Plural Halogens Bonded Directly To Benzene Ring Patents (Class 568/938)
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Patent number: 8399710Abstract: 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: GrantFiled: August 27, 2008Date of Patent: March 19, 2013Assignee: Sumitomo Chemical Company, LimitedInventor: Koji Hagiya
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Publication number: 20130060032Abstract: 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: ApplicationFiled: October 10, 2012Publication date: March 7, 2013Inventors: Koji HAGIYA, Kazuaki SASAKI
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Patent number: 8350091Abstract: 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: GrantFiled: December 30, 2011Date of Patent: January 8, 2013Assignee: Sumitomo Chemical Company, LimitedInventors: Koji Hagiya, Kazuaki Sasaki
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Patent number: 8008504Abstract: 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: GrantFiled: July 12, 2010Date of Patent: August 30, 2011Assignee: Novartis AGInventors: Stephan Abel, Murat Acemoglu, Bernhard Erb, Christoph Krell, Joseph Sclafani, Mark Meisenbach, Mahavir Prashad, Wen-Chung Shieh, Song Xue
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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: 20110040092Abstract: 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: ApplicationFiled: September 5, 2008Publication date: February 17, 2011Applicant: THE SECRETARY OF STATE FOR DEFENSEInventors: Christopher Murray, Graham Sandford
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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: 20100280257Abstract: 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: ApplicationFiled: July 12, 2010Publication date: November 4, 2010Inventors: Stephan Abel, Murat Acemoglu, Bernhard Erb, Christoph Krell, Joseph Sclafani, Mark Meisenbach, Mahavir Prashad, Wen-Chung Shieh, Song Xue
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Publication number: 20080194886Abstract: 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: ApplicationFiled: April 15, 2008Publication date: August 14, 2008Applicant: RHODIA CHIMIEInventors: Vincent Schanen, Henri-Jean Cristau, Marc Taillefer
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Patent number: 7078571Abstract: 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 mediumType: GrantFiled: October 24, 2003Date of Patent: July 18, 2006Assignee: Clariant GmbHInventors: Stefan Brand, Daniel Decker, Thomas Wessel
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Patent number: 6943257Abstract: 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: GrantFiled: September 21, 2001Date of Patent: September 13, 2005Inventors: Woon Phil Baik, Jung Min Kim, Young Sam Kim, Cheol Hun Yoon, Shin Jong Kim, Seok Woo Lee
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Publication number: 20040087816Abstract: 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: ApplicationFiled: October 24, 2003Publication date: May 6, 2004Applicant: Clariant GmbHInventors: Stefan Brand, Daniel Decker, Thomas Wessel
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Patent number: 6353142Abstract: 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: GrantFiled: November 2, 2000Date of Patent: March 5, 2002Assignee: Bayer AktiengesellschaftInventors: Eberhard Zirngiebl, Bernd-Michael König, Hans-Martin Weber, Thomas Linn, Hans-Joachim Raatz
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Patent number: 6329529Abstract: 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: GrantFiled: July 31, 1998Date of Patent: December 11, 2001Assignee: Mitsui Chemicals, Inc.Inventors: Hiroshi Sonoda, Kazunari Okada, Akira Takahashi, Kouki Fukumura, Hidetoshi Hayashi, Teruyuki Nagata, Yasuhiro Takano
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Patent number: 6114589Abstract: 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: GrantFiled: October 13, 1998Date of Patent: September 5, 2000Assignee: Clariant GmbHInventors: Thomas Schach, Thomas Wessel, Maren Gutermuth
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Patent number: 5837761Abstract: 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: GrantFiled: September 30, 1996Date of Patent: November 17, 1998Assignee: Ciba Specialty Chemicals CorporationInventors: Ian Alexander MacPherson, Iain Frank Fraser, Alison MacLennan
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Patent number: 5773651Abstract: 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: GrantFiled: November 27, 1996Date of Patent: June 30, 1998Assignee: Hoechst AktiengesellschaftInventors: Ralf Pfirmann, Friedrich Seitz
