Process Of Forming, Purifying, Or Recovering Triethylene Diamine Per Se, Or Salt Thereof Patents (Class 544/352)
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Patent number: 10266541Abstract: Disclosed are a joint production method and device for aziridine, piperazine and triethylenediamine. The method comprises: reaction 1, preparing piperazine and triethylenediamine by taking ethanol amine as a raw material under the existence of a cyclamine catalyst; reaction 2, preparing aziridine by taking the ethanol amine as the raw material under the existence of a catalyst B; and taking heat released in the reaction 1 as a heat source of heat absorption in the reaction 2. The device comprises a reactor 1 for carrying out the reaction 1 and the heat exchange between reaction materials of the reaction 1 and the raw material of the reaction 2 and a reactor 2 for carrying out the reaction 2.Type: GrantFiled: November 17, 2017Date of Patent: April 23, 2019Assignee: XI'AN MODERN CHEMISTRY RESEARCH INSTITUTEInventors: Jianming Yang, Suning Mei, Qinwei Yu, Feng Hui, Jun Yuan, Wei Wang, Yani Li, Weiqiang Wang, Jian Lu
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Patent number: 9926256Abstract: Disclosed herein is a mixed phosphate catalyst for converting lactic acid to acrylic acid, which is characterized by a high conversion of lactic acid, a high selectivity for acrylic acid, a high yield of acrylic acid, and correspondingly low selectivity and molar yields for undesired by-products. This is achieved with a particular class of catalysts defined by a mixture of metal-containing phosphate salts. Further, the catalyst is believed to be stable and active for lengthy periods heretofore unseen in the art for such dehydration processes.Type: GrantFiled: March 15, 2013Date of Patent: March 27, 2018Assignee: The Procter & Gamble CompanyInventors: Janette Villalobos Lingoes, Dimitris Ioannis Collias
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Patent number: 9150759Abstract: A chemical mechanical polishing composition for polishing silicon wafers is provided, containing: water, optionally, an abrasive; a cation according to formula (I); piperazine or a piperazine derivative according to formula (II); and, a quaternary ammonium compound; wherein the chemical mechanical polishing composition exhibits a pH of 9 to 12. Also provided are methods of making and using the chemical mechanical polishing composition.Type: GrantFiled: September 27, 2013Date of Patent: October 6, 2015Assignees: Rohm and Haas Electronic Materials CMP Holdings, Inc, Nitta Haas IncorporatedInventors: Yasuyuki Itai, Naresh Kumar Penta, Naoko Kawai, Hiroyuki Nakano, Shinichi Haba, Yoshiharu Ota, Takayuki Matsushita, Masashi Teramoto, Sakiko Nakashima, Tomoyuki Toda, Koichi Yoshida, Lee Melbourne Cook
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Patent number: 8952156Abstract: A process is disclosed for separating the output from the reaction of EDDN or EDMN with hydrogen in the presence of THF, a catalyst, TETA or DETA, water, and optionally organic compounds having higher and lower boiling points than TETA or DETA. Hydrogen is removed, and the output is supplied to a distillation column DK1 in which an azeotrope, optionally comprising organic compounds with a boiling point lower than TETA or DETA, is removed from the top. A product comprising TETA or DETA is removed from the bottom and passed into a distillation column DK2, removing THF. A stream comprising TETA or DETA passes from the bottom of DK2. The DK1 azeotrope is condensed. Phase separation is induced by the addition of an organic solvent essentially immiscible with water, and the mixture is separated. The organic phase is recycled into DK1 and the water phase is discharged.Type: GrantFiled: August 30, 2012Date of Patent: February 10, 2015Assignee: BASF SEInventors: Hermann Luyken, Sebastian Ahrens, Gordon Brasche, Jens Baldamus, Robert Baumann, Randolf Hugo, Stephanie Jaegli, Johann-Peter Melder, Jörg Pastre, Boris Buschhaus
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Patent number: 8344141Abstract: Zeolite material of the pentasil type has an alkali metal and alkaline earth metal content of not more than 100 ppm and a molar ratio of Si to Al of from 250 to 1500, at least 90% of the primary particles of the zeolite material being spherical and 95% by weight of the spherical primary particles having a diameter of less than or equal to 1 ?m.Type: GrantFiled: February 18, 2011Date of Patent: January 1, 2013Assignee: BASF SEInventors: Marco Bosch, Ulrich Müller, Matthias Frauenkron
