Patents by Inventor Toshio Hidaka

Toshio Hidaka 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).

  • Patent number: 8093429
    Abstract: Provided are a fluorous-tag-introduced fluoroamine of a general formula (I), its production method, a method of fluorination of a substrate having functional group containing oxygen with the fluoroamine serving as a fluorinating agent, and a method of recovering a fluorous-tag-introduced amide after the fluorination. The fluoroamine and its production method, as well as the fluorination method with the fluoroamine and the method of recovery of a fluorous-tag-introduced amide are ecological and advantageous in industrial use, as the load for separating and collecting the product after the fluorination with the fluoroamine serving as a fluorinating agent is small. (In the formula, R0 is an alkyl group or an aryl group having substituent(s) of Rf—(CH2)m—; Rf is a perfluoroalkyl group; m is from 0 to 2; R1 and R2 each are an alkyl group or an aryl group.
    Type: Grant
    Filed: May 31, 2007
    Date of Patent: January 10, 2012
    Assignees: National University Corporation Hokkaido University, Mitsubishi Gas Chemical Company, Inc.
    Inventors: Toshio Hidaka, Takafumi Yoshimura, Shoji Hara, Tsuyoshi Fukuhara
  • Patent number: 8080676
    Abstract: The present invention provides an industrially available method for efficiently producing high-purity S-(?)-6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid excellent in solid-liquid separability from an S-(?)-6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid ester, and also provides products obtained by the method. Under a temperature condition of 50-80° C. in an aqueous solvent, (A) an S-(?)-6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid ester represented by the general formula (1) is hydrolyzed under a basic condition for 1-3 hours; then (B) the insoluble matters contained in the reaction solution resulting from the hydrolysis are removed; and (C) an acid is added to the resulting solution to effect crystallization; provided that R in the general formula (1) represents an alkyl or aryl group.
    Type: Grant
    Filed: October 25, 2007
    Date of Patent: December 20, 2011
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Akifumi Iida, Youichi Kyuuko, Toshio Hidaka
  • Patent number: 8063205
    Abstract: The present invention is a method for producing a 2-oxazoline analogue or a 1,3-oxazine analogue represented by the following general formula (3) by reacting a 1,2-aminoalcohol compound or a 1,2-aminothiol compound with an ?,?-dihaloamine compound. (In the formula, n represents 0 or 1, and R represents an oxygen atom or a sulfur atom. R1, R2 and R3 each represents an atom or a group shown in Group 1 to Group 3, and R0 represents an atom or a group shown in Group 2 or Group 3. Two or more of R1, R2 and R3 may be bonded to each other to form a ring.
    Type: Grant
    Filed: August 30, 2006
    Date of Patent: November 22, 2011
    Assignees: National University Corporation Hokkaido University, Mitsubishi Gas Chemical Company, Inc.
    Inventors: Shoji Hara, Tsuyoshi Fukuhara, Toshio Hidaka
  • Patent number: 7829741
    Abstract: A process for producing an ?,?-difluoroamine which comprises using hydrogen fluoride and a Lewis base in specific amounts in the halogen-fluorine exchange reaction using an ?,?-dihaloamine as the substrate. The process can be industrially applied, enables to obtain the object compound in a short time at a great yield and can be conducted easily with excellent productivity.
    Type: Grant
    Filed: October 20, 2005
    Date of Patent: November 9, 2010
    Assignees: National University Corporation, Mitsubishi Gas Chemical Company, Inc.
    Inventors: Tsuyoshi Fukuhara, Shoji Hara, Toshio Hidaka
  • Patent number: 7750182
    Abstract: Provided is a production method for an iodine compound in which iodine is reacted with a substrate in the presence of a porous material having a pore diameter of 500 nm or less or in the presence of the above porous material and an oxidizing agent and a production process for high purity 5-iodo-2-methylbenzoic acid comprising an iodination reaction step carried out by the above-mentioned, a crystal precipitation and separation step in which a product is precipitated by adding water or cooling and then separated and a purification step in which crystal separated is recrystallized using an organic solvent. According to the production method for an iodine compound described above, iodine can be introduced into various substrates at a high selectivity. Since expensive metals and specific reagents do not have to be used, it can readily be carried out in an industrially scale, and the product having a high purity can be obtained.
