Preparing Directly By Reacting Carbonyl With Hydroxylamine Or Salt Thereof Patents (Class 564/259)
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Patent number: 12208070Abstract: Described are pharmaceutical compositions in fixed dose combinations containing: a) a dofetilide component; and b) a mexiletine component; wherein the dofetilide component and the mexiletine component are physically separated from each other, along with methods of treating or preventing atrial fibrillation or a symptom associated therewith in a subject in need thereof by administering to the subject such a pharmaceutical composition and methods of preparing such fixed dose combination products.Type: GrantFiled: May 15, 2023Date of Patent: January 28, 2025Assignee: FB-HRS, LLCInventors: Nikhil Khadtare, Aruna Murty, Qun Liu
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Patent number: 11459293Abstract: This invention is directed to, inter alia, compounds, methods, systems, and compositions for the maintenance, enhancement, and expansion of hematopoietic stem cells derived from one or more sources of CD34+ cells. Sources of CD34+ cells include bone marrow, cord blood, mobilized peripheral blood, and non-mobilized peripheral blood. Also provided herein are compounds of Formula I which are useful in maintaining, enhancing, and expanding of hematopoietic stem cells.Type: GrantFiled: October 26, 2018Date of Patent: October 4, 2022Assignee: ImmuneBridge Inc.Inventors: Jesse Cotari, Timothy Webb, Zhan Wang
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Patent number: 9376375Abstract: This invention relates to a process for producing an oxime comprising reacting a ketone and hydroxylamine in the presence of a carboxylic acid and/or its salt in a system consisting of an aqueous phase and a hydrophobic solvent phase.Type: GrantFiled: March 23, 2011Date of Patent: June 28, 2016Assignee: UBE INDUSTRIES, LTD.Inventors: Masahide Okada, Junichi Kugimoto, Kazunori Kurosawa, Joji Funatsu, Katsuyoshi Kudo
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Publication number: 20150011794Abstract: Ketoxime- and amide-functionalized nanomaterials. The nanomaterials including a nanomaterial comprising a carbon nanotube or a carbon nanofiber. At least one ketoxime group coupled to a first location on the nanomaterial, and at least one amide group coupled to a second location on the nanomaterial.Type: ApplicationFiled: July 2, 2013Publication date: January 8, 2015Inventors: Loon-Seng Tan, David Huabin Wang
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Publication number: 20130211036Abstract: A process for oxidizing a composition comprising contacting an alkylbenzene of the general formula (I): where R1 and R2 each independently represents hydrogen or an alkyl group having from 1 to 4 carbon atoms, wherein R1 and R2 may be joined to form a cyclic group having from 4 to 10 carbon atoms, the cyclic group being optionally substituted, and R3 represents hydrogen, one or more alkyl groups having from 1 to 4 carbon atoms or a cyclohexyl group; and (ii) about 0.05 wt % to about 5 wt % of phenol, with oxygen in the presence of a catalyst containing a cyclic imide having the general formula (II): wherein X represents an oxygen atom, a hydroxyl group, or an acyloxy group under conditions effective to convert at least a portion of the alkylbenzene to a hydroperoxide.Type: ApplicationFiled: August 16, 2011Publication date: August 15, 2013Applicant: ExxonMobil Chemical Company - Law TechnologyInventors: Jihad M. Dakka, Edmund J. Mozeleski, Charles Morris Smith, Christopher L. Becker, Stephen Zushma
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Publication number: 20130066112Abstract: The invention relates to multi-amine functional oligomers and multi-oxime functional oligomers in addition to a method for producing the same by means of the co-polymerisation of carbonyl carriers such as olefins or dienes, reaction with hydroxylamine and a subsequent selective catalytic hydrogenation.Type: ApplicationFiled: March 8, 2011Publication date: March 14, 2013Applicant: Bayer Intellectual Property GmbHInventors: Christoph Gürtler, Thomas Ernst Müller, Ewa Gebauer, Henning Vogt, Yevgen Berezhanskyy, Burkhard Köhler, Walter Leitner
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Publication number: 20130035278Abstract: The present invention relates to a process for the production of formyl cyclohexene derivatives which are suitable as odorants as such or as intermediates for the preparation of further odorants.Type: ApplicationFiled: October 8, 2012Publication date: February 7, 2013Applicant: GIVAUDAN SAInventor: Givaudan SA
