Acrylonitrile

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Acrylonitrile

Names

Preferred IUPAC name

Prop-2-enenitrile

Other names

Acrylonitrile

2-Propenenitrile

Cyanoethene

Vinyl cyanide (VCN)

Cyanoethylene[1]

Propenenitrile[1]

Identifiers

CAS Number • 107-13-1

3D model (JSmol) • Interactive image

ChEBI • CHEBI:28217

ChEMBL • ChEMBL445612

ChemSpider • 7567

ECHA InfoCard 100.003.152

EC Number • 608-003-00-4
KEGG • C01998

PubChem CID • 7855

RTECS number • AT5250000

UNII • MP1U0D42PE

UN number 1093

CompTox Dashboard (EPA)• DTXSID5020029

InChI[show]

SMILES[show]

Properties

Chemical formula C3H3N

Molar mass 53.064 g·mol−1

Appearance Colourless liquid

Density 0.81 g/cm3

Melting point −84 °C (−119 °F; 189 K)

Boiling point 77 °C (171 °F; 350 K)

Solubility in water 70 g/L

log P 0.19[2]

Vapor pressure 83 mmHg[1]

Hazards

Main hazards flammable

reactive

toxic

potential occupational carcinogen[1]

Safety data sheet ICSC 0092

NFPA 704 (fire diamond)

3
4
2
Flash point −1 °C; 30 °F; 272 K
 Autoignition 471 °C (880 °F; 744 K)
temperature

Explosive limits 3–17%

Lethal dose or concentration (LD, LC):

LC50 (median concentration) 500 ppm (rat, 4 h)

313 ppm (mouse, 4 h)

425 ppm (rat, 4 h)[3]

LCLo (lowest published) 260 ppm (rabbit, 4 h)

575 ppm (guinea pig, 4 h)

636 ppm (rat, 4 h)

452 ppm (human, 1 h)[3]

NIOSH (US health exposure limits):

PEL (Permissible) TWA 2 ppm C 10 ppm [15-minute]

[skin][1]

REL (Recommended) Ca TWA 1 ppm C 10 ppm [15-minute]

[skin][1]

IDLH (Immediate danger) 85 ppm[1]

Related compounds

Related nitriles acetonitrile

propionitrile

Related compounds acrylic acid

acrolein

Except where otherwise noted, data are given for materials in

their standard state (at 25 °C [77 °F], 100 kPa).

verify (what is ?)

Infobox references

Acrylonitrile is an organic compound with the formula CH2CHCN. It is a colorless

volatile liquid although commercial samples can be yellow due to impurities. It has a
pungent odor of garlic or onions.[4] In terms of its molecular structure, it consists of
a vinyl group linked to a nitrile. It is an important monomer for the manufacture of
useful plastics such as polyacrylonitrile. It is reactive and toxic at low
doses.[5] Acrylonitrile was first synthesized by the French chemist Charles
Moureu (1863–1929) in 1893.[6]

Contents
• 1Occurrence
• 2Production
o 2.1Emerging industrial routes
• 3Uses
• 4Health effects
• 5References
• 6External links

Occurrence[edit]
Acrylonitrile is not naturally formed in the atmosphere of Earth. However it can occur
at levels up to 0.11 ppm at industrial sites. It persists in the air for up to a week. It
decomposes by reacting with oxygen and hydroxyl radical to form formyl
cyanide and formaldehyde.[7] Acrylonitrile is harmful to aquatic life.[8]
Acrylonitrile has been detected in the atmosphere of Titan, a moon
of Saturn.[9][10][11] Computer simulations suggest that on Titan conditions exist such that
the compound could form structures similar to cell membranes and vesicles on
Earth.[9][10]

Production[edit]
Acrylonitrile 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.[5][12] Acetonitrile and hydrogen cyanide are significant byproducts that
are recovered for sale.[5] In fact, the 2008–2009 acetonitrile shortage was caused by
a decrease in demand for acrylonitrile.[13]
2CH3−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. Historically, one of the first successful catalysts
was bismuth phosphomolybdate (Bi9PMo12O52) supported on silica as a
heterogeneous catalyst.[14] Further improvements have since been made.[5]
Emerging industrial routes[edit]
Various green chemistry routes are being developed for the synthesis of
acrylonitrile from renewable feedstocks, such as lignocellulosic
biomass, glycerol (from biodiesel production), or glutamic acid (which can itself
be produced from renewable feedstocks). The lignocellulosic route involves
fermentation of the biomass to propionic acid and 3-hydroxypropionic acid which
are then converted to acrylonitrile by dehydration and ammoxidation.[15] The
glycerol route begins with pyrolysis to acrolein, which undergoes ammoxidation
to give acrylonitrile.[16] The glutamic acid route employs oxidative
decarboxylation to 3-cyanopropanoic acid, followed by a decarbonylation-
elimination to acrylonitrile.[17] Of these, the glycerol route is broadly considered to
be the most viable, although current methods are still unable to compete with the
SOHIO process in terms of cost.[15][16]

Uses[edit]
Acrylonitrile 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+ → NCCH2CH2CH2CH2CN
Small amounts are also used as a fumigant. Acrylonitrile and derivatives,
such as 2-chloroacrylonitrile, are dienophiles in Diels–Alder reactions.
Acrylonitrile is also a precursor in the industrial manufacture
of acrylamide and acrylic acid.[5]

Health effects[edit]
Acrylonitrile is highly flammable and toxic at low doses. It
undergoes explosive polymerization. The burning material releases fumes
of hydrogen cyanide and oxides of nitrogen. It is classified as a Class 2B
carcinogen (possibly carcinogenic) by the International Agency for Research
on Cancer (IARC),[18] and workers exposed to high levels of airborne
acrylonitrile are diagnosed more frequently with lung cancer than the rest of
the population.[19] Acrylonitrile increases cancer in high dose tests in male and
female rats and mice[20] and induces apoptosis in human umbilical
cord mesenchymal stem cells.[21]
It evaporates quickly at room temperature (20 °C) to reach dangerous
concentrations; skin irritation, respiratory irritation, and eye irritation are the
immediate effects of this exposure.[8] Pathways of exposure for humans
include emissions, auto exhaust, and cigarette smoke that can expose the
human subject directly if they inhale or smoke. Routes of exposure include
inhalation, oral, and to a certain extent dermal uptake (tested with volunteer
humans and in rat studies).[22] Repeated exposure causes skin sensitization
and may cause central nervous system and liver damage.[8]
There are two main excretion processes of acrylonitrile. The primary method
is excretion in urine when acrylonitrile is metabolized by being directly
conjugated to glutathione. The other method is when acrylonitrile is
metabolized with 2-cyanoethylene oxide to produce cyanide end products
that ultimately form thiocyanate, which is excreted via urine, and carbon
dioxide and eliminated through the lungs.[22] Metabolites can be detected in
the blood and urine.[18]