Preparing Benzene Ring Containing Compound Patents (Class 570/143)
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Patent number: 6706933Abstract: 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: GrantFiled: December 30, 2002Date of Patent: March 16, 2004Assignee: Air Products and Chemicals, Inc.Inventors: Gauri Sankar Lal, Kathryn Sue Hayes
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Patent number: 6657093Abstract: 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: GrantFiled: June 13, 2002Date of Patent: December 2, 2003Assignee: Clariant GmbHInventors: Andreas Meudt, Michael Erbes, Klaus Forstinger
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Patent number: 6613948Abstract: 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: GrantFiled: September 14, 1998Date of Patent: September 2, 2003Assignee: Bayer AGInventors: Otto Neuner, Norbert Lui, Dietmar Bielefeldt, Michael Holzbrecher
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Publication number: 20030149315Abstract: 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: ApplicationFiled: February 3, 2003Publication date: August 7, 2003Inventors: Axel Klauck-Jacobs, Kathryn Sue Hayes, Reiner Taege, William Casteel, Gauri Sankar Lal
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Publication number: 20030137241Abstract: 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: ApplicationFiled: July 5, 2002Publication date: July 24, 2003Applicant: TDK CORPORATIONInventors: Tetsuji Fujita, Kensuke Ara, Tetsushi Inoue
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Patent number: 6515191Abstract: 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: GrantFiled: July 17, 2002Date of Patent: February 4, 2003Assignee: Air Products and Chemicals, Inc.Inventors: Gauri Sankar Lal, Kathryn Sue Hayes
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Publication number: 20020198417Abstract: 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: ApplicationFiled: July 17, 2002Publication date: December 26, 2002Inventors: Gauri Sankar Lal, Kathryn Sue Hayes
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Patent number: 6455744Abstract: 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: GrantFiled: November 6, 2001Date of Patent: September 24, 2002Assignee: Air Products and Chemicals, Inc.Inventors: Gauri Sankar Lal, Kathryn Sue Hayes
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Publication number: 20020099247Abstract: 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: ApplicationFiled: November 6, 2001Publication date: July 25, 2002Inventors: Gauri Sankar Lal, Kathryn Sue Hayes
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Patent number: 6399835Abstract: 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: GrantFiled: April 6, 2000Date of Patent: June 4, 2002Assignee: Bromine Compounds Ltd.Inventors: Ariel Ewenson, David Itzhak, Miriam Freiberg Bergstein, Asher Shushan, Bertha Croitoru, David Beneish, Naim Faza
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Patent number: 6392097Abstract: 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: GrantFiled: March 20, 2001Date of Patent: May 21, 2002Assignee: Specialty Coating Systems, Inc.Inventors: William R. Dolbier, Jr., Jian-Xin Duan, Alex J. Roche
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Publication number: 20020055662Abstract: 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: 1Type: ApplicationFiled: October 23, 2001Publication date: May 9, 2002Inventors: Ronald Eric. Banks, Mohamed Khalifa Besheesh
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Publication number: 20020045775Abstract: 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: ApplicationFiled: July 16, 2001Publication date: April 18, 2002Inventors: Yongkui Sun, Carl LeBlond, John R. Sowa
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Patent number: 6194620Abstract: 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: GrantFiled: January 27, 1997Date of Patent: February 27, 2001Assignee: Daisan Kasei Kabushiki KaishaInventor: Hiroshi Maruyama
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Patent number: 6150571Abstract: 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: GrantFiled: March 4, 1999Date of Patent: November 21, 2000Assignee: Bayer AktiengesellschaftInventors: Franz-Josef Mais, Robert Horst Bloodworth, Karsten Von Dem Bruch
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Patent number: 6084132Abstract: 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: GrantFiled: December 3, 1999Date of Patent: July 4, 2000Assignee: Rohm and Haas CompanyInventor: Peter J. Heffron
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Patent number: 6066766Abstract: 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: GrantFiled: August 3, 1999Date of Patent: May 23, 2000Assignee: Clariant GmbHInventors: Steffen Haber, Stefan Scherer, Andreas Meudt, Antje Noerenberg
