On Benzene Ring Patents (Class 558/343)
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Patent number: 10647641Abstract: 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: GrantFiled: July 19, 2019Date of Patent: May 12, 2020Assignees: SCG Chemicals Co., Ltd., Sulzer GTC Technology US Inc.Inventors: Alisa Kammafoo, Attapong Thirasak, Zhongyi Ding
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Publication number: 20120004384Abstract: 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: ApplicationFiled: February 25, 2011Publication date: January 5, 2012Inventors: W. Justin Youngblood, Jonathan S. Lindsey
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Patent number: 8049029Abstract: 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: GrantFiled: December 18, 2007Date of Patent: November 1, 2011Assignee: E. I. du Pont de Nemours and CompanyInventors: Joerg Bruening, Gary David Annis, Donald J Dumas, Rafael Shapiro
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Publication number: 20110040115Abstract: 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: ApplicationFiled: December 1, 2006Publication date: February 17, 2011Applicant: FINORGA SASInventors: Alexander Christian Comely, Marta Marfil Sánchez, Llorenc Rafecas Jané, Antoni Riera Escalé
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Patent number: 7595417Abstract: 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: GrantFiled: November 14, 2005Date of Patent: September 29, 2009Assignee: Merck & Co., Inc.Inventor: Steven A. Weissman
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Patent number: 7592452Abstract: 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: GrantFiled: August 27, 2007Date of Patent: September 22, 2009Assignee: SaltigoGmbHInventors: Nikolaus Müller, Wolfgang Mägerlein, Matthias Beller, Thomas Schareina, Alexander Zapf
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Patent number: 7371861Abstract: 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: GrantFiled: July 6, 2005Date of Patent: May 13, 2008Assignee: LANXESS Deutschland GmbHInventors: Axel Pleschke, Albrecht Marhold
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Patent number: 6861448Abstract: 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: GrantFiled: February 22, 2002Date of Patent: March 1, 2005Assignees: Virtual Drug Development, Inc., The UAB Research FoundationInventors: Wayne J. Brouillette, Lawrence DeLucas, Christie Brouillette, Sadanandan E. Velu, Yong-Chul Kim, Liyuan Mou, R. Stephen Porter
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Publication number: 20040236131Abstract: 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: ApplicationFiled: June 29, 2004Publication date: November 25, 2004Inventors: Peter J. Joyce, Roman Bielski, Marc Halpern
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Patent number: 6784308Abstract: 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: GrantFiled: July 8, 2002Date of Patent: August 31, 2004Assignee: Bayer AktiengesellschaftInventor: Markus Eckert
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Publication number: 20030225297Abstract: Compounds of formula VII are described: 1Type: ApplicationFiled: June 5, 2003Publication date: December 4, 2003Applicants: RHODIA CHIMIE, CENTRE NATIONAL DE LA RECHERCHE SCIENTIFIQUE (C.N.R.S.)Inventors: Marc Lemaire, Rob Tel Halle, Emmanuelle Schulz, Michel Spagnol
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Patent number: 6653497Abstract: 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: GrantFiled: May 29, 2002Date of Patent: November 25, 2003Assignee: Lonza AGInventors: Sajal Das, Ulrich Daum, Marion Fengler-Veith, Pascal Willa
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Patent number: 6635780Abstract: 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: GrantFiled: June 14, 2001Date of Patent: October 21, 2003Assignee: Bayer CropScience S.A.Inventors: Michel Casado, Patrick Ratton, Dominique Stephan, Agnès Viauvy
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Publication number: 20030017948Abstract: 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: ApplicationFiled: June 21, 2002Publication date: January 23, 2003Inventor: Achim Hupperts
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Publication number: 20030018209Abstract: 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: ApplicationFiled: July 8, 2002Publication date: January 23, 2003Inventor: Markus Eckert
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Patent number: 6162942Abstract: A process for preparing aromatic nitriles from corresponding chloroaromatics by reaction with cyanides.Type: GrantFiled: August 17, 1999Date of Patent: December 19, 2000Assignee: Bayer AktiengesellschaftInventors: Michael-Harold Rock, Albrecht Marhold
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Patent number: 6156922Abstract: 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: GrantFiled: September 15, 1998Date of Patent: December 5, 2000Assignee: Rhodia ChimieInventors: James Russell, Laurent Gilbert, Jean Pierre Maestro
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Patent number: 6153784Abstract: 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: GrantFiled: February 17, 1998Date of Patent: November 28, 2000Assignee: BASF AktiengesellschaftInventors: Heinz-Josef Kneuper, Hans-Jurgen Weyer, Horst Neuhauser, Johann-Peter Melder, Andreas Henne, Karl-Heinz Ross, Rainer Becker
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Patent number: 5965766Abstract: 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: GrantFiled: February 2, 1998Date of Patent: October 12, 1999Assignee: Rohm and Haas CompanyInventors: Joshua Anthony Chong, Fereydon Abdesaken, Charles Chao Wu
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Patent number: 5917079Abstract: 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: GrantFiled: July 1, 1997Date of Patent: June 29, 1999Assignee: Rohm and Haas CompanyInventors: Joshua Anthony Chong, Fereydon Abdesaken, Charles Chao Wu
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Patent number: 5705674Abstract: 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: GrantFiled: August 16, 1996Date of Patent: January 6, 1998Assignee: Hoechst AktiengesellschaftInventors: Thomas Wessel, Peter Koch
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Patent number: 5478963Abstract: 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: GrantFiled: January 21, 1994Date of Patent: December 26, 1995Assignee: Hoechst AktiengesellschaftInventors: Ralf Pfirmann, Theodor Papenfuhs
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Patent number: 5386051Abstract: 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: GrantFiled: December 10, 1993Date of Patent: January 31, 1995Assignee: Bayer AktiengesellschaftInventors: Gunther Beck, Bernd Kaletta
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Patent number: 5187295Abstract: 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: GrantFiled: February 14, 1992Date of Patent: February 16, 1993Assignee: Hoechst AktiengesellschaftInventor: Thomas Schach
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Patent number: 5175336Abstract: 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: GrantFiled: May 16, 1991Date of Patent: December 29, 1992Assignee: Bayer AktiengesellschaftInventors: Gunther Beck, Wolfgang von der Emden, Helmut Heitzer, Friedrich W. Krock, Ernst Kysela, Albrecht Marhold
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Patent number: 5169972Abstract: 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: GrantFiled: December 3, 1990Date of Patent: December 8, 1992Assignee: Bromine Compounds LimitedInventors: Abram Becker, Hyman Stollar
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Patent number: 4959487Abstract: 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: GrantFiled: March 2, 1989Date of Patent: September 25, 1990Assignee: Idemitsu Kosan Co., Ltd.Inventors: Hirotaka Yamasaki, Yoshio Hironaka
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Patent number: 4925642Abstract: 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: GrantFiled: May 24, 1988Date of Patent: May 15, 1990Assignee: Bromine Compounds LimitedInventors: Hayman Stollar, Abram Becker
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Patent number: 4886936Abstract: 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: GrantFiled: August 15, 1988Date of Patent: December 12, 1989Assignee: ICI Americas Inc.Inventor: Stephen E. Dinizo
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Patent number: 4801728Abstract: 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: GrantFiled: June 25, 1986Date of Patent: January 31, 1989Assignee: M&T Chemicals Inc.Inventors: Charles L. Liotta, Edward M. Burgess