Group Vi Or Viii Metal Containing Catalyst Utilized Patents (Class 564/480)
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Patent number: 5808158Abstract: A process for producing primary amines which comprises reacting primary alcohols branched in position 2 with ammonia in the presence of a metal catalyst/co-catalyst.Type: GrantFiled: May 9, 1996Date of Patent: September 15, 1998Assignee: RWE-DEA Aktiengesellschaft fur Mineraloel und ChemieInventors: Martin Conrads, Albert Thomas Hermann, Erich Scherf, Arwed Wagner
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Patent number: 5696293Abstract: The present invention provides a catalyst composition for producing a polyether polyamine, comprising:(a) ruthenium and(b) at least one of metals selected from the group consisting of palladium, platinum, rhodium, osmium, iridium, rhenium, technetium, molybdenum and tungsten on a carrier.Type: GrantFiled: April 1, 1996Date of Patent: December 9, 1997Assignee: Nippon Paint Co., Ltd.Inventors: Christopher Harold Phillips, Yoji Hirasawa, Keiichi Okajima, Julius John Batty, Brian Lewis Booth
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Patent number: 5696294Abstract: N,N-Dimethyl-N-alkylamine or -alkenylamine is prepared by reacting a higher alcohol and dimethylamine by passing hydrogen gas and dimethylamine into a reactor containing a catalyst for the reaction at a pressure of atmospheric pressure to 100 atm. at 150.degree. C. to 250.degree. C. and removing water produced in the reaction as a component of the mixed hydrogen and unreacted dimethylamine gas which is discharged from the reactor, wherein at the point in the reaction at which from 90 to 99% of the higher alcohol has reacted with dimethylamine, one of the following procedures is followed: i) the introduction of only dimethylamine gas into the reactor is stopped, and the reaction is allowed to continue at a temperature 20.degree. to 150.degree. C. lower than the reaction temperature recited above; ii) the introduction of only dimethylamine gas into the reactor is stopped while the temperature is decreased to a level of 20.degree. to 150.degree. C.Type: GrantFiled: September 19, 1996Date of Patent: December 9, 1997Assignee: Kao CorporationInventors: Hiroshi Abe, Hideki Taniguchi, Tetsuaki Fukushima
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Patent number: 5679862Abstract: A process for the amination of aliphatic alkane derivatives such as alcohols (mono and polyhydric) which uses catalytic distillation to take advantage of the condensing distillate within the distillation reaction zone in the distillation column reactor. The operation of the distillation column reactor results in both a liquid and vapor phase within the distillation reaction zone. The catalyst is prepared in the form of a distillation structure. The reaction is carried out in a distillation column reactor at a low hydrogen partial pressure, e.g. in the range of 0.1 psia to less than 10 psia.Type: GrantFiled: March 25, 1996Date of Patent: October 21, 1997Assignee: Chemical Research & Licensing CompanyInventors: Speros Peter Nemphos, Dennis Hearn
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Patent number: 5646235Abstract: A method is provided for the preparation of tertiary polyamines by alkylating a polyamine having at least two primary amino groups without the use of excess solvent. More particularly, a tertiary amine is produced by reductively alkylating a polyamine with a carbonyl compound, such as formaldehyde, in a reaction zone while in the presence of a hydrogenation catalyst and hydrogen under reductive conditions. The carbonyl compound is continuously supplied to the reaction zone.Type: GrantFiled: June 18, 1996Date of Patent: July 8, 1997Assignee: Huntsman Petrochemical CorporationInventors: Robert LeRoy Zimmerman, Wheeler Conrad Crawford, Rodney Frederick Lloyd
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Patent number: 5625098Abstract: Amines such as methyl amine are reacted with materials such as reducing sugars in aqueous/hydroxy solvents such as water and/or 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: GrantFiled: June 5, 1995Date of Patent: April 29, 1997Assignee: The Procter & Gamble CompanyInventors: Junan Kao, Jeffrey J. Scheibel, Robert E. Shumate, Cynthia M. Stark, Roland G. Severson, Jr., Kevin L. Garber, Scott A. VanDiest
