Two Phenols Bonded Directly To Each Other Patents (Class 568/730)
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Patent number: 4465878Abstract: A process for producing 4,4'-dihydroxydiphenyl which comprises subjecting to alkali fusion 1 mol of 4,4'-diphenyldisulfonic acid and/or potassium 4,4'-diphenyldisulfonate together with 4 to 10 mol of potassium hydroxide and 0.1 to 2 mol of potassium sulfate. Alternatively, the process may comprise subjecting to alkali fusion 4,4'-diphenyldisulfonic acid in the presence of potassium hydroxide, controlling to 20 to 25% the potassium hydroxide concentration in the reaction mixture, and separating dipotassium salt of 4,4'-dihydroxydiphenyl.Type: GrantFiled: July 21, 1982Date of Patent: August 14, 1984Assignee: Sugai Chemical Industry Co., Ltd.Inventors: Takeshi Hashimoto, Terumasa Akashi, Koji Nishihara
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Patent number: 4447656Abstract: Products from the heterogeneously catalyzed oxidative coupling of 2,6-ditertiarybutylphenol are prepared in high yield by the use of an unreactive, non-polar liquid reactive medium.Type: GrantFiled: February 24, 1983Date of Patent: May 8, 1984Assignee: The Dow Chemical CompanyInventors: Larry D. Kershner, Leonard R. Thompson, Robert M. Strom
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Patent number: 4438284Abstract: Self-condensation products are obtained by the oxidative coupling of substituted phenols in the presence of a heterogeneous cobalt-containing catalyst.Type: GrantFiled: May 17, 1982Date of Patent: March 20, 1984Assignee: The Dow Chemical CompanyInventor: Robert M. Strom
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Patent number: 4410736Abstract: Substituted biphenols are produced by the oxidative coupling of phenolic reactants in the presence of a heterogeneous oxidative coupling catalyst and thereafter further contacting the reaction product with additional phenolic reactant in the presence of a heterogeneous reduction catalyst in the substantial absence of oxygen.Type: GrantFiled: April 6, 1981Date of Patent: October 18, 1983Assignee: The Dow Chemical CompanyInventor: Robert M. Strom
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Patent number: 4380676Abstract: A process for the production of 2,2'-dihydroxy-biphenyls of the formula I ##STR1## wherein the symbols are as defined in claim 1. The process consists in the oxidative coupling of a phenol of the formula II ##STR2## in the presence of a strong inorganic base, with hydrogen peroxide as oxidizing agent. The reaction temperature is in the range from 30.degree. to 100.degree. C. and 1.5 to 4 moles of a base are employed per mole of phenol of the formula II.Type: GrantFiled: February 20, 1981Date of Patent: April 19, 1983Assignee: Ciba-Geigy CorporationInventor: Michael Rasberger
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Patent number: 4361708Abstract: Substituted biphenols are produced by heating substituted phenols in nitrobenzene solvent in the presence of a heterogeneous oxidative coupling catalyst without the addition of oxygen-containing gas.Type: GrantFiled: March 6, 1981Date of Patent: November 30, 1982Assignee: The Dow Chemical CompanyInventor: Robert M. Strom
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Patent number: 4354047Abstract: Carbon-to-carbon coupled self-condensation products are obtained by the oxidative coupling of substituted phenols in the presence of a heterogeneous dehydrogenation catalyst comprising nickel.Type: GrantFiled: May 22, 1981Date of Patent: October 12, 1982Assignee: The Dow Chemical CompanyInventor: Robert M. Strom
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Patent number: 4354048Abstract: Carbon-to-carbon coupled self-condensation products are obtained by the oxidative coupling of substituted phenols in the presence of a heterogeneous dehydrogenation catalyst comprising copper chromite.Type: GrantFiled: May 22, 1981Date of Patent: October 12, 1982Assignee: The Dow Chemical CompanyInventor: Robert M. Strom
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Patent number: 4348542Abstract: A process for the production of mixtures of alkylated aromatic polyhydroxy compounds by reacting alkylated phenols with carbonyl compounds, wherein acidic organic ion exchangers are used as catalysts and commercial dialkyl phenols as the phenol and any unreacted starting phenols separated off are completely recycled into the process without intermediate purification, and the application of the thus produced polyhydroxyl compounds for making thermoplastic polycarbonates.Type: GrantFiled: July 9, 1980Date of Patent: September 7, 1982Assignee: Bayer AktiengesellschaftInventors: Volker Serini, Rainer Neumann, Gerhard Friedhofen, Dieter Freitag, Jurgen Heuser, Hans-Helmut Schwarz
