Potential hazard with 2-methoxyprop-2-yl hydroperoxide
Chemical & Engineering News (9 Aug 1993) Vol. 71, No. 32, pp. 2.
We would like to draw attention to a potential hazard associated
with a procedure reported from our laboratories, "2-Methoxyprop-2-yl
Hydroperoxide: A Convenient Reagent for the Synthesis of
Hydroperoxides and Peracids," P. H. Dussault and A. Sahli [J. Org.
Chem., 57, 1009 (1992)]. The procedure, which calls for
room-temperature concentration of the ozonolysis-derived reagent
before redissolution in an appropriate solvent, has been performed
uneventfully on numerous occasions. Recently, however, several
concentrated samples were observed to undergo rapid exothermic
decomposition. In one case, an open vial containing a 2-g sample
emitted a pillar of flame several feet high. We are currently
investigating alternative procedures, including concentration of the
reagent at 0 C. Extreme caution, including the rigorous use
of safety shields, is warranted. The reagent should not be stored,
but should be generated only as needed. Dilute solutions of excess
reagent can be safely quenched with dimethyl sulfide,
triphenylphosphine, or aqueous sodium sulfite.
page last revised December 7, 1998