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Patent number: 5608113Abstract: In a process for preparing diamines from aminoalcohols and nitrogen compounds selected from the group consisting of ammonia and primary and secondary amines at from 80.degree. to 250.degree. C. and pressures of from 1 to 400 bar using hydrogen in the presence of a zirconium, copper, nickel catalyst, the catalytically active composition comprises from 20 to 85% by weight of oxygen-containing zirconium compounds, calculated as ZrO.sub.2, from 1 to 30% by weight of oxygen-containing compounds of copper, calculated as CuO, from 30 to 70% by weight of oxygen-containing compounds of nickel, calculated as NiO, from 0.1 to 5% by weight of oxygen-containing compounds of molybdenum, calculated as MoO.sub.3, and from 0 to 10% by weight of oxygen-containing compounds of aluminum and/or manganese, calculated as Al.sub.2 O.sub.3 and MnO.sub.2 respectively.Type: GrantFiled: August 10, 1995Date of Patent: March 4, 1997Assignee: BASF AktiengesellschaftInventors: Rainer Becker, Volkmar Menger, Wolfgang Reif, Andreas Henne
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Patent number: 5600000Abstract: The present invention relates to improved reductive amination processes whereby monoethanolamine and ammonia are reacted in the presence of hydrogen and various reductive amination catalysts to yield high selectivity to acyclic products such as aminoethylethanol-amine, while reducing the production of cyclic products such as piperazine. When the process of the present invention is carried out in the presence of reductive amination catalyst containing metals such as nickel or nickel-rhenium on transitional alumina carriers, productivity and selectivity to the desired products is increased. Alternatively, the process may be carried out in the presence of hydrotalcite-like or takovite-like catalysts which have been enhanced by the use of promoters to achieve the desired results.Type: GrantFiled: June 5, 1995Date of Patent: February 4, 1997Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Stephen W. King
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Patent number: 5554793Abstract: A process of reforming an alkyleneamine feedstock or a mixture of such feedstocks to an alkyleneamine or a mixture of alkyleneamines which is different from the feedstock or feedstock mixture. The process is catalyzed by one of the following: Group VB metal oxides, Group VB metal phosphates, Group IIA metal silicates, and tungsten oxides. For example, ethylenediamine is contacted with a catalyst of niobic acid or magnesium silicate to yield predominantly diethylenetriamine and non-cyclic triethylenetetramines; whereas high molecular weight polyethylenepolyamines are cracked by the same catalysts to mixtures of lower molecular weight linear and cyclic materials.Type: GrantFiled: December 19, 1994Date of Patent: September 10, 1996Assignee: The Dow Chemical CompanyInventors: George E. Hartwell, Robert G. Bowman, David C. Molzahn
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Patent number: 5530127Abstract: A process for the preparatiion of an amine which comprises reacting a primary or secondary alcohol and a nitrogen compound selected from the group consisting of ammonia and primary and secondary amines, at temperatures of from 80.degree. to 250.degree. C. and pressures of from 1 to 400 bar using hydrogen in the presence of a zirconium/copper/nickel catalyst, wherein the catalytically active material contains from 20 to 85 wt % of oxygen-containing zirconium compounds, calculated as ZrO.sub.2, from 1 to 30 wt % of oxygen-containing compounds of copper, calculated as CuO, from 30 to 70 wt % of oxygen-containing compounds of nickel, calculated as NiO, from 0.1 to 5 wt % of oxygen-containing compounds of molybdenum, calculated as MoO.sub.3 and from 0 to 10 wt % of oxygen-containing compounds of aluminum and/or manganese, calculated as Al.sub.2 O.sub.3 or MnO.sub.2, respectively.Type: GrantFiled: August 1, 1995Date of Patent: June 25, 1996Assignee: BASF AktiengesellschaftInventors: Wolfgang Reif, Lothar Franz, Peter Stops, Volkmar Menger, Rainer Becker, Rudolf Kummer, Siegfried Winderl
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Patent number: 5444099Abstract: A tertiary aminoalcohol having a tert-amino group(s) in the main chain and hydroxyl groups at the terminals. The use of this compound for purposes different from that of ordinary amines and amine derivatives is expected.A process for producing the tertiary aminoalcohol wherein a catalyst comprising copper, a transition metal element of the fourth period and a platinum group element of the group VIII, and further optionally containing an alkali metal or an alkaline earth metal is used.A process for producing polyurethane using the above-mentioned tertiary aminoalcohol which can solve the problems occurring in the production of a polyurethane using a tertiary amine which has a strong irritating odor and is highly irritant to the skin as a catalyst, for example, deteriorations of working atmosphere and sales appeal of the polyurethane.Type: GrantFiled: September 20, 1993Date of Patent: August 22, 1995Assignee: Kao CorporationInventors: Hiroshi Abe, Tetsuaki Fukushima, Kohshiro Sotoya, Shoichiro Harada, Hiroshi Kitagawa, Masayoshi Morii, Yasutoshi Isayama
