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Kinetics of the hydroxymethylation of phenol II: values of rate parameters and results of simulation experiments

Abstract

The reaction course of the sodium hydroxidecatalyzed hydroxymethylation of phenol was analyzed by use of high-performance liquid chromatography (HPLC), and the rate constants for the seven reactions taking place consecutively and competitively were evaluated by means of a computer simulation technique. Calibration was done at the quantification of the six phenolic monomers from the peak areas in the HPLC chromatogram, taking the differences in molar ultraviolet absorption intensities of the six compounds into account. The values of the energies of activation for the seven reactions obtained differed greatly from those reported by Eapen and Yeddanapalli. Simulation experiments carried out by use of the newly obtained rate parameters showed that the amounts of phenol left unreacted and 2,4,6-trihydroxymethylphenol in the final reaction product increased as the reaction temperature was increased and the alkali/phenol molar ratio decreased. These phenomena can be attributed to the differences in the energies of activation for the seven reactions and differences in the acid strengths of the six phenolic monomers.

References

  1. 1.

    Higuchi M, Nohno S, Tohmura S (1998) Kinetics of the hydroxymethylation of phenol. I. Rate equation and method of analysis. J Wood Sci 44:198–203

  2. 2.

    Knop A, Pilato LA (eds) (1985) Phenolic resins: chemistry, applications and performance: future directions. Springer, Berlin, pp 36–40

  3. 3.

    Tohmura S, Higuchi M, Hattori Y, Sakata I (1994) Acceleration of the cure of phenolic resin adhesives. IV. Kinetics of the condensation reaction of 2,4,6-trimethylolphenol. Mokuzai Gakkaishi 40:390–398

  4. 4.

    Eapen KC, Yeddanapalli LM (1968) Kinetics and mechanism of the alkali-catalyzed addition of formaldehyde to phenol and substituted phenols. Mokromol Chem 119:4–16

  5. 5.

    Knop A, Pilato LA (eds) (1985) Phenolic resins: chemistry, applications and performance: future directions. Springer, Berlin, p 26

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Correspondence to Mitsuo Higuchi.

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Higuchi, M., Nohno, S., Morita, M. et al. Kinetics of the hydroxymethylation of phenol II: values of rate parameters and results of simulation experiments. J Wood Sci 45, 306–312 (1999). https://doi.org/10.1007/BF00833495

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Key words

  • Hydroxymethylation of phenol
  • Rate constants
  • Energies of activation
  • Computer simulation