Feed Other Than Hydrocarbon, Hydroxy, Monohalide, Or Ether Patents (Class 585/454)
  • Patent number: 11014076
    Abstract: A catalyst for synthesizing aromatic hydrocarbons, a preparation method thereof and a method for synthesizing aromatic hydrocarbons by using the catalyst. The catalyst comprises acidic molecular sieve particles and zinc-aluminum composite oxide particles. The catalyst has relatively high selectivity to aromatic hydrocarbons, particularly BTX, stable performance, and a long single-pass life.
    Type: Grant
    Filed: August 22, 2017
    Date of Patent: May 25, 2021
    Assignee: Dalian Institute of Chemical Physics, Chinese Academy of Sciences
    Inventors: Youming Ni, Wenliang Zhu, Zhongmin Liu, Zhiyang Chen, Yong Liu, Hongchao Liu, Xiangang Ma, Shiping Liu
  • Patent number: 10246387
    Abstract: A process is described for producing paraxylene, in which an aromatic hydrocarbon feedstock comprising benzene and/or toluene is contacted with an alkylating reagent comprising methanol and/or dimethyl ether in an alkylation reaction zone under alkylation conditions in the presence of an alkylation catalyst to produce an alkylated aromatic product comprising xylenes. The alkylation catalyst comprises a molecular sieve having a Constraint Index ?5, and the alkylation conditions comprise a temperature less than 500° C. The alkylation catalyst may be selectivated to produce a higher than equilibrium amount of paraxylene by using a molar ratio of alkylating agent to aromatic of at least 1:4.
    Type: Grant
    Filed: September 12, 2017
    Date of Patent: April 2, 2019
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventor: Tan-Jen Chen
  • Patent number: 10246383
    Abstract: A process is described for producing paraxylene, in which an aromatic hydrocarbon feedstock comprising benzene and/or toluene is contacted with an alkylating reagent comprising methanol and/or dimethyl ether in an alkylation reaction zone under alkylation conditions in the presence of an alkylation catalyst to produce an alkylated aromatic product comprising xylenes. The alkylation catalyst comprises a molecular sieve having a Constraint Index ?5, and the alkylation conditions comprise a temperature less than 500° C. Paraxylene may then be recovered from the alkylated aromatic product.
    Type: Grant
    Filed: September 12, 2017
    Date of Patent: April 2, 2019
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Tan-Jen Chen, Seth M. Washburn
  • Patent number: 9802876
    Abstract: This invention relates to an alkylating process for alkyl benzenes, including the steps of: a) an alkyl benzene and a first stream of alkylating agent being fed into a first reaction zone, contacting with a catalyst A, to produce a process stream I; b) the process stream I and a second stream of alkylating agent being fed into at least one second reaction zone, contacting with a catalyst B, to produce a process stream II; and c) the process stream II being fed into at least one third reaction zone, contacting with a catalyst C, to produce a process stream III containing an alkylate. The present alkylating process can improve the utilization efficiency of the alkylating agent.
    Type: Grant
    Filed: July 4, 2013
    Date of Patent: October 31, 2017
    Assignees: CHINA PETROLEUM & CHEMICAL CORPORATION, SHANGHAI RESEARCH INSTITUTE OF PETROCHEMICAL TECHNOLOGY, SINOPEC
    Inventors: Jian Jiang, Changxi Miao, Dongyu Jiang
  • Patent number: 9314779
    Abstract: In an embodiment, a method of forming a catalyst can comprises: treating a detemplated pentasil zeolite material with a phosphorus-containing compound to form a phosphorus treated zeolite; combining a hydrogenating material, the phosphorus treated zeolite, and a binder material to form a mixture; forming the mixture into a shaped body, wherein the mixture is formed into the shaped body without the mixture being heat-treated; and calcining the shaped body to form the catalyst. Combining the hydrogenating material with the phosphorus treated zeolite and the binder material occurs prior to forming of the shaped body.
