On Benzene Ring Patents (Class 558/343)
  • Patent number: 10647641
    Abstract: Extractive agent compounds are disclosed, with exemplary compounds having Formula (I): wherein Ra and Rb are independently selected from the group consisting of an oxygen radical, a hydrogen radical, and a hydrocarbyl radical having from about 1 to about 20 carbon atoms, and wherein R2-R6 are independently selected from the group consisting of halo, a hydrogen radical, and a hydrocarbyl radical having from about 1 to about 20 carbon atoms, and further wherein at least two of R2-R6 are halo. Also disclosed are extractive distillation processes, comprising distilling a liquid mixture comprising ethylbenzene, a further C8 aromatic compound, and an extractive agent compound as described herein. The extractive agent contributes to improved separability of ethylbenzene from the further C8 aromatic compound.
    Type: Grant
    Filed: July 19, 2019
    Date of Patent: May 12, 2020
    Assignees: SCG Chemicals Co., Ltd., Sulzer GTC Technology US Inc.
    Inventors: Alisa Kammafoo, Attapong Thirasak, Zhongyi Ding
  • Publication number: 20120004384
    Abstract: The present invention provides an article of manufacture formed from a substrate and a benzazoloporphyrazine bound to the substrate. The article may take a variety of different forms and may be for example an electrochromic display, a molecular capacitor, a battery, a solar cell, or a molecular memory device. Methods of making such articles, along with compounds, methods and intermediates useful for making such benzazoloporphyrazines, are also described.
    Type: Application
    Filed: February 25, 2011
    Publication date: January 5, 2012
    Inventors: W. Justin Youngblood, Jonathan S. Lindsey
  • Patent number: 8049029
    Abstract: Disclosed is a method for preparing a compound of Formula 1 comprising contacting a compound of Formula 2 with a metal cyanide reagent, a copper(I) salt reagent, an iodide salt reagent and at least one compound of Formula 3 wherein R1 is NHR3 or OR4; R2 is CH3 or Cl; R3 is H, C1-C4 alkyl, cyclopropyl, cyclopropylcyclopropyl, cyclopropylmethyl or methylcyclopropyl; R4 is H or C1-C4 alkyl; Y is Br or Cl; X is NR13 or O; n is 0 or 1; and R5, R6, R7, R8, R9, R10, R11, R12 and R13 are as defined in the disclosure. Also disclosed is a method for preparing a compound of Formula 2 wherein Y is Br and R1 is NHR3 comprising introducing a gas containing bromine into a liquid containing a compound of Formula 4, and further disclosed is a method for preparing a compound of Formula 5 wherein R14, R15, R16 and Z are as defined in the disclosure using a compound of Formula 1 characterized by preparing the compound of Formula 1 by the method disclosed above.
    Type: Grant
    Filed: December 18, 2007
    Date of Patent: November 1, 2011
    Assignee: E. I. du Pont de Nemours and Company
    Inventors: Joerg Bruening, Gary David Annis, Donald J Dumas, Rafael Shapiro
  • Publication number: 20110040115
    Abstract: Process for the preparation of aromatic derivatives of 1-adamantane (tricyclo[3.3.1.1 (3,7)]decane), or an acceptable pharmaceutical salt thereof, based on a hydrolysis reaction of a precursor cyano compound. It also comprises different processes for obtaining the cyano compound. It is especially useful for obtaining Adapalene on an industrial scale in high yield and purity. It also comprises new intermediates useful in said preparation process.
    Type: Application
    Filed: December 1, 2006
    Publication date: February 17, 2011
    Applicant: FINORGA SAS
    Inventors: Alexander Christian Comely, Marta Marfil Sánchez, Llorenc Rafecas Jané, Antoni Riera Escalé
  • Patent number: 7595417
    Abstract: A practical, ligand-free cyanation of aryl bromides employs Pd catalyst in combination with a non-toxic cyanide source, Mn[Fe(CN)6] (M=K or Na; n is 3 or 4), or a hydrate thereof, and a base. The reactions are performed in a polar aprotic solvents and provide the corresponding aryl nitrile in 83-96% yield, typically in less than 5 h.
