Of Hydroxy Containing Compound Patents (Class 564/447)
  • Patent number: 8946463
    Abstract: The present invention relates to a chemocatalytic liquid-phase process for the direct one-stage amination of alcohols to primary amines by means of ammonia in high yields using a catalyst system containing at least one transition metal compound and a xantphos ligand.
    Type: Grant
    Filed: December 14, 2011
    Date of Patent: February 3, 2015
    Assignee: Evonik Degussa GmbH
    Inventors: Florian Klasovsky, Thomas Tacke, Jan Christoph Pfeffer, Thomas Haas, Matthias Beller, Andreas Martin, Jens Deutsch, Angela Koeckritz, Sebastian Imm, Juergen Haberland
  • Patent number: 8927773
    Abstract: The invention relates to a process for preparing primary amines which comprises the process steps A) provision of a solution of a secondary alcohol in a fluid, nongaseous phase, B) contacting of the phase with free ammonia and/or at least one ammonia-releasing compound and a homogeneous catalyst and optionally C) isolation of the primary amine formed in process step B), characterized in that the volume ratio of the volume of the liquid phase to the volume of the gas phase in process step B is greater than or equal to 0.25, and/or in that the ammonia is used in process step B) in a molar ratio based on the hydroxyl groups in the secondary alcohol of at least 5:1.
    Type: Grant
    Filed: August 23, 2011
    Date of Patent: January 6, 2015
    Assignee: Evonik Degussa GmbH
    Inventors: Florian Klasovsky, Jan Christoph Pfeffer, Thomas Tacke, Thomas Haas, Andreas Martin, Jens Deutsch, Angela Koeckritz
  • Publication number: 20140288306
    Abstract: The present invention provides novel ruthenium based catalysts, and a process for preparing amines, by reacting a primary alcohol and ammonia in the presence of such catalysts, to generate the amine and water. According to the process of the invention, primary alcohols react directly with ammonia to produce primary amines and water in high yields and high turnover numbers. This reaction is catalyzed by novel ruthenium complexes, which are preferably composed of quinolinyl or acridinyl based pincer ligands.
    Type: Application
    Filed: June 5, 2014
    Publication date: September 25, 2014
    Inventors: David Milstein, Chidambaram Gunanathan
  • Publication number: 20140046054
    Abstract: The invention relates to a process for preparing amines (A) by alcohol amination of alcohols (Al) by means of an aminating agent (Am) with elimination of water, wherein the alcohol amination is carried out in the presence of a complex catalyst comprising iridium and an amino acid.
    Type: Application
    Filed: August 7, 2013
    Publication date: February 13, 2014
    Applicant: BASF SE
    Inventors: Alexander WETZEL, Michael Limbach, Marion Brinks, Mathias Schelwies
  • Patent number: 8637709
    Abstract: Preparing a primary amine by alcohol amination of alcohol with ammonia and elimination of water includes reacting, in a homogeneously catalyzed reaction, a mixture of alcohol, ammonia, nonpolar solvent, and catalyst, in a liquid phase, to obtain a product mixture. The process then includes phase separating the product mixture into a polar product phase and a nonpolar product phase, and separating off the nonpolar product phase. At least some of the nonpolar phase returns to the homogenously catalyzed reaction. The process further includes separating off amination product from the polar product phase. At least some of the catalyst is in the nonpolar phase, and the catalyst accumulates in the nonpolar phase.
    Type: Grant
    Filed: March 8, 2012
    Date of Patent: January 28, 2014
    Assignee: BASF SE
    Inventors: Thomas Schaub, Boris Buschhaus, Marion Kristina Brinks, Mathias Schelwies, Rocco Paciello, Johann-Peter Melder, Martin Merger
  • Publication number: 20130331580
    Abstract: The present invention relates to a chemocatalytic liquid-phase process for the direct one-stage amination of alcohols to primary amines by means of ammonia in high yields using a catalyst system containing at least one transition metal compound and a xantphos ligand.
