Preparing Directly By Amination Patents (Class 564/469)
  • Patent number: 5557011
    Abstract: Process for the preparation of diamines of the general formula I ##STR1## in which A denotes a C.sub.1 -C.sub.20 alkylene chain optionally mono- to penta-substituted by C.sub.1 -C.sub.4 alkyl,R.sup.1, R.sup.2 denote C.sub.1 -C.sub.20 alkyl, C.sub.1 -C.sub.20 hydroxyalkyl, C.sub.3 -C.sub.8 cycloalkyl, C.sub.4 -C.sub.20 alkylcycloalkyl, C.sub.4 -C.sub.20 cycloalkylalkyl, phenyl, C.sub.7 -C.sub.20 phenylalkyl, C.sub.1 -C.sub.20 alkoxyalkyl, C.sub.7 -C.sub.20 phenoxyalkyl or together a saturated or unsaturated C.sub.2 -C.sub.6 alkylene chain optionally monosubstituted, disubstituted, or trisubstituted by C.sub.1 -C.sub.4 alkyl and optionally interrupted by oxygen or nitrogen,by the reaction of dinitriles of the general formula IINC--A--CN (II),in which A has the aforementioned meaning,with secondary amines of the general formula II ##STR2## in which R.sup.1 and R.sup.2 have the aforementioned meanings, with hydrogen at temperatures ranging from 50.degree. to 200.degree. C.
    Type: Grant
    Filed: November 15, 1994
    Date of Patent: September 17, 1996
    Assignee: BASF Aktiengesellschaft
    Inventors: Tom Witzel, Eberhard Fuchs
  • Patent number: 5523478
    Abstract: A method for the manufacture of N,N dialkylglycamine compounds of general formula R.sub.2 NR.sub.1 R.sub.3 (I) by reacting a secondary amine of general formula R.sub.2 NHR.sub.3 (II) in which R.sub.2 is a straight or branched chain alkyl or hydroxyalkyl group having from 1 to 4 carbon atoms and R.sub.3 is a residue from a monosaccharide, with an alkali metal or alkaline earth metal aliphatic sulphate, R.sub.1 SO.sub.4 M, in which R.sub.1 is a straight or branched chain alkyl or alkenyl group having from 8 to 24 carbon atoms.The betaine, suphobetaine and N-oxidised derivatives of (I) are provided for use as mild surfactants.
    Type: Grant
    Filed: November 16, 1994
    Date of Patent: June 4, 1996
    Assignee: Albright & Wilson Limited
    Inventors: Brynley M. Phillips, Ajit Kumar, Alan Smithson
  • Patent number: 5475141
    Abstract: Process for preparing primary amines from aldehydes by mixing an aldehyde with a diluent, where in the case of an alcohol or of water as diluent the mixing temperature is at most 5.degree. C. to prevent the formation of the hemiacetal or the aldehyde hydrate, and bringing the mixture into contact with a mixture of ammonia, hydrogen and hydrogenation catalyst, whereby the formation of an imine is prevented, at temperatures of from 60.degree. to 180.degree. C. and pressures of from 20 to 60 bar, at least 15 mol of ammonia being used per mol of aldehyde group, and also an apparatus for carrying out the process.
    Type: Grant
    Filed: June 3, 1994
    Date of Patent: December 12, 1995
    Assignee: Chemie Linz GmbH
    Inventors: Carlo Kos, Friedrich Hebesberger, Eduard Artner, Engelbert Kloimstein, Robert Haar, Ernst Lust
  • Patent number: 5440049
    Abstract: A compound of the formula: ##STR1## wherein R.sup.11 is hydrogen, lower alkyl, haloloweralkyl, lower alkenyl, lower alkynyl or cycloalkyl and R.sup.21 is a group selected from the group consisting of: ##STR2## wherein R.sup.3 -R.sup.5, R.sup.31, R.sup.32, R.sup.41, R.sup.42 and R.sup.51 are as defined herein, and W is chlorine or bromine, is prepared by reacting a compound of the formula:Z--CH.sub.2 --CH.dbd.CH--W (I)wherein W is as defined above and Z is a leaving group, with an amine of the formula: ##STR3## wherein R.sup.11 and R.sup.21 are as defined above.
