process, and the use thereof in the conversion of a hydrocarbon-containing fluid such as a gasoline-boiling range fluid or coker naphtha. Use of such zeolite in the conversion of a hydrocarbon-containing fluid also includes pre-treating such hydrocarbon-containing fluid with a nitrogen removal medium such as ion-exchange resin.
    Type: Grant
    Filed: September 1, 1998
    Date of Patent: June 20, 2000
    Assignee: Phillips Petroleum Company
    Inventors: Charles A. Drake, An-hsiang Wu, Jianhua Yao, Scott D. Love
  • Patent number: 6063974
    Abstract: A hydrocarbon conversion process in which the rate of coke formation is reduced without a significant sacrifice in light olefin and BTX yield by the use of a silylated, stabilized metal promoted zeolite catalyst. Another embodiment includes a novel silylated spinel/zeolite catalyst. Another embodiment includes a process for producing a zinc or gallium promoted zeolite in which the promoter is stabilized by a high temperature water vapor treatment in the presence of a metal oxide such as alumina and thereafter the stabilized catalyst precursor is calcined and silylated.
    Type: Grant
    Filed: April 15, 1998
    Date of Patent: May 16, 2000
    Assignee: Phillips Petroleum Company
    Inventors: Charles A. Drake, An-hsiang Wu
  • Patent number: 6063975
    Abstract: A catalyst composition, a process for producing the composition, and a hydrotreating process for converting a hydrocarbon stream such as, for example, gasoline, to olefins and C.sub.6 to C.sub.8 aromatic hydrocarbons such as toluene and xylenes are disclosed. The catalyst composition comprises a zeolite, a clay, and a promoter. The process for producing the composition comprises the steps: (1) combining a zeolite with a clay and a promoter under a condition sufficient to bind the clay to the zeolite to produce a clay-bound zeolite; and (2) heating the clay-bound zeolite to produce a modified zeolite. The hydrotreating process comprises contacting a hydrocarbon stream with the catalyst composition under a condition sufficient to effect the conversion of a hydrocarbon to an olefin and a C.sub.6 to C.sub.8 aromatic hydrocarbon.
    Type: Grant
    Filed: October 14, 1998
    Date of Patent: May 16, 2000
    Assignee: Phillips Petroleum Company
    Inventors: Charles A. Drake, An-hsiang Wu
  • Patent number: 6051744
    Abstract: A new process for the hydrodealkylation of ethylbenzene and the isomerization of xylenes at low pressure and at a low hydrogen to ethylbenzene mole ratio as well as a low hydrogen to hydrocarbon feed mole ratio using a catalyst comprising (a) HZSM-5 having a particle size less than 1.0 microns, and (b) a Group VIII metal such as platinum.
    Type: Grant
    Filed: December 17, 1998
    Date of Patent: April 18, 2000
    Assignee: Chevron Chemical Company LLC
    Inventors: Gerald J. Nacamuli, Charles R. Wilson, Roger F. Vogel
  • 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: 5965782
    Abstract: A catalyst composition, a process for producing the composition and a process for transalkylation of C.sub.9 + aromatic compounds to C.sub.6 to C.sub.8 aromatic hydrocarbons are disclosed. The composition comprises a zeolite and tungsten wherein tungsten is preferably present as tungsten carbide which is impregnated on the zeolite. A preferred process for producing the catalyst composition which comprises: (1) contacting a zeolite with an effective amount of an acid under a condition sufficient to produce an acid-leached zeolite; and (2) impregnating acid-leached zeolite with an effective amount of tungsten-containing compound under a condition sufficient to effect the production of a tungsten carbide-promoted zeolite. The transalkylation process comprises contacting, in the presence of the catalyst composition, a fluid which comprises a C.sub.9 + aromatic compound with a hydrogen-containing fluid under a condition sufficient to effect the conversion of a C.sub.9 + aromatic compound to a C.sub.6 to C.sub.
    Type: Grant
    Filed: March 3, 1998
    Date of Patent: October 12, 1999
    Inventors: Charles A. Drake, An-hsiang Wu
  • Patent number: 5952535
    Abstract: This invention is an improved process for the conversion of a C.sub.9 mixed alkyl aromatic feedstream containing ethyl substituted aromatics to a product rich in toluenes and/or xylenes via catalytic transalkylation/disproportionation using a palladium loaded moderately, dealuminated mordenite catalyst in the presence of added hydrogen and benzene.
