And Nitro Patents (Class 564/406)
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Patent number: 10421709Abstract: Production of 2,4,6-triamino-1,3,5-trinitrobenzene (TATB) through a safer, less harmful process while yielding a superior product is disclosed. The biphasic production process may include mixing a solution of 1,3,5-trichloro-2,4,6-trinitrobenzene (TCTNB) and a surfactant into a solvent in a sealed, heated vessel such that TATB is formed in a mixture. The biphasic production process may also include pressurizing the vessel with gaseous ammonia such that aqueous TATB is formed and separating the TATB from the mixture.Type: GrantFiled: April 30, 2019Date of Patent: September 24, 2019Assignee: Triad National Security, LLCInventors: Philip Leonard, Michael Bange
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Publication number: 20140336415Abstract: An inexpensive and convenient production method of diphenylamine compounds is provided, that can solve problems in the conventional technology such as decrease in reactivity, restriction of substituents, high temperature, high pressure, by-products or the like. Further, diphenylamine compounds useful as intermediates of medicine and agricultural chemicals are provided. Diphenylamine compounds are produced, represented by general formula (3): which is characterized by reacting aniline compounds represented by general formula (2): under the presence of base and ethers solvent, with 2,6-dichloronitrobenzene compound represented by general formula (1): and a diphenylamine compound represented by general formula (3).Type: ApplicationFiled: December 5, 2012Publication date: November 13, 2014Inventors: Minoru Ito, Akiko Ikumi
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Publication number: 20130158296Abstract: A process is provided for the preparation of 1-amino-3-halo-4,6-dinitrobenzene and related compounds by monoamination of dihalodinitrobenzenes by ammonia in the presence of solvent and water. Using glycol as a solvent for the dihalodinitrobenzene and feeding ammonia at a rate at which it is consumed allows for the synthesis of high purity product, such as 1-amino-3-chloro-4,6-dinitrobenzene, at high yields.Type: ApplicationFiled: December 21, 2010Publication date: June 20, 2013Applicant: E I DU PONT DE NEMOURS AND COMPANYInventors: Annalisa Hargis, Joachim C. Ritter
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Patent number: 8404898Abstract: An integrated process is provided for preparing 2,3,5,6-tetraminotoluene and salts thereof starting with nitration of 2,6-dihalotoluene. The process design eliminates costly intermediate drying and recrystallization steps. Handling of solid materials with possible skin sensitizing properties and toxicity is avoided, thereby eliminating human and environmental exposure.Type: GrantFiled: December 10, 2009Date of Patent: March 26, 2013Assignee: E I du Pont de Nemours and CompanyInventors: Joachim C. Ritter, Rajiv Dhawan
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Patent number: 7767856Abstract: Improved methods for making hole transport molecules (HTMs) that are incorporated into imaging members, such as layered photoreceptor devices, to increase the photoreceptor's “hole mobility,” or its ability to move charge, across its charge transport layer (CTL). Embodiments pertain to a continuous process for making N,N-diphenyl-4-biphenylamine and a system for performing the same.Type: GrantFiled: January 25, 2007Date of Patent: August 3, 2010Assignee: Xerox CorporationInventors: Timothy P. Bender, Emily L. Moore, Jennifer A. Coggan, Frank Ping-Hay Lee, David Borbely
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Publication number: 20100160678Abstract: An improved process is provided for the preparation of 2,6-diamino-3,5-dinitrotoluene by amination of 2,6-dichloro-3,5-dinitrotoluene. The presence of water unexpectedly results in a highly pure product, free of glycol ether impurities. This product can be used to make highly pure 2,3,5,6-tetraaminotoluene, which in turn can be used to make high molecular weight polybenzimidazoles for high strength fibers.Type: ApplicationFiled: December 10, 2009Publication date: June 24, 2010Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: RAJIV DHAWAN, Joachim C. Ritter
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Publication number: 20100160685Abstract: An integrated process is provided for preparing 2,3,5,6-tetraminotoluene and salts thereof starting with nitration of 2,6-dihalotoluene. The process design eliminates costly intermediate drying and recrystallization steps. Handling of solid materials with possible skin sensitizing properties and toxicity is avoided, thereby eliminating human and environmental exposure.Type: ApplicationFiled: December 10, 2009Publication date: June 24, 2010Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: JOACHIM C. RITTER, Rajiv Dhawan
