Catalyst Utilized Patents (Class 564/479)
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Patent number: 5482909Abstract: 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: GrantFiled: July 21, 1994Date of Patent: January 9, 1996Assignees: 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
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Patent number: 5410086Abstract: 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: GrantFiled: June 25, 1991Date of Patent: April 25, 1995Inventor: Lloyd M. Burgess
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Patent number: 5399769Abstract: 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: GrantFiled: June 3, 1994Date of Patent: March 21, 1995Assignee: Air Products and Chemicals, Inc.Inventors: Frederick C. Wilhelm, Gene E. Parris, Brent A. Aufdembrink, Thomas R. Gaffney
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Patent number: 5382696Abstract: 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: GrantFiled: October 6, 1993Date of Patent: January 17, 1995Assignee: Mitsui Toatsu Chemicals, IncorporatedInventors: Tadamitsu Kiyoura, Kazuhiro Terada
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Patent number: 5364971Abstract: 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: GrantFiled: August 25, 1993Date of Patent: November 15, 1994Assignee: Texaco Chemical Inc.Inventor: Wei-Yang Su
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Patent number: 5362914Abstract: 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: GrantFiled: August 25, 1993Date of Patent: November 8, 1994Assignee: Texaco Chemical Inc.Inventor: Wei-Yang Su
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Patent number: 5354893Abstract: 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: GrantFiled: July 30, 1993Date of Patent: October 11, 1994Assignees: 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
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Patent number: 5344989Abstract: 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: GrantFiled: June 15, 1993Date of Patent: September 6, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventors: David R. Corbin, Stephan Schwarz
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Patent number: 5331102Abstract: 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: GrantFiled: June 28, 1993Date of Patent: July 19, 1994Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Charles A. Gibson
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Patent number: 5256786Abstract: 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: GrantFiled: March 2, 1992Date of Patent: October 26, 1993Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
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Patent number: 5231229Abstract: 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: GrantFiled: December 20, 1990Date of Patent: July 27, 1993Assignee: The Dow Chemical CompanyInventors: Stephen J. Webster, Lester L. Melton
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Patent number: 5231230Abstract: 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: GrantFiled: March 30, 1990Date of Patent: July 27, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Lloyd M. Burgess, Arthur R. Doumaux, Jr., Stephen W. King, David J. Schreck
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Patent number: 5225600Abstract: 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: GrantFiled: August 26, 1992Date of Patent: July 6, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Arthur R. Doumaux, Jr., David J. Schreck
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Patent number: 5225599Abstract: 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: GrantFiled: March 30, 1990Date of Patent: July 6, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Lloyd M. Burgess, Arthur R. Doumax, Jr.
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Patent number: 5225598Abstract: 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: GrantFiled: March 30, 1990Date of Patent: July 6, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Arthur R. Doumaux, Jr., Stephen W. King, Lloyd M. Burgess
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Patent number: 5220071Abstract: 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: GrantFiled: March 30, 1990Date of Patent: June 15, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Lloyd M. Burgess, Arthur R. Doumaux, Jr., Stephen W. King, David J. Schreck
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Patent number: 5214213Abstract: 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: GrantFiled: March 30, 1990Date of Patent: May 25, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Lloyd M. Burgess, Arthur R. Doumaux, Jr.
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Patent number: 5214215Abstract: 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: GrantFiled: March 30, 1990Date of Patent: May 25, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Lloyd M. Burgess, Arthur R. Doumaux, Jr.
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Patent number: 5210307Abstract: 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: GrantFiled: January 31, 1992Date of Patent: May 11, 1993Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
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Patent number: 5210306Abstract: 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: GrantFiled: August 8, 1989Date of Patent: May 11, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Arthur R. Doumaux, Jr., David J. Schreck, Stephen W. King, George A. Skoler
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Patent number: 5210308Abstract: 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: GrantFiled: April 16, 1992Date of Patent: May 11, 1993Assignee: Nitto Chemical Industry Co., Ltd.Inventors: Kouichi Segawa, Azusa Sugiyama, Hiroyasu Tachibana, Yasuhiko Kurusu
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Patent number: 5202489Abstract: 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: GrantFiled: August 8, 1989Date of Patent: April 13, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Arthur R. Doumaux, Jr., David J. Schreck, George A. Skoler, Stephen W. King
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Patent number: 5202491Abstract: 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: GrantFiled: May 25, 1990Date of Patent: April 13, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Lloyd M. Burgess, Charles A. Gibson, David J. Schreck
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Patent number: 5202490Abstract: 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: GrantFiled: May 25, 1990Date of Patent: April 13, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Lloyd M. Burgess, Charles A. Gibson, David J. Schreck
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Patent number: 5202492Abstract: 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: GrantFiled: August 8, 1989Date of Patent: April 13, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Arthur R. Doumaux, Jr., David J. Schreck
