Air, Oxygen, Or Ozone Oxidant Patents (Class 562/421)
  • Patent number: 8304575
    Abstract: 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: Grant
    Filed: April 3, 2008
    Date of Patent: November 6, 2012
    Assignee: Kao Corporation
    Inventors: Akira Matsunaga, Kaoru Ohmae
  • Patent number: 8153840
    Abstract: 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: Grant
    Filed: February 22, 2010
    Date of Patent: April 10, 2012
    Assignee: Grupo Petrotemex, S.A. de C.V.
    Inventors: Thomas Earl Woodruff, Alan George Wonders
  • Publication number: 20110144385
    Abstract: 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: Application
    Filed: July 15, 2009
    Publication date: June 16, 2011
    Applicant: CLARIANT FINANCE (BVI) LIMITED
    Inventors: Oliver Franke, Achim Stankowiak, Rainer Kupfer, Ulf Pruesse, Nadine Decker, Klaus-Dieter Vorlop
  • Patent number: 7728168
    Abstract: 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: Grant
    Filed: November 3, 2008
    Date of Patent: June 1, 2010
    Assignee: Dr. Straetmans Chemische Produkte GmbH
    Inventors: Jan Jänichen, Wilfried Petersen, Rudolf Jenny, Markus Nobis
  • Publication number: 20090131712
    Abstract: 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: Application
    Filed: November 3, 2008
    Publication date: May 21, 2009
    Inventors: Jan Janichen, Wilfried Petersen, Rudolf Jenny, Markus Nobis
  • Patent number: 7534912
    Abstract: 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: Grant
    Filed: October 18, 2004
    Date of Patent: May 19, 2009
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Shinichi Nagao, Hiroshi Ogawa
  • Patent number: 7341972
    Abstract: 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: Grant
    Filed: October 18, 2004
    Date of Patent: March 11, 2008
    Inventor: Anton W. Jensen
  • Patent number: 7342128
    Abstract: 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: Grant
    Filed: October 20, 2005
    Date of Patent: March 11, 2008
    Assignee: Eastman Chemical Company
    Inventors: Robert Lin, Marcel de Vreede, Johannes Wilhelmus Sluijmers, Martin De Boer, Thomas Earl Woodruff
  • Patent number: 7202380
    Abstract: 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: Grant
    Filed: January 13, 2004
    Date of Patent: April 10, 2007
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Tatsuyuki Kumano, Seiji Adachi, Hiroshi Ogawa
  • Patent number: 7126024
    Abstract: 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: Grant
    Filed: October 16, 2002
    Date of Patent: October 24, 2006
    Assignee: Monsanto Technology LLC
    Inventors: David A. Morgenstern, James P. Coleman, James M. Allman
  • Patent number: 6888023
    Abstract: 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: Grant
    Filed: May 19, 2003
    Date of Patent: May 3, 2005
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Kazuo Tanaka, Hiroshi Ogawa, Ikutraro Maruki, Atsushi Okoshi
  • Publication number: 20040158068
    Abstract: 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: Application
    Filed: April 5, 2004
    Publication date: August 12, 2004
    Inventors: Roland Jacquot, Jean-Louis Grieneisen
  • Patent number: 6765113
    Abstract: 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: Grant
    Filed: July 13, 2001
    Date of Patent: July 20, 2004
    Assignee: E.I. Du Pont de Nemours and Company
    Inventors: Derek Alexander Graham, Paul Anthony Hamley, Raymond Oliver, Martyn Poliakoff, Duncan Woodcock, Thomas Ilkenhans
  • Patent number: 6740776
    Abstract: 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: Grant
    Filed: July 15, 2002
    Date of Patent: May 25, 2004
    Assignee: Novartis AG
    Inventors: Ratna Shekhar, Michael John Girgis
  • Publication number: 20030208091
    Abstract: 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: Application
    Filed: May 19, 2003
    Publication date: November 6, 2003
    Inventors: Kazuo Tanaka, Hiroshi Ogawa, Ikutraro Maruki, Atsushi Okoshi
  • Publication number: 20030023115
    Abstract: A low temperature process for preparing an aromatic acid having formula (I), 1
    Type: Application
    Filed: July 15, 2002
    Publication date: January 30, 2003
    Inventors: Ratna Shekhar, Michael John Girgis
  • Patent number: 6476258
    Abstract: 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: Grant
    Filed: July 5, 2000
    Date of Patent: November 5, 2002
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masashi Komatsu, Junichi Ishikawa
  • Publication number: 20020151745
    Abstract: 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: Application
    Filed: February 28, 2002
    Publication date: October 17, 2002
    Inventors: Kazuo Tanaka, Hiroshi Ogawa, Ikutraro Maruki, Atsushi Okoshi
  • Publication number: 20020133043
    Abstract: 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: Application
    Filed: November 7, 2001
    Publication date: September 19, 2002
    Inventors: Yasutaka Sumida, Masahiro Wada, Noritaka Mizuno
  • Publication number: 20010016667
    Abstract: 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: 1
    Type: Application
    Filed: March 19, 2001
    Publication date: August 23, 2001
    Applicant: Toray Industries, Inc.
