CN103588803A - Preparation method of trimethylsilyl trifluoromethanesulfonate - Google Patents
Preparation method of trimethylsilyl trifluoromethanesulfonate Download PDFInfo
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- CN103588803A CN103588803A CN201310476619.5A CN201310476619A CN103588803A CN 103588803 A CN103588803 A CN 103588803A CN 201310476619 A CN201310476619 A CN 201310476619A CN 103588803 A CN103588803 A CN 103588803A
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Abstract
The invention discloses a preparation method of trimethylsilyl trifluoromethanesulfonate, which comprises the following steps: adding anhydrous trifluoromethanesulfonic acid and anhydrous trimethylchlorosilane into a reaction vessel, and reacting at 10-30 DEG C for 12 hours while stirring under an inert gas protective atmosphere; and after the reaction is finished, performing reduced pressure distillation for 1-2 hours, and collecting the distillate of 125-135 DEG C, which is the trimethylsilyl trifluoromethanesulfonate. According to the method, no side reaction exists in the preparation process; the product is high in purity and yield and low in cost; and the purity of the product is up to 99.9%, and the yield of the product is up to 97.8%.
Description
Technical field
The preparation method who the present invention relates to a kind of trimethylsilyl triflate, belongs to field of fine chemical.
Background technology
Trimethylsilyl triflate is frequent catalyzer or cationic initiator as silylation reagent in organic synthesis, at present, conventional preparation method has two kinds, a kind of is to react to prepare with tetramethylsilane by trifluoromethanesulfonic acid, but tetramethylsilane in preparation process often with a large amount of dimethylbutanes, dimethylchlorosilane, the impurity such as dimethyl dichlorosilane (DMCS), above-mentioned impurity and trifluoromethanesulfonic acid are easy to occur side reaction, especially the trifluoromethanesulfonic acid dimethyl silicone grease that dimethylchlorosilane and trifluoromethanesulfonic acid generate and the boiling point of trimethylsilyl triflate are very approaching, be difficult to separate by the method for rectifying, can bring very large difficulty with separated to the purification of trimethylsilyl triflate, another kind of preparation method is by fluoroform sulphonate and silylation reagent react, this kind of preparation method can obtain purity up to 99.9% trimethylsilyl triflate, but this kind of preparation method needs excessive silylation reagent, increased preparation cost.
Summary of the invention
The preparation method who the object of this invention is to provide a kind of trimethylsilyl triflate, does not have side reaction to occur in preparation process, product purity is high, yield is high, cost is low, is applicable to large-scale batch production and produces.
The present invention is achieved through the following technical solutions: in reaction vessel, add anhydrous trifluoromethanesulfonic acid and anhydrous trimethylchlorosilane; stirring reaction 12h under protection of inert gas; temperature of reaction is 10 ℃～30 ℃; after reaction finishes; at underpressure distillation 1-2h, collect 125-135 ℃ of cut and be trimethylsilyl triflate.
Further, described anhydrous trifluoromethanesulfonic acid and anhydrous trimethylchlorosilane mol ratio are 1:1～1.5.
Further, described rare gas element is argon gas or nitrogen.
The preparation method of trimethylsilyl triflate of the present invention, does not have side reaction to occur in preparation process, product purity is high, yield is high, cost is low, and the purity of product is up to 99.9%, and the yield of product is up to 97.8%.
Embodiment
Embodiment mono-: 1 mole of trifluoromethanesulfonic acid and 1 mole of trimethylchlorosilane added in reaction vessel, and stirring reaction 12h under argon shield, temperature of reaction is 20 ℃; after reaction finishes, at underpressure distillation 1-2h, collect 130 ℃ of cuts; product yield is 96.5%, and product purity is 99.4%.
Embodiment bis-: 1 mole of trifluoromethanesulfonic acid and 1.5 moles of trimethylchlorosilanes added in reaction vessel, and stirring reaction 12h under argon shield, temperature of reaction is 20 ℃; after reaction finishes, at underpressure distillation 1-2h, collect 130 ℃ of cuts; product yield is 97.8%, and product purity is 99.9%.
Embodiment tri-: 1 mole of trifluoromethanesulfonic acid and 1 mole of trimethylchlorosilane added in reaction vessel, and stirring reaction 12h under nitrogen protection, temperature of reaction is 10 ℃; after reaction finishes, at underpressure distillation 1-2h, collect 130 ℃ of cuts; product yield is 95.1%, and product purity is 98.7%.
Embodiment tetra-: 1 mole of trifluoromethanesulfonic acid and 1.5 moles of trimethylchlorosilanes added in reaction vessel, and stirring reaction 12h under nitrogen protection, temperature of reaction is 10 ℃; after reaction finishes, at underpressure distillation 1-2h, collect 130 ℃ of cuts; product yield is 95.9%, and product purity is 99.2%.
[0012] embodiment five: 1 mole of trifluoromethanesulfonic acid and 1.5 moles of trimethylchlorosilanes are added in reaction vessel; stirring reaction 12h under nitrogen protection; temperature of reaction is 30 ℃; after reaction finishes; at underpressure distillation 1-2h; collect 130 ℃ of cuts, product yield is 97.8%, and product purity is 99.6%.