    Type: Grant
    Filed: September 18, 1996
    Date of Patent: September 14, 1999
    Assignee: Catalytica, Inc.
    Inventors: David L. King, Eric G. Derouane, Jacques C. DeDeken, Toshihiko Masuda, Shinji Nishikawa, Hiroshi Fujii, Masaaki Adachi
  • Patent number: 5929295
    Abstract: A catalyst composition, a process for producing the composition and a hydrocarbon conversion process for converting a C.sub.9 + aromatic compound to a C.sub.6 to C.sub.8 aromatic hydrocarbon such as a xylene are disclosed. The composition comprises an acid-treated zeolite having impregnated thereon a metal or metal oxide. The composition can be produced by incorporating the metal or metal oxide into the zeolite. The hydrocarbon conversion process comprises contacting a fluid which comprises a C.sub.9 + aromatic compound with the catalyst composition under a condition sufficient to effect the conversion of a C.sub.9 + aromatic compound to a C.sub.6 to C.sub.8 aromatic hydrocarbon.
    Type: Grant
    Filed: August 6, 1997
    Date of Patent: July 27, 1999
    Assignee: Phillips Petroleum Company
    Inventors: An-hsiang Wu, Ralph J. Melton, Charles A. Drake
  • Patent number: 5907074
    Abstract: A catalyst composition and a process for hydrodealkylating a C.sub.9 + aromatic compound such as, for example, 1,2,4-trimethylbenzene to a C.sub.6 to C.sub.8 aromatic hydrocarbon such as a xylene are disclosed. The composition comprises a zeolite, a metal oxide, and an activity modifier selected from the group consisting of silicon oxides, sulfur oxides, phosphorus oxides, boron oxides, magnesium oxides, tin oxides, titanium oxides, zirconium oxides, germanium oxides, indium oxides, lanthanum oxides, cesium oxides, and combinations of any two or more thereof. The process comprises contacting a fluid which comprises a C.sub.9 + aromatic compound with the catalyst composition under a condition sufficient to effect the conversion of a C.sub.9 + aromatic compound to a C.sub.6 to C.sub.8 aromatic hydrocarbon.
    Type: Grant
    Filed: January 13, 1997
    Date of Patent: May 25, 1999
    Assignee: Phillips Petroleum Company
    Inventors: An-hsiang Wu, Charles A. Drake
  • Patent number: 5877374
    Abstract: A new process for the hydrodealkylation of ethylbenzene and the isomerization of xylenes at low pressure and at a low hydrogen to ethylbenzene mole ratio as well as a low hydrogen to hydrocarbon feed mole ratio using a catalyst comprising (a) HZSM-5 having a particle size less than 1.0 microns, (b) a Group VIII metal such as platinum, and (c) an additional element such as magnesium.
    Type: Grant
    Filed: April 2, 1997
    Date of Patent: March 2, 1999
    Assignee: Chevron Chemical Company
    Inventors: Gerald J. Nacamuli, Roger F. Vogel
  • 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: 5866742
    Abstract: A catalyst composition, a process for producing the composition and a hydrocarbon conversion process for converting a C.sub.9 + aromatic compound to a C.sub.6 to C.sub.8 aromatic hydrocarbon such as a xylene are disclosed. The composition comprises a zeolite having incorporated therein a promoter comprising carbon and a metal or metal oxide. The composition can be produced by incorporating a metal compound into the zeolite followed by thermal treatment of the resulting zeolite with a hydrocarbon. The hydrocarbon conversion process comprises contacting a fluid which comprises a C.sub.9 + aromatic compound with the catalyst composition under a condition sufficient to effect the conversion of a C.sub.9 + aromatic compound to a C.sub.6 to C.sub.8 aromatic hydrocarbon.
