Water → HCID 131728043, compound

Temperature

150 °C

Ethylene (56 g) was introduced to an autoclave charged with C4F9(CH2CF2)2I (714 g) and d-(+)-limonene (3.2 g), and the reactor heated at 240° C. for 12 hours. The product was isolated by vacuum distillation to provide C4F9(CH2CF2)2CH2CH2I. A mixture of C4F9(CH2CF2)2CH2CH2I (10 g, 0.02 mol) and N-methylformamide (8.9 mL, 0.15 mol) was heated to 150° C. for 26 hours. The mixture was cooled to 100° C., followed by the addition of water to separate the crude ester. Ethyl alcohol (3 mL) and p-toluene sulfonic acid (0.09 g) were added and the mixture stirred at 70° C. for 0.25 hours. Ethyl formate and ethyl alcohol were removed by distillation to give a crude product. The crude product was dissolved in ether, washed with 10% by weight aqueous sodium sulfate, water and brine, in turn, and dried over magnesium sulfate. Distillation provided the product C4F9(CH2CF2)2CH2CH2OH (6.5 g, 83% yield): bp 94-95° C. at 2 mm Hg (266 Pa).

1. temperatureThe mixture was cooled to 100° C.
2. customto separate the crude ester
3. additionEthyl alcohol (3 mL) and p-toluene sulfonic acid (0.09 g) were added
4. customEthyl formate and ethyl alcohol were removed by distillation
5. customto give a crude product
6. washwashed with 10% by weight aqueous sodium sulfate, water and brine, in turn
7. dry with materialdried over magnesium sulfate
8. distillationDistillation

ORD record

ord-3643c95caf6c4ff8b4b6a89f63b7fd2a

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08173848B2