Ester Patents (Class 203/60)
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Patent number: 5658435Abstract: 2-Methyl-1-propanol is difficult to separate from 2-butanol by conventional distillation or rectification because of the proximity of their boiling points. 2-Methyl-1-propanol can be easily separated from 2-butanol by azeotropic distillation. Effective agents are sulfolane, acetonitrile and acetal.Type: GrantFiled: September 17, 1996Date of Patent: August 19, 1997Inventor: Lloyd Berg
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Patent number: 5645695Abstract: 2-Methyl-1-propanol is difficult to separate from 2-methyl-1-butanol by conventional distillation or rectification because of the proximity of their boiling points. 2-Methyl-1-propanol can be readily separated from 2-methyl-1-butanol by azeotropic distillation. Effective agents are tetrahydrofuran, methyl acetate and toluene.Type: GrantFiled: July 8, 1996Date of Patent: July 8, 1997Inventor: Lloyd Berg
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Patent number: 5645696Abstract: The present invention relates to a process for continuously preparing unsaturated carboxylic acid esters by esterifying an (aliphatic) alcohol having 1 to 8 carbon atoms with an unsaturated carboxylic acid in the presence of a cation exchange resin catalyst, characterized in that the process is conducted by continuously circulating said reactants in contact with said catalyst from the top to the bottom through a reactor which is composed in the form of a fixed bed divided into 1 to 10 steps wherein each step comprises a catalyst bed, a filter and a air inlet, and has a thermal insulating outer wall, supplying a vaporizing heat for extraction of water, which is produced during the reaction, through a heat exchanger outside the reactor, circulating the reactants between the reactor and the heat exchanger by means of a circulating pump, contacting an azeotropic mixture of water vaporized by the heat exchanger and an alcohol with an alcohol circulating in a column tower or a raw alcohol supplied from an alcohol iType: GrantFiled: November 21, 1994Date of Patent: July 8, 1997Assignee: Lucky Ltd.Inventors: Boo Gon Woo, Kwang Ho Park, Hwa Myung Joo, Han Sun Lee
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Patent number: 5602294Abstract: o-Xylene cannot be separated from p-xylene and m-xylene by conventional distillation or rectification because of the proximity of their boiling points. o-Xylene can be readily separated from mixtures of p-xylene and m-xylene by extractive distillation. Effective agents are o-cresol, dichloroacetic acid, methyl salicylate and 1-tetradecanol.Type: GrantFiled: May 31, 1995Date of Patent: February 11, 1997Inventor: Lloyd Berg
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Patent number: 5597455Abstract: 3-Carene and limonene cannot be separated from each other by rectification because of the closeness of their boiling points. They are readily separated by extractive distillation. Effective agents are: diethylene glycol phenyl ether, nonyl phenol, tripropylene glycol methyl ether, ethyl salicylate, 4-ethylphenol and 2-phenoxyethanol.Type: GrantFiled: January 16, 1996Date of Patent: January 28, 1997Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5582693Abstract: 3-Carene and limonene cannot be separated from each other by rectification because of the closeness of their boiling points. They are readily separated by azeotropic distillation. Effective agents are: cyclopentanol, 2-nitropropane, ethyl formate amyl acetate dimethyl carbonate, tetrahydrofuran, acetic acid and 2-amino-amethyl-1-propanol.Type: GrantFiled: January 11, 1996Date of Patent: December 10, 1996Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5580427Abstract: Butyraldehyde cannot be separated from ethanol by conventional distillation or rectification because they form a minimum boiling azeotrope. Butyraldehyde can be readily separated from ethanol by azeotropic distillation. Effective agents are ethyl formate, hexane and isopropyl ether.Type: GrantFiled: November 7, 1995Date of Patent: December 3, 1996Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5562863Abstract: Vinyl aromatic monomer polymerization methods utilizing a composition of 2,6-di-tert-butyl-4-methylphenol and a substituted benzoquinonediimide compound are disclosed. Preferably, the composition is employed in an amount of 1 part to 10,000 parts per million parts monomer during distillation of styrene.Type: GrantFiled: July 18, 1995Date of Patent: October 8, 1996Assignee: Betz Laboratories, Inc.Inventor: Graciela B. Arhancet
