Acrylic Acid Or Ester Patents (Class 203/DIG21)
  • Patent number: 5968322
    Abstract: A process for preparing refined acrylic esters, the process including steps of distilling an acrylic ester containing stream in the presence of hydroquinone or substituted hydroquinone, at a concentration in the range of 200 to 5000 ppmw, wherein the distillation is carried out in the presence of 0.001 to 1.0 % v, on the vapor phase, of oxygen.
    Type: Grant
    Filed: November 26, 1997
    Date of Patent: October 19, 1999
    Inventors: Peter Arnoldy, Eric Kragtwijk, Antoon Paul Michael Kremers
  • Patent number: 5961790
    Abstract: A process for the separation by rectification of (meth)acrylic acid from a mixture containing (meth)acrylic acid and an inert hydrophobic organic liquid having a boiling point higher than that of (meth)acrylic acid as main constituents and also lower aldehydes as secondary constituents, a primary amine and/or a salt thereof are added.
    Type: Grant
    Filed: December 14, 1994
    Date of Patent: October 5, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Holger Herbst, Gerhard Nestler, Jerry Darlington, Ulrich Hammon
  • Patent number: 5916422
    Abstract: A method for purifying acetic acid containing at least one component selected from the group consisting of unsaturated compounds and carbonyl compounds as an impurity involves the step of purifying the acetic acid with a distillation column having at least 30 plates by operating the distillation column at a pressure ranging from 40 to 760 mmHg and a reflux ratio of at least 4, and yields a high-quality acetic acid which rates high in the potassium permanganate test without needing of the addition of any chemical to the acetic acid to be purified and a large amount of energy, and is economical.
    Type: Grant
    Filed: March 7, 1997
    Date of Patent: June 29, 1999
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Satoshi Kimura, Takashi Ueno, Yoshiaki Morimoto
  • Patent number: 5897749
    Abstract: Liquid mixtures which contain (meth)acrylic acid as the main component are continuously separated in a distillation apparatus which comprises a still, a condenser and a connection between still and condenser and to which the liquid mixture to be separated is continuously fed, by a process in which the energy required for evaporation of the liquid mixture is supplied to the distillation apparatus by a procedure in which a part of the liquid content of the still is continuously removed, superheated and recycled to the still.
    Type: Grant
    Filed: October 18, 1996
    Date of Patent: April 27, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Ruprecht Kroker, Manfred Wiedemann
  • Patent number: 5872288
    Abstract: The present invention provides a process for producing (meth)acrylic acid by gas-phase catalytic oxidation, which comprises cooling and condensing a (meth)acrylic acid-containing reaction product gas to obtain a crude aqueous (meth)acrylic acid solution; cooling the aqueous solution to deposit the impurities contained in the aqueous solution, as solid matter; separating the solid matter; and then extracting and separating (meth)acrylic acid from the purified aqueous (meth)acrylic acid solution obtained. Unlike the conventional processes in which (meth)acrylic acid is extracted and separated from a crude aqueous (meth)acrylic acid solution, the present process can avoid various troubles caused by the impurities contained in the crude aqueous (meth)acrylic acid solution, for example, generation of scum and the like, and therefore can produce (meth)acrylic acid at a higher purity than in the conventional processes.
    Type: Grant
    Filed: December 15, 1997
    Date of Patent: February 16, 1999
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Hidefumi Haramaki, Osamu Dodo, Mamoru Takamura
  • Patent number: 5855743
    Abstract: A process is provided for the isolation of (meth)acrylic acid from a mixture containing (meth)acrylic acid as the main component and lower aldehydes as secondary components by rectification in a rectification column having a stripping section and a rectification section, wherein the starting mixture containing the (meth)acrylic acid to be isolated by rectification is not fed directly to the rectification column but is first passed into a heated dwell vessel which is connected to the vapor side of the rectification section of the rectification column and in which the starting mixture is kept at the boil and, instead of the starting mixture as such, the bottom liquid of the dwell vessel is fed to the rectification column.
    Type: Grant
    Filed: July 29, 1997
    Date of Patent: January 5, 1999
    Assignee: BASF Aktiengesellschaft
    Inventors: Holger Herbst, Ulrich Hammon
  • Patent number: 5852201
    Abstract: A process for preparing crude dimethyl terephthalate, comprises oxidizing a mixture comprising para-xylene and methyl para-toluate, esterifying the oxidized mixture with methanol, separating the resulting crude ester into fractions. By separating the crude ester with a distillation column containing structured packing and using a lower bottom temperature, product yield is increased, and the process is made more economical.
