Including Dissolving Reactant In Alcohol Containing Solvent Patents (Class 423/590)
  • Patent number: 10793433
    Abstract: A process for manufacturing hydrogen peroxide by an anthraquinone autoxidation process (AO-process) comprising two alternate (essential) steps of: (a) hydrogenation of a working solution in a hydrogenation unit in the presence of a catalyst, wherein such working solution contains at least one alkylanthraquinone dissolved in at least one organic solvent, to obtain at least one corresponding alkylanthrahydroquinone compound; and (b) oxidation of the at least one alkylanthrahydroquinone compound to obtain hydrogen peroxide in an oxidation unit; and further comprising the step of: (c) extracting the hydrogen peroxide formed in the oxidation step in an extraction unit, wherein the units of step (a) to (c), optionally together with further ancillary units as appropriate, constitute a hydrogen peroxide production site, wherein one or more of said units are equipped with one or more sensors for monitoring one or more AO-process parameters at the hydrogen peroxide production site, said sensors being interconnected wit
    Type: Grant
    Filed: October 2, 2012
    Date of Patent: October 6, 2020
    Assignee: Solvay SA
    Inventors: Alain Vandenbussche, Patrick Markus Dhaese, Stephen Bloomfield, Francine Janssens
  • Patent number: 9617153
    Abstract: A process for manufacturing hydrogen peroxide by an anthraquinone autoxidation process (AO-process) comprising two alternate essential steps of: (a) hydrogenation of a working solution in a hydrogenation unit in the presence of a catalyst, wherein the working solution contains at least one alkylanthraquinone dissolved in at least one organic solvent, to obtain at least one corresponding alkylanthrahydroquinone compound; and (b) oxidation of the at least one alkylanthrahydroquinone compound to obtain hydrogen peroxide in an oxidation unit; and further comprising step (c): extracting the hydrogen peroxide formed in the oxidation step in an extraction unit, wherein the hydrogenation, oxidation and extraction steps are performed in an reactor system which is designed as a compact modular system of a hydrogenation, an oxidation and an extraction unit, and wherein the reactor system is configured to operate without a reversion (regeneration) unit for continuous reversion of the working solution as a small to medium
    Type: Grant
    Filed: October 2, 2012
    Date of Patent: April 11, 2017
    Assignee: SOLVAY SA
    Inventors: Alain Vandenbussche, Patrick Markus Dhaese, Stephen Bloomfield, Francine Janssens
  • Patent number: 8664137
    Abstract: A regenerating method for activated alumina used in regenerating working fluid of hydrogen peroxide comprises the following steps: adding deactivated alumina discharged from a regenerating bed for working fluid of hydrogen peroxide into a reactor through the top of the reactor and settling by gravity, oxidizing atmosphere entering into the reactor from the bottom of the reactor and running upwardly, then discharging exit gas and regenerated alumina through the discharge port on the top and discharging device on the bottom of the reactor respectively. The method is economic, environment-protective, safe, low-costly. The regenerated alumina will not poison palladium catalyst.
    Type: Grant
    Filed: January 28, 2008
    Date of Patent: March 4, 2014
    Assignee: Shanghai Huaming Hi-Tech (Group) Co., Ltd.
    Inventors: Qiufang Wu, Guojian Chen, Fuqing Li, Xinsheng Ma, Gang Chen, Jinghui Yang, Zhiping Zhang
  • Patent number: 8664138
    Abstract: A regenerating method for activated alumina used in regenerating working fluid of hydrogen peroxide comprises the following steps: adding deactivated alumina discharged from a regenerating bed for working fluid of hydrogen peroxide with fire resistant alumina into a reactor through the top of the reactor and settling by gravity, oxidizing atmosphere entering into the reactor from the bottom of the reactor and running upwardly, discharging regenerated alumina and fire resistant alumina through the discharging device on the bottom of the reactor, discharging exit gas through the discharge port on the top of the reactor, the reaction temperature ranging from 360-800° C., the residence time of solid feed in the reactor ranging from 3-15 h. The method is economic, environment-protective, safe, and low-costly. The regenerated alumina will not poison palladium catalyst.
    Type: Grant
    Filed: January 28, 2008
    Date of Patent: March 4, 2014
    Assignee: Shanghai Huaming Hi-Tech (Group) Co., Ltd.
