Halogen Containing Patents (Class 568/936)
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Patent number: 8980937Abstract: The present invention provides novel aryl pyrrolidines having an excellent insecticidal action as insecticides. Aryl pyrrolidines represented by the formula (I) and use thereof as insecticide.Type: GrantFiled: May 15, 2012Date of Patent: March 17, 2015Assignee: Bayer CropScience AGInventors: Jun Mihara, Tetsuya Murata, Daiei Yamazaki, Yasushi Yoneta, Katsuhiko Shibuya, Eiichi Shimojo, Ulrich Görgens
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Publication number: 20130225815Abstract: A method of forming a fluorinated molecular entity includes reacting in a reaction mixture an aromatic halide, copper, a fluoroalkyl group, and a ligand. The aromatic halide includes an aromatic group and a halogen substituent bonded to the aromatic group. The ligand includes at least one group-V donor selected from phosphorus and an amine. The overall molar ratio of copper to aromatic halide in the reaction mixture is from 0.2 to 3. The method further includes forming a fluoroalkylarene including the aromatic group and the fluoroalkyl group bonded to the aromatic group. A composition, which may be used in the method, consists essentially of copper, the fluoroalkyl group, and the ligand, where the molar ratio of copper to the fluoroalkyl group is approximately 1.Type: ApplicationFiled: February 19, 2013Publication date: August 29, 2013Applicant: The Board of Trustees of the University of IllinoisInventors: John F. Hartwig, Hiroyuki Morimoto, Patrick Fier
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Publication number: 20130165658Abstract: This invention is directed to a process for the preparation of high yield alkyl or aryl iodide from its corresponding carboxylic acid using N-iodo amides.Type: ApplicationFiled: June 9, 2011Publication date: June 27, 2013Inventors: Gennady Nisnevich, Mark Gandelman, Kseniya Kulbitski
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Publication number: 20120232278Abstract: The present invention provides novel aryl pyrrolidines having an excellent insecticidal action as insecticides. Aryl pyrrolidines represented by the formula (I) and use thereof as insecticide.Type: ApplicationFiled: May 15, 2012Publication date: September 13, 2012Applicant: Bayer Intellectual Property GmbHInventors: Jun MIHARA, Tetsuya MURATA, Daiei YAMAZAKI, Yasushi YONETA, Katsuhiko SHIBUYA, Eiichi SHIMOJO, Ulrich GÖRGENS
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Patent number: 8188122Abstract: The present invention provides novel aryl pyrrolidines having an excellent insecticidal action as insecticides. Aryl pyrrolidines represented by the formula (I) and use thereof as insecticide.Type: GrantFiled: April 14, 2008Date of Patent: May 29, 2012Assignee: Bayer Cropscience AGInventors: Jun Mihara, Tetsuya Murata, Daiei Yamazaki, Yasushi Yoneta, Katsuhiko Shibuya, Eiichi Shimojo, Ulrich Görgens
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Publication number: 20110245284Abstract: Alkoxy- and alkylthio-substituted anilinopyrimidines of the formula (I) in which R1 to R14 and E1, E2, E3, X and Y have the meanings given in the description, and agrochemically active salts thereof, their use, and methods and compositions for controlling phytopathogenic harmful fungi in and/or on plants or in and/or on seeds of plants, processes for preparing such compositions and treated seeds and also their use for controlling phytopathogenic hal inful fungi in agriculture, horticulture and forestry, in the protection of materials and in the domestic and hygiene field. The present invention furthermore relates to a process for the preparation of alkoxy- and alkylthio-substituted anilinopyrimidines of the formula (I).Type: ApplicationFiled: August 21, 2009Publication date: October 6, 2011Applicant: Bayer CropScience AGInventors: Jörg Nico Greul, Hendrik Helmke, Stefan Hillebrand, Amos Mattes, Pierre Wasnaire, Carl Friedrich Nising, Ulrike Wachendorff-Neumann, Peter Dahmen, Arnd Voerste, Ruth Meissner, Chirstoph Andreas Braun, Martin Kaubmann, Hiroyuki Hadano, Ulrich Heinemann
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Patent number: 7964654Abstract: Compounds represented by the following structural formulas can be used as photoacid generators: Such compounds are useful, for example, in fabricating arrays of polymers.Type: GrantFiled: September 14, 2010Date of Patent: June 21, 2011Assignee: Affymetrix, Inc.Inventors: Glenn H. McGall, Andrea Cuppoletti
