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).
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Publication number: 20230406800Abstract: 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: ApplicationFiled: November 4, 2021Publication date: December 21, 2023Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Yuki WATANABE, Hiroki SUMI, Hideaki FUJITA, Goh NAKAMURA, Tatsuyuki KUMANO
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Publication number: 20230391705Abstract: 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: ApplicationFiled: October 21, 2021Publication date: December 7, 2023Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Hiroki SUMI, Yuki WATANABE, Hideaki FUJITA, Goh NAKAMURA, Tatsuyuki KUMANO
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Publication number: 20230040356Abstract: 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: ApplicationFiled: December 15, 2020Publication date: February 9, 2023Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Emi NOGUCHI, Yukiya IBI, Tatsuyuki KUMANO
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Publication number: 20220363622Abstract: 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: ApplicationFiled: July 27, 2020Publication date: November 17, 2022Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Toru SHISHIMI, Tatsuya UTAMURA, Yutaka MATSUURA, Tatsuyuki KUMANO
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Publication number: 20220252979Abstract: 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: ApplicationFiled: May 27, 2020Publication date: August 11, 2022Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Yumi SATO, Tatsuyuki KUMANO, Tatsuya UTAMURA, Daichi MIYAHARA
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Publication number: 20220153682Abstract: 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: ApplicationFiled: February 28, 2020Publication date: May 19, 2022Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Yukiya IBI, Tatsuyuki KUMANO
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Patent number: 11174269Abstract: 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: GrantFiled: March 22, 2018Date of Patent: November 16, 2021Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Shinyo Shirai, Tatsuyuki Kumano, Shinya Saito
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Patent number: 11021428Abstract: 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: GrantFiled: March 19, 2018Date of Patent: June 1, 2021Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Shinya Saito, Tatsuyuki Kumano
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Publication number: 20200317596Abstract: 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: ApplicationFiled: March 19, 2018Publication date: October 8, 2020Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Shinya SAITO, Tatsuyuki KUMANO
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Publication number: 20200039999Abstract: 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: ApplicationFiled: March 22, 2018Publication date: February 6, 2020Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Shinyo SHIRAI, Tatsuyuki KUMANO, Shinya SAITO
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Publication number: 20200031841Abstract: 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: ApplicationFiled: March 22, 2018Publication date: January 30, 2020Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Shinyo SHIRAI, Tatsuyuki KUMANO, Shinya SAITO
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Patent number: 9822062Abstract: 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: GrantFiled: March 9, 2015Date of Patent: November 21, 2017Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Yukiya Ibi, Tatsuyuki Kumano, Natsumi Wakita
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Publication number: 20170217873Abstract: 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: ApplicationFiled: March 9, 2015Publication date: August 3, 2017Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Yukiya IBI, Tatsuyuki KUMANO, Natsumi WAKITA
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Patent number: 9024070Abstract: 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: GrantFiled: January 30, 2012Date of Patent: May 5, 2015Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tatsuyuki Kumano, Yukiya Ibi, Kuniaki Arasuna, Shinichi Nagao
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Patent number: 8759588Abstract: 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: GrantFiled: August 27, 2009Date of Patent: June 24, 2014Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Shinichi Nagao, Tatsuyuki Kumano, Kenji Nakaya, Ryusuke Shigematsu, Kinji Kato
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Publication number: 20130296609Abstract: 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: ApplicationFiled: January 30, 2012Publication date: November 7, 2013Applicant: Mitsubishi Gas Chemical Company, INC.Inventors: Tatsuyuki Kumano, Yukiya Ibi, Kuniaki Arasuna, Shinichi Nagao
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Patent number: 8212080Abstract: 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: GrantFiled: December 8, 2009Date of Patent: July 3, 2012Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tatsuyuki Kumano, Kenji Nakaya, Shinichi Nagao
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Publication number: 20110245540Abstract: 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: ApplicationFiled: August 27, 2009Publication date: October 6, 2011Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Shinichi Nagao, Tatsuyuki Kumano, Kenji Nakaya, Ryusuke Shigematsu, Kinji Kato
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Publication number: 20100168474Abstract: 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: ApplicationFiled: December 8, 2009Publication date: July 1, 2010Applicant: Mitsubishi Gas Chemical Company, IncInventors: Tatsuyuki KUMANO, Kenji Nakaya, Shinichi Nagao
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Patent number: 7626057Abstract: 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: GrantFiled: June 27, 2007Date of Patent: December 1, 2009Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Tatsuyuki Kumano, Ryusuke Shigematsu, Kinji Kato, Kenji Nakaya