Purification Or Recovery Patents (Class 568/410)
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Patent number: 10358406Abstract: The present invention relates to process and apparatus for removing aldehydes from acetone. More specifically, the present invention relates to a process and apparatus for removing aldehydes from acetone by reacting the aldehydes with caustic in an acetone column and washing the organic phase with a plurality of water streams.Type: GrantFiled: June 29, 2018Date of Patent: July 23, 2019Assignees: UOP LLC, AdvanSix Inc.Inventors: Chad A. Williams, Michael J. Petragnani, Russell C. Schulz, Daniel R. Wright
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Patent number: 9284249Abstract: The present invention provides a method of extracting an asymmetric ?-diketone compound from a ?-diketone compound containing at least one symmetric ?-diketone compound mixed in the asymmetric ?-diketone compound, and the method includes the step (A) of adjusting a pH of a mixed solution of the ?-diketone compound and water at 11.5 or more and dissolving the ?-diketone compound into water to form a ?-diketone compound solution and the step (B) of subsequently adjusting the pH of the ?-diketone compound solution at 9.5 or less and recovering the asymmetric ?-diketone compound of Chemical Formula 1 separated from the ?-diketone compound solution. The present invention further includes at least either (a) a step of setting the upper limit of the pH of the mixed solution to 12.5 to form a ?-diketone compound solution in the step (A) and bringing the ?-diketone compound solution into contact with a hydrophobic solvent or (b) a step of setting the lower limit of the pH of the ?-diketone compound solution to 8.Type: GrantFiled: October 17, 2013Date of Patent: March 15, 2016Assignee: Tanaka Kikinzoku Kogyo K.K.Inventors: Ryosuke Harada, Toshiyuki Shigetomi, Satoshi Miyazaki, Masayuki Saito
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Publication number: 20150018576Abstract: The invention relates to a method for producing a product mixture (2) by means of the technical hydroformylation of a hydrocarbon stream (1) that contains isobutene, and for separating the product mixture (2) that is obtained, as well as to a device for the claimed method and to the use of a claimed device. The problem addressed thereby is that of providing a method and an associated device that allow the amount of high-boiling substances in the product mixture (2) to be kept as low as possible and thus the yield of the reaction to be increased. The problem is solved by the use of a nano-filtration device (M) for separating the catalyst from the product mixture (2), said device having especially high permeability to 3-methylbutanoic acid.Type: ApplicationFiled: February 11, 2013Publication date: January 15, 2015Applicant: Evonik Degussa GmbHInventors: Goetz Baumgarten, Michael Grass, Alfred Kaizik, Markus Winterberg, Hans-Gerd Lueken, Bart Hamers, Markus Priske, Dirk Fridag, Robert Franke, Dieter Hess
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Patent number: 8889915Abstract: Systems and methods for improving crude acetone column energy efficiency and operation are provided. The method for improving crude acetone column energy efficiency and operation can include introducing a crude acetone including acetone and phenol to a fractionation column and introducing cumene, AMS, or a combination thereof to the fractionation column. The method can include fractionating the crude acetone within the fractionation column to produce an acetone containing overhead and a phenol containing bottoms. The method can also include condensing at least a portion of the acetone containing overhead indirectly with a cool heat transfer medium to provide a condensed crude acetone product and a heated heat transfer medium, wherein the heat transfer medium includes cumene.Type: GrantFiled: February 25, 2014Date of Patent: November 18, 2014Assignee: Kellogg Brown & Root LLCInventors: Truc Vu, Theodor Robert Wilks
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Publication number: 20140221688Abstract: Disclosed is a process for recovering a water-soluble complex mixture of organic compounds from an aqueous stream through extraction and/or through contact of the aqueous stream with a sorbent or sorbents selected from the group consisting of polymeric microreticular sorbent resins, zeolite-based adsorbents, clay-based adsorbents, activated carbon-based sorbents, and mixtures thereof; and including methods to recover the removed organic compounds.Type: ApplicationFiled: February 7, 2013Publication date: August 7, 2014Applicant: KIOR, Inc.Inventors: Maria Magdalena Ramirez Corredores, Xiaowei Tong, Rocio Maria Banda, Royce Roemisch