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Publication number: 20110082175Abstract: The present invention provides novel aryl pyrrolidines having an excellent insecticidal action as insecticides. Aryl pyrrolidines represented by the formula (I) and use thereof as insecticide.Type: ApplicationFiled: April 14, 2008Publication date: April 7, 2011Applicant: Bayer CropScience AGInventors: Jun Mihara, Tetsuya Murata, Daiei Yamazaki, Yasushi Yoneta, Katsuhiko Shibuya, Eiichi Shimojo, Ulrich Görgens
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Patent number: 7863344Abstract: Compounds represented by the following structural formulas can be used as photoacid generators: Such compounds are useful, for example, in fabricating arrays of polymers.Type: GrantFiled: November 3, 2008Date of Patent: January 4, 2011Assignee: Affymetrix, Inc.Inventors: Glenn H. McGall, Andrea Cuppoletti
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Publication number: 20100087690Abstract: Compounds of the general formula (I) or salts thereof, for use as a pharmaceutical composition for treating infectious diseases, especially for treating diseases caused by Helicobacter are disclosed. R1 is an H atom, an X atom or a CXmH3-m radical wherein each X can be the same or different and is a halogen selected from F, Cl, Br or I, and m is an integer between 1 and 3; R2 is an NO2 group, a COOR? group or an SO3R? group; R? is a hydrogen (H) atom or a C1-C6 alkyl group; and n is an integer between 1 and 5.Type: ApplicationFiled: February 22, 2008Publication date: April 8, 2010Applicant: UNIVERSIDAD DE ZARAGOZAInventors: Javier Sancho Sanz, Adrián Velazquez Campoy, Nunilo Cremades Casasin
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Patent number: 6930214Abstract: A process to produce 2,5-bis(trifluoromethyl)nitrobenzene in a high yield from an industrially easily available material by using a substance with which the reaction operation is simple and handling is easy, with a small number of steps under moderate reaction conditions, is provided. 1,4-bis(trifluoromethyl)benzene is nitrated by means of nitric acid in a solvent comprising as an essential component an acid selected from sulfuric acid having a sulfuric acid concentration of from 91 to 100 mass % and fuming sulfuric acid having a sulfur trioxide concentration of higher than 0 mass % and at most 20 mass %.Type: GrantFiled: July 6, 2004Date of Patent: August 16, 2005Assignee: Asahi Glass Company, LimitedInventor: Tamaki Shimizu
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Publication number: 20040242942Abstract: A process to produce 2,5-bis(trifluoromethyl)nitrobenzene in a high yield from an industrially easily available material by using a substance with which the reaction operation is simple and handling is easy, with a small number of steps under moderate reaction conditions, is provided. 1,4-bis(trifluoromethyl)benzene is nitrated by means of nitric acid in a solvent comprising as an essential component an acid selected from sulfuric acid having a sulfuric acid concentration of from 91 to 100 mass % and fuming sulfuric acid having a sulfur trioxide concentration of higher than 0 mass % and at most 20 mass %.Type: ApplicationFiled: July 6, 2004Publication date: December 2, 2004Applicant: ASAHI GLASS COMPANY LIMITEDInventor: Tamaki Shimizu
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Patent number: 6806388Abstract: The invention provides polyfluorinated aromatic or heterocyclic compounds comprising at least three ring substituents, at least one of which comprises a sulfurpentafluoride group and at least one of which comprises a labile group; methods for their preparation are also disclosed. Preferably, the compounds comprise either two sulfurpentafluoride groups or one sulfurpentafluoride group and one other polyfluorinated group, such as a trifluoromethyl group. Said labile group preferably comprises an amino, bromo or nitro group. Said compounds are useful in the preparation of medicaments.Type: GrantFiled: November 15, 2002Date of Patent: October 19, 2004Assignee: F2 Chemicals LimitedInventors: Roy Dennis Bowden, Martin Paul Greenhall
