Plural Halogens Bonded Directly To Benzene Ring Patents (Class 568/938)
  • Patent number: 8399710
    Abstract: An alkali metal fluoride dispersion of an alkali metal fluoride and an aprotic organic solvent is obtainable by (A) separating a liquid phase from an alkali metal fluoride dispersion comprising an alcohol solvent and an alkali metal fluoride, and mixing the separated liquid phase with an aprotic organic solvent having a boiling point of 85° C. or higher at normal pressure; (B) obtaining a mixture containing the alkali metal fluoride by (b1) concentrating the mixture containing the alkali metal fluoride to obtain a concentrated fraction and a concentrated residue; (b2) mixing a residue of the alkali metal fluoride dispersion with the concentrated fraction obtained in (b1); and (b3) separating a liquid phase from the mixture containing an alkali metal fluoride obtained in (b2) and mixing the separated liquid phase with the concentrated residue; and (C) removing the alcohol solvent from the mixture containing the alkali metal fluoride.
    Type: Grant
    Filed: August 27, 2008
    Date of Patent: March 19, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventor: Koji Hagiya
  • Publication number: 20130060032
    Abstract: A potassium fluoride dispersion essentially consisting of potassium fluoride and an aprotic organic solvent having a boiling point higher than that of methanol, which is obtainable by mixing a mixture containing potassium fluoride and 5 to 50 parts by weight of methanol per 1 part by weight of potassium fluoride with the aprotic organic solvent followed by concentrating the obtained mixture, and a process for producing a fluorine-containing organic compound comprising contacting an organic compound having at least one group capable of being substituted nucleophilically with a fluorine atom with the potassium fluoride dispersion.
    Type: Application
    Filed: October 10, 2012
    Publication date: March 7, 2013
    Inventors: Koji HAGIYA, Kazuaki SASAKI
  • Patent number: 8350091
    Abstract: A potassium fluoride dispersion essentially consisting of potassium fluoride and an aprotic organic solvent having a boiling point higher than that of methanol, which is obtainable by mixing a mixture containing potassium fluoride and 5 to 50 parts by weight of methanol per 1 part by weight of potassium fluoride with the aprotic organic solvent followed by concentrating the obtained mixture, and a process for producing a fluorine-containing organic compound comprising contacting an organic compound having at least one group capable of being substituted nucleophilically with a fluorine atom with the potassium fluoride dispersion.
    Type: Grant
    Filed: December 30, 2011
    Date of Patent: January 8, 2013
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Koji Hagiya, Kazuaki Sasaki
  • Patent number: 8008504
    Abstract: The present invention provides an efficient, safe and cost effective way to prepare 5-(4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzenamine which is a key intermediate for the preparation of substituted pyrimidinylaminobenzamides of formula (II):
    Type: Grant
    Filed: July 12, 2010
    Date of Patent: August 30, 2011
    Assignee: Novartis AG
    Inventors: Stephan Abel, Murat Acemoglu, Bernhard Erb, Christoph Krell, Joseph Sclafani, Mark Meisenbach, Mahavir Prashad, Wen-Chung Shieh, Song Xue
  • 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: 20110040092
    Abstract: The invention relates to a process for making HOF.RCN and using it to oxidise organic substrates in a quick and safe way. The process comprises passing diluted fluorine through a conduit and RCN in water through another conduit into a microreactor to form HOF.RCN and reacting this with an organic substrates.
    Type: Application
    Filed: September 5, 2008
    Publication date: February 17, 2011
    Applicant: THE SECRETARY OF STATE FOR DEFENSE
    Inventors: Christopher Murray, Graham Sandford
  • 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: 20100280257
    Abstract: The present invention provides an efficient, safe and cost effective way to prepare 5-(4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)-benzenamine which is a key intermediate for the preparation of substituted pyrimidinylaminobenzamides of formula (II):
    Type: Application
    Filed: July 12, 2010
    Publication date: November 4, 2010
    Inventors: Stephan Abel, Murat Acemoglu, Bernhard Erb, Christoph Krell, Joseph Sclafani, Mark Meisenbach, Mahavir Prashad, Wen-Chung Shieh, Song Xue
  • Publication number: 20080194886
    Abstract: The invention concerns novel catalysts for aromatic nucleophilic substitution. Said catalysts are compounds of the general formula (I), wherein: R1, R2, R3, R4, R5, and R6, identical or different, are selected among hydrocarbon radicals; the Pn's, advantageously the same, are selected among metalloid elements of column V of a period higher than nitrogen; Z is a metalloid element of column V, advantageously distinct from Pn; preferably a nitrogen (N, P, As, Sb). The invention is applicable to organic synthesis.