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Patent number: 5198592Abstract: 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: GrantFiled: October 15, 1990Date of Patent: March 30, 1993Assignee: Engelhard De Meern B.V.Inventors: Johannes van Beijnum, Adrianus J. van Dillen, John W. Geus
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Patent number: 5196588Abstract: 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: GrantFiled: May 25, 1990Date of Patent: March 23, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Lloyd M. Burgess, Charles A. Gibson, David J. Schreck
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Patent number: 5166433Abstract: 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: GrantFiled: January 7, 1991Date of Patent: November 24, 1992Assignee: BASF AktiengesellschaftInventors: Matthias Irgang, Juergen Schossig, Wolfgang Schroeder, Siegfried Winderl
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Patent number: 5166415Abstract: 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: GrantFiled: March 30, 1990Date of Patent: November 24, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Arthur R. Doumaux, Jr., Stephen W. King, Lloyd M. Burgess
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Patent number: 5149877Abstract: 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: GrantFiled: June 1, 1990Date of Patent: September 22, 1992Assignee: Tosoh CorporationInventors: Yasushi Hara, Yukio Ito, Kazuhiko Sekizawa
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Patent number: 5118851Abstract: 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: GrantFiled: December 5, 1990Date of Patent: June 2, 1992Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
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Patent number: 5108579Abstract: 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: GrantFiled: June 17, 1991Date of Patent: April 28, 1992Assignee: Imperial Chemical Industries PLCInventor: John L. Casci
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Patent number: 5103058Abstract: 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: GrantFiled: November 5, 1990Date of Patent: April 7, 1992Assignee: Exxon Chemical Patents IncInventors: Roy L. Pruett, Michael J. Keenan, Edmund J. Mozeleski
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Patent number: 5103062Abstract: 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: GrantFiled: April 10, 1987Date of Patent: April 7, 1992Assignee: Texaco Inc.Inventors: Michael Cuscurida, Ernest L. Yeakey
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Patent number: 5101074Abstract: 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: GrantFiled: August 8, 1989Date of Patent: March 31, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Arthur R. Doumaux, Jr., David J. Schreck, George A. Skoler
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Patent number: 5082972Abstract: 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: GrantFiled: July 11, 1990Date of Patent: January 21, 1992Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Tadashi Komiyama, Hisaharu Kuboyama, Takashi Jimbo, Hiroyoshi Watanabe, Shuichi Tokumoto, Yumiko Endoh, Eiichi Sugiyama, Yoshitaro Naganuma
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Patent number: 5073649Abstract: 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: GrantFiled: February 9, 1989Date of Patent: December 17, 1991Assignee: Tosoh CorporationInventors: Yasushi Hara, Nobumasa Suzuki, Yukio Ito, Kazuhiko Sekizawa
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Patent number: 5073635Abstract: 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: GrantFiled: June 22, 1990Date of Patent: December 17, 1991Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
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Patent number: 5068329Abstract: 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: GrantFiled: September 4, 1990Date of Patent: November 26, 1991Assignee: Union Carbide Chemicals and Plastics Technology CorporationInventors: Lloyd M. Burgess, Charles A. Gibson
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Patent number: 5068442Abstract: 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: GrantFiled: May 17, 1989Date of Patent: November 26, 1991Assignee: Nitto Kagaku Kogyo Kabushiki KaishaInventors: Yoshiro Ashina, Takeyuki Fujita, Kiyonobu Niwa, Takeshi Inagaki, Yuko Nikaido
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Patent number: 5068330Abstract: 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: GrantFiled: September 4, 1990Date of Patent: November 26, 1991Assignee: Union Carbide Chemicals and Plastics Technology CorporationInventors: Lloyd M. Burgess, Charles A. Gibson
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Patent number: 5053152Abstract: 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: GrantFiled: August 3, 1989Date of Patent: October 1, 1991Assignee: The Lubrizol CorporationInventor: Thomas F. Steckel
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Patent number: 5019653Abstract: 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: GrantFiled: May 14, 1990Date of Patent: May 28, 1991Assignee: Texaco Chemical CompanyInventors: George P. Speranza, Donald H. Champion
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Patent number: 5015773Abstract: 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: GrantFiled: August 4, 1989Date of Patent: May 14, 1991Assignee: BP Chemicals LimitedInventor: Ian D. Dobson
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Patent number: 5011999Abstract: 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: GrantFiled: February 23, 1989Date of Patent: April 30, 1991Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, George E. Hartwell, David C. Molzahn, Enrique G. Ramirez, John E. Lastovica, Jr.
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Patent number: 5003107Abstract: 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: GrantFiled: December 18, 1989Date of Patent: March 26, 1991Assignee: Texaco Chemical CompanyInventors: Robert L. Zimmerman, John M. Larkin
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Patent number: 4999329Abstract: 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: GrantFiled: October 6, 1989Date of Patent: March 12, 1991Assignee: The Dow Chemical CompanyInventors: Stephen J. Webster, Lester L. Melton
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Patent number: 4994620Abstract: 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: GrantFiled: May 19, 1988Date of Patent: February 19, 1991Assignee: Ethyl CorporationInventors: Pak Y. Fong, Kim R. Smith, Joe D. Sauer
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Patent number: 4994622Abstract: 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: GrantFiled: December 16, 1987Date of Patent: February 19, 1991Assignee: Ethyl CorporationInventors: Pak Y. Fong, Kim R. Smith, Joe D. Sauer
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Patent number: 4992150Abstract: 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: GrantFiled: April 13, 1989Date of Patent: February 12, 1991Assignee: Nippon Oil Co, Ltd.Inventors: Jinichi Igarashi, Harumichi Watanabe