Of Cyano Patents (Class 564/490)
  • Patent number: 4739120
    Abstract: An improved process is disclosed for the catalytic hydrogenation of an organic nitrile group containing compound to a primary aminomethyl group in the presence of a rhodium catalyst, a basic substance, and in a two-phase solvent system comprising an immiscible organic solvent and water.
    Type: Grant
    Filed: August 21, 1986
    Date of Patent: April 19, 1988
    Assignee: The Dow Chemical Company
    Inventor: Marie F. Zuckerman
  • Patent number: 4721811
    Abstract: An improved process for selectively forming aliphatic polyamines from aliphatic polynitriles having 2 to 3 atoms between cyano groups by reacting aliphatic polynitrile, with hydrogen in the presence of a primary or secondary amine, through a fixed bed reactor while continuously contacting the reactants with granular Raney cobalt packed therein.
    Type: Grant
    Filed: August 26, 1985
    Date of Patent: January 26, 1988
    Assignee: W. R. Grace & Co.
    Inventors: Martin B. Sherwin, Shu-Chieh P. Wang, Stewart R. Montgomery
  • Patent number: 4683088
    Abstract: The invention provides a nickel/alumina/silicate catalyst, with an atomic ratio of nickel/aluminium between 20 and 2, a nickel/silicate ratio between 20 and 1, an active nickel surface area between 70 and 150 m.sup.2 /g nickel and an average pore size, depending on the above atomic ratio, between 4 and 20 nanometers. Preferably the nickel/aluminium atomic ratio is between 10 and 4 and the nickel/silicate ratio between 12 and 3. Preferably the catalyst has a specific porous structure.The invention also provides a method for preparing the catalyst by a two step process involving precipitating nickel ions and adding during a second, so-called ageing step a soluble aluminium compound and optionally the silicate. The silicate is preferably added during a second ageing step.The catalyst is useful for hydrogenating unsaturated organic compounds in particular oils.
    Type: Grant
    Filed: September 17, 1986
    Date of Patent: July 28, 1987
    Assignee: Internationale Octrooi Maatschappij "Octropa" BV
    Inventors: Johannes C. Oudejans, Peter Nootenboom, Keshab L. Ganguli, Cornelis M. Lok
  • Patent number: 4658066
    Abstract: Novel diamines of the formula ##STR1## are described, in which R.sub.1 is C.sub.1-12 -alkyl, R.sub.2 is H or C.sub.1-12 -alkyl, R.sub.3 is C.sub.1-12 -alkyl, cycloalkyl having 4-12 ring C atoms, C.sub.7-8 -aralkyl, substituted or unsubstituted aryl or, if R.sub.4 =H, is also --CH.dbd.CH--alkyl or --C(alkyl).dbd.CH-- alkyl each having 1-4 C atoms in the alkyl groups, and R.sub.4 is H, C.sub.1-12 -alkyl, cycloalkyl having 4-12 ring C atoms, C.sub.7-8 -aralkyl or substituted or unsubstituted aryl, or R.sub.1 and R.sub.2 and/or R.sub.3 and R.sub.4 together are C.sub.3-11 -alkylene. The diamines (I) are valuable intermediates and are suitable especially for the preparation of transparent crosslinkable polyamides.
    Type: Grant
    Filed: August 7, 1985
    Date of Patent: April 14, 1987
    Assignee: Ciba-Geigy Corporation
    Inventors: Dieter Reinehr, Josef Pfeifer
  • Patent number: 4598058
    Abstract: Molded catalyst materials contain metallic cobalt and/or nickel particles and a lubricant, the said particles being obtained by reduction of cobalt oxide and/or nickel oxide particles containing less than 0.1% by weight of alkali metal oxides and/or alkaline earth metal oxides at .ltoreq.500.degree. C., and the molded catalyst material having an indentation hardness greater than 300 kp/cm.sup.2.
