Air, Oxygen, Or Ozone Oxidant Patents (Class 562/421)
-
Patent number: 8304575Abstract: The present invention relates to a process for producing an ether carboxylate which includes the steps of (1) reacting an aliphatic monohydric alcohol with an alkylene oxide in the presence of an alkali catalyst; (2) neutralizing a reaction solution obtained in the step (1) with an acid such as hydroxycarboxylic acids to obtain an ether alcohol; and (3-1) reacting the obtained ether alcohol with a monohalogenofatty acid or a salt thereof and an alkali metal hydroxide, or (3-2) subjecting the obtained ether alcohol to catalytic oxidation reaction in the presence of a catalyst. The obtained ether carboxylate has a less odor and a high quality and is therefore suitably used in the applications such as cosmetics and toiletries.Type: GrantFiled: April 3, 2008Date of Patent: November 6, 2012Assignee: Kao CorporationInventors: Akira Matsunaga, Kaoru Ohmae
-
Patent number: 8153840Abstract: Disclosed is an optimized process and apparatus for more efficiently and economically carrying out the liquid-phase oxidation of an oxidizable compound. Such liquid-phase oxidation is carried out in a bubble column reactor that provides for a highly efficient reaction at relatively low temperatures. When the oxidized compound is para-xylene and the product from the oxidation reaction is crude terephthalic acid (CTA), such CTA product can be purified and separated by more economical techniques than could be employed if the CTA were formed by a conventional high-temperature oxidation process.Type: GrantFiled: February 22, 2010Date of Patent: April 10, 2012Assignee: Grupo Petrotemex, S.A. de C.V.Inventors: Thomas Earl Woodruff, Alan George Wonders
-
Method For The Production Of Aryl Polyglycol Carboxylic Acids By Means Of A Direct Oxidation Process
Publication number: 20110144385Abstract: The invention relates to a method for producing compounds of formula (I) in which R1 represents an aromatic group containing 6 to 200 carbon atoms, R2 represents hydrogen, a linear or branched alkyl group containing 1 to 22 carbon atoms, a monounsaturated or polyunsaturated linear or branched alkenyl group containing 2 to 22 carbon atoms, or an aryl group containing 6 to 12 carbon atoms, X represents an alkylene group containing 2 to 4 carbon atoms, n represents a number between 0 and 100, and B represents a cation or hydrogen, and/or the corresponding protonated carboxylic acids, by oxidizing one or more compounds of formula (II) in which R1, R2, X, and n have the meaning indicated above, with oxygen or oxygen-containing gases in the presence of a gold-containing catalyst and at least one alkaline compound.Type: ApplicationFiled: July 15, 2009Publication date: June 16, 2011Applicant: CLARIANT FINANCE (BVI) LIMITEDInventors: Oliver Franke, Achim Stankowiak, Rainer Kupfer, Ulf Pruesse, Nadine Decker, Klaus-Dieter Vorlop -
Patent number: 7728168Abstract: A process to manufacture 4-methoxybenzoic acid from anethole. This raw material can be obtained from a variety of plant materials and thus offers a renewable alternative to fossil raw materials. Another aspect of the present invention is the use of 4-methoxybenzoic acid gained from vegetal anethole as raw material in cosmetic and dermatologic products and/or aroma components in foodstuffs.Type: GrantFiled: November 3, 2008Date of Patent: June 1, 2010Assignee: Dr. Straetmans Chemische Produkte GmbHInventors: Jan Jänichen, Wilfried Petersen, Rudolf Jenny, Markus Nobis
-
Publication number: 20090131712Abstract: A process to manufacture 4-methoxybenzoic acid from anethole. This raw material can be obtained from a variety of plant materials and thus offers a renewable alternative to fossil raw materials. Another aspect of the present invention is the use of 4-methoxybenzoic acid gained from vegetal anethole as raw material in cosmetic and dermatologic products and/or aroma components in foodstuffs.Type: ApplicationFiled: November 3, 2008Publication date: May 21, 2009Inventors: Jan Janichen, Wilfried Petersen, Rudolf Jenny, Markus Nobis
-
Patent number: 7534912Abstract: A process for producing pyromellitic acid which comprises step A for oxidizing durene, thereby obtaining a reaction mixture comprising trimethyl benzoic acid, trimethyl benzyl alcohol and trimethyl benzaldehyde, step B for separating trimethyl benzoic acid, trimethyl benzaldehyde and trimethyl benzyl alcohol from the reaction mixture obtained in step A, and step C for oxidizing trimethyl benzoic acid and/or trimethyl benzaldehyde separated in step B, thereby obtaining pyromellitic acid.Type: GrantFiled: October 18, 2004Date of Patent: May 19, 2009Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Shinichi Nagao, Hiroshi Ogawa