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Patent number: 4340768Abstract: 4,4'-Dihydroxybiphenyl is produced by hydrolyzing 4,4'-dibromobiphenyl in the presence of a copper compound catalyst in an alkaline aqueous solution; extracting by-products from the alkaline aqueous solution with an alcohol or ketone which forms an organic phase; neutralizing or acidifying the alkaline aqueous solution with an acid; extracting the reaction product with the specific solvent; and crystallizing the reaction product from the extracted solution to obtain 4,4'-dihydroxybiphenyl having high purity.Type: GrantFiled: October 14, 1980Date of Patent: July 20, 1982Assignee: Hodogaya Chemical Co., Ltd.Inventors: Susumu Jinbo, Shoichi Kohno, Masatoshi Onishi
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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: 4324926Abstract: A process for purifying 4,4'-dihydroxydiphenyl comprising contacting a solution of 4,4'-dihydroxydiphenyl alkali metal salt with activated carbon followed by removing the activated carbon from the solution and acidifying the solution with sufficient acid to convert essentially all of the 4,4'-dihydroxydiphenyl alkali metal salt to water insoluble 4,4'-dihydroxydiphenyl and 4,4'-dihydroxydiphenyl product containing less than 0.45 weight percent of 4-monohydroxydiphenyl impurity.Type: GrantFiled: March 6, 1980Date of Patent: April 13, 1982Assignee: Buffalo Color CorporationInventors: Walter R. Demler, Krishen L. Nagpal, Richard M. Dollard, Eugene Odin, Donald T. Donahue
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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: 4256596Abstract: Mixtures of (A) hydroxyaromatic compounds (e.g., phenols) having no aliphatic substituents of more than 4 carbon atoms and (B) hydroxyaromatic compounds having at least one aliphatic substituent with at least about 12 carbon atoms may be oxidatively coupled to yield products useful as lubricant and fuel additives.Type: GrantFiled: September 26, 1979Date of Patent: March 17, 1981Assignee: The Lubrizol CorporationInventor: Jerome M. Cohen
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Patent number: 4243822Abstract: A process for the preparation of 4,4' dihydroxydiphenyl by acidifying an alkali metal salt of 4,4' dihydroxydiphenyl. The alkali metal salt of 4,4' dihydroxydiphenyl is prepared by fusion of an alkali metal hydroxide with alkali metal diphenyl 4,4' disulfonic acid. Because the reaction may be carried out in granular form, or in a reaction which is made highly fluid by using potassium hydroxide with potassium diphenyl 4,4' disulfonic acid, or by reacting the alkali metal 4,4' disulfonic acid in increments with the hydroxide, low molar ratios of hydroxide to alkali metal diphenyl 4'4, disulfonic acid may be used. When potassium diphenyl 4,4' disulfonic acid is used in accordance with the invention, it is prepared by reacting 4,4' diphenyl disulfonic acid with an inorganic neutral potassium salt.Type: GrantFiled: August 31, 1979Date of Patent: January 6, 1981Assignee: Buffalo Color CorporationInventors: Walter R. Demler, Krishen L. Nagpal, Richard M. Dollard, Eugene Odin, Donald T. Donahue
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Patent number: 4242527Abstract: A process for purifying crude diphenols via a water co-solvent system is disclosed.Type: GrantFiled: May 23, 1979Date of Patent: December 30, 1980Assignee: General Electric CompanyInventors: Victor Mark, Charles V. Hedges
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Patent number: 4238627Abstract: An oxidative process for preparing 4,4'-bis(2,6-dihydrocarbylphenols) is provided which comprises contacting with good agitation a disubstituted phenol such as 2,6-di-tertiarybutyl phenol with up to stoichiometric amounts of oxygen in the presence of a small catalytic quantity of a catalyst selected from the group consisting of alkali metal and alkaline earth metal hydroxides, alkali metal and alkaline earth metal salts of a weak acid, amine bases, and mixtures of the same at a temperature from about 50.degree. to 240.degree. C. until a reaction product containing a substantial amount of the corresponding biphenol is formed, said reaction product being substantially free of quinones.Type: GrantFiled: November 16, 1978Date of Patent: December 9, 1980Assignee: Union Carbide CorporationInventor: Walter T. Reichle
