Preparation By Carbonylation Patents (Class 562/406)
  • Patent number: 9840451
    Abstract: A carbonylation process for producing acetic acid including: (a) carbonylating methanol or its reactive derivatives in the presence of a Group VIII metal catalyst and methyl iodide promoter to produce a liquid reaction mixture including acetic acid, water, methyl acetate and methyl iodide; (b) feeding the liquid reaction mixture to a flash vessel; (c) flashing the reaction mixture to produce a crude product vapor stream.
    Type: Grant
    Filed: March 9, 2015
    Date of Patent: December 12, 2017
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventor: Jeremy J. Patt
  • Patent number: 9688600
    Abstract: In a process for improving a carbonylation process, iron is removed to maintain an effective Space Time Yield (STY) of the rhodium catalyst of at least 80% of the maximum STY. The process comprises carbonylating methanol in a reactor in a reaction medium comprising water, a rhodium catalyst, methyl iodide and a halide salt, separating a portion of the reaction medium in a flash vessel to form a less volatile stream and a vapor product stream comprising acetic acid, recycling a liquid stream to the reactor, wherein the liquid stream comprises a portion of the less volatile stream and wherein the liquid stream comprises iron, and removing a portion of the iron from the liquid stream to maintain an effective STY of the rhodium catalyst of at least 80% of the maximum STY.
    Type: Grant
    Filed: November 13, 2015
    Date of Patent: June 27, 2017
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: Yaw-Hwa Liu, Mark O. Scates
  • Patent number: 9382183
    Abstract: A process for producing acetic acid is disclosed in which the methyl iodide concentration is maintained in the vapor product stream formed in a flashing step. The methyl iodide concentration in the vapor product stream ranges from 24 to less than 36 wt. %, based on the weight of the vapor product stream. In addition, the acetaldehyde concentration is maintained within the range from 0.005 to 1 wt. % in the vapor product stream. The vapor product stream is distilled in a first column to obtain an acetic acid product stream comprising acetic acid and hydrogen iodide in an amount of less than or equal to 300 wppm and/or methyl iodide in an amount from 0.1 to 6 wt. %, and an overhead stream comprising methyl iodide, water and methyl acetate.
    Type: Grant
    Filed: October 2, 2015
    Date of Patent: July 5, 2016
    Assignee: CELANESE INTERNATIONAL CORPORATION
    Inventors: Ronald D. Shaver, Yaw-Hwa Liu, Mark O. Scates
  • Publication number: 20150025269
    Abstract: The invention provides a simple, efficient, environmental friendly catalytic system for the direct carboxylation reaction using CO2 under mild condition. A single step heterogeneous catalytic process for preparation of alkynyl carboxylic acids of formula I is disclosed.
    Type: Application
    Filed: January 25, 2013
    Publication date: January 22, 2015
    Inventors: Ravindra Dattatray Aher, Madhuri Hanumant Gage, Reddy Santhosh Rekula, Pratibha Uttam Karabal, Gurunath Mallappa Suryavanshi, Arumugam Sudalai
  • Patent number: 8686183
    Abstract: The invention provides a method for the hydroxycarbonylation, alkoxycarbonylation, aryloxycarbonylation or thiocarbonylation of an unsaturated molecule. The method includes a hydroxycarbonylation, alkoxycarbonylation, aryloxycarbonylationor thiocarbonylation reaction on the unsaturated molecule in which a complex including a ligand comprising a [n,n?] cyclophane comprising two non-fused monocyclic aromatic rings bridged by two linear and aliphatic linkages, in which each of the non-fused monocyclic aromatic rings is substituted with a phosphorus atom-containing substituent, is used to catalyse the reaction.
    Type: Grant
    Filed: September 10, 2010
    Date of Patent: April 1, 2014
    Assignee: University Court Of The University of St Andrews
    Inventors: Matthew Lee Clarke, Tina Marie Konrad
  • Patent number: 8664424
    Abstract: Provided is a method for preparing 2,5-dimethylphenylacetic acid, wherein p-xylene is mixed with paraformaldehyde and concentrated hydrochloric acid in a solvent of ion liquid to obtain 2,5-dimethyl benzyl chloride by the chloromethylation reaction. Then, 2,5-dimethyl benzyl chloride is introduced into a reactor with an acid binding agent and a solvent, the carbonylation and hydrolysis reaction is conducted in the presence of a catalyst to obtain 2,5-dimethylphenylacetic acid. The present process has new route, less synthesis steps, simple operation, lower cost, increased yield, and is friendly to the environment. Therefore, the method is suitable for industrial production.