    Type: Grant
    Filed: August 4, 1997
    Date of Patent: February 2, 1999
    Assignee: Phillips Petroleum Company
    Inventors: An-hsiang Wu, Ralph J. Melton, Charles A. Drake
  • Patent number: 5866741
    Abstract: A catalyst composition, a process for producing the composition and a hydrocarbon conversion process for converting a C.sub.9 + aromatic compound to a C.sub.6 to C.sub.8 aromatic hydrocarbon such as a xylene are disclosed. The composition comprises a zeolite having impregnated thereon an activity promoter selected from the group consisting of molybdenum, molybdenum oxides, lanthanum, lanthanum oxides, and combinations of two or more thereof. The composition can be produced by incorporating the activity promoter into the zeolite. The hydrocarbon conversion process comprises contacting a fluid which comprises a C.sub.9 + aromatic compound with the catalyst composition under a condition sufficient to effect the conversion of a C.sub.9 + aromatic compound to a C.sub.6 to C.sub.8 aromatic hydrocarbon.
    Type: Grant
    Filed: July 23, 1997
    Date of Patent: February 2, 1999
    Assignee: Phillips Petroleum Company
    Inventors: An-hsiang Wu, Charles A. Drake
  • Patent number: 5856609
    Abstract: A catalyst composition and a process for hydrodealkylating a C.sub.9 + aromatic compound such as, for example, 1,2,4-trimethylbenzene to a C.sub.6 to C.sub.8 aromatic hydrocarbon such as a xylene are disclosed. The composition comprises an alumina, a metal oxide, and a acid site modifier selected from the group consisting of silicon oxides, sulfur oxides, phosphorus oxides, boron oxides, magnesium oxides, tin oxides, titanium oxides, zirconium oxides, molybdenum oxides, germanium oxides, indium oxides, lanthanum oxides, cesium oxides, and combinations of any two or more thereof. The process comprises contacting a fluid which comprises a C.sub.9 + aromatic compound with the catalyst composition under a condition sufficient to effect the conversion of a C.sub.9 + aromatic compound to a C.sub.6 to C.sub.8 aromatic hydrocarbon.
    Type: Grant
    Filed: September 12, 1996
    Date of Patent: January 5, 1999
    Assignee: Phillips Petroleum Company
    Inventors: An-hsiang Wu, Charles A. Drake
  • Patent number: 5856613
    Abstract: The present invention provides a method for producing .beta.-methylnaphthalene from an inexpensive and easily available feed oil. According to the invention, highly pure .beta.-methylnaphthalene adequate for industrial use can be mass-produced at reduced costs. The method comprises catalytic hydrodealkylation of a feed oil containing an alkyl naphthalene having at least two methyl groups in the presence of a catalyst having at least one metal species of selected from the group consisting of vanadium (V), chromium (Cr), nickel (Ni), rhodium (Rh), platinum (Pt), iridium (Ir), and compounds of these metals as an active component and a carrier therefor containing at least one of alumina and silica as its primary component, with a hydrogen partial pressure of 1 to 50 kgf/cm.sup.2, at a temperature of 450.degree. C. to 650.degree. C., and for a contact time of 3 to 35 seconds. The method of the invention is excellent in that it affords .beta.-methylnaphthalene of a chemical grade with a high yield.
    Type: Grant
    Filed: September 25, 1996
    Date of Patent: January 5, 1999
    Assignee: Fuji Oil Company Limited and Petroleum Energy Center
    Inventors: Masaharu Tashiro, Toshio Tsutsui, Osamu Kubota, Shinichi Okada, Toshihito Nakamura
  • Patent number: 5856608
    Abstract: A catalyst composition and a process for converting a C.sub.9 + aromatic compound such as, for example, 1,2,4-trimethylbenzene to a C.sub.6 to C.sub.8 aromatic hydrocarbon such as a xylene are disclosed. The composition comprises a zeolite, a metal oxide, and optionally a selectivity modifier selected from the group consisting of silicon, sulfur, phosphorus, boron, magnesium, tin, titanium, zirconium, germanium, indium, lanthanum, cesium, oxides thereof and combinations of any two or more thereof. The process comprises contacting a fluid which comprises a C.sub.9 + aromatic compound with the catalyst composition under a condition sufficient to effect the conversion of a C.sub.9 + aromatic compound to a C.sub.6 to C.sub.8 aromatic hydrocarbon.
