Three Or More Amino Nitrogens Containing Patents (Class 564/512)
  • Patent number: 5206394
    Abstract: Disclosed is a process for the manufacture of alkali metal salt complexes of the formula (M.sub.x X.nL).sub.y, where M is an alkali metal, e.g. lithium, X is an anion, e.g. halide or thiocyanate, L is an organic electron-donating ligand (Lewis base), x is the valency of the anion X, n is usually 1,2 or 4 and y is an integer, by the in situ reaction of an alkali metal or an alkali metal hydride or alkyl, for example lithium, lithium hydride or butyl lithium, and an anhydrous ammonium salt comprising the anion X, e.g. an anhydrous ammonium halide, the reaction being performed in solution in an anhydrous solvent in the presence of the ligand (L).
    Type: Grant
    Filed: August 18, 1989
    Date of Patent: April 27, 1993
    Assignee: The Associated Octel Company Limited
    Inventors: Ronald Snaith, Dominic S. Wright
  • Patent number: 5202491
    Abstract: A continuously generated alkyleneamines producers composition comprising, based on 100% of the moles of the composition and exclusive of any MEA and water present,a) about 20 to about 40 mole % DETA,b) about 15 to about 60 mole % EDA (net generated),c) about 5 to about 18 mole % AEEA,d) about 3 to about 25 mole % of the combination of PIP, AEP and HEP,e) less than about 1 to about 5 mole % of one or more of TETAs and TEPAs,f) less than about 1 mole % of other polyalkylene polyamines,g) a DETA to AEEA mole ratio greater than about 1.35, andh) an EDA to DETA mole ratio less than 2.60,and the process of manufacturing it which comprises feeding hydrogen, ammonia, MEA and EDA, preferably provided from a recycle stream, to a reaction zone containing a fixed bed of a reductive amination catalyst in a tubular reactor, wherein the hydrogen comprises about 1 to about 30 mole percent of the feed in the reaction zone, the mole ratio of EDA to MEA is greater than 0.
    Type: Grant
    Filed: May 25, 1990
    Date of Patent: April 13, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Lloyd M. Burgess, Charles A. Gibson, David J. Schreck
  • Patent number: 5202490
    Abstract: A continuously generated alkyleneamines producers composition comprising based on 100% of the moles of the compostion and exclusive of any MEA and water present,a) about 15 to about 35 mole % DETA,b) about 15 to about 55 mole % EDA (net generated),c) about 10 to about 35 mole % AEEA,d) about 3 to about 25 mole % of the combination of PIP, AEP and HEP,e) about 3 to about 10 mole % of one or more of TETAs and TEPAs,f) less than about 1 mole % of other polyalkylene polyamines, andg) a DETA to AEEA mole ratio greater than about 0.77 to less than 1.35,and the process of producing the same, which comprises feeding hydrogen, ammonia, MEA and EDA, preferably provided from a recycle stream, to a reaction zone containing a fixed bed of a reductive amination catalyst in a tubular reactor, wherein the hydrogen comprises about 10 to about 50 mole percent of the feed in the reaction zone, the mole ratio of EDA to MEA is less than about 0.
    Type: Grant
    Filed: May 25, 1990
    Date of Patent: April 13, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Lloyd M. Burgess, Charles A. Gibson, David J. Schreck
  • Patent number: 5202489
    Abstract: Process of making amines by inter alia the (i) intramolecular condensation of an amino compound to an amine having a lower molecular weight or (ii) the intermolecular condensation of an amino compound with one or more of another amino compound or a compound containing an alcoholic hydroxyl group using a Group IVB metal oxide condensation catalyst. The preferred process involves the manufacture of alkyleneamines, most desirably polyalkylenepolyamines, by such condensation reactions utilizing catalysts containing titanium oxide, zirconium oxide or mixtures of them.
