Synthesis of Lignin Monomers

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By:Alexandria N. Tibbs

Introduction

Lignin is the second most abundant organic polymer. It is found in plants, majorly in trees. Its function is to serve in the assistance of water flow throughout the plant. It forms a barrier for the evaporation, trapping the water inside.

The structure of lignin is composed of the seemingly random combination of three monomers: p-coumaryl alcohol, coniferyl alcohol, and sinapyl alcohol.

Lignin Precursors

These lignin monomers are derived from their acid precursors through the reduction of an aldehyde to the corresponding alcohol. While the precursors, p-courmaric acid (4-hydroxycinnamic acid), ferulic acid (4-hydroxy-3-methoxycinnamic acid), and sinapic acid (4-hydroxy-3,5-diethoxycinnamic acid) may not be as abundant in nature, when it comes to the lab setting, these chemicals are easier to come by then their alcohol forms.

Materials

Diisobutylaluminum hydride solution (25 wt.% in toluene)

Product Number: 192724-100G

Quantity: 2

Price: $52.20

Toluene (Anhydrous, 99.8%)

Product Number: 244511-1L

Quantity: 1

Price: $60.50

Experimental

Results

Discussion

References

Lignin Biosynthesis and Structure

Oxidative Coupling during Lignin Polymerization is Determined by Unpaired Electron Delocalization within Parent Phenylpropanoid Radicals

[Overview from Lignin and Lignans: Advances in Chemistry]

Facile Large-Scale Synthesis of Coniferyl, Sinapyl, and p-Coumaryl Alcohol