Acyclic Polycarbon Hydrocarbyl Group Bonded Directly To The Benzene Ring Patents (Class 568/780)
  • Patent number: 4533767
    Abstract: Selective catalytic steam dealkylation of ortho- and para-positions of alkylated phenols is accomplished by reacting ortho- and/or para-alkylated phenols with steam in the presence of a catalyst comprised of magnesium oxide, optionally manganese oxide and optionally an organic binder; said reaction may preferably takes place in the presence of an oxidizing atmosphere to extend catalyst life. High degrees of conversion are obtained without loss of the hydroxyl radical of the alkylated phenols.
    Type: Grant
    Filed: May 3, 1984
    Date of Patent: August 6, 1985
    Assignee: General Electric Company
    Inventor: John J. Talley
  • Patent number: 4517389
    Abstract: By flowing a gaseous stream containing methanol and a phenol through a fluidized bed of particles of a highly attrition resistant catalyst comprising 10 to 80% by weight of silica and 90 to 20% by weight of a metal oxide supported on the silica and have been calcined at 500.degree. to 900.degree. C., the ortho position of the phenol is methylated with high selectivity, whereby various useful ortho-methylated phenol derivatives can be advantageously obtained.
    Type: Grant
    Filed: August 8, 1983
    Date of Patent: May 14, 1985
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Tsutomu Katsumata, Masahisa Yokota
  • Patent number: 4499312
    Abstract: A process is disclosed for separating 3,5-xylenol or 3,4-xylenol from other closely boiling polymethylated phenolics by treating a mixture of the phenolics with a metal halide salt. The metal halide salt preferentially forms a complex with the xylenol over other related phenolics in the mixture. The preferentially-formed complex of the xylenol may then be isolated from the mixture and the complex decomposed to provide a product substantially enriched in, or substantially entirely composed of the xylenol.
    Type: Grant
    Filed: February 21, 1984
    Date of Patent: February 12, 1985
    Assignee: Koppers Company, Inc.
    Inventor: Gerd Leston
  • Patent number: 4496774
    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: July 23, 1984
    Date of Patent: January 29, 1985
    Assignee: Koppers Company, Inc.
    Inventor: Gerd Leston
  • Patent number: 4482758
    Abstract: For the orthomethylation of phenolic compounds containing at least one hydrogen atom in the ortho position, the phenol compound is reacted with methanol in the gaseous phase in the presence of an oxidic catalyst containing iron, chromium, and cerium in an atomic ratio of Fe:Cr:Ce of 1:0.005 to 0.1:0.005 to 0.1, at temperatures of 270.degree.-450.degree. C., pressures of 1-40 bar, and rates per unit volume of 0.05-3 h.sup.-1. The temperature within the catalyst bed is maintained constant within a narrow temperature range .DELTA.T of up to 20.degree. C. The catalyst has a very long service life with a high activity, and provides a high selectivity.
    Type: Grant
    Filed: December 13, 1982
    Date of Patent: November 13, 1984
    Assignee: Chemische Werke Huels AG
    Inventor: Reinhard Seig
  • Patent number: 4480140
    Abstract: 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: Grant
    Filed: March 16, 1983
    Date of Patent: October 30, 1984
    Assignee: Koppers Company, Inc.
    Inventor: Gerd Leston
  • Patent number: 4479019
    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: February 21, 1984
    Date of Patent: October 23, 1984
    Assignee: Koppers Company, Inc.
    Inventor: Gerd Leston
  • Patent number: 4476329
    Abstract: A method is provided for producing o-cresol by simultaneously alkylating phenol with methanol and transalkylating 2,6-xylenol with phenol in the same reactor.
    Type: Grant
    Filed: April 4, 1983
    Date of Patent: October 9, 1984
    Assignee: General Electric Company
    Inventors: Gregory R. Chambers, John J. Talley
  • Patent number: 4475001
    Abstract: Ortho- or para-monoalkylated phenols or 2,4- or 2,6-dialkylphenols can be produced from phenolic compounds in good yields and in the absence of isomers. The starting phenol which has at least two available ortho or para positions unsubstituted is converted to a t-alkylated phenol having at least one ortho or para position unsubstituted. The desired t-alkylated phenolic compound is reacted with an aldehyde having one to four carbon atoms and a secondary aliphatic or alicyclic 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 secondary amine. The reaction is conducted at a temperature in the range of about 0.degree. C., to about 100.degree. C. and the reaction produces an aminoalkylated t-alkylated phenol. The aminoalkylated phenol 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: Grant
    Filed: March 17, 1983
    Date of Patent: October 2, 1984
    Assignee: Koppers Company, Inc.
