Purification Or Recovery Patents (Class 568/492)
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Patent number: 5000832Abstract: Aqueous glyoxal solutions which contain organic acids are purified by means of a membrane cell comprising two or more compartments by passing the glyoxal solution through at least one of the cell compartments separated from the neighboring compartment(s) by anion exchange membranes and by passing the aqueous solution of a base through at least one of the neighboring compartments.Type: GrantFiled: December 11, 1989Date of Patent: March 19, 1991Assignee: BASF AktiengesellschaftInventors: Michael Steiniger, Hartwig Voss, Leopold Hupfer
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Patent number: 4986885Abstract: A process for the separation of butanol and butoxyacetaldehyde which involves subjecting a composition which contains these two compounds to a distillation at a pressure of at most 660 mbar. According to a special embodiment the composition to be distilled contains as essential components water, butanol, butoxyacetaldehyde, butylglycol and, if desired, also butyraldehyde.Type: GrantFiled: March 29, 1989Date of Patent: January 22, 1991Assignee: Hoechst AktiengesellschaftInventors: Robert K. Driscoll, Ingo Leupold, Karl-Heinz Schonwalder
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Patent number: 4987252Abstract: In order to recover methacrolein and/or methacrylic acid by quenching a reaction product gas obtained by catalytic oxidation of isobutylene or the like, the reaction product gas is charged into a quench column through a double-wall pipe and is then brought into contact with a condensate as a cooling medium. Deposition of terephthalic acid and the like inside the column is prevented by controlling the temperature of a bottom in the quench column and that of an overhead gas of a quench column unit. An aromatic carboxylic acid, aromatic aldehyde, metal powder is added to an aqueous solution of methacrylic acid, which contains terephthalic acid and the like, so that the terephthalic acid and the like are caused to precipitate for their removal.Type: GrantFiled: June 27, 1988Date of Patent: January 22, 1991Assignees: Mitsui Toatsu Chemicals, Incorporated, Kyowa Gas Chemical Industry Co., Ltd.Inventors: Morimasa Kuragano, Kozo Iwasaki, Takeshi Isobe, Isao Fukada, Minoru Koshibe, Yoshihiro Sezaki, Hirozo Segawa, Katsuji Yoguchi
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Patent number: 4978778Abstract: A process for producing vinyl acetate which comprises reacting acetic anhydride with hydrogen in the presence of a catalyst comprising(a) a metal belonging to Group VIII of the Periodic Table or a compound of the metal, and(b) (i) an acidic substance, or (ii) a halideis disclosed.Type: GrantFiled: December 13, 1983Date of Patent: December 18, 1990Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tomiya Isshiki, Yasuhiko Kijima, Akiro Ito, Yuh Miyauchi, Takao Konko, Takayuki Watanabe
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Patent number: 4962235Abstract: A process for producing formaldehyde having high purity is disclosed, which comprises: (A) feeding crude formaldehyde containing water and methanol to the middle or lower part of a distillation column, and feeding a polyalkylene oxide compound which is inert to formaldehyde to the upper part of the column in an amount at least 10 times the total weight of the water and methanol contained in the crude formaldehyde; (B) carrying out distillation; and (C) recovering purified formaldehyde gas from the top of the column while withdrawing a solution containing the polyalkylene oxide compound, water and methanol from the bottom of the column. Using this process, formaldehyde having stable high purity can be obtained continuously through simplified steps at low cost.Type: GrantFiled: April 5, 1989Date of Patent: October 9, 1990Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Hirohisa Morishita, Junzo Masamoto, Tadashige Hata
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Patent number: 4950800Abstract: A process for the recovery of 2-methylbutanal from mixtures of isomeric aldehydes having 5 carbon atoms wherein the mixture is distilled in the presence of formaldehyde and an aldolization catalyst. The 2-methylbutanal obtained is useful as an intermediate for the preparation of various useful compounds, including the corresponding alcohol, amine, and acid.Type: GrantFiled: December 20, 1988Date of Patent: August 21, 1990Assignee: Hoechst AktiengesellschaftInventors: Jurgen Weber, Peter Lappe, Helmut Springer
