Identical Phenols Patents (Class 568/723)
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Patent number: 4564691Abstract: A process is provided for preparing a substituted 2,3-dihydrobenzofuran of the general formula ##STR1## in which R.sub.a is hydrogen, halogen, alkyl, straight or branched having from 1 to 4 carbon atoms, aryl, alkaryl, --OH, --OR.sub.3, --N(R.sub.d).sub.2, where R.sub.3 and R.sub.d are alkyl, straight or branched having from 1 to 4 carbon atoms; R.sub.b is alkyl, straight or branched, having from 1 to 6 carbon atoms, aryl, alkaryl; and R.sub.c is hydrogen or the same as R.sub.b, by the rearrangement of a 1,1-bis(2-hydroxybenzene) alkyl and/or aryl-ethane, in the presence of catalytic amounts of a mineral acid or organic acid such as phosphoric, sulfuric or p-toluenesulfonic, at elevated temperatures from 180.degree. to 250.degree. C., and withdrawing the resulting products from the reaction mixture as they are formed. The starting 1,1-bis(2-hydroxybenzene) alkyl and/or aryl-ethane compounds may be obtained by the catalyzed reaction of a substituted biphenol with an aldehyde.Type: GrantFiled: April 19, 1984Date of Patent: January 14, 1986Assignee: Enichimica Secondaria S.p.A.Inventors: Carlo Neri, Villiam Giroldini, Antonio Rinaldi, Mario Traversoni, Mario Clerici
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Patent number: 4554389Abstract: 4-[[4-hydroxy-3,5-bis(1-methylethyl)phenyl]hydrocarbyl]-2, 6-dimethylphenols.The compounds of the invention such as 4-[[4-hydroxy-3,5-bis(1-methylethyl)phenyl]hydrocarbyl]-2,6-dimethylphenol have low melting points and other physical and chemical properties making them valuable as curing agents, antioxidants, and for other purposes.Type: GrantFiled: April 9, 1984Date of Patent: November 19, 1985Assignee: Ethyl CorporationInventors: Kju Hi Shin, Edward F. Tatum
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Patent number: 4546207Abstract: Anhydrous di-(alkali metal) (especially disodium) salts of dihydroxyaromatic compounds such as bisphenol A are prepared by first contacting the solid dihydroxyaromatic compound with an aqueous alkali metal hydroxide solution so as to convert it into the solid di-(alkali metal) salt or hydrate thereof and subsequently separating the solid salt or hydrate from the aqueous system and removing water therefrom, typically by mixing the same with an organic liquid and removing water, including water of hydration, by evaporation. The organic liquid is preferably one such as toluene or o-dichlorobenzene in which water and the anhydrous di-(alkali metal) salt are substantially insoluble. The process may be operated in batch or continuous fashion.Type: GrantFiled: July 23, 1984Date of Patent: October 8, 1985Assignee: General Electric CompanyInventors: Ashok K. Mendiratta, Subhas K. Sikdar
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Patent number: 4535191Abstract: Novel polycarbonates are provided which exhibit rubbery and elastomeric properties which are the polymerized reaction products of:(i) a carbonate precursor; and(ii) at least one dihydric phenol represented by the general formula ##STR1## wherein R is selected from straight chain alkyl radicals containing from 8 to about 30 carbon atoms;each R.sup.1 is independently selected from halogen monovalent hydrocarbon, and monovalent hydrocarbonoxy radicals;each R.sup.2 is independently selected from halogen, monovalent hydrocarbon, and monovalent hydrocarbonoxy radicals; andn and n' are independently selected from whole numbers having a value of from 0 to 4 inclusive.Type: GrantFiled: February 23, 1984Date of Patent: August 13, 1985Assignee: General Electric CompanyInventors: Victor Mark, Charles V. Hedges
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Patent number: 4520187Abstract: Novel heat resistant polycarbonates are provided which are the polymerized reaction products of:(i) a carbonate precursor; and(ii) at least one dihydric phenol selected from dihydric phenols represented by the general formulae ##STR1## wherein: each R.sup.1 is independently selected from halogen radicals, monovalent hydrocarbon radicals, and monovalent hydrocarbonoxy radicals;each R.sup.2 is independently selected from halogen radicals, monovalent hydrocarbon radicals, and monovalent hydrocarbonoxy radicals;R.sup.4 and R.sup.5 are independently selected from monovalent hydrocarbon radicals;R.sup.3 is selected from hydrogen and monovalent hydrocarbon radicals, with the proviso that if R.sup.3 is a hydrogen radical than at least one of the monovalent hydrocarbon radicals represented by R.sup.4 and R.sup.5 contains at least two carbon atoms;R.sup.7 is selected from hydrogen and monovalent hydrocarbon radicals;R.sup.Type: GrantFiled: December 17, 1982Date of Patent: May 28, 1985Assignee: General Electric CompanyInventors: Victor Mark, Charles V. Hedges
