Of Phenol Having Acyclic Polycarbon Hydrocarbyl Group Bonded Directly To The Benzene Ring Patents (Class 568/756)
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Patent number: 11767281Abstract: A process for manufacturing Pure Propofol with a purity of more than 99.90% is disclosed, said process comprising dissolving Crude Propofol in a solvent in which it is soluble to form a solution, treating the solution with aqueous alkali to form an aqueous alkali layer and a solvent layer, separating the aqueous alkali layer from the solvent layer using a phase separation technique, distilling off the solvent from the solvent layer, and distilling a residue of the solvent containing Propofol using steam or boiling water in a presence of dilute alkali and antioxidant like metabisulfite, under normal pressure or mild vacuum.Type: GrantFiled: February 4, 2021Date of Patent: September 26, 2023Inventor: Nandkumar Kashinath Chodankar
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Patent number: 10138194Abstract: A method of producing thymoquinone and/or thymohydroquinone in Monarda by growing Monarda with elevated levels of carvacrol and/or thymol in the fresh plant tissue and vigorous growth, harvesting the Monarda, leaving the Monarda to senesce in the presence of oxygen and extracting the thymoquinone and/or thymohydroquinone from the senesced tissue.Type: GrantFiled: July 11, 2017Date of Patent: November 27, 2018Assignee: KEMIN INDUSTRIES, INC.Inventors: John A. Greaves, Brindha Narasimhamoorthy, Vandana Srivastava, Norman Cloud, Dawn Clark
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Patent number: 9745242Abstract: A method of producing thymoquinone and/or thymohydroquinone in Monarda by growing Monarda with elevated levels of carvacrol and/or thymol in the fresh plant tissue and vigorous growth, harvesting the Monarda, leaving the Monarda to senensce in the presence of oxygen and extracting the thymoquinone and/or thymohydroquinone from the senesced tissue.Type: GrantFiled: November 10, 2016Date of Patent: August 29, 2017Assignee: KEMIN INDUSTRIES, INC.Inventors: John A. Greaves, Brindha Narasimhamoorthy, Vandana Srivastava, Norman Cloud, Dawn Clark
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Patent number: 9029610Abstract: A method for cultivating Monarda fistulosaincludes planting seeds at rates between about 2.5 and about 5 pounds per acre, preferably about 4 pounds per acre. Fuel costs are reduced because seeding, mowing the first season, and harvesting in seasons thereafter are all that is required. Reduction in herbicide use results from the heavy rate of planting, improved germination attributed to rolling, and the plant's natural herbicides which are more highly effective when seeded at the higher rate. The method includes seeding, mowing during a first growing season, and harvesting each season thereafter. This method results in oil without weed contamination and carvacrol levels are high.Type: GrantFiled: January 26, 2012Date of Patent: May 12, 2015Assignee: Prairie Pharms, LLCInventor: William G. Rohlfsen
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Patent number: 8993813Abstract: The present invention relates to a process for the preparation of 4-isopropyl-3-methylphenol (p-thymol) from distillation residues of thymol production.Type: GrantFiled: May 18, 2012Date of Patent: March 31, 2015Assignee: LANXESS Deutschland GmbHInventors: Uwe Boeger, Lutz Heuer, Michael Herzhoff
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Patent number: 8519193Abstract: The present invention relates to a method for producing 4-isopropyl-3-methyl-phenol by alykylizing meta-cresol, distilling, and crystallizing.Type: GrantFiled: July 15, 2008Date of Patent: August 27, 2013Assignee: LANXESS Deutschland GmbHInventor: Lutz Heuer
