Halogen Containing Catalyst, Initiator, Or Promoter Utilized Patents (Class 562/416)
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Patent number: 6670487Abstract: Disclosed is a method for removing impurities from products derived from oxidation of an ortho-dialkylaromatic compound which comprises at least one step selected from the group consisting of extraction of an aqueous solution comprising aromatic dicarboxylic acid product with an organic solvent and extraction of an organic solution comprising aromatic anhydride product with an aqueous bicarbonate solution for a time period insufficient to allow hydrolysis of anhydride to acid.Type: GrantFiled: January 30, 2003Date of Patent: December 30, 2003Assignee: General Electric CompanyInventors: Robert Edgar Colborn, Farid Fouad Khouri
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Patent number: 6657068Abstract: A method for the manufacture of halophthalic acid by liquid phase oxidation of halo-ortho-xylene is disclosed. The halophthalic acid may be dehydrated to form halophthalic anhydride which is useful in the synthesis of polyetherimide.Type: GrantFiled: March 22, 2002Date of Patent: December 2, 2003Assignee: General Electric CompanyInventors: Robert Edgar Colborn, David Bruce Hall, Peter Koch, Gerald Oeckel
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Patent number: 6657067Abstract: A method for the manufacture of chlorophthalic acid by liquid phase oxidation of chloro-ortho-xylene is disclosed. The chlorophthalic acid may be dehydrated to form chlorophthalic anhydride which is useful in the synthesis of polyetherimide.Type: GrantFiled: March 22, 2002Date of Patent: December 2, 2003Assignee: General Electric CompanyInventors: Robert Edgar Colborn, David Bruce Hall, Peter Koch, Gerald Oeckel
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Patent number: 6649791Abstract: The present invention relates to the preparation of an aromatic carboxylic acid by contacting an alkyl aromatic compound with an oxygen containing gas in the presence of a encapsulated oxo-bridged organometallic cluster catalyst.Type: GrantFiled: June 28, 2001Date of Patent: November 18, 2003Assignee: Council of Scientific and Industrial ResearchInventors: Darbha Srinivas, Suhas Arunkumar Chavan, Paul Ratnasamy
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Patent number: 6649773Abstract: A method for the manufacture of halophthalic acid by liquid phase oxidation of halo-ortho-xylene is disclosed. The halophthalic acid may be dehydrated to form halophthalic anhydride which is useful in the synthesis of polyetherimide.Type: GrantFiled: March 22, 2002Date of Patent: November 18, 2003Assignee: General Electric CompanyInventors: Robert Edgar Colborn, David Bruce Hall, Peter Koch, Gerald Oeckel
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Publication number: 20030181757Abstract: A method for the manufacture of halophthalic acid by liquid phase oxidation of halo-ortho-xylene is disclosed. The halophthalic acid may be dehydrated to form halophthalic anhydride which is useful in the synthesis of polyetherimide.Type: ApplicationFiled: March 22, 2002Publication date: September 25, 2003Inventors: Robert Edgar Colborn, David Bruce Hall, Peter Koch, Gerald Oeckel
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Publication number: 20030181758Abstract: A method for the manufacture of halophthalic acid by liquid phase oxidation of halo-ortho-xylene is disclosed. The halophthalic acid may be dehydrated to form halophthalic anhydride which is useful in the synthesis of polyetherimide.Type: ApplicationFiled: March 22, 2002Publication date: September 25, 2003Inventors: Robert Edgar Colborn, David Bruce Hall, Peter Koch, Gerald Oeckel
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Publication number: 20030181756Abstract: A method for the manufacture of chlorophthalic acid by liquid phase oxidation of chloro-ortho-xylene is disclosed. The chlorophthalic acid may be dehydrated to form chlorophthalic anhydride which is useful in the synthesis of polyetherimide.Type: ApplicationFiled: March 22, 2002Publication date: September 25, 2003Inventors: Robert Edgar Colborn, David Bruce Hall, Peter Koch, Gerald Oeckel
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Patent number: 6620966Abstract: There is disclosed a process for continuously producing an aromatic carboxylic acid comprising the steps of (A) subjecting a poly-alkyl aromatic hydrocarbon to a liquid-phase oxidation by continuously supplying an oxidation reactor with said hydrocarbon, a catalyst, a reaction accelerator, acetic acid containing water and a gas containing molecular oxygen; (B) continuously taking out from the oxidation reactor, the reaction products containing aromatic carboxylic acids, and separating the same into crude aromatic carboxylic acids and acetic acid containing water; and (C) continuously taking out from the oxidation reactor, the oxidative reaction exhaust gas containing evaporated acetic acid containing water, introducing the above gas in a condenser, and condensing the above evaporated acid, wherein acetic acid containing water is supplied to an oxidative reaction exhaust gas inlet line leading to the condenser.Type: GrantFiled: January 16, 2002Date of Patent: September 16, 2003Assignees: Mitsubishi Gas Chemical Company, Inc., Toyo Boseki Kabushiki Kaisha, Mizushima Aroma Company, Ltd.Inventors: Fumio Ohkoshi, Ikuo Tsuboi, Nirou Hoshishima
