WO2004002932A1 - 含フッ素アルコールおよびその製造方法 - Google Patents
含フッ素アルコールおよびその製造方法 Download PDFInfo
- Publication number
- WO2004002932A1 WO2004002932A1 PCT/JP2003/007771 JP0307771W WO2004002932A1 WO 2004002932 A1 WO2004002932 A1 WO 2004002932A1 JP 0307771 W JP0307771 W JP 0307771W WO 2004002932 A1 WO2004002932 A1 WO 2004002932A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- compound
- fluorine
- atom
- formula
- fluorine atom
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
- C07C41/01—Preparation of ethers
- C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
- C07C41/06—Preparation of ethers by addition of compounds to unsaturated compounds by addition of organic compounds only
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/12—Saturated ethers containing halogen
- C07C43/126—Saturated ethers containing halogen having more than one ether bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C43/00—Ethers; Compounds having groups, groups or groups
- C07C43/02—Ethers
- C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
- C07C43/04—Saturated ethers
- C07C43/13—Saturated ethers containing hydroxy or O-metal groups
- C07C43/137—Saturated ethers containing hydroxy or O-metal groups containing halogen
Definitions
- the present invention relates to a novel fluorine-containing alcohol and a method for producing the same.
- Examples of the fluorine-containing compound having a hydroxyl group at the terminal include R f (CF 2 CF 2 ) n CH 2 CH 2 OH (R f represents a polyfluoroalkyl group), and a method for producing the fluorine-containing compound There are the following methods.
- a method of converting n CH 2 CH 2 I to R f (CF 2 CF 2 ) n CH 2 CH 2 ⁇ H using a solid acid catalyst supporting an alkali metal Japanese Patent Application Laid-Open No. 2000-79
- R f (CF 2 CF 2) n I is produced by the telomerization reaction, a compound having a distribution of carbon numbers (that is, n in the above chemical formula) is produced, so that R f ( CF 2 CF 2 ) n CH 2 CH 2 OH is also a fluorinated compound having a distribution of carbon numbers. Therefore, in order to obtain a fluorine-containing compound having a hydroxyl group at a terminal portion and a specific number of carbon atoms, it is necessary to perform separation after the reaction.
- an object of the present invention is to provide a novel fluorinated alcohol and a method for producing the same. Disclosure of the invention
- the present invention provides a fluorinated alcohol represented by the following formula 1 (compound 1) or the following formula 2 (compound 2).
- R 1 is a monovalent organic group, a halogen atom or a hydrogen atom.
- R 2 divalent organic group.
- ⁇ 1, ⁇ 2, ⁇ 3 each independently a hydrogen atom or a fluorine atom, 1 when R 1 is not a fluorine atom Upsilon, Upsilon 2, two one at least of the Upsilon 3 is a fluorine atom.
- ⁇ 1 , ⁇ 2 , ⁇ 3 , ⁇ 4 , ⁇ 5 , ⁇ 6 each independently represents a hydrogen atom or a fluorine atom, and at least one of ⁇ 1 , ⁇ 2 , ⁇ 3 is a fluorine atom There, and, Zeta 4, Zeta 5, at least one of the Zeta 6 is fluorine atom.
- Q 1 , Q 2 , Q 3 each independently represents a divalent organic group.
- the present invention is characterized in that a compound having a group represented by the following formula 3 (compound 3) and a diol represented by the following formula 4 (compound 4) are reacted in the presence of an alkali metal compound.
- Equations 3, 4 and 5 have the following meanings.
- X 1 , X 2 , X 3 each independently represents a hydrogen atom or a fluorine atom , X 1 , X 2 , and X 3 are each a fluorine atom.
- R 1 is a monovalent organic group, a halogen atom or a hydrogen atom.
- R 1 is preferably a monovalent hydrocarbon group or a monovalent halogenated hydrocarbon group, particularly preferably a monovalent halogenated hydrocarbon group containing an etheric oxygen atom.
- R 1 may have a straight-chain structure, a branched structure, or a ring structure.
- R 1 is preferably a fluorinated hydrocarbon group, particularly preferably a perfluorohydrocarbon group in which all hydrogen atoms of the hydrocarbon group have been substituted with fluorine atoms, and particularly preferably a perfluorohydrocarbon group containing an etheric oxygen atom. Is preferred. When an etheric oxygen atom is contained, the etheric oxygen atom is preferably present at a terminal portion.
