Patents by Inventor Tatsuyuki Kumano

Tatsuyuki Kumano has filed for patents to protect the following inventions. This listing includes patent applications that are pending as well as patents that have already been granted by the United States Patent and Trademark Office (USPTO).

  • Publication number: 20230406800
    Abstract: A method for producing fluorenone including a pretreatment step of heating fluorene in the presence of a lower aliphatic carboxylic acid, a bromine compound, and a metal catalyst, and an oxidation step of continuously supplying fluorene and oxygen to perform an oxidation reaction, in the order indicated.
    Type: Application
    Filed: November 4, 2021
    Publication date: December 21, 2023
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yuki WATANABE, Hiroki SUMI, Hideaki FUJITA, Goh NAKAMURA, Tatsuyuki KUMANO
  • Publication number: 20230391705
    Abstract: Provided is a method for producing fluorenone comprising an oxidation step of oxidizing fluorene in the presence of an aliphatic carboxylic acid having 2 to 3 carbon atoms, a metal catalyst, a bromine compound, and oxygen, a solvent removal step of removing the aliphatic carboxylic acid, a heating step at 120 to 350° C., and a distillation step in the order indicated.
    Type: Application
    Filed: October 21, 2021
    Publication date: December 7, 2023
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Hiroki SUMI, Yuki WATANABE, Hideaki FUJITA, Goh NAKAMURA, Tatsuyuki KUMANO
  • Publication number: 20230040356
    Abstract: A method for producing bis(aminomethyl)cyclohexane, including hydrogenating xylylenediamine in the presence of a solvent and a catalyst, wherein the catalyst with decreased activity due to use is treated in a catalyst regeneration treatment step including the following step (1) and step (2), and then reused in a reaction system: step (1): maintaining an amount of bis(aminomethyl)cyclohexane in a liquid before the step (2) at 20% by mass or less, step (2): heating the catalyst to 100 to 500° C. and bringing the catalyst into contact with a hydrogen-containing gas.
    Type: Application
    Filed: December 15, 2020
    Publication date: February 9, 2023
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Emi NOGUCHI, Yukiya IBI, Tatsuyuki KUMANO
  • Publication number: 20220363622
    Abstract: An object of the present invention is to provide a method for producing m-dialkylbenzaldehyde by using a reaction starting material containing 1,4-dialkylbenzene. The method for producing m-dialkylbenzaldehyde represented by formula (3), comprising a step of allowing carbon monoxide to react on a reaction starting material containing 1,4-dialkylbenzene represented by formula (1) in the presence of a Bronsted acid and a Lewis acid, wherein the reaction starting material is 1,4-dialkylbenzene represented by formula (1), or a mixture of 1,4-dialkylbenzene represented by formula (1) and 1,3-dialkylbenzene represented by formula (2), containing 10 mol % or more of the 1,4-dialkylbenzene represented by formula (1), wherein in formulae (1) to (3), R1 represents a methyl group or an ethyl group, and R2 represents a chain or cyclic alkyl group having 3 or more and 6 or less carbon atoms that has a tertiary carbon at the benzyl position.
    Type: Application
    Filed: July 27, 2020
    Publication date: November 17, 2022
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Toru SHISHIMI, Tatsuya UTAMURA, Yutaka MATSUURA, Tatsuyuki KUMANO
  • Publication number: 20220252979
    Abstract: A photosensitive resin composition including a polyimide resin (A) having a specific structure and a weight average molecular weight of 70000 or less is provided.
    Type: Application
    Filed: May 27, 2020
    Publication date: August 11, 2022
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yumi SATO, Tatsuyuki KUMANO, Tatsuya UTAMURA, Daichi MIYAHARA
  • Publication number: 20220153682
    Abstract: A method for producing xylylenediamine, including performing a first hydrogenation including hydrogenating a mixed solution including dicyanobenzene and a solvent including liquid ammonia in a fixed-bed reactor such that a reaction product (A) is produced, performing ammonia separation including separating and removing liquid ammonia included in the reaction product (A) or a reaction product (D) such that a reaction product (B) or (E) is produced, performing solid-liquid separation including subjecting the reaction product (B) or (A) to solid-liquid separation and removing a solid component such that a reaction product (C) or the reaction product (D) is produced, and performing a second hydrogenation including hydrogenating the reaction product (C) or (E) in a fixed-bed reactor. After the first hydrogenation is performed, the ammonia separation and the solid-liquid separation are performed in this order or reverse order, followed by the second hydrogenation.
