Halogen Containing Patents (Class 568/936)
  • Patent number: 8980937
    Abstract: 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: Grant
    Filed: May 15, 2012
    Date of Patent: March 17, 2015
    Assignee: Bayer CropScience AG
    Inventors: Jun Mihara, Tetsuya Murata, Daiei Yamazaki, Yasushi Yoneta, Katsuhiko Shibuya, Eiichi Shimojo, Ulrich Görgens
  • Publication number: 20130225815
    Abstract: 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: Application
    Filed: February 19, 2013
    Publication date: August 29, 2013
    Applicant: The Board of Trustees of the University of Illinois
    Inventors: John F. Hartwig, Hiroyuki Morimoto, Patrick Fier
  • Publication number: 20130165658
    Abstract: 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: Application
    Filed: June 9, 2011
    Publication date: June 27, 2013
    Inventors: Gennady Nisnevich, Mark Gandelman, Kseniya Kulbitski
  • Publication number: 20120232278
    Abstract: 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: Application
    Filed: May 15, 2012
    Publication date: September 13, 2012
    Applicant: Bayer Intellectual Property GmbH
    Inventors: Jun MIHARA, Tetsuya MURATA, Daiei YAMAZAKI, Yasushi YONETA, Katsuhiko SHIBUYA, Eiichi SHIMOJO, Ulrich GÖRGENS
  • Patent number: 8188122
    Abstract: 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: Grant
    Filed: April 14, 2008
    Date of Patent: May 29, 2012
    Assignee: Bayer Cropscience AG
    Inventors: Jun Mihara, Tetsuya Murata, Daiei Yamazaki, Yasushi Yoneta, Katsuhiko Shibuya, Eiichi Shimojo, Ulrich Görgens
  • Publication number: 20110245284
    Abstract: 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: Application
    Filed: August 21, 2009
    Publication date: October 6, 2011
    Applicant: Bayer CropScience AG
    Inventors: 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
  • Patent number: 7964654
    Abstract: 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: Grant
    Filed: September 14, 2010
    Date of Patent: June 21, 2011
    Assignee: Affymetrix, Inc.
    Inventors: Glenn H. McGall, Andrea Cuppoletti
  • Publication number: 20110082175
    Abstract: 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: Application
    Filed: April 14, 2008
    Publication date: April 7, 2011
    Applicant: Bayer CropScience AG
    Inventors: Jun Mihara, Tetsuya Murata, Daiei Yamazaki, Yasushi Yoneta, Katsuhiko Shibuya, Eiichi Shimojo, Ulrich Görgens
  • Patent number: 7863344
    Abstract: 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: Grant
    Filed: November 3, 2008
    Date of Patent: January 4, 2011
    Assignee: Affymetrix, Inc.
    Inventors: Glenn H. McGall, Andrea Cuppoletti
  • Publication number: 20100087690
    Abstract: 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: Application
    Filed: February 22, 2008
    Publication date: April 8, 2010
    Applicant: UNIVERSIDAD DE ZARAGOZA
    Inventors: Javier Sancho Sanz, Adrián Velazquez Campoy, Nunilo Cremades Casasin
  • Patent number: 6930214
    Abstract: 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: Grant
    Filed: July 6, 2004
    Date of Patent: August 16, 2005
    Assignee: Asahi Glass Company, Limited
    Inventor: Tamaki Shimizu
  • Publication number: 20040242942
    Abstract: 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: Application
    Filed: July 6, 2004
    Publication date: December 2, 2004
    Applicant: ASAHI GLASS COMPANY LIMITED
    Inventor: Tamaki Shimizu
  • Patent number: 6806388
    Abstract: 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: Grant
    Filed: November 15, 2002
    Date of Patent: October 19, 2004
    Assignee: F2 Chemicals Limited
    Inventors: Roy Dennis Bowden, Martin Paul Greenhall
  • Patent number: 6794549
    Abstract: 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: Grant
    Filed: February 6, 2003
    Date of Patent: September 21, 2004
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ralf Demuth, Matthias Gotta, Thomas Linn, Hans-Martin Weber, Eberhard Zirngiebl
  • Patent number: 6774257
    Abstract: 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: Grant
    Filed: March 19, 2003