    Type: Grant
    Filed: August 8, 1989
    Date of Patent: April 13, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Arthur R. Doumaux, Jr., David J. Schreck, George A. Skoler, Stephen W. King
  • Patent number: 5196588
    Abstract: A continuously generated alkyleneamines producers composition comprising, based on 100% of the moles of the composition and exclusive of any MEA and water present,a) about 14 to about 20 mole % DETA,b) about 45 to about 75 mole % EDA (net generated),c) about 4 to about 10 mole % AEEA,d) about 3 to about 25 mole % of the combination of PIP, AEP and HEP,e) about 0.5 to about 5 mole % of one or more of TETAs and TEPAs,f) less than about 1 mole % of other polyalkylene polymines,g) an EDA to DETA mole ratio greater than about 2.60,h) a DETA to AEEA mole ratio greater than about 1.35, andi) an EDA to AEEA mole ratio greater than about 8,and a process of manufacturing it which comprises feeding hydrogen, ammonia, MEA and EDA, preferably provided from a recycle stream, to a reaction zone containing a fixed bed of a reductive amination catalyst in a tubular reactor, wherein the hydrogen comprises about 1 to about 30 mole percent of the feed in the reaction zone, the mole ratio of EDA to MEA is less than about 0.
    Type: Grant
    Filed: May 25, 1990
    Date of Patent: March 23, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Lloyd M. Burgess, Charles A. Gibson, David J. Schreck
  • Patent number: 5189173
    Abstract: A branched chain polyalkylene polyamine ("PAPA") having plural amine groups, including a secondary amine group intermediate terminal primary amine groups one of which is hindered, and having at least two carbon atoms between each group, is selectively reductively alkylated with a ketone. The reaction provides a convenient method for selectively reductively alkylating a PAPA having a hindered primary amine group, the method comprising contacting the PAPA with hydrogen and the ketone in the presence of a catalytically effective amount of a Group VIII metal on a catalyst support, at a pressure in the range from about 500-1000 psi and a temperature in the range from about 50.degree. C. to about 200.degree. C. for a period of time sufficient to preferentially alkylate the unhindered amine primary terminal amine group. The alkylation proceeds essentially without alkylating either the sterically hindered terminal primary amine group or the intermediate unhindered secondary amine group.
    Type: Grant
    Filed: March 2, 1989
    Date of Patent: February 23, 1993
    Assignee: The BFGoodrich Company
    Inventors: John T. Lai, Pyong-nae Son
  • Patent number: 5177102
    Abstract: There are given disclosures on a polyisoprene compound of the formula ##STR1## wherein Y is S, O, NH or ##STR2## .sub.l is an integer of 2-10, Z is a group of ##STR3## R.sup.1 and R.sup.2 are same or different and each means a hydrogen atom or an alkyl group having C.sub.1-4, m is an integer of 0 or 1, and .sub.n is an integer of 0, 1 or 2,a salt thereof, a process for the preparation of same, and use thereof.
    Type: Grant
    Filed: May 3, 1991
    Date of Patent: January 5, 1993
    Assignee: Sanwa Kagaku Kenkyusho Co., Ltd.
    Inventors: Masayasu Kurono, Yasuaki Kondo, Takuji Yamaguchi, Ryoichi Unno, Hiromoto Kimura, Noboru Kuboyama, Takashi Ito, Mitsuru Oka, Akira Tashita, Kazumasa Nakano, Kiichi Sawai
  • 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: 5132427
    Abstract: A process for the preparation of amines of the formula ##STR1## in which R.sup.1 is the radical H.sub.2 N-CH.sub.2 and R.sup.2 is hydrogen, or R.sup.1 and R.sup.2 together form a bridging group --CH.sub.2 --, by reacting 1,3,6-tricyanohexane at elevated temperature and pressure with hydrogen in contact with a catalyst containing, in addition to cobalt oxide, and oxide of an alkali metal, an oxide of an alkaline earth metal, an oxide of a rare earth or an oxide of scandium or yttrium.
    Type: Grant
    Filed: October 22, 1990
    Date of Patent: July 21, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Koehler, Hardo Siegel, Peter Jaeger, Matthias Irgang
  • 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: 5109024
    Abstract: The present invention relates to certain novel polyamine compounds of the formula: ##STR1## wherein Z is a saturated (C.sub.2 -C.sub.6) alkylene moiety, each R group independently is hydrogen, methyl, ethyl, or n-propyl with the provisos that both R groups cannot be hydrogen and that R is hydrogen or methyl when Z is a branched chain alkylene; or a pharmaceutically acceptable acid addition salt thereof.
