Acrylic Acid Or Ester Patents (Class 203/DIG21)
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Patent number: 5968322Abstract: 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: GrantFiled: November 26, 1997Date of Patent: October 19, 1999Inventors: Peter Arnoldy, Eric Kragtwijk, Antoon Paul Michael Kremers
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Patent number: 5961790Abstract: 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: GrantFiled: December 14, 1994Date of Patent: October 5, 1999Assignee: BASF AktiengesellschaftInventors: Holger Herbst, Gerhard Nestler, Jerry Darlington, Ulrich Hammon
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Patent number: 5916422Abstract: 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: GrantFiled: March 7, 1997Date of Patent: June 29, 1999Assignee: Daicel Chemical Industries, Ltd.Inventors: Satoshi Kimura, Takashi Ueno, Yoshiaki Morimoto
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Patent number: 5897749Abstract: 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: GrantFiled: October 18, 1996Date of Patent: April 27, 1999Assignee: BASF AktiengesellschaftInventors: Ruprecht Kroker, Manfred Wiedemann
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Patent number: 5872288Abstract: 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: GrantFiled: December 15, 1997Date of Patent: February 16, 1999Assignee: Nippon Shokubai Co., Ltd.Inventors: Hidefumi Haramaki, Osamu Dodo, Mamoru Takamura
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Patent number: 5855743Abstract: 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: GrantFiled: July 29, 1997Date of Patent: January 5, 1999Assignee: BASF AktiengesellschaftInventors: Holger Herbst, Ulrich Hammon
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Patent number: 5852201Abstract: 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: GrantFiled: January 17, 1997Date of Patent: December 22, 1998Assignee: Huels AktiengesellschaftInventors: Udo Lenz, Ulrich Neutzler, Anton Schoengen, Reinhard Sigg
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Patent number: 5849161Abstract: 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: GrantFiled: March 19, 1997Date of Patent: December 15, 1998Assignee: Kuraray Co., Ltd.Inventors: Hiroshi Kishimoto, Akira Omura
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Patent number: 5759358Abstract: 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: GrantFiled: October 27, 1995Date of Patent: June 2, 1998Assignee: Rohm and Haas CompanyInventors: William Bauer, Jr., Timothy Allen Hale, Robert Michael Mason, Rita Karina Upmacis, Lori Marie Petrovich
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Patent number: 5746892Abstract: 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: GrantFiled: August 5, 1996Date of Patent: May 5, 1998Assignee: Rohm and Haas CompanyInventors: William Bauer, Jr., Timothy Allen Hale, Robert Michael Mason, Rita Karina Upmacis
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Patent number: 5728272Abstract: 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: GrantFiled: August 13, 1996Date of Patent: March 17, 1998Assignee: BASF AktiengesellschaftInventors: Ulrich Hammon, Volker Schliephake, Wolfgang Pies, Ulrich Rauh
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Patent number: 5571386Abstract: 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: GrantFiled: May 31, 1994Date of Patent: November 5, 1996Assignee: Rohm and Haas CompanyInventors: William Bauer, Jr., Timothy A. Hale, Robert M. Mason, Rita K. Upmacis
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Patent number: 5482597Abstract: 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: GrantFiled: November 23, 1994Date of Patent: January 9, 1996Assignee: BASF AktiengesellschaftInventors: Holger Herbst, Gerhard Nestler, Jerry Darlington, Hans Martan
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Patent number: 5435892Abstract: 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: GrantFiled: August 30, 1993Date of Patent: July 25, 1995Assignees: Mitsubishi Rayon Co., Ltd., Osaka Organic Chemical Ind. Co., Ltd.Inventors: Seiji Miyazaki, Yasutaka Nakashima, Toshihiro Satoh, Tadao Ida, Etsuji Sato, Akio Tani
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Patent number: 5393385Abstract: 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: GrantFiled: March 14, 1994Date of Patent: February 28, 1995Assignee: Lloyd BergInventors: Lloyd Berg, Randi W. Wytcherley
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Patent number: 5358611Abstract: 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: GrantFiled: May 17, 1993Date of Patent: October 25, 1994Assignee: Rohm and Haas CompanyInventors: William Bauer, Jr., Nelson I. Quiros
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Patent number: 5356520Abstract: 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: GrantFiled: February 26, 1993Date of Patent: October 18, 1994Assignee: Mallinckrodt Medical PMCInventors: William Z. McCarthy, Michael J. Gentilcore
