Purification Or Recovery Per Se Patents (Class 562/608)
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Patent number: 4883912Abstract: In a process for the recovery of acetic acid by extracting acetic acid from an aqueous acetic acid solution containing a metallic salt of sulfuric acid with an organic extractant comprising a tertiary amine and an organic diluent and recovering acetic acid from the liquid extract, a mixture of a tertiary amine containing sulfuric acid and an organic diluent is used as an organic extractant so as to suppress energy consumption and to increase extraction efficiency.Type: GrantFiled: May 14, 1986Date of Patent: November 28, 1989Assignee: Daicel Chemical Industries, Ltd.Inventors: Kunio Koga, Koji Shima, Mutsumi Samejima
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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: 4837362Abstract: Pure hydroxylammonium salts of fatty acids of 1 to 4 carbon atoms are prepared by reacting hydroxylammonium sulfate and alkali metal salts of fatty acids with 1 to 4 carbon atoms in solution at elevated temperatures and separating off the hydroxylammonium salts of fatty acids of 1 to 4 carbon atoms by(a) reacting hydroxylammonium sulfate and alkali metal salts of fatty acids of 1 to 4 carbon atoms in solution in water or alkanols of 1 to 3 carbon atoms or mixtures thereof at 20.degree.-70.degree. C.,(b) evaporating the solvent out of the reaction mixture to obtain a dry residue,(c) isolating the hydroxlammonium salts of fatty acids of 1 to 4 carbon atoms from the dry residue thus obtained by sublimation under reduced pressure.Type: GrantFiled: January 15, 1987Date of Patent: June 6, 1989Assignee: BASF AktiengesellschaftInventors: Hugo Fuchs, Franz-Josef Weiss
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Patent number: 4822760Abstract: A process of regenerating a palladium salt catalyst comprising, in combination, steps of:(I) heating an organic residue containing a palladium salt catalyst which has been separated from a reaction solution, at a temperature of not lower than 330.degree. C. under an inert gas atmosphere to produce a reduced and thermally decomposed porous product;(II) firing the porous product produced in the step I under an oxygen-containing atmosphere; and(III) treating the product fired in the step II with an acid to produce a palladium salt.Type: GrantFiled: December 24, 1987Date of Patent: April 18, 1989Assignee: UBE Industries, Ltd.Inventors: Masaki Kashibe, Hideyuki Sugishita, Nobuyoshi Okada
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Patent number: 4801358Abstract: Dioxane cannot be completely removed from dioxane and acetic acid mixtures by distillation because of the presence of the maximum azeotrope. Dioxane can be readily removed from dioxane - acetic acid mixtures by extractive distillation in which the extractive agent is N,N-dimethylacetamide or dimethylformamide, either alone or mixed with certain high boiling organic compounds. Examples of effective agents are N,N-dimethylacetamide; dimethylformamide and heptanoic acid; N,N-dimethylacetamide, heptanoic acid and diethylene glycol diethyl ether.Type: GrantFiled: July 28, 1988Date of Patent: January 31, 1989Inventors: Lloyd Berg, Rudolph J. Szabados
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Patent number: 4801357Abstract: Dioxane cannot be completely removed from dioxane and acetic acid mixtures by distillation because of the presence of the maximum azeotrope. Dioxane can be readily removed from dioxane-acetic 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 1, 1988Date of Patent: January 31, 1989Inventors: Lloyd Berg, Rudolph J. Szabados
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Patent number: 4729818Abstract: Acetic acid cannot be easily removed from acetic acid--water mixtures by distillation because of the closeness of their boiling points and the deviation from ideal solution behavior. Acetic acid can be readily removed from mixtures containing it and water by using extractive distillation in which the extractive distillation agent is a mono carboxylic acid, either singly or admixed with high boiling organic compounds. Typical examples of effective agents are pelargonic acid; heptanoic acid and isophorone; neodecanoic acid, acetophenone and nitrobenzene.Type: GrantFiled: April 16, 1987Date of Patent: March 8, 1988Inventor: Lloyd Berg
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Patent number: 4720577Abstract: The invention relates to a process for the extraction of carboxylic acids from aqueous solutions with a carboxylic acid content below 8% by weight. A mixture of an aliphatic amine with a total carbon number of at least 10 and a phenol or naphthol is used as extracting agent. The molar ratio of phenol:amine or alkylated phenol:amine or naphthol:amine is in the range from 0.1:1 to around 1.1:1.Type: GrantFiled: October 2, 1985Date of Patent: January 19, 1988Assignee: Hoechst AktiengesellschaftInventors: Bernhard Wojtech, Walter Steppich, Dieter Freudenberger, Knut Riedel
