Halogen Containing Patents (Class 568/774)
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Patent number: 5658927Abstract: Diphenylcyclopropyl analogs in which one or more of the phenyl rings includes alkoxy substituents including a dialkylaminoalkoxy group, an unsubstituted piperazine alkoxy group, a substituted piperazine alkoxy group, an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group, and which may have one or two alkyl groups bonded to the cyclopropane. The compounds are useful as antiestrogens and anti-tumor agents.Type: GrantFiled: June 7, 1995Date of Patent: August 19, 1997Assignee: Research Corporation TechnologiesInventors: Robert A. Magarian, Joseph T. Pento, Lynette Overacre
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Patent number: 5658951Abstract: Diphenylcyclopropyl analogs in which one or more of the phenyl rings includes alkoxy substituents including a dialkylaminoalkoxy group, an unsubstituted piperazine alkoxy group, a substituted piperazine alkoxy group, an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group, and which may have one or two alkyl groups bonded to the cyclopropane. The compounds are useful as antiestrogens and anti-tumor agents.Type: GrantFiled: June 7, 1995Date of Patent: August 19, 1997Assignee: Research Corporation TechnologiesInventors: Robert A. Magarian, Joseph T. Pento, Lynette Overacre
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Patent number: 5658914Abstract: Diphenylcyclopropyl analogs in which one or more of the phenyl rings includes alkoxy substituents including a dialkylaminoalkoxy group, an unsubstituted piperazine alkoxy group, a substituted piperazine alkoxy group, an unsubstituted piperidine alkoxy group, and a substituted piperidine alkoxy group, and which may have one or two alkyl groups bonded to the cyclopropane. The compounds are useful as antiestrogens and anti-tumor agents.Type: GrantFiled: June 7, 1995Date of Patent: August 19, 1997Assignee: Research Corporation TechnologiesInventors: Robert A. Magarian, Joseph T. Pento, Lynette Overacre
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Patent number: 5648562Abstract: Process for oxidizing 1,4-dichlorobenzene using a secondary synthesized zeolites or zeolite-like metallosilicates or a primary synthesized zeolite-like metallosilicate and a peroxide.Type: GrantFiled: May 30, 1995Date of Patent: July 15, 1997Assignee: Sandoz Ltd.Inventor: Clive A. Henrick
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Patent number: 5463129Abstract: The present invention relates to a method of cleaving arylethers such as arylethers represented by the formula: ##STR1## wherein R is hydrogen, C.sub.1 -C.sub.6 alkyl, cycloalkyl, phenyl, substituted phenyl or CH.dbd.CH.sub.2 ; each A is independently NO.sub.2, hydroxy, halo, or methoxy; n is an integer from 0 to 5; and x is 1 or 2, comprising contacting the arylether with an amide hydrohalide salt under conditions sufficient to cleave the ether group(s) of the arylether and form a phenol or substituted phenol. The present invention also relates to a method of preparing 4,6-diaminoresorcinol, which is a monomer used for making polybenzoxazoles (PBO).Type: GrantFiled: December 23, 1993Date of Patent: October 31, 1995Assignee: The Dow Chemical CompanyInventors: Zenon Lysenko, Richard G. Pews
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Patent number: 5463108Abstract: The present invention provides a unique and novel way of producing 4-acetoxystyrene. In this new process, 4-hydroxystyrene is acetylated, in the presence of an acetylation agent, under suitable conditions of temperature and pressure and for a sufficient period of time to form acetoxystyrene.Type: GrantFiled: December 19, 1994Date of Patent: October 31, 1995Assignee: Hoechst Celanese CorporationInventors: James R. Sounik, William W. Wilkison, III, Keith M. Russ, Lynn Massarelli
