Of Acyclic Hydroxy Containing Compound Patents (Class 564/401)
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Patent number: 8134030Abstract: A process for preparing a primary amine with a tertiary alpha-carbon atom by reacting a tertiary alcohol with ammonia in the presence of a heterogeneous catalyst, by performing the reaction in the presence of a non-microporous, non-zeolitic aluminosilicate as a catalyst, where the aluminosilicate has a molar Al/Si ratio in the range from 0.1 to 30.Type: GrantFiled: October 14, 2008Date of Patent: March 13, 2012Assignee: BASF SEInventors: Marcus Sigl, Thomas Heidemann
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Patent number: 7754922Abstract: Processes comprising: (i) providing a reactant selected from the group consisting of primary alcohols, secondary alcohols, aldehydes, ketones and mixtures thereof; and (ii) reacting the reactant with hydrogen and a nitrogen compound selected from the group consisting of ammonia, primary amines, secondary amines and mixtures thereof, in the presence of a catalyst comprising a zirconium dioxide- and nickel-containing catalytically active composition, to form an amine; wherein the catalytically active composition, prior to reduction with hydrogen, comprises oxygen compounds of zirconium, copper, nickel and cobalt, and one or more oxygen compounds of molybdenum in an amount of 5.5 to 12% by weight, calculated as MoO3.Type: GrantFiled: July 4, 2007Date of Patent: July 13, 2010Assignee: BASF SEInventors: Petr Kubanek, Bram Willem Hoffer, Ekkehard Schwab, Johann-Peter Melder, Holger Evers, Till Gerlach
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Publication number: 20090054689Abstract: The present invention provides a production method of an allylic amine represented by the formula (III): wherein R3 is as defined in the specification, which comprises reacting by an allylic alcohol represented by the formula (II): wherein R3 is as defined in the specification, with sulfamic acid, in the presence of a phosphoramidite ligand represented by the formula (I): wherein each symbol is as defined in the specification, and an iridium complex. According to the present invention, a primary allylic amine can be produced directly from an allylic alcohol, without use of an activator for an allylic alcohol and conversion of an allylic alcohol into an activated compound thereof.Type: ApplicationFiled: March 10, 2008Publication date: February 26, 2009Applicants: SUMITOMO CHEMICAL COMPANY, LIMITEDInventor: Erick M. CARREIRA
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Patent number: 7183438Abstract: Disclosed are catalysts, the catalytically active mass of which contains 22 to 40 percent by weight of oxygen-containing compounds of zirconium, calculated as ZrO2, 1 to 30 percent by weight of oxygen-containing compounds of copper, calculated as CuO, 15 to 50 percent by weight of oxygen-containing compounds of nickel, calculated as NiO, the molar ratio between nickel and copper being greater than 1, 15 to 50 percent by weight of oxygen-containing compounds of cobalt, calculated as CoO, and less than 1 percent by weight of an alkali metal, calculated as alkali metal oxide, prior to being treated with hydrogen. Also disclosed is a method for the production of amines by reacting primary and secondary alcohols, aldehydes, or ketones with hydrogen and nitrogen compounds selected from the group ammonia, primary and secondary amines, in the presence of said catalysts at an elevated temperature and an elevated pressure.Type: GrantFiled: March 7, 2003Date of Patent: February 27, 2007Assignee: BASF AktiengesellschaftInventors: Till Gerlach, Frank Funke, Johann-Peter Melder, Stefan Iselborn, Martin Rudloff, Michael Hüllmann
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Patent number: 7034186Abstract: Process for preparing an amine by reacting a primary or secondary alcohol, aldehyde or ketone with hydrogen and a nitrogen compound selected from the group consisting of ammonia and primary and secondary amines in the presence of a catalyst whose preparation has involved precipitation of catalytically active components onto monoclinic, tetragonal or cubic zirconium dioxide.Type: GrantFiled: December 10, 2003Date of Patent: April 25, 2006Assignee: BASF AktiengesellschaftInventors: Till Gerlach, Frank Funke, Johann-Peter Melder
