By Condensation Of Entire Cyclic Molecules Or Entire Hydrocarbyl Moieties Thereof, E.g., Polymerization, Etc. Patents (Class 585/422)
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Patent number: 10940425Abstract: A subject of the present invention is the use of a compound having the general formula (I): (I) wherein V, W, X4, X5, X6, X7, X?4, X?5, X?6, X?7, Y, Y?, R3, R?3, R4 and R?4 are as defined in any one of claims 1 to 11, for the detection, capture and/or separation of polluting gases, in particular those selected from the group comprising carbon dioxide, methane, sulfur dioxide, nitrogen oxides, carbon monoxide, linear hydrocarbons, linear mono-olefins and their mixtures, and preferably carbon dioxide. Another subject of the invention is a compound of formula (I) wherein V, W, X4, X5, X6, X7, X?4, X?5, X?6, X?7, Y, Y?, R3, R?3, R4 and R?4 are as defined in any one of claims 12 to 21.Type: GrantFiled: December 23, 2016Date of Patent: March 9, 2021Assignees: Centre National de la Recherche Scientifique, Universite d'Aix-MarseilleInventors: Jean-Manuel Raimundo, Vinicius Demétrio da Silva, Philip Leslie Llewellyn, Julien Rodriguez, Olivier Yves Claude Siri
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Patent number: 9590199Abstract: To provide a novel organic compound suitable for an organic light emitting device. This invention provides an organic compound having the skeleton represented by Formula (1).Type: GrantFiled: November 26, 2012Date of Patent: March 7, 2017Assignee: Canon Kabushiki KaishaInventors: Jun Kamatani, Shigemoto Abe, Masashi Hashimoto, Naoki Yamada, Akihito Saitoh
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Patent number: 9328297Abstract: Integrated systems are provided for the production of higher hydrocarbon compositions, for example liquid hydrocarbon compositions, from methane using an oxidative coupling of methane system to convert methane to ethylene, followed by conversion of ethylene to selectable higher hydrocarbon products. Integrated systems and processes are provided that process methane through to these higher hydrocarbon products.Type: GrantFiled: July 1, 2015Date of Patent: May 3, 2016Assignee: Siluria Technologies, Inc.Inventors: Greg Nyce, Peter Czerpak, Carlos Faz, Jarod McCormick, William Michalak, Bipinkumar Patel, Guido Radaelli, Tim A. Rappold, Ron Runnebaum, Erik C. Scher, Aihua Zhang, Joel Cizeron
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Patent number: 8802908Abstract: Process and systems for alkane bromination and, in one or more embodiments, to separate, parallel methane and higher alkanes bromination in a bromine-based process. An embodiment discloses a bromine-based process for converting alkanes to liquid hydrocarbons that includes alkanes bromination, the process comprising: brominating a methane stream comprising methane and having less than about 2 mol % of ethane to form methane bromination products comprising brominated methane and a first fraction of hydrogen bromide; separately brominating a C2+ alkane stream comprising an alkane having 2 or more carbon atoms to form C2+ methane bromination products comprising brominated alkanes having 2 or more carbon atoms and a second fraction of hydrogen bromide; and catalytically reacting at least a portion of the brominated methane and the brominated alkanes to form higher molecular hydrocarbons.Type: GrantFiled: October 8, 2012Date of Patent: August 12, 2014Assignee: Marathon GTF Technology, Ltd.Inventors: John J. Waycullis, Sagar B. Gadewar, Raphael Thomas
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Patent number: 8772557Abstract: Processes are disclosed that achieve a high conversion of lignin to aromatic hydrocarbons, and that may be carried out without the addition of a base. Depolymerization and deoxygenation, the desired lignin convention steps to yield aromatic hydrocarbons, are carried by contacting a mixture of lignin and a solvent (e.g., a lignin slurry) with hydrogen in the presence of a catalyst. A preferred solvent is a hydrogen transfer solvent such as a single-ring or fused-ring aromatic compound that beneficially facilitates depolymerization and hinders coke formation. These advantages result in favorable overall process economics for obtaining fuel components and/or chemicals from renewable sources.Type: GrantFiled: July 26, 2011Date of Patent: July 8, 2014Assignee: UOP LLCInventors: John Qianjun Chen, Mark Blaise Koch
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Patent number: 8704023Abstract: This disclosure relates to 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: GrantFiled: July 15, 2009Date of Patent: April 22, 2014Assignee: ExxonMobil Chemical Patents Inc.Inventors: Wieslaw J. Roth, Douglas L. Dorset, Gordon J. Kennedy, Thomas Yorke, Terry Eugene Helton, Prasenjeet Ghosh, Joshi V. Yogesh