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Patent number: 6794549Abstract: The present invention relates to a continuous adiabatic process for preparing nitrochlorobenzene in the presence of phosphoric acid. The waste acid produced during the practice of the process is reconcentrated and recycled into the nitration reaction.Type: GrantFiled: February 6, 2003Date of Patent: September 21, 2004Assignee: Bayer AktiengesellschaftInventors: Ralf Demuth, Matthias Gotta, Thomas Linn, Hans-Martin Weber, Eberhard Zirngiebl
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Patent number: 6774257Abstract: A bis(aminostyryl)naphthalene compound represented by the general formula [I] or the like below. General formula [I] (where R2 and R3 each denotes an unsubstituted aryl group; R1 and R4 each denotes an aryl group having a specific substituent such as methoxy group; and R5 and R6 each denotes a cyano group or the like.) A process for producing a bis(aminostyryl)naphthalene compound represented by the general formula [I] by condensation of, for example, 4-(N,N-diarylamino)benzaldehyde with diphosphonic ester or diphosphonium. The bis(aminostyryl)naphthalene compound emits intense yellow or red light. The process permits efficient production of the bis(aminostyryl)naphthalene compound.Type: GrantFiled: March 19, 2003Date of Patent: August 10, 2004Assignee: Sony CorporationInventors: Mari Ichimura, Tadashi Ishibashi, Shinichiro Tamura
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Patent number: 6765108Abstract: A bis(aminostyryl)naphthalene compound represented by the general formula [I] or the like below. General formula [I] (where R2 and R3 each denotes an unsubstituted aryl group; R1 and R4 each denotes an aryl group having a specific substituent such as methoxy group; and R5 and R6 each denotes a cyano group or the like.) A process for producing a bis(aminostyryl)naphthalene compound represented by the general formula [I] by condensation of, for example, 4-(N,N-diarylamino)benzaldehyde with diphosphonic ester or diphosphonium. The bis(aminostyryl)naphthalene compound emits intense yellow or red light. The process permits efficient production of the bis(aminostyryl)naphthalene compound.Type: GrantFiled: March 17, 2003Date of Patent: July 20, 2004Assignee: Sony CorporationInventors: Mari Ichimura, Tadashi Ishibashi, Shinichiro Tamura
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Patent number: 6586645Abstract: The present invention relates to a continuous adiabatic process for preparing nitrochlorobenzene, in which the waste sulfuric acid produced during the practice of the process is reconcentrated and recycled into the nitration reaction.Type: GrantFiled: February 19, 2002Date of Patent: July 1, 2003Assignee: Bayer AktiengesellschaftInventors: Ralf Demuth, Bernd-Michael König, Thomas Linn, Hans-Joachim Raatz, Hans-Martin Weber, Eberhard Zirngiebl, Ricarda Leiberich
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Patent number: 6376726Abstract: The present invention relates to a process for the production of nitro line aromatic compounds from aromatic hydrocarbons using modified clay catalysts. This invention particularly relates to a process for nitration of aromatic hydrocarbons using modified clay catalysts without using H2SO4. The process for the preparation of nitro compounds from aromatic hydrocarbons using modified clay catalysts comprises nitrating aromatic hydrocarbons using fuming nitric acid in the molar ratio of nitric acid to aromatic hydrocarbon 0.3:1 to 1.2:1 in the presence of metal exchanged clay catalyst at 25° C. to 155° C. for 0.25 to 2.0 hours and recovering the corresponding nitro compounds.Type: GrantFiled: March 25, 1998Date of Patent: April 23, 2002Assignee: Council of Scientific & Industrial ResearchInventors: Boyapati Manoranjan Choudary, Mannepalli Lakshmi Kantam, Mutyala Sateesh, Kottapalli Koteswara Rao, Kondapuram Vijaya Raghavan
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Patent number: 6284894Abstract: A process for the preparation of an allylic aromatic compound in which an aromatic amine is reacted first with a nitrite and then with an allylic olefin having an eliminatable terminal substituent. Novel allylic derivatives of disubstituted benzene compounds are also described.Type: GrantFiled: December 17, 1999Date of Patent: September 4, 2001Assignee: Nycomed Imaging ASInventors: Fredrik Ek, Lars Goran Wistrand
