Of Hydrocarbon Patents (Class 564/408)
  • Patent number: 5489711
    Abstract: An oligomer from diarylamines is disclosed which has desirable antioxidant properties in lubricating oils which contain synthetic ester lubricants. The oligomer is desirable for use at higher temperatures where it has less volatility than simple diarylamines. The oligomer has substantial portions of monosubstituted diphenylamine repeat units which result in linear oligomers. Di and polysubstituted diphenylamines may optionally be present as repeat units. These di and polysubstituted diphenylamines generally react as monofunctional reactants in oligomerization and tend to reduce the number of repeat units in the average oligomer.
    Type: Grant
    Filed: December 20, 1994
    Date of Patent: February 6, 1996
    Assignee: The B. F. Goodrich Company
    Inventor: John T. Lai
  • Patent number: 5478548
    Abstract: Methods for synthesis of chemical compounds by catalytic transfer hydrogenation comprise forming a mixture of a starting material, a hydrogen donor material and a catalyst. The catalyst is selected from a catalytic form of carbon, a polyethylene glycol phase transfer agent, and mixtures thereof. The mixture is heated at a temperature of from 30.degree. to 400.degree. C. in the presence of at least one alkali or alkaline earth metal compound to cause reduction of the starting material by catalytic transfer hydrogenation and form the desired chemical compound product.
    Type: Grant
    Filed: February 4, 1994
    Date of Patent: December 26, 1995
    Inventors: Charles J. Rogers, Alfred Kornel
  • Patent number: 5453541
    Abstract: A method of producing 4-ADPA is disclosed wherein aniline or substituted aniline derivatives and nitrobenzene are reacted under suitable conditions to produce 4-nitrodiphenylamine or substituted derivatives thereof and/or 4-nitrosodiphenylamine or substituted derivatives thereof and/or their salts, either or both of which are subsequently reduced to produce 4-ADPA or substituted derivatives thereof. The 4-ADPA or substituted derivatives thereof can be reductively alkylated to produce p-phenylenediamine products or substituted derivatives thereof which are useful as antiozonants.
    Type: Grant
    Filed: December 6, 1993
    Date of Patent: September 26, 1995
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, James K. Bashkin
  • Patent number: 5395971
    Abstract: A process for making unsaturated .alpha.-amines from olefins wherein the process includes adding an aminating agent, an olefin and a molybdenum based catalyst to a reaction vessel having a nitrogen atmosphere. The catalyst may be described by the general formula LL'MoO.sub.2, L.sub.2 L'MoO.sub.2, or LL'MoO(X--Y).
    Type: Grant
    Filed: March 11, 1994
    Date of Patent: March 7, 1995
    Assignee: The Board of Regents of The University of Oklahoma
    Inventors: Kenneth M. Nicholas, Anurag S. Srivastava
  • Patent number: 5349109
    Abstract: A process for making unsaturated .alpha.-amines from olefins wherein the process includes adding an aminating agent, an olefin and a molybdenum based catalyst to a reaction vessel having a nitrogen atmosphere. The catalyst may be described by the general formula LL'MoO.sub.2, L.sub.2 L'MoO.sub.2, or LL'MoO(X-Y).
    Type: Grant
    Filed: August 26, 1993
    Date of Patent: September 20, 1994
    Assignee: The Board of Regents of the University of Oklahoma
    Inventors: Kenneth M. Nicholas, Anurag S. Srivastava
  • Patent number: 5262539
    Abstract: Electrophilic aromatic compounds can be reacted with sulphenamides in the presence of bases to form the corresponding aromatic amines.
    Type: Grant
    Filed: April 9, 1991
    Date of Patent: November 16, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Mieczyslaw Makosza, Maciej Bialecki
  • Patent number: 5243099
    Abstract: Organic polymer additive containing polar functional groups enhances the stability of palladium-containing catalysts for the telomerization of conjugated diolefins in the presence of active hydrogen-containing telomerization agent to produce alpha-substituted alkadienes.
    Type: Grant
    Filed: September 9, 1992
    Date of Patent: September 7, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Diane L. Packett
  • Patent number: 5169981
    Abstract: Organic polymer additive containing polar functional groups enhances the stability of palladium-containing catalysts for the telomerization of conjugated diolefins in the presence of active hydrogen-containing telomerization agent to produce alpha-substituted alkadienes.