    Type: Application
    Filed: April 15, 2008
    Publication date: August 14, 2008
    Applicant: RHODIA CHIMIE
    Inventors: Vincent Schanen, Henri-Jean Cristau, Marc Taillefer
  • Patent number: 7078571
    Abstract: A process for preparing 1,3-di-halo-substituted benzene derivatives (II) from 2,6-di-halo-substituted benzaldehydes (I) (where X1, X2 are each independently F, Cl, Br, and R1, R2, R3 are each independently H, halogen, OH, C1–C12-alkyl, CF3, CHO, C6–C14-aryl, Oalkyl, Oaryl, NO2) by reacting with an alkaline medium, which comprises initially charging the alkaline medium and metering in the 2,6-di-halo-substituted benzaldehyde (I) or initially charging the 2,6-di-halo-substituted benzaldehyde (I) and metering in the alkaline medium
    Type: Grant
    Filed: October 24, 2003
    Date of Patent: July 18, 2006
    Assignee: Clariant GmbH
    Inventors: Stefan Brand, Daniel Decker, Thomas Wessel
  • Patent number: 6943257
    Abstract: The present invention provides a process for preparing an aromatic bromide or aromatic iodide from an aromatic amine derivative using nitrite anion and halodimethylsulfonium halide generated in situ from hydrobromic acid/DMSO or hydriodic acid/DMSO. The process for producing compounds of the formula (1) is disclosed (1) wherein X is bromine or iodine: Y is carbon or nitrogen; R1, R2, R3, R4 and R5 which may be the same or different and are selected independently from the group consisting of a hydrogen, a hologen, a C1-C8 alkyl, a C1-C10 alkoxy, a nitro, a formyl, an aryl, a benzyl, a C2-C10 alkylcarbonyl and an arylcarbonyl, provided that adjacent groups as selected from R1, R2, R3, R4 and R5 may combine to form a ring.
    Type: Grant
    Filed: September 21, 2001
    Date of Patent: September 13, 2005
    Inventors: Woon Phil Baik, Jung Min Kim, Young Sam Kim, Cheol Hun Yoon, Shin Jong Kim, Seok Woo Lee
  • Publication number: 20040087816
    Abstract: A process for preparing 1,3-di-halo-substituted benzene derivatives (II) from 2,6-di-halo-substituted benzaldehydes (I) (where X1, X2 are each independently F, Cl, Br, and R1, R2, R3 are each independently H, halogen, OH, C1-C12-alkyl, CF3, CHO, C6-C14-aryl, Oalkyl, Oaryl, NO2) by reacting with an alkaline medium, which comprises initially charging the alkaline medium and metering in the 2,6-di-halo-substituted benzaldehyde (I) or initially charging the 2,6-di-halo-substituted benzaldehyde (I) and metering in the alkaline medium.
    Type: Application
    Filed: October 24, 2003
    Publication date: May 6, 2004
    Applicant: Clariant GmbH
    Inventors: Stefan Brand, Daniel Decker, Thomas Wessel
  • Patent number: 6353142
    Abstract: 1,2-Dichlorobenzene can be reacted very selectively under adiabatic reaction conditions to give 3,4-dichloronitrobenzene by intensively mixing 1,2-dichlorobenzene with nitric acid, sulphuric acid and water, simultaneously or successively, in their total amount, using a mixing energy of 1-50 watts per litre of the total reaction mixture, preferably 3-30 W/l, and maintaining a temperature of from 0 to 60° C. during mixing.