    Type: Application
    Filed: December 14, 2011
    Publication date: December 12, 2013
    Applicant: EVONIK DEGUSSA GmbH
    Inventors: Florian Klasovsky, Thomas Tacke, Jan Christoph Pfeffer, Thomas Haas, Matthias Beller, Andreas Martin, Jens Deutsch, Angela Koeckritz, Sebastian Imm, Juergen Haberland
  • Patent number: 8486183
    Abstract: An acid gas absorbent comprising an alkylamino alkyloxy (alcohol) monoalkyl ether and a process for the selective removal Of H2S from gaseous mixtures containing H2S and CO2 using an absorbent solution comprising an alkylamino alkyloxy alcohol monoalkyl ether.
    Type: Grant
    Filed: July 21, 2006
    Date of Patent: July 16, 2013
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Michael Siskin, Edmund John Mozeleski, Robert Basil Fedich, Frank Cheng-Yu Wang
  • Publication number: 20130178656
    Abstract: The present application relates to a process for preparing secondary amines by aminating excess primary or secondary alcohols with primary amines in the liquid phase in the presence of copper-comprising catalysts.
    Type: Application
    Filed: January 9, 2013
    Publication date: July 11, 2013
    Inventors: Christof Wilhelm Wigbers, Johann-Peter Melder, Bernd Stein
  • Publication number: 20130165672
    Abstract: The invention relates to a process for preparing primary amines which comprises the process steps A) provision of a solution of a secondary alcohol in a fluid, nongaseous phase, B) contacting of the phase with free ammonia and/or at least one ammonia-releasing compound and a homogeneous catalyst and optionally C) isolation of the primary amine formed in process step B), characterized in that the volume ratio of the volume of the liquid phase to the volume of the gas phase in process step B is greater than or equal to 0.25, and/or in that the ammonia is used in process step B) in a molar ratio based on the hydroxyl groups in the secondary alcohol of at least 5:1.
    Type: Application
    Filed: August 23, 2011
    Publication date: June 27, 2013
    Applicant: Evonik Degussa GmbH
    Inventors: Florian Klasovsky, Jan Christoph Pfeffer, Thomas Tacke, Thomas Haas, Andreas Martin, Jens Deutsch, Angela Koeckritz
  • Publication number: 20120232293
    Abstract: Process for preparing primary amines which have at least one functional group of the formula (—CH2—NH2) and at least one further primary amino group by alcohol amination of starting materials having at least one functional group of the formula (—CH2—OH) and at least one further functional group (—X), where (—X) is selected from among hydroxyl groups and primary amino groups, by means of ammonia with elimination of water, wherein the reaction is carried out homogeneously catalyzed in the presence of at least one complex catalyst comprising at least one element selected from groups 8, 9 and 10 of the Periodic Table and also at least one donor ligand.
    Type: Application
    Filed: March 8, 2012
    Publication date: September 13, 2012
    Applicant: BASF SE
    Inventors: Thomas SCHAUB, Boris Buschhaus, Marion Kristina Brinks, Mathias Schelwies, Rocco Paciello, Johann-Peter Melder, Martin Merger
  • Publication number: 20110152525
    Abstract: The present invention provides novel ruthenium based catalysts, and a process for preparing amines, by reacting a primary alcohol and ammonia in the presence of such catalysts, to generate the amine and water. According to the process of the invention, primary alcohols react directly with ammonia to produce primary amines and water in high yields and high turnover numbers. This reaction is catalyzed by novel ruthenium complexes, which are preferably composed of quinolinyl or acridinyl based pincer ligands.
    Type: Application
    Filed: August 10, 2009
    Publication date: June 23, 2011
    Applicant: Yeda Research and Development Co. Ltd. at the Weizmann Institute of Science
    Inventors: David Milstein, Chidambaram Gunanathan
  • Publication number: 20110009670
    Abstract: Embodiments of the present invention include methods for producing a cyclohexanedimethanamine by a reductive amination process.
