Preparing Directly By Reacting Carbonyl With Hydroxylamine Or Salt Thereof Patents (Class 564/259)
  • Patent number: 11459293
    Abstract: 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: Grant
    Filed: October 26, 2018
    Date of Patent: October 4, 2022
    Assignee: ImmuneBridge Inc.
    Inventors: Jesse Cotari, Timothy Webb, Zhan Wang
  • Patent number: 9376375
    Abstract: 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: Grant
    Filed: March 23, 2011
    Date of Patent: June 28, 2016
    Assignee: UBE INDUSTRIES, LTD.
    Inventors: Masahide Okada, Junichi Kugimoto, Kazunori Kurosawa, Joji Funatsu, Katsuyoshi Kudo
  • Publication number: 20150011794
    Abstract: 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: Application
    Filed: July 2, 2013
    Publication date: January 8, 2015
    Inventors: Loon-Seng Tan, David Huabin Wang
  • Publication number: 20130211036
    Abstract: 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: Application
    Filed: August 16, 2011
    Publication date: August 15, 2013
    Applicant: ExxonMobil Chemical Company - Law Technology
    Inventors: Jihad M. Dakka, Edmund J. Mozeleski, Charles Morris Smith, Christopher L. Becker, Stephen Zushma
  • Publication number: 20130066112
    Abstract: 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: Application
    Filed: March 8, 2011
    Publication date: March 14, 2013
    Applicant: Bayer Intellectual Property GmbH
    Inventors: Christoph Gürtler, Thomas Ernst Müller, Ewa Gebauer, Henning Vogt, Yevgen Berezhanskyy, Burkhard Köhler, Walter Leitner
  • Publication number: 20130035278
    Abstract: 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: Application
    Filed: October 8, 2012
    Publication date: February 7, 2013
    Applicant: GIVAUDAN SA
    Inventor: Givaudan SA
  • Patent number: 8329948
    Abstract: 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: Grant
    Filed: July 30, 2008
    Date of Patent: December 11, 2012
    Inventor: Mikhail Bobylev
  • Patent number: 8278487
    Abstract: 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: Grant
    Filed: February 4, 2010
    Date of Patent: October 2, 2012
    Assignee: DSM IP Assets B.V.
    Inventor: Nirappurackal Raveendran Shiju
  • Patent number: 8083973
    Abstract: 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: Grant
    Filed: January 22, 2009
    Date of Patent: December 27, 2011
    Assignee: DataLase Ltd.
    Inventor: Anthony N Jarvis
  • Publication number: 20110224457
    Abstract: 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: Application
    Filed: December 25, 2009
    Publication date: September 15, 2011
    Inventor: Hiroki Inoue
  • Publication number: 20110178199
    Abstract: 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: Application
    Filed: September 11, 2008
    Publication date: July 21, 2011
    Applicant: M. Technique Co., Ltd.
    Inventor: Masakazu Enomura
  • Patent number: 7785549
    Abstract: 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: Grant
    Filed: September 11, 2007
    Date of Patent: August 31, 2010
    Assignee: China Petrochemical Development Corporation
    Inventors: Jih-Dar Hwang, Hsiu-Li Cheng, Shou-Li Luo
  • Publication number: 20100130784
    Abstract: 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: Application
    Filed: February 13, 2006
    Publication date: May 27, 2010
    Inventors: George Chang, Michael Patrick Pence
  • Publication number: 20100063323
    Abstract: 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: Application
    Filed: September 9, 2008
    Publication date: March 11, 2010
    Applicant: EVONIK DEGUSSA GmbH
    Inventors: Goetz BAUMGARTEN, Martin ROOS, Stephan SCHAEFLEIN, Rolf AUGENSTEIN
  • Patent number: 7671236
    Abstract: 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: Grant
    Filed: November 20, 2007
    Date of Patent: March 2, 2010
    Assignee: China Petrochemical Development Corporation
    Inventors: Jih-Dar Hwang, Kai-Hung Haung, Hsiu-Li Cheng, Shou-Li Luo
  • Publication number: 20090221854
    Abstract: 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: Application
    Filed: July 4, 2006
    Publication date: September 3, 2009
    Inventors: Hendrik Oevering, Olaf Poorter
  • Publication number: 20090143622
    Abstract: 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: Application
    Filed: July 30, 2008
    Publication date: June 4, 2009
    Inventor: Mikhail Bobylev
  • Patent number: 7423178
    Abstract: 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: Grant
    Filed: January 28, 2004
    Date of Patent: September 9, 2008
    Assignee: DSM IP Assets B.V.
    Inventors: Hendrik Oevering, Arno H Benneker, Johannes A L Brouwers
  • Patent number: 7408081
    Abstract: 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: Grant
    Filed: December 4, 2001
    Date of Patent: August 5, 2008
    Assignee: DSM IP Assets B.V.