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Patent number: 4947003Abstract: A process for the hydroformylation of alkenes and other olefinically unsaturated reactants by reaction with carbon monoxide and hydrogen in the presence of a heterogeneous catalyst comprising a solid surface having immobilized thereon a solution of one or more rhodium complexes which is essentially immiscible with the organic reactant. Catalyst is subsequently recovered from the resulting hydroformylation product by one or more solid-liquid separation techniques.Type: GrantFiled: November 28, 1988Date of Patent: August 7, 1990Assignee: Virginia Tech Intellectual Properties, Inc.Inventors: Mark E. Davis, Juan P. Arhancet, Brian E. Hanson
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Patent number: 4935550Abstract: A method for recovering a transition metal, e.g., rhodium, from a non-polar organic solution containing non-polar organic solvent-soluble and polar solvent-insoluble coordination complex of the transition metal and a non-polar organic solvent-soluble and polar solvent-insoluble ligand, e.g., an organophosphorus ligand, by contacting the non-polar organic solution with a polar solution of an ionic organophosphine ligand, the transition metal then can be transferred back into a non-polar solution for reuse. In one embodiment rhodium is rendered amenable for back-extraction by treating the polar solution with a suitable conditioning reagent.Type: GrantFiled: August 12, 1988Date of Patent: June 19, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventors: David J. Miller, David R. Bryant
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Patent number: 4929767Abstract: A process for treating an organic solution of a partially deactivated solubilized rhodium-tertiary organophosphine complex hydroformylation catalyst with an organic reagent in order to improve the extractability of rhodium therefrom into an aqueous solution containing an ionic organophosphine ligand.Type: GrantFiled: October 6, 1988Date of Patent: May 29, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventors: David J. Miller, David R. Bryant, Ernst Billig, Bernard L. Shaw
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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: 4908477Abstract: Organic iodine compounds are separated from carbonylation products of methanol, methyl acetate and dimethyl ether and from mixtures of such carbonylation products by a process wherein the iodine compounds are removed by liquid phase extraction with a non-aromatic hydrocarbon.Type: GrantFiled: March 9, 1987Date of Patent: March 13, 1990Assignee: BASF AktiengesellschaftInventors: Horst Hartmann, Waldhelm Hochstein, Gerd Kaibel, Franz-Josef Mueller
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Patent number: 4902828Abstract: Aqueous glyoxylic acid solutions, essentially free of other acids, are recovered from aqueous solutions which still contain other acids, by a method in which the aqueous solution is mixed with an organic nitrogen compound at as high as 50.degree. C., the phases are separated, and the glyoxylic acid is extracted from the organic phase with water, at a higher temperature.Type: GrantFiled: October 18, 1984Date of Patent: February 20, 1990Assignee: BASF AktiengesellschaftInventors: Gerhard Wickenhaeuser, Bernd Heida, Fritz Graf, Leopold Hupfer
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Patent number: 4871879Abstract: In the hydroformylation of alkenes to aldehydes, rhodium is recovered from the stripped overhead of the hydroformylation reactor by condensing the overhead, removing the bulk of the aldehyde product from the condensed overhead, stripping the residue which remains with nitrogen gas to remove minor amounts of highly volatile aldehyde product remaining in the residue and redistilling the residue to remove components from the condensed overhead which are lower boiling than the catalyst components. The catalyst components including rhodium and phosphine ligand are returned to the hydroformylation reactor.Type: GrantFiled: October 27, 1987Date of Patent: October 3, 1989Assignee: Hoechst Celanese CorporationInventor: Keith A. Laird
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Patent number: 4861918Abstract: A process for improving the catalytic activity of a partially deactivated solubilized rhodium - tertiary organophosphine complex hydroformylation catalyst.Type: GrantFiled: August 12, 1988Date of Patent: August 29, 1989Assignee: Union Carbide CorporationInventors: David J. Miller, David R. Bryant, Ernst Billig, Bernard L. Shaw
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Patent number: 4844721Abstract: An aqueous liquid containing unsaturated vegetable, marine or land animal oil or liquid fat, preferably drying or semidrying oil, is used as a scrubbing liquid to remove pollutant from an air stream. Specifically, styrene constituting an air pollutant is sorbed from the air and polymerized to polystyrene by ultraviolet light radiation to facilitate its separation from the scrubbing liquid.Type: GrantFiled: October 6, 1987Date of Patent: July 4, 1989Inventors: James P. Cox, Robert W. D. Cox