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Patent number: 5416235Abstract: A process for the preparation of aromatic compounds of the general formula I,Ar--X Iin which Ar represents an optionally substituted aryl group and X represents a group OH, Cl, Br or CN, by reaction of an aryl diazoniumsalt of the formula II,Ar--N.dbd.N.sup.+ Y.sup.- IIin which Ar is as defined above and Y represents a suitable counterion, with water, hydrogen chloride or a salt thereof, hydrogen bromide or a salt thereof, or a cyanide in the presence of a copper(I)salt, characterized in that the copper(I)salt is a copper(I)salt derived from an hydroxy carboxylic acid.Type: GrantFiled: November 1, 1993Date of Patent: May 16, 1995Assignee: Octel Chemicals LimitedInventors: Bruce C. Gilbert, Peter Hanson, Jason R. Jones, Allan W. Timms
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Patent number: 5397802Abstract: Gem-Dichlorocyclopropanes (Analog II derivatives) which demonstrate antiproliferative activity toward MCF-7 cells, in vitro and are generally not reversed by estradiol or having intrinsic estrogenicity (except the hydroxyphenyl derivative Compound 30). In general the cyclopropane compounds have the formula: ##STR1## or any pharmaceutically acceptable salt thereof. X is selected from a group consisting of hydrogen and halogen atoms. The group R.sub.1 may be a hydrogen atom, an alkyl group, an acyl group, or an arylalkyl group. The group R.sub.2 may be a hydrogen atom, an unsubstituted aryl group or a substituted aryl group. The group R.sub.3 may be a hydrogen atom, an alkyl group, a cycloalkyl group, a substituted aryl group or an unsubstituted aryl group. The group R.sub.4 may be a hydrogen atom, an unsubstituted aryl group or a substituted aryl group. The R.sub.4 is absent when R.sub.Type: GrantFiled: February 22, 1993Date of Patent: March 14, 1995Assignee: Research Corporation Technologies, Inc.Inventors: Robert A. Magarian, Joseph T. Pento, May T. Griffin
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Patent number: 5393776Abstract: This invention relates to structurally novel acyclic tocotrienol analogs, which are useful for cholesterol/lipid lowering in cases of hypercholesterolemia and hyperlipidemia, and for atherosclerosis. Also provided are pharmaceutical compositions and a method of use employing those compositions.Type: GrantFiled: May 13, 1994Date of Patent: February 28, 1995Assignee: Bristol-Myers Squibb CompanyInventor: Bradley C. Pearce
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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: 5276214Abstract: A biphenyl compound having the formula (I) is newly separated into its optical active compound, and useful as an optically separating agent: ##STR1## wherein W, X and Y are each an atom or atomic group selected from among H, F, Cl, Br, I, CH.sub.3, CF.sub.3, OH, OCH.sub.3, NH.sub.2 and N(CH.sub.3).sub.2 and Z is an atom or atomic group selected from among Cl, Br, I, CH.sub.3 and OCH.sub.Type: GrantFiled: December 18, 1992Date of Patent: January 4, 1994Assignee: Daicel Chemical Industries, Ltd.Inventor: Fumio Toda
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Patent number: 5264151Abstract: Disclosed herein are optically active phenols of formula (V) which are useful as precursors for esters used in liquid crystalline crystalline mixtures: ##STR1## wherein R.sub.2 represents an optically active alkyl or alkoxyalkyl group having 3 to 15 carbon atoms optionally substituted by halogen atoms; k represents a number of 0 or 1; n represents a number of 1 to 6.Type: GrantFiled: March 20, 1992Date of Patent: November 23, 1993Assignee: Sumitomo Chemical Company, LimitedInventors: Takayuki Higashi, Isao Kurimoto, Shoji Toda, Masayoshi Minai, Takeshi Tani, Chizu Kawakami, Koichi Fujisawa, Kiyoshi Imamura
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Patent number: 5196617Abstract: A process for hydrodehalogenating halogenated organic compounds present in a contaminated aqueous environmental source in which the halogenated organic compounds are reacted with hydrogen gas or a source of hydrogen gas in the presence of a catalyst of palladium on carbon.Type: GrantFiled: January 14, 1992Date of Patent: March 23, 1993Assignee: Engelhard CorporationInventors: Suphan Kovenklioglu, Edward N. Balko, Jeffrey B. Hoke, Robert J. Farrauto, Gary A. Gramiccioni