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Patent number: 6562997Abstract: Processes for the production of aromatic carboxylic acids is disclosed. The aromatic acids are produced by the liquid phase oxidation of a suitable acid precursor in a reaction medium comprising benzoic acid. According to one embodiment, the oxidation is carried out under plug-flow reaction conditions in a plug-flow reactor. The plug-flow conditions can be achieved by the use of a series of continuous stirred tank reactors. In another embodiment, the oxidation is carried out in two continuous stirred tank reactors fluidly connected in series. The preferred oxidation products are terephthalic acid, isophthalic acid, trimellitic acid, 2,6-naphthalene dicarboxylic acid, 1,5-napthalene dicarboxylic acid, 2,7-naphthalene dicarboxylic acid and phthalic acid.Type: GrantFiled: January 19, 2001Date of Patent: May 13, 2003Assignee: BP Corporation North America Inc.Inventors: David L. Sikkenga, Alpen K. Pandya, Ian C. Zaenger, Kenneth J. Abrams, Thomas M. Bartos
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Publication number: 20030078451Abstract: A catalytic solution system for manufacturing terephthalic acid is disclosed and its method. The system uses a Co—Mn—Br acetate solution (CMB) that is applied in an oxidation reaction, when the weight ratio of each component is (Co %×2.7)+(Mn %×2.9 %)>Br %. CoBr2 and MnBr2 are introduced as a source of Br for the CMB solution. Compensation for any shortage of Co and Mn, after such a supplement, can be made from cobalt acetate and manganese acetate without using highly corrosive HBr. The present invention provides a method of preparing a catalyst for manufacturing terephthalic, wherein, in the stirring action of para-xylene with a gas containing oxygen, the above catalytic solution system is used.Type: ApplicationFiled: July 5, 2002Publication date: April 24, 2003Applicant: Mechema Chemicals International Corp.Inventor: David Yen
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Patent number: 6521786Abstract: A description is given here of a novel process for the production of monocarboxylic and polycarboxylic aromatic acids by the catalytic oxidation in homogeneous phase of aromatic compounds carrying at least one oxidizable substituent group attached directly to the carbon atom of the corresponding aromatic nucleus. The novel process according to the present invention comprises the steps of: a) catalytically oxidizing the corresponding aromatic precursors in liquid phase in the presence of gaseous oxygen; b) filtering the end product; c) recycling into the oxidation reactor at least part of the mother liquors resulting from the filtration stage, and is characterized by the fact that said steps from (a) to (c) are carried out in a closed and continuous cycle operating substantially under the same pressure and temperature conditions, preferably at 2-10 barg and 100-140° C.Type: GrantFiled: August 8, 2001Date of Patent: February 18, 2003Inventors: Franco Codignola, Antonio Moro
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Publication number: 20020193631Abstract: The present invention relates to a method for preparing aromatic carboxylic acid from alkylaromatics by liquid-phase oxidation. More particularly, the present invention relates to a method for preparing aromatic carboxylic acid from alkylaromatics by oxidation in acetic acid as solvent with oxygen-containing gas in the presence of cobalt/manganese/bromine complex catalyst, wherein nickel and carbon dioxide in an appropriate amount are added to increase an activity of cobalt/manganese/bromine complex catalyst. Especially nickel has a synergistic effect with carbon dioxide and maximize the formation of the desired product having the corresponding carboxylic groups to the number of alkyl groups in a reactant.Type: ApplicationFiled: September 28, 2001Publication date: December 19, 2002Applicant: KOREA INSTITUTE OF SCIENCE AND TECHNOLOGYInventors: Sang-Eon Park, Jin S. Yoo, Ki-Won Jun, David B. Raju, Young-Ho Kim
