Phenols (h Of -oh May Be Replaced By A Group Ia Or Iia Light Metal) Patents (Class 568/706)
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Patent number: 4594459Abstract: Prepare p-isopropenyl phenol and other alkenyl aromatic compounds by contacting a dihydroxydiphenyl alkane or a related substituted diaromatic alkane with an alkaline catalyst and at least one gas under supercritical conditions such that p-isopropenyl phenol or the corresponding related alkenyl aromatic compound is produced.Type: GrantFiled: March 25, 1985Date of Patent: June 10, 1986Assignee: The Dow Chemical CompanyInventor: Kimio Inoue
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Patent number: 4594460Abstract: Substituted phenols of formula ##STR1## in which R.sub.1 is in an ortho or para position relative to the phenol function and denotes ##STR2## R.sub.2 denotes an acyclic radical optionally substituted by alkyl, hydroxy, alkoxycarbonyl, cyano or formyl, or a phenyl or naphthyl radical, and R denotes hydrogen or 1 to 4 substituents chosen from halogen, OH optionally in the form of ether or ester, alkyl, NO.sub.2, CHO optionally in the form of acetal, CH.sub.3 CO--, C.sub.6 H.sub.5 CO--, NH.sub.2, alkylamino, dialkylamino or alkoxycarbonyl, it being understood that 2 symbols R may form with the phenyl nucleus a condensed aromatic ring, which comprises reacting a butadiene of formula ##STR3## with a phenol for formula ##STR4## in water in the presence of a rhodium-based catalyst, a water-soluble phosphine and optionally an inorganic or organic base. The products of formula (I) are intermediates for the synthesis of vitamin E, antioxidants, perfumes or insecticides.Type: GrantFiled: March 19, 1985Date of Patent: June 10, 1986Assignee: Rhone-Poulenc SanteInventors: Gerard Mignani, Didier Morel
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Patent number: 4593129Abstract: A process for making an alkali metal alkoxide (e.g. sodium alkoxide) of a halogen-substituted alcohol (e.g. fluorine-substituted alcohols) by dispersing an alkali metal (e.g. sodium) in a cycloalkane (e.g. cyclohexane) containing a phenol (e.g. o-allylphenol) and adding the resultant dispersion to an ether (e.g. THF) solution of a halogen-substituted alcohol. The resultant alkali metal haloalkoxide solution contains phenoxides and can be reacted with a phosphonitrilic chloride polymer to introduce haloalkoxide and phenoxide substituents.Type: GrantFiled: April 18, 1984Date of Patent: June 3, 1986Assignee: Ethyl CorporationInventors: R. Woodrow Wilson, Jr., Dustin H. Thomas
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Patent number: 4558040Abstract: Certain miticidal (2-alkyl-3,4-dihydro-2H-1-benzopyran-8-yl)diazenecarboxylic acid esters.Type: GrantFiled: December 3, 1984Date of Patent: December 10, 1985Assignee: Shell Oil CompanyInventors: Kurt H. Pilgram, Richard D. Skiles
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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: 4447654Abstract: 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: September 30, 1982Date of Patent: May 8, 1984Assignee: Koppers Company, Inc.Inventor: Gerd Leston
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Patent number: 4435601Abstract: Optionally aldehyde substituted polyphenols are prepared by oxidizing, with hydrogen peroxide, a hydroxybenzaldehyde bearing at least one aldehyde substituent ortho- and/or para- to the nuclear hydroxyl group, in an aqueous reaction medium and in the presence of an alkali or alkaline earth metal base, the process being characterized in that the pH of the reaction medium is continuously maintained at a value no greater than 7 throughout the course of the oxidation reaction.The subject process is well suited for the preparation of, e.g., hydroxy-p-vanillin from guaiacol, and the novel compound 2,4,6-triformylphenol.Type: GrantFiled: July 7, 1981Date of Patent: March 6, 1984Assignee: Rhone-Poulenc IndustriesInventors: Karel Formanek, Daniel Michelet, Dominique Petre
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Patent number: 4396783Abstract: A process for the hydroxylation of aromatic hydrocarbons by hydrogen peroxide, consisting in reacting said compounds in the presence of synthetic zeolites which contain heteroatoms, both replaced and exchanged.The reaction is carried out at a temperature comprised between 80.degree. C. and 120.degree. C. and in the presence of the hydrocarbon only or in the presence of a solvent which permits, at least partially, to admix the aromatic hydrocarbon with the hydrogen peroxide.Type: GrantFiled: September 4, 1981Date of Patent: August 2, 1983Assignee: Anic S.p.A.Inventors: Antonio Esposito, Marco Taramasso, Carlo Neri
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Patent number: 4374293Abstract: Allylbenzene is converted to indene by means of a tungsten-containing catalyst.Type: GrantFiled: August 14, 1981Date of Patent: February 15, 1983Assignee: The Standard Oil Co.Inventors: J. D. Burrington, R. K. Grasselli, C. T. Kartisek
