Chlorination Patents (Class 570/207)
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Patent number: 10044045Abstract: Provided is a process for producing a fuel cell electrode catalyst with high catalytic activity that is alternative to a noble metal catalyst, through a heat treatment at a relatively low temperature. A process for producing a fuel cell electrode catalyst includes a step (I) of obtaining a catalyst precursor, including a step (Ia) of mixing at least a metal compound (1), a nitrogen-containing organic compound (2), and a fluorine-containing compound (3), and a step (II) of heat-treating the catalyst precursor at a temperature of 500 to 1300° C. to obtain an electrode catalyst, a portion or the entirety of the metal compound (1) being a compound containing an atom of a metal element M1 selected from the group consisting of iron, cobalt, chromium, nickel, copper, zinc, titanium, niobium and zirconium, and at least one of the compounds (1), (2) and (3) containing an oxygen atom.Type: GrantFiled: April 13, 2012Date of Patent: August 7, 2018Assignee: SHOWA DENKO K.K.Inventors: Ryuji Monden, Takuya Imai, Yuji Ito, Kunchan Lee, Takashi Sato
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Patent number: 9765849Abstract: A torsional vibration damping arrangement for the drivetrain of a vehicle has an input region driven in rotation around an axis of rotation A and an output region. A first torque transmission path and a second torque transmission path parallel thereto proceed from the input region. A coupling arrangement communicates with the output region for superposing the torques guided via the torque transmission paths, and a phase shifter arrangement for the first torque transmission path generates a phase shift of rotational irregularities guided via the first torque transmission path relative to rotational irregularities guided via the second torque transmission path. The output region includes the planet gear carrier at which a planet gear is rotatably supported, and the planet gear carrier is connected to the output region to be fixed with respect to rotation relative to it.Type: GrantFiled: January 9, 2014Date of Patent: September 19, 2017Assignee: ZF Friedrichshafen AGInventor: Tobias Dieckhoff
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Patent number: 8771605Abstract: Use of a high shear mechanical device incorporated into a process for the production of chlorobenzene is capable of decreasing mass transfer limitations, thereby enhancing the chlorobenzene production process. A system for the production of chlorobenzene from benzene and chlorine, the system comprising a reactor and an external high shear device, the outlet of which is fluidly connected to the inlet of the reactor; the high shear device capable of providing an emulsion of chlorine gas bubbles within liquid benzene.Type: GrantFiled: March 31, 2010Date of Patent: July 8, 2014Assignee: H R D CorporationInventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory G. Borsinger, Aziz Hassan
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Patent number: 8524957Abstract: To provide a novel process for producing p-dichlorobenzene satisfying both of high selectivity of p-dichlorobenzene and high conversion of chlorine at the same time.Type: GrantFiled: October 23, 2009Date of Patent: September 3, 2013Assignee: Tosoh CorporationInventor: Tsuyoshi Okamoto
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Patent number: 8334417Abstract: The present invention relates to a novel process for preparing chloro- or bromoaromatics of the formula (II) by diazotizing the formula (I) by means of sodium nitrite or potassium nitrite in the presence of aqueous hydrochloric or hydrobromic acids and then reacting with an iron(II) or iron(III) compound, optionally in the presence of additional amounts of hydrogen chloride or hydrogen bromide or alkali metal or alkaline earth metal chlorides or bromides.Type: GrantFiled: March 9, 2010Date of Patent: December 18, 2012Assignee: Bayer Cropscience AGInventor: Thomas Himmler
