Formic Acid Per Se Or Salt Thereof Patents (Class 562/609)
  • Patent number: 6555078
    Abstract: The present invention provides an inexpensive process for the preparation of lithium salts of formula LiX having a desired or required level of purity using lithium chloride and lithium sulfate. In the process of the invention, a lithium salt selected from lithium chloride, lithium sulfate, and combinations thereof is reacted with NaX or KX in a aqueous, semiaqueous, or organic solution and the precipitated salts are removed to obtain the LiX solution of desired purity. Preferably, a semiaqueous solution containing water and an organic solvent is used at some point in the reaction. The process of the invention eliminates the use of highly acidic materials and thus reduces the cost of raw materials and the need for specialized equipment.
    Type: Grant
    Filed: September 16, 1997
    Date of Patent: April 29, 2003
    Assignee: FMC Corporation
    Inventor: Vijay Chandrakant Mehta
  • Publication number: 20030050506
    Abstract: The invention relates to a process for the preparation of anhydrous or substantially anhydrous formic acid.
    Type: Application
    Filed: July 18, 2002
    Publication date: March 13, 2003
    Inventors: Heinz Auer, Bernd Bessling, Hans Hammer, Hans Hasse, Friedrich Sauer, Maximilian Vicari, Gerhard Wagner, Till Adrian
  • Publication number: 20030036664
    Abstract: The invention relates to a process for obtaining anhydrous or substantially anhydrous formic acid, in which firstly aqueous formic acid is prepared by hydrolysis of methyl formate and is freed from water in the subsequent work-up. The process has the special feature that steam, which is employed for the hydrolysis of methyl formate and for heating a distillation column serving for work-up, is also used as stripping steam for waste-water stripping. The stripped waste water is produced during work-up.
    Type: Application
    Filed: July 18, 2002
    Publication date: February 20, 2003
    Inventors: Heinz Auer, Bernd Bessling, Hans Hammer, Hans Hasse, Friedrich Sauer, Maximilian Vicari, Till Adrian
  • Publication number: 20030032841
    Abstract: A process for the solid-phase synthesis of salts of organic acids in a granular, free-flowing, and dust-free form particularly suited for use as animal feed additives. A liquid organic acid is applied to an inert, absorbent carrier. A solid base is then added during stirring. The acid is slowly released from the carrier preventing the fast reactions that lead to the formation of clumps. The exothermic reaction releases heat which assists in reducing the moisture content of the product.
    Type: Application
    Filed: July 30, 2001
    Publication date: February 13, 2003
    Inventor: Stefaan Van Dyck
  • Publication number: 20030018216
    Abstract: The invention relates to a process for obtaining anhydrous or substantially anhydrous formic acid, in which firstly aqueous formic acid is produced by hydrolysis of methyl formate, with the methanol content in the methyl formate having been reduced in advance. The process according to the invention has the special feature that—before the hydrolysis of the methyl formate—the methanol content of the methanol-containing methyl formate is reduced in a distillation column, this distillation column simultaneously being employed for other separation functions during work-up of the formic acid.
    Type: Application
    Filed: July 18, 2002
    Publication date: January 23, 2003
    Inventors: Heinz Auer, Bernd Bessling, Hans Hammer, Hans Hasse, Friedrich Sauer, Maximilian Vicari, Till Adrian
  • Publication number: 20030009057
    Abstract: The invention relates to a process for obtaining anhydrous or substantially anhydrous formic acid in which, during the work-up, a compound of the general formula I 1
    Type: Application
    Filed: July 18, 2002
    Publication date: January 9, 2003
    Inventors: Heinz Auer, Bernd Bessling, Hans Hammer, Hans Hasse, Friedrich Sauer, Maximilian Vicari, Gerhard Wagner, Till Adrian
  • Publication number: 20030009062
    Abstract: 1
    Type: Application
    Filed: July 12, 2002
    Publication date: January 9, 2003
    Inventors: Frank Dobert, Alexander Klausener, Paul Wagner
  • Patent number: 6492551
    Abstract: A method for manufacturing alkali metal or alkaline-earth metal formate, starting from a formate anion comprises at least the following sequential steps: A) conversion of a solid anion exchanger to formate form by feeding into it a solution containing a formate anion, B) exchanging the formate anion in the anion exchanger for a replacing anion by feeding into it an alkali metal or alkaline-earth metal salt solution of this replacing anion, C) recovering the alkali metal or alkaline-earth metal formate solution eluted from the anion exchanger during the exchange of the formate anion. The anion exchanger is converted to formate form by feeding into it a sodium formate solution, a formic acid solution or a solution which contains both sodium formate and formic acid. The method can be used for production of potassium formate or calcium formate.
