Formic Acid Per Se Or Salt Thereof Patents (Class 562/609)
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Patent number: 6555078Abstract: 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: GrantFiled: September 16, 1997Date of Patent: April 29, 2003Assignee: FMC CorporationInventor: Vijay Chandrakant Mehta
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Publication number: 20030050506Abstract: The invention relates to a process for the preparation of anhydrous or substantially anhydrous formic acid.Type: ApplicationFiled: July 18, 2002Publication date: March 13, 2003Inventors: Heinz Auer, Bernd Bessling, Hans Hammer, Hans Hasse, Friedrich Sauer, Maximilian Vicari, Gerhard Wagner, Till Adrian
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Publication number: 20030036664Abstract: 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: ApplicationFiled: July 18, 2002Publication date: February 20, 2003Inventors: Heinz Auer, Bernd Bessling, Hans Hammer, Hans Hasse, Friedrich Sauer, Maximilian Vicari, Till Adrian
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Publication number: 20030032841Abstract: 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: ApplicationFiled: July 30, 2001Publication date: February 13, 2003Inventor: Stefaan Van Dyck
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Publication number: 20030018216Abstract: 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: ApplicationFiled: July 18, 2002Publication date: January 23, 2003Inventors: Heinz Auer, Bernd Bessling, Hans Hammer, Hans Hasse, Friedrich Sauer, Maximilian Vicari, Till Adrian
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Publication number: 20030009057Abstract: 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 1Type: ApplicationFiled: July 18, 2002Publication date: January 9, 2003Inventors: Heinz Auer, Bernd Bessling, Hans Hammer, Hans Hasse, Friedrich Sauer, Maximilian Vicari, Gerhard Wagner, Till Adrian
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Publication number: 20030009062Abstract: 1Type: ApplicationFiled: July 12, 2002Publication date: January 9, 2003Inventors: Frank Dobert, Alexander Klausener, Paul Wagner
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Patent number: 6492551Abstract: 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: GrantFiled: April 16, 2001Date of Patent: December 10, 2002Assignee: Kemira Chemicals OYInventors: Erkki Paatero, Marko Lahtinen, Kari Saari, Pekka Vapaaoksa
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Patent number: 6429333Abstract: In a method for preparing formic acid, methyl formate is prepared with methanol as a reactant.Type: GrantFiled: June 19, 2001Date of Patent: August 6, 2002Assignee: Kemira Chemicals OyInventors: Kari Saari, Esko Tirronen, Antti Vuori, Marko Lahtinen
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Patent number: 6258980Abstract: 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: GrantFiled: June 27, 1994Date of Patent: July 10, 2001Assignee: Contracts Chemicals Ltd.Inventor: David Anthony Jones
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Patent number: 6137005Abstract: 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: GrantFiled: February 26, 1998Date of Patent: October 24, 2000Assignee: Norsk Hydro ASAInventor: Leif Hj.o slashed.rnevik
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Patent number: 6127573Abstract: 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: GrantFiled: April 1, 1999Date of Patent: October 3, 2000Assignee: Merck & Co., Inc.Inventors: Jing Li, Zhiguo Song, David M. Tschaen, Mangzu Zhao
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Patent number: 6015535Abstract: 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: GrantFiled: May 19, 1997Date of Patent: January 18, 2000Assignee: Cabot CorporationInventors: Patrick M. Brown, Michael C. Northrup, Bart F. Bakke
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Patent number: 5891921Abstract: 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: GrantFiled: April 18, 1996Date of Patent: April 6, 1999Assignee: Lonza Inc.Inventor: Leigh E. Walker
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Patent number: 5831120Abstract: 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: GrantFiled: November 19, 1996Date of Patent: November 3, 1998Inventors: Derrick John Watson, Bruce Leo Williams, Michael James Muskett, Stephen James Smith, Chuc Tu Nguyen, Larry Irvin Baker
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Patent number: 5639910Abstract: 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: GrantFiled: November 4, 1994Date of Patent: June 17, 1997Assignees: Research Development Corporation of Japan, Takao IkariyaInventors: Takao Ikariya, Philip Gregory Jessop, Ryoji Noyori
