Of Halogen Containing Phenol Patents (Class 568/755)
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Patent number: 8283501Abstract: Disclosed herein are optically active biphenol derivatives represented by the following formulas (1) and (2), a method for optically resolving a biphenol derivative represented by formula (2?), a production method of an optically active biphenol derivative (1) comprising a step for reacting a Brønsted acid with a biphenol derivative (2), and a production method of an optically active biphenol derivative (3) comprising a step for reacting a Lewis acid with an optically active biphenol derivative (1) or an optically active biphenol derivative (2).Type: GrantFiled: January 6, 2009Date of Patent: October 9, 2012Assignee: Nippon Soda Co., Ltd.Inventors: Yoshikazu Ito, Yasushi Kubota, Tsutomu Inoue
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Patent number: 7696389Abstract: A method for reducing contaminants during synthesis of pentachlorophenol includes providing a phenol-based starting material and a catalyst, which form a reaction mixture. A chlorine flow is introduced so that it is in contact with the reaction mixture, and the starting material and chlorine are reacted via a temperature-programmed reaction. The chlorine flow is terminated at a predetermined temperature prior to an end of the temperature-programmed reaction and/or at a point where the yield of pentachlorophenol is less than about 95%.Type: GrantFiled: October 31, 2008Date of Patent: April 13, 2010Assignee: The Regents of The University of MichiganInventors: Phillip E. Savage, Jianli Yu
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Patent number: 7446235Abstract: A method for reducing contaminants during synthesis of pentachlorophenol includes providing a phenol-based starting material and a catalyst, which form a reaction mixture. A chlorine flow is introduced so that it is in contact with the reaction mixture, and the starting material and chlorine are reacted via a temperature-programmed reaction. The chlorine flow is terminated at a predetermined temperature prior to an end of the temperature-programmed reaction and/or at a point where the yield of pentachlorophenol is less than about 95%.Type: GrantFiled: March 24, 2006Date of Patent: November 4, 2008Assignee: The Regents of The University of MichiganInventors: Phillip E. Savage, Jianli Yu
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Patent number: 6586638Abstract: There is provided a process for removing and recovering one or more unassociated phenolic compounds dissolved in aqueous fluid, the process comprising the steps of: (a) transferring the one or more unassociated phenolic compounds from the aqueous fluid to an alkaline stripping solution, wherein transfer of the one or more unassociated phenolic compounds from the aqueous fluid to the alkaline stripping solution occurs across a membrane; wherein the membrane is a non porous, selectively permeable membrane; (b) regulating the volume of alkaline stripping solution employed relative to the volume of aqueous fluid treated so that the total phenolic compound concentration in the alkaline stripping solution, comprising the sum of the dissociated and unassociated phenolic compound concentrations, is above the solubility of the phenolic compounds in the acidified stripping solution of step (d); (c) regulating the pH of the alkaline stripping solution in contact with the membrane to a value at least 0.Type: GrantFiled: August 28, 2002Date of Patent: July 1, 2003Assignee: Membrane Extraction Technology LimitedInventors: Shengfu Zhang, Jean-Pierre Arcangeli, Andrew Guy Livingston, Andrew Timothy Boam
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Publication number: 20020058198Abstract: The present invention includes polymers and photoresist compositions that comprise the polymers as a resin binder component. Photoresists of the invention contain a polymer that has fluorinated phenolic units and photoacid-labile groups. Resists of the invention can be effectively imaged at short wavelengths such as sub-200 nm, particularly 157 nm.Type: ApplicationFiled: September 8, 2001Publication date: May 16, 2002Applicant: Shipley Company, L.L.C.Inventors: Axel Klauck-Jacobs, Anthony Zampini, Sungseo Cho, Shintaro Yamada
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Patent number: 5847236Abstract: 2-Chloro-4-methylphenol is prepared by reacting 4-methylphenol with a chlorinating agent in the presence of a catalyst system of one or more Lewis acids in a total amount of 0.1-10% by weight and one or more diaryl sulphides in a total amount of 0.1-10% by weight, all based on the amount of 4-methylphenol. The reaction temperature is 0.degree.-100.degree. C. The chlorinating agent is used in an amount of 0.5-1.5 mol per mole of 4-methylphenol. The reaction can be carried out until virtually complete consumption of the 4-methylphenol, high isomeric selectivity and high stage selectivity being observed.Type: GrantFiled: September 25, 1996Date of Patent: December 8, 1998Assignee: Bayer AktiengesellschaftInventors: Franz-Josef Mais, Helmut Fiege
