Polycarboxylic Acids Or Salts Thereof Patents (Class 562/480)
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Patent number: 5430181Abstract: Process for improving a controlled oxidation reaction between at least one reactant and oxygen, in which at least one reactant is reacted with oxygen or an oxygen containing gas, constituting a reaction mixture, in the presence of at least one additional gas which is introduced into said reaction mixture and is selected from methane, ethane and helium, and the resulting reaction product from the oxidation reaction is possibly treated so as to give a final product.Type: GrantFiled: February 19, 1993Date of Patent: July 4, 1995Assignee: L'Air Liquide Societe Anonyme Pour L'Etude et L'Exploitation des Procedes Georges ClaudeInventors: Philippe Arpentinier, Jacques Koenig, Yves Torre
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Patent number: 5410078Abstract: An unsaturated acid-functional monomer having the structure: ##STR1## wherein R.sup.1 is hydrogen or methyl and Z is nothing or is a divalent radical of 1 to about 20 carbons.Type: GrantFiled: January 3, 1994Date of Patent: April 25, 1995Assignee: The Sherwin-Williams CompanyInventor: Rodney M. Harris
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Patent number: 5405995Abstract: Disclosed are novel compounds having the formula ##STR1## where A is O or NR, each R' independently selected from hydrogen, R, or M, R is alkyl, aryl, alkaryl, or aralkyl from C.sub.1 to C.sub.12, and M is a cation. Also disclosed is a method of making those compounds and a method of making a mixture of 3,5-difluorobenzoic acid and 1,3-difluorobenzene by reacting 3,5-dichlorophthalic anhydride with a fluorinating agent to produce 3,5-difluorophthalic anhydride, reacting the 3,5-difluorophthalic anhydride with water to produce 3,5-difluorophthalic acid, and decarboxylating the 3,5-difluorophthalic acid.Type: GrantFiled: June 20, 1994Date of Patent: April 11, 1995Assignee: Occidental Chemical CorporationInventors: Lawrence B. Fertel, James J. Maul
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Patent number: 5387725Abstract: Compounds having acidic protons and a molecular structure which can delocalize the electron density of the conjugate base (target compounds) are chlorinated by contacting such compounds with a perchloroalkane and aqueous base in the presence of a phase transfer catalyst which is an tetraalkylammonium hydroxide. Chlorinated products, preferably gem-dichloro compounds, are produced. The gem-dichloro compounds are useful for alkylation of aromatic compounds. For instance fluorene is chlorinated to form 9,9-dichlorofluorene which is reacted with such compounds as phenol or aniline to form such compounds as 9,9-bis(hydroxyphenyl)fluorene, 9,9-bis(aminophenyl)fluorene, or 9-aminophenyl-9-chlorofluorene.Type: GrantFiled: July 12, 1993Date of Patent: February 7, 1995Assignee: The Dow Chemical CompanyInventors: Marlin E. Walters, W. Frank Richey, Katherine S. Clement, Steven L. Brewster, Emmett L. Tasset, Paul M. Puckett, V. Rao Durvasula, Hong A. Nguyen
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Patent number: 5350872Abstract: The subject matter of the invention is a process for the preparation of carboxylic acids and derivatives of them of the general formula ##STR1## wherein R means hydrogen, or a C.sub.1-4 alkyl or a (C.sub.1-5 alkoxy)carbonyl group,R.sub.1 is as defined in claim 1,R.sub.7 stands for hydrogen or a C.sub.1-7 alkyl group andR.sub.8 means hydrogen or a carboxyl group,by reacting a 1,3-dioxane-4,6-dione derivative of the general formula ##STR2## wherein R.sub.9 stands for a C.sub.1-4 alkyl group or a phenyl group, optionally monosubstituted by halogen andR.sub.10 stands for hydrogen or a C.sub.1-5 alkyl group orR.sub.9 and R.sub.10 together form a pentamethylene group,and an aldehyde or ketone of the general formula ##STR3## in the presence of formic acid.Type: GrantFiled: October 29, 1993Date of Patent: September 27, 1994Assignee: Biogal GyogyszergrarInventors: Gyorgy Toth, Janos Balint, Klara Elek nee Herczik, Zsuzsanna Moricz nee Garai, Eva Mudra nee Kantor
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Patent number: 5344970Abstract: A ruthenium-phosphite complex having the formula ##STR1## wherein a is from 1 to 3; b is 1 or 2; c is from 0 to 3; and R is hydrogen, alkyl, aryl, halo, amino, acetylamino, or sulfo; and X is ##STR2## where R.sub.1, R.sub.2, and R.sub.3 are the same or different and are hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl.This complex can be used to effect the reduction of unsaturated organic compounds or, when comprised of ligands having optical activity, can be used as the catalyst for effecting the asymmetric reduction of unsaturated organic compounds.Type: GrantFiled: December 22, 1993Date of Patent: September 6, 1994Assignee: Albemarle CorporationInventor: Charles H. Kolich
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Patent number: 5334754Abstract: Provided is a process for preparing 2,5-diphenylterephthalic acid, which is useful in preparing certain polyesters, especially liquid-crystalline polyesters. In this process, p-xylene is di-alkylated with cyclohexene to provide 2,5-dicyclo-hexyl-p-xylene, which is in turn dehydrogenated to provide 2,5-diphenylxylene. 2,5-Diphenylxylene is then oxidized to provide 2,5-diphenylterephthalic acid by utilization of a cobaltous/manganous/bromide oxidation system.Type: GrantFiled: August 14, 1992Date of Patent: August 2, 1994Assignee: Eastman Chemical CompanyInventors: Charles E. Sumner, Jr., Bruce L. Gustafson, Ernest W. Arnold, III, Eric J. Fugate, Dewey W. Fuller, Jr.