-
Patent number: 7342128Abstract: The present invention relates to a process for oxidizing a slurry composition in a post oxidation zone in the presence of added steam. More specifically, the present invention relates to a process for oxidizing a crude terephthalic acid composition in a post oxidation zone in the presence of added steam in a process for the production of a crystallized post oxidation composition.Type: GrantFiled: October 20, 2005Date of Patent: March 11, 2008Assignee: Eastman Chemical CompanyInventors: Robert Lin, Marcel de Vreede, Johannes Wilhelmus Sluijmers, Martin De Boer, Thomas Earl Woodruff
-
Patent number: 7341972Abstract: The present invention relates to novel singlet oxygen catalysts useful for the production of specialty chemicals. The catalysts include a core material selected from amine coated polymeric beads, amine coated glass beads and multi-generational dendrimers to which condensed carbon molecules are bonded. These catalysts may in turn give rise to other solid phase heterogeneous catalysts useful for stereoselective or regioselective reactions, by way of non-limiting example.Type: GrantFiled: October 18, 2004Date of Patent: March 11, 2008Inventor: Anton W. Jensen
-
Patent number: 7202380Abstract: In a method of producing pyromellitic acid by liquid-phase oxidizing 2,4,5-trimethylbenzaldehyde in a water solvent with molecular oxygen, a recrystallization mother liquor separated in a recrystallization step is recycled to the oxidation step after a part of the water solvent is removed. With this method, the loss of pyromellitic acid and the oxidation catalyst can be minimized and the burden of discharging the waste water is reduced without lowering the efficiency of the liquid-phase oxidation reaction.Type: GrantFiled: January 13, 2004Date of Patent: April 10, 2007Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tatsuyuki Kumano, Seiji Adachi, Hiroshi Ogawa
-
Patent number: 7126024Abstract: This invention is directed to a process for making a salt of a carboxylic acid. The process comprises contacting a catalyst with an alkaline mixture comprising a primary alcohol. In one embodiment, the catalyst comprises a metal supporting structure (preferably a metal sponge supporting structure comprising at least about 10% by weight nickel) having a copper-containing active phase at the surface thereof and iron as a catalyst modifier. The supporting structure is resistant to deformation under the conditions of the dehydrogenation reaction. This invention is also directed to novel nickel-containing catalysts having a copper-containing active phase and iron as a catalyst modifier which may, for example, be used in the above process. This invention is further directed to processes for making such catalysts.Type: GrantFiled: October 16, 2002Date of Patent: October 24, 2006Assignee: Monsanto Technology LLCInventors: David A. Morgenstern, James P. Coleman, James M. Allman
-
Patent number: 6888023Abstract: A process for producing pyromellitic acid which comprises oxidizing 2,4,5-trimethylbenzaldehyde and/or its oxidized derivative in the presence of a catalyst containing iron, manganese and bromine, or additionally containing zirconium or cerium continuously or semi-continuously using aqueous acetic acid solvent and 0.05-2% by weight of bromide ion. The catalyst used in the present invention has high activity, and the catalyst solution has low corrosive because the reaction is performed at low bromide concentration by using a solvent of aqueous acetic acid. So pyromellitic acid is produced industrially advantageously in high yield continuously or semi-continuously which has been a major difficulty up to now.Type: GrantFiled: May 19, 2003Date of Patent: May 3, 2005Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kazuo Tanaka, Hiroshi Ogawa, Ikutraro Maruki, Atsushi Okoshi
-
Publication number: 20040158068Abstract: The present invention concerns a process for oxidising an aromatic aldehyde to the corresponding carboxylic acid. The process of the invention for preparing an aromatic acid by oxidising an aromatic aldehyde consists of carrying out the oxidation of the aromatic aldehyde in a basic medium using molecular oxygen or a gas containing molecular oxygen in the presence of a catalyst, and is characterized in that oxidation is carried out in the presence of an effective quantity of a palladium and/or platinum based catalyst under conditions such that oxidation is carried out in a diffusion regime.Type: ApplicationFiled: April 5, 2004Publication date: August 12, 2004Inventors: Roland Jacquot, Jean-Louis Grieneisen