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Patent number: 8507732Abstract: The present invention is directed to a composition comprising a tris-hydroxyaryl compound having a metal ion impurity content of less than 10 ppm and to a process for the purification of tris-hydroxyaryl compound having a metal ion impurity, comprising at least the following steps: a) conditioning a sulphonic acid group-containing active ion exchanger with a solvent which is suitable for the handling of the tris-hydroxyaryl compounds, b) producing a solution of the tris-hydroxyaryl compounds to be purified in a solvent which is suitable for the handling of the tris-hydroxyaryl compounds, c) contacting the tris-hydroxyaryl compound-containing solution from b) with the conditioned ion exchanger from a), d) separating the tris-hydroxyaryl compound-containing solution from c) from the conditioned ion exchanger, e) removing at least part of the solvent from the solution of the tris-hydroxyaryl compound separated in d) under low temperature stress.Type: GrantFiled: April 7, 2011Date of Patent: August 13, 2013Assignee: Bayer Intellectual Property GmbHInventors: Christian Münnich, Stephan Konrad, Karl-Heinz Köhler
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Publication number: 20130197277Abstract: A method for cultivating Monarda fistulosaincludes planting seeds at rates between about 2.5 and about 5 pounds per acre, preferably about 4 pounds per acre. Fuel costs are reduced because seeding, mowing the first season, and harvesting in seasons thereafter are all that is required. Reduction in herbicide use results from the heavy rate of planting, improved germination attributed to rolling, and the plant's natural herbicides which are more highly effective when seeded at the higher rate. The method includes seeding, mowing during a first growing season, and harvesting each season thereafter. This method results in oil without weed contamination and carvacrol levels are high.Type: ApplicationFiled: January 26, 2012Publication date: August 1, 2013Inventor: William G. Rohlfsen
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Patent number: 8283501Abstract: Disclosed herein are optically active biphenol derivatives represented by the following formulas (1) and (2), a method for optically resolving a biphenol derivative represented by formula (2?), a production method of an optically active biphenol derivative (1) comprising a step for reacting a Brønsted acid with a biphenol derivative (2), and a production method of an optically active biphenol derivative (3) comprising a step for reacting a Lewis acid with an optically active biphenol derivative (1) or an optically active biphenol derivative (2).Type: GrantFiled: January 6, 2009Date of Patent: October 9, 2012Assignee: Nippon Soda Co., Ltd.Inventors: Yoshikazu Ito, Yasushi Kubota, Tsutomu Inoue
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Publication number: 20100331579Abstract: The present invention relates to a method for producing 4-isopropyl-3-methyl-phenol by alykylizing meta-cresol, distilling, and crystallizing.Type: ApplicationFiled: July 15, 2008Publication date: December 30, 2010Applicant: LANXESS DEUTSCHLAND GMBHInventor: Lutz Heuer
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Patent number: 6451879Abstract: A process for producing a phenolic resin of good hue, characterized by reacting a hydroxylated aromatic compound with an unsaturated cyclic hydrocarbon compound in the presence of both active hydrogen and a reducing metal compound with the aid of an acid catalyst, subsequently deactivating the catalyst, and then removing the catalyst, the metal compound, and the starting materials remaining unreacted; and a process for producing an epoxy resin which comprises a step of reacting the phenolic resin with an epihalohydrin. By these processes, a phenolic resin and an epoxy resin are obtained which each is colored little and has an excellent hue. These resins are useful as resins for electrically insulating materials, especially as resins for semiconductor encapsulation materials and for laminated plates.Type: GrantFiled: April 13, 2001Date of Patent: September 17, 2002Assignee: Nippon Petrochemicals Company, LimitedInventors: Satoshi Mori, Fumiaki Oshimi, Ryuichi Ueno
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Patent number: 6407150Abstract: A process for producing phenol resin having good color tone, which process comprises reacting hydroxyl group-containing aromatic compound and unsaturated cyclic hydrocarbon under the condition that the moisture is 100 ppm or less and the concentration of Friedel-Crafts catalyst is 0.07 mass % or less in a reaction system and a process for producing epoxy resin having good color tone, which process comprises reacting the obtained phenol resin and epihalohydrin in the presence of base catalyst, removing remaining catalyst and further removing unreacted epihalohydrin.Type: GrantFiled: August 10, 2000Date of Patent: June 18, 2002Assignee: Nippon Petrochemicals Company, LimitedInventors: Satoshi Mori, Fumiaki Oshimi, Masato Hattori