    Type: Grant
    Filed: November 2, 2000
    Date of Patent: March 5, 2002
    Assignee: Bayer Aktiengesellschaft
    Inventors: Eberhard Zirngiebl, Bernd-Michael König, Hans-Martin Weber, Thomas Linn, Hans-Joachim Raatz
  • Patent number: 6329529
    Abstract: Disclosed are a fluorinating agent represented by the general formula (1): wherein R1 to R4 are a substituted or unsubstituted, saturated or unsaturated alkyl group or a substituted or unsubstituted aryl group, and can be the same or different; R1 and R2 or R3 and R4 can bond to form a ring including a nitrogen atom or a nitrogen atom and other hetero atoms; or R1 and R3 can bond to form a ring including a nitrogen atom or a nitrogen atom and other hetero atoms, for example: a preparation process of the fluorinating agent and a process for preparing fluorine compounds by reacting various compounds with the fluorinating agent. The invention has also disclosed that the fluorinating agent is very effective for fluorinating oxygen containing functional compounds.
    Type: Grant
    Filed: July 31, 1998
    Date of Patent: December 11, 2001
    Assignee: Mitsui Chemicals, Inc.
    Inventors: Hiroshi Sonoda, Kazunari Okada, Akira Takahashi, Kouki Fukumura, Hidetoshi Hayashi, Teruyuki Nagata, Yasuhiro Takano
  • Patent number: 6114589
    Abstract: The invention relates to a process for the preparation of fluorinated compoundsAz.sub.x ArF.sub.w Cl.sub.(y-w) R.sub.z (1)in which Az is a radical --F, --Cl, --Br, --NO.sub.2, --CN, --CF.sub.3, --CCl.sub.3, --CHO, --CO(C.sub.n H.sub.2n+1), --COX or --SO.sub.2 X, where X is F, Cl or Br, x is an integer from 1 to 3, Ar is a phenyl radical, pyridyl radical or naphthyl, w is an integer from 1 to y, y is an integer from 1 to 5, R is H, an alkyl radical or an alkoxy radical having from 1 to 10 carbon atoms, z is an integer from 1 to 5, (x+y+z) is the number of all substitutable valences on the radical Ar, which comprises reacting a compoundAz.sub.x ArCl.sub.y R.sub.z (2),with an alkali metal fluoride in the presence of a component a) or a mixture of component a) and at least one of components b), c), d) and/or e), component a) being one or more quaternary ammonium compounds which contain one or more radicals --(C.sub.m H.sub.2m O)R.sup.
    Type: Grant
    Filed: October 13, 1998
    Date of Patent: September 5, 2000
    Assignee: Clariant GmbH
    Inventors: Thomas Schach, Thomas Wessel, Maren Gutermuth
  • Patent number: 5837761
    Abstract: A plastics composition comprising a high molecular weight material and an effective coloring amount of an azo pigment of formula ##STR1## where M is Mg, Ca, Sr, Ba or Mn or a mixture of two or more thereof, R.sup.1 and R.sup.2 are chlorine or methyl, x is zero or 1, y is zero or 1 and the sum of x and y is 1, with the proviso that when the high molecular weight material is polyvinyl chloride y is zero.
    Type: Grant
    Filed: September 30, 1996
    Date of Patent: November 17, 1998
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Ian Alexander MacPherson, Iain Frank Fraser, Alison MacLennan
  • Patent number: 5773651
    Abstract: Process for the preparation of fluorine-containing compounds by reduction in a container provided with a stirrer, the stirrer being constructed entirely or partly of a carbon material.
    Type: Grant
    Filed: November 27, 1996
    Date of Patent: June 30, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Ralf Pfirmann, Friedrich Seitz
  • Patent number: 5728901
    Abstract: A process for preparing a nitrated arene which comprises reacting an arene and nitric acid in the presence of a water tolerant Lewis acid catalyst under process conditions sufficient to form the nitrated arene and recovering the nitrated arene. Suitable Lewis acid catalysts are represented by the formula M.sup.n (A.sub.1).sub.x (A.sub.2).sub.n-x whereinM is selected from the group consisting of La, Pr, Nd, Sm, Eu, Gd, Dy, Ho, Er, Tm, Yb, Sc, Hf, Lu and Li;A.sub.1 and A.sub.2 are independently selected from a perfluoroalkylsulfonate, a fluorosulfonate, a hexafluorophosphate or a nitrate;n is the common oxidation state of M andx is 1, 2, 3 or 4 with the proviso that x is never greater than n.The catalysts of the process are isolatable from water and can be recycled for subsequent process cycles.
