Process Of Forming, Purifying, Or Recovering Triethylene Diamine Per Se, Or Salt Thereof Patents (Class 544/352)
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Patent number: 5037838Abstract: N-hydroxyethyl piperazine is converted to triethylenediamine using a titania-supported tungstopyrophosphate catalyst.Type: GrantFiled: April 26, 1990Date of Patent: August 6, 1991Assignee: Texaco Chemical CompanyInventors: Robert L. Zimmerman, John F. Knifton
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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: 4970307Abstract: A process for formation of a base from a base precursor, which comprises decomposing the base precursor in the presence of a catalyst. The base precursor has the following formula (I) or (II):(R.sup.1 --C.tbd.C--CO.sub.2 H).sub.x .multidot.B (I)R.sup.2 (--C.tbd.C--CO.sub.2 H).sub.2 .multidot.B.sub.y (II)wherein R.sup.1 is a monovalent group selected from the group consisting of hydrogen, an alkyl group, a cycloalkyl group, an alkenyl group, an alkynyl group, an aryl group, a heterocyclic group, an aralkyl group, an acyl group, an alkoxycarbonyl group, carbamoyl, --CO.sub.2 M (M is an alkali metal) and --CO.sub.2 H.B, each of which may have one or more substituent groups; R.sup.Type: GrantFiled: August 13, 1987Date of Patent: November 13, 1990Assignee: Fuji Photo Film Co., Ltd.Inventors: Keiji Takeda, Jiro Tsukahara, Kozo Sato
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Patent number: 4966969Abstract: The present invention relates to a process for preparing triethylenediamines which comprises contacting an amine compound having, in the molecule, a group represented by the general formula: ##STR1## (wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 are independently a hydrogen atom or an alkyl group having 1 to 4 carbon atoms and X is nitrogen or oxygen) with a catalyst comprising crystalline metallosilicate having a silica (SiO.sub.2)/metal oxide (M.sub.2 O.sub.3) molar ratio of 12/1 or more under a pressure of not less than 4 kg/cm.sup.2 (absolute pressure).According to the present invention, the conversion of the amine compound can be greatly increased and thus the desired triethylenediamines can be produced in a high yield.Type: GrantFiled: February 14, 1990Date of Patent: October 30, 1990Assignee: Idemitsu Kosan Company LimitedInventors: Haruhito Sato, Masanori Tsuzuki
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Patent number: 4804758Abstract: 1,4-Diazabicyclo[2.2.2]octane and C-substituted 1,4-diazabicyclo[2.2.2]octanes of the formula (I) ##STR1## where R.sup.1 and R.sup.2 are each hydrogen or alkyl or alkenyl, each of 1 to 4 carbon atoms, are prepared from a heterocyclic amine of the formula (II) ##STR2## where R.sup.1 and R.sup.2 have the above meanings, R.sup.3 is hydrogen, hydroxyethyl or aminoethyl and X is hydroxyl or amino, in the presence of borosilicate and/or iron silicate zeolites as catalysts. Particularly suitable catalysts are the borosilicate and iron silicate zeolites of the pentasil type.Type: GrantFiled: October 8, 1987Date of Patent: February 14, 1989Assignee: BASF AktiengesellschaftInventors: Wolfgang Hoelderich, Kurt Schneider, Walter Best
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Patent number: 4757143Abstract: Cyclic and acyclic hydroxyethyl ethylenepolyamines are converted to triethylenediamine when using a catalyst composed of zirconia or titania to which from about 0.5 to about 7 wt. % of phosphorous has been thermally chemically bonded in the form of phosphate linkages.Type: GrantFiled: June 9, 1986Date of Patent: July 12, 1988Assignee: Texaco Inc.Inventors: Steven H. Vanderpool, Walter H. Brader, Jr., Ernest L. Yeakey, Edward C. Nieh, Thomas T. McConnell
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Patent number: 4754036Abstract: N-(hydroxypropyl) piperazine and/or N,N'-(dihydroxypropyl) piperazine can conjointly be converted to C-methyl-triethylenediamine and allyl piperazine with excellent conjoint yield and selectivity when using a catalyst composed of titania to which from about 0.5 to about 7 wt. % of phosphorus has been thermally chemically bonded in the form of phosphate linkages.Type: GrantFiled: June 9, 1986Date of Patent: June 28, 1988Assignee: Texaco Inc.Inventors: Steven H. Vanderpool, Thomas T. McConnell
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Patent number: 4742168Abstract: The use of certain oxyalkyl amines as anti-caking agents for triethylenediamine (TEDA) is disclosed. The anti-caking agent comprises polyoxypropylene amines or their amides, the amines having the formula: ##STR1## wherein X is hydrogen, a methyl radical or an ethyl radical, Z is a hydrocarbon radical having from 2 to 5 carbon atoms forming from 2 to 4 external ether linkages; n is a number from 1 to about 40 and r is a number from 2 to 4.Type: GrantFiled: July 31, 1986Date of Patent: May 3, 1988Assignee: Texaco Inc.Inventor: Robert L. Zimmerman