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Patent number: 8710274Abstract: The present invention relates to a method of treating a crude acetone stream. The method generally includes treating a crude acetone stream which has acetone and at least one low-boiling impurity with a catalyst to form a treated acetone stream that has acetone and at least one higher-boiling impurity and then distilling the treated acetone stream to remove at least a portion of the higher-boiling impurity to produce a purified acetone stream. This is particularly helpful in processes where a more pure acetone is desired, including a process for making purified isopropanol.Type: GrantFiled: May 4, 2012Date of Patent: April 29, 2014Assignee: Lyondell Chemical Technology, L.P.Inventors: Daniel B Pourreau, Roger A Grey, Andrew P Kahn
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Publication number: 20140107353Abstract: The present invention provides methods, reactor systems, and catalysts for converting in a continuous process biomass to less complex oxygenated compounds for use in downstream processes to produce biofuels and chemicals. The invention includes methods of converting the components of biomass, such as hemicellulose, cellulose and lignin, to water-soluble materials, including lignocellulosic derivatives, cellulosic derivatives, hemicellulosic derivatives, carbohydrates, starches, polysaccharides, disaccharides, monosaccharides, sugars, sugar alcohols, alditols, polyols, diols, alcohols, ketones, cyclic ethers, esters, carboxylic acids, aldehydes, and mixtures thereof, using hydrogen and a heterogeneous liquefaction catalyst.Type: ApplicationFiled: December 19, 2013Publication date: April 17, 2014Applicant: Virent, Inc.Inventors: Ming Qiao, Randy D. Cortright, John Kania, Elizabeth Woods
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Publication number: 20130045318Abstract: To provide a salty taste enhancer which exerts a flavor enhancing effect comparable to sodium chloride without imparting any undesirable flavor such as harsh taste or odd smell, a method for producing the same, a kelp extract comprising the salty taste enhancer, and a food or drink having enhanced salty taste and flavor which comprises the salty taste enhancer or the kelp extract. A salty taste enhancer which comprises a volatile component with a molecular weight of less than 200 derived from a kelp.Type: ApplicationFiled: April 8, 2011Publication date: February 21, 2013Applicant: TAKASAGO INTERNATIONAL CORPORATIONInventors: Akihiko Watanabe, Azusa Nakatoh, Takeshi Oikawa
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Publication number: 20110266220Abstract: A method of separating components of mixtures of chemical compounds uses a nonporous membrane of copolymer of a perfluorinated cyclic or cyclizable monomer, and a 4 carbon dicarboxyl-containing comonomer, such as maleic anhydride. Optionally, the membrane composition includes an acyclic fluorinated olefin termonomer. The membranes provide a remarkably high selectivity of water relative to organic solvents and inorganic acids compared to dipolymer membranes of perfluorinated comonomers.Type: ApplicationFiled: January 5, 2010Publication date: November 3, 2011Applicant: CMS TECHNOLOGIES HOLDINGS, INC.Inventors: Daniel Campos, Jonathan Lazzeri, Stuart M. Nemser
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Patent number: 7868054Abstract: The present invention concerns photopolymerisable systems comprising reactive oligomers and/or monomers having ethylenically unsaturated groups and at least one phenylglyoxalic ester that, by photochemical decomposition, generates fragments having low migratability and low odor.Type: GrantFiled: May 10, 2006Date of Patent: January 11, 2011Assignee: Lamberti SpAInventors: Stefano Romagnano, Gabriele Norcini, Marco Visconti, Giuseppe Libassi
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Patent number: 7723397Abstract: The invention relates to novel photoinitiators of formula (I) wherein A is —O—, —CH2?, CH(CH3)— or —C(CH3)2?, and R is methyl or trimethylsilyl, and R may in addition be hydrogen when A is simultaneously the group —C(CH3)2?. The invention relates also to compositions comprising (A) at least one ethylenically unsaturated compound, (B) a photoinitiator of formula (I), (C) optionally further binders or additives, (D) optionally further photoinitiators or co-initiators. Compositions comprising (A) an ethylenically unsaturated compound that contains at least one aminoacrylate, (B) a photoinitiator of formula (II) or (III), (C) optionally further binders or additives, (D) optionally further photoinitiators or co-initiators.Type: GrantFiled: July 10, 2003Date of Patent: May 25, 2010Assignee: Ciba Specialty Chemicals CorporationInventors: Rinaldo Hüsler, André Fuchs
