Organic Material Patents (Class 203/38)
  • Patent number: 4664753
    Abstract: The disclosure relates to a process for separating iodine and its compounds from the carbonlyation products acetic acid, acetic anhydride or ethylidene diacetate obtained by subjecting dimethylether, methyl acetate or methanol to a carbonylation reaction. For reducing the quantity of total iodine contaminating the carbonlyation products to less than 20 ppb iodine, the disclosure provides for the carbonylation products to be treated at temperatures of 20.degree. to 250.degree. C. with an alkyl or aryl phosphine or a heterocyclic aromatic nitrogen compound and at least one of the metals copper, silver, zinc or cadmium or their compounds and to be distillatively separated from the iodine thereby fixed in non-volatile form.
    Type: Grant
    Filed: August 6, 1984
    Date of Patent: May 12, 1987
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Heinz Erpenbach, Klaus Gehrmann, Winfried Lork, Peter Prinz
  • Patent number: 4613680
    Abstract: Angelic acid or esters thereof which are useful as perfume materials are prepared by isomerizing tiglic acid or an ester thereof with an organic sulfinic acid as the catalyst, and novel esters of angelic acid represented by the formula ##STR1## wherein R represents 3-hexenyl, 3-methyl-2-butenyl, 3-methyl-3-butenyl, 3-methyl-2-pentenyl, 3-methyl-4-pentenyl, CH.sub.3 (CH.sub.2).sub.l - (in which l is an integer from 5 to 9), cyclopentyl, cyclohexyl, 2-methylpentyl, .alpha.-methylbenzyl, neryl or furfuryl are provided as part of said esters of angelic acid.
    Type: Grant
    Filed: February 24, 1984
    Date of Patent: September 23, 1986
    Assignee: Toray Industries, Inc.
    Inventors: Masanobu Naruto, Hisao Kondo, Go Hata
  • 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: 4569725
    Abstract: A C.sub.4 -hydrocarbon mixture which essentially contains n-butenes and butanes is separated by a process in whichthe mixture is reacted with a carboxylic acid in the presence of an acidic catalyst to form a butyl carboxylate,the reaction mixture obtained from the esterification zone is distilled to give, as the top product, a fraction containing the butanes, and, as the bottom product, a fraction containing the resulting butyl carboxylate,the butyl carboxylate is decomposed at elevated temperatures to give the carboxylic acid and n-butenes, andthe mixture of n-butenes and carboxylic acid is then distilled, the n-butenes being obtained as the top product, and the carboxylic acid as the bottom product.
    Type: Grant
    Filed: May 23, 1984
    Date of Patent: February 11, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Alfred Lindner, Klaus Broellos, Gerhard Sandrock, Klaus Volkamer, Werner Hefner
  • Patent number: 4568429
    Abstract: 2,4-Dihydroxybenzophenone is prepared substantially quantitatively and in a highly purified form by reacting resorcinol with a benzotrihalide in the presence of an aqueous solution of N-methylpyrrolidone and subsequently subjecting the crude reaction product mixture to vacuum distillation.
    Type: Grant
    Filed: March 2, 1984
    Date of Patent: February 4, 1986
    Assignee: GAF Corporation
    Inventor: Kou-Chang Liu
  • Patent number: 4556461
    Abstract: A process for separating a butene-1/isobutene mixture from a C.sub.4 hydrocarbon fraction is provided which comprises subjecting the C.sub.4 hydrocarbon fraction to extractive distillation using a polar solvent to separate components predominantly containing 1,3-butadiene as an extract and obtain an overhead containing butanes, butene-1, isobutene and butene-2 as main components and being substantially free from C.sub.3 -C.sub.4 diolefinic and acetylenic hydrocarbons, feeding the overhead into a first distillation column, removing isobutane as an overhead component from the first distillation column, feeding high-boiling components from the bottom of the first distillation column to a second distillation column, removing n-butane and butene-2 from the bottom of the second distillation column, and obtaining highly pure butene-1 and isobutene from its top.
    Type: Grant
    Filed: December 1, 1982
    Date of Patent: December 3, 1985
    Assignee: Nippon Zeon Co., Ltd.