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Patent number: 8592498Abstract: Disclosed herein are a reaction method and a production method of an organic compound which are capable of achieving high reaction selectivity according to the purpose and a high production rate of a target substance. The methods include at least two fluids, wherein at least one kind of the fluids is a fluid containing at least one organic compound and at least one kind of the fluids other than the above fluid is a fluid containing at least one reactant in the form of a liquid or solution, and the respective fluids join together in a thin film fluid foamed between processing surfaces arranged to be opposite to each other so as to be able to approach to and separate from each other, at least one of which rotates relative to the other, whereby an organic reaction is performed in the thin film fluid.Type: GrantFiled: September 11, 2008Date of Patent: November 26, 2013Assignee: M. Technique Co., Ltd.Inventor: Masakazu Enomura
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Patent number: 8536393Abstract: The present invention provides an integrated process for producing aromatic hydrocarbons and/or C4+ non-aromatic hydrocarbons from low molecular weight alkanes, which includes contacting the low molecular weight alkanes with a halogen and coupling the monohaloalkanes to form aromatic hydrocarbons and/or C4+ non-aromatic hydrocarbons.Type: GrantFiled: May 11, 2010Date of Patent: September 17, 2013Assignee: Shell Oil CompanyInventors: Wayne Errol Evans, Glenn Charles Komplin, Duraisamy Muthusamy
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Publication number: 20130189524Abstract: Novel compositions comprising polymer solutions at various viscosities are provided. The polymer solutions are preferably fugitive, so as to avoid interfering with the properties of the nanomaterials after post-processing of the CNT-containing formulations. Additives, including acid generators, are added to the polymer solutions in order to allow the polymer carrier solutions to be degraded or decomposed at temperatures low enough to allow processing of commonly-used polymer film substrates. The invention further allows the carbon nanotube solutions to be screen printed or printed via inkjet.Type: ApplicationFiled: January 22, 2013Publication date: July 25, 2013Applicant: BREWER SCIENCE INC.Inventor: Brewer Science Inc.
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Patent number: 8471083Abstract: A reforming process using a medium pore zeolite under conditions to facilitate the conversion of C8 paraffinic compounds to para-xylene is provided. Para-xylene is produced at greater than thermodynamic equilibrium concentrations using the process.Type: GrantFiled: January 11, 2013Date of Patent: June 25, 2013Assignee: Chevron U.S.A. Inc.Inventors: Cong-Yan Chen, Ann Jia-Bao Liang, Stephen Joseph Miller, James Nathan Ziemer
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Patent number: 8404775Abstract: A polymerizable ligand comprising, in one embodiment, a polyaromatic compound, with a terminal functional group, non-covalently bonded to the sidewalls of carbon nanotubes. This structure preserves the structural, mechanical, electrical, and electromechanical properties of the CNTs and ensures that an unhindered functional group is available to bond with an extended polymer matrix thereby resulting in an improved polymer-nanotube composite.Type: GrantFiled: November 15, 2010Date of Patent: March 26, 2013Assignee: The Johns Hopkins UniversityInventors: Jennifer L. Sample, Amy A. Hofstra
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Patent number: 8367884Abstract: Processes and systems for synthesizing hydrocarbon products, such as high molecular weight hydrocarbons, olefins or mixtures thereof, from alkyl bromides wherein one or more streams of alkyl bromides may be reacted in sequential or concurrent stages at different temperatures. The catalyst used in the synthesis stages may be the same or different and at least in one instance is chosen to form hydrocarbon products having a significant C6+ paraffin content. The stages may be conducted in one or more reactors and the catalyst may be deployed in fixed beds or fluidized beds.Type: GrantFiled: February 17, 2011Date of Patent: February 5, 2013Assignee: Marathon GTF Technology, Ltd.Inventor: John J Waycuilis
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Publication number: 20120261620Abstract: Functionalized carbon nanotubes and dispersions containing functionalized carbon nanotubes are provided. Exemplary functionalized carbon nanotubes include optionally substituted indene-based moieties. Methods of making functionalized carbon nanotubes and dispersions containing functionalized carbon nanotubes are provided. Methods of making conductive carbon nanotube dispersions, including films, are provided. Such methods include heating carbon nanotubes in a solvent in the absence of externally applied energy, to obtain an adduct that includes the solvent moiety bound to the carbon nanotube. Where the solvent includes an indene-based compound, the carbon nanotube thus prepared includes optionally indene-based moieties bound to the carbon nanotubes.Type: ApplicationFiled: December 19, 2011Publication date: October 18, 2012Inventors: Henning Richter, Ramesh Sivarajan