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Patent number: 5342487Abstract: A process for reducing the amount of unwanted di(meth)acrylate produced during the distillation of hydroxyalkyl acrylates or hydroxyalkyl methacrylates.Type: GrantFiled: October 8, 1991Date of Patent: August 30, 1994Assignee: Rohm and Haas CompnayInventors: Christine McDade, Makarand D. Phadke, William D. Weir
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Patent number: 5300198Abstract: 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: GrantFiled: April 5, 1993Date of Patent: April 5, 1994Assignee: Eastman Kodak CompanyInventors: Donald W. Lane, Ronnie D. Lilly
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Patent number: 5262014Abstract: 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: GrantFiled: June 12, 1992Date of Patent: November 16, 1993Assignee: The British Petroleum Company p.l.c.Inventors: Jeremy B. Cooper, John Dixon-Hall, Stephen J. Smith
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Patent number: 5240567Abstract: 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: GrantFiled: April 2, 1993Date of Patent: August 31, 1993Assignee: Lloyd BergInventors: Lloyd Berg, Randi W. Wytcherley
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Patent number: 5236560Abstract: 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: GrantFiled: March 13, 1992Date of Patent: August 17, 1993Assignee: E. I. Du Pont de Nemours and CompanyInventors: Neville E. Drysdale, Thomas W. Stambaugh, James V. Tarbell
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Patent number: 5236559Abstract: 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: GrantFiled: January 22, 1993Date of Patent: August 17, 1993Assignee: Lloyd BergInventors: Lloyd Berg, Randi W. Wytcherley
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Patent number: 5225049Abstract: 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: GrantFiled: December 13, 1990Date of Patent: July 6, 1993Assignee: Van den Bergh Foods Co., Division of Conopco, Inc.Inventors: Bart Barmentlo, Jan Van Buuren, Alexander M. Hulstaert
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Patent number: 5207874Abstract: 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: GrantFiled: June 20, 1991Date of Patent: May 4, 1993Assignee: AtochemInventors: Raymond Hess, Christian Lacroix
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Patent number: 5183539Abstract: 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: GrantFiled: November 15, 1991Date of Patent: February 2, 1993Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Akihiro Honma, Masahiro Kurokawa
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Patent number: 5154800Abstract: 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: GrantFiled: January 31, 1992Date of Patent: October 13, 1992Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5145989Abstract: 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: GrantFiled: July 14, 1987Date of Patent: September 8, 1992Assignee: Hoechst Celanese CorporationInventors: Edward F. Dougherty, Paul James L.
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Patent number: 5143585Abstract: 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: GrantFiled: September 15, 1989Date of Patent: September 1, 1992Assignee: Konica CorporationInventors: Kazuyoshi Ichikawa, Shinichi Suzuki, Sanae Oyama, Hideaki Kimura
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Patent number: 5028735Abstract: 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: GrantFiled: March 30, 1990Date of Patent: July 2, 1991Assignees: Mitsui Toatsu Chemicals, Inc., Kuraray Company, Ltd.Inventors: Hirozo Segawa, Norio Ishikawa, Katsuji Yoguchi, Morimasa Kuragano, Minoru Koshibe
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Patent number: 4879412Abstract: 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: GrantFiled: March 3, 1986Date of Patent: November 7, 1989Assignees: Mitsui Toatsu Chemicals, Inc., Kyowa Gas Chemical Industry Co., Ltd.Inventors: Kozo Iwasaki, Morimasa Kuragano, Minoru Koshibe, Yoshihiro Sezaki, Katsuji Yoguchi, Yoshio Koyama
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Patent number: 4838997Abstract: 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: GrantFiled: November 13, 1987Date of Patent: June 13, 1989Assignee: Atlas-Danmark A/SInventor: Werner Merk
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Patent number: 4828652Abstract: 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: GrantFiled: December 1, 1987Date of Patent: May 9, 1989Assignee: BASF AktiengesellschaftInventor: Wilhelm K. Schropp
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Patent number: 4755262Abstract: 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: GrantFiled: October 26, 1987Date of Patent: July 5, 1988Assignee: Osaka Yuki Kagaku Kogyo Kabushiki KaishaInventors: Mitsumasa Matsunaga, Yukio Tanaka, Akio Tani, Shigeaki Matsumoto