    Type: Grant
    Filed: August 9, 2012
    Date of Patent: April 19, 2016
    Assignee: SAUDI BASIC INDUSTRIES CORPORATION
    Inventors: Ashim Kumar Ghosh, Neeta Kulkarni, Pamela Lawyer Harvey
  • Patent number: 8981171
    Abstract: The proposed process uses crystallization technology to purify paraxylene simultaneously of large concentrations of C8 aromatics and also small concentrations of oxygenated species.
    Type: Grant
    Filed: April 17, 2013
    Date of Patent: March 17, 2015
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: Mark P. Hagemeister, David L. Johnson, John J. Monson
  • Patent number: 8546633
    Abstract: A method for producing an alkylated aromatic compound includes a step (i) of producing a reaction product (a1) containing the alkylated aromatic compound and water by the reaction of an aromatic compound, a ketone, and hydrogen using a metal component containing at least one metallic element of copper, nickel, cobalt, and rhenium and a solid acid substance; a step (ii) of forming a dehydrated product (a2) from at least a portion of the reaction product (a1) by removing at least a portion of the water in the reaction product (a1); and a step (iii) of producing a reaction product (a3) containing the alkylated aromatic compound by bringing at least a portion of the dehydrated product (a2) into contact with a solid acid substance.
    Type: Grant
    Filed: October 22, 2009
    Date of Patent: October 1, 2013
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Kenji Fujiwara, Tsuneyuki Ohkubo, Terunori Fujita, Shinobu Aoki, Masayasu Ishibashi, Masao Imai, Kozo Yasuda
  • Patent number: 8536394
    Abstract: According to a process of the invention, a ketone, an aromatic compound and hydrogen as starting materials are reacted together in a single reaction step to produce an alkylaromatic compound in high yield. A process for producing phenols in the invention includes a step of performing the above alkylation process and does not increase the number of steps compared to the conventional cumene process. The process for producing alkylated aromatic compounds includes reacting an aromatic compound such as benzene, a ketone such as acetone and hydrogen in the presence of a solid acid substance, preferably a zeolite, and a silver-containing catalyst.
    Type: Grant
    Filed: March 12, 2010
    Date of Patent: September 17, 2013
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Tsuneyuki Ohkubo, Shinobu Aoki, Masayasu Ishibashi, Masao Imai, Terunori Fujita, Kenji Fujiwara
  • Publication number: 20130131415
    Abstract: A method of producing an alkylaromatic by the alkylation of an aromatic with ethanol, such as producing ethylbenzene by an alkylation reaction of benzene, is disclosed.
    Type: Application
    Filed: November 22, 2011
    Publication date: May 23, 2013
    Applicant: FINA TECHNOLOGY, INC.
    Inventors: James R. Butler, Aspen Texada, William Sheets
  • Publication number: 20130053566
    Abstract: Cationic palladium catalysts comprising diamino carbene ligands, wherein the catalysts are of the formula [Pd(X)q(LBX)t(DC)]r+[Ym-]p or [Pd(X)q(LB)n(LBX)t(DC)]2a+[V?]u[Z2?]y, wherein DC is a diamino carbene ligand, X is an anionic ligand, LBX is a combined anionic and neutral ligand, and Y, V, and Z are non-coordinating anions. The compounds are useful in catalytic reactions, including cross-coupling reactions and hydroamination reactions. In particular, the catalysts are used in the following reactions: Suzuki-Miyaura coupling, Kumada coupling, Negishi coupling, Sonogashira coupling, Hartwig-Buchwald amination, and Heck-Mizoroki coupling.
    Type: Application
    Filed: April 14, 2011
    Publication date: February 28, 2013
    Inventors: Kamaluddin Abdur-Rashid, Dino Amoroso, Chi-Wing Tsang, Wenli Jia
  • Patent number: 8329969
    Abstract: A process for the conversion of biomass derived pyrolysis oil to liquid fuel components is presented. The process includes the production of diesel, aviation, and naphtha boiling point range fuels or fuel blending components by two-stage deoxygenation of the pyrolysis oil and separation of the products.
