Process Of Forming, Purifying, Or Recovering Triethylene Diamine Per Se, Or Salt Thereof Patents (Class 544/352)
  • Patent number: 10266541
    Abstract: 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: Grant
    Filed: November 17, 2017
    Date of Patent: April 23, 2019
    Assignee: XI'AN MODERN CHEMISTRY RESEARCH INSTITUTE
    Inventors: Jianming Yang, Suning Mei, Qinwei Yu, Feng Hui, Jun Yuan, Wei Wang, Yani Li, Weiqiang Wang, Jian Lu
  • Patent number: 9926256
    Abstract: 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: Grant
    Filed: March 15, 2013
    Date of Patent: March 27, 2018
    Assignee: The Procter & Gamble Company
    Inventors: Janette Villalobos Lingoes, Dimitris Ioannis Collias
  • Patent number: 9150759
    Abstract: 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: Grant
    Filed: September 27, 2013
    Date of Patent: October 6, 2015
    Assignees: Rohm and Haas Electronic Materials CMP Holdings, Inc, Nitta Haas Incorporated
    Inventors: 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
  • Patent number: 8952156
    Abstract: 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: Grant
    Filed: August 30, 2012
    Date of Patent: February 10, 2015
    Assignee: BASF SE
    Inventors: Hermann Luyken, Sebastian Ahrens, Gordon Brasche, Jens Baldamus, Robert Baumann, Randolf Hugo, Stephanie Jaegli, Johann-Peter Melder, Jörg Pastre, Boris Buschhaus
  • Patent number: 8344141
    Abstract: 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: Grant
    Filed: February 18, 2011
    Date of Patent: January 1, 2013
    Assignee: BASF SE
    Inventors: Marco Bosch, Ulrich Müller, Matthias Frauenkron
  • Publication number: 20110144335
    Abstract: 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: Application
    Filed: February 18, 2011
    Publication date: June 16, 2011
    Applicant: BASF SE
    Inventors: Marco Bosch, Ulrich Müller, Matthias Frauenkron
  • Publication number: 20110077376
    Abstract: 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: Application
    Filed: May 29, 2009
    Publication date: March 31, 2011
    Inventors: Katsumi Tokumoto, Takao Suzuki, Hiroyuki Kiso, Yoshihiro Takahashi, Yutaka Tamano
  • Patent number: 7872131
    Abstract: 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: Grant
    Filed: May 13, 2005
    Date of Patent: January 18, 2011
    Assignee: BASF SE
    Inventors: Ortmund Lang, Matthias Frauenkron
  • Publication number: 20100204438
    Abstract: 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: Application
    Filed: August 29, 2008
    Publication date: August 12, 2010
    Applicant: BASF SE
    Inventors: Gunther Van Cauwenberge, Johann-Peter Melder, Joachim-Thierry Anders, Christoph Benisch, Rainer Klopsch, Gregor Daun, Christian Dully, Boris Buschhaus, Henning Böckemeier, Evelyn Pox
  • Publication number: 20080312439
    Abstract: 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: Application
    Filed: December 7, 2006
    Publication date: December 18, 2008
    Applicant: BASF Aktiengesellschaft
    Inventors: Ortmund Lang, Jurgen Ciprian, Matthias Rauls, Matthias Frauenkron, Gunther van Cauwenberge, Jan Nouwen
  • Publication number: 20080221326
    Abstract: 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: Application
    Filed: June 10, 2005
    Publication date: September 11, 2008
    Inventors: Marco Bosch, Matthias Frauenkron, Milan Kostur, Otto Hofstadt
  • Patent number: 7345173
    Abstract: 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: Grant
    Filed: May 6, 2002
    Date of Patent: March 18, 2008
    Assignee: BASF SE
    Inventors: Ortmund Lang, Bernd Rumpf, Matthias Frauenkron, Dirk Funhoff, Thomas Manderbach, Bernd Stein
  • Patent number: 7151177
    Abstract: 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: Grant
    Filed: September 11, 2002
    Date of Patent: December 19, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Ortmund Lang, Bernd Rumpf, Matthias Frauenkron, Thomas Manderbach, Bernd Stein
  • Patent number: 7132538
    Abstract: Process for purifying triethylenediamine (TEDA) by disillation, in which the fractionation is carried out in a dividing wall column.
