Halogen Containing Patents (Class 568/774)
  • Patent number: 5658927
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: August 19, 1997
    Assignee: Research Corporation Technologies
    Inventors: Robert A. Magarian, Joseph T. Pento, Lynette Overacre
  • Patent number: 5658951
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: August 19, 1997
    Assignee: Research Corporation Technologies
    Inventors: Robert A. Magarian, Joseph T. Pento, Lynette Overacre
  • Patent number: 5658914
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: August 19, 1997
    Assignee: Research Corporation Technologies
    Inventors: Robert A. Magarian, Joseph T. Pento, Lynette Overacre
  • Patent number: 5648562
    Abstract: 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: Grant
    Filed: May 30, 1995
    Date of Patent: July 15, 1997
    Assignee: Sandoz Ltd.
    Inventor: Clive A. Henrick
  • Patent number: 5463129
    Abstract: 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: Grant
    Filed: December 23, 1993
    Date of Patent: October 31, 1995
    Assignee: The Dow Chemical Company
    Inventors: Zenon Lysenko, Richard G. Pews
  • Patent number: 5463108
    Abstract: 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: Grant
    Filed: December 19, 1994
    Date of Patent: October 31, 1995
    Assignee: Hoechst Celanese Corporation
    Inventors: James R. Sounik, William W. Wilkison, III, Keith M. Russ, Lynn Massarelli
  • Patent number: 5416235
    Abstract: 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: Grant
    Filed: November 1, 1993
    Date of Patent: May 16, 1995
    Assignee: Octel Chemicals Limited
    Inventors: Bruce C. Gilbert, Peter Hanson, Jason R. Jones, Allan W. Timms
  • Patent number: 5397802
    Abstract: 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: Grant
    Filed: February 22, 1993
    Date of Patent: March 14, 1995
    Assignee: Research Corporation Technologies, Inc.
    Inventors: Robert A. Magarian, Joseph T. Pento, May T. Griffin
  • Patent number: 5393776
    Abstract: 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: Grant
    Filed: May 13, 1994
    Date of Patent: February 28, 1995
    Assignee: Bristol-Myers Squibb Company
    Inventor: Bradley C. Pearce
  • 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: 5276214
    Abstract: 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: Grant
    Filed: December 18, 1992
    Date of Patent: January 4, 1994
    Assignee: Daicel Chemical Industries, Ltd.
    Inventor: Fumio Toda
  • Patent number: 5264151
    Abstract: 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: Grant
    Filed: March 20, 1992
    Date of Patent: November 23, 1993
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Takayuki Higashi, Isao Kurimoto, Shoji Toda, Masayoshi Minai, Takeshi Tani, Chizu Kawakami, Koichi Fujisawa, Kiyoshi Imamura
  • Patent number: 5196617
    Abstract: 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: Grant
    Filed: January 14, 1992
    Date of Patent: March 23, 1993
    Assignee: Engelhard Corporation
    Inventors: Suphan Kovenklioglu, Edward N. Balko, Jeffrey B. Hoke, Robert J. Farrauto, Gary A. Gramiccioni
  • Patent number: 5164502
    Abstract: 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: Grant
    Filed: November 8, 1991
    Date of Patent: November 17, 1992
    Assignee: DowElanco
    Inventors: Alexander P. Fung, M. Moklesur Rahman, Thomas J. Dietsche
  • Patent number: 5116982
    Abstract: 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: Grant
    Filed: August 6, 1990
    Date of Patent: May 26, 1992
    Assignee: DowElanco
    Inventors: Alexander P. Fung, M. Moklesur Rahman, Thomas J. Dietsche
  • Patent number: 5108647
    Abstract: 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: Grant
    Filed: March 26, 1991
    Date of Patent: April 28, 1992
    Inventor: Friedrich Bolsing
  • Patent number: 5026926
    Abstract: 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: Grant
    Filed: March 7, 1988
    Date of Patent: June 25, 1991
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean-Claude Leblanc, Serge Ratton, Bernard Besson, Jean-Roger Desmurs
  • Patent number: 5019657
    Abstract: A process for the preparation of halophenols. A halobenzene is brought into contact with nitrous oxide on an acidified zeolite.