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Patent number: 5696302Abstract: A highly concentrated aqueous tribromophenolate solution containing a non-hydrophillic solvent and a reducing agent is prepared by dissolving an alkali and a reducing agent in water, adding a non-hydropillic solvent and adding tribromophenol.Type: GrantFiled: December 27, 1995Date of Patent: December 9, 1997Assignee: Dai-Ichi Kogyo Seiyaku Co., Ltd.Inventors: Setsuo Nishibori, Hideto Kondo
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Patent number: 5395994Abstract: This invention provides an environmentally acceptable method for recovery of phenolic and brominated phenolic compounds, alcohol solvent, and bromide values from the a reaction medium liquid mixture formed in the production of a tetrabromobisphenol-A predominant product. The process comprises (a) separating the tetrabromobisphenol-A predominant product and alkyl bromide from the reaction medium thereby forming a liquid mixture containing alcohol, phenolic and brominated phenolic compounds, HBr, and water; (b) treating the liquid mixture with a sufficient amount of alkaline or alkaline earth metal hydroxide so as to form a treated aqueous mixture having a pH in the range of from about 9.5 to about 14.0, and containing MBr.sub.Type: GrantFiled: May 19, 1994Date of Patent: March 7, 1995Assignee: Albemarle CorporationInventors: Robert E. Williams, William J. Cranston, III
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Patent number: 5196617Abstract: A process for hydrodehalogenating halogenated organic compounds present in a contaminated aqueous environmental source in which the halogenated organic compounds are reacted with hydrogen gas or a source of hydrogen gas in the presence of a catalyst of palladium on carbon.Type: GrantFiled: January 14, 1992Date of Patent: March 23, 1993Assignee: Engelhard CorporationInventors: Suphan Kovenklioglu, Edward N. Balko, Jeffrey B. Hoke, Robert J. Farrauto, Gary A. Gramiccioni
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Patent number: 5177268Abstract: A process for hydrodehalogenating halogenated aromatics present in a contaminated aqueous environmental source in which the halogenated aromatics are reacted with hydrogen gas or a source of hydrogen gas in the presence of a basic proton acceptor and a catalyst of palladium on carbon.Type: GrantFiled: April 6, 1992Date of Patent: January 5, 1993Assignee: Engelhard CorporationInventors: Edward N. Balko, Jeffrey B. Hoke, Gary A. Gramiccioni
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Patent number: 5124490Abstract: Acid contaminants leached from acidic ion-exchange resins and carried in process streams with phenol are separated from the phenol by passing the process stream in contact with an anionic exchange resin, whereby the acid contaminants react with and bond to the anionic exchange resin.Type: GrantFiled: June 17, 1991Date of Patent: June 23, 1992Assignee: General Electric CompanyInventor: Michael J. Cipullo
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Patent number: 5118876Abstract: A process for the separation of 2,4 DCP from a hydrocarbon feed mixture comprising 2,4 and 2,6 DCP which process employs an adsorbent comprising a type X or type L zeolite which has been cation exchanged at appropriate conditions with one or more cations selected from the group consisting of alkaline metals, alkaline earths and Group VIII elements of the Periodic Table. The adsorbed DCP isomer(s) thereafter is removed from the adsorbent by contacting it with a desorbent material and is recovered to an extract product stream, likewise the remainder of the feed material is recovered to a raffinate product stream. In a preferred embodiment the process uses a simulated moving-bed countercurrent flow system.Type: GrantFiled: January 18, 1989Date of Patent: June 2, 1992Inventors: Hermann A. Zinnen, Kelly C. Issa
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Patent number: 4855053Abstract: Process for extracting organic compounds which are present in water in the form of solutions or suspensions by a liquid carboxylic acid which is immiscible with water. Branched or unbranched linear acids such as n-heptanoic, n-octanoic, or 2-ethylhexanoic acids make it possible to quantitatively extract compounds such as phenols, amines or amino acids from such aqueous solutions, thereby rendering the process useful for the purification of industrial wastewaters.Type: GrantFiled: December 18, 1986Date of Patent: August 8, 1989Assignee: AtochemInventors: Charles Benedetti, Claude Gluntz, Robert Pascal, Michel Stefanini
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Patent number: 4822922Abstract: Mixtures produced by chlorination of phenol/chlorophenols are effectively stabilized by stirring same in the presence of a stabilizing amount of at least one strong protonic acid and/or a Lewis acid.Type: GrantFiled: September 25, 1987Date of Patent: April 18, 1989Assignee: Rhone-Poulenc ChimieInventors: Jean-Roger Desmurs, Serge Ratton
