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Chemical modification and dechlorination of polyvinyl chloride by substitution with thiocyanate as a nucleophile
Author(s) -
Kameda Tomohito,
Ono Masahiko,
Grause Guido,
Mizoguchi Tadaaki,
Yoshioka Toshiaki
Publication year - 2010
Publication title -
polymer engineering and science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.503
H-Index - 111
eISSN - 1548-2634
pISSN - 0032-3888
DOI - 10.1002/pen.21512
Subject(s) - nucleophilic substitution , thiocyanate , chemistry , substitution reaction , ethylene glycol , solvent , yield (engineering) , medicinal chemistry , dimethyl sulfoxide , dimethylformamide , elimination reaction , organic chemistry , polymer chemistry , materials science , metallurgy
This study examined the chemical modification of polyvinyl chloride (PVC) by substitution with SCN (thiocyanate) 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/tetrahydrofuran (THF)‐DMSO (1:2) proceeded at room temperature, favoring the substitution over elimination. The isomerization of SCN was observed, resulting only in NCS (isothiocyanate) at room temperature and SCN (thiocyanate) at 190°C. POLYM. ENG. SCI., 2010. © 2009 Society of Plastics Engineers