Preparation By Carbonation Patents (Class 562/423)
  • Patent number: 9073844
    Abstract: The invention relates to a process for preparing a propiolic acid or a derivative thereof by reacting a terminal alkyne with carbon dioxide, which comprises performing the reaction in the presence of a base and a copper complex, especially a copper (I) complex having at least one ligand, at least one of the ligands of the copper complex being selected from monodentate ligands which have an aminic or iminic nitrogen atom capable of coordination with copper, and polydentate ligands having at least two atoms or atom groups which are capable of simultaneous coordination with copper and are selected from nitrogen, oxygen, sulfur, phosphorus and carbene carbon.
    Type: Grant
    Filed: August 19, 2011
    Date of Patent: July 7, 2015
    Assignee: BASF SE
    Inventors: Lukas J. Goossen, Nuria Rodriguez Garrido, Filipe Manjolinho Costa, Paul P. Lange
  • Patent number: 9067867
    Abstract: Disclosed is a process for preparing 5-aminosalicylic acid by gas phase catalytic carboxylation, characterized in that carbon dioxide is introduced into a system of p-acetaminophenol and a basic compound at a temperature of 150° C.˜220° C. and a pressure of 0.5˜5.0 MPa in the presence of a catalyst, so as to carry out a gas phase catalytic carboxylation reaction to form a 5-aminosalicylate, and the crude product 5-aminosalicylate is separated, and then acidified to prepare 5-aminosalicylic acid (5-ASA). Since the gas phase catalytic reaction replaces a solid phase thermo-chemical reaction, the reaction is significantly improved in terms of the process flow, reaction conditions, product quality and energy consumption. In addition, the reaction has a short reaction time, good selectivity, high yield and no formation of wastes during the reaction, and is suitable for industrial production.
    Type: Grant
    Filed: October 20, 2011
    Date of Patent: June 30, 2015
    Assignees: Zhejiang Huahai Pharmaceutical Co., Ltd., Huazhong University Of Science And Technology
    Inventors: Guangxing Li, Jinjin Li, Dajian Zhu, Qiang Jiang, Lingli Cai, Yong Xie, Lixin Gan
  • Publication number: 20150099886
    Abstract: The present application relates to a preparation method for solid powder of a carbamic acid derivative, which includes reacting an amine derivative with carbon dioxide at a temperature in a range of from about ?30° C. to about 500° C. and at a pressure in a range of from about 0.3 MPa to about 100 MPa. In addition, the present disclosure relates to a reduction method for solid powder of a carbamic acid derivative to an amine derivative and carbon dioxide, which includes dissolving solid powder of the carbamic acid derivative prepared in a solvent; refluxing the carbamic acid derivative at a temperature in a range of from about 30° C. to about 100° C.; and evaporating the solvent.
    Type: Application
    Filed: December 11, 2014
    Publication date: April 9, 2015
    Inventors: Nam Hwi HUR, Byeong No LEE
  • Patent number: 8816127
    Abstract: The present invention describes a process for converting a terminal alkyne into an alkynoic acid. In this process the alkyne is exposed to carbon dioxide in the presence of a copper (I) species, a base and a complexing agent capable of complexing copper (I).
    Type: Grant
    Filed: December 16, 2010
    Date of Patent: August 26, 2014
    Assignee: Agency for Science Technology and Research
    Inventors: Yugen Zhang, Dingyi Yu
  • Patent number: 8796459
    Abstract: The invention provides synthetic processes and synthetic intermediates that can be used to prepare 4-oxoquinolone compounds having useful integrase inhibiting properties.
    Type: Grant
    Filed: September 14, 2012
    Date of Patent: August 5, 2014
    Assignee: Gilead Sciences, Inc.
    Inventors: Eric Dowdy, Xi Chen, Steven Pfeiffer
  • Patent number: 8759525
    Abstract: The invention provides synthetic processes and synthetic intermediates that can be used to prepare 4-oxoquinolone compounds having useful integrase inhibiting properties.
    Type: Grant
    Filed: April 23, 2013
    Date of Patent: June 24, 2014
    Assignee: Gilhead Sciences, Inc.
