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Hexanedinitrile

Adiponitrile
Structural formula of adiponitrile
Ball-and-stick model of the adiponitrile molecule
Names
IUPAC name
Hexanedinitrile
Other names
  • Adipic acid dinitrile
  • Adipic acid nitrile
  • Adipyldinitrile
  • 1,4-Dicyanobutane
  • Hexanedioic acid dinitrile
  • Nitrile adipico
  • Tetramethylene cyanide
  • Tetramethylene dicyanide
Identifiers
111-69-3 YesY
3D model (Jmol) Interactive image
1740005
ChemSpider 13876621 YesY
ECHA InfoCard 100.003.543
EC Number 203-896-3
MeSH adiponitrile
PubChem 8128
RTECS number AV2625000
UNII SYT33B891I N
UN number 2205
Properties
C6H8N2
Molar mass 108.14 g·mol−1
Appearance Colourless liquid
Density 951 mg mL−1
Melting point 1 to 3 °C; 34 to 37 °F; 274 to 276 K
Boiling point 295.1 °C; 563.1 °F; 568.2 K
50 g/L (20 °C)
Vapor pressure 300 mPa (at 20 °C)
1.438
Thermochemistry
84.5–85.3 kJ mol−1
Hazards
GHS pictograms The skull-and-crossbones pictogram in the Globally Harmonized System of Classification and Labelling of Chemicals (GHS)
GHS signal word DANGER
H301, H315, H319, H330, H335
P260, P284, P301+310, P305+351+338, P310
Toxic T
R-phrases R25, R36/37/38
S-phrases S26, S36, S45
NFPA 704
Flammability code 2: Must be moderately heated or exposed to relatively high ambient temperature before ignition can occur. Flash point between 38 and 93 °C (100 and 200 °F). E.g., diesel fuel Health code 4: Very short exposure could cause death or major residual injury. E.g., VX gas Reactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogen Special hazards (white): no codeNFPA 704 four-colored diamond
Flash point 93 °C; 199 °F; 366 K (open cup)
550 °C (1,022 °F; 823 K)
Explosive limits 1.7–4.99%
Lethal dose or concentration (LD, LC):
LD50 (median dose)
 155 mg kg−1(oral, rat)
US health exposure limits (NIOSH):
PEL (Permissible)
 none
REL (Recommended)
 TWA 4 ppm (18 mg/m3)
IDLH (Immediate danger)
 N.D.
Related compounds
Related alkanenitriles
 Glutaronitrile
Related compounds
 hexanedioic acid
hexanedihydrazide
hexanedioyl dichloride
hexanediamide
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YesYN ?)
Infobox references

Adiponitrile is the organic compound with the formula (CH2)4(CN)2. This dinitrile, a viscous, colourless liquid, is an important precursor to the polymer nylon-6,6. In 2005, about one billion kilograms were produced annually.

Because of the industrial value of adiponitrile, many methods have been developed for its synthesis. Early industrial routes 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:

Adiponitrile has also been produced from adipic acid, by dehydration of the diamide, but this route is rarely employed.

The majority of adiponitrile is prepared by the nickel-catalysed hydrocyanation of butadiene, as discovered at DuPont, pioneered by Drinkard. The net reaction is:

ButadieneHydrocyanation.svg

The process involves several stages, the first of which involves monohydrocyanation (addition of one molecule of HCN), affording isomers of pentenenitriles as well as 2- and 3-methylbutenenitriles. These unsaturated nitriles are subsequently isomerized to the 3-and 4-pentenenitriles. In the final stage, these pentenenitriles are subjected to a second hydrocyanation, in an anti-Markovnikov sense, to produce adiponitrile.

Research has shown that the 3-pentenenitrile, formed in the first hydrocyanation, can undergo alkene metathesis to give dicyanobutenes, which are readily hydrogenated as described above.


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