Preparing Alicyclic Ring Containing Compound Directly By Hydrogenating Benzene Ring Patents (Class 564/450)
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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: 5514716Abstract: This disclosure relates to a novel class of hydroxamic and carboxylic acid based matrix metalloproteinase inhibitor derivatives. The disclosure further relates to pharmaceutical compositions containing such compounds and to the use of such compounds and compositions in the treatment of matrix metalloproteinase induced diseases.Type: GrantFiled: February 25, 1994Date of Patent: May 7, 1996Assignee: Sterling Winthrop, Inc.Inventors: Madhusudhan R. Gowravaram, Jeffrey Johnson, Ewell R. Cook, Robert C. Wahl, Alan M. Mathiowetz, Bruce E. Tomczuk, Ashis K. Saha
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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: 5371294Abstract: Cyclohexylamine and dicyclohexylamine can be prepared as a mixture with one another by reaction of phenol with aniline, ammonia or a mixture of aniline and ammonia in the presence of hydrogen over a catalyst, the reaction being carried out according to the invention over a palladium catalyst which has a support of niobic acid or tantalic acid or a mixture of niobic acid and tantalic acid or a support containing such acids. The reaction is carried out at 100.degree.-220.degree. C. under an H.sub.2 partial pressure of 0.5-500 bar.Type: GrantFiled: October 2, 1992Date of Patent: December 6, 1994Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Hans-Josef Buysch, Gerhard Darsow
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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: 5344990Abstract: Intermediates and a process for their preparation are disclosed which are useful for the preparation of a renin inhibiting compound of the formula: ##STR1## wherein R is a nitrogen-containing heterocycle which is bonded via a nitrogen atom to the sulfonyl group, R.sub.6 is hydrogen, alkoxy, halogen or loweralkyl, R.sub.7 is loweralkyl having 2 to 7 carbon atoms, and R.sub.8 is loweralkyl, cycloalkyl, or aryl or a pharmaceutically acceptable acid addition salt thereof.Type: GrantFiled: October 5, 1993Date of Patent: September 6, 1994Assignee: Abbott LaboratoriesInventors: William R. Baker, Stephen L. Condon
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Patent number: 5322965Abstract: Optionally substituted cyclohexylamine and optionally substituted dicyclohexylamine can be obtained by catalytic hydrogenation of optionally substituted aniline, a catalyst being employed which contains ruthenium, palladium or a mixture of both metals, which are applied to a support of niobic acid or tantalic acid or a mixture of both. The catalyst contains the noble metal(s) in a total amount from 0.05 to 5% by weight, relative to the total weight of the catalyst. In the case of the use of both noble metals, their weight ratio to one another is 1:9-9:1.Type: GrantFiled: August 27, 1993Date of Patent: June 21, 1994Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Gerhard Darsow, Helmut Waldmann, Gerd-Michael Petruck
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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: 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: 5023226Abstract: Substituted or unsubstituted cyclohexylamine and substituted or unsubstituted dicyclohexylamine can be produced by catalytic hydrogenation of substituted or unsubstituted aniline by using a ruthenium catalyst which in addition to ruthenium also contains palladium, platinum or palladium and platinum on a support from the group consisting of Al.sub.2 O.sub.3 and aluminum spinel treated with chromium and manganese and containing the noble metals in a total amount of 0.05-5% by weight and a weight ratio of Ru:Pd, Ru:Pt, or Ru:Pd/Pt of 1:9-9:1. All percentages are based on the total weight of the catalyst.Type: GrantFiled: January 9, 1989Date of Patent: June 11, 1991Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Hans-Helmut Schwarz, Reinhard Thiel
