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Adiponitrile



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 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.

Additional recommended knowledge

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.

 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Adiponitrile". A list of authors is available in Wikipedia.
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