CN gas
Encyclopedia
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.
using chloroacetyl chloride
, with an aluminium chloride
catalyst:
and Second World Wars. Because of its greater toxicity, it has largely been supplanted by CS gas
.
CN is still supplied to paramilitary
and police forces in a small pressurized aerosol can known as “Mace
” or tear gas. Its use has fallen by the wayside 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 paper
s (a phenomenon known as a genericized trademark
).
Like CS gas, this compound irritates the mucous membrane
s (oral, nasal, conjunctiva
l and tracheobronchial). Sometimes it can give rise to more generalized reactions such as syncope, temporary loss of balance and orientation. More rarely, cutaneous irritating outbreaks have been observed and allergic contact permanent dermatitis
.
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
.
Acetophenone
Acetophenone is the organic compound with the formula C6H5CCH3. It is the simplest aromatic ketone. This colourless, viscous liquid is a precursor to useful resins and fragrances.-Production:Acetophenone can be obtained by a variety of methods...
. It is a useful building block in organic chemistry
Organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, composition, reactions, and preparation of carbon-based compounds, hydrocarbons, and their derivatives...
. 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 benzeneBenzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....
using chloroacetyl chloride
Chloroacetyl chloride
Chloroacetyl chloride is a chlorinated acyl chloride. It is a bifunctional compound, making it a useful building block chemical.-Production:Industrially, it is produced by the carbonylation of methylene chloride, oxidation of vinylidene chloride, or the addition of chlorine to ketene...
, with an aluminium chloride
Aluminium chloride
Aluminium chloride is the main compound of aluminium and chlorine. It is white, but samples are often contaminated with iron trichloride, giving it a yellow colour. The solid has a low melting and boiling point. It is mainly produced and consumed in the production of aluminium metal, but large...
catalyst:
Riot control agent
It was investigated, but not used, during the FirstWorld War I
World War I , which was predominantly called the World War or the Great War from its occurrence until 1939, and the First World War or World War I thereafter, was a major war centred in Europe that began on 28 July 1914 and lasted until 11 November 1918...
and Second World Wars. Because of its greater toxicity, it has largely been supplanted by CS gas
CS gas
2-chlorobenzalmalononitrile is the defining component of a "tear gas" commonly referred to as CS gas, which is used as a riot control agent...
.
CN is still supplied to paramilitary
Paramilitary
A paramilitary is a force whose function and organization are similar to those of a professional military, but which is not considered part of a state's formal armed forces....
and police forces in a small pressurized aerosol can known as “Mace
Mace (spray)
Chemical Mace is a tear gas in the form of an aerosol spray which propels a lachrymatory agent mixed with a volatile solvent. It is sometimes used as a self-defense device...
” or tear gas. Its use has fallen by the wayside as pepper spray
Pepper spray
Pepper spray, also known as OC spray , OC gas, and capsicum spray, is a lachrymatory agent that is used in riot control, crowd control and personal self-defense, including defense against dogs and bears...
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
Kleenex
Kleenex is a brand name for a variety of toiletry paper-based products such as facial tissue, bathroom tissue, paper towels, and diapers. The name Kleenex is a registered trademark of Kimberly-Clark Worldwide, Inc. Often used as a genericized trademark, especially in the United States, "Kleenex"...
has become strongly associated with tissue paper
Tissue paper
Tissue paper is a lightweight paper or, light crêpe paper. Tissue can be made both from virgin and recycled paper pulp.-Properties:Key properties are: strength, absorbency, basis weight, thickness , brightness, stretch, appearance and comfort....
s (a phenomenon known as a genericized trademark
Genericized trademark
A genericized trademark is a trademark or brand name that has become the colloquial or generic description for, or synonymous with, a general class of product or service, rather than as an indicator of source or affiliation as intended by the trademark's holder...
).
Like CS gas, this compound irritates the mucous membrane
Mucous membrane
The mucous membranes are linings of mostly endodermal origin, covered in epithelium, which are involved in absorption and secretion. They line cavities that are exposed to the external environment and internal organs...
s (oral, nasal, conjunctiva
Conjunctiva
The conjunctiva covers the sclera and lines the inside of the eyelids. It is composed of rare stratified columnar epithelium.-Function:...
l and tracheobronchial). Sometimes it can give rise to more generalized reactions such as syncope, temporary loss of balance and orientation. More rarely, cutaneous irritating outbreaks have been observed and allergic contact permanent dermatitis
Dermatitis
-Etymology:Dermatitis derives from Greek derma "skin" + -itis "inflammation" and genetic disorder.-Terminology:There are several different types of dermatitis. The different kinds usually have in common an allergic reaction to specific allergens. The term may describe eczema, which is also called...
.
At high concentrations CN has caused corneal epithelial
Corneal epithelium
The corneal epithelium is made up of epithelial tissue and covers the front of the cornea. It acts as a barrier to protect the cornea, resisting the free flow of fluids from the tears, and prevents bacteria from entering the epithelium and corneal stroma.The corneal epithelium consists of several...
damage and chemosis
Chemosis
Chemosis is the swelling of the conjunctiva. In general, chemosis is a nonspecific sign of eye irritation. The outer surface covering appears to have fluid in it. Often, the eye area swells so much that the eyes become difficult or impossible to close fully. It is usually caused by allergies or...
. It has also accounted for at least five deaths, which have resulted from pulmonary injury and/or asphyxia
Asphyxia
Asphyxia or asphyxiation is a condition of severely deficient supply of oxygen to the body that arises from being unable to breathe normally. An example of asphyxia is choking. Asphyxia causes generalized hypoxia, which primarily affects the tissues and organs...
.