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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: 4952549Abstract: Substituted or unsubstituted cyclohexylamine and substituted or substituted dicyclohexylamine can be produced by catalytic hydrogenation of substituted or unsubstituted aniline, for which a catalyst is used containing ruthenium and palladium which are attached to a support and which catalyst furthermore contains a basic alkali metal compound. The catalyst contains the noble metals in a total amount of 0.05 to 5% by weight and in a weight ratio of ruthenium to palladium such as 1:9-9:1. The basic alkali metal compound is present in an amount of 0.1-10% by weight. All percentages are based on the total weight of the catalyst.Type: GrantFiled: January 10, 1989Date of Patent: August 28, 1990Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Hans-Helmut Schwarz
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Patent number: 4914239Abstract: Disclosed is a method for continuous production of a cyclohexylamine compound by liquid phase hydrogenation of an aniline compound selected from aniline, nuclearly lower alkyl-substituted aniline, N-(lower alkyl)aniline and N,N-di(lower alkyl)aniline with hydrogen gas in the presence of a nickel catalyst, which comprises continuously feeding an aniline compound, continuously hydrogenating the aniline compound in the absence of a solvent and in the presence of an ammonia compound at a reaction pressure of about 2 to 10 kg/cm.sup.2 and at about 210.degree. to 240.degree. C.Type: GrantFiled: April 6, 1988Date of Patent: April 3, 1990Assignee: New Japan Chemical Co., Ltd.Inventors: Tatsuo Kiyuma, Isao Naramoto
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Patent number: 4791215Abstract: New derivatives of D,L-glutamic acid and D,L-aspartic acid are described having the formulae: ##STR1## in which n is equal to 1 or 2, R.sub.1 is a phenyl group mono-, di- or tri-substituted with linear or branched C.sub.1 -C.sub.4 alkyl groups, which may be the same or different, or with halogens, with a cyano group or a trifluoromethyl group, and in which R.sub.2 is selected from the group consisting of morpholino, piperidino and amino with one or two linear, branched or cyclic alkyl group substituents containing from 1 to 8 carbon atoms, which may be the same or different, or a pharmaceutically-acceptable salt thereof.The compounds have an antagonistic activity towards bioactive polypeptides and are useful particularly in the treatment of illnesses of the digestive system and the central nervous system, as pain killers, and for the treatment of anorexia and all those affections (for example tumours) in which exogenous or endogenous bioactive polypeptides are involved.Type: GrantFiled: June 18, 1985Date of Patent: December 13, 1988Assignee: Rotta Research Laboratorium S.p.A.Inventors: Luigi Rovati, Francesco Makovec, Rolando Chiste', Paolo Senin
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Patent number: 4533752Abstract: Olefins are produced by containing an organic compound having at least one benzene ring with ethylenediamine and calcium metal, the calcium metal being used in large excess or alternatively in conjunction with an inert abrasive particulate substance. Substantially all of the organic compounds are converted to corresponding cyclic olefins, largely mono-olefins.Type: GrantFiled: August 23, 1984Date of Patent: August 6, 1985Assignee: Purdue Research FoundationInventors: Robert A. Benkeser, James A. Laugal, Angela Rappa
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Patent number: 4513149Abstract: Hydrogenation processes utilizing improved Raney nickel alloy catalysts are disclosed. The catalyst comprises a monolithic mesh type structure of a nickel alloy having an integral Beta phase Raney Ni.sub.x M.sub.1-x coating on its outer surfaces, where M is a catalytic activator selected from the group consisting of molybdenum, ruthenium, tantalum and titanium and where x, the weight fraction of nickel in the combined alloy, is between about 0.80 and about 0.95. The catalyst is effective in processes for hydrogenation of aromatic compounds of the type ##STR1## wherein K is either benzene or naphthalene, R.sub.1 is a hydrogen atom or an aliphatic chain containing from about 1 to about 9 carbon atoms or a phenyl radical, R.sub.2 is a hydrogen atom or an aliphatic chain containing from about 1 to about 3 carbon atoms, and R.sub.3 and R.sub.4 are hydrogen atoms, hydroxy, or nitro groups.Type: GrantFiled: April 5, 1982Date of Patent: April 23, 1985Assignee: Olin CorporationInventors: Thomas J. Gray, Norman G. Masse
