Preparing Compound Which Contains Halogen Bonded Directly To Carbon Patents (Class 564/417)
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Patent number: 5498794Abstract: The invention relates to a process for preparing fluoroanilines of the formula (I)F.sub.n ArNH.sub.2 (I)in which n is 1, 2, 3 or 4, Ar is phenyl, naphthyl or pyridyl, and the remaining substituents on the Ar radical are identical or different and are, independently of each other, hydrogen, halogen, (C.sub.1 -C.sub.1)-alkyl, phenyl, NR.sub.2, OR, CN, CHO, or COR, where R is hydrogen or (C.sub.1 -C.sub.6)-alkyl, wherein fluoronitrobenzenes of the formula (II)X.sub.m F.sub.n ArNO.sub.2 (II)in which n, Ar and the remaining substituents on the Ar radical have the abovementioned meaning, X is chlorine or bromine and m is 1, 2, 3 or 4, are reacted with hydrogen in the presence of a palladium catalyst, of an amine which is not soluble in water and which also does not form water-soluble hydrohalides, and, where appropriate, of an inert solvent.Type: GrantFiled: February 9, 1995Date of Patent: March 12, 1996Assignee: Hoechst AktiengesellschaftInventors: Thomas Schach, Theodor Papenfuhs
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Patent number: 5484953Abstract: Novel o-phenylenediamines of the formula containing fluoroalkyl(ene) groups ##STR1## in which the symbols used have the meaning given in the description, processes for their preparation and their use as intermediates.Type: GrantFiled: June 3, 1994Date of Patent: January 16, 1996Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Bernd Baasner, Folker Lieb
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Patent number: 5449831Abstract: 2-methyl-3-aminobenzo-trifluoride is prepared with high yields and high productivity by first halogenating o-trifluoromethylbenzalhalide, then secondly hydrogenating 2-trifluoromethyl-4-halogeno-benzalhalide formed by the first reaction, then thirdly nitrating 2-methyl-monohalogenobenzotrifluoride formed by the second reaction, and then fourthly hydrogenating 2-methyl-3-nitro-5-halogenobenzotrifluoride formed by the third reaction.Type: GrantFiled: January 5, 1994Date of Patent: September 12, 1995Assignee: Central Glass Company, LimitedInventors: Takayuki Nishimiya, Masatomi Kanai, Toshikazu Kawai
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Patent number: 5442114Abstract: There is disclosed a process for producing an aromatic amide compound of the general formula (4), including the steps of subjecting an o-nitrophenol compound of the general formula (1) to catalytic reduction in acetone or an aromatic hydrocarbon solvent under the presence of a nickel catalyst to give an o-aminophenol compound of the general formula (2); and (b) subjecting the o-aminophenol compound of the general formula (2) to condensation with an acid chloride compound having a sulfur content of 0.5% or less, based on the weight of the acid chloride compound, of the general formula (3) in acetone or an aromatic hydrocarbon solvent under an atmosphere of an inert gas having an oxygen concentration of 1% or less. The acid chloride compound having a sulfur content of 0.5% or less, based on the weight of the acid chloride compound, of the general formula (3) may be obtained by allowing a carboxylic acid compound of the general formula (5) to react with thionyl chloride and by concentrating the reaction mixture.Type: GrantFiled: January 18, 1994Date of Patent: August 15, 1995Assignee: Sumitomo Chemical Company, LimitedInventors: Kan Takamine, Michio Yamato, Akira Murakami, Tooru Tokumaru, Yoshinori Nakayama, Motoo Hazama
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Patent number: 5410084Abstract: A polyimide comprising a requisite structural unit having one or more recurring structural units of the formula: ##STR1## such as the structural units of the formula ##STR2## Further, the present invention relates to a novel aromatic diamine which has a perfluoro radical and can be used as a raw material monomer of the polyimide, and a process for preparing the same.The polyimide can have an extremely low dielectric constant and is colorless, transparent and excellent in processability and heat resistance.Type: GrantFiled: June 2, 1994Date of Patent: April 25, 1995Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Mitsunori Matsuo, Tsutomu Ishida, Keizaburo Yamaguchi, Akihiro Yamaguchi
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Patent number: 5410085Abstract: Chlorine-substituted aromatic amines are prepared by the hydrogenation of chlorine-substituted aromatic nitro compounds in the presence of a catalyst containing platinum and nickel and/or cobalt on an activated charcoal support, the platinum having been simultaneously deposited and reduced on the activated charcoal support in the preparation of the catalyst. Such catalysts are furthermore prepared, as are catalysts containing noble metals on an activated charcoal support, it also being possible for the latter to be used for the reduction of nitronaphthalenes or nitrotoluenes.Type: GrantFiled: October 20, 1993Date of Patent: April 25, 1995Assignee: Bayer AktiengesellschaftInventors: Udo Birkenstock, Walter Kipshagen, Herbert Schmidt, Thomas-Jorn Schulz, Eberhard Zirngiebl
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Patent number: 5347052Abstract: 3,5-Diaminobenzotrifluoride can be produced, in a single step, by reacting 4-chloro-3,5-dinitrobenzotrifluoride, in methanol, with hydrogen gas, in the presence of magnesium oxide, and in the presence of a catalyst comprising palladium on a carbon support.Type: GrantFiled: April 15, 1991Date of Patent: September 13, 1994Assignee: Occidental Chemical CorporationInventor: David E. Albright, Jr.
