Group Vi Or Viii Metal Containing Catalyst Utilized Patents (Class 564/480)
  • Patent number: 5093528
    Abstract: Process for producing a secondary amine terminated polyether from a primary amine terminated polyether in which the primary amine terminated polyether is reacted at elevated temperature with a carbonyl compound in the presence of hydrogen and a catalyst composition comprising nickel, ruthenium and at least one other transition metal selected from the second or third row transition metals. The amount of carbonyl compound employed is in excess of the stoichiometric amount required to react completely with the ether. The secondary amine terminated polyethers are useful in the formation of polyurea elastomers.
    Type: Grant
    Filed: August 14, 1990
    Date of Patent: March 3, 1992
    Assignee: BP Chemicals Limited
    Inventors: Ian D. Dobson, Simon F. T. Froom
  • Patent number: 5091585
    Abstract: A method for continuous production of tertiary aliphatic methyl amines, particularly fatty aliphatic methyl amines such as di-hydrogenated tallow methyl amine from fatty alkyl amines, such as di-hydrogenated tallow amine over a nickel catalyst has been discovered. The reaction gives high selectivity of tertiary methyl amine over the coproduced secondary amines. The reaction may be conducted continuously in the presence of hydrogen and a formaldehyde source. The formaldehyde source may be selected from the group consisting of formaldehyde alone, formalin, a solution of mixed formaldehyde and paraformaldehyde in methanol and water, trioxane and mixtures thereof. The nickel catalyst may be promoted with copper and/or chromium, in one embodiment.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: February 25, 1992
    Assignee: Texaco Chemical Company
    Inventors: Wei-Yang Su, Robert L. Zimmerman
  • 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: 5075505
    Abstract: The process of making N,N-dimethyl-N-alkylamines containing less than 1% of alkanols by hydrogenation of N,N-dimethylalkylamines on a catalyst of the copper chromite type containing an amount of manganese oxide effective to keep the alkanol level below 1%.
    Type: Grant
    Filed: February 26, 1990
    Date of Patent: December 24, 1991
    Assignee: Ceca, S.A.
    Inventors: Christian Forquy, Rene Brouard
  • Patent number: 5073635
    Abstract: A process of preparing linearly-extended polyalkylenepolyamines, such as linear and branched polyethylenepolyamines, comprising contacting a difunctional aliphatic alcohol, such as monoethanolamine, with a reactant aliphatic amine, such as ethylenediamine, in the presence of a metal silicate catalyst wherein the metal is selected from Groups IIIB, IVB, VB and the lanthanide rare earth metals. Reactions of piperazines with alkanolamines to yield alcohol-extended and/or amine-extended piperazines are included in the process of this invention.
    Type: Grant
    Filed: June 22, 1990
    Date of Patent: December 17, 1991
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
  • Patent number: 5073649
    Abstract: A process for producing an alkylenamine, which comprises reacting ammonia and/or a polyalkylene polyamine with an alkanolamine to obtain an alkylenamine having an increased number of alkylene chains over the ammonia and/or the alkylenamine as starting material, wherein a catalyst having a niobium-containing substance supported on a carrier is used for the reaction.
    Type: Grant
    Filed: February 9, 1989
    Date of Patent: December 17, 1991
    Assignee: Tosoh Corporation
    Inventors: Yasushi Hara, Nobumasa Suzuki, Yukio Ito, Kazuhiko Sekizawa
  • Patent number: 5071980
    Abstract: Disclosed is a process for simultaneously producing morpholine and GIGLYCOLAMINE.RTM. amine while suppressing CO.sub.2 formation comprising the steps of:reacting anhydrous diethylene glycol with ammonia in the presence of added hydrogen over a dual nickel/ruthenium catalyst system comprising a nickel-based catalyst plus a supported ruthenium catalyst, andisolating said morpholine compound and said DIGLYCOLAMINE.RTM. amine compound from the reaction products.
    Type: Grant
    Filed: December 21, 1990
    Date of Patent: December 10, 1991
    Assignee: Texaco Chemical Company
    Inventor: John F. Knifton
  • 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: 5030740
    Abstract: A process for preparing linearly-extended polyalkylenepolyamines, such as linear and branched polyethylenepolyamines, comprising contacting a difunctional aliphatic alcohol, such as monoethanolamine, with a reactant amine, such as ethylenediamine, in the presence of a catalyst containing tungsten oxide essentially free of the metals of Groups VIII, IB, and IIB of the Periodic Table. Included among the linearly-extended polyalkylenepolyamines are alcohol-extended piperazines, such as N-(2-hydroxyethyl)-piperazine, and amine-extended piperazines, such as N-(2-aminoethyl)piperazine.
