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Hazard Predictions

• Generates gas: Reaction liberates gaseous products and may cause pressurization
• Potentially hazardous: May be hazardous but unknown

Although no specific evidence was found for a hazardous reaction between amides and weak oxidizing agents, amides and imides can undergo hazardous reactions with strong oxidizing agents, as shown in the examples below. Therefore, we urge chemists to perform testing to ensure that hazards do not occur under conditions appropriate to their scenario.

DMF reacts exothermically with Br2, possibly forming toxic and flammable carbon monoxide gas and toxic HBr gas (Tayim, H.A. et al. 1973. Chemistry and Industry 347.).

DMF reacts exothermically with Cl2, producing toxic and flammable carbon monoxide gas and inert CO2 gas (Woltornist, A. 1983. Chemical and Engineering News 61(6):4.).

Caprolactam reacts explosively with N2O3 in acetic acid unless cooled (Huisgen, R. et al. 1952. Justus Liebigs Annalen der Chemie. 575:174-197.).

DMF can react explosively with CrO3 or KMnO4; dimethylacetamide is suggested as a safer substitute (Pal, B.C. et al. 1981. Chemical and Engineering News 59(17):47.).

Some complex amides also have explosive reactions with CrO3 (Urben, P.G. 1995. Bretherick's Handbook of Reactive Chemical Hazards, 5th Edition. Oxford: Butterworth-Heinemann. pp. 1378-1379.).

Urea ignites in contact with chromyl chloride (Pascal, P. 1959. Nouveau Trait茅 de Chimie Min茅rale. Vol. 14, p. 153. Masson et Cie.).

Urea ignites in contact with nitrosyl perchlorate (Hoffman, K.A. et al. 1909. Berichte. 42:2031.).

DMF can also ignite on contact with CrO3 (Heathcock, C.H. 1981. Chemical and Engineering News 59(8):9.).

Urea reacts with metal hypochlorites to form explosive liquid NCl3 (National Fire Protection Association. 1975. Publication 491M. pp. 213.).

DMF forms an explosive mixture with urea perchlorate (Kukasabe, M. et al. 1980. Chemical Abstracts 92:79028.).

Methylimide may react with O2 gas or the OH- functional group to yield the toxic gas HCN (Smith, P. A. S., Open-Chain Nitrogen Compounds, Vol. I. New York: W. A. Benjamin, Inc., 1965, pp. 311).

Potential Gas Byproducts

• Carbon Monoxide (CO)
• Hydrogen Cyanide (HCN)