Purification Or Recovery Per Se Patents (Class 562/600)
  • Patent number: 10906862
    Abstract: A process for isolating pure butyl acrylate from crude butyl acrylate, which is carried out in a dividing wall column having separation-active internals and a vaporizer, and in which: a dividing wall is arranged in a longitudinal direction of the column to form an upper joint column region, a lower joint column region, an inflow section having a side feed point and an offtake section having a side offtake point; a ratio of an amount of liquid at an upper end of the dividing wall going to an enrichment section and a stripping section of the column is set in the range from 1:0.2 to 1:5; and a ratio of an amount of vapor streams at a lower end of the dividing wall going to the stripping section and the enrichment section of the column is set in a range from 1:0.5 to 1:2.0.
    Type: Grant
    Filed: December 11, 2017
    Date of Patent: February 2, 2021
    Assignee: BASF SE
    Inventors: Ortmund Lang, Bernd Metzen, Claus Hechler
  • Patent number: 10766848
    Abstract: The present invention relates to the use of at least two phenol derivatives jointly with at least one ancillary polymerization inhibitor which is different from these two phenol derivatives and particularly is selected from phenol derivatives, amine derivatives, thiazine derivatives, nitroso compounds, N-oxyl derivatives, metal salts, quinone derivatives, and mixtures thereof, to inhibit the polymerization of ethylenically unsaturated monomers comprising at least one heteroatom, it being also possible for a dispersant to be incorporated. The present invention also relates to a corresponding polymerization-inhibiting composition and to the corresponding process for preparing ethylenically unsaturated monomers comprising at least one heteroatom, and particularly acrylic monomers.
    Type: Grant
    Filed: September 7, 2015
    Date of Patent: September 8, 2020
    Assignee: RHODIA OPERATIONS
    Inventors: Christelle Chretien, Karel Vits, Lars Fischer, Yan Shi
  • Patent number: 10717695
    Abstract: Provided are integrated processes for the conversion of beta propiolactone to acrylic acid. Systems for the production of acrylic acid are also provided.
    Type: Grant
    Filed: August 21, 2018
    Date of Patent: July 21, 2020
    Assignee: Novomer, Inc.
    Inventor: Sadesh H. Sookraj
  • Patent number: 10647657
    Abstract: The invention relates to a method for producing alkyl (meth)acrylate comprising a linear or branched alkyl chain comprising 4 to 10 carbon atoms, by direct esterification of (meth)acrylic acid with a linear or branched alcohol comprising 4 to 10 carbon atoms in the presence of a catalyst, leading to formation of a reaction mixture comprising the desired ester, unreacted acid and alcohol, light by-products, and heavy by-products. The mixture undergoes purification treatment by separation means to obtain purified alkyl (meth)acrylate. The purification treatment comprises a step of membrane separation dehydration applied to at least one of the following: the stream subjected to the final distillation leading to the recovery of the purified (meth)acrylic ester, the aqueous stream originating from the settling out of the reaction mixture, or the stream resulting from the distillation of the light by-products present in the reaction mixture.
    Type: Grant
    Filed: December 9, 2014
    Date of Patent: May 12, 2020
    Assignee: ARKEMA FRANCE
    Inventors: Serge Tretjak, Anne Moreliere
  • Patent number: 10610803
    Abstract: The present invention relates to a method for continuous recovery of (meth)acrylic acid and an apparatus used for the recovery method. The recovery method according to the present invention enables stable recovery of (meth)acrylic acid and the operation of a continuous process, while securing a high (meth)acrylic acid recovery rate through a solvent recovery process.
    Type: Grant
    Filed: November 8, 2017
    Date of Patent: April 7, 2020
    Assignee: LG CHEM, LTD.
    Inventors: Yoon Jae Min, Se Won Baek, Jong Hun Song, Jae Yul Kim
  • Patent number: 10487036
    Abstract: The present invention relates to a method for continuous recovery of (meth)acrylic acid and an apparatus used for the recovery method. The recovery method according to the present invention enables stable recovery of (meth)acrylic acid and the operation of a continuous process, while securing a high (meth)acrylic acid recovery rate through the acetic acid separation process.
    Type: Grant
    Filed: November 8, 2017
    Date of Patent: November 26, 2019
    Assignee: LG CHEM, LTD.
    Inventors: Yoon Jae Min, Se Won Baek, Jong Hun Song, Jae Yul Kim
  • Patent number: 10421905
    Abstract: The invention relates to a process for preparing concentrated solutions of polymerization inhibitor, that can be used for the production, purification and storage of monomer compositions. This process comprises a step in which at least one polymerization inhibitor in the molten state is mixed with a solvent.
    Type: Grant
    Filed: February 22, 2016
    Date of Patent: September 24, 2019
    Assignee: Rhodia Operations
    Inventors: Jacques Cavezzan, Sébastien Lomel, Christian Rouyer, Terry Chamberlain
  • Patent number: 10406452
    Abstract: The invention is directed to an improvement in operation of wash columns, and more in particular to an apparatus for separating solid particles from a slurry and to a process for separating solid particles from a mother liquor slurry. The apparatus of the invention comprises a wash column (1), which comprises a melting circuit (8,10,11,21), wherein means (22,23) are present to introduce a compound or composition to said wash column between a wash front (6b) formed in said wash column in operation and a product outlet and/or in the melting circuit.
