Patents Assigned to Mizushima Aroma Company, Ltd.
  • Patent number: 8957247
    Abstract: In pretreating a pyridine ring-containing chelate resin which is used in the step for adsorption and collection of a heavy metal ion and a bromide ion derived from a catalyst from the oxidation reaction mother liquid in the process of producing an aromatic carboxylic acid, there may occur phenomena such as swelling of the resin, heat generation of the resin, and air bubbles generation, thereby causing fracture and deterioration of the resin. As a first treatment, Br? conversion, under a certain condition, of a pyridine ring-containing chelate resin with an aqueous solution of hydrobromic acid is performed, and then as a second treatment, replacement with acetic acid solvent is performed, thereby making it possible to prevent fracture and deterioration of the resin.
    Type: Grant
    Filed: February 18, 2011
    Date of Patent: February 17, 2015
    Assignees: Toyobo Co., Ltd., Mizushima Aroma Company, Ltd.
    Inventors: Fumiya Zaima, Hideaki Fujita
  • Publication number: 20130281732
    Abstract: Provided is a simple filtering operation method capable of conducting a filtering operation without clogging in a ceramic filter for a long period of time, in the operation of filtering fine crystals of terephthalic acid in an oxidation reaction mother liquor obtained in a process of terephthalic acid production by a cross-flow filtration using the ceramic filter. The present invention can be accomplished by conducting an operation for filtering the fine crystals and a back washing operation with a filtrate while maintaining a flowing circulation operation of the oxidation reaction mother liquor under predetermined conditions.
    Type: Application
    Filed: October 25, 2011
    Publication date: October 24, 2013
    Applicants: MITSUBISHI GAS CHEMICAL COMPANY, INC., MIZUSHIMA AROMA COMPANY, LTD., TOYOBO CO., LTD.
    Inventors: Fumiya Zaima, Nirou Hoshishima, Kazutoshi Uozumi, Hideaki Fujita
  • Patent number: 8247605
    Abstract: A method of replacing a first dispersion medium in a starting slurry composed of the first dispersion medium and isophthalic acid crystals with a second dispersion medium. The starting slurry is tangentially fed to a vertically extending cylindrical portion of a cyclone-shaped nozzle disposed at an upper portion of a replacement tank of a dispersion medium replacement apparatus, from a tangential direction of the cylindrical portion. The fed starting slurry moves circularly along an inner wall of the cylindrical portion. The slurry circularly moving is then discharged from an opening which is disposed at a vertically lower end of the cylindrical portion and dispersed in a second dispersion medium which is fed from a lower portion of the replacement tank. The replaced slurry composed of isophthalic acid crystals and the second dispersion medium is mainly discharged from the lower portion of the replacement tank, and the first dispersion medium is mainly withdrawn from the upper portion of the replacement tank.
    Type: Grant
    Filed: July 19, 2007
    Date of Patent: August 21, 2012
    Assignees: Mitsubishi Gas Chemical Company, Inc., Toyobo Co., Ltd., Mizushima Aroma Company, Ltd.
    Inventors: Masato Inari, Fumiya Zaima
  • Patent number: 8247604
    Abstract: A method of replacing a first dispersion medium in a starting slurry composed of the first dispersion medium and a terephthalic acid crystal with a second dispersion medium. The starting slurry is tangentially fed to a vertically extending cylindrical portion of a cyclone-shaped nozzle disposed at an upper portion of a replacement tank of a dispersion medium replacement apparatus, from a tangential direction of the cylindrical portion. The fed starting slurry moves circularly along an inner wall of the cylindrical portion. The slurry circularly moving is then discharged from an opening which is disposed at a vertically lower end of the cylindrical portion and dispersed in a second dispersion medium which is fed from a lower portion of the replacement tank.
    Type: Grant
    Filed: June 8, 2007
    Date of Patent: August 21, 2012
    Assignees: Mitsubishi Gas Chemical Company, Inc., Toyobo Co., Ltd., Mizushima Aroma Company, Ltd.
