Adiponitrile
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Adiponitrile
IUPAC name	Hexanedinitrile
Other names	1,4-Dicyanobutane, Adipic acid dinitrile, Adipic acid nitrile, Hexanedioic acid dinitrile, Adipyldinitrile, Nitrile adipico, Tetramethylene cyanide, Tetramethylene dicyanide, UN 2205
Identifiers
CAS number	[111-69-3]
SMILES	N#CCCCCC#N
InChI	1/C6H8N2/c7-5-3-1-2-4-6-8/h1-4H2
Properties
Molecular formula	C6H8N2
Molar mass	108.14 g/mol
Appearance	Colourless
Density	0.97 g/cm3
Melting point	1 °C
Boiling point	295 °C
Solubility in water	50 g/l (20 °C)
Vapor pressure	0.003 hPa (20 °C)
Hazards
Main hazards	Toxic, irritant
NFPA 704	2 4 1
R-phrases	R23, R25, R36, R38
S-phrases	S26, S37, S45
Flash point	93 °C (decomposition)
Autoignition temperature	460 °C
Explosive limits	1.7 - 4.9 %V
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Adiponitrile is the chemical compound with the formula (CH₂)₄(CN)₂. This dinitrile is an important precursor to the polymer nylon 6.6.

Because of the industrial value of adiponitrile, many routes have been developed for its synthesis. In one method, acrylonitrile is dimerized via electrosynthesis:

2 CH₂CHCN + 2 e^- + 2 H⁺ → NCCH₂CH₂CH₂CH₂CN

It has also been prepared by the nickel-catalysed hydrocyanation of butadiene:

2 CH₂CHCHCH₂ + 2 HCN → NCCH₂CH₂CH₂CH₂CN

Adiponitrile can be hydrogenated to 1,6-diaminohexane and hydrolysed to adipic acid.

External links

• International Chemical Safety Card 0211
• NIOSH Pocket Guide to Chemical Hazards 0015
• www.chemicalland.com
• www.nist.gov