Of Alkali Metal Phenolates Patents (Class 562/424)
  • Patent number: 8772209
    Abstract: Disclosed herein is a process for preparing a salt of a sulfurized alkyl-substituted hydroxyaromatic composition having a reduced content of unsulfurized alkyl-substituted hydroxyaromatic compound and its unsulfurized metal salt.
    Type: Grant
    Filed: November 20, 2012
    Date of Patent: July 8, 2014
    Assignee: Chevron Oronite Company LLS
    Inventors: Cedrick Mahieux, Richard Dutta, Curtis Campbell
  • Patent number: 8680325
    Abstract: The present invention provides a process for preparing 2,5-dihydroxyterephthalic acid which comprises reacting a dialkali metal salt of hydroquinone with carbon dioxide in a reaction medium in the presence of a potassium salt represented by formula (I): CnH2n+1COOK??(I) wherein n is an integer of 1-17. According to the process for preparing 2,5-dihydroxyterephthalic acid of the present invention, 2,5-dihydroxyterephthalic acid can be produced both safely and at a low cost under industrially advantageous conditions. Further, the process according to the present invention causes less damage to reaction equipment and the like.
    Type: Grant
    Filed: May 29, 2012
    Date of Patent: March 25, 2014
    Assignee: Ueno Fine Chemicals Industry, Ltd.
    Inventors: Yusuke Kita, Ryoichi Otsuka
  • Patent number: 7943796
    Abstract: An overbased salt of an oligomerized alkylhydroxyaromatic compound is disclosed, wherein the alkyl group of the alkylhydroxyaromatic compound is derived from an olefin mixture comprising propylene oligomers having an initial boiling point of at least about 195° C. and a final boiling point of no more than about 325° C. as measured by ASTM D86. Also disclosed is a lubricating oil composition containing at least (a) a major amount of an oil of lubricating viscosity and (b) the overbased salt of the oligomerized alkylhydroxyaromatic compound.
    Type: Grant
    Filed: July 31, 2008
    Date of Patent: May 17, 2011
    Assignee: Chevron Oronise Company LLC
    Inventors: Curtis B. Campbell, Charles Michael Cisson
  • Patent number: 7582787
    Abstract: Charge control agent whose active ingredient is a zinc compound of an alkylsalicylic acid derivative, the compound being a zincified alkylsalicylic acid derivative which is an alkylphenol derivative having a carboxyl group introduced thereto; Toner for developing electrostatic images, comprising said charge control agent, a coloring agent and a binder resin for toner; Charge control resin particles comprising solidified milled particles of a thermally kneaded mixture of at least said charge control agent and a resin.
    Type: Grant
    Filed: December 12, 2002
    Date of Patent: September 1, 2009
    Assignee: Orient Chemical Industries, Ltd.
    Inventors: Akihide Isoda, Tetsuji Kihara, Tohru Tsuruhara
  • Patent number: 7271287
    Abstract: There is provided a process for producing an aromatic hydroxycarboxylic acid which is capable of suppressing the formation of by-products and enhancing the selectivity of the intended product and is free from any purifying step. The process is characterized in that it is obtained by reacting an alkali metal salt of an aromatic hydroxy compound and carbon dioxide in a non-proton polar solvent in the presence of a solid basic catalyst.
    Type: Grant
    Filed: November 9, 2005
    Date of Patent: September 18, 2007
    Assignees: Chiba Institute of Technology, Nippon Oil Corporation
    Inventors: Tatsuaki Yamaguchi, Koichi Sato
  • Patent number: 7102028
    Abstract: The present invention provides a method for producing 3,5-di-tert-butyl-4-hydroxybenzoic acid comprising: (1) providing 2,6-di-tert-butylphenol which may contain up to 0.5% by weight of 3,3?,5,5?-tetra-tert-butyl-4,4?-dihydroxybiphenyl; (2) reacting a basic alkali metal compound with an excess amount of the 2,6-di-tert-butylphenol, which is in excess of the basic alkali metal compound, to give the alkali metal 2,6-di-tert-butylphenolate; and (3) reacting the alkali metal 2,6-di-tert-butylphenolate obtained in step (2) with carbon dioxide to give 3,5-di-tert-butyl-4-hydroxybenzoic acid. According to the method of the present invention, 3,5-di-tert-butyl-4-hydroxybenzoic acid can be obtained with high and stable yield.
