Patents by Inventor Tatsuya Ohtsuka
Tatsuya Ohtsuka 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: 9593058Abstract: An object of the present invention is to provide a production method that makes it possible to produce 1,1-dibromo-1-fluoroethane easily and sustainably. The present invention provides a method for producing 1,1-dibromo-1-fluoroethane, the method comprising step A of reacting 1,1-dibromoethylene with hydrogen fluoride to obtain 1,1-dibromo-1-fluoroethane.Type: GrantFiled: September 3, 2014Date of Patent: March 14, 2017Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Atsushi Shirai, Masatoshi Nose, Yosuke Kishikawa, Tatsuya Ohtsuka, Sumi Ishihara
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Publication number: 20160318842Abstract: An object of the present invention is to provide a process for producing ?-fluoroacrylic acid esters at a high starting material conversion and a high yield. The present invention provides, as a means to achieve the object, a process for producing a compound represented by formula (1): wherein R2 and R2 are the same or different and each represent alkyl, fluoroalkyl, aryl optionally substituted with at least one substituent, halogen, or hydrogen; and R3 represents alkyl, fluoroalkyl, or aryl optionally substituted with at least one substituent, the process comprising step A of reacting a compound represented by formula (2): wherein the symbols are as defined above, with carbon monoxide and an alcohol represented by formula (3): R3—OH ??(3) wherein the symbol is as defined above, in the presence of a transition metal complex catalyst containing at least one bidentate phosphine ligand and a base to thereby obtain the compound represented by formula (1).Type: ApplicationFiled: December 26, 2014Publication date: November 3, 2016Applicant: DAIKIN INDUSTRIES, LTD.Inventors: Akihiro GOTOU, Manaho MIYAZAKI, Sumi ISHIHARA, Takashi NAMIKAWA, Tatsuya OHTSUKA, Yosuke KISHIKAWA
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Publication number: 20160297740Abstract: The object of the present invention is to provide a process for producing ?-fluoroacrylic acid ester at a high starting material conversion, high selectivity, and high yield. The present invention provides a process for producing the compound represented by the formula (1) wherein R represents alkyl optionally substituted with one or more fluorine atoms, the process comprising step A of reacting a compound represented by the formula (2) wherein X represents a bromine atom or a chlorine atom with an alcohol represented by the formula (3) wherein the symbol is as defined above, and carbon monoxide in the presence of a transition metal catalyst and a base to thereby obtain the compound represented by the formula (1).Type: ApplicationFiled: June 15, 2016Publication date: October 13, 2016Applicant: DAIKIN INDUSTRIES, LTD.Inventors: Tatsuya OHTSUKA, Akihiro GOTOU, Sumi ISHIHARA, Yoshihiro YAMAMOTO, Akinori YAMAMOTO, Yoshichika KUROKI, Yuzo KOMATSU, Yousuke KISHIKAWA
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Publication number: 20160221900Abstract: An object of the present invention is to provide a production method that makes it possible to produce 1,1-dibromo-1-fluoroethane easily and sustainably. The present invention provides a method for producing 1,1-dibromo-1-fluoroethane, the method comprising step A of reacting 1,1-dibromoethylene with hydrogen fluoride to obtain 1,1-dibromo-1-fluoroethane.Type: ApplicationFiled: September 3, 2014Publication date: August 4, 2016Applicant: DAIKIN INDUSTRIES, LTD.Inventors: Atsushi SHIRAI, Masatoshi NOSE, Yosuke KISHIKAWA, Tatsuya OHTSUKA, Sumi ISHIHARA