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Patent number: 4845306Abstract: Disclosed is a process for recovering or concentrating active catalyst materials from a substantially homogeneous system comprising:(a) active catalyst materials which comprise(i) triorganophosphine-rhodium complexes, and(ii) free triorganophosphine;(b) oxidized triorganophosphine residues,(c) iron carboxylate salts,(d) pump oils, and(e) aldehydes and aldol condensation products thereof;said processing comprising:(1) admixing a portion of said homogeneous system with about 1 up to 100 volumes (relative to the volume of said portion) of at least one nonpolar hydrophobic hydrocarbon diluent selected from the group consisting of saturated or unsaturated aliphatic hydrocarbon having in the range of 3 up to 20 carbon atoms and aromatic or hydrocarbyl-substituted aromatic hydrocarbons having in the range of 6 up to 22 carbon atoms to produce a diluted homogeneous system,(2) contacting said diluted homogeneous system with 0.Type: GrantFiled: July 12, 1988Date of Patent: July 4, 1989Assignee: Eastman Kodak CompanyInventor: Thomas A. Puckette
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Patent number: 4835320Abstract: This process for the preparation of products of general formula (I): ##STR1## wherein either R.sub.1 and R.sub.2, which are identical, represent a --CHRR.sub.3 group, in which R and R.sub.3, which are identical or different, represent an alkyl, alkenyl or aralkyl group, or R.sub.1 and R.sub.2, which are identical, represent a --CH.sub.2 R group, in which R represents a hydrogen atom, an alkyl, alkenyl or aralkyl radical, or R.sub.1 and R.sub.2 together form a --CH.sub.2 --(CRR).sub.n --CHR-- radical, in which n represents 0 or 1 and R retains the meaning given previously, is characterized by reacting glyoxal in the presence of an acid catalyst with an excess of the corresponding alcohol of general formula (II) RR.sub.3 CHOH, (III) RCH.sub.2 OH or (IV) --(CRR).sub.n --CHROH, in which R, R.sub.3 and n retain the meaning given previously, then stopping the reaction as soon as the concentration of the desired monoacetal of general formula (I) decreases in the reaction medium in favor of bisacetal.Type: GrantFiled: June 1, 1987Date of Patent: May 30, 1989Assignee: Societe Francaise HoechstInventors: Alain Blanc, Farid Hamedi-Sangsari, Francine J. Chastrette
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Patent number: 4827043Abstract: Disclosed is a process for the purification of carbon monoxide and/or hydrogen-containing gas streams employed for chemical conversion reactions by contacting such gas feed streams with the oxygenated organic reaction products obtained in the subject chemical conversion reaction.Type: GrantFiled: January 22, 1988Date of Patent: May 2, 1989Assignee: Eastman Kodak CompanyInventor: Gerald E. Butler
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Patent number: 4792636Abstract: A process is provided for the recovery of an optionally substituted C.sub.7 to C.sub.17 aldehyde from a liquid hydroformylation product medium obtained by rhodium catalyzed hydroformylation of an optionally substituted C.sub.6 to C.sub.16 olefin which contains (i) a rhodium complex hydroformylation catalyst containing rhodium in complex combination with carbon monoxide and with a ligand, (ii) excess ligand, (iii) at least one optionally substituted C.sub.7 to C.sub.17 aldehyde, and (iv) aldehyde condensation products, which process comprises:(a) degassing said liquid hydroformylation medium;(b) passing the degassed liquid hydroformylation medium through an evaporation zone maintained under temperature and pressure conditions conducive to evaporation of said at least one C.sub.7 to C.sub.Type: GrantFiled: June 30, 1987Date of Patent: December 20, 1988Assignee: Davy McKee (London) LimitedInventors: John R. Hensman, Andrew J. Roberts, George E. Harrison
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Patent number: 4786434Abstract: An agent for and the method for its use in the elimination of active chlorine compounds from water comprises a hydroxysulfinate adduct of an aliphatic, aromatic, or heterocyclic mono- or dialdehyde or an ammonia adduct thereof. The agent is used alone or in combination with the corresponding aldehyde.Type: GrantFiled: February 8, 1988Date of Patent: November 22, 1988Assignee: Tetra Werke Dr. rer. nat. U. Baensch GmbHInventor: Ritter Gunter