    Type: Grant
    Filed: April 16, 2001
    Date of Patent: December 10, 2002
    Assignee: Kemira Chemicals OY
    Inventors: Erkki Paatero, Marko Lahtinen, Kari Saari, Pekka Vapaaoksa
  • Patent number: 6429333
    Abstract: In a method for preparing formic acid, methyl formate is prepared with methanol as a reactant.
    Type: Grant
    Filed: June 19, 2001
    Date of Patent: August 6, 2002
    Assignee: Kemira Chemicals Oy
    Inventors: Kari Saari, Esko Tirronen, Antti Vuori, Marko Lahtinen
  • Patent number: 6258980
    Abstract: There is described a process for the production of a substantially anhydrous salt of an organic acid which comprises reacting a basic compound of a metal with the appropriate organic acid, removing a substantial proportion of water present so as to produce the salt or its hydrate as a liquid phase and then dissolving the liquid phase in a non-aqueous solvent.
    Type: Grant
    Filed: June 27, 1994
    Date of Patent: July 10, 2001
    Assignee: Contracts Chemicals Ltd.
    Inventor: David Anthony Jones
  • Patent number: 6137005
    Abstract: A method for manufacture of products containing disalts of formic acid. Potassium hydroxide, carbonate, bicarbonate or formate, sodium hydroxide, carbonate, bicarbonate for formate, cesium hydroxide, carbonate, bicarbonate or formate or ammonium formate or ammonia is mixed with formic acid at 40-100.degree. C., the mixture is cooled and centrifuged. The filtrate containing acid salt is collected. The filter cake is transported to a drier/mixer where other disalts, calcium formate and/or a desiccant can be added.
    Type: Grant
    Filed: February 26, 1998
    Date of Patent: October 24, 2000
    Assignee: Norsk Hydro ASA
    Inventor: Leif Hj.o slashed.rnevik
  • Patent number: 6127573
    Abstract: The present invention relates to a TEMPO-catalyzed oxidation of primary alcohols, RCH.sub.2 OH to corresponding carboxylic acids, RCOOH in the presence of catalytic in the presence of catalytic amount of NaClO and stoichiometric amount of NaClO.sub.2 as an oxidant.
    Type: Grant
    Filed: April 1, 1999
    Date of Patent: October 3, 2000
    Assignee: Merck & Co., Inc.
    Inventors: Jing Li, Zhiguo Song, David M. Tschaen, Mangzu Zhao
  • Patent number: 6015535
    Abstract: Disclosed is a method for producing a predetermined cesium compound. The method comprises treating a cesium-containing material with a suitable reagent to dissolve at least a portion of the cesium contained in the material and form a slurry; adding a base comprising slaked lime or calcium carbonate and an acid containing the anion of the predetermined cesium compound to the slurry comprising the dissolved cesium; and separating the predetermined cesium compound.