    Inventors: Shunichiro Ogura, Masamichi Soumai
  • Patent number: 4555312
    Abstract: A process for separating a butene-1/isobutene mixture from a C.sub.4 hydrocarbon fraction is provided which comprises subjecting the C.sub.4 hydrocarbon fraction to extractive distillation using a polar solvent to separate components predominantly containing 1,3-butadiene as an extract bottom and obtain an overhead containing butanes, butene-1, isobutene and butene-2 as main components and being substantially free from C.sub.3 -C.sub.4 diolefinic and acetylenic hydrocarbons, feeding the overhead into a first distillation column, removing n-butane and butene-2 as bottoms from the column, feeding low-boiling components from the top of the column into a second distillation column, removing isobutane from the top of the second distillation column, and obtaining highly pure butene-1 and isobutene from its bottom.
    Type: Grant
    Filed: November 23, 1982
    Date of Patent: November 26, 1985
    Assignee: Nippon Zeon Co. Ltd.
    Inventors: Shunichiro Ogura, Masamichi Soumai
  • Patent number: 4506091
    Abstract: A process for preparing esters which comprises reacting a polycarboxylic acid with an excess of alcohol and in the presence of an organotitanate catalyst, treating the crude mixture with a suitable chelate compound, removing the unreacted alcohol and hydrolyzing the treated titanium catalyst residues with steam, and recovering the purified ester by filtration.
    Type: Grant
    Filed: September 1, 1983
    Date of Patent: March 19, 1985
    Inventor: Donald L. Deardorff
  • Patent number: 4482775
    Abstract: A method for isomerizing isobutene or n-butene to produce a mixture of isobutene and normal butene, and polymerizing at least a portion thereof to produce isobutene/n-butene codimer, which comprieses feeding at least 80 weight % of either the isobutene or n-butene to a catalytic distillation reactor containing a fixed bed acidic cation exchange resin catalyst packing which provides both the catalyst sites and distillation sites for the reaction products, isomerizing a portion of the isobutene or n-butene to produce a mixture of isobutene and n-butene and reacting at least a portion of the isobutene and n-butene to form codimer of isobutene and n-butene, whereby an overhead fraction containing any unreacted isobutene and n-butene and a bottoms fraction containing codimer is produced. The result of the reaction is substantially the same regardless whether the feed is isobutene or n-butene. Other aspects of the invention, include combinations of procedures to produce high purity isobutene and n-butene.
    Type: Grant
    Filed: September 22, 1982
    Date of Patent: November 13, 1984
    Assignee: Chemical Research & Licensing Company
    Inventor: Lawrence A. Smith, Jr.
  • Patent number: 4481146
    Abstract: The invention relates to a process for the preparation of an ethyl ester from ethanol-containing mixtures of aliphatic alcohols, which comprises esterifying the alcohols with a carboxylic acid in the presence of an acid catalyst in a distilling column and separating in the same column the ethyl ester continuously from the ester mixture obtained. To this purpose, the alcohol mixture is introduced into the sump and the carboxylic acid is introduced into the column at a point located in the central part and the ethyl ester as well as the water formed during esterification are withdrawn continuously at the top of the column and the higher esters are withdrawn continuously at the sump.
    Type: Grant
    Filed: September 29, 1981
    Date of Patent: November 6, 1984
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ernst I. Leupold, Hans-Joachim Schmidt, Knut Popp
  • Patent number: 4465853
    Abstract: 3,4-Diacetoxybutene-1 can be easily isomerized into 1,4-diacetoxybutene-2 by contacting it with a cation exchange resin. This method is capable of providing an excellent reaction result and is free of the problem of corrosion of apparatus as well as the problem of formation of by-products. When acetic acid is present in said isomerization operation, the reaction rate is increased. Further, combination of this isomerization method with separation of 1,4-diacetoxybutene-2 from 3,4-diacetoxybutene-1 by distillation enables production of high-purity 1,4-diacetoxybutene-2 at a high efficiency.
    Type: Grant
    Filed: November 26, 1982
    Date of Patent: August 14, 1984
    Assignee: Japan Synthetic Rubber Co., Ltd.
    Inventors: Yoshinori Yoshida, Hironobu Shinohara
  • Patent number: 4454356
    Abstract: Methanol is reacted with branched monoolefins such as isobutylene, or mixtures of hydrocarbons such as mixed C-4's from or in a refinery, in the presence of methanesulfonic acid. A column (10) operation is described wherein methanesulfonic acid (11) and methanol (12) are fed in countercurrent fashion to hydrocarbons (13). Crude product ether is removed as a liquid sidestream (25) above the feed of methanesulfonic acid (11), while hydrocarbons depleted of the reactive branched monoolefins (24) are removed overhead. The methanesulfonic acid suppresses the vapor pressure of methanol relative to product ether.
