History of acrylonitrile

Acrylonitrile is considered to be the key ingredient in the acrylic fibre as it is used to make clothing
and carpeting also acrylonitrile-butadiene-styrene (ABS) is a durable material used in automobile
components such as telephone and computer casings, and sports equipment. Moreover, nitrile tuber
which is used in the manufacture of hoses for pumping fuel is also made from acrylonitrile. However,
Acrylonitrile is used to produce plastics that are impermeable to gases and are ideal for shatterproof
bottles which hold chemicals and cosmetics and packaging for many other products. It is also a
component in plastic resins, paints, adhesives, and coatings. The acrylonitrile was made by a process
discovered and modified in the 1950s by scientists and engineers at The Standard Oil Company which
became part of British Petroleum (BP) in 1987. The process is a single-step direct method for
manufacturing acrylonitrile from propylene, ammonia, and air over a fluidized bed catalyst. (Hance,
1991)

Acrylic Fibres
ABS/SAN
Carbon Fibre Sweaters Carpet
Pipe
Sweats Blankets
Space Shuttle
Auto Bumpers, Dashboards Socks Draperies
America's Cup
Appliances T.V. Computer Shirts Industrial yarns
Sailboat
suits Dye receptor
Casings

Polyols
Latex
Specialty Products
Caulking
Seat Cushions
Paints
Head Rest

Silicones
Packaging
Speciality
Acrylamide Clear Coat on Auto
Blister Packs
Coupling Agent for chemicals
Water Soluble for Wastewater Treatment
Fiber Glass Gas Impermeable &
Shatterproof Containers
Acrylonitrile was first synthesized in 1893 by a scientist whose name is Charles Moorea, but
unfortunately it did not become important till the end of 1930s as many industries began to use it in
new applications such as acrylic fibres for textiles and synthetic rubber. Furthermore, by the late 1940s
the utility of acrylonitrile was unclear as many existing manufacturing methods were expensive,
multistep processes an according to these factors’ acrylonitrile could well have remained little more
than an interesting, low-volume specialty chemical with limited applications. However, In the late
1950s, Sohio's research into a selective catalytic oxidation led to an entering in acrylonitrile
manufacture. Not only does using the catalytic oxidation had shown such a dramatic lowering of
process costs that all other methods of producing acrylonitrile, predominantly through acetylene,
became more popular, but it also has increased the Worldwide consumption of acrylonitrile o be 52%
between 1976 and 1988, from 2500 to 3800 thousand tonnes per year. Since the 1960s, acrylic fibres
have remained the major outlet for acrylonitrile production in the United States and especially in
Japan and the Far East. Also, they have been classified as Fibres containing 85 wt% or more
acrylonitrile is usually referred to as ‘acrylics’ and fibres containing 35–85 wt% acrylonitrile is called
‘modacrylics’. Now a days, Acrylic fibres are playing a main role in many industries as they are used
primarily for the manufacture of apparel, including sweaters, fleece wear and sportswear, and home
furnishings, including carpets, upholstery and draperies. (langvardt, 1985) (Brazdil, 1985)

Moreover, the production of Acrylonitrile-Butadiene-Styrene and Styrene acrylonitrile resins

consumes the second largest quantity of acrylonitrile as ABS resins are produced by grafting
acrylonitrile and styrene onto polybutadiene or a styrene–butadiene copolymer that contain about 25
wt% acrylonitrile which are used to make components for automotive and recreational vehicles, pipe
fittings, and appliances. The purity of SAN resin allows it to be used in automobile instrument panels,
for instrument lenses and for houseware items. One of the growing specialty applications for
acrylonitrile is the manufacture of carbon fibres that are produced by pyrolysis of oriented
polyacrylonitrile fibres and are used to reinforce composites for high-performance applications in the
aircraft, defence and aerospace industries. On the other hand, one of the minor specialty applications
of acrylonitrile are in the production of fatty amines, ion exchange resins and fatty amine amides used
in cosmetics, adhesives, corrosion inhibitors and water-treatment resins. (Brazdil, 1985)
Table 1 Worldwide acrylonitrile uses and consumption (thousand tonnes)

use 1976 1980 1985 1988

Acrylic fibres 1760 2040 2410 2520
Acrylonitrile– 270 300 435 550
butadiene–styrene
resins

