WO2007126194A1 - Method of preparing fluorinated alkoxytrialkylsilanes - Google Patents

Method of preparing fluorinated alkoxytrialkylsilanes Download PDF

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Publication number
WO2007126194A1
WO2007126194A1 PCT/KR2006/005348 KR2006005348W WO2007126194A1 WO 2007126194 A1 WO2007126194 A1 WO 2007126194A1 KR 2006005348 W KR2006005348 W KR 2006005348W WO 2007126194 A1 WO2007126194 A1 WO 2007126194A1
Authority
WO
WIPO (PCT)
Prior art keywords
fluorinated
formula
reaction
imidazole compound
chlorotrialkylsilane
Prior art date
Application number
PCT/KR2006/005348
Other languages
English (en)
French (fr)
Inventor
Hyun Joo Lee
Hong Gon Kim
Byoung Sung Ahn
Byung Gwon Lee
Hoon Sik Kim
Original Assignee
Korea Institute Of Science And Technology
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Korea Institute Of Science And Technology filed Critical Korea Institute Of Science And Technology
Publication of WO2007126194A1 publication Critical patent/WO2007126194A1/en

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
    • C07F7/1804—Compounds having Si-O-C linkages
    • C07F7/1872—Preparation; Treatments not provided for in C07F7/20
    • C07F7/188—Preparation; Treatments not provided for in C07F7/20 by reactions involving the formation of Si-O linkages
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/12—Organo silicon halides

Definitions

  • the present invention relates to a process for preparing fluorinated
  • alkoxytrialkylsilanes from the reaction of chlorosilanes with fluoro alcohol, and in
  • the first process relates to a reaction between a
  • the second process relates to a reaction between a hexamethyldisilazine and
  • the present invention provides an improved process for the production of
  • an imidazole compound which is used as a reaction medium, reacts with a generated hydrogen chloride to form an
  • alkoxytrialkylsilane and the by-products such as the imidazolium chloride
  • the present invention relates to a process for preparing fluorinated
  • alkoxytrialkylsilanes wherein an imidazole compound is added to the reaction of a
  • R 1 , R 2 and R3 are a Ci-C 6 hydrocarbon or a phenyl group, respectively;
  • R f is a Ci-C 6 fluorinated hydrocarbon containing 1-8 fluorine atoms.
  • chlorotrialkylsilane reacts with a
  • R 4 is a Ci-C 6 alkyl or a C 2 -C 6 alkenyl group.
  • Scheme 1 The process of Scheme 1 comprises two reaction steps as shown in Scheme 2.
  • chlorotrialkylsilane of formula (2) reacts with an imidazole
  • salt of formula (6) is also formed as a by-product.
  • an imidazole compound of formula (4) is used as a
  • reaction vehicle in the present invention to produce a silylimidazolium salt of
  • alkoxytrialkylsilane is manufactured at a relatively high temperature of 80 0 C.
  • imidazolium salt of formula (6) are ionic compounds having a higher specific gravity
  • fluorinated alkoxytrialkylsilane of formula (1) remains in an upper liquid layer
  • fluorinated alkoxytrialkylsilane of formula (1) may also be obtained with
  • ⁇ of formula (6) may be collected after it is converted into an imidazole compound of
  • formula (4) by adding a suitable base.
  • the base include an alkali metal
  • R 4 is a Ci-C 6 alkyl or a C 2 -C 6 alkenyl group; M is an alkali
  • X is a hydroxyl (OH) or a Ci-C 6 alkoxy group.
  • compound of formula (4) may be used in the amount of 1.2 moles, respectively, relative to one mole of the fluorinated alcohol of formula (3). If the amount of the
  • chlorotrialkylsilane of formula (2) or the imidazole compound of formula (4) is less
  • chlorotrialkylsilane may remain unreacted, thus making the separation and
  • reaction may be performed at a
  • reaction temperature is preferred to be as low as possible only if the
  • reaction temperature may be 100%, respectively. However, if the reaction temperature is lower than -
  • the reaction rate may be too low, thus resulting in low economical efficiency.
  • reaction temperature above 50 0 C is not preferred because it would result in
  • reaction of the present invention may be performed in the
  • the solvent may be used in the amount of up to 300 vol%,
  • the reaction may be more stably performed at room temperature due to the
  • alkoxytrialkylsilane and the imidazolium salt, an ionic liquid alkoxytrialkylsilane and the imidazolium salt, an ionic liquid.
  • Example 1 except that the solvent was changed as shown in Table 5. The results are
  • a chlorotrialkylsilane derivative reacts with a
  • the imidazolium salt may be any substantial boiling point.
  • the imidazolium salt may be any substantial boiling point.
  • imidazolium salt may be converted into the initial imidazole compound

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
PCT/KR2006/005348 2006-05-02 2006-12-08 Method of preparing fluorinated alkoxytrialkylsilanes WO2007126194A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
KR10-2006-0039532 2006-05-02
KR1020060039532A KR100744834B1 (ko) 2006-05-02 2006-05-02 함불소알콕시실란 유도체의 제조방법

Publications (1)

Publication Number Publication Date
WO2007126194A1 true WO2007126194A1 (en) 2007-11-08

Family

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/KR2006/005348 WO2007126194A1 (en) 2006-05-02 2006-12-08 Method of preparing fluorinated alkoxytrialkylsilanes

Country Status (2)

Country Link
KR (1) KR100744834B1 (ko)
WO (1) WO2007126194A1 (ko)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103958532A (zh) * 2011-10-11 2014-07-30 汉高美国知识产权有限责任公司 新型含氟化合物制品、其制备方法以及由其制得的组合物

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06108096A (ja) * 1992-09-29 1994-04-19 Agency Of Ind Science & Technol 溶剤組成物

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5493044A (en) 1994-10-20 1996-02-20 Fmc Corporation Process for preparing alkylsilyl or arylsilyl ethers
JP3128193B2 (ja) * 1995-12-06 2001-01-29 信越化学工業株式会社 アルコキシシラン化合物の製造方法

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH06108096A (ja) * 1992-09-29 1994-04-19 Agency Of Ind Science & Technol 溶剤組成物

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
MONTANARI V. ET AL.: "1-Iodo-polyfluoroalkanes from polyfluoroalkoxy trimethylsilanes and iodochloro triphenylphosphorane", TETRAHEDRON LETTERS, vol. 35, no. 12, 1994, pages 1941 - 1944, XP000434499, DOI: doi:10.1016/S0040-4039(00)73201-1 *
PATEL N.R. ET AL.: "Synthesis and Chemistry of Acyclic Mono and Disiloxanes: Useful Precursors to per- and Polyfluoroethers", INORGANIC CHEMISTRY, vol. 33, no. 24, 1994, pages 5463 - 5470 *
UNEYAMA K. ET AL.: "Preparation of 2,2-difluoroenol silyl ethers by electroreductive defluorination of trifluoromethyl ketones", TETRAHEDRON LETTERS, vol. 39, no. 22, 1998, pages 3741 - 3744, XP004118726, DOI: doi:10.1016/S0040-4039(98)00574-7 *

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN103958532A (zh) * 2011-10-11 2014-07-30 汉高美国知识产权有限责任公司 新型含氟化合物制品、其制备方法以及由其制得的组合物
EP2766375A4 (en) * 2011-10-11 2015-09-09 Henkel US IP LLC PREPARATION OF NEW FLUORIN COMPOUNDS, METHOD OF MANUFACTURING AND COMPOSITIONS MADE THEREOF

Also Published As

Publication number Publication date
KR100744834B1 (ko) 2007-08-01

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