    Type: Grant
    Filed: June 7, 2011
    Date of Patent: March 4, 2014
    Assignees: Lianhe Chemical Technology Co., Ltd, Jiangsu Lianhe Chemical Technology Co., Ltd.
    Inventors: Ping Wang, Xiaobin Fan, Xingjun Lin, Zhaohui He
  • Patent number: 8633245
    Abstract: The compound represented by the following formula (I) and the like have PAI-1 inhibition activity; wherein: R1 represents a C6-10 aryl group which may be substituted or the like; T represents a single bond or the like; m represents 0 or 1; when m is 0, G represents —N—C(?O)—CO2H or the like; when m is 1, G represents an oxygen atom or the like; R2 represents a C6-10 aryl group which may be substituted or the like; E represents the following formula (II) wherein one of R31, R32, R33 and R34 represents the formula R1-T-, each of the other three independently represents a hydrogen atom or the like, and R35 represents the formula —X—Y?, a hydrogen atom or the like; X represents —CH2— or the like; Y? represents a carboxy group or the like; M represents a single bond or the like.
    Type: Grant
    Filed: April 10, 2009
    Date of Patent: January 21, 2014
    Assignee: Institute of Medicinal Molecular Design, Inc.
    Inventors: Youichi Yamaguchi, Takeshi Yanase, Susumu Muto, Akiko Itai
  • Patent number: 8575387
    Abstract: The present invention relates to a method for preparing carboxylic acids comprising the step of contacting an aromatic hydrocarbon comprising at least one group including an ? C-atom that is oxidizable to a carboxylic group in liquid phase with an oxygen containing gas in the presence of a heterogeneous catalyst with perovskite structure ABO3 with A being selected from at least one element of groups 1 to 3 of the Periodic Table, lanthanides or actinides, and B being selected from at least one element of the groups 4 to 15 of the periodic table or an oxygen-defective derivative of that catalyst having the formula ABO3?? with 0<?<1.
    Type: Grant
    Filed: May 25, 2012
    Date of Patent: November 5, 2013
    Assignee: King Saud University
    Inventors: Saeed Mohammed Al-Zahrani, Horacio Falcon Richeni, Ainara Aguadero Garin, Jose Antonio Alonso Alonso, Jose Miguel Campos Martin, Jose Luis Garcia Fierro
  • Publication number: 20130281729
    Abstract: Organic synthesis, i.e., the synthesis of carboxylic acids by direct carbonylation of alcohols in a continuous process, and more particularly, the synthesis of phenylalkylic acids, which are synthesis intermediates useful in pharmaceutical chemistry, by direct carbonylation of phenyl alkyl alcohols.
    Type: Application
    Filed: December 13, 2011
    Publication date: October 24, 2013
    Inventors: Raimondo Pilia, Alexandre Trani, Sabrina Marie, Fabrice De Panthou
  • Publication number: 20130281730
    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: Application
    Filed: October 20, 2011
    Publication date: October 24, 2013
    Applicants: 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: 20130046108
    Abstract: Provided is a method for preparing 2,5-dimethylphenylacetic acid, wherein p-xylene is mixed with paraformaldehyde and concentrated hydrochloric acid in a solvent of ion liquid to obtain 2,5-dimethyl benzyl chloride by the chloromethylation reaction. Then, 2,5-dimethyl benzyl chloride is introduced into a reactor with an acid binding agent and a solvent, the carbonylation and hydrolysis reaction is conducted in the presence of a catalyst to obtain 2,5-dimethylphenylacetic acid. The present process has new route, less synthesis steps, simple operation, lower cost, increased yield, and is friendly to the environment. Therefore, the method is suitable for industrial production.