    Type: Grant
    Filed: January 3, 2012
    Date of Patent: September 10, 2019
    Assignee: NEDERLANDSE ORGANISATIE VOOR TOEGEPAST-NATUURWETENSCHAPPELIJK ONDERZOEK TNO
    Inventors: Dirk Verdoes, Johannes van der Meer, Michiel Nienoord, Michael Sell, Jean-Marie Collard
  • Patent number: 10350539
    Abstract: The present invention relates to a method of recovering (meth)acrylic acid and an apparatus used for the recovery method. The recovery method according to the present invention discharges each (meth)acrylic acid aqueous solution of different concentrations at a (meth)acrylic acid absorption tower, and uses an extraction solvent of a specific ratio in the step of extracting (meth)acrylic acid, thus enabling the operation of a continuous process of recovering (meth)acrylic acid that can secure a high (meth)acrylic acid recovery rate, and can simultaneously significantly reduce purification energy cost.
    Type: Grant
    Filed: December 5, 2017
    Date of Patent: July 16, 2019
    Assignee: LG CHEM, LTD.
    Inventors: Jong Hun Song, Se Won Baek, Yoon Jae Min, Jae Yul Kim
  • Patent number: 9783479
    Abstract: The invention relates to the production of (meth)acrylic acid, and to implementation of a step of condensing water contained in a recycled gas effluent and/or in the air feed in a (meth)acrylic acid production process, which further includes a process for purifying a reaction mixture comprising (meth)acrylic acid without using azeotropic solvent and based on the use of two distillation columns.
    Type: Grant
    Filed: March 8, 2017
    Date of Patent: October 10, 2017
    Assignee: Arkema France
    Inventors: Sandeep Jain, Christian Lacroix
  • Patent number: 9546124
    Abstract: Disclosed is a method of preparing acrylic acid from glycerol, including: (a) preparing products including allyl alcohol from reactants including glycerol and carboxylic acid; (b) adding a heterogeneous catalyst and a basic solution to the product including allyl alcohol and then performing oxidation, thus preparing a mixture composed of 3-hydroxypropionic acid and acrylic acid; (c) dehydrating 3-hydroxypropionic acid of the mixture composed of 3-hydroxypropionic acid and acrylic acid, thus producing acrylic acid.
    Type: Grant
    Filed: June 27, 2014
    Date of Patent: January 17, 2017
    Assignee: LG CHEM, LTD.
    Inventors: Won Jae Lee, Yong-Jin Choe, Hyun Nam, Myungjin Kong
  • Patent number: 9458080
    Abstract: A process for obtaining acrylic acid, comprising (a) providing a liquid stream S7 comprising acetic acid and acrylic acid, where the molar ratio of acetic acid to acrylic acid in stream S7 is greater than 1:1, (b-1) crystallizing a portion of the acetic acid present in stream S7 to obtain solid crystallized acetic acid in its mother liquor, (b-2) separating the mother liquor from the acetic acid crystallized in (b-1) to obtain the solid crystallized acetic acid and a liquid stream S8 comprising acrylic acid and acetic acid, (c) separating stream S8 into at least one stream S10 depleted of acrylic acid compared to S8 and a stream S11 enriched in acrylic acid compared to S8.
    Type: Grant
    Filed: December 3, 2015
    Date of Patent: October 4, 2016
    Assignee: BASF SE
    Inventors: Nicolai Tonio Woerz, Lukas Schulz, Tim Blaschke, Marco Hartmann, Feelly Ruether, Yan Li
  • Patent number: 9371261
    Abstract: An aim of the present invention is to produce, from glycerol, a bioresourced acrylic acid, that is to say an acrylic acid essentially based on a carbon source of natural origin, meeting all the quality criteria of monomers customarily used as starting material in processes for polymerization of acrylic acid and of its esters, via an economical process. The process according to the invention comprises a final stage of extraction of acrylic acid by fractional crystallization applied to one of the effluents resulting from the acrylic acid purification chain, the location of this final stage possibly depending on the initial feedstock treated, the nature and the source of the glycerol used in the process, purity specifications to be achieved for the final acrylic acid, or finally economic criteria.
    Type: Grant
    Filed: June 29, 2010
    Date of Patent: June 21, 2016
    Assignee: ARKEMA FRANCE
    Inventor: Michel Fauconet
  • Patent number: 9212122
    Abstract: A process for inhibiting unwanted free-radical polymerization of acrylic acid present in a liquid phase P whose acrylic acid content is at least 10% by weight and which, based on the weight of the acrylic acid present therein, additionally comprises at least 100 ppm by weight of propionic acid and at least 100 ppm by weight of glyoxal, in which at least one chemical compound of the element copper is added to the liquid phase P, and the resulting liquid phases P to which a chemical compound of the element copper has been added.
