Abstract: 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:
Grant
Filed:
February 10, 2000
Date of Patent:
October 24, 2000
Assignee:
Korea Kumho Petrochemical Co., Ltd.
Inventors:
Young J. Joo, Jin Eok Kim, Jeong Im Won, Kum Ui Hwang
Abstract: N,N-disubstituted amines in which the amino nitrogen atom is bound to the carbon atom of an aromatic ring disubstituted in the positions ortho to the carbon atom, are prepared by allowing a primary amine and a compound in which an ortho, ortho-disubstituted aromatic compound carrying a nucleofuge substituent, to react in a basic environment in the presence of a catalytic palladium(0) complex and a ligand, the ratio of palladium complex to ligand being greater than at least 1:1. A typical embodiment involves the reaction of 2-methyl-6-ethylphenyl-trifluoromethylsulfonate and (S)-1-methoxy-2-aminopropane in the presence of bis(dibenzylideneacetone)palladium, tri-tert.-butylphosphine, and sodium tert.-butoxide to yield (S)-N-(1-methoxyprop-2-yl)-2-methyl-6-ethylphenylamine.
Type:
Grant
Filed:
December 14, 1999
Date of Patent:
August 22, 2000
Assignee:
Celgro
Inventors:
Sue L. Lin, Weixia M. Zhou, George W. Matcham
Abstract: Disclosed is a process for the preparation of N-aryl amine compounds, comprising reacting an amine compound with an arylating compound in the presence of a base and a transition metal catalyst under reaction conditions effective to form an N-aryl amine compound, the transition metal catalyst comprising a Group 8 metal and P(t-Bu).sub.3 as a ligand, and wherein the ratio of the ligand to the Group 8 metal is in the range of about 3:1 to about 0.25:1, and wherein the reaction temperature is less than 100.degree. C. The process of the present invention provides a useful general method of N-arylation for the manufacture of pharmaceuticals, polymers, and the like.
Type:
Grant
Filed:
June 30, 1999
Date of Patent:
August 8, 2000
Assignee:
Yale University
Inventors:
John F. Hartwig, Motoi Kawatsura, Sheila I. Hauck, Kevin H. Shaughnessy, Luis M. Alcazar-Roman
Abstract: The present invention relates to a process to aminate electrophilic aromatic compounds by vicarious nucleophilic substitution of hydrogen using quaternary hydrazinium salts. The use of trialkylhydrazinium halide, e.g., trimethylhydrazinium iodide, as well as hydroxylamine, alkoxylamines, and 4-amino-1,2,4-triazole to produce aminated aromatic structures, such as 1,3-diamino-2,4,6-trinitrobenzene (DATB), 1,3,5-triamino-2,4,6-trinitrobenzene (TATB) and 3,5-diamino-2,4,6-trinitrotoluene (DATNT), is described. DATB and TATB are useful insensitive high explosives. TATB is also used for the preparation of benzenehexamine, a starting material for the synthesis of novel materials (optical imaging devices, liquid crystals, ferromagnetic compounds).
Type:
Grant
Filed:
November 12, 1997
Date of Patent:
May 30, 2000
Assignee:
The Regents of the University of California
Inventors:
Alexander R. Mitchell, Philip F. Pagoria, Robert D. Schmidt
Abstract: A catalyst comprises, based on the total weight of the catalyst,0.1-6% by weight of cobalt, nickel or a mixture thereof,0.001-25% by weight of ruthenium,0-10% by weight of copper and0-5% by weight of promoterson a porous metal oxide carrier.It preferably comprises 0.1-3% by weight of cobalt and 0.1-3% by weight of nickel. It can be used in hydrogenation reactions, dehydrogenation reactions or hydrogenation/dehydrogenation reactions, in particular in the amination of alkylene oxides, alcohols, aldehydes or ketones with ammonia or primary or secondary amines.