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Patent number: 6258901Abstract: There is provided a process for efficiently and economically producing a polymer which is superior in transmittances of visible light and far-ultraviolet light, has a high molecular weight and is light-colored. A process for producing a light-colored vinylphenol-based polymer by subjecting p-vinylphenol to homopolymerization or subjecting p-vinylphenol and a vinyl compound copolymerizable with p-vinylphenol to copolymerization, in the presence of a cationic polymerization catalyst or a radical polymerization initiator, which process comprises subjecting a p-vinylphenol-containing raw material to vacuum flash distillation in the presence of a phenolic compound having no unsaturated side chain and water and subjecting the resulting p-vinylphenol-containing fraction to polymerization.Type: GrantFiled: August 7, 2000Date of Patent: July 10, 2001Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Masao Kaneko, Tadashi Matsumoto, Nobuyuki Oka, Kunishige Ohtsu
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Patent number: 5705039Abstract: Impure 2,6-diisopropylphenol (DIP) is purified by use of a distillation process in which a single distillation column is used. The process comprises: (a) subjecting the impure DIP to a first continuous distillation in the column in an inert environment to distill off lower boiling components and produce first column bottoms enriched in DIP; (b) collecting, cooling and storing the first column bottoms while continuously maintaining them in an inert environment; (c) discontinuing the first continuous distillation; (d) subjecting the first column bottoms to a second continuous distillation in an inert environment in the same column to produce a second overhead distillate composed of purified DIP. The process avoids the formation in the distilling mixtures of dose boiling impurities due to seepage of air through standard pipe flanges and fittings and consequent oxidation reactions which occur under the conditions needed for batch distillations conducted in typical industrial distillation facilities.Type: GrantFiled: October 13, 1995Date of Patent: January 6, 1998Assignee: Albemarle CorporationInventors: Sam F. Clarke, Venkataraman Ramachandran, J. Steve Staton, Paul L. Wiggins
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Patent number: 5672776Abstract: Tris(4-hydroxyphenyl)alkanes such as 1,1,1 -tris(4-hydroxyphenyl)ethane are purified by formation of an adduct with a molar excess of a C.sub.1-4 primary alkyl tertiary amine, preferably triethylamine. Adduct formation is preferably effected in a polar organic solvent such as methanol. The pure tris(4-hydroxyphenyl)alkane may be recovered from the adduct by thermal or aqueous acid-promoted cracking.Type: GrantFiled: September 27, 1996Date of Patent: September 30, 1997Assignee: General Electric CompanyInventors: Patrick Joseph McCloskey, Julia Lam Lee
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Patent number: 5591311Abstract: A process for purifying impure 2,6-diisopropylphenol (DIP) mixtures having lower and higher boiling phenolic impurities is described. The process involves washing the mixture with aqueous alkali metal hydroxide solution in an inert atmosphere and separating the aqueous and organic phases, washing the resulting organic phase with water, and then subjecting the water-washed organic phase to distillation in an inert environment to recover purified DIP. Since only one distillation is required rather than two, the development of impurities in the DIP caused by in situ oxidation reactions at elevated temperatures due to the inevitable presence of traces of air in commercial distillation facilities is reduced to acceptable levels.Type: GrantFiled: October 26, 1995Date of Patent: January 7, 1997Assignee: Albemarle CorporationInventor: Venkataraman Ramachandran