    Type: Grant
    Filed: October 5, 2011
    Date of Patent: December 15, 2015
    Assignee: BASF SE
    Inventors: Till Blum, Peter Zurowski, Tobias Johannes Korn, Sylke Haremza, Thorsten Friese, Friedrich-Georg Martin, Ulrich Jäger, Steffen Rissel, Volker Schliephake
  • Patent number: 9162962
    Abstract: The invention relates to a process for reclaiming methacrylic acid from a high-boiler phase in a heterogeneously catalysed gas phase oxidation of a C4-compound to methacrylic acid comprising the following steps a) Providing a high-boiler phase from a heterogeneously catalysed gas phase oxidation of a C4-compound to methacrylic acid b) Providing an aqueous phase, preferably organically loaded, from a heterogeneously catalysed gas phase oxidation of a C4-compound to methacrylic acid c) Mixing of components a) and b) optionally followed by filtration or centrifugation d) Adding an extraction media to the mixture from c) e) Subjecting the multiple-phase mixture from d) to at least one mixer-settler extraction process f) Recycling the organic phase from the last mixer-settler process back into the C4-process
    Type: Grant
    Filed: September 16, 2011
    Date of Patent: October 20, 2015
    Assignee: Evonik Röhm GmbH
    Inventors: Henning Schaefer, Torsten Balduf, Patrick Peter
  • Patent number: 9156769
    Abstract: Improvement in separating lower carboxylic acids from aqueous streams via liquid-liquid extraction with pressurized liquefied propylene and/or propane, wherein carboxylic acid is transferred from the aqueous phase into the liquid solvent phase (extract). The extracted carboxylic acids are recovered as a liquid concentrate by evaporating off the propylene and/or propane solvent from the extract at mild temperatures.
    Type: Grant
    Filed: March 24, 2014
    Date of Patent: October 13, 2015
    Assignee: Arkema Inc.
    Inventor: Steven G. Schon
  • Patent number: 9150483
    Abstract: An aqueous solution comprising acrylic acid and the conjugate base thereof in a total amount of at least 10% by weight, based on the weight of the aqueous solution, and propionic acid and the conjugate base thereof, formic acid and the conjugate base thereof, acetic acid and the conjugate base thereof, benzoic acid and the conjugate base thereof, maleic anhydride, maleic acid and the conjugate bases thereof, phthalic anhydride, phthalic acid and the conjugate bases thereof, acrolein, benzaldehyde, 2-furaldehyde, and at least 20 mol % of at least one alkali metal cation; process for preparing this solution; and the use of this solution for preparation of polymer by free-radical polymerization.
    Type: Grant
    Filed: May 30, 2012
    Date of Patent: October 6, 2015
    Assignee: BASF SE
    Inventors: Frank Huetten, Otto Machhammer, Thomas Daniel, Markus Ottenbacher, Daniel Pfeiffer, Stefanie Herzog, Manfred Heilig, Klaus Joachim Mueller-Engel
  • Patent number: 9096513
    Abstract: A process for inhibiting unwanted free-radical polymerization of acrylic acid present in a liquid phase P whose acrylic acid content is at least 10% by weight and which, based on the weight of the acrylic acid present therein, additionally comprises at least 100 ppm by weight of propionic acid and at least 100 ppm by weight of glyoxal, in which at least one chemical compound of the element copper is added to the liquid phase P, and the resulting liquid phases P to which a chemical compound of the element copper has been added.
    Type: Grant
    Filed: October 5, 2011
    Date of Patent: August 4, 2015
    Assignee: BASF SE
    Inventors: Till Blum, Peter Zurowski, Tobias Johannes Korn, Sylke Haremza, Thorsten Friese, Friedrich-Georg Martin, Ulrich Jäger, Steffen Rissel, Volker Schliephake
  • Patent number: 9029599
    Abstract: A process for producing (meth)acrylic acid comprising the step of repeating a crystallization operation “n” times to produce purified (meth)acrylic acid from crude (meth)acrylic acid, wherein: the each crystallization operation comprises a crystallizing step and a melting step; a polymerization inhibitor is not added to a (meth)acrylic acid melt obtained in the melting step of the first to n?1th crystallization operation(s) and a (meth)acrylic acid solution subjected to the crystallizing step of the second to nth crystallization operation(s); and a concentration of a polymerization inhibitor in a (meth)acrylic acid solution subjected to the crystallizing step of the first crystallization operation is adjusted so that a concentration of the polymerization inhibitor in a (meth)acrylic acid solution subjected to the crystallizing step of the nth crystallization operation is 2 ppm by mass or higher.
    Type: Grant
    Filed: September 3, 2013
    Date of Patent: May 12, 2015
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Takashi Miyamoto, Yoshitake Ishii, Toyofumi Sakai
  • Patent number: 9018416
    Abstract: A thermal separation process between a gas ascending in a separating column and a liquid descending in the separating column, which comprise (meth)acrylic monomers, wherein the separating column comprises a sequence of crossflow mass transfer trays, the crossflow mass transfer trays of which have passage orifices for the ascending gas in crossflow direction both in front of and beyond a downcomer for the descending liquid, and such crossflow mass transfer trays and one such crossflow mass transfer tray in a sequence of crossflow mass transfer trays present in a separating column.