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Patent number: 6689914Abstract: The preparation of amines of the formula (I): R1R2CH—N R3R4 (I) in which R1, R2, R3 and R4, independently of one another, are hydrogen, straight-chain or branched C1-C12-alkyl, C3-C12-cycloalkyl, C6-C10-aryl or C7-C11-aralkyl, takes place by catalytic, reductive amination of mixtures comprising carbonyl compounds of the formula (II) and/or alcohols of the formula (III) R1—C(═O)—R2 (II) R1—CH(OH)—R2 (III) which also comprise at least 50 ppm, based on the mixtures, of halogen, with nitrogen compounds of the formula (IV): H N R3 R4 (IV) with the abovementioned meanings for R1 to R4, in the presence of Co- and/or Ni-containing catalysts, which comprises carrying out the reductive amination additionally in the presence of solid acidic cocatalysts.Type: GrantFiled: September 5, 2002Date of Patent: February 10, 2004Assignee: BASF AktiengesellschaftInventors: Martin Schäfer, Arnd Böttcher, Andreas Kramer, Arthur Höhn, Shelue Liang, Frank Funke
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Patent number: 6525222Abstract: Amines are prepared by reacting aldehydes or ketones at elevated temperature under elevated pressure with nitrogen compounds selected from the group of ammonia, primary and secondary amines, and with hydrogen in the presence of a catalyst, wherein the catalytically active mass of the catalyst contains, after its preparation and before the treatment with hydrogen, 22 to 45% by weight of oxygen-containing compounds of zirconium, calculated as ZrO2, 1 to 30% by weight of oxygen-containing compounds of copper, calculated as CuO, 5 to 50% by weight of oxygen-containing compounds of nickel, calculated as NiO, where the molar ratio of nickel to copper is greater than 1, 5 to 50% by weight of oxygen-containing compounds of cobalt, calculated as CoO, 0 to 5% by weight of oxygen-containing compounds of molybdenum, calculated as MoO3, and 0 to 10% by weight of oxygen-containing compounds of aluminum and/or manganese, calculated as Al2O3 or MnO2.Type: GrantFiled: December 5, 2000Date of Patent: February 25, 2003Assignee: BASF AktiengesellschaftInventors: Jan Nouwen, Arthur Höhn, Horst Neuhauser, Frank Funke, Stephan Andreas Schunk, Johann-Peter Melder, Knut Eger, Michael Hesse, Joachim Wulff-Döring
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Patent number: 6403834Abstract: The invention concerns a method for preparing tris(ether-amines) of formula (I): N[A—O—(B—O)n—R]3 wherein R, A, B and n are as defined in Claim 1, comprising the reaction, in liquid phase, of an alkylene-glycol monoether of formula (II): HO—A—O—(B—O)nR wherein R, A, B and n are as defined in Claim 1, with an ammonolysis agent selected among ammonia and an etheramine of formula (I′): H3-pN[A—O—(B—O)nR]p wherein: A, B, n and R are as defined in Claim 1 and p represent 1 or 2, at a temperature ranging between 100 and 250° C., by contacting reagents with a hydrogenation-dehydrogenation catalyst.Type: GrantFiled: July 23, 2001Date of Patent: June 11, 2002Assignee: Rhodia ChimieInventors: Michel Alas, Albert Bouniot
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Patent number: 6187957Abstract: Amines are prepared by reacting primary or secondary alcohols, aldehydes or ketones with nitrogen compounds selected from the group consisting of ammonia and primary and secondary amines at elevated temperatures and superatmospheric pressures in the presence of hydrogen and of a catalyst containing copper and oxygen-containing compounds of titanium by a process in which the catalyst is used in the form of moldings which have been prepared with the addition of metallic copper powder.Type: GrantFiled: December 14, 1999Date of Patent: February 13, 2001Assignee: BASF AktiengesellschaftInventors: Gerald Meyer, Frank Funke, Gerhard Schulz, Detlef Kratz, Marc Walter, Michael Hesse
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Patent number: 6046359Abstract: 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: GrantFiled: March 4, 1999Date of Patent: April 4, 2000Assignee: BASF AktiengesellschaftInventors: Joachim Wulff-Doring, Johann-Peter Melder, Gerhard Schulz, Guido Voit, Gutshoven Frank, Wolfgang Harder