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Patent number: 5304680Abstract: Aromatic amines which are substituted by C.sub.1 -C.sub.4 -alkoxy in the p-position are prepared by catalytic hydrogenation of the underlying aromatic nitro compounds in a reaction medium comprising sulphuric acid and a C.sub.1 -C.sub.4 -alcohol by a Bamberger type rearrangement at elevated temperature, advantageously by carrying out the catalytic hydrogenation under elevated pressure.Type: GrantFiled: July 10, 1991Date of Patent: April 19, 1994Assignee: Bayer AktiengesellschaftInventors: Heinz Landscheidt, Alexander Klausener, Heinz U. Blank
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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: 5292957Abstract: A process for the preparation of N-alkylhalogenoanilines of the formula (I) 100.degree. ##STR1## in which X is a chlorine or bromine atom and n is the number 1 or 2, R.sup.1 is an alkyl (C.sub.1 -C.sub.4) radical, R.sup.2 an alkyl (C.sub.1 -C.sub.6) radical or R.sup.1 and R.sup.2 together with the carbon atom can form a five- or six-membered cycloalkane ring, by reacting a halogenonitrobenzene of the formula (II) ##STR2## in which X and n have the abovementioned meanings with an at least stoichiometric amount of a carbonyl compound of the formula (III) ##STR3## in which R.sup.1 and R.sup.2 have the meanings mentioned or R.sup.1 and R.sup.2 together with the carbon atom of the carbonyl group can form a five- or six-membered cycloalkane ring, in an inert organic solvent at temperatures of about 10 to about 100.degree. C., at a hydrogen superatmospheric pressure of about 0 to about 50 bar, in the presence of a platinum catalyst on activated carbon.Type: GrantFiled: February 20, 1992Date of Patent: March 8, 1994Assignee: Hoechst AktiengesellschaftInventors: Werner Brodt, Theodor Papenfuhs
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Patent number: 5279714Abstract: A process for the preparation of a compound of Formula A: ##STR1## wherein X.sup.1 and X.sup.2 are independently selected from H or any substituent which does not interfere with the electrochemical reductive fluorination; andZ.sup.1 and Z.sup.2 are each independently selected from H or an electron donating group;which comprises electrochemical reductive fluorination of a compound of Formula B: ##STR2## wherein X.sup.1, X.sup.2, Z.sup.1 and Z.sup.2 are as defined above in a mixture of anhydrous hydrogen fluoride and an alkali metal fluoride.The 4-fluoroanilines find use as intermediates in the manufacture of a wide range of agrochemicals, dyestuffs and pharmaceuticals.Type: GrantFiled: March 18, 1992Date of Patent: January 18, 1994Assignee: Imperial Chemical Industries PLCInventors: John S. Moilliet, Ian K. Jones
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Patent number: 5238818Abstract: This amount of an oxidative substance or a peroxidase-like substance can be determined by using a combined color former comprising 4-aminoantipyrine or a derivative thereof, etc., as a main color former and a p-fluoroaniline derivative or a salt thereof as a color producing component.Type: GrantFiled: November 26, 1991Date of Patent: August 24, 1993Assignee: Wako Pure Chemicals Co., Ltd.Inventors: Kazunari Hashizume, Haruhiko Sugiyama, Mutsuhiro Date
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Patent number: 5235106Abstract: The invention concerns the production of a substituted or unsubstituted aniline by selective hydrogenation of the corresponding nitroaromatic compound. It is characterized by the use of a catalyst based on a metal selected from rhodium and ruthenium and based on a metal selected from the group comprising tin, germanium and lead.Type: GrantFiled: January 7, 1992Date of Patent: August 10, 1993Assignee: Institut Francais Du PetroleInventors: Blaise Didillon, Fabienne Le Peltier, Jean-Pierre Candy, Patrick Sarrazin, Jean-Paul Boitiaux, Jean-Marie Basset
