Preparing From A Phenol And An Aldehyde Or Ketone Patents (Class 568/727)
  • Patent number: 4387251
    Abstract: A process for the preparation of bisphenols, which comprises condensing an aliphatic or cycloaliphatic ketone with a phenol having a free p-position in the presence, as a condensing agent, of from 0.3 to 3 mols, per mol of ketone, of an aromatic sulphonic acid of the formula (III) or (IV): ##STR1## wherein R.sup.3 is an inert organic radical,o represents an integer from 1 to 4, andp represents 0 or an integer from 1 to 4, and in the presence of an organic solvent, in which the aromatic sulphonic acid is effectively soluble and the bisphenol or the phenol adduct which is produced is as slightly soluble as possible, the reaction being carried out at a temperature at which the produced diphenol crystallises as extensively as possible as such or as a phenol adduct during or at the end of the reaction; isolating the crystalline separated bisphenol or its adduct; and removing the adhering phenol or solvent.
    Type: Grant
    Filed: July 20, 1981
    Date of Patent: June 7, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Heinrich Meyer, Ludwig Bottenbruch, Wolfgang Jakob
  • Patent number: 4375567
    Abstract: A method is provided for making bisphenol-A based on the condensation of acetone and phenol in the presence of an ion-exchange resin. Improved yields of 2,2-bis(4-hydroxyphenyl)propane is achieved by recycling bisphenol-A reaction mixture containing significant amounts of 2,4'-dihydroxy-2,2-diphenyl propane based on the use of a macroreticular ion-exchange resin.
    Type: Grant
    Filed: August 21, 1981
    Date of Patent: March 1, 1983
    Assignee: General Electric Company
    Inventor: Gary R. Faler
  • Patent number: 4369293
    Abstract: A catalyst for the preparation of bisphenols from phenols and compounds containing carbonyl groups consisting of a styrene/divinyl benzene copolymer into which are introduced sulphochloride groups which, in turn, have been partly reacted with mercaptoalkylamine and partly hydrolyzed to form sulphonic acid groups.
    Type: Grant
    Filed: June 12, 1981
    Date of Patent: January 18, 1983
    Assignee: Bayer Aktiengesellschaft
    Inventors: Frieder Heydenreich, Claus Wulff, Lothar Klein, Hans-Jurgen Meissner, Norbert Bachem
  • Patent number: 4365099
    Abstract: A method of improving the performance of cationic exchange catalysts used in the production of bisphenols from phenolic compounds and carbonyl compounds by pretreating the phenolic compound with a chelating resin to remove metallic impurities.
    Type: Grant
    Filed: May 12, 1981
    Date of Patent: December 21, 1982
    Assignee: General Electric Company
    Inventors: Gary R. Faler, Ashok K. Mendiratta
  • Patent number: 4365098
    Abstract: Fluorinated bisphenols having a fluorinated alkyl group and a hydrogen atom upon the methylene carbon atom are prepared at atmospheric pressure or at low pressures from a phenol reactant and a fluorinated aldehyde compound in the presence of gaseous hydrogen chloride or gaseous hydrogen bromide catalyst. The fluroinated bisphenols having the fluorinated alkyl group and a hydrogen atom upon the methylene carbon atom are produced in excellent yields and are used for making flame-retardant polycarbonates and polyester-carbonate copolymers.
    Type: Grant
    Filed: December 31, 1980
    Date of Patent: December 21, 1982
    Assignee: General Electric Company
    Inventors: Victor Mark, Charles V. Hedges
  • Patent number: 4348542
    Abstract: 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: Grant
    Filed: July 9, 1980
    Date of Patent: September 7, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Volker Serini, Rainer Neumann, Gerhard Friedhofen, Dieter Freitag, Jurgen Heuser, Hans-Helmut Schwarz
  • Patent number: 4346247
    Abstract: A sulfonated polystyrene ion-exchange resin is provided having organo mercaptan groups attached to backbone sulfone radicals by covalent nitrogen-sulfur linkages. The ion-exchange resin can be used to effect phenol-ketone condensation in the synthesis of bisphenols.