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Patent number: 4699725Abstract: Finely divided ore blends containing chemically active magnesium oxide and calcium oxide are physically combined with a critical amount of water prior to reaction with acetic acid. Intermediate products range in physical consistency from putty-like masses to viscous liquors, depending upon the relative fraction of magnesium oxide in the ore feed. Intermediate products freeze to form hydrates of magnesium calcium acetate, the freeze times being dependent upon a number of chemical and physical parameters. Product drying requirements range from minimal drying to none at all, depending upon the magnesium fraction in the products. Products are non-friable and have excellent crush strength, and are suitable for storage, shipping and application in chemical deicing as well as other end use applications where crude low-cost materials are called for.A unique situation centers around the composition corresponding to the magnesium mol fraction of 0.8.Type: GrantFiled: December 12, 1986Date of Patent: October 13, 1987Inventor: Alan B. Gancy
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Patent number: 4691055Abstract: An improved process is provided for concentrating organic compounds from dilute aqueous solutions such as fermentation liquors. Conventional distillation of the compounds to remove the bulk of the water is eliminated by selective adsorption on adsorbent carbon. The compounds are eluted from the carbon with the vapors of a volatile solvent and then the volatile solvent is evaporated from the eluate to give a concentrated aqueous solution containing at least 30% by weight of the organic compounds.Type: GrantFiled: December 7, 1981Date of Patent: September 1, 1987Assignee: CPC International Inc.Inventor: Branko Urbas
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Patent number: 4678583Abstract: A process for forming a purified solute from an aqueous solution is provided whereby a mixture of an extractant, a hydrate former and the aqueous solution is first formed. The hydrate former forms a hydrate with water while the solute does not form a hydrate. The extractant takes up the solute from the aqueous solution. The mixture is subjected to a temperature and pressure sufficient to form the solid hydrate of the hydrate former, an aqueous solution of the solute and a portion comprising the extractant containing the solute. The solute is recovered from the portion comprising the extractant and the solute.Type: GrantFiled: June 12, 1986Date of Patent: July 7, 1987Assignee: Massachusetts Institute of TechnologyInventors: Richard C. Willson, III, Eric Bulot, Charles L. Cooney
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Patent number: 4673519Abstract: Several novel means are presented of chemically combining calcium/magnesium acetate with calcium chloride to form a series of calcium magnesium acetate-chloride triple-salts. The low-cost processes are carried out using minimal proportions of water, and no co-products or by-products are formed. Products are optionally pelletized for use as roadway deicing agents. By adjusting the relative amount of chloride input, products can be tailored to adequately perform a given deicing or freezing-point depression task with a minimum of environmental pollution by chloride.All product variations are non-deliquescent.In the preferred embodiment, lime is reacted with concentrated acetic acid to form calcium/magnesium acetate. To the acetate is added an aqueous calcium chloride solution. The concentration of water in the reaction batch is critical to the attainment of complete chemical combination to form a flowable solid product.Type: GrantFiled: June 24, 1985Date of Patent: June 16, 1987Inventor: Alan B. Gancy
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Patent number: 4664753Abstract: The disclosure relates to a process for separating iodine and its compounds from the carbonlyation products acetic acid, acetic anhydride or ethylidene diacetate obtained by subjecting dimethylether, methyl acetate or methanol to a carbonylation reaction. For reducing the quantity of total iodine contaminating the carbonlyation products to less than 20 ppb iodine, the disclosure provides for the carbonylation products to be treated at temperatures of 20.degree. to 250.degree. C. with an alkyl or aryl phosphine or a heterocyclic aromatic nitrogen compound and at least one of the metals copper, silver, zinc or cadmium or their compounds and to be distillatively separated from the iodine thereby fixed in non-volatile form.Type: GrantFiled: August 6, 1984Date of Patent: May 12, 1987Assignee: Hoechst AktiengesellschaftInventors: Heinz Erpenbach, Klaus Gehrmann, Winfried Lork, Peter Prinz
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Patent number: 4661208Abstract: The invention provides a means for greatly saving the thermal energy consumption in the dehydrating distillation of an aqueous solution of a carboxylic acid such as acetic acid by use of an azeotropically distilling entrainer boiling at a lower temperature than the carboxylic acid and immiscible with water. The improvement proposed by the invention comprises taking at least a part of the entrainer phase separated from the condensate coming from the column top or at least a part of the side-cut fluid abstracted from the refluxing fluid inside the column, evaporating the thus taken fluid into vapor and introducing the vapor into the distillation column at a stage for the introduction of the starting feed or below.Type: GrantFiled: June 21, 1985Date of Patent: April 28, 1987Assignee: Shin-Etsu Vinyl Acetate Co., Ltd.Inventors: Yoshihiro Honma, Fumiaki Kawamoto, Shozo Tanaka
