To Produce Polycyclic Patents (Class 585/268)
  • Patent number: 10441944
    Abstract: A catalyst composition for isomerization of paraffins includes at least one metal, at least one heteropoly acid and a support material. Further provided are a process for preparation of the catalyst composition and a process for isomerization of paraffins using the catalytic composition.
    Type: Grant
    Filed: December 15, 2015
    Date of Patent: October 15, 2019
    Assignee: Hindustan Petroleum Corporation Ltd.
    Inventors: Raman Ravishankar, Safinaz Saif, Sunil Mehla, Bennet Chellian, Peddy Venkatachallapathy Rao, Choudary Venkateswarlu Nettem, Sriganesh Gandham
  • Patent number: 9452965
    Abstract: A process for producing phenol and/or cyclohexanone is described in which cyclohexylbenzene is contacted with an oxygen-containing gas under conditions effective to produce an oxidation effluent comprising cyclohexylbenzene hydroperoxide and at least part of cyclohexylbenzene hydroperoxide is contacted with a cleavage catalyst under conditions effective to produce a cleavage effluent containing phenol and cyclohexanone. At least one of the oxidation effluent and the cleavage effluent contains at least one phenylcyclohexanol as a by-product and the process further comprises contacting the phenylcyclohexanol with a dehydration catalyst comprising a molecular sieve of the MCM-22 family under conditions effective to convert at least part of the phenylcyclohexanol to phenylcyclohexene.
    Type: Grant
    Filed: September 13, 2013
    Date of Patent: September 27, 2016
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Jihad M. Dakka, Charles Morris Smith, Keith H. Kuechler, Christopher L. Becker, Terry E. Helton, Jason D. Davis, Edmund J. Mozeleski
  • Publication number: 20150126782
    Abstract: In a process for producing cyclohexylbenzene, hydrogen, and benzene are contacted in a first reaction zone under conditions effective to produce a product effluent containing residual benzene in the vapor phase and cyclohexylbenzene in the liquid phase. The product effluent is separated into a first stream that is rich in residual benzene in the vapor phase as compared to the product effluent and a second stream that is rich in cyclohexylbenzene in the liquid phase as compared to the product effluent. At least a portion of the first stream is cooled to condense at least a portion of the residual benzene in the vapor phase to the liquid phase and produce a condensate stream. At least a portion of the condensate stream is recycled to the first reaction zone.
    Type: Application
    Filed: September 5, 2012
    Publication date: May 7, 2015
    Applicant: ExxonMobil Chemical Company - Law Technology
    Inventors: Hari Nair, Christopher L. Becker, James R. Lattner, Jihad M. Dakka
  • Publication number: 20150099910
    Abstract: A process for activating a hydroalkylation catalyst in a first state comprising an acid component and a hydrogenating metal component, including: (i) treatment at a temperature of at least 120° C. in the presence of hydrogen for a first duration to produce a catalyst in a second state having a first hydroalkylation activity; (ii) contacting the catalyst in the second state with an aromatic compound and hydrogen under a hydroalkylation condition effective to convert at least part of the aromatic compound to a cycloalkylaromatic compound and produce a catalyst in a third state; and (iii) treating the catalyst in the third state at a temperature of at least 160° C. in the presence of hydrogen but advantageously in the substantial absence of the aromatic compound for a third duration to produce an activated catalyst in a fourth state having a third hydroalkylation activity greater than the first hydroalkylation activity.
    Type: Application
    Filed: July 9, 2013
    Publication date: April 9, 2015
    Inventors: Gabor Kiss, Tan-Jen Chen, Thomas E. Green
  • Publication number: 20150045596
    Abstract: In a process for producing cyclohexylbenzene, benzene is contacted with hydrogen in the presence of a hydroalkylation catalyst under hydroalkylation conditions effective to form a first effluent stream comprising cyclohexylbenzene, cyclohexane, and benzene. At least a portion of the cyclohexane from the first effluent stream is then contacted with hydrogen in the presence of a dehydrogenation catalyst under dehydrogenation conditions effective to convert at least some of the cyclohexane into benzene contained in a second effluent stream. At least some of the hydrogen is supplied to the process so as to contact the dehydrogenation zone (e.g., the dehydrogenation catalyst) before contacting the hydroalkylation catalyst.
