Processes Patents (Class 564/298)
  • Patent number: 10385260
    Abstract: An aqueous fracturing fluid comprises an environmentally friendly flowback aid. The flowback aid includes an amine oxide having the formula (CH3)NO(R1)(R2), where R1 and R2 are independently selected from linear or branched alkyl groups having from 8 to 16 carbon atoms. Optionally, the fracturing fluid may further comprise an alcohol ethoxylate of the formula R3—(OC2H4)x—OH, wherein R3 is a linear or branched alkyl group having from 6 to 18 carbon atoms, and wherein x ranges from 3 to 25. One example of an amine oxide is didecylmethyl amine oxide, and one example of an alcohol ethoxylate is ethoxylated isodecylalcohol (also known as ethoxylated isodecanol). The fracturing fluid is introduced through a well bore into the subterranean formation and pressurized to fracture the subterranean formation. The fracturing fluid is then allowed to flow back into the well bore from the subterranean formation.
    Type: Grant
    Filed: January 11, 2013
    Date of Patent: August 20, 2019
    Assignee: Ecolab USA Inc.
    Inventors: Youseffi Y. Crick, Greg D. Sutton
  • Patent number: 9085515
    Abstract: A continuous process for making amine oxide surfactant comprising the steps of (a) providing the following components; a tertiary amine composition and an aqueous hydrogen peroxide composition, (b) mixing the components from step a) in a mixing device, (c) passing the mixture exiting the mixing device from step b) into an aqueous amine oxide composition comprising from 65 to 80 wt % amine oxide, (d) adjusting the temperature of the amine oxide composition made in step c) to between 40 and 80° C., (e) collecting the amine oxide surfactant; and wherein, for every 1 part of the component mixture from step b) being passed into the aqueous stream in step c), between 8 and 30 parts of the temperature adjusted amine oxide composition from step d) are recycled back to step b) and passed through the mixing device together with the components from step a).
    Type: Grant
    Filed: July 24, 2013
    Date of Patent: July 21, 2015
    Assignee: The Procter & Gamble Company
    Inventors: Linda Pellens, Christopher Stephen Jones, Rasim Tanbug, Walter Agnes Louis Nuyts, Diederik Emiel Omer Vanhoutte, Joey Jay Schriner
  • Patent number: 8722881
    Abstract: A tetradendate amide based macrocyclic ligand and its Fe(III) complex which act as activators of hydrogen peroxide. The synthetic methodology to develop the ligands is new, simple and provides better yield for each step of the ligand synthesis. The Fe(III)-complexes and hydrogen peroxide together are can perform several environmentally benign oxidation reactions. Organic dye bleaching, bleaching of pulp and paper effluent and N-oxide synthesis may be performed using the newly developed catalyst and hydrogen peroxide. Alcohol oxidation and alkene epoxidation may also be performed using the catalysts and hydrogen peroxide.
    Type: Grant
    Filed: October 13, 2010
    Date of Patent: May 13, 2014
    Assignee: Board of Trustees of the University of Arkansas
    Inventors: Anindya Ghosh, Shane Z. Sullivan, Samuel L. Collom, Sharon Pulla
  • Publication number: 20140031591
    Abstract: A continuous process for making amine oxide surfactant comprising the steps of (a) providing the following components; a tertiary amine composition and an aqueous hydrogen peroxide composition, (b) mixing the components from step a) in a mixing device, (c) passing the mixture exiting the mixing device from step b) into an aqueous amine oxide composition comprising from 65 to 80 wt % amine oxide, (d) adjusting the temperature of the amine oxide composition made in step c) to between 40 and 80° C., (e) collecting the amine oxide surfactant; and wherein, for every 1 part of the component mixture from step b) being passed into the aqueous stream in step c), between 8 and 30 parts of the temperature adjusted amine oxide composition from step d) are recycled back to step b) and passed through the mixing device together with the components from step a).
    Type: Application
    Filed: July 24, 2013
    Publication date: January 30, 2014
    Applicant: The Procter & Gamble Company
    Inventors: Linda PELLENS, Christopher Stephen JONES, Rasim TANBUG, Walter Agnes Louis NUYTS, Diederik Emiel Omer VANHOUTTE, Joey Jay SCHRINER
  • Patent number: 8299304
    Abstract: This invention provides alignment materials for liquid crystal display device of vertical alignment mode and methods for the preparation of the same, and more particularly, it provides diaminobenzene derivatives represented by the following formula 1 (shown in description), capable of aligning liquid crystal in uniform and vertical way and remarkably improving clarity and solubility against organic solvents, methods for the preparation of the same and liquid crystal alignment films using the same.
    Type: Grant
    Filed: February 9, 2007
    Date of Patent: October 30, 2012
    Assignee: Dongjin Semichem Co., Ltd.