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Patent number: 5220070Abstract: A process was developed to prepare 1,3-diamino-5-pentafluorosulfanylbenzene. This process involved two steps: preparing the dinitro compound, 1,3-dinitro-5-pentafluorosulfanylbenzene, and reducing this compound to form the corresponding diamine. This diamine was reacted with various dianhydrides, diacidchlorides, and epoxy resins to form polyimides, polyamides, and crosslinked epoxies. These polymers were used to prepare semi-permeable membranes, wire coatings, and films.Type: GrantFiled: September 5, 1991Date of Patent: June 15, 1993Assignee: The United States of America as represented by the Administrator National Aeronautics and Space AdministrationInventors: Terry L. St. Clair, Anne K. St. Clair, Joseph S. Thrasher
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Patent number: 5157155Abstract: The present invention relates to a novel benzoylurea derivative represented by the formula, ##STR1## its production and insecticides containing it as an active ingredient.Type: GrantFiled: March 11, 1991Date of Patent: October 20, 1992Assignee: Sumitomo Chemical Company, LimitedInventors: Noriyaso Sakamoto, Tatsuya Mori, Tadashi Ohsumi, Toshihiko Yano, Izumi Fujimoto, Yoji Takada
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Patent number: 5144076Abstract: 3,5-Diaminobenzotrifluoride can be produced, in a single step, by reacting 4-chloro-3,5-dinitro benzotrifluoride in a suitable solvent, with hydrogen gas, in the presence of a catalyst comprising palladium on a suitable carrier, and in the presence of a suitable base.Type: GrantFiled: October 1, 1991Date of Patent: September 1, 1992Assignee: Occidental Chemical CorporationInventors: Ramesh Krishnamurti, Lawrence B. Fertel, Henry C. Lin, Mahendra K. Dosi
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Patent number: 5120875Abstract: In the preparation of chlorinated aromatic amines by reaction of corresponding nitro compounds with hydrogen under pressure, at elevated temperature and in the presence of a solvent and small amounts of a basic compound, fewer by-products are formed by using platinum and nickel and/or cobalt on an active charcoal support.Type: GrantFiled: August 13, 1990Date of Patent: June 9, 1992Assignee: Bayer AktiengesellschaftInventors: Udo Birkenstock, Ulrich Kappler, Herbert Schmidt, Jurgen Zander
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Patent number: 5105011Abstract: A process for the preparation of amino halogeno aromatic compounds, according to which a halogenonitro-aromatic compound is brought into the presence of a nickel-, cobalt- or iron-based catalyst, preferably nickel-based, and, more preferably, Raney nickel, in the presence of an effective amount of iodide, at a temperature and hydrogen pressure sufficient to form said halogenoamino-aromatic compound.Type: GrantFiled: July 20, 1990Date of Patent: April 14, 1992Assignee: Rhone-Poulenc ChimieInventors: Georges Cordier, Jean-Michel Grosselin
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Patent number: 5105012Abstract: There is provided an improved process for the reduction of optionally substituted dinitrobenzenes to the corresponding nitroanilines with high yields which comprises contacting the dinitrobenzene with hydrogen in an acidic medium in the presence of a catalytic amount of a combination of a noble metal hydrogenation catalyst, and iron or an iron salt. Isomer specific reductions may be achieved with those compounds containing suitable directing substituents.The 2-halo-5-nitroanilines which may be produced in this process may be converted via a multi-step synthesis to useful 1-aryl-4-substituted 1,4-dihydro-5H-tetrazol-5-one herbicides.Type: GrantFiled: October 11, 1990Date of Patent: April 14, 1992Assignee: FMC CorporationInventor: George Theodoridis
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Patent number: 5087755Abstract: A process for producing an aromatic amine under moderate conditions is provided wherein a catalyst higher in activity than conventional catalysts is used. Reduction of an aromatic nitro compound under a CO/H.sub.2 O system is conducted using a rhodium compound catalyst in the presence of an aqueous alkali solution such as aqueous sodium hydroxide solution. Alternatively, an aromatic nitro compound is reduced under a CO/H.sub.2 O system using a rhodium compound or a ruthenium compound catalyst in the presence of the aqueous alkali solution and additionally at least one compound of amine compounds, diamine compounds, phosphine compounds, phosphite compounds, and diphosphine compounds.Type: GrantFiled: November 15, 1989Date of Patent: February 11, 1992Assignee: Sumitomo Chemical Company, LimitedInventors: Kotohiro Nomura, Masaru Ishino