    Type: Application
    Filed: December 5, 2012
    Publication date: February 12, 2015
    Inventors: Christopher L. Becker, James R. Lattner, Keith H. Kuechler, Hari Nair
  • Publication number: 20140371498
    Abstract: In a process for producing cyclohexylbenzene, benzene is contacted with hydrogen under hydroalkylation conditions effective to form a first effluent stream comprising cyclohexylbenzene, cyclohexane, methylcyclopentane, and unreacted benzene. At least a portion of the first effluent stream is contacted with a dehydrogenation catalyst under dehydrogenation conditions to convert at least a portion of the cyclohexane to benzene thereby forming a second effluent stream. The amount of methylcyclopentane in the second effluent stream is different by no more than 65% of the total amount of the portion of the first effluent stream, said amounts being on a weight basis. A methylcyclopentane-containing stream is removed from either the first or the second effluent stream and at least a portion of the second effluent stream containing benzene is recycled to the hydroalkylation step.
    Type: Application
    Filed: December 2, 2011
    Publication date: December 18, 2014
    Applicant: ExxonMobil Chemical Company - Law Technology
    Inventors: Keith H. Kuechler, James R. Lattner, Christopher L. Becker, Jihad M. Dakka, Tan-Jen Chen
  • Publication number: 20140275605
    Abstract: A composition is described comprising a mixture of (methylcyclohexyl)toluene isomers having the following formula: wherein the mixture comprises at least 50 wt % in total of the 3,3, 3,4 4,3 and 4,4-isomers of (methylcyclohexyl)toluene.
    Type: Application
    Filed: March 7, 2014
    Publication date: September 18, 2014
    Inventors: Jihad M. Dakka, Lorenzo C. DeCaul, Wei Tang
  • Publication number: 20140100400
    Abstract: A method for preparing a phenylcyclohexane of formula I by hydrogenation of a biphenyl of formula II with hydrogen in the presence of Raney nickel, where R1 and R2 both have the same meaning in formulas I and II and independently of one another are hydrogen atoms, C1- to C10-alkyl groups or phenyl groups, wherein the hydrogenation takes place in the presence of 0 to 20 parts by weight of water to 100 parts by weight of Raney nickel.
    Type: Application
    Filed: September 30, 2013
    Publication date: April 10, 2014
    Applicant: BASF SE
    Inventor: Martin BOCK
  • Publication number: 20130289323
    Abstract: A hydroalkylation catalyst comprising a molecular sieve and a compound of a hydrogenation metal is activated by treating the catalyst at a temperature of less than about 250° C. in the presence of hydrogen.
    Type: Application
    Filed: September 20, 2011
    Publication date: October 31, 2013
    Applicant: Exxon Mobil Chemical Company -Law Technology
    Inventors: Teng Xu, Edward Andrew Lemon, JR., Terry Eugene Helton, Tan-Jen Chen, Charles Morris Smith
  • Publication number: 20130202522
    Abstract: The invention relates to hydroalkylation processes. In the processes, a hydrogen stream comprising hydrogen and an impurity is treated to reduce the amount of the impurity in the hydrogen stream. The hydrogen is then hydroalkylated with benzene to form at least some cyclohexylbenzene. The processes also relate to treating a benzene stream comprising benzene and an impurity with an adsorbent to reduce the amount of the impurity in the benzene stream. The hydroalkylation processes described herein may be used as part of a process to make phenol.
    Type: Application
    Filed: April 4, 2011
    Publication date: August 8, 2013
    Inventors: Tan-Jen Chen, Teng Xu, Terry Helton, Francisco M. Benitez, Charles M. Smith
  • Publication number: 20130150623
    Abstract: An object is to provide a process for providing hydrogen or heavy hydrogens conveniently without the necessity of large-scale equipment and a process capable of performing hydrogenation (protiation, deuteration or tritiation) reaction conveniently without the use of an expensive reagent and a special catalyst. The production process includes a process for producing hydrogen or heavy hydrogens, containing subjecting water or heavy water to mechanochemical reaction in the presence of a catalyst metal, and a process for producing a hydrogenated (protiated, deuterated or tritiated) organic compound, containing subjecting an organic compound and water or heavy water to mechanochemical reaction in the presence of a catalyst metal.
    Type: Application
    Filed: August 16, 2011
    Publication date: June 13, 2013
    Applicant: Shiono Chemical Co., Ltd.
