Organic Acid Patents (Class 203/15)
  • Patent number: 11377792
    Abstract: Provided herein are compositions and processes concerning efficient downstream processing of products derived from organic acids pretreatment of plant materials.
    Type: Grant
    Filed: October 26, 2021
    Date of Patent: July 5, 2022
    Assignee: Pierson Capital Environmental (Beijing) Limited
    Inventor: Feng Ling
  • Patent number: 11299447
    Abstract: A method for manufacturing carboxylic acid that includes the following steps is provided. First, subjecting an aqueous mixture, including carboxylic acid and at least 5 wt. % dissolved magnesium chloride, to a forward extraction step using a first organic liquid, including an organic solvent, the organic solvent being selected from the group of C5+ ketones, thereby obtaining an organic carboxylic acid solution and an aqueous waste liquid including magnesium chloride. Second, subjecting the organic carboxylic acid solution to a back extraction step wherein the carboxylic acid is extracted from the organic carboxylic acid solution into an aqueous liquid, thereby obtaining an aqueous carboxylic acid solution and a second organic liquid. Third, subjecting the aqueous waste liquid including magnesium chloride derived from the forward extraction to a thermal decomposition step at a temperature of at least 300° C., thereby decomposing the magnesium chloride to magnesium oxide and HCl.
    Type: Grant
    Filed: December 21, 2012
    Date of Patent: April 12, 2022
    Assignee: PURAC BIOCHEM B.V.
    Inventors: André Banier De Haan, Jan Van Krieken, Tanja Ðekic {hacek over (Z)}ivkovic
  • Patent number: 10519084
    Abstract: Provided herein are methods and systems for converting natural gas, and specifically methane, into higher-value oxycarbon products, such as methanol, methyl formate, and formic acid. The natural gas is introduced into an aqueous solution with hydroxyl radicals and reacted in ambient conditions to form the desired products in the presence of a metal catalyst. The methods described herein overcome the “over-activation” dilemma of prior art methods that lead to the formation of undesirable carbon oxide compounds. Methods and apparatus for forming hydrogen peroxide via electrolysis and for forming hydroxyl radicals from the hydrogen peroxide via reaction with ferrous ions are also provided.
    Type: Grant
    Filed: October 20, 2017
    Date of Patent: December 31, 2019
    Assignees: Wichita State University, Farshad Houtaham
    Inventors: Shuang Gu, Farshad Houtaham
  • Patent number: 10407373
    Abstract: The invention relates to a process to separate formic acid from methyltetrahydrofuran (MTHF) said process comprising subjecting a composition comprising formic acid and MTHF to distillation, characterized in that the process comprises adding water to said distillation. This allows for cost-efficient recovery and recycling of MTHF, for example in process to produce and recover formic acid from a biomass hydrolysate.
    Type: Grant
    Filed: May 15, 2014
    Date of Patent: September 10, 2019
    Assignee: GEORGIA-PACIFIC LLC
    Inventors: Gerardus Wilhelmus Adrianus Hangx, Gerardus Johannes Paulus Krooshof, Arie De Rijke
  • Patent number: 10252970
    Abstract: The invention relates to a process for dehydrating aqueous 3-hydroxypropionic acid to acrylic acid in the liquid phase, wherein aqueous acrylic acid is removed continuously from the liquid phase and the aqueous 3-hydroxypropionic acid and/or the liquid phase have a high content of oligomeric 3-hydroxypropionic acid.
    Type: Grant
    Filed: August 21, 2014
    Date of Patent: April 9, 2019
    Assignee: BASF SE
    Inventors: Tim Blaschke, Ortmund Lang, Nicolai Tonio Wörz, Christian Raith, Marco Hartmann, Marta Zajaczkowski-Fischer
  • Patent number: 10125076
    Abstract: A process comprising subjecting a composition comprising an alpha- or beta-hydroxycarboxylic acid, water, an extraction solvent, and an acid catalyst to extractive dehydration to form an unsaturated carboxylic acid product.
    Type: Grant
    Filed: June 25, 2015
    Date of Patent: November 13, 2018
    Assignee: Dow Global Technologies LLC
    Inventors: Timothy C. Frank, Vishesh H. Shah, Paul A. Larsen
  • Patent number: 10059651
    Abstract: The azeotrope, or near azeotrope, of methanol and MMA is separated via extractive distillation using an extractive distillation solvent comprising cyclohexanone.