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Patent number: 5081288Abstract: Substituted 3,5-dichloro-2,4-difluoro-benzenes of the formula ##STR1## in which R represents nitro, amino (including the corresponding ammonium salts) or isocyanato, which can be prepared from 2,3,4,5-tetrachloro-nitrobenzene by means of the reaction, carried out initially, with alkali metal fluorides at elevated temperature in a polar, aprotic solvent, starting from a crude 2,3,4,5-tetrachloro-nitrobenzene containing 2,3,5,6-tetrachloro-nitrobenzene and/or 2,3,4,6-tetrachloro-nitrobenzene, and substituted 3,5-dichloro-2,4-difluoro-benzene being isolated from the reaction mixture at the nitro stage or, after reduction of the nitro group, at the amino stage or, after reduction and phosgenation of the amino group, at the isocyanate stage.Type: GrantFiled: October 10, 1990Date of Patent: January 14, 1992Assignee: Bayer AktiengesellschaftInventors: Heinz U. Blank, Edwin Ritzer
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Patent number: 5077436Abstract: Bis(3-nitrophenoxy) derivatives of aromatic or bridged aromatic hydrocarbons are derived from m-dinitrobenzene and dihydroxy derivatives of said hydrocarbons and certain substituted derivatives thereof by a condensation reaction in dipolar aprotic solvents in the presence of bases. The bis(3-nitrophenoxy) derivatives and derivatives obtained are successively reduced to afford bis-(3-aminophenoxy)derivatives. This is a new method for reacting the dihydroxy-derivatives with m-dinitrobenzene, and hence can prepare novel bis(3-aminophenoxy) derivatives such as 4,4'-bis(3-amino-phenoxy)biphenyl, 1-[4-(3-aminophenoxy)phenyl]-1,3,3-trimethyl-6-(3-aminophenoxy)indan, 6,6'-bis(3-aminophenoxy)3,3,3',3'-tetramethyl-1,1'spirobiindan, and methyl substituted 2,2'-bis[4-(3-aminophenoxy)phenyl]propane.Type: GrantFiled: February 21, 1986Date of Patent: December 31, 1991Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Yukihiro Yoshikawa, Keizaburo Yamaguchi, Kenichi Sugimoto, Yoshimitsu Tanabe, Akihiro Yamaguchi
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Patent number: 5068436Abstract: A method for inhibiting dehalogenation of fluorinated and chlorinated benzenoid nitro compounds during catalytic hydrogenation to make the corresponding substituted anilines by conducting the hydrogenation reaction in the presence of an acidic catalytic medium.Type: GrantFiled: March 10, 1989Date of Patent: November 26, 1991Assignee: E. I. du Pont de Nemours and CompanyInventor: Donald D. May
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Patent number: 5068437Abstract: 2-(p-chlorophenoxy)aniline is prepared in a process which provides improved yields and reduction of key impurities. A solution comprising 2-(p-chlorophenoxy)nitrobenzene, o-dichlorobenzene, and a platinum catalyst is prepared followed by the addition thereto of hydrazine hydrate in water. The temperature is maintained at 80.degree. C. to 110.degree. C. during the addition and until completion of the reaction. The reaction mixture is then cooled to 20.degree. C. to 40.degree. C. and filtration, washing, and distillation workup steps follow.Type: GrantFiled: June 24, 1987Date of Patent: November 26, 1991Assignee: American Cyanamid CompanyInventors: John Kazan, James J. Kelly