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Patent number: 5410086Abstract: This invention relates to a method for controlling the weight ratio of diethylenetriamine to piperazine in a process in which ethylenediamine, or a mixture of ethylenediamine and monoethanolamine, and hydrogen are maintained in the presence of a hydrogenation catalyst, which method comprises adjusting the hydrogen concentration in the liquid phase in an amount sufficient to effectuate control of the weight ratio of diethylenetriamine to piperazine in said process.Type: GrantFiled: June 25, 1991Date of Patent: April 25, 1995Inventor: Lloyd M. Burgess
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Patent number: 5399769Abstract: This invention relates to a process for producing a nonequilibrium distribution of methylamines by the catalyzed reaction of methanol and/or dimethyl ether with ammonia and by the catalytic reforming of a methylamine containing feedstock. One process selectively affords a reaction product enriched in mono and dimethylamines and low in trimethylamine, at high conversion of methanol or dimethylether. A variation of the process effects reforming a methylamine containing feedstock, optionally containing ammonia over a catalyst. The key to achieving this low TMA selectivity at high conversion resides in the use of a microporous zeolite, preferably chabazite, catalyst having a geometric selectivity index (GSI) less about 3, a shape selectivity index (SSI) greater than about 5 and a sorption capacity for 1-PrOH of at least 0.5 mmol/g.Type: GrantFiled: June 3, 1994Date of Patent: March 21, 1995Assignee: Air Products and Chemicals, Inc.Inventors: Frederick C. Wilhelm, Gene E. Parris, Brent A. Aufdembrink, Thomas R. Gaffney
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Patent number: 5364971Abstract: The present invention relates to a process for the reduction of the color of polyamines by reacting at elevated temperature, e.g. 120.degree.-170.degree. C., and pressure, e.g. 500 to 6000 psig. the colored polyamines, e.g. triethylenetetramine and tetraethylenepentamine, in the presence of a ruthenium on alumina hydrogenation catalyst. The catalyst for the polyamine decolorization process preferably has at least 0.5 wt. % Ru. In the process of the present invention, the polyamines can either be distilled into a narrow product composition and then hydrogenareal, or a crude polyamine product can be hydrogenated and then distilled to produce the desired product composition.Type: GrantFiled: August 25, 1993Date of Patent: November 15, 1994Assignee: Texaco Chemical Inc.Inventor: Wei-Yang Su
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Patent number: 5362914Abstract: The present invention relates to a process for the reduction of the color of polyamines by reacting at elevated temperature, e.g. 120.degree.-170.degree. C., and pressure, e.g. 500 to 6000 psig. the colored polyamines, e.g. triethylenetetramine and tetraethylenepentamine, in the presence of a cobalt on alumina hydrogenation catalyst promoted with copper and chromium. In the process of the present invention, the polyamines can either be distilled into a narrow product composition and then hydrogenated, or a crude polyamine product can be hydrogenated and then distilled to produce the desired product composition.Type: GrantFiled: August 25, 1993Date of Patent: November 8, 1994Assignee: Texaco Chemical Inc.Inventor: Wei-Yang Su
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Patent number: 5362913Abstract: Highly saturated, highly aminated alkoxylated polymers may be reliably made by an improved process involving the steps of (1) polymerizing one or more unsaturated hydrocarbons to form a liquid polymer, where at least one of the unsaturated hydrocarbons is butadiene; (2) providing the liquid polymer with terminal hydroxyl groups; (3) alkoxylating the hydroxylated liquid polymer with one or more alkylene oxides having at least three carbon atoms to provide secondary terminal hydroxyl groups; (4) simultaneously aminating and hydrogenating the alkoxylated liquid polymer to produce an essentially saturated, aminated, alkoxylated liquid polymer in the presence of hydrogen and ammonia and a catalyst. The catalyst preferably contains nickel as the single greatest component, with smaller amounts of copper, chromium and molybdenum. Excesses of hydrogen and ammonia are used in the final step.Type: GrantFiled: November 16, 1992Date of Patent: November 8, 1994Assignee: Huntsman CorporationInventors: John F. Knifton, Michael Cuscurida