    Type: Application
    Filed: June 7, 2011
    Publication date: February 21, 2013
    Applicants: JIANGSU LIANHE CHEMICAL TECHNOLOGY CO., LTD., LIANHE CHEMICAL TECHNOLOGY CO., LTD
    Inventors: Ping Wang, Xiaobin Fan, Xingjun Lin, Zhaohui He
  • Publication number: 20120323038
    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: Application
    Filed: December 16, 2010
    Publication date: December 20, 2012
    Applicant: Agency for Science, Technology and Research
    Inventors: Yugen Zhang, Dingyi Yu
  • Patent number: 8269033
    Abstract: The invention is directed a process of preparing a compound of formula (I), wherein R1, R2, R3 and z are as defined herein.
    Type: Grant
    Filed: July 24, 2009
    Date of Patent: September 18, 2012
    Assignee: Sanofi-Aventis Deutschland GmbH
    Inventors: Joachim-Heiner Jendralla, Matthias Braun, Gerhard Korb
  • Patent number: 8232424
    Abstract: Methods and reagents for photo-initiated carbonylation with carbon-isotope labeled carbon monoxide using alkyl/aryl iodides with sulfoxides and triethylamine are provided. The resultant carbon-isotope labeled acids, and pharmaceutical acceptable salts and solvates are useful as radiopharmaceuticals, especially for use in Positron Emission Tomography (PET). Associated kits and method for PET studies are also provided.
    Type: Grant
    Filed: June 14, 2006
    Date of Patent: July 31, 2012
    Assignee: GE Healthcare Limited
    Inventors: Bengt Langstrom, Oleksiy Itsenko
  • Publication number: 20120178963
    Abstract: The invention provides a method for the hydroxycarbonylation, alkoxycarbonylation, aryloxycarbonylation or thiocarbonylation of an unsaturated molecule. The method includes a hydroxycarbonylation, alkoxycarbonylation, aryloxycarbonylationor thiocarbonylation reaction on the unsaturated molecule in which a complex including a ligand comprising a [n,n?]cyclophane comprising two non-fused monocyclic aromatic rings bridged by two linear and aliphatic linkages, in which each of the non-fused monocyclic aromatic rings is substituted with a phosphorus atom-containing substituent, is used to catalyse the reaction.
    Type: Application
    Filed: September 10, 2010
    Publication date: July 12, 2012
    Inventors: Matthew Lee Clarke, Tina Marie Konrad
  • Publication number: 20110180968
    Abstract: A method for making a carbon nanotube metal composite includes the following steps. A number of carbon nanotubes is dispersed in a solvent to obtain a suspension. Metal powder is added into the suspension, and then the suspension agitated. The suspension containing the metal powder is allowed to stand for a while. The solvent is reduced to obtain a mixture of the number of carbon nanotubes and the metal powder.
    Type: Application
    Filed: October 15, 2010
    Publication date: July 28, 2011
    Applicants: TSINGHUA UNIVERSITY, HON HAI PRECISION INDUSTRY CO., LTD.
    Inventors: CHUN-HUA HU, CHANG-HONG LIU, SHOU-SHAN FAN
  • Publication number: 20100158804
    Abstract: Methods and reagents for photo-initiated carbonylation with carbon-isotope labeled carbon monoxide using alkyl/aryl iodides with alcohols or water treated by photosensitizers are provided. The resultant carbon-isotope labeled esters and acids, and pharmaceutical acceptable salts and solvates are useful as radiopharmaceuticals, especially for use in Positron Emission Tomography (PET). Associated kits and method for PET studies are also provided.
    Type: Application
    Filed: March 2, 2010
    Publication date: June 24, 2010
    Applicant: GE HEALTHCARE LIMITED
    Inventors: BENGT LANGSTROM, OLEKSIY ITSENKO
  • Publication number: 20100022799
    Abstract: A process for the carbonylation of a conjugated diene is described. The process comprises the steps of reacting a conjugated diene with carbon monoxide and a co-reactant having an active hydrogen in the presence of a solvent system and a catalyst system. The solvent system comprises a an aromatic carboxylic acid or, under some conditions, any carboxylic acid. The catalyst system is obtainable by combining: a. a metal of Group 8, 9 or 10 or a compound thereof: and b.
    Type: Application
    Filed: December 20, 2007
    Publication date: January 28, 2010
    Applicant: LUCITE INTERNATIONAL UK LIMITED
    Inventors: Graham Ronald Eastham, Mark Waugh, Philip Ian Richards
  • Patent number: 7629488
    Abstract: The present invention is directed to novel processes for the preparation of opioid modulators (agonists and antagonists) and intermediates in their synthesis. The opioid modulators are useful for the treatment and prevention of as pain and gastrointestinal disorders.
