Diacetyl peroxide explained

Diacetyl peroxide is the organic peroxide with the formula (CH3CO2)2. It is a white solid or oily liquid with a sharp odor. As with a number of organic peroxides, it is explosive.[1] It is often used as a solution, e.g., in dimethyl phthalate.

History

Diacetyl peroxide was discovered in 1858 by Benjamin Collins Brodie,[2] who obtained the compound by treating glacial acetic acid with barium peroxide in anhydrous diethyl ether.[3]

Preparation

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

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.[5] [6]

The threshold quantity for Process Safety Management per Occupational Safety and Health Administration 1910.119 is 5000lb if the concentration of the diacetyl peroxide solution is greater than 70%.[7]

There have been reports of detonation of the pure material. The 25% solution also has explosive potential.[8] The crystalline peroxide is especially shock sensitive and a high explosion risk.[9] [6]

Safety

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.[10] [11] [12] [13]

References

Notes and References

  1. Book: Sax, N. I.. Dangerous Properties of Industrial Materials. registration. 4th. New York, NY. Van Nostrand Reinhold. 1975. 357. 9780442273682.
  2. 30 March 1881 . Anniversary Meeting. Journal of the Chemical Society, Transactions . 39 . 177–201 . 10.1039/CT8813900177 . 17 February 2022.
  3. Brodie . Benjamin Collins . 1 January 1859 . I. Note on the formation of the peroxides of the radicals of the organic acids. Proceedings of the Royal Society of London . 9 . 361–365 . 10.1098/rspl.1857.0087 . 97728118 . free .
  4. Chemical Safety: Synthesis Procedure. Chemical & Engineering News. 89. 2. 2. 2011-01-10.
  5. Chemical Safety: Synthesis Procedure . . 89 . 2 . 2 . 2011-01-10.
  6. Book: National Fire Protection Association. Fire Protection Guide on Hazardous Materials. 7th. Boston, MA. National Fire Protection Association. 1978. 49–110.
  7. Web site: 1910.119 App A - List of Highly Hazardous Chemicals, Toxics and Reactives (Mandatory) | Occupational Safety and Health Administration.
  8. Book: National Research Council. Prudent Practices for Handling Hazardous Chemicals in Laboratories. Washington, DC. National Academy Press. 1981. 106.
  9. Book: Bretherick, L.. Handbook of Reactive Chemical Hazards. 4th. Boston, MA. Butterworth-Heinemann. 1990. 453, 1104.
  10. Book: National Research Council. United States National Research Council. Prudent Practices for Handling Hazardous Chemicals in Laboratories. Washington, DC. National Academy Press. 1981. 106.
  11. Book: International Labour Office. Encyclopaedia of Occupational Health and Safety. 4th. 1–4. 1998. Geneva. International Labour Office. 104.349.
  12. Book: Clayton. G.D.. F.E.. Clayton. Patty's Industrial Hygiene and Toxicology. 2A–2F. 4th. New York, NY. John Wiley & Sons. 1993–1994. 545.
  13. Book: Mackison. F. W.. R. S.. Stricoff. L. J. Jr. Partridge. NIOSH/OSHA - Occupational Health Guidelines for Chemical Hazards. DHHS(NIOSH) Publication No. 81–123. Washington, DC. U.S. Government Printing Office. Jan 1981. 1.

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