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Publication number: 20120215045Abstract: Methods and apparatus of staged injection of an oxidant into a feedstream within a reactor are disclosed. The staged injection of the oxidant can better disperse the catalytic reactions throughout the catalyst bed. The staged injection of the oxidant can lower the content of carbon oxides in the reaction product stream, which can reduce energy release from the reactor.Type: ApplicationFiled: February 22, 2011Publication date: August 23, 2012Applicant: Fina Technology, Inc.Inventor: James R. Butler
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Patent number: 8232441Abstract: A process for converting gaseous alkanes to liquid hydrocarbons wherein a gaseous feed containing alkanes is reacted with a dry bromine vapor to form alkyl bromides and hydrobromic acid vapor. The mixture of alkyl bromides and hydrobromic acid are then reacted over a synthetic crystalline alumino-silicate catalyst, such as a ZSM-5 zeolite, at a temperature of from about 150° C. to about 450° C. so as to form higher molecular weight hydrocarbons and hydrobromic acid vapor. Propane and butane which comprise a portion of the products may be recovered or recycled back through the process to form additional C5+ hydrocarbons. Various methods are disclosed to remove the hydrobromic acid vapor from the higher molecular weight hydrocarbons and to generate bromine from the hydrobromic acid for use in the process.Type: GrantFiled: July 13, 2009Date of Patent: July 31, 2012Assignee: Marathon GTF Technology, Ltd.Inventor: John J. Waycuilis
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Publication number: 20120172597Abstract: The present invention relates to compounds of the formulae (I) to (XII), to the use of the compounds in electronic devices, and to electronic devices comprising the compounds according to the invention.Type: ApplicationFiled: June 17, 2010Publication date: July 5, 2012Inventors: Rocco Fortte, Amir Hossain Parham, Teresa Mujica-Fernaud
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Patent number: 8198495Abstract: Processes and systems for synthesizing alkyl bromides to hydrocarbon products, such as high molecular weight hydrocarbons, olefins or mixtures thereof, wherein one or more streams of alkyl bromides may be synthesized in sequential or concurrent stages at different temperatures. The catalyst used in the synthesis stages may be the same or different and at least in one instance is chosen to form hydrocarbon products having a significant C6+ paraffin content. The stages may be conducted in one or more reactors and the catalyst may be deployed in fixed beds or fluidized beds.Type: GrantFiled: March 2, 2010Date of Patent: June 12, 2012Assignee: Marathon GTF Technology, Ltd.Inventors: John J. Waycuilis, William J. Turner
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Patent number: 8008535Abstract: A process for converting gaseous alkanes to olefins and higher molecular weight hydrocarbons wherein a gaseous feed containing alkanes is reacted with a dry bromine vapor to form alkyl bromides and hydrobromic acid vapor. The mixture of alkyl bromides and hydrobromic acid are then reacted over a synthetic crystalline alumino-silicate catalyst, such as an X or Y type zeolite, at a temperature of from about 250° C. to about 500° C. so as to form olefins, higher molecular weight hydrocarbons and hydrobromic acid vapor. Various methods are disclosed to remove the hydrobromic acid vapor from the olefins and higher molecular weight hydrocarbons and to generate bromine from the hydrobromic acid for use in the process.Type: GrantFiled: April 30, 2008Date of Patent: August 30, 2011Assignee: Marathon GTF Technology, Ltd.Inventor: John J. Waycuilis
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Publication number: 20110178199Abstract: Disclosed herein are a reaction method and a production method of an organic compound which are capable of achieving high reaction selectivity according to the purpose and a high production rate of a target substance. The methods include at least two fluids, wherein at least one kind of the fluids is a fluid containing at least one organic compound and at least one kind of the fluids other than the above fluid is a fluid containing at least one reactant in the form of a liquid or solution, and the respective fluids join together in a thin film fluid foamed between processing surfaces arranged to be opposite to each other so as to be able to approach to and separate from each other, at least one of which rotates relative to the other, whereby an organic reaction is performed in the thin film fluid.Type: ApplicationFiled: September 11, 2008Publication date: July 21, 2011Applicant: M. Technique Co., Ltd.Inventor: Masakazu Enomura