    Type: Grant
    Filed: May 31, 2005
    Date of Patent: September 5, 2006
    Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo
    Inventor: Ryoichi Otsuka
  • Publication number: 20020147363
    Abstract: In one embodiment, the present invention provides a method of producing a homogeneous chemical reaction utilizing multiphase starting materials. The method includes the steps of providing a first reactant system embodied in a liquid and contacting the liquid with a second reactant system embodied in a gas. The liquid is arrayed in a form having dimensions such that the reaction rate of the homogeneous chemical reaction is essentially independent of the mass transport rate of the second reactant system into the liquid. The present invention further provides a method of performing simultaneous homogeneous chemical reactions utilizing multiphase reactant systems. The present invention is also directed to vessels for accommodating homogeneous chemical reactions.
    Type: Application
    Filed: March 28, 2002
    Publication date: October 10, 2002
    Applicant: General Electric Company
    Inventors: James Lawrence Spivack, Bruce Fletcher Johnson, John Yaw Ofori, Eric Douglas Williams
  • Patent number: 6423727
    Abstract: Disclosed as endothelin converting enzyme inhibitors are the compounds of the formula wherein the variables have the meanings as defined hereinbefore.
    Type: Grant
    Filed: October 16, 2000
    Date of Patent: July 23, 2002
    Assignee: Novartis AG
    Inventors: Stéphane De Lombaert, Cynthia Anne Fink, Fariborz Firooznia, Denton Wade Hoyer, Arco Yingcheu Jeng
  • Patent number: 6392090
    Abstract: A process for preparing a hydroxybenzoic acid is herein disclosed which comprises reacting a phenol with an alkali metal compound by the use of an aprotic polar organic solvent as a reaction solvent to form an alkali metal salt of the phenol, and then reacting this alkali metal salt with carbon dioxide to obtain a hydroxybenzoic acid, said process comprising the step of carrying out the reaction under conditions that a molar ratio of the phenol to the total of the alkali metal compound and the aprotic polar organic solvent is larger than 1. Furthermore, the process may contain the steps of precipitating crystals from the reaction solution, separating the solid from the solution to obtain a wet alkali metal salt of the hydroxybenzoic acid, dissolving the wet alkali metal salt in water, and precipitating crystals from the solution by acidification to obtain the hydroxybenzoic acid.
    Type: Grant
    Filed: September 26, 1997
    Date of Patent: May 21, 2002
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Masayuki Furuya, Akinori Nagatomo, Masaru Wada
  • Patent number: 6316665
    Abstract: An oxidation free process for converting a hydroxy substituted aromatic to an aromatic diacid which comprises reacting a hydroxy substituted aromatic with excess basic salt in the presence of carbon dioxide at disproportionation/isomerization reaction conditions.
    Type: Grant
    Filed: August 22, 2000
    Date of Patent: November 13, 2001
    Assignee: Shell Oil Company
    Inventors: Thomas Fairchild Brownscombe, Garo Vaporciyan, Narayana Mysore, Susan Secor Pfrehm
  • Patent number: 6133475
    Abstract: The present invention relates to a process for preparing 2-hydroxynaphthalene-3,6-dicarboxylic acid which comprises reacting potassium 2-naphtholate and carbon dioxide at a temperature 290.degree. C. or higher under a pressure 30 kg/cm.sup.2 (G) or higher. According to this process, 2-hydroxynaphthalene-3,6-dicarboxylic acid can be obtained in high yield.
    Type: Grant
    Filed: June 16, 1998
    Date of Patent: October 17, 2000
    Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo Kenkujo
    Inventors: Ryuzo Ueno, Masaya Kitayama, Yoshiro Uchiyama, Syungo Nara
  • Patent number: 6107516
    Abstract: A process for the production of aromatic hydroxycarboxylic acids such as salicylic acid comprising contacting an aromatic hydroxy compound such as phenol with carbon dioxide in the presence of fluoride ion. The products are useful as pharmaceuticals and chemical intermediates, and as monomers for polymers.