    Inventors: Jin wook Choi, Dal bong Seo, Jae cheol Park, Yong bae Kim
  • Patent number: 8278488
    Abstract: The present invention relates to a process for producing a tertiary amine in the presence of a catalyst containing copper and at least one element selected from the group consisting of elements belonging to Groups 2, 3, 7 and 12 of the Periodic Table (long form of the periodic table), said process including the steps of (a) reducing an amide compound in a hydrogen atmosphere; and (b) introducing a dialkyl amine containing a linear or branched alkyl group having 1 to 6 carbon atoms into a reaction product obtained in the step (a), and treating the reaction product with the dialkyl amine. The present invention provides a process for producing high-purity aliphatic tertiary amines containing a less amount of by-products by reducing aliphatic acid amides under moderate conditions using a chromium-free catalyst, as well as a process for producing amine derivatives such as amine oxide by using the aliphatic tertiary amines, with a good productivity in an economical manner.
    Type: Grant
    Filed: August 7, 2008
    Date of Patent: October 2, 2012
    Assignee: Kao Corporation
    Inventors: Michio Terasaka, Tetsuaki Fukushima, Hideki Taniguchi, Masaharu Jono
  • Publication number: 20110257436
    Abstract: Process for the manufacture of solid Mn+(HDO)n salts wherein HDO is the anion of N?-hydroxy-N-cyclohexyldiazenium oxide, and Mn+ is a metal cation by precipitation with an acid from an alkaline solution of an HDO-salt with monovalent cations in the presence of amines and drying under mild conditions.
    Type: Application
    Filed: December 10, 2009
    Publication date: October 20, 2011
    Applicant: BASF SE
    Inventors: Darren Michael Hodgkinson, James Bullock, Mohammed Shoaib Qureshi
  • Publication number: 20110207964
    Abstract: The present invention relates to a process for producing a tertiary amine in the presence of a catalyst containing copper and at least one element selected from the group consisting of elements belonging to Groups 2, 3, 7 and 12 of the Periodic Table (long form of the periodic table), said process including the steps of (a) reducing an amide compound in a hydrogen atmosphere; and (b) introducing a dialkyl amine containing a linear or branched alkyl group having 1 to 6 carbon atoms into a reaction product obtained in the step (a), and treating the reaction product with the dialkyl amine. The present invention provides a process for producing high-purity aliphatic tertiary amines containing a less amount of by-products by reducing aliphatic acid amides under moderate conditions using a chromium-free catalyst, as well as a process for producing amine derivatives such as amine oxide by using the aliphatic tertiary amines, with a good productivity in an economical manner.
    Type: Application
    Filed: August 7, 2008
    Publication date: August 25, 2011
    Applicant: KAO CORPORATION
    Inventors: Michio Terasaka, Tetsuaki Fukushima, Hideki Taniguchi, Masaharu Jono
  • Patent number: 7935846
    Abstract: The present invention provides a process for producing high-purity aliphatic tertiary amines containing a less amount of by-products by using a chromium-free catalyst with a good productivity in an economically advantageous manner. The present invention relates to a process for producing a tertiary amine by reducing an amide compound in the presence of a catalyst containing copper and magnesium at a molar ratio of magnesium to copper (magnesium/copper) of from 0.01 to 20.
    Type: Grant
    Filed: October 17, 2007
    Date of Patent: May 3, 2011
    Assignee: Kao Corporation
    Inventors: Tetsuaki Fukushima, Hideki Taniguchi, Michio Terasaka
  • Publication number: 20110094043
    Abstract: A tetradendate amide based macrocyclic ligand and its Fe(III) complex which act as activators of hydrogen peroxide. The synthetic methodology to develop the ligands is new, simple and provides better yield for each step of the ligand synthesis. The Fe(III)-complexes and hydrogen peroxide together are can perform several environmentally benign oxidation reactions. Organic dye bleaching, bleaching of pulp and paper effluent and N-oxide synthesis may be performed using the newly developed catalyst and hydrogen peroxide. Alcohol oxidation and alkene epoxidation may also be performed using the catalysts and hydrogen peroxide.
    Type: Application
    Filed: October 13, 2010
    Publication date: April 28, 2011
    Inventors: Anindya Ghosh, Shane Z. Sullivan, Samuel L. Collom, Sharon Pulla
  • Patent number: 7754923
    Abstract: The present invention provides a process for producing high-purity aliphatic tertiary amines containing a less amount of by-products by subjecting aliphatic acid amides to hydrogenation reduction under moderate conditions, as well as a process for producing amine derivatives from the aliphatic tertiary amines, with a good productivity in an economically advantageous manner. The present invention relates to a process for producing an aliphatic tertiary amine by subjecting a specific aliphatic amide to hydrogenation reduction in the presence of a catalyst containing copper and at least one element selected from the group consisting of elements belonging to Groups 2, 3 and 7 of the Periodic Table; the catalyst; and a process for producing amine oxide by reacting the tertiary amide obtained by the above production process with hydrogen peroxide.
    Type: Grant
    Filed: March 8, 2007
    Date of Patent: July 13, 2010
    Assignee: KAO Corporation
    Inventors: Masaharu Jono, Michio Terasaka, Hideki Taniguchi, Tetusaki Fukushima
  • Patent number: 7696383
    Abstract: Embodiments of the invention relate to a compound of formula (1), or a tautomer, stereoisomer, hydrate, or solvate thereof, wherein R1 is H or CH3. Other embodiments of the invention relate to a pharmaceutical composition containing these compound, to methods for preparing these compounds, and to methods for preparing compositions containing these compounds. Yet other embodiments of the invention relate to the uses of these compounds and compositions containing it, such as for the manufacture of medicaments and pharmaceutical compositions for treating a condition chosen from depression, major depressive disorder, generalized anxiety disorder, obsessive compulsive disorder, social anxiety disorder, panic disorder, general depressive disorders, diabetic neuropathy, migraine and hot flashes.
