Preparing By Halogenation Patents (Class 568/779)
  • Patent number: 4723043
    Abstract: Substituted phenols are nitrated by contacting same with a 10 to 70% by weight concentrated aqueous solution of nitric acid. The subject nitration process is well adopted for the preparation, e.g., of 2,6-dichloro-4-nitrophenol, a valuable intermediate in the production of various agrochemicals/pharmaceuticals.
    Type: Grant
    Filed: July 7, 1986
    Date of Patent: February 2, 1988
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Serge Ratton
  • Patent number: 4701568
    Abstract: Tetrabromobisphenol-A is made in high purity by contacting a solution of bisphenol-A dissolved in a C.sub.1 -C.sub.4 alkanol with gaseous bromine.
    Type: Grant
    Filed: June 30, 1986
    Date of Patent: October 20, 1987
    Assignee: Ethyl Corporation
    Inventors: Bonnie G. McKinnie, Olan W. Mitchell
  • 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: 4683346
    Abstract: Hydroquinone is selectively nascently chlorinated to monochlorohydroquinone, by reacting same with an aqueous solution of hydrochloric acid and hydrogen peroxide, in the presence of an organic solvent for, and inert to, said hydroquinone.
    Type: Grant
    Filed: December 19, 1985
    Date of Patent: July 28, 1987
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Serge Ratton
  • 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: 4628124
    Abstract: Tetrabromobisphenol-A is made in high purity by adding a methanol-bromine solution to a methanol-bisphenol-A solution with vigorous agitation. Use of the bromine-methanol solution reduces the amount of by-products compared to use of liquid bromine feed.
    Type: Grant
    Filed: September 23, 1985
    Date of Patent: December 9, 1986
    Assignee: Ethyl Corporation
    Inventors: Bonnie G. McKinnie, Olan W. Mitchell
  • 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: 4612401
    Abstract: 4-Hydroxy-2,4,6-trimethyl-2,5-cyclohexadienone is made by chlorinating 2,4,6-trimethylphenol with chlorine in an organic solvent in the absence of base while the hydrogen chloride formed is removed as it is formed by physical means and hydrolyzing the reaction mixture with water optionally in the presence of an inorganic base.
    Type: Grant
    Filed: March 19, 1985
    Date of Patent: September 16, 1986
    Assignee: Rhone-Poulenc Sante
    Inventors: Michel Costantini, Francoise Igersheim, Leon Krumenacker
  • Patent number: 4575571
    Abstract: A process for the stimulaneous halogenation and fluorination of aromatic derivatives substituted by at least one group containing a halogenoalkyl unit. The aromatic derivative is reacted with the halogen in liquid hydrofluoric acid. The products obtained are useful as intermediates for the synthesis of compounds having a plant-protecting or pharmaceutical activity.
    Type: Grant
    Filed: June 22, 1984
    Date of Patent: March 11, 1986
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventors: Michel Desbois, Camille Disdier
  • Patent number: 4564714
    Abstract: A novel process for the preparation of 2,4,5-trichlorophenol which comprises selectively chlorinating 2,5-dichlorophenol under acidic conditions.
    Type: Grant
    Filed: October 30, 1984
    Date of Patent: January 14, 1986
    Assignee: Givaudan Corporation
    Inventors: Joseph A. Virgilio, Joachim E. Freudewald
  • 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: 4518808
    Abstract: Disclosed is a process for the preparation of certain dichloro-hydroxy and alkoxy aromatic compounds by reacting the corresponding unchlorinated compound with sulfuryl chloride in the presence of acetic acid, propionic acid or lower alkyl esters thereof.
    Type: Grant
    Filed: September 29, 1983
    Date of Patent: May 21, 1985
    Assignee: Eastman Kodak Company
    Inventors: Richard H. S. Wang, Garry L. Myers
  • Patent number: 4517388
    Abstract: This invention is a process for the preparation of para-bromo-phenole derivatives of the formula I ##STR1## wherein R.sub.1, R.sub.2 R.sub.3, R.sub.4 and R.sub.5 each independently represents hydrogen or lower alkyl radical of 1 to 6 carbon atoms, characterized in that a phenol derivative of formula II ##STR2## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are as defined above, is reacted in the presence of a solvent with a compound of the formula ##STR3## or with bromine and a compound of the formula IV ##STR4## wherein R.sub.6 and R.sub.7 in the formulae III and IV being each independently a lower alkyl radical of 1 to 6 carbon atoms, an aryl radical or they form together with the S-atom to which they are attached, a 4 to 6 member ring.