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Patent number: 6242654Abstract: A preparation process of a fluorine substituted aromatic compound comprising reacting an alkali metal or alkali earth metal salt of an aromatic compound having a hydroxy group with an organic fluorinating agent is disclosed. As a representative fluorinating agent, a bis-dialkylamino-difluoromethane compound, for example, 2,2′-difluoro-1,3-dimethylimidazolidine, is exemplified. According to the process, an industrially useful fluorinated aromatic compound, for example, a fluorobenzene, a fluorine substituted benzophenone, a fluorine substituted diarylsulfone can be prepared with ease in economy without specific equipment.Type: GrantFiled: December 21, 1999Date of Patent: June 5, 2001Assignee: Mitsui Chemicals, Inc.Inventors: Kenichi Goto, Kouki Fukumura, Hiroshi Sonoda, Junko Naruse, Hidetoshi Hayashi, Hideaki Oikawa
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Patent number: 6242657Abstract: In the reaction of aromatic compounds with nitrating acids comprising HNO3 and, if appropriate, H2SO4 and/or H2O and/or H3PO4 to form aromatic nitro compounds, according to the invention an amount of from 0.5 to 20,000 ppm of one or more surface-active substances from the group of the anionic, cationic, zwitterionic or nonionic surface-active substances is added to the reaction mixture.Type: GrantFiled: April 26, 2000Date of Patent: June 5, 2001Assignee: Bayer AktiengesellschaftInventors: Bernd-Michael König, Johannes Dühr, Hans-Joachim Raatz, Manfred Kaczorowski
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Patent number: 5977418Abstract: The invention is a process for regioselective nitration of substituted aromatic compounds and the corresponding reaction products. The reaction is conducted in the presence of a solid zeolite with small pores and with nitrogen pentoxide as the nitrating agent. The reaction products have a very high proportion of para-nitro substituted isomer.Type: GrantFiled: January 20, 1998Date of Patent: November 2, 1999Inventors: Reddy Damavarapu, Keerthi Jayasuriya, Thomas J. Kwok
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Patent number: 5946638Abstract: A method is described for the regioselective nitration of substituted aromatic compounds. The reaction is effected by heating the aromatic compound to a temperature within the range of 70-90.degree. C. in the presence of a solid zeolite catalyst and adding concentrated nitric acid to the heated mixture, the concentration of the acid ranging from 90-98%, by weight.Type: GrantFiled: August 7, 1998Date of Patent: August 31, 1999Inventors: Keerthi Jayasuriya, Reddy Damavarapu
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Patent number: 5900502Abstract: According to the present invention there is provided a process for the selective introduction of one or more fluorine atoms into a disubstituted aromatic compound in an acid medium with fluorine gas characterized in that the acid medium has a dielectric constant of at least 20 and a pH of less than 3. The present process provides a cost effective means of selectively introducing one or more fluorine atoms into an aromatic compound in good overall yield.Type: GrantFiled: October 25, 1996Date of Patent: May 4, 1999Assignee: BNFL Fluorochemicals LimitedInventors: Christopher John Skinner, John Hutchinson, Julie Thomson, Richard Dickinson Chambers
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Patent number: 5270309Abstract: 4-Oxo-1,4-dihydroquinoline compounds having a 2-acidic group or a group convertible thereto in vivo, and their pharmaceutically acceptable salts, are potent specific antagonists of N-methyl-D-aspartate (NMDA) receptors and are therefore useful in the treatment of neurodegenerative disorders. 4-Oxo-1,4-dihydroquinoline compounds having a 2-acidic group or a group convertible thereto in vivo, other than carboxy or C.sub.1-6 alkoxycarbonyl, are novel compounds, as also are compounds of formula II ##STR1## wherein R.sup.2 represents carboxy or a group convertible thereto in vivo, R.sup.6 is hydrogen and R.sup.5 and R.sup.7 represent C.sub.1-6 alkyl or halogen, provided that R.sup.5 and R.sup.7 are not simultaneously chlorine or simultaneously bromine; a process for preparing the novel compounds is described, as also are pharmaceutical compositions containing the novel compounds.Type: GrantFiled: July 20, 1992Date of Patent: December 14, 1993Assignee: Merck Sharp & Dohme LimitedInventor: Paul Leeson
