Replacing Halogen With Cyano Patents (Class 558/342)
  • Patent number: 10364214
    Abstract: The invention relates to a method for producing isocyanates, according to which exhaust flows provided for the combustion are guided through an adsorption device before being supplied into the exhaust gas combustion process, and are thereby depleted of solvent, the adsorption device comprising at least two adsorption units connected in parallel, which are alternately (i) exposed to the at least one exhaust flow and (ii) regenerated with water vapor, where, during method step (i), an exhaust flow depleted of solvent is obtained, and during method step (ii), a flow containing water and solvent is obtained, the solvent proportion of which is recycled into a method for producing isocyanates.
    Type: Grant
    Filed: August 29, 2017
    Date of Patent: July 30, 2019
    Assignee: Covestro Deutschland AG
    Inventors: Thomas Knauf, Dirk Manzel, Peter Plathen, J├╝rgen Spriewald
  • Patent number: 10144704
    Abstract: Novel crystal forms of (R)-(+)-verapamil hydrochloride are disclosed.
    Type: Grant
    Filed: March 11, 2018
    Date of Patent: December 4, 2018
    Assignee: Center Laboratories, Inc.
    Inventors: Jui-Pao Hsu, Guang-Tzuu Shane, Yu-Yin Yeh, Meng-Ju Lee
  • Patent number: 9067869
    Abstract: The present invention relates to a method for preparing difluoracetonitrile and the derivatives thereof. The method for preparing difluoroacetonitrile according to the invention is characterized in that it includes reacting halogenodifluoromethane and a source of cyanide anions in an alkaline medium. The invention also relates to the use of difluoroacetonitrile as an intermediate in the manufacture of difluoroacetic acid and the salts, esters, or amide thereof.
    Type: Grant
    Filed: March 8, 2012
    Date of Patent: June 30, 2015
    Assignee: RHODIA OPERATIONS
    Inventor: Olivier Buisine
  • Patent number: 8247593
    Abstract: A one-pot process of preparing a substituted 7-cyano quinone methide in which i) a substituted phenol is chloromethylated to form a substituted 4-chloromethylphenol; ii) converting the substituted 4-chloromethylphenol to a substituted 4-cyanomethylphenol; and iii) oxidizing the substituted 4-cyanomethylphenol to the substituted 7-cyano quinone methide, where steps i)-iii) are carried out in a single reaction vessel in a solvent system comprising water and one or more organic solvents and where after steps i) and ii) the aqueous portion of the reaction mixture is removed and the reagents for the subsequent step are added in aqueous solution. The 7-cyano quinone methides are effective inhibitors of the polymerization of reactive monomers.
    Type: Grant
    Filed: May 13, 2008
    Date of Patent: August 21, 2012
    Assignee: Nalco Company
    Inventors: Christopher F. Morrison, Joseph Paul Street
  • Publication number: 20120083608
    Abstract: The present invention is a process for the preparation of [4-(2-chloro-4-methoxy-5-methylphenyl)-5-methyl-thiazolo-2-yl]-[2-cyclopropyl-1-(3-fluoro-4-methylphenyl)-ethyl]-amine as set forth in formula (I) and new intermediates of the preparation process.
    Type: Application
    Filed: October 27, 2011
    Publication date: April 5, 2012
    Applicant: SANOFI
    Inventors: Janos FAZEKAS, Peter MISKOLCZI, Annamaria MOLNAR, Bela AGAI, Zsolt PARKANYI
  • Publication number: 20090287013
    Abstract: A one-pot process of preparing a substituted 7-cyano quinone methide in which i) a substituted phenol is chloromethylated to form a substituted 4-chloromethylphenol; ii) converting the substituted 4-chloromethylphenol to a substituted 4-cyanomethylphenol; and iii) oxidizing the substituted 4-cyanomethylphenol to the substituted 7-cyano quinone methide, where steps i)-iii) are carried out in a single reaction vessel in a solvent system comprising water and one or more organic solvents and where after steps i) and ii) the aqueous portion of the reaction mixture is removed and the reagents for the subsequent step are added in aqueous solution. The 7-cyano quinone methides are effective inhibitors of the polymerization of reactive monomers.
    Type: Application
    Filed: May 13, 2008
    Publication date: November 19, 2009
    Inventors: Christopher F. Morrison, Joseph Paul Street
  • 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
  • Publication number: 20040214297
    Abstract: The present invention provides methods and compositions for preparing 4-substituted 3-hydroxybutyric acid derivatives by halohydrin dehalogenase-catalyzed conversion of 4-halo-3-hydroxybutyric acid derivatives. The present invention further provides methods and compositions for preparing 4-halo-3-hydroxybutyric acid derivatives by ketoreductase-catalyzed conversion of 4-halo-3-ketobutyric acid derivatives The present invention also provides methods and compositions for preparing vicinal cyano, hydroxyl substituted carboxylic acid esters.
