Potential hazard with 2-methoxyprop-2-yl hydroperoxide

Pat Dussault
University of Nebraska, Lincoln

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.

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