    Inventors: Eric Dowdy, Steven Pfeiffer
  • 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
  • Publication number: 20140012000
    Abstract: The invention relates to a process for preparing a propiolic acid or a derivative thereof by reacting a terminal alkyne with carbon dioxide, which comprises performing the reaction in the presence of a base and a copper complex, especially a copper (I) complex having at least one ligand, at least one of the ligands of the copper complex being selected from monodentate ligands which have an aminic or iminic nitrogen atom capable of coordination with copper, and polydentate ligands having at least two atoms or atom groups which are capable of simultaneous coordination with copper and are selected from nitrogen, oxygen, sulfur, phosphorus and carbene carbon.
    Type: Application
    Filed: August 19, 2011
    Publication date: January 9, 2014
    Applicant: BASF SE
    Inventors: Lukas J Goossen, Nuria Rodriguez Garrido, Filipe Manjolinho Costa, Paul P. Lange
  • Publication number: 20130253200
    Abstract: The invention provides synthetic processes and synthetic intermediates that can be used to prepare 4-oxoquinolone compounds having useful integrase inhibiting properties.
    Type: Application
    Filed: April 23, 2013
    Publication date: September 26, 2013
    Applicant: Gilead Sciences, Inc.
    Inventors: Eric Dowdy, Steven Pfeiffer
  • Publication number: 20130018204
    Abstract: Disclosed is an edge-functionalized graphitic material manufactured by using a mechanochemical process. The edge-functionalized graphitic material is manufactured by pulverizing graphite in the presence of a variety of atmospheric agents in the form of gas phase, liquid phase, or solid phase. The edge-functionalized graphitic material, which is a precursor applicable into various fields, is expected to replace the prior art oxidized graphite.
    Type: Application
    Filed: October 10, 2011
    Publication date: January 17, 2013
    Applicant: UNIST Academy-Industry Research Corporation
    Inventors: In Yup JEON, Jong Beom BAEK
  • Publication number: 20120310008
    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: Application
    Filed: May 29, 2012
    Publication date: December 6, 2012
    Applicant: UENO FINE CHEMICALS INDUSTRY, LTD.
    Inventors: Yusuke KITA, Ryoichi OTSUKA
  • Publication number: 20120142961
    Abstract: A method produces a radiopharmaceutical. In the method, an H—Li exchange is made by adding an alkyllithium to an isocyanide, wherein the ?-H atom of the isocyanide is replaced with an Li atom. 11CO2 is added and bonded to the ?-C atom of the isocyanide. By a two-stage hydrolysis, the Li atom is replaced with an H atom and an amino group is formed from the isocyanide group, for example, by adding NH4Cl and HI. The reaction is continuously performed in particular in a microfluidic structure so that reaction times of less than 300 seconds can be achieved for the partial steps. Because the produced radiopharmaceutical has only a low half-life, the short production time has a positive effect on the yield of radioactive pharmaceutical.
    Type: Application
    Filed: March 31, 2010
    Publication date: June 7, 2012
    Applicant: SIEMENS AKTIENGESELLSCHAFT
    Inventors: Markus Kinzl, Oliver Lade, Christan P. Schultz, Amo Steckenborn, Frank Thalmann
  • Patent number: 8153801
    Abstract: The invention provides synthetic processes and synthetic intermediates that can be used to prepare 4-oxoquinolone compounds having useful integrase inhibiting properties.
    Type: Grant
    Filed: September 11, 2008
    Date of Patent: April 10, 2012
    Assignee: Gilead Sciences, Inc.
    Inventors: Eric Dowdy, Steven Pfeiffer
  • Publication number: 20100292480
    Abstract: The invention provides synthetic processes and synthetic intermediates that can be used to prepare 4-oxoquinolone compounds having useful integrase inhibiting properties.
