Purification Or Recovery Patents (Class 564/264)
  • Patent number: 8974673
    Abstract: The invention relates to a method and apparatus for restoring the extractive potential of organic hydroxyoxime-based extraction solution used in the recovery of metals by liquid-liquid extraction. The method is two-stage, in which an aqueous solution of hydroxylamine or some hydroxylamine compound is used in the reaction stage, and the removal of the undesirable compounds generated in the reaction occurs in the second stage by adsorption purification. The reaction stage and the adsorptive stage are carried out in a mixing tank.
    Type: Grant
    Filed: May 26, 2010
    Date of Patent: March 10, 2015
    Assignee: Outotec Oyj
    Inventors: Erkki Paatero, Kai Jyrkkä, Sami Virolainen
  • Publication number: 20140275627
    Abstract: The present disclosure provides methods for separating ketones and alcohols. In one embodiment, the methods and compositions disclosed are useful in separating cyclohexanol from cyclohexanone. In one embodiment, cyclohexanone is converted to its corresponding oxime by treating the cyclohexanone with hydroxylamine. The resulting cyclohexanone oxime is then separated from the cyclohexanol, providing streams of cyclohexanol and cyclohexanone oxime.
    Type: Application
    Filed: March 11, 2014
    Publication date: September 18, 2014
    Applicant: HONEYWELL INTERNATIONAL INC.
    Inventors: James A. Kweeder, Alan B. Levy
  • Patent number: 8021632
    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: Grant
    Filed: September 9, 2008
    Date of Patent: September 20, 2011
    Assignee: 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
  • Patent number: 7601872
    Abstract: Disclosed are compounds capable of facilitating transport of biologically active agents or substances into cells having the general structure: wherein Q is selected from the group consisting of N, O and S; L is any bivalent organic radical capable of linking each Q, such as C, CH, (CH2)l, or {(CH2)i-Y—(CH2)j}k, wherein Y is selected from the group consisting of CH2, an ether, a polyether, an amide, a polyamide, an ester, a sulfide, a urea, a thiourea, a guanidyl, a carbamoyl, a carbonate, a phosphate, a sulfate, a sulfoxide, an imine, a carbonyl, and a secondary amino group and wherein Y is optionally substituted by —X1-L?-X2-Z or -Z; R1-R6, independently of one another, are selected from the group consisting of H, —(CH2)p-D-Z, an alkyl, an alkenyl, an aryl, and an alkyl or alkyl ether optionally substituted by one or more of an alcohol, an aminoalcohol, an amine, an amide, an ether, a polyether, a polyamide, an ester, a mercaptan, an alkylthio, a urea, a thiourea, a guanidyl, or a carbamoyl group, and w
    Type: Grant
    Filed: January 21, 2005
    Date of Patent: October 13, 2009
    Assignee: Life Technologies Corporation
    Inventors: Yongliang Chu, Malek Masoud, Gulilat Gebeyehu
  • Publication number: 20080242891
    Abstract: A liquid cyclohexanone oxime A is vaporized by heating to obtain a cyclohexanone oxime gas A1 and the remaining residue C is distilled under a pressure lower than the pressure upon vaporization by heating, and then cyclohexanone oxime A2 contained in the residue C is recovered.
    Type: Application
    Filed: March 28, 2008
    Publication date: October 2, 2008
    Inventors: Masashi YOKOTA, Kanji KUWAHARA
  • Publication number: 20080228006
    Abstract: The invention relates to a method for largely eliminating chlorine compounds from organic isocyanates or isocyanate mixtures by contacting said isocyanates or isocyanate mixtures with a water-containing inert gas flow or an organic material having a cation-exchanging effect. The inventive method allows the isocyanates to be gently freed from chorine-containing compounds and is particularly suitable for temperature-sensitive isocyanates.