    Type: Grant
    Filed: December 6, 1991
    Date of Patent: December 8, 1992
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Diane L. Packett
  • Patent number: 5166440
    Abstract: 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: Grant
    Filed: December 12, 1990
    Date of Patent: November 24, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Otto Immel, Helmut Waldmann, Rudolf Braden
  • Patent number: 5155274
    Abstract: New complexes of the elements of Groups VIIA, VIIIA, and IB of the Periodic Table* with the trisodium salt of tris(m-sulfophenyl)phosphane as a complex ligand. The complexes are used as catalysts for hydrogenations for the water gas reactions, hydrocarbonyls, hydroformylations, oxidations, carbon-carbon cross-linking reactions (e.g. allene/alkine coupling), and additions of secondary amines to carbon-carbon double bonds.
    Type: Grant
    Filed: January 21, 1992
    Date of Patent: October 13, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Wolfgang A. Herrmann, Jurgen Kulpe, Jurgen Kellner, Herbert Riepl
  • Patent number: 5117063
    Abstract: A method of producing 4-ADPA is disclosed wherein aniline and nitrobenzene are reacted under suitable conditions to produce 4-nitrodiphenylamine and/or 4-nitrosodiphenylamine and/or their salts, either or both of which are subsequently reduced to produce 4-ADPA. The 4-ADPA can be reductively alkylated to produce p-phenylenediamine products which are useful as antiozonants.
    Type: Grant
    Filed: June 21, 1991
    Date of Patent: May 26, 1992
    Assignee: Monsanto Company
    Inventors: Michael K. Stern, James K. Bashkin
  • Patent number: 4929759
    Abstract: Amines are prepared from an olefin and ammonia or a primary or secondary amine, or a mixture of these, in the presence of a borosilicate or borogermanate zeolite of the pentasil type as a catalyst, by a process in which the amine obtained is isolated from the reaction mixture, and unreacted starting materials are recycled.
    Type: Grant
    Filed: October 6, 1989
    Date of Patent: May 29, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Volker Taglieber, Wolfgang Hoelderich, Rudolf Kummer, Wolf D. Mross, Guenter Saladin
  • Patent number: 4914241
    Abstract: Diamines of the formula ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, alkyl, aryl, alkoxy, aralkyl or cycloalkyl and X is a group of the formula(CR.sup.4 R.sup.5).sub.m (II)where R.sup.4 and R.sup.5 have the meanings given above for R.sup.1 and m is from 1 to 12, are prepared by a process in which a diamine of the formula ##STR2## where R.sup.1, R.sup.2 and X are the groups described above, is reacted with an olefin of the formula ##STR3## where R.sup.6 and R.sup.9 are each hydrogen or alkyl which is straight-chain in the .alpha.-position, in the presence of a zeolite as a catalyst.
    Type: Grant
    Filed: June 15, 1988
    Date of Patent: April 3, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Hesse, Wolfgang Hoelderich, Matthias Schwarzmann
  • Patent number: 4843175
    Abstract: A process for the preparation of alkylaniline having from about 10 to 30 carbon atoms in the alkyl substituent which comprises reacting aniline with an olefin having from about 10 to 30 carbon atoms in the presence of a Friedel-Crafts catalyst.
    Type: Grant
    Filed: October 31, 1986
    Date of Patent: June 27, 1989
    Assignee: Chevron Research Company
    Inventor: Robert Bacskai
  • Patent number: 4827031
    Abstract: The process for preparing aliphatic and aromatic amines by reacting an olefin with either ammonia, a primary amine, or a secondary amine at elevated temperature in the presence of an ammonium halide catalyst, preferably a catalyst-promoter combination, is disclosed herein.
    Type: Grant
    Filed: May 19, 1987
    Date of Patent: May 2, 1989
    Assignee: Pennwalt Corporation
    Inventors: David M. Gardner, Paul J. McElligott, Roger T. Clark
  • Patent number: 4658064
    Abstract: A compound is provided of the formula: ##STR1## wherein R.sub.1 is selected from alkyl, halide, or alkoxy; R.sub.2 is selected from H or alkyl; Y is a number of from 2 to about 200; and Z is selected from H or ##STR2## where W is alkyl.
    Type: Grant
    Filed: October 8, 1985
    Date of Patent: April 14, 1987
    Assignee: Milliken Research Corporation
    Inventors: Patrick D. Moore, Robert L. Mahaffey, Jr.
  • Patent number: 4602088
    Abstract: A method for the preparation of enamines wherein a conjugated diene is reacted with a secondary amine, carbon monoxide and hydrogen (synthesis gas) in solvent solution in the presence of a rhodium catalyst. In accordance with the preferred embodiment, butadiene is reacted with a dialkylamine and synthesis gas in an organic solvent in the presence of a rhodium catalyst to provide the corresponding 1,3-pentadienyl dialkylamine in good yield and with good selectivity.