    Type: Grant
    Filed: April 6, 2009
    Date of Patent: December 11, 2012
    Assignee: UOP LLC
    Inventors: Michael J. McCall, Timothy A. Brandvold, Douglas C. Elliott
  • Publication number: 20120046509
    Abstract: This disclosure relates to a process for manufacturing a mono-alkylaromatic compound, said process comprising contacting a feedstock comprising an alkylatable aromatic compound and an alkylating agent under alkylation reaction conditions with a catalyst comprising EMM-12, wherein said EMM-12 is a molecular sieve having, 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, and non-discrete scattering between about 8.85 to 11.05 Angstroms or exhibit a valley in between the peaks having a d-spacing maximum in the range of 10.14 to 12.0 Angstroms and a d-spacing maximum in the range from 8.66 to 10.13 Angstroms with measured intensity corrected for background at the lowest point being not less than 50% of the point at the same XRD d-spacing on the line connecting maxima in the range of 10.14 to 12.0 Angstroms and in the range from 8.66 to 10.
    Type: Application
    Filed: July 15, 2009
    Publication date: February 23, 2012
    Inventors: Terry E. Helton, Mathew J. Vincent
  • Publication number: 20110245542
    Abstract: Processes and reactor systems are provided for the conversion of oxygenated hydrocarbons to hydrocarbons, ketones and alcohols useful as liquid fuels, such as gasoline, jet fuel or diesel fuel, and industrial chemicals. The process involves the conversion of mono-oxygenated hydrocarbons, such as alcohols, ketones, aldehydes, furans, carboxylic acids, diols, triols, and/or other polyols, to C4+ hydrocarbons, alcohols and/or ketones, by condensation. The oxygenated hydrocarbons may originate from any source, but are preferably derived from biomass.
    Type: Application
    Filed: June 17, 2011
    Publication date: October 6, 2011
    Applicant: Virent Energy Systems, Inc.
    Inventors: Randy D. Cortright, Paul G. Blommel
  • Publication number: 20110144401
    Abstract: This disclosure relates to a process for manufacturing a mono-alkylaromatic aromatic compound, said process comprising contacting a feedstock comprising an alkylatable aromatic compound and an alkylating agent under alkylation reaction conditions with a catalyst comprising EMM-13, wherein said EMM-13 is a molecular sieve comprising 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 3.
    Type: Application
    Filed: July 15, 2009
    Publication date: June 16, 2011
    Inventors: Terry E. Helton, Matthew J. Vincent
  • Publication number: 20110068290
    Abstract: Compounds, compositions, systems and methods for the chemical and electrochemical modification of the electronic structure of graphene and especially epitaxial graphene (EG) are presented. Beneficially, such systems and methods allow the large-scale fabrication of electronic EG devices. Vigorous oxidative conditions may allow substantially complete removal of the EG carbon atoms and the generation of insulating regions; such processing is equivalent to that which is currently used in the semiconductor industry to lithographically etch or oxidize silicon and thereby define the physical features and electronic structure of the devices. However graphene offers an excellent opportunity for controlled modification of the hybridization of the carbon atoms from sp2 to sp3 states by chemical addition of organic functional groups.
    Type: Application
    Filed: May 29, 2009
    Publication date: March 24, 2011
    Applicant: THE REGENTS OF THE UNIVERSITY OF CALIFORNIA
    Inventors: Robert C. Haddon, Mikhail E. Itkis, Palanisamy Ramesh, Elena Bekyarova, Sakhrat Khizroev, Jeongmin Hong
  • Patent number: 7902414
    Abstract: A catalytic process for the selective production of para-xylene comprises the step of reacting an aromatic hydrocarbon selected from the group consisting of toluene, benzene and mixtures thereof with a feed comprising carbon monoxide and hydrogen in the presence of a selectivated catalyst. The process includes a catalyst selectivation phase and a para-xylene production phase. In the catalyst selectivation phase, the aromatic hydrocarbon and the feed are contacted with the catalyst under a first set of conditions effective to increase the para-selectivity of said catalyst. In the para-xylene production phase, the aromatic hydrocarbon and said feed are contacted with the catalyst under a second set of conditions different from the first set of conditions effective to selectively produce para-xylene.