    Inventors: Shotaro Matsuoka, Masaaki Suematsu, Akira Kitamura
  • Patent number: 6255525
    Abstract: 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: Grant
    Filed: December 1, 1998
    Date of Patent: July 3, 2001
    Assignee: BP Amoco Corporation
    Inventors: David Lee Sikkenga, M. Michelle Morie-Bebel, Stephen V. Hoover
  • Patent number: 6245936
    Abstract: 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: Grant
    Filed: April 12, 1999
    Date of Patent: June 12, 2001
    Assignee: Rhodia Chimie
    Inventors: Pascal Metivier, Christian Maliverney, Philippe Denis
  • Patent number: 5998572
    Abstract: 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: Grant
    Filed: May 12, 1998
    Date of Patent: December 7, 1999
    Assignee: RPC Inc.
    Inventors: Ader M. Rostami, Mark W. Dassel, Eustathios Vassiliou, David C. DeCoster
  • Patent number: 5635197
    Abstract: 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: Grant
    Filed: March 21, 1995
    Date of Patent: June 3, 1997
    Assignee: Eli Lilly and Company
    Inventors: James E. Audia, Blake L. Neubauer
  • Patent number: 5629007
    Abstract: 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: Grant
    Filed: March 21, 1995
    Date of Patent: May 13, 1997
    Assignee: ELi Lilly and Company
    Inventors: James E. Audia, Blake L. Neubauer
  • Patent number: 5608106
    Abstract: 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: Grant
    Filed: May 11, 1995
    Date of Patent: March 4, 1997
    Assignee: Shell Oil Company
    Inventors: Herbert E. Fried, David M. Singleton, Raul A. Pabon, Jr.
  • Patent number: 5481032
    Abstract: 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: Grant
    Filed: November 29, 1993
    Date of Patent: January 2, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Ralf Pfirmann
  • Patent number: 5463114
    Abstract: 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: Grant
    Filed: April 13, 1994
    Date of Patent: October 31, 1995
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Wolf-Eckart Noack, Paul Schulz, F. Norman Tuller
  • Patent number: 5292934
    Abstract: 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: Grant
    Filed: June 18, 1992
    Date of Patent: March 8, 1994
    Assignee: Amoco Corporation
    Inventors: David L. Sikkenga, George E. Kuhlmann, Paul K. Behrens, Martin A. Zeitlin, Stephen V. Hoover
  • Patent number: 5239075
    Abstract: This invention relates to a process for the preparation of hexa- and octahydrobenzo[f]quinolin-3-ones.
    Type: Grant
    Filed: August 10, 1992
    Date of Patent: August 24, 1993
    Assignee: Eli Lilly and Company
    Inventors: James E. Audia, David E. Lawhorn
  • Patent number: 5237092
    Abstract: 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: Grant
    Filed: June 16, 1992
    Date of Patent: August 17, 1993
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Toru Tanaka, Kazuo Tanaka, Teruo Aratake
  • Patent number: 5223642
    Abstract: 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: Grant
    Filed: March 30, 1992
    Date of Patent: June 29, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Karl-Heinz Schonwalder
  • Patent number: 5157152
    Abstract: 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: Grant
    Filed: July 9, 1991
    Date of Patent: October 20, 1992
    Assignee: Ortec, Inc.
