Abstract:
Ozonolysis is an attractive, efficient, and green means of introducing oxygen containing functionalities
using only oxygen and electricity. Unfortunately, safety issues associated with the accumulation of
dissolved ozone and potentially explosive ozonides coupled with an oxygen rich reaction atmosphere have
limited its integration into large scale process reactions. Herein we report on the development and testing
of a prototype flow-based ozonolysis reactor which allows on-the-fly removal of ozone and oxygen
negating the need for a downstream degassing step and allowing the continuous processing of
intermediate ozonides in a safe manner. The approach lends itself to being able to telescope directly into
downstream reactions without concern for the effect of residual ozone and minimises contact between
the oxygen rich ozone atmosphere and the reaction mixture. The prototype was shown to remove
between 98.5 and 99.7% of residual ozone-oxygen on-the-fly and its performance was demonstrated
through the ozonolysis of several alkenes to afford a range of oxygen containing functional groups in good
to high yields.
