17983-30-1

Example 1: Conversion of 2-cyclohexen-1-one to 3-cyanocyclohexanone 1. 100 g of 2-cyclohexen-1-one (1.04 mol) was added to a 500 ml glass flask fitted with a stirrer and heated to 140 °C under an inert atmosphere. 2. 1.2 g of sodium methanol (as a 30% sodium solution) was added to the reaction system. 3. 100 g of 2-cyclohexen-1-one (1.04 mol) was mixed with 40.2 g of hydrogen cyanide (1.49 mol) and added slowly and dropwise to the vigorously stirred initial reaction mixture over a period of 5 hours. The reaction mixture changed color to yellow-orange. 4. After completion of the dropwise addition, the reaction mixture was continued to be stirred at 145 °C for 0.5 h. The reaction mixture was then stirred for 0.5 h at 145 °C. 5. The amount of free hydrogen cyanide in the reaction mixture was determined by Volhard titration to confirm that no free hydrogen cyanide (HCN) was present. 6. 1.0 g of 85% phosphoric acid was added to stabilize the reaction mixture, resulting in a final mixture weight of 236 g. The reaction was carried out by Volhard titration. 7. The crude product was transferred to a distillation apparatus (500 ml three-necked flask equipped with a column head and zeolite) for distillation. 8. Fractions were collected at 108-112 °C under 0.1 mbar pressure. 9. The total yield by GC analysis was 160.7 g (87.7% based on hydrogen cyanide), of which the fraction distilled at 10-100 °C contained 98.3 g of product (61% of total product). 10. The purity of the distillation product was 96%.

[1] Patent: US2011/124919, 2011, A1. Location in patent: Page/Page column 8
[2] Journal of the American Chemical Society, 1972, vol. 94, p. 4654 - 4672