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Adiponitrile

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

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

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.

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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.

Category: Nitriles