Type:
Grant
Filed:
March 4, 1999
Date of Patent:
April 4, 2000
Assignee:
BASF Aktiengesellschaft
Inventors:
Joachim Wulff-Doring, Johann-Peter Melder, Gerhard Schulz, Guido Voit, Gutshoven Frank, Wolfgang Harder
Abstract: A heterocyclic aromatic halide or an aryl halide is reacted with an amine compound in the presence of a base to give a heterocyclic aromatic amine or an arylamine, respectively. In this reaction, a catalyst comprising a palladium compound and a tertiary phosphine is used for the preparation of a heterocyclic aromatic amine, and a catalyst comprising a palladium compound and a trialkylphosphine is used for the preparation of an arylamine.
Abstract: Disclosed is a novel intermediate, 3,4-dihydro-6-methyl-4-phenyl-2H-benzopyran-2-ol (IV) ##STR1## and an improved process for the preparation of tolterodine.
Abstract: An (S)-1-phenyl-2-substituted propane derivative shown by the following formula (I) ##STR1## wherein R.sup.1 and R.sup.2 represent a lower alkyl group, etc., or R.sup.1 and R.sup.2 may form together an alkylene group, etc.; R.sup.3, R.sup.4 and R.sup.5 represent a hydrogen atom, etc.; and X represents a hydroxyl group which may be protected with a protective group, or a halogen atom etc., can readily be produced (i) by permitting a microorganism belonging to the genus Torulaspora, the genus Candida, the genus Pichia or the like to act on a phenylacetone derivative and asymmetrically reducing the compound, or (ii) by sterically inverting an (R)-enantiomer. (R,R)-1-phenyl-2-?(2-phenyl-1-methylethyl)amino!ethanol derivative having a high optical purity can easily be obtained from the compound of the formula (I). The ethanol derivative is useful as an anti-obesity agent and the like.
Abstract: A process for the preparation of N,N-bis(3,4-dimethylphenyl)-4-biphenylamine which comprises the reaction of N,N-bis(3,4-dimethylphenyl)amine and an iodobiphenyl in the presence of a ligand copper catalyst, and wherein the ligand is selected from the group consisting of monodentate tertiary amines and bidentate tertiary amines, and which reaction is accomplished at a temperature of, for example, from about 120.degree. C. to about 150.degree. C.
Type:
Grant
Filed:
May 7, 1998
Date of Patent:
May 11, 1999
Assignee:
Xerox Corporation
Inventors:
H. Bruce Goodbrand, George Liebermann, Roger E. Gaynor
Abstract: A process for the preparation of amines by reacting an olefin with ammonia or a primary or secondary amine at a temperature of from 200 to 350.degree. C. and a pressure of from 100 to 300 bar in the presence of at least one zeolite having the specific structure type PSH-3, MCM-22 or SSZ-25, as identified by X-ray diffractogram, or mixtures of these zeolites. These specific catalysts are broadly identified as alumina zeolites and may be modified by ion exchange, doping with other metals, by dealumination to remove or replace the alumina content and by other well known after treatments such as calcination, acid-treatment and the like. Monoolefins are preferred reactants but di- and polyolefins also can be reacted with relatively high selectivity and less tendency toward polymerization.
Type:
Grant
Filed:
July 18, 1996
Date of Patent:
May 4, 1999
Assignee:
BASF Aktiengesellschaft
Inventors:
Karsten Eller, Ulrich Muller, Rudolf Kummer, Peter Stops
Abstract: Tertiary aminoaryl compounds, such as N,N'dialkylaminoaryl compounds, are prepared using successive reductive steps without isolation therebetween, at high temperature and pressure. A nitroaryl compound is reduced using a ketone as both solvent and reactant in a reductive environment, and the resulting intermediate is further reacted with an aldehyde in the same reaction mixture without isolation to provide the second substituent on the amino group.
