Dicumyl peroxide

Dicumyl peroxide
Names
Other names
DCUP
Identifiers
CAS Number
  • 80-43-3 checkY
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL1519055
ChemSpider
  • 6389
ECHA InfoCard 100.001.164 Edit this at Wikidata
EC Number
  • 201-279-3
PubChem CID
  • 6641
RTECS number
  • SD8150000
UNII
  • M51X2J0U9D
UN number 3110
CompTox Dashboard (EPA)
  • DTXSID1025017 Edit this at Wikidata
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
  • 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:[1]
Pictograms
 GHS02: FlammableGHS07: Exclamation markGHS08: Health hazardGHS09: Environmental hazard
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
Chemical compound

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 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 ca. 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

  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.
  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 978-3527306732.


  • v
  • t
  • e