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Patent number: 5633402Abstract: 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: GrantFiled: September 1, 1995Date of Patent: May 27, 1997Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5605669Abstract: 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: GrantFiled: November 24, 1995Date of Patent: February 25, 1997Assignee: Metallgesellschaft AktiengesellschaftInventors: Hartmut Hofmann, Klaus K obele, Horst Prinz, Bernd Phillipp, Gerd Harms, Alexander Schiedt, Ulrike Hecktor
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Patent number: 5599979Abstract: 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: GrantFiled: September 8, 1995Date of Patent: February 4, 1997Assignee: Lloyd BergInventor: Lloyd Berg
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Patent number: 5516406Abstract: 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: GrantFiled: December 15, 1994Date of Patent: May 14, 1996Assignee: Hoechst Celanese CorporationInventors: Nicole G. Wallace, Kenneth A. Windhorst
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Patent number: 5475158Abstract: 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: GrantFiled: December 1, 1993Date of Patent: December 12, 1995Assignee: BASF AktiengesellschaftInventors: Thomas Krug, Rolf Fischer, Rolf Pinkos
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Patent number: 5411725Abstract: 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: GrantFiled: October 18, 1993Date of Patent: May 2, 1995Assignee: Societe Generale Pour les Techniques Nouvelles, SGNInventors: Dominique Pareau, Andre Chesne, Gerard Durand, Michel DeRubercy
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Patent number: 5376293Abstract: 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: GrantFiled: September 9, 1993Date of Patent: December 27, 1994Assignee: State of South Dakota as represented by the Department of TransportationInventor: Daniel P. Johnston
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Patent number: 5373023Abstract: 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: GrantFiled: August 4, 1993Date of Patent: December 13, 1994Assignee: SYNTHELABOInventors: Paul Howard Williams, Christian Hoornaert, Jean Claude Muller
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Patent number: 5334759Abstract: 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: GrantFiled: August 17, 1993Date of Patent: August 2, 1994Assignee: BASF AktiengesellschaftInventors: Ferdinand Lippert, Arthur Hoehn
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Patent number: 5294740Abstract: 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: GrantFiled: March 31, 1993Date of Patent: March 15, 1994Assignee: BASF AktiengesellschaftInventors: Hans Kiefer, Leopold Hupfer, Ferdinand Lippert
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Patent number: 5288904Abstract: 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: GrantFiled: May 4, 1993Date of Patent: February 22, 1994Assignee: Schering CorporationInventors: Maurice Fitzgerald, Eithne Cantwell
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Patent number: 5275702Abstract: 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: GrantFiled: August 12, 1992Date of Patent: January 4, 1994Assignee: Ajinomoto Co., Inc.Inventors: Takehiko Kataoka, Haruo Kawasaki, Harutoshi Ohura, Yoshinobu Uchida, Akihiko Yasaki, Shinichi Kishimoto
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Patent number: 5264086Abstract: 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: GrantFiled: January 29, 1993Date of Patent: November 23, 1993Assignee: Lloyd BergInventors: Lloyd Berg, Randi W. Wytcherley
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Patent number: 5239117Abstract: 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: GrantFiled: September 18, 1991Date of Patent: August 24, 1993Assignee: Board of Regents of the University of OklahomaInventors: Kenneth M. Nicholas, Jing-Cherng Tsai
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Patent number: 5232558Abstract: 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: GrantFiled: October 8, 1992Date of Patent: August 3, 1993Assignee: Lloyd BergInventors: Lloyd Berg, Marc W. Paffhausen
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Patent number: 5228956Abstract: 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: GrantFiled: October 2, 1992Date of Patent: July 20, 1993Assignee: Lloyd BergInventors: Lloyd Berg, Rudolph J. Szabados
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Patent number: 5227029Abstract: 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: GrantFiled: January 29, 1993Date of Patent: July 13, 1993Assignee: Lloyd BergInventors: Lloyd Berg, Randi W. Wytcherley