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Publication number: 20120183468Abstract: Provided herein are water-soluble, functionalized fullerenes, and processes for producing water-soluble, functionalized fullerenes. The process includes sulfonating a fullerene in an acidic solution comprising sulfuric acid to produce a sulfonated fullerene, isolating the sulfonated fullerene from the acidic solution without neutralizing the acidic solution, reacting the sulfonated fullerene with hydrogen peroxide to form a reaction product, and isolating a polyhydroxylated fullerene from the reaction product produced from reacting the sulfonated fullerene with the hydrogen peroxide. The process of producing water-soluble fullerenes further includes functionalizing a polyhydroxylated fullerene with one or more pendant functional groups by reacting the polyhydroxylated fullerene with one or more functional group precursors.Type: ApplicationFiled: January 17, 2012Publication date: July 19, 2012Applicant: MARELLE, LLCInventors: Mark Farrell, Michelle Guaragno
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Publication number: 20120171103Abstract: The invention relates to a method of modifying electrical properties of carbon nanotubes by subjecting a composition of carbon nanotubes to one or more radical initiator(s). The invention also relates to an electronic component such as field-effect transistor comprising a carbon nanotube obtained using the method of the invention. The invention also relates to the use of the modified carbon nanotubes in conductive and high-strength nanotube/polymer composites, transparent electrodes, sensors and nanoelectromechanical devices, additives for batteries, radiation sources, semiconductor devices (e.g. transistors) or interconnects.Type: ApplicationFiled: June 28, 2010Publication date: July 5, 2012Applicant: NANYANG TECHNOLOGICAL UNIVERSITYInventors: Jianwen Zhao, Lain-Jong Li, Peng Chen, Bee Eng Mary Chan
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Publication number: 20120157691Abstract: A practical and efficient method for halogenation of activated carbon atoms using readily available N-haloimides and a Lewis acid catalyst has been disclosed. This methodology is applicable to a range of compounds and any halogen atom can be directly introduced to the substrate. The mild reaction conditions, easy workup procedure and simple operation make this method valuable from both an environmental and preparative point of view.Type: ApplicationFiled: February 24, 2012Publication date: June 21, 2012Applicant: JAPAN SCIENCE AND TECHNOLOGY AGENCYInventors: Yanhua ZHANG, Hisashi YAMAMOTO, Kazutaka SHIBATOMI
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Patent number: 8030529Abstract: The present invention provides a process for the production of intermediate compounds of formula (I), wherein the substituents are as defined herein. The process comprises reacting a substituted aniline with aqueous HX, followed by removal of water by azeotropic distillation and diazotization and pyrolysis with an organic nitrite at elevated temperatures in the absence of a copper catalyst. Alternatively, gaseous HX can be used to substitute aqueous HX in the process. Consequently, a step of water removal by azeotropic distillation can be eliminated. The intermediate compounds of formula I are suitable as intermediates in the preparation of herbicidally active 3-hydroxy-4-aryl-5-oxopyrazoline derivatives.Type: GrantFiled: February 7, 2006Date of Patent: October 4, 2011Assignee: Syngenta Crop Protection, Inc.Inventors: Linhua Wang, Kristine Anderson Dolbeare, Frankie Lee Odom
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Publication number: 20100234652Abstract: The present invention relates to a novel process for preparing chloro- or bromoaromatics of the formula (II) by diazotizing the formula (I) by means of sodium nitrite or potassium nitrite in the presence of aqueous hydrochloric or hydrobromic acids and then reacting with an iron(II) or iron(III) compound, optionally in the presence of additional amounts of hydrogen chloride or hydrogen bromide or alkali metal or alkaline earth metal chlorides or bromides.Type: ApplicationFiled: March 9, 2010Publication date: September 16, 2010Applicant: Bayer CropScience AGInventor: Thomas HIMMLER
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Patent number: 7763760Abstract: A method for ring-halogenating an aromatic compound comprises contacting with chlorine or bromine, a mixture comprising the aromatic compound and a mixed copper salt of formula Cu(Y)X, where Y comprises a counterion derived from an organic acid, where the organic acid has a pKa relative to water of 0 or greater; and X comprises Cl, Br, I, or (SO42?)1/2; to produce a reaction mixture comprising a haloaromatic compound and a copper(II) halide residue.Type: GrantFiled: June 16, 2004Date of Patent: July 27, 2010Assignee: SABIC Innovative Plastics IP B.V.Inventors: Balakrishnan Ganesan, Pradeep Jeevaji Nadkarni