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Patent number: 7332092Abstract: E and Z isomers of alkene alcohols and/or alkene alcohol derivatives are separated by substantially continuously contacting an ion exchange medium which is ion exchanged with silver and/or copper ions with the feed stream comprising the E and Z isomers of at least one alkene alcohol and/or at least one alkene alcohol derivative, then removing a product stream having a higher concentration of the E or Z isomer of at least one alkene alcohol or derivative of the alkene alcohol relative to the concentration of the E or Z isomer of the alkene alcohol or derivative of the alkene alcohol in the feed stream.Type: GrantFiled: March 7, 2007Date of Patent: February 19, 2008Assignees: Calgon Carbon Corporation, InnovaAroma SAInventors: Chen-Chou Chiang, Elad Shabtai
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Patent number: 7084183Abstract: The invention relates to ?-hydroxy ketones of formula I or IIa; or mixtures of compounds of formula I and II; or mixtures of compounds of formulae Ia and IIaType: GrantFiled: October 31, 2002Date of Patent: August 1, 2006Assignee: Ciba Specialty Chemcials Corp.Inventors: André Fuchs, Rinaldo Hüsler, Christian Schregenberger, Martin Kunz
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Patent number: 6939993Abstract: Method for separating reaction product from imide compound catalyst represented by Formula (1) or derivative thereof in reaction mixture obtained by reaction in presence of imide compound catalyst: wherein R1 and R2 are each, for example, a hydrogen atom or an alkyl group, where R1 and R2 may be combined to form a double bond, an aromatic ring, or a non-aromatic ring, and X is an oxygen atom or a hydroxyl group. The method includes an extraction process using two organic solvents separable from each other to thereby separate the reaction product into one organic solvent layer and the imide compound catalyst component into the other organic solvent layer. The disclosed method efficiently and simply separates the reaction product from the catalyst component.Type: GrantFiled: October 25, 2001Date of Patent: September 6, 2005Assignee: Daicel Chemical Industries, Ltd.Inventor: Michihiro Sugahara
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Publication number: 20040192967Abstract: The present invention relates to a method for producing a saturated organic compound bearing at least one functional group from a mixture which comprises this saturated organic compound containing at least one functional group and also one or more other organic compounds, which comprisesType: ApplicationFiled: March 23, 2004Publication date: September 30, 2004Inventors: Dirk Fabritius, Doreen Neumann
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Patent number: 6727391Abstract: A liquid output from a continuous hydroformylation, which comprises essentially aldehydes, high-boiling by-products, a homogeneously dissolved hydroformylation catalyst, unreacted olefins, low-boiling by-products and dissolved synthesis gas, is worked up by a process in which a) the liquid hydroformylation output is depressurized in a first depressurization stage to a pressure which is from 2 to 20 bar below the reactor pressure, resulting in separation into a liquid phase and a gas phase, and b) the liquid phase obtained in the first depressurization stage is depressurized in a second depressurization stage to a pressure which is lower than the pressure of the first depressurization stage, resulting in separation into a liquid phase comprising essentially high-boiling by-products of the hydroformylation, the homogeneously dissolved hydroformylation catalyst and small amounts of hydroformylation product and unreacted olefin and a gas phase comprising essentially the major part of the hydroformylation producType: GrantFiled: August 8, 2002Date of Patent: April 27, 2004Assignee: BASF AktiengesellschaftInventors: Karl-Heinz Walczuch, Rolf Müller, Roland Krokoszinski, Bernhard Geissler