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Patent number: 4347148Abstract: Nitro phenols of the general formula ##STR1## wherein R is an aliphatic substituent of at least about 40 carbon atoms, a, b and c are, for example, each 1, 2 or 3, and Ar is an aromatic moiety such as a benzene nucleus, naphthalene nucleus or linked benzene nuclei, are useful additives for fuels and lubricants and intermediates to such additives. These nitro phenols can be conveniently prepared by nitrating appropriate phenols. Typically nitro phenols are formed by nitration of alkyl phenols having an alkyl group of at least about 50 carbon atoms.Type: GrantFiled: November 19, 1979Date of Patent: August 31, 1982Assignee: The Lubrizol CorporationInventor: Kirk E. Davis
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Patent number: 4290961Abstract: Catalytic reduction of carbonyl compounds by transfer of hydrogen from alcohols to aliphatic, alicyclic, aromatic, homo- and heterocyclic ketones or aldehydes, catalyzed by rhodium or iridium complexes, characterized in that a primary or secondary alcohol of formula (I) or a glycol: ##STR1## is reacted with a ketonic compound of formula (II): ##STR2## in which R and R' and, respectively, R" and R'", optionally linked with each other according to homo- or heterocycles, indifferently represent a hydrogen atom or a hydrocarbyl group having up to 30 atoms of carbon, also substituted, provided that at least one of symbols R" and/or R'" is different respectively from R and/or R', in the presence of a complex catalyst of rhodium or of iridium selected from those having formulas (III) and (IV): ##STR3## wherein: M is selected from Rh and Ir;Chel is a chelating bidentate nitrogenous compound;L-L is a molecule of a preferably non-conjugated diolefin or two molecules of a monoolefin;X.sup.Type: GrantFiled: March 7, 1980Date of Patent: September 22, 1981Assignee: Montedison S.p.A.Inventors: Giovanni Mestroni, Grazia Zassinovich, Annamaria Camus
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Patent number: 4284823Abstract: There is disclosed a process comprising reacting a compound having the general structural Formula II: ##STR1## with a compound having the general Formula III: ##STR2## in the presence of a basic catalyst while dissolved in an organic solvent to yield an aldehyde having the structural Formula I: ##STR3## wherein R.sub.1 and R.sub.2 are the same or different radicals selected from the group consisting of tertiary alkyl radicals having from 4 to 12 carbon atoms, R.sub.3 and R.sub.4 are the same or different radicals selected from the group consisting of alkyl radicals containing from 1 to 12 carbon atoms, cycloalkyl radicals containing from 5 to 12 carbon atoms, phenyl and substituted phenyl radicals or R.sub.3 and R.sub.4 with the carbon atom to which they are joined may form a cycloalkyl ring of from 5 to 12 carbon atoms, R.sub.5 is selected from the group consisting of hydrogen, alkyl radicals containing from 1 to 12 carbon atoms, or a cycloalkyl radical containing 5 or 6 carbon atoms.Type: GrantFiled: October 15, 1979Date of Patent: August 18, 1981Assignee: The Goodyear Tire & Rubber CompanyInventor: Richard H. Kline
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Patent number: 4283565Abstract: There is described an essentially two step process for the preparation of benzylalcohols including those benzylalcohols having substituents on the benzyene ring by reaction of a substituted or unsubstituted benzyl halide with a formate typically an alkali or alkaline earth metal formate to form the corresponding substituted or unsubstituted benzyl formate. In the second step of the process the benzyl formate is contacted with an alcohol whereby the same is converted into the desired benzylalcohol. Both steps can be performed employing catalysts. Described in the specification is the realization of the desired product in exceptionally high yields in a short period of time whereby the process is characterized by high space-time yields.Type: GrantFiled: December 29, 1978Date of Patent: August 11, 1981Assignee: Dynamit Nobel AGInventors: Gunther Bernhardt, Gerhard Daum
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Patent number: 4282160Abstract: The present invention is concerned with novel compounds useful in photographic products and processes comprising triarylmethane dyes possessing in their triaryl structure a 4'-oxo-1'-naphthylidene (or a 4'-oxo-1'-phenylidene) moiety and a phenyl moiety substituted in the ortho-position to the central carbon atom with the group ##STR1## wherein R is an alkyl group or a phenyl group, unsubstituted or substituted with a solubilizing group and Y is an electron-withdrawing group.Type: GrantFiled: May 22, 1980Date of Patent: August 4, 1981Assignee: Polaroid CorporationInventor: James W. Foley
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Patent number: 4278816Abstract: Phenols and thiophenols are produced by reacting the corresponding diphenyl ether compound with hydrogen sulfide in contact with an absorptive catalyst, such as charcoal, activated carbon, calcined petroleum coke, etc. Temperatures in the range of from about 300.degree. to about 900.degree. C. are employed.Type: GrantFiled: August 26, 1977Date of Patent: July 14, 1981Assignee: Stauffer Chemical CompanyInventor: Kyung-sup Shim