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Patent number: 5352835Abstract: Disclosed is a process for the amination of polyols to form primary amines which comprises reacting a polyoxyalkylene alcohol or polyol having a molecular weight of from about 230 to 5000 and ammonia in the presence of hydrogen over a catalyst consisting essentially of 10 to 35 wt % nickel, 1 to 20 wt % copper and 0.1 to 2.0 wt % optionally chromium or molybdenum promoter impregnated onto a .theta.-alumina support at a temperature of 100.degree. C. to 300.degree. C. and a pressure of 1000 psig to 3000 psig wherein the .theta.-alumina support results from calcining .gamma.-alumina or pseudo-boehmite for 2-4 hours at 900.degree.-1100.degree. C.Type: GrantFiled: February 8, 1993Date of Patent: October 4, 1994Assignee: Texaco Chemical CompanyInventors: Pei-Shing E. Dai, Terry L. Renken, Laurence D. Neff
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Patent number: 5344984Abstract: A method for preparing "twin-tailed" tertiary amines which have two moles of alkoxylated phenol bonded to each nitrogen function of a molecule of methylamine and represented by the formula: ##STR1## wherein x represents zero to about 30 which comprises alkylating a mole of methylamine with two moles of alkoxylated alkylphenol over a catalyst comprising:5 to 70% nickel;1 to 20% copper;0.1 to 10% chromium; and0.1 to 10% molybdenum on an alumina support.Type: GrantFiled: April 8, 1993Date of Patent: September 6, 1994Assignee: Texaco Chemical CompanyInventors: John F. Knifton, Carter G. Naylor
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Patent number: 5331101Abstract: A process for preparing amines or imines which comprises contacting an alcohol, aldehyde, or ketone with an aminating agent in the presence of a catalyst under reaction conditions sufficient to form an amine or imine, wherein the catalyst comprises a homogeneous mixture of (a) 10-90 mole percent cobalt or an insoluble salt thereof, (b) 9-89 mole percent copper or an insoluble salt thereof, and (c) 1-20 mole percent of a metal or insoluble salt of a metal selected from the group consisting of a Lanthanum series metal, thorium, uranium, scandium, titanium, and yttrium is described. A process which employs zirconium as component (c) and which is supported on a carrier material, wherein the carrier material has been neutralized with a base, is also disclosed.Type: GrantFiled: January 5, 1990Date of Patent: July 19, 1994Assignee: The Dow Chemical CompanyInventor: Clarence E. Habermann
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Patent number: 5331102Abstract: Color-containing alkanolamines or alkyleneamines, having color numbers of up to 100 PtCo or higher, can be treated with inorganic solid acidic catalysts. Inorganic support materials having bonded inorganic acid functionalities may be used as the inorganic solid acidic catalysts. In the presence of water, these inorganic solid acidic catalysts produce decolorized alkanolamines or alkyleneamines having color numbers of 20 PtCo or less. The process of decolorization can be carried out in batch or continuous mode processes thus providing low cost, high quality and high purity end products.Type: GrantFiled: June 28, 1993Date of Patent: July 19, 1994Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Charles A. Gibson
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Patent number: 5321160Abstract: A process for producing an ethylenamine, which comprises reacting ammonia and/or an ethylenamine with an ethanolamine in the presence of hydrogen to obtain an ethylenamine having an increased number of ethylene chains over the ammonia and/or the ethylenamine used as the starting material, wherein a catalyst comprising Ni, X and M elements wherein X is Re, Ir, Pt or Pd, and when X is Re, Ir or Pb, M is at least one rare earth element selected from the group consisting of scandium, yttrium, praseodymium, neodymium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium and lutetium, and when X is Pd, M is at least one member selected from the group consisting of rare earth elements is used for the reaction.Type: GrantFiled: July 29, 1992Date of Patent: June 14, 1994Assignee: Tosoh CorporationInventors: Toshio Hironaka, Noritaka Nagasaki, Yasushi Hara