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Patent number: 6630075Abstract: Fire extinguishing compositions and methods for extinguishing, controlling, or preventing fires are described wherein the extinguishing agent is a fluorinated ketone having up to two hydrogen atoms, alone, or in admixture with a co-extinguishing agent selected from hydrofluorocarbons, hydrochlorofluorocarbons, perfluorocarbons, perfluoropolyethers, hydrofluoroethers, hydrofluoropolyethers, chlorofluorocarbons, bromofluorocarbons, bromochlorofluorocarbons, iodofluorocarbons, hydrobromofluorocarbons, and mixtures thereof.Type: GrantFiled: October 11, 2002Date of Patent: October 7, 2003Assignee: 3M Innovative Properties CompanyInventors: Fred E. Behr, Daniel R. Vitcak, Richard M. Flynn, Michael G. Costello, Michael J. Parent, Zhongxing Zhang
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Patent number: 6600070Abstract: In industrial production of &ohgr;-hydroxyaliphatic acid being an important intermediate for large cyclic lactone-based perfumes, using dicarboxylate ester which is inexpensive and readily obtainable, a method, with high yield and improved selectively, for making a 2-(&ohgr;-alkoxycarbonylalkanoyl)-4-butanolide and an alkaline metal salt thereof, an ester of &ohgr;-hydroxy-(&ohgr;-3)-ketoaliphatic acid as a novel compound and a derivative thereof, and a method for making the same are provided.Type: GrantFiled: November 29, 2001Date of Patent: July 29, 2003Assignee: Soda Aromatic Co., Ltd.Inventors: Hideaki Takaoka, Sigeru Wada, Nobuhiko Ito, Akio Hasebe, Shinzo Imamura, Hideo Muraoka
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Patent number: 6545186Abstract: Improved, safe process for the purification of ketones obtained by ozonolysis and subsequent reduction of the corresponding terpenes, in which, after the ozonolysis and reduction of acyclic mono-, bi- or tricyclic terpenes with ozonizable double bonds, converting the resulting corresponding crude ketone into a high-purity ketone by means of steam distillation at atmospheric pressure or at reduced pressure, extraction of the steam distillate and subsequent distillation.Type: GrantFiled: December 12, 2001Date of Patent: April 8, 2003Assignee: DSM Fine Chemicals Austria Nfg GmbH & Co., KGInventors: Karlheinz Giselbrecht, Josef Schaller, Rudolf Hermanseder, Klaus Reiter
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Patent number: 6392101Abstract: The invention relates to a process for purifying a crude 1,1,1,5,5,5-hexafluoroacetylacetone dihydrate containing an impurity. The process includes bringing the crude 1,1,1,5,5,5-hexafluoroacetylacetone dihydrate into contact with a poor solvent in which 1,1,1,5,5,5-hexafluoroacetylacetone dihydrate is substantially insoluble, thereby removing the impurity from the crude 1,1,1,5,5,5-hexafluoroacetylacetone dihydrate. Alternatively, the process includes precipitating crystals of 1,1,1,5,5,5-hexafluoroacetylacetone dihydrate from a solution of the crude 1,1,1,5,5,5-hexafluoroacetylacetone dihydrate. Thus, it is possible to produce 1,1,1,5,5,5-hexafluoroacetylacetone dihydrate of high purity. This product makes it easy to produce 1,1,1,5,5,5-hexafluoroacetylacetone of high purity.Type: GrantFiled: December 21, 2000Date of Patent: May 21, 2002Assignee: Central Glass Company, LimitedInventors: Takeo Komata, Nariaki Ii, Yoshiki Hirotsu
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Patent number: 6392102Abstract: A particularly useful process which includes the steps of providing a feedstream comprising providing a source of formaldehyde formed by conversion of dimethyl ether in the presence of a catalyst comprising tungsten oxide; and (i) heating the feedstream with the heterogeneous acidic catalyst in a catalytic distillation column to convert methanol and formaldehyde present to methylal and higher polyoxymethylene dimethyl ethers and to separate the methylal from the higher polyoxymethylene dimethyl ethers is disclosed, and/or (ii) contacting the source of formaldehyde and a predominately dimethyl ether feedstream with a heterogeneous, condensation promoting catalyst capable of hydrating dimethyl ether under conditions of reaction sufficient to form an effluent comprising water, methanol, formaldehyde, dimethyl ether, and polyoxymethylene dimethyl ethers is disclosed. Unreacted dimethyl ether is recovered from the effluent and recycled to the formation of polyoxymethylene dimethyl ethers.Type: GrantFiled: April 12, 2000Date of Patent: May 21, 2002Assignee: BP Corporation North America Inc.Inventors: Gary P. Hagen, Michael J. Spangler
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Patent number: 6383343Abstract: A method of separating methanol and acetone, and methanol and methyl acetate involves distilling a mixture of the components by an extractive distillation process in the presence of an extractive distillation solvent. The extractive distillation solvent may be an amine, a chlorinated hydrocarbon, a brominated hydrocarbon, a paraffin, and an alkylated thiopene.Type: GrantFiled: September 28, 2000Date of Patent: May 7, 2002Inventors: Izak Nieuwoudt, Braam van Dyk
