Phenols (h Of -oh May Be Replaced By A Group Ia Or Iia Light Metal) Patents (Class 568/706)
  • Patent number: 4594459
    Abstract: 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: Grant
    Filed: March 25, 1985
    Date of Patent: June 10, 1986
    Assignee: The Dow Chemical Company
    Inventor: Kimio Inoue
  • Patent number: 4594460
    Abstract: 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: Grant
    Filed: March 19, 1985
    Date of Patent: June 10, 1986
    Assignee: Rhone-Poulenc Sante
    Inventors: Gerard Mignani, Didier Morel
  • Patent number: 4593129
    Abstract: 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: Grant
    Filed: April 18, 1984
    Date of Patent: June 3, 1986
    Assignee: Ethyl Corporation
    Inventors: R. Woodrow Wilson, Jr., Dustin H. Thomas
  • Patent number: 4558040
    Abstract: Certain miticidal (2-alkyl-3,4-dihydro-2H-1-benzopyran-8-yl)diazenecarboxylic acid esters.
    Type: Grant
    Filed: December 3, 1984
    Date of Patent: December 10, 1985
    Assignee: Shell Oil Company
    Inventors: Kurt H. Pilgram, Richard D. Skiles
  • Patent number: 4473713
    Abstract: 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: Grant
    Filed: September 27, 1982
    Date of Patent: September 25, 1984
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Serge Ratton
  • Patent number: 4447654
    Abstract: 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: Grant
    Filed: September 30, 1982
    Date of Patent: May 8, 1984
    Assignee: Koppers Company, Inc.
    Inventor: Gerd Leston
  • Patent number: 4435601
    Abstract: 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: Grant
    Filed: July 7, 1981
    Date of Patent: March 6, 1984
    Assignee: Rhone-Poulenc Industries
    Inventors: Karel Formanek, Daniel Michelet, Dominique Petre
  • Patent number: 4396783
    Abstract: 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: Grant
    Filed: September 4, 1981
    Date of Patent: August 2, 1983
    Assignee: Anic S.p.A.
    Inventors: Antonio Esposito, Marco Taramasso, Carlo Neri
  • Patent number: 4374293
    Abstract: Allylbenzene is converted to indene by means of a tungsten-containing catalyst.
    Type: Grant
    Filed: August 14, 1981
    Date of Patent: February 15, 1983
    Assignee: The Standard Oil Co.
    Inventors: J. D. Burrington, R. K. Grasselli, C. T. Kartisek
  • Patent number: 4347148
    Abstract: 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: Grant
    Filed: November 19, 1979
    Date of Patent: August 31, 1982
    Assignee: The Lubrizol Corporation
    Inventor: Kirk E. Davis
  • Patent number: 4290961
    Abstract: 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: Grant
    Filed: March 7, 1980
    Date of Patent: September 22, 1981
    Assignee: Montedison S.p.A.
    Inventors: Giovanni Mestroni, Grazia Zassinovich, Annamaria Camus
  • Patent number: 4284823
    Abstract: 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: Grant
    Filed: October 15, 1979
    Date of Patent: August 18, 1981
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Richard H. Kline
  • Patent number: 4283565
    Abstract: 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: Grant
    Filed: December 29, 1978
    Date of Patent: August 11, 1981
    Assignee: Dynamit Nobel AG
    Inventors: Gunther Bernhardt, Gerhard Daum
  • Patent number: 4282160
    Abstract: 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: Grant
    Filed: May 22, 1980
    Date of Patent: August 4, 1981
    Assignee: Polaroid Corporation
    Inventor: James W. Foley
  • Patent number: 4278816
    Abstract: 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: Grant
    Filed: August 26, 1977
    Date of Patent: July 14, 1981
    Assignee: Stauffer Chemical Company
    Inventor: Kyung-sup Shim
  • Patent number: 4232175
    Abstract: 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: Grant
    Filed: December 8, 1977
    Date of Patent: November 4, 1980
    Assignee: The Dow Chemical Company
    Inventors: William E. Smith, Thomas W. McGee
  • Patent number: 4229595
    Abstract: 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: Grant
    Filed: September 25, 1978
    Date of Patent: October 21, 1980
    Assignee: Aktiebolaget Bofors
    Inventors: Erik Bengtsson, Boris Holm
  • Patent number: 4215227
    Abstract: 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: Grant
    Filed: October 27, 1978
    Date of Patent: July 29, 1980
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Richard E. Bockrath
  • Patent number: 4120902
    Abstract: 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: Grant
    Filed: March 7, 1977
    Date of Patent: October 17, 1978
    Assignee: Phillips Petroleum Company
    Inventor: Yulin Wu
  • Patent number: 4115652
    Abstract: 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: Grant
    Filed: March 30, 1977
    Date of Patent: September 19, 1978
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl Linhart, Adolf Friedrich
  • Patent number: 4112005
    Abstract: 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 tha
    Type: Grant
    Filed: May 9, 1977
    Date of Patent: September 5, 1978
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Werner Thiem, Adolf Hamers, Josef Heinen
  • Patent number: 4101591
    Abstract: Haloloweralkyl ethynylbenzene compounds and their derivatives which are useful for the treatment for the relief of inflammation, pain and fever.
    Type: Grant
    Filed: November 23, 1976
    Date of Patent: July 18, 1978
    Assignee: William H. Rorer, Inc.
    Inventor: Julius Diamond
  • Patent number: 4097527
    Abstract: 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: Grant
    Filed: December 9, 1971
    Date of Patent: June 27, 1978
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Richard H. Kline