151. Sulfination of acetanilide using liquid coordination complexes as dual catalyst and solvent
- Author
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Xubin Zhang, Jinghua Shen, Tianlei Wang, Gang Wang, Haichao Li, and Fumin Wang
- Subjects
Reaction mechanism ,010405 organic chemistry ,Ligand ,Chemistry ,Process Chemistry and Technology ,010402 general chemistry ,01 natural sciences ,Catalysis ,0104 chemical sciences ,Solvent ,symbols.namesake ,chemistry.chemical_compound ,Polymer chemistry ,symbols ,Physical and Theoretical Chemistry ,Selectivity ,Raman spectroscopy ,Acetanilide ,Acetamide - Abstract
The Freidel-Crafts sulfination reaction of acetanilide with sulfur dioxide was catalyzed by several AlCl3-based liquid coordination complexes (LCCs), and the results were compared with that catalyzed by traditional ILs. Influences of different catalysts, ligand/AlCl3 molar ratios, and reaction conditions on their catalytic performance were investigated. The optimal result was obtained using acetamide-AlCl3-based LCC (molar ratio of acetamide to AlCl3 was 0.65, marked as 0.65 A A/AlCl3) as the catalyst, giving nearly 100% conversion of acetanilide within 60 min and 94.07% of selectivity to 4-acetamidobenzenesulfinic acid. AA/AlBr3 was synthesized and also showed catalytic activity for the sulfination reaction. Then a plausible reaction mechanism was proposed by investigation through the raman spectra.
- Published
- 2019
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