    Type: Grant
    Filed: October 14, 1982
    Date of Patent: June 12, 1984
    Assignee: Allied Corporation
    Inventors: Divakaran Masilamani, Andiappan K. S. Murthy
  • Patent number: 4454358
    Abstract: Ethanol is produced continuously via the carbonylation of methanol, by(a) carbonylating methanol, in a reactor R, in the presence of a carbonyl complex of a metal of group VIII of the periodic table and of a halogen compound,(b) separating, in a distillation column D1, the reactor discharge, into a top fraction comprising methyl acetate, methanol, dimethyl ether and an organohalogen compound, and into a bottom fraction comprising water, small quantities of acetic acid and the catalyst, if the latter is not in a fixed bed, the residence time being so adjusted that the greater part of the acetic acid reacts with the methanol present to give methyl acetate,(c) separating the top fraction from D1, in a distillation column D2, into a top fraction comprising small quantities of methyl acetate, methanol, dimethyl ether and the organo-halogen compound, and a bottom fraction comprising methyl acetate and methanol, and recycling the top fraction to reactor R,(d) distilling off, via the top of distillation column D3, th
    Type: Grant
    Filed: January 7, 1982
    Date of Patent: June 12, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Rudolf Kummer, Volker Taglieber, Heinz-Walter Schneider
  • Patent number: 4448643
    Abstract: A process for isolating isobutene from C.sub.4 -hydrocarbon mixtures containing isobutene by reacting the mixture with a primary alcohol in the presence of an acid condensing agent, to form the tertiary ether, separating off the unconverted hydrocarbons and decomposing the tertiary ether in the presence of an acid catalyst at an elevated temperature, wherein a primary C.sub.3 - or C.sub.4 -alcohol is used and the temperature at which the reaction mixture leaves the etherification stage, in which the tertiary ether is formed, is lower than the mean temperature in the etherification stage.
    Type: Grant
    Filed: July 13, 1981
    Date of Patent: May 15, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Alfred Lindner, Klaus Volkamer, Ulrich Wagner
  • Patent number: 4444881
    Abstract: A process is provided for the recovery of organic acids from dilute aqueous solutions. The acid in the form of its calcium salt is treated with a tertiary amine carbonate and the resulting trialkylammonium salt of the acid is isolated and heated to give the acid plus a tertiary amine.
    Type: Grant
    Filed: June 27, 1983
    Date of Patent: April 24, 1984
    Assignee: CPC International Inc.
    Inventor: Branko Urbas
  • Patent number: 4412086
    Abstract: Ferric iron is removed from chlorinated hydrocarbons having less than 6 carbon atoms per molecule by intimately contacting the latter with an oil that comprises one or more hydrocarbons having at least 6 concatenated aliphatic carbon atoms per molecule. The hydrocarbon oil is present in an amount sufficient to interact with a major portion of the ferric iron. The resulting mixture of the chlorinated hydrocarbon stream and the hydrocarbon oil is heated simultaneously with the intimate contacting, and a precipitate is allowed to form. The chlorinated hydrocarbon stream is then separated from the hydrocarbon oil and from the precipitate, and the precipitate is subsequently separated from the hydrocarbon oil, which may be recycled and re-used.
    Type: Grant
    Filed: June 1, 1981
    Date of Patent: October 25, 1983
    Assignee: Vulcan Materials Company
    Inventors: William Q. Beard, Jr., Richard L. Wilson
  • Patent number: 4405717
    Abstract: A process is provided for the recovery of acetic acid from dilute aqueous solutions. The acid in the form of its calcium salt is treated with a tertiary amine carbonate and the resulting trialkylammonium acetate is isolated and heated to give the acetic acid plus a tertiary amine.
    Type: Grant
    Filed: October 26, 1981
    Date of Patent: September 20, 1983
    Assignee: CPC International Inc.
    Inventor: Branko Urbas
  • Patent number: 4404063
    Abstract: A method for the separation of indole by distilling an indole-containing reaction fluid obtained by the reaction of aniline with ethylene glycol or by the reaction of N-(.beta.-hydroxyethyl)aniline, which comprises bringing the reaction fluid into contact with a basic substance prior to and/or during the distillation. This method can prevent the deterioration of indole during the distillation procedure.