    Type: Grant
    Filed: October 7, 2015
    Date of Patent: August 28, 2018
    Assignees: Dow Global Technologies LLC, Rohm and Haas Company
    Inventors: John G. Pendergast, Jr., Jacinto Lopez-Toledo, William G. Worley, Stacy W. Hoy, IV, Jacob M. Crosthwaite
  • Patent number: 10029976
    Abstract: This invention relates to a process for the purification of acrylic acid from a mixture containing acrylic acid and acetic acid, comprising the following steps: extraction of the mixture containing acrylic acid and acetic acid with an extractant stream, whereby a raffinate stream and an extract stream are obtained, distillation of the extract stream, whereby an acrylic acid stream and a return stream are obtained, wherein the return stream contains acetic acid and is recirculated into the extraction. Furthermore, the invention may include a plant for carrying out this process.
    Type: Grant
    Filed: June 16, 2015
    Date of Patent: July 24, 2018
    Assignee: L'Air Liquide Societe Anonyme Pour L'Etude Et L'Exploitation Des Procedes Georges Claude
    Inventors: Thomas Gutermuth, Markus Kreich, Frank Castillo-Welter
  • Patent number: 9428437
    Abstract: The present invention describes a process for preparing alpha-beta-unsaturated carboxylic acids by dehydration of hydroxycarboxylic or alkoxycarboxylic acids which are substituted in the alpha position, in particular 2-hydroxyisobutyric acid, while avoiding accumulation of by-products and additives.
    Type: Grant
    Filed: April 28, 2014
    Date of Patent: August 30, 2016
    Assignee: EVONIK ROEHM GmbH
    Inventors: Alexander May, Steffen Krill, Joerg Becker, Willi Ploesser, Marcel Treskow, Martin Koestner
  • Patent number: 9353244
    Abstract: Mixture of succinic esters, which is characterized in that the alkyl radical has a proportion of alkyl components having less than 9 carbon atoms of not more than 15% by mass, the alkyl radical has a proportion of alkyl components having more than 9 carbon atoms of not more than 25% by mass and the proportion of 3,5,5-trimethylhexyl radicals is not more than 5 mol % and the proportion of linear n-nonyl radicals is not more than 15 mol %.
    Type: Grant
    Filed: February 27, 2012
    Date of Patent: May 31, 2016
    Assignee: Evonik Degussa GmbH
    Inventors: Hinnerk Gordon Becker, Michael Graβ
  • Patent number: 8864950
    Abstract: A process for producing an acrylate product. The process comprises the step of providing a crude product stream comprising the acrylate product and an alkylenating agent. The process further comprises the step of separating at least a portion of the crude product stream to form an alkylenating agent stream and an intermediate product stream. The alkylenating agent stream comprises at least 1 wt % alkylenating agent and the intermediate product stream comprises acrylate product. The separating is performed in at least one column at an operating pressure ranging from 40 kPa to 80 kPa.
    Type: Grant
    Filed: January 6, 2012
    Date of Patent: October 21, 2014
    Assignee: Celanese International Corporation
    Inventors: Craig Peterson, Josefina Chapman, Jonathan Gallacher
  • Publication number: 20140166469
    Abstract: Disclosed is a process for the separation of water from a liquid phase medium containing an aliphatic carboxylic acid using azeotropic distillation in the presence of an entrainer. The entrainer, water, and organics are subsequently separated, wherein the entrainer is recycled back to the azeotropic distillation column and organics recycled back to the oxidation reactor.
    Type: Application
    Filed: March 14, 2013
    Publication date: June 19, 2014
    Inventor: Alan Macpherson URE
  • Patent number: 8586779
    Abstract: The present invention relates in general terms to a process for preparing alkyl methacrylates, comprising as steps: providing an acetone cyanohydrin by a process according to one of the preceding claims; contacting the acetone cyanohydrin with an inorganic acid to obtain a methacrylamide; contacting the methacrylamide with an alcohol in the presence of an inorganic acid in a reactor to obtain an alkyl methacrylate; continuously discharging at least a portion of the alkyl methacrylate from the reactor into a distillation column as a vapor stream; the discharge being effected by feeding a discharge stream comprising steam into the reactor, to an apparatus for preparing alkyl methacrylates, to a process for preparing polymers based at least partly on alkyl methacrylates, to the use of the alkyl methacrylates obtainable by the process according to the invention in chemical products, and to chemical products based on alkyl methacrylates obtainable by the process according to the invention.