Abstract: A process for preparing N-methyl-2-(3,4-dimethoxyphenyl)-ethylamine comprises hydrogenating 3,4-dimethoxyphenylacetonitrile with a methylamine of the general formula I ##STR1## where R.sup.1 is hydrogen, benzyl or tert-butyl, and hydrogen in the presence of a supported catalyst which comprises from 0.05 to 50% by weight of copper chromite, copper, silver, gold, iron, cobalt, nickel, ruthenium, rhodium, palladium, osmium, iridium, platinum or mixtures thereof, in the presence or absence of water at from 20.degree. to 200.degree. C. under from 1 to 300 bar.
Type:
Grant
Filed:
October 28, 1997
Date of Patent:
November 24, 1998
Assignee:
BASF Aktiengesellschaft
Inventors:
Eberhard Fuchs, Horst Zimmermann, Tom Witzel, Boris Breitscheidel, Rainer Becker, Horst Nauhauser
Abstract: A process for the preparation of N,N-bis(3,4-dimethylphenyl)-4-biphenylamine which comprises the reaction of an aminobiphenyl and an iodoxylene in the presence of a ligand copper catalyst, and wherein the ligand is selected from the group consisting of monodentate tertiary amines and bidentate tertiary amines, and which reaction is accomplished at a temperature of from about 120.degree. C. to about 150.degree. C.
Type:
Grant
Filed:
January 30, 1997
Date of Patent:
March 3, 1998
Assignee:
Xerox Corporation
Inventors:
H. Bruce Goodbrand, Nan-Xing Hu, Beng S. Ong
Abstract: A process for the preparation of N,N-bis(3,4-dimethylphenyl)-4-biphenylamine which comprises the reaction of N-(3,4-dimethylphenyl)-4-biphenylamine and an iodoxylene in the presence of a ligated copper catalyst, and wherein the ligand is selected from the group consisting of monodentate tertiary amines and bidentate tertiary amines, and which reaction is accomplished at a temperature of from about 120.degree. C. to about 150.degree. C.
Type:
Grant
Filed:
January 30, 1997
Date of Patent:
January 6, 1998
Assignee:
Xerox Corporation
Inventors:
H. Bruce Goodbrand, Nan-Xing Hu, Beng S. Ong
Abstract: An oil-soluble lubricating oil and fuel additive, useful as a multifunctional viscosity modifier comprising succinimide and other amine-containing polymers reacted with a quinone or substituted quinone adducts. Suitable polymers are those containing primary or secondary amine groups such as EPSA-PAM and EPDM-amine polymers. The multifunctional viscosity modifier additive provides improved dispersancy and antioxidancy to a lubricating oil or fuel composition.
Abstract: The present invention relates to a process to produce 1,3-diamino-2,4,6-trinitrobenzene (DATB) or 1,3,5-triamino-2,4,6,-trinitrobenzene (TATB) by:(a) reacting at ambient pressure and a temperature of between about 0.degree. and 50.degree. C. for between about 0.1 and 24 hr, a trinitroaromatic compound of structure V: ##STR1## wherein X, Y, and Z are each independently selected from the group consisting of --H and --NH.sub.
Type:
Grant
Filed:
May 12, 1995
Date of Patent:
May 27, 1997
Assignee:
The Regents of the University of California
Inventors:
Alexander R. Mitchell, Philip F. Pagoria, Robert D. Schmidt
Abstract: The present invention is directed to a process for the preparation of deactivated anilines, which comprises the step of reacting a compound of formula ( I ) ##STR1## with a dialkylamide in the presence of a base at elevated temperature, in which:R.sub.1 is chosen from groups whose anions (R.sub.1.sup.-) constitute leaving groups;R.sub.2 and R.sub.4, which may be the same or different, are chosen from hydrogen, hydrocarbon chains, halogens and groups which are electron-attracting (EAG);R.sub.3 is chosen from hydrocarbon chains, halogens and groups which are electron-attracting, preferably through an inductive effect rather than a mesomeric effect;with the proviso that at least one of the groups R.sub.2, R.sub.3, and R.sub.4 is electron-attracting through an inductive effect.A second embodiment of the present invention is directed to a process for the dealkylation of deactivated anilines which comprises the steps of free radical halogenation of the benzyl carbon followed by hydrogenation.