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Patent number: 5728901Abstract: 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: GrantFiled: October 4, 1996Date of Patent: March 17, 1998Assignee: Air Products and Chemicals, Inc.Inventors: Dorai Ramprasad, Francis Joseph Waller, Anthony Gerard Barrett, David Christopher Braddock
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Patent number: 5714647Abstract: 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: GrantFiled: January 21, 1997Date of Patent: February 3, 1998Assignee: Bayer AktiengesellschaftInventors: Heinz Ulrich Blank, Helmut Judat, Bernd-Michael Konig
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Patent number: 5545768Abstract: 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: GrantFiled: December 22, 1992Date of Patent: August 13, 1996Assignee: Hoechet AGInventors: Theodor Papenfhus, Andreas Kanschik-Conradsen, Wilfried Pressler
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Patent number: 5502260Abstract: 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: GrantFiled: July 19, 1994Date of Patent: March 26, 1996Assignee: Hoechst AktiengesellschaftInventors: Thomas Schach, Theodor Papenfuhs
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Patent number: 5476976Abstract: 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: GrantFiled: July 19, 1994Date of Patent: December 19, 1995Assignee: Hoechst AGInventors: Thomas Schach, Theodor Papenfuhs
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Patent number: 5475163Abstract: 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: GrantFiled: January 6, 1995Date of Patent: December 12, 1995Assignee: Bayer AktiengesellschaftInventors: Karl H. Neumann, Wolfram Kissener, Helmut Fiege
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Patent number: 5463148Abstract: 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: GrantFiled: May 5, 1994Date of Patent: October 31, 1995Assignee: Hoechst AktiengesellschaftInventors: Theodor Papenfuhs, Andreas Kanschik-Conradsen, Wilfried Pressler
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Patent number: 5349098Abstract: 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: GrantFiled: December 15, 1992Date of Patent: September 20, 1994Assignee: Asahi Glass Company Ltd.Inventors: Seisaku Kumai, Akihiro Wada, Shinsuke Morikawa
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Patent number: 5315043Abstract: 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: GrantFiled: February 5, 1992Date of Patent: May 24, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventors: Richard E. Fernandez, Mark H. Krackov
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Patent number: 5294742Abstract: 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: GrantFiled: February 18, 1993Date of Patent: March 15, 1994Assignee: Hoechst AtkiengesellschaftInventors: Thomas Schach, Theodor Papenfuhs
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Patent number: 5247124Abstract: 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: GrantFiled: August 25, 1992Date of Patent: September 21, 1993Assignee: Hoechst Celanese CorporationInventors: Mohammad Aslam, Brad L. Smith, George Kvakovszky
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Patent number: 5237077Abstract: 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: GrantFiled: March 27, 1992Date of Patent: August 17, 1993Assignee: Nippon Kayaku Kabushiki KaishaInventors: Hitomi Suzuki, Takashi Murashima, Kenkichi Tsukamoto
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Patent number: 5208394Abstract: 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: GrantFiled: August 6, 1992Date of Patent: May 4, 1993Assignee: Asahi Glass Company Ltd.Inventors: Seisaku Kumai, Akihiro Wada, Shinsuke Morikawa
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Patent number: 5194672Abstract: 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: GrantFiled: May 14, 1991Date of Patent: March 16, 1993Assignee: Hoechst Celanese CorporationInventors: Mohammad Aslam, Brad L. Smith, George Kvakovszky
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Patent number: 5162583Abstract: 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: GrantFiled: September 27, 1990Date of Patent: November 10, 1992Assignee: Kureha Kagaku Kogyo Kabushiki KaishaInventors: Takafumi Shida, Hideo Arabori, Takeo Watanabe, Yoshikazu Kubota, Isao Ichinose, Yoichi Kanda, Shiro Yamazaki, Hiroyasu Shinkawa
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Patent number: 5104491Abstract: 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: GrantFiled: March 12, 1991Date of Patent: April 14, 1992Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Mitsumasa Umemoto, Ryuichi Mita, Yoshitsugu Kono, Hiroshi Maeda