    Type: Grant
    Filed: February 21, 1997
    Date of Patent: January 5, 1999
    Assignee: Phillips Petroleum Company
    Inventors: An-hsiang Wu, Charles A. Drake
  • Patent number: 5851379
    Abstract: A catalytic reforming process is disclosed using a catalyst containing a Group VIII metal, low amounts of bismuth, and a zeolite L. The catalyst is a non-acidic, monofunctional reforming catalyst. Preferably, the catalyst contains one or more halogens. Preferably, the feed includes C.sub.8 hydrocarbons. The addition of small amounts of bismuth increase or substantially maintain catalyst stability. Unexpectedly low dealkylation rates are achieved using the catalyst while reforming to produce aromatics, especially to produce xylenes such as paraxylene.
    Type: Grant
    Filed: December 22, 1997
    Date of Patent: December 22, 1998
    Assignees: Chevron Chemical Company, Idemitsu Kosan Co., Ltd.
    Inventors: Robert A. Innes, Michio Sugimoto, Tetsuya Fukunaga
  • Patent number: 5849969
    Abstract: Carburization and metal-dusting while hydrodealkylating a hydrodealkylatable hydrocarbon are reduced even in the substantial absence of sulfur.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: December 15, 1998
    Assignee: Chevron Chemical Company
    Inventors: John V. Heyse, Bernard F. Mulaskey, Robert A. Innes, Daniel P. Hagewiesche, William J. Cannella, David C. Kramer
  • Patent number: 5847256
    Abstract: An improved process for producing xylene from feedstock containing C.sub.9 alkyl aromatic hydrocarbons with the aid of a catalyst capable of disproportionation, rearrangement, and dealkylation, wherein said improvement comprises performing the reaction in the presence of an aromatic hydrocarbon having one or more ethyl groups in an amount of 5 to 50 wt %.
    Type: Grant
    Filed: October 22, 1997
    Date of Patent: December 8, 1998
    Assignee: Toray Industries, Inc.
    Inventors: Ryoji Ichioka, Shinobu Yamakawa, Hirohito Okino
  • Patent number: 5817903
    Abstract: A catalyst composition and a process for converting a C.sub.9 + aromatic compound to C.sub.6 to C.sub.8 aromatic hydrocarbons such as xylenes are disclosed. The catalyst composition comprises a zeolite and a metal. The process comprises contacting a fluid stream containing a C.sub.9 + aromatic compound with the catalyst composition under a condition sufficient to effect the production of C.sub.6 to C.sub.8 aromatic hydrocarbon. Also disclosed is a process for producing the catalyst composition which can comprise: (1) impregnating a zeolite with an effective and coke-reducing amount of a metal compound under a condition sufficient to effect the production of a metal-promoted zeolite and (2) calcining the metal-promoted zeolite.
    Type: Grant
    Filed: April 4, 1997
    Date of Patent: October 6, 1998
    Assignee: Phillips Petroleum Company
    Inventors: An-hsiang Wu, Charles A. Drake
  • Patent number: 5811615
    Abstract: A catalyst composition and a process for hydrodealkylating a C.sub.9 + aromatic compound to a C.sub.6 to C.sub.8 aromatic hydrocarbon such as a xylene are disclosed. The composition comprises an alumina and hexavalent chromium oxide. The process comprises contacting a fluid which comprises a C.sub.9 + aromatic compound with the catalyst composition under a condition sufficient to effect the conversion of a C.sub.9 + aromatic compound to a C.sub.6 to C.sub.8 aromatic hydrocarbon.
    Type: Grant
    Filed: October 30, 1996
    Date of Patent: September 22, 1998
    Assignee: Phillips Petroleum Company
    Inventors: An-hsiang Wu, Charles A. Drake
  • Patent number: 5789642
    Abstract: A catalyst composition and a process for hydrodealkylating a C.sub.9 + aromatic compound to a C.sub.6 to C.sub.8 aromatic hydrocarbon are disclosed. The composition comprises an alumina, molybdenum oxide, and zinc oxide. The process comprises contacting a fluid which comprises a C.sub.9 + aromatic compound with the catalyst composition under a condition sufficient to effect the conversion of a C.sub.9 + aromatic compound to a C.sub.6 to C.sub.8 aromatic hydrocarbon.