    Type: Grant
    Filed: June 13, 1994
    Date of Patent: August 8, 1995
    Assignee: Banyu Pharmaceutical Co., Ltd.
    Inventors: Susumu Nakagawa, Akira Asai, Satoru Kuroyanagi, Makoto Ishihara, Yoshiharu Tanaka
  • 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: 5334764
    Abstract: Amines such as methyl amine are reacted with materials such as reducing sugars in hydroxy solvents such as methanol to prepare N-alkyl polyhydroxy amines. Accordingly, glucose is reacted with methyl amine and the resulting adduct is hydrogenated to yield N-methylglucamine. The N-alkyl polyhydroxyamines can be subsequently reacted with fatty esters to provide polyhydroxy fatty acid amides useful as detersive surfactants. Thus, detersive surfactants are available from non-petrochemical precursors such as sugars and sugar sources such as corn syrup, and fatty acid esters derivable from various fats and oils.
    Type: Grant
    Filed: May 6, 1993
    Date of Patent: August 2, 1994
    Assignee: The Procter & Gamble Company
    Inventors: Jeffrey J. Scheibel, Daniel S. Connor, Robert E. Shumate, James B. St. Laurent
  • 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: 5296633
    Abstract: The methylated tertiary amines are selectively prepared by reacting a primary or secondary amine, or a nitrile or aminonitrile, including an aminoalcohol, etheramine, a polyamine or fatty polyamine or amidoamine, or amidopolyamine or dinitrile, with hexamethylenetetramine ("HMTA"), under hydrogen pressure at a temperature no greater than about 160.degree. C. and in the presence of a catalytically effective amount of a hydrogenation catalyst, e.g., nickel deposited onto appropriate support substrate therefor.
    Type: Grant
    Filed: December 30, 1992
    Date of Patent: March 22, 1994
    Inventor: Stephane Fouquay
  • Patent number: 5284976
    Abstract: A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMe.sub.2 wherein R is an organo group, R* is a chiral organo group. attached to boron, B is boron and Me is methyl.
    Type: Grant
    Filed: July 19, 1993
    Date of Patent: February 8, 1994
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 5276195
    Abstract: A process for preparing a dimethylorganoborane represented by the formula R*BMe.sub.2 wherein R* is a chiral organyl group attached to the boron, B is boron and Me is methyl comprising treating a chiral boronic ester R*B(OR').sub.2 with a methyl magnesium salt or trimethylaluminum wherein R* is the same chiral organyl group and R' is alkyl.
    Type: Grant
    Filed: July 14, 1993
    Date of Patent: January 4, 1994
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • 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: 5214209
    Abstract: A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMe.sub.2 wherein R is an organo group, R* is a chiral organo group,attached to boron, B is boron and Me is methyl.
    Type: Grant
    Filed: March 26, 1990
    Date of Patent: May 25, 1993
    Assignee: Aldrich Chemical Company, Inc.
    Inventor: Herbert C. Brown
  • Patent number: 5210310
    Abstract: A novel process for producing hindered and unhindered primary amines represented by the formula RNH.sub.2 and R*NH.sub.2 in high yields from novel intermediates RBMe.sub.2 or R*BMe.sub.2 wherein R is an organo group, R* is a chiral organo group, attached to boron, B is boron and Me is methyl.
    Type: Grant
    Filed: March 26, 1990
    Date of Patent: May 11, 1993
    Assignee: Aldrich Chemical Co., Inc.
    Inventor: Herbert C. Brown
  • 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: 5112995
    Abstract: A potassium salt useful in the production of N-substituted-1-alkylthio-2-nitroethenamines is produced by the reaction of the dipotassium salt of nitrodithioacetic acid with certain straight chain alkylamines, thereby converting only one of the KS-groups to an alkylamine group. The resulting monopotassium salt may be alkylated to produce the required N-substituted-1-alkylthio compound which may be reacted with a suitable amine to produce the histamine H.sub.2 -antagonist ranitidine.
