Catalyst Utilized Patents (Class 564/479)
  • Patent number: 5482909
    Abstract: The present invention relates to an improved catalyst for the selective synthesis of monomethylamine (MMA) and dimethylamine (DMA) at the expense of trimethylamine (TMA) for a starting feed of methanol and/or dimethyl ether and ammonia. The current industrial catalyst for this process is a standard SiO.sub.2 /Al.sub.2 O.sub.3 material. The present invention combines this standard catalyst with microporous carbon molecular sieves (CMS) to form a composite material (i.e., a CMS/SiO.sub.2 /Al.sub.2 O.sub.3 material) with higher selectivity for the desired products MMA and DMA. The invention also relates to methods of making the improved catalyst and a process of using the improved catalyst material in the production of MMA and DMA.
    Type: Grant
    Filed: July 21, 1994
    Date of Patent: January 9, 1996
    Assignees: University of Delaware, E. I. Du Pont de Nemours & Co., Inc.
    Inventors: Henry C. Foley, George C. Sonnichsen, Loren D. Brake, Ravindra K. Mariwala, Davis S. Lafyatis
  • Patent number: 5410086
    Abstract: This invention relates to a method for controlling the weight ratio of diethylenetriamine to piperazine in a process in which ethylenediamine, or a mixture of ethylenediamine and monoethanolamine, and hydrogen are maintained in the presence of a hydrogenation catalyst, which method comprises adjusting the hydrogen concentration in the liquid phase in an amount sufficient to effectuate control of the weight ratio of diethylenetriamine to piperazine in said process.
    Type: Grant
    Filed: June 25, 1991
    Date of Patent: April 25, 1995
    Inventor: Lloyd M. Burgess
  • Patent number: 5399769
    Abstract: This invention relates to a process for producing a nonequilibrium distribution of methylamines by the catalyzed reaction of methanol and/or dimethyl ether with ammonia and by the catalytic reforming of a methylamine containing feedstock. One process selectively affords a reaction product enriched in mono and dimethylamines and low in trimethylamine, at high conversion of methanol or dimethylether. A variation of the process effects reforming a methylamine containing feedstock, optionally containing ammonia over a catalyst. The key to achieving this low TMA selectivity at high conversion resides in the use of a microporous zeolite, preferably chabazite, catalyst having a geometric selectivity index (GSI) less about 3, a shape selectivity index (SSI) greater than about 5 and a sorption capacity for 1-PrOH of at least 0.5 mmol/g.
    Type: Grant
    Filed: June 3, 1994
    Date of Patent: March 21, 1995
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Frederick C. Wilhelm, Gene E. Parris, Brent A. Aufdembrink, Thomas R. Gaffney
  • Patent number: 5382696
    Abstract: A method for selectively preparing dimethylamine and monomethylamine, while the production of trimethylamine is inhibited to a sufficiently low level. The method comprises carrying out a gaseous reaction of methanol and ammonia by the use of a mordenite modified with a silylating agent by a silylation treatment in a liquid phase. According to the present invention, recycling trimethylamine is unnecessary, and the amount of steam or the like to be used can be decreased.
    Type: Grant
    Filed: October 6, 1993
    Date of Patent: January 17, 1995
    Assignee: Mitsui Toatsu Chemicals, Incorporated
    Inventors: Tadamitsu Kiyoura, Kazuhiro Terada
  • Patent number: 5364971
    Abstract: The present invention relates to a process for the reduction of the color of polyamines by reacting at elevated temperature, e.g. 120.degree.-170.degree. C., and pressure, e.g. 500 to 6000 psig. the colored polyamines, e.g. triethylenetetramine and tetraethylenepentamine, in the presence of a ruthenium on alumina hydrogenation catalyst. The catalyst for the polyamine decolorization process preferably has at least 0.5 wt. % Ru. In the process of the present invention, the polyamines can either be distilled into a narrow product composition and then hydrogenareal, or a crude polyamine product can be hydrogenated and then distilled to produce the desired product composition.
    Type: Grant
    Filed: August 25, 1993
    Date of Patent: November 15, 1994
    Assignee: Texaco Chemical Inc.
    Inventor: Wei-Yang Su
  • Patent number: 5362914
    Abstract: The present invention relates to a process for the reduction of the color of polyamines by reacting at elevated temperature, e.g. 120.degree.-170.degree. C., and pressure, e.g. 500 to 6000 psig. the colored polyamines, e.g. triethylenetetramine and tetraethylenepentamine, in the presence of a cobalt on alumina hydrogenation catalyst promoted with copper and chromium. In the process of the present invention, the polyamines can either be distilled into a narrow product composition and then hydrogenated, or a crude polyamine product can be hydrogenated and then distilled to produce the desired product composition.
