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Environmental fate & pathways

Hydrolysis

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Description of key information

There is little published information on the hydrolysis of tertiary alkylamines into an amine and alcohol and no guideline-type hydrolysis studies were located. In lieu of experimental data, process chemistry and thermodynamics provide insight on the hydrolysis of amines. Therefore, hydrolysis testing is not indicated for the substance, which is a tertiary alkylamine.

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Additional information

Two factors determine whether a hydrolysis reaction will occur. The first is thermodynamic feasibility. The second is the amount of activation energy needed for reaction at a particular temperature.  In the case of the hydrolysis of the alkylamines, both factors strongly disfavor the reaction. 

Thermodynamically favored reactions of amines with alcohols require high temperature (typically 300°C) and catalysts to occur at useful rates. The thermodynamics of the reverse reaction (hydrolysis) is endothermic by (typically) 10 kcal/mole. As the transition state is the same for the forward and reverse reactions, the activation energy for the reverse reaction will be 10 kcal/mole more than for the forward reaction. This means that the reverse rate is slower than the forward rate by a factor of 107.

Therefore, alkylamines will be hydrolytically stable in the natural environment because their reactions with water are thermodynamically challenged and the activation energy demand is of a magnitude that prevents these reactions from proceeding at ambient temperature.  Therefore, hydrolysis testing is not indicated for the substance, which is a tertiary alkylamine.