By Transamination Patents (Class 564/470)
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Patent number: 5410087Abstract: A process of reforming an alkyleneamine feedstock or a mixture of such feedstocks to an alkyleneamine or a mixture of alkyleneamines which is different from the feedstock or feedstock mixture. The process is catalyzed by one of the following: Group VB metal oxides, Group VB metal phosphates, Group IIA metal silicates, and tungsten oxides. For example, ethylenediamine is contacted with a catalyst of niobic acid or magnesium silicate to yield predominantly diethylenetriamine and non-cyclic triethylenetetramines; whereas high molecular weight polyethylenepolyamines are cracked by the same catalysts to mixtures of lower molecular weight linear and cyclic materials.Type: GrantFiled: November 17, 1993Date of Patent: April 25, 1995Assignee: The Dow Chemical CompanyInventors: George E. Hartwell, David C. Molzahn, Robert G. Bowman
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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: 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: 5288909Abstract: A process of reforming an alkyleneamine feedstock or a mixture of such feedstocks to an alkyleneamine or a mixture of alkyleneamines which is different from the feedstock or feedstock mixture. The process is catalyzed by one of the following: Group VB metal oxides, Group VB metal phosphates, Group IIA metal silicates, and tungsten oxides. For example, ethylenediamine is contacted with a catalyst of niobic acid or magnesium silicate to yield predominantly diethylenetriamine and non-cyclic triethylenetetramines; whereas high molecular weight polyethylenepolyamines are cracked by the same catalysts to mixtures of lower molecular weight linear and cyclic materials.Type: GrantFiled: August 19, 1992Date of Patent: February 22, 1994Assignee: The Dow Chemical CompanyInventors: George E. Hartwell, Robert G. Bowman, David C. Molzahn
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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: 5254737Abstract: A method for producing secondary amines, particularly fatty secondary amines such as ditallowamine from fatty nitriles, such as tallow nitrile over a reduction, hydrogenation catalyst, such as nickel or cobalt, in two steps has been discovered. The reaction gives high selectivity of secondary amine over the coproduced primary and tertiary amines. The first step of the reaction is conducted continuously in the presence of ammonia and hydrogen. The secondary amine proportion is increased by a second stage using the same catalyst as the first stage, but in the absence of ammonia.Type: GrantFiled: September 17, 1990Date of Patent: October 19, 1993Assignee: Texaco Chemical CompanyInventor: Robert L. Zimmerman
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Patent number: 5243078Abstract: A process for selectively preparing predominantly noncyclic polyalkylene polyamines wherein one or more linear alkyleneamines are reacted in the presence of a mordenite catalyst under conditions sufficient to effect a disproportionation reaction. Preferably, the catalyst is prepared by treating the mordenite with an amount of a phosphorus-containing moiety sufficient to provide a catalyst which is impregnated with from about 0.01 to 15 wt % elemental phosphorus based upon the total weight of the impregnated mordenite catalyst. The process is especially useful in the production of diethylenetriamine wherein ethylenediamine is reacted in the presence of LZ-M-8 catalyst which has been treated with an amount of ammonium dihydrogen phosphate sufficient to provide a catalyst which is impregnated with from about 0.1 to 8 wt % elemental phosphorus based upon the total weight of the impregnated mordenite catalyst. The products can be isolated by conventional techniques such as distillation.Type: GrantFiled: June 23, 1989Date of Patent: September 7, 1993Assignee: Air Products and Chemicals, Inc.Inventors: Rakesh Agrawal, John H. Frey
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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: 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: 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: 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: 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: 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: 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: 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: 5166442Abstract: A process of reforming an alkyleneamine feedstock or a mixture of such feedstocks to an alkyleneamine or a mixture of alkyleneamines which is different from the feedstock or feedstock mixture. The process is catalyzed by one of the following: Group VB metal oxides, Group VB metal phosphates, Group IIA metal silicates, and tungsten oxides. For example, ethylenediamine is contacted with a catalyst of niobic acid or magnesium silicate to yield predominantly diethylenetriamine and non-cyclic triethylenetetramines; whereas high molecular weight polyethylenepolyamines are cracked by the same catalysts to mixtures of lower molecular weight linear and cyclic materials.Type: GrantFiled: July 16, 1991Date of Patent: November 24, 1992Assignee: The Dow Chemical CompanyInventors: George E. Hartwell, Robert G. Bowman, David C. Molzahn