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Patent number: 4739108Abstract: 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: GrantFiled: June 25, 1984Date of Patent: April 19, 1988Assignee: Amoco CorporationInventor: Lawrence D. Lillwitz
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Patent number: 4736062Abstract: 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: GrantFiled: June 25, 1984Date of Patent: April 5, 1988Assignee: Amoco CorporationInventors: Gary P. Hagen, Thomas G. Smith
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Patent number: 4698440Abstract: A batch process for preparing n-butyl methacrylate directly from n-butanol and methacrylic acid by employing azeotropic distillation and azeotropic phase separation.Type: GrantFiled: August 5, 1985Date of Patent: October 6, 1987Assignee: E. I. Du Pont de Nemours and CompanyInventors: Leslie M. Blair, Roddy M. Conrad
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Patent number: 4671857Abstract: 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: GrantFiled: September 26, 1986Date of Patent: June 9, 1987Assignee: Eastman Kodak CompanyInventor: Kris A. Johnson
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Patent number: 4642167Abstract: 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: GrantFiled: March 7, 1985Date of Patent: February 10, 1987Inventors: Lloyd Berg, An-I Yeh
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Patent number: 4599144Abstract: Process is disclosed for treating the reaction product of propionic acid and formaldehyde to recover methacrylic acid from an aqueous effluent wherein said effluent contains methacrylic acid, unreacted formaldehyde, unreacted propionic acid, water and by-products.Type: GrantFiled: June 25, 1984Date of Patent: July 8, 1986Assignee: Standard Oil Company (Indiana)Inventors: Marc O. Baleiko, Edward F. Rader
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Patent number: 4595778Abstract: 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: GrantFiled: March 7, 1984Date of Patent: June 17, 1986Assignee: BASF AktiengesellschaftInventors: Gerd Duembgen, Gerd Fouquet, Richard Krabetz, Franz Merger, Friedbert Nees
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Patent number: 4576683Abstract: A method for separating carboxylic acids from mixtures with non-acids by an extractive distillation method using a lactam with a 5- or 6-membered ring, preferably N-methyl-2-pyrrolidone, as an extractant to extract the acids from the mixture with non-acids, followed by separating the extracted acids from the extractant by rectification.Type: GrantFiled: June 6, 1984Date of Patent: March 18, 1986Assignee: Badger B.V.Inventor: Lester R. Cohen
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Patent number: 4563538Abstract: 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: GrantFiled: May 6, 1985Date of Patent: January 7, 1986Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Hiroshi Wakabayashi, Takahisa Iwahara
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Patent number: 4518462Abstract: In purifying methyl methacrylate by feeding a feed mixture containing methanol, methyl methacrylate and 0.Type: GrantFiled: May 25, 1983Date of Patent: May 21, 1985Assignee: Asahi Kasei Kogyo Kabushiki KaishaInventors: Atsushi Aoshima, Yoshio Suzuki, Mikihiko Nakamura
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Patent number: 4480116Abstract: 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: GrantFiled: March 2, 1983Date of Patent: October 30, 1984Assignee: Eastman Kodak CompanyInventors: Ambrose J. Clonce, Michael Palmer, Samuel L. Gott
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Patent number: 4464229Abstract: 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: GrantFiled: June 29, 1982Date of Patent: August 7, 1984Assignee: Nippon Shokubai Kagaku Kogyo Co. Ltd.Inventors: Takahisa Sato, Sumio Nakashima, Masao Baba
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Patent number: 4358347Abstract: 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: GrantFiled: January 26, 1982Date of Patent: November 9, 1982Assignee: The Dow Chemical CompanyInventors: Bonnie K. Mettetal, Richard P. Kolonko, Jr.
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Patent number: 4317926Abstract: 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: GrantFiled: January 15, 1979Date of Patent: March 2, 1982Assignee: Nippon Shokubai Kagaku Kogyo Co., Ltd.Inventors: Takahisa Sato, Masao Baba, Michito Okane
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Patent number: 4260821Abstract: 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: GrantFiled: March 15, 1979Date of Patent: April 7, 1981Assignee: Halcon Research and Development Corp.Inventor: Bruce W. Benjamin
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Patent number: 4253948Abstract: 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: GrantFiled: May 14, 1979Date of Patent: March 3, 1981Assignee: Standard Oil CompanyInventors: Harley F. Hardman, Albert P. Schwerko