Plural Amino Nitrogens Containing Patents (Class 564/451)
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Patent number: 5675035Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and to their use.Type: GrantFiled: March 28, 1996Date of Patent: October 7, 1997Assignee: Bayer AktiengesellschaftInventors: Hartmut Knofel, Michael Brockelt
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Patent number: 5672737Abstract: The invention relates to a process for the fractionation and purification of mixtures of aromatic polyamines and to the use thereof.Type: GrantFiled: March 28, 1996Date of Patent: September 30, 1997Assignee: Bayer AktiengesellschaftInventors: Hartmut Knofel, Michael Brockelt
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Patent number: 5663443Abstract: Novel ruthenium catalysts additionally contain carbonates, hydroxides and/or hydrated oxides of cerium and manganese or of manganese and/or dehydration products thereof. They can optionally be present on a support material and can be prepared by converting soluble compounds of ruthenium, cerium and manganese by treatment with alkaline compounds into insoluble compounds and optionally further treating these. Such catalysts are particularly suitable for the preparation of cycloaliphatic polyamines by hydrogenation of corresponding aromatic amines.Type: GrantFiled: February 3, 1995Date of Patent: September 2, 1997Assignee: Bayer AktiengesellschaftInventors: Wolfgang Kiel, Eberhard Zirngiebl, Joerg-Dietrich Jentsch
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Patent number: 5663424Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and the use thereof.Type: GrantFiled: March 28, 1996Date of Patent: September 2, 1997Assignee: Bayer AktiengesellschaftInventors: Hartmut Knofel, Michael Brockelt
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Patent number: 5648519Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and to the use thereof.Type: GrantFiled: March 28, 1996Date of Patent: July 15, 1997Assignee: Bayer AktiengesesellschaftInventors: Hartmut Knofel, Michael Brockelt
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Patent number: 5648520Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and the use thereof.Type: GrantFiled: March 28, 1996Date of Patent: July 15, 1997Assignee: Bayer AktiengesellschaftInventors: Hartmut Knofel, Michael Brockelt
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Patent number: 5550294Abstract: A process for increasing the rate of catalytic hydrogenation of aromatic amines by reacting aromatic amines with hydrogen in the presence of a noble metal catalyst, a water miscible organic solvent, lithium hydroxide catalyst promoter, and water in an effective amount to increase the rate of the hydrogenation reaction without an appreciable increase in total amounts of by-products.Type: GrantFiled: September 16, 1994Date of Patent: August 27, 1996Assignee: Olin CorporationInventor: Peter J. Whitman
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Patent number: 5545756Abstract: This invention relates to an improved hydrogenation process wherein aromatic amines are hydrogenated to their ring hydrogenated counterparts using an improved rhodium catalyst. The aromatic amines are represented by the formulas: ##STR1## wherein R is hydrogen or C.sub.1-6 aliphatic, R.sub.1 and R.sub.2 are hydrogen or C.sub.1-6 aliphatic, A is C.sub.1-4 alkyl, n is 0 or 1, x is 1-3 and y is 1 to 2 except the sum of the y groups in Formula I excluding A may be 1.The rhodium catalyst is carried on a support selected from the group consisting of TiAl.sub.2 O.sub.5, TiSrO.sub.3 and TiSiO.sub.4.Type: GrantFiled: September 14, 1994Date of Patent: August 13, 1996Assignee: Air Products and Chemicals, Inc.Inventors: Gamini A. Vedage, John N. Armor
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Patent number: 5386060Abstract: A Pd catalyst in which an .alpha.- or .gamma.-Al.sub.2 O.sub.3 as support is first treated with at least one compound of the rare earth metals and with at least one compound of manganese and then with at least one palladium compound is suitable for the preparation of a mixture of optionally substituted cyclohexylamine and optionally substituted dicyclohexylamine by hydrogenation of a correspondingly substituted aniline.Type: GrantFiled: October 23, 1992Date of Patent: January 31, 1995Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Gerhard Darsow, Helmut Waldmann, Gerd-Michael Petruck
