Adiponitrile
From Wikipedia, the free encyclopedia
| 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 |
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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.
