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Updated: Dec 11, 2025

Quantitative 31P NMR Analysis of Lignins and Tannins
Published on: August 2, 2021
Naphthalene Structures Derived from Lignins During Phenolation
Suxiang Li1, Lanlan Shi1, Chen Wang1
1State Key Laboratory of Pulp and Paper Engineering, South China University of Technology, Guangzhou, 510640, P. R. China.
Abstract:
Phenolation is a commonly used method to improve the reactivity of lignin for various applications. In this study, resinol lignin models (syringaresinol and pinoresinol) and eucalyptus alkali lignin were treated under acid-catalyzed phenolation conditions to investigate the products derived from resinol (β-β) structures of lignins. The phenolation products were characterized by means of GC-MS and NMR spectroscopy following separation using flash chromatography and thin-layer chromatography. A series of new naphthalene products were identified from phenolation of syringaresinol, and the corresponding guaiacyl analogs were also identified by GC-MS. The C1-Cα bond of these resinol compounds was cleaved to release syringol or guaiacol during phenolation. In addition, diphenylmethane products formed from phenol or phenol and syringol/guaiacol were found in the phenolation products. Comparatively, more naphthalene products were obtained by phenolation from syringaresinol than those obtained from pinoresinol. HSQC NMR characterization of the phenolated alkali lignin revealed that naphthalene structures formed in the phenolated lignin.
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