    Type: Grant
    Filed: March 14, 2013
    Date of Patent: April 28, 2015
    Assignee: BASF SE
    Inventors: Klaus Joachim Mueller-Engel, Thomas Walter, Frank Huetten, Markus Ottenbacher, Ulrich Hammon
  • Publication number: 20150018576
    Abstract: The invention relates to a method for producing a product mixture (2) by means of the technical hydroformylation of a hydrocarbon stream (1) that contains isobutene, and for separating the product mixture (2) that is obtained, as well as to a device for the claimed method and to the use of a claimed device. The problem addressed thereby is that of providing a method and an associated device that allow the amount of high-boiling substances in the product mixture (2) to be kept as low as possible and thus the yield of the reaction to be increased. The problem is solved by the use of a nano-filtration device (M) for separating the catalyst from the product mixture (2), said device having especially high permeability to 3-methylbutanoic acid.
    Type: Application
    Filed: February 11, 2013
    Publication date: January 15, 2015
    Applicant: Evonik Degussa GmbH
    Inventors: Goetz Baumgarten, Michael Grass, Alfred Kaizik, Markus Winterberg, Hans-Gerd Lueken, Bart Hamers, Markus Priske, Dirk Fridag, Robert Franke, Dieter Hess
  • Patent number: 8932434
    Abstract: There are provided a dividing wall distillation column for producing high-purity acrylic acid, and a fractional distillation method using the same. The dividing wall distillation column includes a condenser, a reboiler and a main column having a dividing wall. Here, the main column is divided into a column-top zone, an upper feed zone, an upper outflow zone, a lower feed zone, a lower outflow zone and a column-bottom zone. Accordingly, since one distillation column can be used to realize the same effect as that obtained from the use of two distillation columns, the dividing wall distillation column can have an effect of reducing the costs of equipment to produce high-purity acrylic acid, as well as an energy-reducing effect, compared to a conventional process system.
    Type: Grant
    Filed: March 19, 2010
    Date of Patent: January 13, 2015
    Assignee: LG Chem, Ltd.
    Inventors: Sung Kyu Lee, Jong Ku Lee, Joon Ho Shin
  • Publication number: 20140378702
    Abstract: In one embodiment, the present invention is directed to a process for producing an acrylate product. The process comprises the step of reacting, optionally in a reaction zone, a reaction mixture comprising an alkanoic acid and an alkylenating agent under conditions effective to form a crude acrylate product. The crude acrylate product comprises acrylate product and acetic acid. The process further comprises the step of reacting, in a separation zone, at least a portion of the acrylate product and at least a portion of the acetic acid to form an intermediate acrylate product. The intermediate acrylate product comprises a Michael addition by-product, e.g., 3-acetoxypropionic acid and/or 3-acetoxypropanoic acid. The process further comprises the step of separating at least a portion of the intermediate acrylate product to form a by-product stream and a purified acrylate product stream.
    Type: Application
    Filed: June 25, 2013
    Publication date: December 25, 2014
    Inventors: Craig J. Peterson, Elizabeth Bowden, Josefina T. Chapman, Sean Mueller
  • Publication number: 20140371488
    Abstract: There are provided a dividing wall distillation column for producing high-purity acrylic acid, and a fractional distillation method using the same. The dividing wall distillation column includes a condenser, a reboiler and a main column having a dividing wall. Here, the main column is divided into a column-top zone, an upper feed zone, an upper outflow zone, a lower feed zone, a lower outflow zone and a column-bottom zone. Also, a crude acrylic acid raw material (F) flows in a middle inflow plate NR1 in which the upper feed zone and the lower teed zone come in contact with each other, a low boiling point component (I)) flows out from the column-top zone, a high boiling point component (B) flows out from the column-bottom zone, and a middle boiling point component (S) flows out through a middle outflow plate NR2 in which the upper outflow zone and the lower outflow zone come in contact with each other. In this case, the middle boiling point component is acrylic acid. Accordingly.
    Type: Application
    Filed: August 28, 2014
    Publication date: December 18, 2014
    Inventors: Sung Kyu LEE, Jong Ku LEE, Joon Ho SHIN
  • Publication number: 20140364646
    Abstract: Provided is a crystallization method by which a highly-pure methacrylic acid crystal can be produced with high productivity. The method for purifying methacrylic acid according to the present disclosure involves using crude methacrylic acid having a maleic acid concentration of 2000 ppm by mass or less and an acrylic acid concentration of 2000 ppm by mass or less and setting the slurry temperature to ?10 to 10° C. in order to crystallize methacrylic acid. A suspension-type jacket-cooling-system crystallization vessel is used as the crystallization apparatus, and an absolute value of the difference between a crystallization temperature and a temperature of a cooling medium in the jacket is preferably 15° C. or less.
    Type: Application
    Filed: December 26, 2012
    Publication date: December 11, 2014
    Inventors: Tomomichi Hino, Shinpei Kato, Hideyuki Sonobe, Manabu Hoshino
  • Patent number: 8895683
    Abstract: In one aspect, a process for the preparation of a superabsorbent polymer is described herein. In some embodiments, the process comprises (I) preparing acrylic acid, wherein the process comprises (a1) provision of a fluid F1 having a composition comprising from about 5 to about 20 wt. % of hydroxypropionic acid, salts thereof, or mixtures thereof; from about 0.1 to about 5 wt. % of inorganic salts; from about 0.1 to about 30 wt. % of organic compounds which differ from hydroxypropionic acid; from 0 to about 50 wt. % of solids; and from about 20 to about 90 wt. % of water; (a2) dehydration of said hydroxypropionic acid to give a fluid F2 containing acrylic acid; and (a3) purification of said fluid F2 to give a purified acrylic acid phase comprising acrylic acid having a purity of at least 70 wt. %; and (II) polymerizing the acrylic acid of (I) to form a superabsorbent polymer.