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Patent number: 5322954Abstract: Disclosed is a method of making a 4-substituted phthalic anhydride. A halomaleic (including halofumaric anhydride (or the acid or ester thereof) is made by the reaction of-maleic anhydride with chlorine or bromine. The halomaleic anhydride is reacted with a conjugated diene to form a first cycloadduct having the formula ##STR1## The first cycloadduct is heated to eliminate HX and produce a second cycloadduct having the formula ##STR2## The second cyclo adduct is dehydrogenated to produce a 4substituted phthalic anhydride which has the formula ##STR3## where R.sub.1, R.sub.2, and R.sub.4 are preferably H and R.sub.3 is preferably Cl or F.Type: GrantFiled: May 28, 1993Date of Patent: June 21, 1994Assignee: Occidental Chemical CorporationInventors: Karl W. Seper, Jeffrey S. Stults, Gary H. Olsen
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Patent number: 5319134Abstract: Disclosed is a process for introducing a carboxyl group to an aromatic carboxylic acid or a derivative thereof, which comprises reacting a starting aromatic carboxylic acid, such as a benzoic acid, a biphenylcarboxylic acid, a naphthalenecarboxylic acid, a diphenylcarboxylic acid, or a derivative thereof, with a carbon tetrahalide in the presence of a cyclodextrin and an alkali metal hydroxide, thereby introducing a carboxyl group to the aromatic ring of the starting aromatic carboxylic acid or the derivative thereof in substitution for a hydrogen atom bonded thereto. By the process of the present invention, a desired aromatic polycarboxylic acid or a derivative thereof can be easily obtained with high selectivity.Type: GrantFiled: October 26, 1992Date of Patent: June 7, 1994Assignee: Hidefumi HiraiInventors: Hidefumi Hirai, Rikinori Terakado, Hisashi Mihori, Tsutomu Nakamura, Kazuhiro Saito
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Patent number: 5294738Abstract: A process for the selective hydrodefluorination of a tetrafluorophthalimide compound of the formula ##STR1## where X is 1 and R is a monovalent organo group; or X is 2 and R is a divalent organo group; comprises reacting (I) the tetrafluorophthalimide with zinc in an aqueous alkali metal hydroxide medium. The product may be hydrolyzed to form 3,4,6-trifluorophthalic acid.Type: GrantFiled: April 3, 1992Date of Patent: March 15, 1994Assignee: Occidental Chemical CorporationInventors: Jeffrey S. Stults, Lawrence B. Fertel, William S. Derwin
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Patent number: 5254666Abstract: Production of alkali metal or alkaline-earth metal terephthalate by reaction of an alkali metal or alkaline-earth metal hydroxide with a polyol polyterephthalate, and optional conversion of the terephthalate into terephthalic acid.The reaction is performed without addition of water or in the presence of an amount of water representing at most, by weight, the amount of polyterephthalate.The invention is useful for the treatment of polyol polyterephthalate waste.Type: GrantFiled: January 29, 1992Date of Patent: October 19, 1993Assignee: Institut Francais du PetroleInventor: Jacques Benzaria
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Patent number: 5250724Abstract: A very selective process for the catalytic air oxidation of pseudocumene to trimellitic acid. Manganese, cobalt, cerium and titanium in the presence of bromine are used as the catalyst.Type: GrantFiled: May 12, 1992Date of Patent: October 5, 1993Assignee: Alusuisse Italia S.p.A.Inventors: Carlo Fumagalli, Lorenzo Capitanio, Giancarlo Stefani
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Patent number: 5243067Abstract: A 3,4,3',4'-substituted biphenyl compound represented by the general formula (II): ##STR1## wherein, one of R.sup.1 and R.sup.2 is a -CH.sub.3 group and the one other is a --COOR.sup.5 group, --COOH group, or --COCl group, and one of R.sup.3 and R.sup.4 is a -CH.sub.3 group and the other one is a --COOR.sup.5 group, --COOH group, or --COCl group, is produced by the steps of oxidatively coupling an o-toluic acid alkyl ester in the presence of a catalyst containing a mixture of palladium salts with 1,10-phenanthroline or .alpha.,.alpha.'-bipyridine, a chelating product of a palladium salt with 1,10-phenanthroline, or a chelating products of a palladium salt with .alpha.,.alpha.Type: GrantFiled: February 20, 1991Date of Patent: September 7, 1993Assignee: Ube Industries, Ltd.Inventors: Akinori Shiotani, Michinori Suzuki, Fumio Matsuo
