Of Ether Containing Compound Patents (Class 564/474)
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Patent number: 6924315Abstract: The present invention provides compounds useful as surfactants having formula (1), including isomers thereof: wherein a and b are integers independently selected from about 3 to about 6; x is an integer from about 1 to about 12; (m+n) is from about 1 to about 4; the R1 groups are independently selected from the group consisting of linear, cyclic, and branched alkyl, alkenyl, aryl, and alkylaryl groups having from about C3 to about C30 atoms; and when (m+n) is equal to or greater than 2, each R1 may be independently R2 or R3, wherein R2 and R3 are independently selected from the group consisting of linear, cyclic, and branched alkyl, alkenyl, aryl, and alkylaryl groups having from about C3 to about C30 atoms. The invention also provides a method for reducing surface tension in a waterborne composition or an industrial process by the incorporation of a surfactant having formula (1) and an aqueous composition comprising a surfactant having formula (1).Type: GrantFiled: March 13, 2003Date of Patent: August 2, 2005Assignee: Air Products and Chemicals, Inc.Inventors: Christine Peck Kretz, Michael Edward Ford, Kevin Rodney Lassila
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Patent number: 6723880Abstract: A process for producing secondary amines of the formula R1R2N—A—NH—A—NR1R2, where R1 and R2 are linear or branched C1-20-alkyl radicals, optionally substituted with from 1 to 5 phenyl groups; or cyclohexyl radicals; or together with the nitrogen atom to which they are bound, form a 3 to 7 membered saturated ring, optionally containing further hetero atoms selected from the group consisting of N, O and S, and optionally substituted with from 1 to 5 C1-2-alkyl groups. The group A is a linear or branched C2-20-alkylene group, optionally containing from 1 to 5 phenylene groups; or a radical of the formula —CH(R3)—[CH2]k—X—[CH(R3)—[CH2]k—X]m—CH(R3)—[CH2]k—, where R3 is H or CH3, X is O, S or NR4, R4 is H or a linear or branched C1-4-alkyl group, k is 1 or 2, and m is an integer from 0 to 4; or a group of the formula where n, o, p, and q are, independently, integers from 1 to 4.Type: GrantFiled: June 19, 2002Date of Patent: April 20, 2004Assignee: BASF AktiengesellschaftInventors: Peter Neumann, Johann-Peter Melder, Christoph Benisch, Arthur Höhn, Joachim Pfeffinger
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Patent number: 6709644Abstract: The present invention relates to zeolites having the crystal structure of chabazite (CHA) and having small crystallite size, to processes using the small crystallite CHA as a catalyst, and to gas separation processes using the small crystallite CHA.Type: GrantFiled: August 30, 2001Date of Patent: March 23, 2004Assignee: Chevron U.S.A. Inc.Inventors: Stacey I. Zones, Lun-Teh Yuen, Stephen J. Miller
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Patent number: 6632968Abstract: A process for preparing amines comprises reacting an epoxide of the formula (I) where R1, R2, R3 and R4 are each, independently of one another, hydrogen or a linear or branched, saturated or unsaturated C2-C200-hydrocarbon radical, with ammonia and hydrogen in the presence of a catalyst, where the molar ratio of ammonia:epoxide is from 5:1 to 500:1 and the hydrogen pressure is from 10 bar to 500 bar.Type: GrantFiled: August 2, 2002Date of Patent: October 14, 2003Assignee: BASF AktiengesellschaftInventors: Christian Ott, Marco Bergemann
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Patent number: 6403834Abstract: The invention concerns a method for preparing tris(ether-amines) of formula (I): N[A—O—(B—O)n—R]3 wherein R, A, B and n are as defined in Claim 1, comprising the reaction, in liquid phase, of an alkylene-glycol monoether of formula (II): HO—A—O—(B—O)nR wherein R, A, B and n are as defined in Claim 1, with an ammonolysis agent selected among ammonia and an etheramine of formula (I′): H3-pN[A—O—(B—O)nR]p wherein: A, B, n and R are as defined in Claim 1 and p represent 1 or 2, at a temperature ranging between 100 and 250° C., by contacting reagents with a hydrogenation-dehydrogenation catalyst.Type: GrantFiled: July 23, 2001Date of Patent: June 11, 2002Assignee: Rhodia ChimieInventors: Michel Alas, Albert Bouniot