Abstract: A process for the preparation of glycoloylanilide of the formula (G) ##STR1## is recited that involves reacting a nitrobenzene with hydrogen and, if desired, with a carbonyl compound, in the presence of a noble metal catalyst and a solvent, reacting the compound produced with chloroacetyl chloride, reacting the resulting product with a benzyl alcohol and with a base, or reacting the resulting compound with an O-benzylglycoloyl chloride, and debenzylating the resulting benzylglycoloylanilide product by reacting with hydrogen in the presence of a noble metal catalyst. The invention also relates to a process for the preparation of O-benzylglycoloylanilide.
Abstract: The present invention relates to a novel process for the production of fuel and lubricant additives useful as dispersants and multifunctional viscosity modifiers wherein a dihydroxyaromatic compound is alkylated with an olefinic polymer and then aminated in such a manner as to oxidize the hydroxyl moieties of the dihydroxyaromatic compound to carbonyl groups.
Abstract: A method of preparing an arylamine compound includes reacting a metal amide comprising a metal selected from the group consisting of tin, boron, zinc, magnesium, indium and silicon, with an aromatic compound comprising an activated substituent in the presence of a transition metal catalyst to form an arylamine. The method is useful in preparing mixtures of arylamines for use in screening for pharmaceutical and biological activity and in preparing poly(anilines).
Abstract: 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.
Abstract: A process for preparing substituted aromatic amines is provided which comprises contacting a nucleophilic compound and an azo containing compound in the presence of a suitable solvent system, reacting the nucleophilic compound and the azo containing compound in the presence of a suitable base and a controlled amount of protic material at a temperature of about 10.degree. C. to about 150.degree. C. in a confined reaction zone wherein the molar ratio of protic material to base is 0:1 to about 5:1 and reducing the product of the reaction of the nucleophilic compound and the azo containing compound under conditions which produce the substituted aromatic amine. In another embodiment, the substituted aromatic amines of the invention are reductively alkylated to produce alkylated diamines or substituted derivatives thereof.
Abstract: A process for producing N,N-disubstituted aminophenol which comprises the steps of:obtaining a reaction mixture containing N-substituted aminophenol by reacting a dihydric phenol and an amine;subjecting said reaction mixture to heat treatment so as to thermally decompose quaternary ammonia salt contained in said reaction mixture into a dihydric phenol and an amine, and removing at least said amine by distillation;separating high-boiling impurities by distillation to separate N-substituted aminophenol; andsubjecting said separated N-substituted aminophenol to reduction alkylation using an aldehyde compound.According to the present invention, high-purity N,N-disubstituted aminophenol can be obtained in a high yield at high selectivity, and a reduction catalyst can be used repeatedly because its activity can be maintained at a high level and yet it can retain high activity for a long period of time.
Abstract: A process for preparing p-nitroaromatic amides is provided which comprises contacting a nitrile, nitrobenzene, a suitable base and water in the presence of a suitable solvent system to form a mixture, and reacting the mixture at a suitable temperature in a confined reaction zone in the presence of a controlled amount of protic material. The p-nitroaromatic amides of the invention can be reduced to p-aminoaromatic amides. In one embodiment, the p-aminoaromatic amide is further reacted with ammonia under conditions which produce the corresponding p-aminoaromatic amine and the amide corresponding to the nitrile starting material or with water in the presence of a suitable basic or acidic catalyst under conditions which produce the corresponding p-aminoaromatic amine and the acid or salt thereof corresponding to the nitrile starting material. In another embodiment, the p-aminoaromatic amine is reductively alkylated to produce alkylated p-aminoaromatic amine.
Abstract: A process of preparing para phenylenediamines, such as, p-aminodiphenylamine. The process involves contacting nitrobenzene or a substituted derivative thereof with hydrogen and an amine, such as aniline, in the presence of a hydrogenation catalyst, a hydrogenation inhibitor, and an acid cocatalyst under reaction conditions.