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Patent number: 6485758Abstract: A cure for a hangover containing the active ingredient ephedrine in powdered form enclosed in a capsule. In a second embodiment this cure contains ephedrine and charcoal, while in a third embodiment, this cure contains Ephedra, charcoal and Vitamin B6. The use of any one of the three embodiments reduces the symptoms associated with alcohol intoxication and hangovers thereby speeding up recovery. The Ephedra, Vitamin B-6 and charcoal may be combined on a wt % ratio of 1:2.5:10. The Ephedra may come in the form of Ma Huang having 6% wt % Ephedra. One type of dosage is in the form of individual capsules having 10 Mg of Ephedra, 25 Mg of Vitamin B-6 and 100 Mg of activated charcoal. The recommended dosage would be two capsules so that users who are experiencing a hangover or alcohol related side effects may take up to 20 Mg of Ephedra, 50 Mg of Vitamin B-6 and 200 Mg of activated charcoal.Type: GrantFiled: February 20, 2001Date of Patent: November 26, 2002Assignee: Vasolabs, Inc.Inventors: M. Ather Mirza, Romi Mirza, James R. Brennan
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Patent number: 6458994Abstract: A process for producing a polycarboxylic acid which comprises performing liquid phase oxidation of polyalkyl-substituted aromatic aldehyde and/or oxide derivative of polyalkyl-substituted aromatic aldehyde as raw material for oxidation with molecular oxygen at two stages in water solvent in the presence of a catalyst comprising bromine or both bromine and a heavy metal(s) at a temperature of 180 to 280 ° C., thereby producing trimellitic acid or pyromellitic acid, wherein said liquid phase oxidation is performed in a continuous operation at the first stage and in a continuous operation or in a batch operation at the second stage and a total amount of bromine in said catalyst is divided to add separately at each the first stage and the second stage.Type: GrantFiled: May 22, 2001Date of Patent: October 1, 2002Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Atsushi Okoshi, Etsuo Urabe, Masashi Yabuno, Hiroshi Ogawa, Kazuo Tanaka
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Patent number: 6437176Abstract: An aromatic carboxylic acid, aromatic aldehyde, and aromatic alcohol are simultaneously and efficiently prepared by liquid phase oxidizing an aromatic compound represented by formula (I) with a gas containing molecular oxygen, in a presence of a catalyst comprising transition metal compound, tertiary amine and bromide compound:Type: GrantFiled: March 19, 2001Date of Patent: August 20, 2002Assignee: Toray Industries, Inc.Inventors: Shotaro Matsuoka, Masaaki Suematsu, Akira Kitamura
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Publication number: 20020016501Abstract: A process for producing a polycarboxylic acid which comprises performing liquid phase oxidation of polyalkyl-substituted aromatic aldehyde and/or oxide derivative of polyalkyl-substituted aromatic aldehyde as raw material for oxidation with molecular oxygen at two stages in water solvent in the presence of a catalyst comprising bromine or both bromine and a heavy metal(s) at a temperature of 180 to 280 ° C., thereby producing trimellitic acid or pyromellitic acid, wherein said liquid phase oxidation is performed in a continuous operation at the first stage and in a continuous operation or in a batch operation at the second stage and a total amount of bromine in said catalyst is divided to add separately at each the first stage and the second stage.Type: ApplicationFiled: May 22, 2001Publication date: February 7, 2002Applicant: Mitsubishi Gas Chemical Company, Inc.Inventors: Atsushi Okoshi, Etsuo Urabe, Masashi Yabuno, Hiroshi Ogawa, Kazuo Tanaka
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Publication number: 20010041811Abstract: Processes for the production of aromatic carboxylic acids is disclosed. The aromatic acids are produced by the liquid phase oxidation of a suitable acid precursor in a reaction medium comprising benzoic acid. According to one embodiment, the oxidation is carried out under plug-flow reaction conditions in a plug-flow reactor. The plug-flow conditions can be achieved by the use of a series of continuous stirred tank reactors. In another embodiment, the oxidation is carried out in two continuous stirred tank reactors fluidly connected in series. The preferred oxidation products are terephthalic acid, isophthalic acid, trimellitic acid, 2,6-naphthalene dicarboxylic acid, 1,5-napthalene dicarboxylic acid, 2,7-naphthalene dicarboxylic acid and phthalic acid.Type: ApplicationFiled: January 19, 2001Publication date: November 15, 2001Inventors: David L. Sikkenga, Alpen K. Pandya, Ian C. Zaenger, Kenneth J. Abrams, Thomas M. Bartos
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Publication number: 20010034459Abstract: The invention relates to a process for preparing a compound of the formula (I) 1Type: ApplicationFiled: December 21, 2000Publication date: October 25, 2001Inventors: Andreas Meudt, Stefan Scherer, Antje Norenberg, Peter Koch, Steffen Haber