    Type: Grant
    Filed: June 23, 2008
    Date of Patent: April 13, 2010
    Assignee: Solvay Pharmaceuticals B.V.
    Inventors: Lechoslaw A. Turski, Axel Stoit, Cornelis G. Kruse, Sander Vader, Martinus Th. M. Tulp
  • Publication number: 20090275763
    Abstract: A catalyst for the manufacture of alkylene oxide, for example ethylene oxide, by the vapor-phase epoxidation of alkene containing impregnated silver and at least one efficiency-enhancing promoter on an inert, refractory solid support, said support incorporating a sufficient amount of zirconium component (present and remaining substantially as zirconium silicate) as to enhance at least one of catalyst activity, efficiency and stability as compared to a similar catalyst which does not contain the zirconium component.
    Type: Application
    Filed: June 2, 2009
    Publication date: November 5, 2009
    Inventors: Juliana G. Serafin, Albert C. Liu, Seyed R. Seyedmonir, Hwaili Soo, Thomas Szymanski
  • Publication number: 20090054688
    Abstract: The present invention provides a process for producing high-purity aliphatic tertiary amines containing a less amount of by-products by subjecting aliphatic acid amides to hydrogenation reduction under moderate conditions, as well as a process for producing amine derivatives from the aliphatic tertiary amines, with a good productivity in an economically advantageous manner. The present invention relates to a process for producing an aliphatic tertiary amine by subjecting a specific aliphatic amide to hydrogenation reduction in the presence of a catalyst containing copper and at least one element selected from the group consisting of elements belonging to Groups 2, 3 and 7 of the Periodic Table; the catalyst; and a process for producing amine oxide by reacting the tertiary amide obtained by the above production process with hydrogen peroxide.
    Type: Application
    Filed: March 8, 2007
    Publication date: February 26, 2009
    Applicant: KAO CORPORATION
    Inventors: Masaharu Jono, Michio Terasaka, Hideki Taniguchi, Tetusaki Fukushima
  • Patent number: 7342136
    Abstract: A process for preparing long chain internal fatty tertiary amines, quaternary amines and amine oxides via the selection of long chain internal olefins.
    Type: Grant
    Filed: November 10, 2005
    Date of Patent: March 11, 2008
    Assignee: Procter & Gamble Company
    Inventors: Corey James Kenneally, Jeffrey John Scheibel
  • Patent number: 7129287
    Abstract: A method for preparing exfoliated clay nanocomposites by in-situ polymerization comprising the steps of (a) providing a mixture of at least one type of monomer and at least one type of organophilic clay; and (b) initiating an in-situ polymerization reaction in the mixture so as to cause the at least one type of monomer to polymerize thereby forming the exfoliated clay nanocomposite. The exfoliated clay nanocomposite produces an x-ray diffraction pattern that is substantially devoid of an intercalation peak. The exfoliated clay nanocomposite may then be used as a masterbatch.
    Type: Grant
    Filed: April 29, 2003
    Date of Patent: October 31, 2006
    Assignee: The Ohio State University
    Inventors: L. James Lee, Changchun Zeng
  • Patent number: 7030257
    Abstract: Disclosed herein are novel high oxidation state metallocene compounds, processes for preparing these compounds and uses of these compounds.
    Type: Grant
    Filed: April 13, 2004
    Date of Patent: April 18, 2006
    Assignee: Agency for Science, Technology and Research
    Inventors: Zhiqiang Gao, Fang Xie, Hong Xie
  • Publication number: 20040122225
    Abstract: Nitrone derivatives are efficiently prepared by increasing reagent concentrations in reaction solutions. Aldehydes and amines may be condensed to prepare an imine intermediate. Elimination of the solution media generally renders the imine formation more efficient. The imine is then reacted with a peroxysulfate oxidizing agent in a solution having at least about 0.1M concentration of the imine. The oxaziridine is rearranged to produce the nitrone derivative in high yield and good purity.
    Type: Application
    Filed: December 20, 2002
    Publication date: June 24, 2004
    Applicant: The Goodyear Tire & Rubber Company
    Inventor: Dane Kenton Parker
  • Patent number: 6706923
    Abstract: Perfluoroalkyl-substituted amines, acids, amino acids and thioether acid compounds containing a perfluoroalkyl-iodoalkyl or perfluoroalkyl-alkene group as well as derivatives thereof, are described. They are useful as surfactants in a variety of applications where low surface tensions are required, including coating formulations for glass, wood, metal, cement, paper, textiles, as foam control agents in polyurethane foams and especially in aqueous fire-fighting formulations.
    Type: Grant
    Filed: July 24, 2002
    Date of Patent: March 16, 2004
    Assignee: Ciba Specialty Chemicals Corporation
    Inventors: Marlon Haniff, Ted Deisenroth, John Jennings, Karl Friedrich Mueller
  • Patent number: 6689911
    Abstract: An integrated process for preparing &agr;-(2,4-disulfophenyl)-N-tert-butylnitrone and its salts is disclosed in which N-tert-butylhydroxylamine acid addition salt is incompletely neutralised so as to leave catalytic amounts of acid and the neutralisation product is condensed with an appropriate aldehyde.
