Skip to main content

Advertisement

Official Journal of the Japan Wood Research Society

Journal of Wood Science Cover Image

Electropolymerization of coniferyl alcohol

Article metrics

  • 193 Accesses

  • 4 Citations

Abstract

Electropolymerization of coniferyl alcohol was carried out in an aqueous system (0.2 M NaOH) and in an organic solvent system [CH2Cl2/methanol (4:1 v/v) in the presence of 0.2 M LiClO4] to produce a dehydrogenation polymer (DHP) - artificial lignin. In both systems, the polymerization of coniferyl alcohol was visually confi rmed. In the aqueous system, no dimer was detected in the reaction medium after electropolymerization, suggesting that endwise polymerization occurred on the electrode surface. Thioacidolysis degradation revealed that the obtained polymers had numerous 8-O-4′ linkages. The electropolymerization products obtained in the organic solvent system also had numerous 8-O-4′ linkages; in particular, the polymers obtained in the initial polymerization stage. This was probably because of the limited area available for reaction and the orientation of coniferyl alcohol on the electrode surface controlled the polymerization.

References

  1. 1.

    Sarkanen KV, Ludwig CH (1971) Definition and nomenclature. In: Sarcanen KV, Ludwig CH (eds) Lignins, occurrence, formation, structure and reactions. Wiley, New York, pp 1–17

  2. 2.

    Monties B, Fukushima K (2002) Occurrence, function and biosynthesis of lignins. In: Hofrichter M, Steinbüchel A (eds) Biopolymers, vol 1. Wiley, Weinheim, Germany, pp 1–64

  3. 3.

    McCarthy JL, Islam A (2000) Lignin chemistry, technology, and utilization: a brief history. In: Glasser WG, Northey RA, Schuultz TP (eds) Lignin: historical, biological, and material perspectives. ACS Symposium Series 742, American Chemical Society, Washington DC, pp 2–99

  4. 4.

    Sarkanen KV (1971) Precursors and their polymerization. In: Sarcanen KV, Ludwig CH (dds) Lignins, occurrence, formation, structure and reactions. Wiley, New York, pp 95–155

  5. 5.

    Tobimatsu Y, Takano T, Kamitakahara H, Nakatsubo F (2006) Studies on the dehydrogenative polymerizations of monolignol β-glycosides. Part 2: horseradish peroxidase-catalyzed dehydrogenative polymerization of isoconiferin. Holzforschung 60:513–518

  6. 6.

    Higuchi T, Ogino K, Tanahashi M (1971) Effect of polysaccharides on dehydropolymerization of coniferyl alcohol. Wood Res 51:1–11

  7. 7.

    Terashima N, Atalla RH, Ralph SA, Landucci LL, Lapierre C, Monties B (1995) New preparations of lignin polymer models under conditions that approximate cell wall lignification. I. Synthesis of novel lignin polymer models and their structural characterization by 13C NMR. Holzforschung 49:521–527

  8. 8.

    Terashima N, Atalla RH, Ralph SA, Landucci LL, Lapierre C, Monties B (1996) New preparations of lignin polymer models under conditions that approximate cell wall lignification. II. Structural characterization of the models by thioacidolysis. Holzforschung 50:9–14

  9. 9.

    Cathala B, Monties B (2001) Influence of pectins on the solubility and the molar mass distribution of dehydrogenative polymer (DHPs, lignin model compounds). Int J Biol Macromol 29:45–51

  10. 10.

    Barakat A, Putaux J-L, Saulnier L, Chabbert B, Cathala B (2007) Characterization of arabinoxylan-dehydrogenation polymer (synthetic lignin polymer) nanoparticles. Biomacromolecules 8:1236–1245

  11. 11.

    Nakamura R, Matsushita Y, Umemoto K, Usuki A, Fukushima K (2006) Enzymatic polymerization of coniferyl alcohol in the presence of cyclodextrins. Biomacromolecules 7:1929–1934

  12. 12.

    Rolando C, Monties B, Lapierre C (1992) Thioacidolysis. In: Lin SY, Dence CW (eds) Methods in lignin chemistry. Springer, Berlin Heidelberg New York, pp 334–349

  13. 13.

    Gattrell M, Kirk DW (1993) A study of electrode passivation during aqueous phenol electrolysis. J Electrochem Soc 140:903–911

  14. 14.

    Gattrell M, Kirk DW (1993) A study of the oxidation of phenol at platinum and preoxidized platinum surfaces. J Electrochem Soc 140:1534–1540

  15. 15.

    Ciszewski A, Milczarek G (2001) Preparation and general properties of chemically modified electrodes based on electrosynthesized thin polymeric films derived from eugenol. Electroanalysis 13:860–867

  16. 16.

    Ezerskis Z, Jusis Z (2001) Electropolymerization of chlorinated phenols on a Pt electrode in alkaline solution part I: a cyclic voltammetry study. J Appl Electrochem 31:1117–1124

  17. 17.

    Milczarek G, Ciszewski A (2003) Permselective properties of electropolymerized guaiacol derivatives. Electroanalysis 15:529–532

  18. 18.

    Ferreira M, Vareka H, Torresi RM, Tremiliosi-Filho G (2006) Electrode passivation caused by polymerization of different phenolic compounds. Electrochim Acta 52:434–442

  19. 19.

    Aminoff H, Brounow G, Falck K, Miksche GE (1974) The dimerization of coniferyl alcohol in aqueous sodium hydroxide. Acta Chem Scand B 28:373–374

  20. 20.

    Soriaga MP, Hubbard AT (1982) Determination of orientation of adsorbed molecules at solid–liquid interfaces by thin-layer electrochemistry: aromatic compounds at platinum electrodes. J Am Chem Soc 104:2735–2742

  21. 21.

    Soriaga MP, Stickney JL, Hubbard AT (1983) Electrochemical oxidation of aromatic compounds adsorbed on platinum electrodes: the influence of molecular orientation. J Electroanal Chem 144:207–215

Download references

Author information

Correspondence to Yasuyuki Matsushita.

Additional information

Part of this report was presented at the 52nd Lignin Symposium, Utsunomiya, Japan, November, 2007

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Matsushita, Y., Sekiguchi, T., Ichino, R. et al. Electropolymerization of coniferyl alcohol. J Wood Sci 55, 344–349 (2009) doi:10.1007/s10086-009-1037-1

Download citation

Key words

  • Electropolymerization
  • Coniferyl alcohol
  • Lignin
  • Dehydrogenation polymers
  • Thioacidolysis