Purification Or Recovery Patents (Class 560/248)
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Patent number: 4314071Abstract: Monoesters of symmetrical dicarboxylic acids and symmetrical diols are prepared in high yield by reacting a diacid or a diol with a monohydric alcohol or monocarboxylic acid, respectively, in an aqueous solution. The resultant monoester is removed from the aqueous solution immediately after its formation by continuous extraction with a nonpolar solvent.Type: GrantFiled: May 12, 1980Date of Patent: February 2, 1982Inventor: James H. Babler
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Patent number: 4311851Abstract: The invention includes a process wherein an olefin is carbonylated with carbon monoxide to form carboxylic acid esters in the presence of a catalyst complex of one mole of BF.sub.3 and one mole of alcohol, and the catalyst is recovered from the desired reaction product and the reaction by-products and is recycled. The carbonylation is carried out until approximately one-half of the alcohol is consumed to form a reaction mass containing the BF.sub.3, the alcohol, and carboxylic acid esters in a 2:1:1 molar ratio. In the first step, the one mole of free BF.sub.3 is vaporized from the reaction mass. The remaining admixture is a 1:1:1 mixture of the aforesaid compounds. To this mixture additional alcohol is added and the mixture is subjected to distillation. An azeotrope of the product carboxylic acid ester and the alcohol and residual alcohol are removed by the distillation, leaving a residue containing a 1:2 BF.sub.Type: GrantFiled: December 19, 1979Date of Patent: January 19, 1982Assignee: Chem Systems Inc.Inventors: John A. Jung, Jimmy Peress
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Patent number: 4304925Abstract: In a process for purifying an ester with little contamination by catalytic metal components in a high yield which comprises treating an esterification reaction mixture with a basic substance, said esterification reaction mixture being obtained by reacting an organic carboxylic acid or its anhydride with an alcohol in the presence of an organometallic compound as an esterification catalyst, and purifying the product in a manner known per se; the improvement wherein prior to said treatment with the basic substance, water is added to the esterification reaction mixture and the mixture is heated.Type: GrantFiled: March 26, 1980Date of Patent: December 8, 1981Assignee: Sekisui Kagaku Kogyo Kabushiki KaishaInventors: Tsutomu Watanabe, Tadayoshi Kawakami
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Patent number: 4297292Abstract: Triglyceride mixture is fractionated to obtain product(s) of Iodine Value different from that of such mixture utilizing particular resin adsorbent and particular solvent.Type: GrantFiled: March 26, 1980Date of Patent: October 27, 1981Assignee: The Procter & Gamble CompanyInventors: Ted J. Logan, Timothy A. Lubsen
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Patent number: 4262138Abstract: In a process wherein ethylene or propylene is carbonylated with carbon monoxide to form carboxylic acid esters in the presence of a catalyst complex of one mole of BF.sub.3 and one mole of alcohol, the invention concerns a technique wherein the catalyst is recovered from the reaction product and recycled. The carbonylation is carried out until approximately one-half of the alcohol is consumed, to form a reaction mass containing the BF.sub.3, the alcohol, and the carboxylic acid ester in a 2:1:1 molar ratio. In the first step, the one mole of the free BF.sub.3 is vaporized from the reaction mass. The remaining admixture is a 1:1:1 mixture of the three aforesaid compounds. To this mixture additional alcohol is added and the mixture is subjected to distillation. A carboxylic acid ester/alcohol azeotrope and residual alcohol are removed by the distillation, to leave a residue containing a 1:2 BF.sub.3 /alcohol complex. This complex is combined with an additional mole of BF.sub.Type: GrantFiled: April 9, 1979Date of Patent: April 14, 1981Assignee: Chem Systems Inc.Inventor: Abraham P. Gelbein
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Patent number: 4260811Abstract: The level of 2-oxazoline or an oxazine impurity in an isocyanatoalkyl ester of an organic carboxylic acid is reduced by (i) reacting the impurity with an organic acid chloride, a chloroformate, a thiochloroformate, a sulfonyl chloride, phosphoryl chloride, sulfuryl chloride or thionyl chloride and (ii) fractionally distilling the reaction mixture to recover the isocyanatoalkyl ester. As an example, crude 2-isocyanatoethyl methacrylate (IEM) containing 0.19 weight percent 2-isopropenyl-2-oxazoline (IPO) is contacted with terephthaloyl chloride for 0.5 hour at 90.degree. C. The reaction mixture is fractionally distilled to recover 97 weight percent of the IEM containing only 0.02 weight percent IPO.Type: GrantFiled: January 14, 1980Date of Patent: April 7, 1981Assignee: The Dow Chemical CompanyInventor: Abel Mendoza