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Patent number: 5470440Abstract: Vinyl aromatic monomer polymerization methods utilizing a composition of 2,6-di-tert-butyl-4-methylphenol and a substituted benzoquinonediimide compound are disclosed. Preferably, the composition is employed in an amount of 1 part to 10,000 parts per million parts monomer during distillation of styrene.Type: GrantFiled: April 19, 1994Date of Patent: November 28, 1995Assignee: Betz Laboratories, Inc.Inventor: Graciela B. Arhancet
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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: 5466345Abstract: o-Xylene cannot be separated from p-xylene and m-xylene by conventional distillation or rectification because of the proximity of their boiling points. o-Xylene can be readily separated from mixtures of p-xylene and m-xylene by azeotropic distillation. Effective agents are 3-methyl-1-butanol, methyl propionate and 3-pentanone.Type: GrantFiled: May 31, 1995Date of Patent: November 14, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5460700Abstract: 1-Hexene is difficult to separate from hexane by conventional distillation or rectification because of the proximity of their boiling points. 1-Hexene can be readily separated from hexane by extractive distillation. Effective agents are hexyl acetate, methyl amyl alcohol and acetophenone.Type: GrantFiled: May 19, 1994Date of Patent: October 24, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5458741Abstract: Benzene is difficult to separate from cyclohexane or cyclohexene by conventional distillation or rectification because of the close proximity of their boiling points. Benzene can be readily separated from cyclohexane or cyclohexene by using extractive distillation. Effective agents are: for benzene from cyclohexane, methyl acetoacetate; for benzene from cyclohexene, ethyl acetoacetate.Type: GrantFiled: January 14, 1994Date of Patent: October 17, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5453167Abstract: p-Xylene cannot be separated from m-xylene by distillation or rectification because of the proximity of their boiling points. p-Xylene can be separated from m-xylene by means of extractive distillation. Effective agents are 3-ethylphenol and isopropyl palmitate. Effective agents for separating mixtures of p-xylene, m-xylene and o-xylene are 2-butoxyethyl acetate and 1,1,1-trichloroethane.Type: GrantFiled: April 7, 1995Date of Patent: September 26, 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: 5447608Abstract: 3-Methyl-2-butanol, 2-pentanol and 1-butanol are difficult to separate by conventional distillation or rectification because of the proximity of their boiling points. Mixtures of these three can be readily separated from each other by azeotropic distillation. Effective agents are hexyl acetate, hexane and 3-methyl pentane.Type: GrantFiled: August 1, 1994Date of Patent: September 5, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5445716Abstract: Ethanol is difficult to separate from isopropanol by conventional distillation or rectification because of the proximity of their boiling points. Ethanol can be readily separated from isopropanol by extractive distillation. Effective agents are dipentene, anisole and ethyl benzene.Type: GrantFiled: October 18, 1994Date of Patent: August 29, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5445715Abstract: m-Xylene is very difficult to separate from mixtures of p-xylene and o-xylene by conventional distillation or rectification because of the proximity of their boiling points. m-Xylene can be readily separated from p-xylene and mixtures of p-xylene and o-xylene by azeotropic distillation. An effective agent is tetraethyl ortho silicate.Type: GrantFiled: March 27, 1995Date of Patent: August 29, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5443697Abstract: Heptane is difficult to separate from 1-heptene by conventional distillation or rectification because of the proximity of their boiling points. Heptane can be readily separated from 1-heptene by extractive distillation. Effective agents are diacetone alcohol, ethyl butyrate and dimethylsulfoxide.Type: GrantFiled: May 19, 1994Date of Patent: August 22, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5441608Abstract: p-Xylene cannot be separated from m-xylene by distillation or rectification because of the proximity of their boiling points. p-Xylene can be separated from m-xylene by means of extractive distillation. Effective agents are 3-ethylphenol and 1,1,2-trichloroethane. Effective agents for separating mixtures of p-xylene, m-xylene and o-xylene are 2-butoxyethyl acetate and 1,1,1-trichloroethane.Type: GrantFiled: May 23, 1994Date of Patent: August 15, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5439561Abstract: 3-Methyl-2-butanol is difficult to separate from 2-pentanol by conventional distillation or rectification because of the proximity of their boiling points. 