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Publication number: 20090216017Abstract: A process for producing a biaryl compound, characterized by reacting an arylhydrazine compound, hydrogen peroxide and an aryl compound. When the reaction is conducted in the presence of a given metal or a compound of the metal or in the presence of a metal oxide obtained by reacting the given metal or a compound of the metal with hydrogen peroxide, then the yield of the biaryl compound is improved.Type: ApplicationFiled: May 1, 2009Publication date: August 27, 2009Inventor: Koji HAGIYA
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Patent number: 7544847Abstract: A method for producing 1,4-bis(dichloromethyl)tetrafluorobenzene is disclosed, which is achieved by reacting tetrafluoroterephthaldehyde, SOCl2 and organic solvents. In the synthesis of 1,4-bis(dichloromethyl)-tetrafluorobenzene by adding formamides as catalyst, there are remarkable advantages which include shortening the reaction time; simplifying the synthesizing steps and raising the yield of the product.Type: GrantFiled: October 10, 2008Date of Patent: June 9, 2009Assignees: Yuan-Shin Materials Technology Corp., Chun-Shan Institute of Science and Technology Araments Bureau, M.N.D.Inventors: Chan-Yuan Ho, Tsair-Feng Lin, Chun-Hsu Lin, Shieh-Jun Wang
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Publication number: 20090023964Abstract: The present invention provides a process for the production of intermediate compounds of formula (I), wherein the substituents are as defined herein. The process comprises reacting a substituted aniline with aqueous HX, followed by removal of water by azeotropic distillation and diazotization and pyrolysis with an organic nitrite at elevated temperatures in the absence of a copper catalyst. Alternatively, gaseous HX can be used to substitute aqueous HX in the process. Consequently, a step of water removal by azeotropic distillation can be eliminated. The intermediate compounds of formula I are suitable as intermediates in the preparation of herbicidally active 3-hydroxy-4-aryl-5-oxopyrazoline derivatives.Type: ApplicationFiled: February 7, 2006Publication date: January 22, 2009Applicants: SYNGENTA CROP PROTECTION, INC., SYNGENTA LIMITEDInventors: Linhua Wang, Kristine Anderson Dolbeare, Frankie Lee Odom
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Patent number: 7282615Abstract: A method for ring-halogenating an aromatic compound comprises contacting the aromatic compound with chlorine or bromine in the presence of a catalyst composition, where the catalyst composition comprises at least one salt comprising a metal selected from the group consisting of Group 13 metal; and a counterion derived from an acid having a pKa relative to water of 0 or greater; and at least one organic sulfur compound.Type: GrantFiled: June 16, 2004Date of Patent: October 16, 2007Inventors: Dan Hancu, Robert Edgar Colborn, Richard Joseph Kilmer, John Patrick Lemmon
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Patent number: 7084317Abstract: A process for the halogenation of an aromatic compound wherein the aromatic compound is admixed with a halogenating agent in the presence of an ionic liquid is described. The method in preferably halide, sulfur or nitrate ionic liquids has significant advantages over conventional halogenation reactions. These are that the reaction starts with, e.g., a halide salt rather than, e.g., a halogen, and is therefore more convenient and safer. Also, when the reaction is performed in a nitrate ionic liquid, the only by-product is water.Type: GrantFiled: October 5, 2001Date of Patent: August 1, 2006Assignee: The Queen's University of BelfastInventors: Martyn John Earle, Suhas Prabhakar Katdare
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Patent number: 6710217Abstract: The invention relates to a process for preparing 4-chlorobiphenyl by (a) reacting biphenyl and chlorine in the presence of one or more ring-chlorination catalysts, and (b) subjecting the reaction mixture obtained in step (a) to fractional distillation to obtain 4-chlorobiphenyl.Type: GrantFiled: November 13, 2001Date of Patent: March 23, 2004Assignee: Bayer AktiengesellschaftInventors: Reinhard Langer, Alexander Klausener, Paul Wagner, Lothar Puppe