    Inventors: David L. Brotherton, Kwok W. Fung, Kam H. Wong
  • Patent number: 5095143
    Abstract: 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: Grant
    Filed: June 13, 1990
    Date of Patent: March 10, 1992
    Assignee: Amoco Corporation
    Inventors: Daniel L. Heberer, Paul R. Schiller, Virginia R. Seemann, Michael J. Yerkes
  • Patent number: 5087742
    Abstract: 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: Grant
    Filed: June 14, 1990
    Date of Patent: February 11, 1992
    Assignee: Kureha Kagaku Kogyo K.K.
    Inventors: Kazuo Yoshida, Nobuyuki Okubo, Toshiharu Matsuda, Yutaka Konai
  • Patent number: 5041634
    Abstract: 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: Grant
    Filed: December 1, 1988
    Date of Patent: August 20, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Martin Clausen, Paul Rys, Junkuan Wang
  • Patent number: 4990660
    Abstract: 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: Grant
    Filed: December 21, 1988
    Date of Patent: February 5, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Neumann, Ulrich Eichenauer
  • Patent number: 4981997
    Abstract: 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: Grant
    Filed: September 29, 1989
    Date of Patent: January 1, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Detlef-Ingo Schutze, Reinold Schmitz
  • Patent number: 4976893
    Abstract: 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: Grant
    Filed: June 18, 1986
    Date of Patent: December 11, 1990
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Ernst I. Leupold
  • Patent number: 4959494
    Abstract: 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: Grant
    Filed: July 6, 1987
    Date of Patent: September 25, 1990
    Assignee: Monsanto Company
    Inventor: Timothy R. Felthouse
  • Patent number: 4952721
    Abstract: 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: Grant
    Filed: March 8, 1989
    Date of Patent: August 28, 1990
    Assignee: Amoco Corporation
    Inventor: Kristi A. Fjare
  • Patent number: 4940808
    Abstract: 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: Grant
    Filed: July 7, 1988
    Date of Patent: July 10, 1990
    Assignee: Henkel Kommanditgesellschaft auf Aktien
    Inventors: Paul Schulz, Michael J. Virnig, Franz J. Carduck
  • Patent number: 4935540
    Abstract: 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: Grant
    Filed: December 12, 1988
    Date of Patent: June 19, 1990
    Inventor: Charles E. Sumner, Jr.
  • Patent number: 4892970
    Abstract: 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: Grant
    Filed: December 30, 1985
    Date of Patent: January 9, 1990
    Assignee: Amoco Corporation
    Inventors: Neal R. Nowicki, James D. Lowry, Jr.
  • Patent number: 4886906
    Abstract: 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: Grant
    Filed: January 6, 1989
    Date of Patent: December 12, 1989
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Toru Tanaka, Masato Inari
  • Patent number: 4804777
    Abstract: 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: Grant
    Filed: October 9, 1987
    Date of Patent: February 14, 1989
    Assignee: Eastman Kodak Company
    Inventors: Charles E. Sumner, Jr., Eric J. Fugate
  • Patent number: 4791224
    Abstract: 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: Grant
    Filed: April 7, 1988
    Date of Patent: December 13, 1988
    Assignee: Eastman Kodak Company
    Inventors: Charles E. Sumner, Jr., Eric J. Fugate
  • Patent number: 4778924
    Abstract: 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: Grant
    Filed: June 15, 1987
    Date of Patent: October 18, 1988
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Haruhisa Harada
  • Patent number: 4764638
    Abstract: 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: Grant
    Filed: August 12, 1986
    Date of Patent: August 16, 1988
    Assignee: Dynamit Nobel AG
    Inventor: Marcel Feld
  • Patent number: 4716245
    Abstract: 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: Grant
    Filed: April 18, 1986
    Date of Patent: December 29, 1987
    Assignee: Teijin Petrochemical Industries, Ltd.
    Inventor: Isao Hirose