    Type: Application
    Filed: September 11, 2008
    Publication date: November 18, 2010
    Applicant: Gilead Sciences, Inc
    Inventors: Eric Dowdy, Steven Pfeiffer
  • Patent number: 7812190
    Abstract: The invention provides improved therapeutic and diagnostic fullerenes and endohedral fullerenes. The fullerenes and endohedral fullerenes of the invention are derivatized with at least two charged functional groups (and preferably more than two charged functional groups) to provide for water-solubility and improved in vivo biodistribution. Improved derivatized fullerenes and endohedral fullerenes carry a plurality of functional groups at least two of which are charged. Preferably at least about ? of the possible derivations sites on the fullerene caged carry derivatives and preferably at least about ½ of the functional groups on the fullerene cage are charged groups. The invention also provides water-soluble endohedral metallofullerene with improved biodistribution which are useful as in vivo imaging agents, including MRI contrast agents.
    Type: Grant
    Filed: April 9, 2003
    Date of Patent: October 12, 2010
    Assignee: TDA Research, Inc.
    Inventors: Robert D. Bolskar, J. Michael Alford
  • Patent number: 7432390
    Abstract: In the production of carboxylic acid or carboxylic acid ester, a reaction product containing the carboxylic acid or carboxylic acid ester which has been produced by the reaction of an olefin, carbon monoxide, and water or an alcohol in the presence of HF is heat-treated in the presence of an acid catalyst and an acid adsorbent. By the heat treatment, the contamination of the carboxylic acid or carboxylic acid ester with HF and/or fluorine compounds such as acyl fluorides can be prevented, to enable the stable production of a high quality and high purity carboxylic acid or carboxylic acid ester without causing troubles such as corrosion of apparatus.
    Type: Grant
    Filed: March 9, 2006
    Date of Patent: October 7, 2008
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Mitsuharu Kitamura, Kinji Kato
  • Patent number: 6562999
    Abstract: Disclosed is a process for purifying 2,6-naphthalene dicarboxylic acid produced by disproportionation and more efficiently recycling byproduct dipotassium salts which includes the steps of: a) Contacting an aqueous solution containing the disalt of 2,6-NDA(2,6-K2NDA) with carbon dioxide to form as a precipitate the monopotassium salt of 2,6-NDA (KHNDA) and an aqueous solution containing 2,3-KHNDA, K2NDA, and potassium bicarbonate; b) Disproportionating said monopotassium salt (KHNDA) to form 2,6-NDA and an aqueous solution containing K2NDA, and potassium bicarbonate; c) Separating said 2,6-NDA and concentrating said aqueous solution containing K2NDA and potassium bicarbonate by reverse osmosis.
    Type: Grant
    Filed: January 9, 2002
    Date of Patent: May 13, 2003
    Assignee: Mossi & Ghisolfi Overseas S.A.
    Inventors: Zaida Diaz, John B. Rodden
  • Publication number: 20030078436
    Abstract: The present invention relates to a process for the catalytic preparation of N-acylglycine derivatives. More particularly, the present invention relates to a process for the catalytic preparation of N-acylglycine derivatives by reacting an aldehyde with a carboxamide and carbon monoxide in the presence of a palladium compound, an ionic halide and an acid as catalyst.
    Type: Application
    Filed: October 25, 2002
    Publication date: April 24, 2003
    Inventors: Holger Geissler, Sandra Bogdanovic, Matthias Beller, Markus Eckert, Frank Vollmuller
  • Publication number: 20020156313
    Abstract: The present invention is a process for the preparation of a compound of formula 1
    Type: Application
    Filed: January 8, 2002
    Publication date: October 24, 2002
    Inventors: Fabienne Hoffmann-Emery, Michelangelo Scalone, Paul Spurr
  • Patent number: 6441224
    Abstract: Disclosed is a method for selective carboxylation of naphthoic acid, or other aromatic mono-acids to form primarily 2,3-naphthalene dicarboxylic acid (2,3-NDA) or other aromatic diacids which comprises reacting said aromatic mono-acid in the presence of one or more metal oxide catalysts, alone, or in combination, and in the presence of about 0.2 to 0.8 moles excess of base over aromatic mono-acid, at a temperature of about 380° C. to about 420° C., and, in a second step, disproportionating the product of said selective carboxylation at a temperature above about 420° C. to form a product with a greatly improved yield of 2,6-naphthalene dicarboxylic acid, or other aromatic dicarboxylic acid.