    Type: Grant
    Filed: May 19, 1997
    Date of Patent: January 18, 2000
    Assignee: Cabot Corporation
    Inventors: Patrick M. Brown, Michael C. Northrup, Bart F. Bakke
  • Patent number: 5891921
    Abstract: Wood preservative systems comprising (a) a biocidal effective amount of (i) at least one di C.sub.8 -C.sub.12 alkyl quaternary ammonium carboxylate having the formula ##STR1## wherein R.sup.1 and R.sup.2 are a C.sub.8 -C.sub.12 alkyl group; R.sup.3 is a substituted or unsubstituted, interrupted or uninterrupted C.sub.1 -C.sub.100 group; l and q independently are 1, 2 or 3 and (l) (q) is 1, 2, or 3; and n is 0 or an integer from 1 to 50; (ii) at least one di C.sub.8 -C.sub.12 alkyl quaternary ammonium borate having the formula ##STR2## wherein R.sup.1 and R.sup.2 are defined as above, and a is 2 or 3, but when a is 2, b is 0 or 1, and when a is 3, b is 0, 1, or 2; or (iii) a combination of (i) and (ii); and (b) a solvent are provided. These carboxylate quats as well as carboxylate quats wherein R.sup.1 is a C.sub.1 -C.sub.20 alkyl or aryl-substituted alkyl group and R.sup.2 is a C.sub.8 -C.sub.20 alkyl group are preferably prepared by an indirect or a direct synthesis.
    Type: Grant
    Filed: April 18, 1996
    Date of Patent: April 6, 1999
    Assignee: Lonza Inc.
    Inventor: Leigh E. Walker
  • Patent number: 5831120
    Abstract: In the process for the production of acetic acid by carbonylation of methanol and/or a reactive derivative thereof the water concentration in the liquid reaction composition is maintained at a steady-state concentration by at least one process step selected from the group consisting of (i) recovery and disposing of water from at least part of the overhead process stream from the light ends column and (ii) replacing at least a portion of the methanol feed with a component selected from the group consisting of methyl acetate, dimethyl ether, acetic anhydride and mixtures thereof. The recovered aqueous effluent from this and other processes may be purified of carboxylic acid by reactive distillation with at least one C.sub.1 to C.sub.3 alcohol.
    Type: Grant
    Filed: November 19, 1996
    Date of Patent: November 3, 1998
    Inventors: Derrick John Watson, Bruce Leo Williams, Michael James Muskett, Stephen James Smith, Chuc Tu Nguyen, Larry Irvin Baker
  • Patent number: 5639910
    Abstract: Formic acid or derivatives thereof are produced from non-toxic carbon dioxide in the supercritical state, using it as raw materials, without using solvents, and at a high efficiency owing to a high reaction velocity, by reacting said carbon dioxide and an active hydrogen group-containing compound.
    Type: Grant
    Filed: November 4, 1994
    Date of Patent: June 17, 1997
    Assignees: Research Development Corporation of Japan, Takao Ikariya
    Inventors: Takao Ikariya, Philip Gregory Jessop, Ryoji Noyori
  • Patent number: 5633402
    Abstract: Formic acid is difficult to separate from acetic acid by conventional distillation or rectification because of the proximity of their boiling points. Formic acid can be readily separated from acetic acid by using azeotropic distillation. Effective agents are acetonitrile and isopropyl acetate.
    Type: Grant
    Filed: September 1, 1995
    Date of Patent: May 27, 1997
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5605669
    Abstract: This invention relates to the preparation of cesium salts from cesium-aluminum-alum in a process in which the cesium-aluminum-alum is reacted in a single vessel in the presence of water with calcium hydroxide in an amount which is equimolar to the amount of aluminum and with a readily water-soluble calcium salt in an amount which is equimolar to the amount of cesium and the precipitated aluminum hydroxide and the precipitated calcium sulfate are separated by filtration or centrifugation.
