Structure via PubChem · Public domain (PubChem)
adiponitrile
Sign in to saveAlso known as 1,4-Dicyanobutane, Hexanedinitrile, Tetramethylene cyanide, Adipic acid dinitrile, Adipic acid nitrile
Adiponitrile is an organic compound with the chemical formula (CH2)4(CN)2. This viscous, colourless dinitrile is an important precursor to the polymer nylon 66. In 2005, about one million tonnes of adiponitrile were produced.
Chemical data
- Formula
- C6H8N2
- Molecular weight
- 108.14 g/mol
- IUPAC name
- hexanedinitrile
- SMILES
- C(CCC#N)CC#N
- InChIKey
- BTGRAWJCKBQKAO-UHFFFAOYSA-N
- XLogP
- -0.3
- Polar surface area
- 47.6 Ų
- H-bond donors
- 0
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
~4 min read
Encyclopedic overview
8 sectionsContents
- Production
- Early methods
- Modern methods
- Applications
- Production
- Safety
- References
- External links
Adiponitrile is an organic compound with the chemical formula (CH2)4(CN)2. This viscous, colourless dinitrile is an important precursor to the polymer nylon 66. In 2005, about one million tonnes of adiponitrile were produced.
==Production== ===Early methods=== Because of the industrial value of adiponitrile, many methods have been developed for its synthesis. Early industrial methods started from furfural and later by the chlorination of butadiene to give 1,4-dichloro-2-butene, which with sodium cyanide, converts to 3-hexenedinitrile, which in turn can be hydrogenated to adiponitrile: ClCH2CH=CHCH2Cl + 2 NaCN → NCCH2CH=CHCH2CN + 2 NaCl NCCH2CH=CHCH2CN + H2 → NC(CH2)4CN Adiponitrile has also been produced from adipic acid, by dehydration of the diamide, but this is rarely employed.
Excerpted from Wikipedia’s “adiponitrile” article, available under the CC BY-SA 4.0 licence.