Azobisisobutyronitrile
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| AIBN | |
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| IUPAC name | 2,2′-Azobis(2-methylpropionitrile) |
| Other names | Azobisisobutyronitrile Azobisisobutylonitrile AIBN |
| Identifiers | |
| CAS number | [78-67-1] |
| SMILES | N#CC(C)(C)N=NC(C)(C)C#N |
| Properties | |
| Molecular formula | C8H12N4 |
| Molar mass | 164.21 g/mol |
| Appearance | white crystalline |
| Density | ? |
| Melting point |
103–105 °C |
| Boiling point |
°C |
| Solubility in water | ? |
| Structure | |
| Dipole moment | (gas) |
| Hazards | |
| Flash point | ? |
| 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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Azobisisobutyronitrile is a toxic compound often used as a foamer in plastics and rubber and as a radical initiator. It is commonly known as AIBN. Its most common chemical reaction is one of decomposition, eliminating a molecule of nitrogen gas to form two 2-cyanoprop-2-yl radicals:
These radicals can be used to to initiate free radical polymerizations and other radical reactions. For instance a mixture of styrene and maleic anhydride in toluene will react if heated, forming the polystyrene polymer, only very slowly unless an initiator such an AIBN is present. Another example of a radical reaction that can be initiated by AIBN is the anti-Markovnikov hydrohalogenation of alkenes.
AIBN is safer to use than benzoyl peroxide (another radical initiator) because the risk of explosion is far smaller. However, it is considered a flammable solid. It is soluble in methanol and ethanol, but is insoluble in water. It can explode if dissolved in acetone. AIBN is highly toxic. Wear a respirator/dust mask, protective gloves, & safety glasses when handling AIBN.
Several water-soluble azo initiators similar to AIBN are manufactured by DuPont[1] and Wako.[2]
[edit] See also
- 1,1'-Azobis(cyclohexanecarbonitrile) or ABCN is another free radical initiator
[edit] References
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