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Publication number: 20110144335Abstract: Zeolite material of the pentasil type has an alkali metal and alkaline earth metal content of not more than 100 ppm and a molar ratio of Si to Al of from 250 to 1500, at least 90% of the primary particles of the zeolite material being spherical and 95% by weight of the spherical primary particles having a diameter of less than or equal to 1 ?m.Type: ApplicationFiled: February 18, 2011Publication date: June 16, 2011Applicant: BASF SEInventors: Marco Bosch, Ulrich Müller, Matthias Frauenkron
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Publication number: 20110077376Abstract: To provide a process for producing a hydroxyalkyltriethylenediamine or hydroxytriethylenediamine simply and in a small number of steps without requiring multi-stage reaction steps; a novel catalyst composition whereby a polyurethane product can be obtained with good productivity and good moldability without bringing about odor problems or environmental problems; and a process for producing a polyurethane resin using the catalyst composition. For example, a hydroxyalkyltriethylenediamine or hydroxytriethylenediamine is produced by subjecting a mono-substituted dihydroxyalkylpiperazine and/or a di-substituted hydroxyalkylpiperazine to an intramolecular dehydration condensation reaction in the presence of an acid catalyst.Type: ApplicationFiled: May 29, 2009Publication date: March 31, 2011Inventors: Katsumi Tokumoto, Takao Suzuki, Hiroyuki Kiso, Yoshihiro Takahashi, Yutaka Tamano
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Patent number: 7872131Abstract: Process for preparing a solution of pure triethylenediamine (TEDA), in which TEDA is vaporized, the gaseous TEDA is passed into a liquid solvent 1 (quench) and the TEDA is crystallized from the resulting solution and separated off (solid-liquid separation), wherein the crystalline TEDA obtained is dissolved in a solvent 2 and a stripping gas is passed through the resulting solution (stripping).Type: GrantFiled: May 13, 2005Date of Patent: January 18, 2011Assignee: BASF SEInventors: Ortmund Lang, Matthias Frauenkron
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Publication number: 20100204438Abstract: The present invention relates to a process for preparing triethylenediamine (TEDA) derivatives, comprising the following steps: a) reacting a dihydropyrazine with an olefin, b) if appropriate hydrogenating after step a). The present invention further also relates to novel TEDA derivatives as such and to their use as incorporable polyurethane catalysts.Type: ApplicationFiled: August 29, 2008Publication date: August 12, 2010Applicant: BASF SEInventors: Gunther Van Cauwenberge, Johann-Peter Melder, Joachim-Thierry Anders, Christoph Benisch, Rainer Klopsch, Gregor Daun, Christian Dully, Boris Buschhaus, Henning Böckemeier, Evelyn Pox
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Publication number: 20080312439Abstract: The present invention relates to a process for working up triethylenediamine (TEDA) in which TEDA is vaporized and the gaseous TEDA is introduced into a solvent, subsequently crystallized and separated off from this and the mother liquor formed is extracted with an extractant, wherein the raffinate phase obtained after the extraction stage is worked up further by adsorption in which extractant and/or by-products and intermediates present in the raffinate phase are removed therefrom.Type: ApplicationFiled: December 7, 2006Publication date: December 18, 2008Applicant: BASF AktiengesellschaftInventors: Ortmund Lang, Jurgen Ciprian, Matthias Rauls, Matthias Frauenkron, Gunther van Cauwenberge, Jan Nouwen
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Publication number: 20080221326Abstract: Process for producing a shaped body comprising a microporous material and at least one silicon-containing binder, which comprises the steps (I) preparing a mixture comprising the microporous material, the binder, a make-up aid and a solvent, (II) mixing and densifying the mixture, (III) shaping the densified mixture to give a shaped body, (IV) drying the shaped body and (V) calcining the dried shaped body, wherein the binder used is an organosilicon compound, shaped bodies which can be produced by this process, their use as catalyst, in particular in organic synthesis and very particularly preferably in a process for preparing triethylenediamine (TEDA).Type: ApplicationFiled: June 10, 2005Publication date: September 11, 2008Inventors: Marco Bosch, Matthias Frauenkron, Milan Kostur, Otto Hofstadt