    Type: Grant
    Filed: September 24, 1982
    Date of Patent: September 13, 1983
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventor: Tadatoshi Honda
  • Patent number: 4365080
    Abstract: This invention provides an improved process for the separation and recovery of byproducts associated with the isolation of C.sub.4 -C.sub.6 dicarboxylic acids contained in a waste byproduct stream derived from an adipic acid manufacturing operation involving nitric acid oxidation of a cyclohexanone/cyclohexanol feedstream.The main byproducts which are recovered are high purity dimethyl succinate, dimethyl glutarate and dimethyl adipate.
    Type: Grant
    Filed: May 20, 1981
    Date of Patent: December 21, 1982
    Assignee: El Paso Products Company
    Inventor: Norbert F. Cywinski
  • 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: 4349417
    Abstract: Ethylene oxide and water are reacted in a reactor and the reaction product is subjected to distillation in a plurality of distillation columns, in the first columns water and components having a boiling point below that of monoethylene glycol and higher ethylene glycols, if any, being distilled off. To obtain extremely pure monoethylene glycol alkali metal compounds are added at a point between the reactor and the monoethylene glycol distillation column in an amount to adjust the pH of the product entering the latter column to a value of from 7 to 10. The monoethylene glycol obtained in this manner is especially pure and has very low UV absorption values. It is, therefore, especially suitable for the manufacture of polyester fibers.
    Type: Grant
    Filed: January 9, 1981
    Date of Patent: September 14, 1982
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Siegfried Rebsdat, Sigmund Mayer, Josef Alfranseder, Iwo Schaffelhofer
  • Patent number: 4340447
    Abstract: Pure acetone is recovered from a crude acetone vapor fraction removed overhead from a first column separating phenol and higher boilers as a bottom fraction from a cumene hydroperoxide cleavage reaction product by partially condensing the crude acetone fraction, returning the condensed portion of the crude acetone fraction to the first column as reflux, feeding the remaining portion as a vapor to an intermediate point in a second distillation column to which there is also fed continuously at a point above the acetone feedpoint a dilute aqueous solution of an alkali, removing from the base of the second column a residue fraction comprising compounds boiling above acetone, removing from a point in the second column intermediate; between the alkali feedpoint and the top of the column as a liquid sidedraw fraction pure acetone having a permanganate time (PT) greater than 4 hours, and removing from the top of the second column as a vapor fraction acetone having a PT less than that of the sidedraw fraction, condens
    Type: Grant
    Filed: May 27, 1981
    Date of Patent: July 20, 1982
    Assignee: BP Chemicals Limited
    Inventors: Robert G. Laverick, James M. Scotland
  • Patent number: 4334042
    Abstract: In the carbonylation of olefinic compounds in the presence of a cobalt carbonyl catalyst, the addition to the reaction system of a secondary phosphine oxide represented by the general formula ##STR1## wherein R.sup.1 and R.sup.2 are the same or different and each is substituted or unsubstituted hydrocarbon residue having not more than about 20 carbon atoms, in an amount of 0.2 to 20 moles per gram atom of the cobalt makes it possible to separate the reaction product from the reaction mixture by direct distillation without any such special operation for the catalyst separation as required in the conventional processes. The distillation residue which contains the catalyst can be recycled for the reuse thereof in the carbonylation.
    Type: Grant
    Filed: July 23, 1979
    Date of Patent: June 8, 1982
    Assignee: Kuraray Co. Ltd.
    Inventors: Mitsuo Matsumoto, Masuhiko Tamura
  • Patent number: 4328075
    Abstract: The present invention relates to a process for removing cyanides from a crude acetonitrile stream. Caustic and formaldehyde are added to an aqueous acetonitrile stream that contains cyanide. The formaldehyde "kills" the cyanides and provides a waste stream that can be conveniently disposed of.
    Type: Grant
    Filed: May 21, 1980
    Date of Patent: May 4, 1982
    Assignee: Standard Oil Company
    Inventors: William O. Fitzgibbons, Andrew J. Barko
  • Patent number: 4297456
    Abstract: This invention relates to a process for working up the distillation residue obtained in the commercial production of tolylene diisocyanate by grinding, optionally accompanied and/or followed by chemical modification reactions. The finely divided powder obtained may be used as a reactive filler in the production of a variety of plastics.