    Type: Grant
    Filed: May 17, 2013
    Date of Patent: November 25, 2014
    Assignee: Evonik Degussa GmbH
    Inventors: Franz-Felix Kuppinger, Axel Hengstermann, Guido Stochniol, Gunther Bub, Jurgen Mosler, Andreas Sabbagh
  • Patent number: 8864950
    Abstract: A process for producing an acrylate product. The process comprises the step of providing a crude product stream comprising the acrylate product and an alkylenating agent. The process further comprises the step of separating at least a portion of the crude product stream to form an alkylenating agent stream and an intermediate product stream. The alkylenating agent stream comprises at least 1 wt % alkylenating agent and the intermediate product stream comprises acrylate product. The separating is performed in at least one column at an operating pressure ranging from 40 kPa to 80 kPa.
    Type: Grant
    Filed: January 6, 2012
    Date of Patent: October 21, 2014
    Assignee: Celanese International Corporation
    Inventors: Craig Peterson, Josefina Chapman, Jonathan Gallacher
  • Patent number: 8859809
    Abstract: A crystallization device and a crystallization process are provided for obtaining (meth)acrylic acid with higher purity without causing leakage of a crude solution by preventing complete clogging in a crystallization tube from occurring. The device for crystallizing (meth)acrylic acid includes a crude (meth)acrylic acid solution supply part, a crystallization tube, a heat medium supply tube, a heat medium discharge tube, a storage part of a crude (meth)acrylic acid solution passed through the crystallization tube, a tube for circulating and supplying the crude (meth)acrylic acid solution to the supply part from the storage part, and a pump for circulating and supplying the crude (meth)acrylic acid solution to the supply part from the storage part, and also includes a pressure meter in the circulate-supply tube.
    Type: Grant
    Filed: June 24, 2010
    Date of Patent: October 14, 2014
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Kazuhiko Sakamoto, Koji Ueno, Yoshitake Ishii, Masatsugu Kitaura
  • Patent number: 8846977
    Abstract: PROBLEM An object of the present invention is to provide a crystallization unit capable of producing a purified acrylic acid having high purity efficiently. SOLUTION The present invention provides a crystallization unit to separate an acrylic acid-containing solution into a mother liquid and a purified acrylic acid, wherein the crystallization unit comprises a crystallizer having an exit to take out the mother liquid and the purified acrylic acid alternately; a supply line to supply the acrylic acid-containing solution to the crystallizer; and a recovery line to recover the mother liquid and the purified acrylic acid alternately from the crystallizer which is connected to the exit, and wherein the recovery line is equipped with an opening and closing unit consisting of a ball valve or a gate valve.
    Type: Grant
    Filed: June 24, 2010
    Date of Patent: September 30, 2014
    Assignee: Nippon Shokubai Co. Ltd.
    Inventors: Kazuhiko Sakamoto, Koji Ueno, Yoshitake Ishii, Masatsugu Kitaura
  • Patent number: 8829134
    Abstract: A process for transporting a liquid monomer phase which has been withdrawn from a storage vessel and comprises methacrylic monomers to an extent of ?90% by weight, in a tank truck or in a tanker ship, in which the liquid monomer phase is subjected to a separating operation on the route from the storage vessel into the tank of a tank truck or of a tanker ship in order to separate polymer of the monomer present in dissolved form in the liquid monomer phase.
    Type: Grant
    Filed: March 21, 2008
    Date of Patent: September 9, 2014
    Assignee: BASF SE
    Inventors: Joerg Heilek, Ulrich Hammon, Volker Schliephake, Klaus Joachim Mueller-Engel, Till Blum
  • Patent number: 8802585
    Abstract: In one embodiment, the invention is to a catalyst composition comprising vanadium and titanium. The catalyst composition has a surface area of at least 22.6 m2/g and a plurality of pores, and the plurality of pores have a pore diameter of less than 11.9 nm.
    Type: Grant
    Filed: September 22, 2011
    Date of Patent: August 12, 2014
    Assignee: Celanese International Corporation
    Inventors: Heiko Weiner, Josefina T. Chapman, Alexandra S. Locke, Craig T. Peterson, Mark O. Scates, Dick Nagaki
  • Publication number: 20140221686
    Abstract: Improvement in separating lower carboxylic acids from aqueous streams via liquid-liquid extraction with pressurized liquefied propylene and/or propane, wherein carboxylic acid is transferred from the aqueous phase into the liquid solvent phase (extract). The extracted carboxylic acids are recovered as a liquid concentrate by evaporating off the propylene and/or propane solvent from the extract at mild temperatures.
    Type: Application
    Filed: March 24, 2014
    Publication date: August 7, 2014
    Applicant: Arkema Inc.