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Patent number: 7345173Abstract: In a process for the purification of triethylenediamine (TEDA) in which TEDA is vaporized and the gaseous TEDA is passed into a liquid solvent and is subsequently crystallized from this, the mother liquor obtained after the TEDA has been crystallized is extracted with an extractant which is immiscible or only slightly miscible with the solvent of the mother liquor and in which TEDA is readily soluble, and the TEDA-depleted mother liquor obtained after extraction and/or the TEDA-enriched extractant which has been used for the extraction are/is returned to the process.Type: GrantFiled: May 6, 2002Date of Patent: March 18, 2008Assignee: BASF SEInventors: Ortmund Lang, Bernd Rumpf, Matthias Frauenkron, Dirk Funhoff, Thomas Manderbach, Bernd Stein
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Patent number: 7151177Abstract: Highly pure triethylenediamine is obtained by a process in which triethylenediamine is freed from high boilers and then the triethylenediamine is vaporized from the mixture thus obtained and is passed into a liquid solvent. The process makes it possible in particular to obtain highly pure solutions of triethylenediamine. Crystallization is generally unnecessary.Type: GrantFiled: September 11, 2002Date of Patent: December 19, 2006Assignee: BASF AktiengesellschaftInventors: Ortmund Lang, Bernd Rumpf, Matthias Frauenkron, Thomas Manderbach, Bernd Stein
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Patent number: 7132538Abstract: Process for purifying triethylenediamine (TEDA) by disillation, in which the fractionation is carried out in a dividing wall column.Type: GrantFiled: April 22, 2004Date of Patent: November 7, 2006Assignee: BASF AktiengesellschaftInventors: Ortmund Lang, Bernd Rumpf, Matthias Frauenkron, Marco Bosch, Helmut Berrsche, Anton Meier
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Patent number: 7115742Abstract: A process for the preparation of triethylenediamine (TEDA) by reaction of ethylenediamine (EDA) in the presence of a zeolite catalyst, wherein the zeolite catalyst contains one or more metals M in oxidation states II, III or IV as oxides. The desired molar ratio of SiO2 to metal oxide of the zeolite catalyst depends on the oxidation state of the metal M as specified herein. The reaction temperature is from 250 to 500° C. TEDA is an important basic chemical and is used, among other things, in the preparation of pharmaceuticals and plastics, in particular as a catalyst in the preparation of polyurethanes.Type: GrantFiled: February 6, 2003Date of Patent: October 3, 2006Assignee: BASF AktiengesellschaftInventors: Matthias Frauenkron, Bernd Stein
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Patent number: 7074926Abstract: The present invention relates to a process for preparing TEDA solutions comprising a solvent selected from the group consisting of polyhydric alcohols and ethers of polyhydric alcohols. The process comprises passing gaseous TEDA into the solvent and subsequently treating the solutions with one or more suitable adsorbents. This gives solutions which have only low color numbers and are color-stable on storage. The solutions can be used as such in preferred applications of TEDA, preferably polyurethane production.Type: GrantFiled: January 29, 2004Date of Patent: July 11, 2006Assignee: BASF AktiengesellschaftInventors: Jürgen Ciprian, Matthias Frauenkron, Stephan Maurer, Johann-Peter Melder
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Patent number: 6958397Abstract: The present invention describes a process for the preparation of triethylenediamine by reacting piperazine over a zeolite catalyst which, in addition to SiO2, contains an oxide of at least one further divalent, trivalent or tetravalent metal M, wherein the zeolite has a molar Si/M ratio of >100. In particular, a zeolite of the ZSM-5 type is used. The use of the zeolites permits suppression of the undesired formation of the byproduct 2-ethylpiperazine and hence considerable simplification of the working-up, in combination with high piperazine conversions and a small excess of water.Type: GrantFiled: July 4, 2002Date of Patent: October 25, 2005Assignee: BASF AGInventors: Matthias Frauenkron, Bernd Stein, Ortmund Lang