    Type: Grant
    Filed: August 25, 1993
    Date of Patent: November 8, 1994
    Assignee: Texaco Chemical Inc.
    Inventor: Wei-Yang Su
  • Patent number: 5354893
    Abstract: The present invention relates to an improved catalyst for the selective synthesis of monomethylamine (MMA) and dimethylamine (DMA) at the expense of trimethylamine (TMA) for a starting feed of methanol and/or dimethyl ether and ammonia. The current industrial catalyst for this process is a standard SiO.sub.2 /Al.sub.2 O.sub.3 material. The present invention combines this standard catalyst with microporous carbon molecular sieves (CMS) to form a composite material (i.e., a CMS/SiO.sub.2 /Al.sub.2 O.sub.3 material) with higher selectivity for the desired products MMA and DMA. The invention also relates to methods of making the improved catalyst and a process of using the improved catalyst material in the production of MMA and DMA.
    Type: Grant
    Filed: July 30, 1993
    Date of Patent: October 11, 1994
    Assignees: The University of Delaware, E. I. Du Pont de Nemours Company, Inc.
    Inventors: Henry C. Foley, George C. Sonnichsen, Loren D. Brake, Ravindra K. Mariwala, David S. Lafyatis
  • Patent number: 5344989
    Abstract: An improved process for production of monomethylamines and dimethylamines, wherein an acidic zeolite H--ZK-5 prepared from K,Sr--ZK-5 is used to increase selectivity of the reaction.
    Type: Grant
    Filed: June 15, 1993
    Date of Patent: September 6, 1994
    Assignee: E. I. Du Pont de Nemours and Company
    Inventors: David R. Corbin, Stephan Schwarz
  • Patent number: 5331102
    Abstract: Color-containing alkanolamines or alkyleneamines, having color numbers of up to 100 PtCo or higher, can be treated with inorganic solid acidic catalysts. Inorganic support materials having bonded inorganic acid functionalities may be used as the inorganic solid acidic catalysts. In the presence of water, these inorganic solid acidic catalysts produce decolorized alkanolamines or alkyleneamines having color numbers of 20 PtCo or less. The process of decolorization can be carried out in batch or continuous mode processes thus providing low cost, high quality and high purity end products.
    Type: Grant
    Filed: June 28, 1993
    Date of Patent: July 19, 1994
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Charles A. Gibson
  • Patent number: 5256786
    Abstract: A process of reforming cyclic alkyleneamines to amine-extended cyclic alkyleneamines involving contacting a cyclic alkyleneamine or mixture of cyclic alkyleneamines in the liquid phase with a catalyst under reaction conditions. The catalyst is selected from the group consisting of (a) Group VB metal oxides, (b) Group VB metal phosphates, (c) silicates of Groups IIA, IIIB, IVB and VB, and (d) specified tungsten oxides. For example, piperazine or a mixture of piperazine and aminoethylpiperazine is contacted with magnesium silicate to yield a mixture of amine-extended piperazines, including 1,2-bis(piperazinyl)-ethane and N,N'-bis(2-piperazinylethyl)piperazine.
    Type: Grant
    Filed: March 2, 1992
    Date of Patent: October 26, 1993
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
  • Patent number: 5231229
    Abstract: A catalyst for making polyalkylenepolyamines by the reaction of a monoalkanolamine with an alkyleneamine which contains phosphorus and fluorine on a metal oxide support, the metal being selected from Groups IIIA, IIIB, IVB and VB of the periodic chart. The surface of a support, e.g. titania, is impregnated with at least one compound which contains fluorine and one which contains phosphorus. The same compound can contain both elements, e.g. a fluorophosphoric acid, or two or more compounds, which together contain the required elements, can be employed.
    Type: Grant
    Filed: December 20, 1990
    Date of Patent: July 27, 1993
    Assignee: The Dow Chemical Company
    Inventors: Stephen J. Webster, Lester L. Melton
  • Patent number: 5231230
    Abstract: This invention relates to a process for making amines having a high yield weight percent of diethylenetriamine (DETA) by condensing an amino compound in the presence of a condensation catalyst selected from a Group IVB metal oxide, a metallic phosphate having a cyclic structure or an acyclic structure which is transformed into a cyclic structure during the process, a metallic polyphosphate having a condensed structure, a Group VIB metal-containing substance and a promoted condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in DETA.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: July 27, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Lloyd M. Burgess, Arthur R. Doumaux, Jr., Stephen W. King, David J. Schreck
  • Patent number: 5225600
    Abstract: This invention relates to a process for making amines by condensing an amino compound in the presence of a Group VIB metal-containing condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in triethylenetetramine (TETA), tetraethylenepentamine (TEPA) and pentaethylenehexamine (PEHA).