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Patent number: 6281268Abstract: A process for making an ink jet ink comprising: a) providing a dispersion containing a pigment, an alcohol carrier and an amine-terminated polyether dispersant; b) mixing the pigment dispersion with rigid milling media less than 100 &mgr;m; c) introducing the mixture of step (b) into a mill; d) milling the mixture from step (c) until the pigment particle size is below about 100 nanometers; e) separating the milling media from the mixture milled in step (d); and f) diluting the mixture from step (e) to obtain an ink jet ink having a pigment concentration suitable for ink jet printers.Type: GrantFiled: December 20, 1999Date of Patent: August 28, 2001Assignee: Eastman Kodak CompanyInventors: Charles E. Romano, Jr., Karen E. Maskasky, Robert A. Guistina
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Patent number: 6232502Abstract: A method for making monomethylamine, dimethylamine and trimethylamine, in which methanol and/or dimethylether and ammonia are contacted in the presence of an acidic zeolite chabazite catalyst is disclosed. The method suppresses the production of trimethylamine and optimizes dimethylamine and monomethylamine yields.Type: GrantFiled: March 24, 2000Date of Patent: May 15, 2001Assignee: E. I. du Pont de Nemours and CompanyInventors: David Richard Corbin, Raul Francisco Lobo, Stephan Schwarz
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Patent number: 6166258Abstract: The present invention relates to the selectivity of production of methylamines from methanol and/or dimethylether and ammonia using at catalytic amount of acidic molecular sieve.Type: GrantFiled: September 30, 1999Date of Patent: December 26, 2000Assignee: E. I. du Pont de Nemours and CompanyInventors: David Richard Corbin, Raul Francisco Lobo, Stephan Schwarz
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Patent number: 5900510Abstract: Diaminodipropyl ethers and hydroxyaminodipropyl ethers are prepared by catalytic amination of dipropylene glycol.Type: GrantFiled: September 26, 1997Date of Patent: May 4, 1999Assignee: Bayer AktiengesellschaftInventors: Helmut Waldmann, Klaus Nachtkamp, Josef Pedain, Anatoly Bazanov, Alexandre Timofeev, Natalja Zubritskaya, Gennady Terechtchenko
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Patent number: 5874623Abstract: Disclosed herein is a method of preparing polyether aminoalcohol by reacting a primary aminoalcohol with a polyether terminated with a good leaving group.Type: GrantFiled: August 2, 1993Date of Patent: February 23, 1999Assignee: Bayer CorporationInventors: Rick L. Adkins, William E. Slack
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Patent number: 5817593Abstract: This invention includes catalysts comprising rhenium (atomic number 75), nickel, cobalt, boron and copper and/or ruthenium impregnated on a support material and a process for preparing said catalyst, said process comprising (i) impregnating a mixture of metals comprising rhenium, cobalt, copper and/or ruthenium, boron and nickel on a support material selected from the group consisting of alpha-alumina, silica, silica-alumina, kieselguhrs or diatomaceous earths, and silica-titanias; and (ii) activating said catalyst by heating the catalyst in the presence of hydrogen at an effective temperature preferably in the range of about 150.degree. C. to about 500.degree. C. for a sufficient period preferably of from about 30 minutes to about 6 hours.Type: GrantFiled: June 2, 1995Date of Patent: October 6, 1998Assignee: The Dow Chemical CompanyInventors: Dane Chang, Fred A. Sherrod
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Patent number: 5763667Abstract: Ether-linked amine-terminated polyethers are produced by reacting (1) a polyether polyol in which substantially all of the hydroxyl groups have been replaced with good leaving groups with (2) an aminoalcohol and/or aminothiol and (3) a deprotonating agent. The aminopolyethers obtained by this process are characterized by low viscosities and excellent reactivities over a wide range of molecular weights and functionalities.Type: GrantFiled: January 31, 1996Date of Patent: June 9, 1998Assignee: Bayer CorporationInventors: Rick L. Adkins, William E. Slack
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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: 5693864Abstract: Disclosed herein is a process for preparing an amine terminated polyether comprising reacting a polyether containing a leaving group with a primary amine or ammonia at a temperature of about 70 to 250 degrees Centigrade.Type: GrantFiled: October 7, 1992Date of Patent: December 2, 1997Assignee: Bayer CorporationInventors: William E. Slack, Rick L. Adkins, Hans Georg Schmelzer