    Type: Application
    Filed: March 9, 2009
    Publication date: January 13, 2011
    Applicant: Huntsman Petrochemical LLC
    Inventors: Terry L. Renken, Howard P. Klein
  • Publication number: 20100029988
    Abstract: The present invention relates to a process for producing an aliphatic primary amine or an aliphatic secondary amine from an aliphatic alcohol with a high catalytic activity and a high selectivity. In the process for producing an aliphatic amine according to the present invention, a linear, branched, or cyclic aliphatic alcohol having 6 to 22 carbon atoms is contacted with ammonia and hydrogen in the presence of a catalyst formed by supporting a ruthenium component on at least one material selected from the group consisting of (B) a zirconia-containing composite oxide and (C) zirconia surface-treated with a metal by hydrolysis of (A) a ruthenium compound.
    Type: Application
    Filed: November 5, 2007
    Publication date: February 4, 2010
    Applicant: KAO CORPORATION
    Inventors: Yuuta Suzuki, Yasuyuki Mimura, Tetsuaki Fukushima
  • Patent number: 7442840
    Abstract: The present invention relates to a process for preparing severely sterically hindered secondary amine ether alcohols and diamine polyalkenyl ethers by reacting a primary amino compound with a polyalkenylether glycol in the presence of a high activity nickel powder hydrogenation catalyst which is marked by high conversion of reactants and increased selectivity to desired final product.
    Type: Grant
    Filed: February 1, 2005
    Date of Patent: October 28, 2008
    Assignee: ExxonMobil Research and Engineering Company
    Inventors: Christine Nicole Elia, Michael Siskin, Michael Charles Kerby, Adeana Richelle Bishop, Edmund John Mozeleski, Andrzej Malek
  • Patent number: 6710210
    Abstract: Novel N-substituted-aminomethyl cyclopropyl ketone derivatives are represented by following Formula (1): wherein R1, R2 and R3 are each a hydrogen atom or an aliphatic hydrocarbon group; and R4 and R5 are each a hydrogen atom or an arylmethyl group which may have a substituent, where at least one hydrogen atom or aryl group as a substituent is combined with a carbon atom in the methyl moiety of the arylmethyl group, and at least one of R4 and R5 is an arylmethyl group which may have a substituent. These compounds are useful for the preparation of aminomethyl cyclopropyl ketone derivatives and 2-amino-1-cyclopropylethanol derivatives or salts thereof.
    Type: Grant
    Filed: April 8, 2002
    Date of Patent: March 23, 2004
    Assignee: Daicel Chemical Industries, Ltd.
    Inventors: Hiroki Tanaka, Li Rui Pan, Kiyoshi Ikura
  • Patent number: 6525222
    Abstract: 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: Grant
    Filed: December 5, 2000
    Date of Patent: February 25, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Jan Nouwen, Arthur Höhn, Horst Neuhauser, Frank Funke, Stephan Andreas Schunk, Johann-Peter Melder, Knut Eger, Michael Hesse, Joachim Wulff-Döring
  • Patent number: 6462092
    Abstract: The invention relates to use of substituted polycyclic aryl and heteroaryl tertiary-heteroalkylamine compounds useful as inhibitors of cholesteryl ester transfer protein (CETP; plasma lipid transfer protein-I) and compounds, compositions and methods for treating atherosclerosis and other coronary artery diseases. Preferred tertiary-heteroalkylamine compounds are substituted N,N-disubstituted reverse aminoalcohols.
    Type: Grant
    Filed: November 14, 2001
    Date of Patent: October 8, 2002
    Assignee: G.D. Searle & Co.