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Patent number: 5589598Abstract: A process for the purification of 2,6-diisopropylphenol (Propofol) by transformation of the crude Propofol into its ester with a carboxylic or sulphonic acid, crystallization and hydrolysis, is described.Type: GrantFiled: June 1, 1995Date of Patent: December 31, 1996Assignee: Zambon Group S.p.A.Inventor: Maurizio Paiocchi
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Patent number: 5476973Abstract: Disclosed herein are a stable m-vinylphenol composition comprising m-vinylphenol and tolylene-2,4-diamine and/or N,N-dimethyl-p-phenylenediamine added thereto, a method of stabilizing m-vinylphenol, which comprises adding tolylene-2,4-diamine and/or N,N-dimethyl-p-phenylenediamine to m-vinylphenol, and a method of purifying m-vinylphenol by distillation, which comprises adding tolylene-2,4-diamine and/or N,N-dimethyl-p-phenylenediamine to m-vinylphenol upon the purification of m-vinylphenol by distillation.Type: GrantFiled: February 17, 1995Date of Patent: December 19, 1995Assignee: Maruzen Petrochemical Co., Ltd.Inventors: Rika Hatano, Tadashi Matsumoto, Teruki Matsukami
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Patent number: 5354429Abstract: A discrete impure cresylic acid distillate fraction derived by fractional distillation of a natural cresylic acid feedstock from which tar bases and/or neutral oils have not been removed is subjected to extractive distillation with a polyhydric alcohol extractant and subsequent separation of the discrete cresylic acid fraction. The extractive distillation removes tar bases, neutral oils, undesirable phenolic substances, sulfur compounds, color-forming impurities and odor-imparting impurities.Type: GrantFiled: July 2, 1993Date of Patent: October 11, 1994Assignee: Dakota Gasification CompanyInventors: David H. Duncan, Gene G. Baker, Dana J. Maas, Kevin M. Mohl, Robert G. Todd
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Patent number: 5202505Abstract: Crude hydroxyphenylalkane, e.g., 1,1,1-tris(4'-hydroxyphenyl)ethane, is purified, to reduce color and prevent caustic solution turbidity, (a) by contacting the hydroxyphenylalkane in alcoholic solution with an alkali metal dithionite, preferably in the presence of an alkalinity agent such as an alkali metal borohydride, more preferably by introducing the dithionite into the alcoholic solution as an alkaline aqueous solution, (b) precipitating the hydroxyphenylalkane from the alcoholic solution, and optionally (c) rinsing the hydroxyphenylalkane with an alkaline aqueous solution of the dithionite.Type: GrantFiled: March 24, 1992Date of Patent: April 13, 1993Assignee: Hoechst Celanese CorporationInventors: Mark A. Murphy, Mike R. Czarny
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Patent number: 5175376Abstract: The object of the invention is a new method for the purification of 2,6-diisopropyl phenol (propofol). The invention is characterized in that the raw product obtained from the alkylation of propene with phenol is crystallized at a temperature where propofol crystallizes but the isomers and other phenol derivatives formed in the reaction are still in liquid form, i.e. at a temperature of -25.degree. to +18.degree. C. especially at -20.degree. to -10.degree. C., without a solvent or using a suitable solvent, such as hexane or petrol ether.Type: GrantFiled: April 30, 1992Date of Patent: December 29, 1992Assignee: Leiras OyInventors: Kauko Nieminen, Peter Essen
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Patent number: 5094722Abstract: A purified desired isomer which is either 3,4- or 3,5-dimethylphenol is separated with a high yield from a dimethylphenol-containing fraction which contains both 3,4- and 3,5-dimethylphenols. The fraction is distilled so as to give a distillate which is enriched with the desired dimethylphenol isomer to be separated and which contains at least 35% by weight of the desired isomer. The desired DMP isomer is crystallized from a melt of the enriched distillate in two stages with at least part of the filtrate separated from the precipitated crystals in the second crystallization stage being circulated to the first crystallization stage. The enriched distillate is introduced into the first crystallization stage when it contains the desired isomer in a concentration of from 35% to less than 70% by weight, or it is introduced into the second crystallization stage when it contains the desired isomer in a concentration of 70% by weight or higher.Type: GrantFiled: August 16, 1990Date of Patent: March 10, 1992Assignee: Sumikin Chemical Co., Ltd.Inventors: Toshio Sato, Koji Tabata, Toshihiko Kashitani