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Patent number: 5164502Abstract: Chloro and bromophenols and N-acylanilines are fluorinated in an ortho or para position with an N-fluoropyridinium salt to obtain fluorohalophenols and N-acylfluorohaloanilines, which can be further converted to fluorophenols and N-acylfluoroanilines by reduction. Thus, o-fluorophenol is obtained by fluorination of p-bromophenol with 2-chloro-6-(trichloromethyl)pyridinium fluoroborate and reduction of the product obtained with sodium formate and a palladium catalyst. N-Fluoropyridinium salts having trichloromethyl substituents are disclosed.Type: GrantFiled: November 8, 1991Date of Patent: November 17, 1992Assignee: DowElancoInventors: Alexander P. Fung, M. Moklesur Rahman, Thomas J. Dietsche
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Patent number: 5116982Abstract: Chloro and bromophenols and N-acylanilines are fluorinated in an ortho or para position with an N-fluoropyridinium salt to obtain fluorohalophenols and N-acylfluorohaloanilines, which can be further converted to fluorophenols and N-acylfluoroanilines by reduction. Thus, o-fluorophenol is obtained by fluorination of p-bromophenol with 2-chloro-6-(trichloromethyl)-pyridinium fluoroborate and reduction of the product obtained with sodium formate and a palladium catalyst. N-fluoropyridinium salts having trichloromethyl substituents are disclosed.Type: GrantFiled: August 6, 1990Date of Patent: May 26, 1992Assignee: DowElancoInventors: Alexander P. Fung, M. Moklesur Rahman, Thomas J. Dietsche
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Patent number: 5108647Abstract: A method of dehalogenating a halogenated hydrocarbon in the presence of a nucleophilic reaction partner, comprising dispersing the halogenated hydrocarbon by chemical reaction (DCR), and dehalogenating the resulting finely dispersed reaction product by means of a strictly chemical conversion with the nucleophilic reaction partner at a temperature between ambient temperature and approximately 510.degree. C.Type: GrantFiled: March 26, 1991Date of Patent: April 28, 1992Inventor: Friedrich Bolsing
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Patent number: 5026926Abstract: The polychlorophenols, e.g., 2,6-dichlorophenol (a known agrochemical intermediate), are effectively prepared by chlorinating ortho-chlorophenol with gaseous chlorine, optionally in the presence of other chlorophenols, characteristically in the molten state, and in the presence of a catalytically effective amount of a primary, secondary or tertiary amine.Type: GrantFiled: March 7, 1988Date of Patent: June 25, 1991Assignee: Rhone-Poulenc ChimieInventors: Jean-Claude Leblanc, Serge Ratton, Bernard Besson, Jean-Roger Desmurs
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Patent number: 5019657Abstract: A process for the preparation of halophenols. A halobenzene is brought into contact with nitrous oxide on an acidified zeolite.Type: GrantFiled: May 2, 1989Date of Patent: May 28, 1991Assignee: Rhone-Poulenc ChimieInventors: Michel Gubelmann, Philippe-jean Tirel
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Patent number: 4965400Abstract: 3-substituted-4-hydroxy- and 4-acetoxystyrene compounds, especially 3,5-di(methyl, bromo or chloro)-4-acetoxystyrene as well as a process for its preparation. 2,6-dimethylphenol is acylated with acetic anhydride and HF catalyzed to produce 3,5-dimethyl-4-hydroxy-acetophenone. After subsequent esterification with acetic anhydride and catalyzed hydrogenation to form 1-(3',5'-dimethyl-4'-acetoxyphenyl)ethanol, this intermediate is then dehydrated with an acid and a polymerization inhibitor to produce 3,5-dimethyl-4-acetoxystyrene.Type: GrantFiled: August 2, 1988Date of Patent: October 23, 1990Inventors: Richard Vicari, Mohammad Aslam, Wilson B. Ray, Kenneth G. Davenport, Ralph Dammel, Juergen Lingnau, Karl-Friedrich Doessel
