WO2001010805A1 - Derives de bis(4-hydroxy-3-perfluoro-alkyle-phenyle)-fluoroalcane et procede d'elaboration - Google Patents

Derives de bis(4-hydroxy-3-perfluoro-alkyle-phenyle)-fluoroalcane et procede d'elaboration Download PDF

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Publication number
WO2001010805A1
WO2001010805A1 PCT/JP2000/004866 JP0004866W WO0110805A1 WO 2001010805 A1 WO2001010805 A1 WO 2001010805A1 JP 0004866 W JP0004866 W JP 0004866W WO 0110805 A1 WO0110805 A1 WO 0110805A1
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WIPO (PCT)
Prior art keywords
bis
group
carbon atoms
hydroxy
formula
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Application number
PCT/JP2000/004866
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English (en)
Japanese (ja)
Inventor
Kenji Adachi
Sumi Ishihara
Satoshi Oishi
Tsukasa Moriya
Original Assignee
Daikin Industries, Ltd.
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Application filed by Daikin Industries, Ltd. filed Critical Daikin Industries, Ltd.
Priority to US09/787,697 priority Critical patent/US6521483B1/en
Publication of WO2001010805A1 publication Critical patent/WO2001010805A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C43/00—Ethers; Compounds having groups, groups or groups
    • C07C43/02—Ethers
    • C07C43/20—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring
    • C07C43/225—Ethers having an ether-oxygen atom bound to a carbon atom of a six-membered aromatic ring containing halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
    • C07C39/24—Halogenated derivatives
    • C07C39/367—Halogenated derivatives polycyclic non-condensed, containing only six-membered aromatic rings as cyclic parts, e.g. halogenated poly-hydroxyphenylalkanes