    Type: Grant
    Filed: November 24, 1995
    Date of Patent: February 25, 1997
    Assignee: Metallgesellschaft Aktiengesellschaft
    Inventors: Hartmut Hofmann, Klaus K obele, Horst Prinz, Bernd Phillipp, Gerd Harms, Alexander Schiedt, Ulrike Hecktor
  • Patent number: 5599979
    Abstract: Formic acid is difficult to separate from acetic acid by conventional distillation or rectification because of the close proximity of their boiling points. Formic acid can be readily separated from acetic acid by using extractive distillation. Effective agents are propionic acid, butyric acid, valeric acid and 2-ethyl hexanoic acid.
    Type: Grant
    Filed: September 8, 1995
    Date of Patent: February 4, 1997
    Assignee: Lloyd Berg
    Inventor: Lloyd Berg
  • Patent number: 5516406
    Abstract: A method of purifying the oxidate product formed by the liquid phase oxidation of C.sub.4 -C.sub.8 paraffinic hydrocarbons comprises adding a strong acid catalyst to the oxidate product to catalyze the break down of Michael addition products of unsaturated carbonyls and carboxylic acids so that the carbonyls can be distilled off during the initial stages of purification.
    Type: Grant
    Filed: December 15, 1994
    Date of Patent: May 14, 1996
    Assignee: Hoechst Celanese Corporation
    Inventors: Nicole G. Wallace, Kenneth A. Windhorst
  • Patent number: 5475158
    Abstract: A process for the preparation of cycloalkanols by the hydrolysis of cycloalkyl C.sub.1 -C.sub.4 fatty acid esters, which comprises the following steps:a) reaction of cycloalkyl C.sub.1 -C.sub.4 fatty acid esters with water at a temperature of from 30.degree. to 250.degree. in the liquid phase yielding a reaction mixture consisting of cycloalkyl C.sub.1 -C.sub.4 fatty acid esters, cycloalkanol, C.sub.1 -C.sub.4 fatty acids, and water.b) separation of the reaction mixture obtained in stage a) at a temperature of from 0.degree. to 200.degree. C. into a top phase consisting substantially of cycloalkanol and cycloalkyl C.sub.1 -C.sub.4 fatty acid esters and a bottom phase consisting substantially of water and C.sub.1 -C.sub.4 fatty acids.c) separation of cycloalkanol from the top phase obtained in stage b) by distillation and recycling unconverted cycloalkyl C.sub.1 -C.sub.4 fatty acid esters to stage a).
    Type: Grant
    Filed: December 1, 1993
    Date of Patent: December 12, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Thomas Krug, Rolf Fischer, Rolf Pinkos
  • Patent number: 5411725
    Abstract: The present invention relates to a process for the continuous conversion of one hydroxylamine salt to another hydroxylamine salt, said process involving a countercurrent liquid-liquid extraction followed by a countercurrent liquid-liquid re-extraction. Characteristically, the extractant is used in the extraction step in the salified form and in the acid form.
    Type: Grant
    Filed: October 18, 1993
    Date of Patent: May 2, 1995
    Assignee: Societe Generale Pour les Techniques Nouvelles, SGN
    Inventors: Dominique Pareau, Andre Chesne, Gerard Durand, Michel DeRubercy
  • Patent number: 5376293
    Abstract: Improved deicer compositions containing crystalline double salts formed from mixtures of relatively low molecular weight carboxylic acids (for example, mixtures of formic acid and acetic acid) are provided. The deicer compositions are generally prepared by neutralizing an aqueous mixture containing at least two carboxylic acids or salts thereof, adjusting the pH to between about 7 and about 10, and drying the aqueous mixture to obtain a double salt crystalline product. Double salts containing sodium cations and double salts containing sodium cations and at least one cation selected from the group consisting of potassium, calcium, and magnesium provide effective deicing compositions which are environmentally safer than conventional deicing compositions.
