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Hazard Predictions

• Flammable: Reaction products may be flammable
• Generates heat: Exothermic reaction at ambient temperatures (releases heat)

Carboxylic esters react with amines to form amides and flammable alcohols (Loudon, Marc. 2002. Organic Chemistry. 4th ed. New York: Oxford University Press. p. 967). However, the rate and corresponding hazard of this reaction depend on the individual reactants.

Test data confirm that certain cyclic esters, such as caprolactone (and possibly other noncyclic esters) and amines such as ethylenediamine react by mixing under mild conditions (25 C) to form the amide and the alcohol along with the generation of heat. However, it has been similarly shown that compounds such as di-isopropylamine and ethylacetate only react at elevated temperatures and pressures. The favorable kinetic nature of the caprolactone reaction may be due to the cyclic structure of the reactant in question. As a precaution it may be best assume amines and esters are incompatible unless testing shows otherwise (personal communication).

Potential Gas Byproducts

• Alcohols