    Type: Grant
    Filed: August 26, 1992
    Date of Patent: July 6, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Stephen W. King, Arthur R. Doumaux, Jr., David J. Schreck
  • Patent number: 5225599
    Abstract: This invention relates to a process for making amines having a high yield weight percent of linear triethylenetetramine (L-TETA) and aminoethylethanolamine (AEEA) by condensing an amino compound in the presence of a condensation catalyst selected from a Group IVB metal oxide, a Group VIB metal-containing substance and a promoted condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in L-TETA and AEEA.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: July 6, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Stephen W. King, Lloyd M. Burgess, Arthur R. Doumax, Jr.
  • Patent number: 5225598
    Abstract: This invention relates to a process for making amines having a high yield weight percent of linear pentaethylenehexamine (L-PEHA) and hydroxyethyldiethylenetriamine (HEDETA) by condensing an amino compound in the presence of a condensation catalyst selected from a Group IVB metal oxide, a Group VIB metal-containing substance and a promoted condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in L-PEHA and HEDETA.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: July 6, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Arthur R. Doumaux, Jr., Stephen W. King, Lloyd M. Burgess
  • Patent number: 5220071
    Abstract: This invention relates to a process for making amines having a high yield weight percent of pentaethylenehexamine (PEHA) and hydroxyethyltriethylenetetramine (HETETA) by condensing an amino compound in the presence of a condensation catalyst selected from a Group IVB metal oxide, a Group VIB metal-containing substance and a promoted condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in PEHA and HETETA.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: June 15, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Lloyd M. Burgess, Arthur R. Doumaux, Jr., Stephen W. King, David J. Schreck
  • Patent number: 5214213
    Abstract: This invention relates to a process for making amines having a high yield weight percent of linear tetraethylenepentamine (L-TEPA) and hydroxyethyldiethylenetriamine (HEDETA) by condensing an amino compound in the presence of a condensation catalyst selected from a Group IVB metal oxide, a Group VIB metal-containing substance and a promoted condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in L-TEPA and HEDETA.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: May 25, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Stephen W. King, Lloyd M. Burgess, Arthur R. Doumaux, Jr.
  • Patent number: 5214215
    Abstract: This invention relates to a process for making amines having a high yield weight percent of aminoethylethanolamine (AEEA) by condensing an amino compound in the presence of a condensation catalyst selected from a Group IVB metal oxide, a Group VIB metal-containing substance and a promoted condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in AEEA.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: May 25, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Stephen W. King, Lloyd M. Burgess, Arthur R. Doumaux, Jr.
  • Patent number: 5210307
    Abstract: A process for reforming alkyleneamines to predominantly linearly-extended polyalkylenepolyamines comprising contacting an alkyleneamine or mixture thereof with a catalyst under conditions such that a mixture of polyalkylenepolyamines enriched in linearly-extended products is formed, said catalyst containing at least one compound selected from the group consisting of (a) Group VB metal oxides, (b) Group VB metal phosphates, (c) silicates of Groups IIA, IIIB, IVB, VB, and the lanthanide and actinide metals, and (d) tungsten oxides, with the proviso that the silicates and tungsten oxides are essentially free of aluminum. For example, ethylenediamine is contacted with a catalyst of niobium phosphate or niobic acid under reaction conditions to yield predominantly non-cyclic polyethylenepolyamines.
    Type: Grant
    Filed: January 31, 1992
    Date of Patent: May 11, 1993
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
  • Patent number: 5210306
    Abstract: This invention relates to a process for making amines by condensing an amino compound in the presence of a condensation catalyst and a condensation catalyst promoter, wherein said condensation catalyst promoter is present in an amount sufficient to promote the condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in triethylenetetramine (TETA), tetraethylenepentamine (TEPA) and pentaethylenehexamine (PEHA).
