Diacetyl peroxide

Diacetyl peroxide
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
PubChem	8040
ChemSpider	7749 Y
EC number	203-748-8
UN number	2084
Jmol-3D images	Image 1
SMILES O=C(OOC(=O)C)C
InChI InChI=1S/C4H6O4/c1-3(5)7-8-4(2)6/h1-2H3 Y Key: ZQMIGQNCOMNODD-UHFFFAOYSA-N Y
Properties
Molecular formula	C4H6O4
Molar mass	118.09 g mol−1
Appearance	Colorless crystals [1]
Density	1.163 g/cm3[2]
Melting point	30 °C, 303 K, 86 °F
Boiling point	121.4° at 760mmHg, 63° at 21mmHg [3]
Solubility in water	slight in cold water [4]
Hazards
Main hazards	Explosive
NFPA 704	2 1 4
Flash point	32.2°C (45°C [5])
Explosive data
Shock sensitivity	Very high / moderate when wet
Friction sensitivity	Very high / moderate when wet
Explosive velocity	m/s ft/s miles per second
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Diacetyl peroxide^[6] as a commercial product is a colourless liquid with a pungent odour. As a solid it is crystalline (sand like) with a sharp odor. ^[7] The commercial product consists of a 25% solution of acetyl peroxide in dimethyl phthalate. ^[8] It is an organic peroxide and a carboxylic peracid derivative. It sinks in water.

Reactivity

Peroxides, such as diacetyl peroxide, are good oxidizing agents.

Organic compounds can ignite on contact with concentrated peroxides.

Strongly reduced material such as sulfides, nitrides, and hydrides may react explosively with peroxides.

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. ^[9] Pure(100%)material is a severe explosion hazard. It should not be stored after preparation, nor heated above 30 C. ^[10]

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. ^[11] 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. ^[12] Application of fluorine to aqueous sodium acetate solution caused an explosion involving the formation of diacetyl peroxide. ^[13] 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. ^[14]

Health hazards

Contact with liquid causes irritation of eyes and skin. If ingested, irritates mouth and stomach.^{[15] [16] [17] [18]}

Fire hazards

Behavior in Fire: May explode. Burns with accelerating intensity. ^[19]

The threshold quantity for Process Safety Management per Occupational Safety and Health Administration 1910.119 is 5,000 lbs if the concentration of the diacetyl peroxide solution is greater than 70%. ^[20]

References

1. ^ Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 13th ed. New York, NY: John Wiley & Sons, Inc. 1997., p. 13
2. ^ Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 13th ed. New York, NY: John Wiley & Sons, Inc. 1997., p. 13
3. ^ Lide, D.R. (ed.). CRC Handbook of Chemistry and Physics. 79th ed. Boca Raton, FL: CRC Press Inc., 1998-1999., p. 3-250
4. ^ Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 13th ed. New York, NY: John Wiley & Sons, Inc. 1997., p. 13
5. ^ Acetyl peroxide
6. ^ [1]
7. ^ Acetyl peroxide
8. ^ Lewis, R.J., Sr (Ed.). Hawley's Condensed Chemical Dictionary. 13th ed. New York, NY: John Wiley & Sons, Inc. 1997., p. 13
9. ^ Sax, N.I. Dangerous Properties of Industrial Materials. 4th ed. New York: Van Nostrand Reinhold, 1975., p. 357
10. ^ Hawley, G.G. The Condensed Chemical Dictionary. 9th ed. New York: Van Nostrand Reinhold Co., 1977., p. 10
11. ^ National Research Council. Prudent Practices for Handling Hazardous Chemicals in Laboratories. Washington, DC: National Academy Press, 1981., p. 106
12. ^ Bretherick, L. Handbook of Reactive Chemical Hazards. 4th ed. Boston, MA: Butterworth-Heinemann Ltd., 1990, p. 453
13. ^ Bretherick, L. Handbook of Reactive Chemical Hazards. 4th ed. Boston, MA: Butterworth-Heinemann Ltd., 1990, p. 1104
14. ^ National Fire Protection Association Fire Protection Guide on Hazardous Materials. 7th ed. Boston, Mass.: National Fire Protection Association, 1978., p. 491M-143
15. ^ National Research Council. Prudent Practices for Handling Hazardous Chemicals in Laboratories. Washington, DC: National Academy Press, 1981., p. 106
16. ^ International Labour Office. Encyclopaedia of Occupational Health and Safety. 4th edition, Volumes 1-4 1998. Geneva, Switzerland: International Labour Office, 1998., p. 104.349
17. ^ Clayton, G.D., F.E. Clayton (eds.) Patty's Industrial Hygiene and Toxicology. Volumes 2A, 2B, 2C, 2D, 2E, 2F: Toxicology. 4th ed. New York, NY: John Wiley & Sons Inc., 1993-1994., p. 545
18. ^ Mackison, F. W., R. S. Stricoff, and L. J. Partridge, Jr. (eds.). NIOSH/OSHA - Occupational Health Guidelines for Chemical Hazards. DHHS(NIOSH) Publication No. 81-123 (3 VOLS). Washington, DC: U.S. Government Printing Office, Jan. 1981., p. 1
19. ^ National Fire Protection Association. Fire Protection Guide on Hazardous Materials. 7th ed. Boston, Mass.: National Fire Protection Association, 1978., p. 49-110
20. ^ [2]

• Peroxide, diacetyl (C4H6O4) Landolt-Boernstein Substance/ Property Index
• Zuordnung der Organischen Peroxide zu Gefahrgruppen nach § 3 Abs. 1 (in German), Berufsgenossenschaft Handel und Warendistribution