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Patent number: 4658057Abstract: In extracting a solute from an aqueous solution using a mixer-settler extractor and an organic extractant comprising a mixture of a tertiary amine and an organic diluent, the extractor is operated while the liquid phase inside the mixer thereof is kept in a state of solvent dispersion. Thus, the mixer-settler extractor can be operated efficiently.Type: GrantFiled: January 10, 1984Date of Patent: April 14, 1987Assignee: Daicel Chemical Industries, Ltd.Inventors: Kunio Koga, Yukihiro Sasaki, Hirotoshi Niwa
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Patent number: 4623432Abstract: The recovery of an acetic acid product of low brominated organics content can be made from the liquid effluent from n-butane oxidation with oxygen gas in the presence of an acetic acid solution containing ion of bromine in combination with ions of cobalt or with ions of manganese and cobalt. Such recovery is made not by the use of a series of separate fractionation towers but rather by the use of a single fractionation tower having a top rectification zone, an intermediate stripping zone with a feed inlet at the top thereof and a bottom reboiler zone below the stripping zone wherein the acetic acid product is removed as a vapor product from said stripping zone below said feed inlet but above the reboiler zone.Type: GrantFiled: April 23, 1984Date of Patent: November 18, 1986Assignee: Amoco CorporationInventor: Moinuddin H. Ali
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Patent number: 4618709Abstract: A process for separation of methacrylic acid from a methacrylic acid-containing, gaseous reaction mixture obtained by subjecting methacrolein or a compound which can afford methacrolein under reaction conditions and molecular oxygen to gas phase reaction in the presence of a catalyst for oxidation under the coexistence of an inert gas for dilution which comprises (a) cooling the gaseous reaction mixture from a reactor wherein the gas phase reaction has been effected to separate into condensable components including methacrylic acid, acetic acid and water vapor as a condensed liquor and non-condensable components including methacrolein as a non-condensed gaseous mixture, (b) eliminating contaminating methacrolein from the condensed liquor and (c) contacting the resulting condensed liquor with an organic solvent to extract methacrylic acid, followed by separation into an organic solvent solution including methacrylic acid and an aqueous solution as waste water, characterized in that (1) the inert gas for dilutiType: GrantFiled: January 30, 1981Date of Patent: October 21, 1986Assignee: Sumitomo Chemical Company, LimitedInventors: Masao Sada, Michio Kato, Masami Ayano, Tadashi Abe, Masanori Moriwaki
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Patent number: 4615806Abstract: The invention relates to a method for removing iodide compounds from a non-aqueous organic medium, such as acetic acid. The medium is contacted with a macroreticulated strong-acid cation exchange resin which is stable in the organic medium and has at least one percent of its active sites converted to the silver or mercury form.Type: GrantFiled: March 7, 1985Date of Patent: October 7, 1986Assignee: Celanese CorporationInventor: Charles B. Hilton
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Patent number: 4606836Abstract: Finely divided lime, at any degree of slaking, is introduced in a steady stream into an agitated reactor designed to produce pellets or aggregates. Concentrated acetic acid is simultaneously introduced in a steady stream at a rate equal to the chemical combining rate required to produce calcium magnesium acetate. Water content of the reaction stream is critical; the mol ratio of water, including water of neutralization, to the calcium magnesium acetate product must fall in the range 3.3-7.0 in order to form the desired pellets and to avoid sticking, caking, and dust emanation from the reactor. Product pellets are drawn off in a stream from the reactor and dried for use as a non-polluting roadway and walkway deicer. Traction agent is optionally incorporated into the deicer pellets by introducing a steady stream of traction agent to the reactor simultaneous with raw materials introduction. Magnesium-to-calcium ratios greater than one are achieved by blending dolime with magnesium-rich ore.Type: GrantFiled: January 22, 1985Date of Patent: August 19, 1986Inventor: Alan B. Gancy
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Patent number: 4599144Abstract: Process is disclosed for treating the reaction product of propionic acid and formaldehyde to recover methacrylic acid from an aqueous effluent wherein said effluent contains methacrylic acid, unreacted formaldehyde, unreacted propionic acid, water and by-products.Type: GrantFiled: June 25, 1984Date of Patent: July 8, 1986Assignee: Standard Oil Company (Indiana)Inventors: Marc O. Baleiko, Edward F. Rader
