Preparing Directly By Nitration Patents (Class 564/411)
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Publication number: 20140371446Abstract: The disclosure is directed to: (a) phosphacycle ligands; (b) methods of using such phosphacycle ligands in bond forming reactions; and (c) methods of preparing phosphacycle ligands.Type: ApplicationFiled: August 25, 2014Publication date: December 18, 2014Applicant: AbbVie Inc.Inventors: Shashank Shekhar, Thaddeus S. Franczyk, David M. Barnes, Travis B. Dunn, Anthony R. Haight, Vincent S. Chan
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Publication number: 20140227792Abstract: Deuterium free, stable isotope labeled hallucinogens and/or stimulants containing a 2-phenylethylamine-based structural unit and containing at least three stable isotopes selected from the group consisting of 13C, 15N and 18O as free bases and as their salts; method of their preparation and their use in the chemical analysis, in particular forensic chemical analysis, and in metabolic studies.Type: ApplicationFiled: July 27, 2012Publication date: August 14, 2014Applicant: CHIRON A/SInventors: Jon Eigill Johansen, Huiling Liu, Morten Karlsen
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Patent number: 8729309Abstract: The invention relates to a process for the continuous production of nitrobenzene by nitration of benzene with a mixture of nitric acid and sulfuric acid under adiabatic conditions, in which unreacted benzene is separated from the crude product obtained after phase separation before washing thereof, using the adiabatic heat of reaction.Type: GrantFiled: July 26, 2011Date of Patent: May 20, 2014Assignee: Bayer Intellectual Property GmbHInventors: Thomas Knauf, Alexandre Racoes, Andreas Karl Rausch, Dietrich Wulf
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Patent number: 8642781Abstract: Aromatic compounds such as o-xylene are selectively nitrated by nitric acid in the presence of polyphosphoric acid and a large pore, acidic zeolite or a large pore, hydrophobic molecular sieve. This is an environmentally friendly, commercially viable, high conversion process for the selective nitration of aromatic compounds in the para position.Type: GrantFiled: August 27, 2010Date of Patent: February 4, 2014Assignee: E I du Pont de Nemours and CompanyInventors: David Richard Corbin, Joachim C. Ritter, James A. Schultz, Sourav Kumar Sengupta, Katelyn Rae Walck
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Patent number: 8592565Abstract: The invention relates to carbon surfaces modified with one or more azide groups. The invention also relates to methods of modifying carbon surfaces with one or more azide groups.Type: GrantFiled: January 10, 2008Date of Patent: November 26, 2013Assignee: The Board of Trustees of the Leland Stanford Junior UniversityInventors: Christopher E. D. Chidsey, Anando Devadoss, Neal K. Devaraj
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Publication number: 20110313158Abstract: The invention describes the development of highly efficient, recyclable two component system, CuAl-hydrotalcite/rac 1,1?-Binaphthalene-2,2?-diol catalytic system for the N-alkylation of electron deficient aryl chlorides in presence of potassium carbonate as a base at room temperature in 3-6 h, wherein the process is provided for the preparation of various secondary amines via C—N coupling reaction of aliphatic amines(aliphatic open chain, acyclic, benzyl amines and heterocyclic amines) with various aryl chlorides.Type: ApplicationFiled: February 26, 2010Publication date: December 22, 2011Inventors: Pravin R. Likhar, R. Arundhati, M. Lakshmi Kantam
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Publication number: 20110306795Abstract: A process for the preparation of mononitroaromatics and dinitroaromatics, in which a hydrate melt of at least one metal nitrate M(NO3)3 is used as a nitrating medium, it being possible for M to be the metals Fe, Cr, Y, La, Ce, Al, Bi and In, and the metal nitrate having a water content of from 4 to 9 mol of water per M(NO3)3, leads to simplifications of the process and improved yields.Type: ApplicationFiled: February 26, 2010Publication date: December 15, 2011Applicant: BASF SEInventors: Wolfgang Mackenroth, Johannes Buettner, Eckhard Stroefer, Wolfgang Voigt, Frank Bok