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Patent number: 5212301Abstract: Introduction of a fluoro substituent into an aromatic ring adjacent an electron donating group is difficult producing mixed isomers and low yields of desired products.A process for the introduction of a fluoro substituent into a substantially adjacent position to an electron-donating group into an aromatic compound in high yield is disclosed.The fluoroaromatic compounds are useful as synthetic intermediates for example in the manufacture of agrochemicals, pharmaceuticals and dyestuffs.Type: GrantFiled: May 8, 1992Date of Patent: May 18, 1993Assignee: Imperial Chemical Industries PLCInventors: John S. Moilliet, Richard D. Chambers, Michael H. Rock
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Patent number: 5118879Abstract: Fluoroalkyl derivatives which are novel compounds represented by the following general formula (I) or (II) of: ##STR1## orR.sub.1 --CH.dbd.CR.sub.2 (CF.sub.2).sub.n F (II)(wherein R.sub.1 stands for ##STR2## (where X stands for a hydrogen atom, a chlorine atom, a bromine atom, a fluorine atom, an iodine atom, a methyl group, an ethyl group, a methoxy group, an ethoxy group or a nitro group), an aroyloxy group, or an alkyl or alkoxycarbonyl group having 1 to 20 carbon atoms, and R.sub.2 stands for a hydrogen atom or a methyl group; and n stands for an integer of from 1 to 20.) A process for the preparation of the derivative is a process comprising reacting an olefin compound and a fluoroalkanesulfonyl chloride in the presence of a metal catalyst, or a process comprising an additional alkali treatment step which follows the aforementioned process.Type: GrantFiled: October 25, 1990Date of Patent: June 2, 1992Assignee: Nippon Oil and Fats Co., Ltd.Inventors: Nobumasa Kamigata, Masato Yoshida, Hideo Sawada, Masaharu Nakayama
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Patent number: 5113013Abstract: A method for the preparation of a fluorine-containing organic compound which comprises reacting a sulphonyl halide of the formula:RfSO.sub.2 Xwhere Rf represents a fluorinated organic radical and X represents a halogen atom, with a reactive organic halide in the presence of a metal known to complex with fluorinated organic radicals.Type: GrantFiled: April 26, 1990Date of Patent: May 12, 1992Assignee: Imperial Chemical Industries PLCInventors: Richard L. Powell, Charles A. Heaton
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Patent number: 4990699Abstract: Despite the instabity of perfluoralkyl anions, it is possible to perfluoroalkylate aromatic compounds if appropriately substituted by suitable electronegative substituents (e.g., nitro, trifluoromethylsulfonyl, etc.). Thus a novel Meisenheimer complex is formed by thermally decomposing a salt of a perfluoroalkanoic acid in the presence of an aromatic compound such as 1,3,5-trinitrobenzene. Oxidation with organic hypochlorite yields the corresponding perfluoroalkylated aromatic compound.Type: GrantFiled: October 17, 1988Date of Patent: February 5, 1991Assignee: Ethyl CorporationInventor: G. Patrick Stahly
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Patent number: 4956123Abstract: Fluorine-containing aromatic derivatives are produced by the reaction of di(haloacyl)peroxide represented by the general formula: ##STR1## (wherein X stands for a fluorine, chlorine, or hydrogen atom and n for an integer of the value of 1 to 10) with aromatic unsaturated monomers represented by the general formula: ##STR2## (wherein Y stands for hydrogen atom, methyl, ethyl, propyl, acetyl, propionyl, acetyloxy, propionyloxy, methoxy, ethoxy, propoxy, vinyl, isopropenyl, or nitro group, or a halogen atom, R.sup.1 for hydrogen atom, methyl, ethyl, propyl, or butyl group, R.sup.2 for hydrogen atom, methyl or phenyl group, and m for an integer of the value of 1 to 5).Type: GrantFiled: September 14, 1988Date of Patent: September 11, 1990Assignee: Nippon Oils & Fats Company, Ltd.Inventors: Hideo Sawada, Michio Kobayashi, Masato Yoshida