    Type: Grant
    Filed: October 3, 2007
    Date of Patent: March 8, 2011
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: John D. Y. Ou, Zongxuan Hong, Songsheng Tan, Timothy E. McMinn
  • Publication number: 20100249477
    Abstract: It is intended to provide a method of rapid methylation of an aromatic compound or an alkenyl compound, which is capable of obtaining an aromatic compound or an alkenyl compound labeled with a methyl group or a fluoromethyl group under a mild condition rapidly in high yield using an organic boron compound whose toxicity is not so high as a substrate; a kit for preparing a PET tracer to be used in the same, and a method of producing a PET tracer using the same. In an aprotic polar solvent, methyl iodide or X—CH2F (wherein X is a functional group which can be easily released as an anion), an organic boron compound in which an aromatic ring or an alkenyl group is attached to boron are subjected to cross-coupling in the presence of a palladium(0) complex, a phosphine ligand, and a base.
    Type: Application
    Filed: August 24, 2007
    Publication date: September 30, 2010
    Applicants: GIFU UNIVERSITY, RIKEN, HAMAMATSU PHOTONICS K.K.
    Inventors: Masaaki Suzuki, Hisashi Doi, Hideo Tsukada
  • Publication number: 20090253949
    Abstract: This invention relates to a process for pretreating a zeolite catalyst, specifically a zeolite which has been modified with phosphorus. The catalyst may be used in a process for alkylation of aromatics, specifically toluene methylation. The pretreatment is first to contact the catalyst with the process reactants used in a process for alkylation of aromatics for at least two hours at conditions to produce an alkylated aromatic product and then with a gaseous stream containing oxygen at a temperature and for a time until there is no oxygen consumption. The zeolite may be a MFI zeolite. This pretreatment procedure for a phosphorus-modified zeolite catalyst produces a catalyst which has increased run time, i.e., decreased deactivation rate, compared to a fresh catalyst, even after successive regenerations.
    Type: Application
    Filed: April 2, 2008
    Publication date: October 8, 2009
    Inventors: Ashim Kumar Ghosh, Mohammad Shafiei, Manuel Castelan, Pamela Harvey, Neeta Kulkarni
  • Patent number: 7473797
    Abstract: A copper(I) bi-dentate ligand complex-catalyzed procedure for synthesis of 1,3-enynes. The methods and/or systems of this invention afford a variety of enynes, tolerate a variety of sensitive functional groups, and can be employed without resort to expensive palladium reagents.
    Type: Grant
    Filed: April 27, 2005
    Date of Patent: January 6, 2009
    Assignee: University of Massachusetts
    Inventors: Dhandapani Venkataraman, Craig G. Bates, Pranorm Saejueng
  • Patent number: 7105467
    Abstract: The present invention provides nickel catalysts and solvents which are useful in a cross-coupling reaction between an organomagnesium compound and an aromatic ether compound, such as an anisole derivative.
    Type: Grant
    Filed: July 8, 2003
    Date of Patent: September 12, 2006
    Assignee: Pharmacore, Inc.
    Inventor: John W. Dankwardt
  • Patent number: 7026478
    Abstract: A process for the production of compounds Ar—R1 by means of a cross-coupling reaction of an organometallic reagent R1-M with an aromatic or heteroaromatic substrate Ar—X catalyzed by one or several iron salts or iron complexes as catalysts or pre-catalysts, present homogeneously or heterogeneously in the reaction mixture. This new invention exhibits substantial advantages over established cross coupling methodology using palladium- or nickel complexes as the catalysts. Most notable aspects are the fact that (i) expensive and/or toxic nobel metal catalysts are replaced by cheap, stable, commercially available and toxicologically benign iron salts or iron complexes as the catalysts or pre-catalysts, (ii) commercially attractive aryl chlorides as well as various aryl sulfonates can be used as starting materials, (iii) the reaction can be performed under “ligand-free” conditons, and (iv) the reaction times are usually very short.