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Publication number: 20110184196Abstract: The invention relates to carbon surfaces modified with one or more azide groups. The invention also relates to methods of modifying carbon surfaces with one or more azide groups.Type: ApplicationFiled: January 10, 2008Publication date: July 28, 2011Applicant: The Board of Trustees of the Leland Stanford Junior UniversityInventors: Christopher E.D. Chidsey, Anando Devadoss, Neal K. Devaraj
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Publication number: 20110054219Abstract: Aromatic compounds such as o-xylene are selectively nitrated by nitric acid in the presence of polyphosphoric acid and a large pore, acidic zeolite or a large pore, hydrophobic molecular sieve. This is an environmentally friendly, commercially viable, high conversion process for the selective nitration of aromatic compounds in the para position.Type: ApplicationFiled: August 27, 2010Publication date: March 3, 2011Applicant: E. I. DU PONT DE NEMOURS AND COMPANYInventors: David Richard Corbin, Joachim C. Ritter, James A. Schultz, Sourav Kumar Sengupta, Katelyn Rae Walck
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Publication number: 20090093655Abstract: The present invention relates to a process and an apparatus for preparing aromatic amines by means of a heterogeneously catalysed hydrogenation, wherein the catalyst required for the reaction is applied to the interior wall of one or more reaction channels which are cooled from the outside.Type: ApplicationFiled: March 1, 2007Publication date: April 9, 2009Applicant: BAYER TECHNOLOGY SERVICES GMBHInventors: Stephan Schubert, Ralph Schellen, Leslaw Mleczko, Stephan Laue, Peter Lehner
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Patent number: 7476699Abstract: The present invention provides compounds having the formula: in which R is hydrogen, hydroxy, halogen, C1-C20-alkyl, C4-C12cycloalkyl, C2-C20alkenyl, C2-C20alkynyl, C1-C20-alkoxy, C4-C12cycloalkoxy, C2-C20alkenoxy, C2-C20alkynoxy or C7-C13aralkyl; R1 and R2, independently, are hydrogen, C1-C20alkyl, C4-C12cycloalkyl, C7-C13 aralkyl, —C(?O)—R4 (in which R4 is C1-C20alkyl, C2-C20alkyl interrupted by 1 to 6 oxygen atoms, hetero-substituted C1-C20alkyl, C4-C12cycloalkyl, C2-C20alkenyl, C2-C20alkynyl, C1-C20-alkoxy, C4-C12cycloalkoxy, C2-C20alkenoxy, C2-C20alkynoxy, C6-C12 aryl, C6-C12 aryloxy or C7-C13 aralkyl), or —C(?O)—NH—R1 in which R1 has its previous significance; and R3 is hydrogen, halogen, hydroxy, C1-C20alkyl, C4-C12cycloalkyl, C2-C20alkenyl, C2-C20alkynyl, C1-C20-alkoxy, C4-C12cycloalkoxy, C2-C20alkenoxy, C2-C20alkynoxy, phenyl, C7-C13 aralkyl or —N(R1)(R2) in which R1 and R2 have their previous significance, or R1 and R2 together form a C4-C12 membered ring.Type: GrantFiled: August 10, 2007Date of Patent: January 13, 2009Assignee: Ciba Specialty Chemicals Corp.Inventors: Dieter Reinehr, Georges Metzger, Peter Michaelis, Helmut Luther
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Patent number: 7005553Abstract: A method for the regioselective ortho-directed nitration of phenolic compounds useful for the preparation of ortho-nitro-phenols according to formula (I) is described.Type: GrantFiled: July 22, 2002Date of Patent: February 28, 2006Assignee: Portela, C.A., S.A.Inventor: David Alexander Learmonth
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Patent number: 6861527Abstract: The present invention relates to a novel process for the nitration of organic compounds, preferably of aromatic and heteroaromatic compounds, using nitrating reagents which are known from the literature and new types of nitrating reagents.Type: GrantFiled: July 5, 2000Date of Patent: March 1, 2005Assignee: Merck Patent GmbHInventors: Kai Fabian, Joeran Stoldt, Hanns Wurziger, Norbert Schwesinger
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Patent number: 6392097Abstract: Processes for the preparation of parylene dimers, and more particularly to processes for the preparation of derivatives of octafluoro-[2,2]paracylophane, otherwise known as AF4.Type: GrantFiled: March 20, 2001Date of Patent: May 21, 2002Assignee: Specialty Coating Systems, Inc.Inventors: William R. Dolbier, Jr., Jian-Xin Duan, Alex J. Roche