    Type: Grant
    Filed: November 17, 1998
    Date of Patent: August 22, 2000
    Assignee: E. I. du Pont de Nemours and Company
    Inventor: Arthur William Anderson
  • Patent number: 6040478
    Abstract: A process is disclosed for dicarboxylating dihydric phenols, notably those where the hydroxyl groups are in the para or the ortho position vis-a-vis one another. More particularly, the invention pertains to a process for preparing 2,5-dihydroxyterephthalic acid (2,5 DHTA). The invention comprises contacting a dihydric phenol with carbon dioxide in the presence of an alkali metal carbonate, the reaction being carried out in the presence of an alkali metal formate, at a temperature above the formate's melting point. The invention has several advantages over the well-known Kolbe-Schmitt reaction and other known carboxylation reactions, such as a lower operating pressure, higher yields, and/or shorter reaction times.
    Type: Grant
    Filed: May 1, 1998
    Date of Patent: March 21, 2000
    Assignee: Akzo Nobel N.V.
    Inventors: Doetze Jakob Sikkema, Adrianus Maria Reichwein
  • Patent number: 6028218
    Abstract: Alkali metal aryloxides may be speedily dried by removing water while the aryloxide is molten. Such dried alkoxides are useful as chemical intermediates. Molten alkali metal aryloxides may be contacted with carbon dioxide to quickly produce the dialkali metal salts of aromatic hydroxycarboxylic acids, which upon acidification yield the corresponding aromatic hydroxycarboxylic acids. Aromatic hydroxycarboxylic acids are useful as chemical intermediates and as monomers for polymers. Solid metal aryloxides may be reacted with carbon dioxide in a reactor in which the contents, even when pasty, may be agitated so that the reaction is more rapid than in prior methods.
    Type: Grant
    Filed: April 4, 1997
    Date of Patent: February 22, 2000
    Assignee: E.I. du Pont de Nemours and Company
    Inventors: Michael Robert Samuels, Ronald M. Yabroff
  • Patent number: 5977405
    Abstract: Alkali metal aryloxides may be speedily dried by removing water while the aryloxide is molten. Such dried alkoxides are useful as chemical intermediates. Molten alkali metal aryloxides may be contacted with carbon dioxide to quickly produce the dialkali metal salts of aromatic hydroxycarboxylic acids, which upon acidification yield the corresponding aromatic hydroxycarboxylic acids. Aromatic hydroxycarboxylic acids are useful as chemical intermediates and as monomers for polymers. Solid metal aryloxides may be reacted with carbon dioxide in a reactor in which the contents, even when pasty, may be agitated so that the reaction is more rapid than in prior methods.
    Type: Grant
    Filed: November 10, 1998
    Date of Patent: November 2, 1999
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Michael Robert Samuels, Ronald M. Yabroff
  • Patent number: 5756853
    Abstract: The subject of the present invention is a process for the preparation of a 4-hydroxybenzaldehyde carrying at least one substituent in the position ortho to the OH group.It more particularly relates to the preparation of 3-methoxy-4-hydroxybenzaldehyde and of 3-ethoxy-4-hydroxybenzaldehyde.The process for the preparation of a substituted 4-hydroxybenzaldlehyde, substituted at least in the 3 position by an alkoxy group, is characterized in that it comprises subjecting a substituted phenol compound, substituted at least in the 2 position by an alkoxy group and in which the 4 and 6 positions are free, to a first stage of carboxylation in the 6 position, then to a stage of hydroxymethylation in the 4 position, followed by a stage of oxidation of the hydroxymethyl group to a formyl group, and finally to a last decarboxylation stage.