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Patent number: 4210765Abstract: An improved process for obtaining halogenated diphenols which can be pure dihalodiphenols or predetermined, statistical mixtures comprising unreacted diphenol, monohalodiphenols and dihalodiphenols.Type: GrantFiled: February 28, 1978Date of Patent: July 1, 1980Assignee: General Electric CompanyInventor: Victor Mark
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Patent number: 4205187Abstract: A process for preparing p,p'-biphenol is provided which comprises heating a 4,4'-bis(substituted phenol) at elevated temperatures below the decomposition temperature of p,p'-biphenol in the absence of a catalyst under an inert, non-reactive atmosphere for the length of time sufficient to obtain a reaction product containing a substantial amount of p,p'-biphenol while, preferably, removing the olefin by-product formed and then recovering the p,p'-biphenol product.Type: GrantFiled: January 2, 1979Date of Patent: May 27, 1980Assignee: Union Carbide CorporationInventors: Jorge N. Cardenas, Walter T. Reichle
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Patent number: 4195189Abstract: 2,6-Dialkylphenols may be oxidized in a molten state with an activated basic cupric oxide having a specific surface area to produce carbon-carbon coupled condensation products.Type: GrantFiled: February 15, 1979Date of Patent: March 25, 1980Assignee: ICI Americas Inc.Inventor: Roger A. Earley
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Patent number: 4191843Abstract: A process for the preparation of bisphenols is described which comprises reacting, in a reaction zone, at least 2 moles of a phenol with a carbonyl compound, at a temperature of from 40.degree. to 95.degree. C., in the presence of an acid ion exchanger, optionally partially modified with a compound having an acidic reacting group and a mercaptan group, and recovering the bisphenols from the reaction zone effluent, characterized in that the reaction zone effluent is contacted with an acid ion exchanger in metal salt form and/or a weak base ion exchanger. As a result, it has been found that the formation of undesirable compounds is substantially reduced.Type: GrantFiled: November 7, 1978Date of Patent: March 4, 1980Assignee: Shell Oil CompanyInventors: Arien Kwantes, Pieter A. Gautier
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Patent number: 4180686Abstract: A method of preparing carbon-carbon coupled condensation products of alkylphenols is disclosed. Briefly, the method comprises oxidation of certain specific alkylphenols using palladium acetate as the catalyst in acetic acid or other suitable solvent.Type: GrantFiled: January 25, 1979Date of Patent: December 25, 1979Assignee: Conoco, Inc.Inventor: John R. Dodd
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Patent number: 4170711Abstract: Monomeric and polymeric halogenated organic compounds derived from 2,2',6,6'-tetrabromo-3,3',5,5' -tetraalkyl-4,4'-biphenols are described. The derivatives are useful in their monomeric and polymeric form as flame retardant additives and/or concentrates for normally flammable resinous materials. The thermal stability at elevated temperatures of the brominated biphenol derivatives advantageously benefits polymeric compositions containing the brominated biphenol derivatives especially when the polymeric compositions are molded into three dimensional articles, or formed into films, sheeting or shaped into fibers, laminates or reinforced plastics by conventional techniques.Type: GrantFiled: September 27, 1976Date of Patent: October 9, 1979Assignee: General Electric CompanyInventors: Charles M. Orlando, Francois A. Lavallee
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Patent number: 4158027Abstract: Compositions stabilized against premature polymerization are disclosed. These compositions contain(a) a vinyl or vinylidene monomer capable of free radical polymerization, and(b) a polymerization inhibitor having the following general formula: ##STR1## wherein R' is hydrogen or an alkyl group containing from 1 to 4 carbon atoms,R.sub.1, r.sub.2, r.sub.3 and R.sub.4 are alkyl groups containing from 1 to 5 carbon atoms, andR.sub.5, r.sub.6, r.sub.7 and R.sub.8 are hydrogen or alkyl groups containing from 1 to 5 carbon atoms provided that only two of these may be a secondary or a tertiary alkyl group.Type: GrantFiled: June 26, 1978Date of Patent: June 12, 1979Assignee: ICI Americas Inc.Inventor: Alfred J. Restaino