    Type: Grant
    Filed: January 17, 1997
    Date of Patent: December 22, 1998
    Assignee: Huels Aktiengesellschaft
    Inventors: Udo Lenz, Ulrich Neutzler, Anton Schoengen, Reinhard Sigg
  • Patent number: 5849161
    Abstract: A solution of an organic compound containing at least a polymer is treated by adding an amount of water to said solution, distilling the organic compound to recover the organic compound, and incinerating the remained aqueous solution containing the polymer.
    Type: Grant
    Filed: March 19, 1997
    Date of Patent: December 15, 1998
    Assignee: Kuraray Co., Ltd.
    Inventors: Hiroshi Kishimoto, Akira Omura
  • Patent number: 5759358
    Abstract: Processes are provided for producing a pure grade of acrylic acid having residual aldehyde levels under 10 parts per million. The processes apply selected groups of amines sequentially and, preferably, continuously in selectively reducing, for example, acrolein and furfural, and may be advantageously conducted in the presence of maleic acid and maleic anhydride impurities.
    Type: Grant
    Filed: October 27, 1995
    Date of Patent: June 2, 1998
    Assignee: Rohm and Haas Company
    Inventors: William Bauer, Jr., Timothy Allen Hale, Robert Michael Mason, Rita Karina Upmacis, Lori Marie Petrovich
  • Patent number: 5746892
    Abstract: A continuous process for producing a pure grade of acrylic acid having residual aldehyde levels under 10 parts per million. The process applies two groups of amines sequentially and continuously in selectively reducing acrolein and furfural and may be advantageously conducted in the presence of maleic acid and maleic anhydride impurities.
    Type: Grant
    Filed: August 5, 1996
    Date of Patent: May 5, 1998
    Assignee: Rohm and Haas Company
    Inventors: William Bauer, Jr., Timothy Allen Hale, Robert Michael Mason, Rita Karina Upmacis
  • Patent number: 5728272
    Abstract: In a process for the separation by rectification of unsaturated carboxylic acids from solvents in which the acids were absorbed after the synthesis reaction, the rectification is briefly interrupted and the rectification column is flushed with a basic solution. The interruption is carried out at regular time intervals. The basic solution used is an aqueous solution of alkali metal and/or alkaline earth metal hydroxide, preferably NaOH, KOH, Ca(OH).sub.2 or their anhydrous oxides; alkaline polar organic solvents as amines or amides can be used, too.
    Type: Grant
    Filed: August 13, 1996
    Date of Patent: March 17, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Hammon, Volker Schliephake, Wolfgang Pies, Ulrich Rauh
  • Patent number: 5571386
    Abstract: The invention provides a continuous process for producing a pure grade of acrylic acid having residual aldehyde levels under 10 parts per million. The process applies two groups of amines sequentially and continuously in selectively reducing acrolein and furfural and may be advantageously conducted in the presence of maleic acid and maleic anhydride impurities.
    Type: Grant
    Filed: May 31, 1994
    Date of Patent: November 5, 1996
    Assignee: Rohm and Haas Company
    Inventors: William Bauer, Jr., Timothy A. Hale, Robert M. Mason, Rita K. Upmacis
  • Patent number: 5482597
    Abstract: In a process for purifying crude (meth)acrylic acid, the crude (meth)acrylic acid is worked up by distillation after addition of an organic carboxylic acid hydrazide and, if desired, an organic sulfonic acid.
    Type: Grant
    Filed: November 23, 1994
    Date of Patent: January 9, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Holger Herbst, Gerhard Nestler, Jerry Darlington, Hans Martan
  • Patent number: 5435892
    Abstract: A distillation process is used to separate methanol from a mixture of methanol with methyl acrylate or methyl methacrylate, as well as from a mixture of methanol and water with methyl acrylate or methyl methacrylate with the use of an azeotropic solvent, which forms an azeotropic mixture with methanol. In distilling such a mixture by the use of a distillation column:(1) part of the condensate of vapors distilled over from the top of the distillation column top is returned to the top of the column;(2) the remaining condensate is separated into two layers;(3) the upper layer essentially composed of an azeotropic solvent from the two separated layers is fed to an intermediate portion of the distillation column;(4) the lower layer essentially composed of methanol from the above two separated layers is withdrawn from the distillation system; and(5) methyl acrylate or methyl methacrylate, or else, methyl acrylate or methyl methacrylate and water, are recovered from the bottom of the column.