    Type: Grant
    Filed: December 12, 1996
    Date of Patent: August 4, 1998
    Assignee: Phillips Petroleum Company
    Inventors: An-hsiang Wu, Charles A. Drake
  • Patent number: 5763721
    Abstract: A catalyst composition and a process for hydrodealkylating a C.sub.9 + aromatic compound such as, for example, 1,2,4-trimethylbenzene to a C.sub.6 to C.sub.8 aromatic hydrocarbon such as a xylene are disclosed. The composition comprises an alumina, a metal oxide, a phosphorus oxide and optionally, an acid site modifier selected from the group consisting of silicon oxides, sulfur oxides, boron oxides, magnesium oxides, tin oxides, titanium oxides, zirconium oxides, molybdenum oxides, germanium oxides, indium oxides, lanthanum oxides, cesium oxides, and combinations of any two or more thereof. The process comprises contacting a fluid which comprises a C.sub.9 + aromatic compound with the catalyst composition under a condition sufficient to effect the conversion of a C.sub.9 + aromatic compound to a C.sub.6 to C.sub.8 aromatic hydrocarbon.
    Type: Grant
    Filed: December 12, 1996
    Date of Patent: June 9, 1998
    Assignee: Phillips Petroleum Company
    Inventors: An-hsiang Wu, Charles A. Drake
  • Patent number: 5744674
    Abstract: A catalyst for the preparation of benzene, toluene and xylene from C.sub.9.sup.+ heavy aromatics consists of zeolite ZSM-5 and .gamma.- or .eta.-Al.sub.2 O.sub.3 as carrier, Re, Sn and Pt or Pd supported on the carrier. Under the conditions of 350.degree.-450.degree. C., 0.5-3.5 MPa, a WHSV of 1-5 h.sup.-1 and a H.sub.2 /HC ratio (v/v) of 500-1200, the catalyst achieves high activity and stability as well as low hydrogen consumption.
    Type: Grant
    Filed: February 6, 1996
    Date of Patent: April 28, 1998
    Assignees: China Petrochemical Corporation, Research Institute of Petroleum Processing
    Inventors: Shouxi Gui, Yuzhi Hao, Yanqing Li, Zhenhua Jing, Haohui Gu, Zhanqiao Liang, Baoyu Cheng
  • Patent number: 5714659
    Abstract: A catalyst composition and a process for hydrodealkylating a C.sub.9 + aromatic compound such as, for example, 1,2,4-trimethylbenzene to a C.sub.6 to C.sub.8 aromatic hydrocarbon such as a xylene are disclosed. The composition comprises an alumina, a metal oxide, and a acid site modifier selected from the group consisting of silicon oxides, boron oxides magnesium oxides, tin oxides, titanium oxides, zirconium oxides, molybdenum oxides, germanium oxides, indium oxides, lanthanum oxides, cesium oxides, and combinations of any two or more thereof. The process comprises contacting a fluid which comprises a C.sub.9 + aromatic compound with the catalyst composition under a condition sufficient to effect the conversion of a C.sub.9 + aromatic compound to a C.sub.6 to C.sub.8 aromatic hydrocarbon.
    Type: Grant
    Filed: August 29, 1996
    Date of Patent: February 3, 1998
    Assignee: Phillips Petroleum Company
    Inventors: An-hsiang Wu, Charles A. Drake
  • Patent number: 5714660
    Abstract: A catalyst composition and a process for hydrodealkylating a C.sub.9 + aromatic compound such as, for example, 1,2,4-trimethylbenzene to a C.sub.6 to C.sub.8 aromatic hydrocarbon such as a xylene are disclosed. The composition comprises an alumina, a metal oxide, and an acid site modifier selected from the group consisting of silicon oxides, phosphorus oxides, boron oxides, magnesium oxides, tin oxides, titanium oxides, zirconium oxides, molybdenum oxides, germanium oxides, indium oxides, lanthanum oxides, cesium oxides, and combinations of any two or more thereof. The process comprises contacting a fluid which comprises a C.sub.9 + aromatic compound with the catalyst composition under a condition sufficient to effect the conversion of a C.sub.9 + aromatic compound to a C.sub.6 to C.sub.8 aromatic hydrocarbon.