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Patent number: 4256912Abstract: A method for the removal of soluble tellurium compounds from vicinal glycol ester solutions, prepared with tellurium-halide ion catalyst systems, by diluting the tellurium-containing vicinal glycol ester solution with water and contacting said glycol-water solution with a strongly acidic sulfonated ion exchange resin leaving an essentially tellurium-free vicinal glycol ester reaction product which may then be processed to recover the desired ester product and by-products without loss of valuable tellurium. The tellurium may be recovered from the ion exchange resin and treated to recover tellurium in a form suitable for reuse.Type: GrantFiled: October 9, 1979Date of Patent: March 17, 1981Assignee: Atlantic Richfield CompanyInventors: Alfred A. Wolsky, Richard B. Papp, James G. Victor
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Patent number: 4255591Abstract: There is provided an improved continuous homogeneous catalytic carbonylation process wherein a mixed gas stream is removed from the carbonylation reactor, condensable liquids separated from said gas stream and said gas stream vented, the improvement comprising contacting said gas stream with a plurality of hollow fiber membranes selectively permeable to hydrogen under conditions substantially non-degrading of the membranes to generate a non-permeated gas stream of higher carbon monoxide content and recycling said non-permeated gas stream to the carbonylation process reactor. There is also provided for the recovery and recycle to the process of carbonylation products such as acetic or propionic acids by adsorption and removal from a solid adsorbent or absorption in a liquid absorbent.Type: GrantFiled: November 20, 1978Date of Patent: March 10, 1981Assignee: Monsanto CompanyInventors: Earle C. Makin, Jerry L. Price, Yu W. Wei
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Patent number: 4250328Abstract: An improved method for separating an ester formed in a reaction mixture is disclosed. The method comprises controlling the ratio of organic acid and alcohol utilized and the removal of unreacted alcohol as an alcohol-ester azeotrope.Type: GrantFiled: February 6, 1979Date of Patent: February 10, 1981Assignee: Kyowa Yuka Co., Ltd.Inventors: Kiyoshi Fujita, Yukiyoshi Ito, Shigeru Kamimori
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Patent number: 4250330Abstract: The invention refers to an improved process for the recovery of the solvent and of the by-produced methylacetate in the synthesis of terephthalic acid, said synthesis being usually consisting of an oxidation of paraxylene with air, in the presence of a catalyst system composed by cobalt, manganese and bromine, in a solvent consisting of acetic acid, according to the equation (1):C.sub.6 H.sub.4 (CH.sub.3).sub.2 +3 O.sub.2 .fwdarw.C.sub.6 H.sub.4 (COOH).sub.2 =2 H.sub.Type: GrantFiled: January 30, 1980Date of Patent: February 10, 1981Assignee: Montedison S.p.A.Inventors: Giuseppe Costantini, Mauro Serafini, Pietro Paoli
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Patent number: 4241219Abstract: In the carbonylation of esters and/or ethers the reaction mixture is separated into fractions to recover components therefrom, gases are withdrawn from the system and halogen values are recovered from said gases by contact with a component recovered from said reaction mixture.Type: GrantFiled: July 30, 1979Date of Patent: December 23, 1980Assignee: Halcon Research and Development Corp.Inventor: Chee-Gen Wan
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Patent number: 4229261Abstract: Water is separated by distillation from organic multiple component mixtures containing at least one component partly miscible with water. The component miscible with water is distilled azeotropically with the water contained in the mixture, the distillate is separated into water and a zeotrope forming agent and the latter is recycled to the distilling column. In the recycling process, one part of the azeotrope forming agent is conducted to the top of the column and the other part is fed into the column at the feed mixture inlet or at a location thereunder.Type: GrantFiled: December 21, 1978Date of Patent: October 21, 1980Assignee: Hoechst AktiengesellschaftInventors: Gunter Heck, Gunter Roscher, Rudolf Donth