3-Methyl-2-butanol can be readily separated from 2-pentanol by azeotropic distillation. Effective agents are 2,2-dimethyl butane, ethyl acetate and dioxane.Type: GrantFiled: November 28, 1994Date of Patent: August 8, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5437770Abstract: Ethanol is difficult to separate from isopropanol by conventional distillation or rectification because of the proximity of their boiling points. Ethanol can be readily separated from isopropanol by azeotropic distillation. Effective agents are sec. butyl acetate, hexene-1 and 1,3-dioxolane.Type: GrantFiled: September 13, 1994Date of Patent: August 1, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5425854Abstract: Methylene chloride is difficult to separate from tetrahydrofuran by conventional distillation or rectification because of the proximity of their vapor pressures. Methylene chloride can be readily separated from tetrahydrofuran by extractive distillation. Effective agents are 1-pentanol, 1,2-butanediol and 3-nitrotoluene.Type: GrantFiled: January 17, 1995Date of Patent: June 20, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Process for recovering column bottom residues produced by fractional distillation of ethylene glycol
Patent number: 5423953Abstract: A process for recovering column bottom residues produced by distillation of ethylene glycol resulting from an aromatic polyester production process, involving treating the residues with an aromatic mono-alkyl ester and distilling the reaction product.Type: GrantFiled: January 27, 1994Date of Patent: June 13, 1995Assignee: Montefibre S.p.A.Inventors: Socrate Contessa, Riccardo Tesser, Salvatore Barrella -
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: 5421965Abstract: Glycerine is difficult to separate from bis(hydroxymethyl)tetrahydrofuran by conventional distillation or rectification because of the proximity of their boiling points. Glycerine can be readily separated from bis(hydroxymethyl)tetrahydrofuran by azeotropic distillation. Effective agents are m-xylene, beta-pinene and dicyclopentadiene.Type: GrantFiled: August 1, 1994Date of Patent: June 6, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5417812Abstract: Ethyl benzene is difficult to separate from xylenes by conventional distillation or rectification because of the proximity of their boiling points. Ethyl benzene can be readily separated from xylenes by azeotropic distillation. Effective agents for separating ethyl benzene from p-xylene are methyl formate, n-butanol and cyclopentanol; from p-xylene and m-xylene, n-butanol.Type: GrantFiled: January 10, 1994Date of Patent: May 23, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5417813Abstract: 1-Butanol is difficult to semarate from 2-pentanol by conventional distillation or rectification because of the proximity of their boiling points. 1-Butanol can be readily separated from 2-pentanol by azeotropic distillation. Effective agents are 1-octene, hexane and methyl cyclohexane.Type: GrantFiled: July 11, 1994Date of Patent: May 23, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5417814Abstract: 3-Methyl-2-butanol is difficult to separate from 2-pentanol by conventional distillation or rectification because of the proximity of their boiling points. 3-Methyl-2-butanol can be readily separated from 2-pentanol by extractive distillation. Effective agents are acetamide or 2,2,2-trichloroethanol.Type: GrantFiled: December 5, 1994Date of Patent: May 23, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5415741Abstract: Ethanol is difficult to separate from isopropanol by conventional distillation or rectification because of the proximity of their boiling points. Ethanol can be readily separated from isopropanol by azeotropic distillation. Effective agents are acetonitrile and methylene chloride.Type: GrantFiled: October 18, 1994Date of Patent: May 16, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5407542Abstract: 3-Methyl-2-butanol is difficult to separate from 1-butanol by conventional distillation or rectification because of the proximity of their boiling points. 