Kinetic and structural features of furan compounds as inhibitors of the radical polymerization of vinyl acetate

Abstract

Some furan compounds bearing a double bond in the side group have been examined as inhibitors of the radical polymerization of vinyl acetate initiated by AIBN in ethyl acetate at 60 ºC. The inhibition effect was found to follow the order: furfurylidenacetone > furylacrolein > furanacrylic acid > furylacrylmorpholinamide as a consequence of the greater stabilization of the radical formed. The site of radical attack can be considered either as the C-5 position of the furan ring or as the double bond of the side group. The compounds taken as models such as 5-methylfuranacrylic acid and furfurylidenbutanal indicate that both positions can participate in the inhibitory process

Synthesis of Novel Chain‐End‐Functionalized Polyethylenes via Thiol‐ene Click Chemistry

“…It was not easy to introduce furfuryl mercaptan into vinyl‐terminated polyethylene because furfuryl mercaptan could act as a free radical reaction inhibitor . Therefore, furfuryl‐terminated functional polyethylene (Cef‐PE 2 ) was obtained by thiol‐ene click chemistry and the yield increased from 19% to more than 95% under optimized experimental conditions.…”

Kinetic and sensitivity approach to the mechanism of inhibited polymerization of vinyl acetate in the presence of furan compounds

“…•The reactivity order obtained from the estimated value of the k trs is the same as the order obtained from the kinetic measurements [8] . It confirms the importance of stabilization of MZ* by conjugation on the strength of the inhibitor.…”

“…Since 1983 Rieumont and co-workers [5][6][7][8] have been studying thoroughly the kinetic features of the retarded and inhibited polymerization of vinyl acetate in the presence of furan compounds. The classical approach was complemented by a sensitivity analysis in order to discriminate between the determining, nondetermining and neglected steps of the mechanism.…”