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Patent number: 4774361Abstract: The use of an organic polymer additive to minimize or prevent the rhodium of a rhodiumorganophosphite complex catalyst from precipitating from solution during a liquid recycle hydroformylation process.Type: GrantFiled: May 11, 1987Date of Patent: September 27, 1988Assignee: Union Carbide CorporationInventors: John M. Maher, David R. Bryant
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Patent number: 4728435Abstract: An aqueous glyoxal solution is decolorized by a process in which the said solution is passed over granulated active carbon which is arranged in a fixed bed and whose differential pore radius distribution has a maximum of from 10 to 100 A, the Peclet number being from 500 to 5000, the decolorized glyoxal solution is discharged, the active carbon bed is then regenerated by treating it with an aqueous solution of an alkaline agent and then with an aqueous acid, and further glyoxal solution to be decolorized is passed over the active carbon regenerated in this manner.Type: GrantFiled: October 6, 1986Date of Patent: March 1, 1988Assignee: BASF AktiengesellschaftInventors: Guenther Mueller, Rolf Ramsteiner, Fritz Graf, Leopold Hupfer
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Patent number: 4714784Abstract: The invention relates to a method for removing n-butyraldehyde from gas streams. It is characterized by washing with dilute aqueous alkali in a mass transfer apparatus. According to the invention, n-butyraldehyde can be removed from gas streams in the proportion of >90%, with operation at 0.degree.-40.degree. C. in the absence of added solubilizing agents.Type: GrantFiled: July 16, 1986Date of Patent: December 22, 1987Assignee: Huls AktiengesellschaftInventors: Eckhard Moeller, Wolfgang H. E. Mueller, Manfred Z. Hausen
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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: 4678857Abstract: A process is disclosed for preparing products such as 4-hydroxybutanal which comprises contacting unsaturated compounds such as allyl alcohol with carbon monoxide and hydrogen in the presence of a rhodium carbonyl-phosphine catalyst and an aromatic solvent. The solvent is an aromatic which causes a large density difference between the resulting aqueous phase and organic phase so that the soluble rhodium catalyst can be easily separated from the 4-hydroxybutanal product and starting material without appreciable loss of the metal. This allows for easy recycle of the catalyst solution.Type: GrantFiled: March 31, 1986Date of Patent: July 7, 1987Assignee: Texaco Inc.Inventors: Roger G. Dureanleau, John F. Knifton
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Patent number: 4658068Abstract: The higher alcohol yield of a hydroformylation process comprising catalytic hydroformylation of olefinic feedstock and hydrogenation of the crude product is improved by separating light materials and desired alcohols from the hydrogenated product, and then subjecting the remaining heavy materials to catalytic steam cracking at 260.degree.-380.degree. C. The fraction of the cracked product which is rich in alcohol/aldehyde is then separated and recycled, preferably to the hydrogenation stage.Type: GrantFiled: November 27, 1985Date of Patent: April 14, 1987Assignee: Exxon Research & Engineering Co.Inventor: Jean A. A. Hanin
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Patent number: 4628122Abstract: Chloral is removed from aqueous hydrochloric acid containing chloral in a stripping zone at superatmospheric pressure and concentrated in a rectifying zone at superatmospheric pressure. The method is particularly suited for the treatment of feed compositions originating from the oxychlorination of ethylene.Type: GrantFiled: November 1, 1985Date of Patent: December 9, 1986Assignee: PPG Industries, Inc.Inventors: Frederick J. Kuntz, Henry W. Schussler
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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: 4605783Abstract: An adsorptive method of separating alcohols and aldehydes or ketones and alcohols of monoterpenes is disclosed. The method uses an X-type zeolite containing sodium and potassium cations to selectively adsorb the alcohols thereby allowing recovery of an aldehyde or ketone raffinate stream and, after desorption, an alcohol extract stream. The method is suitable for feed mixtures containing individual or multiple monoterpenoid components.Type: GrantFiled: March 21, 1985Date of Patent: August 12, 1986Assignee: UOP Inc.Inventor: Hermann A. Zinnen