    Type: Grant
    Filed: February 8, 1991
    Date of Patent: April 28, 1992
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Nellikunja Prakash, David M. Stemerick, Michael L. Edwards, Terry L. Bowlin
  • Patent number: 5105013
    Abstract: A process for the preparation of permethylated amines, particularly pentamethyldiethylenetriamine, by the reductive methylation of diethylenetriamine in the presence of hydrogen, a nickel-containing catalyst, aqueous formaldehyde and methanol, comprising feeding continuously the formalehyde to the reaction system in two phases. In the first phase, a sufficient amount of formaldehyde to mono-methylate the primary amine groups present, is fed to the reaction system at a high flow rate, and thereafter the flow rate of the formaldehyde is substantially reduced, for the reductive methylation of the secondary amine groups. By this method the production of by-products is substantially reduced and preparation times are significantly shorter in comparison to processes where the formaldehyde flow rate remains constantly high for the entirety of the reaction.
    Type: Grant
    Filed: December 19, 1988
    Date of Patent: April 14, 1992
    Assignee: The Dow Chemical Company
    Inventors: Maarten Tanis, Govind Rauniyar
  • Patent number: 5103056
    Abstract: Disclosed is a method for selective formation of amidoamines which comprises reacting a carboxylic acid group, such as, for example, a diacid or an aliphatic acid terminated amide with an aminopropylated disecondary amine which contains a secondary amine terminus in the same molecule at a temperature of about 150.degree. C. to about 260.degree.0 C.
    Type: Grant
    Filed: January 31, 1991
    Date of Patent: April 7, 1992
    Assignee: Texaco Chemical Company
    Inventors: George P. Speranza, Donald H. Champion
  • Patent number: 5101074
    Abstract: This invention relates to vicinal di(hetero)alkylene organometalate compounds comprising one or more metal oxides in association with an alkanolamine, an alkyleneamine, an alkylene glycol or mixtures thereof. This invention also relates to an alkyleneamines producers composition rich in triethylenetetramine (TETA), tetraethylenepentamine (TEPA) and pentaethylenehexamine (PEHA), and to processes for the preparation thereof using the vicinal di(hetero)alkylene organometalates.
    Type: Grant
    Filed: August 8, 1989
    Date of Patent: March 31, 1992
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Stephen W. King, Arthur R. Doumaux, Jr., David J. Schreck, George A. Skoler
  • Patent number: 5091576
    Abstract: The present invention relates to anti-neoplastic and anti-psoriasis pharmaceutical compositions and methods of treatment and to insecticidal compositions and methods of controlling the growth of insects.
    Type: Grant
    Filed: June 23, 1988
    Date of Patent: February 25, 1992
    Assignee: University of Florida
    Inventor: Raymond J. Bergeron
  • Patent number: 5089619
    Abstract: Certain dithiocarbamates are used as reverse demulsifiers, corrosion and scale inhibitors, flocculants, biocides, flotation aids, water clarifiers, interface control agents and antifoaming agents.
    Type: Grant
    Filed: June 30, 1989
    Date of Patent: February 18, 1992
    Assignee: Petrolite Corporation
    Inventors: Neil E. S. Thompson, Robert G. Asperger
  • Patent number: 5082972
    Abstract: At least one of ammonia and ethylenediamine is reacted with monoethanolamine in the presence of a catalyst containing phosphoric acid or its condensate in order to prepare acyclic ethyleneamines, and the catalyst can be improved in performance and the life of the catalyst can be prolonged by feeding a phosphorus-containing material to a reaction system during the reaction. In addition, the catalyst having a deteriorated performance can be reactivated by adding the phosphorus-containing material to the catalyst.
    Type: Grant
    Filed: July 11, 1990
    Date of Patent: January 21, 1992
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Tadashi Komiyama, Hisaharu Kuboyama, Takashi Jimbo, Hiroyoshi Watanabe, Shuichi Tokumoto, Yumiko Endoh, Eiichi Sugiyama, Yoshitaro Naganuma
  • Patent number: 5068329
    Abstract: A continuously generated alkyleneamines produces composition comprising, based on 100% of the moles of the composition and exclusive of any MEA and water present,a) about 50 to about 90 mole % AEEA,b) less than about 3 mole % EDA but more than 0.01 mole % EDA,c) less than about 2 mole % DETA but more than 0.01 mole % DETA,d) about 5 to about 18 mole % of the combination of PIP, AEP and HEP,e) about 5 to about 20 mole % of one or more of TETAs and TEPAs,f) less than about 1 mole % of other polyalkylene polyamines,g) a mole ratio of AEEA to the combination of PIP, AEP, HEP, DETA and EDA is greater than about 2.
