Methyl ethyl ketone peroxide

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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 Edit this at Wikidata
EC Number
  • 215-661-2
MeSH Methyl+ethyl+ketone+peroxide
UNII
UN number 3105
  • InChI=1S/C8H18O6/c1-5-7(3,11-9)13-14-8(4,6-2)12-10/h9-10H,5-6H2,1-4H3 ☒N
    Key: WFUGQJXVXHBTEM-UHFFFAOYSA-N ☒N
  • CCC(C)(OO)OOC(C)(CC)OO
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)[2]
Soluble[1]
Explosive data
Shock sensitivity High
Detonation velocity 5200 m/s
RE factor
 0.9
Hazards
Occupational safety and health (OHS/OSH):
Main hazards
 Explosive, Toxic
GHS labelling:
GHS01: Explosive GHS07: Exclamation mark GHS08: Health hazard
Danger
H202, H205, H241, H300, H315, H318, H335
P102, P220, P243, P250, P261, P264, P280, P283, P370+P380, P372, P404
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 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
2
2
4
Flash point 75 °C (167 °F; 348 K)[2]
NIOSH (US health exposure limits):
PEL (Permissible)
 none[1]
REL (Recommended)
 C 0.2 ppm (1.5 mg/m3)[1]
IDLH
(Immediate danger)
 N.D.[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Methyl ethyl ketone peroxide (MEKP) is an

organic peroxide with the formula [(CH3)(C2H5)C(O2H)]2O2. MEKP is a colorless oily liquid. It is widely used in vulcanization (crosslinking) of polymers.[3]

It is derived from the reaction of

methyl ethyl ketone and hydrogen peroxide under acidic conditions. Several products result from this reaction including a cyclic dimer.[4] The linear dimer, the topic of this article, is the most prevalent.[5] and this is the form that is typically quoted in the commercially available material.[6]

unsaturated polyester resins used in fiberglass, and casting. For this application, MEKP often is dissolved in a phlegmatizer such as dimethyl phthalate, cyclohexane peroxide,[clarification needed] or diallyl phthalate [de] to reduce sensitivity to shock. Benzoyl peroxide can be used for the same purpose.[citation needed
]

Safety

Whereas acetone peroxide is a white powder at STP, MEKP is slightly less sensitive to shock and temperature, and more stable in storage.

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

The volatile decomposition products of MEKP can contribute to the formation of vapor-phase explosions. Ensuring safe storage is important, and the maximum storage temperature should be limited to below 30 °C.[7]

Notes

  1. ^ a b c d NIOSH Pocket Guide to Chemical Hazards. "#0416". National Institute for Occupational Safety and Health (NIOSH).
  2. ^ a b Record of 2-Butanone peroxide in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 10 March 2013.
  3. ISBN 978-3527306732
    .
  4. ^ Pastureau, P. (1907). "Le superoxyde de la méthyléthylcétone". Comptes Rendus. 144 (2): 90–93.
  5. doi:10.1021/ja01530a068
    .
  6. ^ "2-Butanone peroxide". Sigma-Aldrich. Retrieved 5 December 2011.
  7. ^ "Methyl Ethyl Ketone Peroxide (MEKP): Production And Uses". 19 May 2023. Retrieved 29 July 2023.

External links

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