Definitions

  • the present invention relates to bis (4-hydroxy) which is an important intermediate in various organic compounds or polymers (eg, polyester, polyether, polycarbonate, etc.).
  • the present invention relates to a -3- (fluoroalkylphenyl) fluoroalkane derivative and a method for producing the same.
  • Bis (4-hydroxyphenyl) fluoroalkanes are known to be important intermediates of various organic compounds or polymers (Organof luorine Chemistry, Principes and Commercial). Appli icat ions, Banks, RE, Smart, BE, Tat low, J., Eds .; Plenum: New York, 1994; PP413-429, Development and application of fluorine-based polymers, Kazuhiro Takahashi, Inc. technical information Institute, ⁇ 1 ⁇ 234; Recently heat-resistant polymer, Mita us, Ltd.
  • Sogo Gijutsu Center, P14 ⁇ 39) £ deer products et, various organic compounds consisting intermediates or et this or Or polymer has heat resistance, chemical resistance, plasma resistance, corrosion resistance, low refractive index, low water absorption, solvent solubility (formability), electrical insulation, flexibility, Water is oily It is not always sufficient, and in order to develop a high-performance material that has been further developed in the future, even higher heat resistance, chemical resistance, plasma resistance, and resistance than current compounds are required. Corrosion, low refractive index, low water absorption, solvent solubility (moldability), electrical insulation, flexibility, and water repellency are inevitably required.
  • a main object of the present invention is to solve the above-mentioned problems of the prior art in an organic compound or polymer synthesized using bis (4-hydroxyphenyl) fluoroalkane as an intermediate.
  • the present inventors have further improved the performance of organic compounds or polymers using bis (4-hydroxyphenyl) fluoroalkane derivatives as intermediates.
  • the intermediate bis (4-hydroxyphenyl) fur At the stage of the fluoroalkane derivative, a perfluorinated alkylation reaction was carried out, and it was found that a method of introducing a perfluoroalkyl group was industrially superior.
  • a perfluoroalkylation reaction is carried out using a bis (4-hydroxyphene ::: l) fluoroalkane derivative in which the hydroxy group is protected, and the perfluoroalkyl group is converted. Upon introduction, they found that the perfluoroalkylation reaction was carried out with higher yield and selectivity, and completed the present invention.
  • the present invention provides the following bis (4-hydroxyx-3-perfluoroalkylphenyl) fluoroalkane derivative and a method for producing the same.
  • R 1 and R 2 are the same or different and are each a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an octaalkyl group, an alkoxyalkyl group or a carbon atom having 6 to 1 carbon atoms.
  • Two aryl groups, wherein the alkyl group, haloalkyl group and alkoxyalkyl group may have a linear or branched chain structure or a cyclic structure
  • Ri 1 , Rf 2 and Rf 3 Same or different, perfluoroalkyl having 1 to 10 carbon atoms It is a kill group and may have a linear or branched chain structure or a cyclic structure.
  • R f 2 and R f 3 This is these are but it may also be formed a number of 3 to 8 Furuoro Sik b alkyl carbon bound to each other to a carbon atom co binding.
  • Rf 1 is a fluorethyl group
  • R f 3 is a trifluoromethyl group.
  • R 1 and R 2 are the same or different and each represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, an alkyl group having 1 to 10 carbon atoms, an alkoxyalkyl group having 1 to 10 carbon atoms, or a 6 to 12 carbon atom.
  • Ri pieces of ⁇ Li Ichiru group der, an alkyl group, Bruno, mouth alkyl and alkoxy key Shiarukiru group is a linear or even branched chain structure but it may also cyclic structure.
  • Rf 2 and Rf 3 is the same or Is different, is a perfluoroalkyl group having 1 to 10 carbon atoms, and may have a linear or branched chain structure or a cyclic structure.
  • Rf 2 and Ri 3 may be bonded together with the carbon atom to which they are bonded to form a fluorocycloalkyl having 3 to 8 carbon atoms.
  • a general formula (1) characterized in that a perfluoroalkylation reaction is performed on a bis (4-hydroxyphenyl) fluoroalkane derivative represented by the following formula:
  • Rf 1 is a perfluoroalkyl group having 1 to 10 carbon atoms, and may have a linear or branched chain structure or a cyclic structure.
  • R 2 , Rf 2 and Rf 3 are the same as described above.
  • alkyl group having 1 to 10 carbon atoms examples include an alkyl group having a linear or branched chain structure or a cyclic structure.
  • alkyl groups such as cyclosyl, cycloheptyl, and aryl groups.
  • haloalkyl group having 1 to 10 carbon atoms examples include a haloalkyl group having a linear or branched chain structure or a cyclic structure, and include methyl, ethyl, and methyl.
  • alkoxyalkyl group having 1 to 10 carbon atoms examples include an alkoxyalkyl group having a linear or branched chain structure or a cyclic structure, and include methoxymethyl and methoxyalkyl. Shetyl, methoxypropyl, methoxybutyl, ethoxymethyl, ethoxyl, ethoxypropyl, propoxyl, t-butoxymethyl, benzyloxymethyl, 2-- Methoxy-methyl, 2,2,2-triethoxymethyl, bis (2-cycloethoxy) methyl, tetrahydrovinyl Relief, 2- (trimethylsilyl) ethoxymethyl, te Lahydrofuranil, 4-methoxytetralhydrobiranil, 1-ethoxyl, 1-methyll-l-methoxyl, 1- (isopropoxy) ethyl And alkoxyalkyl groups.
  • aryl group having 6 to 12 carbon atoms examples include phenyl, naphthyl, biphenyl, P-cyclophenyl, benzyl, nitrobenzyl, cyanobenzyl, and cyanobenzyl.
  • Examples of the perfluoroalkyl group having 1 to 10 carbon atoms include a linear or branched chain or cyclic perfluoroalkyl group, and include trifluoromethyl, benzoylfluoroethyl, and the like.