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Patent number: 5841001Abstract: The present invention provides an industrially advantageous process for the preparation of an optically active 2-halo-1-(substituted phenyl)ethanol useful as medicines, agricultural chemicals or as intermediates thereof; and a simple process for the preparation of an optically active substituted styrene oxide or 2-amino-1-(substituted phenyl)ethanol useful as medicines, agricultural chemicals or intermediates thereof. A 2-halo-1-(substituted phenyl)ethanol represented by the following general formula (I) is allowed to contact, in the presence of a carboxylic anhydride, with an enzyme stereoselectively catalyzing ester interchange to produce an optically active 2-halo-1-(substituted phenyl)ethanol: ##STR1## (wherein X represents a chlorine atom or a bromine atom, and R.sup.1, R.sup.2 and R.sup.3 may be the same or different and each represent a hydrogen atom, a halogen atom, a C.sub.1-5 alkyl group, a C.sub.1-5 haloalkyl group, a C.sub.Type: GrantFiled: February 28, 1997Date of Patent: November 24, 1998Assignee: Mitsubishi Chemical CorporationInventors: Ken Tanaka, Mari Yasuda, Makoto Ueda
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Patent number: 5684132Abstract: The present invention relates to a process for preparing protected amines or amino acids. The invention furthermore relates to the use of tocopheryl radicals or radicals derived therefrom as protective groups for amines and amino acids, and to compounds obtained in this process as intermediates and to processes for preparing dipeptides and oligopeptides.Type: GrantFiled: December 4, 1995Date of Patent: November 4, 1997Assignee: BASF AktiengsellschaftInventors: Thomas Rosenau, Wolf-Dieter Habicher, Chen-Loung Chen
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Patent number: 5663442Abstract: The invention relates to a process for the preparation of compounds of the formula ##STR1## characterized in that the radical X in sulphones of the formulaX--(CH.sub.2 --CH.sub.2 --O).sub.m --(CH.sub.2).sub.n --SO.sub.2 --CH.sub.2 --CH.sub.2 OH (2)is replaced by ##STR2## or a compound of the formula ##STR3## is added to the sulphone of the formulaCH.sub.2 =CH--SO.sub.2 --CH.sub.2 --CH.sub.2 --OH (3),the substituents having the meanings given in the description.Type: GrantFiled: May 31, 1995Date of Patent: September 2, 1997Assignee: Bayer AktiengesellschaftInventors: Wolfgang Harms, Udo-Winfried Hendricks, Karl-Josef Herd, Klaus Kunde
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Patent number: 5371290Abstract: A process for the preparation of N,N-dialkylarylamines (I) by reacting arylamines (II) with alcohols (IIIa) or dialkyl ethers (IIIb) in the presence of an oxygen acid of phosphorus or in the presence of an ammonium salt thereof as catalyst, comprises reacting the oxygen acid of phosphorus with an arylamine (IV) before the reaction is commenced. The invention also relates to the regeneration of the catalyst by occasionally interrupting the reaction and treating the catalyst phase at from 100.degree. to 300.degree. C. with steam or water.Type: GrantFiled: January 31, 1994Date of Patent: December 6, 1994Assignee: BASF AktiengesellschaftInventors: Peter Reuter, Willi A. Weber, Hans Diem
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Patent number: 5202485Abstract: A process for preparing an N-alkylaminophenol is disclosed, comprising subjecting an aminophenol to reductive alkylation with an aldehyde or a ketone in the presence of an organic solvent and hydrogen, wherein the reductive alkylation is carried out at a temperature of from 20.degree. to 70.degree. C. in the further presence of a catalyst for reduction comprising platinum and at least one metal element selected from metal elements belonging to the IB group, IIB group, IVB group, VB group, and VIB group of the Periodic Table, supported on activated carbon, or comprising palladium and at least one metal element selected from metal elements belonging to the IB group, IIB group, IVB group, VB group and VIB group of the Periodic Table, supported on activated carbon.Type: GrantFiled: April 29, 1991Date of Patent: April 13, 1993Assignee: Sumitomo Chemical Co., Ltd.Inventors: Hiroshi Maki, Michihiro Kawasaki, Horishi Shimizu, Yoshiaki Ito
