Patents by Inventor Yousuke Shinkai
Yousuke Shinkai 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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Patent number: 11970442Abstract: To achieve a method for producing a carbonic ester at a high yield by a simple process while suppressing formation of by-products, for example, a method for producing an aliphatic carbonic ester. The above problem is solved by a method for producing a carbonic ester, the method including a carbonic ester formation reaction in which an alcohol and carbon dioxide are reacted in the presence of an aromatic nitrile compound and a catalyst, wherein the water content in the alcohol used in the carbonic ester formation reaction is 0.10% by mass or less.Type: GrantFiled: January 8, 2019Date of Patent: April 30, 2024Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Hidefumi Harada, Takehiko Isobe, Hongyu Liu, Yousuke Shinkai, Ryotaro Umezu
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Patent number: 11596936Abstract: Realized is a method for restoring the activity of a catalyst for producing a carbonate ester by a simple technique with no use of a complicated step such as calcining or the like to allow the catalyst to be reusable, and a method for producing a carbonate ester at a high yield by use of the catalyst thus regenerated. The above-described problem has been solved by a method for regenerating a catalyst containing CeO2, the catalyst being usable for a carbonate ester generation reaction of generating a carbonate ester from carbon dioxide and an alcohol, the method comprising (a) a separation step of separating the catalyst as a crude catalyst from a reaction solution of carbon dioxide and the alcohol; and (b) a catalyst processing step of washing the crude catalyst with a washing alcohol to provide a purified catalyst.Type: GrantFiled: September 25, 2018Date of Patent: March 7, 2023Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Hidefumi Harada, Takehiko Isobe, Hongyu Liu, Yousuke Shinkai, Ryotaro Umezu
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Publication number: 20220177646Abstract: Provided is a method of manufacturing an aromatic polycarbonate resin composition with high fluidity, particularly during low shear, and a good color. An aromatic polycarbonate resin composition including: an aromatic polycarbonate resin that has a structural unit expressed by general formula (1); a aliphatic cyclic carbonate that is expressed by general formula (2) and is included at a ratio of 10 ppm-10,000 ppm; an aromatic cyclic carbonate that is expressed by general formula (3); and at least one compound selected from the group consisting of compounds expressed by general formulas (4)-(6), wherein the total content of the aromatic cyclic carbonate and the compound(s) expressed by general formula(s) (4)-(6) is 0.1 mass %-2.0 mass % by bisphenol A-converted value.Type: ApplicationFiled: February 9, 2022Publication date: June 9, 2022Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Yoshinori ISAHAYA, Atsushi HIRASHIMA, Hidefumi HARADA, Maki ITO, Jun-ya HAYAKAWA, Takehiko ISOBE, Yousuke SHINKAI, Keisuke SHIMOKAWA
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Publication number: 20220009873Abstract: Provided is a dialkyl carbonate production method that enables a dialkyl carbonate to be produced in a simple manner and in a short reaction time and enables easy processing of by-products. This dialkyl carbonate production method involves generation reaction of a carbonate ester through reaction between carbon dioxide and an alcohol represented by formula (1), wherein the generation reaction of a carbonate ester is performed in the presence of a carbodiimide compound represented by formula (2) (R1-R3 in the formula are as described in the description of the present application).Type: ApplicationFiled: December 4, 2019Publication date: January 13, 2022Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Hongyu LIU, Takehiko ISOBE, Yousuke SHINKAI, Hidefumi HARADA
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Patent number: 11161816Abstract: Provided is a method for regenerating an aromatic amide compound into a corresponding aromatic nitrile compound, the method realizing a dehydration reaction of providing a target compound selectively at a high yield, with generation of a by-product being suppressed. Also provided is a method for producing an aromatic nitrile compound that decreases the number of steps of the dehydration reaction and significantly improves the reaction speed even at a pressure close to normal pressure. In addition, the above-described production method is applied to a carbonate ester production method to provide a method for producing a carbonate ester efficiently. The above-described methods are realized by a method for producing an aromatic nitrile compound including a dehydration reaction of dehydrating an aromatic amide compound, in which the dehydration reaction uses, as a solvent, any of 1,2-dimethoxybenzene, 1,3-dimethoxybenzene and 1,3,5-trimethoxybenzene.Type: GrantFiled: August 28, 2020Date of Patent: November 2, 2021Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Hidefumi Harada, Yousuke Shinkai, Hongyu Liu, Takehiko Isobe, Yoshinori Isahaya