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Publication number: 20110166401Abstract: This disclosure relates to an EMM-12 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: ApplicationFiled: July 15, 2009Publication date: July 7, 2011Inventors: Wieslaw J Roth, Douglas Dorset, Gordon Kennedy, Thomas Yorke, Terry Eugene Bethlehem
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Publication number: 20110166402Abstract: This disclosure relates to 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: ApplicationFiled: July 15, 2009Publication date: July 7, 2011Inventors: Wieslaw J. Roth, Douglas L. Dorset, Gordon J. Kennedy, Thomas Yorke, Terry Eugene Helton, Prasenjeet Ghosh, Yogesh V. Joshi
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Publication number: 20110124934Abstract: The present invention provides a method for preparing a metallosilicate of MFI type, wherein organic templates, seeding techniques, using low aliphatic alcohols miscible with water or homogeneous starting solutions are not required. The present invention relates to a process for making a crystalline metallosilicate with high Si/Metal ratio comprising: a) providing an aqueous medium comprising OH? anions and a metal source, b) providing an aqueous medium comprising an inorganic water insoluble source of silicon, c) optionally providing a non aqueous liquid medium comprising optionally an organic source of silica, d) mixing the medium a), b) and the optional c) at conditions effective to crystallize the desired metallosilicate, e) recovering the desired metallosilicate, wherein in the mixture a)+b)+c), before crystallization, the ratio Si org/Si inorganic is <0.3, advantageously <0.2 and preferably 0, the molar ratio OH?/SiO2 is at least 0.3, advantageously from 0.3 to 0.62, preferably from 0.Type: ApplicationFiled: February 24, 2009Publication date: May 26, 2011Applicant: TOTAL PETROCHEMICALS RESEARCH FELUYInventors: Metin Bulut, Pierre Jacobs, Delphine Minoux, Nikolai Nesterenko, Jean-Pierre Dath, Sander Van Donk
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Patent number: 7935836Abstract: The present application discloses methods for the production of organic compounds comprising a linear series of five fused carbon rings. Such compounds are useful in the production of electronic components, devices and materials. For example the methods disclosed permit the production of 2,9- and 2,10-disubstituted pentacene compounds and 2,6,9,13- and 2,6,10,13-tetrasubstituted compounds that present particularly advantageous properties for the manufacture of semiconductor materials, and may be used in devices such as for example thin film transistors and solar cells. These features are enhanced by ?-? parallel stacking in the solid state. Also disclosed are compounds that are excellent candidates for use in the manufacture of semiconductor materials, and other components of electronic systems, by virtue of their solubility, crystal packing geometries, and electronic properties.Type: GrantFiled: August 6, 2009Date of Patent: May 3, 2011Inventor: Alexander Graham Fallis
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Publication number: 20110086987Abstract: A polymerizable ligand comprising, in one embodiment, a polyaromatic compound, with a terminal functional group, non-covalently bonded to the sidewalls of carbon nanotubes. This structure preserves the structural, mechanical, electrical, and electromechanical properties of the CNTs and ensures that an unhindered functional group is available to bond with an extended polymer matrix thereby resulting in an improved polymer-nanotube composite.Type: ApplicationFiled: November 15, 2010Publication date: April 14, 2011Inventors: Jennifer L. Sample, Amy A. Hofstra
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Publication number: 20110044891Abstract: A process for manufacturing a synthetic porous crystalline molecular sieve requires an aqueous reaction mixture comprising a source of X2O3 (X is a trivalent element), a source of YO2 (Y is a tetravalent element) and a source of MOH (M is an alkali metal). The H2O/MOH molar ratio is within the range of 70 to 126 and the source of X2O3 and YO2 is an amorphous material containing both X2O3 and YO2 and having YO2/X2O3 molar ratio of 15 or less. The molecular sieve products are useful as catalysts and/or absorbents. Such molecular sieves having MFI structure type, TON structure type or the structure type of zeolite beta and a composition involving the molar relationship (n) YO2:X2O3 wherein n is from 2 to less than 15 are novel compositions of matter.Type: ApplicationFiled: January 19, 2009Publication date: February 24, 2011Inventors: Wieslaw Jerzy Roth, Mae Koenig Rubin