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Publication number: 20040259734Abstract: The present invention aims at providing an isoxazoline derivative and a pharmaceutically acceptable salt thereof, both having an excellent herbicidal effect and an excellent selectivity between crop and weed.Type: ApplicationFiled: June 12, 2004Publication date: December 23, 2004Inventors: Masao Nakatani, Minoru Ito, Kyoko Kimijima, Masahiro Miyazaki, Makoto Fujinami, Ryohei Ueno, Satoru Takahashi
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Publication number: 20040254188Abstract: Compounds of formula (I) 1Type: ApplicationFiled: June 12, 2003Publication date: December 16, 2004Inventors: Arthur Gomtsyan, Erol K. Bayburt, John R. Koenig, Chih-Hung Lee
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Publication number: 20040236106Abstract: The present invention describes a process for the preparation of triethylenediamine by reacting piperazine over a zeolite catalyst which, in addition to SiO2, contains an oxide of at least one further divalent, trivalent or tetravalent metal M, wherein the zeolite has a molar Si/M ratio of >100. In particular, a zeolite of the ZSM-5 type is used. The use of the zeolites permits suppression of the undesired formation of the byproduct 2-ethylpiperazine and hence considerable simplification of the working-up, in combination with high piperazine conversions and a small excess of water.Type: ApplicationFiled: January 5, 2004Publication date: November 25, 2004Inventors: Matthias Frauenkron, Bernd Stein, Ortmund Lang
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Publication number: 20040220405Abstract: Highly pure triethylenediamine is obtained by a process in which triethylenediamine is freed from high boilers and then the triethylenediamine is vaporized from the mixture thus obtained and is passed into a liquid solvent. The process makes it possible in particular to obtain highly pure solutions of triethylenediamine. Crystallization is generally unnecessary.Type: ApplicationFiled: March 9, 2004Publication date: November 4, 2004Inventors: Ortmund Lang, Bernd Rumpf, Matthias Frauenkron, Thomas Manderbach, Bernd Stein
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Publication number: 20040220406Abstract: Process for purifying triethylenediamine (TEDA) by disillation, in which the fractionation is carried out in a dividing wall column.Type: ApplicationFiled: April 22, 2004Publication date: November 4, 2004Inventors: Ortmund Lang, Bernd Rumpf, Matthias Frauenkron, Marco Bosch, Helmut Berrsche, Anton Meier
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Patent number: 6627756Abstract: Pure triethylenediamine (TEDA) is prepared by vaporizing TEDA, introducing the gaseous TEDA into a liquid solvent and subsequently crystallizing the TEDA from the solution obtained in this way.Type: GrantFiled: July 11, 2000Date of Patent: September 30, 2003Assignee: BASF AktiengesellschaftInventors: Hartmut Riechers, Arthur Höhn, Joachim Simon, Ortmund Lang, Hartmut Schoenmakers, Matthias Rauls, Koen Claerbout
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Publication number: 20030139598Abstract: A process for the preparation of triethylenediamine (TEDA) by reaction of ethylenediamine (EDA) in the presence of a zeolite catalyst, whereinType: ApplicationFiled: February 6, 2003Publication date: July 24, 2003Inventors: Matthias Frauenkron, Bernd Stein
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Patent number: 6562971Abstract: A process for the preparation of triethylenediamine (TEDA) by reaction of ethylenediamine (EDA) in the presence of a zeolite catalyst, wherein the zeolite catalyst comprises one or more metals M in oxidation states II, III or IV as oxides, and for M=Al, has an SiO2/M2O3 molar ratio of greater than 1400:1, for M=metal in oxidation state II or M=two or more metals in oxidation state II, has an SiO2/MO molar ratio of greater than 100:1, for M=metal in oxidation state III or M=two or more metals in oxidation state III, has an SiO2/M2O3 molar ratio of greater than 100:1 and for M=metal in oxidation state IV or M=two or more metals in oxidation state IV, has an SiO2/MO2 molar ratio of greater than 10:1, and the reaction temperature is from 250 to 500° C.Type: GrantFiled: June 26, 2001Date of Patent: May 13, 2003Assignee: BASF AktiengesellschaftInventors: Matthias Frauenkron, Bernd Stein
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Patent number: 6555688Abstract: The invention in question is concerned with a method for the production of triethylene diamine using ethylene diamine as an educt and zeolite catalysts of the Pentasil type.Type: GrantFiled: July 5, 2000Date of Patent: April 29, 2003Assignee: BASF AktiengesellschaftInventors: Werner Klockemann, Erich Frauendorfer, Matthias Frauenkron, Bernd Stein