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Patent number: 7408085Abstract: A process for forming a tetra(aryl)-biphenyldiamine compound, including reacting a dibromobiphenyl compound and a diarylamine compound in the presence of a palladium ligated catalyst and a base.Type: GrantFiled: November 28, 2006Date of Patent: August 5, 2008Assignee: Xerox CorporationInventors: Timothy P. Bender, Jennifer A. Coggan, Gregory McGuire, Leanne Dawn Murphy, Alan Edward John Toth
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Patent number: 7402700Abstract: A process for forming a diarylamine compound, including reacting an aniline and an arylbromide in the presence of a palladium ligated catalyst and a base.Type: GrantFiled: November 28, 2006Date of Patent: July 22, 2008Assignee: Xerox CorporationInventors: Timothy P. Bender, Jennifer A. Coggan
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Patent number: 7381844Abstract: A hydrogenation process of chloronitrobenzene. The hydrogenation process comprises the steps of producing a nanosized boron-containing nickel catalyst, wherein a ratio of the amount of the boron atom to the amount of the nickel atom in the nanosized boron-containing nickel catalyst is of about 0.1-0.9. Then, the nanosized boron-containing nickel catalyst is placed into a reactor with a chloronitrobenzene an alcohol solvent having carbon number less than four per molecule and a hydrogenation process is performed to hydrogenating the chloronitrobenzene in hydrogen with a reaction pressure of about 5-40 atm and a reaction temperature of about 40-150° C.Type: GrantFiled: August 4, 2006Date of Patent: June 3, 2008Assignee: National Central UniversityInventors: Yu-Chang Liu, Chung-Yin Huang, Yu-Wen Chen
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Patent number: 7332630Abstract: A process for the preparation of a tertiary arylamine compound, comprising reacting an arylhalide, such as an arylbromide, and an arylamine in an alkylene glycol compound in the presence of a catalyst.Type: GrantFiled: November 16, 2005Date of Patent: February 19, 2008Assignee: Xerox CorporationInventors: Jennifer A. Coggan, Timothy P. Bender
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Patent number: 6946577Abstract: The present invention relates to a process for the production of aminodiphenyl-amines, such as 4-aminodiphenylamine (4-ADPA), by reacting nitrohalogenated benzenes with anilines in the presence of a base as well as a copper-phosphorus complex, followed by hydrogenation of the intermediately formed nitrodiphenyl-amines.Type: GrantFiled: January 2, 2004Date of Patent: September 20, 2005Assignee: Bayer AktiengesellschaftInventors: Adolf Sicheneder, Ulrich Scholz, Joachim Haider
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Patent number: 6888029Abstract: The present invention relates to a process for the preparation of N-aryl amine and N-aryl amide compounds. Generally, the process of the present invention involves reacting a compound having a primary or secondary amino or amido group with an arylating compound, in the presence of a weak base and a transition metal catalyst, under reaction conditions effective to form an N-aryl amine or N-aryl amide compound, the transition metal catalyst comprising a Group 8 metal, e.g., Ni, Pd, or Pt, and at least one carbene-containing ligand. Typically, the transition metal catalyst is formed in a preceding step from the conjugate acid form of the carbene ligand, a stoichiometric amount of a strong base, and a Group 8 metal atom or ion.Type: GrantFiled: January 22, 2003Date of Patent: May 3, 2005Assignee: Massachusetts Institute of TechnologyInventors: Stephen L. Buchwald, Joseph M. Fox
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Patent number: 6815562Abstract: The present invention relates to a process for the preparation of nitrodiphenylamines by reaction of nitrohalogens with anilines, a base and a catalyst, and to a process for the preparation of aminodiphenylamine by hydrogenation of the nitrodiphenylamine intermediately prepared.Type: GrantFiled: January 2, 2004Date of Patent: November 9, 2004Assignee: Bayer AktiengesellschaftInventors: Klaus Kunz, Joachim Haider, Dirk Ganzer, Ulrich Scholz, Adolf Sicheneder