    Inventor: Steven G. Schon
  • Publication number: 20140221687
    Abstract: The invention relates to a process for reclaiming methacrylic acid from a high-boiler phase in a heterogeneously catalysed gas phase oxidation of a C4-compound to methacrylic acid comprising the following steps a) Providing a high-boiler phase from a heterogeneously catalysed gas phase oxidation of a C4-compound to methacrylic acid b) Providing an aqueous phase, preferably organically loaded, from a heterogeneously catalysed gas phase oxidation of a C4-compound to methacrylic acid c) Mixing of components a) and b) optionally followed by filtration or centrifugation d) Adding an extraction media to the mixture from c) e) Subjecting the multiple-phase mixture from d) to at least one mixer-settler extraction process f) Recycling the organic phase from the last mixer-settler process back into the C4-process.
    Type: Application
    Filed: September 16, 2011
    Publication date: August 7, 2014
    Applicant: EVONIK ROEHM GMBH
    Inventors: Henning Schaefer, Torsten Balduf, Patrick Peter
  • Patent number: 8791296
    Abstract: The present invention relates to a process for preparing methacrylic acid based on the hydrolysis of methacrylic esters.
    Type: Grant
    Filed: April 24, 2012
    Date of Patent: July 29, 2014
    Assignee: Evonik Roehm GmbH
    Inventors: Dirk Broell, Hermann Siegert, Horst Hiltner, Thomas Krauss
  • Publication number: 20140200366
    Abstract: The present invention provides a method for reducing accumulation of solid materials when manufacturing a (meth)acrylic acid ester having low biacetyl content (less than 2 ppm) by adding an aromatic diamine under conditions which provide sufficient residence time and thorough mixing to react up to 100% by weight of the biacetyl in the crude (meth)acrylic acid ester stream, prior to separation and purification. A feedback method is also provided for reducing solids accumulation in the separation and purification equipment of such processes by measuring the biacetyl content and adjusting the aromatic diamine addition rate so that excess aromatic diamine can be minimized. A third embodiment provides a method for reversing an accumulation of solid materials during such processes, while still producing a (meth)acrylic acid ester having low biacetyl content (less than 2 ppm), by reducing or ceasing the addition rate of aromatic diamine for a period of time.
    Type: Application
    Filed: June 1, 2012
    Publication date: July 17, 2014
    Applicant: ROHM AND HAAS COMPANY
    Inventors: Michael A. Curtis, Michael S. Decourcy, David A. Flosser, Melissa Harris, Jamie J. Juliette, Philippe P. Maillot
  • Publication number: 20140187817
    Abstract: The invention relates to a process for preparation of methacrylic acid, comprising process steps a) providing a crude methacrylic acid-comprising aqueous solution comprising at least one impurity at least partially dissolved therein; b) precipitation of at least a part of the at least one impurity from the crude methacrylic acid-comprising aqueous solution to form at least one solid impurity and a mother liquor; c) separation of at least a part of the at least one solid impurity from the mother liquor to obtain a purified methacrylic acid-comprising aqueous solution and a solid impurity; d) separation of methacrylic acid from the purified methacrylic acid-comprising aqueous solution.
    Type: Application
    Filed: September 16, 2011
    Publication date: July 3, 2014
    Applicant: Evonik Roehm GmbH
    Inventors: Torsten Balduf, Martin Koestner, Wenxing Zhang, Heidi Groen, Axel Hengstermann, Maya Krapfl
  • Patent number: 8735314
    Abstract: In one embodiment, the invention is to a catalyst composition comprising vanadium and titanium. The catalyst composition further comprises ethylene glycol and citric acid. Preferably, the catalyst composition is substantially free of oxalic acid and lactic acid.
    Type: Grant
    Filed: September 29, 2011
    Date of Patent: May 27, 2014
    Assignee: Celanese International Corporation
    Inventors: Dick Nagaki, Craig Peterson, Mark Scates, Heiko Weiner, Josefina T. Chapman, Alexandra S. Locke
  • Patent number: 8716525
    Abstract: The present invention relates to a method and apparatus for continuous recovery of (meth)acrylic acid, and more specifically to a method of continuous recovery of (meth)acrylic acid, including: conducting gas phase oxidation of at least one compound selected from the group consisting of propane, propylene, butane, i-butylene, t-butylene, and (meth)acrolein in the presence of a catalyst to obtain a mixed gas containing (meth)acrylic acid; quenching the (meth)acrylic acid-containing mixed gas to remove high boiling point by-products in the (meth)acrylic acid-containing mixed gas; contacting the high boiling point by-product-free (meth)acrylic acid-containing mixed gas with water or an aqueous solution to obtain an aqueous solution containing (meth)acrylic acid; and purifying the aqueous solution containing (meth)acrylic acid to obtain (meth)acrylic acid.
    Type: Grant
    Filed: July 29, 2013
    Date of Patent: May 6, 2014
    Assignee: LG Chem, Ltd.
    Inventors: Se-Won Baek, Hyun-Kyu Kim, Dong-Hyun Cho, Jun-Seok Ko
  • Patent number: 8704000
    Abstract: PROBLEM There is provided a melting method of (meth)acrylic acid crystal which is capable of providing a higher quality of (meth)acrylic acid without carrying out an additional purification treatment to (meth)acrylic acid obtained by a crystallization operation accompanied by melting of (meth)acrylic acid. In addition, there is provided a simple method for adjusting a content of polymerization inhibitor in a product (meth)acrylic acid. SOLUTION In the crystallization method melting (meth)acrylic acid crystal while wetting with the crystalline molten liquid, a polymerization inhibitor is added to a molten liquid melted after initiation of melting, and all of crystal is melted while circulating and feeding the molten liquid containing said polymerization inhibitor to the crystal.