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Patent number: 5198592Abstract: The invention concerns a method of performing a chemical reaction in which hydrogenation and/or dehydrogenation occurs, in the presence of a supported catalyst comprising a carrier material with copper as active component and iron as a promotor. According to the invention, the proporation of iron, calculated on the amount of copper and iron jointly, on an atomic basis, is no more than 25%. The invention also relates to a catalyst for carrying out the reaction, and to a process for preparing a supported catalyst.Type: GrantFiled: October 15, 1990Date of Patent: March 30, 1993Assignee: Engelhard De Meern B.V.Inventors: Johannes van Beijnum, Adrianus J. van Dillen, John W. Geus
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Patent number: 5166440Abstract: Aromatic amines, alkylated on the N-atom, can be prepared by catalytic alkylation of aromatic amines with alcohols or the corresponding ethers or by transalkylation with aromatic amines alkylated on the N-atom, whereby niobic acid or tantalic acid is used as the catalyst.Type: GrantFiled: December 12, 1990Date of Patent: November 24, 1992Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Helmut Waldmann, Rudolf Braden
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Patent number: 5159115Abstract: Described are processes for the gas-phase mono N-alkylation of an aniline or an aminonaphthalene using a C.sub.1 to C.sub.5 aliphatic alcohol or ether over certain catalyst compositions based upon crystalline molecular sieves or amorphous silica-aluminas.Type: GrantFiled: August 18, 1989Date of Patent: October 27, 1992Assignee: Amoco CorporationInventors: Peter G. Pappas, Judith B. Melville
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Patent number: 5155271Abstract: The invention relates to a process for the preparation of compounds of the formula ##STR1## in which Q is substituted or unsubstituted C.sub.1 -C.sub.6 alkyl, A is a direct bond or a bridging member, s is the number 1 or 2, Z is a radical of the formula --CH.sub.2 CH.sub.2 OH, --CH.dbd.CH.sub.2 or --CH.sub.2 CH.sub.2 --Y, and Y is a leaving group, and the benzene or napthalene nucleus I can be further substituted, which comprises reacting compounds of the formula ##STR2## with compounds of the formulaQ--OH (3)in which A, s, Z and Q are as defined under formula (1), in the presence of hydrogenation catalysts, and then carrying out further conversion reactions where appropriate.The compounds obtained by the process according to the invention are suitable as intermediates for the preparation of reactive dyes.Type: GrantFiled: June 25, 1990Date of Patent: October 13, 1992Assignee: Ciba-Geigy CorporationInventor: Peter Aeschlimann
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Patent number: 5118851Abstract: A process of preparing a mixture of polyalkylenepolyamines and alkanolpolyamines comprising contacting a difunctional aliphatic alcohol with a primary or secondary aliphatic amine in the presence of a metal silicate catalyst wherein the metal is selected from the group consisting of Groups IIA, IIIB, and the lanthanide and actinide metals. For example, monoethanolamine reacts with diethylenetriamine in the presence of magnesium silicate to yield a mixture of higher molecular weight linear and branched polyethylenepolyamines and their corresponding alkanolpolyamines. These product mixtures are useful in the formation of specialty polyurethanes.Type: GrantFiled: December 5, 1990Date of Patent: June 2, 1992Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
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Patent number: 5110928Abstract: 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.Type: GrantFiled: March 15, 1991Date of Patent: May 5, 1992Assignee: BASF AktiengesellschaftInventors: Wolfgang Schroeder, Guenther Ruider
