Preparing Benzene Ring Containing Compound Patents (Class 570/143)
  • Patent number: 6706933
    Abstract: A method of preparing vicinal difluoro aromatic compounds in high yield from hydroxy aromatic compounds and a method of preparing intermediates thereof. The hydroxy aromatic compound can be a mono-, bi- or tricyclic aromatic in which the rings are separate or fused. One or more of the rings can contain heteroatoms, such as oxygen, nitrogen, or sulfur, and can contain one or more substitutions, in addition to the hydroxy substitution.
    Type: Grant
    Filed: December 30, 2002
    Date of Patent: March 16, 2004
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gauri Sankar Lal, Kathryn Sue Hayes
  • Patent number: 6657093
    Abstract: A process for preparing compounds of the formula (II), where the substituents R1 to R5 are each independently H, CH3, straight-chain or branched C1-C8-alkyl, CH(OC1-C5-alkyl)2, CH(C1-C5-alkyl)(OC1-C5-alkyl), CH2(OC1-C5-alkyl), CH(CH3)(OC1-C5-alkyl), C1-C8-alkoxy, N(C1-C5-alkyl)2, phenyl, substituted phenyl, aryl, heteroaryl, S(C1-C5-alkyl) or a radical Caryl, alkyl, and the symbols X1 to 5 are each carbon.
    Type: Grant
    Filed: June 13, 2002
    Date of Patent: December 2, 2003
    Assignee: Clariant GmbH
    Inventors: Andreas Meudt, Michael Erbes, Klaus Forstinger
  • Patent number: 6613948
    Abstract: 2,3,4,5-tetrafluorobenzene derivatives can be obtained in a particularly advantageous manner by reacting the corresponding chlorobenzene or (chloro, fluoro)-benzene derivatives with a fluorinating agent in the presence of a solvent and a catalyst at elevated temperature, which comprises carrying out the reaction initially under temperature and pressure conditions such that the respective 2,3,4,5-tetrafluoro-benzene derivative continuously distills off through a column, and subsequently setting temperature and pressure conditions such that residual fractions of the 2,3,4,5-tetrafluorobenzene derivative distill off with the corresponding 2,3,4-trifluoro-5-chloro compound.
    Type: Grant
    Filed: September 14, 1998
    Date of Patent: September 2, 2003
    Assignee: Bayer AG
    Inventors: Otto Neuner, Norbert Lui, Dietmar Bielefeldt, Michael Holzbrecher
  • Publication number: 20030149315
    Abstract: A method of preparing vicinal difluoro aromatic compounds in high yield from hydroxy aromatic compounds using various bases and a method of preparing intermediates thereof. A method for making a vicinal difluoro halogenated aromatic compound including providing a tetrafluoro derivative of a halogen substituted aromatic compound, wherein the tetrafluoro derivative has two fluorine atoms on each of two adjacent carbons and at least one additional halogen substituent; reacting the tetrafluoro derivative with a reducing agent in presence of a base for a reaction time sufficient to form the vicinal difluoro halogenated aromatic compound containing two vicinal fluorine substituents and the at least one additional halogen substituent, wherein the reducing agent is used in a reducing agent effective amount sufficient to retain the at least one additional halogen substituent.
    Type: Application
    Filed: February 3, 2003
    Publication date: August 7, 2003
    Inventors: Axel Klauck-Jacobs, Kathryn Sue Hayes, Reiner Taege, William Casteel, Gauri Sankar Lal
  • Publication number: 20030137241
    Abstract: The invention aims to provide a perylene derivative preparation process featuring satisfactory yields and improved preparation efficiency, a perylene derivative obtained by the process, and an organic EL device using the same.
    Type: Application
    Filed: July 5, 2002
    Publication date: July 24, 2003
    Applicant: TDK CORPORATION
    Inventors: Tetsuji Fujita, Kensuke Ara, Tetsushi Inoue
  • Patent number: 6515191
    Abstract: A method of preparing vicinal difluoro aromatic compounds in high yield from hydroxy aromatic compounds and a method of preparing intermediates thereof. The hydroxy aromatic compound can be a mono-, bi- or tricyclic aromatic in which the rings are separate or fused. One or more of the rings can contain heteroatoms, such as oxygen, nitrogen, or sulfur, and can contain one or more substitutions, in addition to the hydroxy substitution.