    Type: Grant
    Filed: August 8, 1989
    Date of Patent: May 11, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Arthur R. Doumaux, Jr., David J. Schreck, Stephen W. King, George A. Skoler
  • Patent number: 5210308
    Abstract: A process for the production of a modified H-mordenite which comprises bringing an alkali metal or alkaline earth metal-type mordenite into contact with SiCl.sub.4 under a heating condition and then converting the treated mordenite into an H-type via ion exchange, a catalyst comprising the modified H-mordenite and a process for the production of methylamines using the use of the catalyst.
    Type: Grant
    Filed: April 16, 1992
    Date of Patent: May 11, 1993
    Assignee: Nitto Chemical Industry Co., Ltd.
    Inventors: Kouichi Segawa, Azusa Sugiyama, Hiroyasu Tachibana, Yasuhiko Kurusu
  • Patent number: 5202489
    Abstract: Process of making amines by inter alia the (i) intramolecular condensation of an amino compound to an amine having a lower molecular weight or (ii) the intermolecular condensation of an amino compound with one or more of another amino compound or a compound containing an alcoholic hydroxyl group using a Group IVB metal oxide condensation catalyst. The preferred process involves the manufacture of alkyleneamines, most desirably polyalkylenepolyamines, by such condensation reactions utilizing catalysts containing titanium oxide, zirconium oxide or mixtures of them.
    Type: Grant
    Filed: August 8, 1989
    Date of Patent: April 13, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Arthur R. Doumaux, Jr., David J. Schreck, George A. Skoler, Stephen W. King
  • Patent number: 5202491
    Abstract: A continuously generated alkyleneamines producers composition comprising, based on 100% of the moles of the composition and exclusive of any MEA and water present,a) about 20 to about 40 mole % DETA,b) about 15 to about 60 mole % EDA (net generated),c) about 5 to about 18 mole % AEEA,d) about 3 to about 25 mole % of the combination of PIP, AEP and HEP,e) less than about 1 to about 5 mole % of one or more of TETAs and TEPAs,f) less than about 1 mole % of other polyalkylene polyamines,g) a DETA to AEEA mole ratio greater than about 1.35, andh) an EDA to DETA mole ratio less than 2.60,and the process of manufacturing it which comprises feeding hydrogen, ammonia, MEA and EDA, preferably provided from a recycle stream, to a reaction zone containing a fixed bed of a reductive amination catalyst in a tubular reactor, wherein the hydrogen comprises about 1 to about 30 mole percent of the feed in the reaction zone, the mole ratio of EDA to MEA is greater than 0.
    Type: Grant
    Filed: May 25, 1990
    Date of Patent: April 13, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Lloyd M. Burgess, Charles A. Gibson, David J. Schreck
  • Patent number: 5202490
    Abstract: A continuously generated alkyleneamines producers composition comprising based on 100% of the moles of the compostion and exclusive of any MEA and water present,a) about 15 to about 35 mole % DETA,b) about 15 to about 55 mole % EDA (net generated),c) about 10 to about 35 mole % AEEA,d) about 3 to about 25 mole % of the combination of PIP, AEP and HEP,e) about 3 to about 10 mole % of one or more of TETAs and TEPAs,f) less than about 1 mole % of other polyalkylene polyamines, andg) a DETA to AEEA mole ratio greater than about 0.77 to less than 1.35,and the process of producing the same, which comprises feeding hydrogen, ammonia, MEA and EDA, preferably provided from a recycle stream, to a reaction zone containing a fixed bed of a reductive amination catalyst in a tubular reactor, wherein the hydrogen comprises about 10 to about 50 mole percent of the feed in the reaction zone, the mole ratio of EDA to MEA is less than about 0.
    Type: Grant
    Filed: May 25, 1990
    Date of Patent: April 13, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Lloyd M. Burgess, Charles A. Gibson, David J. Schreck
  • Patent number: 5202492
    Abstract: This invention relates to a process for making amines by condensing an amino compound in the presence of a metallic phosphate condensation catalyst having a cyclic structure or an acyclic structure which is transformed into a cyclic structure during said process. This invention also relates to an alkyleneamines producers composition rich in triethylenetetramine (TETA), tetraethylenepentamine (TEPA) and pentaethylenehexamine (PEHA).
    Type: Grant
    Filed: August 8, 1989
    Date of Patent: April 13, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Arthur R. Doumaux, Jr., David J. Schreck
  • Patent number: 5198592
    Abstract: The invention concerns a method of performing a chemical reaction in which hydrogenation and/or dehydrogenation occurs, in the presence of a supported catalyst comprising a carrier material with copper as active component and iron as a promotor. According to the invention, the proporation of iron, calculated on the amount of copper and iron jointly, on an atomic basis, is no more than 25%. The invention also relates to a catalyst for carrying out the reaction, and to a process for preparing a supported catalyst.