    Type: Grant
    Filed: April 5, 2001
    Date of Patent: February 10, 2004
    Assignees: Centaur Pharmaceuticals, Inc., AstraZeneca AB
    Inventors: Henry Kruk, John McGinley, Sergei Pouhov, John Vajda, Allan Wilcox, Jörgen Blixt, Ulf Larsson
  • Patent number: 6579461
    Abstract: The invention relates to a process for the reprocessing respectively purification of aqueous solutions of a tertiary amine oxide, particularly of process waters, e.g. used precipitation baths, which occur during the production of cellulosic moulded bodies, comprising the separation of turbidifying agents and solid impurities from the solution. The process in accordance with the invention is characterised in that the turbidifying agents and impurities are at least partly separated by means of a flotation process.
    Type: Grant
    Filed: March 13, 2001
    Date of Patent: June 17, 2003
    Assignee: Lenzing Aktiengesellschaft
    Inventors: Johann Männer, Rudolf Emeder, Christian Hager, Franz Nussbaumer, Thomas Endl, Johannes Kneissl
  • Publication number: 20030078424
    Abstract: The present invention relates to a process for the oxidation of tertiary amines and nitrogen-containing aromatic heterocycles to amine oxides.
    Type: Application
    Filed: October 25, 2002
    Publication date: April 24, 2003
    Inventors: Hanns Wurziger, Guido Pieper, Norbert Schwesinger
  • Publication number: 20030060656
    Abstract: This invention provides methods and catalyst systems for catalyzing enantioselective oxidation reactions, including cyclization reactions and enantioselective oxidation reactions of secondary alcohols and other similarly reactive organic substrates. Use of the methods and catalyst systems for kinetic resolution of racemic mixtures of secondary alcohols is also described.
    Type: Application
    Filed: March 4, 2002
    Publication date: March 27, 2003
    Inventors: Eric M. Ferreira, Brian M. Stoltz
  • Patent number: 6538141
    Abstract: The invention concerns a method for preparing nitroxides, which consists in oxidising, in a two-phase medium, using an aliphatic peroxide, secondary amines with steric hindrance or having a —CH in the nitrogen atom &agr;.
    Type: Grant
    Filed: September 24, 2001
    Date of Patent: March 25, 2003
    Assignee: Atofina
    Inventors: Jean-Philippe Gillet, Olivier Guerret, Jean-Pierre Lascombe
  • Patent number: 6455735
    Abstract: The present invention provides a process for the preparation of high quality amine oxide by reacting a tertiary or secondary amine with hydrogen peroxide as an oxidant in presence of a recyclable heterogeneous layered double hydroxide exchanged with one of the anions of transition metal oxides as a catalyst in a solvent selected from the group consisting of water, water containing dodecylbenzenesulfonic acid sodium salt as additive, and a water miscible organic solvent.
    Type: Grant
    Filed: September 27, 2001
    Date of Patent: September 24, 2002
    Assignee: Council of Scientific and Industrial Research
    Inventors: Boyapati M. Choudary, Balagam Bharathi, Mannepalli L. Kantam, Chinta R. V. Reddy, Kondapuram V. Raghavan
  • Publication number: 20020095055
    Abstract: The present invention provides a process for the preparation of high quality amine oxide by reacting a tertiary or secondary amine with hydrogen peroxide as an oxidant in presence of a recyclable heterogeneous layered double hydroxide exchanged with one of the anions of transition metal oxides as a catalyst in a solvent selected from the group consisting of water, water containing dodecylbenzenesulfonic acid sodium salt as additive, and a water miscible organic solvent.
    Type: Application
    Filed: September 27, 2001
    Publication date: July 18, 2002
    Inventors: Boyapati M. Choudary, Balagam Bharathi, Mannepalli L. Kantam, Chinta R.V. Reddy, Kondapuram V. Raghavan
  • Publication number: 20020028971
    Abstract: Nitramines are one of the more expensive and often the more plentiful ingredients found in energetic materials, such as solid rocket motor propellants, explosives, and pyrotechnics. By treating aluminized energetic material with an aqueous nitric acid solution containing not more than 55% by weight aqueous nitric acid at a weight ratio of aqueous nitric acid to energetic material of about 4:1 to about 6:1, most constituents of conventional aluminized energetic materials are digested into solution, with the exception of nitramines, which remain substantially insoluble in the aqueous nitric acid and can be recovered without requiring recrystallization of the nitramines. A mineral acid other than nitric acid, preferably hydrchloric acid, is added to increase the rate of aluminum digestion. Treatment of the energetic material can be performed without volatile organic solvents, thus obviating ecological, cost, and safety concerns raised by the use of volatile organic solvents.
    Type: Application
    Filed: February 15, 2001
    Publication date: March 7, 2002
    Applicant: Cordant Technologies Inc.