    Inventors: Arno Benneker, Henk Oevering, Johannes A. L. Brouwers
  • Patent number: 7408080
    Abstract: 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: Grant
    Filed: May 30, 2003
    Date of Patent: August 5, 2008
    Assignees: China Petroleum & Chemical Corporation, Research Institute of Petroleum Processing, Sinopec
    Inventors: Wei Wu, Bin Sun, Yongxiang Li, Shibiao Cheng, Enquan Wang, Shuzhong Zhang
  • Publication number: 20080167495
    Abstract: 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: Application
    Filed: September 11, 2007
    Publication date: July 10, 2008
    Applicant: China Petrochemical Development Corporation
    Inventors: Jih-Dar Hwang, Hsiu-Li Cheng, Shou-Li Luo
  • Publication number: 20080167496
    Abstract: 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: Application
    Filed: November 20, 2007
    Publication date: July 10, 2008
    Applicant: China Petrochemical Development Corporation
    Inventors: Jih-Dar Hwang, Kai-Hung Haung, Hsiu-Li Cheng, Shou-Li Luo
  • Patent number: 7396959
    Abstract: 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: Grant
    Filed: December 1, 2006
    Date of Patent: July 8, 2008
    Assignee: BASF SE
    Inventors: Gunter Scherhag, Lars Wittenbecher
  • Patent number: 7309801
    Abstract: 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: Grant
    Filed: May 29, 2002
    Date of Patent: December 18, 2007
    Assignee: DSM IP Assets B.V.
    Inventors: Arno Benneker, Henk Oevering, Johannes Antonius Leonardus Brouwers
  • Publication number: 20070243123
    Abstract: 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: Application
    Filed: April 5, 2007
    Publication date: October 18, 2007
    Applicant: China Petrochemical Development Corporation
    Inventors: Shu-Hung Yang, Cheng-Fa Hsieh, Yi-Bau Hung
  • Patent number: 7164047
    Abstract: 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: Grant
    Filed: October 31, 2002
    Date of Patent: January 16, 2007
    Assignee: Kuraray Co., Ltd.
    Inventor: Katsuji Ujita
  • Patent number: 7161037
    Abstract: 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: Grant
    Filed: December 2, 2002
    Date of Patent: January 9, 2007
    Assignee: DSM IP Assets B.V.
    Inventors: Arno Herald Benneker, Hendrik Oevering, Johannes Antonius Leonardus Brouwers
  • Patent number: 7148381
    Abstract: 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: Grant
    Filed: June 12, 2002
    Date of Patent: December 12, 2006
    Assignee: Polimeri Europa S.p.A.
    Inventors: Vittorio Arca, Angelo Boscolo Boscoletto, Nicola Fracasso, Piero Furlan, Laura Meda
  • Patent number: 7005547
    Abstract: 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: Grant
    Filed: May 31, 2001
    Date of Patent: February 28, 2006
    Assignee: DSM IP Assets B.V.
    Inventors: Marc Blaauw, Antonius Jacobus Franciscus Simons, Henk Oevering
  • Patent number: 6958418
    Abstract: 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: Grant
    Filed: June 9, 2005
    Date of Patent: October 25, 2005
    Assignee: Boehringer Ingelheim Pharma KG
    Inventors: Oliver Meyer, Ingo Heddesheimer
  • Patent number: 6927308
    Abstract: 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: Grant
    Filed: December 12, 2003
    Date of Patent: August 9, 2005
    Assignee: Degussa AG
    Inventors: Stefan Leininger, Juergen Herwig, Martin Roos, Georg Oenbrink
  • Patent number: 6906223
    Abstract: 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: Grant
    Filed: July 4, 2001
    Date of Patent: June 14, 2005
    Assignee: BASF AG
    Inventors: Andreas Kramer, Matthias Kiefer, Michael Henningsen, Wolfgang Siegel, Jochen Schröder
  • Patent number: 6844469
    Abstract: 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: Grant
    Filed: May 31, 2001
    Date of Patent: January 18, 2005
    Assignee: DSM Ip Assets B.V.
    Inventors: Arno Benneker, Paulus Johannes Jacobus Pieters, Alex Pit, Henk Oevering
  • Publication number: 20040077895
    Abstract: 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: Application
    Filed: October 15, 2003
    Publication date: April 22, 2004
    Inventors: Rudolf Waditschatka, Rene Zurfluh, Edward Kelsall, Hugo Ziegler, Linhua Wang
  • Patent number: 6664422
    Abstract: 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: Grant
    Filed: August 13, 2001
    Date of Patent: December 16, 2003
    Assignee: Bayer Aktiengesellschaft
    Inventors: Rudolf Waditschatka, René Zurflüh, Edward Kelsall, Hugo Ziegler, Linhua Wang
  • Patent number: 6649140
    Abstract: 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: Grant
    Filed: June 1, 2001
    Date of Patent: November 18, 2003
    Assignees: Eni S.p.A., Enichem S.p.A.