-
Patent number: 6765113Abstract: A process for the production of an aromatic carboxylic acid comprising contacting in the presence of a catalyst, within a continuous flow reactor, one or more precursors of the aromatic carboxylic acid with an oxidant, such contact being effected with said precursor(s) and the oxidant in an aqueous solvent comprising water under supercritical conditions or near supercritical conditions close to the supercritical point such that said one or more precursors, oxidant and aqueous solvent constitute a substantially single homogeneous phase in the reaction zone, wherein the contact of at least part of said precursor with said oxidant is contemporaneous with contact of said catalyst with at least part of said oxidant.Type: GrantFiled: July 13, 2001Date of Patent: July 20, 2004Assignee: E.I. Du Pont de Nemours and CompanyInventors: Derek Alexander Graham, Paul Anthony Hamley, Raymond Oliver, Martyn Poliakoff, Duncan Woodcock, Thomas Ilkenhans
-
Patent number: 6740776Abstract: A low temperature process for preparing an aromatic acid having formula (I), said process comprising reacting an aromatic aldehyde having formula (II) with a gas having an oxygen content of 1 to 100 weight percent, based on the total weight of the gas, at a temperature of about 20° C. to less than 100° C. in the presence of a supported Group VIII metal catalyst, and a solvent having a flash point greater than 95° C. and/or a melting point less than 55° C., provided that the flash point of the solvent is greater than the reaction temperature, wherein R1 and R2 are independently selected from the group consisting of hydrogen and a C1-C8 linear, branched or cyclic alkyl group. The process of the invention yields an aromatic acid in excellent yield, and (i) does not involve the use of deleterious oxidizing agents; (ii) is essentially free of by-products; and (iii) is accomplished at a temperature of less than 100° C.Type: GrantFiled: July 15, 2002Date of Patent: May 25, 2004Assignee: Novartis AGInventors: Ratna Shekhar, Michael John Girgis
-
Publication number: 20030208091Abstract: A process for producing pyromellitic acid which comprises oxidizing 2,4,5-trimethylbenzealdehyde and/or its oxidized derivative in the presence of a catalyst containing iron, manganese and bromine, or additionally containing zirconium or cerium continuously or semi-continuously using aqueous acetic acid solvent and 0.05-2% by weight of bromide ion. The catalyst used in the present invention has high activity, and the catalyst solution has low corrosive because the reaction is performed at low bromide concentration by using a solvent of aqueous acetic acid. So pyromellitic acid is produced industrially advantageously in high yield continuously or semi-continuously which has been a major difficulty up to now.Type: ApplicationFiled: May 19, 2003Publication date: November 6, 2003Inventors: Kazuo Tanaka, Hiroshi Ogawa, Ikutraro Maruki, Atsushi Okoshi
-
Publication number: 20030023115Abstract: A low temperature process for preparing an aromatic acid having formula (I), 1Type: ApplicationFiled: July 15, 2002Publication date: January 30, 2003Inventors: Ratna Shekhar, Michael John Girgis
-
Patent number: 6476258Abstract: An industrially advantageous process for producing an aryloxyacetic acid represented by the formula (2): wherein m represents an integer of 1 or 2, n represents an integer from 0 to 4, Ar represents a aromatic hydrocarbon ring, each Rs independently represents an alkyl group, a cycloalkyl group, an aryl group, an alkoxy group, a cycloalkoxy group, an aryloxy group, a halogen atom, an alkylcarbonyl group, an arylcarbonyl group, a carboxyl group or a nitro group, comprising a step in which an oxygen-containing gas is made act on an aryloxyethanol represented by the formula (1): (R)n-Ar&Parenopenst;O—CH2.CH2.OH)m (1) wherein m, n, Ar, and R, respectively, have the same meanings as defined above, under conditions of using a catalyst comprising palladium and an indium compound and/or a copper compound in an aqueous medium and in the presence of 0.Type: GrantFiled: July 5, 2000Date of Patent: November 5, 2002Assignee: Sumitomo Chemical Company, LimitedInventors: Masashi Komatsu, Junichi Ishikawa
-