    Type: Grant
    Filed: March 6, 2006
    Date of Patent: December 8, 2009
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Chaozhong Cai, Wei He
  • Patent number: 7579500
    Abstract: The invention relates to a method for preparing 2,5-dimethylphenylacetic acid by converting p-xylene with chloroacetyl chloride into 2-chloro-1-(2,5-dimethylphenyl)ethanone, which is reacted with the compound of the formula (II) to give the compound of the formula (III), which is then rearranged to give a mixture of the compounds (IV) and (V), which is then hydrolyzed to 2,5-dimethylphenylacetic acid.
    Type: Grant
    Filed: January 22, 2005
    Date of Patent: August 25, 2009
    Assignee: Archer-Daniels-Midland Company
    Inventor: Thomas Himmler
  • Publication number: 20090030173
    Abstract: Disclosed is a fluorine-containing dicarboxylic acid represented by formula (1), wherein n represents an integer of 1-4, and the two carboxylic groups are not adjacent to each other on the aromatic ring. It is possible to obtain a linear polymer compound by reacting the fluorine-containing dicarboxylic acid with a comonomer (e.g., diaminodiol). By thermal cyclization, this linear polymer compound can be converted into another polymer compound having superior characteristics.
    Type: Application
    Filed: July 16, 2008
    Publication date: January 29, 2009
    Applicant: CENTRAL GLASS COMPANY, LIMITED
    Inventors: Satoru Narizuka, Yuji Hagiwara, Masashi Nagamori, Kazuhiro Yamanaka
  • Patent number: 7470809
    Abstract: The present invention relates to a novel process for the production of [2-(4-fluoro-benzyl)-phenyl]-acetic acid, a compound obtainable from phthalic anhydride. The process comprises the subsequent steps a) through e): a) reacting phthalic anhydride with fluorobenzene or a derivative thereof in appropriate reaction conditions; b) over reducing the product obtained in step a) at the ketone moiety; c) reducing the product obtained in step b) with sodium dihydro-bis(2-methoxyethoxy)aluminate (Red-Al) to the corresponding alcohol; d) chlorinating the alcohol obtained in step c); e) inserting CO into the product obtained in step d) through an appropriate Pd-containing catalytic system. In an alternative embodiment, the step e) is replaced by the steps f1) and f2): f1) reacting the product obtained in step d) with sodium cyanide; f2) hydrolysing the product obtained in step f1).
    Type: Grant
    Filed: August 26, 2005
    Date of Patent: December 30, 2008
    Assignee: Janssen Pharmaceutica N.V.
    Inventors: Michel Joseph Maurice André Guillaume, Yolande Lydia Lang, Armin Roessler, Lars Ulmer, Stefan Marcel Herman Leurs, Dirk De Smaele
  • Patent number: 7439390
    Abstract: The present invention relates to a sequence for the preparation of amino acids, for example alpha-amino acids, in particular methionine, by making use of an amidocarbonylation reaction in the presence of a cobalt carbonyl catalyst and separating the catalyst in the form of a Co(N-amino acid)2 compound.
    Type: Grant
    Filed: May 14, 2005
    Date of Patent: October 21, 2008
    Assignee: Degussa AG
    Inventors: Martin Hateley, Thomas Häussner, Christoph Weckbecker, Klaus Huthmacher, Dieter Buss
  • Patent number: 7414160
    Abstract: A process produces an aromatic compound by bringing an aromatic compound (B) into contact with molecular oxygen (C) in the presence of a catalyst (A) comprising at least one of (A1) a heteropolyacid and/or a salt thereof, and (A2) a mixture of oxoacids and/or salts thereof containing, as a whole, one of P and Si and at least one selected from V, Mo and W to thereby yield another aromatic compound (G) than the aromatic compound (B). The process can produce, for example, a corresponding aromatic hydroxy compound (G1) by allowing the aromatic compound (B) to react with the molecular oxygen (C) further in the presence of a reducing agent (D).