    Type: Application
    Filed: February 18, 2004
    Publication date: October 28, 2004
    Inventors: S. Christopher Davis, John H. Grate, David R. Gray, John M. Gruber, Gjalt W. Huisman, Steven K. Ma, Lisa M. Newman, Roger Sheldon, Li A. Wang
  • Publication number: 20040024238
    Abstract: The invention concerns the use of aliphatic nitriles with relatively high molecular weight, as polar aprotic solvents, in particular in nucleophilic substitution reactions of the aromatic type. Said nitriles have a molecular mass more 79, preferably more than 90. The invention is useful for synthesis of fluorinated aromatic compounds.
    Type: Application
    Filed: August 20, 2003
    Publication date: February 5, 2004
    Inventors: Nathalie Laurain, Samir Zard
  • Publication number: 20030105347
    Abstract: There are provided a method for producing a 4-cyano-3-oxobutanoate by reacting a 4-halo-3-oxobutanoate with an alkaline metal cyanide in methanol, a process for producing 4-cyano-3-hydroxybutanoate therefrom.
    Type: Application
    Filed: October 29, 2001
    Publication date: June 5, 2003
    Inventors: Ryuhei Wakita, Nobuya Ito
  • Publication number: 20030100789
    Abstract: The present invention provides a process for the preparation of pesticidal 1,4-diaryl-2-fluoro-4-cyano-2-butene compounds having the structural formula I 1
    Type: Application
    Filed: July 9, 2002
    Publication date: May 29, 2003
    Inventors: Yulin Hu, David Allen Hunt
  • Patent number: 6444838
    Abstract: The present invention provides a process for the preparation of pesticidal 1,4-diaryl-2-fluoro-4-cyano-2 -butene compounds having the structural formula I and intermediates useful therefor.
    Type: Grant
    Filed: May 4, 2001
    Date of Patent: September 3, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Yulin Hu, David Allen Hunt
  • Patent number: 6355827
    Abstract: In a particularly advantageous process for producing 2-cyanoindan-1-ones from 2-halogenated indan-1-ones by reaction with a cyanide salt, the cyanide salt is dissolved in a dipolar aprotic solvent or in a water-miscible ether and 2-halogenated indan-1-one is metered into this solution.
    Type: Grant
    Filed: February 18, 2000
    Date of Patent: March 12, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Joachim Komoschinski, Helmut Fiege, Guido Steffan
  • Patent number: 6344569
    Abstract: The present invention provides a process which can produce an important intermediate for the production of the HMG coenzyme A reductase inhibitor atrovastatin, 6-cyanomethyl-1,3-dioxane-4-acetic acid derivatives, with ease industrially and in good yields, wherein a 3,5-dihydroxy-6-halohexanoic acid derivative is used as the starting material, and which comprises cyanation by reaction with a cyanating agent for substitution of a cyano group for the halogen atom and an acetal formation reaction of the diol moiety with an acetal forming reagent in the presence of an acid catalyst.
    Type: Grant
    Filed: January 2, 2001
    Date of Patent: February 5, 2002
    Assignee: Kaneka Corporation
    Inventors: Masaru Mitsuda, Makoto Miyazaki, Kenji Inoue
  • 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: 6140527
    Abstract: This invention has its objects to provide a process for producing a butyric acid ester derivative of the above general formula (2) which is capable of removing various impurity byproducts whose formation cannot be avoided by the prior art technology, particularly the compound of the above general formula (1), with good efficiency.This invention is related to a process for producing a butyric acid ester derivative of the general formula (2) which comprises treating a mixture containing a compound of the following general formula (1) with an addition reagent capable of adding itself to said ethylenic bond to thereby convert said compound of the general formula (1) to an addition product which can be easily separated from said butyric acid ester derivative of the general formula (2) and a process for producing a butyric acid ester derivative of the general formula (2) which comprises reacting a compound of the general formula (3) with a salt of prussic acid by a flow method.HOCH.sub.2 --CH.dbd.
    Type: Grant
    Filed: September 7, 1999
    Date of Patent: October 31, 2000
    Assignee: Kaneka Corporation
    Inventors: Shigeki Kunihiro, Fumihiko Kano, Natsuki Mori
  • Patent number: 6130347
    Abstract: Cyanoacetic esters are prepared by reacting a corresponding monochloroacetic ester with hydrogen cyanide in the presence of a base, where the base is a compound selected from the group consisting of tertiary amines, salts of carbonic acid, salts of carbonic acid monoesters, salts of carboxylic acids, amidines, guanidines and aromatic N-heterocyclic compounds.