    Type: Application
    Filed: December 10, 2005
    Publication date: September 18, 2008
    Applicant: LANXESS DEUTSCHLAND GMBH
    Inventors: Andreas Job, Klaus Jost, Hans-Ulrich Dummersdorf
  • Patent number: 7323594
    Abstract: Disclosed are compounds capable of facilitating transport of biologically active agents or substances into cells having the general structure: wherein Q is selected from the group consisting of N, O and S; L is any bivalent organic radical capable of linking each Q, such as C, CH, (CH2)l, or {(CH2)i-Y—(CH2)j}k, wherein Y is selected from the group consisting of CH2, an ether, a polyether, an amide, a polyamide, an ester, a sulfide, a urea, a thiourea, a guanidyl, a carbamoyl, a carbonate, a phosphate, a sulfate, a sulfoxide, an imine, a carbonyl, and a secondary amino group and wherein Y is optionally substituted by -X1-L?-X2-Z or -Z; R1-R6, independently of one another, are selected from the group consisting of H, —(CH2)p-D-Z, an alkyl, an alkenyl, an aryl, and an alkyl or alkyl ether optionally substituted by one or more of an alcohol, an aminoalcohol, an amine, an amide, an ether, a polyether, a polyamide, an ester, a mercaptan, an alkylthio, a urea, a thiourea, a guanidyl, or a carbamoyl group, and
    Type: Grant
    Filed: December 28, 2006
    Date of Patent: January 29, 2008
    Assignee: Invitrogen Corporation
    Inventors: Yongliang Chu, Malek Masoud, Gulilat Gebeyehu
  • Patent number: 7232928
    Abstract: Cycloalkanone oxime is stabilized by a method comprising bringing the cycloalkanone oxime into contact with at least one compound selected from the group consisting of oxoacids, oxoacid salts, oxoacid esters, oxoacid amides and oxides of boron or phosphorus. In accordance with the invention, the thermal stability of cycloalkanone oxime can be improved.
    Type: Grant
    Filed: November 24, 2004
    Date of Patent: June 19, 2007
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Masami Fukao, Noriaki Tanaka
  • Patent number: 7071360
    Abstract: A method is provided for evaporating cyclohexanone oxime in which cyclohexanone oxime is evaporated using a falling-film evaporator with wetting the evaporation surface of the evaporator well with the cyclohexanone oxime at a pressure of less than about 1060 Torr with a falling rate of the cyclohexanone oxime of about 170 kg/hour or more per one meter around the circumference of evaporation surface at the lowest part of the evaporator. In this method, the cyclohexanone oxime is evaporated efficiently with little decomposition thereof, while preventing the plugging of the pipes of the evaporator and continuously carrying out the operation of the evaporator for a long period of time.
    Type: Grant
    Filed: March 26, 2002
    Date of Patent: July 4, 2006
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Yasumoto Shimazu, Kanji Kuwahara, Masaru Kitamura
  • 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: 6843978
    Abstract: The present invention refers to a microporous material formed by oxygen, silicon, germanium, aluminum, boron, gallium, zirconium and/or titanium in its composition, called TIQ-6, to its catalytic applications in oxidation reactions, and to a method of the TIQ-6 material's preparation based on the synthesis of a gel with a titanium and/or zirconium content, its hydrothermal treatment under controlled conditions, and the treatment of the resulting laminar material with a solution of an organic compound containing a proton accepting group. This swollen material is subjected to a specific treatment to obtain a high external area delaminated solid. A material, METIQ-6, similar to the TIQ-6 material, but also having organic groups anchored on its surface incorporated by a post-synthesis process onto the TIQ-6 material is also claimed.
    Type: Grant
    Filed: May 24, 2002
    Date of Patent: January 18, 2005
    Assignees: Consejo Superior De Investigaciones Cientificas, Universidad Politecnica De Valencia
    Inventors: Avelino Corma Canós, Vicente Fornes Segui, Urbano Díaz Morales, Marcelo Eduardo Domine
  • Patent number: 6818794
    Abstract: Process for extracting aqueous ketazine solutions which is carried out using an aqueous ketazine solution having a salt content of 5 to 27% by weight and an ammonia content of 0 to 28% by weight to extract at temperatures of 50 to 120° C., which is characterized in that the ketazine solution to be extracted has a molar excess of 50 to 200% of ketone based on the ketazine to be extracted, and that an aliphatic hydrocarbon extractant is used which has a boiling point of 150 to 300° C. at atmospheric pressure.
    Type: Grant
    Filed: November 27, 2002
    Date of Patent: November 16, 2004
    Assignee: Bayer Aktiengesellschaft
    Inventors: Ottfried Schlak, Hans-Georg Adams, Johannes Kaulen
  • Patent number: 6784316
    Abstract: The invention relates to a purification method of cyclohexanone-oxime in a solution of solvents immiscible with water, which consists in washing said solutions with water or with an aqueous solution of a base having a pK<5 or in passing the solutions of cyclohexanone-oxime through a weakly alkaline ion exchange resin and, optionally, also through a weakly acid ion exchange resin.
    Type: Grant
    Filed: June 27, 2002
    Date of Patent: August 31, 2004
    Assignee: Enichem S.p.A.