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Patent number: 6547899Abstract: A method for producing fine-grained triamino-trinitrobenzene (TATB) powders having improved detonation-spreading performance and hence increased shock sensitivity when compared with that for ultrafine TATB is described. A single-step, sonochemical amination of trichloro-trinitrobenzene using ammonium hydroxide solution in a sealed vessel yields TATB having approximately 6 &mgr;m median particle diameter and increased shock sensitivity.Type: GrantFiled: March 15, 2001Date of Patent: April 15, 2003Assignee: The Regents of the University of CaliforniaInventors: Kien-Yin Lee, James E. Kennedy
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Patent number: 6476265Abstract: In a process for preparing aryl oligoamines, an amine is reacted with an activated aromatic and a base in a temperature range from 0 to 150° C. in the presence of a palladium component and a phosphine ligand. The aryl oligoamines are obtained simply and in good yields.Type: GrantFiled: May 10, 2000Date of Patent: November 5, 2002Assignee: Covion Organic Semiconductors GmbHInventors: Hubert Spreitzer, Willi Kreuder, Heinrich Becker, Ute Neumann
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Patent number: 6316673Abstract: The present invention relates to the production of aminodiphenyl-amines resulting in good yields and high purity levels when aromatic amines are reacted with nitrohalobenzenes in the presence of a palladium catalyst and a base and the product thus obtained is subsequently hydrogenated with hydrogen.Type: GrantFiled: February 2, 2001Date of Patent: November 13, 2001Assignee: Bayer AktiengesellschaftInventors: Henry Giera, Torsten Pohl, Uwe Hugger, Adolf Sicheneder, Fred Schuhmacher, Adolf Brill
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Publication number: 20010012906Abstract: The present invention relates to the production of aminodiphenyl-amines resulting in good yields and high purity levels when aromatic amines are reacted with nitrohalobenzenes in the presence of a palladium catalyst and a base and the product thus obtained is subsequently hydrogenated with hydrogen.Type: ApplicationFiled: February 2, 2001Publication date: August 9, 2001Inventors: Henry Giera, Torsten Pohl, Uwe Hugger, Adolf Sicheneder, Fred Schuhmacher, Adolf Brill
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Patent number: 6235937Abstract: The invention relates to a process for the preparation of nitrodiphenylamines by reaction of nitrohalogenobenzenes with aromatic amines in the presence of a palladium catalyst and a base, the base being ground and/or dried before its use.Type: GrantFiled: August 31, 2000Date of Patent: May 22, 2001Assignee: Bayer AktiengesellschaftInventors: Henry Giera, Walter Lange, Torsten Pohl, Adolf Sicheneder, Christoph Schild
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Patent number: 6137010Abstract: This invention relates to a process for preparing 4-nitrodiphenylamine and 4-nitrosodiphenylamine to be used for 4-aminodiphenylamine as an intermediate of antiozonant, wherein carbanilide is reacted with nitrobenzene in the presence of an appropriate base, while simultaneously adding aniline to the mixture so as to regenerate some amounts of carbanilide as a starting material.According to this invention, 4-nitrodiphenylamine and 4-nitrosodiphenylamine can be prepared in a higher selectivity and conversion rate via a continuous reaction by recycling carbanilide, a starting material, while adding a certain amount of aniline during the process. Further, the amount of waste water can be significantly reduced compared to the conventional method without any corrosive materials harmful to the environment.Type: GrantFiled: February 10, 2000Date of Patent: October 24, 2000Assignee: Korea Kumho Petrochemical Co., Ltd.Inventors: Young J. Joo, Jin Eok Kim, Jeong Im Won, Kum Ui Hwang
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Patent number: 6077973Abstract: Anilines which contain fluorine in a side chain are prepared by reacting chlorinated aromatic compounds with ammonia in the presence of a catalyst and optionally water at 200 to 280.degree. C. Some of the trifluoromethoxyanilines which may be prepared in this way are new compounds.Type: GrantFiled: November 30, 1992Date of Patent: June 20, 2000Assignee: Bayer AktiengesellschaftInventor: Albrecht Marhold
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Patent number: 5728881Abstract: A process is provided for preparing 2,6-dinitro-N,N-dipropyl-4-(trifluoromethyl)benzenamine from 4-chlorotrifluoromethylbenzene. The process includes a two stage nitration and an amination step. Ethylene dichloride is utilized as a diluent and solvent in the nitration steps. Spent acid from the first nitration is reconstituted with sulfur trioxide for use in the second nitration. Spent acid from the second nitration is used directly in the first nitration and evaporation is used to remove nitrosoamines from the final trifluralin product.Type: GrantFiled: March 5, 1997Date of Patent: March 17, 1998Assignee: SRM Chemical, Ltd. Co.Inventors: Stefan Kwiatkowski, Krzysztof Pupek, Miroslaw J. Golinski, Paul D. Smith, Lowell J. Lawrence
