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Mechanism of Microwave‐Assisted Pyrolysis of Glucose to Furfural Revealed by Isotopic Tracer and Quantum Chemical Calculations
Author(s) -
Bao Liwei,
Shi Lei,
Luo Hu,
Kong Lingzhao,
Li Shenggang,
Wei Wei,
Sun Yuhan
Publication year - 2017
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201700621
Subject(s) - furfural , pyrolysis , quantum chemical , tracer , chemistry , mechanism (biology) , microwave , chemical physics , chemical engineering , catalysis , organic chemistry , nuclear physics , physics , molecule , quantum mechanics , engineering
Abstract Glucose labeled with 13 C or 18 O was used to investigate the mechanism of its conversion into furfural by microwaveassisted pyrolysis. The isotopic content and location in furfural were determined from GC–MS and 13 C NMR spectroscopic measurements and data analysis. The results suggest that the carbon skeleton in furfural is mainly derived from C1 to C5 of glucose, whereas the C of the aldehyde group and the O of the furan ring in furfural primarily originate from C1 and O5 of glucose, respectively. For the first time, the source of O in the furan ring of furfural was elucidated directly by experiment, providing results that are consistent with predictions from recent quantum chemical calculations. Moreover, further theoretical calculations indicate substantially lower energy barriers than previous predictions by considering the potential catalytic effect of formic acid, which is one of the pyrolysis products. The catalytic role of formic acid is further confirmed by experimental evidence.