    Inventors: James A. Sikorski, Richard C. Durley, Deborah A. Mischke, Emily J. Reinhard, Yvette M. Fobian, Michael B. Tollefson, Lijuan Wang, Margaret L. Grapperhaus, Brian S. Hickory, Mark A. Massa, Monica B. Norton, William F. Vernier, Barry L. Parnas, Michele A. Promo, Ashton T. Hamme, Dale P. Spangler, Melvin L. Rueppel
  • Patent number: 6403834
    Abstract: 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: Grant
    Filed: July 23, 2001
    Date of Patent: June 11, 2002
    Assignee: Rhodia Chimie
    Inventors: Michel Alas, Albert Bouniot
  • Patent number: 6369274
    Abstract: 1,n-cyclohexanediamines (n=2, 3, 4) of general formula (I), wherein one of the radicals R1 to R3 is an amino group and the two others mean hydrogen, are produced from the corresponding cyclohexanediols and ammonia in the presence of a catalyst containing cobalt, at 100° to 350° C. and 50 to 300 bar. The compounds that can be produced according to the invention are structural elements for polymers, especially polyamides, polyimides, polyurea or polyurethanes, and ligands for cytostatically effective transition metal complexes.
    Type: Grant
    Filed: July 20, 2001
    Date of Patent: April 9, 2002
    Assignee: Lonza AG
    Inventors: Alfons Baiker, Tamas Mallat, Achim Fischer
  • Patent number: 6268533
    Abstract: A method is disclosed for the preparation of optically pure isomers of formoterol by the reaction of an optically pure 4-benzyloxy-3-formamidostyrene oxide with an optically pure 4-methoxy-&agr;-methyl-N-(phenylmethyl)benzeneethanamine followed by debenzylation. Useful intermediates in the process are also disclosed, as are the novel L-tartrate salt of R,R-formoterol and pharmaceutical compositions thereof.
    Type: Grant
    Filed: January 27, 2000
    Date of Patent: July 31, 2001
    Assignee: Sepracor Inc.
    Inventors: Yun Gao, Robert Hett, Kevin Q. Fang, Stephen A. Wald, Chris Hugh Senanayake
  • Patent number: 6187957
    Abstract: 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: Grant
    Filed: December 14, 1999
    Date of Patent: February 13, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerald Meyer, Frank Funke, Gerhard Schulz, Detlef Kratz, Marc Walter, Michael Hesse
  • Patent number: 5789620
    Abstract: The present invention relates to a process for preparing 1,4-bis(aminomethyl)cyclohexane by reacting a 40 to 80 wt. % aqueous solution of 1,4-bis(hydroxymethyl)cyclohexane with a mixture of hydrogen and ammonia in the presence of a nickel/copper/chromium catalyst at a pressure of 100 to 250 bar and a temperature of 150.degree. to 250.degree. C.
    Type: Grant
    Filed: October 31, 1997
    Date of Patent: August 4, 1998
    Assignee: Bayer Aktiengesellschaft
    Inventors: Helmut Waldmann, Jurgen Dahmer, Klaus Nachtkamp, Anatoly Bazanov, Alexandre Timofeev, Natalja Zubritskaya, Gennady Terechtchenko
  • Patent number: 5780686
    Abstract: A process for preparing 4-oxa-amines comprising reacting 1,3-dioxanes with ammonia and hydrogen in the presence of hydrogenation catalysts.
    Type: Grant
    Filed: May 27, 1997
    Date of Patent: July 14, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang Holderich, Marcus Paczkowski, Dieter Heinz
  • Patent number: 5744644
    Abstract: It has been found that certain polyhydroxyalkylamines have a particularly good solubility in water, alcohols and in mixtures of water and alcohols. The concentrated solutions described consist essentially of water, alcohols, preferably C.sub.1 -C.sub.3 -alcohols, or water/alcohol mixtures as solvent and at least one dialkylaminopropylglucamine of the formula 1 belowZ--NH--CH.sub.2 CH.sub.2 CH.sub.2 --NR.sup.1 R.sup.2 ( 1)where R.sup.1 and R.sup.2 are identical or different and are C.sub.1 -C.sub.4 -alkyl or hydroxyalkyl having from 2 to 4 carbon atoms and Z is a linear polyhydroxyhydrocarbon radical having at least three OH groups which may, if desired, be alkoxylated, The concentrated solutions are particularly useful for preparing the corresponding polyhydroxyalkylcarboxamides.