    Type: Grant
    Filed: January 31, 1985
    Date of Patent: July 1, 1986
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Frank, Gerald Neubauer, Paul Duffner, Hans J. Wilfinger
  • Patent number: 4597908
    Abstract: The invention provides a process for the preparation of a transition metal-silicate catalyst in which an insoluble, basic compound of a transition metal having an atomic number between 26 and 30 (in particular nickel which has an atomic number of 28) is rapidly precipitated with an alkaline precipitation agent from an aqueous solution of such a metal salt, as a suspension, which precipitate is allowed to mature for a longer period in a suspended form, and, after the transition metal ions have been practically completely precipitated, soluble silicate is added to the suspension, after which the solids are separated from the liquid, optionally washed, dried and reduced.
    Type: Grant
    Filed: September 23, 1985
    Date of Patent: July 1, 1986
    Assignee: Internationale Octrooi Maatschappij "Octropa" B.V.
    Inventors: Cornelis M. Lok, Keshab L. Ganguli
  • Patent number: 4551441
    Abstract: A finely divided nickel boride hydrogenation catalyst which is stabilized with an organic linear polymer dispersed in a fatty substance like a triglyceride oil or a fatty amide is provided. The catalyst is stable upon storage and has a good selectivity. This catalyst yields excellent results in hydrogenation processes.
    Type: Grant
    Filed: July 11, 1984
    Date of Patent: November 5, 1985
    Assignee: Internationale Octrooi Maatscappij "Octropa" B.V.
    Inventors: Cornelis Van Dijk, Rudolph O. De Jongh
  • Patent number: 4532351
    Abstract: Supported catalysts comprised of one or more metals of Group VIII, optionally one or more metals from Group IB and IIA, aluminum and silicate are used for hydrogenating hydrogenatable organic compounds. The catalysts can be produced by coprecipitating metal ions from Group VIII, optionally metal ions from Groups IB and IIA, aluminum ions, and silicate ions, in the presence of solid porous particles.
    Type: Grant
    Filed: June 16, 1982
    Date of Patent: July 30, 1985
    Assignee: Exxon Research and Engineering Co.
    Inventors: Allan E. Barnett, Albert P. Halluin
  • Patent number: 4521527
    Abstract: Molded iron catalysts which contain metallic iron particles, obtained from anisometric iron oxide particles by contact with hydrogen at .ltoreq.500.degree. C., and a lubricant, are prepared.
    Type: Grant
    Filed: August 18, 1983
    Date of Patent: June 4, 1985
    Assignee: BASF Aktiengesellschaft
    Inventors: Gerhard Frank, Peter Rudolf, Gerald Neubauer, Manfred Ohlinger, Hans J. Wilfinger, Emil Pfannebecker, Paul Duffner
  • Patent number: 4472318
    Abstract: Novel 10-amino-deca-3,7-diene-nitriles of the formula ##STR1## are described, in which R.sub.1 is C.sub.1-12 -alkyl, R.sub.2 is H or C.sub.1-12 -alkyl, R.sub.3 is C.sub.1-12 -alkyl, cycloalkyl having 4-12 ring C atoms, C.sub.7-8 -aralkyl, substituted or unsubstituted aryl or, if R.sub.4 =H, --Ch.dbd.CH--alkyl or --C(alkyl).dbd.CH--alkyl each having 1-4 C atoms in the alkyl groups, and R.sub.4 =H, C.sub.1-12 -alkyl, cycloalkyl having 4-12 ring C atoms, C.sub.7-8 -aralkyl or substituted or unsubstituted aryl, or R.sub.1 and R.sub.2 and/or R.sub.3 and R.sub.4 together are C.sub.3-11 -alkylene. The compounds (I) can be reduced in a manner known per se to give the corresponding 1,11-diamino-undeca-3,7-dienes. The latter are valuable intermediates and are suitable especially for the preparation of transparent crosslinkable polyamides.
    Type: Grant
    Filed: January 26, 1983
    Date of Patent: September 18, 1984
    Assignee: Ciba-Geigy Corporation
    Inventors: Dieter Reinehr, Josef Pfeifer
  • Patent number: 4429159
    Abstract: In the production of amines from nitriles where the nitriles are hydrogenated under pressure in the presence of a Raney Nickel Catalyst using hydrogen produced from methane and containing CO.sub.2, a more efficient separation of the product hexamethylene diamine from the catalyst is obtained by maintaining a specified carbonate concentration. This specific carbonate concentration improves the settling characteristics of the catalyst and reduces catalyst carryover into the crude hexamethylene diamine during decantation.
