Chemical Properties
Hydroperoxide is formed by the oxidation of tetralin, a
DuPont product, and used as a turpentine replacement. The
technical grade hydroperoxide is a liquid and will have a
residual odor of benzene/menthol. No rapid reaction
occurs with air or water. Most alkyl monohydroperoxides
are liquid, the explosivity of the lower members (e.g.,
methyl hydroperoxide or possibly due to traces of the
dialkyl peroxides) decreasing with increasing chain length
and branching. Tetralin hydroperoxide explodes on superheating
the liquid. Its interaction with strong reducing
agents, like lithium tetrahydroaluminate, is vigorously
exothermic (13d).
Uses
Tetralin hydroperoxide has been prepared by the oxidation of
tetralin in the presence of cobalt naphthenate, manganese
stearate, and ceric stearate or naphthenate. Tetralin hydroperoxide,
produced by the oxidation of tetralin, may be
separated from reaction products by formation of its sodium
salt. The kinetics of the liquid-phase oxidation of tetralin
have been studied . Chen and Lin used tetralin hydroperoxide
as an intermediate in the hydroxylation of tetralin to
tetralol in rat liver homogenate.
General Description
Hydroperoxide formed by the oxidation of tetralin, a DuPont product, used as a turpentine replacement. The technical grade hydroperoxide is a liquid and will have a residual odor of benzene/menthol.
Reactivity Profile
Most alkyl monohydroperoxides are liquid, the explosivity of the lower members (e.g., methyl hydroperoxide, or possibly due to traces of the dialkyl peroxides) decreasing with increasing chain length and branching [Bretherick 2nd ed. 1979 p. 10]. 1,2,3,4-tetrahydro-1-naphthyl hydroperoxide explodes on superheating the liquid [Hock et al. Ber. 1933. pp. 66, 61]. It's interaction with strong reducing agents, like lithium tetrahydroaluminate, is vigorously exothermic.
Purification Methods
Crystallise the tetralin hydroperoxide from hexane, toluene at -30o (m 54.0-54.5o). The oxygen content should be ~9.70%. [Knight & Swern Org Synth Coll Vol 1V 895 1963.]