    Type: Grant
    Filed: May 23, 1996
    Date of Patent: April 28, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Bernd Papenfuhs
  • Patent number: 5371294
    Abstract: 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: Grant
    Filed: October 2, 1992
    Date of Patent: December 6, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Immel, Hans-Josef Buysch, Gerhard Darsow
  • Patent number: 5288911
    Abstract: Preparation of .alpha.,.omega.-aminoalcohols of the general formula IHO--CH.sub.2 --X--CH.sub.2 --NH.sub.2 (I),in which x denotes a C.sub.1 -C.sub.20 -alkylene chain optionally substituted by inert radicals and/or optionally interrupted by oxygen or nitrogen,by the reaction of .alpha.,.omega.-alkanediols of the general formula IIHO--CH.sub.2 --X--CH.sub.2 --OH (II),in which the connecting member x has the meanings stated above, with ammonia and a catalyst at a temperature ranging from 150.degree. to 300.degree. C. and under a pressure of from 50 to 300 bar, wherein the catalyst used is one whose catalytically active material consists of iron to an extent of from 5 to 100% w/w.
    Type: Grant
    Filed: April 22, 1992
    Date of Patent: February 22, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Koppenhoefer, Wolfgang Schroeder, Dieter Voges
  • Patent number: 4992150
    Abstract: A process for preparing oil-soluble nitrogen-containing compounds which comprises subjecting nitrogen-containing telogens and alpha-olefin taxogens to radical telomerization reaction. The nitrogen-containing compounds are mixtures of telomers having an average molecular weight not less than 300 and a nitrogen content of from 0.1 to 10 wt %. The compound may be further reacted with boron-bearing compounds or boron compounds to obtain oil-soluble nitrogen and boron-containing compounds. These compounds are useful as additives for fuel oils and lubricating oils.
    Type: Grant
    Filed: April 13, 1989
    Date of Patent: February 12, 1991
    Assignee: Nippon Oil Co, Ltd.
    Inventors: Jinichi Igarashi, Harumichi Watanabe
  • Patent number: 4950690
    Abstract: 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: Grant
    Filed: November 28, 1988
    Date of Patent: August 21, 1990
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Gene E. Parris, Ronald Pierantozzi
  • Patent number: 4942261
    Abstract: An allyl type amine is prepared by reacting an allyl type alcohol represented by the following formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 independently stand for a hydrogen atom, an aliphatic hydrocarbon group or alicyclic hydrocarbon having 1 to 8 carbon atoms, or an aromatic hydrocarbon group,with at least one member selected from the group consisting of ammonia, a primary amine and a secondary amine in the presence of a palladium compound and a multidentate phosphorus compound.
    Type: Grant
    Filed: December 9, 1988
    Date of Patent: July 17, 1990
    Assignee: Showa Denko Kabushiki Kaisha
    Inventors: Yoshimasa Ishimura, Takami Oe, Yuseki Suyama, Nobuyuki Nagato
  • Patent number: 4827035
    Abstract: Primary, secondary and tertiary amines are prepared by reacting ammonia or a primary amine with a primary or secondary monohydric or polyhydric alcohol over a copper catalyst such as that which forms of its own accord from copper formate under the reaction conditions.
    Type: Grant
    Filed: January 23, 1987
    Date of Patent: May 2, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Herbert Mueller, Hartmut Axel
  • Patent number: 4808625
    Abstract: The present invention relates to compounds of formula (I)ArCH.sub.2 R.sup.1 (I)or a monoethyl ether thereof (the compound of formula (I) including these ethers may contain no more than 30 carbon atoms in total); ethers, esters thereof; acid addition salts thereof; wherein Ar is a phenanthrene or substituted phenanthrene ring system; R.sup.1 contains not more than eight carbon atoms and is a group ##STR1## wherein m is 0 or 1; R.sup.5 is hydrogen;R.sup.6 and R.sup.7 are the same or different and each is hydrogen or C.sub.1-3 alkyl optionally substituted by hydroxy;R.sup.8 and R.sup.9 are the same or different and each is hydrogen or C.sub.1-3 alkyl; ##STR2## is a five-or six-membered saturated carbocyclic ring; R.sup.10 is hydrogen, methyl or hydroxymethyl;R.sup.11, R.sup.12 and R.sup.13 are the same or different and each is hydrogen or methyl;R.sup.14 is hydrogen, methyl, hydroxy, or hydroxymethyl.