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Patent number: 6043397Abstract: 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: GrantFiled: August 25, 1998Date of Patent: March 28, 2000Assignee: Nippon Shokubai Co., Ltd.Inventors: Seiichi Teshima, Yoshinobu Asako
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Patent number: 6008407Abstract: 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: GrantFiled: November 3, 1998Date of Patent: December 28, 1999Assignees: 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
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Patent number: 5900502Abstract: 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: GrantFiled: October 25, 1996Date of Patent: May 4, 1999Assignee: BNFL Fluorochemicals LimitedInventors: Christopher John Skinner, John Hutchinson, Julie Thomson, Richard Dickinson Chambers
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Patent number: 5849962Abstract: 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: GrantFiled: November 26, 1997Date of Patent: December 15, 1998Assignee: Specialty Coating Systems, Inc.Inventors: William R. Dolbier, Jr., Xiao X. Rong
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Patent number: 5841005Abstract: 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: GrantFiled: March 14, 1997Date of Patent: November 24, 1998Inventors: William R. Dolbier, Jr., Jian-Xin Duan, Alex J. Roche
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Patent number: 5763700Abstract: 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: GrantFiled: March 16, 1995Date of Patent: June 9, 1998Assignee: British Technology Group LimitedInventors: Bhupinder Pall Singh Khambay, Mu-Guang Liu
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Patent number: 5744656Abstract: 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: GrantFiled: October 25, 1996Date of Patent: April 28, 1998Assignee: Boulder Scientific CompanyInventor: Fredric Askham
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Patent number: 5686608Abstract: 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: GrantFiled: April 24, 1995Date of Patent: November 11, 1997Assignee: Hoechst AktiengesellschaftInventors: Steffen Haber, Javier Manero
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Patent number: 5654490Abstract: 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: GrantFiled: May 1, 1995Date of Patent: August 5, 1997Assignee: Monsanto CompanyInventors: Bruce C. Hamper, Kindrick L. Leschinsky
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Patent number: 5550236Abstract: 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: GrantFiled: April 24, 1995Date of Patent: August 27, 1996Assignee: Hoechst AktiengesellschaftInventors: Hubert Schlosser, Rainer Wingen, Javier Manero
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Patent number: 5536892Abstract: 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: GrantFiled: October 18, 1995Date of Patent: July 16, 1996Assignee: Specialty Coating Systems, Inc.Inventors: William R. Dolbier, Jr., Xiao X. Rong
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Patent number: 5510533Abstract: 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: GrantFiled: June 5, 1991Date of Patent: April 23, 1996Assignee: SDS Biotech K.K.Inventors: Hiroshi Kobayashi, Masaaki Shimizu, Haruaki Ito
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Patent number: 5504264Abstract: 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: GrantFiled: December 20, 1994Date of Patent: April 2, 1996Assignee: Hoechst AktiengesellschaftInventors: Thomas Schach, Theodor Papenfuhs
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Patent number: 5475164Abstract: 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: GrantFiled: November 22, 1994Date of Patent: December 12, 1995Assignee: Bayer AktiengesellschaftInventor: Werner Bussmann
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Patent number: 5416243Abstract: 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: GrantFiled: August 29, 1994Date of Patent: May 16, 1995Assignee: E. I. DuPont de Nemours and CompanyInventors: Paul G. Bekiarian, Paul J. Fagan, Paul J. Krusic
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Patent number: 5387725Abstract: 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: GrantFiled: July 12, 1993Date of Patent: February 7, 1995Assignee: The Dow Chemical CompanyInventors: Marlin E. Walters, W. Frank Richey, Katherine S. Clement, Steven L. Brewster, Emmett L. Tasset, Paul M. Puckett, V. Rao Durvasula, Hong A. Nguyen
