Polystyrene sulfonic acid esters as alkylating agents: preparation of unsymmetrical secondary amines

• Published in: Reactive & functional polymers Vol. 29; no. 2; pp. 123 - 128
• Main Authors: Biçak, Niyazi, Filiz Şenkal, Bahire
• Format: Journal Article
• Language: English
• Published: Amsterdam Elsevier B.V 1996; Elsevier Science
• Subjects: Applied sciences; Chlorosulfonated polystyrene- co-DVB resin; Exact sciences and technology; N-allyl aniline; Organic polymers; Physicochemistry of polymers; Polymer-supported synthesis; Properties and characterization; Propyl benzylamine; Special properties (catalyst, reagent or carrier); Unsymmetrical secondary amines; Polymer-supported synthesis; Propyl benzylamine; N-allyl aniline; Unsymmetrical secondary amines; Chlorosulfonated polystyrene- co-DVB resin; Benzene(divinyl) copolymer; Asymmetric molecule; Reagent polymer; Experimental study; Alkylation; Crosslinked copolymer; Alkylating agent; Chemical modification; Reactivity; Styrenesulfonate copolymer; Preparation; Radical copolymerization; Primary amine; Secondary amine
• ISSN: 1381-5148
• DOI: 10.1016/1381-5148(96)00007-7

Spherical beads (210–290 μ) of styrene-divinyl benzene (10%) copolymer have been chlorosulfonated and reacted with alcohols to give corresponding sulfonate esters. Their reactions with primary amines, i.e. propyl amine and aniline, give the corresponding secondary amines in reasonable yields (67–76%). The resulting secondary amines are obtained by a simple filtration and distillation. Regeneration of the polymeric support can readily be achieved by acidification and subsequent reaction with thionyl chloride. The present method offers an alternative procedure for the preparation of unsymmetrical secondary amines.