    Type: Grant
    Filed: July 24, 1981
    Date of Patent: August 24, 1982
    Assignee: General Electric Company
    Inventors: Gary R. Faler, George R. Loucks
  • Patent number: 4334106
    Abstract: An improved process is provided for the preparation of a certain class of hydroxyphenyl-indanol compounds by the cyclization of a phenol selected from the group consisting of an isopropenylphenol, oligomers thereof, and mixtures of any of said group in any combination and proportion, by dissolving said phenol in a stoichiometric excess of an organic acid selected from the group consisting of trifluoroacetic acid, trichloroacetic acid, difluoroacetic acid, dichloroacetic acid, fluoroacetic acid, chloroacetic acid, formic acid, and mixtures thereof at a temperature falling within a range of from about 0.degree. C. to about 90.degree. C. to form a solution; and maintaining said solution at a temperature falling within the above said range until the formation of said indanol is substantially complete.The dihydroxy compounds produced by the present method are useful in the preparation of epoxy, alkyd, and urethane resins in particular.
    Type: Grant
    Filed: February 5, 1981
    Date of Patent: June 8, 1982
    Assignee: The Upjohn Company
    Inventor: Shenghong A. Dai
  • Patent number: 4320215
    Abstract: A method of preventing scale formation and adhesion onto the surfaces of a polymerization vessel and auxilliary equipment used in polymerization of vinyl chloride monomer, wherein the surfaces are coated prior to polymerization with a coating agent having the concurrent properties of (a) one or more functional groups having the ability to chelate, (b) one or more functional groups having the ability to inhibit action of free radicals, and (c) substantial insolubility to vinyl chloride monomer and insoluble to water. The concurrent presences of these functional characteristics syngergistically act to prevent scale adhesion onto the surfaces after substantial numbers of repeated polymerization charges.
    Type: Grant
    Filed: November 7, 1979
    Date of Patent: March 16, 1982
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Kazuya Yonezawa, Tadashi Osawa
  • Patent number: 4319053
    Abstract: A process for the preparation of a 4,4'-dihydroxy-3,3',5,5'-tetraalkyl-diphenylalkane by reacting a 2,6-dialkyl phenol with a ketone in the presence of an acid organic ion exchanger wherein said acid ion exchanger is a macroporous resin with an average pore diameter of at least 300 A.
    Type: Grant
    Filed: October 11, 1977
    Date of Patent: March 9, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Jurgen Heuser, Gunther Jeromin, Hans-Helmut Schwarz, Gerhard Friedhofen
  • Patent number: 4319052
    Abstract: A method for preparing sterically hindered bis- or polyphenols of the formula: ##STR1## wherein R' is hydrogen, a C.sub.1 -C.sub.4 alkyl; R" and R"' the same or different and are each: ##STR2## wherein R is a tertiary C.sub.4 -C.sub.8 alkyl, R.sub.1 and R.sub.2 are the same or different and represent a C.sub.1 -C.sub.8 alkyl or a C.sub.6 -C.sub.8 cycloalkyl, or a C.sub.7 -C.sub.9 aralkyl, which comprises reacting the starting sterically hindered 2,4,6-trialkylphenols of the formula: ##STR3## wherein A is a C.sub.1 -C.sub.8 alkyl or a C.sub.6 -C.sub.8 cycloalkyl or a C.sub.7 -C.sub.9 aralkyl or a 3,5-dialkyl-2-hydroxybenzyl of the formula: ##STR4## B is a C.sub.1 -C.sub.8 alkyl, or a C.sub.6 -C.sub.8 cycloalkyl, or a C.sub.7 -C.sub.9 aralkyl, or a 3,5-dialkyl-4-hydroxybenzyl of the formula: ##STR5## wherein R.sub.1 and R are as identified above, with acetals, aldehydes or donors of C.sub.1 -C.sub.5 aldehydes in an acidic medium at a temperature within the range of from 60.degree. to 200.degree. C.