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Patent number: 5097071Abstract: The novel copper catalyst on an Al.sub.2 O.sub.3 -containing carrier which is impregnated with compounds of manganese and of one or more rare earth metals, having a Cu content of 0.1-5% by weight, a total content of compounds of manganese and of the rare earth metal or metals of 0.05 to 8% by weight, calculated as metals, is described, the weight ratio of rare earth metal(s) to manganese being 5:1-1:5, calculated as metal, and all percentages being relative to the total weight of the catalyst. Such catalyst is prepared by first impregnating the carrier with compounds of manganese and of the rare earth metal or metals, then fixing the copper salt on the impregnated carrier and activating the catalyst in a preferred manner by treatment with H.sub.2 at 150.degree. to 350.degree. C. Such a catalyst is suitable, for example, for the N-alkylation of aromatic amines with alkanols, where the aromatic amines can be prepared from the parent nitro compounds in an alkylation reactor with simultaneous addition of H.sub.2.Type: GrantFiled: September 20, 1990Date of Patent: March 17, 1992Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Hans-Helmut Schwarz, Rudolf Braden
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Patent number: 5087754Abstract: 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: GrantFiled: August 13, 1990Date of Patent: February 11, 1992Assignee: Bayer AktiengesellschaftInventors: Hans-Josef Buysch, Heinrich Pelster, Lothar Puppe, Peter Wimmer
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Patent number: 5068434Abstract: N-alkylated anilines can be prepared by reaction of anilines with lower alcohols or dialkyl ethers at elevated temperature and in the presence of zeolite catalysts of the pentasil type containing protons and having an SiO.sub.2 /Al.sub.2 O.sub.3 ratio of at least 60.Type: GrantFiled: January 25, 1989Date of Patent: November 26, 1991Assignee: Bayer AktiengesellschaftInventors: Gunter Klug, Hans-Josef Buysch, Lothar Puppe
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Patent number: 5055617Abstract: Anilines or N-alkyl-anilines are advantageously reacted with alkyl alcohols or the associated dialkyl ethers at elevated temperature in the gas phase, if a .gamma.-Al.sub.2 O.sub.3 is used that is prepared by dehydration of an aluminum oxide/hydroxide hydrate and has a BET surface area from 50 to 400 m.sup.2 /g and a surface acidity of 5 to 600 mmol H.sup.+ /kg.Type: GrantFiled: July 12, 1990Date of Patent: October 8, 1991Assignee: Bayer AktiengesellschaftInventors: Peter Wimmer, Hans-Josef Buysch, Lothar Puppe, Christian Froehlich
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Patent number: 5030759Abstract: 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: GrantFiled: April 27, 1989Date of Patent: July 9, 1991Assignee: First Chemical CorporationInventors: Arthur C. Bayer, Charles U. Pittman, Jr., Lichang Wang, Earl G. Alley, Anthony C. Maliyackel
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Patent number: 5015773Abstract: An amine is produced by reacting in the presence of hydrogen at elevated temperature a first reactant which is a compound substantially involatile at the elevated temperature employed and having either one, two or more hydroxyl functions, each of which is independently either a primary or secondary hydroxyl function, with a second reactant which is either ammonia or a primary or a secondary amine in the presence of a reductive amination catalyst wherein the reaction is effected in either a continuously or periodically open system.Type: GrantFiled: August 4, 1989Date of Patent: May 14, 1991Assignee: BP Chemicals LimitedInventor: Ian D. Dobson
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Patent number: 4992587Abstract: Process for preparing a ruthenium promoted, halogen-containing, nickel and/or cobalt catalyst includes impregnating, in one or more steps, a porous metal oxide support with a nickel compound and/or a cobalt compound, and a ruthenium compound to form a catalyst intermediate; reducing the nickel compound and/or cobalt compound, and ruthenium compound, in one or more steps, to the respective metal by reacting the catalyst intermediate with hydrogen gas at an elevated temperature sufficient to reduce the respective compounds to the metal; and introducing halogen by adding a halide compound at any stage in the process. Catalyst prepared by the above process and use thereof.Type: GrantFiled: June 2, 1989Date of Patent: February 12, 1991Assignee: Berol Kemi ABInventor: Juhan Koll
