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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)
• Polymerization hazard: Polymerization reaction may become intense and may cause pressurization
• Toxic: Reaction products may be toxic

Fluorinated amides can react violently with lithium aluminum hydride, potentially causing ignition or gas evolution (Karo, W. 1955. Chemical and Engineering News 33, 1368).

Amides can be reduced by strong reductants (e.g., metal hydrides, NaBH4, BH3) to produce aldehydes, nitriles, and amines, with evolution of hydrogen gas (Zabicky, J., ed. 1970. The Chemistry of Amides. John Wiley & Sons. pp. 795-797).

DMF reacts very violently with NaBH4 at elevated temperatures and after a long induction period. Acetic or formic acids cause the reaction to run immediately. The reaction produces flammable trimethylamine gas (Schwartz, J. et al. 1993. Journal of Organic Chemistry 58(18):2005; Yeowell, A. et al. 1979. Chemical and Engineering News, 57(39), p. 4).

DMF and NaH react exothermically at or slightly above room temperature; the reaction is self-accelerating (Buckley, J. et al. 1982. Chemical and Engineering News 60(28):5).

Amides can be reduced to amines with metal hydrides (Cartolano, A. R. and Vedage, G. A. 2004. Amines by Reduction. Kirk-Othmer Encyclopedia of Chemical Technology. (Online); Johansson, I. 2003. Amides, Fatty Acid. Kirk-Othmer Encyclopedia of Chemical Technology. (Online)).

The reduction of amides by complex metal hydrides can produce aldehydes as well as amines (Kohlpaintner, C., Schulte, M., Falbe, J., Lappe, P. and Weber, J. 2008. Aldehydes, Aliphatic. Ullmann's Encyclopedia of Industrial Chemistry. (Online)).

Sodium hydride can cause the polymerization of caprolactam, a cyclic amide (Sullivan, E. and Wade, R. 1980. Hydrides. Kirk-Othmer Encyclopedia of Chemical Technology, 3rd ed. John Wiley & Sons, Inc.).

Potential Gas Byproducts

• Aldehydes
• Hydrogen (H2)
• Ammonia (NH3)