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).
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Patent number: 8093429Abstract: 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: GrantFiled: May 31, 2007Date of Patent: January 10, 2012Assignees: National University Corporation Hokkaido University, Mitsubishi Gas Chemical Company, Inc.Inventors: Toshio Hidaka, Takafumi Yoshimura, Shoji Hara, Tsuyoshi Fukuhara
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Patent number: 8080676Abstract: 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: GrantFiled: October 25, 2007Date of Patent: December 20, 2011Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Akifumi Iida, Youichi Kyuuko, Toshio Hidaka
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Patent number: 8063205Abstract: 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: GrantFiled: August 30, 2006Date of Patent: November 22, 2011Assignees: National University Corporation Hokkaido University, Mitsubishi Gas Chemical Company, Inc.Inventors: Shoji Hara, Tsuyoshi Fukuhara, Toshio Hidaka
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Patent number: 7829741Abstract: 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: GrantFiled: October 20, 2005Date of Patent: November 9, 2010Assignees: National University Corporation, Mitsubishi Gas Chemical Company, Inc.Inventors: Tsuyoshi Fukuhara, Shoji Hara, Toshio Hidaka
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Patent number: 7750182Abstract: 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: GrantFiled: February 10, 2004Date of Patent: July 6, 2010Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Toshio Hidaka, Takafumi Yoshimura, Yoshifumi Sato, Norio Fushimi, Masaharu Doya
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Publication number: 20100063305Abstract: 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: ApplicationFiled: October 25, 2007Publication date: March 11, 2010Applicant: Mitsubishi Gas ChemcialInventors: Akifumi Iida, Youichi Kyuuko, Toshio Hidaka
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Patent number: 7642374Abstract: 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: GrantFiled: July 1, 2004Date of Patent: January 5, 2010Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takafumi Yoshimura, Toshio Hidaka, Yoshifumi Sato, Norio Fushimi, Kazuhiro Yamada
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Patent number: 7638652Abstract: 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: GrantFiled: July 11, 2007Date of Patent: December 29, 2009Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Takafumi Yoshimura, Toshio Hidaka, Norio Fushimi
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Publication number: 20090281309Abstract: 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: ApplicationFiled: August 30, 2006Publication date: November 12, 2009Inventors: Shoji Hara, Tsuyoshi Fukuhara, Toshio Hidaka
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Patent number: 7615650Abstract: 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: GrantFiled: January 28, 2005Date of Patent: November 10, 2009Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Kazuo Tanaka, Youichi Kyuuko, Toshio Hidaka
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Publication number: 20090247789Abstract: 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: ApplicationFiled: July 11, 2007Publication date: October 1, 2009Inventors: Takafumi Yoshimura, Toshio Hidaka, Norio Fushimi
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Publication number: 20090198086Abstract: 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: ApplicationFiled: May 31, 2007Publication date: August 6, 2009Inventors: Toshio Hidaka, Takafumi Yoshimura, Shoji Hara, Tsuyoshi Fukuhara
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Publication number: 20090177012Abstract: 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: ApplicationFiled: October 20, 2005Publication date: July 9, 2009Inventors: Tsuyoshi Fukuhara, Shoji Hara, Toshio Hidaka
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Patent number: 7405331Abstract: 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: GrantFiled: April 24, 2003Date of Patent: July 29, 2008Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Toshio Hidaka, Norio Fushimi, Takafumi Yoshimura, Takeshi Kawai
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Patent number: 7297821Abstract: 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: GrantFiled: December 9, 2005Date of Patent: November 20, 2007Assignee: Mitsubishi Gas Chemical Company, Inc.Inventors: Toshio Hidaka, Norio Fushimi, Takafumi Yoshimura, Takeshi Kawai
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Publication number: 20070179304Abstract: 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: ApplicationFiled: January 28, 2005Publication date: August 2, 2007Inventors: Kazuo Tanaka, Youichi Kyuuko, Toshio Hidaka
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Publication number: 20060167324Abstract: 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: ApplicationFiled: April 24, 2003Publication date: July 27, 2006Inventors: Toshio Hidaka, Norio Fushimi, Takafumi Yoshimura, Takeshi Kawai
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Publication number: 20060167312Abstract: 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: ApplicationFiled: July 1, 2004Publication date: July 27, 2006Inventors: Takafumi Yoshimura, Toshio Hidaka, Yoshifumi Sato, Norio Fushimi, Kazuhiro Yamada
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Publication number: 20060161028Abstract: 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: ApplicationFiled: February 10, 2004Publication date: July 20, 2006Inventors: Toshio Hidaka, Takafumi Yoshimura, Yoshifumi Sato, Norio Fushimi, Masaharu Doya
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Publication number: 20060141591Abstract: 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: ApplicationFiled: May 31, 2004Publication date: June 29, 2006Inventors: Youichi Kyuuko, Sachiko Koshiishi, Toshio Hidaka