  • R ⁇ 2 and R f 3 are linked together with the carbon atom to which they are attached to form a fluorocycloalkyl. Is assumed to be formed, R f 2 and R f 3 Gath preparative La Furuoroe styrene, to Kisafuruoro Application Benefits methylene, O click evening Furuoro Te DOO La methylene, decamethylene full O b pentamethylene, Kisamechi les into dodeca Furuo port And tetrafluoromethyltrimethylene, decafluorodimethyltrimethylene, dodecafluoromethylpentamethylene, and tetradecafluoromethylmethylpentamethylene.
  • a method for producing a bis (4-hydroxyphenyl) fluoroalkane derivative represented by the general formula (2) (such as a method for protecting a hydroxyl group), and a hydroxyl group which may be used as needed after the perfluoroalkylation reaction
  • the following can be mentioned as methods for deprotection.
  • the bis (4-hydroxyphenyl) fluoroalkane derivative represented by the general formula (2) is a bis (4-methoxyphenyl) fluoroalkane derivative
  • a method for converting a normal hydroxyl group to methyl ether For example, a method using dimethyl sulfate or methyl iodide in the presence of a base, a method using diazomethane), or a method using anisol as a raw material and condensing it with hexafluoroacetone under acidic conditions. It can be manufactured more.
  • the usual reaction for example, boron tribromide, boron trichloride, aluminum chloride, etc.
  • Lewis acid sodium trimethylsilyl, sodium iodide and tetraclosilane, or acetyl chloride or Pivaloy-Look mouth lid, etc.
  • the bis (4-hydroxyphenyl) furylene monoalkane derivative represented by the general formula (2) is a bis- (methoxymethyl) phenyl ⁇ fluoro compound
  • a method for converting a normal hydroxyl group into methoxymethyl ether for example, a method using chloromethyl methyl ether in the presence of a base, a method using pentoxide pentoxide and dimethyoxymethan). , Etc.
  • a usual reaction for example, a method using an acid such as hydrochloric acid, acetic acid, sulfuric acid, boron trifluoride, etc. can be used.
  • the bis (4-hydroxyphenyl) fluoroalkane derivative represented by the general formula (2) is a bis (4-t-butoxyphenyl) fluoroalkane
  • It can be produced by converting ordinary hydroxyl groups to t-butyl ether (for example, using isobutene in the presence of an acid).
  • the deprotection method after the perfluoroalkylation reaction may be a conventional reaction (for example, a method using an acid such as trifluoroacetic acid, hydrogen bromide, hydrochloric acid, or acetic acid, or a method such as trimethylethyl chloride). Silane, etc.) can be used. (P r See otective Groups in Organic Synthes is).
  • Preferred perfluoroalkylating agents capable of performing the perfluoroalkylation reaction used in the production method of the present invention include perfluoroalkylaryl-donium compounds, perfluoroalkyl Group-containing organic peroxides, and a combination of xenon difluoride and perfluorocarboxylic acid.
  • perfluoroalkylaryl nitrogen compounds include trifluoromethyl sulfonate, trifluoromethyl sulfonate, and pentafluor J-lenoethyl phenylene.
  • perfluoroalkyl group-containing organic peroxides include bis (trifluoroacetyl) peroxide, bis (fluorofluoropropionyl) peroxide, bis (hepfluorofluorobutylyl) peroxide, bis (no Penoxide, Nafluo Peroxyd, Bis (Hexanol, dexcafluo) Peroxide, Bis (Heptayl, tridecafluo) Peroxide, Bis (Penyu decaful) Peroxyd, Bis (Deca-Floro Nonanoil), Peroxyd, Bis (Nonadeca Fluorodenoil) Peroxyd, Bis (Henei Kosafolo Undeca Noir), Peroxyd Bis (Hepta Fluoroy Sobutyryl) Peroxide, Bis (Nonafluo Isopentanoyl) Peroxide, Bis (Hepta Fluoro-2-methylbutyril) Peroxide, Bis (Nonafluoros
  • the perfluorocarboxylic acid used in the perfluoroalkylation reaction by the combination includes trifluoroacetic acid, penfuoropropionic acid, hepturofluorobutyric acid, hepufufluoroisobutyric acid, and nonafluorovaleric acid.
  • the amount of the perfluoroalkylating agent used may be 1.5- to 7-fold the molar amount of the bis (4-hydroxyphenyl) fluoroalkane derivative in order to obtain the product in good yield. However, economically, 2 to 4 moles are preferable.
  • reaction conditions conditions suitable for various methods may be appropriately selected.
  • a solvent may be used.
  • the reaction temperature is usually in the range of 100 ° C. (: up to 50 ° C., preferably 0 ° C. to 30 ° C.
  • Perfluoro using an organic peroxide containing a perfluoroalkyl group.
  • the solvents used are dichloromethane, dichloroethane, cro-form, fluor-form trichlorome, 1, 1, and 2 -Trifluoro mouth trifluorene, 2-Macro mouth-1,2-dibromo-1,1,2 -trifluorene, 1,2-dibromohexafluoroprono.
  • Aliphatic halogenated solvents such as 1,1,1,1-trichloro mouth trifluorene, polycyclotrifluoroethylene, getyl ether, dipropyl ether, dibutyl ether It is preferable to use a dialkyl ether such as monoter, and the reaction temperature is usually in the range of 0: to 100 ° C, preferably 20 to 80 ° C.
  • the solvent used is dichloromethane, dichloroethane, or chloromethane.
  • the reaction temperature is usually—20 ° C (: ⁇ 80 ° C, preferably 10 ° C ⁇ ). 50.
  • the range is C.
  • Bis (4-hydroxy-3-perfluoroalkylphenyl) fluoroalkane derivatives can be used as adsorbents such as ordinary column chromatography, distillation or recrystallization, and activated carbon. Purification can be achieved by using these methods or by combining these methods.
  • a desired novel intermediate, bis (4-hydroxy) is obtained from a bis (4-hydroxyphenyl) fluoroalkane derivative in a one-step perfluoroalkylation reaction.
  • a xyl-3-perfluoroalkylphenyl) fluoroalkane derivative is obtained.
  • the reaction mixture was extracted with methylene chloride, the organic layer was washed with water and then with saturated saline, dried over magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure.
  • the spectrum data is shown below.
  • the following shows the production ratios of mono-trifluoromethylated product, bis-trifluoromethylated product, and tris-trifluoromethylated product.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

