Chlorination Patents (Class 570/207)
  • Patent number: 10044045
    Abstract: 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: Grant
    Filed: April 13, 2012
    Date of Patent: August 7, 2018
    Assignee: SHOWA DENKO K.K.
    Inventors: Ryuji Monden, Takuya Imai, Yuji Ito, Kunchan Lee, Takashi Sato
  • Patent number: 9765849
    Abstract: 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: Grant
    Filed: January 9, 2014
    Date of Patent: September 19, 2017
    Assignee: ZF Friedrichshafen AG
    Inventor: Tobias Dieckhoff
  • Patent number: 8771605
    Abstract: 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: Grant
    Filed: March 31, 2010
    Date of Patent: July 8, 2014
    Assignee: H R D Corporation
    Inventors: Abbas Hassan, Ebrahim Bagherzadeh, Rayford G. Anthony, Gregory G. Borsinger, Aziz Hassan
  • Patent number: 8524957
    Abstract: 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: Grant
    Filed: October 23, 2009
    Date of Patent: September 3, 2013
    Assignee: Tosoh Corporation
    Inventor: Tsuyoshi Okamoto
  • Patent number: 8334417
    Abstract: 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: Grant
    Filed: March 9, 2010
    Date of Patent: December 18, 2012
    Assignee: Bayer Cropscience AG
    Inventor: Thomas Himmler
  • Publication number: 20120183468
    Abstract: 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: Application
    Filed: January 17, 2012
    Publication date: July 19, 2012
    Applicant: MARELLE, LLC
    Inventors: Mark Farrell, Michelle Guaragno
  • Publication number: 20120171103
    Abstract: 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: Application
    Filed: June 28, 2010
    Publication date: July 5, 2012
    Applicant: NANYANG TECHNOLOGICAL UNIVERSITY
    Inventors: Jianwen Zhao, Lain-Jong Li, Peng Chen, Bee Eng Mary Chan
  • Publication number: 20120157691
    Abstract: 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: Application
    Filed: February 24, 2012
    Publication date: June 21, 2012
    Applicant: JAPAN SCIENCE AND TECHNOLOGY AGENCY
    Inventors: Yanhua ZHANG, Hisashi YAMAMOTO, Kazutaka SHIBATOMI
  • Patent number: 8030529
    Abstract: 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: Grant
    Filed: February 7, 2006
    Date of Patent: October 4, 2011
    Assignee: Syngenta Crop Protection, Inc.
    Inventors: Linhua Wang, Kristine Anderson Dolbeare, Frankie Lee Odom
  • Publication number: 20100234652
    Abstract: 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: Application
    Filed: March 9, 2010
    Publication date: September 16, 2010
    Applicant: Bayer CropScience AG
    Inventor: Thomas HIMMLER
  • Patent number: 7763760
    Abstract: 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: Grant
    Filed: June 16, 2004
    Date of Patent: July 27, 2010
    Assignee: SABIC Innovative Plastics IP B.V.