    Type: Grant
    Filed: August 28, 1987
    Date of Patent: February 28, 1989
    Assignee: Burroughs Wellcome Co.
    Inventor: Kenneth W. Bair
  • Patent number: 4806690
    Abstract: A method for producing amines, the method comprising contacting at reactive conditions at least one alcohol, aldehyde or ketone, or a mixture thereof, with an aminating agent in the presence of a catalyst, is improved by employing as the catalyst a composition comprising cobalt, copper, and a third component selected from a group consisting of iron, zinc, zirconium and mixtures thereof.
    Type: Grant
    Filed: May 13, 1985
    Date of Patent: February 21, 1989
    Assignee: The Dow Chemical Company
    Inventor: Robert G. Bowman
  • Patent number: 4772750
    Abstract: A method for producing amines, the method comprising contacting at reactive conditions at least one alcohol, aldehyde or ketone, or a mixture thereof, with an aminating agent in the presence of a cobalt/copper catalyst, is improved by employing as the catalyst a composition comprising cobalt and copper, the catalyst being prepared by the molten salt impregnation technique.
    Type: Grant
    Filed: October 3, 1986
    Date of Patent: September 20, 1988
    Assignee: The Dow Chemical Company
    Inventor: Clarence E. Habermann
  • Patent number: 4719055
    Abstract: The present invention relates to compounds of formula (1)ArCH.sub.2 R.sup.1 (1)or a monomethyl ether thereof (the compound of formula (1) including these ethers may contain no more than 30 carbon atoms in total); ethers, esters thereof; acid addition salts thereof; wherein Ar is a phenanthrene or substituted phenanthrene ring system; R.sup.1 contains not more than eight carbon atoms and is a group ##STR1## wherein m is 0 or 1;R.sup.5 is hydrogen;R.sup.6 and R.sup.7 are the same or different and each is hydrogen or C.sub.1-3 alkyl optionally substituted by hydroxy;R.sup.8 and R.sup.9 are the same or different and each is hydrogen or C.sub.1-3 alkyl; ##STR2## is a five- or six-membered saturated carbocyclic ring; R.sup.10 is hydrogen, methyl or hydroxymethyl;R.sup.11, R.sup.12 and R.sup.13 are the same or different and each is hydrogen or methyl;R.sup.14 is hydrogen, methyl, hydroxy, or hydroxymethyl.
    Type: Grant
    Filed: October 10, 1984
    Date of Patent: January 12, 1988
    Assignee: Burroughs Wellcome Co.
    Inventor: Kenneth W. Bair
  • Patent number: 4665195
    Abstract: Disclosed is a process for producing di-amino-polyalkenyl ethers by reacting (a) one or more acyclic or heterocyclic amino compounds with (b) one or more polyalkenyl ether glycols or polyalkenyl amino ether alcohols, in the presence of a hydrogenation catalyst, at elevated temperatures and pressures.
    Type: Grant
    Filed: December 23, 1983
    Date of Patent: May 12, 1987
    Assignee: Exxon Research and Engineering Company
    Inventors: Eugene L. Stogryn, W.S. Winston Ho, Angelo A. Montagna
  • Patent number: 4487967
    Abstract: The present invention relates to a process for selectively preparing severely sterically hindered secondary aminoether alcohols by reacting a primary amino compound with a polyalkenyl ether glycol in the presence of a hydrogenation catalyst at elevated temperatures and pressures. The severely sterically hindered secondary aminoether alcohols are useful in acid gas scrubbing processes, particularly in the selective removal of H.sub.2 S from gaseous streams containing CO.sub.2 and H.sub.2 S.