Publication number: 20020151745Abstract: A process for producing pyromellitic acid which comprises oxidizing 2,4,5-trimethylbenzealdehyde and/or its oxidized derivative in the presence of a catalyst containing iron, manganese and bromine, or additionally containing zirconium or cerium continuously or semi-continuously using aqueous acetic acid solvent and 0.05-2% by weight of bromide ion. The catalyst used in the present invention has high activity, and the catalyst solution has low corrosive because the reaction is performed at low bromide concentration by using a solvent of aqueous acetic acid. So pyromellitic acid is produced industrially advantageously in high yield continuously or semi-continuously which has been a major difficulty up to now.Type: ApplicationFiled: February 28, 2002Publication date: October 17, 2002Inventors: Kazuo Tanaka, Hiroshi Ogawa, Ikutraro Maruki, Atsushi Okoshi
-
Publication number: 20020133043Abstract: A method for oxidizing an aromatic compound possesssing at least one alkyl substituent by using a catalyst avoids containing a corrosive bromine ion, remains stably without being decomposed even in an oxidizing atmospherfe, and permits reclamation is provided. An aromatic compound possessing at least one alkyl substituent is oxidized by using a catalyst which has at least one kind of element selected from the group consisting of phosphorus, silicon, and germanium as a hetero atom and at least one kind of element selected from the group consisting of molybdenum, tungsten, vanadium, and niobium as a poly atom and comprises a heteropoly-oxometalate nion possessing two defective structure site and at least one kind of element selected from the group of elements of Periods 4˜6 of Groups IB, VA, VIIA, and VIII in the Periodic Table of the Elements.Type: ApplicationFiled: November 7, 2001Publication date: September 19, 2002Inventors: Yasutaka Sumida, Masahiro Wada, Noritaka Mizuno
-
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
-
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
-
Patent number: 6245936Abstract: The present invention concerns a process for the preparation of a 2-hydroxybenzoic acid and of a 4-hydroxybenzaldehyde and derivatives thereof from a mixture of two phenolic compounds, one carrying a formyl or hydroxymethyl group in the 2 position, and the other carrying a formyl or hydroxymethyl group in the 4 position. The invention also concerns the preparation of a 4-hydroxybenzaldehyde from said mixture. The invention more particularly concerns the preparation of 3-methoxy-4-hydroxybenzaldehyde and of 3-ethoxy4-hydroxybenzaldehyde, respectively known as “vanillin” and ethylvanillin”.Type: GrantFiled: April 12, 1999Date of Patent: June 12, 2001Assignee: Rhodia ChimieInventors: Pascal Metivier, Christian Maliverney, Philippe Denis
-
Patent number: 5998572Abstract: Methods and devices for controlling the oxidation of a hydrocarbon to an acid by regulating the temperature hold-up time, and conversion in consecutive reaction zones. The temperature in the consecutive reaction zones progressively decreases, while the hold-up time increases. Preferably, the conversion also increases. One of the major advantages of the methods and devices of the present invention is that an outstanding balance between productivity and selectivity/yield of the desired acid may be achieved. In this respect high yields and selectivities may be obtained without sacrificing productivity.Type: GrantFiled: May 12, 1998Date of Patent: December 7, 1999Assignee: RPC Inc.Inventors: Ader M. Rostami, Mark W. Dassel, Eustathios Vassiliou, David C. DeCoster
-
Patent number: 5635197Abstract: A series of benzoquinolin-3-ones are pharmaceuticals effective in preventing the development of prostatic cancer, or preventing or treating the metastasis to bone of prostatic cancer.Type: GrantFiled: March 21, 1995Date of Patent: June 3, 1997Assignee: Eli Lilly and CompanyInventors: James E. Audia, Blake L. Neubauer
-
Patent number: 5629007Abstract: A series of benzoquinolin-3-ones are pharmaceuticals effective in preventing the development of prostatic cancer, or preventing or treating the metastasis to bone of prostatic cancer.Type: GrantFiled: March 21, 1995Date of Patent: May 13, 1997Assignee: ELi Lilly and CompanyInventors: James E. Audia, Blake L. Neubauer
-
Patent number: 5608106Abstract: A process for preparing an alkoxyalkanoic acid by reacting the corresponding alkoxyalkanol with a resin-supported stable free radical nitroxide in the presence of a NO.sub.x -generating compound and, optionally, an oxidant and/or a solvent at a temperature in the range of from about 0.degree. C. to about 100.degree. C. and thereafter separating out the alkoxyalkanoic acid.Type: GrantFiled: May 11, 1995Date of Patent: March 4, 1997Assignee: Shell Oil CompanyInventors: Herbert E. Fried, David M. Singleton, Raul A. Pabon, Jr.