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Patent number: 4950690Abstract: The present invention is a process for selectively aminating alcohols wherein a mixture of an amine and a primary or secondary alcohol or diol is contacted with a catalytically effective amount of a phosphorus-containing catalyst which has been impregnated or titrated with a metal cation salt composition represented by the formula:M.sub.a.sup.m.spsp.+ X.sub.b.sup.n.spsp.-wherein M.sup.m+ is a cation selected from Group Ia and IIa of the Periodic Table of the elements having a valence m, X.sup.n- is an organic or inorganic anionic species having a valence n, and a and b are integers such that the ratio of a to b provides a neutral salt. A typical reaction includes the amination of ethanol with piperidine to form N-ethylpiperidine.Type: GrantFiled: November 28, 1988Date of Patent: August 21, 1990Assignee: Air Products and Chemicals, Inc.Inventors: Gene E. Parris, Ronald Pierantozzi
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Patent number: 4922024Abstract: A process for preparing amines comprising contacting an alcohol with a reactant amine in the presence of hydrogen and a catalyst comprising at least one compound containing an element of Group VIB and at least one non-metallic element of Groups IIIA, IVA, and VA of the Periodic Table, the contacting occurring under conditions such that the hydroxyl moiety of the alcohol is replaced by the reactant amine to form an amine product.Type: GrantFiled: April 14, 1988Date of Patent: May 1, 1990Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, Marvin H. Tegen, George E. Hartwell
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Patent number: 4921980Abstract: A process for the preparation of N-alkylanilines is described, the most essential feature of which comprises reacting corresponding anilines at 150.degree. to 300.degree.C. with corresponding alcohols in the presence of a catalyst consisting of silica gel as carrier, of 0.2 to 10% of platinum and of 0.05 to 3% of a compound of a metal of the groups Ia and/or IIa of the Periodic Table, with the catalyst additionally containing at least one compound of an element of the groups Ib, IVa, IVb, Vb, VIIb and VIII in such an amount that the atomic ratio of platinum to the sum of these elements is 1 to 6.Type: GrantFiled: May 22, 1987Date of Patent: May 1, 1990Assignee: Ciba-Geigy CorporationInventor: Milos Rusek
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Patent number: 4888447Abstract: A process is described for selectively preparing alkoxylated tertiary amine compounds, such as aminated ethoxylated amines, at ambient pressure by reacting an oxyalkylated alcohol with a secondary amine in the presence of a reductive amination catalyst at above ambient temperature using, as a reductive amination catalyst, a combination of Raney nickel and molybdenum.Type: GrantFiled: June 30, 1988Date of Patent: December 19, 1989Assignee: Ethyl CorporationInventor: Kim R. Smith
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Patent number: 4855505Abstract: The invention relates to a ruthenium promoted nickel and/or cobalt dehydrogenation-hydrogenation catalyst. The ruthenium on the catalyst is applied from a solution containing a ruthenium halide compound. The catalyst use in organic reactions and a process performed in its presence are also described. Preferably, the catalyst is used to aminate alkylene oxides, alcohols, phenols, alkanolamines, aldehydes, and ketones.Type: GrantFiled: December 8, 1986Date of Patent: August 8, 1989Assignee: Berol Kemi ABInventor: Juhan Koll
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Patent number: 4801752Abstract: The present invention relates to a vapor phase process for the production of N-alkyl and N,N-dialkylaniline by alkylation of aniline with an alcohol, preferably methanol and ethanol, in the presence of a ZSM-5 catalyst. A modified ZSM-5 catalyst has the advantage of high selectivity for N-alkylation while suppressing the formation of undesired by-products, such as toluidines. The molar ratio of silica to alumina in the catalyst is from about 20:1 to 700:1 and preferably from about 30:1 to 200:1. The silica-alumina may be modified with alkali metal, alkali earth metal or transition metal ions, preferably cesium, potassium, magnesium and iron, to form the finished catalyst. The reactants are contacted in the presence of the catalyst at a temperature of from about 300.degree. to 500.degree. C., at a pressure of from about 1 to 3 atmospheres, and at a molar ratio of alcohol to aniline of from about 1 to 6. The feed rates expressed as weight hourly space velocity (g feed/g catalyst/hour) are broadly from about 0.Type: GrantFiled: February 12, 1987Date of Patent: January 31, 1989Assignee: Industrial Technology Research InstituteInventors: Po Y. Chen, Shiao J. Chu, Mei C. Chen, Nan S. Chang, Wen C. Lin
