Purification Or Recovery Patents (Class 568/492)
  • Patent number: 5000832
    Abstract: 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: Grant
    Filed: December 11, 1989
    Date of Patent: March 19, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Steiniger, Hartwig Voss, Leopold Hupfer
  • Patent number: 4986885
    Abstract: 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: Grant
    Filed: March 29, 1989
    Date of Patent: January 22, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Robert K. Driscoll, Ingo Leupold, Karl-Heinz Schonwalder
  • Patent number: 4987252
    Abstract: 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: Grant
    Filed: June 27, 1988
    Date of Patent: January 22, 1991
    Assignees: 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
  • Patent number: 4978778
    Abstract: 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: Grant
    Filed: December 13, 1983
    Date of Patent: December 18, 1990
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Tomiya Isshiki, Yasuhiko Kijima, Akiro Ito, Yuh Miyauchi, Takao Konko, Takayuki Watanabe
  • Patent number: 4962235
    Abstract: 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: Grant
    Filed: April 5, 1989
    Date of Patent: October 9, 1990
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Hirohisa Morishita, Junzo Masamoto, Tadashige Hata
  • Patent number: 4950800
    Abstract: 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: Grant
    Filed: December 20, 1988
    Date of Patent: August 21, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jurgen Weber, Peter Lappe, Helmut Springer
  • Patent number: 4947003
    Abstract: 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: Grant
    Filed: November 28, 1988
    Date of Patent: August 7, 1990
    Assignee: Virginia Tech Intellectual Properties, Inc.
    Inventors: Mark E. Davis, Juan P. Arhancet, Brian E. Hanson
  • Patent number: 4935550
    Abstract: 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: Grant
    Filed: August 12, 1988
    Date of Patent: June 19, 1990
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventors: David J. Miller, David R. Bryant
  • Patent number: 4929767
    Abstract: 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: Grant
    Filed: October 6, 1988
    Date of Patent: May 29, 1990
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventors: David J. Miller, David R. Bryant, Ernst Billig, Bernard L. Shaw
  • Patent number: 4910344
    Abstract: 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: Grant
    Filed: February 1, 1989
    Date of Patent: March 20, 1990
    Assignee: Texaco Inc.
    Inventors: Mordechai Pasternak, Craig R. Bartels, John Reale, Jr.
  • Patent number: 4908477
    Abstract: 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: Grant
    Filed: March 9, 1987
    Date of Patent: March 13, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Horst Hartmann, Waldhelm Hochstein, Gerd Kaibel, Franz-Josef Mueller
  • Patent number: 4902828
    Abstract: 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: Grant
    Filed: October 18, 1984
    Date of Patent: February 20, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Wickenhaeuser, Bernd Heida, Fritz Graf, Leopold Hupfer
  • Patent number: 4871879
    Abstract: 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: Grant
    Filed: October 27, 1987
    Date of Patent: October 3, 1989
    Assignee: Hoechst Celanese Corporation
    Inventor: Keith A. Laird
  • Patent number: 4861918
    Abstract: A process for improving the catalytic activity of a partially deactivated solubilized rhodium - tertiary organophosphine complex hydroformylation catalyst.