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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: 5672761Abstract: The viscosity of polyether polyols characterized by functionalities greater than or equal to 1, viscosities greater than 500 mPa.multidot.s at 25.degree. C. and at least 20% terminal secondary hydroxyl groups is reduced by converting at least one terminal hydroxyl group of the polyether to a leaving group and then reacting the conversion product with a primary amine or ammonia at a temperature of from about 70.degree. to 250.degree. C.Type: GrantFiled: May 2, 1996Date of Patent: September 30, 1997Assignee: Bayer CorporationInventors: Rick L. Adkins, William E. Slack
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Patent number: 5569785Abstract: This invention provides an attrition resistant catalyst composition and method for producing such composition. The catalyst is comprised of an acidic zeolite, rho or chabazite, and a particulate binder, kaolin, bentonite, alpha-alumina, or titania, which can be optionally modified by treatment with a compound containing Si, Al, P or B.This invention further provides a process for producing methylamines, preferably dimethylamine, comprising reacting methanol and/or dimethyl ether and ammonia in the presence of a catalytic amount of an attrition resistant catalyst of the invention.Type: GrantFiled: May 30, 1995Date of Patent: October 29, 1996Assignee: E. I. Du Pont de Nemours and CompanyInventors: Konstantinos Kourtakis, Horacio E. Bergna, George C. Sonnichsen, David R. Corbin, Loren D. Brake
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Patent number: 5559270Abstract: An improved process of synthesizing gasoline soluble polyolefinic amines or polyether amines comprising the steps of reacting polyolefinic halides or polyether halides with polyamines in a specific sequence of reactions; distilling off non-reactive polyamine; neutralizing the reaction mixture; recovering polyamine(s) and water; and separating polyolefinic amines from the solids with simple filtration or centrifuge or decanting.Type: GrantFiled: December 15, 1994Date of Patent: September 24, 1996Assignee: Petrokleen, Ltd.Inventors: Donald E. Koehler, William J. Claffey
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Patent number: 5510535Abstract: Ether-linked amine-terminated polyethers are produced by reacting (1) a polyether polyol in which substantially all of the hydroxyl groups have been replaced with good leaving groups with (2) an aminoalcohol and/or aminothiol and (3) a deprotonating agent. The aminopolyethers obtained by this process are characterized by low viscosities and excellent reactivities over a wide range of molecular weights and functionalities.Type: GrantFiled: November 22, 1994Date of Patent: April 23, 1996Assignee: Bayer CorporationInventors: Rick L. Adkins, William E. Slack
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Patent number: 5482909Abstract: The present invention relates to an improved catalyst for the selective synthesis of monomethylamine (MMA) and dimethylamine (DMA) at the expense of trimethylamine (TMA) for a starting feed of methanol and/or dimethyl ether and ammonia. The current industrial catalyst for this process is a standard SiO.sub.2 /Al.sub.2 O.sub.3 material. The present invention combines this standard catalyst with microporous carbon molecular sieves (CMS) to form a composite material (i.e., a CMS/SiO.sub.2 /Al.sub.2 O.sub.3 material) with higher selectivity for the desired products MMA and DMA. The invention also relates to methods of making the improved catalyst and a process of using the improved catalyst material in the production of MMA and DMA.Type: GrantFiled: July 21, 1994Date of Patent: January 9, 1996Assignees: University of Delaware, E. I. Du Pont de Nemours & Co., Inc.Inventors: Henry C. Foley, George C. Sonnichsen, Loren D. Brake, Ravindra K. Mariwala, Davis S. Lafyatis
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Patent number: 5354893Abstract: The present invention relates to an improved catalyst for the selective synthesis of monomethylamine (MMA) and dimethylamine (DMA) at the expense of trimethylamine (TMA) for a starting feed of methanol and/or dimethyl ether and ammonia. The current industrial catalyst for this process is a standard SiO.sub.2 /Al.sub.2 O.sub.3 material. The present invention combines this standard catalyst with microporous carbon molecular sieves (CMS) to form a composite material (i.e., a CMS/SiO.sub.2 /Al.sub.2 O.sub.3 material) with higher selectivity for the desired products MMA and DMA. The invention also relates to methods of making the improved catalyst and a process of using the improved catalyst material in the production of MMA and DMA.Type: GrantFiled: July 30, 1993Date of Patent: October 11, 1994Assignees: The University of Delaware, E. I. Du Pont de Nemours Company, Inc.Inventors: Henry C. Foley, George C. Sonnichsen, Loren D. Brake, Ravindra K. Mariwala, David S. Lafyatis