    Type: Grant
    Filed: October 25, 1983
    Date of Patent: May 14, 1985
    Inventor: Samuel Braverman
  • Patent number: 4503268
    Abstract: Disclosed is a process for the preparation of monochlorohydroquinone by treating hydroquinone in hydrochloric acid with chlorine at 100.degree. to 105.degree. C.
    Type: Grant
    Filed: November 14, 1983
    Date of Patent: March 5, 1985
    Assignee: Eastman Kodak Company
    Inventors: James G. Pacifici, Allen J. Blankenship
  • Patent number: 4489210
    Abstract: The invention relates to a process for the halogenation of organic compounds in the liquid phase using gaseous halogenating agents, the gaseous halogenating agents being metered into the reaction vessel at such an entry velocity that a gas jet is formed in the reaction mixture at the point of entry of the halogenating agent and the formation of individual gas bubbles at the point of entry is prevented.
    Type: Grant
    Filed: July 30, 1982
    Date of Patent: December 18, 1984
    Assignee: Bayer Aktiengesellschaft
    Inventors: Helmut Judat, Ulrich Schnegg, Karlfried Wedemeyer
  • Patent number: 4480140
    Abstract: Phenols alkylated in the ortho and/or para positions are produced in good yields and in the absence of isomers from phenolic compounds having at least two alkylateable ortho-ortho or ortho-para positions open. The phenolic compound is first partially chlorinated or brominated and the desired halogenated phenol having at least one open position ortho or para is reacted with an aldehyde having one to four carbon atoms and a secondary non-aromatic amine. The reaction is conducted in the liquid phase with a stoichiometric amount of the phenolic compound and stoichiometric or excess of stoichiometric amounts of the aldehyde and the amine. The reaction is performed at a temperature of from about 0.degree. C. to about 100.degree. C. to produce an aminoalkylated halogenated phenolic compound. This aminoalkylated halogenated phenolic compound is contacted with hydrogen in the presence of a metal catalyst at a temperature of about 100.degree. C. to about 175.degree. C.
    Type: Grant
    Filed: March 16, 1983
    Date of Patent: October 30, 1984
    Assignee: Koppers Company, Inc.
    Inventor: Gerd Leston
  • Patent number: 4451675
    Abstract: The invention is a process for preparing alkylidenebis(dibromophenol) comprising(a) dissolving alkylidenediphenol in between about 17 and 25 moles of methanol for each mole of alkylidenediphenol wherein the methanol has less than 5 percent by weight of water therein;(b) adding to the solution between about 4.0 and 4.1 moles of bromine per mole of alkylidenediphenol at an elevated temperature;(c) adding water to precipitate the alkylidenebis(dibromophenol) remaining in solution after the addition of the bromine in step (b) is completed; and(d) separating the alkylidenebis(dibromophenol) from the methanol solution.
    Type: Grant
    Filed: July 16, 1982
    Date of Patent: May 29, 1984
    Assignee: The Dow Chemical Company
    Inventor: Charles T. Bounds
  • Patent number: 4439596
    Abstract: Chlorination of hydroquinone by reacting sulfuryl chloride with a slurry or solution of hydroquinone in glacial acetic acid can yield a mixture containing a major proportion of monochlorohydroquinone.
    Type: Grant
    Filed: March 21, 1983
    Date of Patent: March 27, 1984
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Robert S. Irwin
  • Patent number: 4439595
    Abstract: Chlorination of hydroquinone by reacting sulfuryl chloride with hydroquinone in an alkyl ester solvent having 2-8 carbon atoms yields a mixture containing a major proportion of monochlorohydroquinone.
    Type: Grant
    Filed: March 21, 1983
    Date of Patent: March 27, 1984
    Assignee: E. I. Du Pont de Nemours & Company
    Inventor: Chih S. Chiang
  • Patent number: 4431847
    Abstract: A process for forming a substantially insoluble solid polymer from halogeneated phenolic compounds dissolved in a liquid medium using an oxidizing agent. NaOCl and NaOBr are used as oxidizing agents to initiate the polymerization reaction among the halogenated phenolic compounds. The polymer precipitates from the system to form a claylike solid. The solid is environmentally safe and may be disposed of in a sanitary landfill.