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Patent number: 4232175Abstract: Aromatic compounds in an acidic, aqueous solution can be economically nitrosated by treatment with the hydration products of oxides of nitrogen at a temperature in the range of -15.degree. C. to 10.degree. C. The oxides of nitrogen are generated as a gas from a separate solution or slurry by the reaction of an alkali metal nitrate with a strong mineral acid at a temperature in the range of 15.degree. C. to 35.degree. C. This method of nitrosation employs relatively inexpensive reagents, but can be carried on continuously and produces unexpectedly high yield of para-nitrosated product from a monosubstituted starting material.Type: GrantFiled: December 8, 1977Date of Patent: November 4, 1980Assignee: The Dow Chemical CompanyInventors: William E. Smith, Thomas W. McGee
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Patent number: 4229595Abstract: Preparation of nitro compounds of phenols and alkyl substituted derivatives thereof which includes nitrosating phenols or alkyl derivative thereof, oxidizing the nitroso compound, separating off nitrogen oxides, separating nitro compounds from reaction mixture, and subjecting mother liquor and washing liquids to destructive oxidation at elevated temperatures and recycling nitrogen oxides and nitric acid.Type: GrantFiled: September 25, 1978Date of Patent: October 21, 1980Assignee: Aktiebolaget BoforsInventors: Erik Bengtsson, Boris Holm
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Patent number: 4215227Abstract: A process for preparing alkali metal salts of para-nitrophenol by contacting para-chloronitrobenzene with an aqueous solution of (1) aqueous caustic and (2) recycled filtrate and washing solution from the preparation of para-nitrophenol containing 5-20% by weight of said alkali metal salts at a temperature of from 180.degree.-250.degree. C. and at autogenous pressure in 30 seconds to 10 minutes with the mole ratio of caustic to chloronitrobenzene of from 2:1-4:1, caustic concentration in the aqueous solution of from 5-20%, the amount of recycle ranging from 5-45% by weight based on the aqueous solution.Type: GrantFiled: October 27, 1978Date of Patent: July 29, 1980Assignee: E. I. Du Pont de Nemours and CompanyInventor: Richard E. Bockrath
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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: 4115652Abstract: A process for the preparation of an amino-nitro-phenol by partial reduction of a polynitrophenol by contacting the polynitrophenol with an aqueous ammonia solution and a sulfide ion, the ammonia being present in an amount of 1 to 8 mols ammonia per mol of polynitrophenol and the sulfide being present in an amount of 2.5 to 6 mols sulfide ion per mol polynitrophenol, the process being conducted at a temperature of from room temperature to 100.degree. C.Type: GrantFiled: March 30, 1977Date of Patent: September 19, 1978Assignee: Bayer AktiengesellschaftInventors: Karl Linhart, Adolf Friedrich
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Patent number: 4112005Abstract: The present invention relates to an improved continuous process for the preparation of mononitro-aromatic compounds which comprises (1) nitrating a reactive aromatic compound in the absence of sulphuric acid until mono-nitration is essentially complete, said nitration being carried out in 40 to 68% strength by weight nitric acid, (2) separating mechanically the nitration reaction mixture into an inorganic phase and an organic phase, (3) washing of the organic phase with water and dilute alkali solution and subsequent separation of the unconverted starting material end of the adhering water by means of rectification (4) feeding the inorganic phase and, if necessary, the wash water of the first water wash of the organic phase, to a rectification column in which (a) water is withdrawn over the top (b) optionally a fraction which has a lower nitric acid content than the feed is withdrawn from a sidestream takeoff in the rectifying section of the column and (c) a fraction which has a higher nitric acid content thaType: GrantFiled: May 9, 1977Date of Patent: September 5, 1978Assignee: Bayer AktiengesellschaftInventors: Karl-Werner Thiem, Adolf Hamers, Josef Heinen
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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: 4097527Abstract: Phenolic antioxidants such as 1,1-dimethyl-2-(3,5-di tert.butyl-4-hydroxyphenyl) ethyl amine and a method of preparing said antioxidants involving the reaction between a 3,5-di tert.alkyl-4-hydroxybenzyl halide; N,N-dialkyl amine or dithiocarbamate such as 3,5-di tert.butyl-4-hydroxybenzyl chloride; 2,6-di tert.butyl-4-dimethylaminomethylphenol or 3,5-di tert.butyl-4-hydroxybenzyl N,N-dimethyldithiocarbamate and a nitroalkane such as 2-nitropropane to produce a nitro compound such as 1,1-dimethyl-2-(3,5-di tert.butyl-4-hydroxyphenyl)-1-nitroethane which can be catalytically reduced to form the aminoalkyl phenol.Type: GrantFiled: December 9, 1971Date of Patent: June 27, 1978Assignee: The Goodyear Tire & Rubber CompanyInventor: Richard H. Kline