A study on reaction pathways for the cyclodehydration of hexedioic acids to 2,5-furandicarboxylic acid

• Published in: Zhejiang da xue xue bao. Journal of Zhejiang University. Sciences edition. Li xue ban Vol. 49; no. 2; pp. 195 - 200
• Main Authors: Lyu, Xilei, Chen, Xujie, Zheng, Liping, Wei, Xiwen, Tian, Penghui, Jiang, Yuxi, Lyu, Xiuyang
• Format: Journal Article
• Language: Chinese
• Published: Hangzhou Zhejiang University 01.03.2022; Zhejiang University Press
• Subjects: 2，5-呋喃二甲酸; Acids; Biodegradability; Carboxylic acids; Fourier transforms; Furoic acid; High performance liquid chromatography; Mass spectrometry; NMR; Nuclear magnetic resonance; Polyethylenes; Qualitative analysis; Sulfuric acid; 反应路径; 己糖二酸; 脱水环合
• ISSN: 1008-9497
• DOI: 10.3785/j.issn.1008-9497.2022.02.008

2,5-furandicarboxylic acid (2,5-FDCA) is a monomer of biodegradable polyethylene 2,5-furandicarboxylate (PEF), however, its cost is high. Production of 2,5-FDCA from the cyclodehydration of hexedioic acids (HAs) is one of promising pathways, but facing the problems that it is difficult to detect the side-products and the reaction pathways is unclear. In this work, the side-products of HAs cyclodehydration were qualitative analyzed by high performance liquid chromatography (HPLC), high-resolution mass spectrometry (HRMS), nuclear magnetic resonance (NMR) and Fourier transform infrared spectroscopy (FTIR). The 2-furoic acid and 3-hydroxy-2-oxopyran-6-carboxylic acid (HOCA) were determined as the two main side-products. The reaction pathways for the cyclodehydration of different hexedioic acids are similar when using H2SO4 as catalysts: the Galactaric acid is tended to be converted to HOCA, while calcium saccharate is more likely to be converted to 2,5-FDCA. Combined with the works already reported and the resul