    Type: Grant
    Filed: October 15, 1990
    Date of Patent: March 30, 1993
    Assignee: Engelhard De Meern B.V.
    Inventors: Johannes van Beijnum, Adrianus J. van Dillen, John W. Geus
  • Patent number: 5196588
    Abstract: A continuously generated alkyleneamines producers composition comprising, based on 100% of the moles of the composition and exclusive of any MEA and water present,a) about 14 to about 20 mole % DETA,b) about 45 to about 75 mole % EDA (net generated),c) about 4 to about 10 mole % AEEA,d) about 3 to about 25 mole % of the combination of PIP, AEP and HEP,e) about 0.5 to about 5 mole % of one or more of TETAs and TEPAs,f) less than about 1 mole % of other polyalkylene polymines,g) an EDA to DETA mole ratio greater than about 2.60,h) a DETA to AEEA mole ratio greater than about 1.35, andi) an EDA to AEEA mole ratio greater than about 8,and a process of manufacturing it which comprises feeding hydrogen, ammonia, MEA and EDA, preferably provided from a recycle stream, to a reaction zone containing a fixed bed of a reductive amination catalyst in a tubular reactor, wherein the hydrogen comprises about 1 to about 30 mole percent of the feed in the reaction zone, the mole ratio of EDA to MEA is less than about 0.
    Type: Grant
    Filed: May 25, 1990
    Date of Patent: March 23, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Lloyd M. Burgess, Charles A. Gibson, David J. Schreck
  • Patent number: 5166433
    Abstract: Catalysts whose active material contains, in addition to from 20 to 85% by weight, calculated as ZrO.sub.2, of oxygen-containing zirconium compounds, from 1 to 30% by weight, calculated as CuO, of oxygen-containing compounds of copper and from 1 to 40% by weight each, calculated as CoO or NiO, respectively, of oxygen-containing compounds of cobalt and of nickel are used for the amination of alcohols under hydrogenating conditions.
    Type: Grant
    Filed: January 7, 1991
    Date of Patent: November 24, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Irgang, Juergen Schossig, Wolfgang Schroeder, Siegfried Winderl
  • Patent number: 5166415
    Abstract: This invention relates to a process for making amines having a high yield weight percent of diethylenetriamine (DETA) and aminoethylethanolamine (AEEA) by condensing an amino compound in the presence of a condensation catalyst selected from a Group IVB metal oxide, a Group VIB metal-containing substance and a promoted condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in DETA and AEEA.
    Type: Grant
    Filed: March 30, 1990
    Date of Patent: November 24, 1992
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Arthur R. Doumaux, Jr., Stephen W. King, Lloyd M. Burgess
  • Patent number: 5149877
    Abstract: A process for producing an alkylenamine, which comprises reacting ammonia and/or an alkylenamine with an alkanolamine in the presence of niobium oxide treated with an acid, to obtain an alkylenamine having an increased number of alkylene chains over the ammonia and/or the alkylenamine as starting material.
    Type: Grant
    Filed: June 1, 1990
    Date of Patent: September 22, 1992
    Assignee: Tosoh Corporation
    Inventors: Yasushi Hara, Yukio Ito, Kazuhiko Sekizawa
  • Patent number: 5118851
    Abstract: A process of preparing a mixture of polyalkylenepolyamines and alkanolpolyamines comprising contacting a difunctional aliphatic alcohol with a primary or secondary aliphatic amine in the presence of a metal silicate catalyst wherein the metal is selected from the group consisting of Groups IIA, IIIB, and the lanthanide and actinide metals. For example, monoethanolamine reacts with diethylenetriamine in the presence of magnesium silicate to yield a mixture of higher molecular weight linear and branched polyethylenepolyamines and their corresponding alkanolpolyamines. These product mixtures are useful in the formation of specialty polyurethanes.
    Type: Grant
    Filed: December 5, 1990
    Date of Patent: June 2, 1992
    Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
  • Patent number: 5108579
    Abstract: A zeolite, designated zeolite NU-86, having a molar composition expressed by the formula 100 XO.sub.2 : equal to or less than 10 Y.sub.2 O.sub.3 : equal to less than 20 R.sub.2/n O where R is one or more cations of valency n, X is silicon and/or germanium, Y is one or more of aluminum, iron, gallium, boron, titanium, vanadium, zirconium, molybdenum, arsenic, antimony, chromium and manganese and having an X-ray diffraction pattern including the lines shown in Table 1 is prepared from a reaction mixture comprising XO.sub.2 (preferably silica), Y.sub.2 O.sub.3 (preferably alumina) and a polymethylene alpha, omega-diammonium cation. This zeolite is a useful catalyst for a variety of reactions.