-
Patent number: 5481032Abstract: A process for the preparation of halogenated benzoic acids of formula (1): ##STR1## in which R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are hydrogen, fluorine, chlorine or bromine atoms or C.sub.1 -C.sub.6 -alkyl, C.sub.1 -C.sub.6 -alkoxy, nitro, cyano, trifluoromethyl, aidehyde, C.sub.1 -C.sub.4 -alkoxycarbonyl, -SO.sub.2 -C.sub.1 -C.sub.4 -alkyl, -SO.sub.2 -phenyl, -CONH.sub.2, -CON(C.sub.1 -C.sub.4 -alkyl).sub.2, hydroxy, carboxy, -NH.sub.2 or -N(C.sub.1 -C.sub.4 - alkyl).sub.2 groups, at least one of the substituents R.sub.1 -R.sub.5 being one of said halogen atoms, which comprises reacting 1 mol of a benzophenone, asymmetrically substituted on the benzene rings A and B, of general formula (2): ##STR2## in which R.sup.1 -R.sup.10 are as defined above for R.sub.1 -R.sub.Type: GrantFiled: November 29, 1993Date of Patent: January 2, 1996Assignee: Hoechst AktiengesellschaftInventor: Ralf Pfirmann
-
Patent number: 5463114Abstract: Ether carboxylic acids of the formula (I):R--(OC.sub.m H.sub.2m).sub.n --O--CH.sub.2 COOM (I)wherein R is an alkyl group having from 1 to about 22 carbon atoms, an aryl group or an aralkyl group; m is 2 or 3; n is a number from 1 to about 200; M is an alkali metal are made by oxidation of an ether alcohol wherein the ether alcohol, oxygen, and an alkali metal hydroxide are continuously added to an aqueous dispersion of a noble metal catalyst under reduced pressure.Type: GrantFiled: April 13, 1994Date of Patent: October 31, 1995Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Wolf-Eckart Noack, Paul Schulz, F. Norman Tuller
-
Patent number: 5292934Abstract: Disclosed is a method for preparing an aromatic carboxylic acid comprising oxidizing in the liquid phase an aromatic feed compound containing at least one alkyl or acyl group with a molecular oxygen-containing gas, in a solvent comprising a low molecular weight aliphatic carboxylic acid, and in the presence of a heavy metal oxidation catalyst, thereby forming an oxidation reaction product mixture comprising an aromatic carboxylic acid; subsequently heating the oxidation reaction product mixture at a temperature of at least about 500.degree. F. to form a second product mixture; and recovering from the second product mixture the aromatic carboxylic acid. The method of this invention provides for purer, larger particle size aromatic carboxylic acid product.Type: GrantFiled: June 18, 1992Date of Patent: March 8, 1994Assignee: Amoco CorporationInventors: David L. Sikkenga, George E. Kuhlmann, Paul K. Behrens, Martin A. Zeitlin, Stephen V. Hoover
-
Patent number: 5239075Abstract: This invention relates to a process for the preparation of hexa- and octahydrobenzo[f]quinolin-3-ones.Type: GrantFiled: August 10, 1992Date of Patent: August 24, 1993Assignee: Eli Lilly and CompanyInventors: James E. Audia, David E. Lawhorn
-
Patent number: 5237092Abstract: A process for efficiently producing aryl formate and aromatic carboxylic acid from aldehyde, which comprises oxidizing an aromatic aldehyde with an oxygen-containing gas in the presence of a volatile solvent up to a reaction ratio of 40 to 70 mol % to convert the aromatic aldehyde to a peracid, adding a stabilizer, and allowing the remaining aromatic aldehyde and the aromatic peracid to react while the volatile solvent is distilled off.Type: GrantFiled: June 16, 1992Date of Patent: August 17, 1993Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Toru Tanaka, Kazuo Tanaka, Teruo Aratake
-