    Type: Grant
    Filed: September 9, 1993
    Date of Patent: December 27, 1994
    Assignee: State of South Dakota as represented by the Department of Transportation
    Inventor: Daniel P. Johnston
  • Patent number: 5373023
    Abstract: The invention provides compounds which are tetrahydronaphthalene derivatives of the formula (I) ##STR1## wherein R.sub.1 represents a halogen atom, a cyano group, a nitro group, an unbranched (C.sub.1 -C.sub.6) alkoxy group, a (C.sub.1 -C.sub.6 cycloalkyl) (C.sub.1 -C.sub.2 alkoxy) group or an aryl (C.sub.1 -C.sub.2 alkoxy) group,R.sub.2 represents a (C.sub.1 -C.sub.4) alkyl group, an aryl group optionally substituted with at least one methoxy group, a pyridyl group or a benzodioxanyl group,R.sub.3 represents a hydrogen atom or a (C.sub.1 -C.sub.2) alkyl group, and n=0 to 3, or are addition salts with pharmaceutically acceptable acids. The compounds of the invention have anti-ischaemic activity.
    Type: Grant
    Filed: August 4, 1993
    Date of Patent: December 13, 1994
    Assignee: SYNTHELABO
    Inventors: Paul Howard Williams, Christian Hoornaert, Jean Claude Muller
  • Patent number: 5334759
    Abstract: A process for the preparation of formic acid by the reaction of carbon monoxide with water at temperatures of from 100.degree. to 250.degree. C. and absolute from 100 to 350 bar, in which tertiary amines of the general formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3 individually denote C.sub.1 -C.sub.14 alkyl, C.sub.3 -C.sub.8 cycloalkyl, aryl, and C.sub.7 -C.sub.16 aralkyl or together denote a 1,4-alkylene group or 1,5-alkylene group optionally mono- to tetra-substituted by C.sub.1 -C.sub.4 alkyl, provided that the total number of carbon atoms in R.sup.1, R.sup.2, and R.sup.3 is from 3 to 40,are added to the reaction mixture.
    Type: Grant
    Filed: August 17, 1993
    Date of Patent: August 2, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Ferdinand Lippert, Arthur Hoehn
  • Patent number: 5294740
    Abstract: A process for preparing formic acid by thermal cleavage of quaternary ammonium formates of the general formula I ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are C.sub.1 - to C.sub.14 -alkyl, C.sub.3 - to C.sub.8 -cycloalkyl, aryl or C.sub.7 - to C.sub.16 -aralkyl, or together are 1,4- or 1,5-alkylene which is unsubstituted or substituted one to four times by C.sub.1 -to C.sub.4 -alkyl, with the proviso that the sum of the carbon atoms of R.sup.1, R.sup.2 and R.sup.3 in the quaternary ammonium formates I is 7 to 40,comprises carrying out the cleavage in the presence of secondary formamides of the general formula II ##STR2## where R.sup.4 and R.sup.5 are C.sub.2 - to C.sub.10 -alkyl, C.sub.3 - to C.sub.8 -cycloalkyl, aryl or C.sub.7 - to C.sub.16 -aralkyl, or together are 1,4- or 1,5-alkylene which is unsubstituted or substituted one to four times by C.sub.1 - to C.sub.4 -alkyl,which formamides boil 30.degree. to 150.degree. C. lower than the tertiary amine of the general formula III ##STR3## where R.sup.1, R.
    Type: Grant
    Filed: March 31, 1993
    Date of Patent: March 15, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans Kiefer, Leopold Hupfer, Ferdinand Lippert
  • Patent number: 5288904
    Abstract: A process for the decomposition of trichloroacetic acid (TCAA) to form chlorides, carbonates and formates is disclosed. The process comprises treating TCAA with 6 or more equivalents of a metal hydroxide at a temperature above 60.degree. C.