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Patent number: 4605791Abstract: Process for purification of technical grade pentachlorophenol by immersing the pentachlorophenol in an aqueous alkaline solution or suspension, separating an insoluble portion from the resultant mixture, dissolving the insoluble portion in an aqueous alkaline solution, treating the solution with active charcoal, removing the active charcoal, adding copper sulfate to the solution, removing the deposit which forms from the solution, and recovering pentachlorophenol from the solution. Alternatively, the steps of treatment with active charcoal and addition of copper sulfate can be reversed.Type: GrantFiled: June 7, 1985Date of Patent: August 12, 1986Assignee: Yonezawa Chemical Industry Co., Ltd.Inventor: Toyozo Yonezawa
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Patent number: 4523041Abstract: A method of efficiently purifying crude 4-fluorophenol containing phenol as impurity. Phthalic acid or its anhydride, or a suitable derivative of phthalic acid, and a dehydrating agent such as sulfuric acid or a metal chloride are mixed with the crude 4-fluorophenol, and the mixture is kept in a liquid state usually with moderate heating to 30.degree.-180.degree. C. until completion of condensation reaction between phenol and the phthal-compound. After that pure 4-fluorophenol can easily be recovered by distillation or recrystallization.Type: GrantFiled: May 25, 1984Date of Patent: June 11, 1985Assignee: Central Glass Company, LimitedInventors: Toshikazu Kawai, Haruo Suzuki, Shouzou Kaneda
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Patent number: 4447541Abstract: A reagent mixture is admixed with soil to first desorb and then hydrolyze and thereby increase the biodegradability of a toxic or otherwise hazardous polyhalogenated organic compound with which the soil is contaminated. Essential constituents of the reagent mixture are: (1) an alkali metal hydroxide, an alkali metal hydroxide/alcohol or alkali metal hyroxide/glycol mixture, or an alkoxide; and (2) a sulfoxide catalyst. The hydrolyzed compounds can be biologically degraded into compounds which pose little if any hazard to the environment or its inhabitants by naturally occurring or artifically introduced Pseudomonas sp. and other microorganisms with adjustment of soil pH (and perhaps orther parameters) to provide a viable environment for the bacteria being carried out after the chemical treatment if inoculation with bacterial cultures is employed.Type: GrantFiled: June 6, 1983Date of Patent: May 8, 1984Assignee: Galson Research CorporationInventor: Robert L. Peterson
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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: 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: 4421937Abstract: Mixtures of crystals and a liquid, ordinarily comprising the mother liquor of the crystals are continuously separated by feeding the mixture into a screw type press having drainage apperatures, thereby subjecting the crystals with the mother liquor entrapped therein to pressures sufficient to substantially reduce the interstitial space between crystals. Reduction of the interstitial space causes the mother liquor to be forced out of the drainage aperatures thus purifying the crystals. This achieves a more effective separation of mother liquor from the crystals than can be achieved by gravity or the use of a device such as a centrifuge and eliminates the need for a foreign solvent to wash the mother liquor from the crystals.Type: GrantFiled: January 4, 1982Date of Patent: December 20, 1983Assignee: Monsanto CompanyInventor: Dan K. Lynch
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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: 4327027Abstract: A method for the reduction of the content of toxic chlorinated aromatic compounds such as chlorinated aromatic dioxins and especially chlorinated dibenzo-p-dioxins in reaction products to virtually zero consisting essentially of reacting a mass containing chlorinated aromatic dioxins with an amount, in excess of stoichiometrical based on the total organic halogen content, of alkaline reactants selected from the group consisting of (1) alkali metal alcoholates of alcohols selected from the group consisting of alkanols having from 1 to 5 carbon atoms, polyalkoxyalkane glycols having 4 to 20 carbon atoms, alkanepolyols having from 2 to 5 carbon atoms and 2 to 3 hydroxyls, and monoalkyl ethers of such alkanepolyols with alkanols having from 1 to 4 carbon atoms, or (2) mixtures of said alcohols with alkaline reactants selected from the group consisting of alkali metal hydroxides and carbonates, at a reaction temperature of from 140.degree. C. to 220.degree. C.Type: GrantFiled: February 7, 1980Date of Patent: April 27, 1982Assignee: Vertac Chemical CorporationInventors: Kenneth J. Howard, Albert E. Sidwell
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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: 4288296Abstract: The decomposition of chlorinated phenols, especially pentachlorophenol, during exposure to high temperatures (e.g., storage and distillation) is markedly reduced by incorporating into the molten chlorinated phenol at least about 0.25 percent by weight of said impure chlorinated phenol of at least one monohydric primary alcohol having at least 14 carbon atoms, one hydroxyl group, and devoid of any other heteroatoms or ether linkages; selected from the group consisting of straight-chain or branched monohydric primary alcohols or a mixture of said straight-chain or branched monohydric primary alcohols.Type: GrantFiled: February 1, 1980Date of Patent: September 8, 1981Assignee: The Dow Chemical CompanyInventor: Leonard R. Thompson