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Publication number: 20210284594Abstract: Provided are a method for producing carbonate esters, and a catalytic structure for producing carbonate esters, whereby solid catalyst powder formation and detachment are suppressed and superior carbonate ester reaction efficiency is yielded when a catalytic structure constituted by a sufficient quantity of a cerium-oxide-containing solid catalyst supported on a substrate is used. The method for producing carbonate esters includes reacting a monohydric alcohol and carbon dioxide in the presence of a catalytic structure and a hydrating agent. The catalytic structure includes a substrate and a catalytic layer that is formed on at least a portion of the surface of the substrate and contains a solid catalyst and an inorganic binder. The solid catalyst contains cerium oxide. The supported quantity of the solid catalyst is 15 g/m2 to 200 g/m2, inclusive. The inorganic binder contains silica and/or alumina.Type: ApplicationFiled: July 8, 2019Publication date: September 16, 2021Applicants: NIPPON STEEL CORPORATION, MITSUBISHI GAS CHEMICAL COMPANY, INC., NIPPON STEEL ENGINEERING CO., LTD.Inventors: Kimihito SUZUKI, Yousuke SHINKAI, Hongyu LIU, Hidefumi HARADA, Yuzuru KATO, Kentaro MORITA, Asuka OHASHI
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Patent number: 11021571Abstract: Provided is a manufacturing method for a high molecular weight aromatic polycarbonate resin that has superior fluidity and for which a good color and a sufficiently high molecular weight can be achieved. A manufacturing method for a high molecular weight aromatic polycarbonate resin includes: a step in which a dialcohol compound expressed by general formula (1) and a catalyst are mixed to obtain a catalyst composition; a step in which the obtained catalyst composition is kept in a molten state, and is mixed with an aromatic polycarbonate prepolymer within ten hours after obtaining the catalyst composition, to obtain a prepolymer mixture; and a high molecular weight achievement step in which the obtained prepolymer mixture is heat-treated under reduced pressure conditions to obtain a high molecular weight aromatic polycarbonate resin.Type: GrantFiled: March 24, 2017Date of Patent: June 1, 2021Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Yoshinori Isahaya, Atsushi Hirashima, Hidefumi Harada, Maki Ito, Jun-ya Hayakawa, Takehiko Isobe, Yousuke Shinkai, Keisuke Shimokawa
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Publication number: 20210061749Abstract: To achieve a method for producing a carbonic ester at a high yield by a simple process while suppressing formation of by-products, for example, a method for producing an aliphatic carbonic ester. The above problem is solved by a method for producing a carbonic ester, the method including a carbonic ester formation reaction in which an alcohol and carbon dioxide are reacted in the presence of an aromatic nitrile compound and a catalyst, wherein the water content in the alcohol used in the carbonic ester formation reaction is 0.10% by mass or less.Type: ApplicationFiled: January 8, 2019Publication date: March 4, 2021Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Hidefumi HARADA, Takehiko ISOBE, Hongyu LIU, Yousuke SHINKAI, Ryotaro UMEZU
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Patent number: 10927216Abstract: Provided is a high molecular weight aromatic polycarbonate resin manufacturing method that suppresses the occurrence of heterogeneous structures and can achieve a sufficiently high molecular weight. A high molecular weight aromatic polycarbonate resin manufacturing method including: a step in which a dialcohol compound expressed by general formula (1) and a catalyst are mixed to obtain a catalyst composition; a step in which the obtained catalyst composition is transferred to a prepolymer mixing tank via a transfer pipe, with a transfer period of 10 hours or less; a step in which the transferred catalyst composition and an aromatic polycarbonate prepolymer are mixed in the prepolymer mixing tank to obtain a prepolymer mixture; and a high molecular weight achievement step in which the obtained prepolymer mixture is heat-treated under reduced pressure conditions to obtain a high molecular weight aromatic polycarbonate resin.Type: GrantFiled: March 24, 2017Date of Patent: February 23, 2021Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Yoshinori Isahaya, Atsushi Hirashima, Hidefumi Harada, Maki Ito, Jun-ya Hayakawa, Takehiko Isobe, Yousuke Shinkai, Keisuke Shimokawa
