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Acrylonitrile (AN) is a colourless, flammable liquid.
Acrylonitrile (AN)'s vapours may explode when exposed to an open flame.
Acrylonitrile does not occur naturally.
CAS: 107-13-1
MF: C3H3N
MW: 53.06
EINECS: 203-466-5
Synonyms
VINYL CYANIDE;CYANOETHYLENE;ACRYLONITRILE;ACRYLONITRILE, 100MG, NEAT;ACRYLONITRILE, 99+%;ACRYLNITRILE OEKANAL, STABILIZED;ACRYLONITRILE, STAB.;ACRYLONITRILE, 1X1ML, MEOH, 5000UG/ML
Acrylonitrile (AN) is produced in very large amounts by several chemical industries in the United States, and its requirement and demand are increasing in recent years.
Acrylonitrile (AN) is a heavily produced, unsaturated nitrile.
Acrylonitrile (AN) is used to make other chemicals such as plastics, synthetic rubber, and acrylic fibres.
Acrylonitrile (AN) has been used as a pesticide fumigant in the past; however, all pesticide uses have been discontinued.
Acrylonitrile (AN) is a major chemical intermediate used in creating products such as pharmaceuticals, antioxidants, and dyes, as well as in organic synthesis.
The largest users of acrylonitrile are chemical industries that make acrylic and modacrylic fibres and high-impact ABS plastics.
Acrylonitrile (AN) is also used in business machines, luggage, construction material, and manufacturing of styrene-acrylonitrile (SAN) plastics for automotive, household goods, and packaging material.
Acrylonitrile (AN) is used to make nylon, dyes, drugs, and pesticides.
Acrylonitrile is a nitrile that is hydrogen cyanide in which the hydrogen has been replaced by an ethenyl group.
Acrylonitrile (AN) is very toxic and irritant but is also a sensitizer.
Acrylonitrile (AN) caused both irritant and allergic contact dermatitis in a production manufacture.
Acrylonitrile (AN) is an organic compound with the formula CH2CHCN and the structure H2C=CH−C≡N.
Acrylonitrile (AN) is a colorless, volatile liquid.
Acrylonitrile (AN) has a pungent odor reminiscent of garlic or onions.
Acrylonitrile (AN)'s molecular structure consists of a vinyl group (−CH=CH2) linked to a nitrile (−C≡N).
Acrylonitrile (AN) is an important monomer for the manufacture of useful plastics such as polyacrylonitrile.
Acrylonitrile (AN) is toxic at low doses.
Acrylonitrile is one of the components of ABS plastic (acrylonitrile butadiene styrene).
Acrylonitrile (AN) is a useful organic monomer and reactant that must be handled very carefully.
As the hazard information table shows, Acrylonitrile (AN) is toxic in multiple ways.
Last year, the National Cancer Institute (Bethesda, MD) reported that, in a 25,000-person study, workers who made or used acrylonitrile in locations that exceeded the regulatory exposure limits had significantly greater lung cancer mortality than those who were protected by the regulations.
The synthesis of Acrylonitrile (AN) was first reported in 1893 by prominent French pharmacist/chemist Charles Moureu in a treatise on acrylic acid and its derivatives.
Moureu dehydrated acrylamide by heating Acrylonitrile (AN) with phosphorus pentoxide using a method developed by Jean Baptiste Dumas ≈60 years earlier.
In 1920, Moureu, along with Ralph I. Brown, made acrylonitrile from 3-hydroxypropionitrile using the same method.
Acrylonitrile (AN) is a colorless to pale yellow liquid and volatile liquid that is soluble in water and most common organic solvents such as acetone, benzene, carbon tetrachloride, ethyl acetate, and toluene.
Acrylonitrile (AN) melts at 84 degrees C and boils at 77 degrees C. Technical-grade Acrylonitrile (AN) is more than 99% pure and always contains a polymerization inhibitor.
Acrylonitrile (AN) is a reactive chemical that polymerizes spontaneously, when heated, or in the presence of a strong alkali unless it is inhibited, usually with ethylhydroquinone.
Acrylonitrile (AN) can explode when exposed to flame.
Acrylonitrile (AN) attacks copper.
Acrylonitrile (AN) is incompatible and reactive with strong oxidizers, acids and alkalis; bromine; and amines.
Synonyms for acrylonitrile are Acrylonitrile (AN), acrylonitrile monomer, cyanoethylene, propenenitrile, vinyl cyanide, and VCN.
Lewis structure shown below.
