Halogen Containing Patents (Class 568/774)
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Patent number: 4526999Abstract: Compounds of the Formula I: ##STR1## and pharmaceutically acceptable salts thereof are inhibitors of leukotriene biosynthesis. These compounds inhibit lipoxygenase, thus preventing the metabolism of arachidonic acid to the leukotrienes. These compounds are thus useful in the treatment of asthma, allergic disorders, inflammation, skin diseases and certain cardiovascular disorders.Type: GrantFiled: April 25, 1983Date of Patent: July 2, 1985Assignee: Merck & Co., Inc.Inventors: Philippe L. Durette, Timothy F. Gallagher
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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: 4489212Abstract: Arenes are reacted with allyl chloride to produce allylarenes and 2-chloropropyl- or propenylarenes using a catalyst comprising a metal oxide substrate having tantalum (V) halide/oxide bound to the surface of the substrate.Type: GrantFiled: October 25, 1983Date of Patent: December 18, 1984Assignee: Shell Oil CompanyInventor: Thomas H. Johnson
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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: 4479019Abstract: A process is disclosed for separating nitrated phenolic compounds from other nitrated and unnitrated phenolics by treating a mixture of the phenolics with a metal halide salt. The metal halide salt preferentially forms a complex with one of the phenolics over other related phenolics in the mixture. The preferentially-formed complex of one of the phenolics may then be isolated from the mixture and the complex decomposed to provide a product substantially enriched in, or substantially entirely composed of, one phenolic. The process is particularly suitable for resolving a mixture comprising phenol or cresol from their ortho-nitrated derivatives, or a mixture of two isomeric nitrated phenols or cresols or a mixture of mono-and dinitrated phenols or cresols.Type: GrantFiled: February 21, 1984Date of Patent: October 23, 1984Assignee: Koppers Company, Inc.Inventor: Gerd Leston
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Patent number: 4473713Abstract: At least one of the other functions comprising an aryl-aliphatic ether, e.g., veratrol, is catalytically hydrolyzed with water, e.g., to guaiacol, in the presence of a catalytically effective amount of a salt of a carboxylic acid.Type: GrantFiled: September 27, 1982Date of Patent: September 25, 1984Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Serge Ratton
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Patent number: 4469900Abstract: A process is disclosed for separating closely-boiling chlorinated phenolic compounds from other chlorinated and unchlorinated phenolics by treating a mixture of the phenolics with a metal halide salt. The metal halide salt preferentially forms a complex with one of the phenolics over other related closely-boiling phenolics in the mixture. The preferentially-formed complex of one of the phenolics may then be isolated from the mixture and the complex decomposed to provide a product substantially enriched in, or substantially entirely composed of, one phenolic. The process is particularly suitable for resolving a mixture comprising phenol or cresol from their closely-boiling ortho-chlorinated derivatives, or a mixture of two isomeric chlorinated phenols or cresols or a mixture of closely-boiling mono- and dichlorinated phenols or cresols.Type: GrantFiled: January 4, 1984Date of Patent: September 4, 1984Assignee: Koppers Company, Inc.Inventor: Gerd Leston
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Patent number: 4447660Abstract: Process for the isomerization of ortho- and para-bromophenols or the ethers thereof into corresponding meta-brominated derivatives by isomerizing ortho- and para-bromophenols in the corresponding ethers in the presence of a liquid superacid at a temperature in the region of ambient temperature.Type: GrantFiled: September 30, 1982Date of Patent: May 8, 1984Assignee: PCUK Produits Chimiques Ugine KuhlmannInventors: Marie-Paule Jouannetaud, Jean-Pierre Gesson, Jean-Claude Jacquessy
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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: 4429168Abstract: A process is disclosed for separating closely-boiling chlorinated phenolic compounds from other chlorinated and unchlorinated phenolics by treating a mixture of the phenolics with a metal halide salt. The metal halide salt preferentially forms a complex with one of the phenolics over other related closely-boiling phenolics in the mixture. The preferentially-formed complex of one of the phenolics may then be isolated from the mixture and the complex decomposed to provide a product substantially enriched in, or substantially entirely composed of, one phenolic. The process is particularly suitable for resolving a mixture comprising phenol or cresol from their closely-boiling ortho-chlorinated derivatives, or a mixture of two isomeric chlorinated phenols or cresols or a mixture of closely-boiling mono- and dichlorinated phenols or cresols.Type: GrantFiled: April 26, 1982Date of Patent: January 31, 1984Assignee: Koppers Company, Inc.Inventor: Gerd Leston