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Patent number: 6426440Abstract: The work-up of the gaseous products from the thermal cracking of 1,2-dichloroethane is simplified if the cracking gases are cooled to a temperature range of about 150 to 180° C., only a subsidiary proportion, which comprises all the coke formed, being condensed and fed to a separate work-up.Type: GrantFiled: December 26, 2000Date of Patent: July 30, 2002Assignee: Vinnolit Monomer GmbH & Co. KGInventors: Thomas Wild, Juergen Eichler, Werner Strang, Peter Widmann
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Patent number: 6211399Abstract: Disclosed is a method of adding 1 to 4 chlorine or bromine atoms to an aromatic ring of compound that has at least one electron-withdrawing groups on that ring. The aromatic compound is reacted with a chlorinating agent or a brominating agent in the presence of about 0.1 to about 10 mole % of a Lewis acid catalyst at a temperature of ambient to about 100° C. and a pressure of about 10 to about 100 psig.Type: GrantFiled: October 5, 1999Date of Patent: April 3, 2001Assignee: Occidental Chemical CorporationInventors: Michael C. Savidakis, David C. Johnson
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Patent number: 6118018Abstract: Disclosed is a method of adding 1 to 4 chlorine or bromine atoms to an aromatic ring of compound that has at least one electron-withdrawing groups on that ring. The aromatic compound is reacted with a chlorinating agent or a brominating agent in the presence of about 0.1 to about 10 mole % of a Lewis acid catalyst and about 0.001 to about 0.1 equivalents of an iodine-containing cocatalyst at a temperature of ambient to about 100.degree. C.Type: GrantFiled: December 6, 1999Date of Patent: September 12, 2000Assignee: Occidental Chemical CorporationInventors: Michael C. Savidakis, Michael J. Fifolt, Daniel R. Thielen, Ronald Spohn, David C. Johnson, William S. Derwin
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Patent number: 6117278Abstract: Disclosed is a method for making high purity .alpha.-chloroxylenes. A composition is formed of about 15 to about 80 wt % of a xylene and about 20 to about 85 wt % of a solvent. The solvent can be toluene, ring halogenated toluene, benzotrichloride, ring halogenated benzotrichloride, benzotrifluoride, ring halogenated benzotrifluoride, .alpha.,.alpha.,.alpha.,.alpha.',.alpha.',.alpha.'-hexafluorometaxylene, .alpha.,.alpha.,.alpha.,.alpha.',.alpha.',.alpha.'-hexafluoroparaxylene, or a mixture thereof. The composition is heated to about 70 to about 160.degree. C. No base is present in the composition. Chlorine gas is sparged through the composition and chlorine free radicals are generated therein. The chlorine free radicals can be generated either with UV light or by means of a chlorine free radical initiator.Type: GrantFiled: December 10, 1998Date of Patent: September 12, 2000Assignee: Occidental Chemical CorporationInventors: Sanjay Mandal, Kevin R. Benson, Michael J. Fifolt, John Hickey, James Franc, George Piotrowski, William S. Derwin
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Patent number: 6028232Abstract: The present invention relates to a catalyst for preparing para-chloro aromatic compounds by the liquid-phase chlorination method. The catalyst is prepared by loading transition metal salts, rare earth metal salts or a mixture thereof, and alkali metal or alkaline earth metal chlorides having a melting point of 300.degree. C. or more, by solid-state method or impregnation method, into zeolite L being ion-exchanged by alkali metal. The present invention also relates to a process for preparing para-isomers of the chlorinated compounds by using the catalyst.Type: GrantFiled: September 23, 1997Date of Patent: February 22, 2000Assignee: Korea Research Institute of Chemical TechnologyInventors: Sang Eon Park, Jung Whan Yoo, Poong Man Lee
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Patent number: 5969200Abstract: Novel routes for the preparation of acetonylbenzamides are provided by the reaction of an amine and acyl chloride. Novel routes to various intermediates used in the manufacture of acetonylbenzamides are also disclosed.Type: GrantFiled: October 22, 1998Date of Patent: October 19, 1999Assignee: Rohm and Haas CompanyInventors: Enrique Luis Michelotti, Heather Lynnette Rayle, Randall Wayne Stephens, William Joseph Zabrodski