    Type: Grant
    Filed: August 29, 1996
    Date of Patent: February 3, 1998
    Assignee: Phillips Petroleum Company
    Inventors: An-hsiang Wu, Charles A. Drake, Ralph J. Melton
  • Patent number: 5689026
    Abstract: A process for hydrodealkylating C.sub.9 -C.sub.12 alkyl-substituted benzenes (preferably trimethylbenzenes) to C.sub.6 -C.sub.8 aromatic hydrocarbons (in particular, toluene and xylenes) and C.sub.1 -C.sub.5 alkanes employs a catalyst containing zeolite Beta, nickel, molybdenum and sulfur (preferably as sulfides of nickel and of molybdenum).
    Type: Grant
    Filed: April 24, 1996
    Date of Patent: November 18, 1997
    Assignee: Phillips Petroleum Company
    Inventors: An-hsiang Wu, Charles A. Drake, Ralph J. Melton
  • Patent number: 5132480
    Abstract: Catalytic hydrodealkylation by means of a catalyst which comprises microporous particles having a catalytic species carried thereon. Particulars of the microporous particles are disclosed.
    Type: Grant
    Filed: February 5, 1990
    Date of Patent: July 21, 1992
    Assignee: Fuji Oil Company, Ltd.
    Inventors: Toshio Tsutsui, Osamu Kubota, Toshihito Nakamura
  • Patent number: 5043513
    Abstract: A process is provided for hydrodealkylation of alkylaromatic hydrocarbons to produce benzene or BTX over catalyst comprising a particular metal and a synthetic zeolite, said zeloite characterized by an X-ray diffraction pattern including interplanar d-spacings at 12.36.+-.0.4, 11.03.+-.0.2, 8.83.+-.0.14, 6.18--0.12, 6.00.+-.0.10, 4.06.+-.0.07, 3.91.+-.0.07 and 3.42.+-.0.06 Angstroms.
    Type: Grant
    Filed: October 9, 1990
    Date of Patent: August 27, 1991
    Assignee: Mobil Oil Corp.
    Inventors: Paul A. Howley, Stuart S. Shih
  • Patent number: 5004854
    Abstract: A process for the production of pseudocumene, mesitylene, xylenes and benzene by upgrading C.sub.9 aromatics or mixtures of C.sub.7 -C.sub.9 aromatics is disclosed. The process is carried out under catalytic upgrading conditions using a catalyst which comprises a crystalline zeolite having a silica-to-alumina ratio of at least about 12 and a constraint index from about 1 to about 12, the zeolite preferably being ZSM-5.
    Type: Grant
    Filed: December 4, 1986
    Date of Patent: April 2, 1991
    Assignee: Mobil Oil Corp.
    Inventor: Tsoung Y. Yan
  • Patent number: 5004855
    Abstract: Ethylbenzene can be substantially hydrode-ethylated to benzene with a minimized loss of xylene by placing a C.sub.8 aromatic hydrocarbon mixture containing ethylbenzene and xylene in the presence of hydrogen in contact with a catalyst comprising 0.6 to 20.0 parts by weight of rhenium, 100 parts by weight of an acid type of a zeolite having a main cavity inlet composed of a 10-membered oxygen ring and 100 to 900 parts by weight of alumina, which has been subjected to sulfiding.
    Type: Grant
    Filed: August 19, 1988
    Date of Patent: April 2, 1991
    Assignee: Toray Industries, Inc.
    Inventors: Kuniyuki Tada, Eiichi Minomiya, Masatoshi Watanabe
  • Patent number: 5001296
    Abstract: A process is provided for hydrodealkylation of alkylaromatic hydrocarbons to produce benzene or BTX over catalyst comprising a noble metal and a synthetic zeolite, said zeolite characterized by an X-ray diffraction pattern including interplanar d-spacings at 12.36.+-.0.4, 11.03.+-.0.2, 8.83.+-.0.14, 6.18.+-.0.12, 6.00.+-.0.10, 4.06.+-.0.07, 3.91.+-.0.07 and 3.42.+-.0.06 Angstroms.
    Type: Grant
    Filed: March 7, 1990
    Date of Patent: March 19, 1991
    Assignee: Mobil Oil Corp.