    Inventors: Giuseppe Paparatto, Franco Rivetti, Pietro Andrigo, Giordano De Alberti
  • Patent number: 6639108
    Abstract: 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: Grant
    Filed: September 3, 2002
    Date of Patent: October 28, 2003
    Assignee: Degussa AG
    Inventors: Thomas Schiffer, Peter Ernst Esser, Martin Roos, Franz-Felix Kuppinger, Günter Stevermüer, Georg Friedrich Thiele
  • Patent number: 6620970
    Abstract: 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: Grant
    Filed: September 3, 2002
    Date of Patent: September 16, 2003
    Assignee: Degussa AG
    Inventors: Thomas Schiffer, Peter Ernst Esser, Jörg Krissmann, Martin Roos, Günter Stevermüer, Georg Friedrich Thiele
  • Publication number: 20030171342
    Abstract: 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: Application
    Filed: October 15, 2002
    Publication date: September 11, 2003
    Inventors: Gary Posner, Mehmet Kahraman, Heung Bae Jeon, Jay A. White, Glenville Jones, Bethany Halford
  • Publication number: 20030163001
    Abstract: 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: Application
    Filed: April 22, 2003
    Publication date: August 28, 2003
    Inventors: Hanns Wurziger, Joeran Stoldt, Guido Pieper, Norbert Schwesinger
  • Patent number: 6566555
    Abstract: 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: Grant
    Filed: September 26, 2001
    Date of Patent: May 20, 2003
    Assignee: Degussa AG
    Inventors: Georg Friedrich Thiele, Steffen Hasenzahl, Thomas Schiffer
  • Patent number: 6462235
    Abstract: 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: Grant
    Filed: November 21, 2001
    Date of Patent: October 8, 2002
    Assignee: Degussa AG
    Inventors: Georg Friedrich Thiele, Thomas Schiffer, Georg Oenbrink
  • Patent number: 6344589
    Abstract: 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: Grant
    Filed: May 3, 2001
    Date of Patent: February 5, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Wassilios Grammenos, Hubert Sauter, Andreas Gypser, Herbert Bayer, Norbert Götz, Roland Götz
  • Patent number: 6342635
    Abstract: Ketoximes, processes for their preparation, compositions containing them, and a copper extraction process using the compositions.
    Type: Grant
    Filed: February 25, 1999
    Date of Patent: January 29, 2002
    Assignee: Henkel Corporation
    Inventors: Michael J. Virnig, Horst Josten, Mary Collins, George Wolfe, Dustin Gordon, Rainer Eskuchen, Eugen Heinrichs, Frank McDonnell, Paul O'Driscoll
  • Patent number: 6288276
    Abstract: 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: Grant
    Filed: May 2, 2000
    Date of Patent: September 11, 2001
    Assignee: Henkel Kommanditgeselschaft auf Aktien
    Inventors: Jeffrey H. Dimmit, Mark A. Kearns, William H. Chambless
  • Patent number: 6284213
    Abstract: 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: Grant
    Filed: August 3, 1999
    Date of Patent: September 4, 2001
    Assignee: Enichem S.p.A.
    Inventors: Giuseppe Paparatto, Rino D'Aloisio, Giordano De Alberti, Piero Furlan, Vittorio Arca, Roberto Buzzoni, Laura Meda
  • Patent number: 6235935
    Abstract: High purity oximes are prepared from aqueous hydroxylamine and ketones reacted at ambient temperature without addition of impurities such as salts or acids.
    Type: Grant
    Filed: November 24, 1998
    Date of Patent: May 22, 2001
    Assignee: Silicon Valley Chemlabs, Inc.
    Inventors: Javad J. Sahbari, Jin Wang Russell
  • Patent number: 6207863
    Abstract: 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: Grant
    Filed: May 25, 1999
    Date of Patent: March 27, 2001
    Assignee: Rohm and Haas Company
    Inventors: John Vincent Berrier, Ashutosh Sumantrai Umarvadia
  • Patent number: 6111139
    Abstract: 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: Grant
    Filed: November 4, 1999
    Date of Patent: August 29, 2000
    Inventor: Michael Van Der Puy
  • Patent number: 5969185
    Abstract: A process for making a phenolic ketone involving reacting a metal aryloxide with an aliphatic aldehyde having from at least 2 to about 25 carbon atoms.
    Type: Grant
    Filed: June 24, 1998
    Date of Patent: October 19, 1999
    Assignee: Henkel Corporation
    Inventor: Sang I. Kang