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Patent number: 4621158Abstract: A method for making amines by reacting alcohols and/or aldehydes with primary and/or secondary amines or with ammonia in the presence of a catalyst at elevated temperature, and optionally at elevated pressure, in the liquid phase, the catalyst being an unsupported catalyst consisting of a combination of copper and tin compounds.Type: GrantFiled: August 21, 1985Date of Patent: November 4, 1986Assignee: Schering AktiengesellschaftInventors: Hans-Juergen Hubert, Klaus D. Tillmetz
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Patent number: 4613705Abstract: Aromatic amines are alkylated by reaction with an alcohol in the presence of a Group V-B metal oxide alkylation catalyst, preferably a major proportion of a Group V-B metal oxide such as V.sub.2 O.sub.5 in combination with a minor proportion of an A-subgroup metal oxide such as SnO.sub.2, so that alkylation of the aromatic amine occurs. Under most reaction conditions a considerable portion of the alcohol alkylating agent such as ethanol not consumed in the alkylation reaction passes through the reaction zone undecomposed and thus can be readily recovered for recycle or other use.Type: GrantFiled: June 25, 1984Date of Patent: September 23, 1986Assignee: Ethyl CorporationInventor: Duane C. Hargis
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Patent number: 4395572Abstract: This invention relates to a process of preparing N-alkyl-nitroanilines selected from the group consisting of N-alkyl-mononitroanilines and N-alkyl-dinitroanilines by the O-alkylation of a nitrophenol to produce the corresponding alkoxy derivative, followed by reaction of the alkoxy derivative with alkylamine to produce the desired N-alkyl-nitroaniline.Type: GrantFiled: April 20, 1981Date of Patent: July 26, 1983Assignee: Union Carbide CorporationInventor: John K. Chan
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Patent number: 4322530Abstract: A process for alkylating a polyamine by contacting, in a liquid media, a polyamine, an olefinic compound, carbon monoxide, and a hydrogen source in the presence of a catalytic amount of a rhodium atom containing compound selected from metallic rhodium, rhodium salts, rhodium oxides, rhodium carbonyls and ligands thereof at a temperature of from about 50.degree. C. to 250.degree. C. and at a pressure of from about 30 to about 300 atmospheres.Type: GrantFiled: February 22, 1980Date of Patent: March 30, 1982Assignee: W. R. Grace & Co.Inventor: Felek Jachimowicz
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Patent number: 4317932Abstract: A process for forming amines by contacting, in a liquid media, an olefinic compound, carbon monoxide, water, and ammonia in the presence of a rhodium atom containing compound selected from metallic rhodium, rhodium salts, rhodium oxides, and rhodium carbonyls and ligands thereof at a temperature of from 50.degree. to 250.degree. C. and at a pressure of from about 10 to about 300 atmospheres.Type: GrantFiled: February 22, 1980Date of Patent: March 2, 1982Assignee: W. R. Grace & Co.Inventor: Felek Jachimowicz
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Patent number: 4289907Abstract: This invention relates to a process of preparing N-alkyl-nitroanilines selected from the group consisting of N-alkyl-mononitroanilines and N-alkyl-dinitroanilines by the O-alkylation of a nitrophenol to produce the corresponding alkoxy derivative, followed by reaction of the alkoxy derivative with alkylamine to produce the desired N-alkyl-nitroaniline.Type: GrantFiled: December 27, 1979Date of Patent: September 15, 1981Assignee: Union Carbide CorporationInventor: John K. Chan