    Inventors: Kirstin F. Warner, Louis F. Cannizzo, Robert M. Hajik, Harold E. Johnston
  • Patent number: 6323367
    Abstract: A process for the preparation of high quality amine oxides by reacting a tertiary or secondary amine with hydrogen peroxide as an oxidant in the presence of a recyclable heterogeneous layered double hydroxide exchanged with one of the anions of transition metal oxides as a catalyst in an organic solvent at a temperature ranging between 10-25° C. for a period of 1-6 hours under continuous stirring and separating the product by simple filtration and subsequently evaporation of solvents by known methods.
    Type: Grant
    Filed: November 22, 2000
    Date of Patent: November 27, 2001
    Assignee: Council of Scientific and Industrial Research
    Inventors: Boyapati Manoranjan Choudary, Balagam Bharathi, Mannepalli Lakshmi Kantam, Chinta Venkat Reddy Reddy, Kondapuram Vijaya Raghavan
  • Patent number: 6294514
    Abstract: Mono-long chain amine oxide surfactants can be prepared containing active levels of greater than about 30%, by weight of amine, and with low nitrite and nitrosamine levels and low levels of residual hydrogen peroxide when oxidized under controlled temperature conditions in the presence of bicarbonate material present at levels less than about 2.5%, by weight of amine, and without the presence of phase-modifying solvents.
    Type: Grant
    Filed: November 24, 1998
    Date of Patent: September 25, 2001
    Assignee: The Procter & Gamble Company
    Inventor: Stanley James Welling
  • Patent number: 6291702
    Abstract: The present invention relates to chromotropic nitrone spin trapping agents, methods of making these agents, compositions comprising same, and methods of their use. In particular, azulenyl nitrones of the present invention are effective agents for trapping free radical species and find use as efficient antioxidants in physicochemical and biological systems. Accordingly, the invention also relates to spin adducts formed from the combination of azulenyl nitrones with free radicals. The compounds of the present invention are readily prepared from available starting materials and find further use in assays and in a number of diagnostic, prophylactic and therapeutic applications, including but not limited to the alleviation, modulation and inhibition of the negative effects of carbon-centered or oxygen-centered radical species and other products of oxidation. Moreover, the combination adducts may be colorimetrically detected and, optionally, isolated and characterized to obtain valuable information (e.g.
    Type: Grant
    Filed: February 8, 2000
    Date of Patent: September 18, 2001
    Assignee: Florida International University
    Inventor: David Alan Becker
  • Patent number: 6281176
    Abstract: This invention provides a process for producing a betaine/amine oxide mixture. This process comprises reacting, in a liquid medium, an alkali metal &ohgr;-halocarboxylate with a first tertiary amine of the formula Ra2RbN, wherein each Ra group is a hydrocarbyl group which independently has from 1 to about 4 carbon atoms, and wherein the Rb group is a hydrocarbyl group which has from about 8 to about 24 carbon atoms, to produce a betaine product solution. To the betaine product solution is added a second tertiary amine of the formula Ra2RbN, wherein each Ra group is a hydrocarbyl group which independently has from 1 to about 4 carbon atoms, and wherein the Rb group is a hydrocarbyl group which has from about 8 to about 24 carbon atoms, to produce an amine/betaine mixture. The first and second tertiary amines can be separate portions of the same amine. Preferably, however, the first and second tertiary amines differ from each other.
    Type: Grant
    Filed: December 3, 1999
    Date of Patent: August 28, 2001
    Assignee: Albemarle Corporation
    Inventors: Rebecca S. Cochran, Patrick C. Hu, Michael S. McCaig, Edmund F. Perkins, Jr., Joe D. Sauer, Dustin H. Thomas
  • Publication number: 20010000039
    Abstract: Disclosed are novel NO-releasing compounds which comprise a stabilized S-nitrosyl group and a free alcohol or a free thiol group. Also disclosed is a method of preparing the NO-releasing compounds. The method comprises reacting a polythiol or a thioalcohol with a nitrosylating agent. Also disclosed are medical devices coated with the disclosed compounds, methods of delivering NO to treatments sites in a subject by utilizing the medical devices and methods of sterilizing surfaces.
    Type: Application
    Filed: November 29, 2000
    Publication date: March 15, 2001
    Inventors: Eric J. Toone, Jonathan S. Stamler
  • Patent number: 6197825
    Abstract: The present invention relates to chromotropic nitrone spin trapping agents, methods of making these agents, compositions comprising same, and methods of their use. In particular, azulenyl nitrones of the present invention are effective agents for trapping free radical species and find use as efficient antioxidants in physicochemical and biological systems. Accordingly, the invention also relates to spin adducts formed from the combination of azulenyl nitrones with free radicals. The compounds of the present invention are readily prepared from available starting materials and find further use in assays and in a number of diagnostic, prophylactic and therapeutic applications, including but not limited to the alleviation, modulation and inhibition of the negative effects of carbon-centered or oxygen-centered radical species and other products of oxidation. Moreover, the combination adducts may be calorimetrically detected and, optionally, isolated and characterized to obtain valuable information (e.g.