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Patent number: 4831193Abstract: This invention relates to a novel process for preparing 3-amino-2-methylbenzotrifluoride from benzotrifluoride. The process comprises nitrating benzotrifluoride to form 3-nitrobenzotrifluoride, reacting this compound with trimethyl sulphoxonium halide to form 3-nitro-2-methylbenzotrifluoride and reducing the nitro group to an amino group.Type: GrantFiled: June 19, 1987Date of Patent: May 16, 1989Assignee: Schering CorporationInventors: Joseph F. Lamendola, Dhiru Vashi, Robert G. Tyson
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Patent number: 4745219Abstract: This invention pertains to chemical intermediates for a new class of 2-haloacetanilide herbicides and a process for preparation of these intermediates. The process generally involves nitration of substituted benzotrifluoride compounds.Type: GrantFiled: August 8, 1986Date of Patent: May 17, 1988Assignee: Monsanto CompanyInventors: Thomas E. Nickson, John P. Chupp, Thomas E. Neumann
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Patent number: 4705650Abstract: Compounds halogenated in the .alpha.-position to an electron-attracting group of formula ##STR1## in which X denotes a halogen atom, R denotes a hydrogen atom or a hydrocarbon radical or a radical --(CH.sub.2).sub.3 --COOR.sub.1 and Z denotes a radical --CHO, --COR.sub.2, --COOR.sub.3, --CONR.sub.4 R.sub.5, --CN, --SO.sub.2 R.sub.6, --NO.sub.2, --CO--(CH.sub.2)p--COO.sub.1 or --COO(CH.sub.2)p--COOR.sub.1 are made by a halogenating deacylation of a compound of formula ##STR2## in which R' denotes a hydrogen atom or a hydrocarbon radical, R" denotes a methyl radical and Z' denotes a radical --CHO, --COR.sub.2, --COOR.sub.3, --CONR.sub.4 R.sub.5, --CN, --SO.sub.2 R.sub.6 or --NO.sub.2 or R' and R" may form a radical --(CH.sub.2)-- or R' and R" may form a radical --CO--(CH.sub.2)p-- or --COO(CH.sub.2)p--, using an alkali metal alcoholate or an alkali or alkaline-earth metal carbonate and a halogenating agent.Type: GrantFiled: July 10, 1985Date of Patent: November 10, 1987Assignee: Rhone-Poulenc SanteInventors: Gerard Mignani, Didier Morel
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Patent number: 4668830Abstract: A process for the preparation of compounds containing a difluoromethylene or trifluoromethyl group. A compound containing a carbonyl group, preferbly an acid, acid halide, amide, ketone or any compound containing a perhaloalkylcarbonyl moiety is placed, in anhydrous liquid hydrofluoric acid, in contact with boron trifluoride in a quantity such that the absolute pressure of boron trifluoride in the reaction system is at least one bar for a time sufficient to convert the carbonyl group to a difluormethylene or trifluoromethyl group.The compounds obtained are useful as synthesis intermediates in the pharmaceutical, plant-protection and dye industries, as anesthetics or as heat-transfer and lubricating fluids.Type: GrantFiled: December 17, 1985Date of Patent: May 26, 1987Assignee: Rhone-Poulenc Specialites ChimiquesInventor: Michel Desbois
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Patent number: 4634771Abstract: There is disclosed a method for the conversion of a carboxylic acid group on the ring of an aromatic or N-heteroaromatic compound to a trichloromethyl group which comprises contacting the aromatic or N-heteroaromatic compound with a phenylphosphonous dichloride, phosphorus trichloride and chlorine.Type: GrantFiled: July 25, 1985Date of Patent: January 6, 1987Assignee: Stauffer Chemical CompanyInventors: Kyung S. Shim, Arthur D. F. Toy, James B. Heather
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Patent number: 4631151Abstract: A fluorine-containing aromatic derivative is produced by causing a di(haloacyl)peroxide to react upon benzene, a mono-substituted benzene, naphthalene, or a mono-substituted naphthalene thereby introducing an X(CF.sub.2).sub.n -group into the benzene ring or the naphthalene ring.Type: GrantFiled: February 19, 1985Date of Patent: December 23, 1986Assignee: Nippon Oil & Fars Co., Ltd.Inventors: Michio Kobayashi, Masato Yoshida, Hideo Sawada, Hidehiko Hagii, Kazuyoshi Aoshima