    Type: Application
    Filed: February 28, 2020
    Publication date: May 19, 2022
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yukiya IBI, Tatsuyuki KUMANO
  • Patent number: 11174269
    Abstract: An object of the present invention is to provide a method for producing 1,2,4,5-cyclohexanetetracarboxylic dianhydride, which is capable of stably achieving a high dehydration rate. The method for producing 1,2,4,5-cyclohexanetetracarboxylic dianhydride of the present invention is a method for producing 1,2,4,5-cyclohexanetetracarboxylic dianhydride by subjecting 1,2,4,5-cyclohexanetetracarboxylic acid to a dehydration reaction in a slurry state in the presence of a dehydrating agent, wherein an average particle size of the 1,2,4,5-cyclohexanetetracarboxylic acid is 20 ?m or more.
    Type: Grant
    Filed: March 22, 2018
    Date of Patent: November 16, 2021
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Shinyo Shirai, Tatsuyuki Kumano, Shinya Saito
  • Patent number: 11021428
    Abstract: An object of the present invention is to provide a method for producing cis,cis-1,2,4-cyclohexanetricarboxylic acid crystals, from which high purity cis,cis-1,2,4-cyclohexanetricarboxylic acid crystals are obtained. The method for producing cis,cis-1,2,4-cyclohexanetricarboxylic acid crystals of the present invention comprises the following steps: Step 1: measuring a mass ratio (cis/trans ratio) of cis,cis-1,2,4-cyclohexanetricarboxylic acid to trans,trans-1,2,4-cyclohexanetricarboxylic acid in an aqueous starting material solution comprising the cis,cis-1,2,4-cyclohexanetricarboxylic acid to give an aqueous starting material solution for crystal precipitation having a cis/trans ratio of 10 or more; and Step 2: subjecting the aqueous starting material solution for crystal precipitation obtained in step 1 to crystal precipitation.
    Type: Grant
    Filed: March 19, 2018
    Date of Patent: June 1, 2021
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Shinya Saito, Tatsuyuki Kumano
  • Publication number: 20200317596
    Abstract: An object of the present invention is to provide a method for producing cis,cis-1,2,4-cyclohexanetricarboxylic acid crystals, from which high purity cis,cis-1,2,4-cyclohexanetricarboxylic acid crystals are obtained. The method for producing cis,cis-1,2,4-cyclohexanetricarboxylic acid crystals of the present invention comprises the following steps: Step 1: measuring a mass ratio (cis/trans ratio) of cis,cis-1,2,4-cyclohexanetricarboxylic acid to trans,trans-1,2,4-cyclohexanetricarboxylic acid in an aqueous starting material solution comprising the cis,cis-1,2,4-cyclohexanetricarboxylic acid to give an aqueous starting material solution for crystal precipitation having a cis/trans ratio of 10 or more; and Step 2: subjecting the aqueous starting material solution for crystal precipitation obtained in step 1 to crystal precipitation.
    Type: Application
    Filed: March 19, 2018
    Publication date: October 8, 2020
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Shinya SAITO, Tatsuyuki KUMANO
  • Publication number: 20200039999
    Abstract: An object of the present invention is to provide a method for producing 1,2,4,5-cyclohexanetetracarboxylic dianhydride, which is capable of stably achieving a high dehydration rate. The method for producing 1,2,4,5-cyclohexanetetracarboxylic dianhydride of the present invention is a method for producing 1,2,4,5-cyclohexanetetracarboxylic dianhydride by subjecting 1,2,4,5-cyclohexanetetracarboxylic acid to a dehydration reaction in a slurry state in the presence of a dehydrating agent, wherein the 1,2,4,5-cyclohexanetetracarboxylic acid is fed in a divided or continuous manner to the dehydrating agent.
