Iodine → 2-Chloro-1,1,1,4,4,4-hexafluorobutane

Temperature

250 °C

2,3-Dichlorohexafluorobut-2-ene (100 g) and iodine (55 g) were added to a 400 mL shaker tube. The tube was sealed, cooled, evacuated, and charged with 1500 psi of hydrogen at room temperature. The tube was then heated to 230° C. for 1 hour, 250° C. for 2 hours, and 260° C. for 15 hours. The tube was then cooled to room temperature, vented, and opened. The purple liquid was washed with water and then analyzed by GC/IR. Analysis of the washed liquid showed that it contained about 84% 2-chloro-1,1,1,4,4,4-hexafluorobutane, about 13% 2,3-dichloro-1,1,1,4,4,4-hexafluorobutane and about 1% 1,1,1,4,4,4-hexafluorobutane. The liquid was distilled on a concentric tube column yielding 35 g (41% isolated yield) of 2-chloro-1,1,1,4,4,4-hexafluorobutane (HCFC-346mdf) as a clear liquid with a b.p. of 50.9-51.4° C. 1H NMR (CHCl3 as internal standard): 4.4 ppm, complex, 1H; 2.9 ppm, complex, 1H; 2.7 ppm, complex, 1H. 19F NMR (CCl3F) as internal standard): 64.7 ppm, t, 1F; -76 ppm, d, 1F. GC/IR showed an identical spectrum to an authentic sample.

1. customThe tube was sealed
2. temperaturecooled
3. customevacuated
4. additioncharged with 1500 psi of hydrogen at room temperature
5. temperatureThe tube was then cooled to room temperature
6. washThe purple liquid was washed with water
7. distillationThe liquid was distilled on a concentric tube column

ORD record

ord-3c7dfa0a7e954db78852163f254175c0

Source dataset

uspto-grants-1992_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05097082