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Patent number: 4582570Abstract: Improvement in an azeotropic distillation process, the improvement being the use of an entrainer characterized in that it is an organic compound in which one or more hydrogen atoms are replaced by halogen atoms, including at least one fluorine atom; it is miscible, under process conditions, with the organic compound being dehydrated; its volatility is sufficiently close to the volatility of the organic compound being dehydrated such that, under the process conditions, it forms an azeotrope with the organic compound; it is less miscible, under process conditions, with water than is the corresponding organic compound in which the halogen atoms are replaced with hydrogen atoms; and it is chemically stable under the process conditions.Type: GrantFiled: June 20, 1983Date of Patent: April 15, 1986Assignee: Merix CorporationInventor: Thomas W. Mix
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Patent number: 4576683Abstract: A method for separating carboxylic acids from mixtures with non-acids by an extractive distillation method using a lactam with a 5- or 6-membered ring, preferably N-methyl-2-pyrrolidone, as an extractant to extract the acids from the mixture with non-acids, followed by separating the extracted acids from the extractant by rectification.Type: GrantFiled: June 6, 1984Date of Patent: March 18, 1986Assignee: Badger B.V.Inventor: Lester R. Cohen
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Patent number: 4562288Abstract: In extracting object material from its aqueous solution by using an organic solvent, a mixer-settler extractor is employed as the extractor and operated while a solvent dispersion is maintained in the mixer, and part of the aqueous phase discharged from the settler is recycled to the mixer so that the organic solvent phase in the mixer is stably maintained as the disperse phase.Type: GrantFiled: January 10, 1984Date of Patent: December 31, 1985Assignee: Daicel Chemical Industries, Ltd.Inventors: Kunio Koga, Yukihiro Sasaki, Mutsumi Samejima
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Patent number: 4544453Abstract: An improved method of stripping unreacted alkylene glycol monoalkyl ethers and unreacted monocarboxylic or halogenated monocarboxylic acids from a mixture containing the monocarboxylic acid ester prepared therefrom by acid catalyzed esterification without any significant loss of the product ester. The method involves the injection of water into the distillate during the stripping and is particularly suitable for the recovery of propylene glycol monomethyl ether and acetic acid from esterification reaction mixtures containing a predominate amount of product propylene glycol monomethyl ether acetate. The process allows for removal and recovery or recycle of the ether and acid and the preparation of a higher purity product ester.Type: GrantFiled: May 31, 1984Date of Patent: October 1, 1985Assignee: Atlantic Richfield CompanyInventor: Vijai P. Gupta
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Patent number: 4529550Abstract: Improvements in efficiencies and yields are achieved in the production of a saturated aliphatic monocarboxylic acid containing 5 to 9 carbon atoms from its corresponding aldehyde by rapidly hydrolyzing the anhydride of the monocarboxylic acid formed in the oxidation. The hydrolysis is accomplished by contacting the anhydride with water at a temperature from about 130.degree. C. to about 215.degree. C. and at a pressure under which the water is maintained in the liquid state to convert the anhydride to its corresponding acid.Type: GrantFiled: January 17, 1983Date of Patent: July 16, 1985Assignee: Celanese CorporationInventors: Olan S. Fruchey, James S. Alder
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Patent number: 4517377Abstract: A process for producing vinyl acetate which comprises decomposing ethylidene diacetate in the presence of at least one compound selected from fluorides, bromides, chlorides, iodides, halogens and mixtures thereof is disclosed. According to this invention decomposition rate of ethylidene diacetate is high and selectivity to vinyl acetate is also high.Type: GrantFiled: June 18, 1982Date of Patent: May 14, 1985Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tomiya Isshiki, Takanari Nawata, Yasuhiko Kijima, Akira Ito, Takayuki Watanabe
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Patent number: 4511485Abstract: A reduced pollutant-containing salt mixture and method of making same is provided wherein a salt mixture partially comprised of calcium acetate and partially comprised of at least one other pollutant salt is produced by mixing a pollutant salt-containing solution and a calcium acetate-containing solution and converting said mixture into a solid salt containing both the pollutant salt and the nonpollutant calcium acetate. A process option involves chemically reacting calcium chloride and calcium acetate in a calcium chloride-to-calcium acetate mole ratio in the range from 0 to 1 to produce a non-deliquescent salt. A further process option includes mixing either dry calcium chloride or dry sodium chloride with dry calcium acetate to obtain a reduced pollutant-containing salt mixture.Type: GrantFiled: April 20, 1983Date of Patent: April 16, 1985Inventor: Alan B. Gancy