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Patent number: 5734073Abstract: A method of halogenating an aromatic compound which comprises the steps of reacting an halogenating agent with the aromatic compound in the presence of fluorine and an acid, wherein the halogenating agent is at least one of an iodinating agent, a brominating agent and an chlorinating agent.Type: GrantFiled: April 18, 1996Date of Patent: March 31, 1998Assignee: BNFL Fluorochemicals LtdInventors: Richard Dickinson Chambers, Christopher John Skinner, Malcolm John Atherton, John Stewart Moilliet
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Patent number: 5369214Abstract: A method for dehalogenating halogenated polyaromatic compounds is provided wherein the polyaromatic compounds are mixed with a hydrogen donor solvent and a carbon catalyst in predetermined proportions, the mixture is maintained at a predetermined pressure, and the mixture is heated to a predetermined temperature and for a predetermined time.Type: GrantFiled: January 7, 1994Date of Patent: November 29, 1994Assignee: The United States of America as represented by the United States Department of EnergyInventors: Malvina Farcasiu, Steven C. Petrosius
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Patent number: 5315049Abstract: Alkylaromatics are subjected to nuclear chlorination in the liquid phase in the presence of Friedel-Crafts catalyst mixtures comprising compounds of iron and antimony and cocatalysts of the formula (II) ##STR1## wherein the substituents have the meaning given in the description.Type: GrantFiled: August 18, 1993Date of Patent: May 24, 1994Assignee: Bayer AktiengesellschaftInventors: Heinrich Schrage, Helmut Fiege
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Patent number: 5210343Abstract: Dichlorobenzene having an increased p-content and a greatly reduced m-content is obtained by ring chlorination of benzene or chlorobenzene in the presence of Friedel-Crafts catalysts if the reaction is carried out in the presence of co-catalysts of the formula (I) ##STR1## wherein X represents fluorine, chlorine, bromine, trifluoromethyl or pentafluoroethyl andA represents 2 hydrogen atoms or the group --CH.dbd.CH--CH.dbd.CH--.Type: GrantFiled: March 19, 1992Date of Patent: May 11, 1993Assignee: Bayer AktiengesellschaftInventors: Franz-Josef Mais, Helmut Fiege
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Patent number: 5157173Abstract: 4-chlorobenzotrichloride was prepared by the chlorination of p-xylene in the vapor phase at a temperature above about 200.degree. C. in the presence of an activated carbon catalyst and water. An approximately 75 percent calculated yield was obtained at 250.degree. C. using a wide-pore activated carbon catalyst.Type: GrantFiled: September 24, 1991Date of Patent: October 20, 1992Assignee: DowElancoInventors: Michael A. DesJardin, Clark P. Allphin
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Patent number: 5149892Abstract: Benzene or a chlorinated benzene feedstock compound represented by the formula C.sub.6 H.sub.6-x Cl.sub.x is chlorinated in the rectifying zone of a catalytic distillation reactor to produce a chlorinated benzene product compound represented by the formula C.sub.6 H.sub.5-x Cl.sub.x+1, where x is an integer in the range of from 0 to 5.Type: GrantFiled: October 22, 1991Date of Patent: September 22, 1992Assignee: PPG Industries, Inc.Inventors: Robert E. Feathers, J. Douglas Mansell
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Patent number: 5107045Abstract: A regioselective process is provided for preparing 4-bromo-o-xylene in an isomer mixture of 4-bromo-o-xylene and 3-bromo-o-xylene by combining a molar excess of bromine with o-xylene. The produced 3-bromo-o-xylene isomer preferentially reacts with the excess bromine to produce dibromo-o-xylenes. The weight ratio of the 4-bromo-o-xylene to the 3-bromo-o-xylene in the product isomer mixture can be as high as about 97:3. Concurrent production of alpha-bromo-o-xylene is avoided by conducting the admixing in either darkness or in sulfur dioxide solution. The dibromo-o-xylene by products are easily separated by subsequent vacuum distillation or similar expedients.Type: GrantFiled: February 22, 1991Date of Patent: April 21, 1992Assignee: Amoco CorporationInventors: Mark W. Meszaros, Ibrahim Ghanayem