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Patent number: 8329948Abstract: An improved method for the synthesis of substituted formylamines and substituted amines via an accelerated Leuckart reaction. The Leuckart reaction is accelerated by reacting formamide or N-alkylformamide and formic acid with an aldehyde or a ketone at a preferred molar ratio that accelerates the reaction. The improved method is applicable to various substituted aldehydes and ketones, including substituted benzaldehydes. An accelerated method for the hydrolysis of substituted formylamines into substituted amines using acid or base and a solvent at an elevated temperature. The improved method is useful for the accelerated synthesis of agrochemicals and pharmaceuticals such as vanillylamine, amphetamine and its analogs, and formamide fungicides.Type: GrantFiled: July 30, 2008Date of Patent: December 11, 2012Inventor: Mikhail Bobylev
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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: 8083973Abstract: A compound which undergoes a color change upon irradiation, and which has the general structure: X—C?C—C?C—Y—(CO)n-QZ wherein X is H, alkyl or —Y—(CO)n-QW; each Y is the same or a different divalent alkylene group; Q is O, S or NR; R is H or alkyl; W is H, alkyl or Z; each Z is the same or a different unsaturated alkyl group; and each n is 0 or 1.Type: GrantFiled: January 22, 2009Date of Patent: December 27, 2011Assignee: DataLase Ltd.Inventor: Anthony N Jarvis
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PROCESS FOR PRODUCING ORGANOLITHIUM COMPOUND AND PROCESS FOR PRODUCING SUBSTITUTED AROMATIC COMPOUND
Publication number: 20110224457Abstract: A method for producing an organolithium compound includes the step of reacting an aromatic compound or a halogenated unsaturated aliphatic compound and a lithiating agent in the presence of a coordinating compound containing three or more elements having a coordinating ability in a molecule, at least one thereof being a nitrogen element, or a coordinating compound containing three or more oxygen elements having a coordinating ability in a molecule, at least one of the groups containing the oxygen elements having a coordinating ability being a tertiary alkoxy group, at a temperature of ?40° C. to 40° C.Type: ApplicationFiled: December 25, 2009Publication date: September 15, 2011Inventor: Hiroki Inoue -
Publication number: 20110178199Abstract: Disclosed herein are a reaction method and a production method of an organic compound which are capable of achieving high reaction selectivity according to the purpose and a high production rate of a target substance. The methods include at least two fluids, wherein at least one kind of the fluids is a fluid containing at least one organic compound and at least one kind of the fluids other than the above fluid is a fluid containing at least one reactant in the form of a liquid or solution, and the respective fluids join together in a thin film fluid foamed between processing surfaces arranged to be opposite to each other so as to be able to approach to and separate from each other, at least one of which rotates relative to the other, whereby an organic reaction is performed in the thin film fluid.Type: ApplicationFiled: September 11, 2008Publication date: July 21, 2011Applicant: M. Technique Co., Ltd.Inventor: Masakazu Enomura
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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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Publication number: 20100130784Abstract: Substituted 1,1,1-trifluoro-3-[(benzyl)-(pyrimidin-2-yl)-amino]-propan-2-ol compounds, pharmaceutical compositions containing such compounds and the use of such compounds to elevate certain plasma lipid levels, including high density lipoprotein-cholesterol and to lower certain other plasma lipid levels, such as LDL-cholesterol and triglycerides and accordingly to treat diseases which are exacerbated by low levels of HDL cholesterol and/or high levels of LDL-cholesterol and triglycerides, such as atherosclerosis and cardiovascular diseases in some mammals, including humans.Type: ApplicationFiled: February 13, 2006Publication date: May 27, 2010Inventors: George Chang, Michael Patrick Pence
