Synthesis and Characterization of Lignin Monomers

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Abstract

Lignin is the second most abundant organic polymer. The structure of lignin is composed of three monomers: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol, which all are found in nature. These natural compounds are not cost friendly for undergraduate research. The carboxylic acid forms of these monomers (p-coumaric acid, ferulic acid, and sinapic acid) can be obtained commercially. This poster will discuss our synthetic approaches to produce the alcohol forms of lignin.

Lignin Monomers

p-Coumaryl alcohol

Coniferyl alcohol

Sinapyl alcohol

Introduction

Ferulates play important roles in plant growth and undergo radical coupling reactions to produce dimers and cross-linking. Significant quantities are now required by cell wall researchers increasing the the large scale production of these ferulates and other lignins similar to their make up.

Lignin Precursors

Methods/Experimentation

Materials

Ferulic acid

p-Coumaric acid

Sinapic acid

Synthesis Mechanism

Synthesis

  • Ethyl Ferulate: 10 g of ferulic acid dissolved in 100 mL ethanol and 5 mL of acetyl chloride. Solution stirred overnight. Volatiles removed by rotary evaporation (rotovap) at 40 C. (Ralph)
  • Esterification: 0.36 M ferulic acid in ethanol (500 mL) with concentrated HCl. Refluxed for two days. Cooled and ethanol evaporated under pressure (rotovap). Crude extract combined with ethyl acetate (250 mL). Solution dried over anhydrous MgSO4.

Results

HPLC Data.jpg

Discusion

Conclusion

References