Acetone peroxide is a very dangerous explosive, easily detonated by mild heating, friction or shock. It appears in the form of small white crystals.

acetone peroxide

This compound forms from the mixture of hydrogen peroxide, acetone and hydrochloric or sulphuric (and maybe any other) acid. The acid, however, is only a catalyst in the reaction.

formation of trimmer acetone peroxide

I'm curious why the acid is required for the reaction to happen. Is it actually necessary? Does the acid change during the reaction?

  • $\begingroup$ May I ask which program you used to generate the first image? (Great question too!) $\endgroup$
    – user15489
    Apr 29 '15 at 7:18
  • $\begingroup$ @santiago Sorry to disappoint you, but that images come from wikipedia. According to it's metadata, it was created using Adobe ImageReady. I have doubts that this is the actual program that generated the image. $\endgroup$ Apr 29 '15 at 7:53
  • 1
    $\begingroup$ Ah, no disappointment, a treasure found on the wilderness of Wikipedia $\endgroup$
    – user15489
    Apr 29 '15 at 7:55
  • 1
    $\begingroup$ Material Studio can be used to generate these type of images $\endgroup$
    – Gowtham
    Apr 29 '15 at 9:05
  • $\begingroup$ You asked whether the acid changed, well no catalyst means it promotes the reaction and does not change itself $\endgroup$
    – user22640
    Nov 6 '15 at 18:00

The role of the acid in this reaction (really a polymerization) is two-fold. First, it protonates the acetone carbonyl oxygen making the acetone carbonyl carbon more electrophilic. This speeds up the rate of attack by the nucleophilic hydrogen peroxide (or other hydroperoxides formed later in the reaction) on this carbon. Second, the acid also protonates hydroxyl groups in intermediates formed later in the reaction. This makes them better leaving groups and allows nucleophiles like hydrogen peroxide or other hydroperoxides formed in the reaction to displace them.

The acid is a catalyst, the more acid the faster the reaction, but the reaction will proceed, albeit more slowly, without the acid. Any proton acid can be used, but as expected, the stronger the acid, the faster the reaction.

Here are links to two articles on the subject (reference 1, reference 2) along with a diagram of the proposed reaction mechanism.

enter image description here


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