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).

  • Patent number: 9593058
    Abstract: 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: Grant
    Filed: September 3, 2014
    Date of Patent: March 14, 2017
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Atsushi Shirai, Masatoshi Nose, Yosuke Kishikawa, Tatsuya Ohtsuka, Sumi Ishihara
  • Publication number: 20160318842
    Abstract: 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: Application
    Filed: December 26, 2014
    Publication date: November 3, 2016
    Applicant: DAIKIN INDUSTRIES, LTD.
    Inventors: Akihiro GOTOU, Manaho MIYAZAKI, Sumi ISHIHARA, Takashi NAMIKAWA, Tatsuya OHTSUKA, Yosuke KISHIKAWA
  • Publication number: 20160297740
    Abstract: 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: Application
    Filed: June 15, 2016
    Publication date: October 13, 2016
    Applicant: DAIKIN INDUSTRIES, LTD.
    Inventors: Tatsuya OHTSUKA, Akihiro GOTOU, Sumi ISHIHARA, Yoshihiro YAMAMOTO, Akinori YAMAMOTO, Yoshichika KUROKI, Yuzo KOMATSU, Yousuke KISHIKAWA
  • Publication number: 20160221900
    Abstract: 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: Application
    Filed: September 3, 2014
    Publication date: August 4, 2016
    Applicant: DAIKIN INDUSTRIES, LTD.
    Inventors: Atsushi SHIRAI, Masatoshi NOSE, Yosuke KISHIKAWA, Tatsuya OHTSUKA, Sumi ISHIHARA
  • Patent number: 9388117
    Abstract: 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: Grant
    Filed: August 30, 2013
    Date of Patent: July 12, 2016
    Assignee: DAIKIN INDUSTRIES, LTD.
    Inventors: Tatsuya Ohtsuka, Akihiro Gotou, Sumi Ishihara, Yoshihiro Yamamoto, Akinori Yamamoto, Yoshichika Kuroki, Yuzo Komatsu, Yousuke Kishikawa
  • Publication number: 20160168060
    Abstract: 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: Application
    Filed: August 7, 2014
    Publication date: June 16, 2016
    Applicant: DAIKIN INDUSTRIES, LTD.
    Inventors: Shingo NAKAMURA, Kanako FUKUMOTO, Yuusuke ETOU, Tatsuya OHTSUKA, Masahiro HIGASHI
  • Publication number: 20150299088
    Abstract: 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: Application
    Filed: November 12, 2013
    Publication date: October 22, 2015
    Inventors: Shingo NAKAMURA, Yuusuke ETOU, Tatsuya OHTSUKA, Kanako FUKUMOTO, Masato NAITOU
  • Publication number: 20150191413
    Abstract: 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: Application
    Filed: August 30, 2013
    Publication date: July 9, 2015
    Inventors: Tatsuya Ohtsuka, Akihiro Gotou, Sumi Ishihara, Yoshihiro Yamamoto, Akinori Yamamoto, Yoshichika Kuroki, Yuzo Komatsu, Yousuke Kishikawa
  • Patent number: 8022245
    Abstract: 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: Grant
    Filed: June 27, 2007
    Date of Patent: September 20, 2011
    Assignee: Daikin Industries, Ltd.
    Inventors: Tatsuya Ohtsuka, Yoshichika Kuroki, Atsushi Suzuki
  • Patent number: 8013182
    Abstract: 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: Grant
    Filed: November 6, 2008
    Date of Patent: September 6, 2011
    Assignee: Daikin Industries, Ltd.
    Inventors: Yoshihiro Yamamoto, Tatsuya Ohtsuka
  • Patent number: 7985877
    Abstract: 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: Grant
    Filed: May 31, 2007
    Date of Patent: July 26, 2011
    Assignee: Daikin Industries, Ltd.
    Inventors: Tatsuya Ohtsuka, Yoshihiro Yamamoto, Yoshichika Kuroki, Atsushi Suzuki, Akinari Sugiyama
  • Publication number: 20100234634
    Abstract: 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: Application
    Filed: November 6, 2008
    Publication date: September 16, 2010
    Inventors: Yoshihiro Yamamoto, Tatsuya Ohtsuka
  • Publication number: 20100010255
    Abstract: 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: Application
    Filed: June 27, 2007
    Publication date: January 14, 2010
    Applicant: Daikin Industries LTd
    Inventors: Tatsuya Ohtsuka, Yoshichika Kuroki, Atsukhi Suzuki
  • Patent number: 7598425
    Abstract: 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: Grant
    Filed: April 8, 2005
    Date of Patent: October 6, 2009
    Assignee: Daikin Industries, Ltd.
    Inventors: Yoshihiro Yamamoto, Yoshichika Kuroki, Daisuke Karube, Tatsuya Ohtsuka
  • Publication number: 20090156861
    Abstract: 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: Application
    Filed: May 31, 2007
    Publication date: June 18, 2009
    Applicant: DAIKIN INDUSTRIES, LTD.
    Inventors: Tatsuya Ohtsuka, Yoshihiro Yamamoto, Yoshichika Kuroki, Atsushi Suzuki, Akinari Sugiyama
  • Publication number: 20080262273
    Abstract: 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: Application
    Filed: April 8, 2005
    Publication date: October 23, 2008
    Inventors: Yoshihiro Yamamoto, Yoshichika Kuroki, Daisuke Karube, Tatsuya Ohtsuka
  • Patent number: 7005545
    Abstract: 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: Grant
    Filed: May 23, 2003
    Date of Patent: February 28, 2006
    Assignee: Daikin Industries, Ltd.
    Inventors: Akinari Sugiyama, Tatsuya Ohtsuka, Kazuyoshi Ichihara, Toshiya Mantani
  • Patent number: 6933413
    Abstract: 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: Grant
    Filed: July 2, 2002
    Date of Patent: August 23, 2005
    Assignee: Daikin Industries, Ltd.
    Inventors: Tatsuya Ohtsuka, Yoshihiro Yamamoto
  • Publication number: 20050177001
    Abstract: 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: Application
    Filed: May 23, 2003
    Publication date: August 11, 2005
    Inventors: Akinari Sugiyama, Tatsuya Ohtsuka, Kazuyoshi Ichihara, Toshiya Mantani
  • Publication number: 20040186322
    Abstract: 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: Application
    Filed: January 9, 2004
    Publication date: September 23, 2004
    Inventors: Tatsuya Ohtsuka, Yoshihiro Yamamoto