Triethylamine hydrochloride → 3-Chloro-1,1,2,3,3-pentafluoro-1-propene

Temperature

0 °C

A 300-mL four-neck flask provided with a Dimroth condenser, a dropping funnel, and a thermometer was charged with triethylamine hydrochloride (97 g, 703 mmol) and 50 mL of diglyme, and the mixture was stirred by a magnetic stirrer. The Dimroth condenser was cooled using a −20° C. refrigerant, and the reaction flask was cooled to 0° C. in an ice bath. With the dropping funnel, perfluoroallyl fluorosulfate (135 g, 586 mmol) was dropped over about one hour in such a manner that the temperature in the flask was maintained at 10° C. or lower. After the dropping, the mixture was stirred for one hour. The Dimroth condenser was replaced by a Liebig distillation apparatus. The flask was allowed to reach room temperature (25° C.), and the resulting product (having a boiling point of 12° C.) was distilled. An amount of 100 mL of water was added to the flask to terminate the reaction. As a result, 90.7 g of the target perfluoroallyl chloride (purity: 99 GC %) was obtained as a distilled component (yield: 93%). The distillation residue was determined by NMR analysis to include carboxylic acids and ammonium fluorosulfate which were probably generated from hydrolysis of unreacted perfluoroallyl fluorosulfate in terminating the reaction, and an excess amount of triethylamine hydrochloride.

1. customA 300-mL four-neck flask provided with a Dimroth condenser, a dropping funnel
2. temperatureThe Dimroth condenser was cooled
3. customusing a −20° C.
4. temperaturewas maintained at 10° C.
5. stirringAfter the dropping, the mixture was stirred for one hour
6. distillationThe Dimroth condenser was replaced by a Liebig distillation apparatus
7. customto reach room temperature
8. custom(25° C.)
9. distillationwas distilled
10. additionAn amount of 100 mL of water was added to the flask
11. customto terminate
12. customthe reaction

ORD record

ord-0e3e10ae9c8e4bb3a998f4071b1fc021

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08816138B2