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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.

Additional recommended knowledge

Daily Sensitivity Test

Essential Laboratory Skills Guide

How to quickly check pipettes?

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