    Inventors: Hironao Sajiki, Yasunari Monguchi, Yoshinari Sawama, Shinichi Kondo
  • Patent number: 8450541
    Abstract: A method for producing products containing cyclic organic compounds from biomass oil includes adding a biomass oil to a vessel; heating the biomass oil to crack the biomass oil; removing undesired or unreacted materials, heavy ends, and light ends from the cracked biomass oil; and extracting components from the cracked biomass oil to produce a mixture of products containing between 5% and 90% cyclic organic compounds by weight. A method for producing a high-octane aviation fuel with low lead content includes cracking a biomass oil, separating a middle distillate mixture from cracked biomass oil, decarboxylating the middle distillate mixture to produce a mixture of products containing at least about 50% cyclic alkane and alkene compounds by weight, and blending the mixture of products with a fuel having an octane number below 95 to produce an aviation fuel having an octane number of at least 100.
    Type: Grant
    Filed: November 25, 2009
    Date of Patent: May 28, 2013
    Assignee: The University of North Dakota
    Inventors: Wayne S. Seames, Darrin S. Muggli, Brian M. Tande
  • Patent number: 8329956
    Abstract: In a process for producing cyclohexylbenzene, benzene and hydrogen are contacted under hydroalkylation conditions with a catalyst system comprising a MCM-22 family molecular sieve and at least one hydrogenation metal. The conditions comprise a temperature of about 140° C. to about 175° C., a pressure of about 135 psig to about 175 psig (931 kPag to 1207 kPag), a hydrogen to benzene molar ratio of about 0.30 to about 0.65 and a weight hourly space velocity of benzene of about 0.26 to about 1.05 hr?1.
    Type: Grant
    Filed: March 1, 2012
    Date of Patent: December 11, 2012
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Jane C. Cheng, Tan-Jen Chen, Prasenjeet Ghosh
  • Patent number: 8309777
    Abstract: An aromatics hydrogenation catalyst composition which comprises a noble metal component and a support comprising zirconia, silica, and, optionally, alumina. The catalyst composition is manufactured by co-mulling silica, a zirconium compound, and, optionally, alumina to form a mixture that is formed into a shape, such as by extrusion to form an extrudate, with the shape being calcined and noble metal being incorporated into the shape. The catalyst composition may be used in the saturation of aromatic compounds.
    Type: Grant
    Filed: April 21, 2010
    Date of Patent: November 13, 2012
    Assignee: Shell Oil Company
    Inventors: John Anthony Smegal, Johannes Anthonius Robert Van Veen
  • Publication number: 20120277472
    Abstract: The present invention relates to a hydrogenation process that may be used in connection with the production of phenol. In the process, a composition comprising: (i) cyclohexylbenzene; and (ii) a hydrogenable component are contacted with hydrogen in the presence of a hydrogenation catalyst under hydrogenation conditions. The hydrogenable component can be one or more of an olefin, a ketone or phenol. The hydrogenation catalyst has hydrogenation component and a support.
    Type: Application
    Filed: November 23, 2010
    Publication date: November 1, 2012
    Inventors: Jihad M. Dakka, Keith H. Kuechler, James R. Lattner, Edmund J. Mozeleski
  • Patent number: 8279435
    Abstract: Metal-polyaniline (PANI) composites are provided together with a process of preparing such composites by an electrodeless process. The metal of the composite can have nanoscale structural features and the composites can be used in applications such as catalysis for hydrogenation reactions and for analytical detection methods employing SERS.
    Type: Grant
    Filed: November 16, 2009
    Date of Patent: October 2, 2012
    Assignee: Los Alamos National Security, LLC
    Inventors: Hsing-Lin Wang, Wenguang Li, James A. Bailey, Yuan Gao
  • Publication number: 20120232266
    Abstract: The present invention relates to a process for the reaction of a compound with hydrogen wherein the reaction is conducted using a hydrogen-containing gas comprising up to about 10 vol. % hydrogen and at least about 90 vol. % of an inert gas and wherein the compound to be reacted with hydrogen is provided in a liquid phase. The process of the present invention is particularly suitable for hydrogenation and hydrogenolysis reactions.
    Type: Application
    Filed: November 26, 2010
    Publication date: September 13, 2012
    Applicant: SANDOZ AG
    Inventor: Martin Decristoforo
  • Publication number: 20120178969
    Abstract: In a process for producing cyclohexylbenzene, benzene and hydrogen are contacted under hydroalkylation conditions with a catalyst system comprising a MCM-22 family molecular sieve and at least one hydrogenation metal. The conditions comprise a temperature of about 140° C. to about 175° C., a pressure of about 135 psig to about 175 psig (931 kPag to 1207 kPag), a hydrogen to benzene molar ratio of about 0.30 to about 0.65 and a weight hourly space velocity of benzene of about 0.26 to about 1.05 hr?1.