    Inventors: Fuqing Li, Xinsheng Ma, Gang Chen, Qiufang Wu, Guojian Chen, Yubao Gan, Jinghui Yang
  • Patent number: 7645438
    Abstract: The invention relates to a process for the production of hydrogen peroxide comprising a liquid-liquid extraction step, said extraction step comprising contacting an organic feed solution containing hydrogen peroxide with an extraction solvent comprising less than about 30 wt % of water to achieve extraction of hydrogen peroxide to said extraction solvent and obtaining an extract containing hydrogen peroxide.
    Type: Grant
    Filed: June 11, 2007
    Date of Patent: January 12, 2010
    Assignee: Akzo Nobel N.V.
    Inventors: Rolf Edvinsson-Albers, Boris Kuzmanovic, Cornald Van Strien
  • Patent number: 7601323
    Abstract: The present invention provides a method for producing hydrogen peroxide, comprising the steps of: alternately reducing and oxidizing a working solution containing anthraquinone compounds as a reaction medium, wherein a mixture of alkyl-substituted anthraquinones and alkyl-substituted tetrahydroanthraquinones in a molar ratio of from 2:1 to 8:1 is used as the anthraquinone compounds in the working solution, in the reduction step all of the tetrahydroanthraquinones and some or all of the anthraquinones in the working solution are reduced; and keeping the content of alkyl-substituted anthrahydroquinones in the working solution after the reduction step and before the oxidation step higher than the content of alkyl-substituted tetrahydroanthrahydroquinones, wherein ethylanthraquinone and ethyltetrahydroanthraquinone are used as anthraquinone compounds in the working solution in a total proportion of both of from 10 to 45 mol % of all of the anthraquinone compounds in the working solution.
    Type: Grant
    Filed: July 13, 2007
    Date of Patent: October 13, 2009
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Hisashi Sakaitani, Katsuhiro Iura, Isao Hagiwara, Hiroshi Hasegawa, Hisashi Matsuda
  • Patent number: 7425316
    Abstract: The invention relates to a process for production of hydrogen peroxide according to the anthraquinone process including altemate hydrogenation and oxidation of one or more quinones selected from anthraquinones and/or tetrahydro anthraquinones in a working solution comprising at least one quinone solvent and at least one hydroquinone solvent, wherein said at least one quinone solvent comprises isodurene in an amount from 15 to 100 wt %. The invention also relates to a composition useful as a working solution at production hydrogen peroxide.
    Type: Grant
    Filed: October 20, 2005
    Date of Patent: September 16, 2008
    Assignee: Akzo Nobel NV
    Inventors: Mats Nystrom, Christina Jarnvik
  • Publication number: 20080213164
    Abstract: The present invention provides a method for producing hydrogen peroxide, comprising the steps of: alternately reducing and oxidizing a working solution containing anthraquinone compounds as a reaction medium, wherein a mixture of alkyl-substituted anthraquinones and alkyl-substituted tetrahydroanthraquinones in a molar ratio of from 2:1 to 8:1 is used as the anthraquinone compounds in the working solution, in the reduction step all of the tetrahydroanthraquinones and some or all of the anthraquinones in the working solution are reduced; and keeping the content of alkyl-substituted anthrahydroquinones in the working solution after the reduction step and before the oxidation step higher than the content of alkyl-substituted tetrahydroanthrahydroquinones, wherein ethylanthraquinone and ethyltetrahydroanthraquinone are used as anthraquinone compounds in the working solution in a total proportion of both of from 10 to 45 mol % of all of the anthraquinone compounds in the working solution.
    Type: Application
    Filed: July 13, 2007
    Publication date: September 4, 2008
    Inventors: Hisashi Sakaitani, Katsuhiro Iura, Isao Hagiwara, Hiroshi Hasegawa, Hisashi Matsuda
  • Patent number: 7416718
    Abstract: Hydrogen peroxide is prepared by an auto-oxidation method via oxidation in a microreactor. A working solution containing a reactive carrier compound is hydrogenated with hydrogen in a first step and is subsequently oxidized in a microreactor to produce hydrogen peroxide.
    Type: Grant
    Filed: August 30, 2006
    Date of Patent: August 26, 2008
    Assignee: FMC Corporation
    Inventors: Dalbir S. Sethi, Emmanuel A. Dada, Kevin Hammack, Xinliang Zhou
  • Patent number: 7238335
    Abstract: The invention concerns a process for the preparation of hydrogen peroxide by the anthraquinone cyclic process. The process includes a regeneration stage in which working solution is regenerated by being brought into contact with an aqueous solution containing an alkyl anthrahydroquinone and/or an alkyl tetrahydroanthrahydroquinone in deprotonated form. The working solution regenerated in the regeneration stage is returned to the cyclic process.
