Patents by Inventor Hidefumi Harada

Hidefumi Harada 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: 20220177646
    Abstract: 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: Application
    Filed: February 9, 2022
    Publication date: June 9, 2022
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yoshinori ISAHAYA, Atsushi HIRASHIMA, Hidefumi HARADA, Maki ITO, Jun-ya HAYAKAWA, Takehiko ISOBE, Yousuke SHINKAI, Keisuke SHIMOKAWA
  • Publication number: 20220009873
    Abstract: 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: Application
    Filed: December 4, 2019
    Publication date: January 13, 2022
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Hongyu LIU, Takehiko ISOBE, Yousuke SHINKAI, Hidefumi HARADA
  • Patent number: 11161816
    Abstract: 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: Grant
    Filed: August 28, 2020
    Date of Patent: November 2, 2021
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Hidefumi Harada, Yousuke Shinkai, Hongyu Liu, Takehiko Isobe, Yoshinori Isahaya
  • Patent number: 11142506
    Abstract: Disclosed are a diaryl carbonate containing a compound of the following formula (I) in an amount of less than 1,000 ppm by mass, and a method for producing the same: wherein Rl represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group, or an aryloxy group. Disclosed methods include reacting urea with an alkyl alcohol to provide a dialkyl carbonate; reacting the dialkyl carbonate with an aryl alcohol to provide an alkylaryl carbonate; subjecting the alkylaryl carbonate to disproportionation to yield a mixture comprising a diaryl carbonate; and purifying the mixture.
    Type: Grant
    Filed: January 9, 2020
    Date of Patent: October 12, 2021
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Hidefumi Harada, Jungo Taguchi, Yoshinori Isahaya
  • Publication number: 20210284594
    Abstract: 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: Application
    Filed: July 8, 2019
    Publication date: September 16, 2021
    Applicants: 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
  • Publication number: 20210261496
    Abstract: The present invention provides a method for producing an aromatic nitrile compound, the method comprising a dehydration reaction wherein a desired compound can be selectively obtained with high yield while suppressing the generation of by-products during the regeneration of an aromatic amide compound into the corresponding aromatic nitrile compound. In addition, the present invention realizes a method for efficiently producing a carbonate ester by applying the abovementioned production method to a method for producing a carbonate ester. The above are achieved by means of a method for producing an aromatic nitrile compound involving a dehydration reaction wherein an aromatic amide compound is dehydrated, the method having a contact step for bringing the aromatic amide compound into contact with a catalyst in a gas phase during the dehydration reaction.
    Type: Application
    Filed: July 25, 2019
    Publication date: August 26, 2021
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Hidefumi HARADA, Takehiko ISOBE, Keisuke SHIMOKAWA, Ryotaro UMEZU
  • Patent number: 11021571
    Abstract: 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: Grant
    Filed: March 24, 2017
    Date of Patent: June 1, 2021
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yoshinori Isahaya, Atsushi Hirashima, Hidefumi Harada, Maki Ito, Jun-ya Hayakawa, Takehiko Isobe, Yousuke Shinkai, Keisuke Shimokawa
  • Patent number: 11014869
    Abstract: The present application addresses the problem of providing a method for efficiently producing a dialkyl carbonate. The problem can be solved by a method for producing a dialkyl carbonate by reacting urea and at least one alkyl carbamate with an aliphatic alcohol in the presence of a catalyst, the method including introducing a gas for expelling ammonia generated by the reaction into a reactor in which the reaction is being conducted and discharging the ammonia generated in the reactor and the introduced gas, the reaction being conducted so that the gas introduction satisfies relationship (1). 52.0<((A+B)×22400+L×M/17.03×22400)/L<91.0??(1) (In formula (1), A, B, L, and M are as defined above.
    Type: Grant
    Filed: August 10, 2018
    Date of Patent: May 25, 2021
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC
    Inventors: Keisuke Shimokawa, Hidefumi Harada, Takehiko Isobe, Hongyu Liu
  • Publication number: 20210087333
    Abstract: A polycarbonate resin composition containing 0.1 to 10 parts by mass of a polycarbonate copolymer (B) having carbonate bonding between (B1) bisphenol A and a (B2) polyalkylene glycol and 0.005 to 0.5 parts by mass of a phosphorus-containing stabilizer (C) relative to 100 parts by mass of a polycarbonate resin (A).