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Patent number: 5684203Abstract: Nitroaromatics can be aminated using urea in the presence of bases and oxygen.Type: GrantFiled: July 26, 1995Date of Patent: November 4, 1997Assignee: Bayer AktiengesellschaftInventor: Manfred Jautelat
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Patent number: 5672754Abstract: The invention relates to a process for the preparation of compounds of formula ##STR1## wherein R.sub.1 is hydrogen, C.sub.1 -C.sub.4 alkyl or sulfo, and R.sub.2 is hydrogen or C.sub.1 -C.sub.4 alkyl, which process comprises reacting a compound of formula ##STR2## wherein Hal is halogen and R.sub.1 has the meaning given above, with a compound of formula ##STR3## wherein Y is a saponifiable group and R.sub.2 has the meaning given above, to give the compound of formula ##STR4## wherein R.sub.1, R.sub.2 and Y have the meanings given above, and saponifying the compound of formula (4) to give the compound of formula (1).The compounds of formula (1) are suitable for the synthesis of dyes.Type: GrantFiled: September 15, 1995Date of Patent: September 30, 1997Assignee: Ciba-Geigy CorporationInventor: Guido Jordine
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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: 5466871Abstract: A process for preparing a nitroaniline derivative comprising a step of reacting an aromatic nitro compound with an O-alkylhydroxylamine or a salt thereof in the presence of a base and optionally a metallic catalyst, which process is industrially advantageous since it provides the nitroaniline derivative from the aromatic nitro compound in a high yield in one step, and the aminating agent used can be obtained from hydroxylamine at a relatively low cost.Type: GrantFiled: July 11, 1994Date of Patent: November 14, 1995Assignee: Sumitomo Chemical Company, LimitedInventor: Shinzo Seko
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Patent number: 5434308Abstract: A method of dehydrogenating 3-amino-2-cyclohexene-1-one with a supported palladium or palladium-platinum catalyst in a solvent in the presence of base to produce 3-aminophenol and its use directly without purification to produce 3,4'-oxydianiline.Type: GrantFiled: January 18, 1994Date of Patent: July 18, 1995Assignee: E. I. Du Pont de Nemours and CompanyInventor: Stephen E. Jacobson
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Patent number: 5414128Abstract: The present invention relates to a process for the preparation of compounds of the general formula I ##STR1## by reaction of compounds of the general formula II ##STR2## with amines of the general formula III ##STR3## wherein R.sup.1 and R.sup.2 independently of one another denote hydrogen, (C.sub.1 -C.sub.4)-alkyl, C.sub.1 -C.sub.4)-hydroxyalkyl or (C.sub.5 -C.sub.6)-cycloalkyl, or, together with the nitrogen atom carrying them, form (C.sub.4 -C.sub.6)-heterocyclyl and R.sup.3 and R.sup.4 independently of one another denote hydrogen, (C.sub.1 -C.sub.4)-alkyl, (C.sub.1 -C.sub.4)-hydroxyalkyl, (C.sub.1 -C.sub.2)-alkylcarbonyl or tosyl.Type: GrantFiled: December 3, 1992Date of Patent: May 9, 1995Assignee: Cassella AGInventors: Willi Steckelberg, Rolf Muller, Peter Koch
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Patent number: 5405999Abstract: A process for the preparation of the unsaturated dinitroaniline, ethalfluralin having a level of nitrosamines lower than 0.5 ppm and essentially free from the compound of addition of halogenhydric acid on the methallyl double bond, by treatment with aqueous halogenhydric acid, wherein crude ethalfluralin is treated under agitation with an aqueous solution of hydrobromic acid in the presence of sulfamic acid and a sulfur compound selected from the group consisting of bisulfites, metabisulfites, hydrosulfites, sulfurous acid and gaseous sulfur dioxide.Type: GrantFiled: November 29, 1993Date of Patent: April 11, 1995Assignee: Finchimica S.p.A.Inventor: Graziello Donadello
