Purification Or Recovery Patents (Class 568/410)
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Patent number: 4994151Abstract: 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 using dimethylamides. Typical effective agents are dimethylformamide; dimethylacetamide and acetyl salicyclic acid; dimethylacetamide, heptanoic acid and methyl benzoate.Type: GrantFiled: July 14, 1989Date of Patent: February 19, 1991Assignee: Lloyd BergInventors: Lloyd Berg, George Bentu
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Patent number: 4978430Abstract: An improved method for dehydration and concentration of an aqueous solution containing an organic compound is disclosed. The solution is evaporated to produce a gaseous mixture comprising an organic compound vapor and a water vapor. The water vapor is selectively removed from the gaseous mixture by permeation through an aromatic polyimide gas separation membrane while the gaseous mixture being kept in contact with a surface on one side of the gas separation membrane at a temperature of 70.degree. C. or higher to obtain a gaseous mixture comprising the organic compound vapor and a reduced amount of a water vapor.Type: GrantFiled: July 24, 1989Date of Patent: December 18, 1990Assignee: UBE Industries, Ltd.Inventors: Kanji Nakagawa, Yoshio Asakura, Shigeru Yamamoto, Kohei Ninomiya, Masayuki Kinouchi
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Patent number: 4957595Abstract: 3-Methyl-2-butanone cannot be separated from formic acid by distillation because of the presence of the maximum boiling azotrope. 3-Methol-2-butanoe can be readily removed from formic acid by extractive distillation using sulfolane. Typical effective agents are: sulfolane and ethylene glycol diacetate; sulfolane, m-toluic acid and anisole.Type: GrantFiled: November 7, 1989Date of Patent: September 18, 1990Assignee: Lloyd BergInventors: Lloyd Berg, George Bentu
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Patent number: 4948471Abstract: 4-Methyl-2-pentanone cannot be easily separated from formic acid or acetic acid by distillation because of the closeness of their boiling points. 4-Methyl-2-pentanone can be readily removed from formic acid or acetic acid by extractive distillation. Typical effective agents are sulfolane; sulfolane and heptanoic acid; sulfolane, azelaic acid and ethylene glycol diacetate.Type: GrantFiled: August 1, 1989Date of Patent: August 14, 1990Assignee: Lloyd BergInventors: Lloyd Berg, George Bentu
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Patent number: 4910344Abstract: Aqueous compositions containing organic oxygenates such as methyl isobutyl ketone are treated by pervaporation through a polyvinyl alcohol/polyacrylic acid membrane to yield retentate containing increased concentration of oxygenate.Type: GrantFiled: February 1, 1989Date of Patent: March 20, 1990Assignee: Texaco Inc.Inventors: Mordechai Pasternak, Craig R. Bartels, John Reale, Jr.
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Patent number: 4885399Abstract: Tischtschenko condensation of aldehydes is used to remove aldehydes from dry ketone-containing streams. The tischtschenko condensation is used to condense the aldehydes into esters whose boiling points are significantly different than the ketones, greatly simplifying the separation of the esters from the ketones. An organic extraction step is used to obtain a substantially dry ketone containing stream. One particularly preferred class of extraction solvents is selected from the group consisting of butane, pentane, hexane, heptane, octane, nonane, decane and mixtures thereof. In particularly preferred embodiments, the Tischtschenko reaction is used in the context of aqueous-phase catalyzed olefin oxidation to ketones. The aldehyde to ester condensation permits easy and efficient removal of the aldehyde analogs of the desired ketones.Type: GrantFiled: July 13, 1988Date of Patent: December 5, 1989Assignee: Catalytica, Inc.Inventors: Stanley F. Newman, Jacques C. De Deken, Michael L. Cook
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Patent number: 4861436Abstract: When 4-methyl-2-pentanone and acetic acid mixtures are subjected to extractive distillation with a dimethyl sulfoxide - pelargonic acid mixture as the agent, the acetic acid is converted to gaseous ketene which is easily recovered from the 4-methyl-2-pentanone.Type: GrantFiled: February 7, 1989Date of Patent: August 29, 1989Assignee: Lloyd BergInventors: Lloyd Berg, Richard R. Rall, Marc W. Paffhausen
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Patent number: 4859285Abstract: 2-Pentanone cannot be completely removed from 2-pentanone and formic acid mixtures by distillation because of the presence of the maximum azeotrope. 2-Pentanone can be readily removed from 2-pentanone-formic acid mixtures by extractive distillation in which the extractive agent is a ketone, either alone or mixed with certain high boiling organic compounds. Examples of effective agents are cyclohexanone; diisobutyl ketone and octanoic acid; isophorone, hexanoic acid and butyl ether.Type: GrantFiled: May 2, 1988Date of Patent: August 22, 1989Assignee: Lloyd BergInventors: Lloyd Berg, Rudolph J. Szabados, Thomas H. Flower