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Patent number: 5105036Abstract: Aromatic hydrocarbons monosubstituted by straight-chain or branched C.sub.1 -C.sub.12 -alkyl or by Chd 3-C.sub.8 -cycloalkyl can be chlorinated in the aromatic ring in the liquid phase in the presence of Friedel-Crafts catalysts if cyclic amidines which are oxy-sustituted on the exocyclic N atom are employed as co-catalysts. An increased proportion of the p-isomer is obtained in this reaction.Type: GrantFiled: February 6, 1991Date of Patent: April 14, 1992Assignee: Bayer AktiengesellschaftInventors: Franz-Josef Mais, Helmut Fiege
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Patent number: 5095157Abstract: In the preparation of 2-chloro-4-nitro-alkylbenzene by reaction of 4-nitro-alkylbenzene with elemental chlorine or chlorine-releasing compounds in the presence of a Friedel-Crafts catalyst in the liquid phase, particularly high selectivities in respect of the target compounds chlorinated exclusively in the 2-position are achieved if a dibenzo-condensed sulphur heterocycle of the formula ##STR1## having the meanings given in the description for R.sup.1 to R.sup.8, X and n, is used as co-catalyst.Type: GrantFiled: May 2, 1990Date of Patent: March 10, 1992Assignee: Bayer AktiengesellschaftInventors: Franz-Josef Mais, Helmut Fiege
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Patent number: 5053566Abstract: Oligophenyls dihalogenated in the 4,4'-position, of the formula ##STR1## can be prepared by catalyzed halogenation of oligophenyls of the formula ##STR2## wherein, in the formulae, X.sup.1 and X.sup.2 independently of one another represent chlorine or bromine, preferably chlorine,X.sup.3 denotes hydrogen, chlorine or bromine, preferably hydrogen or chlorine and particularly preferably hydrogen,R.sup.1, R.sup.2 and R.sup.3 independently of one another represent hydrogen, C.sub.1 -C.sub.4 -alkyl (preferably methyl or ethyl and particularly preferably methyl), C.sub.1 -C.sub.4 -alkoxy (preferably methoxy or ethoxy and particularly preferably methoxy), fluorine, chlorine or bromine anda assumes the value zero or one,with halogenating agents, the preparation being carried out in the presence of methylene chloride or solvent mixtures essentially containing methylene chloride and in the presence of zeolites of the L structure type which contain metal cations.Type: GrantFiled: August 23, 1990Date of Patent: October 1, 1991Assignee: Bayer AktiengesellschaftInventors: Artur Botta, Hans-Josef Buysch, Lothar Puppe
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Patent number: 5026932Abstract: A regioselective process is provided for preparing 4-bromo-o-xylene in an isomer mixture of 4-bromo-o-xylene and 3-bromo-o-xylene by combining bromine with o-xylene in liquid sulfur dioxide medium. A bromine to o-xylene mole ratio of about 0.4:1 to about 1:1 is utilized at a temperature in the range of about -20.degree. C. to about 40.degree. C. While preferred temperatures are in the about -15.degree. C. to about -9.degree. C. range, temperatures above about -9.degree. C. can be used by maintaining the reactant solution under pressure. A product isomer mixture can be isolated by vacuum distillation. A 92:8 weight ratio mixture of 4-bromo-o-xylene and 3-bromo-o-xylene is thus obtainable.Type: GrantFiled: February 22, 1990Date of Patent: June 25, 1991Assignee: Amoco CorporationInventor: Mark W. Meszaros
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Patent number: 5015792Abstract: 4,4'-Dibromobiphenyl is selectively produced in high yields by actively brominating biphenyl in a reaction medium containing at least one strong acid having a pKa of at most 4, e.g., a carboxylic or sulfonic acid, and, optionally, a reaction solvent.Type: GrantFiled: April 24, 1989Date of Patent: May 14, 1991Assignee: Rhone-Poulenc ChimieInventor: Alain Nonn
