Replacing Halogen With Cyano Patents (Class 558/342)
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Patent number: 10364214Abstract: 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: GrantFiled: August 29, 2017Date of Patent: July 30, 2019Assignee: Covestro Deutschland AGInventors: Thomas Knauf, Dirk Manzel, Peter Plathen, Jürgen Spriewald
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Patent number: 10144704Abstract: Novel crystal forms of (R)-(+)-verapamil hydrochloride are disclosed.Type: GrantFiled: March 11, 2018Date of Patent: December 4, 2018Assignee: Center Laboratories, Inc.Inventors: Jui-Pao Hsu, Guang-Tzuu Shane, Yu-Yin Yeh, Meng-Ju Lee
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Patent number: 9067869Abstract: 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: GrantFiled: March 8, 2012Date of Patent: June 30, 2015Assignee: RHODIA OPERATIONSInventor: Olivier Buisine
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Patent number: 8247593Abstract: 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: GrantFiled: May 13, 2008Date of Patent: August 21, 2012Assignee: Nalco CompanyInventors: Christopher F. Morrison, Joseph Paul Street
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Publication number: 20120083608Abstract: 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: ApplicationFiled: October 27, 2011Publication date: April 5, 2012Applicant: SANOFIInventors: Janos FAZEKAS, Peter MISKOLCZI, Annamaria MOLNAR, Bela AGAI, Zsolt PARKANYI
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Publication number: 20090287013Abstract: 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: ApplicationFiled: May 13, 2008Publication date: November 19, 2009Inventors: Christopher F. Morrison, Joseph Paul Street
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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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Publication number: 20040214297Abstract: 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: ApplicationFiled: February 18, 2004Publication date: October 28, 2004Inventors: 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
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Publication number: 20040024238Abstract: 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: ApplicationFiled: August 20, 2003Publication date: February 5, 2004Inventors: Nathalie Laurain, Samir Zard
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Publication number: 20030105347Abstract: 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: ApplicationFiled: October 29, 2001Publication date: June 5, 2003Inventors: Ryuhei Wakita, Nobuya Ito
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Publication number: 20030100789Abstract: 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 1Type: ApplicationFiled: July 9, 2002Publication date: May 29, 2003Inventors: Yulin Hu, David Allen Hunt
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Patent number: 6444838Abstract: 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: GrantFiled: May 4, 2001Date of Patent: September 3, 2002Assignee: BASF AktiengesellschaftInventors: Yulin Hu, David Allen Hunt
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Patent number: 6355827Abstract: 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: GrantFiled: February 18, 2000Date of Patent: March 12, 2002Assignee: Bayer AktiengesellschaftInventors: Joachim Komoschinski, Helmut Fiege, Guido Steffan
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Patent number: 6344569Abstract: 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: GrantFiled: January 2, 2001Date of Patent: February 5, 2002Assignee: Kaneka CorporationInventors: Masaru Mitsuda, Makoto Miyazaki, Kenji Inoue
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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: 6140527Abstract: 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: GrantFiled: September 7, 1999Date of Patent: October 31, 2000Assignee: Kaneka CorporationInventors: Shigeki Kunihiro, Fumihiko Kano, Natsuki Mori
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Patent number: 6130347Abstract: 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: GrantFiled: November 2, 1999Date of Patent: October 10, 2000Assignee: BASF AktiengesellschaftInventors: Manfred Julius, Rolf Schneider, Klaus Mundinger, Jakob Fischer
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Patent number: 5908953Abstract: 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: GrantFiled: December 10, 1997Date of Patent: June 1, 1999Assignee: Mitsubishi Chemical CorporationInventors: Hitoshi Matsuda, Toshiharu Shibata, Hidekichi Hashimoto, Mitsumasa Kitai
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Patent number: 5780665Abstract: 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: GrantFiled: May 6, 1997Date of Patent: July 14, 1998Assignee: BASF AktiengesellschaftInventors: Heinz Isak, Michael Keil, Bernd Wolf, Horst Wingert, Thomas Wettling
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Patent number: 5597941Abstract: 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: GrantFiled: December 29, 1994Date of Patent: January 28, 1997Assignee: Sumitomo Chemical Company, LimitedInventors: Kazuya Minamisaka, Masahito Sekiguchi, Kenji Saito
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Patent number: 5483007Abstract: 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: GrantFiled: April 22, 1993Date of Patent: January 9, 1996Assignee: Minnesota Mining and Manufacturing CompanyInventor: Kim L. Johnson
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Patent number: 5430171Abstract: 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: GrantFiled: July 11, 1994Date of Patent: July 4, 1995Assignee: Takasago International CorporationInventors: Shigeru Mitsuhashi, Kazutoshi Sakurai, Hidenori Kumobayashi
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Patent number: 5302263Abstract: 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: GrantFiled: April 29, 1993Date of Patent: April 12, 1994Assignee: Ethyl CorporationInventor: Thanikavelu Manimaran
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Patent number: 5155251Abstract: 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: GrantFiled: October 11, 1991Date of Patent: October 13, 1992Assignee: Warner-Lambert CompanyInventors: Donald E. Butler, Tung V. Le, Alan Millar, Thomas N. Nanninga
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Patent number: 5001288Abstract: 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: GrantFiled: August 17, 1989Date of Patent: March 19, 1991Assignee: Ethyl CorporationInventor: George A. Knesel
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Patent number: 4994597Abstract: 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: GrantFiled: April 27, 1989Date of Patent: February 19, 1991Assignee: Kanegafuchi Kagaku Kogyo Kabushiki KaishaInventors: Kenji Inoue, Mitsunori Matsumoto, Satomi Takahashi
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Patent number: 4966988Abstract: 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: GrantFiled: February 17, 1989Date of Patent: October 30, 1990Assignee: Chevron Research CompanyInventors: William L. Schinski, Peter Denisevich, Jr.
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Patent number: 4732709Abstract: 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: GrantFiled: June 24, 1986Date of Patent: March 22, 1988Assignee: Lonza Ltd.Inventors: Leander Tenud, Jacques Gosteli
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Patent number: 4697035Abstract: 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: GrantFiled: June 3, 1985Date of Patent: September 29, 1987Assignee: Ludwig Heumann & Co., GmbHInventors: Lothar Kisielowski, Ingomar Grafe, Walter Liebenow, Kurt H. Ahrens
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Patent number: 4692543Abstract: 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: GrantFiled: February 25, 1986Date of Patent: September 8, 1987Assignee: Lonza Ltd.Inventors: Leander Tenud, Jacques Gosteli