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Patent number: 9388117Abstract: The object of the present invention is to provide a process for producing ?-fluoroacrylic acid ester at a high starting material conversion, high selectivity, and high yield. The present invention provides a process for producing the compound represented by the formula (1) wherein R represents alkyl optionally substituted with one or more fluorine atoms, the process comprising step A of reacting a compound represented by the formula (2) wherein X represents a bromine atom or a chlorine atom with an alcohol represented by the formula (3) wherein the symbol is as defined above, and carbon monoxide in the presence of a transition metal catalyst and a base to thereby obtain the compound represented by the formula (1).Type: GrantFiled: August 30, 2013Date of Patent: July 12, 2016Assignee: DAIKIN INDUSTRIES, LTD.Inventors: Tatsuya Ohtsuka, Akihiro Gotou, Sumi Ishihara, Yoshihiro Yamamoto, Akinori Yamamoto, Yoshichika Kuroki, Yuzo Komatsu, Yousuke Kishikawa
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Publication number: 20160168060Abstract: An object of the present invention is to provide a method for producing methane fluoride that is useful, for example, as a dry etching gas, the method being more suitable for industrial production. To achieve this object, the present invention provides a method including reacting (A) dimethyl sulfate and (B) at least one fluorocompound in a liquid phase, the fluorocompound (B) being at least one compound selected from the group consisting of hydrogen fluoride and hydrofluoric acid salts, or a metal fluoride, wherein when the fluoride compound (B) includes hydrogen fluoride or a hydrofluoric acid salt, the reaction is carried out without a solvent or using a polar solvent as a solvent, and when the fluoride compound (B) is a metal fluoride, the reaction is carried out using water as a solvent.Type: ApplicationFiled: August 7, 2014Publication date: June 16, 2016Applicant: DAIKIN INDUSTRIES, LTD.Inventors: Shingo NAKAMURA, Kanako FUKUMOTO, Yuusuke ETOU, Tatsuya OHTSUKA, Masahiro HIGASHI
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Publication number: 20150299088Abstract: Provided is a method for producing fluoromethane and 3,3,3-trifluoro-2-(trifluoromethyl)propanoyl fluoride ((CF3)2CHCOF), which are useful as dry etching gases etc., safely and inexpensively with high purity. According to the method in which 1,1,3,3,3-pentafluoro-2-trifluoromethylpropyl methyl ether is pyrolyzed in a gas phase in the presence of a catalyst, the desired fluoromethane and 3,3,3-trifluoro-2-(trifluoromethyl)propanoyl fluoride can be obtained with high selectivity and high conversion of the starting material by a simple process in which a pyrolysis reaction is performed in a gas phase using the inexpensive starting material.Type: ApplicationFiled: November 12, 2013Publication date: October 22, 2015Inventors: Shingo NAKAMURA, Yuusuke ETOU, Tatsuya OHTSUKA, Kanako FUKUMOTO, Masato NAITOU
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Publication number: 20150191413Abstract: The object of the present invention is to provide a process for producing ?-fluoroacrylic acid ester at a high starting material conversion, high selectivity, and high yield. The present invention provides a process for producing the compound represented by the formula (1) wherein R represents alkyl optionally substituted with one or more fluorine atoms, the process comprising step A of reacting a compound represented by the formula (2) wherein X represents a bromine atom or a chlorine atom with an alcohol represented by the formula (3) wherein the symbol is as defined above, and carbon monoxide in the presence of a transition metal catalyst and a base to thereby obtain the compound represented by the formula (1).Type: ApplicationFiled: August 30, 2013Publication date: July 9, 2015Inventors: Tatsuya Ohtsuka, Akihiro Gotou, Sumi Ishihara, Yoshihiro Yamamoto, Akinori Yamamoto, Yoshichika Kuroki, Yuzo Komatsu, Yousuke Kishikawa