    Type: Grant
    Filed: October 16, 1996
    Date of Patent: May 26, 1998
    Assignee: Rhone-Poulenc Chimie
    Inventors: Pascal Metivier, Isabelle Jouve, Christian Maliverney
  • Patent number: 5643494
    Abstract: A process for the preparation of aromatic hydroxy carboxylic acids by reacting alkali metal phenolates or alkali metal naphtholates with alkali metal carbonates and carbon monoxide, with subsequent acidification, wherein the solid starting materials--alkali metal carbonate and/or alkali metal phenolate or naphtholate--are metered into the reaction mixture in the form of one or more dispersions in an inert organic liquid.The process according to the invention enables the preparation of aromatic hydroxy carboxylic acids in good yields and with high chemical selectivity. Additional measures for increasing the selectivity, as described for example for the Kolbe-Schmitt reaction in EP-A 0 053 824, EP-A 0 081 753 and EP-A 0 254 596, and for the reaction with CO and carbonate in, for example, WO 91/11422, are unnecessary.
    Type: Grant
    Filed: June 1, 1995
    Date of Patent: July 1, 1997
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Siegbert Rittner, Hans-Martin Ruffer, Jorg Schmid, Thomas Wisser
  • Patent number: 5532406
    Abstract: A process for preparing aromatic hydroxycarboxylic acids or di-salts thereof by reaction of alkali metal phenolates or naphtholates with carbon dioxide, in the presence or absence of a further alkali metal salt, which comprises introducing the solid phenolate or naphtholate starting materials and, if desired, the alkali metal salt into the reaction mixture batchwise or continuously, separately or together, in the form of a dispersion in an inert organic liquid.The process of the invention makes possible the preparation of aromatic hydroxycarboxylic acids in good yields and with high chemical selectivity. Additional measures for increasing the selectivity, as are described for the Kolbe-Schmitt reaction in, for example, EP-A 0 053 824, EP-A 0 081 753 and EP-A 0 254 596, can be omitted.
    Type: Grant
    Filed: May 19, 1994
    Date of Patent: July 2, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Siegbert Rittner, Hans-Martin Ruffer, Jorg Schmid, Thomas Wisser
  • Patent number: 5493048
    Abstract: The new fluoro-trifluoromethylbenzoic acid derivatives of the general formula (I) ##STR1## wherein the substituents R, R.sup.1, R.sup.2, R.sup.3, R.sup.4 and R.sup.5 have the meaning given in the description, are suitable as starting substances for the preparation of antibacterial agents and feed additives.
    Type: Grant
    Filed: January 12, 1994
    Date of Patent: February 20, 1996
    Assignee: Bayer Aktiengesellschaft
    Inventors: Albrecht Marhold, Peter Andres
  • Patent number: 5393332
    Abstract: Herein disclosed is a method for preparing a nuclear-substituted salicylic acid or a metal salt thereof represented by the following general formula (1): ##STR1## [wherein R.sub.1 and R.sub.2 each represents a t-butyl group, a t-amyl group, a t-octyl group, an isononyl group or an isododecyl group, provided that at least one of R.sub.1 and R.sub.2 represents an isononyl group or an isododecyl group; M represents a hydrogen atom or a metal atom; and n is the atomic valency of the metal atom M] which comprises the step of subjecting, to a Kolbe-Schmitt reaction, an alkali metal salt of a nuclear-substituted phenol represented by the following general formula (2): ##STR2## [wherein R.sub.1 and R.sub.2 are the same as those defined above] in which 100 to 50% of the alkali metal salt is potassium salt and 0 to 50% thereof is sodium salt, in a substantially water-insoluble solvent as a reaction medium.
    Type: Grant
    Filed: December 9, 1993
    Date of Patent: February 28, 1995
    Assignees: Sanko Kaihatsu Kagaku Kenkyusho, Kanzaki Paper Manufacturing Co., Ltd.
    Inventors: Toranosuke Saito, Takashi Ishibashi, Eiji Kawabata, Masato Tanaka, Toshio Kimura
  • Patent number: 5124477
    Abstract: The improved process for preparing para-hydroxybenzoic acid comprises reacting potassium phenol with carbon dioxide in an inert reaction medium or without using a reaction medium in the presence of at least one compound selected from the group consisting of the compounds represented by the following general formula I or II: ##STR1## at a reaction temperature of 230.degree.-450.degree. C. and at a carbon dioxide pressure ranging from atmospheric pressure to 6 kg/cm.sup.2 (G). The process may comprise two stages and the first-stage reaction described above is followed by the second stage in which the reaction is further continued with the pressure of carbon dioxide in the system being reduced and/or the reaction temperature being elevated within the range specified above.Also, phenol may be used as the starting material instead of potassium phenolate.
