Tetrafluoroethylene reaction with ozone

Tetrafluoroethylene Oxide TFEO has only been prepared by a process employing oxygen or ozone because of its extreme reactivity with ionic reagents. This reactivity may best be illustrated by its low temperature reaction with the weak nucleophile, dimethyl ether, to give either of two products (47) (eq. 10). 

A major area of concern in chemical processes is the use of volatile organic compounds as solvents for reactions. The solvent is not generally consumed in the reaction, but there are unavoidable releases to the atmosphere even in the most carefully controlled processes. Further, the solvent may be toxic or may decompose at least to some extent during reaction, thus creating wastes. The use of supercritical fluids ("Chemistry at Work" box. Section 11.4) represents a way to replace the conventional solvent by CO2, a nontoxic gas already present in the atmosphere that can be recycled. Du Pont chemical company, for example, has invested in a production facility to make polytetrafluoroethylene, — [CF2Cp2] — (Teflon M) and copolymers with tetrafluoroethylene in liquid or supercritical CO2. In this case the CO2 replaces chlorofluorocarbon solvents, which, aside from their costs, have harmful effects on Earth s ozone layer (Section 18.3). 

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