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Patent number: 4514574Abstract: Separate isomers via supercritical gas extraction.Type: GrantFiled: January 9, 1984Date of Patent: April 30, 1985Assignee: The Dow Chemical CompanyInventors: Kimio Inoue, Gale G. Hoyer, Stanley I. Bates
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Patent number: 4492806Abstract: Anhydrous alkali metal (especially sodium) salts of hydroxyaromatic compounds, particularly bisphenols such as bisphenol A, are prepared by forming a solution of the hydroxyaromatic compound in a solvent mixture comprising a relatively high boiling non-polar organic liquid such as toluene or o-dichlorobenzene and an alkanol containing up to about 4 carbon atoms, preferably methanol; contacting said solution with an aqueous solution of a substantially stoichiometric amount of alkali metal hydroxide; and removing substantially all volatile materials from the reaction mixture by evaporation. The product thus obtained is a slurry of the anhydrous alkali metal salt in the non-polar liquid.Type: GrantFiled: November 28, 1983Date of Patent: January 8, 1985Assignee: General Electric CompanyInventors: Ashok K. Mendiratta, Wayne F. Morgan
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Patent number: 4469861Abstract: Aromatic polycarbonates derived from (i) a carbonate precursor, and (ii) at least one dihydric phenol represented by the general formula ##STR1## wherein: R and R' are independently selected from halogen radicals and monovalent hydrocarbon radicals;R.sup.1 is selected from hydrogen and alkyl radicals;R.sup.3 is selected from hydrogen and alkyl radicals;R.sup.2 is selected from alkyl radicals, with the proviso that when both R.sup.1 and R.sup.3 are hydrogen then R.sup.2 is selected from branched alkyl radicals containing at least three carbon atoms; andn and n' are independently selected from whole numbers having a value of from 0 to 4 inclusive.These polycarbonates are useful in the production of molded articles, films, and sheets.Type: GrantFiled: December 27, 1982Date of Patent: September 4, 1984Assignee: General Electric CompanyInventors: Victor Mark, Charles V. Hedges
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Patent number: 4460798Abstract: Asymmetrical bisphenols such as 2-(3-hydroxyphenyl)-2-(4-hydroxyphenyl)propane are prepared by an improved process wherein a hydroxyphenyldialkylcarbinol is reacted with a phenol in the presence of a hydrogen halide catalyst. According to the improved process, the carbinol is added to a mixture of the phenol and hydrogen halide under conditions maintaining a low carbinol concentration in the reaction mixture. This low concentration is preferably maintained by adding the carbinol in the form of a solution in a portion of the phenol.Type: GrantFiled: March 3, 1983Date of Patent: July 17, 1984Assignee: General Electric CompanyInventors: Howard J. Klopfer, Charles M. Orlando
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Patent number: 4447650Abstract: Methylene coupled aromatic compounds are prepared by contacting an aromatic reactant having a reactive hydrogen with chloromethyl methyl carbonate at a temperature from about 25.degree. C. to about 250.degree. C. in the presence of a catalytic amount of a Lewis acid.Type: GrantFiled: July 26, 1982Date of Patent: May 8, 1984Assignee: The Dow Chemical CompanyInventor: James M. Renga
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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: 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: 4380676Abstract: A process for the production of 2,2'-dihydroxy-biphenyls of the formula I ##STR1## wherein the symbols are as defined in claim 1. The process consists in the oxidative coupling of a phenol of the formula II ##STR2## in the presence of a strong inorganic base, with hydrogen peroxide as oxidizing agent. The reaction temperature is in the range from 30.degree. to 100.degree. C. and 1.5 to 4 moles of a base are employed per mole of phenol of the formula II.Type: GrantFiled: February 20, 1981Date of Patent: April 19, 1983Assignee: Ciba-Geigy CorporationInventor: Michael Rasberger
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Patent number: 4371719Abstract: 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 molded materials having valuable mechanical properties.Type: GrantFiled: February 23, 1981Date of Patent: February 1, 1983Assignee: Ciba-Geigy CorporationInventors: Abdul-Cader Zahir, Siegfried Wyler
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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
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Patent number: 4354048Abstract: Carbon-to-carbon coupled self-condensation products are obtained by the oxidative coupling of substituted phenols in the presence of a heterogeneous dehydrogenation catalyst comprising copper chromite.Type: GrantFiled: May 22, 1981Date of Patent: October 12, 1982Assignee: The Dow Chemical CompanyInventor: Robert M. Strom