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Patent number: 4599456Abstract: Novel compositions are disclosed consisting essentially of aldehydes of the structure R--CHO (wherein R is a C.sub.8 -C.sub.30 carbon radical) and about 0.1 to about 5 parts by weight of a triarylphosphine per 100 parts of aldehyde. In addition, a process for the recovery of essentially pure high boiling aldehyde by fractional distillation is provided wherein about 0.1 to about 5 parts by weight of a triarylphosphine per 100 parts of high boiling aldehyde is added to the aldehyde prior to distillation. Further, process for improving the high temperature storage stability of high boiling aldehydes is provided, which comprises adding about 0.1 to about 5 parts by weight of a triarylphosphine per 100 parts high boiling aldehyde to the aldehyde.Type: GrantFiled: December 20, 1984Date of Patent: July 8, 1986Assignee: Phillips Petroleum CompanyInventor: Charles A. Drake
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Patent number: 4599455Abstract: A fluorinated carbonyl compound ##STR1## where x is 2 or 3 and A represents CF.sub.3 or H, coexisting with hydrogen fluoride in a mixed gas is purified by first adjusting the temperature of the mixed gas to 100.degree.-300.degree. C. to cause decomposition of a usually coexisting complex of the fluorinated compound with HF and then bringing the hot mixed gas into contact with concentrated sulfuric acid maintained at 10.degree.-40.degree. C. Almost the entire amount of HF is absorbed in sulfuric acid and subsequently recovered, while the purified compound neither dissolves in sulfuric acid nor reacts with HF present in sulfuric acid.Type: GrantFiled: April 27, 1984Date of Patent: July 8, 1986Inventors: Yutaka Maruyama, Junji Negishi, Katuyoshi Murata, Yutaka Katsuhara
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Patent number: 4577043Abstract: The preparation of aldehydes by the reaction of olefins with carbon monoxide and hydrogen in the presence of water and water-soluble rhodium/phosphine complex compounds as catalysts. The method comprises first cooling the organic part of the liquid phase to 70.degree. to 90.degree. C. in a stripping column by treatment with the carbon monoxide/hydrogen mixture fed into the reactor, further cooling the organic part to 20.degree. to 40.degree. C. by heat exchange with the feed olefin, subsequently relieving the pressure with the consequent formation of waste gas and aqueous and organic phases, and finally separating the phases so as to recover substantially all of the catalyst and the heat of reaction.Type: GrantFiled: November 9, 1984Date of Patent: March 18, 1986Assignee: Ruhrchemie AktiengesellschaftInventors: Heinz Kalbfell, Bernhard Lieder, Herbert Mercamp
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Patent number: 4559111Abstract: Production of essentially pure Z-11-hexadecenal by azeotropic distillation is described. Contacting a mixture of Z-11-hexadecenal, hexadecene and hexadecadiene with dimethylsulfoxide and subjecting the blend to azeotropic distillation allows for the removal of hydrocarbon impurities from the aldehyde. Contacting a mixture of Z-11-hexadecenal and hexadecenol with a C.sub.2 -C.sub.4 glycol and subjecting the blend to azeotropic distillation conditions allows for the recovery of a glycol-aldehyde azeotrope from which essentially pure aldehyde is readily recovered. A mixture comprising Z-11-hexadecenal, hexadecene, hexadecadiene and hexadecenol can be sequentially treated according to the above-described azeotropic distillation steps in order to provide essentially pure Z-11-hexadecenal.Type: GrantFiled: December 20, 1984Date of Patent: December 17, 1985Assignee: Phillips Petroleum CompanyInventor: Charles A. Drake
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Patent number: 4523038Abstract: Linear aldehydes having 7-21 carbon atoms are separated from mixtures (which may contain alcohols and/or branched aldehydes) by converting them into solid adducts with C.sub.2 to C.sub.12 linear alkane diols. The adducts are then separated and decomposed. The adducts are themselves novel compounds.Type: GrantFiled: May 4, 1984Date of Patent: June 11, 1985Assignee: Imperial Chemical Industries PLCInventors: Norman Scott, Paul Hepworth
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Patent number: 4521632Abstract: Aqueous solutions of glyoxal which contain acids are purified by treatment with a solution which contains from 20 to 60% by weight of a tertiary amine and from 80 to 40% by weight of an alcohol which is not infinitely miscible with water, the treatment being carried out by mixing the two solutions during a residence time of less than 5 minutes.Type: GrantFiled: January 23, 1984Date of Patent: June 4, 1985Assignee: BASF AktiengesellschaftInventors: Gerhard Wickenhaeuser, Bernd Heida, Fritz Graf, Leopold Hupfer