    Type: Grant
    Filed: May 4, 1993
    Date of Patent: February 22, 1994
    Assignee: Schering Corporation
    Inventors: Maurice Fitzgerald, Eithne Cantwell
  • Patent number: 5275702
    Abstract: The present invention discloses a method to separate each component from a mixed solution of organic solvents obtained during the production of .alpha.-L-aspartyl-L-phenylalanine methyl ester, which is useful as a sweetener, namely, a mixed solution of acetic acid and toluene or a mixed solution of acetic acid, toluene and formic acid, recovering each component with a high recovery ratio with as small number of operations as possible. The method rationalizes the process and is highly valuable in practical use.
    Type: Grant
    Filed: August 12, 1992
    Date of Patent: January 4, 1994
    Assignee: Ajinomoto Co., Inc.
    Inventors: Takehiko Kataoka, Haruo Kawasaki, Harutoshi Ohura, Yoshinobu Uchida, Akihiko Yasaki, Shinichi Kishimoto
  • Patent number: 5264086
    Abstract: Formic acid difficult to separate from acetic acid by conventional distillation or rectification because of the close proximity of their boiling points. Formic acid can be readily separated from acetic acid by using azeotropic distillation. Effective agents are cyclopentane and tetrachloroethylene.
    Type: Grant
    Filed: January 29, 1993
    Date of Patent: November 23, 1993
    Assignee: Lloyd Berg
    Inventors: Lloyd Berg, Randi W. Wytcherley
  • Patent number: 5239117
    Abstract: Oxidation/reduction processes catalyzed by soluble rhodium complexes of the type (L.sub.4or5 Rh)Z.sup.- wherein each L is selected from a group consisting essentially of monophosphines, diphosphines, olefins and coordinating solvents with the proviso that at least one L is a phosphine and Z is a weakly coordinating anion. In one embodiment, formic acid is produced by the hydrogenation of carbon dioxide. In another embodiment oxygen/carbon dioxide mixtures are used to oxidize organic compounds (ethers, amines, olefins) with coproduction of formic acid. In a third embodiment, these organic compounds are selectively oxidized by oxygen alone, without the coproduction of formic acid.
    Type: Grant
    Filed: September 18, 1991
    Date of Patent: August 24, 1993
    Assignee: Board of Regents of the University of Oklahoma
    Inventors: Kenneth M. Nicholas, Jing-Cherng Tsai
  • Patent number: 5232558
    Abstract: 4-Methyl-2-pentanone cannot be easily separated from formic acid by distillation because of the closeness of their boiling points. 4-Methyl-2-pentanone can be readily removed from formic acid by extractive distillation. Typical effective agents are dimethylsulfoxide (DMSO) and 2-undecanone; DMSO and octanoic acid; DMSO and hexyl acetate.
    Type: Grant
    Filed: October 8, 1992
    Date of Patent: August 3, 1993
    Assignee: Lloyd Berg
    Inventors: Lloyd Berg, Marc W. Paffhausen
  • Patent number: 5228956
    Abstract: 3-Pentanone cannot be completely removed from 3-pentanone and formic acid mixtures by distillation because of the presence of the maximum azeotrope. 3-Pentanone can be readily removed from 3-pentanone-formic acid mixtures by extractive distillation in which the extractive agent is cyclopentanone, either alone or admixed with certain high boiling organic compounds. Examples of effective agents are cyclopentanone; cyclopentanone and 2-methoxyethyl ether; cyclopentanone, adiponitrile and octanoic acid.
    Type: Grant
    Filed: October 2, 1992
    Date of Patent: July 20, 1993
    Assignee: Lloyd Berg
    Inventors: Lloyd Berg, Rudolph J. Szabados
  • Patent number: 5227029
    Abstract: Formic acid cannot be easily removed from formic acid-acetic acid mixtures by distillation because of the closeness of their boiling points. Formic acid can be readily removed from mixtures containing it and acetic acid by extractive distillation. Typical effective agents are 2-nitrotoluene, 1-nitropropane and m-nitrobenzoic acid.