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Patent number: 8022245Abstract: The present invention provides a novel ?-fluoromethoxycarboxylic ester represented by Formula (1): (CF3)2C(OCH2F)COOR wherein R is a hydrocarbon group that may have a substituent; a process for producing 1,1,1,3,3,3-hexafluoroisopropyl fluoromethyl ether, the process including hydrolyzing and decarboxylating the ?-fluoromethoxycarboxylic ester; and a process for producing an ?-fluoromethoxycarboxylic ester represented by Formula (1): (CF3)2C (OCH2F)COOR, the process including reacting an ?-hydroxycarboxylic ester represented by Formula (2): (CF3)2C(OH)COOR with a halofluoromethane in the presence of an alkaline compound. According to the present invention, 1,1,1,3,3,3-hexafluoroisopropyl fluoromethyl ether (sevoflurane), which is known as an anesthetic compound, can be efficiently produced at low cost.Type: GrantFiled: June 27, 2007Date of Patent: September 20, 2011Assignee: Daikin Industries, Ltd.Inventors: Tatsuya Ohtsuka, Yoshichika Kuroki, Atsushi Suzuki
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Patent number: 8013182Abstract: The present invention provides a process for producing a novel compound, i.e., ?-chloromethoxycarboxylic acid ester represented by General Formula (1): (CF3)2C(OCH2Cl)COOR, wherein R is a hydrocarbon group which may be substituted with at least one atom selected from the group consisting of halogen, oxygen, nitrogen, and sulfur atoms, comprising reacting an ?-methoxycarboxylic acid ester represented by General Formula (2): (CF3)2C(OCH3)COOR, wherein R is as defined above, with molecular chlorine; and a process for producing 1,1,1,3,3,3-hexafluoroisopropyl fluoromethyl ether represented by a chemical formula (CF3)2CH(OCH2F), comprising fluorinating and decarboxylating the ?-chloromethoxycarboxylic acid ester. According to the present invention, 1,1,1,3,3,3-hexafluoroisopropyl fluoromethyl ether (sevoflurane), which is known as a compound having an anesthetic property, can be produced efficiently and at a low cost.Type: GrantFiled: November 6, 2008Date of Patent: September 6, 2011Assignee: Daikin Industries, Ltd.Inventors: Yoshihiro Yamamoto, Tatsuya Ohtsuka
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Patent number: 7985877Abstract: The present invention provides a process for producing 1,1,1,3,3,3-hexafluoro-2-methoxypropane, wherein a novel compound, 2-methoxy-2-trifluoromethyl-3,3,3-trifluoropropionic acid or a salt thereof is decarboxylated, or wherein an olefin compound represented by chemical formula (4): CF2?C(CF3)(OCH3) is reacted with a fluorinating agent; and a process for producing 2-methoxy-2-trifluoromethyl-3,3,3-trifluoropropionic acid or a salt thereof by reacting a hydroxycarboxylic ester with a methylating agent and then hydrolyzing the reaction product, or hydrolyzing the hydroxycarboxylic ester and then reacting the resulting product with a methylating agent. In accordance with the invention, 1,1,1,3,3,3-hexafluoro-2-methoxypropane, which is useful as a raw material for, for example, the anesthetic Sevoflurane, can be produced efficiently and at low cost.Type: GrantFiled: May 31, 2007Date of Patent: July 26, 2011Assignee: Daikin Industries, Ltd.Inventors: Tatsuya Ohtsuka, Yoshihiro Yamamoto, Yoshichika Kuroki, Atsushi Suzuki, Akinari Sugiyama
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Publication number: 20100234634Abstract: The present invention provides a process for producing a novel compound, i.e., ?-chloromethoxycarboxylic acid ester represented by General Formula (1): (CF3)2C(OCH2Cl)COOR, wherein R is a hydrocarbon group which may be substituted with at least one atom selected from the group consisting of halogen, oxygen, nitrogen, and sulfur atoms, comprising reacting an ?-methoxycarboxylic acid ester represented by General Formula (2): (CF3)2C(OCH3)COOR, wherein R is as defined above, with molecular chlorine; and a process for producing 1,1,1,3,3,3-hexafluoroisopropyl fluoromethyl ether represented by a chemical formula (CF3)2CH(OCH2F), comprising fluorinating and decarboxylating the ?-chloromethoxycarboxylic acid ester. According to the present invention, 1,1,1,3,3,3-hexafluoroisopropyl fluoromethyl ether (sevoflurane), which is known as a compound having an anesthetic property, can be produced efficiently and at a low cost.Type: ApplicationFiled: November 6, 2008Publication date: September 16, 2010Inventors: Yoshihiro Yamamoto, Tatsuya Ohtsuka
