Methyl ethyl ketone peroxide

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
CAS Number	1338-23-4 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	1759757
ChemSpider	2905622 ;
ECHA InfoCard	100.014.238
EC Number	215-661-2;
MeSH	Methyl+ethyl+ketone+peroxide
PubChem CID	3672772;
UNII	W2545087UL ;
UN number	3105
CompTox Dashboard (EPA)	DTXSID1024671 ;
	InChI InChI=1S/C8H18O6/c1-5-7(3,11-9)13-14-8(4,6-2)12-10/h9-10H,5-6H2,1-4H3 Key: WFUGQJXVXHBTEM-UHFFFAOYSA-N ;
	SMILES CCC(C)(OO)OOC(C)(CC)OO;
Properties
Chemical formula	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)
Solubility in water	Soluble
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:
Pictograms
Signal word	Danger
Hazard statements	H202, H205, H241, H300, H315, H318, H335
Precautionary statements	P102, P220, P243, P250, P261, P264, P280, P283, P370+P380, P372, P404
NFPA 704 (fire diamond)	2 2 4
Flash point	75 °C (167 °F; 348 K)
	NIOSH (US health exposure limits):
PEL (Permissible)	none
REL (Recommended)	C 0.2 ppm (1.5 mg/m3)
IDLH (Immediate danger)	N.D.
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

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]

Solutions of 30 to 40% MEKP are used in industry and by hobbyists as catalyst to initiate the crosslinking of 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

^ ^a ^b ^c ^d NIOSH Pocket Guide to Chemical Hazards. "#0416". National Institute for Occupational Safety and Health (NIOSH).
^ ^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.
^ Klenk, Herbert; Götz, Peter H.; Siegmeier, Rainer; Mayr, Wilfried (2000). "Peroxy Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_199. ISBN 978-3527306732.
^ Pastureau, P. (1907). "Le superoxyde de la méthyléthylcétone". Comptes Rendus. 144 (2): 90–93.
^ 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.
^ "2-Butanone peroxide". Sigma-Aldrich. Retrieved 5 December 2011.
^ "Methyl Ethyl Ketone Peroxide (MEKP): Production And Uses". 19 May 2023. Retrieved 29 July 2023.

External links

Media related to Methyl ethyl ketone peroxide at Wikimedia Commons
CDC - NIOSH Pocket Guide to Chemical Hazards
The Register: Mass murder in the skies: was the plot feasible?
New York Times: Details Emerge in British Terror Case
The Free Information Society: HMTD Synthesis Archived 3 March 2016 at the Wayback Machine
How MEKP cures Unsaturated Polyester Resin (video animation)

[PGCH-1] NIOSH Pocket Guide to Chemical Hazards. "#0416". National Institute for Occupational Safety and Health (NIOSH).

[GESTIS-2] Record of 2-Butanone peroxide in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 10 March 2013.

[3] Klenk, Herbert; Götz, Peter H.; Siegmeier, Rainer; Mayr, Wilfried (2000). "Peroxy Compounds, Organic". Ullmann's Encyclopedia of Industrial Chemistry. Weinheim: Wiley-VCH. doi:10.1002/14356007.a19_199. ISBN 978-3527306732.

[4] Pastureau, P. (1907). "Le superoxyde de la méthyléthylcétone". Comptes Rendus. 144 (2): 90–93.

[5] 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.

[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.

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