Dicumyl peroxide is an
organic compound
Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...
with the formula (Me = CH
3). Classified as a
dialkyl peroxide, it is produced on a large scale industrially for use in
polymer chemistry
Polymer chemistry is a sub-discipline of chemistry that focuses on the structures, chemical synthesis, and chemical and physical properties of polymers and macromolecules. The principles and methods used within polymer chemistry are also applic ...
. It serves as an initiator and crosslinking agent in the production of
low density polyethylene
Low-density polyethylene (LDPE) is a thermoplastic made from the monomer ethylene. It was the first grade of polyethylene, produced in 1933 by John C. Swallow and M.W Perrin who were working for Imperial Chemical Industries (ICI) using a high pr ...
.
Production
It is synthesized as a by-product in the
autoxidation
Autoxidation (sometimes auto-oxidation) refers to oxidations brought about by reactions with oxygen at normal temperatures, without the intervention of flame or electric spark. The term is usually used to describe the gradual degradation of organi ...
of
cumene
Cumene (isopropylbenzene) is an organic compound that contains a benzene ring with an isopropyl substituent. It is a constituent of crude oil and refined fuels. It is a flammable colorless liquid that has a boiling point of 152 °C. Near ...
, which mainly affords
cumene hydroperoxide
Cumene hydroperoxide is the organic compound with the formula C6H5C(CH3)2OOH; this oily liquid is classified as an organic hydroperoxide. Products of decomposition of cumene hydroperoxide are methylstyrene, acetophenone, and 2-phenylpropan-2- ...
. Alternatively, it can be produced by the addition of
hydrogen peroxide
Hydrogen peroxide is a chemical compound with the formula . In its pure form, it is a very pale blue liquid that is slightly more viscosity, viscous than Properties of water, water. It is used as an oxidizer, bleaching agent, and antiseptic, usua ...
to
α-methylstyrene
α-Methylstyrene (AMS) is an organic compound with the formula C6H5C(CH3)=CH2. It is a colorless oil.
Synthesis and reactions
AMS is formed as a by-product of the cumene process. In this procedure, cumene is converted to its radical, through a r ...
.
Of the ca. 60,000 ton/y production of dialkyl peroxides, dicumyl peroxide is dominant.
[{{Ullmann, first1=Herbert, last1=Klenk, first2=Peter H., last2=Götz, first3=Rainer, last3=Siegmeier, first4=Wilfried, last4=Mayr, title=Peroxy Compounds, Organic, doi=10.1002/14356007.a19_199.pub2]
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
Organic peroxides