    Type: Application
    Filed: March 1, 2012
    Publication date: July 12, 2012
    Inventors: Jane C. CHENG, Tan-Jen CHEN, Prasenjeet GHOSH
  • Patent number: 8178728
    Abstract: In a process for producing cyclohexylbenzene, benzene and hydrogen are contacted under hydroalkylation conditions with a catalyst system comprising a MCM-22 family molecular sieve and at least one hydrogenation metal. The conditions comprise a temperature of about 140° C. to about 175° C., a pressure of about 135 psig to about 175 psig (931 kPag to 1207 kPag), a hydrogen to benzene molar ratio of about 0.30 to about 0.65 and a weight hourly space velocity of benzene of about 0.26 to about 1.05 hr?1.
    Type: Grant
    Filed: February 24, 2009
    Date of Patent: May 15, 2012
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Jane C. Cheng, Tan-Jen Chen, Prasenjeet Ghosh
  • Publication number: 20110288341
    Abstract: In a process for producing cyclohexylbenzene, benzene and hydrogen are fed to at least one reaction zone comprising a catalyst system which comprises a molecular sieve and at least one hydrogenation metal. The MCM-22 family molecular sieve having an X-ray diffraction pattern including d-spacing maxima at 12.4±0.25, 6.9±0.15, 3.57±0.07 and 3.42±0.07 Angstrom, and the hydrogenation metal is selected from the group consisting of palladium, ruthenium, nickel, zinc, tin, cobalt, and combinations of any two or more thereof Hydroalkylation conditions of temperature and pressure are selected to produce a hydroalkylation conversion in a range of from about 15% to about 75% The benzene and hydrogen are then contacted in the at least one reaction zone under said selected hydroalkylation condition to produce an effluent containing cyclohexylbenzene.
    Type: Application
    Filed: November 24, 2009
    Publication date: November 24, 2011
    Inventors: Tan-Jen Chen, Francisco M. Benitez, John S. Buchanan, Jane C. Cheng, Jon E. Stanat
  • Publication number: 20110077438
    Abstract: This disclosure relates to a process for manufacturing a mono-cycloalkyl-substituted aromatic compound, said process comprising contacting a feedstock comprising an aromatic compound and hydrogen under hydroalkylation reaction conditions with a catalyst system comprising a molecular sieve, wherein said molecular sieve comprises a framework of tetrahedral atoms bridged by oxygen atoms, the tetrahedral atom framework being defined by a unit cell with atomic coordinates in nanometers shown in Table 2.
    Type: Application
    Filed: July 15, 2009
    Publication date: March 31, 2011
    Inventors: Wieslaw J. Roth, Terry E. Helton, Jane C. Cheng, Michael J. Brennan
  • Publication number: 20110071329
    Abstract: This disclosure relates to a process for manufacturing a mono-cycloalkyl-substituted aromatic compound, said process comprising contacting a feedstock comprising an aromatic compound and hydrogen under hydroalkylation reaction conditions with a catalyst system comprising a molecular sieve and at least one metal with hydrogenation activity, wherein said molecular sieve has, in its as-synthesized form and in calcined form, an X-ray diffraction pattern including peaks having a d-spacing maximum in the range of 14.17 to 12.57 Angstroms, a d-spacing maximum in the range of 12.1 to 12.56 Angstroms.
    Type: Application
    Filed: July 15, 2009
    Publication date: March 24, 2011
    Inventors: Wieslaw J. Roth, Terry E. Helton, Jane C. Cheng, Michael J. Brennan
  • Publication number: 20110028762
    Abstract: In a process for producing cyclohexylbenzene, benzene and hydrogen are fed to at least one reaction zone. The benzene and hydrogen are then contacted in the at least one reaction zone under hydroalkylation conditions with a catalyst system comprising a molecular sieve having an X-ray diffraction pattern including d-spacing maxima at 12.4±0.25, 6.9±0.15, 3.57±0.07 and 3.42±0.07 Angstrom, and at least one hydrogenation metal to produce an effluent containing cyclohexylbenzene. The catalyst system has an acid-to-metal molar ratio of from about 75 to about 750.
    Type: Application
    Filed: October 14, 2010
    Publication date: February 3, 2011
    Inventors: Tan-Jen CHEN, Jane C. Cheng, Terry E. Helton, John Scott Buchanan
  • Publication number: 20110015457
    Abstract: In a process for producing cyclohexylbenzene, benzene and hydrogen are contacted under hydroalkylation conditions with a catalyst system comprising a MCM-22 family molecular sieve and at least one hydrogenation metal. The conditions comprise a temperature of about 140° C. to about 175° C., a pressure of about 135 psig to about 175 psig (931 kPag to 1207 kPag), a hydrogen to benzene molar ratio of about 0.30 to about 0.65 and a weight hourly space velocity of benzene of about 0.26 to about 1.05 hr?1.
