Dicumyl peroxide

Dicumyl peroxide is an organic compound with the formula (C6H5CMe2O)2 (Me = CH3). Classified as a dialky peroxide, it is produced on a large scale industrially for use as an initiator for the production of low density polyethylene.

Dicumyl peroxide
Names
Other names
DCUP
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.001.164
EC Number
  • 201-279-3
RTECS number
  • SD8150000
UNII
UN number 3110
  • InChI=1S/C18H22O2/c1-17(2,15-11-7-5-8-12-15)19-20-18(3,4)16-13-9-6-10-14-16/h5-14H,1-4H3
    Key: XMNIXWIUMCBBBL-UHFFFAOYSA-N
  • CC(C)(C1=CC=CC=C1)OOC(C)(C)C2=CC=CC=C2
Properties
C18H22O2
Molar mass 270.372 g·mol−1
Appearance colorless solid
Density 1.062 g/cm3
Melting point 39 °C (102 °F; 312 K)
Hazards
GHS labelling:[1]
GHS02: FlammableGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
Danger
H242, H315, H319, H360, H411
P203, P210, P234, P240, P264, P264+P265, P273, P280, P302+P352, P305+P351+P338, P318, P321, P332+P317, P337+P317, P362+P364, P370+P378, P391, P403, P405, P410, P411, P420, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Production

It is synthesized as a by-product in the autoxidation of cumene, which mainly affords cumene hydroperoxide. Alternatively, it can be produced by the addition of hydrogen peroxide to α-methylstyrene.

Of the ca. 60,000 ton/y production of dialkyl peroxides, dicumyl peroxide is dominant.[2]

Properties

Dicumyl peroxide is relatively stable compound owing to the steric protection provided by the several substituents adjacent to the peroxide group. Upon heating, it breaks down by homolysis of the relatively weak O-O bond.

References
  1. "Dicumyl peroxide". pubchem.ncbi.nlm.nih.gov.
  2. 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.


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