    Type: Grant
    Filed: December 11, 1989
    Date of Patent: June 23, 1992
    Assignee: Kawasaki Steel Corporation
    Inventors: Toshinobu Suzuki, Makiko Ijiri, Hitoshi Saima, Tadahiro Wakui, Tokio Iizuka, Akinori Matsuura
  • Patent number: 5072036
    Abstract: Para-hydroxybenzoic acid is prepared by reacting an alkali metal salt of phenol except the lithium and sodium salts with carbon dioxide in the presence of at least one compound selected from compounds of the following formulae (I) and (II): ##STR1## In formulae (I) and (II), M is an alkali metal except lithium and sodium; R is any substituent except an aliphatic hydroxy group having up to 4 carbon atoms, an aliphatic mercapto group having up to 4 carbon atoms, a substituent having at least one of them as its structural unit, and a hydrogen atom; R' is any substituent except an aliphatic hydroxy group having up to 4 carbon atoms, an aliphatic mercapto group having up to 4 carbon atoms, and a substituent having at least one of them as its structural unit; in formula (I) n is an integer of 1 to 5, and R groups may be the same or different when n is more than one; in formula (II) m is an integer of 1 to 5 and l is an integer of 0 to 4, and M alkali metals may be the same or different when m is one or more, and R'
    Type: Grant
    Filed: June 14, 1989
    Date of Patent: December 10, 1991
    Assignee: Kawasaki Steel Corporation
    Inventors: Toshinobu Suzuki, Makiko Ijiri, Tokio Iizuka, Hitoshi Saima, Tadahiro Wakui
  • Patent number: 5047422
    Abstract: New 8-substituted 2-aminotetralins can be prepared from the corresponding aminotetralins or tetralones. They can be used in medicaments.
    Type: Grant
    Filed: July 13, 1990
    Date of Patent: September 10, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bodo Junge, Bernd Richter, Thomas Glaser, Jorg Traber, George S. Allen
  • Patent number: 4996354
    Abstract: 2,4-Dihydroxybenzoic acid is prepared in a solids mixer by reacting resorcinol with an alkali metal bicarbonate and/or alklai metal carbonate in a carbon dioxide atmosphere using as the alkali metal bicarbonate or alkali metal carbonate a mixture of the corresponding sodium and potassium salts.
    Type: Grant
    Filed: September 1, 1989
    Date of Patent: February 26, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Peter Neumann, Ulrich Eichenauer
  • Patent number: 4966992
    Abstract: The present invention provides a method of production of aromatic hydroxycarboxylic acids by the reaction of alkaline metal salts of phenols or naphthols with carbon dioxide, in which free phenols or free naphthols produced as by-products in the reaction system are removed from the system so as to control the content of free phenols or free naphthols at a suitable level, by which a purer objective compound can be obtained at high yield under the condition of lower temperature and shorter time.
    Type: Grant
    Filed: January 18, 1989
    Date of Patent: October 30, 1990
    Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo Kenkyujo
    Inventors: Ryuzo Ueno, Yoshiyasu Masada, Yoshihiko Kuwae, Keiji Kawata
  • Patent number: 4950781
    Abstract: A process for the preparation of aromatic hydroxycarboxylic acids by reacting alkali metal salts of phenol with carbon dioxide in organic phosphine oxides containing straight or branched alkyl groups having from 1 to 8 carbon atoms and phenyl groups.