    Type: Grant
    Filed: May 27, 2010
    Date of Patent: April 22, 2014
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Kazuhiko Sakamoto, Koji Ueno, Yoshitake Ishii, Harunori Hirao, Satoshi Nakagawa
  • Patent number: 8680331
    Abstract: The objective of the present invention is to provide a process for production of (meth)acrylic acid with improved production efficiency by efficiently shifting from heating procedure to cooling procedure for a crystallizer. A process for production of (meth)acrylic acid according to the present invention is characterized in comprising the steps of crystallizing (meth)acrylic acid from a crude (meth)acrylic acid solution by using a batch type crystallizer, and melting the obtained (meth)acrylic acid crystal to obtain a (meth)acrylic acid melted liquid; wherein preliminary cooling of the crystallizer for the next crystallization step is started during transferring the (meth)acrylic acid melted liquid from the crystallizer.
    Type: Grant
    Filed: June 24, 2010
    Date of Patent: March 25, 2014
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Kazuhiko Sakamoto, Koji Ueno, Yoshitake Ishii, Satoshi Nakagawa
  • Patent number: 8680330
    Abstract: A process for producing (meth)acrylic acid of the present invention comprises the steps in the following order: a crystallization step of supplying a cooling medium cooled by a heat source device to a crystallizer to obtain a (meth)acrylic acid crystal from a crude (meth)acrylic acid solution; an adjustment step of returning the cooling medium discharged from the crystallizer to the crystallizer without cooling; a sweating step of supplying a heating medium to the crystallizer to partially melt the (meth)acrylic acid crystal, thereby obtaining a melted liquid, and discharging the melted liquid from the crystallizer; and a melting step of supplying the heating medium to the crystallizer to melt the (meth)acrylic acid crystal, thereby obtaining purified (meth)acrylic acid. According to the present invention, purified (meth)acrylic acid with high purity can be obtained.
    Type: Grant
    Filed: January 29, 2010
    Date of Patent: March 25, 2014
    Assignee: Nippon Shokubai Co., Ltd.
    Inventors: Kazuhiko Sakamoto, Koji Ueno, Yoshitake Ishii, Takashi Sugimoto, Masatsugu Kitaura, Satoshi Nakagawa, Kunihiko Suzuki
  • Publication number: 20140066652
    Abstract: A process for producing (meth)acrylic acid comprising the step of repeating a crystallization operation “n” times to produce purified (meth)acrylic acid from crude (meth)acrylic acid, wherein: the each crystallization operation comprises a crystallizing step and a melting step; a polymerization inhibitor is not added to a (meth)acrylic acid melt obtained in the melting step of the first to n?1th crystallization operation(s) and a (meth)acrylic acid solution subjected to the crystallizing step of the second to nth crystallization operation(s); and a concentration of a polymerization inhibitor in a (meth)acrylic acid solution subjected to the crystallizing step of the first crystallization operation is adjusted so that a concentration of the polymerization inhibitor in a (meth)acrylic acid solution subjected to the crystallizing step of the nth crystallization operation is 2 ppm by mass or higher.
    Type: Application
    Filed: September 3, 2013
    Publication date: March 6, 2014
    Applicant: Nippon Shokubai Co., Ltd.
    Inventors: Takashi MIYAMOTO, Yoshitake ISHII, Toyofumi SAKAI
  • Patent number: 8664437
    Abstract: A process for producing (meth)acrylic acid, comprising the step of repeating a crystallization operation “n” times (providing “n” is an integer 2 or more) to produce purified (meth)acrylic acid from crude (meth)acrylic acid, wherein a (meth)acrylic acid solution is crystallized and the crystallized (meth)acrylic acid is melted to obtain a (meth)acrylic acid melt in the crystallization operation; wherein a constant amount Ak of the (meth)acrylic acid solution is subjected to the kth crystallization operation (providing “k” is an integer 1 to n?1), and the (meth)acrylic acid melt obtained by the kth crystallization operation is utilized as the (meth)acrylic acid solution for the k+1th crystallization operation without being discharged from a crystallizer or is transferred from the crystallizer to a k+1th storage tank for storing the (meth)acrylic acid solution to be used in the k+1th crystallization operation depending on the stored amount of the k+1th storage tank.
    Type: Grant
    Filed: June 24, 2010
    Date of Patent: March 4, 2014
    Assignee: Nippon Shokubai Co., Ltd.
    Inventor: Satoshi Nakagawa
  • Patent number: 8658824
    Abstract: In one embodiment, the invention is to a process for producing an acrylate product. The process comprises the step of providing a crude product stream comprising the acrylate product, an alkylenating agent, and water. The process further comprises the step of contacting at least a portion of the crude product stream or a derivative thereof with an extraction agent mixture to form an extract stream and a raffinate stream. The extract stream comprises acrylate product and extraction agent. The raffinate stream comprises alkylenating agent and water. Preferably, the extraction agent mixture comprises at least two extraction agents.