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Patent number: 4508688Abstract: A process for separating lead includes the steps of dissolving a water insoluble lead salt in an acetate solution and precipitating the lead by treating the acetate solution with a sulfite so as to form an insoluble lead sulfite. The acetate is recovered by concentrating the solution and precipitating the acetate therefrom, drying the acetate crystals and dissolving them in methanol. The methanol is then evaporated leaving purified acetate crystals. The process is shown as part of a precious metal recovery system in the treatment of tankhouse slime.Type: GrantFiled: May 31, 1983Date of Patent: April 2, 1985Assignee: AT&T Technologies, Inc.Inventors: Christopher C. Handy, Jr., D'Arcy H. Lorimer
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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: 4447643Abstract: A thermally efficient process for recovering an oxygenated organic material, such as ethanol, present in dilute aqueous solution is disclosed which comprises contacting said dilute aqueous solution with at least one inert extractant which is liquid at ambient temperature and pressure, said extractant being selected from the group consisting of unsubstituted and substituted cyclic secondary amines and unsubstituted and substituted aromatic cyclic amines having a distribution coefficient of at least about 0.70 or a separation factor of at least about 1.0.Type: GrantFiled: August 11, 1982Date of Patent: May 8, 1984Assignee: National Distillers and Chemical CorporationInventor: Julian Feldman
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Patent number: 4444672Abstract: A process of making a calcium acetate-containing solution having a pH value at room temperature between about 7 and about 8 is provided comprising reacting acetic acid with a carbonate compound, adding calcined limestone, and optionally finishing off the acid-base reaction with an amount of an alkali metal hydroxide comprising from about 2% to about 5% of the total stoichiometric complement to the amount of acetic acid. Further process options which may be used in the preparation of deicing agents include adding coarse limestone to the above-prepared calcium acetate-containing solution in amounts up to 10% by weight and converting the solution into solid flakes. The calcium acetate salt product can be mixed with an inert solid material having good anti-slip properties.Type: GrantFiled: April 20, 1983Date of Patent: April 24, 1984Inventor: Alan B. Gancy
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Patent number: 4433165Abstract: The present invention provides for an improved process wherein an olefin, an alcohol, or an ester, halide or ether derivative of said alcohol is reacted with carbon monoxide in a liquid phase in the presence of a catalyst system that contains (a) a rhodium component, and (b) an iodine or bromine component. By passing at least a portion of the liquid reaction mass from the reaction zone to a separation zone of substantially lower CO partial pressure, at least a portion of the carbonylation products, as well as unreacted carbon monoxide, inert gases, and unreacted olefin, alcohol, or alcohol derivatives are vaporized and can be withdrawn from the separation zone. Precipitation of the rhodium catalyst under carbon monoxide deficient conditions is prevented or retarded by addition to the system of a stabilizer component selected from N,N,N',N'-tetramethyl-o-phenylenediamine and 2,3'-dipyridyl.Type: GrantFiled: December 29, 1980Date of Patent: February 21, 1984Assignee: Monsanto CompanyInventor: Thomas C. Singleton
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Patent number: 4433166Abstract: The present invention provides for an improved process wherein an olefin, an alcohol, or an ester, halide or ether derivative of said alcohol is reacted with carbon monoxide in a liquid phase in the presence of a catalyst system containing a rhodium component and an iodine or bromine component. By passing at least a portion of the liquid reaction mass from the reaction zone to a separation zone of substantially lower CO partial pressure, at least a portion of the carbonylation products, as well as unreacted carbon monoxide, inert gases, and unreacted olefin, alcohol, or alcohol derivatives are vaporized and can be withdrawn from the separation zone. Precipitation of the rhodium catalyst under carbon monoxide deficient conditions is prevented or retarded by addition to the system of a stabilizer which is a tin component which may be tin or a tin compound.Type: GrantFiled: December 29, 1980Date of Patent: February 21, 1984Assignee: Monsanto CompanyInventors: Thomas C. Singleton, Frank E. Paulik