    Type: Grant
    Filed: May 10, 2002
    Date of Patent: April 11, 2006
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Alois Fürstner, Andreas Leitner, María Méndez
  • Patent number: 6838585
    Abstract: A palladium catalyzed cross-coupling of aryldiazonium salts with organosilanes is disclosed. New reactions that are user friendly and environmentally friendly are now possible, including some reactions that could not be achieved using prior methods. The organosilanes that may be cross-coupled with aryldiazonium salts include, for example, Ar?—Si(L)3, where Ar?=aryl, and where L?CH3, OCH3, F, Cl, R, or OR.
    Type: Grant
    Filed: November 8, 2001
    Date of Patent: January 4, 2005
    Assignee: Board of Supervisors of Louisiana State University and Agricultural and Mechanical College
    Inventor: David A. Spivak
  • Publication number: 20040097769
    Abstract: A catalytic process for the selective production of para-xylene comprises the step of reacting an aromatic hydrocarbon selected from the group consisting of toluene, benzene and mixtures thereof with a feed comprising carbon monoxide and hydrogen in the presence of a selectivated catalyst. The process includes a catalyst selectivation phase and a para-xylene production phase. In the catalyst selectivation phase, the aromatic hydrocarbon and the feed are contacted with the catalyst under a first set of conditions effective to increase the para-selectivity of said catalyst. In the para-xylene production phase, the aromatic hydrocarbon and said feed are contacted with the catalyst under a second set of conditions different from the first set of conditions effective to selectively produce para-xylene.
    Type: Application
    Filed: November 14, 2002
    Publication date: May 20, 2004
    Inventors: John D. Y. Ou, Zongxuan Hong, Songsheng Tan, Timothy E. McMinn
  • Publication number: 20020198423
    Abstract: A Pd(OAc)2/diazabutadiene system has been developed for the catalytic cross-coupling of aryl halides with arylboronic acids. A combination of the diazabutadiene DAB-Cy (1, N, N′-Dicyclohexyl-1,4-dizabutadiene) and Pd(OAc)2 was found to form an excellent catalyst for the Suzuki-Miyaura cross-coupling of various aryl bromides and activated aryl chlorides with arylboronic acids.
    Type: Application
    Filed: March 7, 2002
    Publication date: December 26, 2002
    Inventors: Steven P. Nolan, Gabriela Grasa
  • Patent number: 6459006
    Abstract: It has been discovered that para-xylene (PX) can be synthesized with improved selectivity by reacting an aromatic compound such as toluene and/or benzene with a reactant(s) from fuel syngas such as a combination of hydrogen and carbon monoxide and/or carbon dioxide and/or methanol,or methylating agents produced therefrom. The combination of the selective methylation technology and a source of fuel syngas creates several advantages including simplification of the selective methylation process and utilization of low cost feeds. The fuel syngas is used on a once-through basis.
    Type: Grant
    Filed: November 3, 1999
    Date of Patent: October 1, 2002
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: John D. Y. Ou, Thomas J. Waddick
  • Publication number: 20020062046
    Abstract: Method of performing alkylation or acylation reactions of aromatic substrates under supercritical or near-critical reaction conditions. In particular, a method of performing Friedel-Crafts alkylation or acylation reactions is disclosed under those conditions. Friedel-Crafts reactions may be effected using a heterogeneous catalyst in a continuous flow reactor containing a super-critical or near-critical reaction medium. Selectivity of product formation can be achieved by varying one or more of the temperature, pressure, catalyst, flow rates and also by varying the ratios of aromatic substrate to acylating or alkylating agent.
    Type: Application
    Filed: August 24, 2001
    Publication date: May 23, 2002
    Inventors: Thomas M. Swan, Stephen K. Ross, Martyn Poliakoff, Martin G. Hitzler, Fiona R. Smail, Thomas Tacke, Stefan Wieland
  • Patent number: 6388156
    Abstract: It has been discovered that para-xylene (PX) can be synthesized with improved selectivity by reacting an aromatic compound such as toluene and/or benzene with a reactant(s) such as a combination of hydrogen and carbon monoxide and/or carbon dioxide and/or methanol or methylating agents produced therefrom. Catalytic reaction systems are employed, such as crystalline or amorphous aluminosilicates having one-dimensional channel structure, para-alkyl selectivated crystalline or amorphous aluminosilicates, para-alkyl selectivated substituted aluminosilicates, crystalline or amorphous substituted silicates having one-dimensional channel structure, para-alkyl selectivated substituted silicates, crystalline or amorphous aluminophosphates, para-alkyl selectivated crystalline or amorphous aluminophosphates, para-alkyl selectivated zeolite-bound zeolite and para-alkyl selectivated substituted aluminophosphates, and mixtures thereof.