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Publication number: 20100063323Abstract: The invention relates to a plant for carrying out chemical reactions, having a reactor (1), the reaction space of which contains hydrogen peroxide (H2O2) and titanium silicalite (TS-1). The object of the invention is to improve such a plant such that continuous separation and recycling of the active catalyst to the reaction space is possible with a long filter service life. This is achieved in that the reaction space contains a solid silicon source, in that the plant comprises a water takeoff line (3) which is set up for drawing off water in addition to components which are dissolved and/or dispersed therein from the reaction space, in that the water takeoff line (3) leads to a filter (4) which separates off the components which are dissolved and/or dispersed in the water, and in that the plant has a return line (5) which is set up for recirculating to the reaction space components which are separated off by means of the filter (4).Type: ApplicationFiled: September 9, 2008Publication date: March 11, 2010Applicant: EVONIK DEGUSSA GmbHInventors: Goetz BAUMGARTEN, Martin ROOS, Stephan SCHAEFLEIN, Rolf AUGENSTEIN
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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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Publication number: 20090221854Abstract: Process and equipment for the continuous production of hydroxyl ammonium by reduction of nitrate ions or nitrogen oxides with hydrogen in the presence of a catalyst whereby the hydroxyl ammonium is produced in 2 or more parallel placed hydroxyl ammonium production units which process is optionally part of a process for the production of cyclohexanone oxime in which an inorganic process liquid is cycled from a hydroxyl ammonium synthesis zone (A) to a cyclohexanone oxime synthesis zone (B) and back to the hydroxyl ammonium synthesis zone for example through an extraction zone (C) and a nitric acid production zone (D), in which hydroxyl ammonium synthesis zone hydroxyl ammonium is formed by reduction of nitrate ions or nitrogen oxides with hydrogen in the presence of a catalyst, and in which cyclohexanone oxime synthesis zone hydroxyl ammonium is reacted with cyclohexanone to form cyclohexanone oxime.Type: ApplicationFiled: July 4, 2006Publication date: September 3, 2009Inventors: Hendrik Oevering, Olaf Poorter
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Publication number: 20090143622Abstract: An improved method for the synthesis of substituted formylamines and substituted amines via an accelerated Leuckart reaction. The Leuckart reaction is accelerated by reacting formamide or N-alkylformamide and formic acid with an aldehyde or a ketone at a preferred molar ratio that accelerates the reaction. The improved method is applicable to various substituted aldehydes and ketones, including substituted benzaldehydes. An accelerated method for the hydrolysis of substituted formylamines into substituted amines using acid or base and a solvent at an elevated temperature. The improved method is useful for the accelerated synthesis of agrochemicals and pharmaceuticals such as vanillylamine, amphetamine and its analogs, and formamide fungicides.Type: ApplicationFiled: July 30, 2008Publication date: June 4, 2009Inventor: Mikhail Bobylev
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Patent number: 7423178Abstract: The invention relates to a process for treating an organic solution comprising cyclohexanone oxime, cyclohexanone and an organic solvent, said process comprising distilling the organic solution such as to obtain (i) a first product comprising organic solvent, (ii) a second product comprising cyclohexanone and (iii) a third product comprising cyclohexanone oxime; and feeding the second product to a cyclohexanone oxime synthesis zone in which hydroxylammonium is reacted with cyclohexanone to form cyclohexanone oxime.Type: GrantFiled: January 28, 2004Date of Patent: September 9, 2008Assignee: DSM IP Assets B.V.Inventors: Hendrik Oevering, Arno H Benneker, Johannes A L Brouwers
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Patent number: 7408081Abstract: The invention relates to a process for treating an aqueous medium containing cyclohexanone oxime and cyclohexanone, said process comprising stripping the aqueous medium with steam, wherein said stripping is carried out at a pressure higher than 0.11 MPa. The invention also relates to a process for the preparation of cyclohexanone oxime, which involves stripping at a pressure higher than 0.11 MPa.Type: GrantFiled: December 4, 2001Date of Patent: August 5, 2008Assignee: DSM IP Assets B.V.Inventors: Arno Benneker, Henk Oevering, Johannes A. L. Brouwers
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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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Publication number: 20080167496Abstract: 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: ApplicationFiled: November 20, 2007Publication date: July 10, 2008Applicant: China Petrochemical Development CorporationInventors: Jih-Dar Hwang, Kai-Hung Haung, Hsiu-Li Cheng, Shou-Li Luo