    Type: Grant
    Filed: July 17, 2002
    Date of Patent: February 4, 2003
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gauri Sankar Lal, Kathryn Sue Hayes
  • Publication number: 20020198417
    Abstract: A method of preparing vicinal difluoro aromatic compounds in high yield from hydroxy aromatic compounds and a method of preparing intermediates thereof. The hydroxy aromatic compound can be a mono-, bi- or tricyclic aromatic in which the rings are separate or fused. One or more of the rings can contain heteroatoms, such as oxygen, nitrogen, or sulfur, and can contain one or more substitutions, in addition to the hydroxy substitution.
    Type: Application
    Filed: July 17, 2002
    Publication date: December 26, 2002
    Inventors: Gauri Sankar Lal, Kathryn Sue Hayes
  • Patent number: 6455744
    Abstract: A method of preparing vicinal difluoro aromatic compounds in high yield from hydroxy aromatic compounds and a method of preparing intermediates thereof. The hydroxy aromatic compound can be a mono-, bi- or tricyclic aromatic in which the rings are separate or fused. One or more of the rings can contain heteroatoms, such as oxygen, nitrogen, or sulfur, and can contain one or more substitutions, in addition to the hydroxy substitution.
    Type: Grant
    Filed: November 6, 2001
    Date of Patent: September 24, 2002
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gauri Sankar Lal, Kathryn Sue Hayes
  • Publication number: 20020099247
    Abstract: A method of preparing vicinal difluoro aromatic compounds in high yield from hydroxy aromatic compounds and a method of preparing intermediates thereof. The hydroxy aromatic compound can be a mono-, bi- or tricyclic aromatic in which the rings are separate or fused. One or more of the rings can contain heteroatoms, such as oxygen, nitrogen, or sulfur, and can contain one or more substitutions, in addition to the hydroxy substitution.
    Type: Application
    Filed: November 6, 2001
    Publication date: July 25, 2002
    Inventors: Gauri Sankar Lal, Kathryn Sue Hayes
  • Patent number: 6399835
    Abstract: Processes for the electrophilic substitution of aromatic compounds, such as alkylation, with a desired substituent are disclosed. The processes include contacting the aromatic compound, a precursor of the desired substituent and an aqueous reagent containing zinc halide at elevated temperatures such as above 50° C.
    Type: Grant
    Filed: April 6, 2000
    Date of Patent: June 4, 2002
    Assignee: Bromine Compounds Ltd.
    Inventors: Ariel Ewenson, David Itzhak, Miriam Freiberg Bergstein, Asher Shushan, Bertha Croitoru, David Beneish, Naim Faza
  • Patent number: 6392097
    Abstract: Processes for the preparation of parylene dimers, and more particularly to processes for the preparation of derivatives of octafluoro-[2,2]paracylophane, otherwise known as AF4.
    Type: Grant
    Filed: March 20, 2001
    Date of Patent: May 21, 2002
    Assignee: Specialty Coating Systems, Inc.
    Inventors: William R. Dolbier, Jr., Jian-Xin Duan, Alex J. Roche
  • Publication number: 20020055662
    Abstract: Unsubstituted aromatic compounds and aromatic compounds having one or more electron-withdrawing substituents are fluorinated, preferably in a nitromethane solvent, by contact with tri(halo- or trifluoromethyl) substituted N-fluorotriazinium salts of the following Formula I: 1
    Type: Application
    Filed: October 23, 2001
    Publication date: May 9, 2002
    Inventors: Ronald Eric. Banks, Mohamed Khalifa Besheesh
  • Publication number: 20020045775
    Abstract: The present invention relates to a process wherein heterogeneous finely dispersed palladium catalysts are used for cross coupling of alkenyl halides and boronic acids in the presence of base in an aprotic solvent to produce aryl- or heteroaryl-olefin compounds. The process provides for use with either electron-withdrawing or electron-donating substituents for cross coupling of alkyl halides with boronic acids.