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Publication number: 20020010373Abstract: The invention relates to a process for purifying a crude 1,1,1,5,5,5-hexafluoroacetylacetone dihydrate containing an impurity. The process includes bringing the crude 1,1,1,5,5,5-hexafluoroacetylacetone dihydrate into contact with a poor solvent in which 1,1,1,5,5,5-hexafluoroacetylacetone dihydrate is substantially insoluble, thereby removing the impurity from the crude 1,1,1,5,5,5-hexafluoroacetylacetone dihydrate. Alternatively, the process includes precipitating crystals of 1,1,1,5,5,5-hexafluoroacetylacetone dihydrate from a solution of the crude 1,1,1,5,5,5-hexafluoroacetylacetone dihydrate. Thus, it is possible to produce 1,1,1,5,5,5-hexafluoroacetylacetone dihydrate of high purity. This product makes it easy to produce 1,1,1,5,5,5-hexafluoroacetylacetone of high purity.Type: ApplicationFiled: December 21, 2000Publication date: January 24, 2002Inventors: Takeo Komata, Nariaki Ii, Yoshiki Hirotsu
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Patent number: 6331654Abstract: Disclosed is a method for the production of product acetone of higher oxidation stability where the product acetone is produced by a multi-step rectification process in the presence of alkali catalyst. The embodiments of the method of present invention utilize a two-column and a one-column scheme of product acetone rectification from an acetone stream. In a two-column embodiment of the present invention, acetone is taken off in a vapor phase as a side-draw in a first column and directed to a partial condenser wherein it is separated into liquid and vapor phases with a simultaneous feed of aqueous sodium hydroxide solution to the first column above the feed tray.Type: GrantFiled: February 10, 2000Date of Patent: December 18, 2001Assignee: Illa International LLCInventors: Vladimir Mikhailovitch Zakoshansky, Irina Ivanovna Vassilieva
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Patent number: 6303826Abstract: A method for purification of acetone containing at least one oxidizable impurity. The method comprises the steps of: (a) contacting acetone containing at least one oxidizable impurity with a heterogeneous oxidation catalyst in the presence of oxygen for a time and at a temperature sufficient to oxidize at least a portion of at least one of the oxidizable impurities; and (b) substantially separating purified acetone from the resulting mixture obtained from step (a).Type: GrantFiled: January 19, 2000Date of Patent: October 16, 2001Assignee: Sunoco, Inc. (R&M)Inventors: Manoj V. Bhinde, Scott R. Keenan
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Process of recovering methyl ethyl ketone from an aqueous mixture of methyl ethyl ketone and ethanol
Patent number: 6121497Abstract: A process for the recovery of methyl ethyl ketone (MEK) from an aqueous mixture of MEK and ethanol comprising extracting the MEK from the mixture using an extractive solvent selected from the group consisting of isopentane, the o-, m-, m-isomers of xylene, and mixed xylenes. Preferably the extractive solvent is separated from the MFK in the extract by fractional distillation and recycled to the extraction step.Type: GrantFiled: October 16, 1998Date of Patent: September 19, 2000Assignee: Celanese International CorporationInventor: Carl David Murphy -
Patent number: 5876569Abstract: Methyl ethyl ketone cannot be separated from ethanol by distillation or rectification because of the closeness of their boiling points. Methyl ethyl ketone is readily separated from ethanol by extractive distillation. Effective agents are methyl benzoate, phenol, glycerol and nitroethane.Type: GrantFiled: June 29, 1998Date of Patent: March 2, 1999Inventor: Lloyd Berg
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Patent number: 5868907Abstract: Methyl ethyl ketone cannot be separated from ethanol by distillation or rectification because of the closeness of their boiling points. Methyl ethyl ketone is readily separated from ethanol by azeotropic distillation. Effective agents are amyl acetate, methyl formate, 2,2-dimethyl butane and 2,3-dimethyl butane.Type: GrantFiled: June 29, 1998Date of Patent: February 9, 1999Inventor: Lloyd Berg