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Publication number: 20100010255Abstract: The present invention provides a novel ?-fluoromethoxycarboxylic ester represented by Formula (1): (CF3)2C(OCH2F)COOR wherein R is a hydrocarbon group that may have a substituent; a process for producing 1,1,1,3,3,3-hexafluoroisopropyl fluoromethyl ether, the process including hydrolyzing and decarboxylating the ?-fluoromethoxycarboxylic ester; and a process for producing an ?-fluoromethoxycarboxylic ester represented by Formula (1): (CF3)2C (OCH2F)COOR, the process including reacting an ?-hydroxycarboxylic ester represented by Formula (2): (CF3)2C(OH)COOR with a halofluoromethane in the presence of an alkaline compound. According to the present invention, 1,1,1,3,3,3-hexafluoroisopropyl fluoromethyl ether (sevoflurane), which is known as an anesthetic compound, can be efficiently produced at low cost.Type: ApplicationFiled: June 27, 2007Publication date: January 14, 2010Applicant: Daikin Industries LTdInventors: Tatsuya Ohtsuka, Yoshichika Kuroki, Atsukhi Suzuki
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Patent number: 7598425Abstract: The present invention relates to a method for producing a compound represented by formula (2): [CF3(CF2)n][CF3(CF2)m]C(OH)2??(2) wherein n and m independently represent 0 to 10, the method comprising reacting with a halogen or a halogen-containing oxidizing agent a salt of a compound represented by formula (1): [CF3(CF2)n][CF3(CF2)m]C(OH)COOH??(1) wherein n and m independently represent 0 to 10.Type: GrantFiled: April 8, 2005Date of Patent: October 6, 2009Assignee: Daikin Industries, Ltd.Inventors: Yoshihiro Yamamoto, Yoshichika Kuroki, Daisuke Karube, Tatsuya Ohtsuka
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Publication number: 20090156861Abstract: The present invention provides a process for producing 1,1,1,3,3,3-hexafluoro-2-methoxypropane, wherein a novel compound, 2-methoxy-2-trifluoromethyl-3,3,3-trifluoropropionic acid or a salt thereof is decarboxylated, or wherein an olefin compound represented by chemical formula (4): CF2?C(CF3)(OCH3) is reacted with a fluorinating agent; and a process for producing 2-methoxy-2-trifluoromethyl-3,3,3-trifluoropropionic acid or a salt thereof by reacting a hydroxycarboxylic ester with a methylating agent and then hydrolyzing the reaction product, or hydrolyzing the hydroxycarboxylic ester and then reacting the resulting product with a methylating agent. In accordance with the invention, 1,1,1,3,3,3-hexafluoro-2-methoxypropane, which is useful as a raw material for, for example, the anesthetic Sevoflurane, can be produced efficiently and at low cost.Type: ApplicationFiled: May 31, 2007Publication date: June 18, 2009Applicant: DAIKIN INDUSTRIES, LTD.Inventors: Tatsuya Ohtsuka, Yoshihiro Yamamoto, Yoshichika Kuroki, Atsushi Suzuki, Akinari Sugiyama
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Publication number: 20080262273Abstract: The present invention relates to a method for producing a compound represented by formula (2): [CF3(CF2)n][CF3(CF2)m]C(OH)2 ??(2) wherein n and m independently represent 0 to 10, the method comprising reacting with a halogen or a halogen-containing oxidizing agent a salt of a compound represented by formula (1): [CF3(CF2)n][CF3(CF2)m]C(OH)COOH ??(1) wherein n and m independently represent 0 to 10.Type: ApplicationFiled: April 8, 2005Publication date: October 23, 2008Inventors: Yoshihiro Yamamoto, Yoshichika Kuroki, Daisuke Karube, Tatsuya Ohtsuka