    Type: Grant
    Filed: November 21, 1989
    Date of Patent: August 21, 1990
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Takehisa Nakanishi, Toshizumi Miura, Masao Hashimoto
  • Patent number: 4814495
    Abstract: In the Kolbe-Schmitt process for the preparation of hydroxybenzoic acid by the reaction of potassium phenolate with carbon dioxide gas followed by precipitation of the hydroxybenzoic acid in the mixture acidified with hydrochloric acid, the potassium value in the acidified mother liquor is conventionally recovered by electrolysis after removing the organic impurities by chlorination with chlorine. The disadvantages in the use of chlorine can be dissolved by replacing the chlorine treatment with (a) dehydration of the acidified mother liquor followed by calcination of the dehydrated product, (b) salting-out by blowing hydrogen chloride gas into the acidified mother liquor, or (c) reverse osmosis treatment prior to the electrolysis to convert potassium chloride into potassium hydroxide, for example, by using an ion exchange membrane.
    Type: Grant
    Filed: June 6, 1988
    Date of Patent: March 21, 1989
    Assignee: Idemitsu Petrochemical Co., Ltd.
    Inventors: Tsunenori Sakai, Toshio Ishiguro, Takaya Ishihara
  • Patent number: 4780567
    Abstract: This invention provides a process for selectively producing aromatic hydroxycarboxylic acids, which comprises subjecting a liquid mixture consisting of a polycyclic aromatic hydrocarbon, an alkali metal salt of an aromatic hydroxy compound and a free aromatic hydroxy compound to a reaction with carbon dioxide. The process permits the production of the intended product with enhanced selectivity.
    Type: Grant
    Filed: July 1, 1986
    Date of Patent: October 25, 1988
    Assignee: Kabushiki Kaisha Ueno Seiyaku Oyo Kenkuyo
    Inventors: Ryuzo Ueno, Toshiharu Kanagae, Mitsuyuki Kishimoto
  • Patent number: 4767768
    Abstract: New Nitro aliphatic compounds and their pharmaceutically acceptable salts are disclosed.
    Type: Grant
    Filed: December 8, 1983
    Date of Patent: August 30, 1988
    Assignee: Fujisawa Pharmaceutical Co., Ltd.
    Inventors: Masanori Okamoto, Morita Iwami, Shigehiro Takase, Itsuo Uchida, Kazuyoshi Umehara, Masanobu Kohsaka, Hiroshi Imanaka
  • Patent number: 4730083
    Abstract: An improved process for the preparation of 3,5-dialkyl-4-hydroxybenzoic acid comprising the reaction of 2,6-dialkylphenol and carbon dioxide in the presence of a mono- or polyalkylene glycol ether.
    Type: Grant
    Filed: August 18, 1986
    Date of Patent: March 8, 1988
    Assignee: Ciba-Geigy Corporation
    Inventors: Stephen D. Pastor, John D. Spivack, Paul Odorisio
  • Patent number: 4529817
    Abstract: Aromatic hydroxycarboxylic acids are prepared by reacting an alkali metal salt of an aromatic hydroxy compound in solid phase with carbon dioxide, by reacting an alkali metal salt of an aromatic hydroxy compound in the form of granules in a fluidized bed with carbon dioxide, if desired under elevated pressure, at first at temperatures of 20.degree. to 130.degree. C. until at least 40% of the hydroxy compound has been converted into the corresponding carbonate, then completing the reaction at temperatures of 135.degree. to 300.degree. C., and then converting the reaction product obtained into the free acid.
    Type: Grant
    Filed: March 7, 1983
    Date of Patent: July 16, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Stopp, Horst Karkossa, Viktor Trescher
  • Patent number: 4508920
    Abstract: Aromatic hydroxycarboxylic acids are prepared by reacting alkali metal salts of aromatic hydroxy compounds in the solid phase with carbon dioxide in a process in which the alkali metal salt of the aromatic hydroxy compound is reacted at temperatures of 120.degree. to 300.degree. C., in the form of granules, in a fluidized bed with carbon dioxide, if appropriate under elevated pressure and, if appropriate, in the presence of the aromatic hydroxy compound in the form of vapor, with continuous removal, by means of excess carbon dioxide, of the aromatic hydroxy compound which is formed, until at least 40% of the hydroxy compound have been converted into the alkali metal salt of the corresponding hydroxycarboxylic acid, and, if appropriate, the resulting alkali metal salt of the hydroxycarboxylic acid is reacted further in a subsequent stage at temperatures of 150.degree. to 300.degree. C.