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Patent number: 5770777Abstract: Disclosed is a method of reducing the UV absorption of a solvent that comprises water, an ethylene glycol, or a mixture thereof, where the solvent contains at least 0.1 ppm of a dione, particularly 3-methyl-2-hydroxy cyclopent-2-eneone or its tautomer, 3-methyl-1, 2-cyclopentanedione. The solvent is passed through an anionic exchange resin containing strong base sites. The UV absorbance of the effluent from the anionic exchange resin can be monitored and, when it increases, the resin can be reactivated by passing an aqueous solution of a base through it.Type: GrantFiled: May 9, 1996Date of Patent: June 23, 1998Assignee: Occidental Chemical CorporationInventors: David E. Albright, Edward A. Dietz
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Patent number: 5741940Abstract: Disclosed is a very economical way to produce vinyl carbonyls such as ethyl vinyl ketone. Disclosed also is a purification process of separating vinyl carbonyls and coreactants. The catalyst and reaction conditions give useful yields of vinyl carbonyls, the thermodynamically unfavorable product along with coreactants that are more thermodynamically favored. Disclosed also is the separation of reactants that takes place at low distillation temperatures and pressures in the presence of antioxidant.Type: GrantFiled: June 28, 1996Date of Patent: April 21, 1998Assignee: Eastman Chemical CompanyInventor: William A. Beavers
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Patent number: 5650540Abstract: Provided is a method of producing a highly pure amide compound in a high yield, wherein a silazane compound and/or a silane compound having at least one silicone-nitrogen bond are added to a reaction mixture obtained by reacting an acylfluoride group-containing compound with an amino compound, wherein the amide compound is present together with hydrogen fluroide and/or the amine hydrofluoride, thereby removing the hydrogen fluoride and/or the amine hydrofluoride from the reaction mixture.Type: GrantFiled: October 30, 1995Date of Patent: July 22, 1997Assignee: Shin-Etsu Chemical Co., Ltd.Inventors: Takashi Matsuda, Shinichi Sato, Noriyuki Koike
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Patent number: 5504239Abstract: A first alkanol having from 1 to 3 carbon atoms can be separated off from other organic compounds of higher carbon number from the group comprising other alcohols, polyalcohols, ethers, oxo compounds, esters of carboxylic acids and of carbonic acid, haloaliphatics, amines, amides, hydrocarbons, carboxylic acids and nitriles, which in each case have at least 1 carbon atom more than the first alkanol, where in the case of halogenoaliphatics, halogen substituents are counted as further carbon atoms, by permeation on membranes, if a water content from 1 to 30% by weight, preferably from 5 to 15% by weight, based on the amount of mixture and water, is maintained.Type: GrantFiled: June 7, 1994Date of Patent: April 2, 1996Assignee: Bayer AktiengesellschaftInventors: Wolf Mehl, Wolfgang Scheinert, Ingo Janisch, Andreas Groschl
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Patent number: 5470443Abstract: Isopropanol is difficult to separate from 2-butanone by conventional distillation or rectification because of the proximity of their boiling points. Isopropanol can be readily separated from 2-butanone by extractive distillation. Effective agents are o-cresol, ethylene glycol and nitroethane.Type: GrantFiled: January 10, 1995Date of Patent: November 28, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5453166Abstract: Ethanol is impossible to separate from 2-butanone by conventional distillation or rectification because of the minimum boiling azeotrope between these two. Ethanol can be readily separated from 2-butanone by extractive distillation. Effective agents are dipromyl amine, phenol and dimethylsulfoxide.Type: GrantFiled: November 7, 1994Date of Patent: September 26, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5423954Abstract: 2-Butanone is difficult to separate from isopropanol by conventional distillation or rectification because of the proximity of their boiling points. 2-Butanone can be readily separated from isopropanol by azeotropic distillation. Effective agents are 3-methyl pentane, methyl t-amyl ether and acetonitrile.Type: GrantFiled: January 9, 1995Date of Patent: June 13, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5414154Abstract: A process for the reduction of methylbenzofuran (MBF) impurities in phenol obtained from the decomposition product of cumene hydroperoxide requires treating the phenol to reduce the level of acetol, contacting the phenol containing a low level of acetol with an acid resin at sufficient temperature and residence time to reduce the level of MBF by conversion to higher boiling compounds, then distilling the phenol to separate phenol from higher boiling compounds. The phenol may be treated in known ways, such as by treatment with an amine, to reduce the level of acetol. The phenol containing a low level of acetol is contacted with a strong acid resin to reduce the level MBF.Type: GrantFiled: June 6, 1994Date of Patent: May 9, 1995Assignee: AlliedSignal Inc.Inventors: Theodore J. Jenczewski, Lamberto Crescentini, James A. Kweeder
