Preparing Directly By Oxidizing A Hydroxyl Amine Patents (Class 564/262)
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Patent number: 8877355Abstract: The present invention provides an organic electroluminescent device exhibiting a long life, a high luminance, and a high efficiency. An organic electroluminescent device comprising on a substrate an anode, a hole transport layer, an organic light-emitting layer, and a cathode, wherein the organic light-emitting layer contains an organic compound having a pyridine ring, a pyrazine ring, or a triazine ring as a partial structure and the hole transport layer contains a monoamine compound represented by the following formula (I): wherein R1 to R9 represent a hydrogen atom, an aryl group, or an alkyl group; R1 to R9 may be the same or different from each other; and R1 to R9 may further have an aryl group or an alkyl group as a substituent in the case where R1 to R9 are an aryl group or an alkyl group.Type: GrantFiled: March 15, 2013Date of Patent: November 4, 2014Assignee: Mitsubishi Chemical CorporationInventors: Masayoshi Yabe, Masayo Fugono, Koichiro Iida, Masako Takeuchi, Tomoyuki Ogata
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Patent number: 8278487Abstract: The present disclosure pertains to a process for preparing an oxime in which a carbonyl compound is reacted in the liquid phase with NH3 and H2O2 in the presence of a catalyst to form the corresponding oxime, wherein the catalyst comprises a catalytic component selected from the oxides of metals of group 5 and group 6. The use of a niobia catalyst is particularly preferred. The process according to the disclosure is suitable for the manufacture of numerous oximes, in particular cyclohexanone oxime.Type: GrantFiled: February 4, 2010Date of Patent: October 2, 2012Assignee: DSM IP Assets B.V.Inventor: Nirappurackal Raveendran Shiju
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Patent number: 7785549Abstract: A recycling system for hydroxylamine formation and oximation is proposed. The recycling system includes a hydroxylamine formation zone, an oximation zone, a purification zone, and an adjusting zone having a nitrate absorption tower. An inorganic process solution, used by the recycling system, partially enters the nitrate absorption tower supplementing nitrate, followed by mixing with the residual inorganic process solution, thereby reducing the loss rate of hydroxylamine in the inorganic process solution due to degradation. In addition, the organic impurities with high boiling point in the inorganic process solution can be effectively removed in the purification zone. As a result, the reduced activity or selectivity of the catalyst for hydroxylamine formation, caused by the toxic effects of these organic impurities on the catalyst, can be avoided, and hence, a high concentration of hydroxylamine can be obtained.Type: GrantFiled: September 11, 2007Date of Patent: August 31, 2010Assignee: China Petrochemical Development CorporationInventors: Jih-Dar Hwang, Hsiu-Li Cheng, Shou-Li Luo
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Patent number: 7671236Abstract: Provided is a process of producing cyclohexanone oxime comprising the steps of: pre-mixing an inorganic process solution containing a high concentration of hydroxylamine phosphate with a first stream of cyclohexanone such that the concentration of hydroxylamine phosphate is reduced to 80% or less of its initial concentration; and subjecting hydroxylamine phosphate in the premixed inorganic process solution to an oximation reaction with a second stream of cyclohexanone. According to the process, oximation is performed after the inorganic process solution containing a high concentration of hydroxylamine phosphate has been pre-mixed with the first stream of cyclohexanone to reduce the concentration of hydroxylamine phosphate. As a result, not only that the efficiency of oximation and the yield of cyclohexanone oxime are increased, but also the organic content of the inorganic process solution discharged from the oximation tower is reduced.Type: GrantFiled: November 20, 2007Date of Patent: March 2, 2010Assignee: China Petrochemical Development CorporationInventors: Jih-Dar Hwang, Kai-Hung Haung, Hsiu-Li Cheng, Shou-Li Luo
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Patent number: 7408080Abstract: The present invention discloses a process for the ammoximation of carbonyl compounds, wherein a reaction in a liquid reaction system comprising a carbonyl compound, ammonia and hydrogen peroxide is carried out in the presence of a sillicon-containing catalyst, characterized in that a liquid silicon-containing assistant is added to the reaction system so that the silicon concentration in the system reaches a range of between 0.1 and 10000 ppm. In the process according to the present invention, the deactivation of catalyst due to dissolution of silicon in the catalyst can be reduced, thus lifetime of the catalyst extended and the stable operation time elongated.Type: GrantFiled: May 30, 2003Date of Patent: August 5, 2008Assignees: China Petroleum & Chemical Corporation, Research Institute of Petroleum Processing, SinopecInventors: Wei Wu, Bin Sun, Yongxiang Li, Shibiao Cheng, Enquan Wang, Shuzhong Zhang