    Type: Grant
    Filed: March 18, 1983
    Date of Patent: January 31, 1984
    Assignee: Monsanto Company
    Inventors: Charles E. Cutchens, Lynn H. Lanier
  • Patent number: 4420648
    Abstract: 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: Grant
    Filed: September 19, 1979
    Date of Patent: December 13, 1983
    Assignee: Exxon Research and Engineering Co.
    Inventors: James L. Carter, Allan E. Barnett
  • Patent number: 4389526
    Abstract: Novel methods are provided for synthesizing 2-amino-2-tetritol, by positive halogen addition to protected 1,4-dioxybutene-2 in the presence of a nitrile, resulting in addition of a halo functionality and the nitrile functionality across the double bond. Upon hydrolysis, the desired erythro-product can be obtained in stereochemically good yield.
    Type: Grant
    Filed: August 3, 1981
    Date of Patent: June 21, 1983
    Assignee: The Regents of the University of California
    Inventors: Milos Sovak, Ramachandran Ranganathan
  • Patent number: 4359585
    Abstract: This is an improvement in a process for the production of an amine such as hexamethylenediamine from a nitrile such as adiponitrile where the nitrile is hydrogenated under pressure in the presence of a Raney nickel catalyst, the reaction being conducted in a reactor from which is discharged a product stream containing both the amine and the Raney nickel catalyst. The improvement comprises charging to the process discharge stream containing the product amine and the Raney nickel catalyst, an inorganic base, whereby the Raney nickel catalyst is passivated and catalytic decomposition of the amine is substantially decreased.
    Type: Grant
    Filed: April 21, 1980
    Date of Patent: November 16, 1982
    Assignee: Monsanto Company
    Inventors: Charles R. Campbell, Charles E. Cutchens
  • Patent number: 4343722
    Abstract: A catalyst for hydrogenation of nitriles with a high activity is produced by heating dicobalt octacarbonyl together with an aromatic nitrile at a temperature of 100.degree.-200.degree. C. in the absence of oxygen gas.
    Type: Grant
    Filed: March 31, 1981
    Date of Patent: August 10, 1982
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Masao Saito, Yuuzi Onda, Yuko Murayama
  • Patent number: 4331557
    Abstract: A ruthenium-containing catalyst is regenerated after use for an organic chemical treatment, e.g., hydrogenation, dehydrogenation, isomerization, disproportionation, hydrocracking, etc., at an elevated temperature and at a considerably reduced pressure of the order of about 600 mm Hg and much lower of the order of about 0.001 mm Hg.
    Type: Grant
    Filed: May 22, 1980
    Date of Patent: May 25, 1982
    Assignee: Phillips Petroleum Company
    Inventor: Charles A. Drake
  • Patent number: 4313004
    Abstract: A method for preparing a diaminoalkoxy compound of the formula: ##STR1## wherein m and n are both numbers from 0 to about 25 and m+n equals at least 1, R.sub.1 is selected from H and a lower alkyl group having from 1 to about 4 carbon atoms; and R.sub.2 is selected from H and an alkyl group containing from 1 to about 10 carbon atoms; which comprises incrementally introducing a dicyanoglycol compound of the formula: ##STR2## wherein m, n, R.sub.1 and R.sub.2 have the values indicated above into a reaction medium at a rate sufficient to minimize cleavage reactions, at a temperature of from about 90.degree. C. to about 160.degree. C. in the presence of hydrogen at a pressure of from about 800 psi to about 2200 psi; ammonia in an amount of from about 10 to about 40 weight percent based on the weight of dicyanoglycol compound; and a nickel catalyst in an amount sufficient to catalyze said reaction, whereby said dicyanoglycol compound is reduced to said diaminoalkoxy compound.