    Type: Grant
    Filed: September 4, 1990
    Date of Patent: November 26, 1991
    Assignee: Union Carbide Chemicals and Plastics Technology Corporation
    Inventors: Lloyd M. Burgess, Charles A. Gibson
  • Patent number: 5068330
    Abstract: A continuously generated alkyleneamines producers composition comprising, based on 100% of the moles of the composition and exclusive of any MEA and water present,a) about 15 to about 50 mole % AEEA,b) about 15 to about 55 mole % EDA,c) about 10 to about 20 mole % DETA,d) about 5 to about 20 mole % of the combination of PIP,AEP and HEP,3) about 3 to about 10 mole % of one or more of TETAs and TEPAs,f) less than about 1 mole % of other polyalkylene polyamines,g) an DETA to AEEA mole ratio less than 0.77, andh) an EDA to AEEA mole ratio less than 8;and a process of manufacturing the same, which comprises feeding hydrogen, ammonia and MEA to a reaction zone containing a fixed bed of a reductive amination catalyst, wherein the hydrogen comprises about 20 to about 60 mole percent of the feed in the reaction zone and the mole ratio of ammonia to MEA is about 1 to about 5, the temperature of the reaction zone is about 120.degree. C. to about 300.degree. C.
    Type: Grant
    Filed: September 4, 1990
    Date of Patent: November 26, 1991
    Assignee: Union Carbide Chemicals and Plastics Technology Corporation
    Inventors: Lloyd M. Burgess, Charles A. Gibson
  • Patent number: 5053152
    Abstract: Improved additives/dispersants for lubricant and fuel compositions are obtained by condensing a hydroxyalkyl or hydroxyaryl compound with an amine compound. The condensates according to the present invention are produced by the acid catalyzed condensation of the amine reactant with the hydroxy reactant.
    Type: Grant
    Filed: August 3, 1989
    Date of Patent: October 1, 1991
    Assignee: The Lubrizol Corporation
    Inventor: Thomas F. Steckel
  • Patent number: 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: 4990633
    Abstract: New fluorinated bisaryloxy-substituted alkenes are prepared by reaction of substituted phenols with perhaloalkenes and can be used as electrical insulating agents.
    Type: Grant
    Filed: May 4, 1989
    Date of Patent: February 5, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventors: Michael Negele, Dietmar Beilefeldt, Thomas Himmler, Albrecht Marhold
  • 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: 4967008
    Abstract: The present invention is directed to polyamines represented by the following general structure: ##STR1## where R is an organic group, R' is H or CH.sub.3, andx=0-3Tri, tetra, penta, and hexa amines, accordingly, are disclosed.The method for making the novel polyamines comprises a multi-step reaction that commences in step (a) with the cyanoethylation of a primary amine, R--NH.sub.2, with acrylonitrile under cyanoethylation conditions to form an aminonitrile of the structure R--NH--CH.sub.2 --CH.sub.2 --CN. The aminonitrile in step (b) is methylated by reaction with formic acid and formaldehyde under Leuckart reaction conditions to form a monomethyl aminonitrile of the structure R--N(CH.sub.3)--CH.sub.2 --CH.sub.2 --CN. The monomethyl aminonitrile then in step (c) is reduced, preferably by hydrogenation under hydrogenation conditions, to form a monomethyl diamine of the structure R--N(CH.sub.3)--CH.sub.2 --CH.sub.2 --CH.sub.2 --NH.sub.2.
    Type: Grant
    Filed: January 12, 1990
    Date of Patent: October 30, 1990
    Assignee: Sherex Chemical Company, Inc.
    Inventors: Floyd E. Friedli, Robert M. Gilbert
  • Patent number: 4939300
    Abstract: Aminic orthoester derivatives of the formulae ##STR1## are effective in stabilizing organic materials against oxidative, thermal and actinic degradation.
    Type: Grant
    Filed: November 16, 1987
    Date of Patent: July 3, 1990
    Assignee: Ciba-Geigy Corporation
    Inventors: Linda A. Benjamin, Joseph E. Barbiarz, Stephen D. Pastor
  • Patent number: 4927971
    Abstract: There is disclosed a desensitizing ink comprising an adduct produced by the addition of 4 to 70 mols of an alkylene oxide to 1 mol of an amine represented by the general formula (I) where 40 mol % or more of said alkylene oxide are butylene oxide: ##STR1##
    Type: Grant
    Filed: May 8, 1989
    Date of Patent: May 22, 1990
    Assignee: Mitsubishi Paper Mills Ltd.