    Type: Grant
    Filed: July 26, 1984
    Date of Patent: July 22, 1986
    Assignee: Texaco Inc.
    Inventor: Jiang-Jen Lin
  • Patent number: 4594454
    Abstract: A compound is provided of the formula: ##STR1## wherein R.sub.1 is selected from alkyl, halide, or alkoxy; R.sub.2 is selected from H or alkyl; Y is a number of from 2 to about 200; and Z is selected from H or ##STR2## where W is alkyl.
    Type: Grant
    Filed: August 27, 1984
    Date of Patent: June 10, 1986
    Assignee: Milliken Research Corporation
    Inventors: Patrick D. Moore, Robert L. Mahaffey, Jr.
  • Patent number: 4536602
    Abstract: The present invention involves the catalytic amination of olefins with ammonia, a primary amine, or a secondary amine using a perfluorinated organic acid catalyst.
    Type: Grant
    Filed: June 1, 1984
    Date of Patent: August 20, 1985
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Michael Deeba
  • Patent number: 4533751
    Abstract: There is provided a process for the addition of a secondary aliphatic amine to myrcene or an 8-substituted myrcene and isomerization to a dialkyl 1,3-dienamine. The process is liquid phase and employs an excess of the amine relative to myrcene or substituted myrcene. The catalyst is an alkali metal amide anion formed from the amine.
    Type: Grant
    Filed: October 9, 1981
    Date of Patent: August 6, 1985
    Assignee: SCM Corporation
    Inventors: Leon Cherney, Charles R. Gorman, Sean G. Traynor, Carlos G. Cardenas
  • Patent number: 4506039
    Abstract: Polymer-containing polyether polyamines containing terminal aromatically-bound amino groups are produced by in situ polymerization of a polyether polyamine with an olefinically unsaturated monomer. The polyether polyamine starting material must have terminal aromatic amino groups, a molecular weight of from 800 to 10,000 and an aromatic amino group content of from 0.3 to 16 wt. %. Suitable olefinically unsaturated monomers include .alpha.,.beta.-unsaturated nitriles, aromatic vinyl compounds, .alpha.,.beta.-unsaturated carboxylic acids and esters thereof, vinyl esters, vinyl halides, vinylidene halides, .alpha.,.beta.-unsaturated carboxylic acid amides and aminoalkyl esters of unsaturated carboxylic acids. Acrylonitrile/styrene mixtures are preferred monomers. The starting materials are employed in quantities such that the product modified polyether polyamine contains from 1 to 60 wt. % polymer or graft-polymer. The product polyamines are particularly useful in the production of polyurethanes.
    Type: Grant
    Filed: December 20, 1982
    Date of Patent: March 19, 1985
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gerhard Balle, Werner Rasshofer, Winfried Schoberth
  • Patent number: 4501922
    Abstract: This invention pertains to a process for preparing mononuclear aromatic amines by reacting an alkali metal amide with a mononuclear aromatic compound, e.g., benzene and toluene. The reaction is carried out in the presence of a metallic hydrogenation catalyst, suitably copper, nickel, rhodium or cobalt, the metal being present in an amount sufficient for catalyzing the reaction. The amine then is formed by adding a protonating agent to the resulting reaction product formed by the reaction of the alkali metal amide with the aromatic compound. The addition of the protonating agent liberates the amine.
    Type: Grant
    Filed: June 29, 1983
    Date of Patent: February 26, 1985
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Roland E. Grandin, Barton Milligan
  • Patent number: 4454321
    Abstract: Aliphatic and aromatic amines are produced by reacting an olefin with either ammonia or a primary or secondary amine in the presence of a catalytic amount of ruthenium or iron compound catalyst. The reaction is carried out in the liquid phase using an inert liquid, a product amine, or one of the reactants as a solvent. The temperatures used are 100.degree. to 250.degree. C. and the pressures are at least autogenous and up to 12,000 psig.
    Type: Grant
    Filed: June 11, 1982
    Date of Patent: June 12, 1984
    Assignee: Pennwalt Corporation
    Inventors: David M. Gardner, Roger T. Clark
  • Patent number: 4322530
    Abstract: 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: Grant
    Filed: February 22, 1980
    Date of Patent: March 30, 1982
    Assignee: W. R. Grace & Co.
    Inventor: Felek Jachimowicz
  • 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