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Patent number: 4157449Abstract: Hydroxy, alkoxy and acyloxy 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: June 5, 1979Assignee: William H. Rorer, Inc.Inventor: Julius Diamond
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Patent number: 4156788Abstract: Substantially pure tetramethylbiphenol may be recovered from a reaction product obtained by the oxidative coupling of xylenol by vaporizing the reaction product and subliming substantially pure tetramethylbiphenol from the vapor.Type: GrantFiled: September 19, 1977Date of Patent: May 29, 1979Assignee: ICI Americas Inc.Inventor: Roger A. Earley
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Patent number: 4139544Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of phenols and naphthols are prepared by contacting an aqueous mixture of phenol or naphthol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 8.5-9.5 during the oxidative coupling reaction and a catalyst system comprising a copper, cobalt, nickel, iron, chromium, cerium, or manganese chelate of a polyimino acid containing more than two nitrogen atoms.Type: GrantFiled: November 26, 1976Date of Patent: February 13, 1979Assignee: ICI Americas Inc.Inventor: Thomas F. Rutledge
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Patent number: 4132722Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols are prepared by contacting an aqueous mixture of an alkyl phenol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 9-9.5 during the oxidative coupling reaction and a catalyst system comprising a copper, cobalt, nickel, iron, chromium, cerium or manganese complex of a diimino acid. The mixture may optionally contain a surfactant.Type: GrantFiled: November 26, 1976Date of Patent: January 2, 1979Assignee: ICI Americas Inc.Inventor: Thomas F. Rutledge
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Patent number: 4112019Abstract: Compositions stabilized against premature polymerization are disclosed. These compositions contain(a) a vinyl or vinylidene monomer capable of free radical polymerization, and(b) a polymerization inhibitor having the following general formula: ##STR1## wherein R' is hydrogen or an alkyl group containing from 1 to 4 carbon atoms,R.sub.1, r.sub.2, r.sub.3 and R.sub.4 are alkyl groups containing from 1 to 5 carbon atoms, andR.sub.5, r.sub.6, r.sub.7 and R.sub.8 are hydrogen or alkyl groups containing from 1 to 5 carbon atoms provided that only two of these may be a secondary or a tertiary alkyl group.Type: GrantFiled: May 13, 1977Date of Patent: September 5, 1978Assignee: ICI Americas Inc.Inventor: Alfred Joseph Restaino
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Patent number: 4108908Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols or 1-naphthols are prepared by contacting an aqueous mixture of an alkylphenol or 1-naphthol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 7.0-9.0 during the oxidative coupling reaction and a catalyst system comprising a cupric, cobaltous, manganous or chromic chelate of a thio-acid compound.The mixture may optionally contain a surfactant.Type: GrantFiled: February 18, 1977Date of Patent: August 22, 1978Assignee: ICI Americas Inc.Inventor: Thomas F. Rutledge
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Patent number: 4105705Abstract: Vinyl- and arylmercuric halide salts undergo reaction with rhodium (I) and (III) catalysts, preferably in the presence of lithium chloride to provide essentially quantitative yields of the corresponding 1,3 dienes and biaryls respectively. Importantly, the reaction is stereospecific and is especially valuable for synthesis of symmetrical functionally substituted dienes, biaryls and polyenes.Type: GrantFiled: December 27, 1976Date of Patent: August 8, 1978Assignee: Iowa State University Research Foundation, Inc.Inventor: Richard C. Larock
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Patent number: 4101561Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols are prepared by contacting an aqueous mixture of an alkyl phenol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 8.5-9.5 during the oxidative coupling reaction and a catalyst system comprising certain imino acid chelates of Cu.sup.2, Ni.sup.2, Co.sup.2, Ce.sup.3, Cr.sup.3, Mn.sup.2 and Fe.sup.3. The mixture may optionally contain a surfactant.Type: GrantFiled: November 26, 1976Date of Patent: July 18, 1978Assignee: ICI Americas Inc.Inventor: Thomas F. Rutledge