    Type: Grant
    Filed: May 14, 1999
    Date of Patent: May 14, 2002
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventors: John D. Y. Ou, Gary F. Janda, Zongxuan Hong, Russell D. Sellen
  • Patent number: 6375832
    Abstract: A method of transforming a normally gaseous composition containing at least one hydrogen source, at least one oxygen source and at least one carbon source into a normally liquid fuel, wherein said gaseous composition consists at least in part of carbon dioxide as said carbon source and said oxygen source, and of methane as said hydrogen source and as a second carbon source; the method comprising the steps of feeding the composition into a reactor including a first electrode means, a second electrode means and at least one layer of a normally solid dielectric material positioned between the first and the second electrode means; submitting the composition within the reactor in the presence of a normally solid catalyst to a dielectric barrier discharge, wherein said normally solid catalyst is a member selected from the group of zeolites, aluminophosphates, silicoaluminophosphates, metalloaluminophosphates and metal oxides containing OH groups; and controlling the dielectric barrier discharge to convert the gaseo
    Type: Grant
    Filed: March 21, 2000
    Date of Patent: April 23, 2002
    Assignee: ABB Research Ltd.
    Inventors: Baldur Eliasson, Eric Killer, Chang-Jun Liu
  • Patent number: 6215035
    Abstract: The invention relates to a process for the preparation of aralkylated aromatic compound with both small and large size aralkylating agents; wherein the catalyst used is heterogeneous solid catalyst removable from the reaction products by simple filtration, thus allowing the separated catalyst to be reused in the process. The catalyst is selected from micro or mesoporous gallosilicates and galloaluminosilicates, having structure similar to that of zeolites known in the prior art.
    Type: Grant
    Filed: January 11, 1999
    Date of Patent: April 10, 2001
    Assignee: Council of Scientific and Industrial Research
    Inventors: Vasant Ramchandra Choudhary, Suman Kumar Jana, B-Phani Kiran
  • 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: 5994603
    Abstract: A process is provided for the production of paraxylene by the methylation of toluene in the presence of a zeolite bound zeolite catalyst. The catalyst comprises first zeolite crystals which are bound together by second zeolite crystals. When used to methylate toluene to para-xylene, the zeolite bound zeolite catalyst has a para-xylene selectivity greater than thermodynamic equilibrium. This selectivity can be enhanced by selectivating the catalyst.
    Type: Grant
    Filed: May 29, 1997
    Date of Patent: November 30, 1999
    Assignee: Exxon Chemical Patents Inc.
    Inventors: Gary D. Mohr, Robert Scott Smith
  • Patent number: 5859302
    Abstract: Described are novel processes which employ reusable aluminum catalysts in Friedel-Crafts reactions.
    Type: Grant
    Filed: October 28, 1996
    Date of Patent: January 12, 1999
    Assignee: Albemarle Corporation
    Inventor: Won S. Park
  • Patent number: 5475176
    Abstract: The present invention relates to a process for preparing vinyl-substituted aromatic compounds of the formula (I) Ar--CH.dbd.CH.sub.2, where Ar is a phenyl group that may bear 1 to 5 substituents, naphthyl or anthryl or a naphthyl radical bearing 1 to 7 substituents or an anthryl radical bearing 1 to 8 substituents, or a mononuclear five-, six- or seven-membered heterocyclic aromatic group which contains an oxygen atom and/or one or two nitrogen atoms in the ring and may bear 1 to 5 substituents, wherein an arylamine of the formula (II) Ar--NH.sub.2, where Ar has the aforementioned meaning, is reacted in an organic acid with an organic nitrite of the formula (III) R--ONO, where R is an alkyl group having 1 to 18 carbon atoms, a phenyl radical which may bear 1 to 3 alkyl groups each having 1 to 4 carbon atoms, or is an alkylcarbonyl group having 2 to 5 carbon atoms, and ethylene in an organic solvent in the presence of a palladium(0) of palladium(II) compound at temperatures of 0.degree. to 35.degree. C.
