Plural Amino Nitrogens Containing Patents (Class 564/451)
  • Patent number: 5675035
    Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and to their use.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: October 7, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5672737
    Abstract: The invention relates to a process for the fractionation and purification of mixtures of aromatic polyamines and to the use thereof.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: September 30, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5663443
    Abstract: 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: Grant
    Filed: February 3, 1995
    Date of Patent: September 2, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfgang Kiel, Eberhard Zirngiebl, Joerg-Dietrich Jentsch
  • Patent number: 5663424
    Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and the use thereof.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: September 2, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5648520
    Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and the use thereof.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: July 15, 1997
    Assignee: Bayer Aktiengesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5648519
    Abstract: The invention relates to a process for the fractionation and purification of aromatic polyamine mixtures and to the use thereof.
    Type: Grant
    Filed: March 28, 1996
    Date of Patent: July 15, 1997
    Assignee: Bayer Aktiengesesellschaft
    Inventors: Hartmut Knofel, Michael Brockelt
  • Patent number: 5550294
    Abstract: 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: Grant
    Filed: September 16, 1994
    Date of Patent: August 27, 1996
    Assignee: Olin Corporation
    Inventor: Peter J. Whitman
  • Patent number: 5545756
    Abstract: 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: Grant
    Filed: September 14, 1994
    Date of Patent: August 13, 1996
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gamini A. Vedage, John N. Armor
  • Patent number: 5386060
    Abstract: 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: Grant
    Filed: October 23, 1992
    Date of Patent: January 31, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Immel, Gerhard Darsow, Helmut Waldmann, Gerd-Michael Petruck
  • Patent number: 5360934
    Abstract: 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: Grant
    Filed: June 25, 1993
    Date of Patent: November 1, 1994
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gamini A. Vedage, John N. Armor
  • Patent number: 5245082
    Abstract: 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: Grant
    Filed: January 14, 1993
    Date of Patent: September 14, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Immel, Gerhard Darsow, Rudolf Braden, Hans-Helmut Schwarz, Helmut Waldmann
  • Patent number: 5214212
    Abstract: 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: Grant
    Filed: February 27, 1992
    Date of Patent: May 25, 1993
    Assignee: Olin Corporation
    Inventor: Peter J. Whitman
  • Patent number: 5196587
    Abstract: 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: Grant
    Filed: May 13, 1991
    Date of Patent: March 23, 1993
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gamini A. Vedage, William W. Henderson, Bernard A. Toseland
  • Patent number: 5126426
    Abstract: 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: Grant
    Filed: April 19, 1990
    Date of Patent: June 30, 1992
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Ryuji Haseyama, Masatoshi Takagi, Kouzou Hayashi, Katsuyoshi Sasagawa, Kazuyuki Kuroda, Taisaku Kano, Kiyoshi Shikai
  • Patent number: 5066764
    Abstract: 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: Grant
    Filed: June 26, 1990
    Date of Patent: November 19, 1991
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Jeremiah P. Casey, Peter A. Lucas, Menas S. Vratsanos
  • Patent number: 5026914
    Abstract: 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: Grant
    Filed: April 11, 1989
    Date of Patent: June 25, 1991
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Richard J. Jenkins, Robert A. Treskot, Gamini A. Vedage, James F. White
  • Patent number: 4960941
    Abstract: 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: Grant
    Filed: March 30, 1988
    Date of Patent: October 2, 1990
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gamini A. Vedage, William W. Henderson, Bernard A. Toseland, Michel Deeba
  • Patent number: 4946998
    Abstract: 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: Grant
    Filed: February 10, 1988
    Date of Patent: August 7, 1990
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Jeremiah P. Casey, Michael J. Fasolka
  • Patent number: 4849544
    Abstract: 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: Grant
    Filed: April 13, 1988
    Date of Patent: July 18, 1989
    Assignee: Ethyl Corporation
    Inventors: Scott A. Culley, Kestutis A. Keblys, Christopher J. Nalepa
  • Patent number: 4754070
    Abstract: 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: Grant
    Filed: January 23, 1986
    Date of Patent: June 28, 1988
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Jeremiah P. Casey, Michael J. Fasolka
  • Patent number: 4716248
    Abstract: 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: Grant
    Filed: October 12, 1984
    Date of Patent: December 29, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Frederick H. Howell, Josef Pfeifer
  • Patent number: 4448995
    Abstract: 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: Grant
    Filed: December 13, 1982
    Date of Patent: May 15, 1984
    Assignee: Mobay Chemical Corporation
    Inventor: Gary F. Allen
  • Patent number: 4394523
    Abstract: 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: Grant
    Filed: June 1, 1981
    Date of Patent: July 19, 1983
    Assignee: Mobay Chemical Corporation
    Inventor: Gary F. Allen
  • Patent number: 4394522
    Abstract: 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: Grant
    Filed: June 1, 1981
    Date of Patent: July 19, 1983
    Assignee: Mobay Chemical Corporation
    Inventor: Gary F. Allen
  • Patent number: 4384142
    Abstract: 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: Grant
    Filed: June 9, 1981
    Date of Patent: May 17, 1983
    Assignee: Monsanto Company
    Inventors: Helmut L. Merten, Gene R. Wilder