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Patent number: 5360934Abstract: This invention relates to an improved hydrogenation process wherein aromatic amines are hydrogenated to their ring hydrogenated counterparts. These aromatic amines are presented by the formulas: ##STR1## wherein R is hydrogen or C.sub.1-6 aliphatic, R1 and R2 are hydrogen or C.sub.1-6 aliphatic, A is C.sub.1-4 or NH; n is 0-2, x is 1-3 and y is 1 to 2 except the sum of the y groups in Formula I may be 1. The improvement resides in the utilization of a catalyst comprising rhodium carried on a support of kappa, theta or delta alumina.Type: GrantFiled: June 25, 1993Date of Patent: November 1, 1994Assignee: Air Products and Chemicals, Inc.Inventors: Gamini A. Vedage, John N. Armor
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Patent number: 5245082Abstract: Di-(4-aminocyclohexyl)-methane containing 15 to 25% by weight of the trans-trans isomer can be obtained by the catalytic hydrogenation of di-(4-aminophenyl)-methane at elevated temperature and elevated hydrogen pressure in the presence of a ruthenium-containing supported catalyst containing 0.05 to 5% by weight ruthenium on an Al.sub.2 O.sub.3 support which has been treated with compounds of rare earth metals and manganese.Type: GrantFiled: January 14, 1993Date of Patent: September 14, 1993Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Gerhard Darsow, Rudolf Braden, Hans-Helmut Schwarz, Helmut Waldmann
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Patent number: 5214212Abstract: A process for increasing the rate of catalytic hydrogenation of aromatic amines by reacting aromatic amines with hydrogen in the presence of a noble metal catalyst, an organic solvent or a mixture of solvents, and at least one salt of a transition or lanthanide metal as a promoter, in an effective amount to increase the rate of the hydrogenation reaction, decrease the induction period, and decrease the amount of higher boiler by-products.Type: GrantFiled: February 27, 1992Date of Patent: May 25, 1993Assignee: Olin CorporationInventor: Peter J. Whitman
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Patent number: 5196587Abstract: This invention relates to an improved process for the catalytic hydrogenation of methylene bridged polyphenylamines using rhodium as th e catalyst to produce the methylene bridged polycyclohexylamine counterparts. The improvement for hydrogenating crude methylene bridged polyphenylamines containing polyphenylamine oligomers and trace amounts of impurities, such as the formamide of the methylene bridged polyphenylamines, comprises contacting the crude polyphenylamine feed with a hydrogenation catalyst, other than rhodium, and one which is not a catalyst poison to rhodium, under conditions sufficient to at least partially hydrogenate the polyphenylamine mixture and then effecting hydrogenation of the methylene bridged polyphenylamine to the polycyclohexylamine counterpart in the presence of a rhodium catalyst.Type: GrantFiled: May 13, 1991Date of Patent: March 23, 1993Assignee: Air Products and Chemicals, Inc.Inventors: Gamini A. Vedage, William W. Henderson, Bernard A. Toseland
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Patent number: 5126426Abstract: Herein disclosed are an .alpha.-(aminocyclohexyl)alkylamine represented by the following general formula (II): ##STR1## wherein R represents hydrogen atom or a lower alkyl group having 1 to 5 carbon atoms, provided that the amino group bonded to the cyclohexyl group may be in either of the 2-, 3- and 4-positions and a method for preparing it; an .alpha.-(isocyanatocyclohexyl)alkylisocyanate of Formula (II) wherein the amino groups are replaced with isocyanato groups and a method for preparing it; polyisocyanato-isocyanurate represented by the following general formula (IV): ##STR2## wherein R.sub.1, R.sub.2 and R.sub.Type: GrantFiled: April 19, 1990Date of Patent: June 30, 1992Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Ryuji Haseyama, Masatoshi Takagi, Kouzou Hayashi, Katsuyoshi Sasagawa, Kazuyuki Kuroda, Taisaku Kano, Kiyoshi Shikai
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Patent number: 5066764Abstract: This invention relates to ditertiary-butyl substituted bridged di(cyclohexylamines) where the tert-butyl substituent is alpha to the amine group and to polyepoxide formulations incorporating the di(cyclohexylamine). The formula of the diamine is: ##STR1## wherein R is tert-butyl. The di(tertiary butyl)methylene bridged cyclohexylamines have delayed reactivity when incorporated in epoxy resins and they also enhance physical properties in high resilience polyurethane foams.Type: GrantFiled: June 26, 1990Date of Patent: November 19, 1991Assignee: Air Products and Chemicals, Inc.Inventors: Jeremiah P. Casey, Peter A. Lucas, Menas S. Vratsanos
