Synthesis of an aromatic N-heterocycle derived from biomass and its use as a polymer feedstock

Yu Qi; Jinyan Wang; Yan Kou; Hongchang Pang; Shouhai Zhang; Nan Li; Cheng Liu; Zhihuan Weng; Xigao Jian

doi:10.1038/s41467-019-10178-0

Synthesis of an aromatic N-heterocycle derived from biomass and its use as a polymer feedstock

Nat Commun. 2019 May 8;10(1):2107. doi: 10.1038/s41467-019-10178-0.

Authors

Yu Qi¹, Jinyan Wang¹, Yan Kou², Hongchang Pang³, Shouhai Zhang¹, Nan Li¹, Cheng Liu¹, Zhihuan Weng⁴, Xigao Jian¹

Affiliations

¹ State Key Laboratory of Fine Chemicals, Liaoning High Performance Resin Engineering Research Center, Department of Polymer Science & Engineering, Dalian University of Technology, Dalian, 116024, China.
² Thermochemistry Laboratory, Liaoning Province Key Laboratory of Thermochemistry for Energy and Materials, Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Chinese Academy of Sciences, Dalian, 116023, China.
³ School of Chemical Engineering, Dalian University of Technology, Dalian, 116024, China.
⁴ State Key Laboratory of Fine Chemicals, Liaoning High Performance Resin Engineering Research Center, Department of Polymer Science & Engineering, Dalian University of Technology, Dalian, 116024, China. zweng@dlut.edu.cn.

Abstract

Aromatic N-heterocyclic compounds are very important chemicals, which are currently produced mostly from petroleum. Here we report that a pyridazine-based compound 6-(4-hydroxy-3-methoxyphenyl)pyridazin-3(2H)-one (GSPZ) can be efficiently synthesized by the Friedel-Crafts reaction of guaiacol and succinic anhydride, both of which can be derived from biomass. GSPZ is then treated with bio-based epichlorohydrin to prepare the epoxy resin precursor GSPZ-EP. With 4,4'-diaminodiphenylmethane as curing agent, GSPZ-EP possesses higher glass transition temperature (187 ^oC vs. 173 ^oC) and shows a 140%, 70 and 93% increase in char yield (in N₂), storage modulus (30 ^oC) and Young's modulus, respectively when compared with a standard petroleum-based bisphenol A epoxy resin. Moreover, the cured GSPZ-EP shows good intrinsic flame retardancy properties and is very close to the V-0 rating of UL-94 test. This work opens the door for production of aromatic N-heterocyclic compounds, which can be derived from biomass and employed to construct high performance polymers.

Publication types

Research Support, Non-U.S. Gov't