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Patent number: 5041671Abstract: Process for the preparation of 4-chloro-2,5-dimethoxyaniline by catalytic reduction of 4-chloro-2,5-dimethoxynitrobenzene with hydrogen in the liquid phase at an elevated temperature and elevated pressure, which comprises carrying out the reduction at temperatures from about 80.degree. to about 110.degree. C. and under a pressure of about 5 to 50 atmospheres gauge in an aromatic solvent in the presence of a modified platinum-on-carbon catalyst in the presence of about 0.01 to about 0.2 mole of a compound which gives a pH of 8 to 10 in aqueous solution, and in the presence of about 0.1 to about 1.0% by weight of an aliphatic, open-chain, primary, secondary or tertiary amine or a cyclic amine, in each case relative to the amount in moles and weight, respectively, of 4-chloro-2,5-dimethoxynitrobenzene employed.Type: GrantFiled: June 21, 1989Date of Patent: August 20, 1991Assignee: Hoechst AktiengesellschaftInventors: Klaus Warning, Kurt Habig
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Patent number: 5041672Abstract: A process for producing p-phenylenediamine or a derivative thereof which comprises reducing p-nitroaniline or a derivative thereof by hydrazine in the presence of an aromatic quinone compound or an aromatic dihydroxy compound.Type: GrantFiled: October 16, 1990Date of Patent: August 20, 1991Assignee: Nippon Kayaku Kabushiki KaishaInventor: Tsukasa Ishikura
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Patent number: 5030761Abstract: A compound of the formula: ##STR1## wherein X is a chlorine atom or a bromine atom, which is useful as a herbicide.Type: GrantFiled: November 21, 1983Date of Patent: July 9, 1991Assignee: Sumitomo Chemical Company, LimitedInventors: Eiki Nagano, Shunich Hashimoto, Ryo Yoshida, Hiromichi Oshio, Katsuzo Kamoshita
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Patent number: 5008456Abstract: Diamino compounds, dinitro compounds, diol compounds and a process for preparing the diamino compounds which are useful as materials of poly-imide compounds for obtaining aligning films having high pretilt angles in liquid crystal display elements are provided.The diamino compounds are represented by the general formula: ##STR1## wherein R.sub.1 -R.sub.6 are a hydrogen atom or an alkyl group having 1 to 22 carbon atoms, respectively, and R.sub.7 -R.sub.12 are a hydrogen atom, an alkyl group having 1 to 3 carbon atoms, F or Cl respectively.Type: GrantFiled: November 8, 1989Date of Patent: April 16, 1991Assignee: Chisso CorporationInventors: Shizuo Murata, Minoru Nakayama, Kenji Furukawa, Ryuji Kobayashi
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Patent number: 5001265Abstract: An aminophenolic compound can be synthesized by contacting a halo-nitro-phenolic compound, such as 2-chloro-4,6-dinitrorescorcinol, with a hydrogenating agent, such as hydrogen, and a catalyst, such as palladium-on-carbon, in an aqueous solution in the presence of an acid such as phosphoric acid.Type: GrantFiled: July 28, 1989Date of Patent: March 19, 1991Assignee: The Dow Chemical CompanyInventors: Ming-Biann Liu, Luke R. Kleiss
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Patent number: 4994576Abstract: This invention relates to a method for reducing a nitro group substituent on an aromatic compound to an amino group and is characterized by treatment of the compound in the presence of iron or zinc and a halogen-containing aliphatic carboxylic acid.Type: GrantFiled: May 30, 1989Date of Patent: February 19, 1991Assignee: Eastman Kodak CompanyInventors: Paul R. Buckland, Robert N. Gourley
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Patent number: 4990670Abstract: Disclosed is a method of making 1,1'-oxybis (3-nitro-5-trifluoromethyl)-benzene by heating a nitro benzofluoride compound having the formula ##STR1## where "X" is selected from the group consisting of NO.sub.2, Cl, and F, with an alkali metal fluoride selected from the group consisting of potassium fluoride, cesium fluoride, and mixtures thereof, in an organic solvent in the presence of water. The corresponding diamine, 5,5'-oxybis (3-trifluoromethyl)-benzamine, can be prepared by reducing the benzene compound.Type: GrantFiled: August 17, 1989Date of Patent: February 5, 1991Assignee: Occidental Chemical CorporationInventors: Jeffrey S. Stults, Henry C. Lin
