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

Author

Listed:
  • 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)

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.

Suggested Citation

  • Yu Qi & Jinyan Wang & Yan Kou & Hongchang Pang & Shouhai Zhang & Nan Li & Cheng Liu & Zhihuan Weng & Xigao Jian, 2019. "Synthesis of an aromatic N-heterocycle derived from biomass and its use as a polymer feedstock," Nature Communications, Nature, vol. 10(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:10:y:2019:i:1:d:10.1038_s41467-019-10178-0
    DOI: 10.1038/s41467-019-10178-0
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