    Type: Grant
    Filed: August 5, 1977
    Date of Patent: March 9, 1982
    Inventors: Evgeny L. Styskin, Yakov A. Gurvich, Simona T. Kumok, Olga F. Starikova, Grigory I. Rutman, Jury I. Michurov, Vladimir A. Yanshevsky, Vladimir K. Gusev, Alexandr G. Liakumovich
  • Patent number: 4317944
    Abstract: The rate of reaction between acetone and phenol in the presence of an acidic catalyst to form 2,2-bis(4-hydroxyphenyl) propane can be accelerated by employing an aliphatic alcohol with the reactants.
    Type: Grant
    Filed: August 15, 1980
    Date of Patent: March 2, 1982
    Assignee: General Electric Company
    Inventor: Gary C. Davis
  • Patent number: 4308405
    Abstract: An improved continuous process for preparing bisphenols from phenols and carbonyl compounds in the presence of an acidic ion-exchange resin is described. The improvement comprises recycling a portion of the stream containing bisphenol to the reaction zone before the bisphenol is recovered therefrom.
    Type: Grant
    Filed: July 5, 1978
    Date of Patent: December 29, 1981
    Assignee: Shell Oil Company
    Inventor: Arien Kwantes
  • Patent number: 4308404
    Abstract: An improved continuous process for preparing bisphenols from phenols and carbonyl compounds in the presence of an acidic ion-exchange resin is described wherein the reaction zone comprises at least two reactors in series and a part the effluent from at least one reactor, with the exception of the last reactor, is recycled.
    Type: Grant
    Filed: July 5, 1978
    Date of Patent: December 29, 1981
    Assignee: Shell Oil Company
    Inventors: Arien Kwantes, Arie Van Dongen, Hendrik A. C. Groeneveld
  • Patent number: 4301305
    Abstract: The dian is prepared by the condensation of phenol with acetone in the presence of acid ion-exchange catalyst of the type of sulfonated co-polymer of styrene and divinylbenzene. The three-stage process is conducted in two reactors packed with a stationary catalyst bed. In each of the reactors the bed height is 5-20 m and in addition, in both reactors the beds are divided into bottom and upper zones.At various stages of the process, a reaction mixture is circulated with a different linear velocity, the first step of the process being conducted at a temperature of 60.degree.-85.degree. C. in the bed of the first reactor, in succession in the bottom and then upper zone of the catalytic bed; the second stage of the process is accomplished in the bottom zone of the second reactor at a temperature of 70.degree.-90.degree. C.; and the third step is carried out in the upper zone of the second reactor at a temperature of 75.degree.-95.degree. C.
    Type: Grant
    Filed: December 28, 1979
    Date of Patent: November 17, 1981
    Assignee: Instytut Ciezkiej Syntezy Organicznej "Blachownia"
    Inventors: Maciej Kiedik, Jozef Kolt, Jerzy Czyz, Edward Grzywa, Anna Niezgoda, Kazimierz Terelak
  • Patent number: 4294995
    Abstract: A sulfonated polystyrene ion-exchange resin is provided having organo mercaptan groups attached to backbone sulfone radicals by covalent nitrogen-sulfur linkages. The ion-exchange resin can be used to effect phenol-ketone condensation in the synthesis of bisphenols.
    Type: Grant
    Filed: December 13, 1979
    Date of Patent: October 13, 1981
    Assignee: General Electric Company
    Inventors: Gary R. Faler, George R. Loucks
  • Patent number: 4278821
    Abstract: This invention describes novel intermediate alkanols for making effective compounds, which intermediates are .omega.,.omega.-bis(dialkylhydroxyphenyl) alkanols having the formula: ##STR1## wherein R.sub.1 is a tertiary alkyl group having 4-8 carbon atoms;R.sub.2 is alkyl having 1-4 carbon atoms;R.sub.3 is a straight chain or branched alkylene group having 1-4 carbon atoms; andx is 1-4.
    Type: Grant
    Filed: August 1, 1979
    Date of Patent: July 14, 1981
    Assignee: GAF Corporation
    Inventor: David J. Tracy
  • Patent number: 4239919
    Abstract: An improved process for obtaining bisphenols by reaction of a phenol, or substituted phenol having a hydrogen in the para position, and an alkenyl ether, wherein the unsaturation in the ether is in the alpha position, in the presence of a strong acid catalyst. The process gives particularly good results when bisisopropenyl ether is reacted with phenol in the presence of a strong acid cation exchange resin in which part of the exchange sites have been neutralized with 2,2-dimethylthiazolidine.