Adiponitrile 90 160 235 310

Other (including 420 240 390 460
nitrile rubber,
styrene–
acrylonitrile resin,
acrylamide, and
barrier resins)

Physical and chemical properties of acrylonitrile

Acrylonitrile is a volatile, flammable, water-soluble liquid at room temperature. The vast majority of
acrylonitrile in Canada is used as a feedstock or chemical aid in the production of nitrile butadiene
rubber and in acrylonitrile-butadiene-styrene and styrene-acrylonitrile polymers. in 1993 the
Estimated world capacity was about 4 million tonnes. the European Union which produce 1.25 million
tonnes per year, the USA that produce approximately 1.5 million tonnes per year and Japan that
produce 0.6 million tonnes per year are considered to be the major areas of production. Acrylonitrile
is released into the environment primarily from chemical production and plastic products industries
There are no known natural sources, but they actually released to nature as Acrylonitrile is distributed
largely to the environmental compartments to which it is principally released with movement to soil,
sediment, or biota as it is being limited reaction, so advection is the major removal mechanism.
Acrylonitrile is rapidly absorbed via all routes of exposure and distributed throughout examined
tissues. Acrylonitrile is also known as acrylic acid nitrile, acrylon, carbaryl, cyanoethylate, fumigant,
propenenitrile,2-propenenitrile, propanoic acid nitrile. Its Chemical Abstracts Service (CAS) number is
107-13-1, its molecular formula, C3H3N, and its relative molecular mass, 53.06. (Martin, 1996)
The molecular structure of acrylonitrile is presented below

Figure 1 chemical structure of acrylonitrile

The physical and chemical properties of acrylonitrile are presented in Table 2. At room temperature,
acrylonitrile is a volatile, flammable, colourless liquid with a weakly pungent odour. Acrylonitrile has
two chemically active sites, at the carbon–carbon double bond and at the nitrile group, where it
undergoes several reactions. It is a polar molecule because of the presence of the (CN) group. It is
soluble in water (75.1 g/litre at 25 °C) and miscible with most organic solvents. The vapours are
explosive, with cyanide gas being produced. Acrylonitrile may polymerize spontaneously and violently
in the presence of concentrated caustic acid, on exposure to visible light, or in the presence of
concentrated alkali Hence, it is stored accordingly, often as an acrylonitrile–water formulation that
acts as a polymerization inhibitor. (Kirk, 1983)
Table 2 physical and chemical properties of acrylonitrile

PROPERTY RANGE

DENSITY AT 20C 806

MELTING POINT 83.55C

BOILING POINT 77.3C

WATER SOLUBILITY AT 25C 75.1

Miscible with most
SOLUBILITY
organic solvents

VAPOUR PRESSURE AT 25C (KPA) 11-15.6

HENRY’S LAW CONSTANT AT 25 °C

8.92-11.14
(PA@M3/MOL)

LOG ORGANIC CARBON/WATER

1.06 (0.09 to 1.1)
PARTITION COEFFICIENT (LOG KOC)

LOG OCTANOL/WATER PARTITION

0.25 (0.92 to 1.2)
COEFFICIENT (LOG KOW)

LOG BIOCONCENTRATION FACTOR

0.48–1.68
(LOG BCF) IN FISH

(Martin, 1996) (Nagel, 1988) (AEL, 1996)

References
AEL, D. &. (1996). Retrieved from pubchem.ncbi.nlm.nih.gov

Brazdil. (1985, 8 22). Retrieved from pubchem.ncbi.nlm.nih.gov

Hance, w. (1991). International journal of chemical kinetics. International journal of chemical

kinetics.

Kirk. (1983, 8 06). Retrieved from pubchem.ncbi.nlm.nih.gov

langvardt. (1985). Time/toxicity relationships. American Society for Testing and Materials.

Martin. (1996, 9 14). Retrieved from pubchem.ncbi.nlm.nih.gov

Nagel, K. &. (1988, 10 03). Retrieved from Koch & Nagel