    Inventors: Balakrishnan Ganesan, Pradeep Jeevaji Nadkarni
  • Publication number: 20090216017
    Abstract: 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: Application
    Filed: May 1, 2009
    Publication date: August 27, 2009
    Inventor: Koji HAGIYA
  • Patent number: 7544847
    Abstract: 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: Grant
    Filed: October 10, 2008
    Date of Patent: June 9, 2009
    Assignees: 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
  • Publication number: 20090023964
    Abstract: 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: Application
    Filed: February 7, 2006
    Publication date: January 22, 2009
    Applicants: SYNGENTA CROP PROTECTION, INC., SYNGENTA LIMITED
    Inventors: Linhua Wang, Kristine Anderson Dolbeare, Frankie Lee Odom
  • Patent number: 7282615
    Abstract: 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: Grant
    Filed: June 16, 2004
    Date of Patent: October 16, 2007
    Inventors: Dan Hancu, Robert Edgar Colborn, Richard Joseph Kilmer, John Patrick Lemmon
  • Patent number: 7084317
    Abstract: 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: Grant
    Filed: October 5, 2001
    Date of Patent: August 1, 2006
    Assignee: The Queen's University of Belfast
    Inventors: Martyn John Earle, Suhas Prabhakar Katdare
  • Patent number: 6710217
    Abstract: 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: Grant
    Filed: November 13, 2001
    Date of Patent: March 23, 2004
    Assignee: Bayer Aktiengesellschaft
    Inventors: Reinhard Langer, Alexander Klausener, Paul Wagner, Lothar Puppe
  • Patent number: 6426440
    Abstract: 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: Grant
    Filed: December 26, 2000
    Date of Patent: July 30, 2002
    Assignee: Vinnolit Monomer GmbH & Co. KG
    Inventors: Thomas Wild, Juergen Eichler, Werner Strang, Peter Widmann
  • Patent number: 6211399
    Abstract: 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: Grant
    Filed: October 5, 1999
    Date of Patent: April 3, 2001
    Assignee: Occidental Chemical Corporation
    Inventors: Michael C. Savidakis, David C. Johnson
  • Patent number: 6118018
    Abstract: 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: Grant
    Filed: December 6, 1999
    Date of Patent: September 12, 2000
    Assignee: Occidental Chemical Corporation
    Inventors: Michael C. Savidakis, Michael J. Fifolt, Daniel R. Thielen, Ronald Spohn, David C. Johnson, William S. Derwin
  • Patent number: 6117278
    Abstract: 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: Grant
    Filed: December 10, 1998
    Date of Patent: September 12, 2000
    Assignee: Occidental Chemical Corporation
    Inventors: Sanjay Mandal, Kevin R. Benson, Michael J. Fifolt, John Hickey, James Franc, George Piotrowski, William S. Derwin
  • Patent number: 6028232
    Abstract: 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: Grant
    Filed: September 23, 1997
    Date of Patent: February 22, 2000
    Assignee: Korea Research Institute of Chemical Technology
    Inventors: Sang Eon Park, Jung Whan Yoo, Poong Man Lee
  • Patent number: 5969200
    Abstract: 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: Grant
    Filed: October 22, 1998
    Date of Patent: October 19, 1999
    Assignee: Rohm and Haas Company
    Inventors: Enrique Luis Michelotti, Heather Lynnette Rayle, Randall Wayne Stephens, William Joseph Zabrodski
  • Patent number: 5734073
    Abstract: 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: Grant
    Filed: April 18, 1996
    Date of Patent: March 31, 1998
    Assignee: BNFL Fluorochemicals Ltd
    Inventors: Richard Dickinson Chambers, Christopher John Skinner, Malcolm John Atherton, John Stewart Moilliet
  • Patent number: 5369214
    Abstract: 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: Grant
    Filed: January 7, 1994
    Date of Patent: November 29, 1994
    Assignee: The United States of America as represented by the United States Department of Energy
    Inventors: Malvina Farcasiu, Steven C. Petrosius
  • Patent number: 5315049
    Abstract: 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: Grant
    Filed: August 18, 1993
    Date of Patent: May 24, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinrich Schrage, Helmut Fiege
  • Patent number: 5210343
    Abstract: 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: Grant
    Filed: March 19, 1992
    Date of Patent: May 11, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Franz-Josef Mais, Helmut Fiege
  • Patent number: 5157173
    Abstract: 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: Grant
    Filed: September 24, 1991
    Date of Patent: October 20, 1992
    Assignee: DowElanco
    Inventors: Michael A. DesJardin, Clark P. Allphin
  • Patent number: 5149892
    Abstract: 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: Grant
    Filed: October 22, 1991
    Date of Patent: September 22, 1992
    Assignee: PPG Industries, Inc.