    Type: Grant
    Filed: July 17, 1980
    Date of Patent: October 27, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Artur Reischl, Kuno Wagner
  • Patent number: 4282071
    Abstract: Process for changing the volatile aluminum chloride complex contained in an ethylbenzene production stream into a non-volatile, aluminum chloride product of a nature such that the ethylbenzene in the stream can be separated from the aluminum chloride catalyst by flash distillation. Conversion of the volatile aluminum chloride complex to a non-volatile aluminum chloride product is accomplished by adding selected alcohols, aldehydes, or ketones to the ethylbenzene stream.
    Type: Grant
    Filed: April 25, 1977
    Date of Patent: August 4, 1981
    Assignee: The Dow Chemical Company
    Inventor: Fred A. Sherrod
  • Patent number: 4271315
    Abstract: This invention provides a process for improving the recovery of byproducts associated with the isolation of C.sub.4 -C.sub.6 dicarboxylic acids contained in a waste byproduct stream, derived from an adipic acid manufacturing operation wherein there is involved nitric acid oxidation of a cyclohexanone/cyclohexanol feedstream.The main byproducts which are isolated are high purity dimethyl succinate, dimethyl glutarate and dimethyl adipate. Monomethyl esters of these dicarboxylic acids are recovered and recycled in the process.
    Type: Grant
    Filed: November 15, 1979
    Date of Patent: June 2, 1981
    Assignee: El Paso Products Company
    Inventor: Norbert F. Cywinski
  • Patent number: 4260827
    Abstract: The invention is directed to a process for the purification of aqueous solutions of low molecular weight polyhydroxyl compounds containing calcium or lead compounds or mixtures thereof. Methanol and a precipitant for calcium and/or lead ions in a quantity equivalent to the ions to be removed are added to the solutions. The deposits thus formed are removed and the residual solutions are treated with a cation exchanger followed by distillation of the low-boiling fractions. The distillation sump which essentially contains the low molecular weight polyhydroxyl compounds is then treated with an anion exchanger.
    Type: Grant
    Filed: December 17, 1979
    Date of Patent: April 7, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Kurt Klinkmann, Raimund Wambach
  • Patent number: 4257851
    Abstract: A crude naphthoquinone produced by an oxidation of naphthalene is purified by a reduced pressure distillation of a crude 1,4-naphthoquinone having an acid content of less than 5 equivalent % calculated as monobasic acid and the crude naphthoquinone is preferably treated by an oxidation of oxidizable impurities.
    Type: Grant
    Filed: March 22, 1979
    Date of Patent: March 24, 1981
    Assignee: Kawasaki Kasei Chemicals Ltd.
    Inventors: Ryo Matsuura, Kazuaki Sakai, Tuneyasu Sato, Yorinobu Yamada, Kowzo Bandow
  • Patent number: 4243493
    Abstract: An improved petroleum distillation process in which methanol is added to the petroleum to be distilled and methanol/hydrocarbon azeotrope is recovered boiling at about 63.degree. C. which can be used as a fuel. The methanol can be derived from natural gas or another fossil fuel source. A methanol crude oil emulsion from a long distance pipeline can be distilled by this process without preliminary treatment.
    Type: Grant
    Filed: February 3, 1978
    Date of Patent: January 6, 1981
    Assignee: Mannesmannrohren-Werke A.G.
    Inventors: Kurt Gruber, Willi Keim, Klaus Hentschel
  • Patent number: 4232177
    Abstract: A method for conducting chemical reactions and fractionation of the reaction mixture comprising feeding reactants to a distillation column reactor into a feed zone and concurrently contracting the reactants with a fixed bed catalytic packing to concurrently carry out the reaction and fractionate the reaction mixture.For example, a method for preparing methyl tertiary butyl ether in high purity from a mixed feed stream of isobutene and normal butene comprising feeding the mixed feed stream to a distillation column reactor into a feed zone at the lower end of a distillation reaction zone, and methanol into the upper end of said distillation reaction zone, which is packed with a properly supported cationic ion exchange resin, contacting the C.sub.4 feed and methanol with the catalytic distillation packing to react methanol and isobutene, and concurrently fractionating the ether from the column below the catalytic zone and removing normal butene overhead above the catalytic zone.
    Type: Grant
    Filed: February 21, 1979
    Date of Patent: November 4, 1980
    Assignee: Chemical Research & Licensing Company
    Inventor: Lawrence A. Smith, Jr.
  • Patent number: 4229262
    Abstract: A process for recovering alkoxyketone compounds from mixtures of the alkoxyketone compound and the corresponding 1-alkoxy-2-alkanol compound by extractive distillation with diols, triols and polyols as extractants, wherein said mixtures contain an organic or inorganic base.
