Preparing Directly By Nitration Patents (Class 564/411)
  • Publication number: 20140371446
    Abstract: 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: Application
    Filed: August 25, 2014
    Publication date: December 18, 2014
    Applicant: AbbVie Inc.
    Inventors: Shashank Shekhar, Thaddeus S. Franczyk, David M. Barnes, Travis B. Dunn, Anthony R. Haight, Vincent S. Chan
  • Publication number: 20140227792
    Abstract: 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: Application
    Filed: July 27, 2012
    Publication date: August 14, 2014
    Applicant: CHIRON A/S
    Inventors: Jon Eigill Johansen, Huiling Liu, Morten Karlsen
  • Patent number: 8729309
    Abstract: 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: Grant
    Filed: July 26, 2011
    Date of Patent: May 20, 2014
    Assignee: Bayer Intellectual Property GmbH
    Inventors: Thomas Knauf, Alexandre Racoes, Andreas Karl Rausch, Dietrich Wulf
  • Patent number: 8642781
    Abstract: 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: Grant
    Filed: August 27, 2010
    Date of Patent: February 4, 2014
    Assignee: E I du Pont de Nemours and Company
    Inventors: David Richard Corbin, Joachim C. Ritter, James A. Schultz, Sourav Kumar Sengupta, Katelyn Rae Walck
  • Patent number: 8592565
    Abstract: 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: Grant
    Filed: January 10, 2008
    Date of Patent: November 26, 2013
    Assignee: The Board of Trustees of the Leland Stanford Junior University
    Inventors: Christopher E. D. Chidsey, Anando Devadoss, Neal K. Devaraj
  • Publication number: 20110313158
    Abstract: 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: Application
    Filed: February 26, 2010
    Publication date: December 22, 2011
    Inventors: Pravin R. Likhar, R. Arundhati, M. Lakshmi Kantam
  • Publication number: 20110306795
    Abstract: 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: Application
    Filed: February 26, 2010
    Publication date: December 15, 2011
    Applicant: BASF SE
    Inventors: Wolfgang Mackenroth, Johannes Buettner, Eckhard Stroefer, Wolfgang Voigt, Frank Bok
  • Publication number: 20110184196
    Abstract: 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: Application
    Filed: January 10, 2008
    Publication date: July 28, 2011
    Applicant: The Board of Trustees of the Leland Stanford Junior University
    Inventors: Christopher E.D. Chidsey, Anando Devadoss, Neal K. Devaraj
  • Publication number: 20110054219
    Abstract: 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: Application
    Filed: August 27, 2010
    Publication date: March 3, 2011
    Applicant: E. I. DU PONT DE NEMOURS AND COMPANY
    Inventors: David Richard Corbin, Joachim C. Ritter, James A. Schultz, Sourav Kumar Sengupta, Katelyn Rae Walck
  • Publication number: 20090093655
    Abstract: 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: Application
    Filed: March 1, 2007
    Publication date: April 9, 2009
    Applicant: BAYER TECHNOLOGY SERVICES GMBH
    Inventors: Stephan Schubert, Ralph Schellen, Leslaw Mleczko, Stephan Laue, Peter Lehner
  • Patent number: 7476699
    Abstract: 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: Grant
    Filed: August 10, 2007
    Date of Patent: January 13, 2009
    Assignee: Ciba Specialty Chemicals Corp.
    Inventors: Dieter Reinehr, Georges Metzger, Peter Michaelis, Helmut Luther
  • Patent number: 7005553
    Abstract: 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: Grant
    Filed: July 22, 2002
    Date of Patent: February 28, 2006
    Assignee: Portela, C.A., S.A.
    Inventor: David Alexander Learmonth
  • Patent number: 6861527
    Abstract: 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: Grant
    Filed: July 5, 2000
    Date of Patent: March 1, 2005
    Assignee: Merck Patent GmbH
    Inventors: Kai Fabian, Joeran Stoldt, Hanns Wurziger, Norbert Schwesinger
  • Patent number: 6392097
    Abstract: 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: Grant
    Filed: March 20, 2001
    Date of Patent: May 21, 2002
    Assignee: Specialty Coating Systems, Inc.
    Inventors: William R. Dolbier, Jr., Jian-Xin Duan, Alex J. Roche
  • Patent number: 6278022
    Abstract: 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 group
    Type: Grant
    Filed: November 1, 1999
    Date of Patent: August 21, 2001
    Assignee: CK Witco Corporation
    Inventor: Haihong Jin
  • Patent number: 6160179
    Abstract: 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: Grant
    Filed: August 31, 1999
    Date of Patent: December 12, 2000
    Inventors: James Giannotti, Huayong Song
  • Patent number: 5981795
    Abstract: 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: Grant
    Filed: April 8, 1999
    Date of Patent: November 9, 1999
    Assignee: Finchimica S.p.A.