    Type: Grant
    Filed: March 15, 2012
    Date of Patent: February 25, 2014
    Assignee: Celanese International Corporation
    Inventors: Craig Peterson, Josefina Chapman, R. Jay Warner, Mark Scates
  • Patent number: 8658823
    Abstract: In one embodiment, the invention is to a process for producing an acrylate product. The process comprises the step of providing a crude product stream comprising the acrylate product and an alkylenating agent. The process further comprises the step of separating at least a portion of the crude product stream to form an alkylenating agent stream and an intermediate product stream. The alkylenating agent stream comprises at least 1 wt % alkylenating agent and the intermediate product stream comprises acrylate product.
    Type: Grant
    Filed: October 3, 2011
    Date of Patent: February 25, 2014
    Assignee: Celanese International Corporation
    Inventors: Craig Peterson, Josefina Chapman, Ilias Kotsianis, Sean Mueller, Dick Nagaki, Tianshu Pan
  • Publication number: 20140031501
    Abstract: A method of extracting (meth)acrylic acid from an aqueous reaction medium into an organic phase in contact therewith is described. The aqueous reaction medium is formed from at least one base catalyst and at least one dicarboxylic acid selected from maleic, fumaric, malic, itaconic, citraconic, mesaconic, and citramalic acid or mixtures thereof in aqueous solution and contains the base catalysed decarboxylation products of the base catalysed reaction. The method includes either the addition of at least one of the said dicarboxylic acids and/or a pre-cursor thereof to the aqueous reaction medium to enhance the solvent extraction of the (meth)acrylic acid into the organic solvent or maintaining the level of base catalyst to dicarboxylic acid and/or pre-cursor at a sub-stoichiometric level during the extraction process. The method extends to a process of producing (meth)acrylic acid, its esters and polymers and copolymers thereof.
    Type: Application
    Filed: February 8, 2012
    Publication date: January 30, 2014
    Applicant: LUCITE INTERNATIONAL UK LIMITED
    Inventors: David William Johnson, Graham Ronald Eastham, Martyn Poliakoff, Thomas Andrew Huddle
  • Patent number: 8637701
    Abstract: A method for efficiently producing (meth)acrylic acid by crystallization using a plurality of crystallizers to purify (meth)acrylic acid and a refrigerator for supplying both of a cooling medium and a heating medium, while the refrigerator is stably operated for supplying media having a proper temperature and the temperature of the crystallizers is maintained.
    Type: Grant
    Filed: April 30, 2010
    Date of Patent: January 28, 2014
    Assignee: Nippon Shokubai Co., Ltd.
    Inventor: Masatsugu Kitaura
  • Publication number: 20130317254
    Abstract: In one embodiment, the invention is to a process for producing an acrylate product. The process comprises the step of providing a crude product stream comprising the acrylate product and an alkylenating agent. The process further comprises the step of separating at least a portion of the crude product stream into an intermediate acrylate product stream and an alkylenating stream. The process further comprises separating at least a portion of the intermediate acrylate product stream by azeotropic distillation in the presences of an entrainer to form a stream containing acrylate product and a stream containing entrainer.
    Type: Application
    Filed: May 25, 2012
    Publication date: November 28, 2013
    Applicant: Celanese International Corporation
    Inventors: Ilias S. Kotsianis, Tianshu Pan, Craig J. Peterson, R. Jay Warner, Josefina T. Chapman
  • Patent number: 8592624
    Abstract: A production process for the manufacture of ethylenically unsaturated acids or esters thereof is described. The process includes the steps of reaction of an alkanoic acid, or ester of an alkanoic acid, of the formula R3—CH2—COOR4 where R3 and R4 are each independently hydrogen or an alkyl group, in the presence of a catalyst system to produce an ethylenically unsaturated acid or ester product. The process is characterised in that the acid or ester product is subsequently contacted with a dienophile to thereby remove discolouration therefrom. An ethylenically unsaturated acid or ester crude product purification process is also described.
    Type: Grant
    Filed: May 15, 2009
    Date of Patent: November 26, 2013
    Assignee: Lucite International UK Limited
    Inventors: David William Johnson, Trevor Huw Morris
  • Patent number: 8592627
    Abstract: A process for producing (meth)acrylic acid comprising the steps of: supplying a cooling medium to a crystallizer (1) from a heat source device (4A), thereby crystallizing (meth)acrylic acid from a crude (meth)acrylic acid solution; discharging the cooling medium from the crystallizer (1) and returning the cooling medium to the heat source device (4A); supplying a heating medium to the crystallizer (1) from a heat source device (4B), thereby melting the (meth)acrylic acid; and discharging the heating medium from the crystallizer (1) and returning the heating medium to the heat source device (4B); wherein temperature of the cooling medium returned to the heat source device (4A) is maintained constant by utilizing a first buffer tank (5); and temperature of the heating medium returned to the heat source device (4B) is maintained constant by utilizing a second buffer tank (6).
    Type: Grant
    Filed: May 7, 2010
    Date of Patent: November 26, 2013
    Assignee: Nippon Shokubai Co., Ltd.
    Inventor: Takashi Sugimoto