    Type: Grant
    Filed: August 12, 1988
    Date of Patent: August 29, 1989
    Assignee: Union Carbide Corporation
    Inventors: David J. Miller, David R. Bryant, Ernst Billig, Bernard L. Shaw
  • Patent number: 4844721
    Abstract: 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: Grant
    Filed: October 6, 1987
    Date of Patent: July 4, 1989
    Inventors: James P. Cox, Robert W. D. Cox
  • Patent number: 4845306
    Abstract: 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: Grant
    Filed: July 12, 1988
    Date of Patent: July 4, 1989
    Assignee: Eastman Kodak Company
    Inventor: Thomas A. Puckette
  • Patent number: 4835320
    Abstract: 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: Grant
    Filed: June 1, 1987
    Date of Patent: May 30, 1989
    Assignee: Societe Francaise Hoechst
    Inventors: Alain Blanc, Farid Hamedi-Sangsari, Francine J. Chastrette
  • Patent number: 4827043
    Abstract: 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: Grant
    Filed: January 22, 1988
    Date of Patent: May 2, 1989
    Assignee: Eastman Kodak Company
    Inventor: Gerald E. Butler
  • Patent number: 4792636
    Abstract: 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: Grant
    Filed: June 30, 1987
    Date of Patent: December 20, 1988
    Assignee: Davy McKee (London) Limited
    Inventors: John R. Hensman, Andrew J. Roberts, George E. Harrison
  • Patent number: 4786434
    Abstract: 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: Grant
    Filed: February 8, 1988
    Date of Patent: November 22, 1988
    Assignee: Tetra Werke Dr. rer. nat. U. Baensch GmbH
    Inventor: Ritter Gunter
  • Patent number: 4774361
    Abstract: 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: Grant
    Filed: May 11, 1987
    Date of Patent: September 27, 1988
    Assignee: Union Carbide Corporation
    Inventors: John M. Maher, David R. Bryant
  • Patent number: 4728435
    Abstract: 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: Grant
    Filed: October 6, 1986
    Date of Patent: March 1, 1988
    Assignee: BASF Aktiengesellschaft
    Inventors: Guenther Mueller, Rolf Ramsteiner, Fritz Graf, Leopold Hupfer
  • Patent number: 4714784
    Abstract: 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: Grant
    Filed: July 16, 1986
    Date of Patent: December 22, 1987
    Assignee: Huls Aktiengesellschaft
    Inventors: Eckhard Moeller, Wolfgang H. E. Mueller, Manfred Z. Hausen
  • Patent number: 4701561
    Abstract: 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: Grant
    Filed: March 13, 1987
    Date of Patent: October 20, 1987
    Assignee: The Goodyear Tire & Rubber Company
    Inventor: Wen-Liang Hsu
  • Patent number: 4678857
    Abstract: 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: Grant
    Filed: March 31, 1986
    Date of Patent: July 7, 1987
    Assignee: Texaco Inc.
    Inventors: Roger G. Dureanleau, John F. Knifton
  • Patent number: 4658068
    Abstract: 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: Grant
    Filed: November 27, 1985
    Date of Patent: April 14, 1987
    Assignee: Exxon Research & Engineering Co.
    Inventor: Jean A. A. Hanin
  • Patent number: 4628122
    Abstract: 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: Grant
    Filed: November 1, 1985
    Date of Patent: December 9, 1986
    Assignee: PPG Industries, Inc.
    Inventors: Frederick J. Kuntz, Henry W. Schussler
  • Patent number: 4618709
    Abstract: 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 diluti
    Type: Grant
    Filed: January 30, 1981
    Date of Patent: October 21, 1986
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masao Sada, Michio Kato, Masami Ayano, Tadashi Abe, Masanori Moriwaki
  • Patent number: 4605783
    Abstract: 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: Grant
    Filed: March 21, 1985
    Date of Patent: August 12, 1986
    Assignee: UOP Inc.