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Patent number: 5315041Abstract: A tertiary aminoalcohol having a tert-amino group(s) in the main chain and hydroxyl groups at the terminals. The use of this compound for purposes different from that of ordinary amines and amine derivatives is expected.A process for producing the tertiary aminoalcohol wherein a catalyst comprising copper, a transition metal element of the fourth period and a platinum group element of the group VIII, and further optionally containing an alkali metal or an alkaline earth metal is used.A process for producing polyurethane using the above-mentioned tertiary aminoalcohol which can solve the problems occurring in the production of a polyurethane using a tertiary amine which has a strong irritating odor and is highly irritant to the skin as a catalyst, for example, deteriorations of working atmosphere and sales appeal of the polyurethane.Type: GrantFiled: March 4, 1992Date of Patent: May 24, 1994Assignee: Kao CorporationInventors: Hiroshi Abe, Tetsuaki Fukushima, Kohshiro Sotoya, Shoichiro Harada, Hiroshi Kitagawa, Masayoshi Morii, Yasutoshi Isayama
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Patent number: 5296631Abstract: A process for producing an N-alkyl-N-methylamine or an N-alkenyl-N-methylamine in a high yield from a higher alcohol and methylamine comprising the step of reacting a higher alcohol with methylamine in the presence of a catalyst comprising copper and a fourth period transition metal of the Periodic Table, except for chromium, or a catalyst comprising copper, a fourth period transition metal of the Periodic Table, except for chromium, and an element of the platinum group VIII of the Periodic Table, at a pressure ranging from atmospheric pressure to 100 atm. G., at a reaction temperature ranging from 100.degree. to 250.degree. C., with hydrogen gas being introduced into the reaction system while water produced in the reaction is removed from the reaction system and the amount of methylamine in the gaseous mixture which contains no matter formed through the reaction and is exhausted from the reaction system is regulated from 5 to 50% by volume.Type: GrantFiled: April 21, 1992Date of Patent: March 22, 1994Assignee: Kao CorporationInventors: Hiroshi Abe, Hideki Taniguchi, Yoshifumi Nishimoto, Kohshiro Sotoya
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Patent number: 5288911Abstract: Preparation of .alpha.,.omega.-aminoalcohols of the general formula IHO--CH.sub.2 --X--CH.sub.2 --NH.sub.2 (I),in which x denotes a C.sub.1 -C.sub.20 -alkylene chain optionally substituted by inert radicals and/or optionally interrupted by oxygen or nitrogen,by the reaction of .alpha.,.omega.-alkanediols of the general formula IIHO--CH.sub.2 --X--CH.sub.2 --OH (II),in which the connecting member x has the meanings stated above, with ammonia and a catalyst at a temperature ranging from 150.degree. to 300.degree. C. and under a pressure of from 50 to 300 bar, wherein the catalyst used is one whose catalytically active material consists of iron to an extent of from 5 to 100% w/w.Type: GrantFiled: April 22, 1992Date of Patent: February 22, 1994Assignee: BASF AktiengesellschaftInventors: Gerhard Koppenhoefer, Wolfgang Schroeder, Dieter Voges
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Patent number: 5283341Abstract: A process for producing a heterocyclic tertiary amine of the formula (III): ##STR1## wherein A is a nitrogen atom or C-R.sup.5, B is a nitrogen atom or C-R.sup.6, is a single bond or a double bond, and each of R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.5 and R.sup.6 which may be the same or different, is a hydrogen atom, an acyl group, a halogen atom, a cyano group, etc., provided that two of R.sup.1, R.sup.2, R.sup.3 and R.sup.4 may together form a 3-membered, 4-membered, 5-membered or 6-membered aliphatic ring, a heterocyclic rig or aromatic ring, and R.sup.7 is a C.sub.1-6 alkyl group which may be substituted, etc., which process comprises reacting a heterocyclic secondary amine of the formula (I): ##STR2## wherein A, B, , R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are as defined above, with an alkylating agent of the formula (II):R.sup.7 --X (II)wherein R.sup.7 is as defined above, and X is a hydroxyl group, a halogen atom, a OSO.sub.3 R.sup.7 group, a OSO.sub.2 R.sup.7 group, a OCO.sub.2 R.sup.7 group, a OCOR.Type: GrantFiled: May 8, 1992Date of Patent: February 1, 1994Assignee: Nissan Chemical Industries Ltd.Inventors: Norio Tanaka, Masataka Hatanaka, Yoshihisa Watanabe