    Type: Application
    Filed: February 25, 2019
    Publication date: March 25, 2021
    Applicants: Mitsubishi Engeering-Platics Corporation, MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Keisuke TOMITA, Hidefumi HARADA, Takehiko ISOBE, Keisuke SHIMOKAWA, Jugo TAGUCHI
  • Publication number: 20210061749
    Abstract: 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: Application
    Filed: January 8, 2019
    Publication date: March 4, 2021
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Hidefumi HARADA, Takehiko ISOBE, Hongyu LIU, Yousuke SHINKAI, Ryotaro UMEZU
  • Patent number: 10927216
    Abstract: 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: Grant
    Filed: March 24, 2017
    Date of Patent: February 23, 2021
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yoshinori Isahaya, Atsushi Hirashima, Hidefumi Harada, Maki Ito, Jun-ya Hayakawa, Takehiko Isobe, Yousuke Shinkai, Keisuke Shimokawa
  • Patent number: 10894860
    Abstract: 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: Grant
    Filed: March 24, 2017
    Date of Patent: January 19, 2021
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yoshinori Isahaya, Atsushi Hirashima, Hidefumi Harada, Maki Ito, Jun-ya Hayakawa, Takehiko Isobe, Yousuke Shinkai, Keisuke Shimokawa
  • Publication number: 20200392085
    Abstract: 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: Application
    Filed: August 28, 2020
    Publication date: December 17, 2020
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Hidefumi HARADA, Yousuke SHINKAI, Hongyu LIU, Takehiko ISOBE, Yoshinori ISAHAYA
  • Patent number: 10793524
    Abstract: 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: Grant
    Filed: November 30, 2017
    Date of Patent: October 6, 2020
    Assignee: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Hidefumi Harada, Yousuke Shinkai, Hongyu Liu, Takehiko Isobe, Yoshinori Isahaya
  • Publication number: 20200282389
    Abstract: 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: Application
    Filed: September 25, 2018
    Publication date: September 10, 2020
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Hidefumi HARADA, Takehiko ISOBE, Hongyu LIU, Yousuke SHINKAI, Ryotaro UMEZU
  • Publication number: 20200239402
    Abstract: The present application addresses the problem of providing a method for efficiently producing a dialkyl carbonate. The problem can be solved by a method for producing a dialkyl carbonate by reacting urea and at least one alkyl carbamate with an aliphatic alcohol in the presence of a catalyst, the method including introducing a gas for expelling ammonia generated by the reaction into a reactor in which the reaction is being conducted and discharging the ammonia generated in the reactor and the introduced gas, the reaction being conducted so that the gas introduction satisfies relationship (1). 52.0<((A+B)×22400+L×M/17.03×22400)/L<91.0??(1) (In formula (1), A, B, L, and M are as defined above.
    Type: Application
    Filed: August 10, 2018
    Publication date: July 30, 2020
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Keisuke SHIMOKAWA, Hidefumi HARADA, Takehiko ISOBE, Hongyu LIU
  • Publication number: 20200216611
    Abstract: 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: Application
    Filed: March 24, 2017
    Publication date: July 9, 2020
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Yoshinori ISAHAYA, Atsushi HIRASHIMA, Hidefumi HARADA, Maki ITO, Jun-ya HAYAKAWA, Takehiko ISOBE, Yousuke SHINKAI, Keisuke SHIMOKAWA
  • Publication number: 20200140399
    Abstract: A diaryl carbonate containing a compound of the following formula (I) in an amount of less than 1,000 ppm by mass, and a method for producing the same: wherein R1 represents a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, an aryl group, or an aryloxy group.
    Type: Application
    Filed: January 9, 2020
    Publication date: May 7, 2020
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Hidefumi HARADA, Jungo TAGUCHI, Yoshinori ISAHAYA
  • Patent number: 10584092
    Abstract: 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: Grant
    Filed: June 20, 2017
    Date of Patent: March 10, 2020
    Assignees: 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
  • Publication number: 20190382345
    Abstract: 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: Application
    Filed: November 30, 2017
    Publication date: December 19, 2019
    Applicant: MITSUBISHI GAS CHEMICAL COMPANY, INC.
    Inventors: Hidefumi HARADA, Yousuke SHINKAI, Hongyu LIU, Takehiko ISOBE, Yoshinori ISAHAYA