    Inventor: Hermann A. Zinnen
  • Patent number: 4599456
    Abstract: 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: Grant
    Filed: December 20, 1984
    Date of Patent: July 8, 1986
    Assignee: Phillips Petroleum Company
    Inventor: Charles A. Drake
  • Patent number: 4599455
    Abstract: 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: Grant
    Filed: April 27, 1984
    Date of Patent: July 8, 1986
    Inventors: Yutaka Maruyama, Junji Negishi, Katuyoshi Murata, Yutaka Katsuhara
  • Patent number: 4577043
    Abstract: 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: Grant
    Filed: November 9, 1984
    Date of Patent: March 18, 1986
    Assignee: Ruhrchemie Aktiengesellschaft
    Inventors: Heinz Kalbfell, Bernhard Lieder, Herbert Mercamp
  • Patent number: 4559111
    Abstract: 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: Grant
    Filed: December 20, 1984
    Date of Patent: December 17, 1985
    Assignee: Phillips Petroleum Company
    Inventor: Charles A. Drake
  • Patent number: 4523038
    Abstract: 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: Grant
    Filed: May 4, 1984
    Date of Patent: June 11, 1985
    Assignee: Imperial Chemical Industries PLC
    Inventors: Norman Scott, Paul Hepworth
  • Patent number: 4521632
    Abstract: 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: Grant
    Filed: January 23, 1984
    Date of Patent: June 4, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Wickenhaeuser, Bernd Heida, Fritz Graf, Leopold Hupfer
  • Patent number: 4513152
    Abstract: 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: Grant
    Filed: October 3, 1983
    Date of Patent: April 23, 1985
    Assignee: Stauffer Chemical Company
    Inventor: Richard D. Schillawski
  • Patent number: 4480139
    Abstract: 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: Grant
    Filed: April 7, 1983
    Date of Patent: October 30, 1984
    Assignee: Imperial Chemical Industries PLC
    Inventors: Norman Scott, Paul Hepworth
  • Patent number: 4479012
    Abstract: 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: Grant
    Filed: March 30, 1982
    Date of Patent: October 23, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Karl Fischer, Armin V. Grenacher, Manfred Herr, Max Strohmeyer
  • Patent number: 4450294
    Abstract: 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: Grant
    Filed: November 1, 1982
    Date of Patent: May 22, 1984
    Assignee: National Distillers and Chemical Corporation
    Inventor: Julian Feldman
  • Patent number: 4447643
    Abstract: 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: Grant
    Filed: August 11, 1982
    Date of Patent: May 8, 1984
    Assignee: National Distillers and Chemical Corporation
    Inventor: Julian Feldman
  • Patent number: 4401834
    Abstract: 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: Grant
    Filed: June 1, 1982
    Date of Patent: August 30, 1983
    Assignee: Exxon Research & Engineering Co.
    Inventor: Terry S. King
  • Patent number: 4399001
    Abstract: 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: Grant
    Filed: October 28, 1981
    Date of Patent: August 16, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Horst Hartmann, Waldhelm Hochstein, Gerd Kaibel, Franz-Josef Mueller
  • Patent number: 4383894
    Abstract: 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: Grant
    Filed: October 29, 1981
    Date of Patent: May 17, 1983
    Assignee: BASF Aktiengesellschaft
    Inventors: Horst Hartmann, Waldhelm Hochstein, Gerd Kaibel, Franz-Josef Mueller
  • Patent number: 4329513
    Abstract: 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: Grant
    Filed: December 5, 1980
    Date of Patent: May 11, 1982
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Atsushi Aoshima, Ryoichi Mitsui, Toshiaki Kaneko
  • Patent number: 4311563
    Abstract: 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: Grant
    Filed: March 31, 1981
    Date of Patent: January 19, 1982
    Assignee: Wacker-Chemie GmbH
    Inventors: Werner Opavsky, Josef Reisner, Alois Maier
  • Patent number: 4306092
    Abstract: 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: Grant
    Filed: July 11, 1980
    Date of Patent: December 15, 1981
    Assignee: Wacker-Chemie GmbH
    Inventors: Werner Opavsky, Josef Reisner
  • Patent number: 4246195
    Abstract: 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: Grant
    Filed: October 6, 1978
    Date of Patent: January 20, 1981
    Assignee: Halcon Research and Development Corporation
    Inventor: Peter L. Szecsi
  • Patent number: 4235926
    Abstract: 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: Grant
    Filed: December 15, 1978
    Date of Patent: November 25, 1980
    Assignee: Commonwealth Scientific and Industrial Research Organization
    Inventors: George Holan, David F. O'Keefe
  • Patent number: 4234519
    Abstract: 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: Grant
    Filed: January 26, 1979
    Date of Patent: November 18, 1980
    Assignee: Halcon Research and Development Corp.
    Inventors: Neil Yeoman, Sidney S. Stern