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Patent number: 5130491Abstract: A method for producing secondary amines, particularly fatty secondary amines such as ditallowamine from fatty nitriles, such as tallow nitrile over a nickel catalyst promoted with copper, chromium and molybdenum has been discovered. The reaction gives high selectivity of secondary amine over the coproduced primary and tertiary amines. The reaction may be conducted continuously in the presence of ammonia and hydrogen. The secondary amine proportion may be increased by a second stage using the same catalyst as the first stage, but in the absence of ammonia. The same catalyst may be used in both steps if a two stage process is used.Type: GrantFiled: September 17, 1990Date of Patent: July 14, 1992Assignee: Texaco Chemical CompanyInventor: Robert L. Zimmerman
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Patent number: 5118850Abstract: 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 oxdies, 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: November 9, 1990Date of Patent: June 2, 1992Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
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Patent number: 5055618Abstract: The object of this invention is the preparation of .alpha.,.omega.-diamines from .alpha., .omega.-dialdehydes in a method which comprises the reaction of a starting mixture of said dialdehyde, a primary amine, and water to form a reaction mixture, followed by treatment of said reaction mixture with excess ammonia and hydrogen in the presence of a hydrogenation catalyst to produce a final mixture.Type: GrantFiled: May 21, 1990Date of Patent: October 8, 1991Assignee: Hoechst AktiengesellschaftInventors: Detlef Kampmann, Jurgen Weber, Claus Kniep
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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: 4996363Abstract: 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: December 20, 1988Date of Patent: February 26, 1991Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
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Patent number: 4940817Abstract: N-Alkylanilines can be prepared by reaction of anilines with N,N-dialkylanilines in the gas or liquid phase at elevated temperature by carrying out the reaction in the presence of zeolites.Type: GrantFiled: January 25, 1989Date of Patent: July 10, 1990Assignee: Bayer AktiengesellschaftInventors: Gunter Klug, Hans-Josef Buysch, Lothar Puppe
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Patent number: 4845295Abstract: Alkylamines are self-alkylated to longer carbon chain alkylamines using a catalyst comprising a Group VIIB or a Group VIII metal supported on a porous inert carrier.Type: GrantFiled: April 29, 1987Date of Patent: July 4, 1989Assignee: Shell Oil CompanyInventor: Kuo-Hua Chao
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Patent number: 4812595Abstract: Alkylamines are self-alkylated to longer carbon chain alkylamines using a catalyst mixture comprising a quaternary ammonium halide in combination with ruthenium carbonyl.Type: GrantFiled: October 23, 1987Date of Patent: March 14, 1989Assignee: Shell Oil CompanyInventor: Kuo-Hua Chao
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Patent number: 4792629Abstract: Alkylamines are self-alkylated to longer carbon chain alkylamines using a catalyst mixture comprising ruthenium carbonyl and a compound of the formula (cyclopentadienyl).sub.n MY.sub.4-n where M is Zr, Hf or Ti, Y is individually selected from hydrogen, C.sub.1 -C.sub.5 alky, C.sub.6 -C.sub.20 aryl, C.sub.1 -C.sub.25 metalalkyl and halogen and n is 1, 2, 3 or 4.Type: GrantFiled: February 24, 1987Date of Patent: December 20, 1988Assignee: Shell Oil CompanyInventor: Kuo-Hua Chao
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Patent number: 4783554Abstract: Alkylamines are self-alkylated to longer carbon chain alkylamines using a catalyst mixture comprising of aluminum chloride in combination with cobalt and/or ruthenium carbonyl.Type: GrantFiled: December 10, 1986Date of Patent: November 8, 1988Assignee: Shell Oil CompanyInventor: Kuo-Hua Chao
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Patent number: 4645837Abstract: In the transalkylation of tertiary amines, unexpected higher yields are achieved requiring substantially less catalyst and much shorter reaction times at lower reaction temperatures using a homogeneous catalyst in the presence of an alcohol solvent and carbon monoxide. The process may be exemplified by reacting triethylamine and tripropylamine in the presence of a homogeneous triosmiumdodecacarbonyl catalyst, ethanol, and carbon monoxide to prepare diethylpropylamine and ethyldipropylamine.Type: GrantFiled: November 5, 1984Date of Patent: February 24, 1987Assignee: SRI InternationalInventors: Richard M. Laine, Youval Shvo
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Patent number: 4547591Abstract: Disclosed is a process for preparing predominantly linear polyethylenepolyamines from the catalyzed reaction of (1) an ethyleneamine and an alkanolamine, (2) ethyleneamines or (3) an alkanolamine and ammonia. The catalyst employed is a silica-alumina catalyst. An acidic phosphorus cocatalyst may be used in conjunction with the silica-alumina catalyst.Type: GrantFiled: December 16, 1983Date of Patent: October 15, 1985Assignee: Texaco Inc.Inventors: Michael E. Brennan, James H. Templeton, Ernest L. Yeakey
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Patent number: 4430513Abstract: Alkylamine compounds which contain at least two alkyl substituents containing from about 2 to about 6 carbon atoms may be alkylated at temperatures ranging from about 50.degree. to about 300.degree. C. and pressures ranging from about 20 to about 300 atmospheres in the presence of a metal carbonyl or a metal compound capable of forming a carbonyl at reaction conditions.Type: GrantFiled: August 31, 1981Date of Patent: February 7, 1984Assignee: UOP Inc.Inventor: Edwin H. Homeier