    Type: Grant
    Filed: November 2, 1999
    Date of Patent: October 10, 2000
    Assignee: BASF Aktiengesellschaft
    Inventors: Manfred Julius, Rolf Schneider, Klaus Mundinger, Jakob Fischer
  • Patent number: 5908953
    Abstract: Crude (R)-4-cyano-3-hydroxybutyric acid lower alkyl ester, obtained by subjecting an (S)-4-halogeno-3-hydroxybutyric acid lower alkyl ester to a cyano-introducing reaction, is purified by distillation carried out in the presence of a solvent having a boiling point within the range of 50.degree. C. to 160.degree. C. at 10 Torr.
    Type: Grant
    Filed: December 10, 1997
    Date of Patent: June 1, 1999
    Assignee: Mitsubishi Chemical Corporation
    Inventors: Hitoshi Matsuda, Toshiharu Shibata, Hidekichi Hashimoto, Mitsumasa Kitai
  • Patent number: 5780665
    Abstract: Halomethylbenzoyl cyanides IPH--CO--CN (I)where Ph is phenyl which is substituted by chloromethyl or bromomethyl and may cary 1-4 other rradicals, are prepared from halomethylbenzoyl chlorides IIPH--CO--Cl (II),by reacting II with a cyanide-donating compound in the presence of a Lewis acid, if required in an inert organic solvent or diluent, and then isolating the product.The halomethylbenzoyl cyanides I are important intermediates for synthesizing crop protection agents.
    Type: Grant
    Filed: May 6, 1997
    Date of Patent: July 14, 1998
    Assignee: BASF Aktiengesellschaft
    Inventors: Heinz Isak, Michael Keil, Bernd Wolf, Horst Wingert, Thomas Wettling
  • Patent number: 5597941
    Abstract: The process for producing 5-amino-3-methylpyrazole includes the steps of reacting 2,3-dichloropropene with a cyanogenating agent in the presence of a cuprous salt and water at a pH of 3-8 to obtain at least one intermediate selected from the group consisting of 3-chloro-3-butenonitrile and 2,3-butadienenitrile; reacting the at least one intermediate with a base in the presence of water at a pH of 12.5 or above to obtain 2-butynenitrile; and reacting the 2-butynenitrile with hydrazine. This process is advantageous in that it enables the production of 5-amino-3-methylpyrazole in high yield without using any reagent which may produce fire. 5-Amino-3-methylpyrazole is a useful intermediate for medicines, agricultural chemicals, photographic chemicals, etc.
    Type: Grant
    Filed: December 29, 1994
    Date of Patent: January 28, 1997
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kazuya Minamisaka, Masahito Sekiguchi, Kenji Saito
  • Patent number: 5483007
    Abstract: A process of making poly(glycidyl azide) and 3,6 -dioxadecyl thiocyanate using a phase transfer catalyst that permits the recovery and recycle of the phase transfer catalyst.
    Type: Grant
    Filed: April 22, 1993
    Date of Patent: January 9, 1996
    Assignee: Minnesota Mining and Manufacturing Company
    Inventor: Kim L. Johnson
  • Patent number: 5430171
    Abstract: T-butyl (R)-(-)-4-cyano-3-hydroxybutyrate having an optical purity of 99%ee or higher and a process for producing the same are disclosed, the process comprising cyanogenation of a t-butyl (S)-(-)-4-halogeno-3-hydroxybutyrate obtained by enantioselective hydrogenation of a t-butyl 4-halogenoacetoacetate. Recrystallization of the resulting crude product gives the optically active compound with high optical purity.
    Type: Grant
    Filed: July 11, 1994
    Date of Patent: July 4, 1995
    Assignee: Takasago International Corporation
    Inventors: Shigeru Mitsuhashi, Kazutoshi Sakurai, Hidenori Kumobayashi
  • Patent number: 5302263
    Abstract: A process for obtaining an aryl-substituted aliphatic nitrile is described. The process utilizes a solution of an aryl-substituted aliphatic halide and an organic or inorganic cyanide substantially insoluble in the solution. The mixture is subjected to ultrasonic vibrations for a time and at a temperature sufficient to produce the aryl-substituted aliphatic nitrile.
    Type: Grant
    Filed: April 29, 1993
    Date of Patent: April 12, 1994
    Assignee: Ethyl Corporation
    Inventor: Thanikavelu Manimaran
  • Patent number: 5155251
    Abstract: An improved process for the preparation of (5R)-1,1-dimethylethyl-6-cyano-5-hydroxy-3-oxo-hexanoate is described where a halo hydroxyester or other activated dihydroxyester is converted in two steps to the desired product.