    Type: Grant
    Filed: November 14, 2005
    Date of Patent: September 29, 2009
    Assignee: Merck & Co., Inc.
    Inventor: Steven A. Weissman
  • Patent number: 7592452
    Abstract: The present invention relates to a process for preparing optionally substituted aromatic or heteroaromatic nitriles starting from haloaromatics. These are reacted in a copper-catalysed reaction with potassium hexacyanoferrate(II) or potassium hexacyanoferrate(III) in the presence of heteroaromatic amines.
    Type: Grant
    Filed: August 27, 2007
    Date of Patent: September 22, 2009
    Assignee: SaltigoGmbH
    Inventors: Nikolaus Müller, Wolfgang Mägerlein, Matthias Beller, Thomas Schareina, Alexander Zapf
  • Patent number: 7371861
    Abstract: The present invention relates to an improved process for preparing ring-fluorinated aromatics of the general formula (I) by a halogen exchange reaction (halex reaction) of a plurality of halogen substituents in one stage in the presence of a catalyst.
    Type: Grant
    Filed: July 6, 2005
    Date of Patent: May 13, 2008
    Assignee: LANXESS Deutschland GmbH
    Inventors: Axel Pleschke, Albrecht Marhold
  • Patent number: 6861448
    Abstract: Disclosed are compounds that inhibit the microbial NAD synthetase enzyme. For example, disclosed are compounds of the formula Ar1—X—Ar2—Y—L—Z—Q, wherein Q is Q1Ar3 or Ar3Q1; Ar1, Ar2, and Ar3 are independently aryl or heteroaryl, optionally substituted with one or more substituents; X, Y, and Z are independently selected from the group consisting of a covalent bond or groups containing one or more of C, H, N, O, S atoms; L is a linker and Q1 is an alkylenyl, alkylenyl carbonyloxy alkyl, or alkylenyl carbonylamino alkyl group, optionally having a substituent; a covalent bond; a group containing amidine or guanidine function wherein the amidine or guanidine may be optionally N-substituted with an alkyl; or a zwitterion; or a pharmaceutically acceptable salt thereof.
    Type: Grant
    Filed: February 22, 2002
    Date of Patent: March 1, 2005
    Assignees: Virtual Drug Development, Inc., The UAB Research Foundation
    Inventors: Wayne J. Brouillette, Lawrence DeLucas, Christie Brouillette, Sadanandan E. Velu, Yong-Chul Kim, Liyuan Mou, R. Stephen Porter
  • Publication number: 20040236131
    Abstract: A method for preparing organic products from aqueous solutions, such as waste or byproduct liquid streams and waste or byproduct gas or vapor streams, uses phase transfer catalysis to transfer a chemical species in low concentration from the aqueous solution to the organic phase or the aqueous-organic interface. The system has little or no organic solvent, and the organic phase contains an electrophile which participates in the reaction. In one embodiment, the aqueous solution is contacted with the electrophile and a phase transfer catalyst and, optionally, a pH adjusting agent in the event that the chemical species in the aqueous solution is not sufficiently ionized to react with the electrophile, and optionally an organic solvent. A method for continuously converting a chemical species involves this contacting step, separating the phases, then dividing the organic phase into the product, the phase transfer catalyst, and the optional organic solvent.
    Type: Application
    Filed: June 29, 2004
    Publication date: November 25, 2004
    Inventors: Peter J. Joyce, Roman Bielski, Marc Halpern
  • Patent number: 6784308
    Abstract: The invention relates to a process for the preparation of aromatic nitriles form halogenoaromatics or aryl perfluorosulfonates and alkali metal cyanides in the presence of palladium catalysts, zinc, and polyethers.
    Type: Grant
    Filed: July 8, 2002
    Date of Patent: August 31, 2004
    Assignee: Bayer Aktiengesellschaft
    Inventor: Markus Eckert
  • Publication number: 20030225297
    Abstract: Compounds of formula VII are described: 1
    Type: Application
    Filed: June 5, 2003
    Publication date: December 4, 2003
    Applicants: RHODIA CHIMIE, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N.R.S.)