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Patent number: 5210292Abstract: A process for purifying a crude terephthalic acid obtained by neutralization of the disodium terephthalate from alkali waste water from a polyester fabric-treatment process, into polymer grade terephthalic acid. The crude terephthalic acid is crushed, and fed to the kiln at 150.degree.-300.degree. C. for thermal treatment in an aqueous solution. The ammoniated, and the impurities in the solution are removed by adsorption followed by deammoniation, which may be accomplished by heating or by treatment with sulfuric acid.Type: GrantFiled: October 12, 1990Date of Patent: May 11, 1993Assignee: Korea Research Institute of Chemical TechnologyInventors: Sang F. Park, Tae S. Chang, Young K. Lee, Kyu W. Choi
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Patent number: 5210289Abstract: Certain ethylenically unsaturated polymerizable monomers having a reactive carboxy group are useful for preparing homo- and copolymers for a variety of uses, including diagnostic assays. The polymers can be supplied as latex particles in aqueous compositions. The monomers are represented by the structure: ##STR1## wherein: R is hydrogen, halo or alkyl of 1 to 3 carbon atoms,M is hydrogen, an alkali metal ion or an ammonium ion, andL is a linking group having from 8 to 50 atoms in its linking chain, and comprises two or more divalent hydrocarbon groups connected or terminated with one or more nitrogen, oxygen or sulfur atoms, or with one or more groups containing such atoms in the linking chain, provided L has at least one arylene which is not directly connected to the terminal ##STR2## group, and further provided that none of the hydrocarbon groups has non-aromatic unsaturation.Type: GrantFiled: March 23, 1992Date of Patent: May 11, 1993Assignee: Eastman Kodak CompanyInventors: Ignazio S. Ponticello, Richard C. Sutton
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Patent number: 5208366Abstract: An improved process is provided for the preparation of esters of polyhalophthalic acids, polyhalobenzoic acids, and polyhalophthalic anhydride useful as flame retardants for thermoplastic and thermosetting resins, which comprises the reaction of the above acids or anhydride with alcohols in the presence of certain metal and metallorganic compounds as catalysts. Also provided are certain esters per se.Type: GrantFiled: August 19, 1991Date of Patent: May 4, 1993Assignee: Elf Atochem North America, Inc.Inventors: Joseph M. Bohen, Anthony J. Mancuso
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Patent number: 5200556Abstract: Process for the preparation of 3,4,6-tetrafluorophthalic acid of the formula (1) ##STR1## or the anhydride thereof in good yields and in an advantageous manner, by dehalogenating tetrafluorophthalic anhydride of the formula (2) ##STR2## or tetrafluorophthalic acid in aqueous-alkaline medium using zinc at temperatures of approximately 20.degree. C. to approximately 160.degree. C. and, if appropriate, converting the resulting 3,4,6-trifluorophthalic acid into the anhydride in a known manner by dehydrating it.Type: GrantFiled: May 21, 1992Date of Patent: April 6, 1993Assignee: Hoechst AktiengesellschaftInventors: Theodor Papenfuhs, Ralf Pfirmann
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Patent number: 5183926Abstract: Aromatic dicarboxylic acids of the formula ##STR1## in which R.sup.1, R.sup.2, m, n, and X have the meaning mentioned in the description,can be prepared from the bisphenols, on which they are based, of the formula ##STR2## if the bisphenols are first reacted to give the bissulphonates, the sulphonate groups are removed catalytically with H.sub.2 and the hydrocarbons obtained in this way are doubly acylated in a known manner and the acyl groups are oxidized to the carboxyl groups.Many of the aromatic dicarboxylic acids which can be prepared in this way are new.Type: GrantFiled: September 13, 1991Date of Patent: February 2, 1993Assignee: Bayer AktiengesellschaftInventors: Richard Weider, Thomas Scholl
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Patent number: 5175354Abstract: The process of this invention for preparing 2,6-naphthalene-dicarboxylic acid comprises a reaction step (Step A) wherein 2,6-naphthalene-dicarboxylic acid potassium salts consisting of 2,6-naphthalene-dicarboxylic acid dipotassium salt and/or 2,6-naphthalene-dicarboxylic acid monopotassium salt are allowed to react with benzene-carboxylic acids in the presence of water to yield 2,6-naphthalene-dicarboxylic acid and benzene-carboxylic acid potassium salts and a separation step (Step B) wherein the crystallized 2,6-naphthalene-dicarboxylic acid is separated from the benzene-carboxylic acid potassium salts dissolved in the aqueous solution and provides 2,6-naphthalene-dicarboxylic acid, useful as raw material for polymers, at low cost on a commerical scale with recycle of potassium.Type: GrantFiled: April 1, 1991Date of Patent: December 29, 1992Assignees: Nippon Steel Chemical Co., Ltd., Nippon Steel CorporationInventors: Shuichi Mitamura, Yasuhisa Tsutsumi, Yoshimi Kata, Atsushi Kawada, Naoya Okabayashi
