Effect of a phase-transfer catalyst on the chemical modification of poly(vinyl chloride) by substitution with thiocyanate as a nucleophile

Tomohito Kameda, Masahiko Ono, Guido Grause, Tadaaki Mizoguchi, Toshiaki Yoshioka

Research output: Contribution to journalArticlepeer-review

8 Citations (Scopus)

Abstract

This study examined the effect of the phase-transfer catalysts tetrabutylammonium bromide (TBAB) and tetrabutylammonium hydrogen sulfate (TBAHS) on the chemical modification of poly(vinyl chloride) (PVC) by substitution with thiocyanate as a nucleophile. TBAB accelerated the dechlorination of PVC in SCN/ethylene glycol (EG) solution. Furthermore, the addition of TBAB to SCN/EG solution improved the substitution of the Cl in PVC with SCN in solution. The addition of TBAB or TBAHS to SCN/H2O solution promoted the dechlorination of PVC, whereas dechlorination did not occur without the catalyst. The catalysts preferred substitution to the elimination of HCl in SCN/H2O solution, and TBAB was slightly superior to TBAHS in terms of the degree and selectivity of the substitution. The addition of nitrobenzene to SCN/H2O solution with TBAB increased the degree of substitution. Consequently, phase-transfer catalysts, particularly TBAB, were very effective at promoting the substitution of Cl in PVC with SCN in solution.

Original languageEnglish
Pages (from-to)362-366
Number of pages5
JournalMaterials Chemistry and Physics
Volume118
Issue number2-3
DOIs
Publication statusPublished - 2009 Dec 15

Keywords

  • Nucleophilic substitution
  • Phase-transfer catalyst
  • Poly(vinyl chloride)
  • Thiocyanate

ASJC Scopus subject areas

  • Materials Science(all)
  • Condensed Matter Physics

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