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Patent number: 4215065Abstract: Differential esterification or hydrolysis is utilized to effect separations of isomeric acids or esters.Type: GrantFiled: January 2, 1979Date of Patent: July 29, 1980Assignee: Monsanto CompanyInventor: A. John Solodar
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Patent number: 4213913Abstract: A process for separating an ester of a polyethanoid fatty acid and an ester of a monoethanoid fatty acid from a mixture comprising an ester of a polyethanoid fatty acid, an ester of a monoethanoid fatty acid and an ester of a saturated fatty acid which process comprises contacting the mixture at first adsorption conditions with a first adsorbent comprising an X or a Y zeolite containing a selected cation at the exchangeable cationic sites thereby selectively adsorbing the ester of a polyethanoid fatty acid and thereafter recovering the ester of a polyethanoid fatty acid by desorption with a desorbent material; removing from the first adsorbent a second mixture comprising an ester of a monoethanoid fatty acid and an ester of a saturated fatty acid; contacting the second mixture at second adsorption conditions with a second adsorbent comprising an X or a Y zeolite containing selected cations at the exchangeable cationic sites thereby selectively adsorbing the ester of a monoethanoid fatty acid and thereafter reType: GrantFiled: March 12, 1979Date of Patent: July 22, 1980Assignee: UOP Inc.Inventor: Armand J. de Rosset
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Patent number: 4190729Abstract: In the cobalt carbonyl-catalyzed carbonylation of methanol to ethanol, acetaldehyde and methyl acetate, a tertiary phosphine oxide is utilized as a stabilizer. Product is distilled from the reaction mixture and the cobalt-containing residue solution is recycled.Type: GrantFiled: September 19, 1977Date of Patent: February 26, 1980Assignee: Monsanto CompanyInventor: Denis Forster
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Patent number: 4189442Abstract: Fatty acid ester mixture is separated according to degree of unsaturation utilizing particular resin adsorbent and particular solvent.Type: GrantFiled: March 12, 1979Date of Patent: February 19, 1980Assignee: The Procter & Gamble CompanyInventors: Timothy A. Lubsen, Gustav A. Maag
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Patent number: 4187153Abstract: According to the present invention an impure liquid containing ethylene glycol or propylene glycol, lower carboxylate esters of the glycol, water, carboxylic acid and glycol-azeotroping agent is treated for removal of substantially all of said glycol-azeotroping agent by a process which comprises distilling the impure liquid in a distillation zone to form an overheads product comprising water and glycol-azeotroping agent and a bottoms product comprising the glycol, esters and carboxylic acid, which is substantially free of said glycol-azeotroping agent, said bottoms product containing water in an amount of at least about 1 weight percent of the amount of water passed to said distillation zone with said impure liquid.Type: GrantFiled: November 14, 1977Date of Patent: February 5, 1980Assignee: Halcon Research & Development CorporationInventors: Alan Peltzman, Charles C. Yang
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Patent number: 4182901Abstract: Diacyloxyolefins are isomerized by contacting one or more diacyloxyolefins with a catalyst system comprising selenium dioxide and a suitable carboxylic acid. There can be additionally present in the catalyst system at least one compound selected from the group consisting of a carboxylic acid anhydride, a polar compound, and an ionic reagent.Type: GrantFiled: October 13, 1977Date of Patent: January 8, 1980Assignee: Phillips Petroleum CompanyInventors: George B. Fozzard, John R. Norell
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Patent number: 4158096Abstract: Synthesis and intermediates for making insect pheromone useful in the control of red scale, Aonidiella aurantii.Type: GrantFiled: March 13, 1978Date of Patent: June 12, 1979Assignee: Zoecon CorporationInventor: Richard J. Anderson
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Patent number: 4131642Abstract: Isobutylene, hydrogen cyanide and sulfuric acid are reacted to produce tertiary butyl formamide, which is hydrolyzed by sodium hydroxide to produce tertiary butyl amine. The tertiary butyl amine is removed by vaporization and the residue is treated with sulphuric acid and methanol and is distilled to recover formate values as methyl formate or sodium formate. There is additionally recovered crystalline sodium sulfate and a water immiscible yellow organic phase.Type: GrantFiled: August 12, 1977Date of Patent: December 26, 1978Assignee: Ciba-Geigy CorporationInventors: Ralph Miller, Harry D. Gregg, Jr.