    Type: Grant
    Filed: June 17, 1991
    Date of Patent: April 28, 1992
    Assignee: Imperial Chemical Industries PLC
    Inventor: John L. Casci
  • Patent number: 5103058
    Abstract: Process for producing aliphatic imines and/or amines from aliphatic monohydric alcohols, such as higher molecular weight oxo alcohols, including ether alcohols, comprising the steps of dehydrogenating the alcohol to an aldehyde in situ in the presence of a zinc oxide and/or zinc salt/metal hydroxide dehydrogenation catalyst and a soluble amount of a primary aliphatic amine which condenses immediately with the aldehyde under reflux conditions, with continuous water removal, to form the corresponding aliphatic imine (Schiff base). The corresponding aliphatic amine can be formed by reducing or reductively aminating the imine in known manner to form corresponding primary, secondary or tertiary amines as desired.
    Type: Grant
    Filed: November 5, 1990
    Date of Patent: April 7, 1992
    Assignee: Exxon Chemical Patents Inc
    Inventors: Roy L. Pruett, Michael J. Keenan, Edmund J. Mozeleski
  • Patent number: 5103062
    Abstract: In accordance with the process of the present invention normally liquid, water-soluble poly(oxyethylene/oxypropylene) polyamine products are prepared using an initiator, which may contain oxyethylene groups. In a series of alkoxylation reaction steps the initiator is reacted with predetermined weight percentages of ethylene oxide and propylene oxide, said process comprising the steps of:a. Charging a predetermined percentage of initiator to an alkoxylation reaction zone,b. Alkoxylating said initiator therein with predetermined percentages of ethylene oxide and propylene oxide to provide an intermediate polyol,c. Propoxylating said intermediate polyol with a predetermined percentage of propylene oxide to provide a normally liquid, water-soluble precursor polyol, andd.
    Type: Grant
    Filed: April 10, 1987
    Date of Patent: April 7, 1992
    Assignee: Texaco Inc.
    Inventors: Michael Cuscurida, Ernest L. Yeakey
  • Patent number: 5101074
    Abstract: This invention relates to vicinal di(hetero)alkylene organometalate compounds comprising one or more metal oxides in association with an alkanolamine, an alkyleneamine, an alkylene glycol or mixtures thereof. This invention also relates to an alkyleneamines producers composition rich in triethylenetetramine (TETA), tetraethylenepentamine (TEPA) and pentaethylenehexamine (PEHA), and to processes for the preparation thereof using the vicinal di(hetero)alkylene organometalates.
    Type: Grant
    Filed: August 8, 1989
    Date of Patent: March 31, 1992
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Stephen W. King, Arthur R. Doumaux, Jr., David J. Schreck, George A. Skoler
  • Patent number: 5082972
    Abstract: At least one of ammonia and ethylenediamine is reacted with monoethanolamine in the presence of a catalyst containing phosphoric acid or its condensate in order to prepare acyclic ethyleneamines, and the catalyst can be improved in performance and the life of the catalyst can be prolonged by feeding a phosphorus-containing material to a reaction system during the reaction. In addition, the catalyst having a deteriorated performance can be reactivated by adding the phosphorus-containing material to the catalyst.
    Type: Grant
    Filed: July 11, 1990
    Date of Patent: January 21, 1992
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Tadashi Komiyama, Hisaharu Kuboyama, Takashi Jimbo, Hiroyoshi Watanabe, Shuichi Tokumoto, Yumiko Endoh, Eiichi Sugiyama, Yoshitaro Naganuma
  • Patent number: 5073649
    Abstract: A process for producing an alkylenamine, which comprises reacting ammonia and/or a polyalkylene polyamine with an alkanolamine to obtain an alkylenamine having an increased number of alkylene chains over the ammonia and/or the alkylenamine as starting material, wherein a catalyst having a niobium-containing substance supported on a carrier is used for the reaction.