    Type: Grant
    Filed: October 14, 1988
    Date of Patent: July 9, 1991
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
  • Patent number: 5023379
    Abstract: A process for the production of hydroxyamines of the formula IR.sup.1 --CH(OH)--CH(NHR.sup.3)--R.sup.2 (I)whereinR.sup.1 and R.sup.2 independently of one another are H or CH.sub.2 OH andR.sup.3 is H, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -hydroxyalkyl comprising reacting an oxo compound with an amine and reducing the resultant ketimine with a reducing agent.
    Type: Grant
    Filed: March 12, 1990
    Date of Patent: June 11, 1991
    Assignee: Merck Patent Gesellschaft mit beschrankter Haftung
    Inventors: Ernst Felder, Michael Romer, Hans Bardonner, Hartmut Hartner, Wolfgang Fruhstorfer
  • Patent number: 5015773
    Abstract: An amine is produced by reacting in the presence of hydrogen at elevated temperature a first reactant which is a compound substantially involatile at the elevated temperature employed and having either one, two or more hydroxyl functions, each of which is independently either a primary or secondary hydroxyl function, with a second reactant which is either ammonia or a primary or a secondary amine in the presence of a reductive amination catalyst wherein the reaction is effected in either a continuously or periodically open system.
    Type: Grant
    Filed: August 4, 1989
    Date of Patent: May 14, 1991
    Assignee: BP Chemicals Limited
    Inventor: Ian D. Dobson
  • Patent number: 5015774
    Abstract: A process for preparing polyoxyalkylene polyamine having secondary amino groups at the end of polymer chain by reaction of polyoxyalkylene polyol with primary amine is disclosed.Polyoxyalkylene polyamine having higher content of the secondary amino groups can be obtained by using a catalyst containing (1) Ni and Zn, (2) Co and Zn, or (3) Ni, Co and Zn; by using a conventionally known catalyst in the presence of monohydric alcohol; or by using the catalyst containing (1) Ni and Zn, (2) Co and Zn, or (3) Ni, Co and Zn, in the presence of monohydric alcohol.
    Type: Grant
    Filed: November 14, 1989
    Date of Patent: May 14, 1991
    Assignee: Mitsui Toatsu Chemicals, Inc.
    Inventors: Ariko Suekane, Fumio Yamazaki, Takayoshi Masuda
  • Patent number: 5011926
    Abstract: Disclosed is a process for simultaneously producing morpholine and DIGLYCOLAMINE.RTM. amine while suppressing CO.sub.2 formation comprising the steps of:reacting diethylene glycol with ammonia in the presence of added hydrogen over a dual nickel-based catalyst comprising a nickel-copper-chromium oxide mix in combination with nickel-on-alumina, aisolating said morpholine compound and said DIGLYCOLAMINE.RTM. amine compound from the reaction products.
    Type: Grant
    Filed: June 25, 1990
    Date of Patent: April 30, 1991
    Assignee: Texaco Chemical Company
    Inventor: John F. Knifton
  • Patent number: 5002922
    Abstract: Catalysts whose active material contains, in addition to from 20 to 85% by weight, calculated as ZrO.sub.2, of oxygen-containing zirconium compounds, from 1 to 30% by weight, calculated as CuO, of oxygen-containing compounds of copper and from 1 to 40% by weight each, calculated as CoO or NiO, respectively, of oxygen-containing compounds of cobalt and of nickel are used for the amination of alcohols under hydrogenating conditions.
    Type: Grant
    Filed: December 27, 1989
    Date of Patent: March 26, 1991
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Irgang, Juergen Schossig, Wolfgang Schroeder, Siegfried Winderl
  • Patent number: 5003107
    Abstract: Poly(oxytetramethylene) diamines useful in the preparation of polyamide and polyurea elastomers are prepared by the catalytic reductive amination of a poly(oxytetramethylene) glycol feedstock under reductive amination conditions in the presence of ammonia and hydrogen using a hydrogenation/dehydrogenation catalyst composed of, on an oxide-free basis, about 70 to 75 wt. % of nickel, about 20 to about 25 wt. % of copper, about 0.5 to 5 wt. % of chromium and about 1 to 5 wt. % of molybdenum.
