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| Names | |||
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| Preferred IUPAC name Prop-2-enenitrile | |||
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| Identifiers | |||
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3D model (JSmol) | |||
| ChEBI | |||
| ChEMBL | |||
| ChemSpider |
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| ECHA InfoCard | 100.003.152 | ||
| EC Number |
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| KEGG |
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| RTECS number |
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| UNII | |||
| UN number | 1093 | ||
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| Properties | |||
| 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) | ||
| 70 g/L | |||
| logP | 0.19[2] | ||
| Vapor pressure | 83 mmHg[1] | ||
| Hazards | |||
| Occupational safety and health (OHS/OSH): | |||
Main hazards | flammable reactive toxic potential occupational carcinogen[1] | ||
| NFPA 704 (fire diamond) | |||
| Flash point | −1 °C; 30 °F; 272 K | ||
| 471 °C (880 °F; 744 K) | |||
| 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] | ||
| Safety data sheet (SDS) | ICSC 0092 | ||
| Related compounds | |||
Relatednitriles | acetonitrile propionitrile | ||
Related compounds | acrylic acid acrolein | ||
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |||
Acrylonitrile is anorganic compound with theformulaCH2CHCN and thestructureH2C=CH−C≡N. It is a colorless,volatile liquid. It has a pungent odor of garlic or onions.[4] Itsmolecular structure consists of avinyl group (−CH=CH2) linked to anitrile (−C≡N). It is an importantmonomer for the manufacture of usefulplastics such aspolyacrylonitrile. It isreactive andtoxic at low doses.[5]
Acrylonitrile is one of the components of ABS plastic (acrylonitrile butadiene styrene).[6]
Acrylonitrile is anorganic compound with theformulaCH2CHCN and thestructureH2C=CH−C≡N. It is a colorless,volatile liquid although commercial samples can be yellow due toimpurities. It has a pungent odor of garlic or onions.[4] Itsmolecular structure consists of avinyl group (−CH=CH2) linked to anitrile (−C≡N). It is an importantmonomer for the manufacture of usefulplastics such aspolyacrylonitrile. It isreactive andtoxic at low doses.[5]
Acrylonitrile was first synthesized by the French chemistCharles Moureu in 1893.[7] Acrylonitrile is produced bycatalyticammoxidation ofpropylene, also known as theSOHIO process. In 2002, world production capacity was estimated at 5 million tonnes per year,[5][8] rising to about 6 million tonnes by 2017.[9]Acetonitrile andhydrogen cyanide are significant byproducts that are recovered for sale.[5] In fact, the2008–2009 acetonitrile shortage was caused by a decrease in demand for acrylonitrile.[10]
In the SOHIO process,propylene,ammonia, and air (oxidizer) are passed through afluidized 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, andammonium sulfate (from excess ammonia). A recovery column removes bulk water, and acrylonitrile and acetonitrile are separated by distillation. One of the first useful catalysts wasbismuthphosphomolybdate (Bi9PMo12O52)supported on silica.[11] Further improvements have since been made.[5]
Variousgreen chemistry routes to acrylonitrile are being explored from renewable feedstocks, such aslignocellulosic biomass,glycerol (frombiodiesel production), orglutamic acid (which can itself be produced from renewable feedstocks). The lignocellulosic route involves fermentation of the biomass topropionic acid and3-hydroxypropionic acid, which are then converted to acrylonitrile by dehydration andammoxidation.[12][9] The glycerol route begins with itsdehydration toacrolein, which undergoes ammoxidation to give acrylonitrile.[13] The glutamic acid route employsoxidative decarboxylation to 3-cyanopropanoic acid, followed by a decarbonylation-elimination to acrylonitrile.[14] Of these, the glycerol route is broadly considered to be the most viable, although none of these green methods are commercially competitive.[12][13]
Acrylonitrile is used principally as amonomer to preparepolyacrylonitrile, ahomopolymer, or several importantcopolymers, such asstyrene-acrylonitrile (SAN),acrylonitrile butadiene styrene (ABS),acrylonitrile styrene acrylate (ASA), and othersynthetic rubbers such asacrylonitrile butadiene (NBR).Hydrodimerization of acrylonitrile[15][16] affordsadiponitrile, used in the synthesis of certainnylons:
Acrylonitrile is also a precursor in the manufacture ofacrylamide andacrylic acid.[5]
Hydrogenation of acrylonitrile is one route to propionitrile. Hydrolysis with sulfuric acid gives acrylamide sulfate,CH=CHC(O)NH2·H2SO4. This salt can be converted toacrylamide with treatment with base or tomethyl acrylate by treatment withmethanol.[5]
The reaction of acrylonitrile with protic nucleophiles is a common route to a variety of specialty chemicals. The process is calledcyanoethylation:
Typical protic nucleophiles arealcohols,thiols, and especiallyamines.[17] Whenhydrogen cyanide is used the product issuccinonitrile.[18]
Acrylonitrile and derivatives, such as 2-chloroacrylonitrile, aredienophiles inDiels–Alder reactions.
