Isopropylidene Diphenol Produced Patents (Class 568/728)
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Patent number: 4443635Abstract: In the production of bisphenols, color bodies which have been adsorbed on cationic exchange resins are removed by washing with at least one phenate selected from phenates of an alkali metal and of ammonia.Type: GrantFiled: December 6, 1982Date of Patent: April 17, 1984Assignee: Shell Oil CompanyInventor: William A. McLaughlin
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Patent number: 4423252Abstract: Bisphenols are prepared by condensation of a phenol with a ketone in the presence of a sulfonic acid type cation exchange resin partially modified with a pyridinealkanethiol of the formula:Py--(CH.sub.2).sub.n SHwherein n is a positive integer and Py is 3-pyridyl when n is 1, or 2-, 3- or 4-pyridyl when n is more than 1.Type: GrantFiled: July 2, 1981Date of Patent: December 27, 1983Assignee: Mitsubishi Chemical Industries LimitedInventors: Takao Maki, Tetsuo Masuyama, Toshiharu Yokoyama, Yoshiko Fujiyama
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Patent number: 4400555Abstract: An improved bis-phenol synthesis reactor system is provided using multiple acetone injection in an ion exchange catalyzed BPA synthesis process. This process results in an improved reactant effluent product distribution and color.Type: GrantFiled: October 6, 1981Date of Patent: August 23, 1983Assignee: General Electric CompanyInventor: Ashok K. Mendiratta
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Patent number: 4400546Abstract: Hexafluoroacetone is prepared by a rearrangement of hexafluoropropene epoxide at an elevated temperature in the presence of hydrogen fluoride as a catalyst and, if appropriate, also as a solvent. In many cases the solution of hexafluoroacetone in hydrogen fluoride obtained in this process can be directly employed without further working-up or purification in further reactions of hexafluoroacetone, for example with phenol and/or o-cresol.Type: GrantFiled: December 9, 1981Date of Patent: August 23, 1983Assignee: Hoechst AktiengesellschaftInventors: Peter-Paul Rammelt, Gunter Siegemund
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Patent number: 4400554Abstract: Bis(hydroxyphenyl)methanes are prepared by reaction of phenol and formaldehyde in a two-phase mixture containing aqueous phosphoric acid. The reaction conditions can be selected to provide high yields of bis(hydroxyphenyl)methanes or to yield bis(hydroxyphenyl)methanes containing a high concentration of the 4,4'-isomer.Type: GrantFiled: March 29, 1982Date of Patent: August 23, 1983Assignee: Monsanto CompanyInventor: Morris R. Ort
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Patent number: 4396728Abstract: A sulfonated aromatic organic polymer, such as sulfonated polystyrene ion-exchange resin, is provided having N-alkylaminoorgano mercaptan groups attached to backbone sulfonyl 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: September 2, 1981Date of Patent: August 2, 1983Assignee: General Electric CompanyInventor: Gary R. Faler
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Patent number: 4391997Abstract: An ion exchange catalyzed bisphenol process is described wherein condensation reaction temperature is increased along the path of the reaction which limits the formation of color bodies, tars and other condensation reaction by-product impurities.Type: GrantFiled: October 23, 1981Date of Patent: July 5, 1983Assignee: General Electric CompanyInventor: Ashok K. Mendiratta
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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
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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
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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
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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
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Patent number: 4337367Abstract: An oligomer of m-isopropenylphenol is produced by subjecting m-isopropenylphenol to thermal polymerization in the absence of a catalyst.Type: GrantFiled: December 26, 1979Date of Patent: June 29, 1982Assignee: Sumitomo Chemical Company, LimitedInventors: Shuichi Kanagawa, Shinji Nakao, Kiyoshi Nakai, Kunimasa Kamio, Shunsuke Matsushima, Kazuhiko Hata, Kentaro Mashita
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Patent number: 4327229Abstract: An improved process is described for recovery of some of the bisphenol-A values present in the waste streams in an acid-catalyzed bisphenol-A synthesis process.Type: GrantFiled: January 19, 1981Date of Patent: April 27, 1982Assignee: General Electric CompanyInventor: Ashok K. Mendiratta
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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
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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
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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
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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
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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
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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
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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