    Type: Grant
    Filed: June 12, 1979
    Date of Patent: December 16, 1980
    Assignee: The Dow Chemical Company
    Inventor: Thomas J. Hairston
  • Patent number: 4233465
    Abstract: A method is provided for fractionation of oil obtained by pyrolysis of lignocellulosic materials to obtain useful chemical fractions, including a phenolic fraction which is suitable as a total or partial replacement for phenol in making phenol-formaldehyde resins. The method comprises mixing the oil with a strong base such as sodium hydroxide to a pH level at which the neutral fraction of the oil is selectively soluble in a solvent such as methylene chloride or ether, and the mixture is extracted with the solvent to obtain a first extract containing the solvent and the neutral fraction, and a first raffinate containing the remaining fractions of the oil, i.e., the phenolic fraction, the organic acids fraction and an amorphous residue. The neutral fraction is recovered by distillation and the first raffinate is mixed with sulfuric acid to lower its pH to a level at which the phenolic fraction is selectively soluble in the solvent.
    Type: Grant
    Filed: November 29, 1978
    Date of Patent: November 11, 1980
    Assignee: American Can Company
    Inventors: Robert M. Gallivan, Peter K. Mattschei
  • Patent number: 4192959
    Abstract: A process for the preparation of pure 2-hydroxybenzyl alcohol, pure 4-hydroxybenzyl alcohol or a mixture of both hydroxybenzyl alcohols by reacting phenol and formaldehyde in the presence of a basic catalyst and subjecting the resulting reaction mixture to an at least 2-stage countercurrent extraction in a solvent system of water/organic solvent which is water-immiscible or water-miscible only to a limited extent.
    Type: Grant
    Filed: June 14, 1978
    Date of Patent: March 11, 1980
    Assignee: Haarmann & Reimer
    Inventors: Kurt Bauer, Alfred Krempel, Reiner Molleken, Karlfried Wedemeyer, Helmut Fiege
  • Patent number: 4191843
    Abstract: 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: Grant
    Filed: November 7, 1978
    Date of Patent: March 4, 1980
    Assignee: Shell Oil Company
    Inventors: Arien Kwantes, Pieter A. Gautier
  • Patent number: 4178466
    Abstract: Phenyl trichloro-ethanes can be prepared by reacting chloral with a phenol compound, such as phenol itself or 2,6-xylenol in HF, which acts both as a catalyst and solvent medium.
    Type: Grant
    Filed: March 15, 1978
    Date of Patent: December 11, 1979
    Assignee: General Electric Company
    Inventors: Russell A. Gardner, Charles M. Orlando
  • Patent number: 4160110
    Abstract: A process is provided for improving the stability of bisphenols under melt or distillation conditions by employing an aromatic anhydride such as phthalic anhydride as a stabilizing agent. A reduction is effected in the rate of formation of phenol and other cracking products which are decomposition by-products of the bisphenol.
    Type: Grant
    Filed: April 17, 1978
    Date of Patent: July 3, 1979
    Assignee: General Electric Company
    Inventor: James C. Carnahan, Jr.
  • Patent number: 4147643
    Abstract: Compositions useful as additives for fuels and lubricants can be made by reacting (A) an aromatic compound having an OH or SH group attached to an aromatic nucleus and an aromatic hydrogen atom (e.g., a substituted phenol wherein the substituent is an alkyl group of at least 50 carbon atoms); (B) an aldehyde or reactive equivalent thereof (e.g., formaldehyde); (C) a non-amino hydrogen, active hydrogen compound (e.g., a phenol, N,N-dimethyl aniline, etc.) and optionally, (D) an aliphatic alkylating agent of at least 12 carbon atoms (e.g., a polyisobutene of about 50 carbon atoms).
    Type: Grant
    Filed: June 17, 1976
    Date of Patent: April 3, 1979
    Assignee: The Lubrizol Corporation
    Inventors: John F. Pindar, Jerome M. Cohen