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
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.
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 :