    Type: Grant
    Filed: February 10, 2004
    Date of Patent: July 6, 2010
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Toshio Hidaka, Takafumi Yoshimura, Yoshifumi Sato, Norio Fushimi, Masaharu Doya
  • Publication number: 20100063305
    Abstract: The present invention provides an industrially available method for efficiently producing high-purity S-(?)-6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid excellent in solid-liquid separability from an S-(?)-6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid ester, and also provides products obtained by the method. Under a temperature condition of 50-80° C. in an aqueous solvent, (A) an S-(?)-6-hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid ester represented by the general formula (1) is hydrolyzed under a basic condition for 1-3 hours; then (B) the insoluble matters contained in the reaction solution resulting from the hydrolysis are removed; and (C) an acid is added to the resulting solution to effect crystallization; provided that R in the general formula (1) represents an alkyl or aryl group.
    Type: Application
    Filed: October 25, 2007
    Publication date: March 11, 2010
    Applicant: Mitsubishi Gas Chemcial
    Inventors: Akifumi Iida, Youichi Kyuuko, Toshio Hidaka
  • Patent number: 7642374
    Abstract: The present invention provides a process for producing 5-iodo-2-methylbenzoic acid through iodination of 2-methylbenzoic acid, the process including, as essential steps, a reaction step of iodinating 2-methylbenzoic acid in the presence of a microporous compound, iodine, an oxidizing agent, and acetic anhydride, and a purification step including sublimation, distillation, crystallization, or a combination of two or more of these. According to the present invention, 5-iodo-2-methylbenzoic acid, which is useful for producing functional chemicals such as drugs, can be produced at high purity and high yield in a simple manner. Since the production process includes a simple reaction step and a simple separation/purification step, the load of purification is mitigated. In addition, the microporous compound such as a zeolite catalyst which has been separated and recovered from the reaction mixture can be repeatedly employed after performing of a simple treatment.
    Type: Grant
    Filed: July 1, 2004
    Date of Patent: January 5, 2010
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takafumi Yoshimura, Toshio Hidaka, Yoshifumi Sato, Norio Fushimi, Kazuhiro Yamada
  • Patent number: 7638652
    Abstract: Provided is a one-step efficient production method for an ?,?-difluoroamine of a general formula (1) below from an amide compound. The method is an economical method capable of producing the intended ?,?-difluoroamine at high yield by reacting a starting amide compound with carbonyl fluoride and/or oxalyl fluoride under a specific condition.
    Type: Grant
    Filed: July 11, 2007
    Date of Patent: December 29, 2009
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Takafumi Yoshimura, Toshio Hidaka, Norio Fushimi
  • Publication number: 20090281309
    Abstract: The present invention is a method for producing a 2-oxazoline analogue or a 1,3-oxazine analogue represented by the following general formula (3) by reacting a 1,2-aminoalcohol compound or a 1,2-aminothiol compound with an ?,?-dihaloamine compound. (In the formula, n represents 0 or 1, and R represents an oxygen atom or a sulfur atom. R1, R2 and R3 each represents an atom or a group shown in Group 1 to Group 3, and R0 represents an atom or a group shown in Group 2 or Group 3. Two or more of R1, R2 and R3 may be bonded to each other to form a ring.
    Type: Application
    Filed: August 30, 2006
    Publication date: November 12, 2009
    Inventors: Shoji Hara, Tsuyoshi Fukuhara, Toshio Hidaka
  • Patent number: 7615650
    Abstract: The invention provides a process for producing a chroman compound represented by formula (1), characterized in that the process includes allowing a phenol, an unsaturated compound, and a formaldehyde to react in the absence of catalyst and in the presence of water in an amount by mole 1 to 10 times that of the phenol. According to the present invention, a high-purity chroman compound can be produced in the absence of catalyst and under mild conditions. In addition, the invention provides an industrial means for producing the compound, without using a large amount of an acid or a base serving as a reaction promoter or a catalyst, which would otherwise cause side reactions, apparatus corrosion, etc.