    Type: Application
    Filed: February 24, 2009
    Publication date: January 20, 2011
    Inventors: Jane C. Cheng, Tan-Jen Chen, Prasenjeet Ghosh
  • Patent number: 7803265
    Abstract: A process is disclosed for converting distillate to gasoline-range hydrocarbons using a two-stage catalyst system including a first catalyst containing platinum, palladium, or platinum and palladium, and an acidic support, and a second catalyst containing iridium and an inorganic oxide support, and optionally nickel.
    Type: Grant
    Filed: February 4, 2009
    Date of Patent: September 28, 2010
    Assignee: ConocoPhillips Company
    Inventors: Tushar V. Choudhary, Paul F. Meier, Edward L. Sughrue, II, Walter E. Alvarez
  • Publication number: 20100060894
    Abstract: Metal-polyaniline (PANI) composites are provided together with a process of preparing such composites by an electrodeless process. The metal of the composite can have nanoscale structural features and the composites can be used in applications such as catalysis for hydrogenation reactions and for analytical detection methods employing SERS.
    Type: Application
    Filed: November 16, 2009
    Publication date: March 11, 2010
    Applicant: LOS ALAMOS NATIONAL SECURITY, LLC
    Inventors: Hsing-Lin Wang, Wenguang Li, James A. Bailey, Yuan Gao
  • Patent number: 6858769
    Abstract: A catalyst for the selective oxidation of hydrogen has been developed. It comprises an inert core such as cordierite and an outer layer comprising a lithium aluminate support. The support has dispersed thereon a platinum group metal and a promoter metal, e.g. platinum and tin respectively. This catalyst is particularly effective in the selective oxidation of hydrogen in a dehydrogenation process.
    Type: Grant
    Filed: October 18, 2002
    Date of Patent: February 22, 2005
    Assignee: UOP LLC
    Inventors: Guy B. Woodle, Andrew S. Zarchy, Jeffery C. Bricker, Andrzej Z. Ringwelski
  • Publication number: 20040024274
    Abstract: A process for the hydrogenation of a monocyclic or polycyclic aromatic which may be unsubstituted or substituted by at least one aikyi group comprises bringing the aromatic into contact with a hydrogen-containing gas in the presence of a catalyst comprising at least one metal of transition group VIII of the Periodic Table as active metal applied to a structured or monolithic support.
    Type: Application
    Filed: April 2, 2003
    Publication date: February 5, 2004
    Inventors: Arnd Bttcher, Jochem Henkelmann, Mathias Haake, Gerd Kaibel
  • Publication number: 20040024273
    Abstract: In a process for hydrogenating unsubstituted monocyclic or polycyclic aromatics or monocyclic or polycyclic aromatics substituted by at least one alkyl group, amino group or hydroxyl group or a combination of two or more thereof to form the corresponding cycloaliphatics by means of gaseous hydrogen in the presence of at least one catalyst in a reaction column (4) in which the reactants are passed over the catalyst(s) (5) fixed in the reaction column (4), the cycloaliphatics are taken off at a side offtake (14) or from the bottom of the column (6) through a line (8) or at the side offtake (14) and from the bottom of the column (6) through a line (8).
    Type: Application
    Filed: April 2, 2003
    Publication date: February 5, 2004
    Inventors: Arnd Bottcher, Carsten Oost, Mathias Haake
  • Patent number: 6506953
    Abstract: There is described a process the hydroalkylation of an aromatic hydrocarbon, particularly benzene, to produce a cycloalkyl-substituted aromatic compound, particularly cyclohexylbenzene, comprising the step of contacting the aromatic hydrocarbon with hydrogen in the presence of a catalyst comprising MCM-68 and at least one metal having hydrogenation activity.
    Type: Grant
    Filed: January 24, 2000
    Date of Patent: January 14, 2003
    Assignee: ExxonMobil Oil Corporation
    Inventors: Jane Chi-Ya Cheng, Ajit B. Dandekar, Michael Alan Steckel, Hye Kyung Cho Timken
  • Patent number: 6037513
    Abstract: There is described a process and a catalyst for the hydroalkylation of an aromatic hydrocarbon, particularly benzene, wherein the catalyst comprises a first metal having hydrogenation activity and a crystalline inorganic oxide material having a X-ray diffraction pattern including the following d-spacing maxima 12.4.+-.0.25, 6.9.+-.0.15, 3.57.+-.0.07 and 3.42.+-.0.07.