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Patent number: 5136055Abstract: A 21-carbon aliphatic branched chain dicarboxylic acid and a 21-carbon lactone are produced by reacting fatty acid (which contains linoleic acid) with acrylic acid via iodine catalysis, and subsequently removing from the low monomer reaction product the resulting C-21 lactone via solvent extraction with acetonitrile and hexane or heptane. The reaction products are distilled to yield dicarboxylic acid and lactone of high purity.Type: GrantFiled: September 3, 1991Date of Patent: August 4, 1992Assignee: Westvaco CorporationInventor: Yvette A. Tramount
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Patent number: 5113015Abstract: There is provided a process for recovering acetic acid from methyl acetate wherein the methyl acetate is hydrolyzed catalytically to methanol and acetic acid in the same tower or column that is used to separate the methanol from the acetic acid and the hydrolysis and separation are carried out coextensively in the vessel. The process is employed suitably in a process for the partial oxidation of a polymethylbenzene to a polycarboxylic acid in the presence of an oxidation catalyst and an acetic acid solvent.Type: GrantFiled: November 20, 1990Date of Patent: May 12, 1992Assignee: Amoco CorporationInventors: David A. Palmer, Keith D. Larson, Kristi A. Fjare
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Patent number: 5107053Abstract: A ruthenium phosphine complex having catalytic, hydrogenation activity is disclosed. The catalyst as the formula ##STR1## wherein R and R' are the same or different and are C.sub.1 to C.sub.6 linear or branched alkyl; R" is hydrogen or C.sub.1 to C.sub.6 linear or branched alkyl; R.sub.1 is C.sub.1 to C.sub.6 linear or branched alkyl; and n is an integer from 1 to 6.The phosphine complex is particularly useful in the asymmetric hydrogenation of unsaturated carboxylic acids or alkyl esters thereof.Type: GrantFiled: October 25, 1991Date of Patent: April 21, 1992Assignee: Ethyl CorporationInventor: Tse-Chong Wu
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Patent number: 5095141Abstract: A process is disclosed for oxidation of pseudocumene to trimellitic acid wherein process residue and bottoms from stripping procedures to recover process solvent are recycled and incorporated in filtrate mother liquor and reinjected into the oxidation reactor at a point in time at least after the first methyl group in the pseudocumene molecule has been oxidized to a carboxy group. Recovery of trimellitic acid is increased, catalyst recovery is increased in a form suitable for immediate recycle to the oxidation reaction, and waste products from the oxidation process are substantially reduced.Type: GrantFiled: December 19, 1990Date of Patent: March 10, 1992Assignee: Amoco CorporationInventors: Wayne P. Schammel, Chang-Man Park, Donald E. Ruedin, John N. Wood, Leo C. Fende
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Patent number: 5095144Abstract: A process for dimerizing an aromatic halogen compound is disclosed, which comprises the step of: subjecting an aromatic halogen compound having at least one halogen atom bonded to an aromatic nucleus carbon to a dehalogenation-dimerization reaction in the presence of a catalyst, water, a reducing agent, and a halogen acceptor, the catalyst comprising a carrier supported thereon palladium and iron.Type: GrantFiled: July 17, 1990Date of Patent: March 10, 1992Assignee: Mitsubishi Kasei CorporationInventors: Keiichi Sato, Takahiko Takewaki, Yoshio Katsuro
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Patent number: 5087742Abstract: A process for preparing aromatic polycarboxylic acids is disclosed, wherein a benzil derivative is oxidized with molecular oxygen in the presence of an oxidation catalyst consisting substantially of at least one heavy metal catalyst selected from cobalt and manganese and a bromine catalyst in a solvent containing at least 50 wt.% of an aliphatic monocarboxylic acid having at most three carbon atoms.According to this invention, there are provided 4,4'-bis(4-alkylphenyl)benzils (wherein alkyl is methyl, ethyl or isopropyl), which are novel benzil derivative.Type: GrantFiled: June 14, 1990Date of Patent: February 11, 1992Assignee: Kureha Kagaku Kogyo K.K.Inventors: Kazuo Yoshida, Nobuyuki Okubo, Toshiharu Matsuda, Yutaka Konai
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Patent number: 5086188Abstract: Plychlorophthalimides, specifically, N-substituted tetrachlorophthalimides and N-substituted trichlorophthalimides may be treated with zinc and a base in aqueous soluction to yield, after acidification, the product 3,5-dichlorophthalic acid or salts thereof.Type: GrantFiled: January 16, 1991Date of Patent: February 4, 1992Assignee: Occidental Chemical CorporationInventors: Lawrence B. Fertel, Neil J. O'Reilly, Henry C. Lin