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Patent number: 5210303Abstract: A process for producing a benzylamine which comprises reacting a benzyl halide with an aqueous ammonia solution in the presence of an aromatic aldehyde represented by the formula: ##STR1## wherein R represents a hydrogen atom, a halogen atom or a lower alkyl group, and n is 1 or 2, separating an oily substance from the reaction mixture, and treating the oily substance with a mineral acid.Type: GrantFiled: April 18, 1991Date of Patent: May 11, 1993Assignee: Ihara Chemical Industry Co., Ltd.Inventor: Tatsuo Sugiyama
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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: 5117064Abstract: A method for synthesizing an aromatic amine, an aromatic alcohol or an aromatic thiol by an aromatic nucleophilic substitution reaction is disclosed, which comprises reacting a compound represented by formula (I): ##STR1## wherein Q.sup.1 represents an aromatic ring; EWG represents a group having a positive Hammett's .sigma..sub.p value; m represents an integer of 1 to 5; n represents an integer of 1 to 3; and X represents a group represented by formula (III): ##STR2## wherein R.sup.4 represents hydrogen atom, an aryl group or an alkyl group; Q.sup.2 represents an atomic group for forming an aromatic ring; and Z.sup.1 and Z.sup.2 each represents an oxygen atom or a sulfur atom with a nucleophilic reagent represented by formula (II):M--Y (II)wherein M represents a hydrogen atom, a metal atom or an ammonium; Y represents a --NHR.sup.1 group, an --OR.sup.1 group, or a --SR.sup.1 group; R.sup.1 represents a hydrogen atom, an alkyl group, an aryl group, a residue of a heterocyclic ring, a --NR.sup.2 R.sup.Type: GrantFiled: January 25, 1991Date of Patent: May 26, 1992Assignee: Fuji Photo Film Co., Ltd.Inventors: Takayuki Ito, Koki Nakamura
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Patent number: 4997987Abstract: Preparation of 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) from 3,5-dichloroanisole. Nitration of 3,5-dichloroanisole under relatively mild conditions gave 3,5-dichloro-2,4,6-trinitroanisole in high yield and purity. Ammonolysis of this latter compound gave the desired TATB. Another route to TATB was through the treatment of the 3,5-dichloro-2,4,6-trinitroanisole with thionyl chloride and dimethylformamide to yield 1,3,5-trichloro-2,4,6-trinitrobenzene. Ammonolysis of this product produced TATB.Type: GrantFiled: June 8, 1990Date of Patent: March 5, 1991Assignee: The United States of America as represented by the United States Department of EnergyInventors: Donald G. Ott, Theodore M. Benziger
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Patent number: 4990673Abstract: Process for the preparation of 4,4'-dinitrodiphenylamine which comprises reacting 1 mole of 4-halonitrobenzene with about 1 to about 3 moles of an alkali metal cyanate in the presence of about 0.5 to about 5 moles of water in dimethylsulfoxide at temperatures of about 150.degree. to about 170.degree. C.Type: GrantFiled: November 16, 1989Date of Patent: February 5, 1991Assignee: Hoechst AktiengesellschaftInventors: Wolfgang Tronich, Peter Hess
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Patent number: 4952733Abstract: Preparation of 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) from 3,5-dichloroanisole. Nitration of 3,5-dichloroanisole under relatively mild conditions gave 3,5-dichloro-2,4,6-trinitroanisole in high yield and purity. Ammonolysis of this latter compound gave the desired TATB. Another route to TATB was through the treatment of the 3,5-dichloro-2,4,6-trinitroanisole with thionyl chloride and dimethylformamide to yield 1,3,5-trichloro-2,4,6-trinitrobenzene. Ammonolysis of this product produced TATB.Type: GrantFiled: December 21, 1988Date of Patent: August 28, 1990Assignee: The United States of America as represented by the United States Department of EnergyInventors: Donald G. Ott, Theodore M. Benziger
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Patent number: 4910341Abstract: The present invention relates to a process for preparing a N,N'-disubstituted nitro-para-phenylenediamine (I) according to the following scheme: ##STR1## X denoting a halogen and R a lower alkyl, lower mono- or polyhydroxyalkyl, lower alkoxyalkyl or lower aminoalkyl group, in which the amino group can be mono- or disubstituted with a lower alkyl or lower mono- or polyhydroxyalkyl group, the nitrogen atom of said amino group being able to form part of a heterocyclic system.The invention also relates to the intermediate oxazolidones of formulae (II) and (III), and the new nitro-para-phenylenediamines in which R denotes a lower alkoxyalkyl, lower polyhydroxyalkyl or lower aminoalkyl group, as well as the dyeing compositions for keratinous fibres containing these new nitro-para-phenylenediamines.Type: GrantFiled: September 6, 1988Date of Patent: March 20, 1990Assignee: L'OrealInventors: Gerard Lang, Alex Junino