    Inventors: Mitsuru Fuchigami, Shingo Tachizawa, Mamoru Ishiguro
  • Patent number: 4900458
    Abstract: A corrosion inhibiting polyalkylenepolyamine composition comprising a mixture of(a) at least one C-alkyl-ethylene diamine, and(b) at least one di-(C-alkyl)-diethylenetriamine or at least one di-(C-alkyl)-piperazine or a mixture thereof;wherein each C-alkyl group on the ethylene diamine, diethylenetriamine and piperazine independently contains from 10 to 28 carbon atoms. Methods for preparing this composition are also disclosed, as well as methods for its use in inhibiting corrosion of corrodible metals.
    Type: Grant
    Filed: January 11, 1988
    Date of Patent: February 13, 1990
    Assignee: Chevron Research Company
    Inventors: Albert H. Schroeder, Ta Y. Ching, Shigeto Suzuki, Kiyoshi Katsumoto
  • Patent number: 4888425
    Abstract: Enhanced production of predominantly linearly extended polyalkylene polyamines from alkylenediamines reacted with alkylene glycols or alkanolamines using a phosphorus-containing catalyst is achieved by removing water during the reaction.
    Type: Grant
    Filed: February 7, 1984
    Date of Patent: December 19, 1989
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventor: William B. Herdle
  • Patent number: 4864062
    Abstract: A process for producing dioctamethylene triamine is disclosed which comprises dimerizing octamethylene diamine in the presence of a zeolite catalyst, characterized in that the catalyst is represented by the formula:Na.sub.2 O.cndot.xSiO.sub.2 .cndot.yAl.sub.2 O.sub.3wherein x and y are so selected that the molar ratio of Na.sub.2 O to Al.sub.2 O.sub.3 is in the range of 0.02 to 0.05 and the molar ratio of SiO.sub.2 to Al.sub.2 O.sub.3 is in the range of 1 to 10.
    Type: Grant
    Filed: September 23, 1988
    Date of Patent: September 5, 1989
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Masao Saito, Koichiro Yamada
  • Patent number: 4855504
    Abstract: High molecular weight amines having reduced low molecular weight amine contents are obtained by reacting a mixture of (1) a high molecular weight amine and (2) a low molecular weight amine with (3) an isocyanate in quantities such that from 0.5 to 10 equivalents of isocyanate are present for each equivalent of low molecular weight amine. The product of high molecular weight amines is particularly useful in the production of isocyanate addition products such as polyurethane plastics and foams.
    Type: Grant
    Filed: September 23, 1985
    Date of Patent: August 8, 1989
    Assignee: Bayer Aktiengesellschaft
    Inventors: Werner Rasshofer, Ernst Grigat, Gerhard Grogler, Heinrich Hess, Richard Kopp
  • Patent number: 4827037
    Abstract: Process for the improvement of the quality of polyalkylene polyamines prepared by the reaction of (i) ammonia and/or an alkyleneamine compound having at least two amino groups and an alkanolamine compound having at least one amino group in the presence of a catalytically effective amount of a metal acid phosphate and at a temperature and pressure sufficient to form the polyalkylene polyamine.
    Type: Grant
    Filed: April 4, 1985
    Date of Patent: May 2, 1989
    Assignee: Union Carbide Corporation
    Inventor: Arthur R. Doumaux, Jr.
  • Patent number: 4803304
    Abstract: Recovery of bis(hexamethylene)triamine from still heels of hexamethylenediamine by extraction using an aliphatic hydrocarbon having a boiling point between about 34.degree. C. and 210.degree. C.
    Type: Grant
    Filed: April 15, 1987
    Date of Patent: February 7, 1989
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Robert A. Smiley
  • Patent number: 4795828
    Abstract: Procainamide and N-acetylprocainamide (NAPA) immunogens, antibodies prepared therefrom, labeled conjugates, synthetic intermediates, and the use of such antibodies and labeled conjugates in immunoassays for determining the respective drugs. The immunogens comprise the drugs coupled at the .alpha.-position of the amide side chain to an immunogenic carrier material. The labeled conjugates and synthetic intermediates similarly are .alpha.-position derivatives of the drugs or precursors thereof. The antibodies and labeled conjugates are particularly useful in homogeneous nonradioisotopic immunoassays for measuring the respective drugs in biological fluids such as serum.