    Type: Grant
    Filed: February 2, 1981
    Date of Patent: January 26, 1982
    Assignee: Milliken Research Corporation
    Inventors: Edward W. Kluger, Andre M. Goineau
  • Patent number: 4313005
    Abstract: This invention relates to a process for reducing amidine formation during reduction of organonitriles. The process comprises including a boron compound in the reaction medium in sufficient amount to complex the amidine compound as it is formed.
    Type: Grant
    Filed: April 3, 1980
    Date of Patent: January 26, 1982
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Michael E. Ford, Randall J. Daughenbaugh
  • Patent number: 4313018
    Abstract: Anthranilic acid has been anchored to polystyrene, and rhodium, palladium, platinum and ruthenium complexes of this modified polystyrene have been prepared. These catalysts will reduce a variety of olefinic and aromatic hydrocarbons, and also nitrile, nitro and carbonyl functional groups, said carbonyl groups being present in either ketones or aldehydes.
    Type: Grant
    Filed: April 7, 1978
    Date of Patent: January 26, 1982
    Assignee: Western Kentucky University
    Inventors: Norman L. Holy, William A. Logan, Karl D. Stein
  • Patent number: 4307248
    Abstract: Supported coprecipitated catalysts comprised of one or more metals of Group VIII, one or more metals of Group IIA, and aluminum are used for hydrogenating hydrogenatable organic compounds. The catalysts are produced by preparing, under agitation; an aqueous mixture containing ions of Group VIII, Group IIA, and aluminum, as well as solid porous particles to form a coprecipitate of the metal ions and aluminum ions with the solid porous support particles; heating the aqueous reaction mixture; and adding precipitating agent to precipitate the metal ions and aluminum ions onto the solid support.
    Type: Grant
    Filed: November 28, 1980
    Date of Patent: December 22, 1981
    Assignee: Exxon Research & Engineering Co.
    Inventors: Allan E. Barnett, Albert P. Halluin
  • Patent number: 4297512
    Abstract: An improved process for the preparation of triethylamine by gas phase catalytic hydrogenation of acetonitrile is disclosed, the improvement residing in employing as the catalyst a supported noble metal of Group VIII of the periodic system catalyst where the support comprises lithium aluminum spinel. The process can be carried out in the presence of up to 5% by weight of monoethylamine and/or diethylamine. The process is conducted at 80.degree.-115.degree. C. and under a pressure of 1 to 60 bars.
    Type: Grant
    Filed: August 22, 1979
    Date of Patent: October 27, 1981
    Assignee: EC Erdolchemie GmbH
    Inventors: Klaus Mainusch, Bernhard Schleppinghoff, Klaus Munter
  • Patent number: 4289908
    Abstract: This invention relates to an improvement in a process for preparing lower acyclic saturated amines by the gas phase hydrogenation of nitriles. To carry out the gas phase hydrogenation, the temperatures utilized in the reaction zone are from about 150.degree. to 350.degree. C., the pressure from about atmospheric to 500 psia, and the space velocity from about 750-20,000. Preferably, the conditions are controlled such that the components in the reaction zone are not exposed to a temperature greater than 380.degree. C. for a period of time in excess of 0.03 seconds.
    Type: Grant
    Filed: July 19, 1979
    Date of Patent: September 15, 1981
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Eckhart R. Becker, Randall J. Daughenbaugh, Barton Milligan
  • Patent number: 4273939
    Abstract: Supported coprecipitated non-ferrous Group VIII metal aluminum catalysts are used for hydrogenating hydrogenatable organic compounds. The catalysts are produced by preparing an aqueous mixture containing the metal ions, aluminum ions and solid porous support particles under agitation to form a coprecipitate of the metal ions and aluminum ions with the solid porous support particles; heating the aqueous reaction mixture; and adding precipitating agent to further precipitate the metal ions and aluminum ions onto the solid support.
    Type: Grant
    Filed: November 6, 1979
    Date of Patent: June 16, 1981
    Assignee: Exxon Research & Engineering Co.
    Inventors: Allan E. Barnett, Albert P. Halluin
  • Patent number: 4271323
    Abstract: Process for hydrogenating unsaturated compounds in the liquid phase in the presence of a soluble catalyst obtained by reacting an organometal derivative or a metal hydride with a synergistic mixture of (a) a compound of zinc, zirconium, manganese, molybdenum, or iron and (b) a nickel or cobalt compound.