    Type: Grant
    Filed: August 31, 2007
    Date of Patent: November 19, 2013
    Assignee: Evonik Röhm GmbH
    Inventors: Udo Gropp, Robert Weber, Thomas Schaefer, Andreas Perl, Rudolf Sing, Thomas Mertz
  • Patent number: 8246790
    Abstract: The present invention provides a (meth)acrylic acid collecting method for collecting a (meth)acrylic acid from a mixed gas that includes an organic byproduct, a steam, and a (meth)acrylic acid that are generated in a production reaction of the (meth)acrylic acid, which includes the steps of a) contacting the mixed gas that includes the organic byproduct, the steam, and the (meth)acrylic acid with a (meth)acrylic acid absorption solvent to obtain a gas that includes the organic byproduct and the steam and the (meth)acrylic acid containing solution while the gas and the (meth)acrylic acid containing solution are separated from each other; b) contacting the gas that includes the organic byproduct and the steam that are obtained in the step a with the organic byproduct absorption solvent to obtain the gas that includes the steam and the organic byproduct containing solution while the gas and the organic byproduct containing solution are separated from each other; c) supplying the gas that includes the steam that
    Type: Grant
    Filed: October 23, 2008
    Date of Patent: August 21, 2012
    Assignee: LG Chem, Ltd.
    Inventors: Se-Won Baek, Kyoung-Su Ha, Sung-Kyoo Park, Jun-Seok Ko, Dong-Hyun Woo, Young-Bae Kim, Jung-Hoon Chang
  • Patent number: 8192589
    Abstract: The invention relates to a method and a device for the purification of an aqueous solution of an organic acid having a boiling point at atmospheric pressure of less than 450° C., which further has approximately 275 g carboxylate ions/l or less, preferably 250 g carboxylate ions/l or less, and preferably less than 1% by weight ionic impurities, calculated on the basis of the total solution. In particular, the invention relates to a method and a device for the continuous purification and concentration, on an industrial scale, of an aqueous solution of an organic acid having a boiling point at atmospheric pressure of less than 450° C. According to the method, this solution is subjected to two or more distillation steps, the first distillation step being carried out at a temperature of from 80° to 150° C. and a pressure of from 50 to 250 mbar, and the second distillation step being carried out at a temperature of from 80° to 200° C. and a pressure of from 0.01 to 50 mbar.
    Type: Grant
    Filed: December 20, 2010
    Date of Patent: June 5, 2012
    Assignee: Purac Biochem B.V.
    Inventors: Hendrik Martinus Winkelaar, Jan Van Breugel, Margarita Camprubi Vilá, José Maria Vidal Lancis
  • Patent number: 8128787
    Abstract: Processes for removing water from organic solvents, such as ethanol. The processes include distillation in two columns operated at sequentially higher pressure, followed by treatment of the overhead vapor by one or two membrane separation steps.
    Type: Grant
    Filed: August 27, 2008
    Date of Patent: March 6, 2012
    Assignee: Nitto Denko Corporation
    Inventors: Nicholas P. Wynn, Yu Huang, Masakatsu Urairi, Richard W Baker
  • Patent number: 8114255
    Abstract: Processes for removing water from organic solvents, such as ethanol. The processes include distillation in two columns operated at sequentially higher pressure, followed by treatment of the overhead vapor by one or two membrane separation steps.
    Type: Grant
    Filed: August 27, 2008
    Date of Patent: February 14, 2012
    Assignee: Membrane Technology & Research, Inc.
    Inventors: Leland M Vane, Franklin R Alvarez, Yu Huang, Richard W Baker
  • Patent number: 7922876
    Abstract: In a method for recovering acid from an aqueous etching mixture containing HF, HNO3, H2SiF6 and HNO2 which has been used for purifying polycrystalline silicon, the used etching mixture is distilled progressively so that approximately from 20 to 50 wt. % of the mixture is distilled off as dilute acid containing more than 90 wt. % of the silicon dissolved as hexafluorosilicic acid in a first fraction, and the water contained in the used etching mixture having been reduced by approximately 10-30 wt. %, this water-depleted mixture is then concentrated by evaporation to a residue of about 1 to 5 wt. % of the initial amount of used etching mixture during which a second fraction is distilled off, and the residue is disposed of.