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Patent number: 4600702Abstract: Catalysts compositions useful to catalyze the nitration of aromatic compounds in the vapor phase to produce nitroaromatic compounds are represented by the empirical formula:(M.sup.1.sub.a M.sup.2.sub.b O.sub.c).sub.x (NO.sub.2).sub.ywherein M.sup.1 is at least one element selected from Group 4b of the Periodic Table of the Elements, M.sup.2 is at least one element selected from Group 3b of the Periodic Table of the Elements, a is 1, b is 0.050 to 20, c is a number taken to satisfy the average valences of M.sup.1 and M.sup.2 in the oxidation states in which they exist in the composition, x is 1, and y is 0 to c. The compositions are particularly effective to catalyze the vapor phase nitration of chlorobenzene and are characterized in such reaction by providing a para/ortho isomer distribution ratio of at least about 1.9/l.Type: GrantFiled: November 14, 1984Date of Patent: July 15, 1986Assignee: Monsanto CompanyInventor: Ignatius Schumacher
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Patent number: 4593144Abstract: This invention pertains to a process for preparing substituted and unsubstituted benzotrichlorides. The process generally involves reacting the starting compound with a perchloroalkane with presence of base and a phase transfer catalyst.Type: GrantFiled: October 10, 1984Date of Patent: June 3, 1986Assignee: Monsanto CompanyInventors: John P. Chupp, Thomas E. Neumann
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Patent number: 4575565Abstract: The invention herein pertains to a novel process for making substituted benzotrifluorides.Type: GrantFiled: April 15, 1985Date of Patent: March 11, 1986Assignee: Monsanto CompanyInventor: William F. Goure
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Patent number: 4562280Abstract: The invention is a process for the chloromethylation of an aromatic compound, substituted with an alkyl group and a deactivating moiety, which comprises contacting an aromatic compound, substituted with an alkyl group and a deactivating group, with a chloromethyl alkyl ether in the presence of a catalytic amount of ferric chloride or stannic chloride, under conditions such that an aromatic compound, substituted with an alkyl group, a chloromethyl group, and a deactivating group, wherein the alkyl and chloromethyl groups are on adjacent carbon atoms, is prepared.Type: GrantFiled: October 18, 1984Date of Patent: December 31, 1985Assignee: The Dow Chemical CompanyInventors: Jo Ann Gilpin, Lowell B. Lindy
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Patent number: 4558166Abstract: Process for the preparation of benzal chlorides from benzotrichlorides, according to which benzotrichlorides are reacted with thiols in the presence of metal salts at elevated temperatures.Type: GrantFiled: March 21, 1984Date of Patent: December 10, 1985Assignee: Bayer AktiengesellschaftInventors: Bernd Baasner, Erich Klauke
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Patent number: 4533776Abstract: In the preparation of an .alpha.-fluorinated nitroalkane of the formula ##STR1## in which R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are identical or different and individually represent hydrogen, fluorine, chlorine, bromine, alkyl, halogenoalkyl or cycloalkyl, orR.sup.1 and R.sup.3 have the meaning indicated andR.sup.2 and R.sup.4 together represent an alkylene group having 3-6 carbon atoms,by conjugated nitrofluorination of the corresponding olefin of the formula ##STR2## the improvement which comprises employing about 1.1 mols of hydrogen fluoride and 1 to 2 mols of nitric acid per mol of olefin and carrying out the reaction in the presence of an agent which binds water, e.g. chlorosulphonic acid, fluorosulphonic acid, sulphur trioxide, sulphur dioxide, thionyl chloride, thionyl fluoride, sulfuryl chloride or sulfuryl fluoride. The end products, some of which are known, are useful as intermediates in synthesizing herbicides.Type: GrantFiled: February 1, 1984Date of Patent: August 6, 1985Assignee: Bayer AktiengesellschaftInventors: Bernd Baasner, Hermann Hagemann, Erich Klauke
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Patent number: 4503276Abstract: This invention pertains to a process for separating nitration isomers of 1,3-disubstituted and 1,2,4-trisubstituted benzene compounds. The separated isomers have a variety of uses including precursors for 2-haloacetanilide herbicides.Type: GrantFiled: January 9, 1984Date of Patent: March 5, 1985Assignee: Monsanto CompanyInventor: Thomas E. Nickson