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Patent number: 4354047Abstract: Carbon-to-carbon coupled self-condensation products are obtained by the oxidative coupling of substituted phenols in the presence of a heterogeneous dehydrogenation catalyst comprising nickel.Type: GrantFiled: May 22, 1981Date of Patent: October 12, 1982Assignee: The Dow Chemical CompanyInventor: Robert M. Strom
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Patent number: 4338470Abstract: Solid, bisphenol F particulates are prepared by first dispersing droplets of bisphenol F in a chemically inert liquid medium having a boiling point in excess of 70.degree. C. and having a temperature of at least 70.degree. but less than the boiling point thereof, said liquid medium being maintained in a state of dispersing agitation, and then cooling the dispersion which results, while continuing to maintain said state of agitation, to a temperature such as to solidify the dispersed droplets of said bisphenol F into solid particles.Type: GrantFiled: August 4, 1980Date of Patent: July 6, 1982Assignee: Rhone-Poulenc IndustriesInventors: Robert Granjon, Michel Fournier
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Patent number: 4302616Abstract: A method is provided for making alkali metal bis-phenoxide salts by refluxing a heterogenous mixture of a non-polar organic solvent and an aqueous solution of an alkali metal bisphenoxide. These bisphenoxide salts can be used thereafter to make aromatic bis(ether phthalimides) by reaction with nuclear ring substituted N-organo phthalimides.Type: GrantFiled: September 5, 1980Date of Patent: November 24, 1981Assignee: General Electric CompanyInventors: Frank J. Williams, III, Brent A. Dellacoletta
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.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: 4261912Abstract: This invention describes novel antioxidant compounds which are esters of .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;x is 1-4,n is 1 or 2, and,Y is a group of the formulas ##STR2## when n is 1, where R.sub.4 is alkyl having from 12 to 24 carbon atoms, phenyl, or phenyl substituted with hydroxy of alkyl having 1 to 4 carbon atoms, or combinations thereof, or ##STR3## when n is 2, where R.sub.5 is a direct bond, a straight chain or branched alkylene having 1 to 8 carbon atoms, or a phenylene group, and m is 0 to 4.Type: GrantFiled: August 1, 1979Date of Patent: April 14, 1981Assignee: GAF CorporationInventor: David J. Tracy
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Patent number: 4257953Abstract: A method is provided for making alkali metal bisphenoxide salts by refluxing a heterogenous mixture of a non-polar organic solvent and an aqueous solution of an alkali metal bisphenoxide. These bisphenoxide salts can be used thereafter to make aromatic bis(ether phthalimides) by reaction with nuclear ring substituted N-organo phthalimides.Type: GrantFiled: May 9, 1979Date of Patent: March 24, 1981Assignee: General Electric CompanyInventors: Frank J. Williams, III, Brent A. Dellacoletta
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Patent number: 4239918Abstract: Meta,para-substituted isopropylidene bisphenols are provided and methods for making such materials. Phenol, or substituted phenol is condensed with a meta-substituted isopropenyl phenol or a meta-hydroxy-.alpha.,.alpha.-dimethylbenzyl alcohol in the presence of an acid catalyst. The resulting meta,para-substituted isopropylidene bisphenols can be used as stabilizers for polyvinyl chloride resins and as intermediates for making high performance thermoplastics having chemically combined meta,para-isopropylidene diphenoxy units.Type: GrantFiled: December 6, 1978Date of Patent: December 16, 1980Assignee: General Electric CompanyInventor: Donald E. Keeley
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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
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Patent number: 4226800Abstract: Phenolic materials containing propargyl groups are prepared by reacting a polyhydric, phenolic material with propargyl bromide, the reaction being conducted in an aqueous sodium hydroxide solution. The products can be thermally polymerized to polymers which are useful as adhesives and as matrix resins in the fabrication of composites.Type: GrantFiled: June 14, 1979Date of Patent: October 7, 1980Assignee: The United States of America as represented by the Secretary of the Air ForceInventor: Lewellyn G. Picklesimer