    Type: Grant
    Filed: December 20, 2005
    Date of Patent: August 19, 2008
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Yasutaka Ishii, Tatsuya Nakano
  • Patent number: 7271285
    Abstract: An aromatic compound (C) is reacted with carbon monoxide (D) and molecular oxygen (E) in the presence of a palladium compound catalyst (A) and a catalyst (B) and thereby yields a aromatic carboxylic acid corresponding to the aromatic compound (C) except with one or more carboxyl groups bonded to its aromatic ring. The catalyst (B) contains a heteropolyacid or a salt thereof (B1) or a mixture of oxo acids and/or salts thereof (B2), and the mixture (B2) contains, as a whole, one of P and Si and at least one selected from V, Mo and W.
    Type: Grant
    Filed: February 26, 2004
    Date of Patent: September 18, 2007
    Assignee: Daicel Chemical Industries Ltd.
    Inventors: Yasutaka Ishii, Tatsuya Nakano
  • 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: 7115782
    Abstract: There is provided a process for producing an aromatic compound by Friedel-Crafts reaction product, which comprises reacting an aromatic compound with an ester compound in the presence of a heteropolyacid-containing solid acid catalyst.
    Type: Grant
    Filed: May 15, 2003
    Date of Patent: October 3, 2006
    Assignee: Showa Denko K.K.
    Inventors: Toshio Okuhara, Tetsuo Nakajo
  • Patent number: 6858753
    Abstract: The present invention provides an improved process for the production of carboxylic acids by the carbonylation of alcohol. The process involves contacting an alcohol with carbon monoxide in the presence of a nickel compound, a heterocyclic organic compound and an iodide promoter to produce the corresponding carboxylic acid. The improvement relates to the use of heterocyclic organic compound as a promoter containing at least two heteroatoms of which at least one is selected independently from S or N, which provides an inexpensive and stable catalyst system.
    Type: Grant
    Filed: March 14, 2002
    Date of Patent: February 22, 2005
    Assignee: Council of Scientific and Industrial Research
    Inventors: Raghunath Vitthal Chaudhari, Sunil Shankar Joshi, Ashutosh Anant Kelkar, Sunil Sadashiv Divekar
  • Patent number: 6818786
    Abstract: The present invention relates to a process for the preparation of ethyl 3-ethoxy-4-ethoxycarbonyl-phenylacetate having formula 1 Ethyl 3-ethoxy-4-ethoxycarbonyl-phenylacetate (1) is an important key intermediate for the synthesis of repaglinide (2) an oral hypoglycemic agent
    Type: Grant
    Filed: March 31, 2003
    Date of Patent: November 16, 2004
    Assignee: Council of Scientific and Industrial Research
    Inventors: Uttam R. Kalkote, Mukund K. Gurjar, Shreerang V. Joshi, Suresh M. Kadam, Sanjay J. Naik
  • Patent number: 6784313
    Abstract: A process for producing a carboxylic acid having (n+1) carbon atoms, which includes carbonylating an alcohol having n carbon atoms, and/or an ester of the alcohol and the carboxylic acid in each alkyl group with carbon monoxide in the presence of a catalytic system containing a rhodium catalyst. The process uses a reaction medium for the carbonylation that includes: (1) a rhodium catalyst, (2) an organic halide corresponding to said alcohol, (3) an ester of the alcohol and the carboxylic acid, (4) the carboxylic acid, optionally (5) water, a haloid acid, an inorganic halogen salt or an acetate, and (6) a cocatalyst selected from arginine, N-acetyl alanine, or nitrogen- and oxygen-containing organic compounds.
    Type: Grant
    Filed: October 4, 2002
    Date of Patent: August 31, 2004
    Assignee: China Petrochemical Development Corporation
    Inventors: Chia Jung Tsai, Yao Lung Liu, Hsi Chin Tsai
  • Patent number: 6660883
    Abstract: The present invention provides an improved process for the preparation of 2-aryl propionic acid which by subjecting an aryl compound selected from an aryl alcohol or aryl halide or an aryl olefin to carbonylation in the presence of a halide source, a protonic acid, water and a heterogeneous metal and a phosphine ligand as a catalyst in an organic solvent.