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Patent number: 7847030Abstract: Provided is a process for making a diphenylamine-functionalized poly-?-olefin. The process has the following step: reacting an amount of a poly-?-olefin having a terminal double bond with a diphenylamine in the presence of a catalyst. The poly-?-olefin has a terminal double bond having a number average molecular weight of 120 to 600. The ratio of poly-?-olefin to diphenylamine is 1.0:1.0 to 10.0:1.0. Provided is also a diphenylamine-functionalized poly-?-olefin product.Type: GrantFiled: February 29, 2008Date of Patent: December 7, 2010Assignee: ExxonMobil Research and Engineering CompanyInventor: Abhimanyu O. Patil
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Publication number: 20100113832Abstract: The invention relates to a particulate substance comprising a particulate porous support coupled to a palladium species. The palladium species may comprise palladium nanoclusters. The particulate substance may be used as a catalyst for conducting a carbon-carbon coupling reaction or a reduction.Type: ApplicationFiled: March 23, 2007Publication date: May 6, 2010Applicant: Agency for Science ,Technology and ResearchInventors: Jackie Y. Ying, Nandanan Erathidiyil
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Patent number: 7560607Abstract: A process for converting gaseous alkanes to liquid hydrocarbons wherein a gaseous feed containing alkanes is reacted with a dry bromine vapor to form alkyl bromides and hydrobromic acid vapor. The mixture of alkyl bromides and hydrobromic acid are then reacted over a synthetic crystalline alumino-silicate catalyst, such as a ZSM-5 zeolite, at a temperature of from about 150° C. to about 450° C. so as to form higher molecular weight hydrocarbons and hydrobromic acid vapor. Propane and butane which comprise a portion of the products may be recovered or recycled back through the process to form additional C5+ hydrocarbons. Various methods are disclosed to remove the hydrobromic acid vapor from the higher molecular weight hydrocarbons and to generate bromine from the hydrobromic acid for use in the process.Type: GrantFiled: December 14, 2007Date of Patent: July 14, 2009Assignee: Marathon GTF Technology, Ltd.Inventor: John J. Waycuilis
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Patent number: 7557060Abstract: The present invention relates to a solid phosphoric acid catalyst and a process for conversion of hydrocarbons using a solid phosphoric acid catalyst. The solid phosphoric acid catalyst comprises silicon orthophosphate, and has a silicon orthophosphate to silicon pyrophosphate ratio of at least about 5:1. The total pore volume of the solid phosphoric acid catalyst is at least about 0.17 cm3 per gram of catalyst, of which at least about 0.15 cm3 per gram is contributed by pores with diameter of at least about 10,000 ?.Type: GrantFiled: June 29, 2007Date of Patent: July 7, 2009Assignee: Sud-Chemie Inc.Inventors: Ling Xu, Wayne Turbeville, Gregory A. Korynta, Jeffrey L. Braden
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Patent number: 7473797Abstract: 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: GrantFiled: April 27, 2005Date of Patent: January 6, 2009Assignee: University of MassachusettsInventors: Dhandapani Venkataraman, Craig G. Bates, Pranorm Saejueng
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Patent number: 7368624Abstract: A process for forming an aryl-aryl bond comprises the step of reacting an arene hydrocarbon compound with either (1) an organic oxidant selected from the group consisting of a quinone, a quinone imine, a quinone diimine, and a nitroarene, or (2) an oxidizing salt selected from the group consisting of a triarylaminium salt, an oxonium salt, and a nitrosium salt, or (3) a hypervalent iodine compound, each in the presence of a Brönsted or Lewis acid.Type: GrantFiled: March 30, 2004Date of Patent: May 6, 2008Assignee: Eastman Kodak CompanyInventors: Christopher T. Brown, Deepak Shukla, Kevin P. Dockery, Jerome R. Lenhard, James R. Matz
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Patent number: 7314962Abstract: The present invention relates to the synthesis of alkylated aromatic compounds using ionic liquids as the solvent. Alkylated aromatic compounds are synthesized by reacting an aromatic compound with a monoolefin in the presence of an acid catalyst.Type: GrantFiled: April 15, 2005Date of Patent: January 1, 2008Assignee: E. I. du Pont de Nemours & Co.Inventors: Mark Andrew Harmer, Christopher P. Junk, Leo Ernest Manzer
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Patent number: 7285205Abstract: In a regenerative reforming facility using a series of moving beds, a direct supply of regenerated catalyst, optionally reduced is passed into at least two of the reactors of the series. Spent catalysts from different reactors are passed into a common mixing apparatus so as to provide a homogeneous degree of coke on the spent catalysts which are thereafter passed to a regenerator. The feedstock and the intermediate effluents continue to circulate in succession relative to the reactors. The invention makes it possible in particular to reduce the operating pressure of the units to less than 0.2 MPa.Type: GrantFiled: March 11, 2004Date of Patent: October 23, 2007Assignee: Institut Francias du PetroleInventors: Eric Sanchez, Dominique Casanave
