Atmosphere dialkyl peroxides

When ethers are stored in the presence of atmospheric oxygen, they slowly oxidize to produce hydroperoxides and dialkyl peroxides, both of which are explosive. Such a spontaneous oxidation by atmospheric oxygen is called an autoxidation. 

The reaction follows a free radical mechanism and gives a hydroperoxide a compound of the type ROOH Hydroperoxides tend to be unstable and shock sensitive On stand mg they form related peroxidic derivatives which are also prone to violent decomposi tion Air oxidation leads to peroxides within a few days if ethers are even briefly exposed to atmospheric oxygen For this reason one should never use old bottles of dialkyl ethers and extreme care must be exercised m their disposal... 

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