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Patent number: 4954662Abstract: Ortho-substituted phenolic compounds, e.g., 2,6-dichlorophenol, are selectively chlorinated, e.g., into 2,4,6-trichlorophenol, with gaseous chlorine in either the molten state or in a solvent medium, in the presence of a selectivity-enhancing effective amount of an organic cation.Type: GrantFiled: July 18, 1988Date of Patent: September 4, 1990Assignee: Rhone-Poulenc ChimieInventors: Jean-Roger Desmurs, Bernard Besson, Isabelle Jouve
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Patent number: 4954653Abstract: The invention discloses a catalyst on the basis of silicon and titanium having the form of microspheres and constituted by oligomeric silica and by titanium-silica-lite crystals having an oligomeric silica/titanium-silicalite molar ratio comprised within the range of from 0.05 to 0.11, wherein the crystals of titanium-silicalite are encaged by means of Si-O-Si bridges.Type: GrantFiled: June 7, 1989Date of Patent: September 4, 1990Assignee: Enichem Sintesi S.p.A.Inventors: Giuseppe Bellussi, Franco Buonomo, Antonio Esposito, Mario Clerici, Ugo Romano, Bruno Notari
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Patent number: 4940821Abstract: Fluorophenols are prepared by heating a chlorofluorobenzene with water in the presence of a copper salt at a pH of from 3.0 to 6.5.Type: GrantFiled: March 20, 1989Date of Patent: July 10, 1990Assignee: The Dow Chemical CompanyInventors: R. Garth Pews, James A. Gall
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Patent number: 4933495Abstract: The present invention relates to a process for the production of 3-mono or 3,5-disubstituted-4-acetoxystyrene wherein the 3- or 3,5-substitution is independently C.sub.1 to C.sub.10 alkyl, chlorine, bromine, iodine, --NO.sub.2, --NH.sub.2, or --SO.sub.3 H, a process for its polymerization, hydrolysis, and use in a variety of compositions.Type: GrantFiled: July 24, 1989Date of Patent: June 12, 1990Assignee: Hoechst Celanese CorporationInventors: Mohammad Aslam, Richard Vicari, Ralph Dammel, Juergen Lingnau, Karl-Friedrich Doessel
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Patent number: 4927956Abstract: 3-substituted-4-hydroxy- and 4-acetoxystyrene compounds, especially 3,5-di(methyl, bromo or chloro)-4-acetoxystyrene as well as a process for its preparation. 2,6-dimethylphenol is acylated with acetic anhydride and HF catalyzed to produce 3,5-dimethyl-4-hydroxy-acetophenone. After subsequent esterification with acetic anhydride and catalyzed hydrogenation to form 1-(3',5'-dimethyl-4'-acetoxyphenyl)ethanol, this intermediate is then dehydrated with an acid and a polymerization inhibitor to produce 3,5-dimethyl-4-acetoxystyrene.Type: GrantFiled: June 2, 1989Date of Patent: May 22, 1990Assignee: Hoechst Celanese CorporationInventors: Richard Vicari, Mohammad Aslam, Wilson B. Ray, Kenneth G. Davenport, Ralph Dammel, Juergen Lingnau, Karl-Friedrich Doessel
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Patent number: 4915875Abstract: Paramethyl-substituted hindered phenols are selectively oxidized by contacting with an oxidizing agent at elevated temperatures in the presence of a heterogeneous oxidative coupling catalyst. In the absence of an optional nucleophile the products comprise carbon-carbon oxidative coupling products. In the presence of a nucleophile, addition products result that may be further oxidized by continued exposure to the oxidizing agent to yield substituted p-hydroxybenzaldehydes.Type: GrantFiled: November 4, 1986Date of Patent: April 10, 1990Assignee: The Dow Chemical CompanyInventors: Timothy R. Diephouse, Robert M. Strom
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Patent number: 4886891Abstract: The present invention provides a process for preparing a 1,1-disubstituted ethylene derivative of the formula ##STR1## which comprises reacting lead with a carbinol derivative of the formula ##STR2## wherein R.sup.1, R.sup.2, R.sup.3, X, Y, m and n are defined in the specification. The reaction is conducted more advantageously in the presence of a metal having higher ionization tendency than lead.Type: GrantFiled: December 18, 1987Date of Patent: December 12, 1989Assignee: Otsuka Kagaku Kabushiki KaishaInventors: Shigeru Torii, Masatoshi Taniguchi, Michio Sasaoka, Yoshihisa Tomotaki, Mitsuo Akada, Hideo Tanaka, Akira Suzuki, Shiro Yamashita