    Inventors: Masato Inari, Fumiya Zaima
  • Patent number: 8242304
    Abstract: A method for producing isophthalic acid, comprising: subjecting a m-phenylene compound and a molecular-oxygen-containing gas to liquid-phase oxidation reaction in the presence of a catalyst comprising a heavy metal compound and a bromine compound, and hydrous acetic acid having a water content of 1 to 15 mass %, to thereby yield a slurry; regulating the temperature of the slurry to 35 to 140° C., to thereby precipitate isophthalic acid; removing the isophthalic acid through solid-liquid separation, to thereby recover a mother liquor; and recovering the catalyst from the mother liquor by following steps (1) to (4) as described.
    Type: Grant
    Filed: March 15, 2011
    Date of Patent: August 14, 2012
    Assignees: Mitsubishi Gas Chemical Company, Inc., Toyobo Co., Ltd., Mizushima Aroma Company, Ltd.
    Inventors: Fumiya Zaima, Nobuo Namiki, Hideaki Fujita, Masato Inari
  • Patent number: 8236982
    Abstract: A method for producing terephthalic acid comprising: subjecting a p-phenylene compound to a liquid-phase oxidation reaction by the use of a molecular-oxygen-containing gas in the presence of a catalyst at least containing a heavy metal compound and a bromine compound, and hydrous acetic acid having a water content of 1 to 15 mass %, to thereby yield a slurry; regulating the temperature of the slurry to 35 to 140° C., to thereby cause terephthalic acid to precipitate; removing the terephthalic acid through solid-liquid separation, to thereby recover a mother liquor; and recovering the catalyst from the mother liquor through a series of operations (1) to (4), as described, for reusing at least a portion of the catalyst in the liquid-phase oxidation reaction.
    Type: Grant
    Filed: March 15, 2011
    Date of Patent: August 7, 2012
    Assignees: Mitsubishi Gas Chemical Company, Inc., Toyobo Co., Ltd., Mizushima Aroma Company, Ltd.
    Inventors: Fumiya Zaima, Masato Inari, Hideaki Fujita, Nobuo Namiki
  • Patent number: 8178716
    Abstract: The present invention relates to a multi-stage crystallization process which comprises the steps of feeding a solution of terephthalic acid or a slurry (raw slurry) containing terephthalic acid partially precipitated to a first crystallization vessel to precipitate the terephthalic acid therein; and feeding a slurry (crystallization slurry) containing the thus precipitated terephthalic acid sequentially to second and subsequent crystallization vessels, wherein while continuously supplying a cleaning solvent to a delivery conduit connecting the former-stage crystallization vessel and the next latter-stage crystallization vessel to each other, the crystallization slurry is fed through the delivery conduit.
    Type: Grant
    Filed: May 2, 2007
    Date of Patent: May 15, 2012
    Assignees: Mitsubishi Gas Chemical Company, Inc., Toyobo Co., Ltd., Mizushima Aroma Company, Ltd.
    Inventors: Fumiya Zaima, Nirou Hoshishima
  • Publication number: 20110213181
    Abstract: A method for producing terephthalic acid comprising: subjecting a p-phenylene compound to a liquid-phase oxidation reaction by the use of a molecular-oxygen-containing gas in the presence of a catalyst at least containing a heavy metal compound and a bromine compound, and hydrous acetic acid having a water content of 1 to 15 mass %, to thereby yield a slurry; regulating the temperature of the slurry to 35 to 140° C., to thereby cause terephthalic acid to precipitate; removing the terephthalic acid through solid-liquid separation, to thereby recover a mother liquor; and recovering the catalyst from the mother liquor through a series of operations (1) to (4), as described, for reusing at least a portion of the catalyst in the liquid-phase oxidation reaction.
    Type: Application
    Filed: March 15, 2011
    Publication date: September 1, 2011
    Applicants: Mitsubishi Gas Chemical Company, Inc., Toyobo Co., LTD., MIZUSHIMA AROMA COMPANY, LTD.