    Type: Grant
    Filed: October 4, 1996
    Date of Patent: March 17, 1998
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Dorai Ramprasad, Francis Joseph Waller, Anthony Gerard Barrett, David Christopher Braddock
  • Patent number: 5714647
    Abstract: Mononitrohalogenobenzenes can be prepared by mixing halogenobenzene, nitric acid, sulphuric acid and water intensively with one another, simultaneously or in succession in their total quantity, and by redispersing them at least twice in the case of continuous preparation, applying a mixing energy of 1-40 watts per liter of the overall reaction mixture, preferably 3-30 W/l, largely suppressing back-mixing in the continuous procedure, and observing adiabatic reaction conditions.
    Type: Grant
    Filed: January 21, 1997
    Date of Patent: February 3, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz Ulrich Blank, Helmut Judat, Bernd-Michael Konig
  • Patent number: 5545768
    Abstract: A process for the preparation of chlorofluoronitrobenzenes and difluoronitrobenzenes, which comprises heating dichloronitrobenzene to not more than 200.degree. C. in excess with an alkali metal fluoride having a total water content of about 0.2 to about 2.5% by weight in the presence of a quaternary ammonium and/or phosphonium salt, crown ether and/or polyethylene glycol dimethyl ether as catalyst in the absence of a solvent.
    Type: Grant
    Filed: December 22, 1992
    Date of Patent: August 13, 1996
    Assignee: Hoechet AG
    Inventors: Theodor Papenfhus, Andreas Kanschik-Conradsen, Wilfried Pressler
  • Patent number: 5502260
    Abstract: Multiply, preferably doubly or triply, fluorinated nitrobenzenes are prepared in an advantageous way from the corresponding chloronitrobenzenes and an alkali metal fluoride in a chlorine-fluorine exchange reaction by catalyzing the reaction with a quaternary ammonium compound comprising at least one alkoxypolyoxyalkyl radical.
    Type: Grant
    Filed: July 19, 1994
    Date of Patent: March 26, 1996
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Thomas Schach, Theodor Papenfuhs
  • Patent number: 5476976
    Abstract: Fluoronitrobenzenes are prepared in an advantageous way from the corresponding chloronitrobenzenes and an alkali metal fluoride by means of a chlorine-fluorine exchange reaction with replacement of a chlorine atom by a fluorine atom, by catalyzing the reaction with a quaternaryammonium compound which comprises at least one alkoxypolyoxyalkyl radical.
    Type: Grant
    Filed: July 19, 1994
    Date of Patent: December 19, 1995
    Assignee: Hoechst AG
    Inventors: Thomas Schach, Theodor Papenfuhs
  • Patent number: 5475163
    Abstract: 2,3-dichloro-nitrobenzene can be prepared by nitration of 1,2-dichlorobenzene using an anhydrous mixture of phosphoric acid, sulphuric acid and nitric acid. The conditions according to the invention displace the ratio of 2,3,-dichloro-nitrobenzene and 3,4-dichloro-nitrobenzene in favor of the 2,3-isomer.
    Type: Grant
    Filed: January 6, 1995
    Date of Patent: December 12, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl H. Neumann, Wolfram Kissener, Helmut Fiege
  • Patent number: 5463148
    Abstract: A process for the preparation of chlorofluoronitrobenzenes in high yields, by reacting dichloronitrobenzenes with alkali metal fluorides having a water content of up to about 2.5% by weight in the presence of a quaternary ammonium and/or phosphonium salt, a crown ether and/or polyethylene glycol dimethyl ether as catalyst in the presence of an aprotic solvent, the boiling point of which is below the reaction temperature under the pressure conditions chosen, at temperatures of about 125.degree. to about 200.degree. C.
    Type: Grant
    Filed: May 5, 1994
    Date of Patent: October 31, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Theodor Papenfuhs, Andreas Kanschik-Conradsen, Wilfried Pressler
  • Patent number: 5349098
    Abstract: A process for producing chlorofluorobenzenes, which comprises reacting fluorine-containing nitrobenzenes of the following formula (1) with chlorine gas to obtain chlorofluorobenzenes of the following formula (2): ##STR1## wherein n and m are integers satisfying 1.ltoreq.n.ltoreq.3, 0.ltoreq.m.ltoreq.2 and 1.ltoreq.n+m.ltoreq.3.