    Type: Grant
    Filed: August 30, 1993
    Date of Patent: July 25, 1995
    Assignees: Mitsubishi Rayon Co., Ltd., Osaka Organic Chemical Ind. Co., Ltd.
    Inventors: Seiji Miyazaki, Yasutaka Nakashima, Toshihiro Satoh, Tadao Ida, Etsuji Sato, Akio Tani
  • Patent number: 5393385
    Abstract: Hexane is difficult to separate from vinyl acetate and/or methyl acrylate by conventional distillation or rectification because of the closeness of their boiling points. Hexane can be readily separated from vinyl acetate and/or methyl acrylate by extractive distillation. Effective agents are dimethylsulfoxide and dimethylformamide.
    Type: Grant
    Filed: March 14, 1994
    Date of Patent: February 28, 1995
    Assignee: Lloyd Berg
    Inventors: Lloyd Berg, Randi W. Wytcherley
  • Patent number: 5358611
    Abstract: A method of reducing the levels of impurities in aqueous monomer solutions is provided. Subjecting aqueous monomer solutions to ultraviolet radiation for from about 2 minutes to about 5 hours, reduces the level of impurities, especially carbonyl-compounds.
    Type: Grant
    Filed: May 17, 1993
    Date of Patent: October 25, 1994
    Assignee: Rohm and Haas Company
    Inventors: William Bauer, Jr., Nelson I. Quiros
  • Patent number: 5356520
    Abstract: A process for the separation of amyl acetate, a high boiling point solvent from various high boiling point corrosive impurities, namely, bromoethyl acetate, in an industrial setting to allow for reuse through continuous recycling thereof.
    Type: Grant
    Filed: February 26, 1993
    Date of Patent: October 18, 1994
    Assignee: Mallinckrodt Medical PMC
    Inventors: William Z. McCarthy, Michael J. Gentilcore
  • Patent number: 5342487
    Abstract: A process for reducing the amount of unwanted di(meth)acrylate produced during the distillation of hydroxyalkyl acrylates or hydroxyalkyl methacrylates.
    Type: Grant
    Filed: October 8, 1991
    Date of Patent: August 30, 1994
    Assignee: Rohm and Haas Compnay
    Inventors: Christine McDade, Makarand D. Phadke, William D. Weir
  • Patent number: 5300198
    Abstract: A distillation process for the separation of acetic anhydride from a mixture thereof with ethylidene diacetate wherein the mixture of acetic anhydride and ethylidene diacetate is fed to the mid section of a distillation column and a small amount of acetic acid is fed separately to the lower section of the column. The addition of the acetic acid suppresses tar formation during the distillation process.
    Type: Grant
    Filed: April 5, 1993
    Date of Patent: April 5, 1994
    Assignee: Eastman Kodak Company
    Inventors: Donald W. Lane, Ronnie D. Lilly
  • Patent number: 5262014
    Abstract: A process for removing acetone from an acetone/methyl acetate/methyl iodide mixture utilizing extractive distillation with water being introduced to the distillation zone above the point of introduction of the mixture and acetic acid being introduced at or above the point of introduction of the mixture. In a preferred embodiment the mixture is subjected to an initial extraction with an aqueous extractant to remove most of the methyl iodide.The process is particularly applicable to removing acetone by-product in carbonylation processes for the production of acetic anhydride.
    Type: Grant
    Filed: June 12, 1992
    Date of Patent: November 16, 1993
    Assignee: The British Petroleum Company p.l.c.
    Inventors: Jeremy B. Cooper, John Dixon-Hall, Stephen J. Smith
  • Patent number: 5240567
    Abstract: The separation of vinyl acetate from methyl acrylate by distillation is difficult because of the closeness of their boiling points. Vinyl acetate can be readily removed from methyl acrylate by extractive distillation. Typical effective agents are phenol, methoxyethanol and isobutyl vinyl ether.
    Type: Grant
    Filed: April 2, 1993
    Date of Patent: August 31, 1993
    Assignee: Lloyd Berg
    Inventors: Lloyd Berg, Randi W. Wytcherley
  • Patent number: 5236559
    Abstract: Hexane cannot be removed from hexane--vinyl acetate--methyl acrylate mixtures because of the ternary azeotrope. Hexane can be readily removed from hexane--vinyl acetate--methyl acrylate mixtures by extractive distillation. Typical effective agents are phenol, diethylene glycol methyl ether and 2-nitropropane.