    Type: Application
    Filed: March 22, 2018
    Publication date: February 6, 2020
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Shinyo SHIRAI, Tatsuyuki KUMANO, Shinya SAITO
  • Publication number: 20200031841
    Abstract: An object of the present invention is to provide a method for producing 1,2,4,5-cyclohexanetetracarboxylic dianhydride, which is capable of stably achieving a high dehydration rate. The method for producing 1,2,4,5-cyclohexanetetracarboxylic dianhydride of the present invention is a method for producing 1,2,4,5-cyclohexanetetracarboxylic dianhydride by subjecting 1,2,4,5-cyclohexanetetracarboxylic acid to a dehydration reaction in a slurry state in the presence of a dehydrating agent, wherein an average particle size of the 1,2,4,5-cyclohexanetetracarboxylic acid is 20 ?m or more.
    Type: Application
    Filed: March 22, 2018
    Publication date: January 30, 2020
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Shinyo SHIRAI, Tatsuyuki KUMANO, Shinya SAITO
  • Patent number: 9822062
    Abstract: The object is to prevent deterioration and loss of dicyanobenzene in producing dicyanobenzene by ammoxidation of xylene to thereby achieve industrial and economical advantage in producing of dicyanobenzene.
    Type: Grant
    Filed: March 9, 2015
    Date of Patent: November 21, 2017
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Yukiya Ibi, Tatsuyuki Kumano, Natsumi Wakita
  • Publication number: 20170217873
    Abstract: The object is to prevent deterioration and loss of dicyanobenzene in producing dicyanobenzene by ammoxidation of xylene to thereby achieve industrial and economical advantage in producing of dicyanobenzene.
    Type: Application
    Filed: March 9, 2015
    Publication date: August 3, 2017
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yukiya IBI, Tatsuyuki KUMANO, Natsumi WAKITA
  • Patent number: 9024070
    Abstract: Provided is a method for stably and economically producing xylylenediamine with a high yield and long catalyst service life by hydrogenating dicyanobenzene that is obtained by ammoxidating xylene. By bringing an aqueous basic solution into contact with a dicyanobenzene-absorbed liquid, which is obtained by bringing an ammoxidation reaction gas into contact with an organic solvent, under specified temperature conditions, and subjecting a base and a carboxylic acid in the dicyanobenzene-absorbed liquid to a neutralization reaction so as to form an aqueous phase that contains a water-soluble salt, and then subjecting an organic phase and the aqueous phase to liquid-liquid separation so as to remove the aqueous phase, it is possible to remove the carboxylic acid contained in the dicyanobenzene-absorbed liquid with high selectivity while inhibiting loss of the dicyanobenzene.
    Type: Grant
    Filed: January 30, 2012
    Date of Patent: May 5, 2015
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Tatsuyuki Kumano, Yukiya Ibi, Kuniaki Arasuna, Shinichi Nagao
  • Patent number: 8759588
    Abstract: The invention provides a process for producing xylylenediamine, including supplying a solution of phthalonitrile dissolved in a solvent to a reactor filled with a catalyst and hydrogenating the phthalonitrile to produce xylylenediamine, characterized in that the process includes halting supply of the solution; (2) bringing a washing liquid into contact with the catalyst, the washing liquid having a phthalonitrile content of 3 mass % or less and a xylylenediamine content of 1 mass % or more; and after completion of the contact, resuming supply of the solution, and employing the catalyst continuously in hydrogenation. Through the production process of the invention, the catalyst can be employed continuously for a long period of time, and the catalyst-related cost can be considerably reduced.
    Type: Grant
    Filed: August 27, 2009
    Date of Patent: June 24, 2014
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Shinichi Nagao, Tatsuyuki Kumano, Kenji Nakaya, Ryusuke Shigematsu, Kinji Kato
  • Publication number: 20130296609
    Abstract: Provided is a method for stably and economically producing xylylenediamine with a high yield and long catalyst service life by hydrogenating dicyanobenzene that is obtained by ammoxidating xylene. By bringing an aqueous basic solution into contact with a dicyanobenzene-absorbed liquid, which is obtained by bringing an ammoxidation reaction gas into contact with an organic solvent, under specified temperature conditions, and subjecting a base and a carboxylic acid in the dicyanobenzene-absorbed liquid to a neutralization reaction so as to form an aqueous phase that contains a water-soluble salt, and then subjecting an organic phase and the aqueous phase to liquid-liquid separation so as to remove the aqueous phase, it is possible to remove the carboxylic acid contained in the dicyanobenzene-absorbed liquid with high selectivity while inhibiting loss of the dicyanobenzene.