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Patent number: 5081252Abstract: A process for the preparation of aromatic carboxylic acids or their salts comprises heating carboxyl-free aromatic compounds and aromatic carboxylic acid salts whose basic structures differ from those of the aromatic compounds, or heating polycyclic aromatic compounds with three or more rings and monocyclic or bicyclic aromatic carboxylic acid salts, under carbon dioxide pressure in the presence of one or more metal compounds selected from group (a) of compounds of zinc, cadmium, and thallium and one or more compounds selected from group (b) of compounds of cesium, Group II metals, And Group IIIa metals to effect the intermolecular transfer of the carboxyl groups.Type: GrantFiled: June 5, 1989Date of Patent: January 14, 1992Assignees: Nippon Steel Corporation, Nippon Steel Chemical Co., Ltd.Inventors: Shuichi Mitamura, Yoshimi Kata, Koichi Fujishiro, Yasuhisa Tsutsumi
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Patent number: 5081291Abstract: A process for the preparation of 3,3',4,4'-biphenyltetracarboxylic acid salt by the dehalodimerization of a 4-halophthalic acid salt. The process uses hydroxylamine or one of its salts as the reducing agent in an alkaline solution, preferably of pH 10 or above, and palladium catalyst. The reaction is carried out between 50.degree. and 150.degree. C.Type: GrantFiled: September 21, 1990Date of Patent: January 14, 1992Assignee: E. I. Du Pont de Nemours and CompanyInventor: John H. Freudenberger
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Patent number: 5081290Abstract: There is provided a process for the partial oxidation of a polymethylbenzene to the corresponding aromatic polycarboxylic acid, which process comprises contacting in a reaction zone said polymethylbenzene with molecular oxygen in the presence of an oxidation catalyst comprising at least one heavy-metal compound, said heavy-metal compound being acetate free, a source of bromine, and a non-metal acetate compound, the concentration of acetate in the reaction zone being employed to control the rate of oxidation and the selectivity of oxidation.There is also provided the catalyst that is employed in the process.Type: GrantFiled: June 21, 1990Date of Patent: January 14, 1992Assignee: Amoco CorporationInventors: Walter Partenheimer, Diane J. Graziano
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Patent number: 5068300Abstract: New Z-stilbene compounds and a process for their preparation are disclosed wherein the compounds correspond to the following formulae: ##STR1##Type: GrantFiled: October 19, 1990Date of Patent: November 26, 1991Assignee: Bayer AktiengesellschaftInventors: Dieter Arlt, Axel Bader, Volker Eckhardt
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Patent number: 5068407Abstract: A process for the production of para-oriented dicarboxylic aromatic acids is disclosed in which an aromatic compound, having a tertiary alkyl group, is oxidized with molecular oxygen in the presence of a catalytic composition comprising a cobalt salt, a minor amount of a manganese salt, and a source of chloride in the presence of a solvent.Type: GrantFiled: January 31, 1990Date of Patent: November 26, 1991Assignee: Monsanto CompanyInventors: Roy A. Periana, George F. Schaefer
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Patent number: 5068409Abstract: The bis(4-halo-phthalic acid) quarter salt of formula ##STR1## wherein M is an alkali metal or ammonium, and X is a halogen atom is descibed. Further described is a process for its preparation and a method of purifying 4-halo-phthalic acid containing impurities, which comprises preparing therefrom a compound of formula I, separating the compound of formula I which precipitates from the mother liquor, washing it and recovering the 4-halo-phthalic acid.Type: GrantFiled: September 7, 1990Date of Patent: November 26, 1991Assignee: Bromine Compounds Ltd.Inventors: Olga Vainberg, Leonard M. Shorr
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Patent number: 5047560Abstract: Highly pure 3,3',4,4'-biphenyltetracarboxylic acid (BPTA) and dianhydride thereof (BPDA) are produced by heating crude BPTA to give BPDA, treating the BPDA with hot water to give highly pure BPTA, and in the case of highly pure BPDA, heat treating the pure BPTA to give highly pure BPDA.Type: GrantFiled: March 9, 1990Date of Patent: September 10, 1991Assignees: Hitachi, Ltd., Japan Carlit Co., Ltd., Kanto KoatsuInventors: Fusaji Shoji, Nobuo Aoki, Jun Kurita, Tsuyoshi Aoyama, Toshiyuki Kiriyu, Yoshinori Matsuzaki
