JP4884982B2 - ビニルシランの製造方法 - Google Patents
ビニルシランの製造方法 Download PDFInfo
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- JP4884982B2 JP4884982B2 JP2006548725A JP2006548725A JP4884982B2 JP 4884982 B2 JP4884982 B2 JP 4884982B2 JP 2006548725 A JP2006548725 A JP 2006548725A JP 2006548725 A JP2006548725 A JP 2006548725A JP 4884982 B2 JP4884982 B2 JP 4884982B2
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- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 title claims description 37
- 238000004519 manufacturing process Methods 0.000 title claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 39
- -1 vinyl halide compound Chemical class 0.000 claims description 32
- 229910052782 aluminium Inorganic materials 0.000 claims description 22
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 22
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 claims description 20
- ZDNBETOXRXGYFH-UHFFFAOYSA-N trimethyl(3,3,3-trifluoroprop-1-en-2-yl)silane Chemical compound C[Si](C)(C)C(=C)C(F)(F)F ZDNBETOXRXGYFH-UHFFFAOYSA-N 0.000 claims description 19
- 229920002554 vinyl polymer Polymers 0.000 claims description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 17
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 14
- QKBKGNDTLQFSEU-UHFFFAOYSA-N 2-bromo-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(Br)=C QKBKGNDTLQFSEU-UHFFFAOYSA-N 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000000962 organic group Chemical group 0.000 claims description 11
- 229910052710 silicon Inorganic materials 0.000 claims description 11
- 239000010703 silicon Substances 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 claims description 8
- 239000000010 aprotic solvent Substances 0.000 claims description 8
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 150000003377 silicon compounds Chemical class 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 14
- 239000000047 product Substances 0.000 description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 238000005481 NMR spectroscopy Methods 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 238000006459 hydrosilylation reaction Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 238000004445 quantitative analysis Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 description 2
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 description 2
- PRDFNJUWGIQQBW-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-yne Chemical compound FC(F)(F)C#C PRDFNJUWGIQQBW-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical group 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000007810 chemical reaction solvent Substances 0.000 description 2
- KWYZNESIGBQHJK-UHFFFAOYSA-N chloro-dimethyl-phenylsilane Chemical compound C[Si](C)(Cl)C1=CC=CC=C1 KWYZNESIGBQHJK-UHFFFAOYSA-N 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- VPXWFEWRBGEQKN-UHFFFAOYSA-N dimethyl-phenyl-(3,3,3-trifluoroprop-1-en-2-yl)silane Chemical compound FC(F)(F)C(=C)[Si](C)(C)C1=CC=CC=C1 VPXWFEWRBGEQKN-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- PQDJYEQOELDLCP-UHFFFAOYSA-N trimethylsilane Chemical compound C[SiH](C)C PQDJYEQOELDLCP-UHFFFAOYSA-N 0.000 description 2