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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: 5344989Abstract: An improved process for production of monomethylamines and dimethylamines, wherein an acidic zeolite H--ZK-5 prepared from K,Sr--ZK-5 is used to increase selectivity of the reaction.Type: GrantFiled: June 15, 1993Date of Patent: September 6, 1994Assignee: E. I. Du Pont de Nemours and CompanyInventors: David R. Corbin, Stephan Schwarz
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Patent number: 5326873Abstract: A method of forming 4-amino-2-buten-1-ol using 3,4-epoxy-1-butene is disclosed. A nitrogen nucleophile (e.g., an amine) is reacted with 3,4-epoxy-1-butene in the presence of a polymer-bound complex of palladium having up to four phosphine ligands.Type: GrantFiled: June 5, 1992Date of Patent: July 5, 1994Assignee: Eastman Kodak CompanyInventors: Stephen A. Godleski, Yann Hung
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Patent number: 5288909Abstract: 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: August 19, 1992Date of Patent: February 22, 1994Assignee: The Dow Chemical CompanyInventors: George E. Hartwell, Robert G. Bowman, David C. Molzahn
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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: 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: 5210307Abstract: 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: GrantFiled: January 31, 1992Date of Patent: May 11, 1993Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
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Patent number: 5183923Abstract: The invention concerns a method for the preparation of polyurethane, polyester, polyamide, and polyurea diols which contain essentially all primary hydroxyl groups without capping by ethylene oxide. The method comprises coupling an alkylene oxide adduct of propylene glycol t-butyl ether or butylene glycol t-butyl ether or its aminated derivative with organic diisocyanates or dibasic acids followed by cleavage of the t-butyl group with an acid catalyst.The resulting diol is useful in many types of urethane applications including foams, elastomers and coatings.Type: GrantFiled: March 28, 1990Date of Patent: February 2, 1993Assignee: Texaco Chemical CompanyInventors: Michael Cuscurida, George P. Speranza
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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: 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: 5118850Abstract: 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: GrantFiled: November 9, 1990Date of Patent: June 2, 1992Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
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Patent number: 5118851Abstract: A process of preparing a mixture of polyalkylenepolyamines and alkanolpolyamines comprising contacting a difunctional aliphatic alcohol with a primary or secondary aliphatic amine in the presence of a metal silicate catalyst wherein the metal is selected from the group consisting of Groups IIA, IIIB, and the lanthanide and actinide metals. For example, monoethanolamine reacts with diethylenetriamine in the presence of magnesium silicate to yield a mixture of higher molecular weight linear and branched polyethylenepolyamines and their corresponding alkanolpolyamines. These product mixtures are useful in the formation of specialty polyurethanes.Type: GrantFiled: December 5, 1990Date of Patent: June 2, 1992Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
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Patent number: 5103062Abstract: In accordance with the process of the present invention normally liquid, water-soluble poly(oxyethylene/oxypropylene) polyamine products are prepared using an initiator, which may contain oxyethylene groups. In a series of alkoxylation reaction steps the initiator is reacted with predetermined weight percentages of ethylene oxide and propylene oxide, said process comprising the steps of:a. Charging a predetermined percentage of initiator to an alkoxylation reaction zone,b. Alkoxylating said initiator therein with predetermined percentages of ethylene oxide and propylene oxide to provide an intermediate polyol,c. Propoxylating said intermediate polyol with a predetermined percentage of propylene oxide to provide a normally liquid, water-soluble precursor polyol, andd.Type: GrantFiled: April 10, 1987Date of Patent: April 7, 1992Assignee: Texaco Inc.Inventors: Michael Cuscurida, Ernest L. Yeakey