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Publication number: 20010016667Abstract: An aromatic carboxylic acid, aromatic aldehyde, and aromatic alcohol are simultaneously and efficiently prepared by liquid phase oxidizing an aromatic compound represented by formula (I) with a gas containing molecular oxygen, in a presence of a catalyst comprising transition metal compound, tertiary amine and bromide compound: 1Type: ApplicationFiled: March 19, 2001Publication date: August 23, 2001Applicant: Toray Industries, Inc.Inventors: Shotaro Matsuoka, Masaaki Suematsu, Akira Kitamura
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Patent number: 6255525Abstract: A process for preparing an aromatic carboxylic acid having improved purity comprising contacting at an elevated temperature and pressure a mixture comprising an impure aromatic carboxylic acid and a solvent in the presence of hydrogen gas with a carbon catalyst which is essentially free of a hydrogenation metal component.Type: GrantFiled: December 1, 1998Date of Patent: July 3, 2001Assignee: BP Amoco CorporationInventors: David Lee Sikkenga, M. Michelle Morie-Bebel, Stephen V. Hoover
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Patent number: 6242643Abstract: An aromatic carboxylic acid, aromatic aldehyde, and aromatic alcohol are simultaneously and efficiently prepared by liquid phase oxidizing an aromatic compound represented by formula (I) with a gas containing molecular oxygen, in a presence of a catalyst comprising transition metal compound, tertiary amine and bromide compound:Type: GrantFiled: May 13, 1997Date of Patent: June 5, 2001Assignee: Toray Industries, Inc.Inventors: Shotaro Matsuoka, Masaaki Suematsu, Akira Kitamura
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Patent number: 6232495Abstract: This invention relates to methods and reactor devices for controlling the oxidation of hydrocarbons to dibasic acids, in the presence of a cobalt catalyst and a monobasic acid, such as acetic acid, by treating the catalyst from the reaction mixture, outside the oxidation zone, after the oxidation has taken place at least partially. In one preferred embodiment, the catalyst is reduced to contain, preferably predominantly and more preferably substantially, cobalt ions in valence II, and at least partially precipitated by de-watering and/or thermal treatment. In a different preferred embodiment, the catalyst in the reaction mixture is first oxidized or maintained, preferably predominantly and more preferably substantially, at valence III, the reaction mixture is de-watered, the catalyst is reduced, preferably predominantly and more preferably substantially, to valence II, causing precipitation either spontaneously at a predetermined temperature or after further thermal treatment.Type: GrantFiled: February 4, 1999Date of Patent: May 15, 2001Assignee: RPC Inc.Inventors: Eustathios Vassiliou, Mark W. Dassel, Ader M. Rostami, Douglas J. Dudgeon, David C. DeCoster
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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: 6114575Abstract: A process for producing 2,6-naphthalenedicarboxylic acid by the liquid phase, exothermic oxidation of 2,6-dimethylnaphthalene comprising adding to a reaction zone oxidation reaction components comprising 2,6-dimethylnaphthalene, a source of molecular oxygen, a solvent comprising an aliphatic monocarboxylic acid, and a catalyst comprising cobalt, manganese and bromine components wherein the atom ratio of cobalt to manganese is at least about 1:1 and the total of cobalt and manganese, calculated as elemental cobalt and elemental manganese added to the reaction zone, is less than about 0.Type: GrantFiled: March 25, 1997Date of Patent: September 5, 2000Assignee: BP Amoco CorporationInventors: Rosemary F. McMahon, James D. Greene, Jr., David A. Peterson
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Patent number: 5895820Abstract: A process for the production of a trimellitic acid by oxidizing dialkyl aromatic aldehyde and/or its oxide derivative in a liquid phase, the oxidation being carried out in a lower aliphatic carboxylic acid solvent having a water content of 5 to 70% by weight in the presence of a catalyst containing a heavy metal and bromine or being carried out in a solvent containing a lower aliphatic carboxylic acid in the presence of a bromine-manganese catalyst system containing zirconium and/or cerium, and a process for the production of high-quality trimellitic acid anhydride from the trimellitic acid.Type: GrantFiled: July 15, 1998Date of Patent: April 20, 1999Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kazuo Tanaka, Masashi Yabuno, Hiroshi Ogawa, Atsushi Ohkoshi