Type:
Grant
Filed:
October 6, 1994
Date of Patent:
May 30, 1995
Assignee:
Uniroyal Chemical Company, Inc.
Inventors:
Russell E. Malz, Gerard V. Smith, Mark P. Ferrandino, Ruozhi Song
Abstract: 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:
Grant
Filed:
December 3, 1992
Date of Patent:
May 9, 1995
Assignee:
Cassella AG
Inventors:
Willi Steckelberg, Rolf Muller, Peter Koch
Abstract: There is provided an improved method for the production of o-aminophenyl ketones of formula I wherein R is C.sub.3 -C.sub.6 cycloalkyl or C.sub.1 -C.sub.6 haloalkyl. ##STR1## Compounds of formula I are key intermediates in the manufacture of sulfamoyl urea herbicides.
Abstract: The present invention is directed to a process for the preparation of deactivated anilines, which comprises the step of reacting a compound of formula (I) ##STR1## with a dialkylamide in the presence of a base at elevated temperature, in which:R.sub.1 is chosen from groups whose anions (R.sub.1.sup.-) constitute leaving groups;R.sub.2 and R.sub.4, which may be the same or different, are chosen from hydrogen, hydrocarbon chains, halogens and groups which are electron-attracting (EAG);R.sub.3 is chosen from hydrocarbon chains, halogens and groups which are electron-attracting, preferably through an inductive effect rather than a mesomeric effect; with the proviso that at least one of the groups R.sub.2, R.sub.3, and R.sub.4 is electron-attracting through an inductive effect.A second embodiment of the present invention is directed to a process for the dealkylation of deactivated anilines which comprises the steps of free radical halogenation of the benzyl carbon followed by hydrogenation.
Abstract: The present invention relates to a novel process for the production of fuel and lubricant additives useful as dispersants and multifunctional viscosity modifiers wherein a dihydroxyaromatic compound is alkylated with an olefinic polymer and then aminated in such a manner as to oxidize the hydroxyl moieties of the dihydroxyaromatic compound to carbonyl groups.
Abstract: Methods for the production of 1,1,1-trihalogeno-2-nitroethanes from 1,1-dihalogenoethylene by using nitric acid or its salt and hydrogen chloride or hydrogen bromide or its salt, and for the production of .alpha.-unsaturated amines from the 1,1,1-trihalogeno-2-nitroethanes which are useful as insecticides.
Abstract: Disclosed is a process for producing 4-amino-3-fluorobenzotrifluoride which comprises reacting 3,4-difluorobenzotrifluoride with anhydrous ammonia (liquid ammonia or gaseous ammonia) under pressure.
Abstract: A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMe.sub.2 wherein R is an organo group, R* is a chiral organo group. attached to boron, B is boron and Me is methyl.
Abstract: A process for preparing a dimethylorganoborane represented by the formula R*BMe.sub.2 wherein R* is a chiral organyl group attached to the boron, B is boron and Me is methyl comprising treating a chiral boronic ester R*B(OR').sub.2 with a methyl magnesium salt or trimethylaluminum wherein R* is the same chiral organyl group and R' is alkyl.
Abstract: A process for preparing an N-alkyl-substituted aminophenol is disclosed, comprising continuously feeding an aldehyde or a ketone to a reaction system containing an organic solvent, a catalyst for reduction, hydrogen, and an aminophenol to conduct a reductive alkylation reaction, wherein said reductive alkylation reaction is carried out while continuously adding an organic carboxylic acid into the reaction system. The process attains a high yield even when the catalyst is repeatedly used and does not cause corrosion of equipment.
Type:
Grant
Filed:
August 1, 1990
Date of Patent:
January 4, 1994
Assignee:
Sumitomo Chemical Co., Ltd.