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Patent number: 4885408Abstract: The ortho-substituted phenols, e.g., 2,6-dichlorophenol, are reacted with gaseous chlorine, in the presence of a catalytically effective amount of a strong or Lewis acid, to produce, e.g., a more pure 2,4,6-trichlorophenol in good yield.Type: GrantFiled: July 2, 1987Date of Patent: December 5, 1989Assignee: Rhone-Poulenc ChimieInventors: Serge Ratton, Jean-Roger Desmurs
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Patent number: 4885388Abstract: New 2-methyl-4-fluoro-phenols and process for their preparation from 2-methyl-4-fluoro-phenol.Type: GrantFiled: September 12, 1988Date of Patent: December 5, 1989Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Reiner Fischer
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Patent number: 4868256Abstract: The present invention relates to a process for the production of 3-mono or 3,5-disubstituted-4-acetoxystyrene wherein the 3- or 3,5-substitution is independently C.sub.1 to C.sub.10 alkyl, chlorine, bromine, iodine, --NO.sub.2, --NH.sub.2, or --SO.sub.3 H, a process for its polymerization, hydrolysis, and use in a variety of compositions.Type: GrantFiled: August 2, 1988Date of Patent: September 19, 1989Assignee: Hoechst CelaneseInventors: Mohammad Aslam, Richard Vicari, Ralph Dammel, Juergen Lingnau, Karl-Friedrich Doessel
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Patent number: 4855513Abstract: The chlorophenols, e.g., 2,4,6-trichlorophenol, are efficiently prepared by chlorinating an ortho-/para-substituted phenolic compound with gaseous chlorine, whether in molten state or in a solvent reaction medium, in the presence of a catalytically effective amount of a primary, secondary or tertiary amine.Type: GrantFiled: March 7, 1988Date of Patent: August 8, 1989Assignee: Rhone-Poulenc ChimieInventors: Bernard Besson, Jean-Roger Desmurs, Isabelle Jouve
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Patent number: 4855514Abstract: A process for producing iodophenols which comprises contacting phenol, a source of iodine and molecular oxygen in an aqueous medium to produce an iodophenol.Type: GrantFiled: August 17, 1988Date of Patent: August 8, 1989Assignee: Eastman Kodak CompanyInventors: Mark Rule, Regina M. Moncier
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Patent number: 4855512Abstract: 2- and 3-fluorophenols are prepared by dehydrating 1,2-dihydroxy-3-fluorocyclohexa-3,5-diene under basic conditions and recovering the desired product, for example by fractional distillation.Type: GrantFiled: March 25, 1988Date of Patent: August 8, 1989Assignee: Shell Oil CompanyInventor: George Ryback
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Patent number: 4849548Abstract: A 4-halomethyl-3,5-dihalo-2,6-dialkylphenol is hydrolyzed by contact with water to form a 4-hydroxy-methyl-3,5-dihalo-2,6-dialkylphenol under conditions to minimize formation of the corresponding bis-(4-hydroxy-3,5-dialkyl-2,6-dihalobenzyl) ether.Type: GrantFiled: March 21, 1988Date of Patent: July 18, 1989Assignee: The Dow Chemical CompanyInventor: Ming-Biann Liu
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Patent number: 4822922Abstract: Mixtures produced by chlorination of phenol/chlorophenols are effectively stabilized by stirring same in the presence of a stabilizing amount of at least one strong protonic acid and/or a Lewis acid.Type: GrantFiled: September 25, 1987Date of Patent: April 18, 1989Assignee: Rhone-Poulenc ChimieInventors: Jean-Roger Desmurs, Serge Ratton
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Patent number: 4754080Abstract: This invention relates to novel compositions comprising a N-halodialkylamine as defined in the specification and an inorganic oxide. The compositions are useful as halogenating agents for phenolic compounds. The compositions have the advantage that they are milder halogenating agents than halogens or hydrogen halides.Type: GrantFiled: April 6, 1987Date of Patent: June 28, 1988Assignee: British Petroleum Company p.l.c.Inventors: Michael Butters, Barry Nay, Keith Smith