    Type: Grant
    Filed: April 22, 2004
    Date of Patent: November 7, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Ortmund Lang, Bernd Rumpf, Matthias Frauenkron, Marco Bosch, Helmut Berrsche, Anton Meier
  • Patent number: 7115742
    Abstract: 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: Grant
    Filed: February 6, 2003
    Date of Patent: October 3, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Frauenkron, Bernd Stein
  • Patent number: 7074926
    Abstract: 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: Grant
    Filed: January 29, 2004
    Date of Patent: July 11, 2006
    Assignee: BASF Aktiengesellschaft
    Inventors: Jürgen Ciprian, Matthias Frauenkron, Stephan Maurer, Johann-Peter Melder
  • Patent number: 6958397
    Abstract: 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: Grant
    Filed: July 4, 2002
    Date of Patent: October 25, 2005
    Assignee: BASF AG
    Inventors: Matthias Frauenkron, Bernd Stein, Ortmund Lang
  • Publication number: 20040259734
    Abstract: 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: Application
    Filed: June 12, 2004
    Publication date: December 23, 2004
    Inventors: Masao Nakatani, Minoru Ito, Kyoko Kimijima, Masahiro Miyazaki, Makoto Fujinami, Ryohei Ueno, Satoru Takahashi
  • Publication number: 20040254188
    Abstract: Compounds of formula (I) 1
    Type: Application
    Filed: June 12, 2003
    Publication date: December 16, 2004
    Inventors: Arthur Gomtsyan, Erol K. Bayburt, John R. Koenig, Chih-Hung Lee
  • Publication number: 20040236106
    Abstract: 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: Application
    Filed: January 5, 2004
    Publication date: November 25, 2004
    Inventors: Matthias Frauenkron, Bernd Stein, Ortmund Lang
  • Publication number: 20040220405
    Abstract: 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: Application
    Filed: March 9, 2004
    Publication date: November 4, 2004
    Inventors: Ortmund Lang, Bernd Rumpf, Matthias Frauenkron, Thomas Manderbach, Bernd Stein
  • Publication number: 20040220406
    Abstract: Process for purifying triethylenediamine (TEDA) by disillation, in which the fractionation is carried out in a dividing wall column.
    Type: Application
    Filed: April 22, 2004
    Publication date: November 4, 2004
    Inventors: Ortmund Lang, Bernd Rumpf, Matthias Frauenkron, Marco Bosch, Helmut Berrsche, Anton Meier
  • Patent number: 6627756
    Abstract: 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: Grant
    Filed: July 11, 2000
    Date of Patent: September 30, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Hartmut Riechers, Arthur Höhn, Joachim Simon, Ortmund Lang, Hartmut Schoenmakers, Matthias Rauls, Koen Claerbout
  • Publication number: 20030139598
    Abstract: A process for the preparation of triethylenediamine (TEDA) by reaction of ethylenediamine (EDA) in the presence of a zeolite catalyst, wherein
    Type: Application
    Filed: February 6, 2003
    Publication date: July 24, 2003
    Inventors: Matthias Frauenkron, Bernd Stein
  • Patent number: 6562971
    Abstract: 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: Grant
    Filed: June 26, 2001
    Date of Patent: May 13, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Matthias Frauenkron, Bernd Stein
  • Patent number: 6555688
    Abstract: 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: Grant
    Filed: July 5, 2000
    Date of Patent: April 29, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Werner Klockemann, Erich Frauendorfer, Matthias Frauenkron, Bernd Stein
  • Patent number: 6552194
    Abstract: 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: Grant
    Filed: January 3, 2002
    Date of Patent: April 22, 2003
    Assignee: BASF Aktiengesellschaft
    Inventors: Ortmund Lang, Bernd Rumpf, Matthias Frauenkron, Dirk Funhoff, Thomas Manderbach, Bernd Stein
  • Patent number: 6531601
    Abstract: 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: Grant
    Filed: September 25, 2001
    Date of Patent: March 11, 2003
    Assignee: Tosoh Corporation
    Inventor: Tsukasa Ogawa
  • Publication number: 20020156278
    Abstract: 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: Application
    Filed: January 3, 2002
    Publication date: October 24, 2002
    Inventors: Ortmund Lang, Bernd Rumpf, Matthias Frauenkron, Dirk Funhoff, Thomas Manderbach, Bernd Stein
  • Publication number: 20020107394
    Abstract: A process for the preparation of triethylenediamine (TEDA) by reaction of ethylenediamine (EDA) in the presence of a zeolite catalyst, wherein
    Type: Application
    Filed: June 26, 2001
    Publication date: August 8, 2002
    Inventors: Matthias Frauenkron, Bernd Stein
  • Patent number: 6350874
    Abstract: 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: Grant
    Filed: March 28, 2000
    Date of Patent: February 26, 2002
    Assignee: Tosoh Corporation
    Inventor: Tsukasa Ogawa
  • Patent number: 6316621
    Abstract: 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: Grant
    Filed: March 23, 2000
    Date of Patent: November 13, 2001
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Hong-Xin Li, Lenore Ann Emig, Richard Paul Underwood
  • Patent number: 6084096
    Abstract: 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: Grant
    Filed: April 9, 1998
    Date of Patent: July 4, 2000
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Hong-Xin Li, Jose Guadalupe Santiesteban, Lenore Ann Emig, John Nelson Armor
  • Patent number: 6057321
    Abstract: 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: Grant
    Filed: June 4, 1999
    Date of Patent: May 2, 2000
    Assignee: Sanofi-Synthelabo
    Inventors: Alistair Lochead, Samir Jegham, Alain Nedelec, Axelle Solignac
  • Patent number: 5792876
    Abstract: 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: Grant
    Filed: November 6, 1996
    Date of Patent: August 11, 1998
    Assignee: Kuraray Co., Ltd.
