Reactivity Documentation
Nitriles |
mixed with |
Metal Hydrides, Metal Alkyls, Metal Aryls, and Silanes |
Summary
- Flammable: Reaction products may be flammable
- Generates gas: Reaction liberates gaseous products and may cause pressurization
- Generates heat: Exothermic reaction at ambient temperatures (releases heat)
-
May produce the following gases:
- Aldehydes
- Hydrogen
- Ammonia
Details
Reactivity Predictions (for each pair of reactive groups)
Metal Hydrides, Metal Alkyls, Metal Aryls, and Silanes
Hazard Predictions
- Flammable: Reaction products may be flammable
- Generates gas: Reaction liberates gaseous products and may cause pressurization
- Generates heat: Exothermic reaction at ambient temperatures (releases heat)
Nitriles can be reduced to amines with lithium aluminum hydride or sodium borohydride (Cartolano, A. R. and Vedage, G. A. 2004. Amines by Reduction. Kirk-Othmer Encyclopedia of Chemical Technology. (Online); Kammermeier, B. 2000. Reduction. Ullmann's Encyclopedia of Industrial Chemistry. (Online)).
Complex metal hydrides can reduce nitriles to aldehydes (Kohlpaintner, C., Schulte, M., Falbe, J., Lappe, P. and Weber, J. 2008. Aldehydes, Aliphatic. Ullmann's Encyclopedia of Industrial Chemistry. (Online); Kammermeier, B. 2000. Reduction. Ullmann's Encyclopedia of Industrial Chemistry. (Online)).
Borohydrides generally reduce nitriles easily (Eggeman, T. 2001. Hydrides. In Kirk-Othmer Encyclopedia of Chemical Technology. John Wiley & Sons, Inc. (Online)).
Diborane readily reduces nitriles (Brown, H.C., W. Korytnyk. 1960. Journal of the American Chemical Society 82:3866).
Lithium aluminum hydride reacts violently with nitriles in the presence of water. Amines may be produced (Lewis, R.J., Sr. 1992. Sax's Dangerous Properties of Industrial Materials, 8th Edition. New York: Van Nostrand Reinhold. pp. 2130).
Potential Gas Byproducts
- Aldehydes
- Hydrogen (H2)
- Ammonia (NH3)