    Type: Grant
    Filed: August 21, 2007
    Date of Patent: April 12, 2011
    Assignee: Wacker Chemie AG
    Inventors: Hanns Wochner, Christian Gossmann, Wolfgang Stoiber
  • Patent number: 7569722
    Abstract: A process is disclosed that relates to the removal of impurities, specifically benzoic acid, from a mother liquor produced in the synthesis of carboxylic acid, typically terephthalic acid.
    Type: Grant
    Filed: August 11, 2005
    Date of Patent: August 4, 2009
    Assignee: Eastman Chemical Company
    Inventors: Robert Lin, Philip Edward Gibson, Kenny Randolph Parker
  • Patent number: 7435318
    Abstract: The invention relates to a process for separating close-boiling, homo- and heteroazeotropic mixtures by using ionic liquids. Due to the selectivity and unusual combination of properties of the ionic liquids the process is superior to conventional extractive rectification from the point of view of costs and energy.
    Type: Grant
    Filed: March 14, 2002
    Date of Patent: October 14, 2008
    Assignee: BASF Aktiengesellschaft
    Inventors: Wolfgang Arlt, Matthias Seiler, Carsten Jork, Thomas Schneider
  • Patent number: 7410556
    Abstract: The invention relates to a method and a device for the purification of an aqueous solution of an organic acid having a boiling point at atmospheric pressure of less than 450° C., which further has approximately 275 g carboxylate ions/1 or less, preferably 250 g carboxylate ions/1 or less, and preferably less than 1% by weight ionic impurities, calculated on the basis of the total solution. In particular, the invention relates to a method and a device for the continuous purification and concentration, on an industrial scale, of an aqueous solution of an organic acid having a boiling point at atmospheric pressure of less than 450° C. According to the method, this solution is subjected to two or more distillation steps, the first distillation step being carried out at a temperature of from 80° to 150° C. and a pressure of from 50 to 250 mbar, and the second distillation step being carried out at a temperature of from 80° to 200° C. and a pressure of from 0.01 to 50 mbar.
    Type: Grant
    Filed: November 27, 2000
    Date of Patent: August 12, 2008
    Assignee: Purac Biochem B.V.
    Inventors: Hendrik Martinus Winkelaar, Jan Van Breugel, Margarita Camprubi Vila, Jose Maria Vidal Lancis
  • Patent number: 7241365
    Abstract: The invention relates to an apparatus and a process for the preparation of anhydrous or substantially anhydrous formic acid. This apparatus is constructed partly or entirely of substantially zirconium-free materials. The extractant employed is a liquid of the general formula I where the radicals R1 and R2 are alkyl, cycloalkyl, aryl or aralkyl groups, or R1 and R2 jointly, together with the N atom, form a heterocyclic 5- or 6-membered ring, and only one of the radicals is an aryl group, and where R3 is hydrogen or a C1–C4-alkyl group. The apparatus has a synthesis reactor (6), a hydrolysis reactor (1), three distillation devices (2,4,5) and an extraction device (3).
    Type: Grant
    Filed: January 24, 2001
    Date of Patent: July 10, 2007
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz Auer, Bernd Bessling, Hans Hammer, Hans Hasse, Friedrich Sauer, Maximilian Vicari, Gerhard Wagner, Till Adrian
  • Patent number: 6793777
    Abstract: The invention relates to a method for separating and purifying an aqueous mixture that mainly consists of acetic acid, formic acid and high-boiling substances by extraction with a solvent in a cyclic process. The inventive method is characterized in that the flow of raffinate is fed to a solvent stripping column (11) with the major part of the water in order to remove the water from the cycle. The flow of extract is fed to a solvent recovery distillation column (8). In a first step, a mixture (A) that consists of water and solvent, is separated by overhead distillation. A mixture (B) that consists of acetic acid, formic acid and high-boiling substances is separated via a sump. Once the formic acid is removed in a column (29), mixture (B) is separated in an acetic acid distillation column to give pure acetic acid and high-boiling substances.