    Type: Grant
    Filed: May 28, 1998
    Date of Patent: March 6, 2001
    Assignee: Florida International University
    Inventor: David Alan Becker
  • Patent number: 6166255
    Abstract: Exothermic oxidation of tertiary amine with aqueous hydrogen peroxide in an aqueous reaction medium formed or being formed from tertiary amine, aqueous hydrogen peroxide, carbon dioxide, and optionally chelating agent and/or additional water, is initiated at about 15 to about 25.degree. C., and while agitating the reaction mixture, the temperature is allowed to rise adiabatically to a temperature in the range of about 50 to about 100.degree. C. In this way, it is possible to produce tertiary amine oxides with very low levels, if any, of nitrosamine impurity, without addition of metal and/or phosphorus-containing components recommended in the prior art. Even though a substantial portion of the reaction is performed at temperatures in the range of about 50-100.degree. C., nitrosamine content, if any, in the resultant tertiary amine oxide product can be well below 30 ppb, and the free amine content, if any, can be well below 0.3 wt %.
    Type: Grant
    Filed: September 11, 1998
    Date of Patent: December 26, 2000
    Assignee: Albemarle Corporation
    Inventors: Rebecca S. Cochran, Andrea P. Wight, Douglas H. Krzystowczyk, Dustin H. Thomas
  • Patent number: 6121490
    Abstract: A process for producing tertiary amine oxide having two methyl or ethyl groups and one long chain primary aliphatic group in a stable, solid form is described. Aqueous 65-90% hydrogen peroxide and tertiary amine having two methyl or ethyl groups and one primary aliphatic hydrocarbyl group of 8-24 carbon atoms are mixed in proportions of ca. 1.1-1.3 moles of hydrogen peroxide per mole of tertiary amine in the presence of carbon dioxide and in the absence of organic solvent. When the conversion of the tertiary amine to tertiary amine oxide in the reaction mass has reached ca. 60-90%, the reaction mass is transferred to a separate vessel and the reaction mass is then allowed to solidify at a temperature of ca. 20-60.degree. C. The process makes possible the production of highly pure solid product without formation of any appreciable amounts of undesirable by-products.
    Type: Grant
    Filed: April 14, 1999
    Date of Patent: September 19, 2000
    Assignee: Albemarle Corporation
    Inventor: Hassan Y. Elnagar
  • Patent number: 6080889
    Abstract: Exothermic oxidation of tertiary amine with aqueous hydrogen peroxide in an aqueous reaction medium formed or being formed from tertiary amine, aqueous hydrogen peroxide, carbon dioxide, and optionally chelating agent and/or additional water, is initiated at about 15 to about 25.degree. C., and while agitating the reaction mixture, the temperature is allowed to rise adiabatically to a temperature in the range of about 50 to about 100.degree. C. In this way, it is possible to produce tertiary amine oxides with very low levels, if any, of nitrosamine impurity, without addition of metal and/or phosphorus-containing components recommended in the prior art. Even though a substantial portion of the reaction is performed at temperatures in the range of about 50-100.degree. C., nitrosamine content, if any, in the resultant tertiary amine oxide product can be well below 30 ppb.
    Type: Grant
    Filed: April 1, 1998
    Date of Patent: June 27, 2000
    Assignee: Albemarle Corporation
    Inventors: Rebecca S. Cochran, Andrea P. Wight, Douglas H. Krzystowczyk, Dustin H. Thomas
  • Patent number: 6054616
    Abstract: The claimed process consists in treating the tertiary amine oxide with a sulphite or a bleach activator.
    Type: Grant
    Filed: March 26, 1999
    Date of Patent: April 25, 2000
    Assignee: Clariant Finance (BVI) Limited
    Inventors: Cheryl Ann Littau, Graham Cox, Michael Neil Holland
  • Patent number: 6037497
    Abstract: A process is described in which tertiary amine is oxidized with hydrogen peroxide in the presence of carbon dioxide until the reaction mass contains (i) about 0.5 to about 6.5%, and preferably about 1 to about 2.5%, of unreacted free amine, (ii) carbon dioxide, and (iii) unreacted hydrogen peroxide. At this point individual portions of the reaction mass are dispensed into a plurality of shipping containers, or alternatively, the reaction mass is transferred to a cooling vessel, cooled therein, and then dispensed into a plurality of shipping containers. Thereafter the reaction is allowed to slowly continue to completion at ambient temperature in the shipping containers with venting of off-gases, as required. The process makes it possible to produce amine oxides with increased plant throughput without need for additional plant reaction equipment such as glass-lined reactors, and the consequent substantial additional capital investment.
    Type: Grant
    Filed: September 29, 1998
    Date of Patent: March 14, 2000
    Assignee: Albemarle Corporation
    Inventors: Dustin H. Thomas, Douglas H. Krzystowczyk, Luc G. Six
  • Patent number: 5955633
    Abstract: A process is provided for the manufacture of free-flowing solid tertiary amine oxides having N-nitrosodimethylamine levels of less than about 250 ppb. The process comprises heating a mixture of a tertiary amine, a polar hydroxy alkyl solvent, an organic acid, and aqueous hydrogen peroxide, followed by removal of the solvent and water, preferably by azeotropic removal. The resultant tertiary amine oxides have good color without bleaching and are useful without further purification.