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Patent number: 7205445Abstract: A method of continuously producing polyalkylbiphenyls involves reacting biphenyl and an olefin in the presence of a solid acid catalyst to obtain a reaction mixture containing monoalkylbiphenyls and dialkylbiphenyls, separating a fraction containing biphenyl and at least a part of the monoalkylbiphenyls, circulating the separated fraction to the reactor such that the ratio of biphenyls to monoalkylbiphenyls is designed to be 0.1 or more and is designed to be less than the soluability of biphenyl to monoalkylbiphenyl at a circulation temperature, and recovering polyalkylbiphenyls.Type: GrantFiled: August 26, 2003Date of Patent: April 17, 2007Assignee: Nippon Petrochemicals, Co., Ltd.Inventors: Shinichiro Yanagawa, Shouzou Hayashi
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Patent number: 7151199Abstract: Hydrocarbon or oxygenate conversion process in which a feedstock is contacted with a non zeolitic molecular sieve which has been treated to remove most, if not all, of the halogen contained in the catalyst. The halogen may be removed by one of several methods. One method includes heating the catalyst in a low moisture environment, followed by contacting the heated catalyst with air and/or steam. Another method includes steam-treating the catalyst at a temperature from 400° C. to 1000° C. The hydrocarbon or oxygenate conversion processes include the conversion of oxygenates to olefins, the conversion of oxygenates and ammonia to alkylamines, the conversion of oxygenates and aromatic compounds to alkylated aromatic compounds, cracking and dewaxing.Type: GrantFiled: June 10, 2002Date of Patent: December 19, 2006Assignee: ExxonMobil Chemical Patents Inc.Inventors: Luc Roger Marc Martens, Stephen N. Vaughn, Albert Edward Schweizer, John K. Pierce, Shun Chong Fung
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Patent number: 7148356Abstract: A process for producing organic substituted aromatic or heteroaromatic compounds including biaryl and biheteroaryl compounds in a two-step reaction. In the first step, the aromatic or heteroaromatic compound is borylated in a reaction comprising a borane or diborane reagent (any boron reagent where the boron reagent contains a B—H, B—B or B—Si bond) and an iridium or rhodium catalytic complex. In the second step, a metal catalyst catalyzes the formation of the organic substituted aromatic or heteroaromatic compound from the borylated compound and an electrophile such as an aryl or organic halide, triflate (OSO2CF3), or nonaflate (OSO2C4F9). The steps in the process can be performed in a single reaction vessel or in separate reaction vessels. The present invention also provides a process for synthesis of complex polyphenylenes starting from halogenated aromatic compounds.Type: GrantFiled: March 14, 2005Date of Patent: December 12, 2006Assignee: Board of Trustees of Michigan State UniversityInventors: Milton R. Smith, III, Robert E. Maleczka
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Patent number: 7141687Abstract: The invention relates to N?-substituted N-acylamidine transition metal complexes of the general formula (I), wherein M represents a transition metal, selected from the group of metals including Ni, Cu, Ru, Rh, Pd, Os, Ir and Pt, X represents Cl, Br, triflate, methane sulfonate or p-toluol sulfonate, m is 0, 1 or 2, n is 1, 2 or 3 and the radicals have the following meanings: R1, R2 is a straight-chain or branched, cyclic hydrocarbon group with 1 to 20 carbon atoms which can be mono or poly-unsaturated, an aromatic group with 3 to 6 chain members, which is linked directly or via a C1 to C6 alkyl or C2 to C6 alkylene group, whereby the mentioned groups can carry one or more substituents. Ar represents C6 to C10 aryl or hetaryl with 5 to 10 ring members, whereby the mentioned groups can be substituted by C1 to C6 alkyl, C1 to C4 halogenalkyl, NR10R11, COOR6, Si(R7)3Si(R7)2R8, OR3 and/or halogen.Type: GrantFiled: November 28, 2003Date of Patent: November 28, 2006Assignee: BASF AktiengesellschaftInventors: Jan Kurt Eberhardt, Ernst-Ulrich Würthwein