    Type: Grant
    Filed: September 14, 2000
    Date of Patent: December 9, 2003
    Assignee: Council of Scientific and Industrial Research
    Inventors: Raghunath Vitthal Chaudhari, Jayasree Seayad, Abdul Seayad
  • Patent number: 6653502
    Abstract: A process for preparing phenylacetic acid derivatives of the formula (I) by reacting benzyl chlorides of the formula (II) with a compound of the formula R6OH and with carbon monoxide in a dipolar aprotic solvent in the presence of a catalyst which comprises at least one compound of a transition metal of subgroup VIII of the Periodic Table of the Elements, where R1, R2, R3, R4, and R5 independently of one another are the following radicals: a hydrogen or fluorine atom; a CH2Cl radical; a HO2CCH═CH—, NC— or CF3— group; an alkyl, alkoxy or acyloxy radical having in each case 1 to 18 carbon atoms; or a C6-C18-aryloxy, aryl or heteroaryl radical.
    Type: Grant
    Filed: November 9, 2001
    Date of Patent: November 25, 2003
    Assignee: Clariant GmbH
    Inventor: Holger Geissler
  • Patent number: 6617469
    Abstract: A process for preparing malonic diesters by carbonylation of haloacetic esters and reaction with monohydric alcohols and a base in the presence of a transition metal catalyst, preferably a catalytic cobalt carbonyl complex, using a stirred reactor with one or more internal heat exchangers. The stirred reactor preferably contains a sparging stirrer.
    Type: Grant
    Filed: December 1, 2000
    Date of Patent: September 9, 2003
    Assignee: Degussa AG
    Inventors: Frank Bauer, Wilfried Latz, Uwe Prange, Christoph Theis
  • Patent number: 6562996
    Abstract: A composition containing isomeric mixtures of arylaldehydes prepared from a mixed alkyl aromatic feedstock. A composition containing isomeric mixtures of dimethylbenzaldehydes prepared from a mixed xylene feedstock using a Gatterman-Koch type reaction. A composition of isomeric mixtures of tolualdehydes prepared from a toluene feedstock using a Gatterman-Koch type reaction.
    Type: Grant
    Filed: August 20, 2001
    Date of Patent: May 13, 2003
    Assignee: ExxonMobil Chemical Patents Inc.
    Inventor: Ramzi Yanni Saleh
  • Patent number: 6555704
    Abstract: A method is provided for the preparation of alpha-aryl-propionic acids such as ibuprofen by carbonylating the corresponding 1-arylethyl halide in an acidic aqueous medium containing a palladium catalyst. In the preparation of ibuprofen, 1-(4′-isobutylphenyl)ethyl halide is reacted with carbon monoxide in an acidic aqueous medium containing a palladium catalyst.
    Type: Grant
    Filed: May 22, 1995
    Date of Patent: April 29, 2003
    Assignee: BASF Corporation
    Inventor: Varadaraj Elango
  • Patent number: 6548698
    Abstract: This invention relates generally to the oxidative carbonylation of toluene, catalyzed by rhodium or iridium complexes in the presence of an oxidant and under mild conditions, whereby toluic acid is produced with para-selectivity up to 98%.
    Type: Grant
    Filed: June 27, 2000
    Date of Patent: April 15, 2003
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Vladimir Grushin, David Lincoln Thorn
  • Publication number: 20030069444
    Abstract: The invention relates to a process for the preparation of ortho-alkylated benzoic acid derivatives of the formula I 1
    Type: Application
    Filed: October 8, 2002
    Publication date: April 10, 2003
    Applicant: MERCK KGAA
    Inventors: Ekkehard Bartmann, Ingeborg Stein
  • Patent number: 6531597
    Abstract: The present invention is a process for the preparation of a compound of formula The compounds of formula I are valuable intermediates for the manufacture of therapeutically active compounds.
    Type: Grant
    Filed: January 8, 2002
    Date of Patent: March 11, 2003
    Assignee: Hoffmann-La Roche Inc.
    Inventors: Fabienne Hoffmann-Emery, Michelangelo Scalone, Paul Spurr
  • Patent number: 6521783
    Abstract: This invention relates in part to a processes for the conversion of a feedstock stream comprising carbon monoxide and hydrogen to a product stream comprising at least one of an ester, acid, acid anhydride and mixtures thereof. This invention also relates in part to processes for converting an alcohol and/or ether feedstock to oxygenated products, e.g., esters, acids, acid anhydrides and mixtures thereof. The processes and catalysts are especially suitable for the production of acetic acid and methyl acetate from a synthesis gas feedstock or from an alcohol and/or ether feedstock.