    Inventors: Paul A. Howley, Stuart S. Shih
  • Patent number: 4654457
    Abstract: A method for selectively dealkylating a 1,4-dialkylbenzene in a dialkylbenzene mixture is disclosed, comprising contacting the mixture with a zeolite catalyst which is prepared by the steps of: (1) hydrothermally synthesizing a zeolite from a system in which an alkali metal cation and an organic cation or its precursor coexist and then calcining the zeolite; and (2) modifying the zeolite with a metal or metalloid oxide. This method permits selective dealkylation of a 1,4-dialkylbenzene while maintaining the yield and purity of olefins formed during the dealkylation at high levels.
    Type: Grant
    Filed: October 17, 1985
    Date of Patent: March 31, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroshi Sato, Norio Ishii, Kenichi Hirose
  • Patent number: 4642409
    Abstract: An industrially excellent method for selectively dealkylating a 1,4-dialkylbenzene in a dialkylbenzene mixture by the use of a specified zeolite catalyst is disclosed, which catalyst is a crystalline zeolite ion-exchanged with sodium ion, potassium ion, potassium ion, rubidium ion, or cesium ion. The specific zeolite catalyst is easy to prepare and allows selective dealkylation of the 1,4-dialkylbenzene and recovery of the formed olefins in a high yield and a high purity.
    Type: Grant
    Filed: February 10, 1986
    Date of Patent: February 10, 1987
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Hiroshi Sato, Norio Ishii, Kenichi Hirose
  • Patent number: 4577049
    Abstract: A process is disclosed for dealkylating durene under elevated temperatures and pressures with a polynuclear aromatic compound. The dealkylation is carried out in the presence of a carbon-containing molecular sieve.
    Type: Grant
    Filed: April 24, 1985
    Date of Patent: March 18, 1986
    Assignee: Mobil Oil Corporation
    Inventor: Leslie R. Rudnick
  • Patent number: 4560820
    Abstract: A process for dealkylating alkylaromatic hydrocarbons using intermediate pore size zeolites substantially free of acidity is disclosed.
    Type: Grant
    Filed: October 25, 1984
    Date of Patent: December 24, 1985
    Assignee: Chevron Research Company
    Inventor: Leslie A. Field
  • Patent number: 4496784
    Abstract: Molybdenum is ion exchanged into a crystalline aluminosilicate zeolite, replacing metals such as sodium, calcium, and potassium, by contacting the zeolite with an aqueous solution containing molybdenyl cations (i.e., MoO.sub.2.sup.2+) and having a pH below 7.0 but higher than that which would substantially affect the crystallinity of the zeolite. The resulting zeolite, when calcined or sulfided, is useful as a catalyst for hydrocarbon conversion reactions, particularly with respect to the hydrodealkylation of toluene to benzene and methane.
    Type: Grant
    Filed: July 20, 1981
    Date of Patent: January 29, 1985
    Assignee: Union Oil Company of California
    Inventor: Eric L. Moorehead
  • Patent number: 4469909
    Abstract: This invention provides a catalytic process for converting to BTX a C.sub.9 + monocyclic aromatic hydrocarbon feed having a prescribed content of alkyl groups with more than one carbon atom. It further provides a process wherein said conversion is coupled with a catalytic xylene isomerization unit. The catalyst used in the process is a steamed composite comprising platinum and a crystalline zeolite such as ZSM-5.
    Type: Grant
    Filed: September 1, 1983
    Date of Patent: September 4, 1984
    Assignee: Mobil Oil Corporation
    Inventors: Arthur W. Chester, Yung-Feng Chu
  • Patent number: 4467129
    Abstract: Xylenes containing ethylbenzene are contacted with a catalyst comprising an acid type mordenite and a specific acid type zeolite such as, for example, ZSM-5, ZSM-8 or ZSM-11, in vapor phase in the presence of hydrogen, whereby there are performed deethylation of ethylbenzene and isomerization of xylenes.
    Type: Grant
    Filed: November 24, 1982
    Date of Patent: August 21, 1984
    Assignee: Toray Industries, Inc.
    Inventors: Kazuyoshi Iwayama, Atsushi Ebitani, Takehisa Inoue, Atsuo Kani
  • Patent number: 4451687
    Abstract: An alkylaromatic hydrocarbon feed stream is hydrodealkylate in the presence of a catalyst having a reduced rate of deactivation, or a lower coking tendency. The catalyst comprises a gamma-alumina support containing 8 to 12 wt. % Cr.sub.2 O.sub.3 and 0.2 to 0.7 wt. % Na.sub.2 O and having a surface area from 175 to 275 m.sup.2 /g and a pore volume from 0.5 to 1.2 cc/g. The catalyst is also useful in the hydrodesulfurization of thiophene containing hydrocarbon streams.