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Patent number: 6930204Abstract: Disclosed is a method for producing a cyclic aliphatic oxime, which comprises subjecting a cyclic aliphatic primary amine to oxidation in the liquid phase under superatmospheric pressure in the presence of molecular oxygen and a solid catalyst, wherein the solid catalyst comprises an oxide of at least one metal (a) selected from the group consisting of metals belonging to Groups 5 and 6 of the Periodic Table.Type: GrantFiled: February 26, 2002Date of Patent: August 16, 2005Assignee: Asahi Kasei Kabushiki KaishaInventors: Mitsuji Ono, Hajime Nagahara
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Patent number: 6927308Abstract: An oxime is synthesized by ammoximation of a carbonyl compound. In stage (i) of the process, a carbonyl compound containing 6 to 20 C atoms is reacted with ammonia and hydrogen peroxide in the presence of a) an organic solvent that is a1) at least partly water-soluble, a2) stable under ammoximation conditions, a3) has a boiling point of higher than 100° C. and/or is capable of forming a two-phase azeotrope with water, and b) a titanium-containing heterogeneous catalyst. After the reaction, the catalyst is separated from the reaction mixture. The oxime is crystallized and separated from the reaction mixture. Water is removed from the remaining mother liquor, provided the mother liquor is a two-phase system in which one of the phases is an aqueous phase. Water or a water-containing two-phase azeotrope is distilled off from the mother liquor, while the distillation bottoms and, optionally, the predominantly organic phase of the azeotrope are recycled to stage (i).Type: GrantFiled: December 12, 2003Date of Patent: August 9, 2005Assignee: Degussa AGInventors: Stefan Leininger, Juergen Herwig, Martin Roos, Georg Oenbrink
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Patent number: 6906223Abstract: The present invention relates to a process for preparing trioxime derivatives of the formula I in which the substituents R1 and R2 are identical or different and each is cyano, alkyl, haloalkyl or cycloalkyl, and R3 and R4 are identical or different and each is alkyl, haloalkyl, cycloalkyl, alkylcarbonyl or arylalkyl, by the following reaction steps in water without isolation of the intermediates: A) nitrosation of 1,3-diketones of the formula II ?to give monooximes of the formula III, B) oximation of III with hydroxylamine derivatives of the formula IV H2N—OR3???IV ?in which R3? is hydrogen or a group R3 to give bisoximes of the formula V, C) alkylation of V with alkylating agents or acylation of V with acylating agents to give compounds of the formula VI and D) subsequent oximation of VI with hydroxylamine to give compounds of the formula I.Type: GrantFiled: July 4, 2001Date of Patent: June 14, 2005Assignee: BASF AGInventors: Andreas Kramer, Matthias Kiefer, Michael Henningsen, Wolfgang Siegel, Jochen Schröder
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Publication number: 20040024252Abstract: The instant invention discloses a process for preparation of compounds of the formula (I), wherein the general symbols are as defined in claim 1, which process comprises reacting a compound of formula (II), wherein the general symbols are as defined in claim 1, with a compound of the formula (III), wherein R5 is as defined in slaim 1. The compounds of the formula (II) are new and useful as stabilizers for protecting organic materials, in particular synthetic polymers, reprographic materials or coating materials against oxidative, thermal or light-induced degradation.Type: ApplicationFiled: May 21, 2003Publication date: February 5, 2004Inventors: Dario Lazzari, Mirko Rossi, Giuseppe Veronesi, Nazzareno Ruggeri, Katharina Fritzsche, Adalbert Braig
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Patent number: 6566555Abstract: Oximes are prepared by reacting carbonyl compounds, hydrogen peroxide and ammonia in the presence of a catalyst system comprising a catalyst comprising titanium, silicon and oxygen and a cocatalyst comprising an acidic solid comprising an organic or inorganic support material, where either the support material itself has Lewis-acid or Brönsted acid properties, or Lewis-acid or Brönsted-acid functional groups are applied to the support material.Type: GrantFiled: September 26, 2001Date of Patent: May 20, 2003Assignee: Degussa AGInventors: Georg Friedrich Thiele, Steffen Hasenzahl, Thomas Schiffer