    Type: Application
    Filed: July 16, 2001
    Publication date: April 18, 2002
    Inventors: Yongkui Sun, Carl LeBlond, John R. Sowa
  • Patent number: 6194620
    Abstract: Dichloro-tetrafluoro-[2,2]-paracyclophane (formula I), which is a novel compound useful as a material for forming a coating film by chemical vapor deposition, and a process for manufacturing thereof and poly-&agr;&agr;-difluoro-chloro-para-xylylene film prepared therefrom are disclosed. Dichloro-tetrafluoro-[2,2]-paracyclophane is manufactured by chlorinating tetrafluoro-[2,2]-paracyclophane. The film to be formed by chemical vapor deposition of dichloro-tetrafluoro-[2,2]-paracyclophane has remarkably improved thermostability, as compared with the conventional products and is expected to be applied in various fields.
    Type: Grant
    Filed: January 27, 1997
    Date of Patent: February 27, 2001
    Assignee: Daisan Kasei Kabushiki Kaisha
    Inventor: Hiroshi Maruyama
  • Patent number: 6150571
    Abstract: A method for preparing 2,4-Dichloro-3,5-dimethylfluorobenzene, wherein the 2,4-Dichloro-3,5-dimethylfluorobenzene can be prepared in highisomeric selectivities when 3,5-dimethylfluorobenzene is chlorinated in the presence of Friedel-Crafts catalysts and a sulfur-containing co-catalyst.The invention is also directed to an intermediary for preparing a pharmaceutically-active compound including 4-dichloro-3,5-dimethyl fluorobenzene.
    Type: Grant
    Filed: March 4, 1999
    Date of Patent: November 21, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventors: Franz-Josef Mais, Robert Horst Bloodworth, Karsten Von Dem Bruch
  • Patent number: 6084132
    Abstract: Fluorescent dyes which fluoresce in a variety of colors are produced from substituted and un-substituted 6-ring and 8-ring aromatic diketones by reductive alkylation with alkyl halides in the presence of zinc.
    Type: Grant
    Filed: December 3, 1999
    Date of Patent: July 4, 2000
    Assignee: Rohm and Haas Company
    Inventor: Peter J. Heffron
  • Patent number: 6066766
    Abstract: 4-Chlorobiphenyls are prepared by reacting a haloaromatic with an aryl Grignard compound, where halogen is chlorine, bromine or iodine, in the presence of a palladium catalyst of the formula (IV) ##STR1##
    Type: Grant
    Filed: August 3, 1999
    Date of Patent: May 23, 2000
    Assignee: Clariant GmbH
    Inventors: Steffen Haber, Stefan Scherer, Andreas Meudt, Antje Noerenberg
  • Patent number: 6043397
    Abstract: A method for the production of a fluorine-containing aromatic compound is provided which allows the relevant reaction to proceed in a standard reaction vessel such as, for example, a glass vessel at room temperature under an ambient pressure without requiring provision of such special devices as have been necessary heretofore or adoption of harsh reaction conditions. This method comprises causing an aromatic compound (A) having a cyclic skeletal part of 6 to 16 carbon atoms containing a plurality of --C(.dbd.O)X groups, wherein X stands for a hydrogen atom, a halogen atom, or an alkyl group of 1 to 10 carbon atoms, and having the remaining hydrogen atoms unsubstituted or partly or wholly substituted with at least one species of halogen atom to react with a compound (B) represented by the formula: ##STR1## wherein R.sup.1 and R.sup.2 independently stand for an alkyl group of 1 to 6 carbon atoms or a phenyl group.
    Type: Grant
    Filed: August 25, 1998
    Date of Patent: March 28, 2000
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Seiichi Teshima, Yoshinobu Asako
  • Patent number: 6008407
    Abstract: The present invention provides a method of preparing ortho-difluorobenzene derivatives, which comprises (a) providing a mixture of cyclohexenes by reacting chlorotrifluoroethylene (CTFE) and 1.3-diene in a flow reactor and distilling the resultant, and (b) dehydrohalogenating the mixture of cyclohexenes with a phase transition catalyst in :he presence of alkali metal hydroxide at temperature range of 40 to 150.degree. C. without using any organic solvent. The distillate having low boiling point, which is obtained during distillation of the resultant, is recycled into the flow reactor. The present invention also provides a method of preparing 2-chloro-4,5-difluorobenzoic acid, which comprises (a) providing a mixture of 4-chloro-1-methyl-4,5,5-trifluorocyclohexene and 5-chloro-1-methyl-4,4,5-trifluorocyclohexene by reacting chlorotrifluoroethylene (CTFE) and isoprene and distilling the resultant.