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Patent number: 7005545Abstract: The present invention provides a process for producing a fluorinated fluorosulfonylalkyl vinyl ether represented by general formula (2): CF2?CFO(CF2CF(CF3)O)nCF2CF2SO2F??(2) wherein n is an integer from 0 to 10, comprising fluorinating a perfluorovinylether sulfonate with SF4 and HF, the perfluorovinylether sulfonate being represented by general formula (1): CF2?CFO(CF2CF(CF3)O)nCF2CF2SO3M??(1) wherein M is Ma or Mb1/2, provided that Ma is an alkali metal and Mb is an alkaline earth metal; and n is as defined above. According to the process of the invention, the fluorinated fluorosulfonylalkyl vinyl ether can be produced in high yield in an industrially advantageous manner.Type: GrantFiled: May 23, 2003Date of Patent: February 28, 2006Assignee: Daikin Industries, Ltd.Inventors: Akinari Sugiyama, Tatsuya Ohtsuka, Kazuyoshi Ichihara, Toshiya Mantani
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Patent number: 6933413Abstract: The present invention provides a process for the preparation of hexafluoroacetone characterized by bringing hexafluoro-1,2-epoxypropane into contact with at least one catalyst selected from the group consisting of titanium oxide catalysts and fluorinated titanium oxide catalysts to isomerize hexafluoro-1,2-epoxypropane; and a process for the preparation of hexafluoroacetone hydrate characterized by absorbing the hexafluoroacetone prepared by the above process into water to produce crude hexafluoroacetone hydrate, neutralizing the crude hexafluoroacetone hydrate with an alkali, and distilling the resulting mixture. According to the invention, high-purity hexafluoroacetone can be obtained by isomerization of hexafluoro-1,2-epoxypropane with little formation of by-products, and substantially acid-free high-purity hexafluoroacetone hydrate can also be obtained.Type: GrantFiled: July 2, 2002Date of Patent: August 23, 2005Assignee: Daikin Industries, Ltd.Inventors: Tatsuya Ohtsuka, Yoshihiro Yamamoto
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Publication number: 20050177001Abstract: The present invention provides a process for producing a fluorinated fluorosulfonylalkyl vinyl ether represented by general formula (2): CF2=CFO(CF2CF(CF3)O)nCF2CF2SO2F??(2) wherein n is an integer from 0 to 10, comprising fluorinating a perfluorovinylether sulfonate with SF4 and HF, the perfluorovinylether sulfonate being represented by general formula (1): CF2=CFO(CF2CF(CF3)O)nCF2CF2SO3M??(1) wherein M is Ma or Mb1/2, provided that Ma is an alkali metal and Mb is an alkaline earth metal; and n is as defined above. According to the process of the invention, the fluorinated fluorosulfonylalkyl vinyl ether can be produced in high yield in an industrially advantageous manner.Type: ApplicationFiled: May 23, 2003Publication date: August 11, 2005Inventors: Akinari Sugiyama, Tatsuya Ohtsuka, Kazuyoshi Ichihara, Toshiya Mantani
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Publication number: 20040186322Abstract: The present invention provides a process for the preparation of hexafluoroacetone characterized by bringing hexafluoro-1,2-epoxypropane into contact with at least one catalyst selected from the group consisting of titanium oxide catalysts and fluorinated titanium oxide catalysts to isomerize hexafluoro-1,2-epoxypropane; and a process for the preparation of hexafluoroacetone hydrate characterized by absorbing the hexafluoroacetone prepared by the above process into water to produce crude hexafluoroacetone hydrate, neutralizing the crude hexafluoroacetone hydrate with an alkali, and distilling the resulting mixture. According to the invention, high-purity hexafluoroacetone can be obtained by isomerization of hexafluoro-1,2-epoxypropane with little formation of by-products, and substantially acid-free high-purity hexafluoroacetone hydrate can also be obtained.Type: ApplicationFiled: January 9, 2004Publication date: September 23, 2004Inventors: Tatsuya Ohtsuka, Yoshihiro Yamamoto