    Type: Grant
    Filed: September 25, 1986
    Date of Patent: January 3, 1989
    Assignee: Miles Inc.
    Inventors: Robert T. Buckler, Frederick E. Ward
  • Patent number: 4720588
    Abstract: This invention pertains to an improved process for preparing noncyclic polyalkylene polyamine compounds in high selectivity by reacting an alkanolamine and an alkylene amine in the presence of an inert gas and an acidic catalyst. The improvement resides in effecting the reaction under fixed bed catalytic conditions and maintaining the reaction conditions such that a vapor phase condition exists for the reaction mixture comprising both reactants and products. To accomplish the formation of vapor phase conditions sufficient inert gas is injected into the feedstream along with alkanolamine and alkylene amine so that the dew point temperature of the reaction product mix is below the reaction temperature at reaction pressure.
    Type: Grant
    Filed: January 16, 1986
    Date of Patent: January 19, 1988
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Michael G. Turcotte, Cawas A. Cooper, Michael E. Ford, Thomas A. Johnson
  • Patent number: 4718918
    Abstract: Polymeric compounds (A) obtained by the reaction of epihalo-hydrin with a polyalkylene polyamine are useful as textile treatment agents. As pretreatment agents they improve the color yield of the subsequent dyeing, as aftertreatment agents they improve fastness properties. Certain of the products (A) are novel.
    Type: Grant
    Filed: June 16, 1986
    Date of Patent: January 12, 1988
    Assignee: Sandoz Ltd.
    Inventors: Jurg Heller, Bruno Kissling, Tibor Robinson, Salvatore Valenti
  • Patent number: 4719313
    Abstract: Gem-dihalo and gem-tetrahalo-1,12-diamino-4,9-diaza-dodecane derivatives useful as antiproliferative or antitumor agents.
    Type: Grant
    Filed: February 12, 1986
    Date of Patent: January 12, 1988
    Assignee: Merrell Dow Pharmaceuticals Inc.
    Inventors: Fritz Gerhart, Pierre Mamont
  • Patent number: 4698428
    Abstract: It has been surprisingly discovered in accordance with the present invention that N-methylethanolamine may be converted to N,N'-dimethylpiperazine when using a catalyst composed of titania to which from about 0.5 to about 7 wt. % of phosphorus has been thermally chemically bonded in the form of phosphate linkages.
    Type: Grant
    Filed: June 9, 1986
    Date of Patent: October 6, 1987
    Assignee: Texaco Inc.
    Inventors: Robert L. Zimmerman, Steven H. Vanderpool
  • Patent number: 4698427
    Abstract: Ethylenediamine and diethanolamine and/or hydroxyethyldiethylenetriamine can be converted to N-aminoethylpiperazine and tetraethylenepenetamine when using a catalyst composed of titania to which from about 0.5 to about 7 wt. % of phosphorus has been thermally chemically bonded in the form of phosphate linkages.
    Type: Grant
    Filed: June 9, 1986
    Date of Patent: October 6, 1987
    Assignee: Texaco Inc.
    Inventor: Steven H. Vanderpool
  • Patent number: 4650906
    Abstract: Ethyleneamines are recovered from an aqueous solution of carbonates of ethyleneamines by distilling an aqueous solution of carbonates of ethyleneamines including ethylenediamine, in which the molar ratio of the carbon dioxide component to the ethyleneamines including ethylenediamine is 0.01 to 0.5, whereby ethylenediamine is distilled out together with water. The aqueous solution to be distilled is advantageously prepared by heating an aqueous solution of carbonates of ethyleneamines including ethylenediamine to effect decarboxylation.
    Type: Grant
    Filed: February 29, 1984
    Date of Patent: March 17, 1987
    Assignee: Toyo Soda Manufacturing Co., Ltd.
    Inventors: Tsugio Murakami, Taizo Kawamoto
  • Patent number: 4647701
    Abstract: Ethanolamine is subjected to reductive amination in a continuous process to produce diethylenetriamine with less than 10 weight percent piperazine contained in the reaction products. The reductive amination conditions include the use of a catalyst, an ethanolamine feed rate of at least about 400 kilograms of ethanolamine per hour per cubic meter of catalyst, and a temperature sufficient to react between about 35 and 60 percent of the ethanolamine fed.