- Y 1 , Y 2 , and Y 3 are preferably fluorine atoms, and all are preferably fluorine atoms.
- Q 1 is preferably a divalent hydrocarbon group, and particularly preferably an alkylene group. Further, as Q 1 , a group represented by 1 (CH 2 ) t — (where t is an integer of 1 or more) is preferable, a group where t is 2 to 12 is particularly preferable, Certain groups are preferred.
- R 'CFHCF 2 O (CH 2 ) m OH (where R' is a monovalent fluorine-containing organic group containing an etheric oxygen atom having 1 to 16 carbon atoms, m Represents an integer of 2 to 12.
- a compound represented by the following formula (compound 6) is preferable.
- R ′ may have a linear structure or a branched structure. When the compound has a branched structure, the branched portion is preferably present at the terminal, and the branched portion is preferably (CF 3 ) 2 CF—.
- R ' is preferably a fluorinated hydrocarbon group, particularly a perfluorohydrocarbon group in which all hydrogen atoms of the hydrocarbon group are substituted with fluorine atoms.
- a perfluorohydrocarbon group containing an etheric oxygen atom is particularly preferable.
- the etheric oxygen atom is preferably present at a terminal portion.
- Specific examples of the compound 1 include the following compounds.
- R 2 is preferably a divalent hydrocarbon group or a divalent halogenated hydrocarbon group, particularly preferably a divalent halogenated hydrocarbon group containing an etheric oxygen atom.
- R 2 may have a linear structure, a branched structure, or a ring structure.
- R 2 is preferably a fluorinated hydrocarbon group, particularly preferably a perfluorohydrocarbon group in which all hydrogen atoms of the hydrocarbon group have been substituted with fluorine atoms, and especially a perfluorohydrocarbon group containing an etheric oxygen atom. Is preferred. When an etheric oxygen atom is contained, the etheric oxygen atom is preferably present at a terminal portion.
- Z 1 Z 2 , Z 3 , Z 4 , Z 5 , and Z 6 are preferably fluorine atoms, and all are preferably fluorine atoms. Further, Q 2 and Q 3 are preferably the same as Q 1 in the compound 1.
- R ′ ′′ [CFHCF 2 O (CH 2 ) q OH] 2 (where R ′ ′′ is a divalent containing an etheric oxygen atom having 1 to 16 carbon atoms) The fluorine-containing organic group, and Q represents an integer of 2 to 12.)
- R ′ ′′ may have a linear structure or a branched structure. In the case of having a branched structure, the branched portion is preferably present at the terminal, and the branched portion is preferably (CF 3 ) 2 CF ⁇ .
- R ′′ is preferably a fluorinated hydrocarbon group, particularly preferably a perfluorohydrocarbon group in which all hydrogen atoms of the hydrocarbon group have been substituted with fluorine atoms, and particularly preferably a perfluorohydrocarbon containing an etheric oxygen atom. Groups are preferred. When an etheric oxygen atom is contained, the etheric oxygen atom is preferably present at a terminal portion.
- compound 2 include the following compounds.
- X 1 X 2 X 3 is preferably a fluorine atom, and all of them are preferably fluorine atoms.
- Compound 3 can be synthesized by the production method described in J. Am. Chem. Soc75, 4525 (1953) and the like.
- R p-valent organic group.
- p an integer of 14.
- X 1 X 2 X 3 each independently represents a hydrogen atom or a fluorine atom, and at least one of X 1 X 2 X 3 is a fluorine atom.
- R is preferably the same as R 1 in Compound 1 or R 2 in Compound 2.
- X 1 X 2 X 3 Is preferably a fluorine atom, and all are preferably fluorine atoms.
- P is preferably 1 or 2.
- compound 3 include the following compounds.
- Q is preferably the same as in Q 1 in compound 1.
- compound 4 preferably include H ⁇ (CH 2 ) 2 ⁇ H, HO (CH 2 ) 3 ⁇ H, HO (CH 2 ) 4 ⁇ H, HO (CH 2 ) 6 OH, and the like.