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Patent number: 5068442Abstract: There is provided a method for maintaining the activity of a zeolite catalyst in the catalytic production of methylamines from methanol and ammonia using a zeolite catalyst as at least one of catalysts applied, which comprises controlling the amount of aldehyde compounds as impurities flowing into a zeolite catalyst layer to about 0.15 g/hr.kg-cat. or lower, as calculated in terms of formaldehyde.Type: GrantFiled: May 17, 1989Date of Patent: November 26, 1991Assignee: Nitto Kagaku Kogyo Kabushiki KaishaInventors: Yoshiro Ashina, Takeyuki Fujita, Kiyonobu Niwa, Takeshi Inagaki, Yuko Nikaido
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Patent number: 5015774Abstract: 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: GrantFiled: November 14, 1989Date of Patent: May 14, 1991Assignee: Mitsui Toatsu Chemicals, Inc.Inventors: Ariko Suekane, Fumio Yamazaki, Takayoshi Masuda
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Patent number: 5015773Abstract: 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: GrantFiled: August 4, 1989Date of Patent: May 14, 1991Assignee: BP Chemicals LimitedInventor: Ian D. Dobson
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Patent number: 5011999Abstract: A process for the preparation of predominantly non-cyclic polyalkylenepolyamines comprising contacting a difunctional aliphatic alcohol with ammonia or a primary or secondary aliphatic amine in the presence of a catalyst selected from the group consisting of Group VB metal oxides, niobium phosphates, tantalum phosphates, and mixtures thereof. For example, monoethanolamine is aminated by ethylenediamine to predominantly linear and branched polyethylenepolyamines in the presence of a catalyst containing niobium oxide supported on boehmite alumina.Type: GrantFiled: February 23, 1989Date of Patent: April 30, 1991Assignee: The Dow Chemical CompanyInventors: Robert G. Bowman, George E. Hartwell, David C. Molzahn, Enrique G. Ramirez, John E. Lastovica, Jr.
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Patent number: 4983736Abstract: 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: GrantFiled: August 8, 1989Date of Patent: January 8, 1991Assignee: Union Carbide Chemicals and Plastic Company Inc.Inventors: Arthur R. Doumaux, Jr., David J. Schreck
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Patent number: 4973761Abstract: Aminomono- or di-[(poly-n-butoxy)-n-butylamino]-(poly-n-butoxy)-n-butylamines of the general formula IH.sub.2 N--[(CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 O).sub.x --(CH.sub.2).sub.4 --NH].sub.y --(CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 O).sub.x --(CH.sub.2).sub.4 --NH.sub.2 (I)where x is from 1 to 150 and y is 1 or 2, are prepared by a process in which a hydroxy-(poly-n-butoxy)-butanol of the formula IIHO--(CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.2 O).sub.x --(CH.sub.2).sub.4 --OH (II)where x is from 1 to 150, is reacted with from 1.01 to 300 mole equivalents of ammonia per hydroxyl group in the presence of a hydrogenation/dehydrogenation catalyst and hydrogen at from 150.degree. to 300.degree. C. and under from 20 to 400 bar.Type: GrantFiled: July 21, 1989Date of Patent: November 27, 1990Assignee: BASF AktiengesellschaftInventors: Willibald Schoenleben, Herbert Mueller
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Patent number: 4952734Abstract: A process for the preparation of methylamines by the reaction of amines, formaldehyde and hydrogen as starting materials on a fixed-bed catalyst in the liquid phase under pressure and preferably at elevated temperature. The starting materials contain a reduced percentage of water. They are heated to a predetermined temperature apart from each other, and then mixed with each other in the presence of the fixed-bed catalyst.Type: GrantFiled: June 23, 1988Date of Patent: August 28, 1990Assignee: Hoechst AG Werk RuhrchemieInventors: Jurgen Weber, Detlef Kampmann, Claus Kniep
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Patent number: 4940818Abstract: A process for the preparation of 2,2'-oxybis[N,N-dimethylethanamine] by reaction of 2,2'oxybisethanamine, hydrogen and formaldehyde having a reduced percentage of water on conventional fixed-bed hydrogenation catalysts. The reactants, especially the amine and formaldehyde, are heated to a predetermined temperature separate from each other, and then mixed with each other in the presence of the fixed-bed catalyst.Type: GrantFiled: June 23, 1988Date of Patent: July 10, 1990Assignee: Hoechst AktiengesellschaftInventors: Jurgen Weber, Detlef Kampmann, Franz Thonnessen, Claus Kniep
