Highly functionalized polystyrene by direct metalation-carboxylation

Sándor Nemes, János Borbély, Jenö Borda, Tibor Kelen

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Polystyrene was directly metalated using 1:1 mixture of n-butyllithium (n-BuLi) and potassium-t-butoxide (t-BuOK) in cyclohexane/hexanes at ambient temperature. The metalated polymer on reaction with solid carbon dioxide followed by a metal-proton exchange gave a carboxylated polymer containing 6.38-6.57 mmol acid/g polymer which corresponds to the introduction of carboxyl groups on 94-97% of the repeat units of polystyrene. Based on 13C nMR spectra meta, para and ortho aromatic ring substitution was proposed. No detectable backbone carboxylation occurs. the distribution of carboxylated sites on the aromatic ring: 9% ortho, 58% meta and 33% para. Quantitative 13C NMR analyses indicates essentially quantitative functionalization.

Original languageEnglish
Pages (from-to)123-128
Number of pages6
JournalPolymer Bulletin
Volume27
Issue number2
DOIs
Publication statusPublished - Nov 1 1991

    Fingerprint

ASJC Scopus subject areas

  • Chemistry(all)
  • Condensed Matter Physics
  • Polymers and Plastics
  • Materials Chemistry

Cite this