Acrylonitrile istoxic withLD50 = 81 mg/kg (rats). It undergoesexplosivepolymerization. The burning material releases fumes ofhydrogen cyanide andoxides of nitrogen. It is classified as aClass 1 carcinogen (carcinogenic) by theInternational Agency for Research on Cancer (IARC),[19] and workers exposed to high levels of airborne acrylonitrile are diagnosed more frequently withlung cancer than the rest of the population.[20] Acrylonitrile is one of seventoxicants incigarette smoke that are most associated withrespiratory tractcarcinogenesis.[21] The mechanism of action of acrylonitrile appears to involve oxidative stress and oxidative DNA damage.[22] Acrylonitrile increases cancer in high dose tests in male and female rats and mice[23] and inducesapoptosis in human umbilical cordmesenchymal stem cells.[24]
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.[25] Pathways of exposure for humans includeemissions,auto exhaust, andcigarette 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).[26] Repeated exposure causes skin sensitization and may cause central nervous system andliver damage.[25]
There are two main excretion processes of acrylonitrile. The primary method is excretion in urine when acrylonitrile is metabolized by being directly conjugated toglutathione. The other method is when acrylonitrile is enzymatically converted into 2-cyanoethylene oxide which will producecyanide end products that ultimately formthiocyanate, which is excreted via urine.[26] Exposure can thus be detected via blood draws and urine sampling.[19]
In July 2024, theInternational Agency for Research on Cancer upgraded acrylonitrile's classification from 'possibly carcinogenic' tocarcinogenic for humans. The Agency foundsufficient evidence linking it tolung cancer.[27][28]
In June 1974Coca-Cola introduced the acrylonitrile/styrene 32oz Easy‐Goer plastic bottle, offering energy savings during manufacture, increased durability, and weight savings over glass.[29] In March 1977 after a suit filed by theNatural Resources Defense Council the FDA rescinded approval of acrylonitrile bottles citing adverse effects on test animals.[30]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.[31][32]
A large amount of acrylonitrile (approximately 6500 tons) leaked from an industrial polymer plant owned byAksa Akrilik after the violent17th August 1999 earthquake in Turkey. Over 5000 people were affected and the exposed animals had died.[33] 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.[34] One lawyer, Ayşe Akdemir, sued the company with 44 families as the plaintiffs.[34] Aksa Akrilik was sued by 200 residents who were affected by acrylonitrile.[35] An increase in cancer cases in the area was confirmed by theTurkish Medical Association,[35] as the cancer rate in the affected area has increased by 80%, from 1999 to April 2002.[34] In 2003, the owner of Aksa Akrilik died from lung cancer related to acrylonitrile exposure.[34] As of 2001, this is the largest known acrylonitrile leak.[33]
Acrylonitrile is not naturally formed on Earth. It has been detected at the sub-ppm level at industrial sites. It persists in the air for up to a week. It decomposes by reacting with oxygen and hydroxyl radical to formformyl cyanide andformaldehyde.[36] Acrylonitrile isharmful to aquatic life.[25] Acrylonitrile has been detected in the atmosphere ofTitan, a moon ofSaturn.[37][38][39] Computer simulations suggest that on Titan conditions exist such that the compound could form structures similar tocell membranes andvesicles on Earth, calledazotosomes.[37][38]
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