    Type: Grant
    Filed: January 28, 2005
    Date of Patent: November 10, 2009
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Kazuo Tanaka, Youichi Kyuuko, Toshio Hidaka
  • Publication number: 20090247789
    Abstract: Provided is a one-step efficient production method for an ?,?-difluoroamine of a general formula (1) below from an amide compound. The method is an economical method capable of producing the intended ?,?-difluoroamine at high yield by reacting a starting amide compound with carbonyl fluoride and/or oxalyl fluoride under a specific condition.
    Type: Application
    Filed: July 11, 2007
    Publication date: October 1, 2009
    Inventors: Takafumi Yoshimura, Toshio Hidaka, Norio Fushimi
  • Publication number: 20090198086
    Abstract: Provided are a fluorous-tag-introduced fluoroamine of a general formula (I), its production method, a method of fluorination of a substrate having functional group containing oxygen with the fluoroamine serving as a fluorinating agent, and a method of recovering a fluorous-tag-introduced amide after the fluorination. The fluoroamine and its production method, as well as the fluorination method with the fluoroamine and the method of recovery of a fluorous-tag-introduced amide are ecological and advantageous in industrial use, as the load for separating and collecting the product after the fluorination with the fluoroamine serving as a fluorinating agent is small. (In the formula, R0 is an alkyl group or an aryl group having substituent(s) of Rf—(CH2)m—; Rf is a perfluoroalkyl group; m is from 0 to 2; R1 and R2 each are an alkyl group or an aryl group.
    Type: Application
    Filed: May 31, 2007
    Publication date: August 6, 2009
    Inventors: Toshio Hidaka, Takafumi Yoshimura, Shoji Hara, Tsuyoshi Fukuhara
  • Publication number: 20090177012
    Abstract: A process for producing an ?,?-difluoroamine which comprises using hydrogen fluoride and a Lewis base in specific amounts in the halogen-fluorine exchange reaction using an ?,?-dihaloamine as the substrate. The process can be industrially applied, enables to obtain the object compound in a short time at a great yield and can be conducted easily with excellent productivity.
    Type: Application
    Filed: October 20, 2005
    Publication date: July 9, 2009
    Inventors: Tsuyoshi Fukuhara, Shoji Hara, Toshio Hidaka
  • Patent number: 7405331
    Abstract: The process for producing a (fluoroalkyl)benzene derivative according to the present invention comprises a step of reducing the total content of group 3 to group 12 transition metals in an alkylbenzene derivative to 500 ppm or less in terms of metal atoms; a step of halogenating the branched alkyl group of the purified alkylbenzene derivative by a photohalogenation to obtain a (haloalkyl)benzene derivative; and a step of subjecting the (haloalkyl)benzene derivative to a halogen-fluorine exchange using HF in an amount of 10 mol or higher per one mole of the (haloalkyl)benzene derivative. The (fluoroalkyl)benzene derivative produced by the process is reduced in the content of impurities such as residual halogens and residual metals, and is useful as intermediates for functional chemical products for use in applications such as medicines and electronic materials.
    Type: Grant
    Filed: April 24, 2003
    Date of Patent: July 29, 2008
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Toshio Hidaka, Norio Fushimi, Takafumi Yoshimura, Takeshi Kawai
  • Patent number: 7297821
    Abstract: A fluorine compound represented by Formula (1) is provided. The above fluorine compound is effective for introducing a fluorine atom into a compound having an active group such as an oxygen-containing functional group, and it can be used for uses of surface treatment, cleaning and coating. Further, after the fluorination reaction, the above compound is recovered and can be reused as a starting material for producing the above fluorine compound, and it is useful for various fluorination processes. (wherein X represents a nitrogen or phosphorus atom; R0, R1, and R2 represent hydrogen, an alkyl group or aryl group which may have a substituent, and they each may be the same or different; and R0, R1, and R2 may be combined with each other to form a ring).
    Type: Grant
    Filed: December 9, 2005
    Date of Patent: November 20, 2007
    Assignee: Mitsubishi Gas Chemical Company, Inc.
    Inventors: Toshio Hidaka, Norio Fushimi, Takafumi Yoshimura, Takeshi Kawai
  • Publication number: 20070179304
    Abstract: The invention provides a process for producing a chroman compound represented by formula (1), characterized in that the process includes allowing a phenol, an unsaturated compound, and a formaldehyde to react in the absence of catalyst and in the presence of water in an amount by mole 1 to 10 times that of the phenol. According to the present invention, a high-purity chroman compound can be produced in the absence of catalyst and under mild conditions. In addition, the invention provides an industrial means for producing the compound, without using a large amount of an acid or a base serving as a reaction promoter or a catalyst, which would otherwise cause side reactions, apparatus corrosion, etc.
