over liquid-phase reactions since the catalyst can be more Reactions of aniline with 1-bromobutane to form N-butylaniline easily recovered for recycle or disposal. Catalysts that have and N,N-dibutylaniline were performed in single-phase aqueous been studied include oxides, supported oxides, zeolites, and surfactant systems. Reaction rate, yield, and selectivity of the Nsolid acids (6, 7). Effects of temperature, pressure and cataalkyl product were monitored for different initial compositions, lyst have been reported in Narayanan et al. (6), Bayer et and much higher reaction rate, yield, and selectivity were observed al. (8), and Chen et al. (9). Selective syntheses of monoin comparison to reactions of neat components. Excess aniline
or dialkylated by reaction with aldehyde or ketone have also increased yield and selectivity, while excess 1-bromobutane had been reported (10,11).
the opposite effect. The lipophilic reactant (1-bromobutane) and
Alkylation can also be carried out by reacting aniline with both products are solubilized almost entirely in the surfactant micelles. The formation of relatively small amounts of N,N-dibutyl-alkyl halide. Although not feasible for the preparation of aniline effectively inhibited further alkylation of N-butylaniline, so primary or secondary amines (12), this reaction is useful for that high selectivities (ΓΊ20) of the N-alkyl were obtained. Added the preparation of tertiary amines and quaternary ammonium sodium hydroxide caused small decreases in yield and selectivity salts. In the present investigation, the alkylation of aniline and showed that pH-dependent dissociation equilibria of the variby 1-bromobutane in aqueous surfactant solutions was invesous amine species do not have a major influence on reaction chartigated. In the absence of catalysts or protective groups, the acteristics.