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Publication number: 20080167495Abstract: 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: ApplicationFiled: September 11, 2007Publication date: July 10, 2008Applicant: China Petrochemical Development CorporationInventors: Jih-Dar Hwang, Hsiu-Li Cheng, Shou-Li Luo
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Patent number: 7396959Abstract: A process for preparing N,N-dihydrocarbylhydroxylamines of the general formula (I) where R1, R2, R3 and R4 are selected independently from among hydrogen, aliphatic, cycloaliphatic, heteroaromatic and aromatic radicals, or R1 and R2 and/or R3 and R4 are joined to form a ring, and not more than one radical among R1, R2, R3 and R4 is hydrogen, which comprises the steps a) reaction of hydroxylamine H2NOH or a salt of hydroxylamine with a compound of the general formula (II) or (III) where R1, R2, R3 and R4 are as defined in formula (I), b) hydrogenation of the compound formed in step a) in the presence of a catalyst, c) further reaction of the compound formed in step b) with a compound of the general formula (II) or (III) and hydrogenation of the reaction mixture in the presence of a catalyst and d), if appropriate, reaction of the salt of the dihydrocarbylhydroxylamine formed in step c) with a base.Type: GrantFiled: December 1, 2006Date of Patent: July 8, 2008Assignee: BASF SEInventors: Gunter Scherhag, Lars Wittenbecher
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Patent number: 7309801Abstract: The invention relates to a process for treating an aqueous medium containing (i) phosphate and (ii) cyclohexanone and/or cyclohexanone oxime, said process comprising: feeding the aqueous medium to a stripping zone; passing steam through the aqueous medium in the stripping zone; and discharging a vapor stream from said stripping zone; wherein the joint content cyclohexanone and cyclohexanone oxime in the aqueous medium entering the stripping zone is less than 0.08 wt. %.Type: GrantFiled: May 29, 2002Date of Patent: December 18, 2007Assignee: DSM IP Assets B.V.Inventors: Arno Benneker, Henk Oevering, Johannes Antonius Leonardus Brouwers
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Publication number: 20070243123Abstract: Provided is a method for manufacturing hydroxylamine. In this method, an aqueous reaction medium containing acidic buffer agent and nitrate ions in the presence of a limited amount of metal impurities such as Fe or Cu is introduced into a hydroxylamine synthesis reactor in the presence of catalyst to proceed hydroxylamine synthesis by reduction of nitrate ions with hydrogen gas as reducing agent in the aqueous reaction medium to produce hydroxylamine. The reaction is processed in the aqueous reaction medium with a limited amount of metal impurities or even without metal impurities, such that the selection rate of the hydroxylamine product is increased.Type: ApplicationFiled: April 5, 2007Publication date: October 18, 2007Applicant: China Petrochemical Development CorporationInventors: Shu-Hung Yang, Cheng-Fa Hsieh, Yi-Bau Hung
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Patent number: 7164047Abstract: A process for preparation of cyclopropylethanol, which comprises subjecting a 3-cyclopropyl-2,3-epoxypropionic acid ester to solvolysis, treating the product of the solvolysis with an acid to obtain cyclopropylacetaldehyde, and reducing the obtained cyclopropylacetaldehyde; and a process for preparation of cyclopropylacetonitrile, which comprises subjecting a 3-cyclopropyl-2,3-epoxypropionic acid ester to solvolysis in the presence of a base, treating the product of the solvolysis with an acid to obtain cyclopropylacetaldehyde, reacting the obtained cyclopropylacetaldehyde with hydroxylamine or salts thereof to obtain cyclopropaneacetaldehyde oxime, and reacting the obtained cyclopropaneacetaldehyde oxime with acetic anhydride. According to the present invention, cyclopropylethanol and cyclopropylacetonitrile can be prepared at low costs and industrially advantageously.Type: GrantFiled: October 31, 2002Date of Patent: January 16, 2007Assignee: Kuraray Co., Ltd.Inventor: Katsuji Ujita
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Patent number: 7161037Abstract: The invention relates to a process for preparing nitric acid by treating an aqueous medium containing organic compounds and phosphate, said process comprising: feeding the aqueous medium to a nitric acid synthesis zone; forming nitric acid by contacting the aqueous medium with a gaseous medium in said nitric acid synthesis zone, said gaseous medium containing NO2; discharging an off-gas from said nitric acid synthesis zone; wherein the total organic carbon concentration in the aqueous medium entering the nitric acid synthesis zone is less than 0.03 wt. %.Type: GrantFiled: December 2, 2002Date of Patent: January 9, 2007Assignee: DSM IP Assets B.V.Inventors: Arno Herald Benneker, Hendrik Oevering, Johannes Antonius Leonardus Brouwers