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Patent number: 5091058Abstract: Method of preparing para-cumylphenol including reacting an excess of phenol with alpha-methylstyrene by the slow addition of alpha-methylstyrene to a 50% to 200% molar excess of phenol at a temperature from about 80.degree. C. to about 90.degree. C. in the presence of an acid catalyst and thereafter maintaining the temperature at about 95.degree. to about 100.degree. C. to obtain a crude cumylphenol reaction product containing acid derived from the catalyst, and distilling the reaction product in the presence of an amount of base sufficient to neutralize the acid therein.Type: GrantFiled: January 25, 1991Date of Patent: February 25, 1992Assignee: Aristech Chemical CorporationInventor: William R. Davie
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Patent number: 4992598Abstract: A process for the purificationof 1,1,1-tris(4'-hydroxyphenyl)ethane by washing a crude admixture containing both it and impurities with a saturated solution of 1,1,1-tris(4'-hydroxyphenyl)ethane in water and methanol; and isolating the washed crude admixture from the effluent and dissolving the washed crude admixture in methanol, and adding water and sodium borohydride to the dissolved, washed crude admixture to form a precipitate of 1,1,1-tris(4'-hydroxyphenyl)ethane, and filtering the precipitate to form a resultant purified 1,1,1-tris(4'-hydroxyphenyl)ethane and a filtrate. Another embodiment of the invention provides iteratively repeating the process by washing an additional crude admixture batch with the filtrate from a prior purification.Type: GrantFiled: February 9, 1990Date of Patent: February 12, 1991Assignee: Hoechst Celanese CorporationInventors: Heinz Strutz, Werner Mueller
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Patent number: 4987273Abstract: The invention relates to a process for the separation of a phenol from a mixture obtained by the carboxylation of the phenol and containing phenol, phenolate and the carboxylation products thereof, which process comprises separation carried out by selectively absorbing the phenol into the wall of a membrane, solubilizing the phenol in the membrane matrix, diffusing the phenol through the membrane and desorbing the phenol from the other wall.Type: GrantFiled: November 21, 1989Date of Patent: January 22, 1991Assignee: Shell Oil CompanyInventors: Johan G. A. Bitter, Johannes L. W. C. den Boestert, Wilhelmus J. M. Weeres
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Patent number: 4929770Abstract: Aluminum phenoxide catalyst is removed from a phenolic alkylation mixture by adding 15-30 moles of water per mole of aluminum phenoxide to the alkylation mixture and holding at about 30.degree.-100.degree. C. for 10-60 minutes to form solids and heating the wet mixture to 120.degree.-160.degree. C. and holding at that temperature until filterable particulates form. The particulates can be readily filtered to obtain a substantially aluminum-free filtrate.Type: GrantFiled: March 8, 1989Date of Patent: May 29, 1990Assignee: Ethyl CorporationInventors: Charles W. Matthews, Eric S. Batman, Jeffrey F. King
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Patent number: 4910334Abstract: Centrifugates obtained by centrifuging the reaction product of a process in which organic acids selected from the group consisting of higher alkyl benzene sulfonic acids, higher alkyl naphthenic acids, higher alkyl salicylic acids and higher alkyl phenols or alkali metal salts of the acids are contacted with a base acting alkaline earth metal compound to produce an alkaline earth metal salt of the selected acid are mixed with a quantity of an aqueous solution of an acid having an ionization constant greater than 1.times.10.sup.-5 sufficient to bring the pH of the centrifugate-acid mixture to a level in the range about 2 to 10 and settling the mixture to separate a lower aqueous phase and an upper liquid product phase and recovering the upper phase.Type: GrantFiled: December 17, 1984Date of Patent: March 20, 1990Assignee: Claypro CorporationInventors: Frank A. Stuart, William H. Tyson, Jr.