    Type: Grant
    Filed: December 18, 1989
    Date of Patent: March 26, 1991
    Assignee: Texaco Chemical Company
    Inventors: Robert L. Zimmerman, John M. Larkin
  • Patent number: 4992587
    Abstract: Process for preparing a ruthenium promoted, halogen-containing, nickel and/or cobalt catalyst includes impregnating, in one or more steps, a porous metal oxide support with a nickel compound and/or a cobalt compound, and a ruthenium compound to form a catalyst intermediate; reducing the nickel compound and/or cobalt compound, and ruthenium compound, in one or more steps, to the respective metal by reacting the catalyst intermediate with hydrogen gas at an elevated temperature sufficient to reduce the respective compounds to the metal; and introducing halogen by adding a halide compound at any stage in the process. Catalyst prepared by the above process and use thereof.
    Type: Grant
    Filed: June 2, 1989
    Date of Patent: February 12, 1991
    Assignee: Berol Kemi AB
    Inventor: Juhan Koll
  • 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: 4982003
    Abstract: A mixed oxide catalyst comprising niobium oxide and a member selected from the group consisting of titania, alumina, silica, zirconia and oxides of elements in Groups IIA, VA, VIA, IB, IIB, IIIB, VB, VIB, VIIB and VIII of the Periodic Table. A process for producing an alkylenamine, which comprise reacting ammonia and/or an alkylenamine with an alkanolamine in the presence of such a mixed oxide.
    Type: Grant
    Filed: November 2, 1988
    Date of Patent: January 1, 1991
    Assignee: Tosoh Corporation
    Inventors: Yasushi Hara, Nobumasa Suzuki, Yukio Ito, Kazuhiko Sekizawa
  • Patent number: 4977266
    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,(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,(g) an DETA to AEEA mole ratio less than 0.77, and(h) 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 30, 1987
    Date of Patent: December 11, 1990
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventors: Lloyd M. Burgess, Charles A. Gibson
  • Patent number: 4973692
    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 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 30, 1987
    Date of Patent: November 27, 1990
    Assignee: Union Carbide Chemicals and Plastics Company Inc.
    Inventors: Lloyd M. Burgess, Charles A. Gibson
  • Patent number: 4967005
    Abstract: A process is described for the conversion of oxyalkylated alcohols to the corresponding alkoxylated tertiary amines, such as aminated ethoxylated amines, by reaction with a secondary amine at ambient pressure and at above ambient temperature in the presence of hydrogen and a reductive amination catalyst using, as a reductive amination catalyst, metallic iridium.
    Type: Grant
    Filed: October 20, 1988
    Date of Patent: October 30, 1990
    Assignee: Ethyl Corporation
    Inventor: Kim R. Smith
  • Patent number: 4942261
    Abstract: An allyl type amine is prepared by reacting an allyl type alcohol represented by the following formula: ##STR1## wherein R.sub.1, R.sub.2 and R.sub.3 independently stand for a hydrogen atom, an aliphatic hydrocarbon group or alicyclic hydrocarbon having 1 to 8 carbon atoms, or an aromatic hydrocarbon group,with at least one member selected from the group consisting of ammonia, a primary amine and a secondary amine in the presence of a palladium compound and a multidentate phosphorus compound.
    Type: Grant
    Filed: December 9, 1988
    Date of Patent: July 17, 1990
    Assignee: Showa Denko Kabushiki Kaisha
    Inventors: Yoshimasa Ishimura, Takami Oe, Yuseki Suyama, Nobuyuki Nagato
  • Patent number: 4937383
    Abstract: A process for the manufacture of amines by reacting at an elevated temperature an olefin selected from a monoolefin, the alcohol corresponding to its hydration, or a mixture of the monoolefin and the alcohol with ammonia or a primary or secondary amine in the presence of a catalyst and a solvent, said catalyst being ammonium sulfate of a double sulfate of ammonium and a transition metal.
    Type: Grant
    Filed: September 20, 1988
    Date of Patent: June 26, 1990
    Assignee: Atochem
    Inventors: Yves Brigandat, Jacques Kervennal
  • Patent number: 4935546
    Abstract: A process for the production of a primary alkylamine or a dimethylalkylamine in a single stage comprising heating a reaction medium comprising a long chain carboxylic acid ester with ammonia and hydrogen in the presence of a mixed catalyst of the oxide-metal type; said oxide being titanium dioxide and the metal being a combination of copper and cobalt or of copper, chromium, and cobalt; and the mixed oxide-metal catalyst.
