Dicumyl peroxide

Dicumyl peroxide
Names
	Preferred IUPAC name 1,1′-[peroxydi(propane-2,2-diyl)]dibenzene
	Other names DCUP
Identifiers
CAS Number	80-43-3 ;
3D model (JSmol)	Interactive image;
ChEMBL	ChEMBL1519055;
ChemSpider	6389;
ECHA InfoCard	100.001.164
EC Number	201-279-3;
PubChem CID	6641;
RTECS number	SD8150000;
UNII	M51X2J0U9D;
UN number	3110
CompTox Dashboard (EPA)	DTXSID1025017 ;
	InChI 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;
	SMILES CC(C)(C1=CC=CC=C1)OOC(C)(C)C2=CC=CC=C2;
Properties
Chemical formula	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:
Pictograms
Signal word	Danger
Hazard statements	H242, H315, H319, H360, H411
Precautionary statements	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

Dicumyl peroxide is an organic compound with the formula (C₆H₅CMe₂O)₂ (Me = CH₃). Classified as a dialkyl peroxide, it is produced on a large scale industrially for use in polymer chemistry. It serves as an initiator and crosslinking agent in the production of low density polyethylene.^[2]

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 approximately 60,000 ton/y production of dialkyl peroxides, dicumyl peroxide is dominant.^[3]

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

^ "Dicumyl peroxide". pubchem.ncbi.nlm.nih.gov.
^ Stevens, Malcolm P. (1993). "Polymer Additives: III. Surface Property and Processing Modifiers". Journal of Chemical Education. 70 (9): 713. Bibcode:1993JChEd..70..713S. doi:10.1021/ed070p713.
^ 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 978-3-527-30673-2.

[1] "Dicumyl peroxide". pubchem.ncbi.nlm.nih.gov.

[2] Stevens, Malcolm P. (1993). "Polymer Additives: III. Surface Property and Processing Modifiers". Journal of Chemical Education. 70 (9): 713. Bibcode:1993JChEd..70..713S. doi:10.1021/ed070p713.

[Ullmann-3] 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 978-3-527-30673-2.

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