Of Hydrocarbon Patents (Class 564/408)
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Patent number: 5489711Abstract: 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: GrantFiled: December 20, 1994Date of Patent: February 6, 1996Assignee: The B. F. Goodrich CompanyInventor: John T. Lai
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Patent number: 5478548Abstract: 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: GrantFiled: February 4, 1994Date of Patent: December 26, 1995Inventors: Charles J. Rogers, Alfred Kornel
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Patent number: 5453541Abstract: 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: GrantFiled: December 6, 1993Date of Patent: September 26, 1995Assignee: Monsanto CompanyInventors: Michael K. Stern, James K. Bashkin
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Patent number: 5395971Abstract: 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: GrantFiled: March 11, 1994Date of Patent: March 7, 1995Assignee: The Board of Regents of The University of OklahomaInventors: Kenneth M. Nicholas, Anurag S. Srivastava
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Patent number: 5349109Abstract: 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: GrantFiled: August 26, 1993Date of Patent: September 20, 1994Assignee: The Board of Regents of the University of OklahomaInventors: Kenneth M. Nicholas, Anurag S. Srivastava
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Patent number: 5262539Abstract: Electrophilic aromatic compounds can be reacted with sulphenamides in the presence of bases to form the corresponding aromatic amines.Type: GrantFiled: April 9, 1991Date of Patent: November 16, 1993Assignee: Bayer AktiengesellschaftInventors: Mieczyslaw Makosza, Maciej Bialecki
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Patent number: 5243099Abstract: 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: GrantFiled: September 9, 1992Date of Patent: September 7, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Diane L. Packett
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Patent number: 5169981Abstract: 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: GrantFiled: December 6, 1991Date of Patent: December 8, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Diane L. Packett
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Patent number: 5166440Abstract: 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: GrantFiled: December 12, 1990Date of Patent: November 24, 1992Assignee: Bayer AktiengesellschaftInventors: Otto Immel, Helmut Waldmann, Rudolf Braden
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Patent number: 5155274Abstract: 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: GrantFiled: January 21, 1992Date of Patent: October 13, 1992Assignee: Hoechst AktiengesellschaftInventors: Wolfgang A. Herrmann, Jurgen Kulpe, Jurgen Kellner, Herbert Riepl
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Patent number: 5117063Abstract: 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: GrantFiled: June 21, 1991Date of Patent: May 26, 1992Assignee: Monsanto CompanyInventors: Michael K. Stern, James K. Bashkin
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Patent number: 4929759Abstract: 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: GrantFiled: October 6, 1989Date of Patent: May 29, 1990Assignee: BASF AktiengesellschaftInventors: Volker Taglieber, Wolfgang Hoelderich, Rudolf Kummer, Wolf D. Mross, Guenter Saladin
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Patent number: 4914241Abstract: 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: GrantFiled: June 15, 1988Date of Patent: April 3, 1990Assignee: BASF AktiengesellschaftInventors: Michael Hesse, Wolfgang Hoelderich, Matthias Schwarzmann
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Patent number: 4843175Abstract: 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: GrantFiled: October 31, 1986Date of Patent: June 27, 1989Assignee: Chevron Research CompanyInventor: Robert Bacskai
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Patent number: 4827031Abstract: 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: GrantFiled: May 19, 1987Date of Patent: May 2, 1989Assignee: Pennwalt CorporationInventors: David M. Gardner, Paul J. McElligott, Roger T. Clark
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Patent number: 4658064Abstract: 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: GrantFiled: October 8, 1985Date of Patent: April 14, 1987Assignee: Milliken Research CorporationInventors: Patrick D. Moore, Robert L. Mahaffey, Jr.
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Patent number: 4602088Abstract: 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: GrantFiled: July 26, 1984Date of Patent: July 22, 1986Assignee: Texaco Inc.Inventor: Jiang-Jen Lin
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Patent number: 4594454Abstract: 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: GrantFiled: August 27, 1984Date of Patent: June 10, 1986Assignee: Milliken Research CorporationInventors: Patrick D. Moore, Robert L. Mahaffey, Jr.
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Patent number: 4536602Abstract: 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: GrantFiled: June 1, 1984Date of Patent: August 20, 1985Assignee: Air Products and Chemicals, Inc.Inventor: Michael Deeba
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Patent number: 4533751Abstract: 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: GrantFiled: October 9, 1981Date of Patent: August 6, 1985Assignee: SCM CorporationInventors: Leon Cherney, Charles R. Gorman, Sean G. Traynor, Carlos G. Cardenas
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Patent number: 4506039Abstract: 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: GrantFiled: December 20, 1982Date of Patent: March 19, 1985Assignee: Bayer AktiengesellschaftInventors: Gerhard Balle, Werner Rasshofer, Winfried Schoberth
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Patent number: 4501922Abstract: 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: GrantFiled: June 29, 1983Date of Patent: February 26, 1985Assignee: Air Products and Chemicals, Inc.Inventors: Roland E. Grandin, Barton Milligan
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Patent number: 4454321Abstract: 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: GrantFiled: June 11, 1982Date of Patent: June 12, 1984Assignee: Pennwalt CorporationInventors: David M. Gardner, Roger T. Clark
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Patent number: 4322530Abstract: 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: GrantFiled: February 22, 1980Date of Patent: March 30, 1982Assignee: W. R. Grace & Co.Inventor: Felek Jachimowicz
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Patent number: 4317932Abstract: 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: GrantFiled: February 22, 1980Date of Patent: March 2, 1982Assignee: W. R. Grace & Co.Inventor: Felek Jachimowicz