    Inventor: Gerd Leston
  • Patent number: 4475002
    Abstract: An improved process for preparing m-alkylhydroxybenzene which comprises heating alkylbenzene or an isomeric mixture of alkylbenzenesulfonic acid in the presence of sulfuric acid and an inorganic salt at a temperature of from 150.degree. to 210.degree. C. to form an isomeric mixture of alkylbenzenesulfonic acid which is rich in the m-isomer, selectively hydrolyzing the isomers of alkylbenzenesulfonic acid other than the m-isomer, and caustically fusing the unhydrolyzed alkylbenzenesulfonic acid.
    Type: Grant
    Filed: November 26, 1982
    Date of Patent: October 2, 1984
    Assignee: Taoka Chemical Company, Limited
    Inventors: Mitsuhiro Wada, Seizi Maki
  • 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: 4451676
    Abstract: p-Alkenyl phenols are prepared by reacting an alkylated phenol having a replaceable hydrogen atom at the 4- position with an aliphatic aldehyde having two carbon atoms up to at least 20 carbon atoms in the molecule and a secondary amine.
    Type: Grant
    Filed: August 27, 1982
    Date of Patent: May 29, 1984
    Assignee: Ethyl Corporation
    Inventor: Charles R. Everly
  • Patent number: 4419529
    Abstract: 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: Grant
    Filed: March 3, 1982
    Date of Patent: December 6, 1983
    Assignee: Riedel-de Haen Aktiengesellschaft
    Inventor: Arthur Steinmetz
  • Patent number: 4398047
    Abstract: 2-Substituted-4,6-di-t-butylresorcinol represented by the general formula: ##STR1## wherein R represents a straight or branched alkyl group having 1 to 20 carbon atoms, a straight or branched alkenyl group having 2 to 20 carbon atoms and at least one double bond, or an aralkyl group, wherein no tertiary carbon atom of R is directly bonded to the benzene nucleus, is prepared by allowing 4,6-di-t-butylresorcinol to react with a halogen compound represented by the general formula:RXwherein R has the same meaning as defined above, and X represents a halogen atom, excluding the X bonded to a tertiary carbon of R, in an aqueous alkali solution. By further debutylization of the 2-substituted-4,6-t-butylresorcinol, 2-substituted resorcinol represented by the general formula: ##STR2## wherein R has the same meaning as defined above, but the tertiary carbon of R is free from direct bonding to the benzene nucleus, is prepared.
    Type: Grant
    Filed: February 23, 1982
    Date of Patent: August 9, 1983
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yukihisa Takisawa, Shinichi Hasegawa
  • Patent number: 4394526
    Abstract: Para-cresol is separated from a mixture comprising meta-cresol and various other methylated and ethylated phenols by preferentially complexing the para-cresol with one or more anhydrous or dehydrated inorganic salts selected from the group consisting of calcium bromide, lithium bromide, manganese bromide and magnesium chloride. The anhydrous inorganic salt is added to the phenolic mixture in an amount to give a mole ratio of salt to para-cresol in the mixture in the range of about 0.5 mole to one to about 1.5 mole to one. The para-cresol and salt form a complex and the complex is removed from the mixture of methylated and ethylated phenols. Then the complex is decomposed to recover the para-cresol and salt; the recovered salt may be recycled to complex with more para-cresol.
    Type: Grant
    Filed: September 26, 1980
    Date of Patent: July 19, 1983
    Assignee: Koppers Company, Inc.
    Inventor: Gerd Leston
  • Patent number: 4386224
    Abstract: A method for stabilizing color, inhibiting color development, and reducing color of monoalkyl phenols by incorporation of N,N-diethylhydroxylamine, preferably from about 5 parts per million to about 50 parts per million. Also a color stabilized monoalkyl phenol composition comprising a monoalkyl phenol and a color stabilizing amount of N,N-diethylhydroxylamine.