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Patent number: 5041674Abstract: 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: GrantFiled: June 14, 1990Date of Patent: August 20, 1991Assignee: DowElancoInventors: R. Garth Pews, James A. Gall
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Patent number: 4978769Abstract: 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: GrantFiled: August 7, 1989Date of Patent: December 18, 1990Assignee: Bayer AktiengesellschaftInventors: Ernst Kysela, Rudolf Braden
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Patent number: 4973772Abstract: 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: GrantFiled: February 7, 1987Date of Patent: November 27, 1990Assignee: Mallinckrodt, Inc.Inventor: Gary L. Cantrell
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Patent number: 4973771Abstract: 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: GrantFiled: February 9, 1987Date of Patent: November 27, 1990Assignee: Mallinckrodt, Inc.Inventor: Gary L. Cantrell
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Patent number: 4927980Abstract: 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: GrantFiled: February 9, 1987Date of Patent: May 22, 1990Assignee: Mallinckrodt Inc.Inventor: Gary L. Cantrell
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Patent number: 4898996Abstract: 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: GrantFiled: June 23, 1988Date of Patent: February 6, 1990Assignee: Nippon Kayaku Kabushiki KaishaInventors: Tsukasa Ishikura, Tatuharu Fukushima
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Patent number: 4876404Abstract: 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: GrantFiled: August 11, 1987Date of Patent: October 24, 1989Assignee: Central Glass Company, LimitedInventors: Takeshi Kondo, Toshikazu Kawai, Hideki Oshio
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Patent number: 4876376Abstract: 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: GrantFiled: December 15, 1987Date of Patent: October 24, 1989Assignee: Rhone-Poulenc Specialistes ChimiquesInventors: Michael Desbois, Camille Disdier
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Patent number: 4868347Abstract: 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: GrantFiled: December 9, 1987Date of Patent: September 19, 1989Assignee: Bayer AktiengesellschaftInventors: Heinz U. Blank, Edwin Ritzer
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Patent number: 4855292Abstract: 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: GrantFiled: July 23, 1987Date of Patent: August 8, 1989Assignee: Otsuka Pharmaceutical Company, LimitedInventors: Hiraki Ueda, Hisashi Miyamoto, Shinji Aki, Tatsuya Otsuka
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Patent number: 4849552Abstract: 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: GrantFiled: February 5, 1987Date of Patent: July 18, 1989Assignee: Mallinckrodt, Inc.Inventor: Gary L. Cantrell
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Patent number: 4842696Abstract: 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: GrantFiled: October 8, 1987Date of Patent: June 27, 1989Assignee: Quimica Organica De Mexico, S.A. De C.Y.Inventor: Arturo S. Cazares
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Patent number: 4826982Abstract: 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: GrantFiled: September 2, 1986Date of Patent: May 2, 1989Assignee: Kyorin Pharmaceutical Co., Ltd.Inventors: Kuniyoshi Masuzawa, Seigo Suzue, Keiji Hirai, Takayoshi Ishizaki
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Patent number: 4780559Abstract: 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: GrantFiled: January 1, 1986Date of Patent: October 25, 1988Assignee: Imperial Chemical Industries PLCInventors: Stephen J. Brown, James H. Clark
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Patent number: 4704483Abstract: 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: GrantFiled: December 9, 1985Date of Patent: November 3, 1987Assignee: Occidental Chemical CorporationInventors: David Y. Tang, Byron R. Cotter, Fredrick J. Goetz
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Patent number: 4684734Abstract: 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: GrantFiled: September 13, 1985Date of Patent: August 4, 1987Assignee: Nippon Shokubai KK Co., Ltd.Inventors: Osamu Kaieda, Masaru Awashima, Isao Okitaka, Toshiaki Nakamura
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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