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Patent number: 4990663Abstract: This invention relates to a process for the hydrogenation of halogenated aromatic nitro compounds to the corresponding halogenated amines using a platinum catalyst in the presence of certain aminoalkyl ethers or alkanolamines. It relates in addition to halogenated aromatic amines containing an amount of such aminoalkyl ether or alkanolamine effective to stabilize said halogenated aromatic amine. The storage stabilizers and dehalogenation inhibitors contain a total of 2 to 6 carbon atoms and can be represented by the formula:R.sup.1 --(R.sup.2)--N--(CH.sub.2).sub.n --O--R.sup.3wherein R.sup.1 and R.sup.2 may be the same or different --H or --CH.sub.2 CH.sub.2 OH, n is an integer from 2 to 3, and R.sup.3 is either --H or --CH.sub.3.Type: GrantFiled: May 15, 1989Date of Patent: February 5, 1991Assignee: E. I. Du POnt de Nemours and CompanyInventors: Yu-Wei Chang, Robert L. Seagraves
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Patent number: 4960936Abstract: The catalytic hydrogenation of halogenated nitro aromatics using Raney nickel in the presence of a formamidine salt as dehalogenation inhibitor affords halogenated aromatic primary amines in high yields and high chemical purity within short reaction times even at elevated temperatures.Type: GrantFiled: December 19, 1988Date of Patent: October 2, 1990Assignee: Ciba-Geigy CorporationInventors: Peter Baumeister, Wilfried Scherrer
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Patent number: 4929737Abstract: Disclosed is an improved process for the preparation of haloaromatic amines by the catalytic hydrogenation of halonitroaromatic compounds in the presence of a chromium-containing Raney cobalt catalyst. The catalyst gives good hydrogenation rates while minimizing formation of dehalogenated by-products.Type: GrantFiled: February 3, 1988Date of Patent: May 29, 1990Assignee: Eastman Kodak CompanyInventors: Carl M. Lentz, Edward T. Mullins, Charles L. Gibson
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Patent number: 4885388Abstract: New 2-methyl-4-fluoro-phenols and process for their preparation from 2-methyl-4-fluoro-phenol.Type: GrantFiled: September 12, 1988Date of Patent: December 5, 1989Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Reiner Fischer
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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: 4831193Abstract: This invention relates to a novel process for preparing 3-amino-2-methylbenzotrifluoride from benzotrifluoride. The process comprises nitrating benzotrifluoride to form 3-nitrobenzotrifluoride, reacting this compound with trimethyl sulphoxonium halide to form 3-nitro-2-methylbenzotrifluoride and reducing the nitro group to an amino group.Type: GrantFiled: June 19, 1987Date of Patent: May 16, 1989Assignee: Schering CorporationInventors: Joseph F. Lamendola, Dhiru Vashi, Robert G. Tyson
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Patent number: 4760187Abstract: A process for reducing chloronitrobenzenes to the corresponding chloroanilines using a combination ruthenium-platinum catalyst is disclosed. The ratio of ruthenium to platinum in the catalyst is from 75:1 to 30:1. The pressure used is from 200 to 800 psi with from 400 to 600 psi being the preferred range. The temperature used is from 70.degree. to 160.degree. C. with from 110.degree. to 150.degree. C. being the preferred range.Type: GrantFiled: June 17, 1987Date of Patent: July 26, 1988Assignee: E. I. Du Pont de Nemours and CompanyInventor: John R. Kosak
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Patent number: 4749813Abstract: 4-Alkyl-2-trifluoromethylanilines, in particular the 4-isopropyl derivative, are starting materials for preparing valuable azo dyestuffs. While the nonionic dyestuff types can preferably be used in transfer printing synthetic hydrophobic fibre materials, the sulpho-containing dyestuffs--in particular those based on "gamma acid"--are suitable for dyeing polyamides.Type: GrantFiled: December 30, 1982Date of Patent: June 7, 1988Assignee: Bayer AktiengesellschaftInventors: Albrecht Marhold, Gerhard Wolfrum