    Type: Grant
    Filed: August 6, 2004
    Date of Patent: July 3, 2007
    Assignee: Degussa AG
    Inventors: Gustaaf Goor, Eugen Staab, Jürgen Glenneberg
  • Patent number: 7056485
    Abstract: The invention is directed to a continuous hydrogenation process in which a hydrogenable compound is dissolved in a working solution with hydrogen and a heterogeneous catalyst. At least part of the hydrogen-containing waste hydrogenation gas generated in the reaction is compressed and then recycled into the hydrogenation reactor. A jet pump is used for the compression of the waste hydrogenation gas and a liquid or gaseous feedstock of the hydrogenation process is used as the motive agent. Preferred motive agents are the hydrogenation gas or a working solution recycled into the process. The process is particularly suitable for performing the hydrogenation step in the anthraquinone process for the production of hydrogen peroxide.
    Type: Grant
    Filed: October 14, 2003
    Date of Patent: June 6, 2006
    Assignee: Degussa AG
    Inventors: Matthias Creutz, Hubertus Eickhoff, Bernhard Maurer
  • Patent number: 7001584
    Abstract: The invention relates to a process for production of hydrogen peroxide according to the anthraquinone process including alternate hydrogenation and oxidation of one or more quinones selected from anthraquinones and/or tetrahydro anthraquinones in a working solution comprising at least one quinone solvent and at least one hydroquinone solvent, wherein said at least one quinone solvent comprises isodurene in an amount from 15 to 100 wt %. The invention also relates to a composition useful as a working solution at production of hydrogen peroxide.
    Type: Grant
    Filed: June 12, 2001
    Date of Patent: February 21, 2006
    Assignee: Akzo Nobel N.V.
    Inventors: Mats Nyström, Christina Järnvik
  • Patent number: 6861042
    Abstract: A continuous catalytic hydrogenation process, in which a reaction mixture containing the substance to be hydrogenated, the hydrogenation product, hydrogen and the hydrogenation catalyst suspended in the reaction mixture is recirculated in a reactor. Part of the hydrogenation product is removed from the reactor and the substance to be hydrogenated and hydrogen are fed into the reaction. In this process the substance to be hydrogenated and the hydrogen are mixed before entering the reactor. A venturi nozzle is particularly suitable as the mixing device.
    Type: Grant
    Filed: December 16, 2003
    Date of Patent: March 1, 2005
    Assignee: Degussa AG
    Inventors: Peter Korl, Bernhard Maurer
  • Patent number: 6524547
    Abstract: The invention concerns a process for production of hydrogen peroxide according to the anthraquinone process comprising the steps of alternate hydrogenation and oxidation of anthraquinones and tetrahydro anthraquinones in a working solution comprising a mixture of alkyl-substituted anthraquinones and alkyl-substituted tetrahydro anthraquinones dissolved in at least one organic solvent, wherein from 10 to 55 mole % of the anthraquinones and the tetrahydro anthraquinones are substituted with one amyl group, and the molar ratio of alkyl-substituted tetrahydro anthraquinones to alkyl-substituted anthraquinones is at least 1:1. The invention also concerns a composition useful as a working solution in said process.
    Type: Grant
    Filed: November 20, 2000
    Date of Patent: February 25, 2003
    Assignee: Akzo Nobel N.V.
    Inventors: Mats Nyström, Christina Järnvik, Hans Thor, Seppo Saari
  • Patent number: 6464954
    Abstract: A process for hydrogenating an anthraquinone compound or a mixture of two or more thereof utilizes specific catalysts comprising, as active metal, a metal of transition group VIII of the Periodic Table of the Elements.
    Type: Grant
    Filed: April 26, 2000
    Date of Patent: October 15, 2002
    Assignee: BASF Aktiengesellschaft
    Inventors: Arnd Böttcher, Jochem Henkelmann, Franz Josef Bröcker
  • Patent number: 6342196
    Abstract: A method for synthesizing hydrogen peroxide comprises the steps of: synthesizing an analog of anthraquinone that is miscible or soluble in carbon dioxide; reacting the analog of anthraquinone with hydrogen in carbon dioxide to produce a corresponding analog of tetrahydroquinone; and reacting the analog of tetrahydroquinone with oxygen to produce the hydrogen peroxide and regenerate the analog of anthraquinone. A chemical compound having the formula: wherein R1, R2, R3, R4, R5, R6, R7, and R8 are independently, the same or different, H, RC, or RSRC, wherein RS is a spacer group and RC is a fluoroalkyl group, a fluoroether group, a silicone group, an alkylene oxide group, a fluorinated acrylate group, or a phosphazine group, and wherein at least one of R1, R2, R3, R4, R5, R6, R7, and R8 is not H.