- X 1 , X 2 , X 3 , and Q are preferably the same as in compound 3 or compound 4.
- R p-valent organic group.
- X 1 , X 2 and X 3 each independently represents a hydrogen atom or a fluorine atom, and at least one of X 1 , X 2 and X 3 is a fluorine atom.
- p an integer from 1 to 4.
- R, X 1 , X 2 , X 3 , Q, and p are preferably the same as those in compound 4 or compound 8.
- Compound 5 is preferably Compound 1 or Compound 2 described above.
- the alkali metal compound used in the reaction between the compound 3 and the compound 4 include an alkali metal, an alkali metal hydride, an alkali metal hydroxide, and an alkali metal amide.
- alkali metals such as Na, K, Cs, etc.
- alkali metal hydroxides such as Na ⁇ H, KOH
- alkali metal hydrides such as NaH, KH, NaNH 2 , KNH 2 etc.
- alkali metal amides are preferred.
- the amount of the metal compound used is not particularly limited. However, it is preferable to use 0.01 to 1.0 mole per 1 mole of the compound 3, particularly considering the reaction rate. It is preferable to use a molar amount of 0.05 to 0.5 times. Use in this range is preferable because the generation of by-products is small and the reaction proceeds at an appropriate reaction rate.
- the amount of the compound 4 when producing a compound having one group represented by the formula 5, that is, the compound 1, the amount of the compound 4 is preferably 1 to 5 moles per 1 mole of the compound 3.
- the molar ratio is particularly preferably 2 to 4 times.
- the amount of the compound 4 is preferably 2 to 10 moles per 1 mole of the compound 3.
- 4 to 8 times mol is preferable. It is preferable to carry out the reaction in this range, since a product obtained by reacting only one hydroxyl group of compound 4 with compound 3 is likely to be produced.
- the temperature of the above reaction is preferably from 0 to 150, and particularly preferably from 40 to 120. If the reaction is carried out in this range, the reaction proceeds at an appropriate reaction rate, This is preferable because the polymerization reaction of only the product 3 is not performed.
- a solvent may or may not be used, but it is preferable to use a solvent.
- a solvent that dissolves Compound 4 a solvent that dissolves Compound 5, and a solvent that is substantially inert in the above reaction are preferable.
- the solvent is preferably an ether, a nitrile compound, or the like, and specifically, dimethyl ether, glyme, dioxane, tetrahydrofuran, acetate nitrile, or propionitrile, particularly preferably dioxane, tetrahydrofuran or Acetonitrile is preferred.
- the amount of the solvent to be used is not particularly limited. However, considering the reaction rate and the productivity, it is preferable to use an amount of 1 to 60% by mass of the product compound 5, particularly 3 to 50% by mass. It is preferred to use a certain amount.
- a polymerization inhibitor in the above reaction in order to prevent the polymerization reaction.
- the polymerization inhibitor may be added to the reaction system before the raw materials, or may be added to the reaction system together with the raw materials.
- the polymerization inhibitor can be used without any particular limitation, and preferred examples thereof include limonene, binene, cymene and terpinene.
- the mechanism by which compound 5 is produced is presumed as follows. That is, the diol (compound 4) is converted into an alkoxide compound by the alkali metal compound, the alkoxide compound is added to the compound 3, and the metal portion is replaced with a hydrogen atom to produce the compound 5.
- the diol compound 4
- the alkoxide compound is added to the compound 3, and the metal portion is replaced with a hydrogen atom to produce the compound 5.
- a novel fluorine-containing alcohol can be synthesized.
- the fluorinated alcohol is useful as a detergent and an intermediate of various compounds.
- a fluorinated acrylate obtained by reacting compound 1 with acrylic acid is useful as a raw material for a UV-curable resin and as a water / oil repellent.
- Compound 2 When used as a copolymerization component of a condensation resin such as urethane, the surface of the resin can be modified.
