Preparing By Halogenation Patents (Class 568/779)
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Patent number: 4723043Abstract: 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: GrantFiled: July 7, 1986Date of Patent: February 2, 1988Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Serge Ratton
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Patent number: 4701568Abstract: 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: GrantFiled: June 30, 1986Date of Patent: October 20, 1987Assignee: Ethyl CorporationInventors: Bonnie G. McKinnie, Olan W. Mitchell
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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: 4683346Abstract: 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: GrantFiled: December 19, 1985Date of Patent: July 28, 1987Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Serge Ratton
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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: 4628124Abstract: 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: GrantFiled: September 23, 1985Date of Patent: December 9, 1986Assignee: Ethyl CorporationInventors: Bonnie G. McKinnie, Olan W. Mitchell
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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: 4612401Abstract: 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: GrantFiled: March 19, 1985Date of Patent: September 16, 1986Assignee: Rhone-Poulenc SanteInventors: Michel Costantini, Francoise Igersheim, Leon Krumenacker
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Patent number: 4575571Abstract: 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: GrantFiled: June 22, 1984Date of Patent: March 11, 1986Assignee: Rhone-Poulenc Specialites ChimiquesInventors: Michel Desbois, Camille Disdier
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Patent number: 4564714Abstract: A novel process for the preparation of 2,4,5-trichlorophenol which comprises selectively chlorinating 2,5-dichlorophenol under acidic conditions.Type: GrantFiled: October 30, 1984Date of Patent: January 14, 1986Assignee: Givaudan CorporationInventors: Joseph A. Virgilio, Joachim E. Freudewald
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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: 4518808Abstract: 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: GrantFiled: September 29, 1983Date of Patent: May 21, 1985Assignee: Eastman Kodak CompanyInventors: Richard H. S. Wang, Garry L. Myers
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Patent number: 4517388Abstract: 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: GrantFiled: October 25, 1983Date of Patent: May 14, 1985Inventor: Samuel Braverman
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Patent number: 4503268Abstract: 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: GrantFiled: November 14, 1983Date of Patent: March 5, 1985Assignee: Eastman Kodak CompanyInventors: James G. Pacifici, Allen J. Blankenship
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Patent number: 4489210Abstract: 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: GrantFiled: July 30, 1982Date of Patent: December 18, 1984Assignee: Bayer AktiengesellschaftInventors: Helmut Judat, Ulrich Schnegg, Karlfried Wedemeyer
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Patent number: 4480140Abstract: 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: GrantFiled: March 16, 1983Date of Patent: October 30, 1984Assignee: Koppers Company, Inc.Inventor: Gerd Leston
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Patent number: 4451675Abstract: 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: GrantFiled: July 16, 1982Date of Patent: May 29, 1984Assignee: The Dow Chemical CompanyInventor: Charles T. Bounds
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Patent number: 4439596Abstract: 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: GrantFiled: March 21, 1983Date of Patent: March 27, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventor: Robert S. Irwin
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Patent number: 4439595Abstract: 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: GrantFiled: March 21, 1983Date of Patent: March 27, 1984Assignee: E. I. Du Pont de Nemours & CompanyInventor: Chih S. Chiang
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Patent number: 4431847Abstract: 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: GrantFiled: July 29, 1982Date of Patent: February 14, 1984Assignee: Ethyl CorporationInventors: Joseph A. Bossier, Julio J. Vega
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Patent number: 4400556Abstract: 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: GrantFiled: June 22, 1981Date of Patent: August 23, 1983Assignee: Reichhold Chemicals, IncorporatedInventors: William H. Wetzel, Hsi-Lung Pan, Robert J. Goodwin, John E. Wilkinson
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Patent number: 4374262Abstract: 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: GrantFiled: October 6, 1980Date of Patent: February 15, 1983Assignee: Celanese CorporationInventors: James L. McGinnis, Anthony B. Conciatori
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Patent number: 4310702Abstract: 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: GrantFiled: July 28, 1980Date of Patent: January 12, 1982Assignee: Allied CorporationInventors: Divakaran Masilamani, Milorad M. Rogic
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Patent number: 4294996Abstract: 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: GrantFiled: June 9, 1980Date of Patent: October 13, 1981Assignee: Reichhold Chemicals, IncorporatedInventors: William H. Wetzel, Hsi-Lung Pan, Robert J. Goodwin, John E. Wilkinson
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Patent number: 4284830Abstract: 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: GrantFiled: February 1, 1980Date of Patent: August 18, 1981Assignee: Phillips Petroleum Co.Inventors: Ronald D. Knudsen, Darryl R. Fahey
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Patent number: 4277629Abstract: 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: GrantFiled: June 7, 1977Date of Patent: July 7, 1981Assignee: Lankro Chemicals LimitedInventors: John S. Binns, Malcolm J. Braithwaite, George Dignum
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Patent number: 4245127Abstract: 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: GrantFiled: October 27, 1976Date of Patent: January 13, 1981Assignee: Seitetsu Kagaku Co., Ltd.Inventors: Teiziro Matsumoto, Moriyasu Matsuda, Hiroshi Mizokami, Tsuneo Kibamoto, Katsuma Hatta
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Patent number: 4223166Abstract: 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: GrantFiled: February 23, 1979Date of Patent: September 16, 1980Assignees: Societe Anonyme pour l'Industrie Chimique, Ciba-Geigy CorporationInventors: Roland Jaeger, Kurt Huber
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Patent number: 4221893Abstract: 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: GrantFiled: December 20, 1978Date of Patent: September 9, 1980Assignee: Makhteshim Chemical Works LimitedInventors: Meir Behar, Ori Peshes, Aharon Liebersohn
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Patent number: 4210766Abstract: 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: GrantFiled: August 22, 1978Date of Patent: July 1, 1980Assignee: Ciba-Geigy CorporationInventors: Tibor Somlo, Anton Hungerbuhler
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Patent number: 4160114Abstract: 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: GrantFiled: July 20, 1977Date of Patent: July 3, 1979Assignee: Reichhold Chemicals, Inc.Inventors: Frederic J. Shelton, William H. Wetzel, John E. Wilkinson, Robert J. Goodwin
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Patent number: 4098828Abstract: 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: GrantFiled: May 7, 1973Date of Patent: July 4, 1978Assignee: ChrysaInventors: Robert Marc Perrin, Gisele Aureille, Marie-Francoise Vincent-Falquet, Edmond Collange