    Inventors: Marc Lemaire, Rob Tel Halle, Emmanuelle Schulz, Michel Spagnol
  • Patent number: 6653497
    Abstract: Dicyanatochalcones of general formula: wherein R1 to R8, independent of one another, represent hydrogen, C1-4-alkyl, C1-4-alkoxy or halogen. The compounds can be produced from corresponding dicyanatochalcones by reacting them with chlorine cyanide or bromine cyanide and with a tertiary amine. The compounds are suited for producing polytriazine resins exhibiting good mechanical properties, a low dielectric constant and a good behavior in fire.
    Type: Grant
    Filed: May 29, 2002
    Date of Patent: November 25, 2003
    Assignee: Lonza AG
    Inventors: Sajal Das, Ulrich Daum, Marion Fengler-Veith, Pascal Willa
  • Patent number: 6635780
    Abstract: The invention relates to a process for the preparation of a compound of formula (I) wherein: R1 represents C1-4 haloalkyl, fluorine, chlorine or bromine; and R2 represents hydrogen or C1-4 alkoxy; which process comprises the reaction of the corresponding ortho-nitrohalobenzene of formula (II): wherein R1 and R2 are as hereinbefore defined and X represents a fluorine or bromine atom, with, when X represents a fluorine atom: (a) an alkali metal cyanide, in a non aqueous solvent, optionally in the presence of a catalyst; or when X represents a bromine atom: (b) cuprous cyanide, in a non aqueous solvent, optionally in the presence of a catalyst selected from an alkali metal bromide or an alkaline earth metal bromide; or (c) an alkali metal cyanide, in a non aqueous solvent, in the presence of a catalytic amount of cuprous cyanide and a phase transfer catalyst.
    Type: Grant
    Filed: June 14, 2001
    Date of Patent: October 21, 2003
    Assignee: Bayer CropScience S.A.
    Inventors: Michel Casado, Patrick Ratton, Dominique Stephan, Agnès Viauvy
  • Publication number: 20030017948
    Abstract: The invention relates to a novel process for preparing N-substituted 2,4-diamino-5-fluoro-benzonitriles which are known as intermediates in the preparation of herbicides, to novel N-substituted 4-bromo-6-fluoro-1,3-phenylenediamines, to novel N-substituted 2-bromo-4-fluoro-5-nitro-anilines and to novel N-substituted 2-bromo-4-fluoro-anilines as intermediates for this process, and to processes for their preparation.
    Type: Application
    Filed: June 21, 2002
    Publication date: January 23, 2003
    Inventor: Achim Hupperts
  • Publication number: 20030018209
    Abstract: The invention relates to a process for the preparation of aromatic nitrites from halogenoaromatics or aryl perfluorosulfonates and alkali metal cyanides in the presence of palladium catalysts, zinc, and polyethers.
    Type: Application
    Filed: July 8, 2002
    Publication date: January 23, 2003
    Inventor: Markus Eckert
  • Patent number: 6162942
    Abstract: A process for preparing aromatic nitriles from corresponding chloroaromatics by reaction with cyanides.
    Type: Grant
    Filed: August 17, 1999
    Date of Patent: December 19, 2000
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael-Harold Rock, Albrecht Marhold
  • Patent number: 6156922
    Abstract: The present invention relates to a method for the synthesis of a halogen substituted aryl nitrile, where the halogens are selected from Cl, Br, or I, by reacting an aryl dihalide with a halogen/fluoride exchange reactant to produce a halogen substituted aryl fluoride which is then reacted with a fluoride/cyanide exchange reactant to produce the halogen substituted aryl nitrile.