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Patent number: 5047553Abstract: Chlorinated phthalic anhydrides are converted to fluorinated phthalic acids without dilactone formation by reacting an anhydride with a primary amine under anhydrous conditions to form the corresponding chlorinated-N-substituted phthalimide which in turn is reacted with a fluorinating agent under anhydrous conditions to form the corresponding fluorinated phthalimide which is hydrolyzed to form the corresponding fluorinated phthalic acid.In a preferred embodiment tetrachlorophthalic anhydride is refluxed with aniline in the presence of glacial acetic acid for 5 to 10 hours to form tetrachloro-N-phenylphthalimide which is reacted with KF in sulfolane in the presence of tributylhexadecylophosphonium bromide under nitrogen at 140.degree. C. to 160.degree. C. for 10 to 15 hours to form tetrafluoro-N-phenylphthalimide which in turn is hydrolyzed by refluxing with 50% H.sub.2 SO.sub.4 for 15 to 25 hours. The tetrafluoro-N-phenylphthalimide is a novel compound.Type: GrantFiled: February 27, 1989Date of Patent: September 10, 1991Assignee: Occidental Chemical CorporationInventors: Deanne M. Nowak, Henry C. Lin
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Patent number: 5041610Abstract: Ring-opened resorcyclic acid lactone derivatives of the formla ##STR1## wherein X is ethylene or ethenylene; Y and Z, which may be the same or different, are methylene, hydroxymethylene or carbonyl; R.sub.1 is hydrogen or lower alkyl of from 1 to about 6 carbon atoms; R.sub.2, R.sub.3, R.sub.4 and R.sub.5, which may be the same or different, are hydrogen, hydroxyl, halogen, nitro, amino or a radical selected from the group consisting of --R', --OR', --COOR' and --OCOR' wherein R' is lower alkyl of from 1 to about 6 carbon atoms, lower cycloalkyl of from 3 to about 8 carbon atom, alkenyl of from 2 to about 6 carbon atoms, substituted or unsubstituted aryl of from 6 to about 8 carbon atoms, or substituted or unsubstituted aralkyl wherein the alkyl portion contains from 1 to about 6 carbon atoms and the aryl portion contains from 6 to about 8 carbon atoms. These compounds are useful as growth-promotants in food-producing animals.Type: GrantFiled: November 28, 1986Date of Patent: August 20, 1991Assignee: International Minerals & Chemical Corp.Inventor: Keith A. Drengler
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Patent number: 5004830Abstract: A process is disclosed for liquid phase oxidation of alkyl aromatic hydrocarbons to aromatic carboxylic acids in presence of a multivalent catalyst promoted by a source of bromine. The oxidation is conducted in at least two oxidation reactions. Exothermic heat of reaction is controlled by means of a liquid phase heat exchanger to control temperature and pressure. Oxygen partial pressure in each stage is at least 1.5 psia to minimize oxygen starvation and improve selectivity. Low reactor temperature, high reactor pressure and improved selectivity improve product yield and product quality.Type: GrantFiled: November 29, 1989Date of Patent: April 2, 1991Assignee: Amoco CorporationInventors: Chang M. Park, Wayne P. Schammel
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Patent number: 4999441Abstract: Tetrakis(dialkylamino)aromatics Ia to Ic ##STR1## where the radicals A may be identical or different and are n-C.sub.1 -C.sub.6 -alkyl and the radicals R may be identical or different and are hydrogen or C.sub.1 -C.sub.6 -alkyl, and their charge transfer complexes with electron acceptors, and the preparation of Ia to Ic from the corresponding N-unsubstituted amines by alkylation with A'--CHO (where A'.dbd.H or N-C.sub.1 -C.sub.5 -alkyl) and reduction with NaBH.sub.3 CN.The charge transfer complexes of Ia and Ic are used to prepare electrically conductive polymers.Type: GrantFiled: April 17, 1989Date of Patent: March 12, 1991Assignee: Max-Planck-Gesellschaft zur Foerderung der Wissenschaften e.V.Inventors: Heinz A. Staab, Karin Elbl
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Patent number: 4992579Abstract: A process for the manufacture of trimelitic acid from pseudocumene is disclosed. The pseudocumene is oxidized in the presence of a cerium, cobalt, manganese, and optionally zirconium, bromine catalyst wherein all of the cerium is added in the second stage of the oxidation, and wherein most of the bromine is also added during the second oxidation stage. Trimellitic acid is useful in the manufacture of polyester and polyamide-imides.Type: GrantFiled: December 18, 1989Date of Patent: February 12, 1991Assignee: Amoco CorporationInventor: Wayne P. Schammel