In the space provided, draw a 3D hybrid orbital bonding picture of acrylonitrile.
Label the hybridization of each atomic orbital.
Show overlap of orbitals to give bonds and label the type of bond.
Indicate what type of orbital the lone pair is in.
Acrylonitrile (AN) Chemical Properties
Melting point: -83 °C (lit.)
Boiling point: 77 °C (lit.)
density: 0.806 g/mL at 20 °C
vapor density: 1.83 (vs air)
vapor pressure: 86 mm Hg ( 20 °C)
refractive index: n20/D 1.391(lit.)
Fp: 32 °F
storage temp.: 2-8°C
solubility: 73g/l
form: Liquid
color: Clear
PH: 6.0-7.5 (50g/l, H2O, 20℃)
Odor: Mild pyridine-like odor at 2 to 22 ppm
Odor Threshold: 8.8ppm
explosive limit: 2.8-28%(V)
Water Solubility: Soluble. 7.45 g/100 mL
Thermal Conductivity: 0.166 W/(m·K) at 25 ℃
Sensitive: Light Sensitive
Merck: 14,131
BRN: 605310
Henry's Law Constant: 1.30 at 30.00 °C (headspace-GC, Hovorka et al., 2002)
Dielectric constant: 33.009999999999998
Exposure limits ACGIH TLV-TWA:2 ppm (4.3 mg/m3)
OSHA PEL-TWA:2 ppm,15-min;PEL-Ceiling:10 ppm
NIOSH REL-TWA:1 ppm;REL-Ceiling:10 ppm[15 min];IDLH:85 ppm
Major Application: agriculture
environmental
InChI: 1S/C3H3N/c1-2-3-4/h2H,1H2
InChIKey: NLHHRLWOUZZQLW-UHFFFAOYSA-N
LogP: 0.017 at 21℃
CAS DataBase Reference: 107-13-1(CAS DataBase Reference)
NIST Chemistry Reference: 2-Propenenitrile(107-13-1)
IARC: 2B (Vol. 71) 1999
EPA Substance Registry System: Acrylonitrile (AN) (107-13-1)
Chemical properties
Acrylonitrile (AN) is a clear, colorless to pale-yellow liquid with molecular formula C3H3N and molecular weight of 53.06.
The yellowing color is upon exposure to light and indicate photo-alteration to saturate derivate.
Acrylonitrile (AN) is practically odorless, or with a very slight odor that may be describe as sweet, irritating, unpleasant, onion or garlic-like or pungent.
Odor can only be detected above PEL.
Boiling point of 77.3°C and melting point of −82 °C.
Usage History
On the eve of World War II, Acrylonitrile (AN) was discovered that acrylonitrile copolymer can improve the oil resistance and solvent resistance of synthetic rubber and people began to be taken Acrylonitrile (AN) seriously.
During the war, Acrylonitrile (AN) was developed in Germany of the manufacturing process through epoxidation of ethylene, followed by addition with hydrogen cyanide to produce cyanide ethanol, and finally dehydration.
Acrylonitrile (AN) was later developed of addition of hydrogen cyanide to acetylene under the catalysis of cuprous chloride.
After 1960, Acrylonitrile (AN) had been developed of new production process in the Ohio standard oil company, using propylene as raw material for ammoxidation reaction to obtain it.
This process has led to great changes in industrial production.
Owing to the availability of raw materials and the reduction in the cost, there is a sudden surge in production of acrylonitrile.
In 1983, the world's annual output reached 3 million tons, of which the production amount of Ohio standard oil can account for 90%.
Acrylonitrile (AN) is easy to undergo polymerization, being able to produce polyacrylonitrile fiber (under the trade name of acrylic or bulk).
Acrylonitrile (AN)'s short fiber is similar to wool, also known as artificial wool.
Acrylonitrile (AN) feels soft by hand with excellent elasticity.
Acrylonitrile (AN) can co-polymerize with vinyl acetate to generate synthetic fibers (under the commercial name of Austrian Lun).
In 1950, Acrylonitrile (AN) was first put into industrial production by the United States DuPont.
The majority of Acrylonitrile (AN) is used for synthetic fiber with the amount accounting for about 40~60% of the total.
With copolymerization with butadiene copolymerization, Acrylonitrile (AN) can generate oil-resistant nitrile rubber.
Acrylonitrile (AN) dimerization and hydrogenation can be lead to adiponitrile, with then hydrogenation being able to obtain hexamethylene diamine, which is one of the raw materials of polyamide (nylon 66).