    Inventors: Hideharu Iwasaki, Masahiko Kitayama, Takashi Onishi
  • Patent number: 5756741
    Abstract: 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: Grant
    Filed: November 15, 1996
    Date of Patent: May 26, 1998
    Assignee: Air Products and Chemicals, Inc.
    Inventors: John Nelson Armor, Jose Guadalupe Santiesteban, Hong-Xin Li
  • Patent number: 5741906
    Abstract: 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: Grant
    Filed: November 15, 1996
    Date of Patent: April 21, 1998
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Jose Guadalupe Santiesteban, Hong-Xin Li, John Nelson Armor
  • Patent number: 5731449
    Abstract: 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: Grant
    Filed: September 23, 1996
    Date of Patent: March 24, 1998
    Assignee: Air Products and Chemicals, Inc.
    Inventors: Hong-Xin Li, Jose Guadalupe Santiesteban, John Nelson Armor
  • Patent number: 5631372
    Abstract: 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: Grant
    Filed: May 6, 1996
    Date of Patent: May 20, 1997
    Assignee: AlliedSignal Inc.
    Inventors: Andrew J. Poss, George A. Shia, Dennis M. Lavery
  • Patent number: 5606084
    Abstract: 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: Grant
    Filed: June 7, 1995
    Date of Patent: February 25, 1997
    Assignee: AlliedSignal Inc.
    Inventors: Andrew J. Poss, George Shia
  • Patent number: 5472984
    Abstract: 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: Grant
    Filed: December 29, 1993
    Date of Patent: December 5, 1995
    Assignee: Toyama Chemical Co., Ltd.
    Inventors: Satoshi Ono, Tetsuo Yamafuji, Hisaaki Chaki, Mutsuko Maekawa, Yozo Todo, Hirokazu Narita
  • Patent number: 5288909
    Abstract: 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: Grant
    Filed: August 19, 1992
    Date of Patent: February 22, 1994
    Assignee: The Dow Chemical Company
    Inventors: George E. Hartwell, Robert G. Bowman, David C. Molzahn
  • Patent number: 5280120
    Abstract: 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: Grant
    Filed: December 2, 1992
    Date of Patent: January 18, 1994
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Stephen W. King
  • Patent number: 5210307
    Abstract: 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: Grant
    Filed: January 31, 1992
    Date of Patent: May 11, 1993
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
  • Patent number: 5210306
    Abstract: 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: Grant
    Filed: August 8, 1989
    Date of Patent: May 11, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Arthur R. Doumaux, Jr., David J. Schreck, Stephen W. King, George A. Skoler
  • Patent number: 5194613
    Abstract: 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: Grant
    Filed: September 20, 1990
    Date of Patent: March 16, 1993
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Stephen W. King
  • Patent number: 5164497
    Abstract: A decarboxylation process which comprises contacting a carboxylated compound with a metal oxide catalyst under conditions effective to decarboxylate the carboxylated compound.
    Type: Grant
    Filed: September 20, 1990
    Date of Patent: November 17, 1992
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventors: Stephen W. King, Kurt D. Olson, Bernard C. Ream
  • Patent number: 5162531
    Abstract: 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: Grant
    Filed: September 20, 1990
    Date of Patent: November 10, 1992
    Assignee: Union Carbide Chemicals & Plastics Technology Corporation
    Inventor: Stephen W. King
  • Patent number: 5118850
    Abstract: 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: Grant
    Filed: November 9, 1990
    Date of Patent: June 2, 1992
    Assignee: The Dow Chemical Company
    Inventors: Robert G. Bowman, David C. Molzahn, George E. Hartwell
  • Patent number: 5041548
    Abstract: 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: Grant
    Filed: June 17, 1987
    Date of Patent: August 20, 1991
    Assignee: Idemitsu Kosan Company Limited
    Inventors: Haruhito Sato, Masanori Tsuzuki