Above-mentioned example just, for explanation technical conceive of the present invention and technical characterstic, can not limit the scope of the invention with this.Equivalent transformation or modification that all essence according to the present invention is done, within all should being encompassed in protection scope of the present invention.
Claims (3)
1. the preparation method of a trimethylsilyl triflate; it is characterized in that; in reaction vessel, add anhydrous trifluoromethanesulfonic acid and anhydrous trimethylchlorosilane; stirring reaction 12h under protection of inert gas; temperature of reaction is 10 ℃～30 ℃; after reaction finishes, underpressure distillation 1-2h, collects 125-135 ℃ of cut and is trimethylsilyl triflate.
2. the preparation method of trimethylsilyl triflate according to claim 1, is characterized in that, described anhydrous trifluoromethanesulfonic acid and anhydrous trimethylchlorosilane mol ratio are 1:1～1.5.
3. the preparation method of trimethylsilyl triflate according to claim 1, is characterized in that, described rare gas element is argon gas or nitrogen.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201310476619.5A CN103588803A (en) | 2013-10-14 | 2013-10-14 | Preparation method of trimethylsilyl trifluoromethanesulfonate |
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| CN201310476619.5A CN103588803A (en) | 2013-10-14 | 2013-10-14 | Preparation method of trimethylsilyl trifluoromethanesulfonate |
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| CN103588803A true CN103588803A (en) | 2014-02-19 |
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| CN201310476619.5A Pending CN103588803A (en) | 2013-10-14 | 2013-10-14 | Preparation method of trimethylsilyl trifluoromethanesulfonate |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112094289A (en) * | 2020-10-06 | 2020-12-18 | 中船重工（邯郸）派瑞特种气体有限公司 | Production method and equipment of trimethylsilyl trifluoromethanesulfonate |
| CN114195817A (en) * | 2021-12-24 | 2022-03-18 | 江苏笃行致远新材料科技有限公司 | Synthesis method of trifluoromethanesulfonic acid silicone ester |
| CN114394989A (en) * | 2022-03-08 | 2022-04-26 | 中船(邯郸)派瑞特种气体股份有限公司 | Preparation method of triisopropyl silicon-based trifluoromethanesulfonate |
Citations (3)
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| WO2006012425A2 (en) * | 2004-07-21 | 2006-02-02 | Corixa Corporation | Processes for the production of aminoalkyl glucosaminide phosphate and disaccharide immunoeffectors, and intermediates therefor |
| CN1847250A (en) * | 2005-04-15 | 2006-10-18 | 大连思谱精工有限公司 | Silane reagent with high reaction activity and its prepn process |
| CN102911196A (en) * | 2012-11-19 | 2013-02-06 | 江西国化实业有限公司 | Preparation method of trifluoromethanesulfonic acid trimethylsilyl ester |
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2013
- 2013-10-14 CN CN201310476619.5A patent/CN103588803A/en active Pending
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006012425A2 (en) * | 2004-07-21 | 2006-02-02 | Corixa Corporation | Processes for the production of aminoalkyl glucosaminide phosphate and disaccharide immunoeffectors, and intermediates therefor |
| CN1847250A (en) * | 2005-04-15 | 2006-10-18 | 大连思谱精工有限公司 | Silane reagent with high reaction activity and its prepn process |
| CN102911196A (en) * | 2012-11-19 | 2013-02-06 | 江西国化实业有限公司 | Preparation method of trifluoromethanesulfonic acid trimethylsilyl ester |
Non-Patent Citations (2)
| Title |
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| HANSJIIRG WETTER等: "THEXYLDIMETHYLSILY CHLORIDE’ AN EASILY ACCESSIBLE REAGENTF OR THE PROTECTiON OF ALCOHOLS", 《TETRAHEDRON LETTERS》 * |
| 李增春: "三氟甲磺酸三甲硅酯的回收重制", 《化学试剂》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112094289A (en) * | 2020-10-06 | 2020-12-18 | 中船重工（邯郸）派瑞特种气体有限公司 | Production method and equipment of trimethylsilyl trifluoromethanesulfonate |
| CN112094289B (en) * | 2020-10-06 | 2023-05-09 | 中船(邯郸)派瑞特种气体股份有限公司 | Production method and equipment of trifluoromethane sulfonate trimethyl silicone ester |
| CN114195817A (en) * | 2021-12-24 | 2022-03-18 | 江苏笃行致远新材料科技有限公司 | Synthesis method of trifluoromethanesulfonic acid silicone ester |
| CN114195817B (en) * | 2021-12-24 | 2024-04-16 | 江苏笃行致远新材料科技有限公司 | Synthesis method of trifluoro methyl sulfonate |
| CN114394989A (en) * | 2022-03-08 | 2022-04-26 | 中船(邯郸)派瑞特种气体股份有限公司 | Preparation method of triisopropyl silicon-based trifluoromethanesulfonate |
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Application publication date: 20140219 |