    Type: Grant
    Filed: December 23, 1983
    Date of Patent: December 11, 1984
    Assignee: Exxon Research & Engineering Co.
    Inventors: Eugene L. Stogryn, W. S. Winston Ho, Angelo A. Montagna, Guido Sartori
  • Patent number: 4479009
    Abstract: The production of cyclic amines by the amination of cyclic alcohols is made more efficient by carrying out the reaction in the presence of certain amine solvents.
    Type: Grant
    Filed: November 29, 1982
    Date of Patent: October 23, 1984
    Assignee: Phillips Petroleum Company
    Inventor: Tod K. Shioyama
  • Patent number: 4434299
    Abstract: A process for the preparation of aniline by reaction of alicyclic alcohols or ketones with ammonia in the presence of a crystalline silicate catalyst having the structure of ZSM-5. Especially preferred alicyclic charge stocks are the mononuclear naphthenic type compounds such as cyclohexanol and cyclohexanone or mixtures thereof.
    Type: Grant
    Filed: November 12, 1982
    Date of Patent: February 28, 1984
    Assignee: Mobil Oil Corporation
    Inventors: Clarence D. Chang, William H. Lang
  • Patent number: 4429155
    Abstract: Aromatic amines (anilines) are obtained directly or via the corresponding cycloaliphatic amines by an aminating/hydrogenating reaction of phenols with ammonia and hydrogen over a supported palladium catalyst which also contains elements from group 1b, 2b or 7b of the periodic table as well as iron, cobalt or nickel, as such or in the form of their compounds, and, preferably, an inorganic base, said catalysts also having dehydrogenating properties.
    Type: Grant
    Filed: December 1, 1981
    Date of Patent: January 31, 1984
    Assignee: BASF Aktiengesellschaft
    Inventors: Norbert Goetz, Peter Jacobs, Leopold Hupfer, Herbert Toussaint, Wolfgang Reiss
  • Patent number: 4317932
    Abstract: 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: Grant
    Filed: February 22, 1980
    Date of Patent: March 2, 1982
    Assignee: W. R. Grace & Co.
    Inventor: Felek Jachimowicz
  • Patent number: 4293687
    Abstract: New biscyclohexylamine derivatives represented by the following formula ##STR1## wherein R.sup.1 to R.sup.4 represent identical or different alkyl groups having 1 to 6 carbon atoms;X is a single bond,a divalent aliphatic straight-chain or branched-chain group having from 2 to 10 carbon atoms,a methylene group, when at least one of the substituents R.sup.1 to R.sup.4 has more than 1 carbon atom,a divalent cycloaliphatic group having from 6 to 12 carbon atoms,a divalent aliphatic straight-chain or branched-chain group with cycloaliphatic substituents having from 6 to 8 carbon atoms,a divalent straight-chain or branched-chain dialkyl cyclohexane group having from 8 to 12 carbon atoms and a divalent straight-chain or branched-chain dialkyl benzene group having from 8 to 12 carbon atoms.
    Type: Grant
    Filed: May 5, 1980
    Date of Patent: October 6, 1981
    Assignee: Bayer Aktiengesellschaft
    Inventors: Oskar Weissel, Volker Serini, Hans-Josef Buysch
  • Patent number: 4252742
    Abstract: A process for preparing 2,6-dialkylcyclohexylamine, e.g., 2,6-dimethylcyclohexylamine, from a corresponding dialkylphenol, e.g., 2,6-dimethylphenol, by passing the phenol over a bed of a hydrogen-transfer catalyst in the presence of ammonia at elevated temperatures and pressures.
    Type: Grant
    Filed: July 13, 1979
    Date of Patent: February 24, 1981
    Assignee: Ciba-Geigy Corporation
    Inventors: Joseph T. Blackwell, III, Henry C. Grace, James B. Nabors, Harris E. Petree