The co-polymer of acrylonitrile and butadiene, styrene terpolymer is a high-quality engineering plastics, referred to as ABS resin.
Uses
Acrylonitrile (AN) is primarily used in the manufacture of acrylic and modacrylic fibers.
Acrylonitrile (AN) is also used as a raw material in the manufacture of plastics (acrylonitrile-butadiene-styrene and styrene-acrylonitrile resins), adiponitrile, acrylamide, and nitrile rubbers and barrier resins.
A mixture of acrylonitrile and carbon tetrachloride was used as a pesticide in the past; however, all pesticide uses have stopped.
Acrylonitrile is a commercially important industrial chemical that has been used extensively since 1940s with the rapid expansion of the petrochemical industry.
The production of ABS and SAN resins consumes the second largest quantity of acrylonitrile.
The ABS resins are produced by grafting acrylonitrile and styrene onto polybutadiene or a styrene–butadiene copolymer and contain about 25 wt% acrylonitrile.
These products are used to make components for automotive and recreational vehicles, pipe fittings, and appliances.
The SAN resins are styrene–acrylonitrile copolymers containing 25–30 wt% of acrylonitrile.
The superior clarity of SAN resin allows it to be used in automobile instrument panels, for instrument lenses and for houseware items (Langvardt, 1985; Brazdil, 1991).
Acrylonitrile (AN) is used in the production of acrylic fibers, resins, and surface coating; as an intermediate in the production of pharmaceuticals and dyes; as a polymer modifier; and as a fumigant.
Acrylonitrile (AN) may occur in fire-effluent gases because of pyrolyses of polyacrylonitrile materials.
Acrylonitrile (AN) was found to be released from the acrylonitrile–styrene copolymer and acrylonitrile–styrene–butadiene copolymer bottles when these bottles were filled with food-simulating solvents such as water, 4% acetic acid, 20% ethanol, and heptane and stored for 10 days to 5 months (Nakazawa et al. 1984).
The release was greater with increasing temperature and was attributable to the residual Acrylonitrile (AN) monomer in the polymeric materials.
Acrylonitrile (AN) is produced commercially by propylene ammoxidation, in which propylene,ammonia, and air are reacted by catalyst in a fluidized bed.
Acrylonitrile (AN) is used primarily as a co-monomer in the production of acrylic and modacrylic fibers.
Uses include the production of plastics, surface coatings, nitrile elastomers, barrier resins, and adhesives.
Acrylonitrile (AN) is also a chemical intermediate in the synthesis of various antioxidants, pharmaceuticals, dyes, and surface-active agents.
Formerly, acrylonitrile was used as a fumigant for food commodities, flour milling, and bakery food processing equipment (HSDB, 1994).
The annual statewide industrial emissions from facilities reporting under the Air Toxics Hot Spots Act in California based on the most recent inventory were estimated to be 3948 pounds of acrylonitrile (CARB, 2000). US EPA
Acrylonitrile (AN) is used principally as a monomer to prepare polyacrylonitrile, a homopolymer, or several important copolymers, such as styrene-acrylonitrile (SAN), acrylonitrile butadiene styrene (ABS), acrylonitrile styrene acrylate (ASA), and other synthetic rubbers such as acrylonitrile butadiene (NBR).
Hydrodimerization of acrylonitrile affords adiponitrile, used in the synthesis of certain nylons:
2 CH2=CHCN + 2 e− + 2 H+ → NCCH2−CH2−CH2−CH2CN
Hydrolysis with sulfuric acid gives acrylamide sulfate, CH=CHC(O)NH2·H2SO4.
This salt can be converted to acrylamide and to methyl acrylate.
Hydrogenation of acrylonitrile is one route to propionitrile.
The reaction of acrylonitrile with protic nucleophiles is called cyanoethylation:
YH + H2C=CHCN → Y−CH2−CH2CN
Typical protic nucleophiles are alcohols, thiols, and especially amines.
When hydrogen cyanide is used the product is succinonitrile.
Acrylonitrile (AN) and derivatives, such as 2-chloroacrylonitrile, are dienophiles in Diels–Alder reactions.
Use in plastic bottles
In June 1974 Coca-Cola introduced the acrylonitrile/styrene 32oz Easy‐Goer plastic bottle, offering energy savings during manufacture, increased durability, and weight savings over glass.
In March 1977 after a suit filed by the Natural Resources Defense Council the FDA rescinded approval of acrylonitrile bottles citing adverse effects on test animals.