    Type: Grant
    Filed: April 4, 1994
    Date of Patent: December 12, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Matthias Beller, Heinz Strutz
  • Patent number: 4714794
    Abstract: A synthetic oil having excellent oxidation stability, comprising a mixture of monoalkylnaphthalenes which have each a secondary alkyl group of 6 to 24 carbon atoms and in which the specific molar ratio of .alpha.- to .beta.-substituted monalkylnaphthalenes is at least 1.0. The synthetic oil is useful as a thermal medium oil or as the main component of a synthetic lubricating oil.
    Type: Grant
    Filed: May 15, 1987
    Date of Patent: December 22, 1987
    Assignee: Nippon Oil Co., Ltd.
    Inventors: Toshio Yoshida, Harumichi Watanabe
  • Patent number: 4620921
    Abstract: Substitution of aluminum or gallium for boron or iron contained in the framework of a high silica content zeolite is effected by treating the zeolite in liquid water in the presence of a compound of aluminum or gallium. Catalyst comprising the treated zeolite is used for conducting acid-catalyzed reactions of organic compounds, e.g. cracking of hydrocarbon compounds.
    Type: Grant
    Filed: October 15, 1985
    Date of Patent: November 4, 1986
    Assignee: Mobil Oil Corporation
    Inventors: Clarence D. Chang, Joseph N. Miale
  • Patent number: 4551572
    Abstract: A process for reacting an aromatic compound, water and carbon monoxide in the presence of a cadmium-containing catalyst is disclosed.
    Type: Grant
    Filed: August 17, 1984
    Date of Patent: November 5, 1985
    Assignee: Standard Oil Company (Indiana)
    Inventors: Jeffrey T. Miller, Albert L. Hensley, Jr.
  • Patent number: 4530756
    Abstract: A process is provided for conducting organic compound conversion over a catalyst composition comprising a crystalline zeolite having a high initial silica-to-alumina mole ratio, said zeolite being prepared by calcining the zeolite, contacting said calcined zeolite with solid aluminum fluoride, and coverting said aluminum fluoride contacted material to hydrogen form.
    Type: Grant
    Filed: February 17, 1984
    Date of Patent: July 23, 1985
    Assignee: Mobil Oil Corporation
    Inventors: Clarence D. Chang, Joseph N. Miale
  • Patent number: 4517075
    Abstract: A process is provided for conducting organic compound conversion over a catalyst comprising a high silica crystalline zeolite which has been treated by contact with aluminum chloride vapor.
    Type: Grant
    Filed: December 28, 1983
    Date of Patent: May 14, 1985
    Assignee: Mobil Oil Corporation
    Inventors: Ralph M. Dessau, George T. Kerr
  • Patent number: 4515682
    Abstract: A process is provided for conducting organic compound conversion over a catalyst composition comprising a specially treated crystalline zeolite having a high initial silica-to-alumina mole ratio, said zeolite having been synthesized from a reaction mixture comprising a diamine as a cation source. The treatment of the zeolite material comprises the sequential steps of reacting the zeolite with a dilute hydrogen fluoride solution, contacting the hydrogen fluoride solution reacted material with aluminum chloride vapor, and then treating the aluminum chloride contacted material to convert it to hydrogen form.
    Type: Grant
    Filed: February 17, 1984
    Date of Patent: May 7, 1985
    Assignee: Mobil Oil Corporation
    Inventors: Clarence D. Chang, Joseph N. Miale
  • Patent number: 4487983
    Abstract: A process for reacting an aromatic compound, hydrogen and at least one of carbon monoxide and an alcohol containing from 1 to 6 carbon atoms in the presence of a cadmium-containing catalyst is disclosed.