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Patent number: 10894860Abstract: A high molecular weight aromatic polycarbonate resin manufacturing method that can achieve good quality and sufficiently high molecular weight includes: a step in which a dialcohol compound expressed by general formula (1) and a catalyst are mixed to obtain a catalyst composition; a step in which the obtained catalyst composition is transferred to a prepolymer mixing tank via a transfer pipe; a step in which the transferred catalyst composition and an aromatic polycarbonate prepolymer are mixed in the prepolymer mixing tank, under a pressure that is greater than or equal to the vapor pressure of the dialcohol compound at the temperature of the prepolymer mixing tank and is less than or equal to 5 MPa, to obtain a prepolymer mixture; and a high molecular weight achievement step in which the obtained prepolymer mixture is heat-treated under reduced pressure conditions to obtain a high molecular weight aromatic polycarbonate resin.Type: GrantFiled: March 24, 2017Date of Patent: January 19, 2021Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Yoshinori Isahaya, Atsushi Hirashima, Hidefumi Harada, Maki Ito, Jun-ya Hayakawa, Takehiko Isobe, Yousuke Shinkai, Keisuke Shimokawa
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Publication number: 20200392085Abstract: Provided is a method for regenerating an aromatic amide compound into a corresponding aromatic nitrile compound, the method realizing a dehydration reaction of providing a target compound selectively at a high yield, with generation of a by-product being suppressed. Also provided is a method for producing an aromatic nitrile compound that decreases the number of steps of the dehydration reaction and significantly improves the reaction speed even at a pressure close to normal pressure. In addition, the above-described production method is applied to a carbonate ester production method to provide a method for producing a carbonate ester efficiently. The above-described methods are realized by a method for producing an aromatic nitrile compound including a dehydration reaction of dehydrating an aromatic amide compound, in which the dehydration reaction uses, as a solvent, any of 1,2-dimethoxybenzene, 1,3-dimethoxybenzene and 1,3,5-trimethoxybenzene.Type: ApplicationFiled: August 28, 2020Publication date: December 17, 2020Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Hidefumi HARADA, Yousuke SHINKAI, Hongyu LIU, Takehiko ISOBE, Yoshinori ISAHAYA
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Patent number: 10793524Abstract: Provided is a method for regenerating an aromatic amide compound into a corresponding aromatic nitrile compound, the method realizing a dehydration reaction of providing a target compound selectively at a high yield, with generation of a by-product being suppressed. Also provided is a method for producing an aromatic nitrile compound that decreases the number of steps of the dehydration reaction and significantly improves the reaction speed even at a pressure close to normal pressure. In addition, the above-described production method is applied to a carbonate ester production method to provide a method for producing a carbonate ester efficiently. The above-described methods are realized by a method for producing an aromatic nitrile compound including a dehydration reaction of dehydrating an aromatic amide compound, in which the dehydration reaction uses, as a solvent, any of 1,2-dimethoxybenzene, 1,3-dimethoxybenzene and 1,3,5-trimethoxybenzene.Type: GrantFiled: November 30, 2017Date of Patent: October 6, 2020Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Hidefumi Harada, Yousuke Shinkai, Hongyu Liu, Takehiko Isobe, Yoshinori Isahaya
