Diacetyl peroxide is the

organic peroxide In organic chemistry, organic peroxides are organic compounds containing the peroxide functional group (). If the R′ is hydrogen, the compounds are called hydroperoxides, which are discussed in that article. The O−O bond of peroxides easily b ...

with the formula (CH₃CO₂)₂. It is a white solid or oily liquid with a sharp odor. As with a number of

s, it is explosive. It is often used as a solution, e.g., in dimethyl phthalate.

History

Diacetyl peroxide was discovered in 1858 by Benjamin Collins Brodie, who obtained the compound by treating

glacial acetic acid Acetic acid , systematically named ethanoic acid , is an acidic, colourless liquid and organic compound with the chemical formula (also written as , , or ). Vinegar is at least 4% acetic acid by volume, making acetic acid the main compone ...

with

barium peroxide Barium peroxide is an inorganic compound with the formula . This white solid (gray when impure) is one of the most common inorganic peroxides, and it was the first peroxide compound discovered. Being an oxidizer and giving a vivid green colour upo ...

in anhydrous

diethyl ether Diethyl ether, or simply ether, is an organic compound with the chemical formula , sometimes abbreviated as . It is a colourless, highly Volatility (chemistry), volatile, sweet-smelling ("ethereal odour"), extremely flammable liquid. It belongs ...

Preparation

Diacetyl peroxide forms upon combining

hydrogen peroxide Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscosity, viscous than Properties of water, water. It is used as an oxidizer, bleaching agent, and antiseptic, usua ...

and excess

acetic anhydride Acetic anhydride, or ethanoic anhydride, is the chemical compound with the chemical formula, formula . Commonly abbreviated , it is one the simplest organic acid anhydride, anhydrides of a carboxylic acid and is widely used in the production of c ...

Peracetic acid Peracetic acid (also known as peroxyacetic acid, or Percidine) is an organic compound with the formula CH3CO3H. This peroxy acid is a colorless liquid with a characteristic acrid odor reminiscent of acetic acid. It can be highly corrosive. Perac ...

is an intermediate.

Safety

Consisting of both an oxidizer, the O-O bond and reducing agents, the C-C and C-H bonds, diacetyl peroxide is shock sensitive and explosive. The threshold quantity for

Process Safety Management Process safety management (PSM) is a practice to manage business operations critical to process safety. It can be implemented using the established OSHA scheme or others made available by the EPA, AIChE's Center for Chemical Process Safety, or ...

per

Occupational Safety and Health Administration The Occupational Safety and Health Administration (OSHA; ) is a regulatory agency of the United States Department of Labor that originally had federal visitorial powers to inspect and examine workplaces. The United States Congress established ...

1910.119 is if the concentration of the diacetyl peroxide solution is greater than 70%. There have been reports of detonation of the pure material. The 25% solution also has explosive potential. The crystalline peroxide is especially shock sensitive and a high explosion risk. Organic peroxides are all prone to exothermic decomposition, potentially leading to explosions and fire. Contact with liquid causes irritation of the exposed area. If ingested, it irritates the mouth and stomach.

References

* *{{cite web, url=http://www.bge.de/asp2/dms.asp?url=%2Fuvv%2F58%2Fanh2.htm, title=Zuordnung der Organischen Peroxide zu Gefahrgruppen nach § 3 Abs. 1, language=German, website=Berufsgenossenschaft Handel und Warendistribution, access-date=2010-12-22, archive-date=2011-07-18, archive-url=https://web.archive.org/web/20110718202451/http://www.bge.de/asp2/dms.asp?url=%2Fuvv%2F58%2Fanh2.htm, url-status=dead Organic peroxides Explosive chemicals Liquid explosives Organic peroxide explosives Carbonyl compounds