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Patent number: 4430242Abstract: A process of reacting aqueous acetic acid and crushed raw limestone in such a way as to produce a mixture of calcium acetate, calcium acid-acetate, and unreacted raw limestone devoid of undesirable fine limestone. Such a product is useful in winter highway treatment, where the environmentally safe soluble acetates function to depress the freezing point of water, and the limestone acts as a roadway traction agent. When as much as 3 mols of acetic acid per mol of active calcium carbonate in limestone are used, all the limestone is consumed, with virtually 100% yield of calcium acid-acetate.Type: GrantFiled: August 2, 1982Date of Patent: February 7, 1984Inventor: Alan B. Gancy
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Patent number: 4426308Abstract: A process of making a calcium acetate-containing solution having a pH value at room temperature between about 7 and about 8 is provided comprising reacting acetic acid with a carbonate compound, adding calcined limestone, and optionally finishing off the acid-base reaction with an amount of an alkali metal hydroxide comprising from about 2% to about 5% of the total stoichiometric complement to the amount of acetic acid. Further process options which may be used in the preparation of deicing agents include adding coarse limestone to the above-prepared calcium acetate-containing solution in amounts up to 10% by weight and converting the solution into solid flakes.Type: GrantFiled: March 18, 1983Date of Patent: January 17, 1984Inventor: Alan B. Gancy
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Patent number: 4413140Abstract: A solvent comprising at least one aromatic hydrocarbon and/or halogenated paraffin is used in a liquid extraction process for extracting diesters from mixtures comprising diesters, the corresponding monoesters and acids, diols and water.Type: GrantFiled: April 26, 1977Date of Patent: November 1, 1983Assignee: Phillips Petroleum CompanyInventor: George B. Fozzard
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Patent number: 4410449Abstract: A process for the recovery and reuse of a heavy-metal oxidation catalyst solution from a high-boiling distillation residue having a cobalt content of 1-10 g/kg of residue is disclosed. The distillation residue is obtained in the production of dimethyl terephthalate by the oxidation of mixtures containing p-xylene and/or methyl p-toluate in the liquid phase with oxygen or an oxygen-containing gas under an elevated pressure and at an elevated temperature in the presence of dissolved heavy-metal oxidation catalyst, by subsequent esterification of the oxidation product with methanol and by a distillatory separation of the esterification product into a fraction rich in methyl p-toluate, a fraction rich in dimethyl terephthalate, and the high-boiling distillation residue.Type: GrantFiled: August 12, 1982Date of Patent: October 18, 1983Assignee: Dynamit Nobel AktiengesellschaftInventors: Karl-Heinz Diessel, Rudolf Modic, Friedrich Struss
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Patent number: 4405717Abstract: A process is provided for the recovery of acetic acid from dilute aqueous solutions. The acid in the form of its calcium salt is treated with a tertiary amine carbonate and the resulting trialkylammonium acetate is isolated and heated to give the acetic acid plus a tertiary amine.Type: GrantFiled: October 26, 1981Date of Patent: September 20, 1983Assignee: CPC International Inc.Inventor: Branko Urbas
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Patent number: 4401514Abstract: A method of recovering or extracting chemicals, such as furfural, formic acid, acetic acid and other organic compounds from acidic hydrolysates of plants or vegetable matter, especially spent sulfite liquors after conversion of the pentosans into pentoses and then into furfural by heating the hydrolysate in an acidic environment. The conversion of the pentosans pentoses into furfural, preferably with acidulation, is accomplished in a counterflow or countercurrent flow heat exchanger and a reactor, preferably a tubular reactor. The hydrolysate which has additionally been heated and converted in the reactor is used as a heating medium or heat carrier for heating up the hydrolysate which is converted in the counterflow heat exchanger, whereupon there is recovered as the distillate furfural in conjunction with the formic acid, acetic acid and the like.Type: GrantFiled: March 18, 1981Date of Patent: August 30, 1983Assignee: Vereinigte Edelstahlwerke AG (VEW)Inventors: Walter Kanzler, Johannes Schedler
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Patent number: 4389323Abstract: A process of making different grades of calcium magnesium acetate deicing agents, having substantially uniform but different calcium-to-magnesium mole ratios, from limestone having varying proportions of calcium carbonate and magnesium carbonate, is provided wherein limestone containing calcium and magnesium carbonates is finely divided, mixed with water to form an aqueous suspension of limestone, vigorously agitated and reacted with excess acetic acid. The reaction is completed by adding to the reaction batch about 30% of the molar equivalent of calcined finely divided limestone base to produce a calcium magnesium acetate salt solution having a calcium-to-magnesium mole ratio much greater than one. The insolubles from this first reaction are removed, calcined and reacted with acetic acid in a second reaction to produce a calcium magnesium acetate salt solution having a calcium-to-magnesium mole ratio substantially equal to one.Type: GrantFiled: November 2, 1981Date of Patent: June 21, 1983Inventor: Alan B. Gancy