    Type: Grant
    Filed: September 15, 1998
    Date of Patent: December 5, 2000
    Assignee: Rhodia Chimie
    Inventors: James Russell, Laurent Gilbert, Jean Pierre Maestro
  • Patent number: 6153784
    Abstract: Halides are removed from halide-containing nitrile mixtures by(a) thermally treating the halide-containing nitrile mixture,(b) subsequently adding a base to the thermally treated nitrile mixture and(c) subsequently separating off the base from the nitrile mixture.Amines are prepared by(A) reacting alkyl halides with metal cyanides in an at least two-phase reaction medium in the presence of halide-containing phase-transfer catalysts to give alkanenitriles,(B) separating off the resulting halide-containing alkanenitrile mixture phase and(C) further treating the halide-containing alkanenitrile mixture phase, as described in the stages(a)-(c) removing halides from halide-containing nitrile mixtures and(d) hydrogenating nitrites obtained in stage (c) to give amines, in the presence of suspended or fixed-bed catalysts.
    Type: Grant
    Filed: February 17, 1998
    Date of Patent: November 28, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz-Josef Kneuper, Hans-Jurgen Weyer, Horst Neuhauser, Johann-Peter Melder, Andreas Henne, Karl-Heinz Ross, Rainer Becker
  • Patent number: 5965766
    Abstract: Nucleophilic substitution reactions on halobenzenes or triflyl substituted benzenes are carried out in the presence of catalysts. In particular the present invention provides a process leading to optionally substituted hydroxybenzoic, alkanoyloxybenzoic, formyloxybenzoic and alkoxybenzoic acids and optionally substituted hydroxybenzonitriles and alkoxybenzonitriles from substituted 2,6-dihalobenzenes, 2-halo-6-triflylbenzene and 2,6-ditriflylbenzenes.
    Type: Grant
    Filed: February 2, 1998
    Date of Patent: October 12, 1999
    Assignee: Rohm and Haas Company
    Inventors: Joshua Anthony Chong, Fereydon Abdesaken, Charles Chao Wu
  • Patent number: 5917079
    Abstract: Nucleophilic substitution reactions on halobenzenes are carried out in the presence of catalysts. In particular the present invention provides a process leading to optionally substituted hydroxybenzoic and alkoxybenzoic acids and optionally substituted hydroxybenzonitriles and alkoxybenzonitriles from substituted 2,6-dihalobenzenes.
    Type: Grant
    Filed: July 1, 1997
    Date of Patent: June 29, 1999
    Assignee: Rohm and Haas Company
    Inventors: Joshua Anthony Chong, Fereydon Abdesaken, Charles Chao Wu
  • Patent number: 5705674
    Abstract: The present invention relates to a process for preparing ortho-nitrobenzonitriles of the formula I, ##STR1## where R.sup.1 and R.sup.2 are as defined in claim 1, by reacting the corresponding ortho-fluoronitrobenzenes with alkali metal cyanides or cyanide-donating substances in the presence of phase transfer catalysts.
    Type: Grant
    Filed: August 16, 1996
    Date of Patent: January 6, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Thomas Wessel, Peter Koch
  • Patent number: 5478963
    Abstract: The present invention describes the novel intermediates 2,3-difluoro-6-nitrobenzonitrile and 2-chloro-5,6-difluorobenzonitrile, a process for their preparation and their advantageous use for the preparation of 2,3,6-trifluorobenzoic acid, which in turn is a valuable intermediate for the preparation of insecticides and antibacterial agents. The intermediates according to the invention are prepared from 2,3,4-trifluoronitrobenzene by fluorine/cyanide exchange and subsequent denitrating chlorination. 2,3,6-Trifluorobenzoic acid can be prepared from the novel intermediates, in a manner known per se in the literature, by simple chlorine/fluorine exchange and subsequent hydrolysis in a process which overall is industrially advantageous and economically favorable.
    Type: Grant
    Filed: January 21, 1994
    Date of Patent: December 26, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ralf Pfirmann, Theodor Papenfuhs
  • Patent number: 5386051
    Abstract: 1,2,3-Tricyanobenzene can be prepared in a good yield from fluorobenzonitriles by reaction with an alkali metal cyanide. This product can be converted into metal-free tetracyanophthalocyanines or into the corresponding metal complexes by tetramerisation, if appropriate in the presence of metals or metal compounds. These products are excellent organic pigments.