    Type: Grant
    Filed: October 7, 1983
    Date of Patent: May 29, 1984
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Francis P. Daly, Frederick C. Wilhelm
  • Patent number: 4436836
    Abstract: An alkylaromatic hydrocarbon feed stream is hydrodealkylate in the presence of a catalyst having a reduced rate of deactivation, or a lower coking tendency. The catalyst comprises a gamma-alumina support containing 8 to 12 wt % Cr.sub.2 O.sub.3 and 0.2 to 0.7 wt % Na.sub.2 O and having a surface area from 175 to 275 m.sup.2 /g and a pore volume from 0.5 to 1.2 cc/g. The catalyst is also useful in the hydrodesulfurization of thiophene containing hydrocarbon streams.
    Type: Grant
    Filed: July 6, 1982
    Date of Patent: March 13, 1984
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Francis P. Daly, Frederick C. Wilhelm
  • Patent number: 4431857
    Abstract: Incorporation of above about 50 ppm water into feed of a hydrocarbon conversion process using an AMS-1B crystalline borosilicate-based catalyst alters the product distribution produced in such process.
    Type: Grant
    Filed: August 2, 1982
    Date of Patent: February 14, 1984
    Assignee: Standard Oil Company (Indiana)
    Inventor: Allen I. Feinstein
  • Patent number: 4409413
    Abstract: A mixture of xylene isomers containing ethyl benzene is contacted with a catalyst comprising a mordenite type zeolite and rhenium or phosphorus in the presence of hydrogen to isomerize xylenes and at the same time dealkylate ethyl benzene into mainly benzene.
    Type: Grant
    Filed: June 16, 1981
    Date of Patent: October 11, 1983
    Assignee: Toray Industries, Incorporated
    Inventors: Kazuyoshi Iwayama, Takehisa Inoue
  • Patent number: 4399051
    Abstract: A method for regenerating of rhodium-containing catalysts exhausted and sulphur-poisoned in the course of dealkylating alkyl benzenes or mixture thereof with steam or hydrogen, comprising the steps of burning out coke deposits by an oxygen-containing gas and chlorinating the catalyst with chlorine or with a chlororganic compound in a flow of hydrogen, an inert gas or a mixture of an inert gas with oxygen and moisture. The catalyst is additionally treated with ammonia or with a nitrogen-containing compound capable of decomposing under the treatment to yield ammonia in the presence of at least one component selected from the group consisting of: water, hydrogen, and nitrogen-oxygen mixture. The treatment can be conducted both in the liquid and the gaseous phases at temperatures ranging between 20.degree. and 650.degree. C. and at a pressure between 1 and 50 atm.The present invention can be used for regeneration of rhodium-containing catalysts and used for dealkylating alkyl benzenes with steam or hydrogen.
    Type: Grant
    Filed: February 17, 1981
    Date of Patent: August 16, 1983
    Inventors: Georgy L. Rabinovich, Zoya P. Lukina, Kira L. Volkova, Viktor N. Mozhaiko
  • Patent number: 4387261
    Abstract: A process is disclosed for the dealkylation of durene resulting from a methanol to gasoline conversion by contacting a durene-containing fraction with zeolite ZSM-12 at elevated temperatures and pressures.
    Type: Grant
    Filed: April 9, 1982
    Date of Patent: June 7, 1983
    Assignee: Mobil Oil Corporation
    Inventors: Arthur W. Chester, Yung F. Chu
  • Patent number: 4341622
    Abstract: Benzene, toluene and xylenes are prepared from heavy reformate in substantially the proportion in said reformate of single ring aromatic compounds bearing none, one or two methyl groups by contacting said heavy reformate at 800.degree.-1000.degree. F. with a zeolite of low acid activity.
    Type: Grant
    Filed: December 4, 1980
    Date of Patent: July 27, 1982
    Assignee: Mobil Oil Corporation
    Inventors: Samuel A. Tabak, Roger A. Morrison