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Patent number: 7008526Abstract: When a pitch composition prepared by mixing 100 parts by weight of mesophase pitch with 10 to 1,000 parts by weight of coal tar pitch, is heat-treated at a temperature of 500° C. or higher, it is possible to produce a high-density coke at a high yield while avoiding the foaming of the mesophase pitch. In addition, when the coke is graphitized at a temperature of 2,000° C. or higher, it is possible to obtain an artificial graphite having a high graphitization degree. Further, when the coke is first pulverized and then graphitized at a temperature of 2,000° C. or higher, it is possible to obtain a high-crystallinity graphite powder which can be suitably used as a carbon material for a negative electrode of non-aqueous solvent type secondary battery having a high discharge capacity and a high charge-discharge efficiency.Type: GrantFiled: August 8, 2001Date of Patent: March 7, 2006Assignee: Mistubishi Gas Chemical Company, Inc.Inventors: Koichi Kanno, Hirotaka Tsuruya, Ryuji Fujiura
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Patent number: 6914154Abstract: A production process, especially a continuous production process, for a biphenyltetracarboxylic acid tetraester characterized by carrying out, in parallel, a step of preliminarily mixing a phthalic acid diester and a palladium compound-containing catalyst to prepare a starting mixture, a step of continuously or intermittently supplying the starting mixture to a reactor, a step of conducting oxidative dimerization reaction of the phthalic acid diester in a temperature range of from 140° C. and lower than 250° C. while supplying molecular oxygen to the reactor to form a reaction mixture in the reactor, and a step of continuously or intermittently removing a portion of the reaction mixture from the reactor.Type: GrantFiled: August 12, 2003Date of Patent: July 5, 2005Assignee: Ube Industries, Ltd.Inventors: Yasushi Yamamoto, Tetsuro Tsuji, Jun Haruta, Kikuo Ataka, Noboru Kakeya
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Patent number: 6914152Abstract: A method for producing biphenyl and its derivative comprising oxidatively coupling a benzene aromatic compound in the presence of a catalyst comprising a palladium salt, a copper salt, and a bidentate ligand compound capable of forming a complex with the palladium salt via the nitrogen atom and the oxygen atom in the molecule thereof in an atmosphere containing molecular oxygen. In particular, an improved method for selectively producing an asymmetrically substituted biphenyl derivative, such as a 2,3,3?,4?-biphenyltetracarboxylic acid tetraester, which comprises oxidatively coupling a substituted aromatic compound, such as a phthalic diester, in the presence of the catalyst in an atmosphere containing molecular oxygen without replenishing with a ligand.Type: GrantFiled: October 2, 2002Date of Patent: July 5, 2005Assignee: Ube Industries, Ltd.Inventors: Yasushi Yamamoto, Tetsuro Tsuji, Jun Haruta
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Patent number: 6867302Abstract: A process for producing organic substituted aromatic or heteroaromatic compounds including biaryl and biheteroaryl compounds in a two-step reaction. In the first step, the aromatic or heteroaromatic compound is borylated in a reaction comprising a borane or diborane reagent (any boron reagent where the boron reagent contains a B—H, B—B or B—Si bond) and an iridium or rhodium catalytic complex. In the second step, a metal catalyst catalyzes the formation of the organic substituted aromatic or heteroaromatic compound from the borylated compound and an electrophile such as an aryl or organic halide, triflate (OSO2CF3), or nonaflate (OSO2C4F9). The steps in the process can be performed in a single reaction vessel or in separate reaction vessels. The present invention also provides a process for synthesis of complex polyphenylenes starting from halogenated aromatic compounds.Type: GrantFiled: July 12, 2002Date of Patent: March 15, 2005Assignee: Board of Trustees of Michigan State UniversityInventors: Milton R. Smith, III, Robert E. Maleczka
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Publication number: 20040267072Abstract: A cross-coupling synthesis of 2-alkyl-4-(2,6-dialkylphenyl)indenes is described. A 2-alkylidene is treated with a dialkylboronic acid in the presence of a catalyst. A feature of the invention is the use of a cross-coupling catalyst comprising palladium dichloride (1,5-cyclooctadiene) as a cross-coupling catalyst.Type: ApplicationFiled: June 4, 2002Publication date: December 30, 2004Inventor: Hamlin H. Barnes
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Publication number: 20040267011Abstract: The present invention relates to dihydrofolate reductase inhibitors having an aromatic group and a heteroaromatic group linked by a methylene group; methods of preparation of dihydrofolate reductase inhibitors that include metal mediated cross coupling of an aromatic halide or heteroaromatic halide with an organozinc reagent; and methods of treatment and pharmaceutical compositions that utilize or comprise one or more of such dihydrofolate reductase inhibitors.Type: ApplicationFiled: April 12, 2004Publication date: December 30, 2004Applicant: Dana-Farber Cancer InstituteInventors: Andre Rosowsky, Han Chen