    Type: Grant
    Filed: May 4, 1979
    Date of Patent: October 21, 1980
    Assignee: Union Carbide Corporation
    Inventors: Denvil E. Reed, Richard C. Grimm
  • Patent number: 4190729
    Abstract: In the cobalt carbonyl-catalyzed carbonylation of methanol to ethanol, acetaldehyde and methyl acetate, a tertiary phosphine oxide is utilized as a stabilizer. Product is distilled from the reaction mixture and the cobalt-containing residue solution is recycled.
    Type: Grant
    Filed: September 19, 1977
    Date of Patent: February 26, 1980
    Assignee: Monsanto Company
    Inventor: Denis Forster
  • Patent number: 4170521
    Abstract: A method for purifying benzotriazole, tolyl-triazole or mixtures of the two is disclosed. The method includes the steps of vacuum distillation of crude triazole and collection of the condensate. The crude triazole contains color bodies, diazotizable impurities which are color body precursors, or both. The color of the distilled triazole is improved by adding to the crude triazole, prior to vacuum distillation, an amount of formaldehyde sufficient for reaction with an appreciable proportion of the color bodies, the color body precursors, or both.
    Type: Grant
    Filed: May 22, 1978
    Date of Patent: October 9, 1979
    Assignee: The Sherwin-Williams Company
    Inventor: Richard P. Carr
  • Patent number: 4168210
    Abstract: A method for reducing losses due to reactions between hydrogen halides and olefinically unsaturated organic compounds in the presence of transition metals which act as catalysts for hydrohalogenation in mixtures containing same by adding to said mixtures a compound selected from the class consisting of alkyl diketones. The present invention is of particular value in the separation of components of said mixtures by distillation, but may also be usefully employed in any operation in which these mixtures are maintained in the presence of said catalytic materials. The present method offers advantages over the prior art because of the relative low toxicity and flammability of diketones and the fact that no undesirable solids are formed to foul process equipment as with some known methods.
    Type: Grant
    Filed: March 25, 1977
    Date of Patent: September 18, 1979
    Assignee: The Dow Chemical Company
    Inventors: Theodore S. Boozalis, John B. Ivy
  • Patent number: 4142943
    Abstract: The decomposition of pentachlorophenol during distillation to remove impurities is markedly reduced by incorporating into the distilling molten pentachlorophenol a hydroxyl or polyhydroxyl containing organic compound having a boiling point above about 100.degree. C. in the presence or absence of water.
    Type: Grant
    Filed: September 23, 1974
    Date of Patent: March 6, 1979
    Assignee: The Dow Chemical Company
    Inventors: Erwin H. Kobel, deceased, Masao Yoshimine
  • Patent number: 4119497
    Abstract: The present invention refers to a process for the purification of acetonitrile from crude acetonitrile or mixtures containing the same, which comprises the following operations:(a) transformation of hydrogen cyanide and acrylonitrile into compounds of higher molecular weight,(b) removal of most of the water in an azeotropic distillation column, and(c) separation of acetonitrile from the compounds of higher molecular weight and residual water in rectifying columns.
    Type: Grant
    Filed: October 12, 1976
    Date of Patent: October 10, 1978
    Assignee: Instituto Mexicano del Petroleo
    Inventors: Felipe Ocampo, Francisco Meza, Francisco Aguirre
  • Patent number: 4115530
    Abstract: Process for the production of gaseous hydrogen chloride by extraction of dilute aqueous hydrochloric acid with amines.(a) The aqueous hydrochloric acid is extracted with an amine or with a mixture of an amine and an inert organic solvent which is immiscible with water and has a lower boiling point than the amine employed, the amines utilized being tertiary alkyl amines, tertiary aryl dialkyl amines, secondary arylalkyl amines, primary alkylaryl amines, or mixtures thereof, which contain 14-32 carbon atoms in the nitrogen-bound side chains, and among these at most one nitrogen-bound methyl group and at least one aliphatic residue containing at least 6 carbon atoms, and wherein the acid constant K.sub.a of the amine is smaller than 10.sup.-3.(b) An inert, water-immiscible organic solvent which has a lower boiling point than the amine employed is added to the extract, unless the solvent has already been added in stage (a).
