3,4,5,6-Tetrafluorophthalonitrile synthesis
- Product Name:3,4,5,6-Tetrafluorophthalonitrile
- CAS Number:1835-65-0
- Molecular formula:C8F4N2
- Molecular Weight:200.09
126-33-0
1953-99-7
1835-65-0
Example A Synthesis of 3,4,5,6-tetrafluorophthalonitrile: Anhydrous potassium fluoride (11.0 kg) was added to a 50 gallon stainless steel reactor. The salt was dried at 115°-138°C for 48 hours under 28 inches of vacuum. After the salt was cooled to 100°C, cyclobutanesulfone (19 liters) and tetrachlorophthalonitrile (4.74 kg) were added sequentially. The mixture was heated to 156°C within 30 minutes with stirring, followed by continued heating at 135°-162°C for 2.5 hours with vigorous stirring. Upon completion of the reaction, the mixture was cooled to 31°C (taking 15 minutes) and ice (69 kg) and softened water (119 liters) were added. After stirring the resulting mixture for 1.5 hours, the crude product was collected by centrifugation and washed with softened water (120 liters). The crude product was retransferred to a 50-gallon stainless steel still with deionized water (100 liters). Steam distillation was performed until 80 liters of distillate were collected. The distillate was cooled to 0°-5°C and the product was collected by centrifugation. The crystals were washed with softened water (2 x 90 l) to give 2.82 kg of wet product (LOD 6.4%; calculated yield: 74%). A small amount of the sample was vacuum dried at room temperature for two days and the melting point was measured to be 81°-83°C.
Yield:1835-65-0 74%
Reaction Conditions:
with potassium fluoride in water
Steps:
A 3,4,5,6-Tetrafluorophthalonitrile
Example A 3,4,5,6-Tetrafluorophthalonitrile Anhydrous potassium fluoride (11.0 kg) is added to a 50 gallon stainless steel reactor. The salt is dried under 28 inches vacuum at 115°-138° C. for 48 hours. The salt is cooled to 100° C. and tetramethylenesulfone (19 liters) added followed by tetrachlorophthalonitrile (4.74 kg). The mixture is heated with stirring to 156° C. over a 30 minute period. Heating with vigorous agitation is continued for another 2.5 hours at 135°-162° C. The mixture was cooled to 31° C. (15 minutes) and ice (69 kg) and demineralized water (119 liters) were added. The resulting mixture was stirred 1.5 hours before centrifuging to collect crude product which was washed with demineralized water (120 liters). The crude product was transferred back into the 50 gallon stainless steel still and demineralized water (100 liters) added. The mixture was steam distilled until 80 liters of distillate were collected. The distillate was cooled to 0°-5° C. and the product collected on a centrifuge. The crystals were washed with demineralized water (2*90 liters) to give 2.82 kg wet product: LOD 6.4%; calculated yield: 74%. A small sample was dried under vacuum for two days at room temperature; mp 81°-83° C.
References:
Warner-Lambert Company US4782180, 1988, A
1953-99-7
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