    Type: Grant
    Filed: December 10, 1993
    Date of Patent: January 31, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunther Beck, Bernd Kaletta
  • Patent number: 5187295
    Abstract: Process for the preparation of 2,4-dichloro-5-fluorobenzonitrile, by reacting 5-bromo-2,4-dichlorofluorobenzene with about 10 to about 300 mol % of copper(I) cyanide in the presence of about 10 to about 2,000 mol % of a polar aprotic solvent at temperatures from about 100.degree. to about 250.degree. C. to give 2,4-dichloro-5-fluorobenzonitrile.
    Type: Grant
    Filed: February 14, 1992
    Date of Patent: February 16, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Thomas Schach
  • Patent number: 5175336
    Abstract: The invention relates to new fluoromethylated polycyanobenzenes of the formula ##STR1## in which X represents hydrogen, fluorine or chlorine,m is 1 or 2 andn is (6-m),to a process for their preparation and to the salt-like alkali metal cyanide adducts of the fluoromethylated polycyanobenzenes formed as intermediates in this preparation process and to the use of the fluoromethylated polycyanobenzenes for the detection of anions.
    Type: Grant
    Filed: May 16, 1991
    Date of Patent: December 29, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunther Beck, Wolfgang von der Emden, Helmut Heitzer, Friedrich W. Krock, Ernst Kysela, Albrecht Marhold
  • Patent number: 5169972
    Abstract: In a process for the preparation and the isolation of p-hydroxybenzonitrile (HBN), in which a p-halogenated phenol is reacted with cuprous cyanide in a suitable solvent, the reaction mixture obtained after the reaction of the p-halogenated phenol with cuprous cyanide has been substantially completed is contacted with an aqueous solution of a bromide salt and, optionally, an organic diluent, the aqueous and organic phases are separated, HBN is distilled out from the organic phase, an alkali metal cyanide is added to the aqueous phase and CuCN is filtered off from the resulting aqueous phase.
    Type: Grant
    Filed: December 3, 1990
    Date of Patent: December 8, 1992
    Assignee: Bromine Compounds Limited
    Inventors: Abram Becker, Hyman Stollar
  • Patent number: 4959487
    Abstract: A process for producing aromatic nitrile, comprising reacting aromatic halide substituted by a nitro group in the ortho position relative to the halogen atom with 0.1 to 0.99 mol of cuprous cyanide and 0.1 to 2.0 mol of alkali cyanide, both being per mol of said aromatic halide, in a polar solvent, the amount of said aprotic solvent being 0.1 to 30 parts by weight per 100 parts by weight of said aromatic halide.
    Type: Grant
    Filed: March 2, 1989
    Date of Patent: September 25, 1990
    Assignee: Idemitsu Kosan Co., Ltd.
    Inventors: Hirotaka Yamasaki, Yoshio Hironaka
  • Patent number: 4925642
    Abstract: A process is provided by means of which aromatic nitriles can be isolated in high yield. The process comprises reacting an aromatic halogenated compound with cuprous cyanide in a suitable solvent.The process is suitable for preparing many important materials, such as p-hydroxybenzonitrile.
    Type: Grant
    Filed: May 24, 1988
    Date of Patent: May 15, 1990
    Assignee: Bromine Compounds Limited
    Inventors: Hayman Stollar, Abram Becker
  • Patent number: 4886936
    Abstract: Ortho-nitrobenzonitriles are produced from the corresponding ortho-nitrochlorobenzenes by reaction with cuprous cyanide and an alkali metal bromide, an alkaline earth metal bromide, or zinc bromide or with a combination of lithium cyanide and cuprous bromide, optionally in the presence of a solvent.
    Type: Grant
    Filed: August 15, 1988
    Date of Patent: December 12, 1989
    Assignee: ICI Americas Inc.
    Inventor: Stephen E. Dinizo
  • Patent number: 4801728
    Abstract: The present invention relates to reaction mixtures and processes which employ an .omega.-phase catalyst for carrying out displacement reactions at a substantially enhanced rate.
    Type: Grant
    Filed: June 25, 1986
    Date of Patent: January 31, 1989
    Assignee: M&T Chemicals Inc.
    Inventors: Charles L. Liotta, Edward M. Burgess