    Date of Patent: August 10, 2004
    Assignee: Sony Corporation
    Inventors: Mari Ichimura, Tadashi Ishibashi, Shinichiro Tamura
  • Patent number: 6765108
    Abstract: 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: Grant
    Filed: March 17, 2003
    Date of Patent: July 20, 2004
    Assignee: Sony Corporation
    Inventors: Mari Ichimura, Tadashi Ishibashi, Shinichiro Tamura
  • Patent number: 6586645
    Abstract: 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: Grant
    Filed: February 19, 2002
    Date of Patent: July 1, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ralf Demuth, Bernd-Michael König, Thomas Linn, Hans-Joachim Raatz, Hans-Martin Weber, Eberhard Zirngiebl, Ricarda Leiberich
  • Patent number: 6376726
    Abstract: 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: Grant
    Filed: March 25, 1998
    Date of Patent: April 23, 2002
    Assignee: Council of Scientific & Industrial Research
    Inventors: Boyapati Manoranjan Choudary, Mannepalli Lakshmi Kantam, Mutyala Sateesh, Kottapalli Koteswara Rao, Kondapuram Vijaya Raghavan
  • Patent number: 6284894
    Abstract: 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: Grant
    Filed: December 17, 1999
    Date of Patent: September 4, 2001
    Assignee: Nycomed Imaging AS
    Inventors: Fredrik Ek, Lars Goran Wistrand
  • Patent number: 6242654
    Abstract: 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: Grant
    Filed: December 21, 1999
    Date of Patent: June 5, 2001
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Kenichi Goto, Kouki Fukumura, Hiroshi Sonoda, Junko Naruse, Hidetoshi Hayashi, Hideaki Oikawa
  • Patent number: 6242657
    Abstract: 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: Grant
    Filed: April 26, 2000
    Date of Patent: June 5, 2001
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd-Michael König, Johannes Dühr, Hans-Joachim Raatz, Manfred Kaczorowski
  • Patent number: 5977418
    Abstract: 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: Grant
    Filed: January 20, 1998
    Date of Patent: November 2, 1999
    Inventors: Reddy Damavarapu, Keerthi Jayasuriya, Thomas J. Kwok
  • Patent number: 5946638
    Abstract: 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: Grant
    Filed: August 7, 1998
    Date of Patent: August 31, 1999
    Inventors: Keerthi Jayasuriya, Reddy Damavarapu
  • Patent number: 5900502
    Abstract: 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: Grant
    Filed: October 25, 1996
    Date of Patent: May 4, 1999
    Assignee: BNFL Fluorochemicals Limited
    Inventors: Christopher John Skinner, John Hutchinson, Julie Thomson, Richard Dickinson Chambers
  • Patent number: 5270309
    Abstract: 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: Grant
    Filed: July 20, 1992
    Date of Patent: December 14, 1993
    Assignee: Merck Sharp & Dohme Limited
    Inventor: Paul Leeson
  • Patent number: 5212301
    Abstract: 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: Grant
    Filed: May 8, 1992
    Date of Patent: May 18, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: John S. Moilliet, Richard D. Chambers, Michael H. Rock
  • Patent number: 5118879
    Abstract: 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: Grant
    Filed: October 25, 1990
    Date of Patent: June 2, 1992
    Assignee: Nippon Oil and Fats Co., Ltd.
    Inventors: Nobumasa Kamigata, Masato Yoshida, Hideo Sawada, Masaharu Nakayama
  • Patent number: 5113013
    Abstract: 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: Grant
    Filed: April 26, 1990
    Date of Patent: May 12, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventors: Richard L. Powell, Charles A. Heaton
  • Patent number: 4990699
    Abstract: 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: Grant
    Filed: October 17, 1988
    Date of Patent: February 5, 1991
    Assignee: Ethyl Corporation
    Inventor: G. Patrick Stahly
  • Patent number: 4956123
    Abstract: 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: Grant
    Filed: September 14, 1988
    Date of Patent: September 11, 1990
    Assignee: Nippon Oils & Fats Company, Ltd.
