2,2,2-TRIFLUOROETHYL VINYL ETHER

Description

Fluroxene , 2,2,2-trifluoro-1- vinyloxyethane, is a colorless liquid with a pungent odor. It is inflammable and, at concentrations above 4 %, explosive in air. Fluroxene (MAC3.4) generally is used in a mixture with oxygen and nitrous oxide. Several cases of liver damage have been observed.

Description

Fluroxene， 2,2,2-trifluoro-1- vinyloxyethane, is a colorless liquid with a pungent odor. It is inflammable and, at concentrations above 4 %, explosive in air. Fluroxene (MAC3.4) generally is used in a mixture with oxygen and nitrous oxide. Several cases of liver damage have been observed.

Originator

Fluoromar, Ohio Medical, US ,1961

The Uses of 2,2,2-TRIFLUOROETHYL VINYL ETHER

Ca channel blocker, coronary vasodilator

Definition

ChEBI: Fluroxene is an organofluorine compound.

Manufacturing Process

The following process description is taken from US Patent 2,830,007.
270 grams 2,2,2-trifluoroethanol was added slowly to 15 grams of a cooled suspension of potassium metal in 250 ml of ethyl ether with stirring. When all the potassium metal had reacted, the resulting solution was fractionally distilled in order to remove the ethyl ether. The residue was placed in a bomb and the air was removed from the bomb by flushing with acetylene. The bomb was sealed and heated to 150°C. Acetylene was then introduced at 245 to 260 psi and the gas pressure was maintained for a period of 5 hours under mechanical agitation throughout the reaction. At the end of this time, heating was discontinued, the flow of acetylene was shut off and the bomb was allowed to cool to room temperature. The excess pressure in the bomb was reduced to atmospheric pressure by venting any gases through a dry ice cooled trap.
The reaction mixture comprising 2,2,2-trifluoroethyl vinyl ether, 2.2.2trifluoroethanol and potassium 2,2,2-trifluoroethylate was fractionally distilled, whereupon crude 2,2,2-trifluoroethyl vinyl ether was obtained which boiled at 42° to 45°C at 760 mm. More 2,2,2-trifluoroethyl vinyl ether was obtained when the distillation residue was returned to the bomb and reacted with acetylene in the same manner as hereinabove described.
The alkali metal hydroxides, instead of the alkali metals per se, can be employed to produce the alkali metal 2,2,2-trifluoroethanolate. However, this introduces water in the reaction mixture which requires removal prior to vinylation with acetylene. The crude products, on further distillation, yielded 2,2,2-trifluoroethyl vinyl ether having a boiling point of 43.1°C at 759 mm.

Therapeutic Function

Inhalation anesthetic

General Description

Volatile Liquid. Bp: 43°C. Density: 1.14 g cm-3 . Formerly used as an inhalation anesthetic.

Reactivity Profile

2,2,2-TRIFLUOROETHYL VINYL ETHER is non-flammable but combustible. Can form explosive mixtures with air. Reacts with strong oxidizing agents.

Safety Profile

Poison by inhalation. Moderately toxic by intraperitoneal route. An experimental teratogen. Human systemic effects by inhalation: jaundice and liver function tests impaired. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of F-. Used as an anesthetic. See also FLUORIDES and ETHERS.

Synthesis

The compound is prepared by catalytic vinylation of 2,2,2-trifluoroethanol in the presence of alkali-metal trifluoroethoxide :