    Type: Grant
    Filed: December 5, 2001
    Date of Patent: September 21, 2004
    Assignee: Consortium für Elektrochemische Industrie GmbH
    Inventors: Christoph Rüdinger, Harald Herbert Voit, Michael Hallmann, Mehmet Günaltay, Barbara Reil, Hans-Jürgen Eberle
  • Patent number: 6695952
    Abstract: A method for the separation and purification of an aqueous mixture of main components, namely acetic acid and formic acid and non-volatiles by extraction, uses a solvent in a circulatory system. A raffinate stream is mixed with the larger proportion of water from a solvent stripper column (11) for the removal of water. The extraction stream is introduced into a solvent distillation column (8), from which in a first step involving the use of a mixture (A) containing a larger proportion of the solvent is separated out via a header and a mixture (B) of formic acid, water and solvent is separated out via a side offtake and a mixture (C) of acetic acid and non-volatiles is also separated out. A mixture (B) is introduced into a formic acid distillation column (4) for further processing, and a mixture (C) is introduced into an acetic acid distillation column (5), and purified acetic acid is subsequently isolated in the acetic acid distillation column (5) from the header.
    Type: Grant
    Filed: January 9, 2002
    Date of Patent: February 24, 2004
    Assignee: Consortium fur Elektrochemische Industrie GmbH
    Inventors: Christoph Rüdinger, Harald Herbert Voit, Michael Hallmann, Mehmet Günaltay, Barbara Geborene Neé Reil Wild, Hans Jürgen Eberle
  • Publication number: 20030150705
    Abstract: A method of recovering acrylic acid from a mixture comprising acrylic acid, water and acetic acid is disclosed, which includes:
    Type: Application
    Filed: December 30, 2002
    Publication date: August 14, 2003
    Inventors: Sanjeev D. Deshpande, Tao Wang, Olan Stanley Fruchey, Roger L. Roundy, Nathan K. Powell, Rafael G. Morales, Joseph E. Goins
  • Patent number: 6179966
    Abstract: The present invention concerns a method for producing acrylic acid which involves subjecting an acrylic acid-containing aqueous solution obtained by catalytic vapor phase oxidation of propylene and/or acrolein to evaporation whereby an acrylic acid-containing vapor is obtained; and subjecting the acrylic acid-containing vapor to azeotropic dehydration. The present invention offers a number of advantages including a reduce amount of polymer that may adhere to the surface of an azeotropic dehydration column, a low-blowing separation column or an in a high-boiling separation column in a plant for producing acrylic acid. Consequently, the production plant can be operated for a long time without stopping operations.
    Type: Grant
    Filed: November 17, 1998
    Date of Patent: January 30, 2001
    Assignee: Sumitomo Chemical Company, Ltd.
    Inventors: Toyomitsu Shimizu, Osamu Moriya, Kunihiko Shigematsu, Ryuji Matsushita
  • Patent number: 5980696
    Abstract: An improved process for preparing an aromatic dicarboxylic acid wherein the improvement resides in dehydrating and recovering solvent from a feed stream having from 20% to 40% by weight water via azeotropic distillation with organic phase reflux using an entrainer selected from isobutyl acetate, n-propyl acetate or an entrainer with a boiling point between isobutyl acetate and n-propyl acetate.
    Type: Grant
    Filed: February 5, 1997
    Date of Patent: November 9, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: William David Parten, Alan Macpherson Ure
  • Patent number: 5976324
    Abstract: A process as been found for the removal of water from reaction mixtures of acids or acid anhydrides or of aqueous alkali metal hydroxide solutions with alcohols using vapor permeation/pervaporation at the boiling point of the reaction mixture, which includes initially introducing the lowest-boiling educt in less than the stoichiometric amount, based on the other particular educt, together with this other educt, heating the reaction mixture to the boiling point and freeing the vapor mixture, which is formed from the boiling reaction mixture and includes chiefly water and the lowest-boiling component, from water on a membrane, recycling the vapor mixture which has been freed from water into the reaction mixture and topping up the reaction mixture with the lowest-boiling educt in the course of the reaction.
    Type: Grant
    Filed: October 7, 1997
    Date of Patent: November 2, 1999
    Assignee: Bayer Aktiengesellschaft
    Inventors: Andreas Groschl, Adolf Winkler, Josef Bremen
  • Patent number: 5873981
    Abstract: A is a process for removing water from an alkanesulfonic acid such as methanesulfonic acid or ethanesulfonic acid by mixing an azeotropic excess of a phenolic compound with water and the alkanesulfonic acid, then boiling off substantially all of the water, and leaving as a remnant substantially all the alkanesulfonic acid and some of the phenol. This process is particularly useful for recycling an alkanesulfonic acid for a reaction which requires the phenolic compound as one of the reagents. One such reaction is the alkanesulfonic acid catalyzed condensation reaction of a phenolic compound with an .alpha.haloketone to form a chlorinated intermediate of a dihydroxy-.alpha.-alkylstilbene such as 4,4'-dihydroxy-.alpha.-alkylstilbene (DHAMS).