3-Methyl-2-butanol can be readily separated from 1-butanol by azeotropic distillation. Effective agents are methyl acetoacetate and dioxane.Type: GrantFiled: September 13, 1994Date of Patent: April 18, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5407540Abstract: 3-Methyl-2-butanol is difficult to separate from 1-butanol by conventional distillation or rectification because of the proximity of their boiling points. 3-Methyl-2-butanol can be readily separated from 1-butanol by extractive distillation. Effective agents are ethyl n-valerate, dimethylacetamide and dimethylsulfoxide.Type: GrantFiled: September 23, 1994Date of Patent: April 18, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5405505Abstract: Benzene is difficult to separate from cyclohexane or cyclohexene by conventional distillation or rectification because of the close proximity of their boiling points. Benzene can be readily separated from cyclohexane or cyclohexene by using azeotropic distillation. Effective agents are: for benzene from cyclohexane, dimethoxymethane; for benzene from cyclohexene, methanol.Type: GrantFiled: January 14, 1994Date of Patent: April 11, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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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: 5399244Abstract: Benzene and other aromatics are separated from a stream of mixed hydrocarbons containing both aromatics and non-aromatics by extractive distillation with a solvent system containing dimethyl sulfoxide and optionally a co-solvent, preferably water, followed by distillation stripping of the aromatics from the enriched solvent system, and recycle of the lean solvent system to the extractive distillation step.Type: GrantFiled: December 6, 1993Date of Patent: March 21, 1995Assignee: Glitsch, Inc.Inventors: Joseph C. Gentry, Lloyd Berg, John C. McIntyre, Randa W. Wytcherley
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Patent number: 5399751Abstract: Disclosed is a method for recovering carboxylic acids having from one to ten carbon atoms, and particularly formic acid, acetic acid and mixtures of formic and acetic acids, from aqueous solutions, in which the aqueous solution is contacted with solvent consisting essentially of mixed trialkylphosphine oxides in counter-current liquid-liquid extraction flow in a contacting step to thereby transfer the acids from the aqueous solution to the solvent, thus producing a raffinate relatively low in acid content and a rich solvent. The rich solvent is preferably dehydrated to separate water therefrom and yield a dehydrated rich solvent. The dehydrated rich solvent then has the acids stripped from it and the resulting lean solvent is then returned to the liquid-liquid extraction step, while the separated acids are split into their constituent components in a distillation operation.Type: GrantFiled: November 5, 1993Date of Patent: March 21, 1995Assignee: Glitsch, Inc.Inventors: Joseph C. Gentry, John C. McIntyre, Timothy L. Holmes, Ronald G. Gualy
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Patent number: 5393385Abstract: Hexane is difficult to separate from vinyl acetate and/or methyl acrylate by conventional distillation or rectification because of the closeness of their boiling points. Hexane can be readily separated from vinyl acetate and/or methyl acrylate by extractive distillation. Effective agents are dimethylsulfoxide and dimethylformamide.Type: GrantFiled: March 14, 1994Date of Patent: February 28, 1995Assignee: Lloyd BergInventors: Lloyd Berg, Randi W. Wytcherley
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Patent number: 5391263Abstract: Separation of ethylene glycol and diethylene glycol from dimethyl terephthalate is accomplished by distillation using methyl benzoate or the methyl ester of p-toluic acid as an azeotropic agent.Type: GrantFiled: January 26, 1994Date of Patent: February 21, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventors: Richard R. Hepner, Robert E. Michel, Robert E. Trotter
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Patent number: 5391264Abstract: alpha-Phellandrene is difficult to separate from d-limonene by conventional distillation or rectification because of the proximity of their boiling points. alpha-Phellandrene can be readily separated from d-limonene by azeotropic distillation. Effective agents are n-butyl acetate and sulfolane.Type: GrantFiled: March 14, 1994Date of Patent: February 21, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5382329Abstract: 1-Decene is difficult to separate from decane by conventional distillation or rectification because of the proximity of their boiling points. 