2026-10-11T16:39:05Z https://www.scidb.cn/oai

10.57760/sciencedb.38456 2026-05-29T17:51:40Z

2026-05-29 Mechanism of the β-Hydroxyethylation of Hydroquinone Catalyzed by Imidazole doi:10.57760/sciencedb.38456 en The catalytic performance of a series of imidazole derivatives in the β-hydroxyethylation reaction of hydroquinone (HQ) with ethylene carbonate (EC) to prepare hydroquinone bis(β-hydroxyethyl) ether (HQEE) was investigated. The results showed that the hydroxyethylation reaction occurs first on the imidazole ring to generate 1-(2-hydroxyethyl)imidazole derivative when the nitrogen atom at position 1 of the imidazole ring has a hydrogen atom. There are no significant differences for the catalytic performance of 1-substituted, 2-substituted, and multi-substituted imidazoles. Imidazole catalysts activate EC through a nucleophilic catalysis mechanism rather than activating HQ via a basic mechanism. The nitrogen atom at position 3 of the imidazole ring is the active site for activating EC ring-opening. The results of hectogram-scale synthesis show that the substituent effect of 1-substituted alkyl imidazoles was not significant, the by-product CO2 gas could remove reaction heat from the system in a timely manner, and the recrystallized HQEE product yield could reach approximately 94%.  imidazole; hydroxyethylation; hydroquinone; ethylene carbonate; nucleophilic catalysis Zhou Qing Wang Shuo Wang Rui Jiang Heng Jin Changzi PUBLIC https://creativecommons.org/licenses/by-nc-nd/4.0/ dataset http://www.doi.org/10.3724/j.issn1001-3555.2026.03.006 Science Data Bank