    Inventors: Hideo Sawada, Michio Kobayashi, Masato Yoshida
  • Patent number: 4831193
    Abstract: 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: Grant
    Filed: June 19, 1987
    Date of Patent: May 16, 1989
    Assignee: Schering Corporation
    Inventors: Joseph F. Lamendola, Dhiru Vashi, Robert G. Tyson
  • Patent number: 4745219
    Abstract: 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: Grant
    Filed: August 8, 1986
    Date of Patent: May 17, 1988
    Assignee: Monsanto Company
    Inventors: Thomas E. Nickson, John P. Chupp, Thomas E. Neumann
  • Patent number: 4705650
    Abstract: 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: Grant
    Filed: July 10, 1985
    Date of Patent: November 10, 1987
    Assignee: Rhone-Poulenc Sante
    Inventors: Gerard Mignani, Didier Morel
  • Patent number: 4668830
    Abstract: 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: Grant
    Filed: December 17, 1985
    Date of Patent: May 26, 1987
    Assignee: Rhone-Poulenc Specialites Chimiques
    Inventor: Michel Desbois
  • Patent number: 4634771
    Abstract: 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: Grant
    Filed: July 25, 1985
    Date of Patent: January 6, 1987
    Assignee: Stauffer Chemical Company
    Inventors: Kyung S. Shim, Arthur D. F. Toy, James B. Heather
  • Patent number: 4631151
    Abstract: 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: Grant
    Filed: February 19, 1985
    Date of Patent: December 23, 1986
    Assignee: Nippon Oil & Fars Co., Ltd.
    Inventors: Michio Kobayashi, Masato Yoshida, Hideo Sawada, Hidehiko Hagii, Kazuyoshi Aoshima
  • Patent number: 4600702
    Abstract: 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: Grant
    Filed: November 14, 1984
    Date of Patent: July 15, 1986
    Assignee: Monsanto Company
    Inventor: Ignatius Schumacher
  • Patent number: 4593144
    Abstract: 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: Grant
    Filed: October 10, 1984
    Date of Patent: June 3, 1986
    Assignee: Monsanto Company
    Inventors: John P. Chupp, Thomas E. Neumann
  • Patent number: 4575565
    Abstract: The invention herein pertains to a novel process for making substituted benzotrifluorides.
    Type: Grant
    Filed: April 15, 1985
    Date of Patent: March 11, 1986
    Assignee: Monsanto Company
    Inventor: William F. Goure
  • Patent number: 4562280
    Abstract: 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: Grant
    Filed: October 18, 1984
    Date of Patent: December 31, 1985
    Assignee: The Dow Chemical Company
    Inventors: Jo Ann Gilpin, Lowell B. Lindy
  • Patent number: 4558166
    Abstract: 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: Grant
    Filed: March 21, 1984
    Date of Patent: December 10, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd Baasner, Erich Klauke
  • Patent number: 4533776
    Abstract: 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: Grant
    Filed: February 1, 1984
    Date of Patent: August 6, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Bernd Baasner, Hermann Hagemann, Erich Klauke
  • Patent number: 4503276
    Abstract: 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: Grant
    Filed: January 9, 1984
    Date of Patent: March 5, 1985
    Assignee: Monsanto Company
    Inventor: Thomas E. Nickson
  • Patent number: 4467125
    Abstract: 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: Grant
    Filed: June 10, 1983
    Date of Patent: August 21, 1984
    Assignee: Monsanto Company
    Inventors: John P. Chupp, Gerhard H. Alt
  • Patent number: 4454360
    Abstract: 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: Grant
    Filed: December 1, 1982
    Date of Patent: June 12, 1984
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: William B. McCormack
  • Patent number: 4419514
    Abstract: 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: Grant
    Filed: May 18, 1981
    Date of Patent: December 6, 1983
    Assignee: The Dow Chemical Company
    Inventors: Lennon H. McKendry, Michael J. Ricks, Richard B. Rogers
  • Patent number: 4400563
    Abstract: 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: Grant
    Filed: June 20, 1979
    Date of Patent: August 23, 1983
    Assignee: Daikin Kogyo Co., Ltd.
    Inventors: Yohnosuke Ohsaka, Uji Hiramatsu, Toshihide Honda
  • Patent number: 4395577
    Abstract: 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: Grant
    Filed: October 22, 1981
    Date of Patent: July 26, 1983
    Assignee: American Cyanamid Company
    Inventor: Donald R. Maulding
  • Patent number: 4393257
    Abstract: 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: Grant
    Filed: June 20, 1979
    Date of Patent: July 12, 1983
    Assignee: Daikin Kogyo Co., Ltd.
    Inventors: Tsuneo Nakagawa, Uji Hiramatsu, Toshihide Honda
  • Patent number: 4350824
    Abstract: 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: Grant
    Filed: February 23, 1981
    Date of Patent: September 21, 1982
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hans-Jochem Riebel, Fritz Maurer, Uwe Priesnitz