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Patent number: 6552194Abstract: The invention relates to the preparation of pure triethylenediamine (TEDA) by evaporating TEDA from the mixture comprising a solvent or diluent, where the solvent or diluent has a boiling point at atmospheric pressure in the range from 175 to 250° C., passing the vapor-form TEDA into a liquid solvent, and subsequently crystallizing the TEDA out of the resultant solution.Type: GrantFiled: January 3, 2002Date of Patent: April 22, 2003Assignee: BASF AktiengesellschaftInventors: Ortmund Lang, Bernd Rumpf, Matthias Frauenkron, Dirk Funhoff, Thomas Manderbach, Bernd Stein
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Patent number: 6531601Abstract: A molded catalyst for production of triethylenediamine, wherein (1) the main components are silica and crystalline aluminosilicate, (2) the silica is amorphous, and the content of the silica is from 5 to 70 wt %, (3) the molar ratio of silica to alumina in the crystalline aluminosilicate is at least 12, and the content of the crystalline aluminosilicate is from 30 to 95 wt %, and (4) the hardness is at least 1 kg.Type: GrantFiled: September 25, 2001Date of Patent: March 11, 2003Assignee: Tosoh CorporationInventor: Tsukasa Ogawa
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Publication number: 20020156278Abstract: The invention relates to the preparation of pure triethylenediamine (TEDA) by evaporating TEDA from the mixture comprising a solvent or diluent, where the solvent or diluent has a boiling point at atmospheric pressure in the range from 175 to 250° C., passing the vapor-form TEDA into a liquid solvent, and subsequently crystallizing the TEDA out of the resultant solution.Type: ApplicationFiled: January 3, 2002Publication date: October 24, 2002Inventors: Ortmund Lang, Bernd Rumpf, Matthias Frauenkron, Dirk Funhoff, Thomas Manderbach, Bernd Stein
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Publication number: 20020107394Abstract: A process for the preparation of triethylenediamine (TEDA) by reaction of ethylenediamine (EDA) in the presence of a zeolite catalyst, whereinType: ApplicationFiled: June 26, 2001Publication date: August 8, 2002Inventors: Matthias Frauenkron, Bernd Stein
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Patent number: 6350874Abstract: A method for producing triethylenediamines and piperazines, which comprises contacting an amine compound having a group of the formula (1): wherein each of R1 to R4 which are independent of one another, is a hydrogen atom or a C1-3 alkyl group which may have a substituent, with a catalyst consisting of a crystalline aluminosilicate calcinated at a temperature of from 500 to 950° C. and then contacted with an inorganic acid, and having a molar ratio of silica to alumina of at least 12.Type: GrantFiled: March 28, 2000Date of Patent: February 26, 2002Assignee: Tosoh CorporationInventor: Tsukasa Ogawa
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Patent number: 6316621Abstract: A new method of making phosphate-based catalysts by mixing phosphoric acid with a substantially water insoluble alkaline earth metal salt such that the phosphorus to alkaline earth metal molar ratio is less than 1. The product, containing alkaline earth metal hydrogen phosphate and the starting alkaline earth metal salt, is filtered and dried. The product can be used as a catalyst in the production of triethylenediamine from, for example, mono- and di-substituted piperazines, such as hydroxyethylpiperazine and aminoethylpiperazine, ethanolamines and substituted ethanolamines, and crude hydroxyethylpiperazine containing piperazine, hydroxyethylpiperazine, bis-hydroxyethylpiperazine, and water.Type: GrantFiled: March 23, 2000Date of Patent: November 13, 2001Assignee: Air Products and Chemicals, Inc.Inventors: Hong-Xin Li, Lenore Ann Emig, Richard Paul Underwood
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Patent number: 6084096Abstract: A process for preparing triethylenediamine and piperazine by passing an ethanolamine, ethyleneamine, piperazine or morpholine over a pentasil-type zeolite at elevated temperature characterized by employing a ZSM-5 zeolite in the hydrogen or ammonium form which has been treated with a passivating agent which is a silicon-containing compound capable of deactivating the acidic sites on the zeolite surface.Type: GrantFiled: April 9, 1998Date of Patent: July 4, 2000Assignee: Air Products and Chemicals, Inc.Inventors: Hong-Xin Li, Jose Guadalupe Santiesteban, Lenore Ann Emig, John Nelson Armor