    Type: Grant
    Filed: October 9, 1987
    Date of Patent: June 19, 1990
    Assignee: Ceca, S.A.
    Inventors: Joel Barrault, Mongi Seffen, Christian Forquy
  • Patent number: 4922024
    Abstract: A process for preparing amines comprising contacting an alcohol with a reactant amine in the presence of hydrogen and a catalyst comprising at least one compound containing an element of Group VIB and at least one non-metallic element of Groups IIIA, IVA, and VA of the Periodic Table, the contacting occurring under conditions such that the hydroxyl moiety of the alcohol is replaced by the reactant amine to form an amine product.
    Type: Grant
    Filed: April 14, 1988
    Date of Patent: May 1, 1990
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, Marvin H. Tegen, George E. Hartwell
  • Patent number: 4918234
    Abstract: This invention relates to the catalytic preparation of C.sub.2 to C.sub.4 alkyl amines by the reaction of a C.sub.2-4 alkanol with ammonia in the presence of hydrogen, the reaction being carried out utilizing a crystalline alumino-silicate catalyst system where the ions in the crystalline alumino-silicate catalyst system are predominately cobalt or nickel.
    Type: Grant
    Filed: October 13, 1987
    Date of Patent: April 17, 1990
    Assignee: Air Products and Chemicals, Inc.
    Inventor: Michel Deeba
  • Patent number: 4912260
    Abstract: Amines are produced by reacting at elevated temperature a first reactant which is either an alcohol, an aldehyde or a ketone with a second reactant which is either ammonia, a primary or secondary amine or a nitrile in the presence as catalyst of a composition comprising (i) nickel, (ii) ruthenium, and (iii) at least one other transition metal selected from either the second or third row transition metals, for example palladium, rhenium or iridium.
    Type: Grant
    Filed: March 21, 1988
    Date of Patent: March 27, 1990
    Assignee: BP Chemicals Limited
    Inventors: Ian D. Dobson, Werner A. Lidy, Peter S. Williams
  • 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: 4888447
    Abstract: A process is described for selectively preparing alkoxylated tertiary amine compounds, such as aminated ethoxylated amines, at ambient pressure by reacting an oxyalkylated alcohol with a secondary amine in the presence of a reductive amination catalyst at above ambient temperature using, as a reductive amination catalyst, a combination of Raney nickel and molybdenum.
    Type: Grant
    Filed: June 30, 1988
    Date of Patent: December 19, 1989
    Assignee: Ethyl Corporation
    Inventor: Kim R. Smith
  • Patent number: 4874896
    Abstract: This invention relates to a process for preparing an alkylamine by contacting an alcohol and at least one of ammonia, a primary amine, a secondary amine or a tertiary amine with a non-zeolitic molecular sieve under conditions effective to produce the alkylamine.
    Type: Grant
    Filed: December 23, 1987
    Date of Patent: October 17, 1989
    Assignee: UOP
    Inventors: Kurt D. Olson, Steven W. Kaiser
  • Patent number: 4855425
    Abstract: The present invention is a process for the selective synthesis of alkanediamines by reacting a secondary amine with an alkanediol. High conversions and high selectivity for the production of alkanediamines is achieved by carrying out the reaction in the presence of a compound or complex of ruthenium in the absence of an organic phosphine co-catalyst.
    Type: Grant
    Filed: April 29, 1988
    Date of Patent: August 8, 1989
    Assignee: Air Products and Chemicals, Inc.
    Inventor: John A. Marsella
  • Patent number: 4855505
    Abstract: The invention relates to a ruthenium promoted nickel and/or cobalt dehydrogenation-hydrogenation catalyst. The ruthenium on the catalyst is applied from a solution containing a ruthenium halide compound. The catalyst use in organic reactions and a process performed in its presence are also described. Preferably, the catalyst is used to aminate alkylene oxides, alcohols, phenols, alkanolamines, aldehydes, and ketones.
    Type: Grant
    Filed: December 8, 1986
    Date of Patent: August 8, 1989
    Assignee: Berol Kemi AB
    Inventor: Juhan Koll
  • Patent number: 4851578
    Abstract: Trialkylamines are prepared by reacting primary alcohols with ammonia or a primary alkylamine in the presence of a hydrogenation/dehydrogenation catalyst and in the presence of hydrogen by(a) operating in liquid phase(b) using the alcohol in a stoichiometric excess of from 1 to 15 moles per mole of ammonia or primary alkylamine,(c) carrying out the reaction in the presence of the water formed in the course of the reaction, and(d) using a hydrogenation/dehydrogenation catalyst which substantially contains only copper as the catalytically hydrogenating/dehydrogenating metal.
