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 () and Xigao Jian
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Yu Qi: Dalian University of Technology
Jinyan Wang: Dalian University of Technology
Yan Kou: Chinese Academy of Sciences
Hongchang Pang: Dalian University of Technology
Shouhai Zhang: Dalian University of Technology
Nan Li: Dalian University of Technology
Cheng Liu: Dalian University of Technology
Zhihuan Weng: Dalian University of Technology
Xigao Jian: Dalian University of Technology

Nature Communications, 2019, vol. 10, issue 1, 1-9

Abstract: 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.

Date: 2019
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DOI: 10.1038/s41467-019-10178-0

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