Patent number: 5223642Abstract: A process for the preparation of ether carboxylic acids by ethoxylation of carbohydrates followed by catalytic oxidation and the use of the products in detergents or cleaning agents.Type: GrantFiled: March 30, 1992Date of Patent: June 29, 1993Assignee: Hoechst AktiengesellschaftInventor: Karl-Heinz Schonwalder
-
Patent number: 5157152Abstract: A process for oxidation of a tetrahydro compound of the formula ##STR1## wherein R and R' independently are H, alkyl, aryl or halo, to a glycol of the formula ##STR2## comprises treating the tetrahydro compound with hydrogen peroxide at an elevated temperature under reflux conditions in the absence of a catalyst. The thus-formed glycol can be further oxidized to a butanetetracarboxylic acid of the formula ##STR3## with hydrogen peroxide in the presence of a catalyst selected from the group consisting of a manganese salt, an iron salt, a chromium salt, a cerium salt, a persulfate, a perborate, a silicate, tungstic acid or an ammonium or alkali metal salt or heteropolyacid thereof, or molybdic acid or an ammonium or alkali metal salt or heteropolyacid thereof.Type: GrantFiled: July 9, 1991Date of Patent: October 20, 1992Assignee: Ortec, Inc.Inventors: David L. Brotherton, Kwok W. Fung, Kam H. Wong
-
Patent number: 5095143Abstract: A method to oxidize an oxidizable component in a liquid phase with an oxygen-containing gas is disclosed. The method comprises mixing the liquid phase and gas phase in a reactor with a rotating agitator element operated at constant power.Type: GrantFiled: June 13, 1990Date of Patent: March 10, 1992Assignee: Amoco CorporationInventors: Daniel L. Heberer, Paul R. Schiller, Virginia R. Seemann, Michael J. Yerkes
-
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
-
Patent number: 5041634Abstract: Process for the preparation of compounds of the formula HO-Ar-COOH in which Ar is a substituted or unsubstituted aromatic ring system, by oxidizing, by means of oxygen or compounds which donate oxygen, compounds of the formula HO-Ar-R.sub.1 in which R.sub.1 is alkyl having 1 to 5 carbon atoms and Ar is as defined above, or the O-acyl derivatives of these compounds, in an organic solvent at 80.degree. to 130.degree. C. and in the presence of an acylating agent, a cobalt and/or manganese compound and a compound which donates bromide, ions, and subsequently hydrolysing the products in a conventional manner. In the presence of the acylating agent, a selective oxidation of the hydroxyl-substituted aromatic compounds to carboxylated hydroxy compounds, which are obtained in a good state of purity and yield, is obtained without the application of pressure.The compounds obtained in accordance with the process are, for example, valuable intermediates for the preparation of dyes, plastics and pharmaceuticals.Type: GrantFiled: December 1, 1988Date of Patent: August 20, 1991Assignee: Ciba-Geigy CorporationInventors: Martin Clausen, Paul Rys, Junkuan Wang
-
Patent number: 4990660Abstract: Aromatic hydroxycarboxylic acids of the formula(HO--).sub.n A--COOHwhere n is 1 or 2 and A is a radical from the benzene, naphthalene, biphenyl, diphenyl ether, diphenyl sulfide or diphenyl sulfone series, are prepared by a process in which an acylated aromatic compound of the formula(R.sup.1 --CO--O--).sub.n A--CO--R.sup.2where R.sup.1 and R.sup.2 independently of one another are each unsubstituted or substituted C.sub.1 -C.sub.4 -alkyl and n and A each have the abovementioned meanings, is oxidized with oxygen in the presence of a catalyst and of a solvent at from 20.degree. to 250.degree. C. to give a carboxylic acid of the formula(R.sup.1 --CO--O--).sub.n A--COOHwhere R.sup.1, n and A have the abovementioned meanings, and the acyl group or groups is or are then eliminated.Type: GrantFiled: December 21, 1988Date of Patent: February 5, 1991Assignee: BASF AktiengesellschaftInventors: Peter Neumann, Ulrich Eichenauer