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Patent number: 4812596Abstract: A process is provided for converting waste distillation bottoms containing t-alkylphenols with substantial unknown constituents to useable para-t-alkylphenols. The process comprises heating the waste distillation bottoms with phenol and an acid catalyst to effect transalkylation. The waste distillation bottoms typically result from the production of para-t-alkylphenol and/or 2,4-di-t-alkylphenol.Type: GrantFiled: March 31, 1987Date of Patent: March 14, 1989Assignee: Pennwalt CorporationInventors: Altaf Husain, Stanley R. Sandler
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Patent number: 4547596Abstract: A method is provided for separating alkylated phenols based on differences in their dissociation constants without the consumption of neutralizing acid or base. This is accomplished by selectively reacting the mixed alkylated phenol having the having dissociation constant to the salt form and isolating the salts from the mixture in an aqueous solution. The alkylated phenols are then recovered from the aqueous solution in unreacted form with an organic solvent. Essentially all solvents and solutions can be recycled.Type: GrantFiled: October 30, 1984Date of Patent: October 15, 1985Assignee: General Electric CompanyInventors: Ashok K. Mendiratta, John J. Talley
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Patent number: 4503267Abstract: Polyethylene glycols have been found to be selective solvents for the extraction of phenolic compounds from admixture with hydrocarbons.Type: GrantFiled: October 24, 1983Date of Patent: March 5, 1985Assignee: Union Camp CorporationInventor: Mark S. Pavlin
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Patent number: 4496774Abstract: 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: GrantFiled: July 23, 1984Date of Patent: January 29, 1985Assignee: Koppers Company, Inc.Inventor: Gerd Leston
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Patent number: 4487987Abstract: A method of eliminating color-causing impurities in mixtures of aminoethylpiperazine, polyoxypropylenediamines and alkylphenols by treatment with N,N-diethylhydroxylamine is described. These alkylphenols such as nonylphenol are used in epoxy resins in the automotive and electronics industry. Discoloration of the phenol and subsequent resin occurs if the phenol is not treated with N,N-diethylhydroxylamine. Quantities on the order of 20 to 500 ppm are effective. The decolorization reaction may be conducted at a temperature in the range from about 25.degree. to 50.degree. C.Type: GrantFiled: June 9, 1983Date of Patent: December 11, 1984Assignee: Texaco Inc.Inventors: James H. Paslean, Charles S. Steele
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Patent number: 4433181Abstract: A process is provided for recovering the crystallization medium used for separating a 2,6-disubstituted phenol (DSP) from a feedstock containing it and a phenol in which only one of the 2 or 6 carbon positions are substituted (MSP).Type: GrantFiled: January 28, 1982Date of Patent: February 21, 1984Assignee: Koppers Company, Inc.Inventor: Samuel N. Holter
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Patent number: 4429169Abstract: A process is disclosed for separating 5-isopropyl-m-cresol from other isopropylated m-cresols by treating a mixture of the isopropylated m-cresols with a metal halide salt. The metal halide salt preferentially forms a complex with 5-isopropyl-m-cresol over other related closely-boiling isopropylated m-cresols in the mixture. The preferentially-formed complex of 5-isopropyl-m-cresol may then be isolated from the mixture and the complex decomposed to provide a product substantially enriched in, or substantially entirely composed of, 5-isopropyl-m-cresol. The process is particularly suitable for isolating 5-isopropyl-m-cresol from closely-boiling isomers, and diisopropylated m-cresols.Type: GrantFiled: April 26, 1982Date of Patent: January 31, 1984Assignee: Koppers Company, Inc.Inventor: Gerd Leston
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Patent number: 4423253Abstract: A process is disclosed for separating t-butylated phenolic compounds from other t-butylated and unbutylated 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-t-butylated derivatives, or a mixture of two isomeric t-butylated phenols or cresols or a mixture of mono- and di-t-butylated phenols or cresols.Type: GrantFiled: April 26, 1982Date of Patent: December 27, 1983Assignee: Koppers Company, Inc.Inventor: Gerd Leston
