WO2001010815A1 - Bis(4-hydroxy-3-nitro-5-perfluoroalkylphenyl)fluoro-alcanes et procede de preparation dudit compose - Google Patents

Bis(4-hydroxy-3-nitro-5-perfluoroalkylphenyl)fluoro-alcanes et procede de preparation dudit compose Download PDF

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Publication number
WO2001010815A1
WO2001010815A1 PCT/JP2000/004865 JP0004865W WO0110815A1 WO 2001010815 A1 WO2001010815 A1 WO 2001010815A1 JP 0004865 W JP0004865 W JP 0004865W WO 0110815 A1 WO0110815 A1 WO 0110815A1
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WO
WIPO (PCT)
Prior art keywords
bis
hydroxy
perfluoroalkylphenyl
formula
carbon atoms
Prior art date
Application number
PCT/JP2000/004865
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English (en)
Japanese (ja)
Inventor
Kenji Adachi
Sumi Ishihara
Satoshi Oishi
Original Assignee
Daikin Industries, Ltd.
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 Daikin Industries, Ltd. filed Critical Daikin Industries, Ltd.
Publication of WO2001010815A1 publication Critical patent/WO2001010815A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/13—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups
    • C07C205/26—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by hydroxy groups and being further substituted by halogen atoms

Definitions

  • the present invention relates to bis (4-hydroxy-3), which is an important intermediate in various organic compounds or polymers (for example, polyesters, polyethers, polycarbonates, etc.).
  • the present invention relates to a 5-nitro-perfluoroalkylphenyl) fluoroalkane and a method for producing the same.
  • Bis (4-hydroxy-3--2-phenyl) fluoroalkane is known to be an important intermediate of various organic compounds or polymers.
  • this intermediate force which consists of various organic compounds or polymers, has heat resistance, chemical resistance, plasma resistance, corrosion resistance, low refractive index, low water absorption, and solvent solubility. (Molding processability), electrical insulation, flexibility, water repellency Water is not always sufficient for oil repellency, and in order to become a high-performance material developed further in the future, Higher heat resistance, chemical resistance, plasma resistance, corrosion resistance, lower refractive index, lower water absorption, solvent solubility (moldability), electrical insulation, flexibility, It is inevitable that water must be oily. Disclosure of the invention
  • a main object of the present invention is to provide an organic compound or polymer synthesized using bis (4-hydroxy-3-2-trifluorophenyl) fluoroalkane as an intermediate.
  • a new screw (4-hydroxy-3-nitro-5
  • Rf 1 Rf 2 and Rf 3 are the same or different and are perfluoroalkyl groups having 1 to 10 carbon atoms, and may have a cyclic structure even in a linear or branched chain structure. Further, Rf 2 and Rf 3 may be bonded to each other together with the carbon atom to which they are bonded to form a fluorocycloalkyl having 3 to 8 carbon atoms.
  • Rf 2 and Rf 3 are the same or different and each is a perfluoroalkyl group having 1 to 10 carbon atoms, and may be a linear or branched chain structure or a cyclic structure.
  • the Rf 2 and Rf 3 may be bonded to each other together with the carbon atom to which they are bonded to form a fluorocycloalkyl having 3 to 8 carbon atoms. Is a bromine atom or an iodine atom.
  • Rf 1 is the same or different and is a perfluoroalkyl group having 1 to 10 carbon atoms, and may be a linear or branched chain structure or a cyclic structure.
  • R f 2 and R f 3 is Ru same Jidea above.
  • the bis (4-hydroxy-3-2-to-5-perfluoroalkylphenyl) fluoroalkanes of the above-mentioned items 1 to 3 are novel compounds not described in the literature.
  • perfluoroalkyl group having 1 to 10 carbon atoms examples include a linear or branched perfluoroalkyl group having a chain structure or a cyclic structure, such as trifluoromethyl, benzoylfluoroethyl, n-Heptane Fluoro mouth Propyrile, Hep evening Fluoroysopropyl, n-Nonafluorobutyl, Nonafluoroyl butyl, sec Nonafluorobutyl, tert-Nonafluorobutyl, Ndecafluoropentyl, Nonafluorocyclopentyl, Tridecafluoro Perflux such as hexyl mouth, pendecafluorocyclohexyl, pen-decafluorocyclohexyl, tridecafluorocyclohexylmethyl, heptadecafluorooctyl, nonadecafluorononyl, henicosafluor
  • R f 2 and R f 3 is the is assumed that they are the shape formed the Furuoro a cycloalkyl bonded to each other together with the carbon atoms to which they are attached Kisafuruoro preparative R f 2 and R f 3 Gath preparative La Furuoroe styrene to, Rimethylene, octafluorotetramethylene, decafluoropentamethylene, dodecafluorohexamethylene, ophthalmic fluoromethyl trimethylene, decafluorodimethyl trimethylene, dodecaf Examples thereof include fluoromethylpentamethylene and tetradecafluorodimethylpentamethylene.
  • the bis (4-hydroxy-3-nitro-5-halophenyl) fluoroalkane represented by the general formula (2) is, for example, a bis represented by the following general formula (3) It is easily produced from (4-hydroxy-3-nitrophenyl) fluoroalkane by bromination or iodination according to a conventional method.
  • bromination method for example, there is a method using bromine. If necessary, a catalyst such as iron may be added. Examples of the method for iodination include a method in which iodine is reacted with periodic acid under acidic conditions.
  • a perfluoroalkylation by a combination of a perfluoroalkyltrialkylsilane, a fluoride and a copper reagent is used.
  • fluoride alkali metal fluoride and ammonium fluoride are preferred, and lithium fluoride, sodium fluoride, and lithium fluoride are preferred.
  • examples include cesium fluoride, tetrabutylammonium fluoride, and the like.
  • the copper reagent include copper, cuprous chloride, cuprous bromide, cuprous iodide, cuprous cyanide, and the like.
  • the amount of perfluoroalkyltrialkylsilane used is equivalent to the amount of bis (4-hydroxy-3--3-to-5-halophenyl) fluoroalkane used to obtain the product in good yield. It is sufficient to use a 2- to 10-fold molar amount, and economically a 2- to 7-fold molar amount is preferred.
  • the copper reagent and the fluoride may be used in the same amount as or slightly in excess of the perfluoroalkyl trialkylsilane.
  • the reaction solvent is, for example, N, N-dimethylformamide (DMF), N, N-dimethylethylamide, N, N-dimethylethylacetamide (DMAc), N, N-dimethylethylamide.
  • DMF N, N-dimethylformamide
  • DMAc N, N-dimethylethylacetamide
  • reaction temperature is usually in the range of 0 ° C to 150 ° C, preferably in the range of 50 ° C to 100 ° C.
  • Bis (4-hideoxy-3--3-nitole-5-perfluoroalkylphenyl) fluoroalkanes can be used as ordinary column chromatography, distillation or recrystallization, activated carbon, etc. Purification can be achieved by a method using an adsorbent or a combination of these methods.
  • a bis (4-hydroxy-3-2-to-5-amino-5-phenyl) fluoroalkane compound is used as a novel intermediate for a perfluoroalkylation reaction.
  • Certain bis (4-hydroxy-3-2-to-mouth-5- ⁇ ) can be obtained in high yield.