    Inventors: Masami Fukao, Francesco Cainelli, Roberto Tessari, Piero Furlan
  • 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: 20030105356
    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: Application
    Filed: September 3, 2002
    Publication date: June 5, 2003
    Applicant: DEGUSSA AG
    Inventors: Thomas Schiffer, Peter Ernst Esser, Martin Roos, Franz-Felix Kuppinger, Gunter Stevermuer, Georg Friedrich Thiele
  • 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
  • Publication number: 20030065220
    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: Application
    Filed: September 3, 2002
    Publication date: April 3, 2003
    Applicant: DEGUSSA AG
    Inventors: Thomas Schiffer, Peter Ernst Esser, Jorg Krissmann, Martin Roos, Gunter Stevermuer, Georg Friedrich Thiele
  • Publication number: 20030013916
    Abstract: The invention relates to a purification method of cyclohexanone-oxime in a solution of solvents immiscible with water, which consists in washing said solutions with water or with an aqueous solution of a base having a pK<5 or in passing the solutions of cyclohexanone-oxime through a weakly alkaline ion exchange resin and, optionally, also through a weakly acid ion exchange resin.
    Type: Application
    Filed: June 27, 2002
    Publication date: January 16, 2003
    Applicant: ENICHEM S.p.A.
    Inventors: Masami Fukao, Francesco Cainelli, Roberto Tessari, Piero Furlan
  • Patent number: 6329359
    Abstract: The present invention relates to benzyloxyimino compounds of the formula I, where: R1 to R4, X, Y, and Z are as defined in the specification.
    Type: Grant
    Filed: October 13, 1999
    Date of Patent: December 11, 2001
    Assignee: BASF Aktiengesellschaft
    Inventors: Wassilios Grammenos, Hubert Sauter, Herbert Bayer, Thomas Grote, Andreas Gypser, Reinhard Kirstgen, Bernd Müller, Arne Ptock, Franz Röhl, Roland Götz, Gisela Lorenz, Eberhard Ammermann, Siegfried Strathmann, Volker Harries
  • Publication number: 20010021791
    Abstract: The present invention is related to a novel intermediates and processes which are useful in the preparation of certain antihistaminic piperidine derivatives of the formula 1
    Type: Application
    Filed: December 8, 2000
    Publication date: September 13, 2001
    Applicant: Merrell Pharmaceuticals Inc.
    Inventors: Richard C. Krauss, Robert M. Strom, Carey L. Scortichini, William J. Kruper, Richard A. Wolf, Weishi W. Wu, Albert A. Carr, David A. Hax, Duane E. Rudisill, Gianbattista Panzone
  • Patent number: 5411936
    Abstract: Cyclohexenone oxime ethers of the general formula I ##STR1## where R.sup.1 is C.sub.1 -C.sub.6 -alkyl, A is substituted or unsubstituted C.sub.4 -alkylene or C.sub.4 -alkenylene,x is nitro, cyano, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkylthio, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, substituted or unsubstituted benzyloxycarbonyl and/or phenyl,n is from 0 to 3 or from 1 to 5 when X is halogen,R.sup.2 is C.sub.1 -C.sub.6 -alkoxy-C.sub.1 -C.sub.6 -alkyl or C.sub.1 -C.sub.4 -alkylthio-C.sub.1 -C.sub.6 -alkyl, substituted or unsubstituted C.sub.3 -C.sub.7 -cycloalkyl or C.sub.5 -C.sub.
    Type: Grant
    Filed: January 19, 1993
    Date of Patent: May 2, 1995
    Assignee: BASF Aktiengesellschaft
    Inventors: Juergen Kast, Dieter Kolassa, Norbert Meyer, Ulrich Schirmer, Albrecht Harreus, Jochen Wild, Karl-Otto Westphalen, Bruno Wuerzer
  • Patent number: 5130486
    Abstract: Isomerization of an unsymmetrical ketoxime ether is effected using at least one Lewis acid selected from titanium chloride, titanium bromide, aluminum chloride, aluminum bromide, boron chloride, and boron bromide as isomerizing agents. Examples of the Lewis acid are titanium tetrachloride, titanium trichloride, aluminum trichloride, aluminum tribromide, boron trichloride, and boron tribromide. The ketoxime ether is preferably an anti-isomer or a syn-isomer of a compound represented by the formula (I) or a mixture of the anti-isomer and the syn-isomer: ##STR1## wherein R.sub.1 represents an aryl group, an aralkyl group or an alkyl group and R.sub.2 and R.sub.3 each represents an aralkyl group or an alkyl group, with a proviso that R.sub.1 and R.sub.2 are not identical.