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Patent number: 4420643Abstract: A process for the extraction of phenolic compounds from aqueous solutions is disclosed. The process comprises contacting said aqueous solution with an organic solution comprising at least one tertiary phosphine oxide and a high boiling organic solvent.Type: GrantFiled: September 30, 1982Date of Patent: December 13, 1983Assignee: American Cyanamid CompanyInventors: Christos Savides, John H. Bright
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Patent number: 4408083Abstract: Disclosed is a method of treating hydroperoxide mixtures, which comprises bringing an oily hydroperoxide mixture containing (A) an aromatic hydroperoxide having a hydroperoxymethyl group directly bonded to the aromatic nucleus and (B) an aromatic hydroperoxide having a 2-hydroperoxy-2-propyl group bonded directly to the aromatic nucleus into contact with an aqueous alkali solution, separating the aqueous phase from the oil phase and decomposing at least a part of the component (A) extracted in the aqueous phase.According to this method, the starting oily hydroperoxide mixture can be converted to a mixture in which the primary hydroperoxide content is reduced without substantial loss of the tertiary hydroperoxide. Therefore, aromatic hydroperoxide mixtures suitable for production of phenols can advantageously be proceeded.Type: GrantFiled: August 17, 1981Date of Patent: October 4, 1983Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Masakazu Toyoura, Koichi Shomura, Hirotoshi Tsuchida, Tadateru Murakami
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Patent number: 4385191Abstract: Drastic molecular weight degradation of a p-(polybutyl-substituted phenol occurs when it is heated above 65.degree. C. in the presence of BF.sub.3 -phenolate catalyst used in the preparation of said substituted phenol by the alkylation of phenol with a butylene polymer of 500 to 3000 molecular weight. Such molecular weight degradation can be substantially suppressed by providing 20 to 30 weight percent dissolved phenol in the mixture resulting from such catalytic alkylation reaction and then rapidly heating the mixture with such amount of dissolved phenol to a temperature of from 182.degree. C. up to 200.degree. C. at extant atmospheric pressure whereat the catalyst dissociates and liberated BF.sub.3 is stripped out by phenol vapors.Type: GrantFiled: December 19, 1979Date of Patent: May 24, 1983Assignee: Standard Oil Company (Indiana)Inventors: Dennis G. Petrille, Chester G. Gunter, Frederick S. Jerome
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Patent number: 4356330Abstract: A method of eliminating color-causing impurities in mixtures of t-butyl alkylphenols by treatment with N-(2-hydroxyethyl)oxazolidine at 90.degree. C. and at atmospheric pressure is described. These phenols are used as peroxide inhibitors in polyoxyalkylene glycols for polyurethane foams. Discoloration of the polyol occurs if the phenol mixture is not treated with N-(2-hydroxyethyl)oxazolidine. The t-butyl alkylphenol mixture is derived from an alkylphenol made over an acid catalyst.Type: GrantFiled: July 20, 1981Date of Patent: October 26, 1982Assignee: Texaco Inc.Inventors: Michael Cuscurida, George P. Speranza
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Patent number: 4352944Abstract: The components of cashew nut shell liquid have such similar physical characteristics that their separation into relatively pure components has been difficult and has prevented use of the oil in many technological areas. The reaction of certain components with bases prior to distillation enables increased separation efficiency.Type: GrantFiled: January 8, 1981Date of Patent: October 5, 1982Assignee: Minnesota Mining and Manufacturing CompanyInventors: John H. P. Tyman, Mahesh S. Patel, Anthony P. Manzara
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Patent number: 4337369Abstract: A method of eliminating color-causing impurities in mixtures of t-butylalkyl phenols by treatment with trioxane at 100.degree. C. and 1 atmospheric pressure is described. These phenols are used as peroxide inhibitors in polyol formulations for polyurethane foams. Discoloration of the polyol occurs if the phenol mixture is not treated with trioxane. It is an essential part of the invention that the t-butyl alkylphenol mixture be derived from an alkylphenol made over an acid resin catalyst. Mixtures made by a BF.sub.3 process may not be decolorized by this method. Generally, the color decreases with increasing amounts of trioxane.Type: GrantFiled: January 30, 1981Date of Patent: June 29, 1982Assignee: Texaco Inc.Inventors: Steven H. Vanderpool, Ernest L. Yeakey
