Synthesis method of silyl trifluoromethanesulfonate

A technology of silicon trifluoromethanesulfonate and synthesis method, which is applied in the direction of silicon organic compounds, chemical instruments and methods, compounds of group 4/14 elements of the periodic table, etc., which can solve the problems of expensive raw materials, low activity and reaction, and limited Application and other issues, to achieve the effect of improved reaction safety, simple operation of reaction steps, and low production cost

Pending Publication Date: 2022-03-18
江苏笃行致远新材料科技有限公司
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The earliest synthesis method of trimethylsilyl trifluoromethanesulfonate is to react silver trifluoromethanesulfonate with trimethylchlorosilane (Chemische Berichte-Recueil 1970,103,868-879), and subsequently develop trifluoromethanesulfonic anhydride and The method of trimethylsilyl ether reaction preparation (Synthesis-Stuttgart 1985,2,206-207), but the raw material price of this kind of method is expensive, has limited its application in industry
[0005] Trifluoromethanesulfonic acid is generally obtained from the corresponding alkylsulfonyl chloride or alkylsulfonyl fluoride by electrolysis to obtain trifluoromethanesulfonyl fluoride, and then through alkali hydrolysis to obtain trifluoromethanesulfonate, which is acidified with concentrated sulfuric acid to obtain trifluoromethanesulfonyl sulfonate Fluoromethanesulfonic acid, the trifluoromethylsulfonyl fluoride in its production process itself is an acylating agent, but its own activity is low and it is difficult to react with silanol and siloxane

Method used

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  • Synthesis method of silyl trifluoromethanesulfonate
  • Synthesis method of silyl trifluoromethanesulfonate
  • Synthesis method of silyl trifluoromethanesulfonate

Examples

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Embodiment 1

[0040] Add 486g (3mol) of hexamethyldisiloxane and 11.2g (0.1mol) of DMAP into a 2L stainless steel reactor, cool down to -30°C under nitrogen protection, and evacuate the reactor to -0.09MPa. 532 g (3.5 mol) of trifluoromethanesulfonyl fluoride was slowly passed through, and the reaction vessel was closed after the passage was completed, and the temperature was raised to 20° C. for 8 hours. After the reaction, slowly open the outlet valve of the reactor, control the temperature of the condenser at -20°C, and collect the unreacted trifluoromethanesulfonyl fluoride at the temperature of the receiving tank at -30°C. Subsequently, the temperature of the condenser was controlled to 16° C., and the temperature of the receiving tank was 0° C. to collect the by-product trimethylfluorosilane. Increase the vacuum degree of the reactor to -0.08MPa, heat up to 60°C for distillation, collect the fraction at 42-44°C, and obtain 642g of the product trimethylsilyl trifluoromethanesulfonate, ...

Embodiment 2

[0043] Add 493g (2mol) hexaethyldisiloxane and 11.2g (0.1mol) DMAP into a 2L stainless steel reactor, cool down to -10°C under nitrogen protection, and evacuate the reactor to -0.09MPa. 380 g (3.5 mol) of trifluoromethanesulfonyl fluoride was slowly passed through, and the reactor was closed after the passage was completed, and the reaction was carried out at this temperature for 12 hours. After the reaction, slowly open the outlet valve of the reactor, control the temperature of the condenser at -20°C, and collect the unreacted trifluoromethanesulfonyl fluoride at the temperature of the receiving tank at -30°C. Increase the vacuum of the reactor to -0.085MPa, collect the fraction at 55-58°C to obtain triethylfluorosilane; raise the temperature to 90°C, collect the fraction at 85-87°C to obtain the product triethylsilyl trifluoromethanesulfonate 501g, 94.9% yield, 99.2% purity, 0.02% acid content.

[0044]Put 80g of calcium hydroxide (purity 95%) in 1000mL water suspension in...

Embodiment 3

[0046] Add 162 g (1 mol) of hexamethyldisiloxane and 5.6 g (0.05 mol) of DMAP into a 1 L four-necked flask, and replace with nitrogen. The temperature was lowered to -30°C under nitrogen protection, and the reaction bottle was evacuated to -0.09MPa. 182.4 g (1.2 mol) of trifluoromethanesulfonyl fluoride was slowly introduced, and a white solid gradually precipitated in the reaction bottle, and the reaction was carried out at this temperature for 24 hours, and the reaction was stopped. Set up the distillation device, slowly raise the temperature of the reaction bottle to 0°C, control the temperature of the condenser tube at -20~-15°C, and collect the unreacted trifluoromethanesulfonyl fluoride at the temperature of the receiving tank at -35~-30°C. Then raise the temperature of the reaction bottle to 25°C, control the temperature of the condenser tube at 16-20°C, and collect the by-product trimethylfluorosilane at the temperature of the receiving tank at 0°C. Increase the vacuu...

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Abstract

The invention discloses a synthesis method of silyl trifluoromethanesulfonate, which comprises the following steps: mixing siloxane with a catalyst dimethylaminopyridine (DMAP), and introducing trifluoromethanesulfonyl fluoride at a low temperature of-40 to 0 DEG C for reaction under the protection of inert gas. According to the synthesis method of the silyl trifluoromethanesulfonate, the product purity is easy to control, the product quality requirement can be met only through simple distillation, and the product purity is gt; the content is 99%, and acid lt is contained; the method has the advantages that the process is simple, the purity is 0.05%, the self-circulation of the process is realized, no solvent is used, the generated fluorosilane can be used as the raw material siloxane for mechanical application only by simple treatment, and the unique by-product is the purity gt; 95% of calcium fluoride can be used for waste resource utilization.

Description

technical field [0001] The invention belongs to the technical field of fine chemicals, relates to the technical field of organic synthesis, in particular to a method for synthesizing silicon trifluoromethanesulfonate. Background technique [0002] Silicon trifluoromethanesulfonate is generally a colorless liquid and is easily hydrolyzed in air. It is a commonly used siliconization reagent and can be used for the conversion and protection of functional groups such as alcohols, amines, ketones, aldehydes, and carboxylic acids. At the same time, It is also often used as a catalyst for Dieckmann reaction and Morita-Baylis-Hillman reaction, and also as an initiator for cationic polymerization. It is widely used in the fields of medicine, pesticides, liquid crystals, and silicon materials. [0003] Silicon trifluoromethanesulfonate mainly includes trimethylsilyl trifluoromethanesulfonate, triethyl silicon trifluoromethanesulfonate, triisopropyl silicon trifluoromethanesulfonate, t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F7/08
CPCC07F7/0898
Inventor 刘智慧崔志鹏刘文娟崔晓雷李欣
Owner 江苏笃行致远新材料科技有限公司
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