    Type: Grant
    Filed: January 22, 1993
    Date of Patent: August 17, 1993
    Assignee: Lloyd Berg
    Inventors: Lloyd Berg, Randi W. Wytcherley
  • Patent number: 5236560
    Abstract: A dimeric cyclic ester of an alpha-hydroxycarboxylic acid (lactide) is separated and recovered from a vapor product stream containing the cyclic ester, the corresponding lower-boiling hydroxycarboxylic acid (lactic), higher-boiling oligomeric hydroxycarboxylic acid and water without the use of solvents. More specifically, the vapor stream is condensed to obtain a condensate containing substantially all the cyclic ester, and the condensate is refined by distillation means alone to recover the cyclic ester substantially free of water, the alpha-hydroxycarboxylic acid and the higher-boiling oligomers.
    Type: Grant
    Filed: March 13, 1992
    Date of Patent: August 17, 1993
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Neville E. Drysdale, Thomas W. Stambaugh, James V. Tarbell
  • Patent number: 5225049
    Abstract: A process for refining organic-solvent containing crude polyol fatty-acid polyester reaction product, including the steps of distilling the crude reaction product to substantially remove the organic solvent, and subsequently subjecting the distilled reaction product to a bleaching treatment. The process allows an economic use of bleaching agents while achieving good color and color stability of the refined product.
    Type: Grant
    Filed: December 13, 1990
    Date of Patent: July 6, 1993
    Assignee: Van den Bergh Foods Co., Division of Conopco, Inc.
    Inventors: Bart Barmentlo, Jan Van Buuren, Alexander M. Hulstaert
  • Patent number: 5207874
    Abstract: The purification by distillation of glycidyl (meth)acrylate containing light products containing epichlorohydrin and light impurities, and heavy impurities comprises: in a first stage, a distillation of the glycidyl (meth)acrylate to be purified is conducted in the presence of a first solvent, e.g., water, capable of forming a low boiling point heteroazeotrope with the light impurities and epichlorohydrin, so as to obtain a head fraction which consists essentially of a solvent-light products heteroazeotrope; and, in a second stage, the glycidyl (meth)acrylate thus freed from the light products is subjected to a distillation in the presence of a second solvent, e.g.
    Type: Grant
    Filed: June 20, 1991
    Date of Patent: May 4, 1993
    Assignee: Atochem
    Inventors: Raymond Hess, Christian Lacroix
  • Patent number: 5183539
    Abstract: A method of purifying a crude glycidyl (meth)acrylate, by (1) subjecting a crude glycidyl (meth)acrylate containing epichlorohydrin and other chlorine compounds as impurities to a stripping treatment with a mixed gas containing oxygen gas in the presence of a quaternary ammonium salt, and then (2) distilling the treated product to obtain a purified glycidyl (meth)acrylate.
    Type: Grant
    Filed: November 15, 1991
    Date of Patent: February 2, 1993
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Akihiro Honma, Masahiro Kurokawa
  • Patent number: 5154800
    Abstract: Acrylic acid cannot be completely separated from water by conventional distillation or rectification because of the minimum boiling azeotrope. Acrylic acid can be readily separated from water by extractive distillation. Effective agents are dimethylsulfoxide, sulfolane, dimethylformamide or dimethylacetamide.
    Type: Grant
    Filed: January 31, 1992
    Date of Patent: October 13, 1992
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5145989
    Abstract: Black acid or the sulfuric acid residue obtained in the manufacture of ethyl acrylate by reaction of ethylene and acrylic acid in the presence of sulfuric acid is heated and distilled in the presence of a solvent for recovery of acrylic acid and ethyl acrylate.
    Type: Grant
    Filed: July 14, 1987
    Date of Patent: September 8, 1992
    Assignee: Hoechst Celanese Corporation
    Inventors: Edward F. Dougherty, Paul James L.
  • Patent number: 5143585
    Abstract: An organic solvent having a boiling point lower than that of water is removed from liquid containig water and the organic solvent contained in a tank by exhausting air in the tank, wherein an air pressure in the tank is kept about vapor pressure level of the liquid.