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Patent number: 4419529Abstract: A 2-alkylphenol is prepared by reduction of a 2-acylphenol in the presence of a metallic catalyst. The reaction is carried out at a temperature of 80.degree. to 200.degree. C. and under a pressure of 10 to 100 bars, and a base metal, in particular copper, is used as a catalyst. It is particularly advantageous to use the catalyst in combination with a support. The hydrogenation of the acylphenol is advantageously carried out in the presence of an inert solvent. The process can be carried out continuously or discontinuously. The alkylphenols obtained are suitable for use in the synthesis of active substances having biocidal properties.Type: GrantFiled: March 3, 1982Date of Patent: December 6, 1983Assignee: Riedel-de Haen AktiengesellschaftInventor: Arthur Steinmetz
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Patent number: 4410738Abstract: Meta-chlorophenols useful as intermediates in various organic syntheses are prepared by selectively catalytically hydrodechlorinating a polychlorophenol in liquid phase in an acid solvent medium which is at least partially aqueous, in the presence of a Group VIII noble metal catalyst and at least one Group 1b to 5a heavy metal, said polychlorophenol bearing chlorine substituents in both the meta- and ortho- and/or para-positions.Type: GrantFiled: December 21, 1981Date of Patent: October 18, 1983Assignee: Rhone-Poulenc IndustriesInventor: Georges Cordier
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Patent number: 4410737Abstract: Meta-chlorophenols useful as intermediates in various organic syntheses are prepared by selectively catalytically hydrodechlorinating a polychlorophenol in liquid phase in an acid solvent medium which is at least partially aqueous and which comprises halide ions, in the presence of a Group VIII noble metal catalyst, said polychlorophenol bearing chlorine substituents in both the meta- and ortho- and/or para-positions.Type: GrantFiled: December 21, 1981Date of Patent: October 18, 1983Assignee: Rhone-Poulenc IndustriesInventor: Georges Cordier
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Patent number: 4410739Abstract: Meta-chlorophenols useful as intermediates in various organic syntheses are prepared by selectively catalytically hydrodechlorinating a polychlorophenol in liquid organic phase and in the presence of a nobel metal catalyst and a Lewis acid, said polychlorophenol bearing chlorine substituents in both the meta- and ortho- and/or para-positions.Type: GrantFiled: December 21, 1981Date of Patent: October 18, 1983Assignee: Rhone-Poulenc IndustriesInventor: Georges Cordier
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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: 4376220Abstract: 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: March 8, 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: 4366329Abstract: Disclosed is a novel process for the separation of meta and para isomers of the sodium salt of bromophenol. Derivatives of the sodium salt of metabromophenol are useful chemical intermediates.Type: GrantFiled: June 22, 1981Date of Patent: December 28, 1982Assignee: Eastman Kodak CompanyInventor: Peter W. Raynolds
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Patent number: 4351969Abstract: Chlorophenols are prepared by thermally dehydrochlorinating a corresponding chlorocyclohexanone in the presence of a catalyst having the formula: ##STR1## wherein A is phosphorus or arsenic, R.sub.1 and R.sub.2, which are identical or different, are each hydrogen, an alkyl radical having from 1 to 12 carbon atoms, a phenyl radical or a radical --NR.sub.4 R.sub.5, in which R.sub.4 and R.sub.5, which are identical or different, are each H or an alkyl radical having from about 1 to 5 carbon atoms, R.sub.3 is an alkyl radical having from 1 to 12 carbon atoms, a phenyl radical or a radical --NR.sub.4 R.sub.5, in which R.sub.4 and R.sub.5 are as defined above, and n is equal to 0 or 1.Type: GrantFiled: March 17, 1981Date of Patent: September 28, 1982Assignee: Rhone-Poulenc IndustriesInventor: Jacques Bourdon