- CSRZQMIRAZTJOY-UHFFFAOYSA-N trimethylsilyl iodide Chemical compound C[Si](C)(C)I CSRZQMIRAZTJOY-UHFFFAOYSA-N 0.000 description 2
- VJGCZWVJDRIHNC-UHFFFAOYSA-N 1-fluoroprop-1-ene Chemical compound CC=CF VJGCZWVJDRIHNC-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- OQISUJXQFPPARX-UHFFFAOYSA-N 2-chloro-3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C(Cl)=C OQISUJXQFPPARX-UHFFFAOYSA-N 0.000 description 1
- LHRSMHZCHIDYBT-UHFFFAOYSA-N 3,3,3-trifluoro-2-iodoprop-1-ene Chemical compound FC(F)(F)C(I)=C LHRSMHZCHIDYBT-UHFFFAOYSA-N 0.000 description 1
- ZOYDPLAHKCEZIE-UHFFFAOYSA-N FC(C(F)(F)F)(C(=C)[Si](C)(C)C)F Chemical compound FC(C(F)(F)F)(C(=C)[Si](C)(C)C)F ZOYDPLAHKCEZIE-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 150000001343 alkyl silanes Chemical class 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- IYYIVELXUANFED-UHFFFAOYSA-N bromo(trimethyl)silane Chemical compound C[Si](C)(C)Br IYYIVELXUANFED-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000012039 electrophile Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000010813 internal standard method Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 125000005004 perfluoroethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 238000001577 simple distillation Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- MWKJTNBSKNUMFN-UHFFFAOYSA-N trifluoromethyltrimethylsilane Chemical compound C[Si](C)(C)C(F)(F)F MWKJTNBSKNUMFN-UHFFFAOYSA-N 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
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/0825—Preparations of compounds not comprising Si-Si or Si-cyano linkages
- C07F7/0827—Syntheses with formation of a Si-C bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
Description
で示されるビニルシランの製造方法に関しては、アセチレン系化合物を少なくとも1個の水素原子を含むシラン化合物と反応させるヒドロシリル化反応により合成する方法が公知である。その製造方法として、UV光照射下で3,3,3−トリフルオロプロピンとトリメチルシランを反応させて(E)−3,3,3−トリフルオロプロペニル−1−トリメチルシラン、(Z)−3,3,3−トリフルオロプロペニル−1−トリメチルシラン、(1−トリフルオロメチルビニル)トリメチルシランの混合物、又は(E)−3,3,3−トリフルオロプロペニル−1−トリメチルシラン、1,1,1−トリフルオロ−3,3−ビストリメチルシリルプロパン、(1−トリフルオロメチルビニル)トリメチルシランの混合物を合成した例があるのみである(非特許文献2参照)。
Synlett.,641(1995) J.Chem.Soc.Perkin Trans.1,20,2293(1974) Tetrahedron Lett.,44,707(2003)
(1) 一般式(1)
で示されるビニルシランの製造方法であり、非プロトン性溶媒中、アルミニウム存在下、一般式(2)
で示されるビニルハロゲン化合物と、一般式(3)
で示されるハロゲン化ケイ素化合物を反応させて、上記一般式(1)で示されるビニルシランを生成することを特徴とするビニルシランの製造方法。
前記一般式(3)において、A1,A2及びA3はメチル基を表し、X2は塩素原子を表すハロゲン化ケイ素化合物であることを特徴とする前記一般式(1)のRが炭素数1〜4の含フッ素有機基、A1,A2およびA3がメチル基を表すビニルシランである(1)に記載のビニルシランの製造方法。
A3は前記一般式(1)に同じである。またX2で表されるハロゲン原子は塩素、臭素、ヨウ素が好ましく、さらに塩素が好ましい。
以下、実施例により本発明をさらに詳細に説明するが、本発明は下記の実施例に限定されるものではない。
1H−NMR(CDCl3,内部基準TMS)δ0.13(s,9H),5.74(d,1H,J=1.6Hz),6.25(m,1H)
19F−NMR(CDCl3,内部基準CFCl3)δ−62.3(s,CF3)
Claims (6)
- 一般式(1)
で示されるビニルシランの製造方法であり、非プロトン性溶媒中、アルミニウム存在下、一般式(2)
で示されるビニルハロゲン化合物と、
一般式(3)
で示されるハロゲン化ケイ素化合物を反応させて、上記一般式(1)で示されるビニルシランを生成することを特徴とするビニルシランの製造方法。 - 前記一般式(2)において、X1は臭素原子、Rは炭素数1〜4の含フッ素有機基を表すビニルハロゲン化合物であり、