    Type: Grant
    Filed: July 27, 1987
    Date of Patent: July 25, 1989
    Assignee: BASF Aktiengesellschaft
    Inventors: Roman Fischer, Herbert Mueller
  • Patent number: 4847417
    Abstract: A method for converting a bis(polyalkoxy)-N-alkylamine to a bis(diaminopolyalkoxy)-N-alkylamine has been discovered. The method comprises alkoxylating an alkylamine to a bis(polyalkoxy)-N-alkylamine. The alkylamine is selected to sterically hinder the resulting tertiary amine. The alkoxylate is then catalytically aminated according to well known procedures with a high yield of the diamine resulting.Compounds prepared by this method are of the formula:R--N--(PO.sub.x --NH.sub.2).sub.2wherein:PO is propylene oxide,x ranges from 2 to 40, andR is a sterically hindering alkyl such as isopropyl or tertiary butyl.The compounds are useful for curing epoxy thermoset resins. They are uniquely suited to reactions with polyisocyanates to prepare plastic parts, such as automobile body panels, by reaction injection molding.
    Type: Grant
    Filed: October 26, 1988
    Date of Patent: July 11, 1989
    Assignee: Texaco Inc.
    Inventors: John M. Larkin, George P. Speranza
  • 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: 4806690
    Abstract: A method for producing amines, the method comprising contacting at reactive conditions at least one alcohol, aldehyde or ketone, or a mixture thereof, with an aminating agent in the presence of a catalyst, is improved by employing as the catalyst a composition comprising cobalt, copper, and a third component selected from a group consisting of iron, zinc, zirconium and mixtures thereof.
    Type: Grant
    Filed: May 13, 1985
    Date of Patent: February 21, 1989
    Assignee: The Dow Chemical Company
    Inventor: Robert G. Bowman
  • Patent number: 4795834
    Abstract: The catalytic alkylation of primary and secondary amino groups in linear polyamines using an "activated" copper catalyst.
    Type: Grant
    Filed: March 2, 1987
    Date of Patent: January 3, 1989
    Assignee: Stepan Company
    Inventors: Zdzislaw Dudzinski, Phillip Adams
  • Patent number: 4792622
    Abstract: A secondary amine is effectively prepared by reacting an alcohol or an aldehyde with a primary amine in the presence of a catalyst of copper, nickel and a metal element belonging to the platinum group VIII at a pressure of the atmospheric pressure to 5 kg/cm.sup.2 G at a temperature of 150.degree. to 250.degree. C., while water produced in the reaction is being removed out, and separating the resulting secondary amine from the product mixture.
    Type: Grant
    Filed: November 21, 1986
    Date of Patent: December 20, 1988
    Assignee: Kao Corporation
    Inventors: Yukinaga Yokota, Yuzi Sawamoto, Hideki Taniguchi, Kazuhiko Okabe
  • Patent number: 4772750
    Abstract: A method for producing amines, the method comprising contacting at reactive conditions at least one alcohol, aldehyde or ketone, or a mixture thereof, with an aminating agent in the presence of a cobalt/copper catalyst, is improved by employing as the catalyst a composition comprising cobalt and copper, the catalyst being prepared by the molten salt impregnation technique.
    Type: Grant
    Filed: October 3, 1986
    Date of Patent: September 20, 1988
    Assignee: The Dow Chemical Company
    Inventor: Clarence E. Habermann
  • Patent number: 4766245
    Abstract: An improved method for the manufacture of high molecular weight polyoxyalkylene amines wherein a hydroxy-terminated polyoxyalkylene compound having a molecular weight of at least 500 is reacted with ammonia in the presence of hydrogen and Raney nickel/aluminum under anhydrous reductive amination conditions to provide the corresponding polyoxyalkylene amine in good yield and selectivity.The Raney nickel/aluminum is a nickel/aluminum alloy treated with a base, such as sodium hydroxide, so as to only partially leach the aluminum from the alloy, such that the final product contains from about 60 wt. % to about 75 wt. % of nickel and, correspondingly, from about 25 wt. % to about 40 wt. % of aluminum and is preferably used in nugget form.
    Type: Grant
    Filed: March 1, 1985
    Date of Patent: August 23, 1988
    Assignee: Texaco Inc.