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Patent number: 4219508Abstract: This invention relates to an improved process for the preparation of a mixture of various low molecular weight hydroxyaldehydes, hydroxyketones and polyhydric alcohols by the condensation of formaldehyde with itself. The essential feature of the improvement is that unpurified synthesis gases of the kind obtained from the large scale industrial production of formaldehyde can be used directly as the source of formaldehyde.Type: GrantFiled: August 30, 1977Date of Patent: August 26, 1980Assignee: Bayer AktiengesellschaftInventor: Kuno Wagner
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Patent number: 4202993Abstract: A method is provided for making substantially pure anhydrous sodium salts of aromatic bisphenols, such as the disodium salt of 2,2-bis(p-hydroxyphenyl)propane. Rapid separation of water from a sodium salt of an aromatic bisphenol hydrate, or as an aqueous mixture having stoichiometric quantities of sodium hydroxide and bisphenol has been found to provide substantially pure anhydrous bisphenol alkali metal salts useful as intermediates for making polyetherimides.Type: GrantFiled: May 9, 1979Date of Patent: May 13, 1980Assignee: General Electric CompanyInventor: Tohru Takekoshi
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Patent number: 4201878Abstract: Bisphenols substantially free of by-products, are produced rapidly by reacting a phenol and a compound of the formulae: ##STR1## wherein R and R' are hydrogen, lower alkyl or aryl; X is lower alkoxy or the same as X'; Y is chlorine or the same as X; X' is aryloxy; Z is a 1,2- or 1,3-propylenedioxy (that may optionally carry hydroxy, lower alkyl or lower hydroxyalkyl substituents), or arylenedioxy radical; n is integer from three to nine; m is (n-1).Type: GrantFiled: February 10, 1978Date of Patent: May 6, 1980Assignee: General Electric CompanyInventors: Victor Mark, Lawrence C. Mitchell, Charles V. Hedges
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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: 4163116Abstract: Bisphenols, substantially free of by-products, are produced rapidly by reacting a phenol and a compound of the formula ##STR1## wherein R and R' are independently selected from the group consisting of hydrogen, lower alkyl or aryl; X is lower acyloxy; Y is lower alkoxy, aryloxy or the same as X; Z is the divalent radical ##STR2## wherein R" and R'" are selected from the same category as R and R', and n is an integer from 3 to 9; m=(n-1).Type: GrantFiled: February 10, 1978Date of Patent: July 31, 1979Assignee: General Electric CompanyInventors: Charles V. Hedges, Victor Mark
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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.
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Patent number: 4133965Abstract: Tricyclo(5,2,1,O.sup. 2,6)-3-decene-8 (or 9)-ol is prepared by hydration of dicyclopentadiene using a heteropoly acid as a catalyst.Type: GrantFiled: August 31, 1977Date of Patent: January 9, 1979Assignee: Hitachi Chemical Company, Ltd.Inventors: Mitsuharu Kato, Toru Kikuchi, Takayuki Saito
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Patent number: 4097538Abstract: 1,1,1-Trichloro-2,2-bis(4-hydroxyphenyl)ethane can be dehydrohalogenated to 1,1-dichloro-2,2-bis(4-hydroxyphenyl)ethylene by treating the former with liquid ammonia.Type: GrantFiled: February 23, 1977Date of Patent: June 27, 1978Assignee: General Electric CompanyInventors: Arnold Factor, Michael R. MacLaury, Jimmy L. Webb
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Patent number: 4087469Abstract: A method of producing 2,2'-methylenebis(4,6-dialkylphenols) residing in that 2,4-dialkylphenols interact with acetals in the presence of an acid catalyst at a temperature from 30.degree. C to 140.degree. C with the formation of a reaction mixture containing the desired product and with subsequent separation of the desired product from said mixture, the starting reagents being taken in amounts of 1 mole of 2,4-dialkylphenol per 1-10 moles of acetal.The method is technologically simple and accomplished without the formation of waste water.Type: GrantFiled: December 16, 1975Date of Patent: May 2, 1978Inventors: Yakov Abramovich Gurvich, Alexandr Afroimovich Grinberg, Alexandr Grigorievich Liakumovich, Jury Ivanovich Michurov, Olga Fedorovna Starikova, Vladimir Avgustovich Yanshevsky, Simona Tevievna Kumok, Evgeny Lvovich Styskin, Grigory Iosifich Rutman
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Patent number: 4087463Abstract: Hydrogenolysis of hydrobenzoins [1,2-bis(aryl)ethane-1,2-diols] in the presence of a catalyst comprising cobalt carbonyl yields 1,2-bis(aryl)ethanes. The process is particularly directed to the production of 1,2-bis(4-hydroxyphenyl)ethane from 4,4-dihydroxyhydrobenzoin [1,2-bis(4-hydroxyphenyl)ethane-1,2-diol].Type: GrantFiled: December 22, 1976Date of Patent: May 2, 1978Assignee: Monsanto CompanyInventors: Denis Forster, George F. Schaefer