Carbon Dioxide → 2,2-Bis(trifluoromethyl)-4-hydroxymethyl-1,3-dioxolane

Temperature

118 °C

118 Grams glycerol carbonate (1 mole) is placed in a 500 ml three neck flask, fitted with a thermometer, magnetic stirrer, gas-inlet tube, and a condenser cooled with a dry ice-isopropyl alcohol bath. Hexafluoroacetone gas is added to the vigorously stirred glycerol carbonate at 27° to 60° C. until 142 grams (0.85 moles) has been absorbed. The dry ice condenser is now replaced by a water condenser which is connected to a dry ice trap so that hexafluoroacetone which escapes during reaction may be condensed. The temperature is raised slowly to about 118° C. at which point CO2 evolution begins. The temperature is allowed to rise to 148° C. during a 40 hour reaction period. The resulting product is mixed with water (50 ml) and the organic layer separated and diluted with chloroform. The chloroform solution is washed several times with water and 5% NaHCO3 solution. Vacuum stripping gives crude 2,2-bis(trifluoromethyl)-4-hydroxymethyl-1,3-dioxolane. This is distilled at 78° - 80° C./25 mm Hg and the yield of pure product is 92%, based on utilized hexafluoroacetone. The twice distilled product has a refractive index of 1.35046 (20° C.) and upon analysis contained 47.19% fluorine, 30.02% carbon, and 2.22% hydrogen.

1. customfitted with a thermometer, magnetic stirrer, gas-inlet tube, and a condenser
2. temperaturecooled with a dry ice-isopropyl alcohol bath
3. customhas been absorbed
4. customThe dry ice condenser is now replaced by a water condenser
5. customwhich is connected to a dry ice trap so that hexafluoroacetone which
6. customescapes during reaction
7. customcondensed
8. customreaction period
9. customthe organic layer separated
10. additiondiluted with chloroform
11. washThe chloroform solution is washed several times with water and 5% NaHCO3 solution

ORD record

ord-a77cf2c362964cb5b85c43f632dc0b6f

Source dataset

uspto-grants-1976_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US03996376