    Type: Grant
    Filed: December 26, 1996
    Date of Patent: February 23, 1999
    Assignee: The Dow Chemical Company
    Inventors: Son T. Nguyen, Louis L. Walker, Katherine S. Clement
  • Patent number: 5624566
    Abstract: A method for recovering carboxylic acids from a dilute aqueous solution thereof having a concentration below about ten percent (10%) by weight, which includes passing the dilute acid solution through a reverse osmosis separator, thereby producing a permeate substantially free of acid and a retentate having an acid concentration above about ten percent (10%) by weight. The retentate is contacted with a liquid extractant for acids to produce an acid-rich extractate and an acid-free raffinate. The acid is then recovered from the acid-rich extractate.
    Type: Grant
    Filed: June 7, 1995
    Date of Patent: April 29, 1997
    Assignee: Glitsch, Inc.
    Inventors: Randa W. Wytcherley, Joseph C. Gentry, Ronald G. Gualy
  • Patent number: 5603813
    Abstract: Vinyl formate containing formic acid, acetaldehyde and water following synthesis is separated from formic acid and water in a first distillation stage and from acetaldehyde in a second stage to give pure vinyl formate.
    Type: Grant
    Filed: August 2, 1995
    Date of Patent: February 18, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Ruhl, Marc Heider, Jochem Henkelmann, Ralf-Thomas Rahn, Harald Rust
  • Patent number: 5492625
    Abstract: A method for recovering carboxylic acids from a dilute aqueous solution thereof having a concentration below about ten percent (10%) by weight, which includes passing the dilute acid solution through a reverse osmosis separator, thereby producing a permeate substantially free of acid and a retentate having an acid concentration above about ten percent (10%) by weight. The retentate is contacted with a liquid extractant for acids to produce an acid-rich extractate and an acid-free raffinate. The acid is then recovered from the acid-rich extractate.
    Type: Grant
    Filed: April 7, 1994
    Date of Patent: February 20, 1996
    Assignee: Glitsch, Inc.
    Inventors: Randa W. Wytcherley, Joseph C. Gentry, Ronald G. Gualy
  • Patent number: 5399751
    Abstract: Disclosed is a method for recovering carboxylic acids having from one to ten carbon atoms, and particularly formic acid, acetic acid and mixtures of formic and acetic acids, from aqueous solutions, in which the aqueous solution is contacted with solvent consisting essentially of mixed trialkylphosphine oxides in counter-current liquid-liquid extraction flow in a contacting step to thereby transfer the acids from the aqueous solution to the solvent, thus producing a raffinate relatively low in acid content and a rich solvent. The rich solvent is preferably dehydrated to separate water therefrom and yield a dehydrated rich solvent. The dehydrated rich solvent then has the acids stripped from it and the resulting lean solvent is then returned to the liquid-liquid extraction step, while the separated acids are split into their constituent components in a distillation operation.
    Type: Grant
    Filed: November 5, 1993
    Date of Patent: March 21, 1995
    Assignee: Glitsch, Inc.
    Inventors: Joseph C. Gentry, John C. McIntyre, Timothy L. Holmes, Ronald G. Gualy
  • Patent number: 5384413
    Abstract: The present invention relates to a process for the preparation of tetrafluorophthalic acid and/or tetrafluorophthalic anhydride by reacting a compound of the formula ##STR1## in which X is a radical ##STR2## which is optionally mono- or polysubstituted on the aromatic nucleus by fluorine and/or chlorine and/or alkyl groups having 1 to 4 carbon atoms, or is a radical ##STR3## in which R.sub.1, R.sub.2 and R.sub.3 are as defined, with water, and subsequently removing the water still present by azeotropic distillation or extracting the tetrafluorophthalic acid and/or its anhydride with a water-insoluble solvent or solvent mixture.