    Type: Grant
    Filed: July 14, 1977
    Date of Patent: September 19, 1978
    Assignee: Chemische Werke Huls AG
    Inventors: Alfred Coenen, Kurt Kosswig, Gunter Prominski
  • Patent number: 4105688
    Abstract: Malonic acid dinitrile is prepared by reacting acetonitrile and cyanogen chloride in the gaseous phase at temperatures from 740.degree. to 780.degree. C. Temperatures from 750.degree. to 760.degree. C. with molar ratios of 1:1 to 1:5 of cyanogen chloride to acetonitrile are preferred. The crude mixture containing malonic acid dinitrile may be purified by conversion of the principal impurities to easily separable compounds by a Diels-Alder or selective hydrogenation reaction.
    Type: Grant
    Filed: April 26, 1971
    Date of Patent: August 8, 1978
    Assignee: Lonza, Ltd.
    Inventors: Urs Arni, Adriano Faucci, August Stocker
  • Patent number: 4082617
    Abstract: Recovery of the chemical components of a cellulosic organic solvent regenerating solution containing a dialkylacylamide, a lower aliphatic monohydric alcohol, a nitrite of the alcohol and nitric acid. The process comprises distilling the solution to remove the alcohol nitrite and alcohol, leaving the dialkylacylamide and nitric acid, recovering the alcohol, hydrolyzing to convert the alcohol nitrite to the alcohol and nitrous acid, neutralizing the nitric and nitrous acid with an alkali or alkaline earth metal oxide or hydroxide and distilling the solution to remove water and to separate and recover the remaining alcohol, the dialkylacylamide and the nitrate and nitrite salts. The nitrite and nitrate salts are converted by pyrolysis to nitrogen dioxide. The process results in substantially total recovery of the process chemicals.
    Type: Grant
    Filed: August 18, 1976
    Date of Patent: April 4, 1978
    Assignee: International Telephone and Telegraph Corporation
    Inventors: Norman A. Portnoy, David Paul Anderson
  • Patent number: 4065362
    Abstract: The present invention provides a process for purifying an organic isocyanate which comprises heating an organic isocyanate in admixture with a treating agent selected from the group consisting of a metal salt of mercaptobenzothiazol, a dithiocarbamic acid derivative, an alkyl-substituted phenol, a thio-bisphenol, and a triaryl phosphite at a temperature not lower than 100.degree. C and subsequently distilling the thusly treated mixture to recover a purified organic isocyanate.
    Type: Grant
    Filed: June 2, 1975
    Date of Patent: December 27, 1977
    Assignee: Sumitomo Bayer Urethane Co., Ltd.
    Inventors: Yushin Kataoka, Tetsuo Harada, Kenji Takagi
  • Patent number: 4065267
    Abstract: This invention relates to an improved apparatus for preparing alkylated urea or melamine formaldehyde resins from alcohols having a boiling point higher than water, which apparatus permits the return of substantially dry alcohol from the water distillation system to the reactor.The apparatus comprises a reactor connected to a fractionating column, having a rectifying section above a stripping section, at the junction of the rectifying section and the stripping section; a reboiler at the bottom of the fractionating column, which returns substantially dry alcohol to the reactor; a condenser which condenses the alcohol-water vapor mixture exiting the rectifying section of the column; and a separator device which separates the condensed mixture into an alcohol phase and a water phase, and from which the alcohol phase is returned to the top portion of the column.Use of the apparatus of the invention results in a substantial reduction in reaction times.
    Type: Grant
    Filed: September 13, 1976
    Date of Patent: December 27, 1977
    Assignee: PPG Industries, Inc.
    Inventors: Lawrence Ladage, Hilary E. Holste
  • Patent number: 4059492
    Abstract: Waste water resulting from the production of acrylonitrile by gas phase oxidation of propylene and ammonia with oxygen as washing water in the recovery section is purified by treating the waste water with 0.4 to 1 ton of steam per ton of waste water in a detoxification column attached to or following the separation column (for the separation of acetonitrile and acrylonitrile from the waste water in the acrylonitrile process) at a temperature from 100.degree. to 125.degree. C, at a pressure of 0 to 2 (gauge) atmospheres; separating the non-volatile resinous organic compounds from the thus treated waste water in an evaporator and using the vapors from the top of said evaporator to heat the said separation column and detoxification column; and optionally adding an organic amine to said distillation column or to said evaporator.