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Patent number: 4725681Abstract: An ethanolamine, preferably diethanolamine, is converted to triethylenediamine or 1,4-bis(2-hydroxyethyl)piperazine, or both by pyrolysis using a B-subgroup metal oxide such as titanium dioxide or zirconium dioxide, as catalyst. In addition it has also been discovered that 1,4-bis(2-hydroxyethyl)piperazine and N-(2-hydroxyethyl)piperazine can be converted in high yields and conversions into triethylenediamine by pyrolysis using the same type of catalyst. When using an ethanolamine as the feedstock and a Group IV-B metal oxide as the catalyst, the process usually results in the coproduction of triethylenediamine and 1,4-bis(2-hydroxyethyl)piperazine, and the latter can be recovered and used as a raw material for the production of additional triethylenediamine, as by recycle to the same reactor or as feedstock to an additional pyrolysis reactor.Type: GrantFiled: August 19, 1985Date of Patent: February 16, 1988Assignee: Ethyl CorporationInventors: Ronald L. Shubkin, Duane C. Hargis
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Patent number: 4625030Abstract: The present invention concerns a potentiated nickel catalyst and its use for the catalytic amination of lower aliphatic alkane derivatives.Type: GrantFiled: May 23, 1984Date of Patent: November 25, 1986Assignee: Union Carbide CorporationInventor: Donald C. Best
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Patent number: 4621036Abstract: Certain solid organic depolarizers are disclosed for use in non-aqueous active metal cells which allow such cells to achieve both high voltage and high capacity with greater enhanced stability. The depolarizers include halogen adducts of triethylenediamine, also known as 1,4 diazabicyclo [2.2.2] octane such as N,N'-tetrachloro triethylenediamine.Type: GrantFiled: September 6, 1985Date of Patent: November 4, 1986Assignee: Honeywell Inc.Inventor: Narayan Doddapaneni
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Patent number: 4605762Abstract: A process for the neutral hydrolytic depolymerization of condensation polymers is described. The process is conducted in a continuous manner and comprises introducing condensation polymer waste material into an aqueous hydrolysis zone at a temperature of between 200.degree. C. and 300.degree. C. and superatmospheric pressure of at least 15 atmospheres. High pressure steam is introduced into the lower portion of the hydrolysis zone underneath the level of the condensation polymer waste material. The steam serves as the principal source of heat for the hydrolysis zone. By being introduced underneath the level of the condensation polymer waste material, the steam agitates the waste material to provide heat transfer to accelerate the hydrolysis reaction. Further, a portion of the steam condenses to provide water which is a reactant in the hydrolysis reaction. An aqueous solution of the product(s) of the hydrolysis reaction is withdrawn from an upper portion of the hydrolysis zone.Type: GrantFiled: December 21, 1983Date of Patent: August 12, 1986Assignee: Celanese Mexicana S.A.Inventor: Jorge W. Mandoki
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Patent number: 4582904Abstract: Synthesis of organic amines by condensation of organic hydroxy compound with ammonia or a primary or secondary amine in the presence of a rare earth metal hydrogen phosphate catalyst.Type: GrantFiled: January 6, 1984Date of Patent: April 15, 1986Assignee: Air Products and Chemicals, Inc.Inventors: James E. Wells, Victoria Eskinazi
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Patent number: 4521600Abstract: Certain hydrogen phosphate and pyrophosphate compositions are employed as catalysts for organic condensation reactions. Particularly high conversions and selectivities are obtained by the use of synergistic mixtures of in cyclization reactions such as in the conversion of hydroxyethylpiperazine to triethylenediamine and morpholine to dimethylaminoethylmorpholine.Type: GrantFiled: May 24, 1982Date of Patent: June 4, 1985Assignee: Air Products and Chemicals, Inc.Inventors: James E. Wells, Victoria Eskinazi
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Patent number: 4514567Abstract: Strontium pyro-, monohydrogen, and dihydrogen phosphates are employed as catalysts for acid catalyzed organic condensation reactions. High conversion and exceptionally high selectivity are obtained by use of such catalysts in cyclization reactions such as in the conversion of hydroxyethylpiperazine to triethylenediamine.Type: GrantFiled: April 22, 1983Date of Patent: April 30, 1985Assignee: Air Products and Chemicals, Inc.Inventor: James E. Wells