    Type: Grant
    Filed: August 22, 2000
    Date of Patent: August 27, 2002
    Assignee: Mossi & Ghisolfi Overseas, S. A.
    Inventors: Thomas Fairchild Brownscombe, Donn Anthony DuBois, Susan Secor Pfrehm, William Larry King
  • Publication number: 20020091286
    Abstract: The invention relates to a process for the preparation of ortho-alkylated benzoic acid derivatives of the formula I 1
    Type: Application
    Filed: January 8, 2002
    Publication date: July 11, 2002
    Applicant: Merck GmbH
    Inventor: Ekkehard Bartmann
  • Patent number: 6350904
    Abstract: The invention relates to a process for the preparation of ortho-alkylated benzoic acid derivatives of the formula I characterized in that an aryl bromide of the formula II is reacted with a secondary or tertiary organolithium compound and CO2.
    Type: Grant
    Filed: April 5, 2001
    Date of Patent: February 26, 2002
    Assignee: Merck KGaA
    Inventors: Ekkehard Bartmann, Ingeborg Stein
  • Patent number: 6348624
    Abstract: The subject invention involves processes for making 2,4-difluoro-3-Q1-benzoic acid, wherein Q1 is derived from an electrophilic reagent, comprising the steps of: (a) treating 1-bromo-2,4-difluorobenzene with a strong, non-nucleophilic base; then treating with an electrophilic reagent which provides Q1, or a functional moiety which is then transformed to Q1, producing 1-bromo-2,4-difluoro-3-Q1-benzene; (b) treating the 1-bromo-2,4-difluoro-3-Q1-benzene with an alkali or alkaline earth metal or organometallic reagent; then treating with carbon dioxide, or with a formylating agent followed by oxidation, to produce 2,4-difluoro-3-Q1-benzoic acid. The subject invention also involves optional additional steps to further modify Q1, or to substitute a non-hydrogen moiety at the 5-position, at the 6-position, or at both, of the phenyl ring of the 2,4-difluoro-3-Q1-benzoic acid.
    Type: Grant
    Filed: December 17, 1998
    Date of Patent: February 19, 2002
    Assignee: The Procter & Gamble Co.
    Inventors: Benoit Ledoussal, Xiaomin Sharon Zheng, Ji-In Kim Almstead, Jeffrey Lyle Gray
  • Publication number: 20010036653
    Abstract: The invention provides a multistep synthesis for the preparation of 4,5-diamino shikimic acid derivatives of formula 1
    Type: Application
    Filed: March 19, 2001
    Publication date: November 1, 2001
    Inventors: Hans Iding, Beat Wirz, Ulrich Zutter
  • 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: 5616787
    Abstract: The invention relates to a process for the preparation of polyalkylated aromatic carboxylic acids of formula I ##STR1## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are each independently of one another hydrogen, C.sub.1 -C.sub.20 alkyl, halogen or C.sub.5 -C.sub.8 cycloalkyl, with the proviso that at least two of the substituents R.sub.1, R.sub.2, R.sub.3, R.sub.4 or R.sub.5 are alkyl and/or cycloalkyl, by reacting corresponding aromatic hydrocarbons with carbon dioxide, which reaction is carried out observing special ratios of temperature and pressure. The invention furthermore relates to a one-pot process for the preparation of the corresponding acyl halides.
    Type: Grant
    Filed: October 11, 1995
    Date of Patent: April 1, 1997
    Assignee: Ciba-Geigy Corporation
    Inventors: Rinaldo Husler, Ivan Orban, Martin Holer
  • Patent number: 5312975
    Abstract: A process for the preparation of 5-(2,4-difluorophenyl)-salicylic acid comprising the reaction of an organometallic derivative with a suitable substituted benzene in the presence of a transition-metal based catalyst is described.
    Type: Grant
    Filed: December 27, 1991
    Date of Patent: May 17, 1994
    Assignee: Zambon Group S.p.A.