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Patent number: 6057321Abstract: The invention concerns compounds of general formula (I) ##STR1## in which R.sub.1 represents a methyl group, X.sub.1 represents a hydrogen atom, or OR.sub.1 and X.sub.1 together form a group of formula --O(CH.sub.2).sub.2 --,--O(CH.sub.2).sub.3 --, --O(CH.sub.2).sub.2 O-- or --O(CH.sub.2).sub.3 O--, X.sub.2 represents a hydrogen atom or an amino group, and X.sub.3 representing a halogen atom. The compounds are ligands of serotoninergic receptors of the 5-HT.sub.3 and/or 5-HT.sub.4 types, and act as 5-HT.sub.4 agonists and/or 5-HT.sub.3 antogonists.Type: GrantFiled: June 4, 1999Date of Patent: May 2, 2000Assignee: Sanofi-SynthelaboInventors: Alistair Lochead, Samir Jegham, Alain Nedelec, Axelle Solignac
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Patent number: 5792876Abstract: A process is described for producing acetals comprising reacting an aldehyde or a ketone with an alcohol in the presence of a titanium compound having an acetylacetone as a ligand, or in the presence of a compound selected from the group consisting of stannous chloride dihydrate, cerium chloride hexahydrate and bismuth chloride. The process can be used in the synthesis of unstable acetals or when water exists in the reaction mixture, and therefore the process can be used for a wide variety of applications.Type: GrantFiled: November 6, 1996Date of Patent: August 11, 1998Assignee: Kuraray Co., Ltd.Inventors: Hideharu Iwasaki, Masahiko Kitayama, Takashi Onishi
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Patent number: 5756741Abstract: A process for preparing triethylenediamine by passing an amine compound over a catalyst at elevated temperature to afford a reaction product containing triethylenediamine and piperazine, the amine compound having, in the molecule, a moiety represented by the following general formula ##STR1## where 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 oxygen or nitrogen characterized by adding an ethylating compound containing at least one nitrogen and/or oxygen atom to the reaction product and contacting the reaction product, under conditions sufficient to produce triethylenediamine from the ethylating compound and piperazine, with a condensation/cyclization shape-selective zeolite catalyst demonstrating a triethylenediamine/piperazine weight ratio uptake value of at least 6:1.Type: GrantFiled: November 15, 1996Date of Patent: May 26, 1998Assignee: Air Products and Chemicals, Inc.Inventors: John Nelson Armor, Jose Guadalupe Santiesteban, Hong-Xin Li
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Patent number: 5741906Abstract: A process for preparing triethylenediamine by passing an ethanolamine, ethyleneamine, piperazine or morpholine over a pentasil-type zeolite at elevated temperature characterized by employing a ZSM-5 zeolite in the hydrogen or ammonium form which has been pretreated with an aqueous solution of a chelating agent capable of forming a chelate-aluminum complex.Type: GrantFiled: November 15, 1996Date of Patent: April 21, 1998Assignee: Air Products and Chemicals, Inc.Inventors: Jose Guadalupe Santiesteban, Hong-Xin Li, John Nelson Armor
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Patent number: 5731449Abstract: A process for preparing triethylenediamine by passing an ethanolamine, ethyleneamine, piperaziHe or morpholine over a pentasil-type zeolite at elevated temperature characterized by employing a ZSM-5 zeolite in the hydrogen or ammonium form which has been pretreated with an aqueous caustic solution.Type: GrantFiled: September 23, 1996Date of Patent: March 24, 1998Assignee: Air Products and Chemicals, Inc.Inventors: Hong-Xin Li, Jose Guadalupe Santiesteban, John Nelson Armor
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Patent number: 5631372Abstract: A process for producing 1-substituted-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts having the formula ##STR1## wherein the Z substituent is OH, OR, OC(O)R, SO.sub.3, SO.sub.2 R, NO.sub.2, NO, or PO(OR).sub.2, wherein R is an aryl or C.sub.1 -C.sub.8 alkyl group; n is 0, 1 or 2; each of R.sub.1, R.sub.2, R.sub.3, P.sub.4 and R.sub.5 independently represent hydrogen, C.sub.1 to C.sub.8 alkyl, or aryl 1-substituted-1,4-diazoniabicyclo[2.2.2]octane or 1,4-diazoniabicyclo[2.2.2]octane mono-N-oxide is reacted to attach the Z group and then the result is reacted with molecular fluorine in the presence of a solvent that substantially does not react with fluorine and a fluoride scavenger that results in an X counter ion. These compounds are useful as fluorinating agents for the introduction of fluorine into organic compounds.Type: GrantFiled: May 6, 1996Date of Patent: May 20, 1997Assignee: AlliedSignal Inc.Inventors: Andrew J. Poss, George A. Shia, Dennis M. Lavery