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Patent number: 5405504Abstract: 1-Decene is impossible to separate from 2-octanone by conventional distillation or rectification because the two compounds form a minimum boiling azeotrope. 1-Decene can be readily separated from 2-octanone by azeotropic distillation. Effective agents are 1-propanol, 2-ethoxyethanol, and methanol.Type: GrantFiled: January 31, 1994Date of Patent: April 11, 1995Assignee: Lloyd BergInventors: Lloyd Berg, Randy W. Wytcherley
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Patent number: 5403448Abstract: 1-Decene is difficult to separate from 2-octanone by conventional distillation or rectification because of the proximity of their boiling points. 1-Decene can be readily separated from 2-octanone by azeotropic distillation. Effective agents are butyl propionate and 1-propanol.Type: GrantFiled: January 14, 1994Date of Patent: April 4, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5380755Abstract: The present invention provides alkyl and alkylbenzyl ethers of substituted hydroquinones and pharmaceutical compositions containing them. The present invention further provides methods of using these compounds and compositions to inhibit monoamine oxidase, particularly monoamine oxidase B. The present invention further provides methods for the treatment of diseases involving monoamine oxidase.Type: GrantFiled: July 24, 1992Date of Patent: January 10, 1995Assignee: The Du Pont Merck Pharmaceutical CompanyInventors: Argyrios G. Arvanitis, Everett L. Scholfield
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Patent number: 5304684Abstract: sec-Butylbenzene hydroperoxide obtained by oxidizing sec-butylbenzene is decomposed into phenol and methyl ethyl ketone, a resulting liquid comprising a methyl ethyl ketone as the main component is washed with an aqueous alkali solution to remove carboxylic acids, carboxylic acid esters, unsaturated ketones, and aldehydes, and the washed liquid is further subjected to neutralization, dehydration, and distillation.A methyl ethyl ketone can be obtained which has a high quality with regard to purity and potassium permanganate fading.Type: GrantFiled: July 7, 1993Date of Patent: April 19, 1994Assignee: Sumitomo Chemical Company, Ltd.Inventors: Hiroshi Nishida, Kazuo Kimura, Shouji Hamada, Masaaki Toma, Hirooki Nagaoka
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Patent number: 5302759Abstract: The invention relates to a process for separating ketones from alcohols by chemical interaction. More specifically, a difference in chemical reactivity between ketones and alcohols with a third compound is used as a basis for the separation. The third compound in this case is an organo-metallic compound of the general formula M(X).sub.n. Herein is M a polyvalent metal atom, n equals the valence of the metal and X is an organic or inorganic group or atom, with the proviso that at least one organic group is present in the organo-metallic compounds according to the invention. If the ketone-alcohol mixture is subjected to the organo-metallic compounds according to the invention under suitable conditions, an exchange reaction between the alcohols and the groups X takes place, and the ketones can be isolated from the reaction mixture in a conventional way.Type: GrantFiled: October 7, 1992Date of Patent: April 12, 1994Assignee: Unilever Patent Holdings B.V.Inventor: Christopher K. Bradley
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Patent number: 5264634Abstract: An alkaline earth metal chelate complex of 2,2,6,6-tetramethylheptanedione of the formula (I)M.sup.2+ (C.sub.11 H.sub.19 O.sub.2).sup.-.sub.2.L.sub.k (I)is described, in which M is calcium, strontium or barium, L is a ligand and k is a number from 1 to 3, the complex being free of water of hydration and the ligand L being an aliphatic ether having at least two oxygen atoms in the molecule. A process for the preparation of the chelate complex and its use for the production of coated substrates are also described.Type: GrantFiled: April 7, 1992Date of Patent: November 23, 1993Assignee: Hoechst AktiengesellschaftInventors: Winfried Becker, Stephan Weidlich