    Type: Grant
    Filed: November 3, 1998
    Date of Patent: December 28, 1999
    Assignees: Zelinsky Institute of Organic Chemistry, Samsung General Chemicals Co., Ltd.
    Inventors: Oleg Matveyevich Nefedov, Nikolay Vasiljcvich Volchkov, Mariya Borisovna Lipkind, Ho Seong Lee, Young Jun Park, Min Hwan Kim
  • Patent number: 5900502
    Abstract: According to the present invention there is provided a process for the selective introduction of one or more fluorine atoms into a disubstituted aromatic compound in an acid medium with fluorine gas characterized in that the acid medium has a dielectric constant of at least 20 and a pH of less than 3. The present process provides a cost effective means of selectively introducing one or more fluorine atoms into an aromatic compound in good overall yield.
    Type: Grant
    Filed: October 25, 1996
    Date of Patent: May 4, 1999
    Assignee: BNFL Fluorochemicals Limited
    Inventors: Christopher John Skinner, John Hutchinson, Julie Thomson, Richard Dickinson Chambers
  • Patent number: 5849962
    Abstract: A process for the preparation of octafluoro-?2,2!paracyclophane includes contacting a reactant selected from the group consisting of 1,4-bis(bromodifluoromethyl)benzene (dibromide), 1,4-bis(chlorodifluoromethyl)benzene (dichloride), and 1,4-bis(iododifluoromethyl)benzene (diiodide) with trimethylsilyltributyltin (TMSTBT) (a reducing agent) and fluoride ions in a refluxing solution of hexamethylphosphoramide (HMPA) or dimethylsulfoxide (DMSO) in tetrahydrofuran (THF) at conditions effective to promote a reaction product comprising octafluoro-?2,2!paracyclophane.
    Type: Grant
    Filed: November 26, 1997
    Date of Patent: December 15, 1998
    Assignee: Specialty Coating Systems, Inc.
    Inventors: William R. Dolbier, Jr., Xiao X. Rong
  • Patent number: 5841005
    Abstract: Methods of making parylene AF4 using novel that result in reduced cost. Low dilution technology may used to provide parylene AF4 in substantially improved yields. The relative amount of transition metal catalyst can be decreased. The amount of undesired byproduct is also reduced.
    Type: Grant
    Filed: March 14, 1997
    Date of Patent: November 24, 1998
    Inventors: William R. Dolbier, Jr., Jian-Xin Duan, Alex J. Roche
  • Patent number: 5763700
    Abstract: A pesticidal compound, suitable for combating soil borne insect pests has formula I: ##STR1## in which formula: Ar.sub.A represents a phenyl or naphthyl group optionally substituted by one or more groups selected from halogen, alkoxy, haloalkoxy, methylenedioxy, C.sub.1 -C.sub.6 alkyl and C.sub.1 -C.sub.6 haloalkyl; andAr.sub.B represents a phenoxy, phenyl, benzyl or benzoyl-substituted phenyl group which is optionally further substituted;the configuration of the aryl cyclopropyl group and the group CH.sub.2 Ar.sub.B about the double bond being mutually trans.
    Type: Grant
    Filed: March 16, 1995
    Date of Patent: June 9, 1998
    Assignee: British Technology Group Limited
    Inventors: Bhupinder Pall Singh Khambay, Mu-Guang Liu
  • Patent number: 5744656
    Abstract: A method for producing tetrakis (pentafluorophenyl) borates is described. Hexafluorobenzene is converted to bromopentafluorobenzene which may be isolated and then reacted with an alkyl lithium to produce pentafluorophenyl lithium which in turn is reacted directly with an appropriate reagent to produce the desired borate.
    Type: Grant
    Filed: October 25, 1996
    Date of Patent: April 28, 1998
    Assignee: Boulder Scientific Company
    Inventor: Fredric Askham
  • Patent number: 5686608
    Abstract: A process for preparing polycyclic aromatic compounds by cross-coupling aromatic boron compounds with aromatic halogen compounds or perfluoroalkylsulfonates in the presence of metallic palladium as catalyst comprises adding to the reactiona) at least one water-soluble complexing ligand andb) sufficient water for the reaction mixture to form an aqueous phase.The reaction of the invention proceeds chemoselectively so that even electrophilic groups such as esters or nitriles do not have an adverse effect on the course of the reaction.The use according to the invention of a water-soluble complexing ligand in an aqueous phase enables polycyclic aromatic compounds to be prepared in very good yields and at the same time very high purity, in particular without contamination by the complexing ligands.