    Type: Grant
    Filed: April 4, 1990
    Date of Patent: May 12, 1992
    Assignee: Glaxo Group Limited
    Inventors: James I. Grayson, Graham Heyes, Arthur Jackson, Paul E. Rowney
  • 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: 4983736
    Abstract: This invention relates to a process for making amines by condensing an amino compound in the presence of a metallic polyphosphate condensation catalyst having a condensed structure. This invention also relates to an alkyleneamines producers composition rich in triethylenetetramine (TETA), tetraethylenepentamine (TEPA) and pentatethylenehexamine (PEHA).
    Type: Grant
    Filed: August 8, 1989
    Date of Patent: January 8, 1991
    Assignee: Union Carbide Chemicals and Plastic Company Inc.
    Inventors: Arthur R. Doumaux, Jr., David J. Schreck
  • Patent number: 4914241
    Abstract: Diamines of the formula ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, alkyl, aryl, alkoxy, aralkyl or cycloalkyl and X is a group of the formula(CR.sup.4 R.sup.5).sub.m (II)where R.sup.4 and R.sup.5 have the meanings given above for R.sup.1 and m is from 1 to 12, are prepared by a process in which a diamine of the formula ##STR2## where R.sup.1, R.sup.2 and X are the groups described above, is reacted with an olefin of the formula ##STR3## where R.sup.6 and R.sup.9 are each hydrogen or alkyl which is straight-chain in the .alpha.-position, in the presence of a zeolite as a catalyst.
    Type: Grant
    Filed: June 15, 1988
    Date of Patent: April 3, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Michael Hesse, Wolfgang Hoelderich, Matthias Schwarzmann
  • 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: 4625030
    Abstract: The present invention concerns a potentiated nickel catalyst and its use for the catalytic amination of lower aliphatic alkane derivatives.
    Type: Grant
    Filed: May 23, 1984
    Date of Patent: November 25, 1986
    Assignee: Union Carbide Corporation
    Inventor: Donald C. Best
  • Patent number: 4618716
    Abstract: This invention relates to a process for producing linear polyethylene polyamines. In the process ammonia or an ethylene polyamine is reacted with 2-aminoethyl sulfuric acid to form a higher polyethylene polyamine salt. This salt is subsequently neutralized with a base liberating the free polyethylene polyamine. This product can be recovered from the reaction mixture by filtration and the product polyethylene polyamine purified by distillation.
    Type: Grant
    Filed: November 8, 1985
    Date of Patent: October 21, 1986
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Michael E. Ford, Thomas A. Johnson
  • Patent number: 4605770
    Abstract: A process for preparing predominantly noncyclic polyalkylene polyamine compounds is disclosed wherein an alkanolamine compound and an alkyleneamine compound in a molar ratio of alkanolamine compound:alkyleneamine compound of 1:5 to 3:1, preferably less than 1, is reacted in the presence of a catalytically effective amount of a Group IIA or Group IIIB metal acid phosphate at a temperature from about 200.degree. to 400.degree. C. under a pressure sufficient to maintain the reaction mixture substantially in liquid phase.
    Type: Grant
    Filed: December 22, 1983
    Date of Patent: August 12, 1986
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Michael E. Ford, Thomas A. Johnson
  • 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: 4510331
    Abstract: There are disclosed a process for producing 7-octen-1-al which comprises isomerizing 2,7-octadien-1-ol in the presence of a catalyst comprising oxides of at least two metals selected from the group consisting of copper, chromium and zinc and processes for producing derivatives of 7-octen-1-al.
    Type: Grant
    Filed: June 22, 1982
    Date of Patent: April 9, 1985
    Assignee: Kuraray Company, Ltd.
    Inventors: Noriaki Yoshimura, Masuhiko Tamura
  • 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