    Type: Grant
    Filed: January 29, 1993
    Date of Patent: July 13, 1993
    Assignee: Lloyd Berg
    Inventors: Lloyd Berg, Randi W. Wytcherley
  • 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: 5190619
    Abstract: 3-Methyl-2-butanone cannot be separated from formic acid by distillation because of the presence of the maximum boiling azeotrope. 3-Methyl-2-butanone can be readily removed from formic acid by extractive distillation using dimethylsulfoxide (DMSO). Typical effective agents are: DMSO and heptanoic acid; DMSO, octanoic acid and butyl benzoate.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: March 2, 1993
    Assignee: Lloyd Berg
    Inventors: Lloyd Berg, George Bentu
  • Patent number: 5189216
    Abstract: A process for the isolation of a carboxylic acid of the general formula (I)R.sup.1 --COOH (I),in which R.sup.1 denotes hydrogen, methyl, ethyl, or vinyl, from a dilute aqueous solution thereof by extraction with a secondary amide of the general formula (II) ##STR1## in which R.sup.1 has the meanings stated, and R.sup.2 and R.sup.3 are independently of each other C.sub.1 -C.sub.8 -alkyl, C.sub.3 -C.sub.8 -cycloalkyl, C.sub.4 -C.sub.20 -cycloalkylalkyl, aryl, C.sub.7 -C.sub.20 -aralkyl, or R.sup.2 and R.sup.3 together form a 1,4- or 1,5-alkylene group which may be mono- to penta-substituted by C.sub.1 -C.sub.4 -alkyl, wherein the losses of secondary amide (II) are compensated by the addition of the corresponding amine of the general formula (III) ##STR2## in which R.sup.2 and R.sup.3 have the meanings stated above.
    Type: Grant
    Filed: July 16, 1991
    Date of Patent: February 23, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Hans Kiefer, Werner Reutemann
  • 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: 5047583
    Abstract: A carboxylic acid of formula RCO.sub.2 H, for example acetic acid, is prepared from a formate ester of formula HCO.sub.2 R, for example methyl formate, by heating the ester at elevated temperature with an iridium catalyst, a halide promoter and a strong acid. The strong acid is one having a pKa of not greater than 0 in aqueous media for example a sulphonic acid. Addition of the strong acid to the reaction mixture causes an increase in the rate of conversion of formate ester to carboxylic acid.
    Type: Grant
    Filed: July 13, 1984
    Date of Patent: September 10, 1991
    Assignee: BP Chemicals Limited
    Inventor: Peter S. Williams
  • Patent number: 5019652
    Abstract: An improved catlayst and method for the oxyhydrochlorination of methane is disclosed. The catalyst includes a pyrogenic porous support on which is layered as active material, cobalt chloride in major proportion, and minor proportions of an alkali metal chloride and of a rare earth chloride. On contact of the catalyst with a gas flow of methane, HC1 and oxygen, more than 60% of the methane is converted and of that converted more than 40% occurs as monochloromethane. Advantageously, the monochloromethane can be used to produce gasoline boiling range hydrocarbons with the recycle of HCl for further reaction. This catalyst is also of value for the production of formic acid as are analogous catalysts with lead, silver or nickel chlorides substituted for the cobalt chloride.
    Type: Grant
    Filed: April 30, 1990
    Date of Patent: May 28, 1991
    Assignee: The United States as represented by the United States Department of Energy
    Inventors: Charles E. Taylor, Richard P. Noceti
  • 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: 4994151
    Abstract: 4-Methyl-2-pentanone cannot be easily separated from formic acid by distillation because of the closeness of their boiling points. 4-Methyl-2-pentanone can be readily removed from formic acid by extractive distillation using dimethylamides. Typical effective agents are dimethylformamide; dimethylacetamide and acetyl salicyclic acid; dimethylacetamide, heptanoic acid and methyl benzoate.