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Patent number: 5001290Abstract: A method for producing p-dichlorobenzene using a reactor containing a catalyst/reagent to convert chlorobenzene (or benzene) to p-dichlorobenzene, the reactor having an inlet and an outlet for introducing reactants and removing product; introducing a pulse of gaseous chlorobenzene (or benzene) into the reactor and reacting the chlorobenzene with the catalyst/reagent whereby p-dichlorobenzene is formed; introducing a pulse of inert gas into the reactor; introducing a pulse of gaseous chlorine into the reactor and reacting the chlorine with the catalyst/reagent; introducing a pulse of inert gas into the reactor; repeating the pulsing steps in a sequential manner, whereby mixing of the vaporized benzene or chlorobenzene, and the chlorine gas is prevented; and continuously removing product containing p-dichlorobenzene from the outlet of the reactor.Type: GrantFiled: January 19, 1990Date of Patent: March 19, 1991Assignee: Battelle Memorial InstituteInventors: Melville Hillman, James D. Browning
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Patent number: 4990706Abstract: As zeolite L is used as catalyst for the chlorination of benzene, chlorobenzene, ortho-dichlorobenzene, and/or meta-dichlorobenzene, its catalytic activity diminishes. Zeolite L which has been used for such chlorinations may be reactivated by contact with steam.Type: GrantFiled: June 30, 1989Date of Patent: February 5, 1991Assignee: PPG Industries, Inc.Inventor: Eugene Laukonen
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Patent number: 4990707Abstract: Aromatic hydrocarbons which are monosubstituted by straight-chain or branched C.sub.1 -C.sub.12 -alkyl or by C.sub.3 -C.sub.8 -cycloalkyl can be chlorinated in the presence of Friedel-Crafts Catalysts in liquid phase on the aromatic ring if cyclic benzo-fused imines or benzo[f]-1,4-thiazepines are used as co-catalysts. This makes it possible to obtain a higher proportion of p-isomers.Type: GrantFiled: October 26, 1989Date of Patent: February 5, 1991Assignee: Bayer AktiengesellschaftInventors: Franz-Josef Mais, Helmut Fiege
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Patent number: 4942268Abstract: A process for producing a halobenzene represented by the formula: ##STR1## where R is a lower alkyl group, a lower alkoxy group or a halogen atom, and X is a halogen atom, which comprises halogenating a benzene represented by the formula: ##STR2## where R is as defined above, in a liquid phase in the presence of a catalyst, characterized in that the catalyst is a combination of an aliphatic carboxylic acid component and a zeolite having a SiO.sub.2 /Al.sub.2 O.sub.3 molar ratio of from 3 to 8 and a pore size of from 6 to 10 .ANG..Type: GrantFiled: March 15, 1989Date of Patent: July 17, 1990Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Toshihiro Suzuki, Chizu Komatsu
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Patent number: 4925994Abstract: Aromatic hydrocarbons which are monosubstituted by straight-chain or branched C.sub.1 -C.sub.12 -alkyl or by C.sub.3 -C.sub.8 -cycloalkyl can be chlorinated in the presence of Friedel-Crafts Catalysts in liquid phase on the aromatic ring if 1,6-benzothiazocins are used as co-catalysts. This makes it possible to obtain a higher proportion of p-isomers.Type: GrantFiled: April 24, 1989Date of Patent: May 15, 1990Assignee: Bayer AktiengesellschaftInventors: Franz-Josef Mais, Helmut Fiege
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Patent number: 4914247Abstract: A para-substituted halogenobenzene derivative is prepared by halogenating a benzene derivative in the liquid phase in the presence of a molded zeolite catalyst body comprising, based on the weight of the molded zeolite catalyst body, 10 to 95% by weight of an L-type zeolite as the anhydrous state and 5 to 90% by weight of amorphous silica.Type: GrantFiled: June 30, 1989Date of Patent: April 3, 1990Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Kazuhiko Sekizawa, Toshio Hironaka, Masao Nakano, Yukihiro Tsutsumi
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Patent number: 4898999Abstract: A process for the preparation of cyclobutenohaloarenes is described in which a cyclobutenoarene such as benzocyclobutene is reacted with a halogen in the organic phase of a two-phase organic/aqueous system to form a cyclobutenohaloarene and hydrogen halide, the latter which migrates into the aqueous phase. The process has the advantages of low acidity of the reaction phase, and the consequent reduced side halogenation product formation and necessity for the introduction of caustic in the recovery step, and relatively simple recovery of the cyclobutenohaloarene from the reaction mixture.Type: GrantFiled: June 3, 1988Date of Patent: February 6, 1990Assignee: Shell Oil CompanyInventor: Larry S. Corley