    Type: Grant
    Filed: August 31, 1981
    Date of Patent: May 31, 1983
    Assignee: Monsanto Company
    Inventor: Gerbrand Deetman
  • Patent number: 4371714
    Abstract: A process for the selective alkylation of phenol or its alkyl ethers, in the presence of a particular type of zeolite catalyst, to produce a product rich in 4-alkyl phenyl alkyl ethers (e.g. 4-methylanisole). The zeolite is characterized by a Constraint Index of 1 to 12 and a silica to alumina mole ratio of at least 12, and may optionally contain a minor amount of a difficultly reducible oxide.
    Type: Grant
    Filed: December 30, 1980
    Date of Patent: February 1, 1983
    Assignee: Mobil Oil Corporation
    Inventor: Lewis B. Young
  • Patent number: 4316995
    Abstract: Described in a process for preparing food grade paravinyl phenol using as a starting material parahydroxybenzaldehyde whereby the parahydroxybenzaldehyde is first reacted with malonic acid and is then decarboxylated in one step to form an impure paravinyl phenol. The impure paravinyl phenol is then acetylated to form paraacetoxy phenol which is separated from the impurities and hydrolyzed thereby yielding food grade, substantially pure, paravinyl phenol.
    Type: Grant
    Filed: February 5, 1981
    Date of Patent: February 23, 1982
    Assignee: International Flavors & Fragrances Inc.
    Inventors: Alan O. Pittet, Ranya Muralidhara
  • Patent number: 4306097
    Abstract: Cycloalkanones, cycloalkanols and unsaturated analogs thereof, 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: Grant
    Filed: September 8, 1980
    Date of Patent: December 15, 1981
    Assignee: Pfizer Inc.
    Inventors: Charles A. Harbert, Michael R. Johnson, Lawrence S. Melvin, Jr.
  • Patent number: 4288583
    Abstract: Curable mixtures of(a) maleimides of the general formula I ##STR1## wherein R is an n-valent aliphatic or aromatic radical, and n is the number 1,2 or 3; and(b) mono- or polyvalent phenols which contain in the molecule at least one 1-propenyl group in the ortho- or para-position with respect to the hydroxyl group, or isomeric mixtures of mono- or polyvalent phenols which are propenyl-substituted in the ortho- or para-position and mono- or polyvalent phenols which are allyl-substituted in the ortho- or para-position, the proportion of propenyl groups in the isomeric mixture having to be at least 5 equivalent-%, relative to the sum of the equivalents of propenyl and allyl groups.The novel mixtures cure at elevated temperatures relatively rapidly, and produce moulded materials having valuable mechanical properties.
    Type: Grant
    Filed: December 17, 1979
    Date of Patent: September 8, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Abdul-Cader Zahir, Siegfried Wyler
  • Patent number: 4283572
    Abstract: A process for the conversion of an alkyl phenyl ether to the corresponding alkylphenol, involving heating in the presence of a dehydrated sulfonic acid type cation exchange resin having a macroreticular structure. The process has particular application to the recovery of unreacted alkylphenol from a product mixture resulting from a reaction in which the alkylphenol is used (in stoichiometrically excessive amounts) as a reactant.
    Type: Grant
    Filed: December 27, 1979
    Date of Patent: August 11, 1981
    Assignee: Borg-Warner Corporation
    Inventor: James D. Klicker
  • 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: 4272637
    Abstract: A catalyst for oxidation of isobutylene which has a composition of the general formulaMo.sub.a Bi.sub.b Fe.sub.c Co.sub.d Ni.sub.e P.sub.f Pb.sub.g X.sub.h O.sub.iwherein X is at least one alkali metal element selected from K, Rb and Cs; a, b, c, d, e, f, g and h respectively represent the number of Mo, Bi, Fe, Co, Ni, P, Pb and X atoms, and when a is 12, b is 0.1-10, c is 9-20, d is 0-12, e is 0-12 with the proviso that the sum of d and e is 0.5-15, f is 0.1-5, g is 0.05-8 and h is 0.01-5; and i is the number of oxygen atoms which satisfies the atomic valences of the other elements.