    Inventors: Guido Ravetta, Gianluca Bernardi
  • Patent number: 5922913
    Abstract: 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: Grant
    Filed: November 6, 1998
    Date of Patent: July 13, 1999
    Assignee: SRM Chemical, Ltd., Co.
    Inventors: Lowell J. Lawrence, Stefan Kwiatkowski, Paul D. Smith
  • Patent number: 5907062
    Abstract: 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: Grant
    Filed: November 19, 1997
    Date of Patent: May 25, 1999
    Assignee: Finchimica S.p.A.
    Inventors: Alberto Villanti, Giacomo Ravetta
  • Patent number: 5136041
    Abstract: 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: Grant
    Filed: May 14, 1991
    Date of Patent: August 4, 1992
    Assignee: Rockwell International Corporation
    Inventor: James F. Weber
  • Patent number: 5081303
    Abstract: 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: Grant
    Filed: April 21, 1989
    Date of Patent: January 14, 1992
    Assignee: First Chemical Corporation
    Inventors: Harold Greenfield, Arthur C. Bayer, Earl G. Alley
  • Patent number: 4723040
    Abstract: 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: Grant
    Filed: December 19, 1986
    Date of Patent: February 2, 1988
    Assignee: Uniroyal Chemical Company, Inc.
    Inventor: Wadim Batorewicz
  • Patent number: 4675445
    Abstract: 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: Grant
    Filed: November 12, 1985
    Date of Patent: June 23, 1987
    Assignee: BASF Corporation
    Inventors: Pauls Davis, Donald C. Mente
  • Patent number: 4638090
    Abstract: 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: Grant
    Filed: December 12, 1984
    Date of Patent: January 20, 1987
    Assignee: Hoechst Aktiengesellschat
    Inventors: Rudolf Heinrich, Konrad Albrecht
  • Patent number: 4621157
    Abstract: 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: Grant
    Filed: May 7, 1984
    Date of Patent: November 4, 1986
    Assignee: Jerome A. Gross
    Inventor: Larry A. McDaniel
  • Patent number: 4618714
    Abstract: 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: Grant
    Filed: May 2, 1983
    Date of Patent: October 21, 1986
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Keizaburo Yamaguchi, Kenichi Sugimoto, Yoshimitsu Tanabe, Saburo Kawashima, Akihiro Yamaguchi
  • Patent number: 4600797
    Abstract: 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: Grant
    Filed: February 18, 1983
    Date of Patent: July 15, 1986
    Assignee: Bayer Aktiengesellschaft
    Inventor: Willi Schossler
  • Patent number: 4556738
    Abstract: 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: Grant
    Filed: January 3, 1983
    Date of Patent: December 3, 1985
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Saburo Kawashima, Akihiro Yamaguchi
  • Patent number: 4552981
    Abstract: 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: Grant
    Filed: November 27, 1981
    Date of Patent: November 12, 1985
    Assignee: Mobay Chemical Corporation
    Inventors: Karl W. Thiem, Daniel P. Vanderpool
  • Patent number: 4532353
    Abstract: 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: Grant
    Filed: June 16, 1983
    Date of Patent: July 30, 1985
    Assignee: Monsanto Co.
    Inventors: John P. Chupp, Audrey Y. Ku, Thomas E. Neumann, Thomas E. Nickson
  • Patent number: 4531013
    Abstract: 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: Grant
    Filed: August 3, 1984
    Date of Patent: July 23, 1985
    Assignee: The United States of America as represented by the Secretary of the Navy
    Inventors: Albert A. De Fusco, Arnold T. Nielsen
  • Patent number: 4370502
    Abstract: 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: Grant
    Filed: March 13, 1981
    Date of Patent: January 25, 1983
    Assignee: Mitsui Petrochemical Industries Ltd.
    Inventors: Taira Harada, Toyozi Shimizu, Takenori Nagaoka
  • Patent number: 4234470
    Abstract: 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: Grant
    Filed: April 23, 1979
    Date of Patent: November 18, 1980
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Frederick R. Lawrence
  • Patent number: RE33168
    Abstract: 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: Grant
    Filed: July 5, 1988
    Date of Patent: February 20, 1990
    Assignee: Jerome A. Gross
    Inventor: Larry A. McDaniel