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Patent number: 4751332Abstract: Resorcinol and substituted resorcinols are converted in one single step reaction into 1,2,3- and 1,2,4-trihydroxybenzenes and substituted hydroxy resorcinol compounds with a benzene solution of peroxypropionic acid.Type: GrantFiled: September 14, 1987Date of Patent: June 14, 1988Assignee: Degussa AktiengesellschaftInventors: Guenter Prescher, Gebhard Ritter, Holger Sauerstein
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Patent number: 4740636Abstract: Included is a process to prepare a 4-HALOmethyl-3,5-dihalo-2,6-disubstitutedphenol from a 4-methyl(substituted)phenol and a HALOgenating agent, in an aprotic organic diluent. The process is highly selective and efficient. For example, high purity 4-bromomethyl-3,5-dibromo-2,6-dimethylphenol can be prepared from 2,4,6-trimethylphenol and bromine, in bromochloromethane at high conversion.Type: GrantFiled: May 15, 1987Date of Patent: April 26, 1988Assignee: The Dow Chemical CompanyInventor: Abel Mendoza
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Patent number: 4705901Abstract: Prepare novel ring-brominated derivatives of tetraalkyl dihydroxy diaromatic compounds, e.g. 4,4'-(1,2-ethanediyl)bis(3,5-dibromo-2,6-dimethyl-phenol).Type: GrantFiled: August 26, 1986Date of Patent: November 10, 1987Assignee: The Dow Chemical CompanyInventor: Abel Mendoza
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Patent number: 4691057Abstract: The reaction of alkali metal with aromatic hydroxy compounds is promoted by inclusion of an alcohol in the reaction mixture. The alkali metal aryloxide formed can be reacted with phosphonitrilic chloride polymers to make polyaryloxyphosphazenes.Type: GrantFiled: September 19, 1984Date of Patent: September 1, 1987Assignee: Ethyl CorporationInventor: Allan A. Eisenbraun
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Patent number: 4690948Abstract: Ring opened halogenated Resorcyclic Acid Lactone (RAL) derivatives having the structure: ##STR1## are used to increase rumen fermentation efficiency.Type: GrantFiled: December 1, 1986Date of Patent: September 1, 1987Assignee: International Minerals & Chemical Corp.Inventor: Jing-Jong Lu
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Patent number: 4684752Abstract: Included is a process to prepare a 4-HALOmethyl-3,5-dihalo-2,6-disubstitutedphenol from a 4-methyl(substituted)phenol and a HALOgenating agent, in an aprotic organic diluent. The process is highly selective and efficient. For example, high purity 4-bromomethyl-3,5-dibromo-2,6-dimethylphenol can be prepared from 2,4,6-trimethylphenol and bromine, in bromochloromethane at high conversion.Type: GrantFiled: April 30, 1986Date of Patent: August 4, 1987Assignee: The Dow Chemical CompanyInventor: Abel Mendoza
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Patent number: 4670610Abstract: 2,5-Dichlorophenol is readily and facilely prepared from 2,5-dichloro-4-hydroxybenzenesulfonic acid or salt thereof, said sulfonic acid/sulfonate itself being characteristically produced by hydrolysis of a precursor trichlorobenzenesulfonic acid, by cleaving the sulfo/sulfonate moiety therefrom by treatment, e.g., under reflux, with a constant boiling point hydrobromic acid.Type: GrantFiled: March 11, 1985Date of Patent: June 2, 1987Assignee: Sandoz, Inc.Inventor: Richard H. Sehring
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Patent number: 4668831Abstract: 3-tert-Butyl-4-halophenols which are useful as intermediates for preparing compounds having medical or agricultural activities.Type: GrantFiled: March 14, 1986Date of Patent: May 26, 1987Assignee: Toyo Soda Manufacturing Co., Ltd.Inventors: Hideo Morinaka, Akira Nakanishi, Yuji Nonaka