    Inventors: Fumiya ZAIMA, Masato Inari, Hideaki Fujita, Nobuo Namiki
  • Publication number: 20100016629
    Abstract: The invention provides a method for producing terephthalic acid, characterized by including subjecting a p-phenylene compound to liquid-phase oxidation reaction by use of a molecular-oxygen-containing gas in the presence of a catalyst at least containing a heavy metal compound and a bromine compound, and hydrous acetic acid having a water content of 1 to 15 mass %, to thereby yield a slurry; regulating the temperature of the slurry to 35 to 140° C., to thereby cause terephthalic acid to precipitate; removing the terephthalic acid through solid-liquid separation, to thereby recover a mother liquor; and recovering the catalyst from the mother liquor through a series of the following steps (1) to (4) for reusing at least a portion of the catalyst in the liquid-phase oxidation reaction: (1) an adsorption step including regulating the ratio “amount by mole of bromide ions in the mother liquor/total amount by mole of heavy metal ions in the mother liquor” to 0.
    Type: Application
    Filed: December 7, 2007
    Publication date: January 21, 2010
    Applicants: Mitsubishi Gas Chemical Company, Inc., Toyobo Co., Ltd., Mizushima Aroma Company, Ltd.
    Inventors: Fumiya Zaima, Masato Inari, Hideaki Fujita, Nobuo Namiki
  • Patent number: 7262323
    Abstract: A method for producing high purity terephthalic acid wherein a slurry having an acetic acid solvent and, dispersed therein, crude terephthalic acid crystals which has been prepared by subjecting a p-alkyl benzene to a liquid phase oxidation in a solvent of acetic acid is continuously converted to a water slurry by the mother liquid exchange, and then the resultant water slurry is subjected to a hydrogenation treatment, which comprises introducing the above acetic acid slurry to a tower having a center axis having a plurality of agitating blades at the top thereof, to form a region having a high concentration of terephthalic acid crystals in the tower through the sedimentation of the terephthalic acid crystals, supplying the water for substitution to the bottom of the tower in such a manner to form an upward water flow while generating a revolving flow of the high concentration region by the rotation of the agitation blade, to thereby subject said terephthalic acid crystals and said upward water flow to a coun
    Type: Grant
    Filed: September 30, 2004
    Date of Patent: August 28, 2007
    Assignees: Mitsubishi Gas Chemical Company, Inc., Toyo Boseki Kabushiki Kaisha, Mizushima Aroma Company, Ltd.
    Inventors: Hideaki Fujita, Hiroshi Machida, Nobuo Namiki, Yoshio Waguri
  • Patent number: 7102029
    Abstract: The present invention proposes a crystallization process comprising the steps of feeding a slurry solution in which a terephthalic acid solution or a part of the terephthalic acid is precipitated to a crystallization vessel, precipitating the terephthalic acid in the crystallization vessel, generating a slurry containing crystals and solvent, discharging the slurry, and further comprising the steps of introducing the slurry in a tangential the direction of a hydrocyclone, returning the slurry flowing out as a downward swirling flow from a lower part of the hydrocyclone to the vessel, and discharging the slurry overflowing from the upper part of the hydrocyclone. According to the present invention, crystals of large particle size is obtained and a stable driving ranging long term can be achieved because any adhesion or accumulation of the terephthalic acid crystals does not appear at all in the crystallization vessel.
    Type: Grant
    Filed: September 21, 2001
    Date of Patent: September 5, 2006
    Assignees: Mitsubishi Gas Chemical Company, Inc., Toyo Boseki Kabushiki Kaisha, Mizushima Aroma Company, Ltd.