    Type: Grant
    Filed: May 2, 1989
    Date of Patent: May 28, 1991
    Assignee: Rhone-Poulenc Chimie
    Inventors: Michel Gubelmann, Philippe-jean Tirel
  • Patent number: 4965400
    Abstract: 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: Grant
    Filed: August 2, 1988
    Date of Patent: October 23, 1990
    Inventors: Richard Vicari, Mohammad Aslam, Wilson B. Ray, Kenneth G. Davenport, Ralph Dammel, Juergen Lingnau, Karl-Friedrich Doessel
  • Patent number: 4954662
    Abstract: 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: Grant
    Filed: July 18, 1988
    Date of Patent: September 4, 1990
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean-Roger Desmurs, Bernard Besson, Isabelle Jouve
  • Patent number: 4954653
    Abstract: 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: Grant
    Filed: June 7, 1989
    Date of Patent: September 4, 1990
    Assignee: Enichem Sintesi S.p.A.
    Inventors: Giuseppe Bellussi, Franco Buonomo, Antonio Esposito, Mario Clerici, Ugo Romano, Bruno Notari
  • Patent number: 4940821
    Abstract: 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: Grant
    Filed: March 20, 1989
    Date of Patent: July 10, 1990
    Assignee: The Dow Chemical Company
    Inventors: R. Garth Pews, James A. Gall
  • Patent number: 4933495
    Abstract: 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: Grant
    Filed: July 24, 1989
    Date of Patent: June 12, 1990
    Assignee: Hoechst Celanese Corporation
    Inventors: Mohammad Aslam, Richard Vicari, Ralph Dammel, Juergen Lingnau, Karl-Friedrich Doessel
  • Patent number: 4927956
    Abstract: 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: Grant
    Filed: June 2, 1989
    Date of Patent: May 22, 1990
    Assignee: Hoechst Celanese Corporation
    Inventors: Richard Vicari, Mohammad Aslam, Wilson B. Ray, Kenneth G. Davenport, Ralph Dammel, Juergen Lingnau, Karl-Friedrich Doessel
  • Patent number: 4915875
    Abstract: 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: Grant
    Filed: November 4, 1986
    Date of Patent: April 10, 1990
    Assignee: The Dow Chemical Company
    Inventors: Timothy R. Diephouse, Robert M. Strom
  • Patent number: 4886891
    Abstract: 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: Grant
    Filed: December 18, 1987
    Date of Patent: December 12, 1989
    Assignee: Otsuka Kagaku Kabushiki Kaisha
    Inventors: Shigeru Torii, Masatoshi Taniguchi, Michio Sasaoka, Yoshihisa Tomotaki, Mitsuo Akada, Hideo Tanaka, Akira Suzuki, Shiro Yamashita
  • Patent number: 4885408
    Abstract: 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: Grant
    Filed: July 2, 1987
    Date of Patent: December 5, 1989
    Assignee: Rhone-Poulenc Chimie
    Inventors: Serge Ratton, Jean-Roger Desmurs
  • Patent number: 4885388
    Abstract: New 2-methyl-4-fluoro-phenols and process for their preparation from 2-methyl-4-fluoro-phenol.
    Type: Grant
    Filed: September 12, 1988
    Date of Patent: December 5, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albrecht Marhold, Reiner Fischer
  • Patent number: 4868256
    Abstract: 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: Grant
    Filed: August 2, 1988
    Date of Patent: September 19, 1989
    Assignee: Hoechst Celanese
    Inventors: Mohammad Aslam, Richard Vicari, Ralph Dammel, Juergen Lingnau, Karl-Friedrich Doessel
  • Patent number: 4855513
    Abstract: 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: Grant
    Filed: March 7, 1988
    Date of Patent: August 8, 1989
    Assignee: Rhone-Poulenc Chimie
    Inventors: Bernard Besson, Jean-Roger Desmurs, Isabelle Jouve
  • Patent number: 4855514
    Abstract: 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: Grant
    Filed: August 17, 1988
    Date of Patent: August 8, 1989
    Assignee: Eastman Kodak Company
    Inventors: Mark Rule, Regina M. Moncier
  • Patent number: 4855512
    Abstract: 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: Grant
    Filed: March 25, 1988
    Date of Patent: August 8, 1989
    Assignee: Shell Oil Company
    Inventor: George Ryback
  • Patent number: 4849548
    Abstract: 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: Grant
    Filed: March 21, 1988
    Date of Patent: July 18, 1989
    Assignee: The Dow Chemical Company
    Inventor: Ming-Biann Liu
  • Patent number: 4822922
    Abstract: 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: Grant
    Filed: September 25, 1987
    Date of Patent: April 18, 1989
    Assignee: Rhone-Poulenc Chimie
    Inventors: Jean-Roger Desmurs, Serge Ratton
  • Patent number: 4754080
    Abstract: 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: Grant
    Filed: April 6, 1987
    Date of Patent: June 28, 1988
    Assignee: British Petroleum Company p.l.c.