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Patent number: 4625062Abstract: 4-Alkoxyanilines are obtained industrially advantageously by catalytically hydrogenating a nitrobenzene in the presence of a noble metal catalyst in a mixed solvent containing a lower aliphatic alcohol, sulfuric acid, and water or a lower aliphatic carboxylic acid or both to induce hydrogenation and a Bamberger-type rearrangement reaction. The mixed solvent contains at least 10 moles, preferably 30 to 60 moles, of the lower aliphatic alcohol per mole of the nitrobenzene, 1 to 10 moles, preferably 2 to 7 moles, of sulfuric acid per mole of the nitrobenzene, and 2 to 30% by weight, preferably 3 to 10% by weight, of water, the lower aliphatic carboxylic acid or both.Type: GrantFiled: November 27, 1984Date of Patent: November 25, 1986Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Teruyuki Nagata, Akihiro Tamaki, Hiroki Ohnishi, Hideki Mizuta
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Patent number: 4590263Abstract: Novel diazonium salts which possess excellent photo speed, good thermal stability, exceptional resistance to discoloration in the D.sub.min areas, rapid development, and allow a wide range of azo dye colors are provided. The diazonium salts are of the following formula: ##STR1## wherein R.sub.1 is tertiary butyl or tertiary amyl; Y is hydrogen, alkyl, hydroxyalkyl, cyanoalkyl, cycloalkyl, aralkyl, alkoxy, aryloxy, aralkoxy, aralkylthio, arylthio, alkylthio, halogen, allyl, allyloxy, allylthio, cyanoalkoxy, hydroxyalkoxy, methoxyalkoxy, trifluoroalkyl, alkylacetylamino, morpholino, or dialkyl carbonamido;R.sub.2 and R.sub.3 are the same or different, and are alkyl, aralkyl, allyl, cyanoalkyl, hydroxyalkyl, hydrogen, acyl, cycloalkyl, beta-chloroalkyl, branched alkyl, or a structure wherein R.sub.2 and R.sub.3 may be linked together to form a heterocyclic structure; andX is an anion.Type: GrantFiled: September 30, 1982Date of Patent: May 20, 1986Assignee: James River Graphics, Inc.Inventors: Robert C. Desjarlais, Everett W. Bennett
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Patent number: 4582935Abstract: Disclosing a process for making meta-aminobenzotrifluoride comprising:reacting meta-nitrobenzotrichloride with hydrogen fluoride in the presence of ammonium ions under a pressure of at least about 35 psig and at a temperature of at least about 55.degree. C. for sufficient time in the presence of water and a metal catalyst to form meta-aminobenzotrifluoride, wherein the amount of water added is at least one mole percent of the meta-nitrobenzotrichloride.Type: GrantFiled: December 21, 1984Date of Patent: April 15, 1986Assignee: Olin CorporationInventor: Max M. Boudakian
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Patent number: 4535154Abstract: A method for the reduction of nitrogen compounds containing an N--N or N.dbd.N bond, which are soluble in water or lower alcohols, particularly nitrosamines, hydrazines, nitramines, azo- and azoxy-compounds, to the corresponding amines; comprising contacting the nitrogen compounds with a hydroxide solution and a nickel-aluminum alloy in the absence of a hydrogen atmosphere, at room temperature and at atmospheric pressure, for a sufficient time to produce the corresponding amine in a single step.Type: GrantFiled: July 13, 1983Date of Patent: August 13, 1985Assignee: United States of AmericaInventors: Larry K. Keefer, George Lunn
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Patent number: 4532350Abstract: Process for the selective preparation of metachloroanilines.It is carried out by the hydrodechlorination of polychloroanilines or polychloronitrobenzenes with hydrogen, in the liquid phase and in an acid medium, under the action of heat and under pressure, in the presence of a noble metal used in association with a heavy metal.These meta-chloroanilines are intermediates especially for active plant-protection substances.Type: GrantFiled: December 30, 1982Date of Patent: July 30, 1985Assignee: Rhone-Poulenc AgrochimieInventors: Georges Cordier, Pierre Fouilloux
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Substituted benzotrifluoride compounds as chemical intermediates and a process for their preparation