1-Decene can be readily separated from decane by azeotropic distillation. Effective agents are methyl propionate, ethyl butyrate and methyl t-butyl ether.Type: GrantFiled: March 11, 1994Date of Patent: January 17, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5382330Abstract: 1-Octene is difficult to separate from octane by conventional distillation or rectification because of the proximity of their boiling points. 1-Octene can be readily separated from octane by azeotropic distillation. Effective agents are ethyl formate, ethyl acetate and t-amyl methyl ether.Type: GrantFiled: March 14, 1994Date of Patent: January 17, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5380405Abstract: alpha-Phellandrene is difficult to separate from 3-carene by conventional distillation or rectification because of the proximity of their boiling points. alpha-phellandrene can be readily separated from 3-carene by azeotropic distillation. Effective agents are methyl formate, nitroethane and acetal.Type: GrantFiled: January 24, 1994Date of Patent: January 10, 1995Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5360520Abstract: 2-Butanol is difficult to separate from t-amyl alcohol by conventional distillation or rectification because of the proximity of their boiling points. 2-Butanol can be readily separated from t-amyl alcohol by extractive distillation. Effective agents are methyl caproate, adiponitrile and cyclopentanone.Type: GrantFiled: January 18, 1994Date of Patent: November 1, 1994Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5358608Abstract: 1-Propanol is difficult to separate from 2-butanol by conventional distillation or rectification because of the proximity of their boiling points. 1-Propanol can be readily separated from 2-butanol by extractive distillation. Effective agents are isobutyl acetate, isobornyl methyl acetate and ethyl butyrate.Type: GrantFiled: January 18, 1994Date of Patent: October 25, 1994Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5348625Abstract: Ethanol is difficult to separate from isopropanol by conventional distillation or rectification because of the proximity of their boiling points. Ethanol can be readily separated from isopropanol by extractive distillation. Effective agents are methyl caproate, cyclopentane and isobutyl acetate.Type: GrantFiled: January 14, 1994Date of Patent: September 20, 1994Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5338410Abstract: 2-Butanol is difficult to separate from t-amyl alcohol by conventional distillation or rectification because of the proximity of their boiling points. 2-Butanol can be readily separated from t-amyl alcohol by azeotropic distillation. Effective agents are ethyl acetoacetate, nitroethane and 3-pentanone.Type: GrantFiled: January 18, 1994Date of Patent: August 16, 1994Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5338411Abstract: Ethanol is difficult to separate from isopropanol by conventional distillation or rectification because of the proximity of their boiling points. Ethanol can be readily separated from isopropanol by azeotropic distillation. Effective agents are methyl ethyl ketone, cyclopentane and 2-pyrrolidinone.Type: GrantFiled: January 14, 1994Date of Patent: August 16, 1994Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5332478Abstract: 1-Propanol is difficult to separate from 2-butanol by conventional distillation or rectification because of the proximity of their boiling points. 1-Propanol can be readily separated from 2-butanol by azeotropic distillation. Effective agents are t-butyl methyl ether, 1,4-dioxane and ethyl formate.Type: GrantFiled: January 14, 1994Date of Patent: July 26, 1994Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5288370Abstract: For the separation of butenes and butanes by extractive distillation, a charge mainly containing butenes and butanes is contacted in an extractive distillation column under pressure with a first selective polar solvent, S1 (e.g., dimethyl formamide), the butanes being collected at the top. The solvent S1 containing the butenes and passing out at the bottom is mixed with a second solvent, S2, having a boiling point intermediate between that of butenes and that of the solvent S1, the mixture passing into a desorption column under pressure, where the butenes are collected at the top. The mixture of solvent S1 and S2 is separated in a purification column under atmospheric pressure, the solvent S2 passing out at the top is recycled to the desorption column, and the solvent S1 passing out at the bottom is recycled to the extractive distillation column.Type: GrantFiled: March 20, 1992Date of Patent: February 22, 1994Assignee: Institut Francais Du PetroleInventors: Lionel Asselineau, Alexandre Rojey