    Type: Grant
    Filed: June 29, 1998
    Date of Patent: January 29, 2002
    Assignee: University of Pittsburgh
    Inventors: Eric J. Beckman, Dan Hâncu
  • Patent number: 6333018
    Abstract: Process for the industrial production of hyperpure hydrogen peroxide also having high titre up to 60-70% by weight characterized in that the hydrogen peroxide produced in an industrial plant is directly fed to a purification unit, being part of the same production plant, in which the inverted osmosis, separation of the the high purity permeate flow and direct recycle of the concentrated flow to the production plant, are carried out.
    Type: Grant
    Filed: January 15, 1999
    Date of Patent: December 25, 2001
    Inventors: Ugo Piero Bianchi, Umberto Leone, Mauro Lucci
  • Publication number: 20010007045
    Abstract: A method for synthesizing hydrogen peroxide comprises the steps of: synthesizing an analog of anthraquinone that is miscible or soluble in carbon dioxide; reacting the analog of anthraquinone with hydrogen in carbon dioxide to produce a corresponding analog of tetrahydroquinone; and reacting the analog of tetrahydroquinone with oxygen to produce the hydrogen peroxide and regenerate the analog of anthraquinone.
    Type: Application
    Filed: June 29, 1998
    Publication date: July 5, 2001
    Inventors: ERIC J. BECKMAN, DAN HANCU
  • Patent number: 6153169
    Abstract: A cyclic anthraquinone process for producing hydrogen peroxide using at least two differently substituted 2-alkylanthraquinones and/or their tetrahydro derivatives. The working solution to be used contains (i) at least one reaction carrier from the series 2-(4-methyl-3-pentenyl) anthraquinone (IHEAQ), 2-(4-methylpentyl) anthraquinone (IHAQ) and their di- and tetrahydro derivatives such as, in particular 2-(4-methylpentyl)-.beta.-tetrahydroanthraquinone (THIHAQ), and (ii) at least one reaction carrier from the series of the 2-(C.sub.1 - to C.sub.5)-alkylanthraquinones, especially 2-ethylanthraquinone (EAQ), and their tetrahydro derivatives. The reaction carriers according to (i) make up 5 to 95 molar %, especially 20 to 50 molar % of all reaction carriers. The method is distinguished by greater H.sub.2 O.sub.2 capacity, improved hydrogenation kinetics and lesser susceptibility to disturbances. A method for making THIHAQ is also disclosed.
    Type: Grant
    Filed: October 20, 1998
    Date of Patent: November 28, 2000
    Assignee: Degussa-Huls Aktiengesellschaft
    Inventors: Jurgen Glenneberg, Gustaf Goor, Eugen Staab, Hubert Angert
  • Patent number: 5853693
    Abstract: A method for preparing hydrogen peroxide in accordance with an anthraquinone method, comprising hydrogenating at least one anthraquinone with a hydrogenation catalyst comprising palladium and at least one alkali metal, supported on a silica carrier, wherein the at least one alkali metal is in an amount of 0.1% to 5 wt % based on the weight of the silica carrier.
    Type: Grant
    Filed: March 19, 1997
    Date of Patent: December 29, 1998
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Kazuharu Ogasawara, Tomio Kato, Norikazu Okuda, Tetsuya Konishi, Kenji Kato
  • Patent number: 5827493
    Abstract: A method using auto-oxidation of an anthraquinone derivative in three successive steps, comprising hydrogenating the working solution (at 1), oxidizing the hydrogenated working solution (at 2), and removing hydrogen peroxide using water (at 3). The hydrogenation step is performed in such a way that a hydrogen peroxide equivalent of around 7.9 g/l is achieved at the inlet of the oxidizer (2), and the oxidation step (b) is performed in such a way that the temperature at the top of the oxidizer (2) is below about 50.degree. C., and preferably around 35.degree.-40.degree. C. The method is useful for producing hydrogen peroxide in situ in a paper pulp bleaching plant.
    Type: Grant
    Filed: October 15, 1996
    Date of Patent: October 27, 1998
    Assignee: Chemoxal S.A.
    Inventor: Henry Ledon
  • Patent number: 5674797
    Abstract: The invention relates to a method for regenerating a hydrogenation catalyst employed in the production of hydrogen peroxide, being characterized in that the catalyst to be regenerated is treated with an oxidized working solution used in the production of hydrogen peroxide.