    Type: Grant
    Filed: July 14, 1989
    Date of Patent: February 19, 1991
    Assignee: Lloyd Berg
    Inventors: Lloyd Berg, George Bentu
  • 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: 4957595
    Abstract: 3-Methyl-2-butanone cannot be separated from formic acid by distillation because of the presence of the maximum boiling azotrope. 3-Methol-2-butanoe can be readily removed from formic acid by extractive distillation using sulfolane. Typical effective agents are: sulfolane and ethylene glycol diacetate; sulfolane, m-toluic acid and anisole.
    Type: Grant
    Filed: November 7, 1989
    Date of Patent: September 18, 1990
    Assignee: Lloyd Berg
    Inventors: Lloyd Berg, George Bentu
  • Patent number: 4948471
    Abstract: 4-Methyl-2-pentanone cannot be easily separated from formic acid or acetic acid by distillation because of the closeness of their boiling points. 4-Methyl-2-pentanone can be readily removed from formic acid or acetic acid by extractive distillation. Typical effective agents are sulfolane; sulfolane and heptanoic acid; sulfolane, azelaic acid and ethylene glycol diacetate.
    Type: Grant
    Filed: August 1, 1989
    Date of Patent: August 14, 1990
    Assignee: Lloyd Berg
    Inventors: Lloyd Berg, George Bentu
  • Patent number: 4948469
    Abstract: Dioxane cannot be completely removed from dioxane and formic acid mixtures by distillation because of the presence of the maximum azeotrope. Dioxane can be readily removed from dioxane - formic acid mixtures by extractive distillation in which the extractive agent is dimethylformamide, dimethylacetamide or these with certain high boiling organic compounds.
    Type: Grant
    Filed: December 5, 1988
    Date of Patent: August 14, 1990
    Assignee: Lloyd Berg
    Inventors: Lloyd Berg, Richard R. Rall
  • 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: 4909907
    Abstract: Formic acid cannot be easily removed from acetic acid by distillation because of the closeness of their vapor pressures. Formic acid can be readily removed from acetic acid by extractive distillation. Typical extractive distillation agents are acetyl salicylic acid and butyl benzoate; acetyl salicylic acid and ethylene carbonate.
    Type: Grant
    Filed: January 17, 1989
    Date of Patent: March 20, 1990
    Assignee: Hoechst Celanese Chemical Co.
    Inventor: Lloyd Berg
  • Patent number: 4902828
    Abstract: Aqueous glyoxylic acid solutions, essentially free of other acids, are recovered from aqueous solutions which still contain other acids, by a method in which the aqueous solution is mixed with an organic nitrogen compound at as high as 50.degree. C., the phases are separated, and the glyoxylic acid is extracted from the organic phase with water, at a higher temperature.
    Type: Grant
    Filed: October 18, 1984
    Date of Patent: February 20, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Wickenhaeuser, Bernd Heida, Fritz Graf, Leopold Hupfer
  • Patent number: 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: 4894482
    Abstract: A process is provided for removing water from a mixture of hydrogen fluoride (HF), a carboxylic acid, e.g., acetic acid, and water by extractive distillation in the presence of a Lewis base as solvent, which does not azeotrope with water, forms bonds with the HF and carboxylic acid which can be broken by heat and has a boiling point at atmospheric pressure at least about 20.degree. C. above that of the carboxylic acid, e.g., N-methyl-2-pyrrolidone, and taking off an overhead vapor comprising a major proportion of the water in said mixture. The extractive distillation may be advantageously integrated in an overall process with the production of an aromatic ketone, e.g., 4-hydroxyacetophone, by the Friedel-Crafts acylation of an aromatic compound, e.g., phenol, with the carboxylic acid, using HF as catalyst, to produce a product mixture comprising the aromatic ketone, HF, carboxylic acid and water, and the removal of aromatic ketone from the product mixture by means of a solvent assisted distillation.
    Type: Grant
    Filed: December 6, 1988
    Date of Patent: January 16, 1990
    Assignee: Hoechst Celanese Corporation
    Inventors: Daniel D. Lindley, Carl D. Murphy