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.

Aromatic N-heterocyclic compounds are important chemicals, but produced from petroleum. Here the authors show a pyridazine-based compound 6-(4-hydroxy-3-methoxyphenyl)pyridazin-3(2H)-one, used as polymer feedstocks, can be synthesized by a Friedel-Crafts reaction from biomass starting materials.

Details

Title
Synthesis of an aromatic N-heterocycle derived from biomass and its use as a polymer feedstock
Author
Yu, Qi 1 ; Wang, Jinyan 1 ; Kou, Yan 2 ; Pang Hongchang 3 ; Zhang Shouhai 1 ; Li, Nan 1 ; Liu, Cheng 1   VIAFID ORCID Logo  ; Weng Zhihuan 1 ; Xigao, Jian 1 

1  Dalian University of Technology, State Key Laboratory of Fine Chemicals, Liaoning High Performance Resin Engineering Research Center, Department of Polymer Science & Engineering, Dalian, China (GRID:grid.30055.33) (ISNI:0000 0000 9247 7930) 
2  Chinese Academy of Sciences, Thermochemistry Laboratory, Liaoning Province Key Laboratory of Thermochemistry for Energy and Materials, Dalian National Laboratory for Clean Energy, Dalian Institute of Chemical Physics, Dalian, China (GRID:grid.9227.e) (ISNI:0000000119573309) 
3  Dalian University of Technology, School of Chemical Engineering, Dalian, China (GRID:grid.30055.33) (ISNI:0000 0000 9247 7930) 
Publication year
2019
Publication date
2019
Publisher
Nature Publishing Group
e-ISSN
20411723
Source type
Scholarly Journal
Language of publication
English
DOI
https://doi.org/10.1038/s41467-019-10178-0
ProQuest document ID
2221814301
Copyright
© The Author(s) 2019. This work is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.