    Inventors: Claudio Giordano, Laura Coppi, Francesco Minisci
  • Patent number: 5210322
    Abstract: A process for preparing ethers which comprises contacting a carboxylated ether with a metal oxide catalyst under conditions effective to produce the ether.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: May 11, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Stephen W. King, Kurt D. Olson
  • Patent number: 5183934
    Abstract: Disclosed is a novel compound 2-trifluoromethyl-4-hydroxybenzoic acid represented by the formula: ##STR1##
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: February 2, 1993
    Assignee: Showa Shell Sekiyu Kabushiki Kaisha
    Inventor: Yoshiichi Suzuki
  • 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: 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: 4942257
    Abstract: A method of manufacturing an alkali metal salt of 2,3,6,7-naphthalenetetracarboxylic acid. Either a sodium salt or a mixture of sodium salt and potassium salt of at least one naphthalenecarboxylic acid selected form the group consisting of naphthoic acids and naphthalenepolycarboxylic acids is heated to an elevated temperature in an inert gas atmosphere in the presence of a Henkel reaction catalyst and halogenated sodium.
    Type: Grant
    Filed: August 31, 1989
    Date of Patent: July 17, 1990
    Assignee: NKK Corporation
    Inventors: Yakudo Tachibana, Kazuhiko Tate, Toshifumi Suzuki, Kouji Chiba
  • Patent number: 4853414
    Abstract: Compounds of formula (I), useful as insecticides and knockdown agents: ##STR1## where Y is C.sub.1-6 alkoxy, Z is halo or C.sub.1-6 alkoxy; R is --(CH.sub.2).sub.p --(O).sub.m --R.sup.3 where m and p may be 0 or 1; R.sup.3 is C.sub.1-6 alkyl, phenyl or benzyl, or when m is 0, R.sup.3 is C.sub.1-6 alkenyl, haloalkenyl, alkynyl or haloalkynyl, and either (a) A and B are both C.sub.1-4 alkyl or (b) A is hydrogen and B is (R.sup.1)(R.sup.2)C.dbd.CH-- where R.sup.1 and R.sup.2 are selected from methyl, chloro, bromo, fluoro and trifluoromethyl.
    Type: Grant
    Filed: October 30, 1987
    Date of Patent: August 1, 1989
    Assignee: Imperial Chemical Industries PLC
    Inventors: Michael J. Robson, John Williams
  • Patent number: 4845276
    Abstract: 2,6-dialkoxybenzoic acid is made by metalation of 1,3-dialkoxybenzene by reaction with potassium dialkylamide. The metalated dialkoxybenzene is carbonated and acidified to form the dialkoxybenzoic acid.
    Type: Grant
    Filed: August 22, 1988
    Date of Patent: July 4, 1989
    Assignee: Mine Safety Appliances Company
    Inventor: Lin-Chen Yu
  • Patent number: 4845277
    Abstract: 2,6-dialkoxybenzoic acid is made by direct metalation of 1,3-dialkoxybenzene by potassium. The metalated dialkoxybenzene is carbonated and acidified to form the dialkoxybenzoic acid.
    Type: Grant
    Filed: August 22, 1988
    Date of Patent: July 4, 1989
    Assignee: Mine Safety Appliances Company
    Inventor: Lin-Chen Yu
  • Patent number: 4820868
    Abstract: Disclosed is a process for the preparation of a naphthalene-2,6-dicarboxylic acid dialkali metal salt which comprises heating an alkali metal salt of naphthoic acid and/or a dialkali metal salt of naphthalene-dicarboxylic acid under pressure with carbon dioxide gas in the presence of a catalyst, wherein an aprotic polycyclic aromatic compound having 2 or 3 rings is used as a reaction medium. Naphthalene-2,6-dicarboxylic acid dialkali metal salt can be obtained in high yield and selectivity with a good reproducibility of the reaction.