    Type: Grant
    Filed: July 9, 1998
    Date of Patent: March 14, 2000
    Assignee: Mobil Oil Corporation
    Inventors: Clarence D. Chang, Jane C. Cheng, Terry E. Helton, Michael A. Steckel, Scott A. Stevenson
  • Patent number: 5986154
    Abstract: The invention concerns a process for the hydrogenation of aromatic compounds contained in feeds with an initial boiling point of more than 100.degree. C. and which contain at least 10% by weight of aromatic compounds. It consists of introducing chlorine in a concentration of 0.5-500 ppm by weight with respect to the feed at a temperature of between 200.degree. C. and 450.degree. C., a pressure in the range 1 MPa to 25 MPa, an HSV of between 0.1 h.sup.-1 and 10 h.sup.-1 and a volume ratio of hydrogen to feed of 100-2000. The catalyst used is a noble metal type and contains less than 1% of at least one halogen. Preferably, the catalyst is fluorinated or chlorinated.
    Type: Grant
    Filed: June 26, 1998
    Date of Patent: November 16, 1999
    Assignee: Institut Francais du Petrole
    Inventors: Samuel Mignard, Virginie Harle, Slavik Kasztelan, Nathalie Marchal-George
  • Patent number: 5789637
    Abstract: The invention concerns a process for the hydrogenation of aromatic compounds contained in feeds with an initial boiling point of more than 100.degree. C. and which contain at least 10% by weight of aromatic compounds. It consists of introducing chlorine in a concentration of 0.5-500 ppm by weight with respect to the feed at a temperature of between 200.degree. C. and 450.degree. C., a pressure in the range 1 MPa to 25 MPa, an HSV of between 0.1 h.sup.-1 and 10 h.sup.-1 and a volume ratio of hydrogen to feed of 100-2000. The catalyst used is a noble metal type and contains less than 1% of at least one halogen. Preferably, the catalyst is fluorinated or chlorinated.
    Type: Grant
    Filed: June 27, 1996
    Date of Patent: August 4, 1998
    Assignee: Institut Francais du Petrole
    Inventors: Samuel Mignard, Virginie France Harle, Slavik Kasztelan, Nathalie Marchal-George
  • Patent number: 5449847
    Abstract: There is provided a process for preparing tercyclohexane by reacting benzene with hydrogen. The process involves the use of a catalyst comprising an acidic solid and a hydrogenation component. The acidic solid may comprise a Group IVB metal oxide, such as zirconia, modified with an oxyanion of a Group VIB metal, such as tungsten. The hydrogenation component may comprise platinum.
    Type: Grant
    Filed: April 18, 1994
    Date of Patent: September 12, 1995
    Assignee: Mobil Oil Corporation
    Inventors: Clarence D. Chang, Scott Han, John D. Lutner, Jose G. Santiesteban
  • Patent number: 5350504
    Abstract: Non-acidic tin-, lead-, or indium-modified Pt/ZSM-5 catalysts are effective catalysts for the shape selective preferential hydrogenation of certain aromatic hydrocarbons in admixture with others. These catalysts can be used to reduce the aromatic content of gasoline and distillates.
    Type: Grant
    Filed: December 18, 1992
    Date of Patent: September 27, 1994
    Assignee: Mobil Oil Corporation
    Inventor: Ralph M. Dessau
  • Patent number: 5146024
    Abstract: A process for converting aromatic hydrocarbons (in particular benzene) to cycloalkyl-substituted aromatic hydrocarbons (in particular cyclohexylbenzene) in the presence of free hydrogen and a palladium-promoted zeolite catalyst is carried out in the presence of carbon monoxide as process modifier (so as to enhance the selectivity to the cycloalkyl-substituted aromatic hydrocarbon).
    Type: Grant
    Filed: May 20, 1991
    Date of Patent: September 8, 1992
    Assignee: Phillips Petroleum Company
    Inventor: Larry E. Reed
  • Patent number: 4950386
    Abstract: It has now been discovered that hydrocarbon feeds containing a polycyclic aromatic compound or mixtures thereof can be selectively hydrogenated by contacting the feed with a transition metal catalyst and hydrogen in the presence of an acid to provide a hydrocarbon mixture in which the aromatic content consists substantially of mono- and di-aromatic compounds. Useful acids include Lewis acids and acids having a pKa in the range of 0 to about -10.