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Patent number: 5256786Abstract: A process of reforming cyclic alkyleneamines to amine-extended cyclic alkyleneamines involving contacting a cyclic alkyleneamine or mixture of cyclic alkyleneamines in the liquid phase with a catalyst under reaction conditions. The catalyst is selected from the group consisting of (a) Group VB metal oxides, (b) Group VB metal phosphates, (c) silicates of Groups IIA, IIIB, IVB and VB, and (d) specified tungsten oxides. For example, piperazine or a mixture of piperazine and aminoethylpiperazine is contacted with magnesium silicate to yield a mixture of amine-extended piperazines, including 1,2-bis(piperazinyl)-ethane and N,N'-bis(2-piperazinylethyl)piperazine.Type: GrantFiled: March 2, 1992Date of Patent: October 26, 1993Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
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Patent number: 5254736Abstract: The process for the preparation of aliphatic amines of general formula R-NH-R' in which R is an aliphatic residue with 10 to 22 carbon atoms and R' is an aliphatic residue with 1 to 8 carbon atoms, comprising reacting under a hydrogen pressure an alkanol with a monoalkylamine in the presence of a catalytic system constituted by a supported nickel catalyst and an alkaline carbonate, more specifically potassium carbonate.Type: GrantFiled: July 28, 1992Date of Patent: October 19, 1993Assignee: CECA, S.A.Inventor: Christian Forquy
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Patent number: 5248827Abstract: A process for producing an ethylenamine, which comprises reacting ammonia and/or an ethylenamine with an ethanolamine in the presence of hydrogen to obtain an ethylenamine having an increased number of ethylene chains over the ammonia and/or the ethyelenamine used as the starting material, wherein a catalyst comprising Ni and M elements wherein M is at least one rare earth element selected from the group consisting of scandium, yttrium, praseodymium, neodymium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium and lutetium, is used for the reaction.Type: GrantFiled: September 17, 1991Date of Patent: September 28, 1993Assignee: Tosoh CorporationInventors: Yasushi Hara, Toshio Hironaka, Noritaka Nagasaki, Nobuyuki Kanai, Nobumasa Suzuki, Yukio Ito, Takanori Miyake
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Patent number: 5231229Abstract: A catalyst for making polyalkylenepolyamines by the reaction of a monoalkanolamine with an alkyleneamine which contains phosphorus and fluorine on a metal oxide support, the metal being selected from Groups IIIA, IIIB, IVB and VB of the periodic chart. The surface of a support, e.g. titania, is impregnated with at least one compound which contains fluorine and one which contains phosphorus. The same compound can contain both elements, e.g. a fluorophosphoric acid, or two or more compounds, which together contain the required elements, can be employed.Type: GrantFiled: December 20, 1990Date of Patent: July 27, 1993Assignee: The Dow Chemical CompanyInventors: Stephen J. Webster, Lester L. Melton
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Patent number: 5231230Abstract: This invention relates to a process for making amines having a high yield weight percent of diethylenetriamine (DETA) by condensing an amino compound in the presence of a condensation catalyst selected from a Group IVB metal oxide, a metallic phosphate having a cyclic structure or an acyclic structure which is transformed into a cyclic structure during the process, a metallic polyphosphate having a condensed structure, a Group VIB metal-containing substance and a promoted condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in DETA.Type: GrantFiled: March 30, 1990Date of Patent: July 27, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Lloyd M. Burgess, Arthur R. Doumaux, Jr., Stephen W. King, David J. Schreck
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Patent number: 5225600Abstract: This invention relates to a process for making amines by condensing an amino compound in the presence of a Group VIB metal-containing condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in triethylenetetramine (TETA), tetraethylenepentamine (TEPA) and pentaethylenehexamine (PEHA).Type: GrantFiled: August 26, 1992Date of Patent: July 6, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Arthur R. Doumaux, Jr., David J. Schreck
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Patent number: 5225599Abstract: This invention relates to a process for making amines having a high yield weight percent of linear triethylenetetramine (L-TETA) and aminoethylethanolamine (AEEA) by condensing an amino compound in the presence of a condensation catalyst selected from a Group IVB metal oxide, a Group VIB metal-containing substance and a promoted condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in L-TETA and AEEA.Type: GrantFiled: March 30, 1990Date of Patent: July 6, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Lloyd M. Burgess, Arthur R. Doumax, Jr.