    Type: Grant
    Filed: September 29, 1986
    Date of Patent: April 11, 1989
    Assignee: Nippon Steel Corporation
    Inventors: Shuichi Mitamura, Koichi Fujishiro, Hiroharu Inoue
  • 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: 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: 4697037
    Abstract: The preparation of dibenzo[b,f]thiepin compounds by a process comprising the direct carboxylation of an ortho-toluyl-aryl sulfide to introduce a phenylacetic acid side chain is disclosed.
    Type: Grant
    Filed: October 11, 1985
    Date of Patent: September 29, 1987
    Assignee: Merck & Co., Inc.
    Inventor: Thomas R. Verhoeven
  • Patent number: 4658054
    Abstract: A process for the preparation of 5,6-dialkoxyanthranilic acids is described. The 5,6-dialkoxyanthranilic acids are useful in the preparation of substituted quinazolinediones which are active cardiotonic agents.
    Type: Grant
    Filed: July 29, 1985
    Date of Patent: April 14, 1987
    Assignee: Ortho Pharmaceutical Corporation
    Inventor: Richard A. Conley
  • Patent number: 4564700
    Abstract: An improved process for the preparation of fluorene-9-carboxylic acid comprising reacting fluorene and a dialkyl carbonate with alkyls of 1 to 5 carbon atoms in the presence of a member of the group consisting of alkali metal hydrides or potassium alcoholate of an aliphatic alcohol of 1 to 5 carbon atoms, neutralizing the mixture and saponifying the resulting fluorene-9-carboxylic acid ester to obtain fluorene-9-carboxylic acid in good yields.
    Type: Grant
    Filed: November 16, 1983
    Date of Patent: January 14, 1986
    Assignee: Rutgerswerke Aktiengesellschaft
    Inventors: Winfried Orth, Emmerich Pastorek, Werner Fickert
  • Patent number: 4533500
    Abstract: N-acyliminodiacetic acids are manufactured by reacting formaldehyde or a formaldehyde generator compound with a N-unsubstituted amide or a generator thereof and with carbon monoxide in contact with a carbonylation catalyst, for example, a cobalt compound, the ratio of the aldehyde groups to the amide groups being at least 2:1. The formaldehyde generator can be a polymeric form of formaldehyde and the amide generator can be a carboxylic ester, acid or anhydride.
    Type: Grant
    Filed: March 17, 1983
    Date of Patent: August 6, 1985
    Assignees: Institut Francais du Petrole, Societe Nationale Elf-Aquitaine (Production)
    Inventors: Yves Chauvin, Dominique Commereuc, Andre Hirschauer, Dominique Reffet, Robert Stern
  • 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: 4518799
    Abstract: Novel processes for making arylpropionic acids are described. One process comprises carboxylating particular Grignard compounds which are the products of a catalyzed reaction between corresponding arylmagnesium bromides and ethylene. Furthermore, the reaction making the particular Grignard compounds is itself novel. Also, an improved method is disclosed for making coupled aryl compounds useful as intermediates for making compounds having a pharmaceutical use. For example, particular biaryls may be used to make some of the Grignard compounds herein from which the arylpropionic acids are made. Finally, an improved bromination is disclosed giving high yields of 4-bromo-2-fluoroaniline, which is thereafter coupled with benzene, then used to make the arylmagnesium bromide reacted with ethylene to obtain the particular Grignard compound and subsequent desired arylpropionic acid, i.e. 2-(2-fluoro-4-biphenylyl)propionic acid.
    Type: Grant
    Filed: June 8, 1982
    Date of Patent: May 21, 1985
    Assignee: The Upjohn Company
    Inventor: Thomas A. Hylton
  • 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: 4405640
    Abstract: Insecticides of the formula ##STR1## wherein R.sup.1 and R.sup.2 are each selected from methyl, halomethyl, and halo; X is oxygen, sulphur, sulphonyl or a group NR.sup.4 where R.sup.4 represents hydrogen, lower alkyl or lower carboxylic acyl; R.sup.3 is lower alkyl, lower alkenyl or benzyl; m has the value zero or one, and n has a value from one to four.
    Type: Grant
    Filed: December 1, 1980
    Date of Patent: September 20, 1983
    Assignee: Imperial Chemical Industries PLC
    Inventor: Nazim Punja
  • 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