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Acrylonitrile

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


Acrylonitrile
volatile liquid, although commercial samples can be yellow due to impurities. 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.[4] Acrylonitrile was first
synthesized by the French chemistCharles Moureu (1863–1929) in 1893.[5]

Contents
Occurrence
Production Names
Emerging industrial routes Preferred IUPAC name
Uses Prop-2-enenitrile
Health effects Other names
References Acrylonitrile
External links 2-Propenenitrile
Cyanoethene,
Vinyl cyanide (VCN)
Occurrence Cyanoethylene[1]
Propenenitrile[1]
Acrylonitrile is not naturally formed in the atmosphere of Earth. However it can
Identifiers
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 CAS Number 107-13-1
cyanide and formaldehyde.[6] Acrylonitrile is harmful to aquatic life.[7] 3D model (JSmol) Interactive

Acrylonitrile has been detected in the atmosphere of Titan, a moon of


image
Saturn.[8][9][10] Computer simulations suggest that on Titan conditions exist such Interactive
that the compound could form structures similar to cell membranes and vesicles on image
Earth.[8][9] ChEBI CHEBI:28217
ChEMBL ChEMBL445612
Production
Acrylonitrile is produced by catalytic ammoxidation of propylene, also known as ChemSpider 7567
the SOHIO process. In 2002, world production capacity was estimated at 5 million
tonnes per year.[4][11] Acetonitrile and hydrogen cyanide are significant byproducts
ECHA InfoCard 100.003.152
that are recovered for sale.[4] In fact, the 2008–2009 acetonitrile shortage was EC Number 608-003-00-4
caused by a decrease in demand for acrylonitrile.[12] KEGG C01998

2CH3-CH=CH2 + 2NH3 + 3O2 → 2CH2=CH-C≡N + PubChem CID 7855


6H2O RTECS number AT5250000

In the SOHIO process, propylene, ammonia, and air (oxidizer) are passed through a UNII MP1U0D42PE
fluidized bed reactor containing the catalyst at 400–510 °C and 50–200 kPag. The UN number 1093
reactants pass through the reactor only once, before being quenched in aqueous
InChI
sulfuric acid. Excess propylene, carbon monoxide, carbon dioxide, and dinitrogen
that do not dissolve are vented directly to the atmosphere, or are incinerated. The SMILES
aqueous solution consists of acrylonitrile, acetonitrile, hydrocyanic acid, and Properties
ammonium sulfate (from excess ammonia). A recovery column removes bulk water,
Chemical formula C3H3N
and acrylonitrile and acetonitrile are separated by distillation. Historically, one of
the first successful catalysts was bismuth phosphomolybdate supported on silica as Molar mass 53.06 g·mol−1
[4]
a heterogeneous catalyst. Further improvements have since been made. Appearance Colourless liquid
Density 0.81 g/cm3

Emerging industrial routes Melting point −84 °C (−119 °F;


189 K)
Various green chemistry routes are being developed for the synthesis of acrylonitrile
from renewable feedstocks, such as lignocellulosic biomass, glycerol (from Boiling point 77 °C (171 °F;
biodiesel production), or glutamic acid (which can itself be produced from 350 K)
renewable feedstocks). The lignocellulosic route involves fermentation of the Solubility in water 70 g/L
biomass to propionic acid and 3-hydroxypropionic acid which are then converted to log P 0.19[2]
acrylonitrile by dehydration and ammoxidation.[13] The glycerol route begins with
Vapor pressure 83 mmHg[1]
pyrolysis to acrolein, which undergoes ammoxidation to give acrylonitrile.[14] The
glutamic route employs oxidative decarboxylation to 3-cyanopropanoic, followed Hazards
by a decarbonylation-elimination to acrylonitrile.[15] Of these the glycerol route is Main hazards flammable,
broadly considered to be the most viable, although current methods are still unable reactive,
[13][14]
to compete with the SOHIO process in terms of cost. toxic,
potential