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Patent number: 5225598Abstract: This invention relates to a process for making amines having a high yield weight percent of linear pentaethylenehexamine (L-PEHA) and hydroxyethyldiethylenetriamine (HEDETA) by condensing an amino compound in the presence of a condensation catalyst selected from a Group IVB metal oxide, a Group VIB metal-containing substance and a promoted condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in L-PEHA and HEDETA.Type: GrantFiled: March 30, 1990Date of Patent: July 6, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Arthur R. Doumaux, Jr., Stephen W. King, Lloyd M. Burgess
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Patent number: 5220071Abstract: This invention relates to a process for making amines having a high yield weight percent of pentaethylenehexamine (PEHA) and hydroxyethyltriethylenetetramine (HETETA) by condensing an amino compound in the presence of a condensation catalyst selected from a Group IVB metal oxide, a Group VIB metal-containing substance and a promoted condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in PEHA and HETETA.Type: GrantFiled: March 30, 1990Date of Patent: June 15, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Lloyd M. Burgess, Arthur R. Doumaux, Jr., Stephen W. King, David J. Schreck
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Patent number: 5214215Abstract: This invention relates to a process for making amines having a high yield weight percent of aminoethylethanolamine (AEEA) by condensing an amino compound in the presence of a condensation catalyst selected from a Group IVB metal oxide, a Group VIB metal-containing substance and a promoted condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in AEEA.Type: GrantFiled: March 30, 1990Date of Patent: May 25, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Lloyd M. Burgess, Arthur R. Doumaux, Jr.
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Patent number: 5214213Abstract: This invention relates to a process for making amines having a high yield weight percent of linear tetraethylenepentamine (L-TEPA) and hydroxyethyldiethylenetriamine (HEDETA) by condensing an amino compound in the presence of a condensation catalyst selected from a Group IVB metal oxide, a Group VIB metal-containing substance and a promoted condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in L-TEPA and HEDETA.Type: GrantFiled: March 30, 1990Date of Patent: May 25, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Lloyd M. Burgess, Arthur R. Doumaux, Jr.
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Patent number: 5210306Abstract: This invention relates to a process for making amines by condensing an amino compound in the presence of a condensation catalyst and a condensation catalyst promoter, wherein said condensation catalyst promoter is present in an amount sufficient to promote the condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in triethylenetetramine (TETA), tetraethylenepentamine (TEPA) and pentaethylenehexamine (PEHA).Type: GrantFiled: August 8, 1989Date of Patent: May 11, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Arthur R. Doumaux, Jr., David J. Schreck, Stephen W. King, George A. Skoler
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Patent number: 5202489Abstract: 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: GrantFiled: August 8, 1989Date of Patent: April 13, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Arthur R. Doumaux, Jr., David J. Schreck, George A. Skoler, Stephen W. King
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Patent number: 5202490Abstract: 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: GrantFiled: May 25, 1990Date of Patent: April 13, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Lloyd M. Burgess, Charles A. Gibson, David J. Schreck
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Patent number: 5202492Abstract: This invention relates to a process for making amines by condensing an amino compound in the presence of a metallic phosphate condensation catalyst having a cyclic structure or an acyclic structure which is transformed into a cyclic structure during said process. This invention also relates to an alkyleneamines producers composition rich in triethylenetetramine (TETA), tetraethylenepentamine (TEPA) and pentaethylenehexamine (PEHA).Type: GrantFiled: August 8, 1989Date of Patent: April 13, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Arthur R. Doumaux, Jr., David J. Schreck
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Patent number: 5202491Abstract: 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: GrantFiled: May 25, 1990Date of Patent: April 13, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Lloyd M. Burgess, Charles A. Gibson, David J. Schreck
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Patent number: 5202485Abstract: A process for preparing an N-alkylaminophenol is disclosed, comprising subjecting an aminophenol to reductive alkylation with an aldehyde or a ketone in the presence of an organic solvent and hydrogen, wherein the reductive alkylation is carried out at a temperature of from 20.degree. to 70.degree. C. in the further presence of a catalyst for reduction comprising platinum and at least one metal element selected from metal elements belonging to the IB group, IIB group, IVB group, VB group, and VIB group of the Periodic Table, supported on activated carbon, or comprising palladium and at least one metal element selected from metal elements belonging to the IB group, IIB group, IVB group, VB group and VIB group of the Periodic Table, supported on activated carbon.Type: GrantFiled: April 29, 1991Date of Patent: April 13, 1993Assignee: Sumitomo Chemical Co., Ltd.Inventors: Hiroshi Maki, Michihiro Kawasaki, Horishi Shimizu, Yoshiaki Ito