Inventors:
Hiroshi Maki, Michihiro Kawasaki, Hiroshi Shimizu, Yoshiaki Ito
Abstract: A process for preparing a 3- or 4-aminobenzocyclobutene comprises aminating a 3- or 4-halo- or sulfonyloxybenzocyclobutene reactant with an aminating agent by heating at a temperature from about 80.degree. C. to a temperature at which dimerization or oligomerization of a benzocyclobutene reactant or product is a significant side reaction, in the presence of a metal-containing catalyst, for a time sufficient to aminate the halo- or sulfonyloxybenzocyclobutene reactant. In another aspect, this invention relates to a process for making a 3- or 4-phthalimido- or maleimidobenzocyclobutene, comprising reacting a 3- or 4-halobenzocyclobutene reactant with a phthalimide or maleimide compound in the presence of a metal-containing catalyst. The resulting phthalimido- or maleimidobenzocyclobutene can be hydrolyzed to a 3- or 4-aminobenzocyclobutene.
Type:
Grant
Filed:
September 20, 1991
Date of Patent:
December 28, 1993
Assignee:
The Dow Chemical Company
Inventors:
Kenneth J. Bruza, Arnold E. Young, Kurt A. Bell
Abstract: The process for preparing a compound of the formula:Cp'YNHRwherein: Cp' is a cyclopentadienyl or a substituted cyclopentadienyl group, Y is a covalent bridging group which contains one or more group 14 elements, and R is a C.sub.1 to C.sub.20 hydrocarbyl or substituted hydrocarbyl group, the process comprising reacting a ligand of the formula Cp'YX, wherein Cp' and Y are as defined above and X is halogen, with a substantially equimolar amount of a primary amine of the formula NH.sub.2 R, wherein R is as defined above, in an inert solvent in the presence of a HX scavenger at an elevated temperature of at least about 35.degree. C., so as to form said compound.
Type:
Grant
Filed:
December 7, 1992
Date of Patent:
October 19, 1993
Assignee:
Ethyl Corporation
Inventors:
Jamie R. Strickler, John M. Power, Meng-Sheng Ao
Abstract: A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMe.sub.2 wherein R is an organo group, R* is a chiral organo group,attached to boron, B is boron and Me is methyl.
Abstract: A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMe.sub.2 wherein R is an organo group, R* is a chiral organo group, attached to boron, B is boron and Me is methyl.
Abstract: N-Aryl-substituted 2-amino-alkyl-2-hydroxyalkylamines and N-aryl-substituted piperazines Ia and Ib respectively ##STR1## (Ar=aryl; R.sup.1 =hydrogen, methyl, identical or different, R.sup.2 =hydrogen, alkyl) are prepared by reacting an N,N-di(2-hydroxyalkyl)-N-arylamine II ##STR2## with ammonia or a primary amine IIIH.sub.2 N-R.sup.2 IIIat elevated temperature and under elevated pressure in the presence of hydrogen and of a catalyst which is a supported catalyst whose active mass predominantly contains copper and/or nickel and/or cobalt in the form of the metal or an oxide.
Abstract: N,N-dialkylanilines can be prepared by reacting the anilines on which they are based with lower alcohols or with the corresponding ethers, at an increased temperature in the gas phase in the presence of a proton-containing zeolite catalyst of the pentasil type having an SiO.sub.2 /Al.sub.2 O.sub.3 ratio of >60, it being advantageous to carry out the alkylation process under a pressure of 2-30 bar.
Type:
Grant
Filed:
August 13, 1990
Date of Patent:
February 11, 1992
Assignee:
Bayer Aktiengesellschaft
Inventors:
Hans-Josef Buysch, Heinrich Pelster, Lothar Puppe, Peter Wimmer
Abstract: The selective N-alkylation of anilines comprising providing a mixture of a lower alkanol and an aniline, exposing said mixture to a temperature of from 250.degree. C. to 350.degree. C. in the presence of an acidic zeolite having a pore size of from 6 to 8 angstroms with a three-dimensional tubular shape, such as S-115 zeolite, is described. These zeolites are predominantly selective to the formation of N-alkylanilines.