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Patent number: 4247721Abstract: A process for purifying p-isopropyl phenol (PIPP) by distilling the impure phenol at a pot temperature below about 475.degree. F. under sufficient vacuum to permit separation of a heart cut, and washing the separated heart cut with liquid hydrocarbon containing from about 5 to about 10 carbon atoms.Type: GrantFiled: November 5, 1979Date of Patent: January 27, 1981Assignee: Sun Oil Company of PennsylvaniaInventor: Donald F. Rugen
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Patent number: 4236030Abstract: A process for recovering phenols from a hydrocarbon mixture containing the same which comprises extracting such mixture with an aqueous formaldehyde solution.Type: GrantFiled: January 2, 1979Date of Patent: November 25, 1980Assignee: Gulf Research & Development CompanyInventors: Charles M. Selwitz, John G. McNulty
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Patent number: 4232176Abstract: Method of removing aluminum-containing catalyst from phenol alkylation products comprises treating phenol alkylation products with water at a temperature of 165.degree.-250.degree. C., with water being in molar excess to aluminum in a range of 3-20. The resulting residue of meta-aluminate is easily separated by filtration.The present invention allows eliminating constant control of aluminum content in alkylation products, easily removing the catalyst therefrom and eliminating the loss of phenol alkylation products.Type: GrantFiled: June 14, 1976Date of Patent: November 4, 1980Inventors: Engel R. Adigamov, Yakov A. Gurvich, Alexandr G. Liakumovich, Igor J. Logutov, Jury I. Michurov, Alexei S. Polenov, Vladimir A. Yanshevsky
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Patent number: 4138591Abstract: Alkylphenols are manufactured by reacting phenols with olefins, stripping the reaction mixture by means of an inert gas, cooling the phenol-containing gas mixture and removing the unconverted phenol. The products are starting materials for the manufacture of dyes, pesticides, pharmaceuticals, emsulfiers, dispersing agents, stabilizers, antioxidants, plasticizers, corrosion inhibitors, disinfectants, seed dressings, stabilizers against ageing, crop protection agents and scents.Type: GrantFiled: October 19, 1977Date of Patent: February 6, 1979Assignee: BASF AktiengesellschaftInventors: Karl G. Baur, Hans Hellbach, Rolf Platz, Kurt Taglieber
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Patent number: 4113975Abstract: A process for the removal of acids and potential acid-forming agents from a composition containing such acids and potential acid-forming agents and an alkylphenol which composition is obtained by reacting phenols with alkenes in the presence of sulfuric acid or a sulfonic acid, and for treating the effluent thereby obtained, the process being characterized by the steps of:(a) extracting a major amount of the acid constituents from the alkylphenol mixture by means of water;(b) treating the alkylphenol mixture with a dilute aqueous alkali solution in an amount such that the alkali is insufficient to neutralize all the acid originally present in the alkylphenol mixture,(c) separating the alkylphenol mixture from the aqueous alkali solution;(d) combining the aqueous phases obtained from steps (a) and (b);(e) heating the combined aqueous phases to a temperature of 100.degree. to 200.degree. C,(f) separating off the organic phase obtained in step (e); and(g) discharging the aqueous phase.Type: GrantFiled: January 6, 1977Date of Patent: September 12, 1978Assignee: Bayer AktiengesellschaftInventors: Helmut Fiege, Josef Haydn, Johann Renner, Karlfried Wedemeyer
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Patent number: 4101590Abstract: A process for the separation and purification of vinylphenol which comprises contacting crude vinylphenol containing vinylphenol and impurities such as phenol, alkylphenols, vinylphenol polymers and hydrocarbons countercurrently with an aqueous alkali solution together with a specific organic solvent.Vinylphenol obtained is useful as the raw material for the production of polyvinylphenol or a vinylphenol copolymer which is utilized as a thermoplastic resin, an ion exchange membrane, an adhesive, a glass fiber-reinforced composite or the like.Type: GrantFiled: August 23, 1976Date of Patent: July 18, 1978Assignee: Maruzen Oil Co., Ltd.Inventors: Mikio Sato, Kinya Tawara, Shinpachiro Iwaki, Kohji Matsumoto, Kenichi Sekine
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Patent number: 4096175Abstract: Covers a method of separating a nonionic surfactant from an anionic surfactant by use of methylal.Type: GrantFiled: December 1, 1976Date of Patent: June 20, 1978Assignee: Texaco Development CorporationInventors: Carter G. Naylor, Simon P. Burns