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Patent number: 6278022Abstract: Disclosed herein is an improvement in a method for making compounds having the structural formulae (I) or (II): wherein: X is a) phenyl; lower phenylalkoxy; phenoxy; or benzyl; or b) one substituent from group a) and one or more substituents selected from C1-C4 alkoxy; hydroxyl; halogen; lower alkyl; and lower alkylthio; or c) along with the phenyl to which it is attached, forms a multiple fused ring heterocycle such as dibenzofuranyl; Y is H, C1-C4 alkanoyl, C1-C4 haloalkenoyl, dialkoxyphosphoryl, alkylaminocarbonyl, haloalkylsulfonyl, or C1-C4 alkoxy carbonyl; and R is H, C1-C6 alkyl, C1-C6 alkoxy, C3-C6 cycloalkoxy, haloalkyl, alkoxyalkyl, arylalkoxy, alkenyl, alkylthio, alkoxycarbonyl, alkylamino, heteroaryl, arylalkyl, haloalkoxy, aryloxy, or C3-C6 cycloalkyl; and Z is O or S, wherein the improvement comprises the steps of: A) selecting as a starting material a compound of the structural formula B) dissolving compound III in an organic solvent selected from the groupType: GrantFiled: November 1, 1999Date of Patent: August 21, 2001Assignee: CK Witco CorporationInventor: Haihong Jin
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Patent number: 6160179Abstract: A method of manufacture of 4-nitro-m-phenylenediamine sulfate is taught. The resultant compound is useful in the dyeing of keratinic fibers, particularly, human hair. It exhibits reduced toxicity and potential for damage to such fibers, and is easier to remove than are other known compounds.Type: GrantFiled: August 31, 1999Date of Patent: December 12, 2000Inventors: James Giannotti, Huayong Song
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Patent number: 5981795Abstract: A method of purifying dinitroaniline of the general formula: ##STR1## in which: R is linear or branched C.sub.1 -C.sub.6 alkyl, C.sub.4 -C.sub.6 cycloalkyl, C.sub.1 -C.sub.4 monohaloalkyl or C.sub.1 -C.sub.4 alkoxy(C.sub.2 -C.sub.4)alkyl,Y is C.sub.1 -C.sub.4 alkyl, halogen or CF.sub.3, andX is hydrogen, halogen, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 monohaloalkyl, or C.sub.1 -C.sub.4 alkoxy(C.sub.1 -C.sub.4)alkyl, by N-denitration of the impurities of N-2,6-dinitroaniline contained therein, in the presence of a base selected from alkali-metal hydroxides, alkali-metal carbonates and ammonium hydroxide, at neutral or basic pH, comprising the treatment, with stirring, of the dinitroaniline to be purified, with an alcoholic organic solvent.Type: GrantFiled: April 8, 1999Date of Patent: November 9, 1999Assignee: Finchimica S.p.A.Inventors: Guido Ravetta, Gianluca Bernardi
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Patent number: 5922913Abstract: Disclosed is a process of nitrating or dinitrating an aromatic amine compound that involves reacting the aromatic amine and nitric acid in the presence of acetic acid such that the molar ratio of the aromatic amine compound to acetic acid is from about 1:2 to about 1:16, and the molar ratio of nitric acid to the aromatic amine is between about 1.0 to about 1.5 times the nitric acid needed to complete the reaction. More particularly, the invention is a process of forming Pendimethalin, N-(1-ethylpropyl)-2,6-dinitro-3,4-xylidine, from N-(1-ethylpropyl)-3,4-xylidine (4-NAX) that involves reacting 4-NAX and nitric acid in the presence of acetic acid such that the molar ratio of nitric to the 4-NAX is between about 2:1 and about 3:1, preferably between about 2:1 and about 2.6:1, and such that the molar ratio of 4-NAX to acetic acid is between about 1:2 to about 1:16, preferably between about 1:4 and about 1:8.Type: GrantFiled: November 6, 1998Date of Patent: July 13, 1999Assignee: SRM Chemical, Ltd., Co.Inventors: Lowell J. Lawrence, Stefan Kwiatkowski, Paul D. Smith
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Patent number: 5907062Abstract: A continuous process for the dinitration of alkyl-substituted derivatives of phenol and aniline, using nitric acid substantially free of sulphuric acid, characterized in which the dinitration is conducted in a single step in a tubular reactor in the presence of a catalytically-effective amount of a catalyst capable of reacting with the nitric acid to form nitrous acid in situ.Type: GrantFiled: November 19, 1997Date of Patent: May 25, 1999Assignee: Finchimica S.p.A.Inventors: Alberto Villanti, Giacomo Ravetta
