Acrylonitrile

Base Information

• Chemical Name: Acrylonitrile
• CAS No.: 107-13-1
• Deprecated CAS: 29754-21-0,63908-52-1,769126-92-3,769134-66-9,1006710-56-0,1197872-06-2,1221168-60-0,1309882-90-3,1538611-90-3,2015239-29-7,1006710-56-0,1197872-06-2,1221168-60-0,1309882-90-3,63908-52-1,769126-92-3,769134-66-9
• Molecular Formula: C3H3N
• Molecular Weight: 53.0635
• Hs Code.: 29261000
• European Community (EC) Number: 203-466-5,613-396-0
• ICSC Number: 0092
• NSC Number: 7763,6362
• UN Number: 1093
• UNII: MP1U0D42PE
• DSSTox Substance ID: DTXSID5020029
• Nikkaji Number: J1.971.960J,J4.055J
• Wikipedia: Acrylonitrile
• Wikidata: Q342968
• NCI Thesaurus Code: C28130
• Metabolomics Workbench ID: 51626
• ChEMBL ID: CHEMBL445612
• Mol file: 107-13-1.mol

Synonyms:Acrylonitrile;Cyanide, Vinyl;Vinyl Cyanide

Chemical Property of Acrylonitrile

Chemical Property:

• Appearance/Colour: clear liquid
• Vapor Pressure: 86 mm Hg ( 20 °C)
• Melting Point: -83.5 °C
• Refractive Index: n20/D 1.391(lit.)
• Boiling Point: 77.349 °C at 760 mmHg
• Flash Point: 32 °F
• PSA: 23.79000
• Density: 0.798 g/cm³
• LogP: 0.69598
• Storage Temp.: 2-8°C
• Sensitive.: Light Sensitive
• Solubility.: 73g/l
• Water Solubility.: Soluble. 7.45 g/100 mL
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 53.026549100
• Heavy Atom Count: 4
• Complexity: 54.9
• Transport DOT Label: Flammable Liquid Poison

Purity/Quality:

95+% ^*data from raw suppliers

Acrylonitrile(1mg/mLinMethanol) ^*data from reagent suppliers

Safty Information:

• Pictogram(s): F,T,N
• Hazard Codes: F,T,N,Xn
• Statements: 45-11-23/24/25-37/38-41-43-51/53-39/23/24/25-62-63
• Safety Statements: 53-9-16-45-61-36/37

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Nitrogen Compounds -> Nitriles
• Canonical SMILES: C=CC#N
• Inhalation Risk: A harmful contamination of the air can be reached very quickly on evaporation of this substance at 20 °C.
• Effects of Short Term Exposure: The substance and the vapour are irritating to the eyes, skin and respiratory tract. The substance may cause effects on the central nervous system. Exposure far above the OEL could cause death. The effects may be delayed. Medical observation is indicated.
• Effects of Long Term Exposure: Repeated or prolonged contact may cause skin sensitization. The substance may have effects on the central nervous system and liver. This substance is possibly carcinogenic to humans.
• Description: Acrylonitrile is a colourless, flammable liquid. Its vapours may explode when exposed to an open flame. Acrylonitrile does not occur naturally. It 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 is a heavily produced, unsaturated nitrile. It is used to make other chemicals such as plastics, synthetic rubber, and acrylic fibres. It has been used as a pesticide fumigant in the past; however, all pesticide uses have been discontinued. This compound 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 is also used in business machines, luggage, construction material, and manufacturing of styrene-acrylonitrile (SAN) plastics for automotive, household goods, and packaging material. Adiponitrile is used to make nylon, dyes, drugs, and pesticides. Acrylonitrile-3D-balls
• Uses: Acrylonitrile is primarily used in the manufacture of acrylic and modacrylic fibers. It 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 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. It may occur in fire-effluent gases because of pyrolyses of polyacrylonitrile materials. Acrylonitrile 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 monomer in the polymeric materials.