    Inventors: Fumio Ohkoshi, Takahisa Furuya
  • Patent number: 6620966
    Abstract: There is disclosed a process for continuously producing an aromatic carboxylic acid comprising the steps of (A) subjecting a poly-alkyl aromatic hydrocarbon to a liquid-phase oxidation by continuously supplying an oxidation reactor with said hydrocarbon, a catalyst, a reaction accelerator, acetic acid containing water and a gas containing molecular oxygen; (B) continuously taking out from the oxidation reactor, the reaction products containing aromatic carboxylic acids, and separating the same into crude aromatic carboxylic acids and acetic acid containing water; and (C) continuously taking out from the oxidation reactor, the oxidative reaction exhaust gas containing evaporated acetic acid containing water, introducing the above gas in a condenser, and condensing the above evaporated acid, wherein acetic acid containing water is supplied to an oxidative reaction exhaust gas inlet line leading to the condenser.
    Type: Grant
    Filed: January 16, 2002
    Date of Patent: September 16, 2003
    Assignees: Mitsubishi Gas Chemical Company, Inc., Toyo Boseki Kabushiki Kaisha, Mizushima Aroma Company, Ltd.
    Inventors: Fumio Ohkoshi, Ikuo Tsuboi, Nirou Hoshishima
  • Patent number: 6500347
    Abstract: A process for recovering crystals from a slurry which comprises supplying a slurry comprising crystals and a solvent to a rotary vacuum filter and successively conducting filtration under suction, washing, filtration under suction and cleavage of a cake continuously by rotation of a cylindrical filter medium, wherein a vapor having a same composition as that of the solvent is supplied as a blowing gas for cleaving the cake. The crystals can be continuously recovered for a long period of time without clogging of a filter medium when the crystals are recovered from a slurry by using a rotary vacuum filter.
    Type: Grant
    Filed: July 3, 2001
    Date of Patent: December 31, 2002
    Assignees: Mitsubishi GAs Chemical Company, Inc., Toyo Boseki Kabushiki Kaisha, Mizushima Aroma Company, Ltd.
    Inventors: Fumio Ohkoshi, Masato Inari
  • Patent number: 5959140
    Abstract: There is disclosed a process for producing an aromatic carboxylic acid (e.g.iso-or-tere-phthalic acid) by liquid-phase oxidation of an alkyl-group-substituted aromatic compound (e.g. p-or-m-xylene) in acetic acid which comprises dehydrating water-containing acetic acid by azeotropic distillation in an azeotropic distillation dehydration tower to recycle the dehydrated acetic acid as the solvent, and suppressing the concentration of the alkyl-group-substituted aromatic compound in the entrainer (e.g. n-butyl acetate) which is fed at the top portion of the above tower, to at most 10% by weight by removing the above aromatic compound. The process makes it possible to proceed with efficient dehydration of water-containing acetic acid for a long period of time by preventing the separation efficiency between acetic acid and an azeotropic component from being deteriorated by the alkyl-group-substituted aromatic compound remaining in the azeotropic component.
    Type: Grant
    Filed: September 28, 1998
    Date of Patent: September 28, 1999
    Assignees: Mitsubishi Gas Chemical Company, Inc., Toyo Boseki Kabushiki Kaisha, Mizushima Aroma Company, Ltd.
    Inventor: Fumio Okoshi
  • Patent number: 5777161
    Abstract: There is disclosed a process for producing highly pure terephthalic acid by the use of a dispersion medium replacement apparatus equipped with a stirring unit at the bottom portion for uniform dispersion, wherein an original slurry comprising a first dispersion medium and terephthalic acid crystals is introduced into a dispersion medium replacement apparatus at the top portion, a second dispersion medium is introduced into the apparatus at the bottom portion, a replaced slurry comprising principally the second dispersion medium and the terephthalic acid crystals is taken out from the apparatus at the bottom portion, and the first dispersion medium as a major component is taken out from the apparatus at the top portion, which process comprises maintaining a uniformly dispersed slurry at the bottom portion of the apparatus at a concentration higher than that of a slurry at the intermediate portion; maintaining the upper portion at a higher temperature in a vertical temperature distribution therein to form a tem
    Type: Grant
    Filed: July 7, 1997
    Date of Patent: July 7, 1998
    Assignees: Mitsubishi Gas Chemical Company, Inc., Toyo Boseki Kabushiki Kaisha, Mizushima Aroma Company, Ltd.