    Type: Grant
    Filed: July 29, 1982
    Date of Patent: February 14, 1984
    Assignee: Ethyl Corporation
    Inventors: Joseph A. Bossier, Julio J. Vega
  • Patent number: 4400556
    Abstract: The invention covers the use of novel co-catalysts as inhibitors that reduce the formation of undesirable chlorinated dioxins during the preparation of pentachlorophenol and tetrachlorophenol from phenol or lower chlorinated phenols.
    Type: Grant
    Filed: June 22, 1981
    Date of Patent: August 23, 1983
    Assignee: Reichhold Chemicals, Incorporated
    Inventors: William H. Wetzel, Hsi-Lung Pan, Robert J. Goodwin, John E. Wilkinson
  • Patent number: 4374262
    Abstract: A process for preparing hydroxy aromatic carboxylic acids, or the ester derivatives thereof, comprises carbonylating a hydroxy aromatic halide in the presence of a reactive alcohol solvent and a catalytic amount of a Group VIII metal catalyst. The process has particular applicability to the preparation of 6-hydroxy-2-naphthoic acid from 6-bromo-2-naphthol, which can be easily prepared from .beta.-naphthol, a readily available and inexpensive starting material.
    Type: Grant
    Filed: October 6, 1980
    Date of Patent: February 15, 1983
    Assignee: Celanese Corporation
    Inventors: James L. McGinnis, Anthony B. Conciatori
  • Patent number: 4310702
    Abstract: Sulfuryl chloride is reacted in the liquid phase with an organic reactant which is a ketone or aromatic alcohol unsubstituted on both ortho carbons in the presence of a moderator selected from the group consisting of aliphatic alcohols of 1-3 carbons and aliphatic ethers of 2-6 carbons, with sufficient moderator being present to selectively produce a product substantially free of compounds with more than one chlorine atom per carbonyl or aromatic hydroxy. The products, such as monochloroacetone, monochlorocyclohexanone, monochlorophenol and 2,2-bis(3-chloro-4-hydroxyphenyl)propane, are useful as chemical intermediates and as monomers for flame retardant polymers.
    Type: Grant
    Filed: July 28, 1980
    Date of Patent: January 12, 1982
    Assignee: Allied Corporation
    Inventors: Divakaran Masilamani, Milorad M. Rogic
  • Patent number: 4294996
    Abstract: The invention covers the use of novel co-catalysts as inhibitors that reduce the formation of undesirable chlorinated dioxins during the preparation of pentachlorophenol and tetrachlorophenol from phenol or lower chlorinated phenols.
    Type: Grant
    Filed: June 9, 1980
    Date of Patent: October 13, 1981
    Assignee: Reichhold Chemicals, Incorporated
    Inventors: William H. Wetzel, Hsi-Lung Pan, Robert J. Goodwin, John E. Wilkinson
  • Patent number: 4284830
    Abstract: Monohalogenated hydrocarbyl substituted phenols can be produced by reacting hydrocarbyl substituted phenols with a halogen carrying out the reaction in a diluent such as benzene, alkyl substituted benzenes, and halosubstituted hydrocarbons of 1-3 carbon atoms.
    Type: Grant
    Filed: February 1, 1980
    Date of Patent: August 18, 1981
    Assignee: Phillips Petroleum Co.
    Inventors: Ronald D. Knudsen, Darryl R. Fahey
  • Patent number: 4277629
    Abstract: The invention relates to the batch or continuous para-chlorination of para-unsubstituted phenols, especially ortho-cresol, using sulphuryl chloride in the presence of one or more rate and selectivity catalysts, and to the avoidance of the reaction mixture going solid. It concerns specifically the carrying out of the chlorination process in stages, each stage involving only part of the sulphuryl chloride needed for the chlorination and being carried to completion before there is added to the mixture the sulphuryl chloride for the next stage. In addition, the invention concerns specifically the selection and control of reaction temperature, throughout the reaction, in order to minimize by-product formation and the likelihood of freeze-up.
    Type: Grant
    Filed: June 7, 1977
    Date of Patent: July 7, 1981
    Assignee: Lankro Chemicals Limited
    Inventors: John S. Binns, Malcolm J. Braithwaite, George Dignum
  • Patent number: 4245127
    Abstract: Chlorination of xylenols with a chlorinating agent such as sulfuryl chloride in the presence of a metal chloride catalyst is conducted in further presence of 0.001 to 1% by weight of a sulfur compound, based on the xylenols, whereby industrially useful xylenols are obtained safely with a high selectivity and high yield.
    Type: Grant
    Filed: October 27, 1976
    Date of Patent: January 13, 1981
    Assignee: Seitetsu Kagaku Co., Ltd.