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Patent number: 5206433Abstract: 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: GrantFiled: May 9, 1985Date of Patent: April 27, 1993Assignee: BASF AktiengesellschaftInventors: Heinz Hohenschutz, Johannes E. Schmidt, Hans Kiefer
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Patent number: 5190619Abstract: 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: GrantFiled: March 30, 1992Date of Patent: March 2, 1993Assignee: Lloyd BergInventors: Lloyd Berg, George Bentu
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Patent number: 5189216Abstract: 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: GrantFiled: July 16, 1991Date of Patent: February 23, 1993Assignee: BASF AktiengesellschaftInventors: Hans Kiefer, Werner Reutemann
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Patent number: 5173156Abstract: 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: GrantFiled: December 9, 1991Date of Patent: December 22, 1992Assignee: Lloyd BergInventors: Lloyd Berg, Kraig M. Wendt, Rudolph J. Szabados
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Patent number: 5047583Abstract: 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: GrantFiled: July 13, 1984Date of Patent: September 10, 1991Assignee: BP Chemicals LimitedInventor: Peter S. Williams
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Patent number: 5019652Abstract: 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: GrantFiled: April 30, 1990Date of Patent: May 28, 1991Assignee: The United States as represented by the United States Department of EnergyInventors: Charles E. Taylor, Richard P. Noceti
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Patent number: 5006205Abstract: 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: GrantFiled: January 17, 1989Date of Patent: April 9, 1991Assignee: Lloyd BergInventors: Lloyd Berg, Kraig M. Wendt, Rudolph J. Szabados
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Patent number: 4994151Abstract: 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: GrantFiled: July 14, 1989Date of Patent: February 19, 1991Assignee: Lloyd BergInventors: Lloyd Berg, George Bentu
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Patent number: 4978430Abstract: 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: GrantFiled: July 24, 1989Date of Patent: December 18, 1990Assignee: UBE Industries, Ltd.Inventors: Kanji Nakagawa, Yoshio Asakura, Shigeru Yamamoto, Kohei Ninomiya, Masayuki Kinouchi
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Patent number: 4957595Abstract: 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: GrantFiled: November 7, 1989Date of Patent: September 18, 1990Assignee: Lloyd BergInventors: Lloyd Berg, George Bentu
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Patent number: 4948471Abstract: 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: GrantFiled: August 1, 1989Date of Patent: August 14, 1990Assignee: Lloyd BergInventors: Lloyd Berg, George Bentu
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Patent number: 4948469Abstract: 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: GrantFiled: December 5, 1988Date of Patent: August 14, 1990Assignee: Lloyd BergInventors: Lloyd Berg, Richard R. Rall
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Patent number: 4935100Abstract: 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: GrantFiled: May 30, 1989Date of Patent: June 19, 1990Assignee: Lloyd BergInventors: Lloyd Berg, Kraig M. Wendt, Rudolph J. Szabados
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Patent number: 4909907Abstract: 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: GrantFiled: January 17, 1989Date of Patent: March 20, 1990Assignee: Hoechst Celanese Chemical Co.Inventor: Lloyd Berg
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Patent number: 4902828Abstract: 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: GrantFiled: October 18, 1984Date of Patent: February 20, 1990Assignee: BASF AktiengesellschaftInventors: Gerhard Wickenhaeuser, Bernd Heida, Fritz Graf, Leopold Hupfer
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Patent number: 4898644Abstract: 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: GrantFiled: May 2, 1988Date of Patent: February 6, 1990Assignee: QO Chemicals, Inc.Inventor: Wendell E. Van Horn
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Patent number: 4894482Abstract: 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: GrantFiled: December 6, 1988Date of Patent: January 16, 1990Assignee: Hoechst Celanese CorporationInventors: Daniel D. Lindley, Carl D. Murphy