Azobisisobutyronitrile

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:

Additional recommended knowledge

Daily Sensitivity Test

How to ensure accurate weighing results every day?

Recognize and detect the effects of electrostatic charges on your balance

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 a 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]

See also

• 1,1'-Azobis(cyclohexanecarbonitrile) or ABCN is another free radical initiator

References

1. ^ http://www2.dupont.com/Vazo/en_US/products/grades/grades.html
2. ^ http://www.wako-chem.co.jp/specialty/waterazo/index.htm