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Patent number: 4405784Abstract: Strontium diorthophosphate is employed as catalyst for acid catalyzed organic condensation reactions. High conversion and exceptionally high selectivity are obtained by use of strontium diorthophosphate in cyclization reactions such as in the conversion of hydroxyethylpiperazine to triethylenediamine.Type: GrantFiled: June 29, 1981Date of Patent: September 20, 1983Assignee: Air Products and Chemicals, Inc.Inventor: James E. Wells
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Patent number: 4289881Abstract: A process for the preparation of 1,4-diazobicyclo-(2,2,2)-octane by contacting piperazine with a catalyst at an elevated temperature, the catalyst containing silicon dioxide.Type: GrantFiled: October 15, 1979Date of Patent: September 15, 1981Assignee: Bayer AktiengesellschaftInventors: Laszlo Imre, Walter Horstmann, Hans-Gerhard Leopold
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Patent number: 4233447Abstract: A process is provided for recovering substantially pure triethylenediamine in liquid lower alkylene diol solutions directly from the crude triethylenediamine reaction mixture without resort to a need to purify the triethylenediamine by crystallization. The process includes initially admixing a lower alkylene diol with a crude triethylenediamine liquid reaction product mixture. The admixture thus formed is then heated to remove water and other low boiling impurities. The crude triethylene diaminediol bottoms mixture is then codistilled to recover a pure triethylene diamine product in diol solvent which can be used directly to catalyze urethane systems.Type: GrantFiled: December 21, 1978Date of Patent: November 11, 1980Assignee: Texaco Development Corp.Inventors: Edward C. Y. Nieh, Kenneth P. Keating
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Patent number: 4216322Abstract: There is disclosed a novel process for the preparation of 1,4-diazabicyclooctane dihydrohalides having the formula ##STR1## wherein each R is independently selected from the group consisting of hydrogen, lower alkyl, aryl, aralkyl, and cycloalkyl, and X is chlorine or bromine, said process comprising heating at a temperature of at least about 100.degree. C. and in a dipolar aprotic solvent certain novel dihaloalkylene diamines. Neutralization of the dihydrohalides provides the corresponding 1,4-diazabicyclooctane free bases.Also disclosed are certain novel 1,4-diazabicyclooctane diammonium dihalides formed as intermediates in the above process and a process for their conversion to the 1,4-diazabicyclooctane dihydrohalides and free bases thereof.The 1,4-diazabicyclo compounds produced in accordance with the invention find particular utility as catalysts in the preparation of polyurethanes from organic polyols and polyisocyanates.Type: GrantFiled: October 30, 1978Date of Patent: August 5, 1980Assignee: The Upjohn CompanyInventor: George H. Temme
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Patent number: 4216323Abstract: 1,4-Diazabicyclo-(2,2,2)-octane is separated and recovered by adding water to a crude 1,4-diazabicyclo-(2,2,2)-octane including an alkyl pyrazine and other amines and then, separating 1,4-diazabicyclo-(2,2,2)-octane by a distillation of water and the alkyl pyrazine and a crystallization.Type: GrantFiled: November 7, 1978Date of Patent: August 5, 1980Assignee: Toyo Soda Manufacturing Company, LimitedInventors: Susumi Otsuki, Shizuo Yamada, Yaichro Ono
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Patent number: 4182864Abstract: A process is provided for recovering substantially pure triethylenediamine in liquid tertiary amine solutions directly from the crude triethylenediamine reaction mixture without resort to a need to purify the triethylenediamine by crystallization. The process includes initially admixing a tertiary amine with a crude triethylenediamine liquid reaction product mixture. The admixture thus formed is then distilled under conditions such that the triethylenediamine and tertiary amine codistill as a substantially pure triethylenediamine solute in liquid tertiary amine solution. The collected codistillate being substantially free of reaction by-products can be used directly to catalyze urethane systems.Type: GrantFiled: September 21, 1978Date of Patent: January 8, 1980Assignee: Texaco Development CorporationInventors: Edward C. Y. Nieh, George P. Speranza