biostudies-literatureNomoura TJST-Mirai Program21544-21552https://www.ebi.ac.uk/biostudies/studies/S-EPMC11229084biostudies-literatureUnknown14(30)The authors previously proposed that 5-hydroxymethylfurfural (5-HMF) can be produced from the reducing ends of cellulose as a key intermediate during carbonization. The present work investigated the mechanisms by which furan and benzene rings are formed in cellulose char based on carbonization at 280 °C using ¹³C-labeled 5-HMF together with ¹³C-labeled glucose (as a model for the cellulose reducing ends). Glycerol was added to the 5-HMF to prevent the formation of stable glassy polymers. The resulting char was subjected to pyrolysis gas chromatography/mass spectrometry (764 °C, 5 s hold time) and the incorporation of ¹³C in furan-, phenol-, benzofuran- and benzene-type fragments was assessed. The apparent formation mechanisms include a direct rearrangement RSC advancesFuran and benzene ring formation in cellulose char: the roles of 5-HMF and reducing ends.PMC11229084JPMJMI20E3Nomoura TMinami EKawamoto HfalseFuran and benzene ring formation in cellulose char: the roles of 5-HMF and reducing ends.The authors previously proposed that 5-hydroxymethylfurfural (5-HMF) can be produced from the reducing ends of cellulose as a key intermediate during carbonization. The present work investigated the mechanisms by which furan and benzene rings are formed in cellulose char based on carbonization at 280 °C using ¹³C-labeled 5-HMF together with ¹³C-labeled glucose (as a model for the cellulose reducing ends). Glycerol was added to the 5-HMF to prevent the formation of stable glassy polymers. The resulting char was subjected to pyrolysis gas chromatography/mass spectrometry (764 °C, 5 s hold time) and the incorporation of ¹³C in furan-, phenol-, benzofuran- and benzene-type fragments was assessed. The apparent formation mechanisms include a direct rearrangement 2024-01-01T00:00:00Z2024 Jul2025-04-04T11:25:41.272Z2025-04-04T11:25:41.272ZS-EPMC112290843897947010.1039/d4ra03344b