-
Patent number: 4981997Abstract: A process for the preparation of 2,5-diarylaminoterephthalic acids by oxidation of 2,5-diarylamino-3,6-dihydroterephthalic acid esters using oxygen or oxygen-containing gases, preferably air, in alcoholic-alkaline or alcoholic-aqueous-alkaline solution or suspension in the presence of an oxygen-transferring agent and working up to give the 2,5-diarylaminoterephthalic acids, characterized in that the oxidation is carried out in the presence of quaternary ammonium compound.Type: GrantFiled: September 29, 1989Date of Patent: January 1, 1991Assignee: Bayer AktiengesellschaftInventors: Detlef-Ingo Schutze, Reinold Schmitz
-
Patent number: 4976893Abstract: The invention relates to a process for preparing carboxylic acids by platinum-catalyzed oxidation of primary alcohols of limited water solubility with oxygen in a mixture of water and a solubilizer. The solubilizer used is an ether of the general formula R.sub.1 O(CH.sub.2 CH.sub.2 O).sub.n R.sub.2, where n is 1-4 and R.sub.1 and R.sub.2 are alkyl radicals having 1-4 carbon atoms.Type: GrantFiled: June 18, 1986Date of Patent: December 11, 1990Assignee: Hoechst AktiengesellschaftInventor: Ernst I. Leupold
-
Patent number: 4959494Abstract: A method for oxidizing organic compounds by contacting organic compounds with molecular oxygen in the presence of a noble metal pyrochlore having the formula:A.sub.2+x B.sub.2-x O.sub.7-ywherein A is a pyrochlore structure metal cation, and B is one or more of Ru, Rh, Ir, Os, and Pt; x and y are greater than or equal to 0 and less than or equal to 1.0, at a temperature up to about 200.degree. C.Type: GrantFiled: July 6, 1987Date of Patent: September 25, 1990Assignee: Monsanto CompanyInventor: Timothy R. Felthouse
-
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
-
Patent number: 4940808Abstract: A process for the ozonization of unsaturated organic compounds in a reaction column through which the unsaturated compounds--in solution in a protic solvent--and an ozone-containing carrier gas and an inert coolant are passed downward in co-current flow to provide for an improved coolant effect and an increased ozonization yield where the coolant comprises a compound gaseous or liquid at ambient temperature with a boiling point preferably in the range from +20.degree. C. to -200.degree. C. The boiling point of the coolant is preferably at least 5.degree. C. below the ozonization temperature.Type: GrantFiled: July 7, 1988Date of Patent: July 10, 1990Assignee: Henkel Kommanditgesellschaft auf AktienInventors: Paul Schulz, Michael J. Virnig, Franz J. Carduck
-
Patent number: 4935540Abstract: Process for the preparation of an aryloxyacetic acid by oxidation of aryloxyethanol of the formula: ##STR1## wherein m represents 1 or 2,n represents the numeral which results from the difference between 6 and m and R either individually or independently of one another represents hydrogen, alkyl, cycloalkyl, aryl, aralkyl, alkoxy, cycloalkoxy, aryloxy, halogen, alkylcarbonyl, arylcarbonyl, carboxyl or nitro, or represents a benzene ring fused to the phenyl ring, in an aqueous alkaline reaction medium at a temperature in the range of 0.degree. C. to the boiling point of the reaction medium in the presence of a catalytic amount of a catalyst comprised of palladium, thallium and carbon to form the corresponding alkali metal ester and contacting the alkali metal ester with a mineral acid.Type: GrantFiled: December 12, 1988Date of Patent: June 19, 1990Inventor: Charles E. Sumner, Jr.
-
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.