    Type: Grant
    Filed: December 15, 1992
    Date of Patent: September 20, 1994
    Assignee: Asahi Glass Company Ltd.
    Inventors: Seisaku Kumai, Akihiro Wada, Shinsuke Morikawa
  • Patent number: 5315043
    Abstract: A process for halogen exchange fluorination or fluoro-denitration of aromatic compounds having at least one replaceable non-fluorine halogen or nitro substituent with an anhydrous substantially molten alkali metal acid fluoride composition wherein the alkali metal is potassium, rubidium or cesium.
    Type: Grant
    Filed: February 5, 1992
    Date of Patent: May 24, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: Richard E. Fernandez, Mark H. Krackov
  • Patent number: 5294742
    Abstract: Process for preparing 3,5-difluoroaniline, wherein(1) 2,4,5-trichloronitrobenzene is reacted with an alkali metal fluoride in the presence or absence of a polar aprotic solvent at temperatures of about 100.degree. C. to about 250.degree. C., and, after filtering off precipitated salts and fractional distillation of the crude solution,(2) the resulting 5-chloro-2,4-difluoronitrobenzene is chlorinated with denitration to give 1,3-dichloro-4,6-difluorobenzene in the absence of a Lewis acid or of another chlorination catalyst, using anhydrous chlorine gas at temperatures of about 80.degree. to about 250.degree. C., and(3) this compound is nitrated to give 2,6-dichloro-3,5-difluoronitrobenzene in oleum with mixed acid (sulfuric acid/nitric acid) at temperatures of about 15.degree. to about 80.degree. C., and(4) this compound is reduced with hydrogen in the presence of palladium as catalyst and in the presence of an inorganic or organic base at temperatures of about 40.degree. to about 250.degree. C.
    Type: Grant
    Filed: February 18, 1993
    Date of Patent: March 15, 1994
    Assignee: Hoechst Atkiengesellschaft
    Inventors: Thomas Schach, Theodor Papenfuhs
  • Patent number: 5247124
    Abstract: A process for preparing a substituted styrene by reacting a bisarylalkyl ether in the presence of an acid catalyst is disclosed. The process is preferably used for the preparation of 4-acetoxystyrene from 4,4'-(oxydiethylidene)bisphenol diacetate and 4-methoxystyrene from 4,4'-(oxydiethylidene)bisphenol dimethyl ether. A process for preparing a bisarylalkyl ether by reacting a corresponding arylalkanol in the presence of an acid catalyst is also disclosed.
    Type: Grant
    Filed: August 25, 1992
    Date of Patent: September 21, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Mohammad Aslam, Brad L. Smith, George Kvakovszky
  • Patent number: 5237077
    Abstract: The present invention relates to a process for producing an aromatic nitro compound by introducing a nitrogen oxide gas and ozone-containing oxygen or air into a halogenated organic solvent dissolving or suspending therein an aromatic compound, thereby subjecting the aromatic compound to nitration. By the use of a system comprising the nitrogen oxide and ozone-containing oxygen or air as the nitrating agent, the aromatic nitro compound can be produced under mild conditions without using any mineral acid. In addition, the various disadvantages due to the use of mineral acid in the conventional process can be avoided by the process of the present invention.
    Type: Grant
    Filed: March 27, 1992
    Date of Patent: August 17, 1993
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Hitomi Suzuki, Takashi Murashima, Kenkichi Tsukamoto
  • Patent number: 5208394
    Abstract: A process for producing chlorofluorobenzenes, which comprises reacting fluorine-containing nitrobenzenes of the following formula (1) with chlorine gas to obtain chlorofluorobenzenes of the following formula (2): ##STR1## wherein n and m are integers satisfying 1.ltoreq.n.ltoreq.3, 0.ltoreq.m.ltoreq.2 and 1.ltoreq.n+m.ltoreq.3.
    Type: Grant
    Filed: August 6, 1992
    Date of Patent: May 4, 1993
    Assignee: Asahi Glass Company Ltd.
    Inventors: Seisaku Kumai, Akihiro Wada, Shinsuke Morikawa
  • Patent number: 5194672
    Abstract: A process for preparing a substituted styrene by reacting a bisarylalkyl ether in the presence of an acid catalyst is disclosed. The process is preferably used for the preparation of 4-acetoxystyrene from 4,4'-(oxydiethylidene)bisphenol diacetate and 4-methoxystyrene from 4,4'-(oxydiethylidene)bisphenol dimethyl ether. A process for preparing a bisarylalkyl ether by reacting a corresponding arylalkanol in the presence of an acid catalyst is also disclosed.
