Preparing From A Phenol And An Aldehyde Or Ketone Patents (Class 568/727)
-
Patent number: 4387251Abstract: 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: GrantFiled: July 20, 1981Date of Patent: June 7, 1983Assignee: Bayer AktiengesellschaftInventors: Karl-Heinrich Meyer, Ludwig Bottenbruch, Wolfgang Jakob
-
Patent number: 4375567Abstract: 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: GrantFiled: August 21, 1981Date of Patent: March 1, 1983Assignee: General Electric CompanyInventor: Gary R. Faler
-
Patent number: 4369293Abstract: 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: GrantFiled: June 12, 1981Date of Patent: January 18, 1983Assignee: Bayer AktiengesellschaftInventors: Frieder Heydenreich, Claus Wulff, Lothar Klein, Hans-Jurgen Meissner, Norbert Bachem
-
Patent number: 4365099Abstract: 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: GrantFiled: May 12, 1981Date of Patent: December 21, 1982Assignee: General Electric CompanyInventors: Gary R. Faler, Ashok K. Mendiratta
-
Patent number: 4365098Abstract: 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: GrantFiled: December 31, 1980Date of Patent: December 21, 1982Assignee: General Electric CompanyInventors: Victor Mark, Charles V. Hedges
-
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
-
Patent number: 4346247Abstract: 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: GrantFiled: July 24, 1981Date of Patent: August 24, 1982Assignee: General Electric CompanyInventors: Gary R. Faler, George R. Loucks
-
Patent number: 4334106Abstract: 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: GrantFiled: February 5, 1981Date of Patent: June 8, 1982Assignee: The Upjohn CompanyInventor: Shenghong A. Dai
-
Patent number: 4320215Abstract: 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: GrantFiled: November 7, 1979Date of Patent: March 16, 1982Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Kazuya Yonezawa, Tadashi Osawa
-
Patent number: 4319053Abstract: 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: GrantFiled: October 11, 1977Date of Patent: March 9, 1982Assignee: Bayer AktiengesellschaftInventors: Jurgen Heuser, Gunther Jeromin, Hans-Helmut Schwarz, Gerhard Friedhofen
-
Patent number: 4319052Abstract: 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: GrantFiled: August 5, 1977Date of Patent: March 9, 1982Inventors: 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: 4317944Abstract: 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: GrantFiled: August 15, 1980Date of Patent: March 2, 1982Assignee: General Electric CompanyInventor: Gary C. Davis
-
Patent number: 4308405Abstract: 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: GrantFiled: July 5, 1978Date of Patent: December 29, 1981Assignee: Shell Oil CompanyInventor: Arien Kwantes
-
Patent number: 4308404Abstract: 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: GrantFiled: July 5, 1978Date of Patent: December 29, 1981Assignee: Shell Oil CompanyInventors: Arien Kwantes, Arie Van Dongen, Hendrik A. C. Groeneveld
-
Patent number: 4301305Abstract: 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: GrantFiled: December 28, 1979Date of Patent: November 17, 1981Assignee: Instytut Ciezkiej Syntezy Organicznej "Blachownia"Inventors: Maciej Kiedik, Jozef Kolt, Jerzy Czyz, Edward Grzywa, Anna Niezgoda, Kazimierz Terelak
-
Patent number: 4294995Abstract: 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: GrantFiled: December 13, 1979Date of Patent: October 13, 1981Assignee: General Electric CompanyInventors: Gary R. Faler, George R. Loucks
-
.omega.,.omega.-Bis(dialkylhydroxyphenyl) alkanols as intermediates in making effective antioxidants
Patent number: 4278821Abstract: 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: GrantFiled: August 1, 1979Date of Patent: July 14, 1981Assignee: GAF CorporationInventor: David J. Tracy -
Patent number: 4239919Abstract: 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: GrantFiled: June 12, 1979Date of Patent: December 16, 1980Assignee: The Dow Chemical CompanyInventor: Thomas J. Hairston
-
Patent number: 4233465Abstract: 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: GrantFiled: November 29, 1978Date of Patent: November 11, 1980Assignee: American Can CompanyInventors: Robert M. Gallivan, Peter K. Mattschei
-
Patent number: 4192959Abstract: 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: GrantFiled: June 14, 1978Date of Patent: March 11, 1980Assignee: Haarmann & ReimerInventors: Kurt Bauer, Alfred Krempel, Reiner Molleken, Karlfried Wedemeyer, Helmut Fiege
-
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
-
Patent number: 4178466Abstract: 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: GrantFiled: March 15, 1978Date of Patent: December 11, 1979Assignee: General Electric CompanyInventors: Russell A. Gardner, Charles M. Orlando
-
Patent number: 4160110Abstract: 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: GrantFiled: April 17, 1978Date of Patent: July 3, 1979Assignee: General Electric CompanyInventor: James C. Carnahan, Jr.
-
Patent number: 4147643Abstract: 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: GrantFiled: June 17, 1976Date of Patent: April 3, 1979Assignee: The Lubrizol CorporationInventors: John F. Pindar, Jerome M. Cohen