Uses occupational
carcinogen[1]
Acrylonitrile is used principally as a monomer to prepare polyacrylonitrile, a
Safety data sheet ICSC 0092
homopolymer, or several important copolymers, such as styrene-acrylonitrile
NFPA 704
(SAN), acrylonitrile butadiene styrene (ABS), acrylonitrile styrene acrylate (ASA), 3
and other synthetic rubbers such as acrylonitrile butadiene (NBR). Dimerization of 4 2
acrylonitrile affords adiponitrile, used in the synthesis of certain polyamides. Small
amounts are also used as afumigant. Acrylonitrile and derivatives, such as 2-chloro-
acrylonitrile, are dienophiles in Diels-Alder reactions. Acrylonitrile is also a Flash point −1 °C; 30 °F;
precursor in the industrial manufacture ofacrylamide and acrylic acid.[4] 272 K
Autoignition 471 °C (880 °F;
temperature
Health effects 744 K)
Explosive limits 3–17%
Acrylonitrile is highly flammable and toxic at low doses. It undergoes explosive
Lethal dose or concentration (LD,
polymerization. The burning material releases fumes of hydrogen cyanide and
LC):
oxides of nitrogen. It is classified as a Class 2B carcinogen (possibly carcinogenic)
by the International Agency for Research on Cancer (IARC),[16] and workers LC50 (median 500 ppm (rat, 4
exposed to high levels of airborne acrylonitrile are diagnosed more frequently with
concentration) hr)
lung cancer than the rest of the population.[17] It evaporates quickly at room 313 ppm
temperature (20 °C) to reach dangerous concentrations; skin irritation, respiratory (mouse, 4 hr)
irritation, and eye irritation are the immediate effects of this exposure.[7] 425 ppm (rat, 4
hr)[3]
Acrylonitrile increases cancer in high dose tests in male and female rats and
LCLo (lowest 260 ppm (rabbit,
mice.[18] published) 4 hr)
Pathways of exposure for humans include emissions, auto exhaust, and cigarette 575 ppm (guinea
smoke that can expose the human subject directly if they inhale or smoke. Routes of pig, 4 hr)
exposure include inhalation, oral, and to a certain extent dermal uptake (tested with 636 ppm (rat, 4
volunteer humans and in rat studies).[19] Repeated exposure causes skin hr)
sensitization and may cause central nervous system andliver damage.[7] 452 ppm
(human, 1 hr)[3]
There are two main excretion processes of acrylonitrile. The primary method is
US health exposure limits (NIOSH):
excretion in urine when acrylonitrile is metabolized by being directly conjugated to
glutathione. The other method is when acrylonitrile is metabolized with 2- PEL TWA 2 ppm C
(Permissible) 10 ppm [15-
cyanoethylene oxide to produce cyanide end products that ultimately forms
thiocyanate, which is excreted via urine, or carbon dioxide and eliminated through minute] [skin][1]
the lungs.[19] Metabolites can be detected in the blood and urine.
[16]
REL Ca TWA 1 ppm
(Recommended) C 10 ppm [15-
Acrylonitrile induces apoptosis in human umbilical cord mesenchymal stem cells
[20]
minute] [skin][1]
IDLH 85 ppm[1]
(Immediate
References danger)
Related compounds
1. "NIOSH Pocket Guide to Chemical Hazards #0014"(https://www.cdc.go Related acrylic acid,
v/niosh/npg/npgd0014.html). National Institute for Occupational Safety compounds acrolein
and Health (NIOSH).
2. "Acrylonitrile_msds" (https://www.chemsrc.com/en/cas/107-13-1_11868
Except where otherwise noted, data
are given for materials in their
93.html).
standard state (at 25 °C [77 °F],
3. "Acrylonitrile" (https://www.cdc.gov/niosh/idlh/107131.html). 100 kPa).
Immediately Dangerous to Life and Health Concentrations (IDLH).
verify (what is ?)
National Institute for Occupational Safety and Health(NIOSH).
4. James F. Brazdil (2005), "Acrylonitrile",Ullmann's Encyclopedia of Infobox references
Industrial Chemistry, Weinheim: Wiley-VCH,
doi:10.1002/14356007.a01_177.pub3(https://doi.org/10.1002/1435600
7.a01_177.pub3)
5. See:

C. Moureu (1893) "Contribution à l'étude de l'acide acrylique et de


ses dérivés" (http://babel.hathitrust.org/cgi/pt?id=uc1.31822017842
394;view=1up;seq=149)(Contribution to the study of acrylic acid
and of its derivatives),Annales de chimie et de physique, 7th series,
2 : 145-212 ; see especially pp. 187-189 ("Nitrile acrylique ou
cyanure de vinyle (Propène-nitrile)").
Moureu (1893) "Nitrile acrylique, cyanure de vinyle (propène-
nitrile)," (http://gallica.bnf.fr/ark:/12148/bpt6k282008w/f436.image.r=
BulletindelaSocieteChimiquedeParis.langFR)Bulletin de la Société
chimique de France, 3rd series, 9 : 424-427.
6. Grosjean, Daniel (December 1990). "Atmospheric Chemistry of oxic T
Contaminants. 3. Unsaturated Aliphatics: Acrolein, Acrylonitrile, Maleic
Anhydride". Journal of the Air & Waste Management Association. 40
(12): 1664–1669. doi:10.1080/10473289.1990.10466814(https://doi.or
g/10.1080/10473289.1990.10466814).
7. "CDC - ACRYLONITRILE - International Chemical Safety Cards -
NIOSH" (https://www.cdc.gov/niosh/ipcsneng/neng0092.html).
www.cdc.gov. Retrieved 2015-07-31.
8. Wall, Mike (28 July 2017)."Saturn Moon Titan Has Molecules That
Could Help Make Cell Membranes"(https://www.space.com/37653-satu
rn-moon-titan-cell-membrane-molecules.html) . Space.com. Retrieved
29 July 2017.
9. Palmer, Maureen Y.; et al. (28 July 2017). "ALMA detection and
astrobiological potential of vinyl cyanide on T
itan" (http://advances.scien
cemag.org/content/3/7/e1700022). Science Advances. 3 (7).
doi:10.1126/sciadv.1700022 (https://doi.org/10.1126/sciadv.1700022).
Retrieved 29 July 2017.
10. Kaplan, Sarah (8 August 2017)."This weird moon of Saturn has some
essential ingredients for life"(https://www.washingtonpost.com/news/sp
eaking-of-science/wp/2017/08/08/this-weird-moon-of-saturn-has-some-
essential-ingredients-for-life/). Washington Post. Retrieved 8 August
2017.
11. "The Sohio Acrylonitrile Process"(https://archive.is/20130223214113/ht
tp://portal.acs.org/portal/PublicWebSite/education/whatischemistry/land
marks/acrylonitrile/index.htm). American Chemical Society National
Historic Chemical Landmarks. Archived fromthe original (http://portal.ac
s.org/portal/PublicWebSite/education/whatischemistry/landmarks/acrylo
nitrile/index.htm) on 2013-02-23. Retrieved 2013-05-13.
12. A. Tullo. "A Solvent Dries Up".Chemical & Engineering News. 86: 27.
doi:10.1021/cen-v086n047.p027(https://doi.org/10.1021/cen-v086n047.
p027).
13. Grasselli, Robert K.; Trifirò, Ferruccio (2016)."Acrylonitrile from
Biomass: Still Far from Being a Sustainable Process".Topics in
Catalysis. 59 (17-18): 1651–1658. doi:10.1007/s11244-016-0679-7(http
s://doi.org/10.1007/s11244-016-0679-7). ISSN 1022-5528 (https://www.
worldcat.org/issn/1022-5528).
14. Guerrero-Pérez, M. Olga; Bañares, Miguel A. (2015). "Metrics of
acrylonitrile: From biomass vs. petrochemical route".Catalysis Today.
239: 25–30. doi:10.1016/j.cattod.2013.12.046(https://doi.org/10.1016/j.
cattod.2013.12.046). ISSN 0920-5861 (https://www.worldcat.org/issn/09
20-5861).
15. Le Nôtre, Jérôme; Scott, Elinor L.; Franssen, Maurice C. R.; Sanders,
Johan P. M. (2011). "Biobased synthesis of acrylonitrile from glutamic
acid". Green Chemistry. 13 (4): 807. doi:10.1039/c0gc00805b (https://d
oi.org/10.1039/c0gc00805b). ISSN 1463-9262 (https://www.worldcat.or
g/issn/1463-9262).
16. "Re-evaluation of Some Organic Chemicals, Hydrazine and Hydrogen
Peroxide"
(http://monographs.iarc.fr/ENG/Monographs/vol71/index.php)
. IARC
Monographs, Volume 71 (1999)
17. Acrylonitrile Fact Sheet (CAS No. 107-13-1)(http://www.epa.gov/chemf
act/acry-fs.txt). epa.gov
18. "Acrylonitrile: Carcinogenic Potency Database"(http://potency.berkeley.
edu/chempages/ACRYLONITRILE.html). berkeley.edu.
19. Acrylonitrile Fact Sheet: Support Document (CAS No. 107-13-1)(http://
www.epa.gov/chemfact/acry-sd.txt). epa.gov
20. Sun X (Jan 2014). "Cytotoxic effects of acrylonitrile on human umbilical
cord mesenchymal stem cells in vitro"(http://www.spandidos-publication
s.com/mmr/9/1/97). J Mol Med Rep. 9 (1): 97–102.
doi:10.3892/mmr.2013.1802 (https://doi.org/10.3892/mmr.2013.1802).
PMID 24248151 (https://www.ncbi.nlm.nih.gov/pubmed/24248151).

External links
National Pollutant Inventory – Acrylonitrile
Comparing Possible Cancer Hazards from Human Exposures to Rodent Carcinogens
Acrylonitrile – Integrated Risk Information System
, U.S. Environmental Protection Agency
CDC – NIOSH Pocket Guide to Chemical Hazards – Acrylonitrile
OSHA Table Z-1 for Air Contaminants

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