    Type: Application
    Filed: January 30, 2012
    Publication date: November 7, 2013
    Applicant: Mitsubishi Gas Chemical Company, INC.
    Inventors: Tatsuyuki Kumano, Yukiya Ibi, Kuniaki Arasuna, Shinichi Nagao
  • Patent number: 8212080
    Abstract: A method of producing xylylenediamine by the hydrogenation of dicyanobenzene obtained by the ammoxidation of xylene in a high yield while prolonging the catalyst life. In the method, a molten dicyanobenzene from which compounds having a boiling point lower than that of dicyanobenzene have been removed but compounds having a boiling point higher than that of dicyanobenzene are not removed is dissolved in a solvent containing liquid ammonia. By this dissolution, at least part of dicyanobenzene polymers precipitates as insolubles. The precipitates are removed by a solid-liquid separation. By subjecting the resulting solution containing the dicyanobenzene polymers in a reduced amount to hydrogenation, xylylenediamine is produced in a high yield and the life time of hydrogenation catalyst is prolonged.
    Type: Grant
    Filed: December 8, 2009
    Date of Patent: July 3, 2012
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Tatsuyuki Kumano, Kenji Nakaya, Shinichi Nagao
  • Publication number: 20110245540
    Abstract: The invention provides a process for producing xylylenediamine, including supplying a solution of phthalonitrile dissolved in a solvent to a reactor filled with a catalyst and hydrogenating the phthalonitrile to produce xylylenediamine, characterized in that the process includes halting supply of the solution; (2) bringing a washing liquid into contact with the catalyst, the washing liquid having a phthalonitrile content of 3 mass % or less and a xylylenediamine content of 1 mass % or more; and after completion of the contact, resuming supply of the solution, and employing the catalyst continuously in hydrogenation. Through the production process of the invention, the catalyst can be employed continuously for a long period of time, and the catalyst-related cost can be considerably reduced.
    Type: Application
    Filed: August 27, 2009
    Publication date: October 6, 2011
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Shinichi Nagao, Tatsuyuki Kumano, Kenji Nakaya, Ryusuke Shigematsu, Kinji Kato
  • Publication number: 20100168474
    Abstract: A method of producing xylylenediamine by the hydrogenation of dicyanobenzene obtained by the ammoxidation of xylene in a high yield while prolonging the catalyst life. In the method, a molten dicyanobenzene from which compounds having a boiling point lower than that of dicyanobenzene have been removed but compounds having a boiling point higher than that of dicyanobenzene are not removed is dissolved in a solvent containing liquid ammonia. By this dissolution, at least part of dicyanobenzene polymers precipitates as insolubles. The precipitates are removed by a solid-liquid separation. By subjecting the resulting solution containing the dicyanobenzene polymers in a reduced amount to hydrogenation, xylylenediamine is produced in a high yield and the life time of hydrogenation catalyst is prolonged.
    Type: Application
    Filed: December 8, 2009
    Publication date: July 1, 2010
    Applicant: Mitsubishi Gas Chemical Company, Inc
    Inventors: Tatsuyuki KUMANO, Kenji Nakaya, Shinichi Nagao
  • Patent number: 7626057
    Abstract: A method of producing xylylenediamine by a two-stage hydrogenation of a starting phthalonitrile in a solvent. The main steps of the method are a hydrogenation step 1 and a hydrogenation step 2. In the hydrogenation step 1, a solution of the starting phthalonitrile in the solvent containing liquid ammonia is fed to an inlet of a first reaction zone and the hydrogenation is carried out in the first reaction zone in the presence of a heterogeneous catalyst, to hydrogenate nitrile groups in the starting phthalonitrile to aminomethyl groups. A part of the hydrogenation product solution from the first reaction zone is circulated to the inlet of the first reaction zone and the rest is introduced into the hydrogenation step 2 where further undergoes the hydrogenation.
    Type: Grant
    Filed: June 27, 2007
    Date of Patent: December 1, 2009
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Tatsuyuki Kumano, Ryusuke Shigematsu, Kinji Kato, Kenji Nakaya