    Type: Grant
    Filed: October 10, 1975
    Date of Patent: June 2, 1981
    Assignee: Institut Francais du Petrole
    Inventors: Daniel Durand, Gerard Hillion, Christian Lassau, Lucien Sajus
  • Patent number: 4263225
    Abstract: 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: Grant
    Filed: September 19, 1979
    Date of Patent: April 21, 1981
    Assignee: Exxon Research & Engineering Co.
    Inventors: James L. Carter, Allan E. Barnett, John H. Sinfelt
  • Patent number: 4260748
    Abstract: Morpholine is produced by the catalytic hydrogenation of bis (cyanomethyl) ether.
    Type: Grant
    Filed: March 7, 1980
    Date of Patent: April 7, 1981
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Dale D. Dixon, Randall J. Daughenbaugh
  • Patent number: 4257984
    Abstract: The present invention relates to epoxy resin compositions and in particular to curing agents for such resin compositions. The present invention thus embraces monotertiarymonosecondarydiprimarytetramines and the precursor from which this amine is manufactured namely monotertiarymonosecondarydinitrilodiamines.
    Type: Grant
    Filed: April 4, 1977
    Date of Patent: March 24, 1981
    Assignee: Henkel Corporation
    Inventor: Stuart A. Harrison
  • Patent number: 4254059
    Abstract: A novel process is described for the homogeneous hydrogenation of nitriles to primary amines utilizing anionic Group VIII metal hydride compositions as catalysts which contain phosphorus, arsenic or antimony organoligands. Use of these anionic catalysts allows the high yield hydrogenation of nitriles to primary amines to be conducted under mild conditions of temperature and pressure with high selectivity and eliminates the need for the presence of ammonia to suppress the formation of significant amounts of secondary and tertiary amines.
    Type: Grant
    Filed: August 1, 1979
    Date of Patent: March 3, 1981
    Assignee: Allied Chemical Corporation
    Inventors: Roger A. Grey, Guido P. Pez
  • Patent number: 4248801
    Abstract: Tertiary monomethylamines having long chain alkyl groups are advantageously prepared from unsaturated aliphatic nitriles under a low pressure at a high yield by the steps of:(a) reducing the nitriles with hydrogen in the presence of a nickel hydrogenation catalyst at 200.degree. through 230.degree. C. and under a hydrogen pressure of 0 through 10 kg/cm.sup.2 G, while the formed ammonia is removed;(b) reacting the resultant amines with a hydroxymethylation agent in the presence of the nickel catalyst at 150.degree. through 180.degree. C., while hydrogen is passed through the reaction zone under 0.3 through 7 kg/cm.sup.2 G and the formed water is removed, and;(c) reducing the resultant tertiary amines with hydrogen in the presence of the nickel catalyst at 175.degree. through 210.degree. C. and under a hydrogen pressure of 5 through 10 kg/cm.sup.2 G.
    Type: Grant
    Filed: July 3, 1979
    Date of Patent: February 3, 1981
    Assignee: The Lion Fat & Oil Co., Ltd.
    Inventors: Susumu Tomidokoro, Michito Sato, Daini Saika
  • Patent number: 4239653
    Abstract: The present invention relates to a process for the preparation of non-pyrophoric catalyst having controlledparticle size and activity comprising suspending active charcoal of homogeneous pore distribution in a diluted solution of a palladium salt or salt complex, if desired in the presence of an aliphatic alcohol, stirring the solution, filtering the catalyst coal, followed by treatment of the sorbed palladium salt or salt complex with alkali if desired and stirring it as long as required for the accumulation of the sorbed palladium compounds, reducing same by methods known, repeating the above mentioned steps, if desired any number of times and drying the obtained catalyst after washing.
    Type: Grant
    Filed: November 27, 1978
    Date of Patent: December 16, 1980
    Assignee: Chinoin Gyogyszer
    Inventors: Janos Bodnar, Gyorgy Lugosi, Gyorgy L. Nagy