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Patent number: 4467125Abstract: The invention herein pertains to nitro-methyl or ethyl substituted benzotrifluoride compounds useful as chemical intermediates and a process for their preparation. The chemical intermediates are useful for the preparation of substituted anilines which are precursors for a new class of 2-haloacetanilide herbicides.Type: GrantFiled: June 10, 1983Date of Patent: August 21, 1984Assignee: Monsanto CompanyInventors: John P. Chupp, Gerhard H. Alt
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Patent number: 4454360Abstract: Para-nitrobenzotrichloride is prepared by chlorinating nitrotoluene using an activated carbon catalyst. The process can use various cocatalysts such as bromine, iodine, PCl.sub.3, S.sub.2 Cl.sub.2, bromide salts, chloranil, air bubbles and phthalimide. The reaction is carried out at from 20.degree. C., to 220.degree. C., with from 150.degree. to 200.degree. C. being the preferred range and a pressure of 1 to 5 Atm.Type: GrantFiled: December 1, 1982Date of Patent: June 12, 1984Assignee: E. I. Du Pont de Nemours and CompanyInventor: William B. McCormack
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Patent number: 4419514Abstract: Method for converting carboxylic acid groups to trichloromethyl groups which comprises contacting a compound containing a carboxylic acid group with a phenylphosphonic dichloride and phosphorus pentachloride and recovering the thus produced product.Type: GrantFiled: May 18, 1981Date of Patent: December 6, 1983Assignee: The Dow Chemical CompanyInventors: Lennon H. McKendry, Michael J. Ricks, Richard B. Rogers
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Patent number: 4400563Abstract: A process for preparing perfluoro(lower)alkylbenzenes and derivatives thereof which comprises contacting a lower alkylbenzene or the corresponding derivative with hydrogen fluoride in the presence of chlorine in the gaseous phase at an elevated temperature to give the corresponding perfluoro(lower)alkylbenzene or its derivative thereof.Type: GrantFiled: June 20, 1979Date of Patent: August 23, 1983Assignee: Daikin Kogyo Co., Ltd.Inventors: Yohnosuke Ohsaka, Uji Hiramatsu, Toshihide Honda
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Patent number: 4395577Abstract: A method for the preparation of 3-chloromethyl derivatives of 4-alkylnitrobenzenes from the corresponding amidomethyl derivatives with phosphorus oxychloride or with phosphorous oxychloride and inert solvents. This process also relates to 3-chloromethyl-4-alkylnitrobenzenes which are useful intermediates for the preparation of certain substituted 2,6-dinitroaniline pre-emergence herbicides.Type: GrantFiled: October 22, 1981Date of Patent: July 26, 1983Assignee: American Cyanamid CompanyInventor: Donald R. Maulding
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Patent number: 4393257Abstract: A process for preparing benzotrifluoride or derivatives thereof by contacting benzotrichloride or the corresponding derivatives with hydrogen fluoride in a gaseous phase in the absence of any catalyst, the contact being carried out in the presence of chlorine at an elevated temperature so as to accelerate the reaction rate.Type: GrantFiled: June 20, 1979Date of Patent: July 12, 1983Assignee: Daikin Kogyo Co., Ltd.Inventors: Tsuneo Nakagawa, Uji Hiramatsu, Toshihide Honda
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Patent number: 4350824Abstract: A process for the preparation of a 1,1-dichloroalkene of the formula ##STR1## in which R.sup.1 is hydrogen, or an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, andR.sup.2 is an optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aralkyl, aralkenyl or aryl radical, orR.sup.1 and R.sup.2 together form an optionally branched and/or optionally benzo-fused hydrocarbon chain,comprising reacting a carbonyl compound of the formula ##STR2## with a trichloromethanephosphonic acid ester of the formula ##STR3## in which R.sup.3 each individually is an alkyl or phenyl radical, or the two radicals R.sup.3 together are alkanediyl,in the presence of at least an equimolar amount of a phosphorous acid triamide of the formulaP(NR.sup.4.sub.2).sub.3in whichR.sup.4 each independently is an alkyl radical, or the two radicals R.sup.4 together are alkanediyl.Advantageously,R.sup.1 is hydrogen,R.sup.2 a C.sub.2 to C.sub.Type: GrantFiled: February 23, 1981Date of Patent: September 21, 1982Assignee: Bayer AktiengesellschaftInventors: Hans-Jochem Riebel, Fritz Maurer, Uwe Priesnitz