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Patent number: 7148381Abstract: A process is described for the activation of zeolitic catalysts containing titanium having the formula: xTiO2(1-x)SiO2 wherein x ranges from 0.0001 to 0.4, which consists in treating said materials with a solution of an ammonium salt of a carboxylic acid and subsequently subjecting them to calcination. The catalysts thus treated have higher catalytic performances with respect to those not treated, in oxidation processes of organic substrates.Type: GrantFiled: June 12, 2002Date of Patent: December 12, 2006Assignee: Polimeri Europa S.p.A.Inventors: Vittorio Arca, Angelo Boscolo Boscoletto, Nicola Fracasso, Piero Furlan, Laura Meda
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Patent number: 7005547Abstract: The invention relates to a process for the production of cyclohexanone oxime in which a phosphate-containing aqueous reaction medium is cycled from a hydroxylammonium synthesis zone to a cyclohexanone oxime synthesis zone and back to the hydroxylammonium synthesis zone, in which hydroxylammonium synthesis zone hydroxylammonium is formed by catalytic reduction of nitrate with hydrogen, and in which cyclohexanone oxime synthesis zone hydroxylammonium is reacted with cyclohexanone to form cyclohexanone oxime, the cyclohexanone and an organic solvent being fed into the cyclohexanone oxime synthesis zone, an organic medium comprising the organic solvent and cyclohexanone oxime being withdrawn from the cyclohexanone oxime synthesis zone, characterized in that the ratio fh/fc<1.Type: GrantFiled: May 31, 2001Date of Patent: February 28, 2006Assignee: DSM IP Assets B.V.Inventors: Marc Blaauw, Antonius Jacobus Franciscus Simons, Henk Oevering
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Patent number: 6958418Abstract: Process for preparing vanillylamine or one of the salts thereof by reacting vanillin with hydroxylamine or the salts thereof in the presence of an organic salt, which may optionally be produced in situ, wherein the reaction is carried out in an inorganic or organic acid as diluent, and subsequently hydrogenating the resulting vanillyloxime with hydrogen in the presence of a suitable catalyst and an organic and/or inorganic acid.Type: GrantFiled: June 9, 2005Date of Patent: October 25, 2005Assignee: Boehringer Ingelheim Pharma KGInventors: Oliver Meyer, Ingo Heddesheimer
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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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Patent number: 6844469Abstract: The invention relates to a process for the production of cyclohexanone oxime in which a phosphate-containing aqueous reaction medium is cycled from a hydroxylammonium synthesis zone to a cyclohexanone oxime synthesis zone and back to the hydroxylammonium synthesis zone, in which hydroxylammonium synthesis zone hydroxylammonium is formed by catalytic reduction of nitrate with hydrogen, and in which cyclohexanone oxime synthesis zone hydroxylammonium is reacted with cyclohexanone to form cyclohexanone oxime, where the concentration hydroxylammonium in the aqueous reaction medium entering the cyclohexanone oxime synthesis zone is higher than 1.0 mol/l.Type: GrantFiled: May 31, 2001Date of Patent: January 18, 2005Assignee: DSM Ip Assets B.V.Inventors: Arno Benneker, Paulus Johannes Jacobus Pieters, Alex Pit, Henk Oevering
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Publication number: 20040077895Abstract: The present invention relates to a novel improved process and intermediates for the process of preparing the oxime intermediates of formula (II) wherein R1 is hydrogen, fluoro or chloro, and R2 is methyl, ethyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, cyano, fluoro, chloro or bromo. The novel process comprises diazotizing an aniline of formula (VI) reacting the resulting diazonium salt with isopropenylacetate of formula (X) and reacting the resulting ketone of formula (XI) with an organic nitrite in the presence of hydrogene chloride, and methylating the resulting ketooxime of formula (VIII) with a methylating agent and reacting the resulting O-methyl ketooxime of formula (IX) with hydroxylamine. The compounds of formula (II) are intermediates for highly active fungicides from the class of the atrobilurins.Type: ApplicationFiled: October 15, 2003Publication date: April 22, 2004Inventors: Rudolf Waditschatka, Rene Zurfluh, Edward Kelsall, Hugo Ziegler, Linhua Wang
