POLYSTYRENE SULFONIC-ACID ESTERS AS ALKYLATING-AGENTS - PREPARATION OF UNSYMMETRICAL SECONDARY-AMINES

Spherical beads (210-290 mu) of styrene-divinyl benzene (10%) copolyme r have been chlorosulfonated and reacted with alcohols to give corresp onding sulfonate eaters. Their reactions with primary amines, i.e. pro pyl amine and aniline, give the corresponding secondary amines in reas onable yields (67-76%). The resulting secondary amines are obtained by a simple filtration and distillation. Regeneration of the polymeric s upport can readily be achieved by acidification and subsequent reactio n with thionyl chloride. The present method offers an alternative proc edure for the preparation of unsymmetrical secondary amines.