TY - JOUR
T1 - Tuning lignin properties by mild ionic-liquid-mediated selective alcohol incorporation
AU - Wang, Zhiwen
AU - Zhang, Zhenlei
AU - Wang, Hongqi
AU - Deuss, Peter J.
N1 - Funding Information:
Z.W. and Z.Z. acknowledge the China Scholarship Council, China for funding (grant number 201706300138 and 201704910922 , respectively). The authors would like to acknowledge Johanna H.L. Kaelen and Lambert J. Deuss for providing the walnut shells; A. Bakker, Harkstede for providing birch wood; Prof. Gert Jan Euverink for providing reed for lignin isolation; Ciaran W. Lahive for valuable discussion; and Xianyuan Wu for synthesis of 4-(3-hydroxypropyl)-2,6-dimethoxphenol. Analytical support was provided by Leon Rohrbach, Johan Kemmink, Gert-Jan Boer, Johan Kemmink, and Pieter vd Meuien.
Publisher Copyright:
© 2022 Elsevier Inc.
PY - 2022/6/16
Y1 - 2022/6/16
N2 - The synthesis of ideal, well-defined, functionalized lignins is of great significance for realizing the full valorization potential of lignocellulosic biomass. Here, the application of acidified triethylammonium triflate is reported, allowing for the selective benzylic alkoxylation of different lignins at room temperature. Full benzylic alkoxylation of typically hard-to-process, high-molecular-weight lignin was achieved in this medium by simple mixing with different alcohols. Limited lignin degradation was observed, and lignin modification was also achieved within the lignocellulosic matrix. This allows the method to be used as a biomass pretreatment, which was shown to also enhance enzymatic saccharification. The reactivity, stability, and hydrophobicity of the lignin can be tuned based on the alcohol used. Effective recovery of the ionic liquid and recycling of the ionic liquid was achieved. Thus, a straightforward mild method is demonstrated to introduce new functionality in lignin, allowing it to be tuned towards novel applications.
AB - The synthesis of ideal, well-defined, functionalized lignins is of great significance for realizing the full valorization potential of lignocellulosic biomass. Here, the application of acidified triethylammonium triflate is reported, allowing for the selective benzylic alkoxylation of different lignins at room temperature. Full benzylic alkoxylation of typically hard-to-process, high-molecular-weight lignin was achieved in this medium by simple mixing with different alcohols. Limited lignin degradation was observed, and lignin modification was also achieved within the lignocellulosic matrix. This allows the method to be used as a biomass pretreatment, which was shown to also enhance enzymatic saccharification. The reactivity, stability, and hydrophobicity of the lignin can be tuned based on the alcohol used. Effective recovery of the ionic liquid and recycling of the ionic liquid was achieved. Thus, a straightforward mild method is demonstrated to introduce new functionality in lignin, allowing it to be tuned towards novel applications.
KW - benzylic alkoxylation
KW - biomass pretreatment
KW - enzymatic saccharification
KW - ionic liquid
KW - lignin modification
KW - reductive hydrogenolysis
KW - residual enzyme lignin
KW - SDG9: Industry innovation and infrastructure
UR - http://www.scopus.com/inward/record.url?scp=85132773366&partnerID=8YFLogxK
U2 - 10.1016/j.checat.2022.04.005
DO - 10.1016/j.checat.2022.04.005
M3 - Article
AN - SCOPUS:85132773366
SN - 2667-1107
VL - 2
SP - 1407
EP - 1427
JO - Chem Catalysis
JF - Chem Catalysis
IS - 6
ER -