Monsanto, Coca-Cola's bottle manufacturer, refuted the decision, stating "repeated tests have demonstrated that there is no detectable migration of acrylonitrile into the bottle's content."
After several appeals in court by September 1977 the FDA finalized their ban.
Incidents
A large amount of acrylonitrile (approximately 6500 tons) leaked from an industrial polymer plant owned by Aksa Akrilik after the violent 17 August 1999 earthquake in Turkey.
Over 5000 people were affected and the exposed animals had died.
The leak was only noticed by the company 8 hours after the incident.
Healthcare workers did not know about the health effects of acrylonitrile and tried to treat the victims with painkillers and IV fluids.
One lawyer, Ayşe Akdemir, sued the company with 44 families as the plaintiffs.
Aksa Akrilik was sued by 200 residents who were affected by acrylonitrile.
An increase in cancer cases in the area was confirmed by the Turkish Medical Association, as the cancer rate in the affected area has increased by 80%, from 1999 to April 2002.
In 2003, the owner of Aksa Akrilik died from lung cancer related to acrylonitrile exposure.
Production Methods
Acrylonitrile (AN) is produced in commercial quantities almost exclusively by the vapor-phase catalytic propylene ammoxidation process developed by Sohio.
C3H6 + NH3 + 2/3O2→ C3H3N +3H2O
The one-step, fluid bed Acrylonitrile (AN) manufacturing process was developed by scientists of The Standard Oil Company (Sohio), one of INEOS's predecessors in the U.S. in the 1950s.
Today, over 95 percent of the world's Acrylonitrile is manufactured using INEOS's exclusive technology.
Reactivity Profile
Acrylonitrile (AN) produces poisonous hydrogen cyanide gas on contact with strong acids or when heated to decomposition.
Reacts violently with strong oxidizing agents (dibenzoyl peroxide, di-tert-butylperoxide, bromine).
Rapidly ignites in air and forms explosive mixtures with air.
Polymerizes violently in the presence of strong bases or acids. Underwent a runaway reaction culminating in an explosion on contact with a small amount of bromine or solid silver nitrate.
Health Hazard
Acrylonitrile (AN) is a highly toxic compound, an irritant to the eyes and skin, mutagenic, teratogenic, and causes cancer in test animals.
Acrylonitrile (AN) is a moderate to severe acute toxicant via inhalation, oral intake, dermal absorption, and skin contact.
Inhalation of this compound can cause asphyxia and headache.
Fire fighters exposed to acrylonitrile have reported chest pains, headache, shortness of breath, lightheadedness, coughing, and peeling of skin from their lips and hands (Donohue 1983).
These symptoms were manifested a few hours after exposure and persisted for a few days. Inhalation of 110 ppm for 4 hours was lethal to dogs.
In humans, inhalation of about 500 ppm for an hour could be dangerous.
The toxicity symptoms in humans from inhaling high concentrations of acrylonitrile were somnolence, diarrhea, nausea, and vomiting (ACGIH 1986).
Production
Acrylonitrile (AN) was first synthesized by the French chemist Charles Moureu in 1893.
Acrylonitrile (AN) is produced by catalytic ammoxidation of propylene, also known as the SOHIO process.
In 2002, world production capacity was estimated at 5 million tonnes per year, rising to about 6 million tonnes by 2017.
Acrylonitrile (AN) and hydrogen cyanide are significant byproducts that are recovered for sale.
In fact, the 2008–2009 Acrylonitrile (AN) shortage was caused by a decrease in demand for acrylonitrile.
2 CH3−CH=CH2 + 2 NH3 + 3 O2 → 2 CH2=CH−C≡N + 6 H2O
In the SOHIO process, propylene, ammonia, and air (oxidizer) are passed through a fluidized bed reactor containing the catalyst at 400–510 °C and 50–200 kPag.
The reactants pass through the reactor only once, before being quenched in aqueous sulfuric acid.
Excess propylene, carbon monoxide, carbon dioxide, and dinitrogen that do not dissolve are vented directly to the atmosphere, or are incinerated.
The aqueous solution consists of acrylonitrile, acetonitrile, hydrocyanic acid, and ammonium sulfate (from excess ammonia).
A recovery column removes bulk water, and acrylonitrile and acetonitrile are separated by distillation.
One of the first useful catalysts was bismuth phosphomolybdate (Bi9PMo12O52) supported on silica.
Further improvements have since been made.
