Diacetyl peroxide

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Diacetyl peroxide
Diacetyl peroxide.svg
Diacetyl-peroxide-3D-balls.png
Names
Preferred IUPAC name
Acetic peroxyanhydride [1]
Other names
acetyl peroxide (2:1); diacetyl peroxide; Peroxide, diacetyl; ethanoyl peroxide; acetyl ethaneperoxoate; ethanoyl ethane peroxoate; peracetic acid acetyl ester
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.409 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-748-8
PubChem CID
UNII
UN number 2084
  • InChI=1S/C4H6O4/c1-3(5)7-8-4(2)6/h1-2H3 Yes check.svgY
    Key: ZQMIGQNCOMNODD-UHFFFAOYSA-N Yes check.svgY
  • O=C(OOC(=O)C)C
Properties
C4H6O4
Molar mass 118.088 g·mol−1
AppearanceColorless crystals [2]
Density 1.163 g/cm3 [2]
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 [3]
slight in cold water [2]
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
Explosive, oxidizer
NFPA 704 (fire diamond)
NFPA 704.svgHealth 1: Exposure would cause irritation but only minor residual injury. E.g. turpentineFlammability 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 fuelInstability 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g. nitroglycerinSpecial hazards (white): no code
1
2
4
Flash point 32.2 °C (90.0 °F; 305.3 K) (45 °C [113 °F; 318 K] [4] )
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).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Diacetyl peroxide is the organic peroxide with the formula (CH3CO2)2. It is a white solid or oily liquid with a sharp odor. [4] As with a number of organic peroxides, it is explosive. [5] It is often used as a solution, e.g., in dimethyl phthalate. [2]

Contents

History

Diacetyl peroxide was discovered in 1858 by Benjamin Collins Brodie, [6] who obtained the compound by treating glacial acetic acid with barium peroxide in anhydrous diethyl ether. [7]

Preparation

Diacetyl peroxide forms upon combining hydrogen peroxide and excess acetic anhydride. Peracetic acid is an intermediate. [8]

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. [8] [9] [2]

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%. [10]

There have been reports of detonation of the pure material. The 25% solution also has explosive potential. [11] The crystalline peroxide is especially shock sensitive and a high explosion risk. [12] [9]

Safety

Organic peroxides are all prone to exothermic decomposition, potentially leading to explosions and fire. [13]

Contact with liquid causes irritation of the exposed area. If ingested, it irritates the mouth and stomach. [14] [15] [16] [17]

Related Research Articles

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Butanone, also known as methyl ethyl ketone (MEK) or ethyl methyl ketone, is an organic compound with the formula CH3C(O)CH2CH3. This colorless liquid ketone has a sharp, sweet odor reminiscent of acetone. It is produced industrially on a large scale, but occurs in nature only in trace amounts. It is partially soluble in water, and is commonly used as an industrial solvent. It is an isomer of another solvent, tetrahydrofuran.

<span class="mw-page-title-main">Dimethylaniline</span> Chemical compound

N,N-Dimethylaniline (DMA) is an organic chemical compound, a substituted derivative of aniline. It is a tertiary amine, featuring a dimethylamino group attached to a phenyl group. This oily liquid is colourless when pure, but commercial samples are often yellow. It is an important precursor to dyes such as crystal violet.

<span class="mw-page-title-main">Tetrahydrofuran</span> Cyclic chemical compound, (CH₂)₄O

Tetrahydrofuran (THF), or oxolane, is an organic compound with the formula (CH2)4O. The compound is classified as heterocyclic compound, specifically a cyclic ether. It is a colorless, water-miscible organic liquid with low viscosity. It is mainly used as a precursor to polymers. Being polar and having a wide liquid range, THF is a versatile solvent. It is an isomer of another solvent, butanone.

<span class="mw-page-title-main">Phthalic anhydride</span> Chemical compound

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<span class="mw-page-title-main">Acetic anhydride</span> Organic compound with formula (CH₃CO)₂O

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<span class="mw-page-title-main">Diisopropyl ether</span> Chemical compound

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<span class="mw-page-title-main">Hexamethylphosphoramide</span> Chemical compound

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n-Butyl acetate is an organic compound with the formula CH3CO2(CH2)3CH3. A colorless, flammable liquid, it is the ester derived from n-butanol and acetic acid. It is found in many types of fruit, where it imparts characteristic flavors and has a sweet smell of banana or apple. It is used as an industrial solvent.

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<span class="mw-page-title-main">1-Propanol</span> Primary alcohol compound

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<i>sec</i>-Butyl acetate Chemical compound

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References

  1. ↑ International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 829. doi:10.1039/9781849733069. ISBN   978-0-85404-182-4.
  2. 1 2 3 4 5 Lewis, R. J. Sr, ed. (1997). Hawley's Condensed Chemical Dictionary (13th ed.). New York, NY: John Wiley & Sons. p. 13.
  3. ↑ Lide, D. R., ed. (1998–1999). CRC Handbook of Chemistry and Physics (79th ed.). Boca Raton, Florida: CRC Press. pp. 3–250.
  4. 1 2 "Acetyl peroxide" (PDF). NJ.gov.
  5. ↑ Sax, N. I. (1975). Dangerous Properties of Industrial Materials (4th ed.). New York, NY: Van Nostrand Reinhold. p.  357. ISBN   9780442273682.
  6. ↑ "Anniversary Meeting". Journal of the Chemical Society, Transactions. 39: 177–201. 30 March 1881. doi:10.1039/CT8813900177 . Retrieved 17 February 2022.
  7. ↑ 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. doi: 10.1098/rspl.1857.0087 . S2CID   97728118.
  8. 1 2 "Chemical Safety: Synthesis Procedure". Chemical & Engineering News . 89 (2): 2. 2011-01-10.
  9. 1 2 National Fire Protection Association (1978). Fire Protection Guide on Hazardous Materials (7th ed.). Boston, MA: National Fire Protection Association. pp. 49–110.
  10. ↑ "1910.119 App A - List of Highly Hazardous Chemicals, Toxics and Reactives (Mandatory) | Occupational Safety and Health Administration".
  11. ↑ National Research Council (1981). Prudent Practices for Handling Hazardous Chemicals in Laboratories. Washington, DC: National Academy Press. p. 106.
  12. ↑ Bretherick, L. (1990). Handbook of Reactive Chemical Hazards (4th ed.). Boston, MA: Butterworth-Heinemann. pp. 453, 1104.
  13. ↑ Klenk, Herbert; Götz, Peter H.; Siegmeier, Rainer; Mayr, Wilfried. "Peroxy Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_199.pub2. ISBN   978-3527306732.
  14. ↑ National Research Council (1981). Prudent Practices for Handling Hazardous Chemicals in Laboratories. Washington, DC: National Academy Press. p. 106.
  15. ↑ International Labour Office (1998). Encyclopaedia of Occupational Health and Safety. Vol. 1–4 (4th ed.). Geneva: International Labour Office. p. 104.349.
  16. ↑ Clayton, G.D.; Clayton, F.E., eds. (1993–1994). Patty's Industrial Hygiene and Toxicology. Vol. 2A–2F (4th ed.). New York, NY: John Wiley & Sons. p. 545.
  17. ↑ 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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