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Patent number: 4981999Abstract: Disclosed is a method of selectively removing chlorine atoms in the order of fifth position first, fourth position second, and third position third from a chlorophthalic compound having at least two ring chlorine atoms such as a chlorophthalic acid or a chlorophthalic anhydride. The chlorophthalic compound is reacted in solution with a hydrodechlorinating metal in the presence of a base.Type: GrantFiled: November 20, 1989Date of Patent: January 1, 1991Assignee: Occidental Chemical CorporationInventors: Neil J. O'Reilly, William S. Derwin, Henry C. Lin
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Patent number: 4959488Abstract: Polyfunctional hexasubstituted benzene derivatives wherein at least three of the substituents are saturated carbon chains having from 1 to 21 carbon atoms and functional groups containing hetero functionalities at the ends of the carbon chains and the remainder of the 6 substituents are either saturated carbon chains containing from 1 to 21 carbon atoms or saturated carbon chains containing from 1 to 21 carbon atoms having a functional group including a hetero functional group containing N, O, S, P, or Si at the end of the chains. These derivatives are made by reacting a disubstituted alkyne wherein one or both of the substituents are saturated carbon chains having 1 to 21 carbon atoms to which hetero functional groups are attached with a palladium catalyst and isolating the resulting hexasubstituted benzene derivative.Type: GrantFiled: May 17, 1989Date of Patent: September 25, 1990Assignee: Henkel Research CorporationInventors: James M. Renga, Alan G. Olivero, Mark Bosse
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Patent number: 4952721Abstract: A process is disclosed for the oxidation of esters of para- and meta-methyl-substituted phenols to the corresponding aromatic carboxylic acid in the presence of a promoter comprising an anhydride of a lower aliphatic carboxylic acid and a heavy metal catalyst with or without the presence of bromine. The resulting carboxylic acids are useful in liquid crystal polymers and polymers useful in engineering plastics.Type: GrantFiled: March 8, 1989Date of Patent: August 28, 1990Assignee: Amoco CorporationInventor: Kristi A. Fjare
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Patent number: 4897473Abstract: This invention produces higher homologs, i.e., differing by at least a --CH.sub.2 -unit, of carbonyloxy-containing compounds by treating the carbonyloxy-containing compounds with carbon monoxide and hydrogen in the presence of a ruthenium-containing compound, a proton donor, an iodide promoter, and optionally, a manganese-containing compound.Type: GrantFiled: May 1, 1981Date of Patent: January 30, 1990Assignee: Union Carbide Chemicals and Plastics Company Inc.Inventor: Bernard D. Dombek
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Patent number: 4892970Abstract: Improved acid yield and product quality are realized in the oxidation of aromatic hydrocarbons in a two-stage process, employing an aqueous solvent system and an increased proportion of bromine, and, optionally, of catalytic metals, in the second stage.Type: GrantFiled: December 30, 1985Date of Patent: January 9, 1990Assignee: Amoco CorporationInventors: Neal R. Nowicki, James D. Lowry, Jr.
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Patent number: 4885384Abstract: A process for the production of aromatic carboxylic acids which comprises carbonylating substituted iodoaromatic compounds in the presence of carbon monoxide, a catalytic amount of a transition metal catalyst, and a Bronsted base in a mixture of a carboxylic acid and water under aromatic carboxylic acid forming conditions of temperature and pressure.Type: GrantFiled: March 14, 1988Date of Patent: December 5, 1989Inventors: Guy R. Steinmetz, Kevin J. Edgar, Stephen N. Falling
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Patent number: 4845110Abstract: There are provided anti-allergic pharmaceutical compounds of formula: ##STR1## in which n is 0, 1 or 2; R.sup.1 is a hydrocarbyl group containing 6 to 30 carbon atoms and optionally substituted with an optionally substituted phenyl group; R.sup.2 is (i) optionally optionally protected tetrazolyl, --COR.sup.6 where R.sup.6 is C.sub.1-4 alkyl, C.sub.1-4 alkoxy, an optionally protected amino acid residue or --NR.sub.2.sup.7 where each R.sup.7 is hydrogen or C.sub.1-4 alkyl, and --NHR.sup.8 where R.sup.8 is hydrogen, a protecting group, an optionally protected amino acid residue, C.sub.1-4 alkyl or --COR.sup.9 where R.sup.9 is C.sub.1-4 alkyl or C.sub.1-4 alkoxy, or (iii) C.sub.1-10 alkyl substituted with a group selected from ##STR2## where each R.sup.10 is hydrogen or C.sub.1-4 alkyl; and R.sup.3, R.sup.4 and R.sup.5 are each selected from hydrogen, carboxyl, C.sub.2-5 alkoxycarbonyl, C.sub.1-4 alkyl, hydroxyl, optionally protected tetrazolyl, halo, trifluoromethyl, nitrile, nitro and --CONR.sub.2.sup.Type: GrantFiled: December 4, 1986Date of Patent: July 4, 1989Assignee: Lilly Industries LimitedInventors: Stephen R. Baker, Alec Todd