- Compound 3 which is a raw material of the fluorinated alcohol of the present invention, was synthesized using the direct fluorination described in Adv. Synth. Cata 1.2001, 343, No. 2. In direct fluorination, the structure of the raw material can be selected, so that the obtained fluorinated alcohols can have various structures.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2004548900A JPWO2004002932A1 (ja) | 2002-06-27 | 2003-06-19 | 含フッ素アルコールおよびその製造方法 |
AU2003244294A AU2003244294A1 (en) | 2002-06-27 | 2003-06-19 | Fluorine-containing alcohols and process for production thereof |
EP03761767A EP1522536A4 (en) | 2002-06-27 | 2003-06-19 | FLUORINE-CONTAINING ALCOHOLS AND THEIR PRODUCTION PROCESS |
US11/017,871 US20050107645A1 (en) | 2002-06-27 | 2004-12-22 | Fluorine-containing alcohol and method for its production |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP2002188062 | 2002-06-27 | ||
JP2002-188062 | 2002-06-27 | ||
JP2002-195905 | 2002-07-04 | ||
JP2002195905 | 2002-07-04 |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11/017,871 Continuation US20050107645A1 (en) | 2002-06-27 | 2004-12-22 | Fluorine-containing alcohol and method for its production |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2004002932A1 true WO2004002932A1 (ja) | 2004-01-08 |
Family
ID=30002304
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/JP2003/007771 WO2004002932A1 (ja) | 2002-06-27 | 2003-06-19 | 含フッ素アルコールおよびその製造方法 |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP1522536A4 (ja) |
JP (1) | JPWO2004002932A1 (ja) |
CN (1) | CN1665768A (ja) |
AU (1) | AU2003244294A1 (ja) |
WO (1) | WO2004002932A1 (ja) |
Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007238583A (ja) * | 2006-03-13 | 2007-09-20 | National Institute Of Advanced Industrial & Technology | 含フッ素ポリエーテル化合物およびその製造方法 |
CN100392001C (zh) * | 2006-05-18 | 2008-06-04 | 中国科学技术大学 | 一种含氟聚醚二元醇的制备方法 |
JP2011527308A (ja) * | 2008-07-08 | 2011-10-27 | ソルヴェイ・ソレクシス・エッセ・ピ・ア | フルオロ界面活性剤の製造方法 |
JP2011530565A (ja) * | 2008-08-11 | 2011-12-22 | ソルヴェイ・ソレクシス・エッセ・ピ・ア | 熱安定性及び化学的安定性が改善されたハイドロフルオロアルコール |
JP2017512198A (ja) * | 2014-02-21 | 2017-05-18 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | フッ素化界面活性剤 |
JP2019523803A (ja) * | 2016-06-17 | 2019-08-29 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | フッ素含有ポリマー |
JP2021528529A (ja) * | 2018-06-20 | 2021-10-21 | ソルベイ スペシャルティ ポリマーズ イタリー エス.ピー.エー. | (パー)フルオロポリエーテルポリマー |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8173848B2 (en) * | 2008-07-01 | 2012-05-08 | E.I. Du Pont De Nemours And Company | Fluorinated alcohols |
ES2911353T3 (es) | 2014-12-19 | 2022-05-18 | Merck Patent Gmbh | Compuestos con grupos terminales fluorados y su uso en revestimientos que repelen la suciedad |
CN106748670B (zh) * | 2016-12-19 | 2020-11-17 | 衢州氟硅技术研究院 | 一种含醚键氟醇及其制备方法 |
WO2021171745A1 (ja) * | 2020-02-27 | 2021-09-02 | ユニマテック株式会社 | 含フッ素アルコールコンポジット |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2409274A (en) * | 1943-04-23 | 1946-10-15 | Du Pont | Polyfluoro organic ethers and their preparation |
US2631975A (en) * | 1947-01-08 | 1953-03-17 | American Viscose Corp | Photopolymerization of vinyl trifluorochloroethyl ether |
JPS53113028A (en) * | 1977-03-14 | 1978-10-03 | Kansai Paint Co Ltd | Solid state materials having controlling action against harmful organisms |