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Patent number: 6664422Abstract: The present invention relates to a novel improved process and intermediates for the process of preparing the oxime intermediates of formula (II) wherein R1 is hydrogen, fluoro or chloro, and R2 is methyl, ethyl, methoxy, ethoxy, trifluoromethyl, trifluoromethoxy, cyano, fluoro, chloro or bromo. The novel process comprises diazotizing an aniline of formula (VI) reacting the resulting diazonium salt with isopropenylacetate of formula (X) and reacting the resulting ketone of formula (XI) with an organic nitrite in the presence of hydrogene chloride, and methylating the resulting ketooxime of formula (VIII) with a methylating agent and reacting the resulting O-methyl ketooxime of formula (IX) with hydroxylamine. The compounds of formula (II) are intermediates for highly active fungicides from the class of the strobilurins.Type: GrantFiled: August 13, 2001Date of Patent: December 16, 2003Assignee: Bayer AktiengesellschaftInventors: Rudolf Waditschatka, René Zurflüh, Edward Kelsall, Hugo Ziegler, Linhua Wang
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Patent number: 6649140Abstract: A process is described for the continuous production of alcoholic or hydro-alcoholic solutions of hydrogen peroxide in a concentration ranging from 2 to 10% by weight and their direct use in oxidation processes. The process operates under high safety conditions and with a high productivity and molar selectivity towards the formation of H2O2.Type: GrantFiled: June 1, 2001Date of Patent: November 18, 2003Assignees: Eni S.p.A., Enichem S.p.A.Inventors: Giuseppe Paparatto, Franco Rivetti, Pietro Andrigo, Giordano De Alberti
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Patent number: 6639108Abstract: A process for the work-up of a reaction mixture formed by ammoximation of a ketone, in particular an alkanone or cycloalkanone, by means of hydrogen peroxide and ammonia in homogeneous solution over a titanium-containing catalyst. It comprises the substeps removal of the catalyst, selective separation of the oxime formed in the ammoximation from the reaction mixture, removal of water of reaction and recirculation of the solvent. The work-up is carried out using at least one membrane separation step and is also successful in the case of incomplete ketone conversion and in the presence of dissolved salts.Type: GrantFiled: September 3, 2002Date of Patent: October 28, 2003Assignee: Degussa AGInventors: Thomas Schiffer, Peter Ernst Esser, Martin Roos, Franz-Felix Kuppinger, Günter Stevermüer, Georg Friedrich Thiele
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Patent number: 6620970Abstract: The present invention relates to a process for working up an ammoximation reaction mixture, by separating a catalyst from the reaction mixture, removing the ketone oxime product, discharging the water of the reaction, and recirculating a solvent, where the ketone oxime formed is removed in a liquid phase with at least one liquid-liquid extraction in a ternary solvent system.Type: GrantFiled: September 3, 2002Date of Patent: September 16, 2003Assignee: Degussa AGInventors: Thomas Schiffer, Peter Ernst Esser, Jörg Krissmann, Martin Roos, Günter Stevermüer, Georg Friedrich Thiele
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Publication number: 20030171342Abstract: The present invention provides novel 16-ene-C25-oxime and 16-ene-C-25-oxime ether analogs of 1&agr;,25-dihydroxy vitamin D3, compositions comprising these compounds and methods of using these compounds as inhibitors of CYP24. In particular, the compound of Formula I are useful for treating diseases which benefit from a modulation of the levels of 1&agr;,25-dihydroxy vitamin D3, for example, cell-proliferative disorders.Type: ApplicationFiled: October 15, 2002Publication date: September 11, 2003Inventors: Gary Posner, Mehmet Kahraman, Heung Bae Jeon, Jay A. White, Glenville Jones, Bethany Halford
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Publication number: 20030163001Abstract: The invention relates to a method for oximating organic carbonyl compounds and/or CH-acid compounds, wherein at least one organic carbonyl compound and/or CH-acid compound in a liquid or dissolved form is mixed with at least one oximating agent in a liquid or dissolved form in at least one microreactor, is reacted during a residence time and the organic oxime thus formed is optionally isolated from the reaction mixture.Type: ApplicationFiled: April 22, 2003Publication date: August 28, 2003Inventors: Hanns Wurziger, Joeran Stoldt, Guido Pieper, Norbert Schwesinger