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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: 4100205Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols or 1-naphthols are prepared by contacting an aqueous mixture of an alkylphenol or 1-naphtol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 7.5-10 during the oxidative coupling reaction and a catalyst system comprising a cupric, cobaltous, nickelous, ferric, manganous or chromic chelate of an aminoketone compund.The mixture may optionally contain a surfactant.Type: GrantFiled: February 18, 1977Date of Patent: July 11, 1978Assignee: ICI Americas Inc.Inventor: Thomas F. Rutledge
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Patent number: 4100202Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols or 1-naphthols are prepared by contacting an aqueous mixture of an alkylphenol or 1-naphthol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 8.5-9.5 during the oxidative coupling reaction and a catalyst system comprising a cupric chelate of a compound selected from the group consisting of quanidines, amides, salens, dihydrazides, triazenes, dihydroxy substituted aromatics, macrocylic polyamines and alpha, delta-polyketones.The mixture may optionally contain a surfactant.Type: GrantFiled: February 18, 1977Date of Patent: July 11, 1978Assignee: ICI Americas Inc.Inventor: Thomas F. Rutledge
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Patent number: 4100203Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols or 1-naphthols are prepared by contacting an aqueous mixture of an alkylphenol or 1-naphthol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 8.0-9.5 during the oxidative coupling reaction and a catalyst system comprising a cupric, cobaltous or manganous chelate of an oxime of a keto or aldehyde compound.The mixture may optionally contain a surfactant.Type: GrantFiled: February 18, 1977Date of Patent: July 11, 1978Assignee: ICI Americas Inc.Inventor: Thomas F. Rutledge
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Patent number: 4100206Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols or 1-naphthols are prepared by contacting an aqueous mixture of an alkyl phenol or 1-naphthol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 7.0-9.5 during the oxidative coupling reaction and a catalyst system comprising a cupric or manganous chelate of a keto alcohol compound.The mixture may optionally contain a surfactant.Type: GrantFiled: February 18, 1977Date of Patent: July 11, 1978Assignee: ICI Americas Inc.Inventor: Thomas F. Rutledge
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Patent number: 4100204Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols or 1-naphthols are prepared by contacting an aqueous mixture of an alkylphenol or 1-naphthol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 7.0-9.5 during the oxidative coupling reaction and a catalyst system comprising a cupric, cobaltous or manganous chelate of a hydroxy- or keto- acid compound.The mixture may optionally contain a surfactant.Type: GrantFiled: February 18, 1977Date of Patent: July 11, 1978Assignee: ICI Americas Inc.Inventor: Thomas F. Rutledge
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Patent number: 4098830Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols or 1-naphthols are prepared by contacting an aqueous mixture of an alkylphenol, alkoxyphenyl, or 1-naphthol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 7.0-9.5 during the oxidative coupling reaction and a catalyst system comprising a cupric, cobaltous, manganous, nickelous, chromic or ferric chelate of a dicarboxylic acid compound.The mixture may optionally contain a surfactant.Type: GrantFiled: February 18, 1977Date of Patent: July 4, 1978Assignee: ICI Americas Inc.Inventor: Thomas F. Rutledge
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Patent number: 4096190Abstract: Carbon-carbon coupled self-condensation products obtained by the oxidative coupling of alkylphenols are prepared by contacting an aqueous mixture of an alkyl phenol with oxygen in the presence of sufficient alkaline material to sustain a pH in the range of 6-9.5 during the oxidative coupling reaction and a catalyst system comprising an ammonia complex of monovalent copper; divalent copper, cobalt, nickel or manganese; or trivalent chromium or iron. The mixture may optionally contain a surfactant.Type: GrantFiled: November 26, 1976Date of Patent: June 20, 1978Assignee: ICI Americas Inc.Inventor: Thomas F. Rutledge