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Regioselective synthesis of lignin-derived dianilines for high-performance polyurethane-urea elastomers
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DOI：10.1039/D6GC00757K.png)
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Abstract
En 中文
Primary anilines; especially dianilines; are the fundamental building blocks in the field of fine chemicals and materials. Lignin is an abundant renewable aromatic compound resource in nature; its high-value utilization plays a crucial role in enhancing the economic feasibility of biorefinery. Efficient production of dianilines from lignin is highly desired; but extremely challenging. In this study; an innovative strategy for the sustainable production of dianilines from lignin-derived phenolic monomers was reported. Regioselective synthesis of m; m′-; o; m′- and o; o′-dianilines via a Smiles rearrangement–condensation sequence or a condensation–Smiles rearrangement sequence was systematically compared. The hitherto unconsidered isomerization and acid-catalyzed cleavage mechanism among m; m′-; o; m′- and o; o′-bisphenols was reported. The “stepwise amination” process was proposed for the Smiles rearrangement of bisphenols according to density functional theory (DFT) calculations. Furthermore; the lignin-derived m; m′-; o; m′- and o; o′-dianilines were applied as sustainable chain extenders in the manufacture of polyurethane-urea elastomers and their effects on the properties of the polymers were investigated. Lignin-derived o; m′-dianiline exhibited superior mechanical properties compared to the traditional petroleum-based dianiline chain extenders methylene diphenylamine (MDA) and 4; 4′-methylene-bis-(2-chloroaniline) (MOCA); suggesting the application potential of lignin-derived dianilines in the field of materials.
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