La présente invention concerne des dérivés de bis(4-hydroxy-3-perfluoro-alkyle-phényle)-fluoroalcane représentés par la formule générale (I). Dans cette formule, R1 et R2 sont chacun indépendamment hydrogène, C¿1?-C10 alkyle, haloalkyle, alcoxyalkyle ou C6-C12 aryle. Toutefois, les groupes alkyle, haloalkyle et alcoxyalkyle peuvent chacun présenter une structure cyclique ou une structure caténaire droite ou ramifiée. En outre, Rf?1, Rf2 et Rf3¿ sont chacun C¿1?-C10 perfluoroalkyle droit, ramifié ou cyclique. Avec l'atome de carbone auquel ils sont liés, Rf?2 et Rf3¿ peuvent également former un C¿3?-C8 fluoro-cycloalkyle.
PCT/JP2000/004866 1999-07-22 2000-07-21 Derives de bis(4-hydroxy-3-perfluoro-alkyle-phenyle)-fluoroalcane et procede d'elaboration WO2001010805A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US09/787,697 US6521483B1 (en) 1999-07-22 2000-07-21 Semiconductor device, method of manufacture thereof, circuit board, and electronic device

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP11220508A JP2001048820A (ja) 1999-08-03 1999-08-03 ビス（４−ヒドロキシ−３−ペルフルオロアルキルフェニル）フルオロアルカン誘導体およびその製造方法
JP11/220508 1999-08-03

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114149751A (zh) * 2021-12-29 2022-03-08 泰州亚德胶粘制品有限公司 一种耐高温耐反翘光学胶粘剂及其制备方法

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6461706A (en) * 1987-09-01 1989-03-08 Teijin Ltd Light transmittable plastic fiber
JPH0345907A (ja) * 1989-07-14 1991-02-27 Furukawa Electric Co Ltd:The 耐熱性プラスチック光ファイバ
EP0464472A2 (fr) * 1990-06-25 1992-01-08 Hoechst Aktiengesellschaft Biphényles partiellement fluorés, procédé pour leur fabrication et leur utilisation
JPH0482855A (ja) * 1990-07-25 1992-03-16 Nippon Oil & Fats Co Ltd ポリフルオロアルキル基含有芳香族アルデヒド誘導体及びその製造方法
JPH04283524A (ja) * 1991-03-13 1992-10-08 Sagami Chem Res Center トリフルオロメチル置換芳香族化合物の製造法
JPH06116555A (ja) * 1992-10-09 1994-04-26 Mitsui Toatsu Chem Inc ビスフェノール系シアニン色素の光安定化剤及び該光安定化剤を含有する光記録媒体
JPH08179112A (ja) * 1994-12-22 1996-07-12 Mitsui Toatsu Chem Inc フタロシアニン色素、該色素を含有するフィルター用組成物およびカラーフィルター
EP0650949B1 (fr) * 1993-10-29 1998-01-21 Nippon Mektron, Ltd. Procédé pour la préparation de 2,2-diphénylhexafluoropropanes
JP2000105472A (ja) * 1998-09-29 2000-04-11 Konica Corp 電子写真感光体及び画像形成方法

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6461706A (en) * 1987-09-01 1989-03-08 Teijin Ltd Light transmittable plastic fiber
JPH0345907A (ja) * 1989-07-14 1991-02-27 Furukawa Electric Co Ltd:The 耐熱性プラスチック光ファイバ
EP0464472A2 (fr) * 1990-06-25 1992-01-08 Hoechst Aktiengesellschaft Biphényles partiellement fluorés, procédé pour leur fabrication et leur utilisation
JPH0482855A (ja) * 1990-07-25 1992-03-16 Nippon Oil & Fats Co Ltd ポリフルオロアルキル基含有芳香族アルデヒド誘導体及びその製造方法
JPH04283524A (ja) * 1991-03-13 1992-10-08 Sagami Chem Res Center トリフルオロメチル置換芳香族化合物の製造法
JPH06116555A (ja) * 1992-10-09 1994-04-26 Mitsui Toatsu Chem Inc ビスフェノール系シアニン色素の光安定化剤及び該光安定化剤を含有する光記録媒体
EP0650949B1 (fr) * 1993-10-29 1998-01-21 Nippon Mektron, Ltd. Procédé pour la préparation de 2,2-diphénylhexafluoropropanes
JPH08179112A (ja) * 1994-12-22 1996-07-12 Mitsui Toatsu Chem Inc フタロシアニン色素、該色素を含有するフィルター用組成物およびカラーフィルター
JP2000105472A (ja) * 1998-09-29 2000-04-11 Konica Corp 電子写真感光体及び画像形成方法

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN114149751A (zh) * 2021-12-29 2022-03-08 泰州亚德胶粘制品有限公司 一种耐高温耐反翘光学胶粘剂及其制备方法

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