    Type: Grant
    Filed: July 10, 2000
    Date of Patent: February 18, 2003
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Richard William Wegman, David McNeill Somerville, Barry Brent Fish, Raymond Edwin Rooks, Chinsoo Stephen Lee, Paul Frank Bryan, William J. Bartley, David Michael Anthony Minahan, Fungau Ho
  • Publication number: 20020137964
    Abstract: The present invention relates to a process for the preparation of a carboxylic acid ester of the general formula II, 1
    Type: Application
    Filed: March 20, 2001
    Publication date: September 26, 2002
    Applicant: COUNCIL OF SCIENTIFIC & INDUSTRIAL RESEARCH
    Inventors: Jayasree Seayad, Abdul Majeed Seayad, Bibhas Ranjan Sarkar, Raghunath Vitthal Chaudhari
  • Patent number: 6444844
    Abstract: The present invention relates to a process for the preparation of a carboxylic acid of the formula III, wherein R1 is aryl, substituted aryl, naphthyl, substituted naphthyl or alkyl, R2, R3, R4 and R5 are independently hydrogen or alkyl, by reacting the corresponding olefin of formula I or the corresponding organic halide or alcohol of the formula II, wherein R1 is selected from the group consisting of aryl, substituted aryl, naphthyl, substituted naphthyl or alkyl, R2, R3, R4 and R5 are independently hydrogen or alkyl and X is a halogen atom or a —OH group, using a novel water soluble palladium complex catalyst of general formula IV wherein R1, R2 and R3 are substituents on the phosphine ligand and selected from the group consisting of alkyl, aryl, arylalkyl, and cycloaliphatic, at least one of which carries a sulfonic acid and salts thereof, X is aryl or alkyl sulfonato or aryl or alkyl carboxylate or formato or a halide,
    Type: Grant
    Filed: March 20, 2001
    Date of Patent: September 3, 2002
    Assignee: Council of Scientific and Industrial Research
    Inventors: Abdul Majeed Seayad, Jayasree Seayad, Raghunath Vitthal Chaudhari
  • Patent number: 6388141
    Abstract: The present invention relates to processes for the preparation of oxo products by the hydroformylation of substrates having C═C double bonds using unmodified rhodium catalysts in a reaction mixture essentially consisting of the substrates, the catalyst and carbon dioxide in a supercritical state (scCO2). In particular, the invention relates to such processes for the preparation of products which contain substantial proportions of branched i-oxo products. Further, the invention relates to such processes for the hydroformylation of substrates which do not correspond to the general formula CnH2n. The invention further relates to such processes in which the separation of product and catalyst is effected using the special solvent properties of scCO2.
    Type: Grant
    Filed: January 13, 2000
    Date of Patent: May 14, 2002
    Assignee: Studiengesellschaft Kohle mbH
    Inventors: Walter Leitner, Daniel Koch
  • Publication number: 20020012631
    Abstract: This invention relates to novel highly functionalized phosphine ligands as ancillary ligands in radiopharmaceuticals. Also, this invention provides radiopharmaceuticals comprised of highly functionalized phosphine ligated 99mTc labeled HYNIC-conjugated biomolecules that selectively localize at sites of disease and thus allow an image to be obtained of the loci using gamma scintigraphy. The invention also provides methods of use of the radiopharmaceuticals as imaging agents for the diagnosis of cardiovascular disorders such as thromboembolic disease or atherosclerosis, infectious disease and cancer.
    Type: Application
    Filed: April 5, 2001
    Publication date: January 31, 2002
    Inventor: Shuang Liu
  • Publication number: 20010031888
    Abstract: A method and catalyst system for producing aromatic carbonates from aromatic hydroxy compounds. In one embodiment, the method includes the step of contacting at least one aromatic hydroxy compound with oxygen and carbon monoxide in the presence of a carbonylation catalyst system having an effective amount of an iron source in the absence of a Group VIII B metal source. In various alternative embodiments, the carbonylation catalyst system can include at least one inorganic co-catalyst, as well as a halide composition and/or a base.