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Patent number: 4212997Abstract: The compound 2,2-bis(4-hydroxyphenyl)propane is recovered in the form of rhombic crystals from an essentially non-crystalline mixture comprising 2,2-bis(4-hydroxyphenyl)propane, organic by-products of the condensation reaction of phenol and acetone, and phenol by lowering the temperature of the mixture from an elevated state to a temperature which is low enough to cause the separation of the phenol and 2,2-bis(4-hydroxyphenyl)propane in equimolar proportions as a crystalline adduct, recovering the adduct, forming a mixture of the adduct and water at an elevated temperature sufficient to completely melt the adduct, and thereafter lowering the temperature of the mixture of water and melted adduct to cause the separation of the 2,2-bis(4-hydroxyphenyl)propane in the form of rhombic crystals substantially free of the phenol. The crystals are easily handled and recovered by means such as filtration or centrifugation, and they can be formed into high quality polycarbonate molding resins.Type: GrantFiled: June 27, 1978Date of Patent: July 15, 1980Assignee: General Electric CompanyInventors: John N. Adams, Gaylord M. Kissinger, Michael C. Lee
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Patent number: 4192955Abstract: 2,2-Bis(4-hydroxyphenyl) propane, herein referred to as bisphenol-A, is recovered from crude or partially purified adducts with phenol by dissolving in a solvent in which the bisphenol-A phenol adduct is soluble and which is miscible with water, mixing the resulting adduct-solvent solution with water at a temperature at which the adduct is soluble therein, cooling the mixture to a temperature where substantially all of the bisphenol-A precipitates substantially without co-precipitation of the phenol, and physically recovering said precipitated bisphenol-A. Also contemplated is an embodiment wherein such a solvent solution of bisphenol-A or the adduct thereof with phenol is added to the water, rather than vice-versa, and high purity, easy to handle rhombic crystals of bis-phenol-A are produced.Type: GrantFiled: December 18, 1977Date of Patent: March 11, 1980Assignee: General Electric CompanyInventor: Clayton W. Reinitz
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Patent number: 4192954Abstract: A process is disclosed for the production of 2,2-bis(4-hydroxyphenyl) propane, herein referred to as bisphenol-A, from by-products remaining after purification distillation of bisphenol-A produced from a condensation reaction of phenol and acetone. The process comprises mixing the by-products with phenol and adding anhydrous hydrogen chloride under superatmospheric pressure to the resulting mixture to isomerize those by-products isomerizable to bisphenol-A for subsequent recovery.Type: GrantFiled: December 23, 1977Date of Patent: March 11, 1980Assignee: General Electric CompanyInventors: Henry P. Barker, Lawrence C. Mitchell
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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
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Patent number: 4188496Abstract: A process is disclosed for the production of 2,2-bis(4-hydroxyphenyl) propane, herein referred to as bisphenol-A, from by-products remaining after purification distillation of bisphenol-A produced from a condensation reaction of phenol and acetone. The process comprises mixing the by-products with phenol and treating the resulting mixture with anhydrous hydrogen bromide to isomerize those by-products isomerizable to bisphenol-A for subsequent recovery.Type: GrantFiled: December 23, 1977Date of Patent: February 12, 1980Assignee: General Electric CompanyInventors: Donald B. G. Jaquiss, Lawrence C. Mitchell
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Patent number: 4180683Abstract: A process is disclosed for the recovery of 2,2-bis(4-hydroxyphenyl)propane, herein referred to as bisphenol-A, from residues remaining after purification distillation of bisphenol-A produced from a condensation reaction of phenol and acetone. The process comprises mixing the residues with phenol in the absence of acidic reagents to precipitate a bisphenol-A-phenol crystalline adduct and recovering bisphenol-A from the separated adduct.Type: GrantFiled: December 23, 1977Date of Patent: December 25, 1979Assignee: General Electric CompanyInventor: Lawrence C. Mitchell
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Patent number: 4169211Abstract: Process for the production of 2,2-(4,4'-dihydroxydiphenyl) propane comprising reacting phenol with acetone in a molar ratio of at least 2:1 but not exceeding 10:1 in the presence of an acidic agent at a temperature not exceeding 80.degree. C. to substantially complete reaction of the acetone, separating the acidic agent from the reaction product, bringing the product freed from acidic agent into contact with a material chosen from between activated carbon and active earths at a temperature in the range of from about 60.degree. to 120.degree. C. for a time in the range of from about 1 to 120 minutes and distilling the product obtained in the treatment with the active material to recover the 2,2-(4,4'-dihydroxydiphenyl-propane.Type: GrantFiled: July 13, 1977Date of Patent: September 25, 1979Assignee: Societa' Italiana Resine S.I.R. S.p.A.Inventors: Ferdinando Ligorati, Vittorio E. Nova, Giancarlo Aglietti
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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.