Diacetyl peroxide

Diacetyl peroxide

Skeletal formula
Ball-and-stick model
Names
IUPAC name acetyl ethaneperoxoate
Other names acetylperoxide; diacetyl peroxide; Peroxide, diacetyl; ethanoyl peroxide; acetyl ethaneperoxoate; ethanoyl ethaneperoxoate; peracetic acid acetyl ester
Identifiers
CAS Number	110-22-5 Y
ChemSpider	7749 Y
EC Number	203-748-8
Jmol 3D model	Interactive image
PubChem	8040
UN number	2084
InChI InChI=1S/C4H6O4/c1-3(5)7-8-4(2)6/h1-2H3 Y Key: ZQMIGQNCOMNODD-UHFFFAOYSA-N Y
SMILES O=C(OOC(=O)C)C
Properties
Chemical formula	C4H6O4
Molar mass	118.09 g·mol−1
Appearance	Colorless crystals
Density	1.163 g/cm3
Melting point	30 °C (86 °F; 303 K)
Boiling point	121.4 °C (250.5 °F; 394.5 K) at 760 mmHg; 63 °C (145 °F; 336 K) at 21 mmHg
Solubility in water	slight in cold water
Vapor pressure	{{{value}}}
Explosive data
Shock sensitivity	Very high / moderate when wet
Friction sensitivity	Very high / moderate when wet
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Y verify (what is YN ?)
Infobox references

Diacetyl peroxide is an organic peroxide that is a crystalline, sandlike solid with a sharp odor. The commercial product consists of a 25% solution of acetyl peroxide in dimethyl phthalate.

Reactivity

Peroxides, such as diacetyl peroxide, are good oxidizing agents. Organic compounds can ignite on contact with concentrated peroxides, while strongly reduced material such as sulfides, nitrides, and hydrides may react explosively.

There are few chemical classes that do not at least produce heat when mixed with peroxides. Many produce explosions or generate gases (toxic and nontoxic). Generally, dilute solutions of peroxides (< 70%) are safe, but the presence of a catalyst (often a transition metal such as cobalt, iron, manganese, nickel, or vanadium) as an impurity may even then cause rapid decomposition, a buildup of heat, and even an explosion. Solutions of peroxides often become explosive when evaporated to dryness or near-dryness. Pure (100%) material is a severe explosion hazard. It should not be stored after preparation, nor heated above 30 °C (86 °F).

There have been reports of detonation of the pure material. The 25% solution also has explosive potential when inadvertent partial evaporation of a weak solution can create an explosive solution or a shock-sensitive crystalline material. It is essential to prevent the separation of the crystalline peroxide even in traces, since when dry, it is shock sensitive and is a high explosion risk. Application of fluorine to aqueous sodium acetate solution caused an explosion involving the formation of diacetyl peroxide. Dry acetyl peroxide is unpredictable. Five grains of it were removed from an ice chest and detonated violently. Solid acetyl peroxide in contact with ether or any volatile solvent may explode violently. Diacetyl peroxide can be formed when a mixture of hydrogen peroxide, and excess acetic anhydride reacts with one of the reaction products peracetic acid.

Health hazards

Contact with liquid causes irritation of eyes and skin. If ingested, irritates mouth and stomach.

Fire hazards

This compound may explode in a fire, and burn with accelerating intensity.

The threshold quantity for Process Safety Management per Occupational Safety and Health Administration 1910.119 is 5,000 lb (2,300 kg) if the concentration of the diacetyl peroxide solution is greater than 70%.