    Type: Application
    Filed: December 4, 2000
    Publication date: October 18, 2001
    Inventors: Ben Purushotam Patel, Grigorii Lev Soloveichik, Donald Wayne Whisenhunt, Kirill Vladimirovich Shalyaev
  • Patent number: 6294687
    Abstract: The present invention discloses this invention relates to a process for the conversion of olefinically unsaturated compounds to corresponding carboxylic acids and their esters of formula III wherein R1, R2, R3 and R4 may independently be hydrogen, alkyl, aryl, arylalkyl, cycloaliphatic with or without substituents, R and R5 may be H and COOR′ or vice versa wherein R′ may be H in the case of acids and may be alkyl, aryl, arylalkyl, cycloaliphatic with or without substituents, in the case of esters, wherein said conversion is carried out in the presence of a transition metal complex catalyst of the formula.
    Type: Grant
    Filed: December 30, 1999
    Date of Patent: September 25, 2001
    Assignee: Council of Scientific and Industrial Research
    Inventors: Raghunath Vitthal Chaudhari, A. Seayad, Jayasree Seayad
  • Patent number: 6268527
    Abstract: The invention relates to a method for producing a benzoic acid derivative represented by the general formula (1). The method includes the step of reacting an aromatic compound represented by the general formula (2), with carbon monoxide and a hydroxy compound (i.e., water or an alcohol), in the presence of (a) a metal compound containing a metal of 8, 9 and 10 groups of periodic table, (b) a first phosphine derivative represented by the general formula (R1)2P—Q—P(R1)2, and (c) a base, It is possible to easily and efficiently produce the benzoic acid derivative by the method.
    Type: Grant
    Filed: December 2, 1999
    Date of Patent: July 31, 2001
    Assignee: Central Glass Company, Limited
    Inventors: Makoto Koide, Michio Ishida, Yuzuru Morino, Seiji Hasegawa, Satoru Narizuka, Takashi Kume
  • Patent number: 6268526
    Abstract: A mixture formed from an aromatic substituted alcohol and/or an aromatic substituted alkyl halide, and a copper-free palladium catalyst is carbonylated with carbon monoxide. Extremely high yields of the desired alpha-substituted carboxylic acid can be obtained in very short reaction periods by use of a palladium catalyst that is formed from a palladium compound with a valence of zero to two and a cycloalkyldiarylphosphine ligand, such as neomenthyldiphenylphosphine.
    Type: Grant
    Filed: December 16, 1998
    Date of Patent: July 31, 2001
    Assignee: Albemarle Corporation
    Inventor: Tse-Chong Wu
  • Patent number: 6197997
    Abstract: A loaded ion-exchange resin, which resin has been loaded in its shrunken form. Also a process for removing iodide compounds from a liquid carboxylic acid and/or carboxylic acid anhydride obtained from the Group VIII noble metal catalysed, alkyl iodide co-catalysed carbonylation of alcohols and/or their reactive derivatives which process comprises contacting the liquid carboxylic acid and/or carboxylic acid anhydride with a metal loaded ion-exchange resin as described above wherein the metal is one or more of the metals silver, palladium or mercury.
    Type: Grant
    Filed: July 9, 1998
    Date of Patent: March 6, 2001
    Assignee: BP Chemicals Limited
    Inventors: John Laurence Carey, Michael David Jones, Andrew David Poole
  • Patent number: 6169201
    Abstract: Process for the preparation of N-acetyl protected amino acids of Formula I by amido carbonylation utilizing carbon monoxide, nitrile, and an aldehyde in the presence of a metal catalyst.
    Type: Grant
    Filed: May 13, 1999
    Date of Patent: January 2, 2001
    Assignee: Degussa-Huels AG
    Inventors: Matthias Beller, Markus Eckert, Wahed Moradi
  • Patent number: 6121500
    Abstract: A mixture of water and a glycol, such as ethylene glycol, is employed as the solvent for the reaction between 1,6-dibromo-2-naphthol and an alkali metal sulfite in the preparation of 6-bromo-2-naphthol and its derivatives to effect a substantial reduction in reaction time. The glycol/water mol ratio is ordinarily in the range of 0.1-0.5/1, preferably 0.3/0.5/1.
    Type: Grant
    Filed: March 4, 1999
    Date of Patent: September 19, 2000
    Assignee: Albemarle Corporation
    Inventor: Mahmood Sabahi