    Type: Grant
    Filed: September 15, 1989
    Date of Patent: September 1, 1992
    Assignee: Konica Corporation
    Inventors: Kazuyoshi Ichikawa, Shinichi Suzuki, Sanae Oyama, Hideaki Kimura
  • Patent number: 5028735
    Abstract: A purification process for methyl methacrylate (MMA) and a recovery process for methanol are disclosed. A mixture, which contains water, methanol and methyl methacrylate (MMA) as principal components along with at least one of methyl acrylate, methyl propionate and methacrylic acid, is azeotropically distilled together with hexane to obtain MMA in a form substantially free of water, methanol methyl acrylate, methyl propionate and hexane and a low boiling-point fraction. The low boiling-point fraction is cooled and separated into a water phase and an oil phase. Methanol can be recovered from the water phase by adding an alkaline substance to it and then distilling the resultant mixture. A preparation process of MMA is also disclosed. MMA can be prepared by esterifying methacrylic acid or methacrylamide with methanol and then applying the above purification process.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: July 2, 1991
    Assignees: Mitsui Toatsu Chemicals, Inc., Kuraray Company, Ltd.
    Inventors: Hirozo Segawa, Norio Ishikawa, Katsuji Yoguchi, Morimasa Kuragano, Minoru Koshibe
  • Patent number: 4879412
    Abstract: Disclosed herein is a process for bringing methacrylic acid, which has been obtained by the catalytic oxidation of compound having 4 carbon atoms, into contact with a basic anion-exchange resin so as to remove byproduced dibasic acids and the like from the methacrylic acid and to purify the same.
    Type: Grant
    Filed: March 3, 1986
    Date of Patent: November 7, 1989
    Assignees: Mitsui Toatsu Chemicals, Inc., Kyowa Gas Chemical Industry Co., Ltd.
    Inventors: Kozo Iwasaki, Morimasa Kuragano, Minoru Koshibe, Yoshihiro Sezaki, Katsuji Yoguchi, Yoshio Koyama
  • Patent number: 4838997
    Abstract: Process for deodorizing triglyceride oil comprises passing dry steam through the oil, the oil being at a temperature between 160.degree. and 280.degree. C. and under a pressure of between 0.1 to 8.0 mbar and condensing by indirect condenser means a vapor phase having a Reynolds number less than 2300 and comprising steam, volatile materials from the oil and less than 100 mg neutral oil per m.sup.3 of steam when measured under the conditions prevailing in the headspace above the oil. The condensate can be solid or liquid form. In either case the condensate can be readily removed from the condenser.
    Type: Grant
    Filed: November 13, 1987
    Date of Patent: June 13, 1989
    Assignee: Atlas-Danmark A/S
    Inventor: Werner Merk
  • Patent number: 4828652
    Abstract: Aldehydes are removed from .alpha.,.beta.-olefinically unsaturated monocarboxylic acids of 3 or 4 carbon atoms by adding hydrazine derivatives and distilling the unsaturated monocarboxylic acids if the hydrazine derivatives used are aminoguanidine and/or aminoguanidine salts in amounts of from 1 to 3 moles per mole of aldehyde.
    Type: Grant
    Filed: December 1, 1987
    Date of Patent: May 9, 1989
    Assignee: BASF Aktiengesellschaft
    Inventor: Wilhelm K. Schropp
  • Patent number: 4755262
    Abstract: This invention relates to a method for the purification of glycidyl acrylate or glycidyl methacrylate. Specifically, the invention effects the purification by using a residual catalyst-inactivating additive and consequently produces highly purified glycidyl acrylate or glycidyl methacrylate containing substantially no epichlorohydrin and having a low chlorine content.
    Type: Grant
    Filed: October 26, 1987
    Date of Patent: July 5, 1988
    Assignee: Osaka Yuki Kagaku Kogyo Kabushiki Kaisha
    Inventors: Mitsumasa Matsunaga, Yukio Tanaka, Akio Tani, Shigeaki Matsumoto
  • Patent number: 4739108
    Abstract: A process is disclosed for separation of propionic acid and methacrylic acid and esterification of methacrylic acid with an aliphatic alcohol of from 1 to 4 carbon atoms in presence of a suitable catalyst wherein separation and esterification is obtained with minimal polymerization of methacrylic acid.