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Patent number: 5770764Abstract: Economical processes are disclosed for preparing relatively pure polycarboxylic acid from typical crude products of liquid phase oxidation, which do not involve intermediate steps of ester formation or require any alkanol containing solvent, for purification of "crude" polycarboxylic acid containing impurities which include one or more monofunctional aromatic compounds, trifunctional aromatic compounds, and/or color causing organic compounds formed by oxidation of a corresponding substituted aromatic compound in a liquid phase, e.g. 2,6-naphthalene dicarboxylic acid by liquid phase oxidation of 2,6-dimethyl naphthalene. The invention provides integrate processes which comprise reacting crude oxidation product with a polyalkyl amine amine, e.g. trialkylamine, forming an aqueous solution of the salts thus obtained, separating deleterious compounds from the solution, and recovering the polyalkyl amine and a relatively pure polycarboxylic acid product.Type: GrantFiled: May 19, 1997Date of Patent: June 23, 1998Assignee: Amoco CorporationInventors: Martin A. Zeitlin, David L. Sikkenga, Stephen V. Hoover, Paul K. Behrens
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Patent number: 5763649Abstract: A process for producing aromatic carboxylic acids by subjecting an aromatic compound having one or more substituent alkyl groups and/or partially oxidized substituent alkyl groups to a liquid phase oxidation with a molecular oxygen-containing gas in a reaction solvent containing a lower aliphatic carboxylic acid in the presence of a catalyst composed of a heavy metal compound and a bromine compound, under a condition of a weight proportion of said reaction solvent to said aromatic compound within the range from 6.5 to 70 parts by weight per one part by weight of said aromatic compound, a reaction time within the range from 45 to 4.5 minutes and a product of the numerical value of said weight proportion of the reaction solvent to the aromatic compound multiplied by the numerical value of said reaction time expressed in munute within the range from 270 to 330.Type: GrantFiled: July 8, 1997Date of Patent: June 9, 1998Assignee: Mitsui Petrochemical Industries, Ltd.Inventor: Hiroshi Fukuhara
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Patent number: 5756858Abstract: The invention relates to novel processes for the preparation of phenyl acetic acid derivatives of the formula (I) some of which are known ##STR1## in which R.sup.1, R.sup.2 and R.sup.3 independently of each other each represent hydrogen, alkyl or alkoxy by ozonolysis of compounds of the formula (II) ##STR2## in which R.sup.4 represents hydrogen or methyl and oxidation of the reaction products obtained therefrom. The invention further relates to novel intermediates and a process for the preparation thereof.Type: GrantFiled: March 30, 1995Date of Patent: May 26, 1998Assignee: Bayer AktiengesellschaftInventors: Reinhard Lantzsch, Rainer Fuchs
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Patent number: 5731466Abstract: A method for preparing an alkylbenzoic acid is herein disclosed which comprises subjecting an alkylbenzene having at least two alkyl groups of 1 to 3 carbon atoms to a liquid phase oxidative reaction with a molecular oxygen-containing gas in the presence of a soluble heavy metal catalyst to convert one alkyl group into a carboxylic acid, thereby preparing the alkylbenzoic acid, and impurities contained in the alkylbenzene recovered from the reaction solution are removed therefrom by distillation, water washing, alkali washing, a treatment with an anion exchange resin or a treatment with a solid adsorbent, and the impurities-free fraction is reused as a raw material.Furthermore, the conversion of the desired product is regulated to 25% or less in the liquid phase oxidative reaction, whereby the reaction is carried out in a boiling heat removal state and reaction heat is removed as the heat of vaporization.Type: GrantFiled: October 16, 1996Date of Patent: March 24, 1998Assignee: Mitsubishi Gas Chemical Company, Inc.Inventor: Koichi Kida
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Patent number: 5723656Abstract: A process for preparing aromatic carboxylic acids by the exothermic liquid-phase oxidation reaction of an aromatic feedstock compound, wherein energy is efficiently recovered from the exothermic oxidation reaction.Type: GrantFiled: February 22, 1996Date of Patent: March 3, 1998Assignee: Amoco CorporationInventor: Kenneth J. Abrams
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Patent number: 5696285Abstract: The production of terephthalic acid by the oxidation of p-xylene is carried out in such a manner that the oxygen concentration in the liquid phase is maximized through the use of pure or nearly pure oxygen, while simultaneously the hydrocarbon feed concentration is minimized through rapid dilution with the reactor contents.Type: GrantFiled: December 29, 1995Date of Patent: December 9, 1997Assignee: Praxair Technology, Inc.Inventor: Anne Katherine Roby