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Patent number: 5026914Abstract: This invention relates to an improved hydrogenation process wherein aromatic amines are hydrogenated to their ring hydrogenated counterparts using an improved rhodium catalyst and to the catalyst. The aromatic amines are represented by the formulas: ##STR1## wherein R is hydrogen or C.sub.1-6 aliphatic, R.sub.1 and R.sub.2 are hydrogen or C.sub.1-6 aliphatic, A is C.sub.1-4 alkylene, NH, or ##STR2## n is 0-2, x is 1-3 and y is 1 to 2 except the sum of the y groups in Formula I excluding A may be 1.The rhodium catalyst is supported on titania bonded to silica or zirconia or bonded with silica, zirconia or titania from a sol or zirconia bonded with silica or alumina. The resulting catalyst has greater activity and attrition resistance. Zirconia bonded with silica or alumina also results in a catalyst with increased attrition resistance.Type: GrantFiled: April 11, 1989Date of Patent: June 25, 1991Assignee: Air Products and Chemicals, Inc.Inventors: Richard J. Jenkins, Robert A. Treskot, Gamini A. Vedage, James F. White
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Patent number: 4960941Abstract: This invention relates to an improved hydrogenation process wherein aromatic amines are hydrogenated to their ring hydrogenated counterparts. These aromatic amines are presented by the formulas: ##STR1## wherein R is hydrogen or C.sub.1-6 aliphatic, R.sub.1 and R.sub.2 are hydrogen or C.sub.1-6 aliphatic, A is C.sub.1-4, NH or ##STR2## n is 0-2, x is 1-3 and y is 1 to 2 except the sum of the y groups in Formula I excluding A may be 1.The improvement resides in the use of a rhodium catalyst carried on titania support.Type: GrantFiled: March 30, 1988Date of Patent: October 2, 1990Assignee: Air Products and Chemicals, Inc.Inventors: Gamini A. Vedage, William W. Henderson, Bernard A. Toseland, Michel Deeba
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Patent number: 4946998Abstract: This invention relates to an improved hydrogenation process wherein methylenedianiline is reduced to form bis(para-aminocyclohexyl)methane (PACM). The process contemplates contacting methylenedianiline and hydrogen in the presence of a two component metal catalyst comprising rhodium and ruthenium under mild hydrogenation conditions. Use of the mixed metal catalyst system allows one to obtain a preselected isomer ratio having from about 5-40% by weight, typically 14`28% by weight of the trans,trans- configurational isomer.Type: GrantFiled: February 10, 1988Date of Patent: August 7, 1990Assignee: Air Products and Chemicals, Inc.Inventors: Jeremiah P. Casey, Michael J. Fasolka
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Patent number: 4849544Abstract: Sterically hindered 1,3-diaminocyclohexanes which can be used in the preparation of polyurethane, polyurea, polyurethaneurea, and epoxy resins are prepared by hydrogenating a metaphenylenediamine having alkyl substituents of 1-6 carbons in the 4- and 6-positions and optionally also in the 2-position, at least one of the alkyl substituents containing at least two carbons, and the total number of carbons in the alkyl substituents being at least five, at a temperature of about 170.degree.-200.degree. C. and a pressure of at least about 6.9 MPa, preferably about 20-30 MPa, in the presence of a supported ruthenium catalyst and an activating amount of a modifier selected from alkali metal hydroxides and alkoxides and alkali metal amide salts of the meta-phenylenediamine to form the corresponding 1,3-diaminocyclohexane.Type: GrantFiled: April 13, 1988Date of Patent: July 18, 1989Assignee: Ethyl CorporationInventors: Scott A. Culley, Kestutis A. Keblys, Christopher J. Nalepa
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Patent number: 4754070Abstract: This invention relates to an improved hydrogenation process wherein methylenedianiline is reduced to form bis(para-aminocyclohexyl)methane (PACM). The process contemplates contacting methylenedianiline and hydrogen in the presence of a two component metal catalyst comprising rhodium and ruthenium under mild hydrogenation conditions. Use of the mixed metal catalyst system allows one to obtain a preselected isomer ratio having from about 5-40% by weight, typically 14-28% by weight of the trans,trans- configurational isomer.Type: GrantFiled: January 23, 1986Date of Patent: June 28, 1988Assignee: Air Products and Chemicals, Inc.Inventors: Jeremiah P. Casey, Michael J. Fasolka