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Patent number: 5136041Abstract: The compound 7-amino-4,6-dinitrobenzofuroxan is prepared by reacting 2,3,4,6-tetranitroaniline in a solvent with aqueous sodium azide under controlled exotherm conditions.Type: GrantFiled: May 14, 1991Date of Patent: August 4, 1992Assignee: Rockwell International CorporationInventor: James F. Weber
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Patent number: 5081303Abstract: A two-stage process for the co-production of aniline and m-phenylenediamine where, in the first stage, benzene, nitric acid, and sulfuric acid are reacted in a liquid phase to produce in greater amounts nitrobenzene (approximately 70%) and m-dinitrobenzene (approximately 30%), and in lesser or trace amounts o-dinitrobenzene and p-dinitrobenzene, and water; and in the second stage the products of the first stage are reacted with hydrogen in the liquid phase to produce aniline (approximately 70%) and m-phenylenediamine (approximately 30%) in greater amounts, and o-phenylenediamine and p-phenylenediamine in lesser amounts, and water. The reaction products are separated by distillation.Type: GrantFiled: April 21, 1989Date of Patent: January 14, 1992Assignee: First Chemical CorporationInventors: Harold Greenfield, Arthur C. Bayer, Earl G. Alley
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Patent number: 4723040Abstract: A process for preparing an N-mono-substituted-p-phenylenediamine by reacting the corresponding p-nitroso-N-mono-substituted aniline compound with a primary or secondary alcohol in the presence of a base.Type: GrantFiled: December 19, 1986Date of Patent: February 2, 1988Assignee: Uniroyal Chemical Company, Inc.Inventor: Wadim Batorewicz
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Patent number: 4675445Abstract: A process for eliminating N-nitrosamines, particularly N,N-dialkyl-N-nitrosamines and N-alkyl-N-aryl-N-nitrosamines from N-nitrosamine containing compositions through the addition of organic carboxylic acid halides. The process eliminates N-nitroso compounds without rearrangement to C-nitroso compounds.Type: GrantFiled: November 12, 1985Date of Patent: June 23, 1987Assignee: BASF CorporationInventors: Pauls Davis, Donald C. Mente
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Patent number: 4638090Abstract: Processes for the preparation of nitrosamine-free N,N-disubstituted nitroaromatic amines by degradation of their nitrosamine components formed during their preparation, and by stabilization of the products against renewed formation of nitrosamines, by treating the amines in liquid or molten form with a sulfonic acid, where necessary in the presence of inert organic solvents or diluents.Type: GrantFiled: December 12, 1984Date of Patent: January 20, 1987Assignee: Hoechst AktiengesellschatInventors: Rudolf Heinrich, Konrad Albrecht
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Patent number: 4621157Abstract: The present invention relates to improvements in processes of preparing dinitrated aromatic compounds, particularly dinitrated aniline and dinitrated substituted aniline compounds, employing relatively dilute and then more concentrated nitric acid as the nitrating agent.Type: GrantFiled: May 7, 1984Date of Patent: November 4, 1986Assignee: Jerome A. GrossInventor: Larry A. McDaniel
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Patent number: 4618714Abstract: Preparation of 3,3'- or 3,4'-diaminobenzophenone by nitrating a chloronitrobenzophenone mixture obtained by the Friedel-Crafts reaction between 3- or 4-nitrobenzoyl chloride and chlorobenzene, and catalytically reducing and dechlorinating the resulting chlorodinitrobenzophenone mixture in the presence of a reduction catalyst and a dehydrochlorinating agent.Type: GrantFiled: May 2, 1983Date of Patent: October 21, 1986Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Keizaburo Yamaguchi, Kenichi Sugimoto, Yoshimitsu Tanabe, Saburo Kawashima, Akihiro Yamaguchi