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Patent number: 5679847Abstract: There is disclosed a process for producing terephthalic acid which comprises oxidizing in a liquid-phase a starting raw material comprising p-xylene incorporated with 3 to 35% by weight of p-tolualdehyde based on the same at a temperature in the range of 120.degree. to 240.degree. C. by means of a molecular oxygen-containing gas by using a lower aliphatic monocarboxylic acid as a solvent in the presence of a catalyst comprising a manganese compound having 50 to 1000 ppm by weight of manganese atoms, a cobalt compound having 50 to 2000 ppm by weight of cobalt atoms and a bromine compound having 100 to 4000 ppm by weight of bromine atoms, each based on the solvent. By virtue of the above specific constitution, it is made possible to produce high-quality terephthalic acid with a high residual rate of the lower aliphatic monocarboxylic acid as a solvent minimized in its loss, thereby enabling the production of high-quality polyester with high whiteness from the above terephthalic acid and a glycol.Type: GrantFiled: May 6, 1996Date of Patent: October 21, 1997Assignees: Mitsubishi Gas Chemical Company, Inc., Toyo Boseki Kabushiki Kaisha, Mizushima Aroma Company, Ltd.Inventors: Fumio Ohkoshi, Masato Inary, Fumiya Zaima
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Patent number: 5663428Abstract: A method for producing aromatic carboxylic acids which comprises oxidizing a starting compound selected from the group consisting of alkyl substituted aromatic hydrocarbons and partially oxidized alkyl substituted aromatic hydrocarbons with a molecular oxygen containing gas in the presence of at least one additive selected from the group consisting of aliphatic hydrocarbons, alicyclic hydrocarbons, aliphatic alcohols, alicyclic alcohols, aldehydes, carboxylic acids and ketones and in the presence of a catalyst comprising a heavy metal compound and a bromine compound in a reaction solvent. The aliphatic alcohols, alicyclic alcohols, aldehydes, carboxylic acids and ketones have ten to thirty carbon atoms in the molecule.Type: GrantFiled: December 26, 1995Date of Patent: September 2, 1997Assignee: Mitsui Petrochemical Industries, Ltd.Inventors: Hideo Oikawa, Hiroshi Fukuhara
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Patent number: 5637764Abstract: Process for the preparation of brominated or chlorinated aromatic carboxylic acidsThe invention relates to a process for the preparation of bromine- or chlorine-substituted aromatic carboxylic acids by oxidation of the correspondingly halogenated alkylaromatics with oxygen or an oxygen-containing gas in the solvent acetic acid and in the presence of a transition metal bromide catalyst, which comprises a procedure in whicha) the reaction mixture comprises a sodium and/or potassium salt of a weak acid,b) when the reaction has ended, the reaction solution is cooled and the product which has crystallized is filtered off from the reaction solution,c) the combined mother and wash liquors are dehydrated to a water content of .ltoreq.1.0% by distillation,d) the alkali metal halide which has precipitated is filtered off from the mother liquor ande) the mother liquor is reused as the reaction medium.Type: GrantFiled: November 22, 1995Date of Patent: June 10, 1997Assignee: Hoechst AktiengesellschaftInventors: Freimund Rohrscheid, Georg Grotsch
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Patent number: 5587508Abstract: A process for producing 2,6-naphthalenedicarboxylic acid (NDCA) is disclosed. This process comprises oxidizing a 2,6-dialkylnaphthalene with a gas containing molecular oxygen in a solvent containing a lower aliphatic carboxylic acid in the presence of a catalyst comprising heavy metal compounds and a bromine compound, and is characterized in that an ester mixture containing dimethyl 2,6-naphthalenedicarboxylate (NDCM) is added to the oxidation reaction. The low boiling distillate, the high boiling still residue, and the residue of the mother liquor after recrystallization, occurring during purification of the crude NDCM, are also used as additives to the oxidation reaction. According to the present invention, NDCA with large particle size and bulk density can be obtained. Therefore, solid-liquid separation of the crystals, drying of the separated crystals and transportation of the dried crystals are made easier.Type: GrantFiled: January 3, 1996Date of Patent: December 24, 1996Assignee: Mitsubishi Gas Chemical Company, Inc.Inventor: Hiroshi Machida