    Type: Grant
    Filed: May 23, 1984
    Date of Patent: March 3, 1987
    Assignee: Union Carbide Corporation
    Inventor: Charles A. Gibson
  • 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: 4631337
    Abstract: Dense star polyamines having terminal group densities greater than extended conventional star polyamines exhibit greater and more uniform reactivity than their corresponding extended conventional star polyamines. For example, a second generation, amine-terminated polyamine dense star polyamine prepared from tri(2-aminoethyl)amine and aziridine has 4.7.times.10.sup.-3 amine moieties per unit volume (cubic Angstrom units) in contrast to the 1.7.times.10.sup.-3 amine moieties per unit volume contained by an extended conventional star polyamine. Such dense star polyamines are useful as calibration standards, high efficiency proton scavengers and in making size selective membranes.
    Type: Grant
    Filed: July 15, 1985
    Date of Patent: December 23, 1986
    Assignee: The Dow Chemical Company
    Inventors: Donald A. Tomalia, James R. Dewald
  • Patent number: 4617418
    Abstract: This invention pertains to an improved process for preparing noncyclic polyalkylene polyamine compounds in high selectivity by reacting ammonia, an alkanolamine and an alkylene amine in the presence of an acidic catalyst. The improvement resides in effecting the reaction under fixed bed catalytic conditions and maintaining the reaction conditions such that a vapor phase condition exists for the reaction mixture comprising both reactants and products. To accomplish the formation of vapor phase conditions, sufficient ammonia is injected into the feedstream along with alkanolamine and alkylene amine so that the dew point temperature of the reaction product mix is below the reaction temperature at reaction pressure.
    Type: Grant
    Filed: November 26, 1984
    Date of Patent: October 14, 1986
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Michael E. Ford, Thomas A. Johnson
  • Patent number: 4612397
    Abstract: This invention is directed to thermally activated pelletted catalyst compositions comprising titania having phosphorous derived from a diaminohydrogen phosphate deposited thereon and to their preparation and their use in the production of predominantly linear polyethylenepolyamines from ethylenediamine and monoethanolamine.
    Type: Grant
    Filed: April 25, 1985
    Date of Patent: September 16, 1986
    Assignee: Texaco, Inc.
    Inventor: Terry L. Renken
  • Patent number: 4609761
    Abstract: This invention is directed to pelletted thermally activated catalyst compositions comprising titania having phosphorous derived from a trialkyl phosphate or phosphite deposited thereon and to their use in the production of predominantly linear polyethylenepolyamines from ethylenediamine and monoethanolamine.
    Type: Grant
    Filed: April 16, 1985
    Date of Patent: September 2, 1986
    Assignee: Texaco Inc.
    Inventors: Lewis W. Watts, Jr., Steven H. Vanderpool
  • 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: 4599087
    Abstract: Polymeric compounds (A) obtained by the reaction of epihalohydrin with a polyalkylene polyamine are useful as textile treatment agents. As pretreatment agents they improve the color yield of the subsequent dyeing, as aftertreatment agents they improve fastness properties. Certain of the products (A) are novel.
    Type: Grant
    Filed: December 24, 1984
    Date of Patent: July 8, 1986
    Assignee: Sandoz Ltd.
    Inventors: Jurg Heller, Bruno Kissling, Tibor Robinson, Salvatore Valenti
  • Patent number: 4588842
    Abstract: This invention is directed to thermally activated pelletted catalyst compositions comprising phosphorous compounds deposited on group IVb transition metal oxides and their use in the production of predominately linear polyethylenepolyamines from ethylenediamine and monoethanolamine.
    Type: Grant
    Filed: December 22, 1983
    Date of Patent: May 13, 1986
    Assignee: Texaco Inc.
    Inventor: Steven H. Vanderpool
  • Patent number: 4584406
    Abstract: This invention is directed to pelletted catalyst compositions supported on group IVb transition metal oxides that contain phosphorous derived from phosphoryl chloride or phosphorous bromide and their use in the production of predominantly linear polyethylenepolyamines from ethylenediamine and monoethanolamine.
    Type: Grant
    Filed: December 6, 1984
    Date of Patent: April 22, 1986
    Assignee: Texaco Inc.
    Inventors: Steven H. Vanderpool, Terry L. Renken