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Patent number: 4513152Abstract: The invention is a process for drying and purifying wet crude chloral which process comprises contacting the wet crude chloral with sulfuric acid solution in such manner that the solution in contact with the chloral has a concentration of about 50 percent or below, recovering the chloral, contacting the recovered chloral with concentrated sulfuric acid and utilizing the effluent acid recovered from the second contacting operation in first contacting of a subsequent process operation. Multistage, countercurrent flow arrangements are described. Hydrogen chloride and other acidic impurities are also substantially removed.Type: GrantFiled: October 3, 1983Date of Patent: April 23, 1985Assignee: Stauffer Chemical CompanyInventor: Richard D. Schillawski
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Patent number: 4480139Abstract: Linear aldehydes having 7-21 carbon atoms are separated from mixtures (which may contain alcohols and/or branched aldehydes) by converting them into solid adducts with C.sub.2 to C.sub.12 linear alkane diols. The adducts are then separated and decomposed. The adducts are themselves novel compounds.Type: GrantFiled: April 7, 1983Date of Patent: October 30, 1984Assignee: Imperial Chemical Industries PLCInventors: Norman Scott, Paul Hepworth
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Patent number: 4479012Abstract: Aldehydes are obtained from the gaseous product of the hydroformylation of olefinically unsaturated compounds using a rhodium catalyst by a process (cf. FIG. 2) in which(a) this gaseous product is introduced, without being cooled or depressured, into a distillation column D,(b) the top fraction from this column is cooled in a condenser K so that the greater part of the aldehydes contained therein is condensed,(c) the condensate is separated, in a separator A, into a gas phase and a liquid phase,(d) the gas phase from A, after waste gas has been separated off, is again brought to the hydroformylation pressure by means of a compressor P, and is returned to the reactor as a recycle gas,(e) the liquid phase from A is returned to D, and(f) the aldehydes are taken off from column D as liquid bottom products and/or as a vaporous side stream.Type: GrantFiled: March 30, 1982Date of Patent: October 23, 1984Assignee: BASF AktiengesellschaftInventors: Karl Fischer, Armin V. Grenacher, Manfred Herr, Max Strohmeyer
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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: 4401834Abstract: An improved process for producing alcohols which comprises passing a demetalled hydroformylation liquid effluent comprising aldehyde and alcohol and containing acetal impurities to a thermal treatment zone; subjecting the demetalled hydroformylation effluent in the thermal treatment zone in the absence of added acidic compounds and in the presence of water to a temperature of from about 350.degree. to 500.degree. F. for a time sufficient to convert at least a major portion of the acetal impurities to the corresponding aldehydes and alcohols and to form an aldehyde-containing liquid containing substantially reduced levels of the acetal impurities; withdrawing the aldehyde-containing liquid from the thermal treatment zone and rapidly cooling the liquid to a temperature of about 300.degree. F.Type: GrantFiled: June 1, 1982Date of Patent: August 30, 1983Assignee: Exxon Research & Engineering Co.Inventor: Terry S. King
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Patent number: 4399001Abstract: A process for separating off organic iodine compounds from acetaldehyde-free carbonylation products of methanol, methyl acetate and dimethyl ether by removing the iodine compounds by azeotropic distillation with a hydrocarbon having a boiling point, under atmospheric pressure, of 25-55.degree. C.Type: GrantFiled: October 28, 1981Date of Patent: August 16, 1983Assignee: BASF AktiengesellschaftInventors: Horst Hartmann, Waldhelm Hochstein, Gerd Kaibel, Franz-Josef Mueller
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Patent number: 4383894Abstract: A process for separating off organic iodine compounds from acetaldehyde by subjecting the acetaldehyde to azeotropic distillation with a hydrocarbon boiling at from 25.degree. to 55.degree. C. under atmospheric pressure.Type: GrantFiled: October 29, 1981Date of Patent: May 17, 1983Assignee: BASF AktiengesellschaftInventors: Horst Hartmann, Waldhelm Hochstein, Gerd Kaibel, Franz-Josef Mueller