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Patent number: 4656311Abstract: A process for preparing hydroxylated aromatic compounds optionally bearing at least one trifluoromethyl, trifluoromethoxy or trifluoromethylthio group. A chloroformate or fluoroformate, optionally bearing at least one trihalomethyl-, trihalomethoxy- or trihalomethylthiophenyl group, is reacted with liquid hydrofluoric acid.The aromatic compounds obtained are useful as synthesis intermediates in the pharmaceutical or the plant-protection industry.Type: GrantFiled: July 21, 1986Date of Patent: April 7, 1987Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Michel Desbois
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Patent number: 4621159Abstract: Prepare novel ring-brominated derivatives of tetraalkyl dihydroxy diaromatic compounds, e.g. 4,4'-(1,2-ethanediyl)bis(3,5-dibromo-2,6-dimethyl-phenol).Type: GrantFiled: September 9, 1985Date of Patent: November 4, 1986Assignee: The Dow Chemical CompanyInventor: Abel Mendoza
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Patent number: 4620042Abstract: 2-Chloro-4-fluorophenol is obtained with good yield by direct chlorination of 4-fluorophenol with chlorine gas at 0.degree.-185.degree. C. in the absence of catalyst. In a combination of these reactants, the selectivity to the substitution chlorination reaction at the 2-position of 4-fluorophenol is uncommonly high and reaches about 99% under optimum conditions. 4-Fluorophenol is subjected to the reaction as either pure liquid or solution in a suitable organic solvent such as carbon tetrachloride or acetic acid.Type: GrantFiled: March 7, 1985Date of Patent: October 28, 1986Assignee: Central Glass Company, LimitedInventors: Toshikazu Kawai, Ysunobu Nishimura, Katumi Kanesaki
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Patent number: 4593129Abstract: A process for making an alkali metal alkoxide (e.g. sodium alkoxide) of a halogen-substituted alcohol (e.g. fluorine-substituted alcohols) by dispersing an alkali metal (e.g. sodium) in a cycloalkane (e.g. cyclohexane) containing a phenol (e.g. o-allylphenol) and adding the resultant dispersion to an ether (e.g. THF) solution of a halogen-substituted alcohol. The resultant alkali metal haloalkoxide solution contains phenoxides and can be reacted with a phosphonitrilic chloride polymer to introduce haloalkoxide and phenoxide substituents.Type: GrantFiled: April 18, 1984Date of Patent: June 3, 1986Assignee: Ethyl CorporationInventors: R. Woodrow Wilson, Jr., Dustin H. Thomas
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Patent number: 4568777Abstract: The invention relates to a process for isomerizing monochlorophenols or dichlorophenols in which one or more monochlorophenol or dichlorophenol is passed in the gas phase over a zeolite catalyst. In particular, the invention relates to a process for preparing 3-chlorophenol by isomerizing 2-chlorophenol and/or 4-chlorophenol and to a process for preparing 2,5-dichlorophenol by isomerizing 2,4-dichlorophenol using said method.Type: GrantFiled: November 9, 1984Date of Patent: February 4, 1986Assignee: Hoechst AktiengesellschaftInventors: Herbert Baltes, Ernst I. Leupold
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Patent number: 4547597Abstract: Halogenated phenolic compounds are prepared by forming a low melting point complex of the phenolic compound and contacting the low melting point complex with a halogenating agent under halogenating conditions.Type: GrantFiled: May 17, 1983Date of Patent: October 15, 1985Assignee: The Dow Chemical CompanyInventors: David H. Louks, Leonard R. Thompson, Wayne C. Muench
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Patent number: 4540834Abstract: The invention relates to a process for the preparation of metachlorophenols.The process consists in selectively hydrodechlorinating, under the action of heat and in the liquid phase, polychlorophenols containing at least one chlorine atom in the meta position relative to the phenolic hydroxyl, by reacting these polychlorophenols with hydriodic acid in a quantity which is sufficient in relation to the chlorine atoms to be removed.The metachlorophenols obtained are organic synthesis intermediates.Type: GrantFiled: March 2, 1984Date of Patent: September 10, 1985Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Georges Cordier