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Issue 12, 2020
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Statistical design of experiments for production and purification of vanillin and aminophenols from commercial lignin

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Abstract

Lignin is a complex polyphenolic substance that collectively represents the largest renewable source of aromatic carbon on Earth. Despite low yield and purity from depolymerized lignin, bio-derived vanillin (4-hydroxy-3-methoxybenzaldehyde) is a desirable molecule in the food/beverage and fragrance industries. To maximize vanillin yield from commercially-available softwood lignin, a series of oxidation reactions were conducted using a Box-Behnken statistical design. By varying time, temperature and O2 pressure, optimal conditions were selected using the Response Surface Method, and a maximum vanillin yield of 5.3 wt% was achieved. Flash chromatography of depolymerized lignin was investigated by comparing anion exchange and reversed-phase resins and fractions were characterized by GC-MS, GPC-HPLC, FT-IR and NMR. Anion exchange separations using 1M NaCl as the sole mobile phase reached a vanillin purity of 55 wt %. Lastly, the vanillin mixture was reacted via reductive amination, and facile acid-base work up led to the formation of 4-((diethylamino)methyl)-2-methoxyphenol at 94.3 wt % purity. The aminophenol is an intermediate in the synthesis of pharmaceutical agents, ionic liquids and benzalkonium salts.

Graphical abstract: Statistical design of experiments for production and purification of vanillin and aminophenols from commercial lignin

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Supplementary files

Article information


Submitted
08 Apr 2020
Accepted
15 May 2020
First published
15 May 2020

Green Chem., 2020,22, 3917-3926
Article type
Paper

Statistical design of experiments for production and purification of vanillin and aminophenols from commercial lignin

S. Liu, L. Das, D. N. Blauch, C. Veronee, C. Dou, J. Gladden, N. Sun and A. M. Socha, Green Chem., 2020, 22, 3917
DOI: 10.1039/D0GC01234C

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