    Type: Grant
    Filed: July 12, 1993
    Date of Patent: January 24, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ralf Pfirmann, Theodor Papenfuhs
  • Patent number: 5312935
    Abstract: Fluorinated carboxylic acids which do not have the required purity for use as emulsifier in the polymerization of fluorinated monomers can, if necessary after prior de-watering, be treated with oxidants, whereupon the isolation of the pure product is carried out by crystallisation or, preferably, by distillation.
    Type: Grant
    Filed: April 21, 1993
    Date of Patent: May 17, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ludwig Mayer, Gernot Lohr
  • Patent number: 5296639
    Abstract: A process for purification of adipic acid during crystallization by modifying the crystal morphology to decrease incorporation of impurities through the introduction of an effective amount of an additive to the crystallizing solution.
    Type: Grant
    Filed: December 18, 1992
    Date of Patent: March 22, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Diana L. Klug, Johannus H. Van Mil
  • Patent number: 5206433
    Abstract: Anhydrous or substantially anhydrous formic acid is prepared by hydrolyzing methyl formate in the presence of a formamide and then obtaining the formic acid from the hydrolysis mixture by distillation, by a method in which the hydrolysis is carried out in the presence of 0.5-3 moles, per mole of methyl formate, of a water-soluble formamide of the general formula I ##STR1## where R.sup.1 and R.sup.2 are each alkyl or together form an alkylene group, giving a 5-membered to 7-membered ring, with the proviso that the sum of the carbon atoms in R.sup.1 and R.sup.2 is 5 or 6 and, in the case of an alkylene group, a carbon atom which is not directly bonded to the N atom can be replaced by an oxygen atom.
    Type: Grant
    Filed: May 9, 1985
    Date of Patent: April 27, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz Hohenschutz, Johannes E. Schmidt, Hans Kiefer
  • Patent number: 5173156
    Abstract: Formic acid cannot be completely removed from formic acid--water mixtures by distillation because of the presence of the maximum azeotrope. Formic acid can be readily removed from mixtures containing it and water by using extractive distillation in which the extractive distillation agent is cyclohexanone, isophorone or a mixture of these with certain organic compounds. Typical examples of effective agents are cyclohexanone; isophorone; cyclohexanone and neodecanoic acid; isophorone and diisobutyl ketone.
    Type: Grant
    Filed: December 9, 1991
    Date of Patent: December 22, 1992
    Assignee: Lloyd Berg
    Inventors: Lloyd Berg, Kraig M. Wendt, Rudolph J. Szabados
  • 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: 5104492
    Abstract: Carboxylic acids are recovered from wet organic solutions by reducing the solutions' water content thus causing the acids to precipitate as recoverable crystals.
    Type: Grant
    Filed: July 11, 1990
    Date of Patent: April 14, 1992
    Assignee: The Regents of the University of California
    Inventors: C. Judson King, John Starr
  • Patent number: 5059327
    Abstract: A preparation membrane for pervaporation which comprises a crosslinked reaction mixture of a polyvinyl alcohol or polyvinyl alcohol copolymer and a polystyrene sulfonic acid or polystyrene sulfonic acid copolymer. A method for separating a mixture of water and an organic compound by using the membrane is also disclosed.
    Type: Grant
    Filed: August 25, 1987
    Date of Patent: October 22, 1991
    Assignee: Director-General, Agency of Industrial Science and Technology
    Inventor: Shinsuke Takegami
  • Patent number: 5006205
    Abstract: Formic acid cannot be completely removed from formic acid and water mixtures by distillation because of the presence of the maximum azeotrope. Formic acid can be readily removed from formic acid - water mixtures by extractive distillation in which the extractive agent is a mono carboxylic acid mixed with certain high boiling organic compounds. Examples of effective agents are: hexanoic acid and butyl benzoate; octanoic acid and nitrobenzene; heptanoic acid, benzyl benzoate and pelargonic acid.
    Type: Grant
    Filed: January 17, 1989
    Date of Patent: April 9, 1991
    Assignee: Lloyd Berg
    Inventors: Lloyd Berg, Kraig M. Wendt, Rudolph J. Szabados
  • Patent number: 4978430
    Abstract: An improved method for dehydration and concentration of an aqueous solution containing an organic compound is disclosed. The solution is evaporated to produce a gaseous mixture comprising an organic compound vapor and a water vapor. The water vapor is selectively removed from the gaseous mixture by permeation through an aromatic polyimide gas separation membrane while the gaseous mixture being kept in contact with a surface on one side of the gas separation membrane at a temperature of 70.degree. C. or higher to obtain a gaseous mixture comprising the organic compound vapor and a reduced amount of a water vapor.
