WO2007126194A1 - Method of preparing fluorinated alkoxytrialkylsilanes - Google Patents
Method of preparing fluorinated alkoxytrialkylsilanes Download PDFInfo
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 31
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 52
- 238000006243 chemical reaction Methods 0.000 claims abstract description 32
- -1 imidazole compound Chemical class 0.000 claims abstract description 21
- 150000001298 alcohols Chemical class 0.000 claims description 20
- 239000006227 byproduct Substances 0.000 claims description 9
- 150000004693 imidazolium salts Chemical class 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 150000002430 hydrocarbons Chemical class 0.000 claims description 5
- BOIWNSUZFFJEKL-UHFFFAOYSA-O 1H-imidazol-3-ium-3-ylsilane Chemical class [SiH3][n+]1cc[nH]c1 BOIWNSUZFFJEKL-UHFFFAOYSA-O 0.000 claims description 3
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 239000013067 intermediate product Substances 0.000 claims 1
- 239000012454 non-polar solvent Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 6
- 230000007797 corrosion Effects 0.000 abstract description 3
- 238000005260 corrosion Methods 0.000 abstract description 3
- 230000002708 enhancing effect Effects 0.000 abstract description 2
- 239000002516 radical scavenger Substances 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000047 product Substances 0.000 description 8
- 238000000926 separation method Methods 0.000 description 7
- MCTWTZJPVLRJOU-UHFFFAOYSA-N 1-methyl-1H-imidazole Chemical compound CN1C=CN=C1 MCTWTZJPVLRJOU-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- KGFLFWRAHYKYEA-UHFFFAOYSA-N trimethyl(2,2,2-trifluoroethoxy)silane Chemical compound C[Si](C)(C)OCC(F)(F)F KGFLFWRAHYKYEA-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical group [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000012459 cleaning agent Substances 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- 230000005484 gravity Effects 0.000 description 2
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 150000008040 ionic compounds Chemical class 0.000 description 2
- 239000002608 ionic liquid Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- JPVQCHVLFHXNKB-UHFFFAOYSA-N 1,2,3,4,5,6-hexamethyldisiline Chemical compound CC1=C(C)[Si](C)=[Si](C)C(C)=C1C JPVQCHVLFHXNKB-UHFFFAOYSA-N 0.000 description 1
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 1
- 239000005046 Chlorosilane Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- KOPOQZFJUQMUML-UHFFFAOYSA-N chlorosilane Chemical class Cl[SiH3] KOPOQZFJUQMUML-UHFFFAOYSA-N 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- AQYSYJUIMQTRMV-UHFFFAOYSA-N hypofluorous acid Chemical compound FO AQYSYJUIMQTRMV-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000009972 noncorrosive effect Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000013077 target material Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
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)
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
ID=38601545
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)
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)
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)
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 |
-
2006
- 2006-05-02 KR KR1020060039532A patent/KR100744834B1/ko not_active IP Right Cessation
- 2006-12-08 WO PCT/KR2006/005348 patent/WO2007126194A1/en active Application Filing
Patent Citations (1)
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)
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)
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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