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Patent number: 4346248Abstract: A process for the preparation of 2,4,5-trichlorophenol and 2,4,5-trichlorophenoxyacetic acid free of 2,3,7,8-tetrachloro-dibenzo-p-dioxin contamination by the steps of nitrating 1,2,4-trichlorobenzene, reducing the resulting 1,2,4-trichloro-5-nitrobenzene, diazotizing the resulting 2,4,5-trichloroaniline, hydrolyzing the resulting 2,4,5-trichlorobenzenediazonium salt and recovering 2,4,5-trichlorophenol. The 2,4,5-trichlorophenol is reacted with monochloroacetic acid to give 2,4,5-trichlorophenoxyacetic acid. Both the 2,4,5-trichlorophenol and the 2,4,5-trichlorophenoxyacetic acid produced by the process are analytically free of 2,3,7,8-tetrachloro-dibenzo-p-dioxin in analytical tests sensitive to 1 part per billion.Type: GrantFiled: May 22, 1981Date of Patent: August 24, 1982Assignee: Vertac Chemical CorporationInventors: Dennis L. Deavenport, Kenneth J. Howard, Albert E. Sidwell
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Patent number: 4337368Abstract: A reagent, comprising the product of the reaction of an alkali metal with a polyglycol or a polyglycol monoalkyl ether and oxygen, effects complete decomposition of halogenated organic compounds, such as polychlorinated biphenyls (PCBs), when mixed therewith in the presence of oxygen.Type: GrantFiled: June 11, 1980Date of Patent: June 29, 1982Assignee: The Franklin InstituteInventors: Louis L. Pytlewski, Kenneth Krevitz, Arthur B. Smith
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Patent number: 4328361Abstract: A process is disclosed for converting p-isopropenylphenol and derivatives thereof and, more particularly, oligomers of p-isopropenylphenol and derivatives thereof, to hydroquinone via monomeric intermediates [e.g. p-(2-haloisopropyl)phenol in the case of p-isopropenylphenol and oligomers thereof]. The process involves reacting the starting materials with a hydrogen halide (e.g. gaseous hydrogen chloride) in the presence of an organic solvent and subjecting the product so obtained to oxidation with hydrogen peroxide or an organic hydroperoxide.Type: GrantFiled: January 16, 1981Date of Patent: May 4, 1982Assignee: The Upjohn CompanyInventor: Shenghong A. Dai
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Patent number: 4326882Abstract: This invention provides as new compositions of matter 2,4,5-trichlorophenoxy acetic acid (2,4,5-T) and (2-2,4,5-trichlorophenoxy) propionic acid (Silvex) including the hydrolyzable salts, aliphatic esters and amides of these acids, which compositions are free of chlorinated dibenzo-p-dioxins.Type: GrantFiled: April 26, 1979Date of Patent: April 27, 1982Assignee: PPG Industries, Inc.Inventors: Sidney B. Richter, William S. Grove
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Patent number: 4308407Abstract: Phenols with a methyl group substituted on the phenolic benzene ring, such as 2,6-di-tert-butyl-p-cresol, can be produced by reacting a halomethyl group substituted on a phenol such as 2,6-di-tert-butyl-4-chloromethylphenol, with hydrogen in the presence of a hydrogenation catalyst, such as palladium.Type: GrantFiled: August 18, 1980Date of Patent: December 29, 1981Assignee: Ethyl CorporationInventors: Bernard R. Meltsner, Joseph D. Odenweller
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Patent number: 4306098Abstract: A method of producing 2,4,5-trichlorophenol with low levels of the impurity 2,3,7,8-tetrachlorodibenzo-.rho.-dioxin.Type: GrantFiled: July 7, 1980Date of Patent: December 15, 1981Assignee: Ivon Watkins-Dow LimitedInventor: Edgar G. Brooker
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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: 4262152Abstract: A process for preparing trifluoromethylphenyl nitro phenylethers which comprises treating a trifluoromethylhalobenzene with a base in a cosolvent system to afford a trifluoromethyl phenolate which may be isolated as its free phenol or reacted with an appropriately substituted halobenzene to afford a diphenylether herbicide or a precursor thereto.Type: GrantFiled: May 2, 1979Date of Patent: April 14, 1981Assignee: Rohm and Haas CompanyInventor: Wayne O. Johnson
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Patent number: 4228308Abstract: 1,1,1-trichloro-2,2-bis(4-hydroxyphenyl)ethane can be dehydrohalogenated to 1,1-dichloro-2,2-bis(4-hydroxyphenyl) ethylene by treating the former with a dehydrochlorinating agent comprising liquid methyl amine and an effective amount of an additive to accelerate the dehydrochlorinating effect of the liquid methyl amine selected from the class consisting of a certain class of inorganic and organic salts.Type: GrantFiled: May 9, 1979Date of Patent: October 14, 1980Assignee: General Electric CompanyInventor: Michael R. Mac Laury
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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: 4205176Abstract: Oxazolines having at least one 3,5-dialkyl-4-hydroxypheny l alkanoic acid ester substituent are provided. Such oxazolines are found to be useful an antioxidants in organic substances normally susceptible to oxidative deterioration.Type: GrantFiled: October 18, 1978Date of Patent: May 27, 1980Assignee: Cincinnati Milacron Chemicals Inc.Inventors: Mary J. Zestermann, John F. Hussar