-
Patent number: 4886906Abstract: A process for producing 2,6-naphthalene dicarboxylic acid which comprises oxidizing a 2-alkyl-6-acyl naphthalene with molecular oxygen-containing gas in the presence of a catalyst containing cobalt, manganese, bromine and at least one metal selected from the group consisting of iron, copper and mixtures thereof in an acetic acid solvent is disclosed.Type: GrantFiled: January 6, 1989Date of Patent: December 12, 1989Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Toru Tanaka, Masato Inari
-
Patent number: 4804777Abstract: Process for the preparation of an aryloxyacetic acid by oxidation of aryloxyethanol of the formula: ##STR1## wherein m represents 1 or 2,n represents the numeral which results from the difference between 6 and m and R either individually or independently of one another represents hydrogen, alkyl, cycloalky, aryl, aralkyl, alkoxy, cycloalkoxy, aryloxy, halogen, alkylcarbonyl, arylcarbonyl, carboxyl or nitro, or represents a benzene ring fused to the phenyl ring, in an aqueous alkaline reaction medium at a temperature in the range of 0.degree. C. to the boiling point of the reaction medium in the presence of a catalytic amount of a catalyst comprised of palladium, silver and optionally antimony, and carbon to form the corresponding alkali metal ester and contacting the alkali metal with a mineral acid.Type: GrantFiled: October 9, 1987Date of Patent: February 14, 1989Assignee: Eastman Kodak CompanyInventors: Charles E. Sumner, Jr., Eric J. Fugate
-
Patent number: 4791224Abstract: Process for the preparation of an aryloxyacetic acid/hydroxyethyl ether by oxidation of aryloxyethanol of the formula: ##STR1## wherein R either individually or independently of one another represents hydrogen, alkyl, cycloalkyl, aryl, aralkyl, alkoxy, cycloalkoxy, aryloxy, halogen, alkylcarbonyl, arylcarbonyl, carboxyl or nitro, or represents a benzene ring fused to the phenyl ring, in an aqueous alkaline reaction medium at a temperature in the range of 0.degree. C. to the boiling point of the reaction medium in the presence of a catalytic amount of a catalyst comprised of palladium, bismuth, and carbon in the presence of a phenol corresponding to the structure: ##STR2## wherein R is as described above and p is 0, 1 or 2, to form the corresponding alkali metal ester/hydroxyethyl ether after catalyst removal the alkali metal ester is contacted with a mineral acid.Type: GrantFiled: April 7, 1988Date of Patent: December 13, 1988Assignee: Eastman Kodak CompanyInventors: Charles E. Sumner, Jr., Eric J. Fugate
-
Patent number: 4778924Abstract: Cynnamic aldehyde disolved in an aromatic hydrocarbon is oxidized in the liquid phase with molecular oxygen at a temperature in the range of 30.degree.-80.degree. C. in the presence of a cobalt compound and water.Type: GrantFiled: June 15, 1987Date of Patent: October 18, 1988Assignee: Sumitomo Chemical Company, LimitedInventor: Haruhisa Harada
-
Patent number: 4764638Abstract: Disclosed is a method for the preparation of 2,6-naphthalene dicarboxylic acid from 2-acyl-6-alkyl naphthalene, especially 2-acetyl-6-methylnaphthalene, by oxidation in two steps with oxygen or air. The catalyst in the first oxidation is based on manganese. The catalyst in the second oxidation is based on cobalt with bromine added. The addition of 6-alkyl-2-naphthoic acid to the reaction in the second oxidation, in portions or in a continuous manner, results in very good yields having high purities.Type: GrantFiled: August 12, 1986Date of Patent: August 16, 1988Assignee: Dynamit Nobel AGInventor: Marcel Feld
-
Patent number: 4716245Abstract: A process for producing 2,6-naphthalenedicarboxylic acid which comprises oxidizing 2,6-diisopropylnaphthalene or its oxidation derivative with molecular oxygen in a reaction medium containing at least 70% by weight of an aliphatic monocarboxylic acid selected from actic acid, propionic acid and a mixture of these in the presence of an oxidation catalyst comprising (A) at least one compound of a heavy metal element selected from cobalt and manganese and (B) bromine or a bromine compound; characterized in that said oxidation is carried out in the presence of 1.1 to 15 gram-atoms, per gram-atom of bromine, of an alkali metal.Type: GrantFiled: April 18, 1986Date of Patent: December 29, 1987Assignee: Teijin Petrochemical Industries, Ltd.Inventor: Isao Hirose