    Type: Grant
    Filed: October 11, 1991
    Date of Patent: October 13, 1992
    Assignee: Warner-Lambert Company
    Inventors: Donald E. Butler, Tung V. Le, Alan Millar, Thomas N. Nanninga
  • Patent number: 5001288
    Abstract: A monoalkylaromatic hydrocarbon is haloethylated to a 1-halo-1-arylethane with minimal co-formation of diarylalkane by-product by reacting it with hydrogen chloride or bromide and acetaldehyde at a temperature in the range of abaout +10.degree. C. to about -35.degree. C. in the presence of at least about 1.4 mols of hydrogen sulfate per mol of the aromatic hydrocarbon and in the absence of more than about 15% by weight of water, based on the weight of the hydrogen sulfate; the temperature being not higher than about -10.degree. C. when hydrogen chloride is employed.
    Type: Grant
    Filed: August 17, 1989
    Date of Patent: March 19, 1991
    Assignee: Ethyl Corporation
    Inventor: George A. Knesel
  • Patent number: 4994597
    Abstract: The present invention presents a method for preparation of S-3,4-dihydroxy butyronitrile expressed by the structural formula (II) ##STR1## characterized by causing R-3-chloro-1,2-propanediol expressed by the structural formula (I) ##STR2## to react with a cyanating agent. According to this invention, optically active 3,4-dihydroxy butyronitrile and 3,4-dihydroxy butyric acid derivatives may be manufactured economically and efficiently.
    Type: Grant
    Filed: April 27, 1989
    Date of Patent: February 19, 1991
    Assignee: Kanegafuchi Kagaku Kogyo Kabushiki Kaisha
    Inventors: Kenji Inoue, Mitsunori Matsumoto, Satomi Takahashi
  • Patent number: 4966988
    Abstract: A method is provided for forming (3-trifluoromethylphenyl)acetonitrile through the intermediate .alpha.,.alpha.,.alpha.-trifluoro-.alpha.'-chloro-m-xylene. This intermediate is formed by selective chlorination of .alpha.,.alpha.,.alpha.'-trichloro-m-xylene under conditions which maximize yield and minimize the formation of undesired, non-recyclable chlorinated by-products.
    Type: Grant
    Filed: February 17, 1989
    Date of Patent: October 30, 1990
    Assignee: Chevron Research Company
    Inventors: William L. Schinski, Peter Denisevich, Jr.
  • Patent number: 4732709
    Abstract: Process for the production of optically-active di-[3-chloro-2-oxy-propyltrimethylammonium]-tartrate. Racemic 3-chloro-2-oxy-propyltrimethylammonium-chloride is converted by racemate resolution with optically-active tartaric acid into the optically-active di-[3-chloro-2-oxy-propyltrimethylammonium]-tartrate. Such optically-active tartrate compound is dissociated in tartaric acid and optically-active 3-chloro-2-oxy-propyltrimethylammonium-chloride and the latter is converted with inorganic cyanides. From the product, the production of optically-active carnitine nitrile chloride can be achieved.
    Type: Grant
    Filed: June 24, 1986
    Date of Patent: March 22, 1988
    Assignee: Lonza Ltd.
    Inventors: Leander Tenud, Jacques Gosteli
  • Patent number: 4697035
    Abstract: A simplified process for the preparation of basically substituted phenylacetonitriles, in particular of verapamil, is described. This process is carried out with fewer stages and higher yields than the known processes according to the state of the art.
    Type: Grant
    Filed: June 3, 1985
    Date of Patent: September 29, 1987
    Assignee: Ludwig Heumann & Co., GmbH
    Inventors: Lothar Kisielowski, Ingomar Grafe, Walter Liebenow, Kurt H. Ahrens
  • Patent number: 4692543
    Abstract: Process for the production of optically-active di-[3-chloro-2-oxy-propyltrimethylammonium]-tartrate. Racemic 3-chloro-2-oxy-propyltrimethylammonium-chloride is converted by racemate resolution with CaCl.sub.2, for example, into the optically-active di-[3-chloro-2-oxy-propyltrimethylammonium]-tartrate. Such optically-active tartrate compound is dissociated into calcium tartrate and optically-active 3-chloro-2-oxy-propyltrimethylammonium-chloride, and the latter is converted with inorganic cyanides. From the product, the production of optically-active carnitine nitrile chloride can be achieved.
    Type: Grant
    Filed: February 25, 1986
    Date of Patent: September 8, 1987
    Assignee: Lonza Ltd.
    Inventors: Leander Tenud, Jacques Gosteli