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Patent number: 4886923Abstract: A process for the chlorination of the benzene rings of tricyclo 8.2.2.2 hexadeca 4,6,10,12,13,15 hexane (or (2,2)-paracyclophane) having the formula (I): ##STR1## by gaseous chlorine, by operating in the presence of at least one metal chloride as a catalyst, and at least one co-catalyst having the formula V:R--OH (V)whereinR=hydrocarbon or alkylcarboxylic radical with linear or branched chain, containing from 1 to 6 carbon atoms is taught.Type: GrantFiled: September 16, 1988Date of Patent: December 12, 1989Assignee: Montedison S.p.A.Inventors: Raffaele Ungarelli, Maurizio A. Beretta, Loris Sogli
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Patent number: 4885417Abstract: Off-color liquid ortho-chloro-para-xylene compositions are decolorized by contacting the compositions with particles of diatomaceous silica, magnesium oxide or soda ash.Type: GrantFiled: September 19, 1988Date of Patent: December 5, 1989Assignee: Occidental Chemical CorporationInventor: Kenneth F. Kubiak
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Patent number: 4851596Abstract: Aromatic hydrocarbons are chlorinated in the nucleus in the presence of Friedel-Crafts catalysts and in the presence of co-catalysts in the liquid phase by using thiazepines as co-catalysts.Type: GrantFiled: May 11, 1988Date of Patent: July 25, 1989Assignee: Bayer AktiengesellschaftInventors: Franz-Josef Mais, Helmut Fiege, Kai Rohlk, Karlfried Wedemeyer
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Patent number: 4849560Abstract: p-Substituted halogenated benzene derivatives are prepared at a high selectivity by halogenating benzene and/or benzene derivatives by using as a catalyst a zeolite modified with a metal salt.Type: GrantFiled: August 24, 1988Date of Patent: July 18, 1989Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Kazuhiko Sekizawa, Takanori Miyake, Toshio Hironaka, Yukihiro Tsutsumi
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Patent number: 4835327Abstract: 1,2,4-Trichlorobenzene is produced by chlorinating benzene, chlorobenzene, meta-dichlorobenzene, ortho-dichlorobenzene, or a mixture of two or more thereof in a reaction medium comprising a liquid phase and a catalytic amount of zeolite L, zeolite Y, or a mixture thereof.Type: GrantFiled: December 5, 1986Date of Patent: May 30, 1989Assignee: PPG Industries, Inc.Inventors: Joseph E. Milam, William E. Wimer
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Patent number: 4831199Abstract: A process for producing a halobenzene represented by the formula: ##STR1## where R is a lower alkyl group, a lower alkoxy group or a halogen atom, and X is a halogen atom, which comprises halogenating a benzene represented by the formula: ##STR2## where R is as defined above, in a liquid phase in the presence of a catalyst, characterized in that the catalyst is a combination of an aliphatic carboxylic acid component and a zeolite having a SiO.sub.2 /Al.sub.2 O.sub.3 molar ratio of from 3 to 8 and a pore size of from 6 to 10 .ANG..Type: GrantFiled: June 9, 1987Date of Patent: May 16, 1989Assignee: Ihara Chemical Industry Co., Ltd.Inventors: Toshihiro Suzuki, Chizu Komatsu
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Patent number: 4827058Abstract: m-Chlorotoluene is removed from chlorotoluene mixtures with a content of up to 10% by weight of m-chlorotoluene, with reference to the total amount of chlorotoluene in the mixture, by chlorinating a substantially toluene-free chlorotoluene mixture in the presence of a Friedel-Crafts catalyst and if appropriate a co-catalyst at from 0.degree. C. up to the boiling point of the mixture, until the content of m-chlorotoluene has decreased to a value of <1.0% by weight in the chlorotoluene mixture.Type: GrantFiled: March 10, 1988Date of Patent: May 2, 1989Assignee: Bayer AktiengesellschaftInventors: Franz-Josef Mais, Helmut Fiege
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Patent number: 4822930Abstract: Monobrominated cyclobutarenes are prepared by brominating a cyclobutarene in the presence of an organic complexing agent, an acid scavenger, or water. Faster reaction rates highly selective to monobrominated cyclobutarenes are obtained without conventional heavy metal or halogen catalysts.Type: GrantFiled: June 22, 1987Date of Patent: April 18, 1989Assignee: The Dow Chemical CompanyInventor: Ming-Biann Liu