Diacetyl peroxide

Diacetyl peroxide is the organic peroxide with the formula (CH3CO2)2. It is a white solid or oily liquid with a sharp odor.[3] Since the pure material poses an explosion hazard, it is often used as a solution, e.g., in dimethyl phthalate as a solvent.[1]

Diacetyl peroxide
Names
IUPAC name
acetyl ethaneperoxoate
Other names
acetylperoxide; diacetyl peroxide; Peroxide, diacetyl; ethanoyl peroxide; acetyl ethaneperoxoate; ethanoyl ethaneperoxoate; peracetic acid acetyl ester
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.409
EC Number
  • 203-748-8
UNII
UN number 2084
Properties
C4H6O4
Molar mass 118.088 g·mol−1
Appearance Colorless crystals[1]
Density 1.163 g/cm3[1]
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[2]
slight in cold water [1]
Hazards
Main hazards Explosive
NFPA 704 (fire diamond)
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g. diesel fuelHealth code 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineReactivity code 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g. nitroglycerinSpecial hazards (white): no code
2
1
4
Flash point 32.2 °C (90.0 °F; 305.3 K) (45 °C [113 °F; 318 K][3])
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).
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Infobox references

Preparation

Diacetyl peroxide forms upon combining hydrogen peroxide and excess acetic anhydride. Peracetic acid is an intermediate.[4]

Safety

Organic peroxides are typically explosive since they contain both the oxidizer, the O-O bond, and reducing agents, the C-C and C-H bonds.[5]

It is shock sensitive and explosive.[6][7][1]

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%.[8]

There have been reports of detonation of the pure material. The 25% solution also has explosive potential.[9] The crystalline peroxide is especially shock sensitive and a high explosion risk.[10][7]

Health hazards

Contact with liquid causes irritation of eyes and skin. If ingested, irritates mouth and stomach.[11][12][13][14]

References
  1. Lewis, R. J., Sr, ed. (1997). Hawley's Condensed Chemical Dictionary (13th ed.). New York, NY: John Wiley & Sons. p. 13.
  2. Lide, D. R., ed. (1998–1999). CRC Handbook of Chemistry and Physics (79th ed.). Boca Raton, Florida: CRC Press. pp. 3–250.
  3. "Acetyl peroxide" (PDF). NJ.gov.
  4. "Chemical Safety: Synthesis Procedure". Chemical & Engineering News. 89 (2): 2. 2011-01-10.
  5. Sax, N. I. (1975). Dangerous Properties of Industrial Materials (4th ed.). New York, NY: Van Nostrand Reinhold. p. 357.
  6. "Chemical Safety: Synthesis Procedure". Chemical & Engineering News. 89 (2): 2. 2011-01-10.
  7. National Fire Protection Association (1978). Fire Protection Guide on Hazardous Materials (7th ed.). Boston, MA: National Fire Protection Association. pp. 49–110.
  9. National Research Council (1981). Prudent Practices for Handling Hazardous Chemicals in Laboratories. Washington, DC: National Academy Press. p. 106.
  10. Bretherick, L. (1990). Handbook of Reactive Chemical Hazards (4th ed.). Boston, MA: Butterworth-Heinemann. pp. 453, 1104.
  11. National Research Council (1981). Prudent Practices for Handling Hazardous Chemicals in Laboratories. Washington, DC: National Academy Press. p. 106.
  12. International Labour Office (1998). Encyclopaedia of Occupational Health and Safety. 1–4 (4th ed.). Geneva: International Labour Office. p. 104.349.
  13. Clayton, G.D.; Clayton, F.E., eds. (1993–1994). Patty's Industrial Hygiene and Toxicology. 2A–2F (4th ed.). New York, NY: John Wiley & Sons. p. 545.
  14. Mackison, F. W.; Stricoff, R. S.; Partridge, L. J., Jr, eds. (Jan 1981). NIOSH/OSHA - Occupational Health Guidelines for Chemical Hazards. DHHS(NIOSH) Publication No. 81–123. Washington, DC: U.S. Government Printing Office. p. 1.
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