High yields of tert-butyl hydroperoxide, an equimolar mixture of tertbutyl hydroperoxide and tert-butyl alcohol, or tert-butyl alcohol can be obtained, depending on the conversion and the concentration of metal ions capable of decomposing hydroperoxides
The reaction of halogens with olefins containing a double bond in an unbranched carbon chain is changed from addition to substitution by operating at elevated temperatures. This substitution, unlike the induced reaction described in the first paper (4), occurs exclusively into the olefin with the formation principally of allyl-type unsaturated monohalides. The optimum temperature ranges from 300°to 600°C ., depending on the nature of the olefin and halogen.Operating conditions have been examined in some detail so that the work can serve as a basis which will make this class of products easily available.ALTHOUGH it is known that the reaction between /A chlorine and olefins containing a tertiary carbon atom at the double bond leads predominantly to chlorine substitution in the allyl position, the only observation of formation of allyl-type chlorides from straight-chain olefins is that of Stewart and Weidenbaum (9). These investigators found pentenyl chlorides in the chlorination product of 2-pentene, but only in small amounts. In general, the main chlorination product of straight-chain olefin is the di-
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