JPS63192732A (ja) * | 1987-02-05 | 1988-08-10 | Canon Inc | 光学活性物質およびそれを含む液晶組成物 |
JPH01226844A (ja) * | 1988-03-05 | 1989-09-11 | Tokuyama Soda Co Ltd | 含フッ素エーテル化合物及びその製造方法 |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP1427694A4 (en) * | 2001-06-18 | 2005-06-22 | Honeywell Int Inc | FLUORINE-CONTAINING COMPOUNDS AND POLYMERS DERIVED THEREFROM |
-
2003
- 2003-06-19 JP JP2004548900A patent/JPWO2004002932A1/ja not_active Withdrawn
- 2003-06-19 EP EP03761767A patent/EP1522536A4/en not_active Withdrawn
- 2003-06-19 WO PCT/JP2003/007771 patent/WO2004002932A1/ja not_active Application Discontinuation
- 2003-06-19 AU AU2003244294A patent/AU2003244294A1/en not_active Abandoned
- 2003-06-19 CN CN 03815064 patent/CN1665768A/zh active Pending
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2409274A (en) * | 1943-04-23 | 1946-10-15 | Du Pont | Polyfluoro organic ethers and their preparation |
US2631975A (en) * | 1947-01-08 | 1953-03-17 | American Viscose Corp | Photopolymerization of vinyl trifluorochloroethyl ether |
JPS53113028A (en) * | 1977-03-14 | 1978-10-03 | Kansai Paint Co Ltd | Solid state materials having controlling action against harmful organisms |
JPS63192732A (ja) * | 1987-02-05 | 1988-08-10 | Canon Inc | 光学活性物質およびそれを含む液晶組成物 |
JPH01226844A (ja) * | 1988-03-05 | 1989-09-11 | Tokuyama Soda Co Ltd | 含フッ素エーテル化合物及びその製造方法 |
Non-Patent Citations (4)
Title |
---|
BREY M.L. ET AL.: "The preparation and properties of some vinyl and glycidyl fluoroethers", J. AM. CHEM. SOC., vol. 79, 1957, pages 6533 - 6536, XP002973316 * |
CIRKVA V. ET AL.: "Radical additions to fluoroolefins", J. FLUORINE CHEM., vol. 80, 1996, pages 135 - 144, XP004071321 * |
PARK J.D. ET AL.: "Preparation of 3-(1,1,2-trifluoro-2-chloroethoxy) propanol and some of its derivatives", J. ORG. CHEM., vol. 23, 1958, pages 1394 - 1395, XP002973317 * |
See also references of EP1522536A4 * |
Cited By (10)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2007238583A (ja) * | 2006-03-13 | 2007-09-20 | National Institute Of Advanced Industrial & Technology | 含フッ素ポリエーテル化合物およびその製造方法 |
CN100392001C (zh) * | 2006-05-18 | 2008-06-04 | 中国科学技术大学 | 一种含氟聚醚二元醇的制备方法 |
JP2011527308A (ja) * | 2008-07-08 | 2011-10-27 | ソルヴェイ・ソレクシス・エッセ・ピ・ア | フルオロ界面活性剤の製造方法 |
JP2011530565A (ja) * | 2008-08-11 | 2011-12-22 | ソルヴェイ・ソレクシス・エッセ・ピ・ア | 熱安定性及び化学的安定性が改善されたハイドロフルオロアルコール |
JP2017512198A (ja) * | 2014-02-21 | 2017-05-18 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | フッ素化界面活性剤 |
US10464874B2 (en) | 2014-02-21 | 2019-11-05 | Merck Patent Gmbh | Fluorinated tensides |
JP2019523803A (ja) * | 2016-06-17 | 2019-08-29 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングMerck Patent Gesellschaft mit beschraenkter Haftung | フッ素含有ポリマー |
JP7068200B2 (ja) | 2016-06-17 | 2022-05-16 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング | フッ素含有ポリマー |
JP2021528529A (ja) * | 2018-06-20 | 2021-10-21 | ソルベイ スペシャルティ ポリマーズ イタリー エス.ピー.エー. | (パー)フルオロポリエーテルポリマー |
JP7370346B2 (ja) | 2018-06-20 | 2023-10-27 | ソルベイ スペシャルティ ポリマーズ イタリー エス.ピー.エー. | (パー)フルオロポリエーテルポリマー |
Also Published As
Publication number | Publication date |
---|---|
JPWO2004002932A1 (ja) | 2005-10-27 |
EP1522536A1 (en) | 2005-04-13 |
CN1665768A (zh) | 2005-09-07 |
AU2003244294A1 (en) | 2004-01-19 |
EP1522536A4 (en) | 2006-08-09 |
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