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Patent number: 5250157Abstract: Toluene cannot be separated from methyl isobutyl ketone by conventional distillation or rectification because of the minimum boiling azeotrope. Toluene can be readily separated from methyl isobutyl ketone by using azeotropic distillation. Typical examples of effective agents are 1-butanol, 2-methoxyethanol and n-heptane.Type: GrantFiled: February 22, 1993Date of Patent: October 5, 1993Assignee: Lloyd BergInventors: Lloyd Berg, Randi W. Wytcherley
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Patent number: 5232558Abstract: 4-Methyl-2-pentanone cannot be easily separated from formic acid by distillation because of the closeness of their boiling points. 4-Methyl-2-pentanone can be readily removed from formic acid by extractive distillation. Typical effective agents are dimethylsulfoxide (DMSO) and 2-undecanone; DMSO and octanoic acid; DMSO and hexyl acetate.Type: GrantFiled: October 8, 1992Date of Patent: August 3, 1993Assignee: Lloyd BergInventors: Lloyd Berg, Marc W. Paffhausen
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Patent number: 5228956Abstract: 3-Pentanone cannot be completely removed from 3-pentanone and formic acid mixtures by distillation because of the presence of the maximum azeotrope. 3-Pentanone can be readily removed from 3-pentanone-formic acid mixtures by extractive distillation in which the extractive agent is cyclopentanone, either alone or admixed with certain high boiling organic compounds. Examples of effective agents are cyclopentanone; cyclopentanone and 2-methoxyethyl ether; cyclopentanone, adiponitrile and octanoic acid.Type: GrantFiled: October 2, 1992Date of Patent: July 20, 1993Assignee: Lloyd BergInventors: Lloyd Berg, Rudolph J. Szabados
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Patent number: 5221797Abstract: A process for the purification of pseudo-ionone, which comprises preparing pseudo-ionone by a reaction of citral with acetone, followed by bringing the reaction medium into contact with a metal derivative and thereafter distilling the pseudo-ionone.Type: GrantFiled: April 17, 1992Date of Patent: June 22, 1993Assignee: Rhone-Poulenc Nutrition AnimaleInventors: Pierre Chabardes, Noel Crenne
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Patent number: 5194123Abstract: 4-Methyl-2-pentanone cannot be easily separated from acetic acid by distillation because of the closeness of their boiling points. 4-Methyl-2-pentanone can be readily removed from acetic acid by extractive distillation. Typical effective agents are dimethlsulfoxide (DMSO); DMSO and adipic acid; DMSO, adipic acid and adiponitrile.Type: GrantFiled: July 6, 1992Date of Patent: March 16, 1993Assignee: Lloyd BergInventors: Lloyd Berg, Marc W. Paffhausen
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Patent number: 5190619Abstract: 3-Methyl-2-butanone cannot be separated from formic acid by distillation because of the presence of the maximum boiling azeotrope. 3-Methyl-2-butanone can be readily removed from formic acid by extractive distillation using dimethylsulfoxide (DMSO). Typical effective agents are: DMSO and heptanoic acid; DMSO, octanoic acid and butyl benzoate.Type: GrantFiled: March 30, 1992Date of Patent: March 2, 1993Assignee: Lloyd BergInventors: Lloyd Berg, George Bentu
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Patent number: 5147512Abstract: The higher boiling ketone isomers are difficult to separate one from another by conventional distillation or rectification because of the close proximity of their boiling points. Ketone isomers can be readily separated from each other by extractive distillation. Typical examples of effective agents are: for 3-pentanone from 2-pentanone, dipropylene glycol; 3-hexanone from 2-hexanone, butoxypropanol; 3-heptanone from 2-heptanone, 50% ethylene glycol--50% butoxypropanol; 3-octanone from 2-octanone, ethylene glycol diacetate.Type: GrantFiled: June 28, 1991Date of Patent: September 15, 1992Assignee: Lloyd BergInventors: Lloyd Berg, Thomas A. Edison
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Patent number: 5092965Abstract: 4-Methyl-2-pentanone cannot be easily separated from acetic acid by distillation because of the closeness of their boiling points. 4-Methyl-2-phentanone can be readily removed from acetic acid by extractive distillation. Typical effective agents are dimethylformamide (DMFA); DMFA and m-toluic acid; DMFA, p-toluic acid and isobutyl heptyl ketone.Type: GrantFiled: May 2, 1991Date of Patent: March 3, 1992Assignee: Lloyd BergInventors: Lloyd Berg, Marc W. Paffhausen