    Type: Grant
    Filed: April 24, 1995
    Date of Patent: November 11, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Steffen Haber, Javier Manero
  • Patent number: 5654490
    Abstract: The present invention relates to novel 4-halo-2-fluoro-5-alkylbenzoyl compounds and their methods of manufacture. These compounds are useful for the preparation of agricultural chemicals and medicines, particularly as intermediates for an active class of aryl-haloalkylpyrazole and aryl alkylsulfonylpyrazole herbicides.
    Type: Grant
    Filed: May 1, 1995
    Date of Patent: August 5, 1997
    Assignee: Monsanto Company
    Inventors: Bruce C. Hamper, Kindrick L. Leschinsky
  • Patent number: 5550236
    Abstract: A process for preparing polycyclic aromatic compounds by cross-coupling aromatic boronic acids with aromatic halogen compounds or perfluoroalkylsulfonates in the presence of metallic palladium, if desired applied to a support material, as catalyst, wherein the coupling is carried out in the presence of a ligand and a base. The process of the invention allows the yield of polycyclic aromatic compounds to be significantly increased in comparison with processes not using a ligand and thus allows a yield optimum for the Pd(0)-catalyzed cross-coupling of aromatic boronic acids with aromatic halogen compounds to be achieved.
    Type: Grant
    Filed: April 24, 1995
    Date of Patent: August 27, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hubert Schlosser, Rainer Wingen, Javier Manero
  • Patent number: 5536892
    Abstract: A process for the preparation of octafluoro-[2,2]paracyclophane includes contacting a reactant selected from the group consisting of 1,4-bis (bromodifluoromethyl)benzene (dibromide), 1,4-bis (chlorodifluoromethyl)benzene (dichloride), and 1,4-bis (iododifluoromethyl)benzene (diiodide) with trimethylsilyltributyltin (TMSTBT) (a reducing agent) and fluoride ions in a refluxing solution of hexamethylphosphoramide (HMPA) or dimethylsulfoxide (DMSO) in tetrahydrofuran (THF) at conditions effective to promote a reaction product comprising octafluoro-[2,2]paracyclophane.
    Type: Grant
    Filed: October 18, 1995
    Date of Patent: July 16, 1996
    Assignee: Specialty Coating Systems, Inc.
    Inventors: William R. Dolbier, Jr., Xiao X. Rong
  • Patent number: 5510533
    Abstract: A process for production of a 3,5-difluoroaniline compound with ease is disclosed, which comprise reacting an aminating agent with a 1,3,5-trifluorobenzene compound.
    Type: Grant
    Filed: June 5, 1991
    Date of Patent: April 23, 1996
    Assignee: SDS Biotech K.K.
    Inventors: Hiroshi Kobayashi, Masaaki Shimizu, Haruaki Ito
  • Patent number: 5504264
    Abstract: Process for preparing 1,3-difluorobenzene by means of the catalytic elimination of halogen from a 1,3-difluorohalobenzene, by reacting a 1,3-difluorohalobenzene of the formula (1) ##STR1## in which R.sup.1 to R.sup.4 are H, Cl or Br, and at least one of the radicals R.sup.1 to R.sup.4 is Cl or Br, in the presence of a palladium catalyst and of an amine, where appropriate in the presence of water or of an organic solvent which is inert towards the reactants and the reaction conditions, with hydrogen under pressure and at temperatures from about 70.degree. to about 140.degree. C.
    Type: Grant
    Filed: December 20, 1994
    Date of Patent: April 2, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Thomas Schach, Theodor Papenfuhs
  • Patent number: 5475164
    Abstract: 3-Fluoro-4,6-dichlorotoluene is prepared with reduced formation of 3-fluoro-2,6-dichlorotoluene by chlorinating 3-fluorotoluene in the presence of a catalyst system to give a mixture containing 3-fluoro-6-chlorotoluene and 3-fluoro-4-chlorotoluene and chlorinating this in the presence of another catalyst system to give 3-fluoro-4,6-dichlorotoluene.