    Inventors: Michael Butters, Barry Nay, Keith Smith
  • Patent number: 4751332
    Abstract: 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: Grant
    Filed: September 14, 1987
    Date of Patent: June 14, 1988
    Assignee: Degussa Aktiengesellschaft
    Inventors: Guenter Prescher, Gebhard Ritter, Holger Sauerstein
  • Patent number: 4740636
    Abstract: 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: Grant
    Filed: May 15, 1987
    Date of Patent: April 26, 1988
    Assignee: The Dow Chemical Company
    Inventor: Abel Mendoza
  • Patent number: 4705901
    Abstract: 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: Grant
    Filed: August 26, 1986
    Date of Patent: November 10, 1987
    Assignee: The Dow Chemical Company
    Inventor: Abel Mendoza
  • Patent number: 4691057
    Abstract: 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: Grant
    Filed: September 19, 1984
    Date of Patent: September 1, 1987
    Assignee: Ethyl Corporation
    Inventor: Allan A. Eisenbraun
  • Patent number: 4690948
    Abstract: Ring opened halogenated Resorcyclic Acid Lactone (RAL) derivatives having the structure: ##STR1## are used to increase rumen fermentation efficiency.
    Type: Grant
    Filed: December 1, 1986
    Date of Patent: September 1, 1987
    Assignee: International Minerals & Chemical Corp.
    Inventor: Jing-Jong Lu
  • Patent number: 4684752
    Abstract: 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: Grant
    Filed: April 30, 1986
    Date of Patent: August 4, 1987
    Assignee: The Dow Chemical Company
    Inventor: Abel Mendoza
  • Patent number: 4670610
    Abstract: 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: Grant
    Filed: March 11, 1985
    Date of Patent: June 2, 1987
    Assignee: Sandoz, Inc.
    Inventor: Richard H. Sehring
  • Patent number: 4668831
    Abstract: 3-tert-Butyl-4-halophenols which are useful as intermediates for preparing compounds having medical or agricultural activities.
    Type: Grant
    Filed: March 14, 1986
    Date of Patent: May 26, 1987
    Assignee: Toyo Soda Manufacturing Co., Ltd.
    Inventors: Hideo Morinaka, Akira Nakanishi, Yuji Nonaka
  • Patent number: 4656311
    Abstract: 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: Grant
    Filed: July 21, 1986
    Date of Patent: April 7, 1987
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Michel Desbois
  • Patent number: 4621159
    Abstract: 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: Grant
    Filed: September 9, 1985
    Date of Patent: November 4, 1986
    Assignee: The Dow Chemical Company
    Inventor: Abel Mendoza
  • Patent number: 4620042
    Abstract: 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: Grant
    Filed: March 7, 1985
    Date of Patent: October 28, 1986
    Assignee: Central Glass Company, Limited
    Inventors: Toshikazu Kawai, Ysunobu Nishimura, Katumi Kanesaki
  • Patent number: 4593129
    Abstract: 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: Grant
    Filed: April 18, 1984
    Date of Patent: June 3, 1986
    Assignee: Ethyl Corporation
    Inventors: R. Woodrow Wilson, Jr., Dustin H. Thomas
  • Patent number: 4568777
    Abstract: 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: Grant
    Filed: November 9, 1984
    Date of Patent: February 4, 1986
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Herbert Baltes, Ernst I. Leupold
  • Patent number: 4547597
    Abstract: 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: Grant
    Filed: May 17, 1983
    Date of Patent: October 15, 1985
    Assignee: The Dow Chemical Company
    Inventors: David H. Louks, Leonard R. Thompson, Wayne C. Muench
  • Patent number: 4540834
    Abstract: 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: Grant
    Filed: March 2, 1984
    Date of Patent: September 10, 1985
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Georges Cordier