    Inventor: Masato Inary
  • Patent number: 5712412
    Abstract: There are disclosed a method for replacing a dispersion medium wherein an original slurry comprising solid particles and an original dispersion medium is introduced in a dispersion medium replacement column at the top thereof, a replacing dispersion medium is introduced in the column at the bottom thereof to replace the original dispersion medium with the replacing dispersion medium, the resultant replaced slurry comprising the solid particles and the replacing dispersion medium is taken out from the column at the bottom thereof, and the original dispersion medium is taken out from the column at the top thereof, which method comprises dividing the fluid in the intermediate portion into a plurality of parallel streams, stirring the slurry in the bottom of the column to uniformize the slurry, and controlling the feed rates of the replacing dispersion medium and the replaced slurry to maintain the slurry in the bottom portion of the column at a concentration higher than that of the slurry in the intermediate por
    Type: Grant
    Filed: November 27, 1995
    Date of Patent: January 27, 1998
    Assignees: Mitsubishi Gas Chemical Co., Inc., Toyo Boseki Kabushiki Kaisha, Mizushima Aroma Company, Ltd.
    Inventors: Masato Inary, Fumio Ohkoshi, Fumiya Zaima
  • Patent number: 5705682
    Abstract: A process for producing highly pure terephthalic acid comprising: (a) oxidizing a p-phenylene compound in the liquid phase in the presence of acetic acid, to produce a liquid-phase oxidation product, (b) separating the liquid-phase oxidation product into the following: (i) a first mother liquid containing acetic acid and (ii) a crude terephthalic acid, (c) evaporating, in whole or in part, the first mother liquid, to produce a vapor, (d) feeding the vapor, or a condensate thereof, to an intermediate stage of a distillation tower, carrying out an azeotropic distillation and withdrawing through a bottom of the distillation tower a concentrated acetic acid, (e) subjecting the crude terephthalic acid to a refining treatment, which is a catalytic hydrotreatment, a catalytic treatment or a recrystallization, which is carried out in the presence of is water, (f) cooling and crystallizing the resultant liquid from step (e), to produce a pure terephthalic acid and a second mother liquor, (g) subjecting the second moth
    Type: Grant
    Filed: September 3, 1996
    Date of Patent: January 6, 1998
    Assignees: Mitsubishi Gas Chemical Company, Inc., Toyo Boseki Kabushiki Kaisha, Mizushima Aroma Company, Ltd.
    Inventors: Fumio Ohkoshi, Masato Inary, Fumiya Zaima
  • Patent number: 5679847
    Abstract: There is disclosed a process for producing terephthalic acid which comprises oxidizing in a liquid-phase a starting raw material comprising p-xylene incorporated with 3 to 35% by weight of p-tolualdehyde based on the same at a temperature in the range of 120.degree. to 240.degree. C. by means of a molecular oxygen-containing gas by using a lower aliphatic monocarboxylic acid as a solvent in the presence of a catalyst comprising a manganese compound having 50 to 1000 ppm by weight of manganese atoms, a cobalt compound having 50 to 2000 ppm by weight of cobalt atoms and a bromine compound having 100 to 4000 ppm by weight of bromine atoms, each based on the solvent. By virtue of the above specific constitution, it is made possible to produce high-quality terephthalic acid with a high residual rate of the lower aliphatic monocarboxylic acid as a solvent minimized in its loss, thereby enabling the production of high-quality polyester with high whiteness from the above terephthalic acid and a glycol.
    Type: Grant
    Filed: May 6, 1996
    Date of Patent: October 21, 1997
    Assignees: Mitsubishi Gas Chemical Company, Inc., Toyo Boseki Kabushiki Kaisha, Mizushima Aroma Company, Ltd.
    Inventors: Fumio Ohkoshi, Masato Inary, Fumiya Zaima