Effect of the nucleophilicity and solvent on the chemical modification of flexible poly(vinyl chloride) by substitution

Tomohito Kameda, Yuuzou Fukuda, Guido Grause, Toshiaki Yoshioka

Research output: Contribution to journalArticlepeer-review

6 Citations (Scopus)


The chemical modification might become an alternative to the thermal degradation of waste polyvinylchloride (PVC). Therefore, the nucleophile substitution of chlorine from flexible PVC by hydroxide (OH-), thiocyanate (SCN-), azide (N3-), and iodide (I-) was investigated in ethylene glycol (EG) at 190°C. With the exception of I-, all nucleophiles used resulted in substitution yields of about 20%. However, also high elimination yields were observed. When SCN was used as the nucleophile, the substitution/elimination ratio increased with decreasing temperature. The product at 150°C contained a mixed structure of thiocyanate and isothiocyanate groups, while at 190°C, only the structure of isothiocyanate was present the product, due to the isomerization of the S-C=N group under the formation of N=C=S at elevated temperatures. The substitution and dehydrochlorination yields increased with an increasing molar SCN/Cl ratio. When EG was replaced by diethylene glycol (DEG) or triethylene glycol (TEG), the dehydrochlorination was found to proceed more rapidly. The use of a solvent with a lower polarity improved the contact between the solvent and the polymer; however, solvents with a lower polarity favor the elimination over the substitution. Therefore, the substitution-elimination ratio increased in the order EG > DEG > TEG. POLYM. ENG. SCI., 2011.

Original languageEnglish
Pages (from-to)1108-1115
Number of pages8
JournalPolymer Engineering and Science
Issue number6
Publication statusPublished - 2011 Jun

ASJC Scopus subject areas

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


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