    Type: Grant
    Filed: June 25, 1984
    Date of Patent: April 19, 1988
    Assignee: Amoco Corporation
    Inventor: Lawrence D. Lillwitz
  • Patent number: 4736062
    Abstract: A process is disclosed for producing an alpha-, beta-ethylenically unsaturated monocarboxylic acid compound which comprises the aldol-type condensation of a saturated aliphatic monocarboxylic acid compound under vapor phase conditions in the presence of a hydrocarbon of 6 to 12 carbon atoms and a solid catalyst.
    Type: Grant
    Filed: June 25, 1984
    Date of Patent: April 5, 1988
    Assignee: Amoco Corporation
    Inventors: Gary P. Hagen, Thomas G. Smith
  • Patent number: 4698440
    Abstract: A batch process for preparing n-butyl methacrylate directly from n-butanol and methacrylic acid by employing azeotropic distillation and azeotropic phase separation.
    Type: Grant
    Filed: August 5, 1985
    Date of Patent: October 6, 1987
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Leslie M. Blair, Roddy M. Conrad
  • Patent number: 4671857
    Abstract: The distillative separation of methacrylic acid from isobutyric acid is significantly improved by the introduction into the distillation system of a third component selected from the group consisting of methyl methacrylate, methyl isobutyrate and dimethylformamide.
    Type: Grant
    Filed: September 26, 1986
    Date of Patent: June 9, 1987
    Assignee: Eastman Kodak Company
    Inventor: Kris A. Johnson
  • Patent number: 4642167
    Abstract: Isobutyl acetate cannot be completely removed from isobutyl acetate--isobutanol--water mixtures by distillation because of the presence of the minimum ternary azeotrope. Isobutyl acetate can be readily removed from mixtures containing it, isobutanol and water by using extractive distillation in which the extractive distillation agent is a higher boiling oxygenated, nitrogenous and/or sulfur containing organic compound or a mixture of these. Typical examples of effective agents are N,N-dimethylacetamide; dimethylformamide and dimethylsulfoxide; acetamide, dimethylformamide and dipropylene glycol.
    Type: Grant
    Filed: March 7, 1985
    Date of Patent: February 10, 1987
    Inventors: Lloyd Berg, An-I Yeh
  • Patent number: 4599144
    Abstract: 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: Grant
    Filed: June 25, 1984
    Date of Patent: July 8, 1986
    Assignee: Standard Oil Company (Indiana)
    Inventors: Marc O. Baleiko, Edward F. Rader
  • Patent number: 4595778
    Abstract: Oxidation catalysts of the general formulaW.sub.6 Mo.sub.a V.sub.b P.sub.c Cu.sub.d As.sub.e Sb.sub.f X.sub.g Y.sub.h O.sub.xwhere X is K, Rb and/or Cs, Y is Nb, Fe, Mn, Sn, Li, Na, Sr, Rh, Ce, Ti and/or Cr, a is from 2.0 to 6, b is from 0 to 3, c is from 0.1 to 3, d is from 0.01 to 1, e is from 0 to 1, f is from 0 to 2, g is from 0.01 to 3, h is from 0 to 1 and x is the number of oxygen atoms formally required to saturate the valencies of the catalyst components, give high conversions and particularly high selectivity in the oxidation of methacrolein in the gas phase to methacrylic acid.
    Type: Grant
    Filed: March 7, 1984
    Date of Patent: June 17, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerd Duembgen, Gerd Fouquet, Richard Krabetz, Franz Merger, Friedbert Nees
  • Patent number: 4576683
    Abstract: 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: Grant
    Filed: June 6, 1984
    Date of Patent: March 18, 1986
    Assignee: Badger B.V.
    Inventor: Lester R. Cohen
  • Patent number: 4563538
    Abstract: A process for stabilizing a silicon-containing methacrylate having the formula (I): ##STR1## wherein X is Si(OCH.sub.3).sub.3, Si(OCH.sub.3).sub.2 CH.sub.3, Si(OCH.sub.3)(CH.sub.3).sub.2 or Si(CH.sub.3).sub.3 which comprises adding 2,5-di-t-butylbenzoquinone to the silicon-containing methacrylate, whereby polymerization of the silicon-containing methacrylate can be inhibited. As a result, the silicon-containing methacrylate can be stabilized without any trouble in distillation step.
    Type: Grant
    Filed: May 6, 1985
    Date of Patent: January 7, 1986
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Hiroshi Wakabayashi, Takahisa Iwahara
  • Patent number: 4518462
    Abstract: In purifying methyl methacrylate by feeding a feed mixture containing methanol, methyl methacrylate and 0.