    Type: Grant
    Filed: August 20, 1998
    Date of Patent: September 21, 1999
    Assignee: General Electric Company
    Inventor: Vaikunth S. Prabhu
  • Patent number: 5892117
    Abstract: Oxidation of secondary amines with hydrogen peroxide and sodium tungstate is reported to give good yields of nitrones. However, when using dimethylamine in this manner, a considerable amount of N,N-dimethylformamide was produced as a co-product. To more selectively produce N-methylnitrone from dimethylamine, a two-step process is used which comprises (a) mixing together dimethylamine and a peroxidic compound, and subjecting the resultant mixture to reaction conditions effective to form a reaction mixture in which N,N-dimethylhydroxylamine has been formed; and (b) mixing together (i) reaction mixture from (a), (ii) a peroxidic compound, and (iii) a transition metal-containing oxidation catalyst, and subjecting the resultant mixture to reaction conditions effective to form a reaction mixture in which N-methylnitrone has been formed. Highest yields of N-methylnitrone are achieved by conducting step (b) at a pH in the range of 7 to about 12, and at a temperature in the range of about -10.degree. to about 100.
    Type: Grant
    Filed: June 12, 1997
    Date of Patent: April 6, 1999
    Assignee: Albemarle Corporation
    Inventor: Kevin J. Theriot
  • Patent number: 5866718
    Abstract: A process is provided for the manufacture of free-flowing solid tertiary amine oxides having N-nitrosodimethylamine levels of less than about 250 ppb. The process comprises heating a mixture of a tertiary amine, a polar hydroxy alkyl solvent, an organic acid, and aqueous hydrogen peroxide, followed by removal of the solvent and water, preferably by azeotropic removal. The resultant tertiary amine oxides have good color without bleaching and are useful without further purification.
    Type: Grant
    Filed: March 20, 1997
    Date of Patent: February 2, 1999
    Assignee: General Electric Company
    Inventor: Vaikunth S. Prabhu
  • Patent number: 5773655
    Abstract: The invention is concerned with a process for the purification of an aqueous solution of a tertiary amine-oxide containing impurities partially present in a dissolved and partially in a non-dissolved, colloidal state, and is characterized by a combination of the steps of(A) removing from the aqueous solution substantially all of said impurities present in a non-dissolved, colloidal state and(B) contacting said aqueous solution obtained in step (A) with an ion exchanger.
    Type: Grant
    Filed: April 15, 1997
    Date of Patent: June 30, 1998
    Assignee: Lenzing Aktiengesellschaft
    Inventors: Eduard Mulleder, Bruno Mangeng, Franz Schwenninger, Johann Manner
  • Patent number: 5710333
    Abstract: Process for the preparation of tertiary amine oxides by reaction of a tertiary amine with a compound which splits off oxygen. To avoid gel and foam formation, a portion of the amine oxide to be prepared is added before the start of this reaction.
    Type: Grant
    Filed: August 6, 1996
    Date of Patent: January 20, 1998
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Georg Bader, Ramon Joglar Tamargo
  • Patent number: 5710332
    Abstract: A method for the manufacture of N,N dialkylglycamine compounds of general formula R.sub.2 NR.sub.1 R.sub.3 (I) by reacting a secondary amine of general formula R.sub.2 NHR.sub.3 (II) in which R.sub.2 is a straight or branched chain alkyl or hydroxyalkyl group having from 1 to 4 carbon atoms and R.sub.3 is a residue from a monosaccharide, with an alkali metal or alkaline earth metal aliphatic sulphate, R.sub.1 SO.sub.4 M, in which R.sub.1 is a straight or branched chain alkyl or alkenyl group having from 8 to 24 carbon atoms.The betaine, suphobetaine and N-oxidised derivatives of (I) are provided for use as mild surfactants.
    Type: Grant
    Filed: July 12, 1996
    Date of Patent: January 20, 1998
    Assignee: Albright & Wilson Limited
    Inventors: Brynley Morris Phillips, Ajit Kumar, Alan Smithson
  • Patent number: 5693861
    Abstract: A highly pure, white, solid amine oxide is prepared in high yield with minimal decomposition of the solvent by (A) reacting a tert-amine with a 15-20% stoichiometric excess of concentrated hydrogen peroxide at 50.degree.-55.degree. C. in the presence of controlled amounts of carbon dioxide and ethyl acetate until the reaction mixture contains 35-45 % by weight of ethyl acetate and less than 0.8% by weight of unreacted amine, (B) catalytically decomposing residual hydrogen peroxide, (C) separating the reaction mixture from the decomposition catalyst, (D) cooling the reaction mixture to 0.degree. C. to form a slurry, (E) centrifuging the slurry to separate the amine oxide, and (F) vacuum drying the amine oxide at ambient temperature--the reaction mixture being diluted to an amine oxide content of 25-30% by weight with additional ethyl acetate or a mixture thereof with a co-solvent, such as a low-boiling n-alkane, after the completion of Step A and prior to the beginning of Step D.
    Type: Grant
    Filed: June 21, 1993
    Date of Patent: December 2, 1997
    Assignee: Albemarle Corporation
    Inventors: Rebecca F. Smith, Y.-D. Mark Chen, R. Woodrow Wilson, Jr., Mayur P. Shah, Kim R. Smith, Sharon B. McGee
  • Patent number: 5668281
    Abstract: A process for preparing a tertiary amine-N-oxide which comprises reacting a tertiary amine with a peroxide in the presence of a catalyst comprising an oxide containing silicon and titanium atoms. According to the process of the present invention, a tertiary amine-N-oxide can be obtained in a high yield, and since the catalyst can easily be separated from the reaction mixture, the tertiary amine-N-oxide can be obtained in a high purity without the contamination by the catalyst.