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Patent number: 4782185Abstract: With a far shorter reaction time, azeotropic distillation of the water in the condensation of 4-nitrohalogenobenzenes and primary aromatic amines or formyl derivatives thereof in the presence of potassium carbonate and, if appropriate, copper compounds can be dispensed with if the reaction is carried out in the presence of Al metal, Mg metal or Zn metal or mixtures or alloys of these metals.Type: GrantFiled: February 9, 1987Date of Patent: November 1, 1988Assignee: Bayer AktiengesellschaftInventor: Ernst W. Muller
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Patent number: 4771067Abstract: 4-nitrodiphenylamines may be produced by an improved process from 4-halo nitrobenzenes and primary aromatic amines in the presence of potassium carbonate and copper compounds, wherein(1) mono- and di-carboxylic acid amides or nitriles are added;(2) from 3 to 5 mol of amine are introduced per mol of halo nitrobenzene; and(3) from 1.2 to 2 mol of the amine are added prior to the reaction and the remainder during the reaction so that the molar excess of amine relative to halo nitrobenzene is always from 100 to 400%.Type: GrantFiled: August 26, 1987Date of Patent: September 13, 1988Assignee: Bayer AktiengesellschaftInventors: Chiraranjan Podder, Harro Schlesmann
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Patent number: 4683332Abstract: There is disclosed a process for the synthesis of para-nitrodiphenylamines via the Formanilide Process wherein the improvement is characterized in that a specific catalyst is utilized. More specifically, a zinc (II) compound (zinc in the plus two oxidation or valence state), is used as a catalyst in the preparation of para-nitrodiphenylamines via the formanilide process.Type: GrantFiled: May 20, 1985Date of Patent: July 28, 1987Assignee: The Goodyear Tire & Rubber CompanyInventor: Budd H. Sturm
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Patent number: 4670595Abstract: The reaction of 4-nitrohalogenbenzenes with primary aromatic amines in the presence of potassium carbonate and copper compounds to 4-nitrodiphenylamines gives better yield of purer products when synthetic polyamides are added.Type: GrantFiled: February 3, 1986Date of Patent: June 2, 1987Assignee: Bayer AktiengesellschaftInventors: Chiraranjan Podder, Harro Schlesmann
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Patent number: 4665233Abstract: An improved process for the preparation of 4-nitrodiphenylamines by the reaction of 4-nitrohalobenzenes with primary aromatic amines in the presence of potassium carbonate and copper compounds is characterized in that sulpholane dimethylsulphone, dimethylacetamide, diethylacetamide, tetramethylurea, tetraethylurea or mixtures thereof are used as solvents and 3 to 5 mol of amine are used per mol of halogenated nitrobenzene, from 1.2 to 2 mol of said amine being added before the beginning of the reaction and the remainder during the reaction at such a rate that the molar excess of unreacted amine over unreacted halogenated nitrobenzene is constantly at least 100%.Type: GrantFiled: November 18, 1985Date of Patent: May 12, 1987Assignee: Bayer AktiengesellschaftInventors: Chiraranjan Podder, Harro Schlesmann
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Patent number: 4665232Abstract: The reaction of 4-nitrohalobenzenes with primary aromatic amines in the presence of potassium carbonate and copper compounds to produce 4-nitrodiphenylamine results in products with improved purity and yield if (1) carbonic acid amides or their derivatives are added, (2) 3 to 5 mol of amine are used per mole of halonitrobenzene and (3) 1.2 to 2 mol of the amine are added before the beginning of the reaction and the remainder during the reaction at such a rate that the molar excessive amine over halonitrobenzene is always from 100 to 400%.Type: GrantFiled: January 9, 1986Date of Patent: May 12, 1987Assignee: Bayer AktiengesellschaftInventors: Chiraranjan Podder, Harro Schlesmann
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Patent number: 4614817Abstract: Nitrodiarylamines, useful as intermediates, are produced by combining a formyl derivative of an aromatic primary amine with a nitrohaloarene, at condensation temperature for forming nitrodiarylamine, and adding an alkoxide or cycloalkoxide of an alkali metal, excluding lithium.Type: GrantFiled: December 19, 1983Date of Patent: September 30, 1986Assignee: Monsanto CompanyInventors: Otto W. Maender, Helmut L. Merten