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Patent number: 4381407Abstract: A process for the continuous production of triacetin consisting essentially of continuously charging liquid glycerol into a first liquid reaction area through which acetic acid vapors and water vapors flow, said liquid reaction area being divided into a number of separate individual areas through which liquid glycerol and liquid acetin reaction products flow in one direction and gaseous acetic acid and water flow in a countercurrent direction, continuously charging acetic acid vapor to a separate individual area where said liquid mixture has an OH number of less than 600, continuously separating a liquid mixture of acetins and water having an OH number of less than 600, continuously passing said liquid mixture into a second liquid reaction area, continuously adding thereto liquid acetic acid anhydride in an amount sufficient to react with water dissolved in said liquid mixture to form acetic acid and to react with monoacetin and diacetin present to form triacetin and continuously recovering triacetin.Type: GrantFiled: January 26, 1981Date of Patent: April 26, 1983Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Norbert Bremus, Gerhard Dieckelmann, Lutz Jeromin, Wolfgang Rupilius, Hartwig Schutt
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Patent number: 4377488Abstract: A process of making a calcium acetate-containing solution having a pH value at room temperature between about 7 and about 8 is provided comprising reacting acetic acid with a carbonate compound, adding calcined limestone, and optionally finishing off the acid-base reaction with an amount of an alkali metal hydroxide comprising from about 2% to about 5% of the total stoichiometric complement to the amount of acetic acid. Further process options which may be used in the preparation of deicing agents include adding coarse limestone to the above-prepared calcium acetate-containing solution in amounts up to 10% by weight and converting the solution into solid flakes.Type: GrantFiled: December 21, 1981Date of Patent: March 22, 1983Inventor: Alan B. Gancy
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Patent number: 4358609Abstract: A process for the recovery of carboxylic acids from mixtures containing glycol esters derived from these acids. The process comprises reacting these mixtures at boiling with water to form carboxylic acid and entraining the carboxylic acid formed by means of the water by azeotropic distillation, so as to separate off a mixture of carboxylic acid and water. This mixture is subjected to extractive distillation by means of an organic solvent which is insoluble in water and in which water is insoluble. A mixture of water and organic solvent is thereby separated from a solution of carboxylic acid in the organic solvent.Type: GrantFiled: October 1, 1980Date of Patent: November 9, 1982Assignee: Propylox (Societe Anonyme)Inventor: Nicolas Hardy
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Patent number: 4353784Abstract: Disclosed is a method of recovering acetic acid by extracting from an acetic acid-containing aqueous solution with an organic extracting agent and subjecting the extract to distillation, said method comprising the first step of performing extraction by using a tertiary amine having a boiling point higher than that of acetic acid and being capable of forming a non-aqueus phase as the organic extracting agent in combination with an oxygen-containing, high-boiling-point organic solvent selected from the group consisting of di-isobutylcarbinol, isophorene, methyl benzoate, tributyl phosphate, 3,3,5-trimethylcyclohexanone and 2-ethoxyethyl acetate, the second step of performing dehydration by subjecting the extract to distillation, and the third step of subjecting the dehydrated mixture to distillation in a reduced pressure distillation column at a column bottom temperature of 120.degree. to 170.degree. C. to distill acetic acid and separate it from the organic extracting agent.Type: GrantFiled: September 21, 1981Date of Patent: October 12, 1982Assignee: Daicel Chemical Industries, Ltd.Inventors: Kunio Koga, Ryoichi Kishimoto
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Patent number: 4352940Abstract: In the hydrolysis of methyl acetate to acetic acid, the improvement comprising a flasher or stripper to separate methyl acetate and water from the hydrolyzer product stream and the recycle of these directly to the hydrolyzer.Type: GrantFiled: April 28, 1980Date of Patent: October 5, 1982Assignee: E. I. Du Pont de Nemours and CompanyInventors: Robert L. Adelman, Roy Segars, Jr.