    Type: Grant
    Filed: December 20, 1978
    Date of Patent: June 9, 1981
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Haruhisa Yamamoto, Nobuaki Yoneyama, Shinichi Akiyama
  • Patent number: 4258221
    Abstract: Alkylenebisphenols are converted or cleaved to phenols and alkyl- and/or alkenyl-substituted phenols in good yields by contacting with hydrogen in the presence of a nickel oxide/manganese oxide/metal oxide supported catalyst. In a specific embodiment, bisphenol A is converted to isopropylphenol at high selectivity and high conversion by contacting with hydrogen in the presence of a nickel oxide/manganese oxide/magnesium oxide catalyst.
    Type: Grant
    Filed: April 11, 1979
    Date of Patent: March 24, 1981
    Assignee: Phillips Petroleum Company
    Inventors: Ronald D. Knudsen, Geir Bjornson
  • Patent number: 4215229
    Abstract: Ortho- and para-monoalkylated phenols and 2,4- and 2,6-dialkylphenols can be produced from phenolic compounds in good yields. The phenolic compound is reacted with an aldehyde having one to ten carbon atoms and a secondary aliphatic amine having a basic dissociation constant, pK.sub.b, of less than about 3.6 measured at 25.degree. C. The reaction is conducted in the liquid phase with at least a stoichiometric amount of the phenolic compound, the aldehyde and the secondary amine, or with an excess of the phenolic compound with the stoichiometric amounts of the aldehyde and the secondary amine. The reaction is conducted at a temperature in the range of around 0.degree. C. to about 25.degree. C., and the reaction produces an aminoalkylated phenol. The aminoalkylated phenol is contacted with hydrogen in the presence of a metal catalyst at a temperature of about 120.degree. C. to about 140.degree. C.
    Type: Grant
    Filed: June 15, 1978
    Date of Patent: July 29, 1980
    Assignee: Koppers Company, Inc.
    Inventor: Nicholas P. Greco
  • Patent number: 4196089
    Abstract: Preparation of overbased magnesium sulfurized phenates having total base members in the range of about 200 to about 275 by a two-stage procedure, the first stage of which involves dissolving a sulfurized oil-soluble aliphatic hydrocarbyl-substituted phenol, particularly a C.sub.6 -C.sub.30 alkyl phenol, in certain types of high boiling organic polar solvents, exemplified particularly by methyl "Cellosolve," and admixing therewith magnesium oxide in an amount such that, upon refluxing the mixture, a fully neutralized sulfurized alkyl phenol results; and wherein, in the second stage of said procedure, the composition produced in the first stage of the procedure is overbased by admixing therewith a magnesium alkoxide carbonate complex in an amount such as to produce the final overbased magnesium sulfurized phenate compositions having the aforesaid total base number.
    Type: Grant
    Filed: June 20, 1978
    Date of Patent: April 1, 1980
    Assignee: Witco Chemical Corporation
    Inventors: Charles L. Pitzer, Norman Jacobson
  • Patent number: 4147726
    Abstract: 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: Grant
    Filed: November 8, 1976
    Date of Patent: April 3, 1979
    Assignee: Phillips Petroleum Company
    Inventor: Yulin Wu
  • 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: 4113973
    Abstract: A process is disclosed for the preparation of anhydrous solutions of alkaline phenates in organic solvents, comprising the steps:(a) synthesis in water of alkaline phenates by the reaction of sodium sulphate or potassium sulphate with calcium hydroxide and a phenol of the general formula: ##STR1## wherein R and R', which may be the same or different from each other, are hydrogen atoms or linear alkyl groups having up to 4 carbon atoms, at a temperature substantially lower than 30.degree. C;(b) filtering the calcium sulphate;(c) quantitatively decalcifying the residual aqueous solution by the addition of an aqueous solution of NaOH or KOH, until a total concentration is reached which is at least equal to about 30% by weight of the total solution;(d) filtering the precipitated calcium hydroxide and alkaline sulphate;(e) extracting in countercurrent, at a temperature between 50.degree. and about 90.degree.
    Type: Grant
    Filed: July 19, 1977
    Date of Patent: September 12, 1978
    Assignee: Montedison S.p.A.
    Inventors: Enzo Alneri, Giorgio Bottaccio, Stefano Campolmi, Luigi Cassar
  • 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: 4096175
    Abstract: Covers a method of separating a nonionic surfactant from an anionic surfactant by use of methylal.
    Type: Grant
    Filed: December 1, 1976
    Date of Patent: June 20, 1978
    Assignee: Texaco Development Corporation
    Inventors: Carter G. Naylor, Simon P. Burns