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Publication number: 20040220438Abstract: A process for producing a monoalkylation aromatic product, such as ethylbenzene and cumene, utilizing an alkylation reactor zone and a transalkylation zone in series or a combined alkylation and transkylation reactor zone.Type: ApplicationFiled: July 17, 2003Publication date: November 4, 2004Inventors: Shiou-Shan Chen, Shy-Yuan H. Hwang
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Publication number: 20040073074Abstract: Th invention provides a method of producing dialkylbiphenyls and trialkylbiphenyle efficiently using a continuous flow system. The method of continuously producing polyalkylbiphenyls comprises the following four steps: (1) a step of supplying reaction raw materials containing at least biphenyl and an olefin to a flow system reactor wherein the mol ratio of olefin/biphenyl is 0.3 to 3 at the inlet of the reactor and reacting the raw materials in the presence of a solid acid catalyst to obtain a reaction mixture containing monoalkylbiphenyls and dialkylbiphenyls, (2) a step of separating a fraction containing biphenyl and at least a part of monoalkylbiphenyls from the above reaction mixture, (3) a step of circulating the fraction separated in the step (2) to the reactor such that the ratio by weight of biphenyl to monoalkylbiphenyls is designed to be 0.Type: ApplicationFiled: August 26, 2003Publication date: April 15, 2004Inventors: Shinichiro Yanagawa, Shouzou Hayashi
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Patent number: 6720468Abstract: A process for the separation of conjugated olefins from monoolefins in a fluid comprising such conjugated olefins and monoolefins using a Diels-Alder reaction to provide a fluid comprising a Diels-Alder adduct and monoolefins. The fluid comprising such Diels-Alder adduct and monoolefins can be subjected to a separating means to thereby recover a resulting monoolefin-containing fluid containing less than about 50 parts per million conjugated olefins. The process is particularly useful for purification of fluids containing normal alpha olefins.Type: GrantFiled: June 26, 2001Date of Patent: April 13, 2004Assignee: Chevron Phillips Chemical Company LPInventors: Saleh A. Elomari, Richard N. Reynolds, Jr., Steven J. Herron
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Patent number: 6710188Abstract: Chemically amplified resist is produced on the basis of vinyl polymer having 3-oxo-4-oxabicyclo[3.2.1]octane-2-yl group expressed by general formula (1) where each of L1, L2, L3, L4, L5 and L6 is selected from the group consisting of hydrogen atom and alkyl groups having the carbon number from 1 to 8, and the hydrogen atom and/or the alkyl group at L5 and L6 are replaced with alkylene groups having the carbon number from 1 to 10 and bonded to each other for forming a ring so that the resist exhibits high transparency to light equal to or less than 220 nm wavelength, large resistance against dry etching and good adhesion to substrates.Type: GrantFiled: June 18, 2003Date of Patent: March 23, 2004Assignee: NEC CorporationInventors: Katsumi Maeda, Kaichiro Nakano
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Publication number: 20030220498Abstract: 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: ApplicationFiled: May 10, 2002Publication date: November 27, 2003Inventors: Alois Furstner, Andreas Leitner, Maria Mendez
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Publication number: 20030158447Abstract: Process for preparing alkylaryl hydroperoxide containing product, which process comprises:Type: ApplicationFiled: February 6, 2003Publication date: August 21, 2003Inventors: Antoon Paul Michael Kremers, Eduardus Petrus Simon Schouten, Cornelis Willem Adriaan Schram
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Publication number: 20030153793Abstract: The invention relates to a process for the preparation of cumene by reacting isopropanol or a mixture of isopropanol and propene with benzene in presence of a &bgr;-zeolite catalyst having a SiO2/Al2O3 molar ratio greater than 10:1 that can be integrated in a process for preparing phenol, which comprises the steps I. preparation of cumene as described above, II. oxidation of cumene to cumene hydroperoxide, III. acid-catalyzed cleavage of cumene hydroperoxide to give phenol and acetone and IV. hydrogenation of acetone to form isopropanol. In the reaction of isopropanol with benzene, propene is formed by dehydration of isopropanol simultaneously with the alkylation of benzene to cumene by means of isopropanol and the propene formed is likewise used for the alkylation of benzene to cumene. Formation of n-propylbenzene in this process step according to the invention is barely observed or is in the range below 150 wppm.Type: ApplicationFiled: January 27, 2003Publication date: August 14, 2003Inventors: Michael Sakuth, Uwe Tanger, Markus Weber