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Patent number: 4503249Abstract: Iron (II) hexacyanocobaltate and ruthenium (III) hexacyanocobaltate have been found to be useful in the catalytic hydrogenation of organic materials.Type: GrantFiled: September 21, 1982Date of Patent: March 5, 1985Assignee: Phillips Petroleum CompanyInventors: Gerhard P. Nowack, Marvin M. Johnson, Donald C. Tabler
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Patent number: 4503251Abstract: Hydrogenation processes utilizing improved Raney nickel alloy catalysts are disclosed. The catalyst comprises a monolithic mesh type structure of a nickel alloy having an integral Beta phase Raney Ni.sub.x M.sub.1-x coating on its outer surfaces, where M is a catalytic activator selected from the group consisting of molybdenum, ruthenium, tantalum and titanium and where x, the weight fraction of nickel in the combined alloy, is between about 0.80 and about 0.95. The catalyst is effective in processes for hydrogenating an amine-substituted aromatic compound of the type ##STR1## wherein K is either benzene or naphthalene, R.sub.1 is a hydrogen atom or an aliphatic chain containing from about 1 to about 12 carbon atoms or a phenyl radical, R.sub.2 is a hydrogen atom, an amine group or an aliphatic chain containing from about 1 to about 3 carbon atoms, R.sub.3 is hydrogen or an amine group, and R.sub.4 is an amine group.Type: GrantFiled: April 5, 1982Date of Patent: March 5, 1985Assignee: Olin CorporationInventors: Thomas J. Gray, Norman G. Masse, Richard A. Hagstrom
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Patent number: 4487965Abstract: Trans-3-(4'-tert.-Butylcyclohex-1'-yl)-2-methyl-1-dialkylaminopropanes of the formula I ##STR1## where R.sup.1 and R.sup.2 are each alkyl and the sum of the carbon atoms in R.sup.1 and R.sup.2 is 5, 6, or 7, and their salts with physiologically tolerated acids, and their preparation, are described. The novel compounds are useful as active compounds for drugs.Type: GrantFiled: June 27, 1983Date of Patent: December 11, 1984Assignee: BASF AktiengesellschaftInventors: Walter Himmele, Wolfgang Heberle, Friedrich-Wilhelm Kohlmann, Walter Wesenberg
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Patent number: 4420648Abstract: Supported coprecipitated cobalt-silica hydrogenation catalysts are disclosed. The catalysts are prepared by: preparing an aqueous reaction mixture containing cobalt cations, silicate anions and solid porous carrier particles under agitation to form a coprecipitate of the cobalt and silicate ions onto said solid porous support particles; heating the aqueous reaction mixture; and adding an alkaline precipitating agent to further precipitate the cobalt and silicate ions onto said solid porous carrier particles. The aqueous reaction mixture may additionally include copper cations.Type: GrantFiled: September 19, 1979Date of Patent: December 13, 1983Assignee: Exxon Research and Engineering Co.Inventors: James L. Carter, Allan E. Barnett
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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
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Patent number: 4263225Abstract: Supported coprecipitated nickel-cobalt-silica and nickel-cobalt-copper-silica hydrogenation catalysts are disclosed. The catalysts are prepared by preparing an aqueous reaction mixture containing nickel and cobalt cations (and optionally copper cations), silicate anions and solid porous carrier particles under agitation to form a coprecipitate of the nickel, cobalt (and optionally copper) and silicate ions onto said solid porous support particles; heating the aqueous reaction mixture; and adding an alkaline precipitating agent to further precipitate the nickel, cobalt (and optionally copper) and silicate anions onto said solid porous carrier particles.Type: GrantFiled: September 19, 1979Date of Patent: April 21, 1981Assignee: Exxon Research & Engineering Co.Inventors: James L. Carter, Allan E. Barnett, John H. Sinfelt