    Type: Grant
    Filed: February 22, 1995
    Date of Patent: October 7, 1997
    Assignee: Finnish Chemicals Oy
    Inventors: Reijo Seppanen, Vesa Jokinen
  • Patent number: 5540906
    Abstract: Hydrogen peroxide is produced by oxidizing alkylammonium salts of sulfonic acid-substituted anthrahydroquinones. As said salts are highly soluble in protic polar solvents such as water and lower aliphatic alcohols, the concentration of hydrogen peroxide in the reaction product thereby obtained may be advantageously high. The anthraquinone salt co-product generated by such oxidation may be readily converted in high yield back to the starting anthrahydroquinone salt by hydrogenation.
    Type: Grant
    Filed: September 28, 1994
    Date of Patent: July 30, 1996
    Assignee: ARCO Chemical Technology, L.P.
    Inventors: Carmen L. Rodriguez, John G. Zajacek
  • Patent number: 5399333
    Abstract: A process for producing hydrogen peroxide by subjecting a working solution containing anthraquinones as the reaction medium, to reduction and oxidation alternately, which process is characterized in that (1) the anthraquinones as the reaction medium contained in the working solution are a mixture of an alkyl-substituted anthraquinone and an alkyl-substituted tetrahydroanthraquinone, (2) in the reduction step, the total amount of the alkyl-substituted tetrahydroanthraquinone in the working solution and part or the total amount of the alkyl-substituted anthraquinone in the working solution are reduced, and (3) in the working solution after the reduction step, the content of the alkyl-substituted anthrahydroquinone formed is kept higher than the content of the alkyl-substituted tetrahydroanthrahydroquinone formed.
    Type: Grant
    Filed: December 6, 1993
    Date of Patent: March 21, 1995
    Assignee: Mitsubishi Chemical Gas Co., Ltd.
    Inventors: Tomio Kato, Yukio Ishiuchi, Hiroshi Takamiya, Kazuharu Ogasawara, Kazuyuki Minato
  • Patent number: 5302367
    Abstract: Process for obtaining aqueous hydrogen peroxide solutions by the alkylanthraquinone process, providing a concentrated aqueous hydrogen peroxide solution with a low content of impurities, according to which a continuous addition of acidifying compounds and/or of stabilising compounds is performed, consisting in recycling towards the oxidation unit at least a part of the purge leaving the distillation unit.
    Type: Grant
    Filed: August 20, 1992
    Date of Patent: April 12, 1994
    Assignee: Interox International (Societe Anonyme)
    Inventors: Lido Signorini, Konstantin Glinos, Philippe Deroisy, Fabienne Banneux
  • Patent number: 4668436
    Abstract: A process is provided to regenerate and purify a working solution for the manufacture of hydrogen peroxide by the reduction and oxidation of a solution of alkylated anthraquinones and derivatives. The regeneration and purification is effected by removing inerts by contacting the working solution and an noncyclic hydrocarbon to form a liquid first phase and a second phase, separating the two phases and recovering both the noncyclic hydrocarbon and the purified working solution by distillation.
    Type: Grant
    Filed: December 13, 1985
    Date of Patent: May 26, 1987
    Assignee: FMC Corporation
    Inventor: Dalbir S. Sethi
  • Patent number: 4544543
    Abstract: The invention is for a process for removing unalkylated anthraquinones from alkylated anthraquinone by forming a solution thereof, reducing the solution sufficiently so that at least part of the unalkylated anthraquinone is in the reduced form, and extracting the reduced solution in the absence of an oxidizing agent with an aqueous alkaline solution. The process is especially suited for removing anthraquinone from an alkylated anthraquinone for use in the manufacture of hydrogen peroxide by reducing and oxidizing a solution of the alkylated anthraquinone.
    Type: Grant
    Filed: April 25, 1983
    Date of Patent: October 1, 1985
    Assignee: FMC Corporation
    Inventors: Nathan D. Lee, Dalbir S. Sethi
  • Patent number: 4374820
    Abstract: An alkylanthraquinone working solution as used in the manufacture of hydrogen peroxide, in the oxidized form is cooled to from 20.degree. to 40.degree. C. and fed to a slurry type catalytic hydrogenator maintained at from 38.degree. to 60.degree. C., and 10 to 100 psig. From 10 to 90% of the catalyst free hydrogenated working solution is cooled to from 20.degree. to 40.degree. C. and recycled to the hydrogenator.
    Type: Grant
    Filed: July 29, 1981
    Date of Patent: February 22, 1983
    Assignee: E. I. Du Pont de Nemours and Company
    Inventor: Thomas E. Guenter