Journal of Wood Science

, Volume 54, Issue 4, pp 329–331 | Cite as

Mechanism of formaldehyde adsorption of (+)-catechin

  • Toshiyuki Takano
  • Tomomi Murakami
  • Hiroshi Kamitakahara
  • Fumiaki Nakatsubo
Note

Abstract

The reaction of (+)-catechin with formaldehyde vapor was investigated as a model reaction of formaldehyde adsorption of (+)-catechin. It was found by H nuclear magnetic resonance spectroscopy, matrix-assisted laser desorption/ionization time-of-flight mass spectrometry, and gel permeation chromatography of the product that the vapor reaction of (+)-catechin with formaldehyde without a solvent or a catalyst proceeds via methylolation, condensation, and polymerization. This is the same as the reaction in a solvent in the presence of an acid or a base. The formation of polyoxymethylenes such as paraformaldehyde was not confirmed.

Key words

Adsorption (+)-Catechin Bark tannin Formaldehyde Vapor reaction 

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References

  1. 1.
    Takano R, Karasawa R (1978) Bark molded board Part 4. Reaction of bark with formaldehyde (in Japanese). Mokuzai to Gijyutsu 32:7–10Google Scholar
  2. 2.
    Hemingway RW, McGraw GW (1978) Formaldehyde condensation products of model phenols for conifer bark tannins. J Liq Chromatogr 1:163–179CrossRefGoogle Scholar
  3. 3.
    Pizzi A, Stephanou A (1993) A comparative 13C NMR study of polyflavonoid tannin extracts for phenolic polycondensates. J Appl Polym Sci 50:2105–2113CrossRefGoogle Scholar
  4. 4.
    Thompson D, Pizzi A (1995) Simple 13C-NMR methods for quantitative determinations of polyflavonoid tannin characteristics. J Appl Polm Sci 55:107–112CrossRefGoogle Scholar
  5. 5.
    Hillis WE, Urbach G (1959) The reaction of (+)-catechin with formaldehyde. J Appl Chem 9:474–482CrossRefGoogle Scholar
  6. 6.
    Kiatgrajai P, Wellons J, Gollob L, White JD (1982) Kinetics of polymerization of (+)-catechin with formaldehyde. J Org Chem 47:2913–2917CrossRefGoogle Scholar
  7. 7.
    Fechtal M, Riedl B, Calve L (1993) Modeling of tannins as adhesives. I Condensation of the (+)-catechin with formaldehyde. Holzforschung 47:419–424CrossRefGoogle Scholar
  8. 8.
    Takagaki A, Fukai K, Nanjo F, Hara Y (2000) Reactivity of green tea catechins with formaldehyde. J Wood Sci 46:334–338CrossRefGoogle Scholar
  9. 9.
    Saito N, Reilly M, Yazaki Y (2001) Chemical structures of (+)-catechin-formaldehyde reaction products (Stiasny precipitates) under strong acid conditions. Part 1. Solid-state 13C-NMR analysis. Holzforschung 55:205–213CrossRefGoogle Scholar
  10. 10.
    Ohara S (1997) Aldehyde compounds adsorbing capacity of bark tannins (in Japanese). Abstracts of the 47th Annual Meeting of the Japan Wood Research Society, p 410Google Scholar
  11. 11.
    Watanabe M (1999) Application of green tea catechins (in Japanese). Kagaku 54:30–32Google Scholar
  12. 12.
    Takagaki A, Fukai K, Nanjo F, Hara Y, Watanabe M, Sakuragawa S (2000) Application of green tea catechins as formaldehyde scavengers (in Japanese). Mokuzai Gakkaishi 46:231–237Google Scholar
  13. 13.
    Boyer F-D, Ducrot P-H (2005) Hydrogenation of substituted aromatic aldehydes: nucleophilic trapping of the reaction intermediate, application to the efficient synthesis of methylene linked flavanol dimers. Tetrahedron Lett 46:5177–5180CrossRefGoogle Scholar
  14. 14.
    Fisher T, Chao P, Upton G, Day A (2002) A 13C NMR study of the methylol derivatives of 2,4′— and 4,4′-dihydroxydiphenylmethanes found in resol phenol-formaldehyde resins. Magn Reson Chem 40:747–751CrossRefGoogle Scholar
  15. 15.
    Goetzky P, Pasch H (1986) Untersuchungen zur synthese und härtung von phenol-formaldehyd-harzen. Acta Polymerica 37:510–512CrossRefGoogle Scholar
  16. 16.
    Katano S, Hirose Y, Nakatsuka T (1974) Resorcinol resin VI. Intermediate products of resorcinol-formaldehyde reaction (2) (in Japanese) Mokuzai Gakkaishi 20:133–137Google Scholar
  17. 17.
    Fukuda W (1965) Polymerization of formaldehyde. In: Imoto M, Kakiuchi H, Kou K (eds) Formaldehyde — chemistry and application. Asakura Shoten, Tokyo, pp 47–100Google Scholar

Copyright information

© The Japan Wood Research Society 2008

Authors and Affiliations

  • Toshiyuki Takano
    • 1
  • Tomomi Murakami
    • 1
  • Hiroshi Kamitakahara
    • 1
  • Fumiaki Nakatsubo
    • 1
  1. 1.Division of Forest and Biomaterials Science, Graduate School of AgricultureKyoto UniversitySakyo-ku, KyotoJapan

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