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Patent number: 5523474Abstract: The oxidation of p-xylene to produce terephthalic acid is carried out using pure or nearly pure oxygen and evaporative cooling. By-product and waste generation are reduced, oxygen utilization is enhanced, desirable operating conditions are employed, and the need for direct contact heat exchange surfaces in the reactor vessel is obviated.Type: GrantFiled: May 11, 1994Date of Patent: June 4, 1996Assignee: Praxair Technology, Inc.Inventors: Jeffrey P. Kingsley, Anne K. Roby
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Patent number: 5523473Abstract: A method of producing naphthalenedicarboxylic acids by the oxidation of dialkyl-substituted naphthalene with a gas containing molecular oxygen in an organic solvent and in the presence of a catalyst comprising copper and bromine, or a catalyst comprising copper, bromine and at least one kind of element/compound selected from the group of consisting of amine compounds and heavy metallic elements which are vanadium, manganese, iron, nickel, palladium and cerium. And a method of producing diaryldicarboxylic acids by the oxidation of dialkyl-substituted diaryl compounds with a gas containing molecular oxygen in an organic solvent and in the presence of the same catalyst. These methods permit high yields of naphthalenedicarboxylic acids of high purity and of diaryldicarboxylic acids of high purity with the use of small amounts of catalyst.Type: GrantFiled: May 25, 1995Date of Patent: June 4, 1996Assignee: Nippon Shokubai Co., Ltd.Inventors: Noboru Saitou, Koichi Hirota, Ren Hasebe, Norimasa Okuda, Ikuyo Katsumi
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Patent number: 5473101Abstract: A process for the controlled oxidation of alkyaromatic compounds comprises reacting said compounds with an oxidising system, comprising cobalt (II) ions, bromide ions, and hydrogen peroxide, in the presence of an appropriate protic solvent.The process is particularly useful in the selective oxidation of poly(alkyl)aromatic compounds.Type: GrantFiled: April 13, 1994Date of Patent: December 5, 1995Assignee: Solvay Interox LimitedInventors: Alexander Johnstone, Kenneth T. Rowbottom, William R. Sanderson, Martin Jeff, Miranda Service
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Patent number: 5463113Abstract: A process and an apparatus for producing terephthalic acid economically by oxidizing paraxylene supplied to an oxidizing reactor connected with a compactly designed distillation column in an acetic acid-based solvent, while effecting the distillatory recovery of the paraxylene and acetic acid efficiently without suffering from stuffing of the distillation column.Type: GrantFiled: March 2, 1994Date of Patent: October 31, 1995Assignee: Mitsui PetrochemicalIndustries, Ltd.Inventors: Ryoichi Yamamoto, Fujimasa Nakao, Etsurou Okamoto, Yasuhiko Yagi
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Patent number: 5453538Abstract: A process for the manufacture of aromatic dicarboxylic acids is disclosed using a low bromine to metals ratio facilitated by the use of cerium along with the cobalt and manganese catalyst. Aromatic dicarboxylic acids such as terephthalic acid are useful in the manufacture of fiber, films, bottles and molded products.Type: GrantFiled: February 14, 1994Date of Patent: September 26, 1995Assignee: Amoco CorporationInventors: Jeffrey L. Broeker, Walter Partenheimer, Bruce I. Rosen
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Patent number: 5442103Abstract: A process for producing 2,6-naphthalenedicarboxylic acid by oxidizing 2,6-dimethylnaphthalene by molecular oxygen in the presence of a catalyst including cobalt, manganese and bromine. The oxidation reaction is performed by using a 2,6-dialkylnaphthalene mixture of 2,6-dimethynaphthalene and a small amount of 2,6-diisopropylnaphthalene as a raw material. Thus, the desired 2,6-naphthalenedicarboxylic acid can be produced at a high yield.Type: GrantFiled: November 16, 1993Date of Patent: August 15, 1995Assignee: Mitsubishi Petrochemical Co., Ltd.Inventors: Hiroshi Iwane, Takahiro Sugawara, Katsufumi Kujira, Naoki Suzuki, Tomoya Sakata
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Patent number: 5416256Abstract: An improved process for manufacturing 5-hydroxyisophthalic acid by means of oxidizing 5-acyloxy-m-xylene or its oxidation intermediate with molecular oxygen in a solvent consisting of lower aliphatic carboxylic acid and acetic anhydride in the presence of catalyst consisting of heavy metal comprising cobalt as the main component, and a bromine compound, and hydrolyzing the product thereby obtained. The improvement is characterized in that the oxidation is carried out under a pressure of 2-15/cm.sup.2 gauge in the presence of an alkali metal compound corresponding to 0.1-1.1 gram atom in terms of alkali metal atom based upon 1 gram atom of the heavy metal used for the catalyst.The present invention produces a high-quality 5-hydroxyisophthalic acid having excellent color from 5-acyloxy-m-xylene.Type: GrantFiled: October 4, 1994Date of Patent: May 16, 1995Assignee: Sumikin Chemical Co., Ltd.Inventors: Takeshi Namekata, Ikuo Ito, Kazuhiko Maeda, Toshio Sato, Keiichi Yokota