Abstract

L'invention concerne des bis(4-hydroxy-3-nitro-5-perfluoroalkylphényl)fluoro-alcanes de la formule générale (1). Dans ladite formule, Rf?1, Rf2 et Rf3¿ sont chacun, indépendamment, un perfluoroalkyle C¿1?-C10 à chaîne droite, ramifiée ou cyclique, ou bien Rf?2 et Rf3¿ peuvent former ensemble, avec l'atome de carbone auquel ils sont liés, un groupe fluorocycloalkyle C¿3?-C8.
PCT/JP2000/004865 1999-08-03 2000-07-21 Bis(4-hydroxy-3-nitro-5-perfluoroalkylphenyl)fluoro-alcanes et procede de preparation dudit compose WO2001010815A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP11/220509 1999-08-03
JP11220509A JP2001048844A (ja) 1999-08-03 1999-08-03 ビス（４−ヒドロキシ−３−ニトロ−５−ペルフルオロアルキルフェニル）フルオロアルカンおよびその製造方法

Publications (1)

Publication Number Publication Date
WO2001010815A1 true WO2001010815A1 (fr) 2001-02-15

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2000/004865 WO2001010815A1 (fr) 1999-08-03 2000-07-21 Bis(4-hydroxy-3-nitro-5-perfluoroalkylphenyl)fluoro-alcanes et procede de preparation dudit compose

Country Status (2)

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JP (1) JP2001048844A (fr)
WO (1) WO2001010815A1 (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP5072679B2 (ja) * 2008-03-25 2012-11-14 公益財団法人相模中央化学研究所 ベンゾトリフルオリド類の製造方法

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11100356A (ja) * 1997-08-01 1999-04-13 Nippon Kayaku Co Ltd ビス（３−アミノ−４−ヒドロキシフェニル）類の精製方法
JPH11106365A (ja) * 1997-10-02 1999-04-20 Nippon Kayaku Co Ltd ビス（３−ニトロ−４−ヒドロキシフェニル）類の製造方法

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH11100356A (ja) * 1997-08-01 1999-04-13 Nippon Kayaku Co Ltd ビス（３−アミノ−４−ヒドロキシフェニル）類の精製方法
JPH11106365A (ja) * 1997-10-02 1999-04-20 Nippon Kayaku Co Ltd ビス（３−ニトロ−４−ヒドロキシフェニル）類の製造方法

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JP2001048844A (ja) 2001-02-20

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