    Type: Grant
    Filed: September 28, 1983
    Date of Patent: December 11, 1984
    Assignee: Standard Oil Company (Indiana)
    Inventors: Jeffrey T. Miller, Thomas D. Nevitt
  • Patent number: 4487984
    Abstract: Alkylaromatic compounds may be synthesized by reacting an aromatic compound with a mixture of carbon monoxide and hydrogen at alkylation conditions in the presence of a dual-function catalyst. The catalyst system will comprise (1) a composite of oxides of copper, zinc and aluminum or chromium, and (2) an alumino-silicate which may be either in crystalline or amorphous form.
    Type: Grant
    Filed: February 28, 1984
    Date of Patent: December 11, 1984
    Assignee: UOP Inc.
    Inventor: Tamotsu Imai
  • Patent number: 4443643
    Abstract: A process for the production of styrene wherein ethylene oxide and benzene are added to a reactor at a temperature between about 600.degree. F. and about 825.degree. F. in the presence of an aluminosilicate type catalyst. The reaction proceeds directly to form styrene within the reactor.
    Type: Grant
    Filed: May 23, 1983
    Date of Patent: April 17, 1984
    Assignee: Cosden Technology, Inc.
    Inventors: James M. Watson, Cleve Forward
  • Patent number: 4409412
    Abstract: A process for alkylating aromatic compounds wherein the product aromatics are provided with one or more alkyl groups possessing at least two carbon atoms is disclosed wherein starting aromatic compound(s) and an alkylating atent which is a mixture of hydrogen and/or a hydrogen-containing substance which provides hydrogen under process conditions and a carbon oxide, e.g., a mixture of syngas (hydrogen and carbon monoxide) are reacted at elevated temperature in the presence of an activated catalyst containing metal values selected from the group consisting of iron, cobalt, ruthenium, manganese, rhodium and osmium, and a zeolite having a constraint index of 12 or less, e.g., ZSM-5. The alkylated aromatics can be dealkylated by known and conventional means to provide olefin and the dealkylated aromatics can be recycled to the alkylation zone.
    Type: Grant
    Filed: September 24, 1982
    Date of Patent: October 11, 1983
    Assignee: Mobil Oil Corporation
    Inventors: Werner O. Haag, Tracy J. Huang
  • Patent number: 4251675
    Abstract: Diphenylmethane is synthesized by reacting benzene and benzyl chloride at elevated temperatures in a Friedel-Crafts type reaction using catalytic amounts of a Friedel-Crafts metal halide catalyst such as ferric chloride whereby the desired product is obtained with a good selectivity and a high conversion rate.
    Type: Grant
    Filed: March 15, 1979
    Date of Patent: February 17, 1981
    Assignee: UOP Inc.
    Inventor: Dusan J. Engel
  • Patent number: 4238630
    Abstract: Alkylation of aromatic hydrocarbons, especially toluene methylation, is carried out in the presence of a catalyst comprising an aluminosilicate zeolite of the ZSM-5 type in which some or all of the protons of the zeolite have been replaced by monovalent cations. Preferably, the replacement cations are sodium ions, the catalyst preferably containing more than 2% by weight of sodium.
    Type: Grant
    Filed: April 9, 1979
    Date of Patent: December 9, 1980
    Assignee: Imperial Chemical Industries Limited
    Inventor: David G. Parker
  • Patent number: 4152364
    Abstract: Process for the selective production of para-xylene by methylation of toluene in the presence of a catalyst comprising a crystalline aluminosilicate zeolite, said zeolite having a silica to alumina ratio of at least about 12 and a constraint index, as hereinafter defined, within the approximate range of 1 to 12, which catalyst has undergone prior modification by treatment with an ammonium hydrogen phosphate to deposit at least about 0.5 weight percent of phosphorus thereon.
    Type: Grant
    Filed: January 19, 1978
    Date of Patent: May 1, 1979
    Assignee: Mobil Oil Corporation
    Inventor: Chin-Chiun Chu