    Type: Grant
    Filed: July 24, 1989
    Date of Patent: December 18, 1990
    Assignee: UBE Industries, Ltd.
    Inventors: Kanji Nakagawa, Yoshio Asakura, Shigeru Yamamoto, Kohei Ninomiya, Masayuki Kinouchi
  • Patent number: 4938846
    Abstract: A process for the removal of water from a lower alkanesulfonic acid-water mixture by causing the mixture to run down the internal walls of two vertical evaporator columns operated in series, is disclosed herein.
    Type: Grant
    Filed: December 8, 1986
    Date of Patent: July 3, 1990
    Assignee: Atochem, North America, Inc.
    Inventors: Perry D. Comstock, Karen M. Keys
  • Patent number: 4935100
    Abstract: Formic acid cannot be completely removed from formic acid and water mixtures by distillation because of the presence of the maximum azeotrope. Formic acid can be readily removed from formic acid - water mixtures by extractive distillation in which the extractive agent is a benzoic acid derivative mixed with certain higher boiling organic compounds. Examples of effective agents are: o-toluic acid and heptanoic acid; 2-benzoylbenzoic acid and methyl salicylate; p-hydroxybenzoic acid, pelargonic acid and 2-hydroxyacetophenone.
    Type: Grant
    Filed: May 30, 1989
    Date of Patent: June 19, 1990
    Assignee: Lloyd Berg
    Inventors: Lloyd Berg, Kraig M. Wendt, Rudolph J. Szabados
  • Patent number: 4898644
    Abstract: A process for removing volatile acids from aqueous solutions which involves steam stripping a volatile acid from an aqueous solution and contacting the vaporized acid with a reactable cation to form a salt of the acid. A preferred embodiment of apparatus comprises an elongated distillation column having therein a plurality of zones or stages wherein the volatile acid in the aqueous feed stream is vaporized by steam and then the vaporized acid is carried by the steam into a salt formation zone or stage to react with a reactable cation to form a salt of the acid.
    Type: Grant
    Filed: May 2, 1988
    Date of Patent: February 6, 1990
    Assignee: QO Chemicals, Inc.
    Inventor: Wendell E. Van Horn
  • Patent number: 4877490
    Abstract: Formic acid cannot be completely removed from formic acid and water mixtures by distillation because of the presence of the maximum azeotrope. Formic acid can be readily removed from formic acid--water mixtures by extractive distillation in which extractive agent is a dicarboxylic acid mixed with certain high boiling organic compounds. Examples of effective agents are: itaconic acid and diethylene glycol diethyl ether; azelaic acid, heptanoic acid and 2-hydroxyacetophenone.
    Type: Grant
    Filed: January 23, 1989
    Date of Patent: October 31, 1989
    Assignee: Lloyd Berg
    Inventors: Lloyd Berg, Kraig M. Wendt, Rudolph J. Szabados
  • Patent number: 4838998
    Abstract: The amount of water required to effect efficient separation of a mixture of sulfuric acid and carboxylic acids by distillation, is reduced, by diluting the mixture while in the distillation column in a prescribed manner with sufficient water to provide a water:sulfuric acid mole ratio of about 1:1. The heat generated by the internal dilution reduces the energy requirement of the column. Feeding the dilution water to the column below the feed mixture is a key element of the process.
    Type: Grant
    Filed: December 4, 1987
    Date of Patent: June 13, 1989
    Assignee: Rohm and Haas Company
    Inventors: Philip D. T. Davies, Lawrence S. Kirch
  • Patent number: 4786370
    Abstract: Formic acid cannot be completely removed from formic acid and water mixtures by distillation because of the presence of the maximum azeotrope. Formic acid can be readily removed from formic acid - water mixtures by extractive distillation in which the extractive agent is ethylene carbonate or propylene carbonate, either alone or mixed with certain high boiling organic compounds. Examples of effective agents are ethylene carbonate and heptanoic acid; propylene carbonate, benzoic acid and isophorone; propylene carbonate, heptanoic acid and 2-hydroxyacetophenone.
    Type: Grant
    Filed: January 4, 1988
    Date of Patent: November 22, 1988
    Inventor: Lloyd Berg
  • 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