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Patent number: 5606084Abstract: The present invention relates to the preparation and uses of 1-substituted-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts, specifically 1-hydroxyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane salts as reagents for the introduction of fluorine in organic compounds.Type: GrantFiled: June 7, 1995Date of Patent: February 25, 1997Assignee: AlliedSignal Inc.Inventors: Andrew J. Poss, George Shia
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1,2-ethanediol derivative and salt thereof and cerebral function-improving agent comprising the same
Patent number: 5472984Abstract: This invention relates to a 1,2-ethanediol derivative and a salt thereof, a process for producing the same, and a cerebral function-improving agent comprising the same. The cerebral function-improving agent of this invention is useful for treating cerebrovascular dementia, senile dementia, Alzheimer's dementia, sequelae of ischemic encephalopathy and cerebral apoplexy.Type: GrantFiled: December 29, 1993Date of Patent: December 5, 1995Assignee: Toyama Chemical Co., Ltd.Inventors: Satoshi Ono, Tetsuo Yamafuji, Hisaaki Chaki, Mutsuko Maekawa, Yozo Todo, Hirokazu Narita -
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: 5280120Abstract: A process for preparing bridged nitrogen-containing compounds which comprises contacting a carboxylated cyclic nitrogen-containing compound with a mixed metal oxide catalyst under conditions effective to produce the bridged nitrogen-containing compound.Type: GrantFiled: December 2, 1992Date of Patent: January 18, 1994Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Stephen W. King
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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: 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: 5194613Abstract: A process for preparing bridged nitrogen-containing compounds which comprises contacting a carboxylated cyclic nitrogen-containing compound with a mixed metal oxide catalyst under conditions effective to produce the bridged nitrogen-containing compound.Type: GrantFiled: September 20, 1990Date of Patent: March 16, 1993Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Stephen W. King
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Patent number: 5164497Abstract: A decarboxylation process which comprises contacting a carboxylated compound with a metal oxide catalyst under conditions effective to decarboxylate the carboxylated compound.Type: GrantFiled: September 20, 1990Date of Patent: November 17, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventors: Stephen W. King, Kurt D. Olson, Bernard C. Ream
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Patent number: 5162531Abstract: A process for preparing bridged nitrogen-containing compounds which comprises contacting a cyclic nitrogen-containing compound reactant with a mixed metal oxide catalyst under conditions effective to produce the bridged nitrogen-containing compound.Type: GrantFiled: September 20, 1990Date of Patent: November 10, 1992Assignee: Union Carbide Chemicals & Plastics Technology CorporationInventor: Stephen W. King
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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: 5041548Abstract: Triethylene diamines are prepared in a high yield with an amine compound having a specific group as the starting material by bringing the same into contact with a catalyst formed of a crystalline metal silicate of which the molar ratio (SiO.sub.2 /M.sub.2 O.sub.3) of silicon dioxide (SiO.sub.2) to the oxide of a tervalent metal (M.sub.2 O.sub.3, M being the tervalent metal) is at least 12. Particularly high efficiency can be obtained by using a crystalline metal silicate crystallized in the presence of an organic crystallizing agent.Type: GrantFiled: June 17, 1987Date of Patent: August 20, 1991Assignee: Idemitsu Kosan Company LimitedInventors: Haruhito Sato, Masanori Tsuzuki