    Type: Grant
    Filed: December 27, 1990
    Date of Patent: July 14, 1992
    Assignee: Sumitomo Chemical Company Limited
    Inventors: Naoto Konyo, Yukio Yoneyoshi, Gohfu Suzukamo
  • Patent number: 4931592
    Abstract: The storability of molten cyclohexanone oxime containing 0.5-15% by weight of cyclohexanone and 1-8% by weight of aqueous ammonium bisulfate solution is improved by washing the molten cyclohexanone oxime with a 10-42% strength by weight aqueous ammonium sulfate solution and maintaining a pH of 4.5-5.8.
    Type: Grant
    Filed: October 31, 1989
    Date of Patent: June 5, 1990
    Assignee: BASF Aktiengesellschaft
    Inventors: Hugo Fuchs, David Agab, Gerald Neubauer, Josef Ritz
  • Patent number: 4873369
    Abstract: Cyclohexanone oxime containing ammonium sulfate is purified by a process in which cyclohexanone oxime in the molten state is passed over an acidic ion exchanger and a basic ion exchanger.
    Type: Grant
    Filed: March 5, 1987
    Date of Patent: October 10, 1989
    Assignee: BASF Aktiengesellschaft
    Inventor: Hugo Fuchs
  • Patent number: 4868334
    Abstract: The present invention provides a simple process for the production of anhydrous oxime by the separation of the oxime from an aqueous solution. The process is advantageous because the potential explosive hazards of current processes are eliminated and the oxime is easily separated from the aqueous phase. The process comprises the steps of:(a) vaporizing an aqueous oxime solution;(b) vaporizing a water-immiscible organic solvent for the oxime wherein the boiling point of the solvent is lower than the boiling point of the oxime;(c) combining the vapors together;(d) condensing the collected vapors;(e) removing the organic phase of the condensate from the aqueous phase; and(f) recovering anhydrous oxime from the removed organic phase.The anhydrous oxime produced by the present process if useful in applications such as isocyanate condensation and carbamate formation.
    Type: Grant
    Filed: July 11, 1988
    Date of Patent: September 19, 1989
    Assignee: Allied-Signal Inc.
    Inventors: Chempolil T. Mathew, Stephen E. Belsky, Earl E. McKnight
  • Patent number: 4619823
    Abstract: A radioactive diagnostic agent which comprises platelets labeled with radioactive iodine atom-labeled metaraminol in an aqueous medium.
    Type: Grant
    Filed: December 22, 1983
    Date of Patent: October 28, 1986
    Assignee: Nihon Medi-Physics Co., Ltd.
    Inventors: Akira Yokoyama, Yoshiro Ohmomo
  • Patent number: 4323706
    Abstract: Acetaldehyde oxime, a commercially useful intermediate in the production of pesticides, is prepared by oximating acetaldehyde with an aqueous hydroxylamine-containing solution to form an aqueous oximation reaction mixture and recovering acetaldehyde oxime from the aqueous oximation reaction mixture by distilling a mixture of acetaldehyde oxime and water directly from the aqueous oximation reaction mixture.
    Type: Grant
    Filed: December 18, 1980
    Date of Patent: April 6, 1982
    Assignee: Allied Corporation
    Inventors: John H. Bonfield, Stephen E. Belsky, Donald Pickens
  • Patent number: 4256668
    Abstract: An organic, substantially water-insoluble oxime product is recovered from the liquid reaction mixture of water, ammonium sulfate and the oxime product. First the reaction mixture is separated into a first liquid layer containing an aqueous ammonium sulfate solution and a second liquid layer containing an emulsion of the oxime product as the continuous phase and aqueous ammonium sulfate as the discontinuous phase. These layers are separated and the second liquid layer is contacted with solid ammonium sulfate for a time sufficient to agglomerate the discontinuous phase. The agglomerated discontinuous phase is then removed from the continuous phase. Thereafter, either a lites fraction can be distilled from the continuous phase or the oxime product can be distilled from the continuous phase, or both. The process is particularly applicable to the production of oximes such as Aldicarb oxime, cyclohexanone oxime and methylethylketoxime from aqueous reaction mixtures in which by-product ammonium sulfate is formed.
    Type: Grant
    Filed: June 20, 1979
    Date of Patent: March 17, 1981
    Assignee: Allied Chemical Corporation
    Inventors: Chempolil T. Mathew, Donald Pickens