    Type: Grant
    Filed: February 9, 1989
    Date of Patent: December 17, 1991
    Assignee: Tosoh Corporation
    Inventors: Yasushi Hara, Nobumasa Suzuki, Yukio Ito, Kazuhiko Sekizawa
  • Patent number: 5073635
    Abstract: A process of preparing linearly-extended polyalkylenepolyamines, such as linear and branched polyethylenepolyamines, comprising contacting a difunctional aliphatic alcohol, such as monoethanolamine, with a reactant aliphatic amine, such as ethylenediamine, in the presence of a metal silicate catalyst wherein the metal is selected from Groups IIIB, IVB, VB and the lanthanide rare earth metals. Reactions of piperazines with alkanolamines to yield alcohol-extended and/or amine-extended piperazines are included in the process of this invention.
    Type: Grant
    Filed: June 22, 1990
    Date of Patent: December 17, 1991
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
  • Patent number: 5068329
    Abstract: A continuously generated alkyleneamines produces composition comprising, based on 100% of the moles of the composition and exclusive of any MEA and water present,a) about 50 to about 90 mole % AEEA,b) less than about 3 mole % EDA but more than 0.01 mole % EDA,c) less than about 2 mole % DETA but more than 0.01 mole % DETA,d) about 5 to about 18 mole % of the combination of PIP, AEP and HEP,e) about 5 to about 20 mole % of one or more of TETAs and TEPAs,f) less than about 1 mole % of other polyalkylene polyamines,g) a mole ratio of AEEA to the combination of PIP, AEP, HEP, DETA and EDA is greater than about 2.
    Type: Grant
    Filed: September 4, 1990
    Date of Patent: November 26, 1991
    Assignee: Union Carbide Chemicals and Plastics Technology Corporation
    Inventors: Lloyd M. Burgess, Charles A. Gibson
  • Patent number: 5068442
    Abstract: There is provided a method for maintaining the activity of a zeolite catalyst in the catalytic production of methylamines from methanol and ammonia using a zeolite catalyst as at least one of catalysts applied, which comprises controlling the amount of aldehyde compounds as impurities flowing into a zeolite catalyst layer to about 0.15 g/hr.kg-cat. or lower, as calculated in terms of formaldehyde.
    Type: Grant
    Filed: May 17, 1989
    Date of Patent: November 26, 1991
    Assignee: Nitto Kagaku Kogyo Kabushiki Kaisha
    Inventors: Yoshiro Ashina, Takeyuki Fujita, Kiyonobu Niwa, Takeshi Inagaki, Yuko Nikaido
  • Patent number: 5068330
    Abstract: A continuously generated alkyleneamines producers composition comprising, based on 100% of the moles of the composition and exclusive of any MEA and water present,a) about 15 to about 50 mole % AEEA,b) about 15 to about 55 mole % EDA,c) about 10 to about 20 mole % DETA,d) about 5 to about 20 mole % of the combination of PIP,AEP and HEP,3) about 3 to about 10 mole % of one or more of TETAs and TEPAs,f) less than about 1 mole % of other polyalkylene polyamines,g) an DETA to AEEA mole ratio less than 0.77, andh) an EDA to AEEA mole ratio less than 8;and a process of manufacturing the same, which comprises feeding hydrogen, ammonia and MEA to a reaction zone containing a fixed bed of a reductive amination catalyst, wherein the hydrogen comprises about 20 to about 60 mole percent of the feed in the reaction zone and the mole ratio of ammonia to MEA is about 1 to about 5, the temperature of the reaction zone is about 120.degree. C. to about 300.degree. C.
    Type: Grant
    Filed: September 4, 1990
    Date of Patent: November 26, 1991
    Assignee: Union Carbide Chemicals and Plastics Technology Corporation
    Inventors: Lloyd M. Burgess, Charles A. Gibson
  • Patent number: 5053152
    Abstract: Improved additives/dispersants for lubricant and fuel compositions are obtained by condensing a hydroxyalkyl or hydroxyaryl compound with an amine compound. The condensates according to the present invention are produced by the acid catalyzed condensation of the amine reactant with the hydroxy reactant.
    Type: Grant
    Filed: August 3, 1989
    Date of Patent: October 1, 1991
    Assignee: The Lubrizol Corporation
    Inventor: Thomas F. Steckel
  • Patent number: 5019653
    Abstract: Disclosed is a method for purification of polyamines which comprises contacting said polyamines with a treating agent selected from the group consisting of oxides, hydroxides or alkoxides of elements from the group consisting of silicon or Group IIA, IIIA, IIB, IIIB, IVB or VB at a temperature of about 150.degree. C. to 250.degree. C. and a pressure of subatomspheric to 10 atmospheres for a period of time sufficient to lower the hydroxyl impurity level of said amines.