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Patent number: 6433225Abstract: A process is described for the preparation of substantially pure fluvoxamine maleate, an important antidepressant drug of the formula I, for use as an active pharmaceutical ingredient (API), from the corresponding oxime viz 5-methoxy-4′-trifluoromethylvalerophenone oxime of formula II.Type: GrantFiled: October 25, 2000Date of Patent: August 13, 2002Assignee: Sun Pharamaceutical Industries, Ltd.Inventors: Trinadha Rao Chitturi, Rajamannar Thennati, Kanaksinh Jesingbhai Jadav, Hemant Ashvinbhai Shah
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Patent number: 5696407Abstract: In the production of spherulitic nitroguanidine having a high bulk and tap ensity nitroguanidine is dissolved in dipolar, aprotic solvents, e.g. DMF, DMSO, NMP, etc., by heating to above the saturation temperature t.sub.s and the supersaturated solution is cooled with a controlled temperature gradient (.degree.C./min), crystallization being assisted by the addition of particulate, spherulitic material. In order to obtain spherical nitroguanidine with high yield in a continuous process and with mother liquor reuse, during the heating to above the saturation temperature t.sub.s, spherical control particles with a diameter of 5 to 500 .mu.m are regularly added to the solution in a quantity of 0.05 to 5.00 mass %. The particle size is chosen in such a way that, as a function of the solution behaviour of the nitroguanidine used and its concentration, on dropping below the saturation temperature spherical control particles are still present in the indicated quantity in the supersaturated solution.Type: GrantFiled: October 7, 1996Date of Patent: December 9, 1997Assignee: Fraunhofer-Gesellschaft zur Forderung der angewandten Forschung e.V.Inventors: Klaus-Dieter Thiel, Herbert Heinisch
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Patent number: 5502254Abstract: A method for the preparation of a 2-hydroxyarylaldoxime which comprises reacting hydroxylamine with a 2-hydroxyarylaldehyde, said reaction being performed in the presence of a compound of a metal of Group II, Group III, Group IVA or Group VIA of the Periodic Table and/or under such conditions that the 2-hydroxyarylaldehyde is at least partially in the form of a salt and/or complex of a metal of Group II, Group III, Group IVA or Group VIA of the Periodic Table.Type: GrantFiled: March 15, 1995Date of Patent: March 26, 1996Assignee: Zeneca LimitedInventor: Daniel Levin
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Patent number: 5434307Abstract: A process for producing 12-oxododecanoic acid oxime, a novel compound which can be used as a raw material in several industrial processes, is disclosed. The disclosed process relies on a renewable raw material, vernolic (cis-12,13-epoxy-cis-9-octadecenoic) acid. The process utilizes readily available chemical technology which does not involve the use of gaseous hydrocarbon or petrochemical-base feedstock. Hydrogenation of vernolic acid produces 12,13-epoxystearic acid, which can be oxidized with periodic acid to give 12-oxododecanoic acid, which can be reacted with hydroxylamine to yield 12-oxododecanoic acid oxime. A process for reducing the 12-oxododecanoic acid oxime to yield 12-aminododecanoic acid, the monomer for nylon-12, is also disclosed.Type: GrantFiled: May 21, 1993Date of Patent: July 18, 1995Assignee: Howard UniversityInventors: Chukwuma P. Nwaonicha, Folahan O. Ayorinde
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Patent number: 5399761Abstract: A method for the preparation of a 2-hydroxyarylaldoxime which comprises reacting hydroxylamine with a 2-hydroxyarylaldehyde, said reaction being performed in the presence of a compound of a metal of Group II, Group III, Group IVA or Group VIA of the Periodic Table and/or under such conditions that the 2-hydroxyarylaldehyde is at least partially in the form of a salt and/or complex of a metal of Group II, Group III, Group IVA or Group VIA of the Periodic Table.Type: GrantFiled: August 19, 1993Date of Patent: March 21, 1995Assignee: Zeneca LimitedInventor: Daniel Levin
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Patent number: 4497727Abstract: This invention relates to novel polymers of dipropargylamine and derivatives thereof, a process for preparing same and the electrically conductive polymers resulting from doping poly(dipropargylamine) and derivatives thereof.Type: GrantFiled: February 13, 1984Date of Patent: February 5, 1985Assignee: W. R. Grace & Co.Inventors: Yoshiyuki Okamoto, Edward F. Hwang