反应详情

816 grams of 3-mercapto-1-propyltrimethoxysilane, 871 grams of 25 weight percent methanolic solution of sodium methoxide, and 1,724 grams of toluene were charged to a 5-liter flask under an atmosphere of nitrogen. The stirred mixture developed a pinkish color. Methanol was removed from the flask by distilling off a methanol-toluene azeotrope, during which time the contents of the flask turned colorless. The appearance of a strong density current in the distillate which coincided with an increased in distillation head temperature from 63° C. to 108° C. signaled the point at which methanol removal from the flask was complete. With continued stirring, the contents of the flask were allowed to cool and were placed in an ice-water bath. 361 grams of propionyl chloride was added to the flask dropwise and/or in small portions with continued stirring in an ice-water bath until the reaction was complete. Aliquots of the stirred mixture were taken periodically and placed onto pH paper. An alkaline reading indicated the completion of the reaction. The final mixture was a white suspension of NaCl in a toluene solution of the product. This mixture was filtered and the solvent was removed from the filtrate to yield a light brown product. Gas chromatography indicated 5 percent 3-mercapto-1-propyltrimethoxysilane, 25 percent of 3-(methylthio)-1-propyltrimethoxysilane, and 70 percent of 3-(acetylthio)-1-propyltrimethoxysilane (product). Flash distillation from one to two grams of powdered sodium methoxide yielded a colorless product. The sodium methoxide was added to ensure that any remaining acidity was neutralized. Further optional fractional distillation yielded a product in excess of 98 percent purity by GC.

1. customMethanol was removed from the flask
2. distillationby distilling off a methanol-toluene azeotrope
3. temperaturean increased in distillation head temperature from 63° C. to 108° C.
4. customat which methanol removal from the flask
5. temperatureto cool
6. customwere placed in an ice-water bath
7. addition361 grams of propionyl chloride was added to the flask dropwise
8. stirringin small portions with continued stirring in an ice-water bath until the reaction
9. customthe completion of the reaction
10. filtrationThis mixture was filtered
11. customthe solvent was removed from the filtrate
12. customto yield a light brown product
13. distillationFlash distillation from one to two grams of powdered sodium methoxide
14. customyielded a colorless product
15. distillationFurther optional fractional distillation
16. customyielded a product in excess of 98 percent purity by GC