    Inventors: Teiziro Matsumoto, Moriyasu Matsuda, Hiroshi Mizokami, Tsuneo Kibamoto, Katsuma Hatta
  • Patent number: 4223166
    Abstract: A process for the production of 4-bromo-2-chloro-phenols of the formula ##STR1## wherein X represents hydrogen or chlorine is disclosed which process comprises the bromination of a 2-chlorphenol of the formula ##STR2## wherein X has the meaning given above in the presence of a compound of the formula ##STR3## in which R.sub.1 represents an alkyl group having 1 to 8 carbon atoms, or the phenyl or benzyl group,R.sub.2 and R.sub.3 independently of one another represent an alkyl group having 1 to 8 carbon atoms,R.sub.4 represents hydrogen, or an alkyl group having 1 to 8 carbon atoms, andX represents chlorine, bromine, or iodine or the hydrogen sulfate anion.The new process substantially avoids the undesired formation of the 2,6-isomers and the 4-bromo-2-chlorophenols are obtained in excellent purity.
    Type: Grant
    Filed: February 23, 1979
    Date of Patent: September 16, 1980
    Assignees: Societe Anonyme pour l'Industrie Chimique, Ciba-Geigy Corporation
    Inventors: Roland Jaeger, Kurt Huber
  • Patent number: 4221893
    Abstract: According to the present invention there are provided novel flame retardant brominated bisphenol epoxy compositions comprising the reaction product of the residue of the production of tetrabromo-bisphenol A (TBBA) with epichlorohydrin, and a process for the production of such compositions which comprises dissolving such residue in an excess of aqueous alkali, reacting the residue with epichlorohydrin at elevated temperature, neutralizing excess of alkali remaining after the reaction and recovering the brominated epoxy compositions.The compositions thus obtained are useful as flame retardants. There may be optionally incorporated in same compounds such as antimony trioxide.
    Type: Grant
    Filed: December 20, 1978
    Date of Patent: September 9, 1980
    Assignee: Makhteshim Chemical Works Limited
    Inventors: Meir Behar, Ori Peshes, Aharon Liebersohn
  • Patent number: 4210766
    Abstract: A process for the production of 2-halo-4-bromophenols of the formula ##STR1## in which X represents chlorine or bromine, is disclosed, which process comprises reacting a brominating agent with a 2-halophenol in the presence of a mixed catalyst consisting of a halide of zinc, iron, aluminium or cobalt, and a diphenyl sulfide of the formula ##STR2## in which R represents methyl or halogen, and n represents 0 to 3. The new process substantially avoids the formation of undesired 2,6-isomers and the 2-halo-4-bromophenols of the above formula are obtained in excellent yield and purity.
    Type: Grant
    Filed: August 22, 1978
    Date of Patent: July 1, 1980
    Assignee: Ciba-Geigy Corporation
    Inventors: Tibor Somlo, Anton Hungerbuhler
  • Patent number: 4160114
    Abstract: In a process for producing relatively pure commercially acceptable pentachlorophenol, comprising reacting, at a temperature ranging from about 10.degree. to about 190.degree. C., (A) a phenol consisting essentially of raw or commercial phenol which may contain, as impurities from other processes, some lower chlorophenols such as mono and dichlorophenols and mixtures thereof, and (B) chlorine, in the presence of (C) an acid catalyst from about 0.005 moles to about 0.
    Type: Grant
    Filed: July 20, 1977
    Date of Patent: July 3, 1979
    Assignee: Reichhold Chemicals, Inc.
    Inventors: Frederic J. Shelton, William H. Wetzel, John E. Wilkinson, Robert J. Goodwin
  • Patent number: 4098828
    Abstract: Chloromethylisopropylphenois, namely 4-chloro-3-methyl-2-isopropyl phenol, 4-chloro-3-methyl-5-isopropyl phenol and their 6,6'-methylene and 2,2'-methylene bis derivatives, effective as a bactericide and fungicide, especially against staphylococcus, pneumococcus and tricoccus. They are effective in doses as low as 5 ppm, are stable, substantially odor-free and can be readily prepared by conventional chemical reactions to obtain a substantially nontoxic white product.
    Type: Grant
    Filed: May 7, 1973
    Date of Patent: July 4, 1978
    Assignee: Chrysa
    Inventors: Robert Marc Perrin, Gisele Aureille, Marie-Francoise Vincent-Falquet, Edmond Collange