反応 #304601

反応方程式

potassium fluoride

diethyl sulfate

diethyl sulfate

potassium fluoride

KOH

perfluorovaleryl fluoride

C3F7OCF═CF2

→

C3F7OCF(CF3)CF(OC2H5)C4F9

溶媒

diglyme

diglyme

water

反応条件

後処理

1. 1
   その他A clean, dry
2. 2
   その他The reactor was sealed
3. 3
   温度cooled with a dry ice-acetone bath
4. 4
   その他evacuated
5. 5
   温度The reactor was cooled to below 0° C. with a dry ice-acetone bath
6. 6
   workup.ADDITIONThe reactor contents were added to a clean,
7. 7
   その他dry 2 L round bottom flask
8. 8
   その他equipped with a mechanical stirrer
9. 9
   温度heated to 52° C.
10. 10
    workup.WAITheld for 20 hours
11. 11
    温度The flask was cooled to ambient temperature
12. 12
    温度The flask was heated to 65° C.
13. 13
    workup.WAITheld for 4 hours
14. 14
    その他The resulting crude product was isolated by steam distillation
15. 15
    洗浄washed one time with an equal weight of water
16. 16
    workup.DISTILLATIONfractionally distilled

実験手順

A clean, dry, 600 mL, stainless steel, Parr pressure reactor was charged with spray-dried potassium fluoride (8.4 grams, 0.14 mole), anhydrous diglyme (128 grams), and Adogen™ 464 phase transfer catalyst (2.2 grams). The reactor was sealed, cooled with a dry ice-acetone bath, evacuated, and charged with perfluorovaleryl fluoride (130.0 grams, 0.49 mole) and C3F7OCF═CF2 (125.0 grams, 0.47 mole). The reactor was then heated to 85° C. and held for 20 hours with agitation. The reactor was cooled to below 0° C. with a dry ice-acetone bath and vented. The reactor contents were added to a clean, dry 2 L round bottom flask equipped with a mechanical stirrer, a heating mantle, a temperature probe, and a water condenser. The flask was charged with spray-dried potassium fluoride (16.0 grams, 0.28 mole), diethyl sulfate (61.0 grams, 0.40 mole), anhydrous diglyme (48 grams), and catalyst (2.5 grams). The contents of the flask were stirred, heated to 52° C., and held for 20 hours. The flask was cooled to ambient temperature, and water (35 grams) and 45 percent KOH (75 grams, 0.60 mole) were added. The flask was heated to 65° C. and held for 4 hours to neutralize excess diethyl sulfate. The resulting crude product was isolated by steam distillation, washed one time with an equal weight of water, and fractionally distilled to provide 91.0 grams of 99.3 percent purity product C3F7OCF(CF3)CF(OC2H5)C4F9. The boiling point of this product was 178° C., and its structure was confirmed by GCMS. The viscosity of the product was 7.3×10−5 m2/s (73 centistokes) at −50° C. (measured using a Cannon-Fenske viscometer and a Wescan Model 221 viscosity timer).

出典