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  • The effect of coumaryl alcohol incorporation on the structure and composition of lignin dehydrogenation polymers.

The effect of coumaryl alcohol incorporation on the structure and composition of lignin dehydrogenation polymers.

Biotechnology for biofuels (2017-12-08)
Anne E Harman-Ware, Renee M Happs, Brian H Davison, Mark F Davis
ABSTRACT

Lignin dehydrogenation polymers (DHPs) are polymers generated from phenolic precursors for the purpose of studying lignin structure and polymerization processes. Here, DHPs were synthesized using a Zutropfverfahren method with horseradish peroxidase and three lignin monomers, sinapyl (S), coumaryl (H), and coniferyl (G) alcohols, in the presence of hydrogen peroxide. The H monomer was reacted with G and a 1:1 molar mixture of S:G monomers at H molar compositions of 0, 5, 10, and 20 mol% to study how the presence of the H monomer affected the structure and composition of the recovered polymers. At low H concentrations, solid-state NMR spectra suggest that the H and G monomers interact to form G:H polymers that have a lower average molecular weight than the solely G-based polymer or the G:H polymer produced at higher H concentrations. Solid-state NMR and pyrolysis-MBMS analyses suggest that at higher H concentrations, the H monomer primarily self-polymerizes to produce clusters of H-based polymer that are segregated from clusters of G- or S:G-based polymers. Thioacidolysis generally showed higher recoveries of thioethylated products from S:G or S:G:H polymers made with higher H content, indicating an increase in the linear ether linkages. Overall, the experimental results support theoretical predictions for the reactivity and structural influences of the H monomer on the formation of lignin-like polymers.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
Sinapyl alcohol, technical grade, 80%
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100 mg
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HUF 89,200.00
Sigma-Aldrich
Allyl methyl sulfone, 96%
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5 g
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HUF 66,800.00
Sigma-Aldrich
Coniferyl alcohol, 98%
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100 mg
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HUF 48,800.00
1 g
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HUF 151,000.00