    Type: Grant
    Filed: November 22, 1994
    Date of Patent: December 12, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventor: Werner Bussmann
  • Patent number: 5416243
    Abstract: Cyclofluoralkylated fullerene compounds are prepared by reacting the fullerenes with a fluoroalkene as exemplified by tetrafluoroethylene or perfluoromethyl vinyl ether under thermolysis conditions as exemplified by temperatures of 200.degree. C., pressure and a halocarbon solvent, the products being useful as lubricants or additive thereto as well as in cooling systems, adhesives and polymers.
    Type: Grant
    Filed: August 29, 1994
    Date of Patent: May 16, 1995
    Assignee: E. I. DuPont de Nemours and Company
    Inventors: Paul G. Bekiarian, Paul J. Fagan, Paul J. Krusic
  • Patent number: 5387725
    Abstract: Compounds having acidic protons and a molecular structure which can delocalize the electron density of the conjugate base (target compounds) are chlorinated by contacting such compounds with a perchloroalkane and aqueous base in the presence of a phase transfer catalyst which is an tetraalkylammonium hydroxide. Chlorinated products, preferably gem-dichloro compounds, are produced. The gem-dichloro compounds are useful for alkylation of aromatic compounds. For instance fluorene is chlorinated to form 9,9-dichlorofluorene which is reacted with such compounds as phenol or aniline to form such compounds as 9,9-bis(hydroxyphenyl)fluorene, 9,9-bis(aminophenyl)fluorene, or 9-aminophenyl-9-chlorofluorene.
    Type: Grant
    Filed: July 12, 1993
    Date of Patent: February 7, 1995
    Assignee: The Dow Chemical Company
    Inventors: Marlin E. Walters, W. Frank Richey, Katherine S. Clement, Steven L. Brewster, Emmett L. Tasset, Paul M. Puckett, V. Rao Durvasula, Hong A. Nguyen
  • Patent number: 5387727
    Abstract: Disclosed is a production method of generating pentafluorophenyl alkali metal salt represented by a general formula C.sub.6 F.sub.5 M (M denotes an alkali metal ion) by reacting pentafluorobenzene represented by C.sub.6 HF.sub.5 with an organometallic compound represented by a general formula RM (R denotes a hydrocarbon group of 1.about.10 carbon number which may contain a functional group having no influence on the reaction.
    Type: Grant
    Filed: December 17, 1993
    Date of Patent: February 7, 1995
    Assignee: Tosoh Akzo Corporation
    Inventors: Yoshihiko Ikeda, Takeo Yamane, Eiichi Kaji, Kenji Ishimaru
  • Patent number: 5382718
    Abstract: Mixtures of cyclofluoroalkylated fullerenes are provided by the thermal 2+2 cycloaddition of fluoroalkenes to a solution or slurry of a fullerene. The cyclofluoroalkylated fullerene mixtures are useful as lubricants or additives to lubricants; in fluorocarbon and/or chlorofluorocarbon based cooling systems; in adhesives for fluorocarbon based polymers and in gas separation membranes.
    Type: Grant
    Filed: September 16, 1993
    Date of Patent: January 17, 1995
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Paul G. Bekiarian, Paul J. Fagan, Paul J. Krusic
  • Patent number: 5334788
    Abstract: Substrate compounds are reacted by passing them through an eductor with fluorine gas optionally in the presence of a liquid medium and preferably in a loop reactor with cooling means thereby providing rapid but controlled reaction suitable for industrial scale production. Vinylidene chloride, for example, smoothly produces dichlorodifluoroethane and dichlorotrifluoroethane in good yield.
    Type: Grant
    Filed: May 1, 1992
    Date of Patent: August 2, 1994
    Assignee: PCR Group, Inc.
    Inventors: Keith B. Baucom, Adam C. Alty, Earl J. Kimmel
  • Patent number: 5313001
    Abstract: Process for the preparation of .alpha.-fluorostyrene from fluoroolefins: ##STR1## Z=hydrogen, fluorine, chlorine X=iodine, bromine, chlorine.A halogenated aromatic (I) is reacted with a fluorine-substituted ethylene (II) in the presence of a palladium catalyst to give an .alpha.-fluorostyrene (III), it being possible for R to be a hydrogen atom, a halogen atom, a C.sub.1 -C.sub.4 -alkyl group, a C.sub.1 -C.sub.5 -alkoxy group, an amino, alkylamino or dialkylamino group, an aryl radical or a fused aryl or heteroaryl ring, a hydroxyl or hydroxyalkyl group, a trifluoromethyl or perfluoroalkyl group or a nitro group.