    Type: Application
    Filed: January 28, 2005
    Publication date: August 2, 2007
    Inventors: Kazuo Tanaka, Youichi Kyuuko, Toshio Hidaka
  • Publication number: 20060167324
    Abstract: The process for producing a (fluoroalkyl)benzene derivative according to the present invention comprises a step of reducing the total content of group 3 to group 12 transition metals in an alkylbenzene derivative to 500 ppm or less in terms of metal atoms; a step of halogenating the branched alkyl group of the purified alkylbenzene derivative by a photohalogenation to obtain a (haloalkyl)benzene derivative; and a step of subjecting the (haloalkyl)benzene derivative to a halogen-fluorine exchange using HF in an amount of 10 mol or higher per one mole of the (haloalkyl)benzene derivative. The (fluoroalkyl)benzene derivative produced by the process is reduced in the content of impurities such as residual halogens and residual metals, and is useful as intermediates for functional chemical products for use in applications such as medicines and electronic materials.
    Type: Application
    Filed: April 24, 2003
    Publication date: July 27, 2006
    Inventors: Toshio Hidaka, Norio Fushimi, Takafumi Yoshimura, Takeshi Kawai
  • Publication number: 20060167312
    Abstract: The present invention provides a process for producing 5-iodo-2-methylbenzoic acid through iodination of 2-methylbenzoic acid, the process including, as essential steps, a reaction step of iodinating 2-methylbenzoic acid in the presence of a microporous compound, iodine, an oxidizing agent, and acetic anhydride, and a purification step including sublimation, distillation, crystallization, or a combination of two or more of these. According to the present invention, 5-iodo-2-methylbenzoic acid, which is useful for producing functional chemicals such as drugs, can be produced at high purity and high yield in a simple manner. Since the production process includes a simple reaction step and a simple separation/purification step, the load of purification is mitigated. In addition, the microporous compound such as a zeolite catalyst which has been separated and recovered from the reaction mixture can be repeatedly employed after performing of a simple treatment.
    Type: Application
    Filed: July 1, 2004
    Publication date: July 27, 2006
    Inventors: Takafumi Yoshimura, Toshio Hidaka, Yoshifumi Sato, Norio Fushimi, Kazuhiro Yamada
  • Publication number: 20060161028
    Abstract: Provided is a production method for an iodine compound in which iodine is reacted with a substrate in the presence of a porous material having a pore diameter of 500 nm or less or in the presence of the above porous material and an oxidizing agent and a production process for high purity 5-iodo-2-methylbenzoic acid comprising an iodination reaction step carried out by the above-mentioned, a crystal precipitation and separation step in which a product is precipitated by adding water or cooling and then separated and a purification step in which crystal separated is recrystallized using an organic solvent. According to the production method for an iodine compound described above, iodine can be introduced into various substrates at a high selectivity. Since expensive metals and specific reagents do not have to be used, it can readily be carried out in an industrially scale, and the product having a high purity can be obtained.
    Type: Application
    Filed: February 10, 2004
    Publication date: July 20, 2006
    Inventors: Toshio Hidaka, Takafumi Yoshimura, Yoshifumi Sato, Norio Fushimi, Masaharu Doya
  • Publication number: 20060141591
    Abstract: In the method for producing an optically active chromancarboxylate of the present invention, one of the enantiomers of racemic chromancarboxylic acid is esterified in a solvent containing an alcohol in the presence of a biocatalyst. After the esterification, the other enantiomer, i.e., the non-reacted chromancarboxylic acid is separated out of the reaction mixture to obtain the aimed optically active ester. The optically active chromancarboxylate is useful as the material for medicines, agricultural chemicals, etc. The invention provides an efficient production method thereof which is industrially applicable.
    Type: Application
    Filed: May 31, 2004
    Publication date: June 29, 2006
    Inventors: Youichi Kyuuko, Sachiko Koshiishi, Toshio Hidaka