    Type: Grant
    Filed: May 14, 1990
    Date of Patent: May 28, 1991
    Assignee: Texaco Chemical Company
    Inventors: George P. Speranza, Donald H. Champion
  • Patent number: 5015773
    Abstract: An amine is produced by reacting in the presence of hydrogen at elevated temperature a first reactant which is a compound substantially involatile at the elevated temperature employed and having either one, two or more hydroxyl functions, each of which is independently either a primary or secondary hydroxyl function, with a second reactant which is either ammonia or a primary or a secondary amine in the presence of a reductive amination catalyst wherein the reaction is effected in either a continuously or periodically open system.
    Type: Grant
    Filed: August 4, 1989
    Date of Patent: May 14, 1991
    Assignee: BP Chemicals Limited
    Inventor: Ian D. Dobson
  • Patent number: 5011999
    Abstract: A process for the preparation of predominantly non-cyclic polyalkylenepolyamines comprising contacting a difunctional aliphatic alcohol with ammonia or a primary or secondary aliphatic amine in the presence of a catalyst selected from the group consisting of Group VB metal oxides, niobium phosphates, tantalum phosphates, and mixtures thereof. For example, monoethanolamine is aminated by ethylenediamine to predominantly linear and branched polyethylenepolyamines in the presence of a catalyst containing niobium oxide supported on boehmite alumina.
    Type: Grant
    Filed: February 23, 1989
    Date of Patent: April 30, 1991
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, George E. Hartwell, David C. Molzahn, Enrique G. Ramirez, John E. Lastovica, Jr.
  • Patent number: 5003107
    Abstract: Poly(oxytetramethylene) diamines useful in the preparation of polyamide and polyurea elastomers are prepared by the catalytic reductive amination of a poly(oxytetramethylene) glycol feedstock under reductive amination conditions in the presence of ammonia and hydrogen using a hydrogenation/dehydrogenation catalyst composed of, on an oxide-free basis, about 70 to 75 wt. % of nickel, about 20 to about 25 wt. % of copper, about 0.5 to 5 wt. % of chromium and about 1 to 5 wt. % of molybdenum.
    Type: Grant
    Filed: December 18, 1989
    Date of Patent: March 26, 1991
    Assignee: Texaco Chemical Company
    Inventors: Robert L. Zimmerman, John M. Larkin
  • Patent number: 4999329
    Abstract: A catalyst for making polyalkylenepolyamines by the reaction of a monoalkanolamine with an alkyleneamine which contains phosphorus and fluorine on a metal oxide support, the metal being selected from Groups IIIA, IIIB, IVB and VB of the periodic chart. The surface of a support, e.g. titania, is impregnated with at least one compound which contains fluorine and one which contains phosphorus. The same compound can contain both elements, e.g. a fluorophosphoric acid, or two or more compounds, which together contain the required elements, can be employed.
    Type: Grant
    Filed: October 6, 1989
    Date of Patent: March 12, 1991
    Assignee: The Dow Chemical Company
    Inventors: Stephen J. Webster, Lester L. Melton
  • Patent number: 4994620
    Abstract: Alkylamines such as methylamine and dimethylamine react with alcohols and aldehydes at 150.degree.-275.degree. C. in the presence of hydrogen and a catalyst initially consisting essentially of (1) a copper compound selected from copper carbonate, copper oxide, copper hydroxide or mixtures thereof, (2) a zinc compound selected from zinc carbonate, zinc oxide, zinc hydroxide or mixtures thereof and (3) a metal compound selected from carbonates, oxides and hydroxides of a Group IIA metal and mixtures thereof at least one of said copper compound and zinc compound being a carbonate. Conversions and yields are high and the amount of heavy by-product is low.
    Type: Grant
    Filed: May 19, 1988
    Date of Patent: February 19, 1991
    Assignee: Ethyl Corporation
    Inventors: Pak Y. Fong, Kim R. Smith, Joe D. Sauer
  • Patent number: 4994622
    Abstract: Mono- and di-lower alkylamines, e.g. methylamine or dimethylamine, are alkylated by reaction with C.sub.8-22 alcohol in the presence of hydrogen at a temperature of about 150.degree.-275.degree. C. in contact with a copper-zinc-alkaline earth metal base containing catalyst (e.g., CuO-ZnO-Ba(OH).sub.2) while removing water formed in the reaction.
    Type: Grant
    Filed: December 16, 1987
    Date of Patent: February 19, 1991
    Assignee: Ethyl Corporation
    Inventors: Pak Y. Fong, Kim R. Smith, Joe D. Sauer
  • 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