    Type: Grant
    Filed: November 17, 1992
    Date of Patent: May 17, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Walter Heitz, Arno Knebelkamp
  • Patent number: 5306849
    Abstract: Halogenated aromatics are prepared by heating halogenoformic acid esters to 80.degree. to 280.degree. C. in the presence of hydrogen fluoride or a catalytic amount of one or more Lewis acids from the group comprising aluminium halides, iron halides and antimony halides, and in the liquid phase.
    Type: Grant
    Filed: July 28, 1993
    Date of Patent: April 26, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Norbert Lui, Dietmar Bielefeldt, Albrecht Marhold
  • Patent number: 5283378
    Abstract: Fluorine- and chlorine- and/or bromine-containing aromatic compounds are dechlorinated and/or debrominated with hydrogen in an industrially advantageous and selective manner, if the palladium catalyst is present in stationary phase and the aromatic compound in gas phase.
    Type: Grant
    Filed: September 29, 1992
    Date of Patent: February 1, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Dietmar Bielefeldt, Albrecht Marhold
  • Patent number: 5262556
    Abstract: The invention relates to a process for the reaction of fluorinated or chlorinated aromatics with electrophiles at the ortho position relative to the fluorine or chlorine atom, characterized in that a strong base is added to a mixture of the fluorinated or chlorinated aromatic and the electrophile.
    Type: Grant
    Filed: May 6, 1992
    Date of Patent: November 16, 1993
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Bernard Riefling, Jurgen Seubert, Volker Reiffenrath, Reinhard Hittich
  • Patent number: 5247124
    Abstract: A process for preparing a substituted styrene by reacting a bisarylalkyl ether in the presence of an acid catalyst is disclosed. The process is preferably used for the preparation of 4-acetoxystyrene from 4,4'-(oxydiethylidene)bisphenol diacetate and 4-methoxystyrene from 4,4'-(oxydiethylidene)bisphenol dimethyl ether. A process for preparing a bisarylalkyl ether by reacting a corresponding arylalkanol in the presence of an acid catalyst is also disclosed.
    Type: Grant
    Filed: August 25, 1992
    Date of Patent: September 21, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Mohammad Aslam, Brad L. Smith, George Kvakovszky
  • Patent number: 5233074
    Abstract: The invention describes a process for selectively preparing ortho-fluorinated substituted aromatic compounds wherein an aromatic compound containing a substituent capable of directing ortho metalation is contacted with a metalating reagent under reaction conditions sufficient to form an ortho-metalated substituted aromatic compound. The ortho-metalated substituted aromatic compound is reacted with an electrophilic fluorinating reagent under reaction conditions sufficient to form the desired ortho-fluorinated substituted aromatic compound which is then recovered from the reaction mixture. The process which utilizes a metalation intermediate prior to effecting the electrophilic fluorination step overcomes problems associated with prior art electrophilic fluorination processes which do not proceed through a regiospecifically controlled intermediate.
    Type: Grant
    Filed: June 1, 1992
    Date of Patent: August 3, 1993
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Gauri S. Lal
  • Patent number: 5227545
    Abstract: Process for the preparation of 2,4-dichlorofluorobenzene in high yield and purity without intermediate separation of the isomers formed,(1) by nitrating 1 mol of fluorobenzene to give nitrofluorobenzene using a mixture comprising 35 to 65 parts by weight of 50 to 90% strength sulfuric acid and 35 to 65 parts by weight of a nitrating acid comprising 35 to 55 parts by weight of 95 to 98% strength sulfuric acid and 45 to 65 parts by weight of 96 to 98% strength nitric acid, with the proviso that 0.8 to 2.0 equivalents of the nitrating agent NO.sub.2.sup.+ are used per mol of fluorobenzene, at 20.degree. to 90.degree. C., (2) allowing 25 g to 150 g of chlorine, in the presence of a ring chlorinating catalyst, to act on each 100 g of the crude nitrofluorobenzene mixture obtained, at 20.degree. to 100.degree. C.