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Publication number: 20200282389Abstract: Realized is a method for restoring the activity of a catalyst for producing a carbonate ester by a simple technique with no use of a complicated step such as calcining or the like to allow the catalyst to be reusable, and a method for producing a carbonate ester at a high yield by use of the catalyst thus regenerated. The above-described problem has been solved by a method for regenerating a catalyst containing CeO2, the catalyst being usable for a carbonate ester generation reaction of generating a carbonate ester from carbon dioxide and an alcohol, the method comprising (a) a separation step of separating the catalyst as a crude catalyst from a reaction solution of carbon dioxide and the alcohol; and (b) a catalyst processing step of washing the crude catalyst with a washing alcohol to provide a purified catalyst.Type: ApplicationFiled: September 25, 2018Publication date: September 10, 2020Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Hidefumi HARADA, Takehiko ISOBE, Hongyu LIU, Yousuke SHINKAI, Ryotaro UMEZU
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Publication number: 20200216611Abstract: Provided is a manufacturing method for a high molecular weight aromatic polycarbonate resin that has superior fluidity and for which a good color and a sufficiently high molecular weight can be achieved. A manufacturing method for a high molecular weight aromatic polycarbonate resin includes: a step in which a dialcohol compound expressed by general formula (1) and a catalyst are mixed to obtain a catalyst composition; a step in which the obtained catalyst composition is kept in a molten state, and is mixed with an aromatic polycarbonate prepolymer within ten hours after obtaining the catalyst composition, to obtain a prepolymer mixture; and a high molecular weight achievement step in which the obtained prepolymer mixture is heat-treated under reduced pressure conditions to obtain a high molecular weight aromatic polycarbonate resin.Type: ApplicationFiled: March 24, 2017Publication date: July 9, 2020Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Yoshinori ISAHAYA, Atsushi HIRASHIMA, Hidefumi HARADA, Maki ITO, Jun-ya HAYAKAWA, Takehiko ISOBE, Yousuke SHINKAI, Keisuke SHIMOKAWA
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Patent number: 10584092Abstract: Provided is a method for regenerating an aromatic amide compound into a corresponding aromatic nitrile compound, the method realizing a dehydration reaction of providing a target compound selectively at a high yield with generation of a by-product being suppressed. Also provided is a method for producing an aromatic nitrile compound that decreases the number of steps of dehydration reaction and significantly improves the reaction speed at a pressure close to normal pressure. Furthermore, the above-described production method is applied to a carbonate ester production method to provide a method for producing carbonate ester efficiently. The above-described objects are achieved by a method for producing an aromatic nitrile compound including a dehydration reaction of dehydrating an aromatic amide compound, in which the dehydration reaction uses diphenylether.Type: GrantFiled: June 20, 2017Date of Patent: March 10, 2020Assignees: MITSUBISHI GAS CHEMICAL COMPANY, INC., TOHOKU UNIVERSITY, NIPPON STEEL CORPORATION, NIPPON STEEL ENGINEERING CO., LTD.Inventors: Yousuke Shinkai, Hongyu Liu, Hidefumi Harada, Yoshinori Isahaya, Keiichi Tomishige, Yoshinao Nakagawa, Masazumi Tamura, Kimihito Suzuki, Yasuki Namiki
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Publication number: 20190382345Abstract: Provided is a method for regenerating an aromatic amide compound into a corresponding aromatic nitrile compound, the method realizing a dehydration reaction of providing a target compound selectively at a high yield, with generation of a by-product being suppressed. Also provided is a method for producing an aromatic nitrile compound that decreases the number of steps of the dehydration reaction and significantly improves the reaction speed even at a pressure close to normal pressure. In addition, the above-described production method is applied to a carbonate ester production method to provide a method for producing a carbonate ester efficiently. The above-described methods are realized by a method for producing an aromatic nitrile compound including a dehydration reaction of dehydrating an aromatic amide compound, in which the dehydration reaction uses, as a solvent, any of 1,2-dimethoxybenzene, 1,3-dimethoxybenzene and 1,3,5-trimethoxybenzene.Type: ApplicationFiled: November 30, 2017Publication date: December 19, 2019Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Hidefumi HARADA, Yousuke SHINKAI, Hongyu LIU, Takehiko ISOBE, Yoshinori ISAHAYA