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Patent number: 4840707Abstract: 3-Methyl-2-butanone cannot be removed from 3-methyl-2-butanone and formic acid mixtures by distillation because of the presence of the maximum azeotrope between 3-methyl-2-butanone and formic acid. 3-Methyl-2-butanone can be readily removed from 3-methyl-2-butanone - formic acid mixtures by extractive distillation in which the extractive agent is dimethylacetamide, dimethylformamide or these with certain high boiling organic compounds.Type: GrantFiled: December 30, 1988Date of Patent: June 20, 1989Assignee: Lloyd BergInventors: Lloyd Berg, Richard R. Rall
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Patent number: 4793901Abstract: 2-Pentanone cannot be completely removed from 2-pentanone and formic acid mixtures by distillation because of the presence of the maximum azeotrope. 2-Pentanone can be readily removed from 2-pentanone formic acid mixtures by extractive distillation in which the extractive agent is dimethylsulfoxide, either alone or mixed with certain high boiling organic compounds. Examples of effective agents are dimethylsulfoxide; DMSO and octanoic acid; DMSO, hexanoic acid and isophorone.Type: GrantFiled: April 11, 1988Date of Patent: December 27, 1988Assignee: Hoechst Celanese Chemical Co.Inventors: Lloyd Berg, Rudolph J. Szabados
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Patent number: 4775448Abstract: A process of isolating dihydroxyacetone which is a useful intermediate in organic chemistry as well as being a sun-tanning agent. The process comprises passing a reaction mixture containing dihydroxyacetone in an organic solvent through at least one thin film evaporator to distil dihydroxyacetone separately from the solvent.Type: GrantFiled: April 30, 1987Date of Patent: October 4, 1988Assignee: Imperial Chemical Industries PLCInventors: Martin E. Fakley, Robert J. Lindsay
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Patent number: 4701561Abstract: This invention is directed to the discovery that a mixture of aldehydes and ketones where the boiling points of the aldehyde and the ketone are very close can be easily separated through the acid-catalyzed cyclotrimerization of the aldehyde and the subsequent distillation of the ketone and unreacted aldehyde from the reaction mixture. The trimerized aldehyde is cracked back to the starting aldehyde in high purity at elevated temperatures in the presence of an acid catalyst.Type: GrantFiled: March 13, 1987Date of Patent: October 20, 1987Assignee: The Goodyear Tire & Rubber CompanyInventor: Wen-Liang Hsu
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Patent number: 4678544Abstract: This invention is directed to the discovery that the distillative separation of 2-methylbutanal (2MBA) from a mixture containing methylisopropylketone (MIPK) and 2MBA can be greatly enhanced by the addition of water to the mixture.Type: GrantFiled: February 28, 1986Date of Patent: July 7, 1987Assignee: The Goodyear Tire & Rubber CompanyInventor: Lawson G. Wideman
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Patent number: 4670606Abstract: A mixture of linear and branched-chain detergent oxo-alcohols, containing from 11 to 16 carbon atoms in the molecule, is dissolved in a hydrocarbon or ether solvent, and the solution thus obtained is cooled to obtain a dispersion of a solid phase in a liquid phase.The solid phase constituting the linear-chain oxo-alcohol fraction is separated and recovered. The branched-chain oxo-alcohol fraction is separated and recovered from the liquid phase.Type: GrantFiled: February 8, 1985Date of Patent: June 2, 1987Assignee: Chimica Augusta, S.p.A.Inventors: Ugo Romano, Giacomo Sasselli, Luigi Raisa
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Patent number: 4564477Abstract: There are provided polyprenyl compounds of the formula ##STR1## wherein ##STR2## represent a trans-isoprene unit and a cis-isoprene unit, respectively, n is an integer of 11-19, Z.sup.1 and Z.sup.2 combinedly represent .dbd.O, .dbd.CH--COOH,.dbd.CH--COOR.sup.1, .dbd.CH--CN, .dbd.C(CN)COOR.sup.2, .dbd.CH--CO--NH.sub.2, .dbd.CH--CO--N(R.sup.3) (R.sup.4), .dbd.CH--CO--NHR.sup.5, .dbd.CH--CH.sub.2 --N(R.sup.3) (R.sup.4), .dbd.CH--CH.sub.2 --NHR.sup.5 or .dbd.CH--CHO or Z.sup.1 is a hydrogen atom and Z.sup.2 is --CH.sub.2 COOH, --CH.sub.2 COOR.sup.6, --CH(CN)COOR.sup.2, --CH.sub.2 CN, --CH.sub.2 --CO--NH.sub.2, --CH.dbd.CH--N(R.sup.3) (R.sup.4) or --CH.sub.2 --CH.dbd.N--R.sup.5, R.sup.1, R.sup.2 and R.sup.6 each being a lower alkyl group, R.sup.3 and R.sup.4 each independently being a lower-alkyl, cycloalkyl, aryl or aralkyl group or R.sup.3 and R.sup.4 combinedly representing an alkylene group containing 2-5 carbon atoms, and R.sup.5 being a lower-alkyl, cycloalkyl, aryl or aralkyl group.Type: GrantFiled: February 17, 1983Date of Patent: January 14, 1986Assignee: Kuraray Co., Ltd.Inventors: Tetsuo Takigawa, Koichi Ibata, Masafumi Okada, Masao Mizuno, Takashi Nishida