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Patent number: 5198592Abstract: The invention concerns a method of performing a chemical reaction in which hydrogenation and/or dehydrogenation occurs, in the presence of a supported catalyst comprising a carrier material with copper as active component and iron as a promotor. According to the invention, the proporation of iron, calculated on the amount of copper and iron jointly, on an atomic basis, is no more than 25%. The invention also relates to a catalyst for carrying out the reaction, and to a process for preparing a supported catalyst.Type: GrantFiled: October 15, 1990Date of Patent: March 30, 1993Assignee: Engelhard De Meern B.V.Inventors: Johannes van Beijnum, Adrianus J. van Dillen, John W. Geus
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Patent number: 5196588Abstract: 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: GrantFiled: May 25, 1990Date of Patent: March 23, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Lloyd M. Burgess, Charles A. Gibson, David J. Schreck
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Patent number: 5175369Abstract: This invention relates to a process for separating methoxyisopropylamine and particularly to an improvement in the process for the recovery of methoxyisopropylamine from the reaction of methoxyisopropanol with ammonia under amination conditions. In this process water is produced as a byproduct and in the separation process an azeotrope is formed which comprises about 14% water and 86% methoxyisopropylamine at atmospheric pressure. The process for enhancing separation of the azeotrope comprises contacting the azeotrope of methoxyisopropylamine and water with diisopropylamine in sufficient amount to form the azeotrope of water and diisopropylamine and separating the azeotrope from the other materials in a distillation column. The overheads in this column is charged to a decanter where water is removed as a bottoms phase and the diisopropylamine as the upper phase and returned as reflux to the distillation volumn.Type: GrantFiled: November 1, 1990Date of Patent: December 29, 1992Assignee: Air Products and Chemicals, Inc.Inventor: Robert L. Fowlkes
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Patent number: 5166415Abstract: This invention relates to a process for making amines having a high yield weight percent of diethylenetriamine (DETA) and aminoethylethanolamine (AEEA) by condensing an amino compound in the presence of a condensation catalyst selected from a Group IVB metal oxide, a Group VIB metal-containing substance and a promoted condensation catalyst. This invention also relates to an alkyleneamines producers composition rich in DETA and AEEA.Type: GrantFiled: March 30, 1990Date of Patent: November 24, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Arthur R. Doumaux, Jr., Stephen W. King, Lloyd M. Burgess
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Patent number: 5166433Abstract: 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: GrantFiled: January 7, 1991Date of Patent: November 24, 1992Assignee: BASF AktiengesellschaftInventors: Matthias Irgang, Juergen Schossig, Wolfgang Schroeder, Siegfried Winderl
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Patent number: 5108579Abstract: A zeolite, designated zeolite NU-86, having a molar composition expressed by the formula 100 XO.sub.2 : equal to or less than 10 Y.sub.2 O.sub.3 : equal to less than 20 R.sub.2/n O where R is one or more cations of valency n, X is silicon and/or germanium, Y is one or more of aluminum, iron, gallium, boron, titanium, vanadium, zirconium, molybdenum, arsenic, antimony, chromium and manganese and having an X-ray diffraction pattern including the lines shown in Table 1 is prepared from a reaction mixture comprising XO.sub.2 (preferably silica), Y.sub.2 O.sub.3 (preferably alumina) and a polymethylene alpha, omega-diammonium cation. This zeolite is a useful catalyst for a variety of reactions.Type: GrantFiled: June 17, 1991Date of Patent: April 28, 1992Assignee: Imperial Chemical Industries PLCInventor: John L. Casci
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Patent number: 5103058Abstract: Process for producing aliphatic imines and/or amines from aliphatic monohydric alcohols, such as higher molecular weight oxo alcohols, including ether alcohols, comprising the steps of dehydrogenating the alcohol to an aldehyde in situ in the presence of a zinc oxide and/or zinc salt/metal hydroxide dehydrogenation catalyst and a soluble amount of a primary aliphatic amine which condenses immediately with the aldehyde under reflux conditions, with continuous water removal, to form the corresponding aliphatic imine (Schiff base). The corresponding aliphatic amine can be formed by reducing or reductively aminating the imine in known manner to form corresponding primary, secondary or tertiary amines as desired.Type: GrantFiled: November 5, 1990Date of Patent: April 7, 1992Assignee: Exxon Chemical Patents IncInventors: Roy L. Pruett, Michael J. Keenan, Edmund J. Mozeleski
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Patent number: 5099070Abstract: A process for producing neopentyldiamine is provided. This process entails contacting a feedstream containing neopentanolamine with ammonia and hydrogen in the presence of a support nickel catalyst under amination conditions.Type: GrantFiled: December 7, 1990Date of Patent: March 24, 1992Assignee: Eastman Kodak CompanyInventors: Garrett C. Luce, Anthony W. McCollum