    Inventors: Robert E. Feathers, J. Douglas Mansell
  • Patent number: 5107045
    Abstract: 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: Grant
    Filed: February 22, 1991
    Date of Patent: April 21, 1992
    Assignee: Amoco Corporation
    Inventors: Mark W. Meszaros, Ibrahim Ghanayem
  • Patent number: 5105036
    Abstract: 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: Grant
    Filed: February 6, 1991
    Date of Patent: April 14, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Franz-Josef Mais, Helmut Fiege
  • Patent number: 5095157
    Abstract: 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: Grant
    Filed: May 2, 1990
    Date of Patent: March 10, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Franz-Josef Mais, Helmut Fiege
  • Patent number: 5053566
    Abstract: 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: Grant
    Filed: August 23, 1990
    Date of Patent: October 1, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Artur Botta, Hans-Josef Buysch, Lothar Puppe
  • Patent number: 5026932
    Abstract: 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: Grant
    Filed: February 22, 1990
    Date of Patent: June 25, 1991
    Assignee: Amoco Corporation
    Inventor: Mark W. Meszaros
  • Patent number: 5015792
    Abstract: 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: Grant
    Filed: April 24, 1989
    Date of Patent: May 14, 1991
    Assignee: Rhone-Poulenc Chimie
    Inventor: Alain Nonn
  • Patent number: 5001290
    Abstract: 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: Grant
    Filed: January 19, 1990
    Date of Patent: March 19, 1991
    Assignee: Battelle Memorial Institute
    Inventors: Melville Hillman, James D. Browning
  • Patent number: 4990706
    Abstract: 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: Grant
    Filed: June 30, 1989
    Date of Patent: February 5, 1991
    Assignee: PPG Industries, Inc.
    Inventor: Eugene Laukonen
  • Patent number: 4990707
    Abstract: 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: Grant
    Filed: October 26, 1989
    Date of Patent: February 5, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Franz-Josef Mais, Helmut Fiege
  • Patent number: 4942268
    Abstract: 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: Grant
    Filed: March 15, 1989
    Date of Patent: July 17, 1990
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Toshihiro Suzuki, Chizu Komatsu
  • Patent number: 4925994
    Abstract: 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: Grant
    Filed: April 24, 1989
    Date of Patent: May 15, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Franz-Josef Mais, Helmut Fiege
  • Patent number: 4914247
    Abstract: 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: Grant
    Filed: June 30, 1989
    Date of Patent: April 3, 1990
    Assignee: Toyo Soda Manufacturing Co., Ltd.
    Inventors: Kazuhiko Sekizawa, Toshio Hironaka, Masao Nakano, Yukihiro Tsutsumi
  • Patent number: 4898999
    Abstract: 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: Grant
    Filed: June 3, 1988
    Date of Patent: February 6, 1990
    Assignee: Shell Oil Company
    Inventor: Larry S. Corley
  • Patent number: 4886923
    Abstract: 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: Grant
    Filed: September 16, 1988
    Date of Patent: December 12, 1989
    Assignee: Montedison S.p.A.
    Inventors: Raffaele Ungarelli, Maurizio A. Beretta, Loris Sogli
  • Patent number: 4885417
    Abstract: 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: Grant
    Filed: September 19, 1988
    Date of Patent: December 5, 1989
    Assignee: Occidental Chemical Corporation
    Inventor: Kenneth F. Kubiak
  • Patent number: 4851596
    Abstract: 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: Grant
    Filed: May 11, 1988
    Date of Patent: July 25, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Franz-Josef Mais, Helmut Fiege, Kai Rohlk, Karlfried Wedemeyer
  • Patent number: 4849560
    Abstract: 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: Grant
    Filed: August 24, 1988
    Date of Patent: July 18, 1989
    Assignee: Toyo Soda Manufacturing Co., Ltd.
    Inventors: Kazuhiko Sekizawa, Takanori Miyake, Toshio Hironaka, Yukihiro Tsutsumi
  • Patent number: 4835327
    Abstract: 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: Grant
    Filed: December 5, 1986
    Date of Patent: May 30, 1989
    Assignee: PPG Industries, Inc.
    Inventors: Joseph E. Milam, William E. Wimer
  • Patent number: 4831199
    Abstract: 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: Grant
    Filed: June 9, 1987
    Date of Patent: May 16, 1989
    Assignee: Ihara Chemical Industry Co., Ltd.
    Inventors: Toshihiro Suzuki, Chizu Komatsu
  • Patent number: 4827058
    Abstract: 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: Grant
    Filed: March 10, 1988
    Date of Patent: May 2, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Franz-Josef Mais, Helmut Fiege
  • Patent number: 4822930
    Abstract: 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: Grant
    Filed: June 22, 1987
    Date of Patent: April 18, 1989
    Assignee: The Dow Chemical Company
    Inventor: Ming-Biann Liu