Patent number: 4532353Abstract: This invention pertains to two substituted benzotrifluoride compounds useful as chemical intermediates for a new class of 2-haloacetanilide herbicides and a process for making these intermediates. The process generally involves nitration and reduction of the corresponding benzotrifluoride compound.Type: GrantFiled: June 16, 1983Date of Patent: July 30, 1985Assignee: Monsanto Co.Inventors: John P. Chupp, Audrey Y. Ku, Thomas E. Neumann, Thomas E. Nickson -
Patent number: 4500736Abstract: There is disclosed a process for the conversion of 3-trichlorovinylnitrobenzene to 3-trichlorovinylaniline by catalytic reduction in an alcoholic acidic medium, using a supported palladium catalyst in a hydrogen atmosphere. The process is carried out without any appreciable hydrogenolysis of the trichlorovinyl group.Type: GrantFiled: June 28, 1983Date of Patent: February 19, 1985Assignee: Merck & Co., Inc.Inventor: Jean M. Wyvratt
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Patent number: 4469890Abstract: This invention relates to a process for the preparation of ortho-aminobenzotrifluoride (OABT) from benzotrifluoride (BTF). The process provides an overall route employing non-isolation of intermediates which can be run smoothly and which results in the preparation of OABT in high yields with less contamination. This process includes a catalytic halogenation step in which BTF is converted to meta-halo BTF and other mono and di-halo isomers of BTF followed by nitration in the same reaction vessel under conditions which do not favor nitration of the di-halo isomers of BTF to produce a mixture which predominates in 5-halo-2-nitro BTF. In the final step the 5-halo-2-nitro BTF present is reduced and hydrodehalogenated with H.sub.2 in the presence of a catalyst to form OABT. Recyclable BTF is also obtained from the final reaction.Type: GrantFiled: September 7, 1983Date of Patent: September 4, 1984Assignee: Monsanto CompanyInventors: John P. Chupp, Thomas E. Neumann, Michael J. Miller
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Patent number: 4452981Abstract: A condensed phenylurazol of the formula: ##STR1## wherein X is a chlorine atom or a bromine atom, Y and Z are each an oxygen atom or a sulfur atom and R is a C.sub.1 -C.sub.3 alkyl group, an allyl group or a propargyl group and n is an integer of 4 or 5, which is useful as a herbicide.Type: GrantFiled: September 15, 1982Date of Patent: June 5, 1984Assignee: Sumitomo Chemical Company, LimitedInventors: Eiki Nagano, Shunichi Hashimoto, Ryo Yoshida, Hiroshi Matsumoto, Katsuzo Kamoshita
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Patent number: 4426538Abstract: The invention relates to a process for the preparation of optionally p-chlorine-substituted 2,6-diaminotoluene, which is characterized in that 3,4-dichlorotoluene is dinitrated in the presence of an inert, water-immiscible, organic solvent and/or diluent at temperatures of -10.degree. to +100.degree. C. and is subsequently reduced, optionally after intermediate isolation of the dinitro compound, in the presence of an inert organic solvent and/or diluent and/or of water, with partial or complete splitting-off of the chlorine atoms, to give the diamino compound.2,6-Diaminotoluenes are valuable intermediates for the preparation of diisocyanates and polyurethanes; the 2,6-diaminotoluene is furthermore used for the preparation of dyestuffs and antioxidants.Type: GrantFiled: January 21, 1982Date of Patent: January 17, 1984Assignee: Bayer AktiengesellschaftInventors: Klaus-Peter Heise, Ernst Schneider, Karlfried Wedemeyer
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Patent number: 4418213Abstract: Process for the selective preparation of meta-chloroanilines.It is carried out by the hydrodechlorination of polychloroanilines or polychloronitrobenzenes with hydrogen, in the liquid phase, under the action of heat, at atmospheric pressure or under pressure, in the presence of a noble metal, in an anhydrous organic medium and in the presence of a Lewis acid.These meta-chloroanilines are intermediates especially for active plant-protection substances.Type: GrantFiled: July 14, 1981Date of Patent: November 29, 1983Assignee: Rhone-Poulenc AgrochimieInventors: Georges Cordier, Pierre Fouilloux