Type:
Grant
Filed:
April 27, 1989
Date of Patent:
July 9, 1991
Assignee:
First Chemical Corporation
Inventors:
Arthur C. Bayer, Charles U. Pittman, Jr., Lichang Wang, Earl G. Alley, Anthony C. Maliyackel
Abstract: A hydroxy arylamine compound is disclosed represented by the formula: ##STR1## wherein: m is 0 or 1,Z is selected from the group consisting of: ##STR2## n is 0 or 1, Ar is selected from the group consisting of: ##STR3## R is selected from the group consisting of --CH.sub.3, --CH.sub.2 H.sub.5, --C.sub.3 H.sub.7, and --C.sub.4 H.sub.9,Ar' is selected from the group consisting of: ##STR4## X is selected from the group consisting of: ##STR5## s is 0, 1 or 2, the dihydroxy arylamine compound being free of any direct conjugation between the --OH groups and the nearest nitrogen atom through one or more aromatic rings. The dihydroxy arylamine compound may be employed in an electrophotographic imaging member and the member may be used in an electrophotographic imaging process.
Type:
Grant
Filed:
May 23, 1989
Date of Patent:
April 30, 1991
Assignee:
Xerox Corporation
Inventors:
William W. Limburg, John F. Yanus, Dale S. Renfer, Richard L. Schank, Beng S. Ong
Abstract: High molecular weight amines having reduced low molecular weight amine contents are obtained by reacting a mixture of (1) a high molecular weight amine and (2) a low molecular weight amine with (3) an isocyanate in quantities such that from 0.5 to 10 equivalents of isocyanate are present for each equivalent of low molecular weight amine. The product of high molecular weight amines is particularly useful in the production of isocyanate addition products such as polyurethane plastics and foams.
Type:
Grant
Filed:
September 23, 1985
Date of Patent:
August 8, 1989
Assignee:
Bayer Aktiengesellschaft
Inventors:
Werner Rasshofer, Ernst Grigat, Gerhard Grogler, Heinrich Hess, Richard Kopp
Abstract: Polyamines are produced by hydrolyzing isocyanate compounds having an NCO content of from 0.5 to 40 wt. % with from 0.75 to 40 moles of water per equivalent of NCO groups in the presence of from 0.021 to 0.099 wt. % sodium hydroxide and at least 10 wt. % water-miscible polar organic solvent containing nitrile, ketone, sulfoxide or ether groups having a boiling point of from 56.degree. to 250.degree. C. The reaction mixture is maintained in a homogeneous phase. The reaction is carried out at 40.degree. to 170.degree. C. These polyamines are useful in the production of polyurethane(urea)s.
Type:
Grant
Filed:
March 24, 1988
Date of Patent:
June 27, 1989
Assignee:
Bayer Aktiengesellschaft
Inventors:
Andreas Ruckes, Werner Rasshofer, Klaus Konig, Richard Kopp
Abstract: Polyamines containing primary amino groups are made by a one-shot process for the hydrolysis of prepolymers containing isocyanate end groups and having an isocyanate content of from 0.5 to 40 weight % with 0.75 to 40 mol of water per equivalent of isocyanate groups in the presence of very small quantities of sodium hydroxide in certain organic, polar solvents. The compounds containing isocyanate groups used for this process are isocyanate prepolymers (preferably containing urethane groups). Hydrolysis according to this process leads directly to the polyamines with elimination of carbon dioxide. These polyamines may be isolated by the usual methods and the removal of the small quantities of catalyst may advantageously be omitted. These polyamines are useful for the preparation of polyurethane(urea)s.
Type:
Grant
Filed:
March 24, 1988
Date of Patent:
June 27, 1989
Assignee:
Bayer Aktiengesellschaft
Inventors:
Andreas Ruckes, Werner Rasshofer, Klaus Konig, Richard Kopp
Abstract: A two-step process for the preparation of secondary amines in good yield from olefins, carbon monoxide, hydrogen and primary amines is described. The intermediate imine may be isolated in good yield as well.
Abstract: 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.