    Type: Grant
    Filed: May 14, 1991
    Date of Patent: March 16, 1993
    Assignee: Hoechst Celanese Corporation
    Inventors: Mohammad Aslam, Brad L. Smith, George Kvakovszky
  • Patent number: 5162583
    Abstract: Disclosed herein are the derivative of benzyl ether represented by the formula (I) ##STR1## which is useful as an intermediate compound of the derivatives of 1,5-diphenyl-1H-1,2,4- triazole-3-carboxamide represented by the formula (II), ##STR2## wherein R is a straight-chain alkyl group having 1 to 10 carbon atoms which is non-substituted or substituted with 1 to 19 fluorine atoms, a branched alkyl group having 3 to 10 carbon atoms which is non-substituted or substituted with 1 to 19 fluorine atoms, a cyclic alkyl group having 3 to 10 carbon atoms, an alkyl group having 1 to 3 carbon atoms which is substituted with an alicyclic structure having 3 to 7 carbon atoms, a phenyl group or an aralkyl group having 7 to 9 carbon atoms; X.sup.1 is a halogen or an alkyl group having 1 to 3 carbon atoms; X.sup.2 is a hydrogen, a halogen or an alkyl group having 1 to 3 carbon atoms; Y.sup.1 is a hydrogen or a fluorine; Y.sup.2 is a hydrogen or a fluorine; and Z is a nitro group or an amino group.
    Type: Grant
    Filed: September 27, 1990
    Date of Patent: November 10, 1992
    Assignee: Kureha Kagaku Kogyo Kabushiki Kaisha
    Inventors: Takafumi Shida, Hideo Arabori, Takeo Watanabe, Yoshikazu Kubota, Isao Ichinose, Yoichi Kanda, Shiro Yamazaki, Hiroyasu Shinkawa
  • Patent number: 5104491
    Abstract: Crude pentachloronitrobenzene containing hexachlorobenzene and small amounts of acids is treated in the molten state or in a mixture solution of nitrobenzene or chloronitrobenzenes with an inorganic basic substance and then subjected to a distillation under reduced pressure.
    Type: Grant
    Filed: March 12, 1991
    Date of Patent: April 14, 1992
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Mitsumasa Umemoto, Ryuichi Mita, Yoshitsugu Kono, Hiroshi Maeda
  • Patent number: 5041674
    Abstract: 1-Chloro-3,5-difluorobenzene is chlorinated to give 4,6-difluoro-1,2,3-trichlorobenzene which in turn is nitrated and reduced to the corresponding novel aniline, 2,6-difluoro-3,4,5-trichloroaniline. Further reduction of this aniline provides 2,6-difluoroaniline with high selectivity.
    Type: Grant
    Filed: June 14, 1990
    Date of Patent: August 20, 1991
    Assignee: DowElanco
    Inventors: R. Garth Pews, James A. Gall
  • Patent number: 4978769
    Abstract: Aromatic, ring-fluorinated compounds are particularly advantageously prepared by nucleophilic exchange in the course of reaction wih potassium fluoride in the presence of phase transfer catalysts and, if desired, solvents by carrying out the reaction in the additional presence of metal salts.
    Type: Grant
    Filed: August 7, 1989
    Date of Patent: December 18, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ernst Kysela, Rudolf Braden
  • Patent number: 4973772
    Abstract: A process is disclosed for preparing fluoroaromatic compounds (such as fluoronitrobenzene compounds) by reaction of corresponding chloroacromatic compounds (such as chloronitrobenzene compounds) with alkali metal fluoride salts in the presence of alkyldiorganoaminopyridinium salts as phase transfer catalysts. A tertiary carbon atom is directly attached to the alkyl carbon atom which is directly attached to the ring nitrogen atom. A preferred catalyst is N-neopentyl-4-(4'-methylpiperidinyl)pyridinium chloride.
    Type: Grant
    Filed: February 7, 1987
    Date of Patent: November 27, 1990
    Assignee: Mallinckrodt, Inc.