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Patent number: 4716248Abstract: New compounds having the formula:X--(YQNH.sub.2).sub.p Iwherein p is 1 or 2 and the residues QNH.sub.2 are the same or different and each is a residue of formula: ##STR1## wherein n is an integer from 1 to 15; R.sub.1 is C.sub.1 -C.sub.8 alkyl; R.sub.2 is C.sub.1 -C.sub.4 alkyl; or R.sub.1 and R.sub.2 ; together with the carbon atom to which they are attached, from a C.sub.5 -C.sub.8 cycloalkylene residue; R.sub.3 is H or C.sub.1 -C.sub.6 alkyl, C.sub.3 -C.sub.8 cycloalkyl or C.sub.6 -C.sub.10 aryl; and Y is a divalent residue of formula: ##STR2## wherein R.sub.4 and R.sub.5 are H or C.sub.1 -C.sub.4 alkyl or, when p is 1, the group R.sub.4, together with the group X, can form a tetramethylene chain substituted by the group QNH.sub.2, X is NH.sub.2 or QNH.sub.2 or X may be combined with R.sub.4 as hereinbefore defined; and, when p is 2, X is a direct bond or a --CH.sub.Type: GrantFiled: October 12, 1984Date of Patent: December 29, 1987Assignee: Ciba-Geigy CorporationInventors: Frederick H. Howell, Josef Pfeifer
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Patent number: 4448995Abstract: The present invention is directed to a process for the catalytic hydrogenation of di(4-aminophenyl)methane to a liquid di(4-aminocyclohexyl)methane containing from 15 to 40% by weight of the trans,trans isomer comprising hydrogenating di(4-aminophenyl)methane at a hydrogen pressure of at least 500 psi and at a temperature of from 100.degree. to 300.degree. C., in the presence of a ruthenium catalyst supported on an inert carrier, said catalyst being moderated with from 65 to 700% by weight, based on the weight of the ruthenium of a compound selected from the group consisting of nitrates and sulfates of alkali metals and alkaline earth metals.Type: GrantFiled: December 13, 1982Date of Patent: May 15, 1984Assignee: Mobay Chemical CorporationInventor: Gary F. Allen
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Patent number: 4394522Abstract: The present invention relates to an improved process for the catalytic hydrogenation of di(4-amino-phenyl)methane to a liquid di(4-aminocyclohexyl)methane mixture containing from 15 to 40% by weight and preferably from 18.5 to 23.5% by weight, of the trans, trans isomer. The invention resides in the use of an unsupported ruthenium dioxide catalyst under specific process conditions. During the hydrogenation reaction, a pressure of at least 2500 psi and a temperature of from 150.degree. to 210.degree. C. must be maintained.Type: GrantFiled: June 1, 1981Date of Patent: July 19, 1983Assignee: Mobay Chemical CorporationInventor: Gary F. Allen
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Patent number: 4394523Abstract: The present invention relates to an improved process for the catalytic hydrogenation of di(4-aminophenyl) methane to a liquid di(4-aminocyclohexyl) methane mixture containing from 15 to 40% by weight of the trans, trans isomer. The invention resides in the use of a ruthenium-on-alumina catalyst, the use of an aliphatic alcohol during hydrogenation and the use of ammonia during hydrogenation, with the hydrogenation being conducted under specific process conditions. The hydrogenation reaction is conducted for no more than about sixty minutes at a temperature of from 150.degree. to 217.degree. C. and at a hydrogen pressure of at least 500 psi.Type: GrantFiled: June 1, 1981Date of Patent: July 19, 1983Assignee: Mobay Chemical CorporationInventor: Gary F. Allen
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Patent number: 4384142Abstract: Cyclohexylamine is produced by the catalytic hydrogenation of aniline. In contact with a ruthenium catalyst and in the presence of from about one to about 8 parts by weight of ammonia, aniline is hydrogenated under an absolute pressure of from about 2 to about 5 MPa at a temperature of from about 160.degree. to about 180.degree. C. High yields and a minimum of byproducts result. The catalyst can be recycled.Type: GrantFiled: June 9, 1981Date of Patent: May 17, 1983Assignee: Monsanto CompanyInventors: Helmut L. Merten, Gene R. Wilder