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Patent number: 4609759Abstract: This invention pertains to a process for producing 2,6 dinitroaniline derivates which are suited as intermediates for herbicides. The process involves the formation of a 1,2,6-trinitro-aromatic isomer and the subsequent nucleophilic displacement of the 1-nitrosubstituent with an amine. The reaction products can easily be separated from other organics by forming an amine salt and extracting with water.Type: GrantFiled: May 2, 1984Date of Patent: September 2, 1986Assignee: Air Products and Chemicals, Inc.Inventor: Richard V. C. Carr
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Patent number: 4521622Abstract: A process for producing an aromatic amine from an aromatic halide and ammonia, characterized by comprising the following steps (1), (2) and (3):step (1): reacting the aromatic halide with ammonia in the presence of water by using a catalyst comprising a copper compound as the main constituent,step (2): extracting the aromatic amine from the reaction mixture obtained in step (1) without depositing or separating the copper component contained in the reaction mixture, andstep (3): adding an alkali metal hydroxide and/or an alkaline earth metal hydroxide to the raffinate aqueous solution obtained by the extraction procedure in step (2) to deposit copper compounds and separating the same.This process is good in reaction efficiency and permits easy recovery of the catalyst.Type: GrantFiled: February 3, 1984Date of Patent: June 4, 1985Assignee: Japan Synthetic Rubber Co., Ltd.Inventors: Naoki Andoh, Shuetsu Fujiwara
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Patent number: 4481371Abstract: A method of forming a fine-grained species of the insensitive high explosive sym-triaminotrinitrobenzene (TATB) without grinding. In accordance with the method, 1,3,5-trichloro-2,4,6-trinitrobenzene (TCTNB) is aminated by reaction with gaseous ammonia in an emulsion of toluene in water. The ratio of water to toluene in the emulsion is selected so that toluene is the dispersed phase in the emulsion. The size of the dispersed TCTNB-containing toluene droplets determines the particle size of the resulting TATB. The emulsion is preferably formed with an emulsifier such as ammonium oleate, which may be generated in situ from oleic acid, and stabilized with a protective colloid such as polyvinyl alcohol.Type: GrantFiled: July 26, 1983Date of Patent: November 6, 1984Assignee: The United States of America as represented by the United States Department of EnergyInventor: Theodore M. Benziger
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Patent number: 4443630Abstract: 2-Amino-5-nitrotoluene is obtained in high yield by reacting 2-chloro-5-nitrotoluene with excess aqueous ammonia which has a concentration of at least 30% by weight. The product is used as a diazo component for preparing azo compounds.Type: GrantFiled: December 27, 1982Date of Patent: April 17, 1984Assignee: Hoechst AktiengesellschaftInventors: Theodor Papenfuhs, Rudiger Berthold
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Patent number: 4439622Abstract: A process for the manufacture of 1,3,5-triaminotrinitrobenzene having a large crystal size by aminating 1,3,5-trichlorotrinitrobenzene with an agent at atmospheric pressure at a temperature of at least about 160.degree. C. with an antioxidant added to the reaction mixture.Type: GrantFiled: January 18, 1982Date of Patent: March 27, 1984Assignee: Fraunhofer-Gesellschaft Zur Forderung Der Angewandten Forschung e. V.Inventors: Rolf Hansen, Walter Engel, Hiltmar Schubert
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Patent number: 4421694Abstract: The invention relates to a process for the preparation of nitroanilines by the reaction of chloronitrobenzenes with ammonia at elevated temperature and under elevated pressure, and in the presence of chlorinated aromatic hydrocarbons.Nitroanilines are important precursors and intermediate products for the preparation of dyestuffs, pharmaceuticals and plant protection agents.Type: GrantFiled: January 20, 1982Date of Patent: December 20, 1983Assignee: Bayer AktiengesellschaftInventors: Bruno Kruger, Adolf Winkler, Gunter Hentze
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Patent number: 4404400Abstract: The invention relates to a process for the preparation of 4-nitrodiphenylamines by the reaction of halogenonitrobenzenes with primary aromatic amines in the presence of copper or a copper compound, a neutralizing agent and a cyclic diaza compound.Type: GrantFiled: September 2, 1982Date of Patent: September 13, 1983Assignee: Bayer AktiengesellschaftInventors: Klaus-Peter Heise, Karlfried Wedemeyer