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Patent number: 4131742Abstract: A process for the liquid phase oxidation of hydrocarbons with a molecular oxygen-containing gas in the presence of a dissolved cobalt salt catalyst characterized in that the oxidation is carried out in the substantial absence of chromium in the reaction medium i.e. a concentration of chromium in the liquid phase of not greater than 400 ppm.Type: GrantFiled: November 3, 1976Date of Patent: December 26, 1978Assignee: BP Chemicals LimitedInventor: Barry Hudson
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Patent number: 4131741Abstract: In a process for the production of oxygenated organic compounds including a substantial proportion of acetic acid by oxidizing a C.sub.3 to C.sub.7 saturated aliphatic hydrocarbon in the liquid phase with molecular oxygen in the presence of an inert reaction medium and a cobalt catalyst, between 5 and 90% in a continuous reaction and 11 and 90% in a batch reaction of the cobalt being introduced in the +3 oxidation state, the improvement comprising separating the catalyst solution fraction from the fraction comprising oxygen-containing compounds and water by distillation while limiting the residence time of the catalyst solution fraction in the distillation zone so that it is the minimum consistent with substantially complete separation of the fractions thereby minimizing the reduction of Co.sup.+3 to Co.sup.+2.Type: GrantFiled: December 29, 1976Date of Patent: December 26, 1978Assignee: BP Chemicals LimitedInventors: John S. Bartlett, Barry Hudson
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Patent number: 4116955Abstract: An inclusion complex compound comprising (a) meta-cyclophane and (b) a trans-terpenoid of the formula ##STR1## wherein n is an integer of 1 to 9; A.sub.1 and A.sub.2 each represent (1) a hydrogen atom, (2) a halogen atom, (3) an inorganic group containing an oxygen, nitrogen or sulfur atom, (4) an organic group containing 1 to 5 carbon atoms, or (5) an organic group containing an oxygen, nitrogen or sulfur atom and 1 to 5 carbon atoms; and C* is the carbon atom of a carbonyl or methylene group,Included by the meta-cyclophane. This inclusion complex compound can be prepared by contacting the meta-cyclophane with a mixture containing the trans-terpenoid. A trans-terpenoid can be separated from a mixture containing it by utilizing an inclusion complex compound of it with meta-cyclophane.Type: GrantFiled: May 31, 1977Date of Patent: September 26, 1978Assignee: Teijin LimitedInventors: Yataro Ichikawa, Mamoru Yamamoto, Hideki Tsuruta, Kenichi Kato, Teizo Yamaji, Eishin Yoshisato, Toshiyuki Hiramatsu
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Patent number: 4105701Abstract: A liquid contaminated with a carbonyl compound, especially an aldehyde, is purified by being contacted with a bed of solid polyvinyl alcohol particles or fibers. The carbonyl compound is adsorbed or chemisorbed onto the solid polyvinyl alcohol surface with resulting reaction in the carbonyl content of the liquid.Type: GrantFiled: April 28, 1975Date of Patent: August 8, 1978Assignee: Celanese CorporationInventor: Donald R. Larkin
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Patent number: 4100189Abstract: Acetic acid is recovered from its dilute aqueous solutions by extracting same with an organic solvent, neutralizing the acidic extract with aqueous ammonia, whereby there are separated an organic phase and an ammonium acetate containing aqueous phase, and thence thermally decomposing said ammonium acetate.Type: GrantFiled: January 21, 1976Date of Patent: July 11, 1978Assignee: Rhone-Poulenc IndustriesInventor: Jules Mercier
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Patent number: 4097507Abstract: The present invention relates to a process for separating straight and branched chain soaps and their acids comprising adding to a solution of said soaps a water-soluble lithium compound in at least an amount stoichiometrically sufficient to convert the straight chain soaps present into the corresponding lithium salts, separating such lithium salts from such solution, treating such salts to recover straight chain organic acids and a lithium salt, and recovering branched chain organic acids from the solution.Type: GrantFiled: December 28, 1976Date of Patent: June 27, 1978Assignee: Produits Chimiques Ugine KuhlmannInventor: Lucien Person
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Patent number: 4086267Abstract: A process for the production of oxygenated organic compounds including a substantial proportion of acetic acid by oxidizing a C.sub.3 to C.sub.7 saturated aliphatic hydrocarbon in the liquid phase with molecular oxygen in the presence of an inert reaction medium and a cobalt catalyst, between 5 and 90% in a continuous reaction and 11 and 90% in a batch reaction of the cobalt being introduced in the +3 oxidation state. The process is particularly applicable to the embodiment wherein the catalyst solution is recycled to the oxidation reaction. In order to achieve this a low-residue time distillation unit is preferably employed.Type: GrantFiled: July 19, 1976Date of Patent: April 25, 1978Assignee: BP Chemicals LimitedInventors: John Stanley Bartlett, Barry Hudson, John Pennington
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Patent number: 4083931Abstract: A process for treating and recovering components from aldol-condensation polyol waste liquor containing sodium formate, water, polyol, and organic by-products comprising A. vacuum crystallizing and removing sodium formate; B. introducing methanol and sulfuric acid; C. distilling to remove and recover methyl formate; D. increasing the pH to about 6.5 to 7.0; E. cooling to precipitate Glauber's salt, polyol and organics; and F. adding water to dissolve and separate the Glauber's salt and recover substantially pure polyol and organics.Type: GrantFiled: August 23, 1976Date of Patent: April 11, 1978Assignee: Industrial Sales and Factoring CorporationInventor: Fu-Ming Lee
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Patent number: 4082788Abstract: Organic acids contained in aqueous solution are separated and/or recovered by a process comprising adding an alcohol to the aqueous solution to esterify the acids present, while preferably simultaneously contacting the alcoholic mixture with a water-immiscible solvent and separating layers into an aqueous phase and an organic phase, whereby extraction with the water-immiscible solvent shifts the equilibrium toward the formation of more esters. The esters of the acids may than be recovered as by distillation.Type: GrantFiled: August 19, 1969Date of Patent: April 4, 1978Assignee: El Paso Products CompanyInventor: Samuel S. Mims