    Type: Grant
    Filed: August 15, 1988
    Date of Patent: August 21, 1990
    Assignee: Exxon Research and Engineering Company
    Inventor: Manuel A. Francisco
  • Patent number: 4840745
    Abstract: A stable fluid composition is provided by this invention which contains a cis-o-tercyclohexyl compound and a trans-o-tercyclohexyl compound at a weight ratio of 25:75-65:35. This composition is useful as a fluid for traction drive.
    Type: Grant
    Filed: November 20, 1987
    Date of Patent: June 20, 1989
    Assignee: Idemitsu Kosan Company Limited
    Inventors: Toshiyuki Tsubouchi, Kazuaki Abe, Hitoshi Hata
  • Patent number: 4795840
    Abstract: The present invention provides a method for preparing a hydrocarbon mixture solvent comprising 1 to 15 wt % of alkyl tetralins and 0 to 10 wt % of aromatic hydrocarbons and having a boiling point of 160.degree. to 300.degree. C., the solvent being substantially free from naphthalene and biphenyl; the method being characterized by comprising the steps of subjecting a kerosene fraction having a boiling point of 150.degree. to 300.degree. C. to a nucleus hydrogenation treatment at a temperature of 100.degree. to 300.degree. C. at a pressure of 30 to 100 kg/cm.sup.2 in the presence of a metallic catalyst for nucleus hydrogenation of aromatic nuclei; separating and removing at least a part of n-paraffins in the kerosene therefrom by the use of a molecular sieve made from a synthesized zeolite having pores of 5 .ANG. in diameter in order to obtain a residual oil; and subjecting the latter to a rectification.
    Type: Grant
    Filed: July 2, 1987
    Date of Patent: January 3, 1989
    Assignee: Nippon Petrochemicals Co., Ltd.
    Inventors: Michiaki Torii, Seiji Hirooka
  • Patent number: 4783565
    Abstract: A cis-isomer of perhydroacenaphthene is selectively prepared through hydrogenation of acenaphthene by effecting hydrogenation of 80.degree. to 200.degree. C. in the presence of a Ru and/or Rh based catalyst. A cis-isomer having the highest boiling point is obtained as a major product.
    Type: Grant
    Filed: May 4, 1987
    Date of Patent: November 8, 1988
    Assignee: Kawasaki Steel Corporation
    Inventors: Yoshihiro Naruse, Toshihide Suzuki
  • Patent number: 4774013
    Abstract: This invention provides a novel perhydrofluorene derivative which is represented by the following general formula and which is useful as a fluid for traction drive and a process for production of the derivative. ##STR1## wherein R.sup.1, R.sup.2 and R.sup.3 each represents a hydrogen atom or an alkyl group of 1-4 carbon atoms, X represents (CH.sub.2).sub.p or ##STR2## wherein R.sup.4 represents a hydrogen atom or an alkyl group of 1-4 carbon atoms, p represents a real number of 2-6, q represents a real number of 1-4 and s represents 1 or 0 and k, m and n each represents a real number of 1-4.
    Type: Grant
    Filed: November 24, 1987
    Date of Patent: September 27, 1988
    Assignee: Idemitsu Kosan Company Limited
    Inventors: Kazuaki Abe, Toshiyuki Tsubouchi, Hitoshi Hata
  • Patent number: 4761510
    Abstract: Trans-isomers of perhydroacenaphthene are selectively prepared through hydrogenation of acenaphthene by effecting hydrogenation at 200.degree. to 300.degree. C. in the presence of a nickel catalyst on a kieselguhr carrier.
    Type: Grant
    Filed: May 4, 1987
    Date of Patent: August 2, 1988
    Assignee: Kawasaki Steel Corporation
    Inventors: Yoshihiro Naruse, Toshihide Suzuki
  • Patent number: 4751335
    Abstract: A process for preparing a fluid for traction drive from a fraction containing compounds having at least four aromatic rings is disclosed. The fraction is a by-product produced at the time of the preparation of alpha-methyl-benzylalkylbenzenes by alkylation of at least one compound selected from C.sub.7 -C.sub.10 alkylbenzenes with styrene in the presence of an acid catalyst. The process comprises the steps of decomposing the fraction in an atmosphere of hydrogen at a predetermined temperature and pressure, collecting a decomposition product having a boiling range not higher than 450.degree. C. and then subjecting the decomposition product to nuclear hydrogenation at aromatic rings thereof in the presence of a catalyst capable of nuclear hydrogenation.
