Chemical modification and dechlorination of polyvinyl chloride by substitution with thiocyanate as a nucleophile

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

Research output: Contribution to journalArticle

10 Citations (Scopus)

Abstract

This study examined the chemical modification of polyvinyl chloride (PVC) by substitution with SCN (thiocya-nate) as a nucleophile. The effects of temperature, molar SCN/Cl ratio, and solvent on the substitution by SCN and the elimination of HCl were investigated. In SCN/EG (ethylene glycol) solution, the substitution/dechlorination ratio increased with decreasing temperature. The dechlorination yield increased with an increasing molar SCN/Cl ratio, favoring the substitution over the elimination. When N,N-dimethylformamide (DMF) and dimethyl sulfoxide (DMSO) solutions were used as solvents, DMF favored the substitution, whereas DMSO favored the elimination. In the SCN/DMF solution, the substitution yield and the substitution/dechlorination ratio increased with increasing temperature. Higher temperatures favored the substitution over the elimination in SCN/ DMF. Furthermore, the reaction of PVC in SCN/tetrahy-drofuran (THF)-DMSO (1:2) proceeded at room temperature, favoring the substitution over elimination. The isomerization of SCN was observed, resulting only in - N=C=S (isothiocyanate) at room temperature and - S - C≡N (thiocyanate) at 190°C.

Original languageEnglish
Pages (from-to)69-75
Number of pages7
JournalPolymer Engineering and Science
Volume50
Issue number1
DOIs
Publication statusPublished - 2010 Jan 1

ASJC Scopus subject areas

  • Chemistry(all)
  • Polymers and Plastics
  • Materials Chemistry

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