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Patent number: 4803294Abstract: This invention relates to novel intermediate compounds which are useful for producing the halogenated protease inhibitors that are the subject matter of U.S. Pat. No. 4,469,885. In particular, the invention relates to novel methods and intermediates for making said protease inhibitors, the intermediate compounds being of the formula: ##STR1## wherein R.sub.1 is: (a) straight or branched chain lower alkyl having 1-6 carbon atoms; or(b) H;wherein R.sub.6 is:(a) straight or branched chain higher alkyl having 13-25 carbon atoms; or(b) straight or branched chain higher alkenyl having 13-25 carbon atoms;wherein R.sub.5 is:(a) straight or branched chain lower alkyl having 1-6 carbon atoms; or(b) benzyl;wherein R.sub.7 is:(a) straight or branched chain lower alkyl having 1-6 carbon atoms; or(b) H;wherein R.sub.2 is:(a) --Cl, --Br, or --I; or(b) --CF.sub.3.Type: GrantFiled: October 29, 1987Date of Patent: February 7, 1989Assignee: G. D. Searle & Co.Inventors: Richard A. Mueller, Richard A. Partis
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Patent number: 4801407Abstract: In the present invention, hydrated magnesium salts of the carboxylate group in certain aromatic or olefinically unsaturated peroxyacids such as monoperoxyphthalic acid or monoperoxymaleic acid are made by reacting the corresponding anhydride with aqueous hydrogen peroxide and a magnesium base, in the absence of a significant amount of free iron. By so doing, the process avoids the use of non-aqueous solvents such as ethyl acetate. Solid product can be obtained by using no more than enough hydrogen peroxide and water for solely a damp product to be obtained or by crystallization from an aqueous solution, preferably with recycle of the mother liquor. Preferably the reaction temperature is maintained at 5.degree. to 25.degree. C., employing 1.8 to 2.2 moles anhyhdride per mole of magnesium base, and 0.95 to 1.2 moles of hydrogen peroxide per mole of anhydride.The product can be used as a bleach and as a disinfectant.Type: GrantFiled: May 25, 1982Date of Patent: January 31, 1989Assignee: Interox Chemicals LimitedInventors: Geoffrey J. Hignett, Iain S. MacKirdy
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Patent number: 4786753Abstract: A novel method of oxidizing di- and trimethylbenzenes with molecular oxygen to the corresponding di- or tricarboxylic acid under liquid-phase conditions is disclosed. The process is conducted at a temperature of about 100.degree. C. to 260.degree. C. This process comprises conducting the oxidation in the presence of a catalyst system comprising a source of bromine with nickel, manganese and zirconium. The benzene di- and tricarboxylic acids have wide industrial application, including the manufacture of polyesters, polyamides, and fibers and films.Type: GrantFiled: May 18, 1987Date of Patent: November 22, 1988Assignee: Amoco CorporationInventors: Walter Partenheimer, Wayne P. Schammel
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Patent number: 4783547Abstract: The difunctional polyfluoroaromatic compounds represented by the formula ##STR1## wherein X and Y are identical and are selected from the class consisting of --COOR.sup.1, --CH.sub.2 NH.sub.2, --CH.sub.2 NCO and ##STR2## wherein R.sup.1 is --H, alkyl and R.sup.2 and R.sup.3 independently are either --H, X or alkyl and n is either 0 or 1 are disclosed. These compounds are derived from those wherein X and Y are --CN which are produced in a solvent specific reaction. The process comprises reacting pentafluorobenzonitrile with a Grignard reagent of the formula CH.sub.3 MgHal, wherein Hal is --Cl or --Br, in the presence of either tetrahydrofuran, 1,3-dioxolane, dimethoxyethane or diglyme. When the solvent employed is tetrahydrofuran, the cyano compound wherein n is 1 is obtained. When the solvent is 1,3-dioxolane, the cyano compound wherein n is 0 is obtained.Type: GrantFiled: April 18, 1986Date of Patent: November 8, 1988Assignee: ICI Americas Inc.Inventors: Ludwig A. Hartmann, John F. Stephen
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Patent number: 4782180Abstract: An improved process for the preparation of 2,3,4,5-tetrafluorobenzoic acid is described which involves decarboxylation of tetrafluorophthalic acid in the presence of a base catalyst. Also described is an improved method for preparing tetrafluorophthalic acid and, in turn, a one-pot process for tetrafluorobenzoic acid using the combination of the two improvements.Type: GrantFiled: May 7, 1986Date of Patent: November 1, 1988Assignee: Warner-Lambert CompanyInventors: James N. Wemple, Timothy P. Puls, James Vande Vusse