    Type: Grant
    Filed: February 2, 1987
    Date of Patent: June 14, 1988
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Junichi Kubo, Kenji Suzuki, Kozo Kamiya, Eiji Akiyama, Masao Nambu
  • Patent number: 4696733
    Abstract: A process is disclosed for hydrogenating or partially hydrogenating polynuclear aromatics by contacting them with manganese nodules in the presence of hydrogen at elevated temperatures. The resulting partially hydrogenated products are useful as hydrogen donors in processes such as thermal cracking.
    Type: Grant
    Filed: September 17, 1984
    Date of Patent: September 29, 1987
    Assignee: Mobil Oil Corporation
    Inventor: Ying-Yen P. Tsao
  • Patent number: 4684754
    Abstract: The working fluid for traction drive comprises (A) a compound having, in a molecule, two decahydronaphthalene rings bonded either directly to each other or to the same or different carbon atoms in an alkane molecule or a compound having, in a molecule, one decahydronaphthalene ring and one cyclohexane ring bonded either directly to each other or to the same carbon atom in an alkane molecule and (B) a compound having two cyclohexane rings bonded either to the terminal carbon atoms of a C.sub.2-3 alkane molecule or to the carbon atoms of cyclopentane. The working fluid has a high traction coefficient with stability over a wide range of temperature, especially, in low temperatures.
    Type: Grant
    Filed: November 14, 1986
    Date of Patent: August 4, 1987
    Assignee: Idemitsu Kosan Company Limited
    Inventors: Toshiyuki Tsubouchi, Hitoshi Hata
  • Patent number: 4380683
    Abstract: Mononuclear aromatic hydrocarbons, e.g. benzene and analogs, are converted by hydroalkylation to the corresponding cycloalkyl aromatics by contacting the mononuclear aromatic hydrocarbons in the presence of hydrogen with a catalyst comprising a rare earth-exchanged Y-type zeolite support carrying a promoter comprising at least one of ruthenium, iridium, rhodium and palladium, the catalyst being calcined in an oxygen-containing atmosphere at a temperature of 250.degree. to 600.degree. C. prior to the hydroalkylation reaction.
    Type: Grant
    Filed: December 22, 1981
    Date of Patent: April 19, 1983
    Assignee: The Standard Oil Company
    Inventors: Serge R. Dolhyj, Louis J. Velenyi
  • Patent number: 4329529
    Abstract: Traction fluids for traction drive transmissions, prepared by hydrogenating an alkylation product obtained by the reaction of xylene and/or toluene, together with or without ethylbenzene, with styrene.
    Type: Grant
    Filed: March 2, 1981
    Date of Patent: May 11, 1982
    Assignee: Nippon Oil Co., Ltd.
    Inventor: Masao Nambu
  • Patent number: 4329531
    Abstract: An aromatic hydrocarbon is contacted under suitable hydroalkylation conditions with a composition comprising a calcined, acidic, nickel and rare earth-treated crystalline zeolite.
    Type: Grant
    Filed: May 29, 1980
    Date of Patent: May 11, 1982
    Assignee: Phillips Petroleum Company
    Inventors: Timothy P. Murtha, Ernest A. Zuech
  • Patent number: 4322284
    Abstract: Ash-containing raw coal is converted to a liquid fuel product by contacting the coal with hydrogen and an OHP-enriched solvent containing OHP and THP in a ratio of OHP/THP greater than 0.4, wherein the OHP is present in an amount of at least 5 weight percent of the solvent, to produce a liquid stream and a coal minerals stream, and recycling at least a portion of the coal minerals stream.A portion of the liquid stream (64) is catalytically hydrogenated (68), preferably with a tungsten-containing catalyst, to increase the ratio of OHP/THP to a value greater than 0.4 or preferably greater than l. The OHP-enriched liquid stream solvent is passed as solvent to a mixing zone (11) where it is admixed with raw coal (10) and recycled coal minerals (38), admixed with hydrogen (58) and passed to a preheater (20) and dissolver (24).
    Type: Grant
    Filed: February 5, 1980
    Date of Patent: March 30, 1982
    Assignee: Gulf Research & Development Company
    Inventors: Shirley C. Tsai, Howard G. McIlvried, III
  • Patent number: 4313017
    Abstract: Polynuclear aromatic reactants are selectively hydrogenated in the presence of hydrogen gas with a zinc titanate catalyst.
    Type: Grant
    Filed: December 29, 1980
    Date of Patent: January 26, 1982
    Assignee: Phillips Petroleum Co.
    Inventors: Roger N. McGinnis, Lloyd E. Gardner, Floyd Farha, Jr.