Acrylonitrile → 3-(n-Decylthio)propionitrile

Temperature

10 °C

To a 250 mL round-bottomed flask fitted with an overhead mechanical stirrer, a thermometer and an addition funnel were charged 87 g of 1-decanethiol and 20 drops of a 21% by weight solution of sodium ethoxide in ethanol. The mixture was cooled to 10° C. using an ice bath. Then the dropwise addition of 53 g of acrylonitrile was started. After addition of a portion of the acrylonitrile, 10 drops of 21% by weight solution of sodium ethoxide in ethanol were added. The temperature of the reaction mixture during the addition of the remaining acrylonitrile ranged between 30° C. and 35° C. The reaction mixture was then kept at room temperature overnight (~19 hours). The unreacted acrylonitrile was then removed by distillation at atmospheric pressure. The remaining material was then distilled at ~1 mm pressure. A first fraction was collected from 150° C. to 160° C. Fraction one had a strong odor of thiol. A second and final fraction was collected at 160° C. The second fraction had a faint odor of thiol. An NMR spectrum indicated the second fraction to be the desired product 83.5% of theoretical (94.9 g) based upon the weight of 1-decanethiol employed.

1. customTo a 250 mL round-bottomed flask fitted with an overhead mechanical stirrer
2. additionwere added
3. customranged between 30° C. and 35° C
4. custom(~19 hours)
5. customThe unreacted acrylonitrile was then removed by distillation at atmospheric pressure
6. distillationThe remaining material was then distilled at ~1 mm pressure
7. customA first fraction was collected from 150° C. to 160° C
8. customA second and final fraction was collected at 160° C

ORD record

ord-94864048d2574671bf6b2fdae4cd2713

Source dataset

uspto-grants-1991_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05004558