Sodium Chloride → 3-(Propionylthio)-1-propyltrimethoxysilane

Temperature

32.5 °C

1035 grams of 3-mercapto-1-propyltrimethoxysilane, 1096 grams of a 25 weight percent methanolic solution of sodium methoxide, and 1764 grams of toluene were charged to a 5-liter flask under an atmosphere of nitrogen. The stirred mixture developed a pinkish color. The flask was placed into a water bath at 64° C. Methanol was removed from the flask by distilling off a methanol-toluene azeotrope under a partial vacuum. The vacuum was kept such that the temperature in the distillation head was maintained at 30 to 35° C. during which time 1500 ml of distillate, consisting of a toluene-methanol azeotrope, was collected. During this time the contents of the flask turned colorless. An additional 429 grams of toluene was added and the distillation resumed. The appearance of a strong density current in the distillate which coincided with an increase in distillation head temperature from 35 to 55° C. and the appearance of a changing liquid surface tension in the condenser signaled the point at which methanol removal from the flask was complete. The contents of the flask had become a viscous fluid. With continued stirring, the contents of the flask were allowed to cool. The flask was placed in an ice-water bath resulting in what appeared to be a thick paste. 457 grams of propionyl chloride was added to the flask drop-wise 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. 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 nearly colorless product. Gas chromatography indicated (by weight) 3 percent of 3-mercapto-1-propyltrimethoxysilanec, 1 percent of 3-(methylthio)-1-propyltrimethoxysilane, and 96 percent of 3-(acetylthio)-1-propyltrimethoxysilane (product). Flash distillation from 1 to 2 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. customThe flask was placed into a water bath at 64° C
2. customMethanol was removed from the flask
3. distillationby distilling off a methanol-toluene azeotrope under a partial vacuum
4. customwas collected
5. additionAn additional 429 grams of toluene was added
6. distillationthe distillation
7. temperaturean increase in distillation head temperature from 35 to 55° C.
8. customat which methanol removal from the flask
9. temperatureto cool
10. customThe flask was placed in an ice-water bath
11. customresulting in what
12. stirringin small portions with continued stirring in an ice-water bath until the reaction
13. customthe completion of the reaction
14. filtrationThis mixture was filtered
15. customthe solvent was removed from the filtrate
16. customto yield a nearly colorless product
17. distillationFlash distillation from 1 to 2 grams of powdered sodium methoxide
18. customyielded a colorless product
19. distillationFurther optional fractional distillation
20. customyielded a product in excess of 98 percent purity by GC

ORD record

ord-fd4db197d5a642f5827683c7232f4eba

Source dataset

uspto-grants-2002_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06414061B1