    Type: Grant
    Filed: October 8, 1992
    Date of Patent: July 13, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Theodor Papenfuhs, Georg Folz, Ralf Pfirmann
  • Patent number: 5212301
    Abstract: Introduction of a fluoro substituent into an aromatic ring adjacent an electron donating group is difficult producing mixed isomers and low yields of desired products.A process for the introduction of a fluoro substituent into a substantially adjacent position to an electron-donating group into an aromatic compound in high yield is disclosed.The fluoroaromatic compounds are useful as synthetic intermediates for example in the manufacture of agrochemicals, pharmaceuticals and dyestuffs.
    Type: Grant
    Filed: May 8, 1992
    Date of Patent: May 18, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: John S. Moilliet, Richard D. Chambers, Michael H. Rock
  • Patent number: 5194672
    Abstract: A process for preparing a substituted styrene by reacting a bisarylalkyl ether in the presence of an acid catalyst is disclosed. The process is preferably used for the preparation of 4-acetoxystyrene from 4,4'-(oxydiethylidene)bisphenol diacetate and 4-methoxystyrene from 4,4'-(oxydiethylidene)bisphenol dimethyl ether. A process for preparing a bisarylalkyl ether by reacting a corresponding arylalkanol in the presence of an acid catalyst is also disclosed.
    Type: Grant
    Filed: May 14, 1991
    Date of Patent: March 16, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Mohammad Aslam, Brad L. Smith, George Kvakovszky
  • Patent number: 5185454
    Abstract: Symmetrical diaryl-acetylenes can be prepared by reacting an aryl halide with acetylene in the presence of a palladium catalyst and a base. If the acetylene is introduced into the liquid reaction mixture using a high intensity gas dispersion means, the aryl halide used can be an aryl bromide.
    Type: Grant
    Filed: October 2, 1990
    Date of Patent: February 9, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Axel Bader, Dieter Arlt
  • Patent number: 5177275
    Abstract: Substrate compounds are reacted by passing them through an eductor with fluorine gas optionally in the presence of a liquid medium and preferably in a loop reactor with cooling means thereby providing rapid but controlled reaction suitable for industrial scale production. Vinylidene chloride, for example, smoothly produces dichlorodifluoroethane and dichlorotrifluoroethane in good yield.
    Type: Grant
    Filed: May 1, 1989
    Date of Patent: January 5, 1993
    Assignee: PCR Group, Inc.
    Inventors: Keith B. Baucom, Adam C. Alty, Earl J. Kimmel
  • Patent number: 5159082
    Abstract: A process for producing an aromatic compound is disclosed, which comprises coupling an aromatic sulfinic acid or a salt thereof with an aromatic halogen compound having at least one halogen atom attached to the carbon atom of the aromatic nucleus thereof or a vinyl group-containing halogen compound having at least one halogen atom attached to the carbon atom of said vinyl group in the presence of a catalyst compound containing an element selected from platinum metals.
    Type: Grant
    Filed: June 25, 1990
    Date of Patent: October 27, 1992
    Assignee: Mitsubishi Kasei Corporation
    Inventors: Keiichi Sato, Toru Okoshi
  • Patent number: 5157169
    Abstract: In a process for producing a 3-halo-halobenzene or a 1-halo-3,5-dihalobenzene, a 2-halo-4-haloaniline or 2-halo-4,6-dihaloaniline is mixed with a deaminating agent. The 2-halo-4-haloaniline or 2-halo-4,6-dihaloaniline is deaminated so as to form a corresponding 3-halo-halobenzene or 1-halo-3,5-dihalobenzene.
    Type: Grant
    Filed: March 26, 1992
    Date of Patent: October 20, 1992
    Assignee: Mallinckrodt Specialty Chemicals Company
    Inventor: Jerry R. Patton
  • Patent number: 5146018
    Abstract: A process for the hydrogenolysis and/or dehydrohalogenation of fluorohalocarbons and/or fluorohalohydrocarbons by reacting the fluorohalocarbons and/or fluorohalohydrocarbons with a source of hydrogen in the presence of a catalyst, the improvement comprising utilizing a rhenium-containing catalyst, which may, optionally, contain at least one Group VIII metal and may, optionally, be supported.
    Type: Grant
    Filed: June 26, 1991
    Date of Patent: September 8, 1992
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Carl S. Kellner, V. N. Mallikarjuna Rao, Frank J. Weigert