Phenacyl chloride is a substituted
acetophenone. It is a useful building block in
organic chemistry. Apart from that, it has been historically used as a
riot control agent, where it is designated
CN.
Preparation
Phenacyl chloride is readily available commercially. It may be synthesized by the
Friedel-Crafts acylation of
benzene using
chloroacetyl chloride, with an
aluminium chloride catalyst:
[1]
Riot control agent
It was investigated, but not used, during the
First and
Second World Wars.
Because of its significantly greater toxicity,
[2] it has largely been supplanted by
CS gas. Even though CN is still supplied to
paramilitary and police forces in a small pressurized aerosol known as “
Mace” or
tear gas, its use is falling as
pepper spray both works and disperses more quickly than CN.
The term "Mace" came into being because it was the brand-name invented by one of the first American manufacturers of CN aerosol sprays. Subsequently, Mace became
synonymous with tear-gas sprays in the same way that
Kleenex has become strongly associated with
tissue papers (a phenomenon known as a
genericized trademark).[
citation needed]
Like CS gas, this compound irritates the
mucous membranes (oral, nasal,
conjunctival and
tracheobronchial). Sometimes it can give rise to more generalized reactions such as
syncope, temporary loss of balance and orientation.
[2] More rarely, cutaneous irritating outbreaks have been observed and allergic contact permanent
dermatitis.
[3]
At high concentrations CN has caused
corneal epithelial damage and
chemosis. It has also accounted for at least five deaths, which have resulted from
pulmonary injury and/or
asphyxia.
[4]