    Inventor: Gary L. Cantrell
  • Patent number: 4973771
    Abstract: N-secondary-alkyldiorganoaminopyridinium salts are disclosed which are useful as phase transfer catalysts for facilitating preparation of fluoroaromatic compounds (such as fluoronitrobenzene compounds) from the corresponding chloroaromatic compounds (such as chloronitrobenzene compounds).
    Type: Grant
    Filed: February 9, 1987
    Date of Patent: November 27, 1990
    Assignee: Mallinckrodt, Inc.
    Inventor: Gary L. Cantrell
  • Patent number: 4927980
    Abstract: A process is disclosed for preparing fluoroaromatic compounds (such as fluoronitrobenzene compounds) by reaction of corresponding chloroaromatic compounds (such as chloronitrobenzene compounds) with alkali metal fluoride salts in the presence of alkyldiorganoaminopyridinium salts as phase transfer catalysts. A secondary carbon atom is directly attached to the alkyl carbon atom which is directly attached to the ring nitrogen atom. A preferred catalyst is N-(2-ethylhexyl)-4-(N',N'- dimethylamino)pyridinium chloride.
    Type: Grant
    Filed: February 9, 1987
    Date of Patent: May 22, 1990
    Assignee: Mallinckrodt Inc.
    Inventor: Gary L. Cantrell
  • Patent number: 4898996
    Abstract: A process for producing 3-chloro-4-fluoronitrobenzene which is characterized by chlorinating 4-fluoronitrobenzene in the presence of:(1) iodine or an iodide in combination with iron or an iron compound or(2) iodine or an iodide in combination with antimony or an antimony compound.
    Type: Grant
    Filed: June 23, 1988
    Date of Patent: February 6, 1990
    Assignee: Nippon Kayaku Kabushiki Kaisha
    Inventors: Tsukasa Ishikura, Tatuharu Fukushima
  • Patent number: 4876404
    Abstract: Dichlorotrifluoromethyltoluenes useful in producing some medicines and agricultural chemicals are formed with good yields by reacting dichlorotrichloromethyltoluenes with hydrogen fluoride usually at 0.degree.-100.degree. C. under pressure of 3-20 kg/cm.sup.2. Besides known 3,4-dichloro-6-trifluoromethyltoluene and 3,4-dichloro-5-trifluoromethyltoluene, novel isomers are also obtained by this method.
    Type: Grant
    Filed: August 11, 1987
    Date of Patent: October 24, 1989
    Assignee: Central Glass Company, Limited
    Inventors: Takeshi Kondo, Toshikazu Kawai, Hideki Oshio
  • Patent number: 4876376
    Abstract: A process for the halogenation (bromination or chlorination)/nitration/fluorination of aromatic derivatives substituted by at least one group containing a halogenoalkyl unit. The aromatic derivative is reacted with a halogen and a nitrating agent in liquid hydrofluoric acid. The products obtained are useful as intermediates for the synthesis of compounds having a plant-protecting or pharmaceutical activity.
    Type: Grant
    Filed: December 15, 1987
    Date of Patent: October 24, 1989
    Assignee: Rhone-Poulenc Specialistes Chimiques
    Inventors: Michael Desbois, Camille Disdier
  • Patent number: 4868347
    Abstract: Substituted fluorobenzenes which are produced in aprotic, polar solvents or in mixtures which contain such solvents can be obtained by extracting the substituted fluorobenzenes from the solvents or solvent mixtures with aliphatic extracting agents and then seaprating the extracting agents from the substituted fluorobenzenes.
    Type: Grant
    Filed: December 9, 1987
    Date of Patent: September 19, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Heinz U. Blank, Edwin Ritzer
  • Patent number: 4855292
    Abstract: Novel 4-oxoquinoline-3-carboxylic acid compounds of the formula: ##STR1## wherein R.sup.2 is 1-pyrrolidinyl which may have 1 to 2 substituents selected from the group consisting of (i) C.sub.1 -C.sub.6 alkyl, (ii) amino-(C.sub.1 -C.sub.6)alkyl, said amino being optionally substituted by 1 or 2 substituents selected from C.sub.1 -C.sub.6 alkyl, C.sub.1 -C.sub.6 alkanoyl, and C.sub.1 -C.sub.6 alkoxycarbonyl, (iii) amino which may be substituted by 1 or 2 substituents selected from C.sub.1 -C.sub.6 alkyl, phenyl(C.sub.1 -C.sub.6)alkyl, C.sub.1 -C.sub.6 alkoxycarbonyl, and C.sub.1 -C.sub.6 alkanoyl, and (iv) 2-oxo-1,3-dioxolenemethylamino which is substituted by C.sub.1 -C.sub.6 alkyl; or 1-piperidinyl which may have 1 to 3 substituents selected from oxo, hydroxy, halogen and C.sub.1 -C.sub.6 alkyl, and R.sup.3 is C.sub.1 -C.sub.