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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: 4338464Abstract: Acetic acid can be prepared in high conversions and selectively by the oxidation of liquid n-butane at temperatures of from 120.degree. C. up to 230.degree. C. in the presence of an acetic acid solution containing bromine ions in combination with ions of cobalt or cobalt and manganese. The debutanized effluent of such oxidation consists mainly of acetic acid and water but also contains esters and ketones boiling lower than acetic acid, some higher carbon content aliphatic acids and metal salts boiling higher than acetic acid and rather small amounts of 3-bromo-2-butanone which, although boiling higher than acetic acid, cannot be separated by simple distillation as can be the other non-acetic acid organic impurities. The present inventive technique for removal of said bromo-ketone has for its concept the use of a combination of cryogenic crystallization and removal of adhering mother liquor which can be practiced continuously in known apparatus devised for other fractional crystallizations.Type: GrantFiled: December 17, 1979Date of Patent: July 6, 1982Assignee: Standard Oil Company (Indiana)Inventors: Jon J. Harper, Martin A. Zeitlin
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Patent number: 4337356Abstract: The continuous cobalt catalyzed liquid-phase oxidation of butane to acetic acid with oxygen has been improved by limiting the amount of iron, water and succinic acid present and maintaining a minimum of about 0.1% of cobalt acetate catalyst in the reaction medium.Type: GrantFiled: March 20, 1980Date of Patent: June 29, 1982Assignee: Union Carbide CorporationInventors: John E. Logsdon, Ben W. Kiff
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Patent number: RE32609Abstract: Finely divided lime, at any degree of slaking, is introduced in a steady stream into an agitated reactor designed to produce pellets or aggregates. Concentrated acetic acid is simultaneously introduced in a steady stream at a rate equal to the chemical combining rate required to produce calcium magesium acetate. Water content of the reaction stream is critical; the mol ratio of water, including water of neutralization, to the calcium magnesium acetate product must fall in the range 3.3-7.0 in order to form the desired pellets and to avoid sticking, caking, and dust emanation from the reactor. Product pellets are drawn off in a stream from the reactor and dried for use as a non-polluting roadway and walkway deicer. Traction agent is optionally incorporated into the deicer pellets by introducing a steady stream of traction agent to the reactor simultaneous with raw materials introduction. Magnesium-to-calcium ratios greater than one are achieved by blending dolime with magnesium-rich ore.Type: GrantFiled: November 6, 1986Date of Patent: February 23, 1988Inventor: Alan B. Gancy
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Patent number: RE33095Abstract: Finely divided ore blends containing chemically active magnesium oxide and calcium oxide are physically combined with a critical amount of water prior to reaction with acetic acid. Intermediate products range in physical consistency from putty-like masses to viscous liquors, depending upon the relative fraction of magnesium oxide in the ore feed. Intermediate products freeze to form hydrates of magnesium calcium acetate, the freeze times being dependent upon a number of chemical and physical parameters. Product drying requirements range from minimal drying to none at all, depending upon the magnesium fraction in the products. Products are non-friable and have excellent crush strength, and are suitable for storage, shipping and application in chemical deicing as well as other end use applications where crude low-cost materials are called for.A unique situation centers around the composition corresponding to the magnesium mol fraction of 0.8.Type: GrantFiled: March 15, 1988Date of Patent: October 17, 1989Inventor: Alan B. Gancy