Technology Process of Acrylonitrile

There total 300 articles about Acrylonitrile which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 4.0%

2-β-cyanoethyl-1,2,4-triazol-3(2H)-one (537698-45-6) → acrylonitrile (107-13-1,25014-41-9) + 2,4-dihydro-1,2,4-triazol-3-one (930-33-6,5311-58-0)

Guidance literature:

at 800 ℃; under 0.01 Torr;

DOI:10.1002/hc.10086

Reference yield:

4-chlorobenzonitrile (100-00-5) + 3-dimethylaminopropiononitrile (1738-25-6) → hydrochloride of 3-dimethylaminopropionitrile (18076-02-3) + acrylonitrile (107-13-1,25014-41-9) + N,N-Dimethyl-4-nitroaniline (100-23-2)

Guidance literature:

In i-Amyl alcohol; at 130 ℃; for 130h; Product distribution;

Reference yield:

2-cyanoethyl p-nitrophenyl sulfoxide → di(p-nitrophenyl) disulfide (100-32-3) + acrylonitrile (107-13-1,25014-41-9)

Guidance literature:

In 1,4-dioxane; at 100 ℃; Rate constant; sealed tube;

DOI:10.1246/bcsj.60.2491

upstream raw materials:

oxirane

hydrogen cyanide

3-buten-1-yne

methanol

Downstream raw materials:

1-(2-cyanoethyl)aziridine

3-(piperidin-1-yl)propionitrile

3-(piperazin-1-yl)propan-1-amine

1,4-bis(3-aminopropyl)piperazine

Refernces

• 1、 Tsuji, Hideto,Koyasu, Yukio. "Synthesis of MoVNbTe(Sb)Ox composite oxide catalysts via reduction of polyoxometalates in an aqueous medium". . p. 5608 - 5609. Retrieved 2002.
• 2、 Wu, Li-Bin,Wu, Liang-Hua,Yang, Wei-Min,Frenkel, Anatoly I.. "Study of the local structure and oxidation state of iron in complex oxide catalysts for propylene ammoxidation". . p. 2512 - 2519. Retrieved 2014.
• 3、 Guillon, Cyrille,Liebig, Carsten,Paul, Sebastien,Mamede, Anne-Sophie,Hoelderich, Wolfgang F.,Dumeignil, Franck,Katryniok, Benjamin. "Ammoxidation of allyl alcohol-a sustainable route to acrylonitrile". . p. 3015 - 3019. Retrieved 2013.
• 4、 Bilde,Janke,Brückner,Millet. "Catalytic properties of nitrided V/Al/O-mixed oxides in the ammoxidation of propane and new efficient preparation method for the catalysts". . p. 10 - 15. Retrieved 2012.
• 5、 Lopez-Medina, R.,Rojas, E.,Banares, M. A.,Guerrero-Perez, M. O.. "Highly active and selective supported bulk nanostructured MoVNbTeO catalysts for the propane ammoxidation process". . p. 67 - 71,5. Retrieved 2012.
• 6、 Stepanov,Astakhov,Kruglyakova,Pekhotin. "Kinetics and mechanism of liquid-phase thermal decomposition of β-cyanoethyl-N-nitramines". . p. 1256 - 1258. Retrieved 2002.
• 7、 Doughty, Alan,Mackie, John C.. "Kinetics of Pyrolysis of the Isomeric Butenenitriles and Kinetic Modeling". . p. 272 - 281. Retrieved 1992.
• 8、 Raabová, Kate?ina,Bulánek, Roman,Bad'Urová, Eva. "High temperature pretreatment of Fe-silicalite for the ammoxidation of propane". . p. 54 - 59. Retrieved 2013.
• 9、 Atalla,Hussein,Badr. "Pyrolysis and Photolysis Processes of Pyran and Thiopyran Derivatives". . p. 29 - 35. Retrieved 1997.
• 10、 Pasupulety, Nagaraju,Driss, Hafedh,Zaman, Sharif F.,Alhamed, Yahia Abobakor,Alzahrani, Abdulrahim Ahmed,Daous, Muhammad A.,Petrov, Lachezar. "Influence of alumina precursor on the physico-chemical properties of V-Sb-P-W/Al2O3 catalyst studied for the ammoxidation of propane". . p. 52 - 62. Retrieved 2016.