    Type: Grant
    Filed: July 23, 1987
    Date of Patent: August 8, 1989
    Assignee: Otsuka Pharmaceutical Company, Limited
    Inventors: Hiraki Ueda, Hisashi Miyamoto, Shinji Aki, Tatsuya Otsuka
  • Patent number: 4849552
    Abstract: An improved process is disclosed for preparing fluoroaromatic compounds (such as fluoronitrobenzene compounds) wherein chloroaromatic compounds (such as chloronitrobenzene compounds) are reacted with potassium fluoride in a solvent dispersion thereof prepared from a mixture including the solvent, the fluoride, methanol and an aromatic compound.
    Type: Grant
    Filed: February 5, 1987
    Date of Patent: July 18, 1989
    Assignee: Mallinckrodt, Inc.
    Inventor: Gary L. Cantrell
  • Patent number: 4842696
    Abstract: Pentachloronitrobenzene (PCNB) which initially contains in excess of 0.5% hexachlorobenzene (HCB) is purified by distilling the impure PCNB at a temperature between 100.degree.-250.degree. C. and a pressure below or at atmospheric pressure to obtain a PCNB product having a HCB content lower than 0.5%, and preferably lower than 0.1%.
    Type: Grant
    Filed: October 8, 1987
    Date of Patent: June 27, 1989
    Assignee: Quimica Organica De Mexico, S.A. De C.Y.
    Inventor: Arturo S. Cazares
  • Patent number: 4826982
    Abstract: Quinolonecarboxylic acid derivatives of the following formula, ##STR1## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are each independently hydrogen atom or lower alkyl group; the hydrates or the pharmaceutically acceptable acid addition or alkali salts thereof are useful as an antibacterial agent.
    Type: Grant
    Filed: September 2, 1986
    Date of Patent: May 2, 1989
    Assignee: Kyorin Pharmaceutical Co., Ltd.
    Inventors: Kuniyoshi Masuzawa, Seigo Suzue, Keiji Hirai, Takayoshi Ishizaki
  • Patent number: 4780559
    Abstract: A method for the preparation of organic fluorides which comprises reacting a quaternary phosphonium fluoride or bifluoride with an organic substrate having at least one atom or group capable of being replaced by a fluorine atom.
    Type: Grant
    Filed: January 1, 1986
    Date of Patent: October 25, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventors: Stephen J. Brown, James H. Clark
  • Patent number: 4704483
    Abstract: A process for the preparation of 3-chloro-4-fluoro-5-nitrobenzotrifluoride and 3,4-difluoro-5-nitrobenzotrifluoride by reaction of 3,4-di-chloro-5-nitrobenzotrifluoride and 4-chloro-3,5-dinitrobenzotrifluoride, respectively, with an alkali metal fluoride.
    Type: Grant
    Filed: December 9, 1985
    Date of Patent: November 3, 1987
    Assignee: Occidental Chemical Corporation
    Inventors: David Y. Tang, Byron R. Cotter, Fredrick J. Goetz
  • Patent number: 4684734
    Abstract: Organic fluorine compounds such as pentafluorobenzonitrile, tetrafluorophthalonitriles, and pentafluoropyridine are produced by a method which comprises causing a chloro- or bromo-organic compound to react with a fluorinating agent such as an alkali metal fluoride in benzonitrile as a solvent at temperatures in the range of 190.degree. to 400.degree. C. under at least spontaneously generated pressure.
    Type: Grant
    Filed: September 13, 1985
    Date of Patent: August 4, 1987
    Assignee: Nippon Shokubai KK Co., Ltd.
    Inventors: Osamu Kaieda, Masaru Awashima, Isao Okitaka, Toshiaki Nakamura
  • 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