    Type: Grant
    Filed: March 7, 1983
    Date of Patent: April 2, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Stopp, Horst Karkossa, Viktor Trescher
  • Patent number: 4376867
    Abstract: An improved process for the production of sodium salicylate and salicylic acid from phenol at a high degree of conversion with a concomitant reduction in undesirable by-products. The process comprises reacting a sodium phenolate with carbon dioxide in a direct, single step at a temperature above about 165.degree. C. to produce directly sodium salicylate, which is then converted by conventional means to the salicylic acid.
    Type: Grant
    Filed: July 7, 1981
    Date of Patent: March 15, 1983
    Inventors: Gert Jansen, Per Wolff
  • Patent number: 4345095
    Abstract: The production of 6-hydroxy-2-naphthoic acid from anhydrous potassium 2-naphthoxide and carbon dioxide is improved by forming a mixture of 0.8-1.45 moles of 2-hydroxynaphthalene per equivalent of potassium base, dehydrating the mixture, adding carbon dioxide at about 20 to 90 psi at about 255.degree.-280.degree. C. and agitating and heating at said pressure and temperature.
    Type: Grant
    Filed: June 11, 1981
    Date of Patent: August 17, 1982
    Assignee: American Cyanamid Company
    Inventors: Michael J. Mueller, Carroll S. Montgomery
  • Patent number: 4345094
    Abstract: The production of 6-hydroxy-2-naphthoic acid from anhydrous potassium 2-naphthoxide and carbon dioxide is improved by forming a mixture of 0.8-1.2 moles of 2-hydroxynaphthalene per equivalent of potassium base, dehydrating the mixture, adding carbon dioxide at about 20 to 90 psi at about 255.degree.-280.degree. C. and agitating and heating it at said pressure and temperature.
    Type: Grant
    Filed: June 2, 1981
    Date of Patent: August 17, 1982
    Assignee: American Cyanamid Company
    Inventors: Michael J. Mueller, Carroll S. Montgomery
  • Patent number: 4287357
    Abstract: The production of 6-hydroxy-2-naphthoic acid from anhydrous potassium 2-naphthoxide and carbon dioxide is improved by forming a mixture of 0.8-1.2 moles of 2-hydroxynaphthalene per equivalent of potassium base, dehydrating the mixture, adding carbon dioxide at about 20 to 90 psi at about 255.degree.-280.degree. C. and agitating and heating it at said pressure and temperature.
    Type: Grant
    Filed: March 6, 1980
    Date of Patent: September 1, 1981
    Assignee: American Cyanamid Company
    Inventors: Michael J. Mueller, Carroll S. Montgomery
  • Patent number: 4239913
    Abstract: A process for preparing 2-hydroxynaphthalenecarboxylic acids which comprises reacting a liquid mixture of 1 mole of an alkali .beta.-naphtholate, 0.05 to 3 moles of .beta.-naphthol, and 0.1 to 5 times the weight of the alkali .beta.-naphtholate of light oil or kerosene with carbon dioxide under a carbon dioxide pressure of not more than 15 kg/cm.sup.2.G at a temperature of at least 180.degree. C.
    Type: Grant
    Filed: August 15, 1978
    Date of Patent: December 16, 1980
    Assignee: Kabushiki Kaisha Veno Seiyaku Oyo Kenkyujo
    Inventors: Ryuzo Ueno, Hiroaki Tsuchiya, Yasukazu Muramoto, Yoshihiko Kuwae
  • Patent number: 4232172
    Abstract: An improved process for the preparation of 3,6-dichlorosalicylic acid by carboxylation of potassium 2,5-dichlorophenolate with carbon dioxide in xylene at elevated pressure, where the improvement consists of adding finely powdered, anhydrous potassium carbonate to the reaction mixture, whereby the yield of 3,6-dichloro-salicylic acid is significantly increased.
    Type: Grant
    Filed: February 15, 1978
    Date of Patent: November 4, 1980
    Assignee: Celamerck GmbH & Co. KG
    Inventors: Manfred Becher, Richard Sehring