By Transamination Patents (Class 564/470)
  • Patent number: 5410087
    Abstract: 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: Grant
    Filed: November 17, 1993
    Date of Patent: April 25, 1995
    Assignee: The Dow Chemical Company
    Inventors: George E. Hartwell, David C. Molzahn, Robert G. Bowman
  • 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: 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: 5288909
    Abstract: 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: Grant
    Filed: August 19, 1992
    Date of Patent: February 22, 1994
    Assignee: The Dow Chemical Company
    Inventors: George E. Hartwell, Robert G. Bowman, David C. Molzahn
  • 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: 5254737
    Abstract: 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: Grant
    Filed: September 17, 1990
    Date of Patent: October 19, 1993
    Assignee: Texaco Chemical Company
    Inventor: Robert L. Zimmerman
  • Patent number: 5243078
    Abstract: 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: Grant
    Filed: June 23, 1989
    Date of Patent: September 7, 1993
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Rakesh Agrawal, John H. Frey
  • 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: 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: 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: 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: 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: 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: 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: 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: 5166442
    Abstract: 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: Grant
    Filed: July 16, 1991
    Date of Patent: November 24, 1992
    Assignee: The Dow Chemical Company
    Inventors: George E. Hartwell, Robert G. Bowman, David C. Molzahn
  • Patent number: 5130491
    Abstract: 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: Grant
    Filed: September 17, 1990
    Date of Patent: July 14, 1992
    Assignee: Texaco Chemical Company
    Inventor: Robert L. Zimmerman
  • Patent number: 5118850
    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 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: Grant
    Filed: November 9, 1990
    Date of Patent: June 2, 1992
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
  • Patent number: 5055618
    Abstract: 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: Grant
    Filed: May 21, 1990
    Date of Patent: October 8, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Detlef Kampmann, Jurgen Weber, Claus Kniep
  • 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: 4996363
    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: December 20, 1988
    Date of Patent: February 26, 1991
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
  • Patent number: 4940817
    Abstract: 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: Grant
    Filed: January 25, 1989
    Date of Patent: July 10, 1990
    Assignee: Bayer Aktiengesellschaft
    Inventors: Gunter Klug, Hans-Josef Buysch, Lothar Puppe
  • Patent number: 4845295
    Abstract: 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: Grant
    Filed: April 29, 1987
    Date of Patent: July 4, 1989
    Assignee: Shell Oil Company
    Inventor: Kuo-Hua Chao
  • Patent number: 4812595
    Abstract: Alkylamines are self-alkylated to longer carbon chain alkylamines using a catalyst mixture comprising a quaternary ammonium halide in combination with ruthenium carbonyl.
    Type: Grant
    Filed: October 23, 1987
    Date of Patent: March 14, 1989
    Assignee: Shell Oil Company
    Inventor: Kuo-Hua Chao
  • Patent number: 4792629
    Abstract: 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: Grant
    Filed: February 24, 1987
    Date of Patent: December 20, 1988
    Assignee: Shell Oil Company
    Inventor: Kuo-Hua Chao
  • Patent number: 4783554
    Abstract: 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: Grant
    Filed: December 10, 1986
    Date of Patent: November 8, 1988
    Assignee: Shell Oil Company
    Inventor: Kuo-Hua Chao
  • Patent number: 4645837
    Abstract: 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: Grant
    Filed: November 5, 1984
    Date of Patent: February 24, 1987
    Assignee: SRI International
    Inventors: Richard M. Laine, Youval Shvo
  • Patent number: 4547591
    Abstract: 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: Grant
    Filed: December 16, 1983
    Date of Patent: October 15, 1985
    Assignee: Texaco Inc.
    Inventors: Michael E. Brennan, James H. Templeton, Ernest L. Yeakey
  • Patent number: 4430513
    Abstract: 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: Grant
    Filed: August 31, 1981
    Date of Patent: February 7, 1984
    Assignee: UOP Inc.
    Inventor: Edwin H. Homeier