前記一般式(3)において、A1,A2およびA3はメチル基を表し、X2は塩素原子を表すハロゲン化ケイ素化合物であることを特徴とする前記一般式(1)のRが炭素数1〜4の含フッ素有機基、A1,A2及びA3がメチル基を表すビニルシランである請求項1に記載のビニルシランの製造方法。 - 前記一般式(2)で示されるビニルハロゲン化合物が2−ブロモ−3,3,3−トリフルオロプロペンであり、前記一般式(3)で示されるハロゲン化ケイ素化合物がクロロトリメチルシランであることを特徴とする前記一般式(1)で示される化合物が(1−トリフルオロメチルビニル)トリメチルシランである請求項1又は2に記載のビニルシランの製造方法。
- 前記非プロトン性溶媒が、1,3−ジメチル−2−イミダゾリジノン、N−メチル−2−ピロリドンおよびN,N−ジメチルホルムアミドからなる群より選ばれる少なくとも1種である請求項1ないし3のいずれか1項に記載のビニルシランの製造方法。
- 反応温度が0〜60℃である請求項1ないし3のいずれか1項に記載のビニルシランの製造方法。
- 反応圧力が0〜0.20MPa(ゲージ圧力)である請求項1ないし3のいずれか1項に記載のビニルシランの製造方法。
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
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JP2006548725A JP4884982B2 (ja) | 2004-12-15 | 2005-11-18 | ビニルシランの製造方法 |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
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JP2004362599 | 2004-12-15 | ||
JP2004362599 | 2004-12-15 | ||
PCT/JP2005/021207 WO2006064628A1 (ja) | 2004-12-15 | 2005-11-18 | ビニルシランの製造方法 |
JP2006548725A JP4884982B2 (ja) | 2004-12-15 | 2005-11-18 | ビニルシランの製造方法 |
Publications (2)
Publication Number | Publication Date |
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JPWO2006064628A1 JPWO2006064628A1 (ja) | 2008-06-12 |
JP4884982B2 true JP4884982B2 (ja) | 2012-02-29 |
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JP2006548725A Active JP4884982B2 (ja) | 2004-12-15 | 2005-11-18 | ビニルシランの製造方法 |
Country Status (2)
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JP (1) | JP4884982B2 (ja) |
WO (1) | WO2006064628A1 (ja) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
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JP5170987B2 (ja) * | 2006-06-27 | 2013-03-27 | 東ソ−・エフテック株式会社 | 新規な含フッ素不飽和シリルエーテル化合物及び該化合物を中間体とする含フッ素不飽和アルコール誘導体の製造方法 |
GB0623110D0 (en) | 2006-11-21 | 2006-12-27 | Ciba Sc Holding Ag | Microcapules, their use and processes for their manufacture |
Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63188687A (ja) * | 1987-01-30 | 1988-08-04 | Sagami Chem Res Center | 有機ケイ素化合物の製造方法 |
JPH02235888A (ja) * | 1989-03-09 | 1990-09-18 | Agency Of Ind Science & Technol | アルケニルシラン類の製造方法 |
JPH0352892A (ja) * | 1989-07-17 | 1991-03-07 | Dow Corning Corp | アルケニルシラン調製方法 |
JP2005008630A (ja) * | 2003-05-28 | 2005-01-13 | Nissan Chem Ind Ltd | シクロアルキル置換ベンズアニリド化合物及び有害生物防除剤 |
-
2005
- 2005-11-18 JP JP2006548725A patent/JP4884982B2/ja active Active
- 2005-11-18 WO PCT/JP2005/021207 patent/WO2006064628A1/ja not_active Application Discontinuation
Patent Citations (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS63188687A (ja) * | 1987-01-30 | 1988-08-04 | Sagami Chem Res Center | 有機ケイ素化合物の製造方法 |
JPH02235888A (ja) * | 1989-03-09 | 1990-09-18 | Agency Of Ind Science & Technol | アルケニルシラン類の製造方法 |
JPH0352892A (ja) * | 1989-07-17 | 1991-03-07 | Dow Corning Corp | アルケニルシラン調製方法 |
JP2005008630A (ja) * | 2003-05-28 | 2005-01-13 | Nissan Chem Ind Ltd | シクロアルキル置換ベンズアニリド化合物及び有害生物防除剤 |
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JPWO2006064628A1 (ja) | 2008-06-12 |
WO2006064628A1 (ja) | 2006-06-22 |
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