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Patent number: 4280012Abstract: A method of removing an impurity of the group chlorinated dibenzo-p-dioxins, chlorinated dibenzofurans, chlorinated hydroxydiphenylethers and chlorinated diphenylethers from a substance containing the same which comprises contacting said substance with an agent which is hydrazine, acetylene, an acetylene derivative or a compound which under the processing conditions is a source of hydrazine or acetylene.Type: GrantFiled: March 1, 1979Date of Patent: July 21, 1981Assignee: Dynamit Nobel AktiengesellschaftInventors: Albino Pastura, Gerhard Kelbch, Hans-Leo Hulsmann
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Patent number: 4272636Abstract: In an improved process for preparing chlorinated phenol by the reaction of molten phenol with chlorine in the presence of a Friedel-Crafts catalyst, the improvement comprises adding to the molten chlorinated phenol product, immediately on completion of the chlorination process, at least 0.5 weight percent of a glycol ether thereby inhibiting dioxin formation, inhibiting decomposition of the technical grade chlorinated phenol and most importantly, imparting mold release properties to the final product which is cast in corrosion-resistant molds, preferably stainless steel or plastic-lined steel molds.Type: GrantFiled: December 26, 1979Date of Patent: June 9, 1981Assignee: The Dow Chemical CompanyInventors: Leonard R. Thompson, J. Kevin Kearney
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Patent number: 4228309Abstract: Chlorodibenzo-p-dioxin impurities are removed from a polychlorophenol that contains at least one chlorodibenzo-p-dioxin as an impurity by preparing an aqueous solution of a water-soluble alkaline salt of the polychlorophenol, mixing the aqueous solution with cyclohexane to extract the dioxins therefrom, decanting the purified aqueous solution from the cyclohexane phase, neutralizing the purified aqueous solution to precipitate the purified polychlorophenol, and separating the precipitate.Type: GrantFiled: April 20, 1979Date of Patent: October 14, 1980Inventor: David B. Hatcher
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Patent number: 4216342Abstract: A novel process for the purification of 2,4,5-trichlorophenol which comprises selectively reacting the major impurities with formaldehyde.Type: GrantFiled: March 30, 1979Date of Patent: August 5, 1980Assignee: Givaudan CorporationInventors: Joseph A. Virgilio, Joachim E. Freudewald
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Patent number: 4160112Abstract: A process for isolating crude pentabromophenol containing occluded bromine and hydrogen bromide as impurities comprising the steps of contacting the crude pentabromophenol with a strong acid such as hydrobromic acid, sulfuric acid, hydrochloric acid and phosphoric acid; heating the mixture in order to remove excess bromine; and recovering of the pentabromophenol, whereby formation of carbonyl-group-containing impurities during isolation is minimized.Type: GrantFiled: February 13, 1978Date of Patent: July 3, 1979Assignee: Great Lakes Chemical CorporationInventors: Robert P. Levek, Rastko I. Mamuzic, John L. Sands
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Patent number: 4147872Abstract: Azacycloalkanes, and derivatives thereof, including unsaturated analogs, each of which has at the 3-position a 2-hydroxy-4-substituted phenyl group wherein the 4-position substituent is alkyl which can have an oxygen atom as part of the chain, or aralkyl which can have an oxygen atom as part of the alkyl chain, their use for pharmacological and medicinal purposes, intermediates therefor and processes for their preparation.Type: GrantFiled: September 13, 1977Date of Patent: April 3, 1979Assignee: Pfizer Inc.Inventors: Thomas H. Althuis, Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
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Patent number: 4142943Abstract: The decomposition of pentachlorophenol during distillation to remove impurities is markedly reduced by incorporating into the distilling molten pentachlorophenol a hydroxyl or polyhydroxyl containing organic compound having a boiling point above about 100.degree. C. in the presence or absence of water.Type: GrantFiled: September 23, 1974Date of Patent: March 6, 1979Assignee: The Dow Chemical CompanyInventors: Erwin H. Kobel, deceased, Masao Yoshimine
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Patent number: 4113974Abstract: A process for improving the quality of diphenols by recrystallization from aqueous solvent systems.Type: GrantFiled: December 30, 1976Date of Patent: September 12, 1978Assignee: General Electric CompanyInventors: Victor Mark, Charles Vernon Hedges
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Patent number: 4096175Abstract: Covers a method of separating a nonionic surfactant from an anionic surfactant by use of methylal.Type: GrantFiled: December 1, 1976Date of Patent: June 20, 1978Assignee: Texaco Development CorporationInventors: Carter G. Naylor, Simon P. Burns