Methyl ethyl ketone peroxide

Methyl ethyl ketone peroxide (MEKP) is an organic peroxide, a high explosive similar to acetone peroxide. MEKP is a colorless, oily liquid whereas acetone peroxide is a white powder at STP; MEKP is slightly less sensitive to shock and temperature, and more stable in storage. Depending on the experimental conditions, several different adducts of methyl ethyl ketone and hydrogen peroxide are known. The first to be reported was a cyclic dimer, C8H16O4, in 1906.[3] Later studies found that a linear dimer is the most prevalent in the mixture of products typically obtained,[4] and this is the form that is typically quoted in the commercially available material from chemical supply companies.[5]

Methyl ethyl ketone peroxide
Names
Preferred IUPAC name
2,2'-Peroxydi(butane-2-peroxol)
Other names
2-[(2-Hydroperoxybutan-2-yl)peroxy]butane-2-peroxol
2-Hydroperoxy-2-[(2-hydroperoxybutan-2-yl)peroxy]butane
Ketonox
Mepox
Thermacure
Identifiers
3D model (JSmol)
1759757
ChemSpider
ECHA InfoCard 100.014.238
EC Number
  • 215-661-2
MeSH Methyl+ethyl+ketone+peroxide
UNII
UN number 3105
Properties
C8H18O6
Molar mass 210.226 g·mol−1
Appearance Colorless liquid
Density 1.170 g cm−3
Boiling point Decomposition beyond 80 °C (176 °F) [1]
Soluble[2]
Explosive data
Shock sensitivity High
Detonation velocity 5200 m/s
RE factor 0.9
Hazards
Main hazards Explosive, Toxic
GHS pictograms
GHS Signal word Danger
H202, H205, H241, H300, H315, H318, H335
P102, P220, P243, P250, P261, P264, P280, P283, P370+380, P372, P404
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 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformReactivity code 4: Readily capable of detonation or explosive decomposition at normal temperatures and pressures. E.g. nitroglycerinSpecial hazards (white): no code
2
2
4
Flash point 75 °C (167 °F; 348 K)[1]
NIOSH (US health exposure limits):
PEL (Permissible)
 none[2]
REL (Recommended)
 C 0.2 ppm (1.5 mg/m3)[2]
IDLH (Immediate danger)
 N.D.[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)
Infobox references

Dilute solutions of 30 to 40% MEKP are used in industry and by hobbyists as the catalyst which initiates the crosslinking of unsaturated polyester resins used in fiberglass, and casting. For this application, MEKP is dissolved in dimethyl phthalate, cyclohexane peroxide, or diallyl phthalate to reduce sensitivity to shock. Benzoyl peroxide can be used for the same purpose.

MEKP is a severe skin irritant and can cause progressive corrosive damage or blindness.

See also

Notes
  1. Record of 2-Butanone peroxide in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 10 March 2013.
  2. NIOSH Pocket Guide to Chemical Hazards. "#0416". National Institute for Occupational Safety and Health (NIOSH).
  3. Pastureau, P. (1907). "Le superoxyde de la méthyléthylcétone". Comptes Rendus. 144 (2): 90–93.
  4. Milas, N. A.; Golubović, A. (1959). "Studies in Organic Peroxides. XXV. Preparation, Separation and Identification of Peroxides Derived from Methyl Ethyl Ketone and Hydrogen Peroxide". Journal of the American Chemical Society. 81 (21): 5824–5826. doi:10.1021/ja01530a068.
  5. "2-Butanone peroxide". Sigma-Aldrich. Retrieved 5 December 2011.
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