Condensation reactions of phenolic resins VII: Catalytic effect of sodium bicarbonate for the condensation of hydroxymethylphenols

Naruyuki Kamo, Jun Tanaka, Mitsuo Higuchi, Tetsuo Kondo, Mitsuhiro Morita

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

This article describes the catalytic effect of NaHCO3 on condensation reactions of monomeric hydroxymethylphenols (HMPs) to elucidate the cure-acceleration mechanism. By comparison of the kinetics of self-condensations of HMPs, NaHCO3 was proved to increase the reactivity of para-hydroxymethyl groups. The changes of 13C nuclear magnetic resonance (NMR) chemical shifts on each HMP system with the additive indicated that the addition of NaHCO3 enhanced some molecular interactions between HMPs and NaHCO3, facilitating a resonance effect that might play a similar role in dissociation of the phenolic hydroxyl groups of HMPs. In addition, computational modeling by molecular orbital calculations elucidated that hydrogen carbonate anion (HCO 3 - ) forms an interaction between either the para-hydroxymethyl group and the phenolic hydroxyl group or between the two para-hydroxymethyl groups of HMPs by hydrogen bonds. From the experimental results, the authors proposed the mechanism of the catalytic action of NaHCO3: it appears to be due to the delocalization of an electron initiated by the interaction of the para-hydroxymethyl groups and the phenolic hydroxyl of HMPs with HCO 3 - through hydrogen bonds, which results in facilitating the formation of active species.

Original languageEnglish
Pages (from-to)325-330
Number of pages6
JournalJournal of Wood Science
Volume52
Issue number4
DOIs
Publication statusPublished - Aug 1 2006

All Science Journal Classification (ASJC) codes

  • Plant Science
  • Forestry
  • Chemical Engineering(all)

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