Description
Triisopropyl chlorosilane is an important sterically hindered organosilicon protective agent, which is mainly used to protect various types of hydroxyl groups, especially in polyfunctional hydroxyl compounds, which can be selectively protected and deprotected. It is very important to synthesize nucleosides, nucleotides and carbohydrates. Triisopropylchlorosilane is a good hydroxyl protecting agent, and its silanization reaction is carried out in a slight excess of imidazole solution. The acid hydrolytic stability of the protected intermediate is between TBDMS and TBDPS and the alkaline hydrolytic stability is higher than the former two.
Chemical Properties
Triisopropylsilyl chloride is colorless clear liquid
Physical properties
bp 198 °C/739 mmHg; d 0.901 g cm?3.
Application
Triisopropyl chlorosilane is mainly used as a basic intermediate in the synthesis of organic silicon materials and a blocking agent for silicone oil or silicone rubber. These triisopropylchlorosilanes can be used as raw materials for preparing functional silanes or silane coupling agents. In the reaction with organometallic compounds, the chlorine atoms of triisopropylchlorosilane are replaced by corresponding organic groups to form organochlorosilanes or organofunctional silanes.
Triisopropyl chlorosilane is mainly used in the production of aminosilane and methacryloxysilane, and can also be used as a rubber processing additive to couple inorganic fillers in various halogenated rubbers, such as neoprene rubber, chlorobutyl rubber , chlorosulfonated polyethylene and other halogenated rubbers. The existence of triisopropylchlorosilane can greatly improve various physical and mechanical properties of composites. Triisopropylchlorosilane can also be used to prepare antifungal and deodorant finishes with special bactericidal, deodorant, antistatic and surface-active properties.
Preparation
There are two main methods for synthesizing triisopropyl chlorosilane. One is to use triisopropyl silane as a raw material, and hydrochloric acid and other reagents are used to chlorinate the hydrogen on the silicon. Another method uses silicon tetrachloride as raw material, and reacts with isopropyl lithium to obtain triisopropyl chlorosilane.
Synthesis
GENERAL STEPS: In a 500 mL four-necked flask equipped with a stirrer, thermometer and Dimroth condenser, 37.7 g (0.2 mol) of triisopropylmethoxysilane was added. Subsequently, 150 g of 35% hydrochloric acid was added to the flask and the reaction mixture was stirred at 20 °C for 10 hours. Upon completion of the reaction, the mixture was left to stratify and the aqueous and organic layers were separated. The organic layer was distilled and the fractions with boiling points of 78 °C - 80 °C/10 mmHg were collected to give 38 g of triisopropylchlorosilane (yield: 99%).
Example 14: The operation of Example 13 was repeated, with the difference that 83.3 g (0.2 mol) of triisopropyl n-butoxysilane was used instead of triisopropylmethoxysilane for the reaction with 35% hydrochloric acid. Again the organic layer was separated and distilled to give 38 g of triisopropylchlorosilane (yield: 99%).
(d) Synthesis of triisopropylchlorosilane (using the method of the third aspect of the present invention): triisopropylmethoxysilane in the organic layer obtained in step (c) above was reacted with 35% hydrochloric acid in the same manner as in Example 15 (d). After separating the organic layer from the aqueous layer, the organic layer was subjected to fractional distillation under reduced pressure, and a fraction of 78° C. - 80° C. / 10 mmHg was collected to obtain 27 g of triisopropylchlorosilane (yield: 69%).
Again using the method of the third aspect of the present invention, the organic layer obtained in step (c) was treated with 35% hydrochloric acid, operating as in Example 15 (d). The organic layer was separated and fractionated under reduced pressure to obtain 24 g of triisopropylchlorosilane with a boiling point of 78°C-80°C/10 mmHg (yield: 60%).
(b) Synthesis of triisopropylchlorosilane (using the method of the third aspect of the present invention): the organic layer obtained in step (a) was treated with 35% hydrochloric acid according to the method of Example 15 (d). After separation of the organic layer, fractional distillation under reduced pressure was carried out to obtain 24 g of triisopropylchlorosilane with a boiling point of 78°C-80°C/10 mmHg (yield: 60%).
References
[1] Organometallics, 2012, vol. 31, # 8, p. 3199 - 3206
[2] Patent: US2005/70730, 2005, A1. Location in patent: Page/Page column 23-26
[3] Journal of Organometallic Chemistry, 2006, vol. 691, # 1-2, p. 174 - 181
[4] Journal of Organometallic Chemistry, 2006, vol. 691, # 1-2, p. 174 - 181