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Patent number: 4203925Abstract: This invention concerns processes for preparing compounds having the structure ##STR1## wherein each of R.sub.1, R.sub.2, R.sub.3, R.sub.4, R.sub.5 and R.sub.6 is the same or different and represents hydrogen or a lower alkyl group and wherein each dashed line represents a carbon-carbon single bond or a carbon-carbon double bond. Those compounds in which all three dashed lines represent carbon-carbon double bonds are prepared by reacting phenols and 2-alkylidene-1,4-disubstituted butanes. Selective reduction of these compounds yields those in which at least one dashed line represents a carbon-carbon single bond. Most of the compounds so prepared are new compounds. All are useful as fragrance materials either directly and/or in compositions and/or have useful fixative properties in fragrance compositions.Type: GrantFiled: June 9, 1978Date of Patent: May 20, 1980Assignee: Fritzsche Dodge & Olcott Inc.Inventors: Derek H. R. Barton, Brian J. Willis
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Patent number: 4154968Abstract: 4-Chloro-3-methyl-2-isopropyl and 4-chloro-3-methyl-5-isopropyl phenols are effective as bactericides and fungicides, especially against staphylococcus, pneumococcus and tricoccus microorganisms in doses as low as 5 parts per million.Type: GrantFiled: February 17, 1978Date of Patent: May 15, 1979Assignee: ChrysaInventors: Robert M. Perrin, Gisele Aureille, Marie-Francoise Vincent-Falquet, Edmond Collange
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Patent number: 4147726Abstract: An organic hydroperoxide is hydrolyzed by acid-catalysis in a reaction medium comprising essentially a mixture of a polar solvent, e.g. a low boiling, low molecular weight alcohol and/or sulfolane and phenol. Specifically cyclohexanone and phenol are obtained from cyclohexylbenzene hydroperoxide.Type: GrantFiled: November 8, 1976Date of Patent: April 3, 1979Assignee: Phillips Petroleum CompanyInventor: Yulin Wu
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Patent number: 4145362Abstract: A process for arylating an olefinic compound by addition of an aryl group to a double bond of said olefinic compound consisting in diazotizing an arylamine in an aqueous acidic solution comprising a lower alkanoic acid to form a solution of an aryldiazonium salt and reacting said aryldiazonium salt solution with an olefinic compound in an organic solvent in the presence of a catalytically effective amount of a copper halide.The amount of alkanoic acid is about 15 to 37% by volume of the total solvents used. The alkanoic acid is preferably acetic acid and the copper halide cuprous chloride.Type: GrantFiled: May 10, 1977Date of Patent: March 20, 1979Assignee: S.A. P R B en Neerlandais PRB N.V.Inventors: Joseph R. Brepoels, Jean-Marie Vaneghem
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Patent number: 4138411Abstract: Aromatic alkenyl compounds, for example, eugenol and safrole, are isomerized, for example to isoeugenol and isosafrole, by contact with a ruthenium or osmium catalyst.Type: GrantFiled: April 14, 1976Date of Patent: February 6, 1979Assignee: Rhone-Poulenc S. A.Inventor: Pierre Gandilhon
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Patent number: 4120902Abstract: A process for the separation and purification of reaction product from the oxidation of hydrocarbyl aromatic compounds to hydrocarbyl aromatic hydroperoxides is provided comprising (1) extracting the oxidation effluent with an aqueous alcoholic base, (2) contacting the aqueous phase thus produced with a paraffin hydrocarbon solvent to remove residual unoxidized hydrocarbyl aromatic, (3) extracting the aqueous hydrocarbyl aromatic hydroperoxide phase remaining with an aromatic solvent, and (4) washing of the hydroperoxide-containing aromatic phase with water to remove base. The resulting hydroperoxide phase substantially free of unoxidized hydrocarbyl aromatic can be subjected to acid-catalyzed cleavage to produce hydroxy aromatic and carbonyl compound products without encountering the problem of azeotrope formation between unoxidized hydrocarbyl aromatic reactant with cleavage product.Type: GrantFiled: March 7, 1977Date of Patent: October 17, 1978Assignee: Phillips Petroleum CompanyInventor: Yulin Wu
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Patent number: 4101591Abstract: Haloloweralkyl ethynylbenzene compounds and their derivatives which are useful for the treatment for the relief of inflammation, pain and fever.Type: GrantFiled: November 23, 1976Date of Patent: July 18, 1978Assignee: William H. Rorer, Inc.Inventor: Julius Diamond
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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