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Patent number: 5387727Abstract: 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: GrantFiled: December 17, 1993Date of Patent: February 7, 1995Assignee: Tosoh Akzo CorporationInventors: Yoshihiko Ikeda, Takeo Yamane, Eiichi Kaji, Kenji Ishimaru
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Patent number: 5382718Abstract: 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: GrantFiled: September 16, 1993Date of Patent: January 17, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventors: Paul G. Bekiarian, Paul J. Fagan, Paul J. Krusic
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Patent number: 5334788Abstract: 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: GrantFiled: May 1, 1992Date of Patent: August 2, 1994Assignee: PCR Group, Inc.Inventors: Keith B. Baucom, Adam C. Alty, Earl J. Kimmel
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Patent number: 5313001Abstract: 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: GrantFiled: November 17, 1992Date of Patent: May 17, 1994Assignee: Hoechst AktiengesellschaftInventors: Walter Heitz, Arno Knebelkamp
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Patent number: 5306849Abstract: 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: GrantFiled: July 28, 1993Date of Patent: April 26, 1994Assignee: Bayer AktiengesellschaftInventors: Norbert Lui, Dietmar Bielefeldt, Albrecht Marhold
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Patent number: 5283378Abstract: 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: GrantFiled: September 29, 1992Date of Patent: February 1, 1994Assignee: Bayer AktiengesellschaftInventors: Dietmar Bielefeldt, Albrecht Marhold
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Patent number: 5262556Abstract: 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: GrantFiled: May 6, 1992Date of Patent: November 16, 1993Assignee: Merck Patent Gesellschaft mit beschrankter HaftungInventors: Bernard Riefling, Jurgen Seubert, Volker Reiffenrath, Reinhard Hittich
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Patent number: 5247124Abstract: 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: GrantFiled: August 25, 1992Date of Patent: September 21, 1993Assignee: Hoechst Celanese CorporationInventors: Mohammad Aslam, Brad L. Smith, George Kvakovszky
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Patent number: 5233074Abstract: 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: GrantFiled: June 1, 1992Date of Patent: August 3, 1993Assignee: Air Products and Chemicals, Inc.Inventor: Gauri S. Lal
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Patent number: 5227545Abstract: 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: GrantFiled: October 8, 1992Date of Patent: July 13, 1993Assignee: Hoechst AktiengesellschaftInventors: Theodor Papenfuhs, Georg Folz, Ralf Pfirmann
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Patent number: 5212301Abstract: 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: GrantFiled: May 8, 1992Date of Patent: May 18, 1993Assignee: Imperial Chemical Industries PLCInventors: John S. Moilliet, Richard D. Chambers, Michael H. Rock
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Patent number: 5194672Abstract: 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: GrantFiled: May 14, 1991Date of Patent: March 16, 1993Assignee: Hoechst Celanese CorporationInventors: Mohammad Aslam, Brad L. Smith, George Kvakovszky
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Patent number: 5185454Abstract: 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: GrantFiled: October 2, 1990Date of Patent: February 9, 1993Assignee: Bayer AktiengesellschaftInventors: Axel Bader, Dieter Arlt
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Patent number: 5177275Abstract: 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: GrantFiled: May 1, 1989Date of Patent: January 5, 1993Assignee: PCR Group, Inc.Inventors: Keith B. Baucom, Adam C. Alty, Earl J. Kimmel
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Patent number: 5159082Abstract: 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: GrantFiled: June 25, 1990Date of Patent: October 27, 1992Assignee: Mitsubishi Kasei CorporationInventors: Keiichi Sato, Toru Okoshi
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Patent number: 5157169Abstract: 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: GrantFiled: March 26, 1992Date of Patent: October 20, 1992Assignee: Mallinckrodt Specialty Chemicals CompanyInventor: Jerry R. Patton
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Patent number: 5146018Abstract: 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: GrantFiled: June 26, 1991Date of Patent: September 8, 1992Assignee: E. I. du Pont de Nemours and CompanyInventors: Carl S. Kellner, V. N. Mallikarjuna Rao, Frank J. Weigert