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Patent number: 4914241Abstract: Diamines of the formula ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, alkyl, aryl, alkoxy, aralkyl or cycloalkyl and X is a group of the formula(CR.sup.4 R.sup.5).sub.m (II)where R.sup.4 and R.sup.5 have the meanings given above for R.sup.1 and m is from 1 to 12, are prepared by a process in which a diamine of the formula ##STR2## where R.sup.1, R.sup.2 and X are the groups described above, is reacted with an olefin of the formula ##STR3## where R.sup.6 and R.sup.9 are each hydrogen or alkyl which is straight-chain in the .alpha.-position, in the presence of a zeolite as a catalyst.Type: GrantFiled: June 15, 1988Date of Patent: April 3, 1990Assignee: BASF AktiengesellschaftInventors: Michael Hesse, Wolfgang Hoelderich, Matthias Schwarzmann
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Patent number: 4888446Abstract: The invention concerns a method for the preparation of polyoxyalkylene compounds wherein each compound has one primary amine group and one primary hydroxyl group. The method comprises alkoxylating a t-butyl ethylene, propylene or butylene glycol then aminating the product. Finally the t-butyl group is cleaved by an acid. The compounds of the method of this invention are useful in urethane/urea plastics including foams, elastomers and coatings.Type: GrantFiled: April 11, 1988Date of Patent: December 19, 1989Assignee: Texaco Chemical Co.Inventors: Howard P. Klein, Michael Cuscurida
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Patent number: 4888447Abstract: 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: GrantFiled: June 30, 1988Date of Patent: December 19, 1989Assignee: Ethyl CorporationInventor: Kim R. Smith
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Patent number: 4847417Abstract: 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: GrantFiled: October 26, 1988Date of Patent: July 11, 1989Assignee: Texaco Inc.Inventors: John M. Larkin, George P. Speranza
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Patent number: 4814503Abstract: Improved acidic zeolite rho and ZK-5 catalysts for conversion of methanol and ammonia to dimethylamine are disclosed. The acidic zeolite rho catalyst is prepared by calcining zeolite NH.sub.4 -rho or H-rho in the presence of steam. The acidic zeolite ZK-5 catalyst is prepared by calcining zeolite NH.sub.4 -ZK-5 or H-ZK-5 in the presence of steam. An acidic zeolite rho which has been prepared by calcining zeolite NH.sub.4 -rho in a vertical furnace in the presence of ammonia is disclosed. Processes for producing dimethylamine with the specified catalysts are also disclosed.Type: GrantFiled: June 27, 1986Date of Patent: March 21, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventors: Lloyd Abrams, David R. Corbin, Robert D. Shannon
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Patent number: 4806689Abstract: A process is provided for producing dimethylamine, comprising reacting methanol and/or dimethylether and ammonia, in amounts sufficient to provide a carbon/nitrogen (C/N) ratio of from about 0.2 to about 1.5, at a temperature from about 250.degree. C. to about 450.degree. C., in the presence of a catalytic amount of an acidic zeolite rho.Type: GrantFiled: October 3, 1985Date of Patent: February 21, 1989Assignee: E. I. Du Pont de Nemours and CompanyInventors: Thurman E. Gier, Robert D. Shannon, George C. Sonnichsen, David R. Corbin, Michael Keane, Jr.
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Patent number: 4792630Abstract: A process for preparing an aminoacetaldehyde dialkyl acetal which comprises reacting a halogenoacetaldehyde dialkyl acetal with ammonia or an alkylamine in an aqueous medium in the simultaneous presence of an alkali metal hydroxide or of an alkaline earth metal hydroxide, and distilling the resulting reaction mixture.Type: GrantFiled: February 13, 1987Date of Patent: December 20, 1988Assignee: Nippon Gosei Kagaku Kogyo Kabushiki KaishaInventors: Akira Taisha, Takeo Kawabata, Takehiko Kakimoto, Kazumasa Hirata
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Patent number: 4766245Abstract: 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: GrantFiled: March 1, 1985Date of Patent: August 23, 1988Assignee: Texaco Inc.Inventors: John M. Larkin, Terry L. Renken