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Publication number: 20190185408Abstract: Provided is a method for regenerating an aromatic amide compound into a corresponding aromatic nitrile compound, the method realizing a dehydration reaction of providing a target compound selectively at a high yield with generation of a by-product being suppressed. Also provided is a method for producing an aromatic nitrile compound that decreases the number of steps of dehydration reaction and significantly improves the reaction speed at a pressure close to normal pressure. Furthermore, the above-described production method is applied to a carbonate ester production method to provide a method for producing carbonate ester efficiently. The above-described objects are achieved by a method for producing an aromatic nitrile compound including a dehydration reaction of dehydrating an aromatic amide compound, in which the dehydration reaction uses diphenylether.Type: ApplicationFiled: June 20, 2017Publication date: June 20, 2019Applicants: Mitsubishi Gas Chemical Company, Inc., Tohoku University, Nippon Steel & Sumitomo Metal Corporation, Nippon Steel & Sumikin Engineering Co., Ltd.Inventors: Yousuke SHINKAI, Hongyu LIU, Hidefumi HARADA, Yoshinori ISAHAYA, Keiichi TOMISHIGE, Yoshinao NAKAGAWA, Masazumi TAMURA, Kimihito SUZUKI, Yasuki NAMIKI
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Publication number: 20190119441Abstract: A high molecular weight aromatic polycarbonate resin manufacturing method that can achieve good quality and sufficiently high molecular weight includes: a step in which a dialcohol compound expressed by general formula (1) and a catalyst are mixed to obtain a catalyst composition; a step in which the obtained catalyst composition is transferred to a prepolymer mixing tank via a transfer pipe; a step in which the transferred catalyst composition and an aromatic polycarbonate prepolymer are mixed in the prepolymer mixing tank, under a pressure that is greater than or equal to the vapor pressure of the dialcohol compound at the temperature of the prepolymer mixing tank and is less than or equal to 5 MPa, to obtain a prepolymer mixture; and a high molecular weight achievement step in which the obtained prepolymer mixture is heat-treated under reduced pressure conditions to obtain a high molecular weight aromatic polycarbonate resin.Type: ApplicationFiled: March 24, 2017Publication date: April 25, 2019Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Yoshinori ISAHAYA, Atsushi HIRASHIMA, Hidefumi HARADA, Maki ITO, Jun-ya HAYAKAWA, Takehiko ISOBE, Yousuke SHINKAI, Keisuke SHIMOKAWA
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Publication number: 20190092901Abstract: Provided is a high molecular weight aromatic polycarbonate resin manufacturing method that suppresses the occurrence of heterogeneous structures and can achieve a sufficiently high molecular weight. A high molecular weight aromatic polycarbonate resin manufacturing method including: a step in which a dialcohol compound expressed by general formula (1) and a catalyst are mixed to obtain a catalyst composition; a step in which the obtained catalyst composition is transferred to a prepolymer mixing tank via a transfer pipe, with a transfer period of 10 hours or less; a step in which the transferred catalyst composition and an aromatic polycarbonate prepolymer are mixed in the prepolymer mixing tank to obtain a prepolymer mixture; and a high molecular weight achievement step in which the obtained prepolymer mixture is heat-treated under reduced pressure conditions to obtain a high molecular weight aromatic polycarbonate resin.Type: ApplicationFiled: March 24, 2017Publication date: March 28, 2019Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Yoshinori ISAHAYA, Atsushi HIRASHIMA, Hidefumi HARADA, Maki ITO, Jun-ya HAYAKAWA, Takehiko ISOBE, Yousuke SHINKAI, Keisuke SHIMOKAWA
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Publication number: 20190085123Abstract: Provided is an aromatic polycarbonate resin composition with high fluidity, particularly during low shear, and a good color. An aromatic polycarbonate resin composition including: an aromatic polycarbonate resin that has a structural unit expressed by general formula (1); a aliphatic cyclic carbonate that is expressed by general formula (2) and is included at a ratio of 10 ppm-10,000 ppm; an aromatic cyclic carbonate that is expressed by general formula (3); and at least one compound selected from the group consisting of compounds expressed by general formulas (4)-(6), wherein the total content of the aromatic cyclic carbonate and the compound(s) expressed by general formula(s) (4)-(6) is 0.1 mass %-2.0 mass % by bisphenol A-converted value.Type: ApplicationFiled: March 24, 2017Publication date: March 21, 2019Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.Inventors: Yoshinori ISAHAYA, Atsushi HIRASHIMA, Hidefumi HARADA, Maki ITO, Jun-ya HAYAKAWA, Takehiko ISOBE, Yousuke SHINKAI, Keisuke SHIMOKAWA