    Type: Grant
    Filed: May 3, 1976
    Date of Patent: November 22, 1977
    Assignees: Erdolchemie GmbH, Bayer Aktiengesellschaft
    Inventors: Arnold Hausweiler, Adolf Mayer, Feliks Bitners
  • Patent number: 4045506
    Abstract: A process for separating mixtures of close boiling alkenes and alkanes which employs catalytic dealkylation of alkylphenols.
    Type: Grant
    Filed: April 1, 1976
    Date of Patent: August 30, 1977
    Assignee: Chevron Research Company
    Inventors: Milutin Simic, William A. Sweeney
  • Patent number: 4039428
    Abstract: A process is provided for producing ultra-pure propionic acid, i.e., acid containing less than 20 parts by weight of iodine per billion parts by weight of acid, wherein crude acid containing water and iodine contaminants is distilled in a single distillation zone and no waste streams requiring treatment or disposal are obtained.
    Type: Grant
    Filed: January 2, 1976
    Date of Patent: August 2, 1977
    Assignee: Monsanto Company
    Inventor: YuWen Wei
  • Patent number: 4039395
    Abstract: A process is provided for purification and drying of acetic acid containing water and methyl iodide and hydrogen iodide as contaminants. The process comprises distillation in a two-zone system wherein the major part of the methyl iodide and hydrogen iodide and some water are removed as overhead and bottoms, respectively, from the first zone; a stream from the middle section of the first zone is introduced into a second zone into which there is also introduced a stream of methanol; and a stream of dry purified acid is recovered from the bottom of said second zone. The process provides both for the recovery of the iodine components and the methanol added for re-use in production of additional acetic acid by the reaction of methanol and/or methyl acetate with carbon monoxide in contact with a catalyst system formed on mixing of a rhodium or iridium component and an iodine component in the presence of carbon monoxide.
    Type: Grant
    Filed: August 11, 1975
    Date of Patent: August 2, 1977
    Assignee: Monsanto Company
    Inventor: Roy T. Eby
  • Patent number: 4033617
    Abstract: Crude ethylene oxide present in the dilute aqueous solution resulting from the extraction with an aqueous solvent of ethylene oxide from the gaseous stream obtained by catalytic oxidation of ethylene is purified by desorption, liquefaction, distillation in a fractionating column and final desorption treatment to remove absorbed non-condensable gases. The fractionating column is heated by condensation of the water vapor evolved during desorption and a liquid stream of ethylene oxide rich in acetaldehyde is discharged from the bottom, treated to convert a fraction of said acetaldehyde into high-boiling products, distilled to remove the latter as bottoms and returned to the fractionating column.
    Type: Grant
    Filed: July 8, 1976
    Date of Patent: July 5, 1977
    Assignee: Societa' Italiana Resine S.I.R. S.p.A.
    Inventors: Gioacchino Cocuzza, Gianni Torreggiani, Michele Sfregola
  • Patent number: 4028195
    Abstract: Ethylene glycol or 1,2-propylene glycol contained in mixtures with lower carboxylate esters of the glycol are separated from such mixtures by fractional distillation of the mixtures with the addition to the lower portion of the distillation zone of aqueous formic acid and/or acetic acid.
    Type: Grant
    Filed: September 12, 1975
    Date of Patent: June 7, 1977
    Assignee: Halcon International, Inc.
    Inventors: Mitchell Becker, Charles C. Yang
  • Patent number: 4018657
    Abstract: A process for separating mixtures of close boiling, high-molecular weight alkenes and alkanes which employs phenoxide-catalyzed alkyl displacement.
    Type: Grant
    Filed: April 1, 1976
    Date of Patent: April 19, 1977
    Assignee: Chevron Research Company
    Inventors: William A. Sweeney, Milutin Simic
  • Patent number: 4017421
    Abstract: Aqueous solutions and suspensions of solid particles, even those containing less than one percent of organic materials, may be combusted with air, oxygen, or their mixtures in a process which provides for preheating in countercurrent batches of the raw original liquid by either open (direct contact) or closed (heat transfer surface) condensation of steam generated by multiple flash evaporations which cool earlier batches of hot liquid after the wet combustion. Excess heat may often be withdrawn from the process for power generation or other use as high pressure steam, with or without combustion gases and other non-condensibles. No pumps are necessary, liquid batches are pressurized by steam generated in the flash evaporations for which only one pressure vessel is required instead of the many in the continuous processes.
    Type: Grant
    Filed: December 16, 1975
    Date of Patent: April 12, 1977
    Inventor: Donald F. Othmer