Abstract
Reactions of aniline with 1-bromobutane to formN-butylaniline andN,N-dibutylaniline were performed in single-phase aqueous surfactant systems. Reaction rate, yield, and selectivity of theN-alkyl product were monitored for different initial compositions, and much higher reaction rate, yield, and selectivity were observed in comparison to reactions of neat components. Excess aniline increased yield and selectivity, while excess 1-bromobutane had the opposite effect. The lipophilic reactant (1-bromobutane) and both products are solubilized almost entirely in the surfactant micelles. The formation of relatively small amounts ofN,N-dibutylaniline effectively inhibited further alkylation ofN-butylaniline, so that high selectivities (>20) of theN-alkyl were obtained. Added sodium hydroxide caused small decreases in yield and selectivity and showed that pH-dependent dissociation equilibria of the various amine species do not have a major influence on reaction characteristics.
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