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Patent number: 5414113Abstract: Processes are disclosed for recovery and purification of dibasic aromatic acids from waste polyester film, fiber, bottles, manufacturing residues, and other manufactured articles. The processes comprises: depolymerizing polyester resin in a solvent under conditions suitable for hydrolysis of ester bonds to obtain a mixture containing a solution of aromatic acid and impurities consisting of alcohol and/or other components of the resin; burning impurities in a liquid-phase oxidation with an oxygen-containing gas in the presence of an oxidation catalyst at elevated pressures and temperatures, to obtain an oxidation product containing the desired aromatic acid; and crystallizing and separating from the oxidation system a resulting crude dibasic aromatic acid.Type: GrantFiled: October 18, 1993Date of Patent: May 9, 1995Assignee: Amoco CorporationInventors: Jeffrey L. Broeker, John A. Macek, Mossman: Allen B., Bruce I. Rosen, Thomas M. Bartos
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Patent number: 5371283Abstract: Oxygen or an oxygen-rich gas is used in the production of terephthalic acid in a reaction system that mitigates the flammability hazards associated therewith. Lower reactant and solvent consumption is achieved, with lower production of unwanted by-products, lower gas handling costs and lower environmental impact concerns than with conventional air based terephthalic acid production.Type: GrantFiled: December 22, 1993Date of Patent: December 6, 1994Assignee: Praxair Technology, Inc.Inventors: Jeffrey P. Kingsley, Anne K. Roby, Lawrence M. Litz
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Patent number: 5359134Abstract: Provided is a facile three step process for preparing 2-phenylterephthalic acid starting with p-xylene, followed by alkylation, dehydrogenation, and oxidation of the methyl groups corresponding to the origional p-xylene. The product, 2-phenylterephthalic acid, is useful as an intermediate in the synthesis of polyesters comprised of residues of 2-phenylterephthalic acid.Type: GrantFiled: August 14, 1992Date of Patent: October 25, 1994Assignee: Eastman Chemical CompanyInventors: Bruce L. Gustafson, Charles E. Sumner, Jr., Michael Bellas, Gether Irick, Jr., Dewey W. Fuller, Jr., Ernest W. Arnold, Eric J. Fugate
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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: 5288908Abstract: Compounds of the formula ##STR1## in which X represents hydrogen, --NO.sub.2 or --NH.sub.2 and Y represents --CH.sub.3, --COOH, --CONH.sub.2, --NH.sub.2 or --N.dbd.N--Z, in which the group --Z is ##STR2## with the proviso that if Y represents the group --N.dbd.N--Z, X is only --NO.sub.2, and if Y represents the group --CH.sub.3, X is only hydrogen, are described. A compound of the formula ##STR3## the preparation of which in a multi-stage process, in which the compounds of the general formula (I) are also obtained, is described, is preferred.The resulting 3,4'-diamino compound is suitable for the preparation of polycondensates and shaped articles, films and fibers of high heat resistance.Type: GrantFiled: July 19, 1993Date of Patent: February 22, 1994Assignee: Hoechst AktiengesellschaftInventors: Jurgen Lau, Gunter Siegemund, Freimund Rohrscheid
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Patent number: 5274126Abstract: A compound of the formula ##STR1## and the dianhydride thereof are prepared by air oxidation in the presence of a catalyst mixture composed of at least 2 heavy metal salts and also bromine in an acid organic medium. The compounds can be employed for the preparation of partially fluorinated polycondensates, such as polyimides, polycarboxamides, esters of polyamidecarboxylic acids, polyamides and imide-oligomers.Type: GrantFiled: June 5, 1992Date of Patent: December 28, 1993Assignee: Hoechst AGInventors: Freimund Rohrscheid, Wolfgang Appel, Gunter Siegemund
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Patent number: 5256817Abstract: A method for purifying a naphthalenedicarboxylic acid comprising contacting an impure naphthalenedicarboxylic acid with hydrogen in the presence of a hydrogenation catalyst and a solvent comprising a low molecular weight carboxylic acid, at a temperature of at least about 500.degree. F., and a pressure sufficient to maintain the solvent at least partially in the liquid phase and thereafter recovering purified naphthalenedicarboxylic acid.Type: GrantFiled: June 18, 1992Date of Patent: October 26, 1993Assignee: Amoco CorporationInventors: David L. Sikkenga, Stephen V. Hoover