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Patent number: 4600797Abstract: Process for the preparation of a nitroaminobenzene by nitrating an aminobenzene which is protected at the nitrogen wherein the nitration is carried out by the simultaneous combination of nitric acid and the aminobenzene to be nitrated, in the presence of inert solvents such as methylene chloride.Type: GrantFiled: February 18, 1983Date of Patent: July 15, 1986Assignee: Bayer AktiengesellschaftInventor: Willi Schossler
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Patent number: 4556738Abstract: 3,3'- or 3,4'-diamino benzophenone is prepared by catalytically reducing and dehalogenating, in the presence of a reduction catalyst and a dehydrohalogenation agent, a benzophenone compound or benzophenone compounds of the general formula ##STR1## in which X is a halogen atom at position 2 or 4 of the benzene ring and Y is hydrogen or a halogen atom and in which the nitro group is at position 3' or 4' of the benzene ring if Y is hydrogen, while Y is at position 4' and the nitro group is at position 3' of the benzene ring if Y is a halogen atom.Type: GrantFiled: January 3, 1983Date of Patent: December 3, 1985Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Saburo Kawashima, Akihiro Yamaguchi
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Patent number: 4552981Abstract: The present invention is directed to a process for preparing 5-nitro-acet-2,4-xylidine comprising:(a) dissolving acet-2,4-xylidine in an aqueous sulfuric acid solution, said aqueous solution containing from 86 to 92% by weight of sulfuric acid, the weight ratio of sulfuric acid to acet-2,4-xylidine being from 3.5:1 to 6.5:1;(b) nitrating the resultant solution at a temperature of from 0.degree. to 15.degree. C. in a mixed acid containing nitric acid, sulfuric acid, and from 10 to 25% by weight water; and(c) recovering 5-nitro-acet-2,4-xylidine.Type: GrantFiled: November 27, 1981Date of Patent: November 12, 1985Assignee: Mobay Chemical CorporationInventors: Karl W. Thiem, Daniel P. Vanderpool
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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: 4531013Abstract: A new compound 2,6-diamino-1,4,5,8-tetranitronaphthalene is disclosed and a method of preparation thereof. The new compound is useful as a high energy, high density explosive.Type: GrantFiled: August 3, 1984Date of Patent: July 23, 1985Assignee: The United States of America as represented by the Secretary of the NavyInventors: Albert A. De Fusco, Arnold T. Nielsen
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Patent number: 4370502Abstract: A process for producing p-nitroaniline, which comprises nitrating an .alpha.-methylbenzalaniline of the formula ##STR1## wherein R represents an alkyl group having 1 to 5 carbon atoms, and n is 0 or 1,with nitric acid in the presence of a halogenated aliphatic hydrocarbon solvent and sulfuric acid to form a p-nitro-.alpha.-methylbenzalaniline of the formula ##STR2## wherein R and n are as defined above, and hydrolyzing the p-nitro-.alpha.-methylbenzalaniline.Type: GrantFiled: March 13, 1981Date of Patent: January 25, 1983Assignee: Mitsui Petrochemical Industries Ltd.Inventors: Taira Harada, Toyozi Shimizu, Takenori Nagaoka
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Patent number: 4234470Abstract: A process for the continuous catalytic vapor-phase mononitration of aromatic compounds, especially benzene, using as the catalyst an .alpha.-fluorosulfonic acid polymer admixed with a complement inert to the nitration reaction and dimensionally stable under the reaction conditions.Type: GrantFiled: April 23, 1979Date of Patent: November 18, 1980Assignee: E. I. Du Pont de Nemours and CompanyInventor: Frederick R. Lawrence
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Patent number: RE33168Abstract: The present invention relates to improvements in processes of preparing dinitrated .[.aromatic compounds, particularly dinitrated aniline and dinitrated substituted aniline compounds, employing relatively dilute and then more concentrated nitric acid as the nitrating agent.]. .Iadd.aniline and substituted phenol compounds in a two-step process, employing, in the first or mononitration step the spent nitric acid from the second of dinitration step. .Iaddend.Type: GrantFiled: July 5, 1988Date of Patent: February 20, 1990Assignee: Jerome A. GrossInventor: Larry A. McDaniel