    Type: Grant
    Filed: January 19, 1996
    Date of Patent: September 16, 1997
    Assignee: Koei Chemical Co., Ltd.
    Inventors: Shinkichi Shimizu, Nanao Watanabe, Hideki Kuranishi
  • Patent number: 5639880
    Abstract: A process for preparing amine oxides of the general formula I ##STR1## where R.sup.1, R.sup.2 and R.sup.3 are each C.sub.1 -C.sub.30 -alkyl, C.sub.3 -C.sub.12 -cycloalkyl, C.sub.1 -C.sub.30 -hydroxyalkyl, C.sub.1 -C.sub.30 -aminoalkyl, C.sub.2 -C.sub.30 -alkoxyalkyl, aryl, C.sub.7 -C.sub.20 -aralkyl, C.sub.7 -C.sub.20 -alkylaryl, C.sub.1 -C.sub.8 -alkyl-, C.sub.1 -C.sub.8 -alkoxy- or halogen-monosubstituted, -disubstituted, -trisubstituted, -tetrasubstituted or -pentasubstituted C.sub.3 -C.sub.12 -cycloalkyl, aryl, C.sub.7 -C.sub.20 -aralkyl, C.sub.7 -C.sub.20 -alkylaryl, --[(CH.sub.2).sub.2 --O].sub.n --R.sup.4, --{[CH(CH.sub.3)CH.sub.2 ]--O}.sub.m --R.sup.5, or R.sup.1 and R.sup.2 are together an uninterrupted or oxygen-, nitrogen- or sulfur-interrupted C.sub.3 -C.sub.12 -alkylene diradical chainR.sup.4 and R.sup.5 are each C.sub.1 -C.sub.12 -alkyl, C.sub.3 -C.sub.12 -cycloalkyl, hydroxyl, --COR.sup.6 or --CH.sub.2 --COOR.sup.7, C.sub.3 -C.sub.12 -cycloalkyl, aryl, C.sub.7 -C.sub.20 -aralkyl or C.sub.7 -C.
    Type: Grant
    Filed: May 30, 1996
    Date of Patent: June 17, 1997
    Assignee: BASF Aktiengesellschaft
    Inventors: Ulrich Muller, Klemens Massonne, Karsten Eller, Michael Schulz
  • Patent number: 5628941
    Abstract: The invention is concerned with a process for the production of cellulose moulded bodies. In this process, cellulose is first dissolved in an aqueous solution of a tertiary amine-oxide, in particular N-methylmorpholine-N-oxide (NMMO), to produce a mouldable cellulose solution. Second, the cellulose solution is molded and conducted into an aqueous precipitation bath, wherein the cellulose is precipitated, which produces a moulded body and a spent precipitation bath. Next, the spent precipitation bath is regenerated. This regenerated aqueous amine-oxide solution is re-used to dissolve cellulose, thereby repeating the process. In the above process, the repeated aqueous amine-oxide solution has a pH within certain defined limits.
    Type: Grant
    Filed: June 5, 1995
    Date of Patent: May 13, 1997
    Assignee: Lenzing Aktiengesellschaft
    Inventors: Wolfram Kalt, Heinrich Firgo, Johann Manner, Eduard Mulleder, Bruno Mangeng, Arnold Nigsch, Franz Schwenninger, Christoph Schrempf
  • Patent number: 5621118
    Abstract: A process for oxidizing a substrate susceptible to nucleophilic oxidation by reacting a bicaroate or monopersulfate solution with the substrate is disclosed. In one aspect, the substrate is introduced into the reaction mixture in an inert carrier gas, which can also serve to sweep the product out of the mixture. In a second aspect the oxidation solution is obtained by a two stage neutralization of a Caro's acid solution, the first stage to e.g. 0.5 to 2.0 and the second stage to about 7 to 9. In preferred embodiments, the substrate is introduced into partially neutralized Caro's acid, and the second stage neutralization in the presence of the substrate is most preferably carried out with an alkali salt such as sodium bicarbonate. The process can employ relatively low ratios of substrate: Caro's acid oxidant and homogeneous reaction conditions. The process is particularly useful for preparing dioxiranes from ketones.
    Type: Grant
    Filed: April 14, 1994
    Date of Patent: April 15, 1997
    Assignee: Solvay Interox Limited
    Inventors: Craig W. Jones, William R. Sanderson, John P. Sankey
  • Patent number: 5583258
    Abstract: Mono-long chain amine oxide surfactants can be prepared containing active levels of greater than about 30%, by weight of amine, and with low nitrite and nitrosamine levels when oxidized in the presence of bicarbonate material present at levels less than about 2.5%, by weight of amine, and without the presence of phase-modifying solvents.
    Type: Grant
    Filed: February 15, 1995
    Date of Patent: December 10, 1996
    Assignee: The Procter & Gamble Company
    Inventor: Gene P. Hawkins