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Patent number: 4329513Abstract: Methanol is allowed to flow downwardly and contacted countercurrently with an unsaturated aldehyde-containing gas obtained from gas phase catalytic oxidation of the starting gas containing at least one gas selected from the group consisting of propylene, isobutylene and t-butanol, said methanol being supplied in such an amount that substantially the whole thereof can be gasified in the treatment. According to this method, the water content in said unsaturated aldehyde-containing gas can be rendered smaller than that in the azeotropic mixture of the unsaturated aldehyde and water, and also there takes place no polymerization of the unsaturated aldehyde.Type: GrantFiled: December 5, 1980Date of Patent: May 11, 1982Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Atsushi Aoshima, Ryoichi Mitsui, Toshiaki Kaneko
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Patent number: 4311563Abstract: The invention relates to a process for the isolation of chloroacetaldehyde which is obtained as a by-product during the synthesis of acetaldehyde from ethylene and air in an aqueous palladium/cupric chloride solution by the 2-stage process. The mixture to be worked-up to chloroacetaldehyde is taken from the acetaldehyde distillation column and transferred to a distillation and extraction system, where it is fractionally condensed. The chloroacetaldehyde-containing fraction is extracted with water and the aqueous extract is subjected to purification distillation.Type: GrantFiled: March 31, 1981Date of Patent: January 19, 1982Assignee: Wacker-Chemie GmbHInventors: Werner Opavsky, Josef Reisner, Alois Maier
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Patent number: 4306092Abstract: The invention provides a process by which acetaldehyde can be separated off from mixtures with chloroform, methylene chloride and chlorofuran. In this process, the aldehyde is separated off by adding water to separate the mixture into an aldehyde-containing phase and a phase comprising chloroform, methylene chloride and chlorofuran.Type: GrantFiled: July 11, 1980Date of Patent: December 15, 1981Assignee: Wacker-Chemie GmbHInventors: Werner Opavsky, Josef Reisner
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Patent number: 4246195Abstract: Carbonylation products of methyl acetate such as acetic anhydride are purified with respect to iodine contaminants by treatment with cesium acetate, potassium acetate or sodium acetate.Type: GrantFiled: October 6, 1978Date of Patent: January 20, 1981Assignee: Halcon Research and Development CorporationInventor: Peter L. Szecsi
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Patent number: 4235926Abstract: Compounds of the general formula I ##STR1## wherein R.sup.1 is hydrogen or a methoxy, ethoxy, propoxy, butoxy, tetrafluoroethoxy, methylthio, ethylthio, propylthio, fluoro, chloro, bromo, methyl, ethyl, or nitro group, and R.sup.2 is hydrogen or a methyl group, or R.sup.1 and R.sup.2 together form a methylenedioxy group;R.sup.3 is hydrogen, or a lower alkyl group, or one of the following groups (a) to (f):(a) 3-phenoxybenzyl(b) 2-benzyl-4-furylmethyl(c) .alpha.-cyano-3-phenoxybenzyl(d) 3,4-methylenedioxybenzyl(e) .alpha.-ethynyl-3-phenoxybenzyl(f) .alpha.-cyano-3-(4'-chlorophenoxy)-benzyland Y.sup.1, Y.sup.2, Y.sup.3, Y.sup.4, Y.sup.5 and Y.sup.6 are the same or different groups and each is hydrogen or a fluoro, bromo or chloro group, with the proviso that when R.sup.1 is hydrogen, fluoro, chloro, bromo or methyl and R.sup.2 is hydrogen, then one of Y.sup.1 to Y.sup.6 is other than hydrogen.The compounds in which R.sup.3 is one of groups (a) to (f) are insecticides.Type: GrantFiled: December 15, 1978Date of Patent: November 25, 1980Assignee: Commonwealth Scientific and Industrial Research OrganizationInventors: George Holan, David F. O'Keefe
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Patent number: 4234519Abstract: In the catalytic oxidation of isobutylene and/or tertiary butyl alcohol to methacrolein, the product methacrolein is recovered as an aqueous solution, which thereafter is stripped of methacrolein by contacting the solution with recycle gases from the subsequent oxidation of methacrolein to methacrylic acid. In a preferred embodiment, the oxidation reactor effluent gases are quenched to near ambient temperatures by direct contact with a recirculating stream of partially condensed effluent to provide an aqueous solution of methacrolein and thereafter the methacrolein remaining in the effluent gases is absorbed into a refrigerated water stream to provide a second aqueous solution. The aqueous solutions are combined and stripped by recycle gases, thereby supplying methacrolein as feed to the subsequent oxidation process.Type: GrantFiled: January 26, 1979Date of Patent: November 18, 1980Assignee: Halcon Research and Development Corp.Inventors: Neil Yeoman, Sidney S. Stern