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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: 6462235Abstract: Oximes are produced in high yields and with high selectivity by reacting aldehydes or ketones with hydrogen peroxide and ammonia in the presence of a heterogeneous catalyst and an ammonium salt or substituted ammonium salt. The heterogeneous catalyst is synthesized on the basis of titanium, silicon and oxygen. Optionally, a Lewis-acid and/or Brnsted-acid cocatalyst can be present.Type: GrantFiled: November 21, 2001Date of Patent: October 8, 2002Assignee: Degussa AGInventors: Georg Friedrich Thiele, Thomas Schiffer, Georg Oenbrink
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Patent number: 6344589Abstract: A process for preparing bis(oxime) monoethers of the formula I, where: R1 is unsbustituted C1-C4-alkyl or C2-C4-alkenyl-, C2-C4-alkynyl- or phenyl-substituted methyl; R2,R4 independently of one another are hydrogen or methyl; R3,R5 independently of one another are hydrogen or C1-C4-alkyl, trifluoromethyl or phenyl, and intermediates which are obtainable by this process are described.Type: GrantFiled: May 3, 2001Date of Patent: February 5, 2002Assignee: BASF AktiengesellschaftInventors: Wassilios Grammenos, Hubert Sauter, Andreas Gypser, Herbert Bayer, Norbert Götz, Roland Götz
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Patent number: 6342635Abstract: Ketoximes, processes for their preparation, compositions containing them, and a copper extraction process using the compositions.Type: GrantFiled: February 25, 1999Date of Patent: January 29, 2002Assignee: Henkel CorporationInventors: Michael J. Virnig, Horst Josten, Mary Collins, George Wolfe, Dustin Gordon, Rainer Eskuchen, Eugen Heinrichs, Frank McDonnell, Paul O'Driscoll
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Patent number: 6288276Abstract: Process for making Oximes of the formula IV wherein each of R2-R5 is hydrogen, a halogen, an alkyl or cycloalkyl group having from 1 to 36 carbon atoms, an aryl or alkaryl group having from 1 to 36 carbon atoms, an alkoxy or an aryloxy group having from 1 to 30 carbon atoms, an acyl group having from 1 to 24 carbon atoms and intermediates leading thereto are described.Type: GrantFiled: May 2, 2000Date of Patent: September 11, 2001Assignee: Henkel Kommanditgeselschaft auf AktienInventors: Jeffrey H. Dimmit, Mark A. Kearns, William H. Chambless
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Patent number: 6284213Abstract: The present invention relates to a catalyst consisting of a metal of the VIII group supported on acid activated carbon functionalized with sulfonic groups, a process for the synthesis of hydrogen peroxide from hydrogen and oxygen which uses said catalyst and the use of the hydrogen peroxide solution in oxidation processes catalyzed by titanium-silicalite.Type: GrantFiled: August 3, 1999Date of Patent: September 4, 2001Assignee: Enichem S.p.A.Inventors: Giuseppe Paparatto, Rino D'Aloisio, Giordano De Alberti, Piero Furlan, Vittorio Arca, Roberto Buzzoni, Laura Meda
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Patent number: 6235935Abstract: High purity oximes are prepared from aqueous hydroxylamine and ketones reacted at ambient temperature without addition of impurities such as salts or acids.Type: GrantFiled: November 24, 1998Date of Patent: May 22, 2001Assignee: Silicon Valley Chemlabs, Inc.Inventors: Javad J. Sahbari, Jin Wang Russell
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Patent number: 6207863Abstract: Disclosed is an improved method for the preparation of highly pure haloformimine compounds in high yields by reacting a formimine compound in a solvent with a halogenating agent while maintaining the pH of the halogenation reaction in the range of 2 to 5. The pH of the reaction may be maintained by a variety of means, such as by the addition of a base.Type: GrantFiled: May 25, 1999Date of Patent: March 27, 2001Assignee: Rohm and Haas CompanyInventors: John Vincent Berrier, Ashutosh Sumantrai Umarvadia
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Patent number: 6111139Abstract: A compound having the formula 3,3,3-trifluoropropanal oxime, and an improved process for forming 3,3,3-trifluoropropanal and its oxime. The process for producing 3,3,3-trifluoropropanal involves reacting an alkali or alkaline earth metal salt of an alcohol, which alcohol has the formula ROH, where R is a C.sub.1 -C.sub.4 alkyl, with CF.sub.3 CH.dbd.CHCl under conditions sufficient to yield a product mixture comprising at least one of CH.sub.3 CH.dbd.CHOR and CF.sub.3 CH.sub.2 CH(OR).sub.2 ; and then reacting the product mixture of with a C.sub.3 -C.sub.16 alkanoic acid, and heating under conditions sufficient to form 3,3,3-trifluoropropanal. The oxime is prepared by reacting hydroxylamine with 3,3,3-trifluoropropanal under conditions sufficient to produce 3,3,3-trifluoropropanal oxime.Type: GrantFiled: November 4, 1999Date of Patent: August 29, 2000Inventor: Michael Van Der Puy