    Inventors: John M. Larkin, Terry L. Renken
  • Patent number: 4760190
    Abstract: Alkylamines are produced by reacting an alcohol with an amino compound, especially ammonia, using a catalyst containing nickel and/or cobalt and at least one difficulty reducible metal oxide, e.g. alumina, particularly alumina plus a rare earth, and having a high nickel/cobalt content.
    Type: Grant
    Filed: July 23, 1986
    Date of Patent: July 26, 1988
    Assignee: Imperial Chemical Industries PLC
    Inventor: Martyn V. Twigg
  • Patent number: 4745190
    Abstract: Selective mono- or di-amination of alkanediols is controllably obtained by catalytic reaction with secondary amines at moderate temperature and autogenous pressure, by selection of the catalyst employed. Ruthenium complexes compounded or admixed with selected organic phosphines, such as triphenylphosphine, favor high yields of alkanolamines, while ruthenium complexes in the absence of organic phosphines favor production of alkylenediamines. Iridium complexes with or without organic phosphines in admixture or chemical combination, also promote production of alkylenediamines.
    Type: Grant
    Filed: March 31, 1986
    Date of Patent: May 17, 1988
    Assignee: Air Products and Chemicals, Inc.
    Inventor: John A. Marsella
  • Patent number: 4709034
    Abstract: The present invention comprises a process for the synthesis of hydroxyalkyl amines, hydroxyalkyl piperazines, or alkyl piperazines from alkylene glycols and ammonia or alkyl amines using a substantially soluble transition metal carbonyl complex catalyst precursor.
    Type: Grant
    Filed: February 14, 1986
    Date of Patent: November 24, 1987
    Assignee: Air Products and Chemicals, Inc.
    Inventor: John A. Marsella
  • Patent number: 4683335
    Abstract: This invention is directed to novel catalyst compositions based on titania pellets on which a minor amount of tungstophosphoric acid or molybdophosphoric acid is deposited. Also, the invention is directed to a process for preparing predominantly linear polyethylenepolyamines from ethylenediamine and monoethanolamine using the novel catalyst compositions.
    Type: Grant
    Filed: September 18, 1986
    Date of Patent: July 28, 1987
    Assignee: Texaco Inc.
    Inventors: John F. Knifton, Neal J. Grice
  • Patent number: 4683336
    Abstract: Amines are produced by reacting an aliphatic alcohol and/or an aliphatic aldehyde with an aminating agent in the presence of a catalyst containing copper carbonate and nickel carbonate and/or cobalt carbonate.
    Type: Grant
    Filed: December 13, 1985
    Date of Patent: July 28, 1987
    Assignee: Sherex Chemical Company Inc.
    Inventor: Clarence W. Blackhurst
  • Patent number: 4680393
    Abstract: The present invention is a process for the synthesis of tertiary alkanolamines by reacting a secondary amine with an alkanediol. High selectivity for the production of alkanolamines is achieved by carrying out the reaction in the presence of a compound or complex of ruthenium in chemical combination or in admixture with an organic phosphine ligand. The organic phosphine ligand is present in an amount such that the ratio of gram mole ligand/gram atom ruthenium is greater than 5.
    Type: Grant
    Filed: May 8, 1986
    Date of Patent: July 14, 1987
    Assignee: Air Products and Chamicals, Inc.
    Inventor: John A. Marsella
  • Patent number: 4665195
    Abstract: Disclosed is a process for producing di-amino-polyalkenyl ethers by reacting (a) one or more acyclic or heterocyclic amino compounds with (b) one or more polyalkenyl ether glycols or polyalkenyl amino ether alcohols, in the presence of a hydrogenation catalyst, at elevated temperatures and pressures.
    Type: Grant
    Filed: December 23, 1983
    Date of Patent: May 12, 1987
    Assignee: Exxon Research and Engineering Company
    Inventors: Eugene L. Stogryn, W.S. Winston Ho, Angelo A. Montagna
  • 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: 4642381
    Abstract: This invention relates to an improved catalyst and method for the selective production of methylamines. More particularly, it is concerned with the preparation of stable highly active catalysts for producing methylamines by a catalytic reaction of ammonia or substituted amines and binary synthesis gas (CO+H.sub.2).
    Type: Grant
    Filed: November 28, 1983
    Date of Patent: February 10, 1987
    Assignee: Lehigh University
    Inventors: Kamil Klier, Richard G. Herman, Gamini A. Vedage