    Type: Grant
    Filed: May 25, 1983
    Date of Patent: May 21, 1985
    Assignee: Asahi Kasei Kogyo Kabushiki Kaisha
    Inventors: Atsushi Aoshima, Yoshio Suzuki, Mikihiko Nakamura
  • Patent number: 4480116
    Abstract: The present invention provides an improvement in methods for preparing and processing readily polymerizable acrylate monomers. The improvement comprises employing phenyl-para-benzoquinone, 2,5-di-phenyl-para-benzoquinone, and mixtures thereof as process inhibitors. The process inhibitors are present in a concentration of about 50 to 3000 ppm, preferably about 250 to 2000 ppm, and most preferably about 500 ppm.
    Type: Grant
    Filed: March 2, 1983
    Date of Patent: October 30, 1984
    Assignee: Eastman Kodak Company
    Inventors: Ambrose J. Clonce, Michael Palmer, Samuel L. Gott
  • Patent number: 4464229
    Abstract: In a process for producing an acrylic or methacrylic ester by esterifying acrylic or methacrylic acid with a lower aliphatic alcohol having 1 to 3 carbon atoms in the presence of an acidic catalyst, the improvement which comprises(1) distilling the resulting esterification reaction mixture while feeding the acrylic or methacrylic ester into a distillation column from outside the system, thereby to yield as a distillate a mixture composed of the acrylic or methacrylic ester, water and the unreacted alcohol and being substantially free from acrylic or methacrylic acid, and (2) recycling the residue in the distillation column, from which the ester and water formed have been substantially removed, to the esterification reaction in such a proportion that the mole ratio of acrylic or methacrylic acid to the alcohol in the entire starting materials fed to the esterification reaction is kept at 1:0.5-1.0.
    Type: Grant
    Filed: June 29, 1982
    Date of Patent: August 7, 1984
    Assignee: Nippon Shokubai Kagaku Kogyo Co. Ltd.
    Inventors: Takahisa Sato, Sumio Nakashima, Masao Baba
  • Patent number: 4358347
    Abstract: Carbonyl impurities in acrylic acid are removed by reacting them with a 1,2-glycol prior to distillation. The acetal-type products remain as heavies in the distillation bottoms.
    Type: Grant
    Filed: January 26, 1982
    Date of Patent: November 9, 1982
    Assignee: The Dow Chemical Company
    Inventors: Bonnie K. Mettetal, Richard P. Kolonko, Jr.
  • Patent number: 4317926
    Abstract: In a process for producing acrylic acid which comprises contacting with water an acrylic acid-containing reaction product gas which has been obtained by the catalytic vapor phase oxidation of an olefinic compound of a general formula, CH.sub.2 .dbd.CHX, wherein X represents at least one group selected from the group consisting of CH.sub.
    Type: Grant
    Filed: January 15, 1979
    Date of Patent: March 2, 1982
    Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.
    Inventors: Takahisa Sato, Masao Baba, Michito Okane
  • Patent number: 4260821
    Abstract: The presence of solid polymer in distillation columns and their associated reboilers used for the recovery of methacrylic and acetic acids produced by the oxidation of methacrolein may be minimized by the use of inhibitors and introduction of molecular oxygen at a rate above a predetermined threshold value, which is a function of the operating temperature of the equipment. For a given temperature, the amount of solids has been found to be greatly increased below the threshold value of oxygen, while above the threshold value, the rate of appearance of solids has been found to be minimized and further increases in oxygen rate have only a minimal effect. At a typical operation temperature of 120.degree. C., the threshold value of about 0.1 SLH O.sub.2 /100 gm of liquid. A gas containing a relatively high concentration of oxygen is preferred.
    Type: Grant
    Filed: March 15, 1979
    Date of Patent: April 7, 1981
    Assignee: Halcon Research and Development Corp.
    Inventor: Bruce W. Benjamin
  • Patent number: 4253948
    Abstract: Separation of certain water soluble organic monomers such as acrylic acid from an aqueous solution can be accomplished by extraction with carbon dioxide, crystallizing the extract to remove carbon dioxide hydrate, and flashing off the remaining carbon dioxide solvent from the extract.
    Type: Grant
    Filed: May 14, 1979
    Date of Patent: March 3, 1981
    Assignee: Standard Oil Company
    Inventors: Harley F. Hardman, Albert P. Schwerko