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Patent number: 4544454Abstract: Isopropyl ether cannot be completely removed from isopropyl ether - methyl ethyl ketone mixtures by distillation because of the presence of the minimum binary azeotrope. Isopropyl ether can be readily removed from mixtures containing it and methyl ethyl ketone by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated and/or nitrogenous organic compound or a mixture of these. Typical examples of effective agents are adiponitrile; ehtylene carbonate plus dimethylformamide; adiponitrile plus dimethylformamide plus glycerine.Type: GrantFiled: February 10, 1984Date of Patent: October 1, 1985Inventors: Lloyd Berg, An-I Yeh
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Patent number: 4450294Abstract: An oxygenated organic compound, such as ethanol, is recovered from a dilute aqueous stream thereof by contacting said stream with crosslinked polyvinylpyridine resin or nuclear substituted derivative thereof to effect selective sorption of the compound by said resin. The sorbed compound is thereafter removed from the resin by stripping with an inert gas such as carbon dioxide.Type: GrantFiled: November 1, 1982Date of Patent: May 22, 1984Assignee: National Distillers and Chemical CorporationInventor: Julian Feldman
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Patent number: 4415409Abstract: An extractive distillation process is provided for the separation of phenol and/or cresol from mixtures with high boiling oxygenated compounds such as alkanols, alkanones, cycloalkanones, cycloalkanols, aryl alcohols, aryl ketones or mixtures thereof that have a boiling point of at least about 175.degree. C. The process involves distilling the phenol and/or cresol-high boiling oxygenated compound mixture in the presence of at least one extractive solvent comprising a substituted phenol and/or substituted cresol that has a boiling point between about 195.degree. C. and about 400.degree. C.Type: GrantFiled: February 22, 1983Date of Patent: November 15, 1983Assignee: Allied CorporationInventors: David Zudkevitch, Stephen E. Belsky
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Patent number: 4349415Abstract: Process and apparatus for extracting an organic liquid from an organic liquid solute/solvent mixture. The mixture is contacted with a fluid extractant which is at a temperature and pressure to render the extractant a solvent for the solute but not for the solvent. The resulting fluid extract of the solute is then depressurized to give a still feed which is distilled to form still overhead vapors and liquid still bottoms. The enthalpy required to effect this distillation is provided by compressing the still overhead vapors to heat them and indirectly to heat the still feed. The process is particularly suitable for separating mixtures which form azeotropes, e.g., oxygenated hydrocarbon/water mixtures. The energy required in this process is much less than that required to separate such mixtures by conventional distillation techniques.Type: GrantFiled: September 28, 1979Date of Patent: September 14, 1982Assignee: Critical Fluid Systems, Inc.Inventors: Richard P. DeFilippi, J. Edward Vivian
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Patent number: 4329510Abstract: In a process for recovering a purified ketone substantially free from aldehydes which comprises contacting a crude ketone containing small amounts of aldehydes with an alkali and then distilling the treated crude ketone, the improvement wherein said alkali is a solid alkali composition composed of an alkali metal compound selected from alkali metal oxides and hydroxides, an alkaline earth metal compound selected from alkaline earth metal oxides and hydroxides and silicon dioxide in which the mole ratio of the alkali metal to the alkaline earth metal is in the range of from 1:1 to 1:15, and the mole ratio of the alkali metal to silicon is in the range of from 1:0.25 to 1:5.Type: GrantFiled: August 6, 1980Date of Patent: May 11, 1982Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Kazutoyo Uno, Hisaya Miki
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Patent number: 4213832Abstract: A process for separating the constituents of azeotropic mixtures of acetone and other lower ketones from lower halogenated hydrocarbons. Water is added to the azeotropic mixture of acetone and the lower halogenated hydrocarbon for breaking up of the azeotrope, and the halogenated halohydrocarbon is distilled off.Type: GrantFiled: June 21, 1978Date of Patent: July 22, 1980Assignee: Allied Chemical CorporationInventors: David Zudkevitch, Nirmal K. Khanna, Robert F. Raczynski