Ionic liquid functionalized silica gel: novel catalyst and fixed solvent

Tetrahedron Letters

Volumn 47, Issue 39, 2006, Pages 6951-6953

  Lai, Guoqiao ^a,b   Peng, Jiajian ^b   Li, Jiayun ^b   Qiu, Huayu ^b   Jiang, Jianxiong ^b   Jiang, Kezhi ^b   Shen, Yongjia ^a  

^a EAST CHINA UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b BEIJING UNIVERSITY OF POSTS AND TELECOMMUNICATIONS   (China)

Author keywords

Cycloaddition; Ionic liquid functionalized silica gel; Knoevenagel condensation; Recyclable

Indexed keywords

CARBON DIOXIDE; IMIDAZOLE DERIVATIVE; IONIC LIQUID; PROPYLENE OXIDE; SILICA GEL; SOLVENT;

ARTICLE; CATALYST; CYCLOADDITION; KNOEVENAGEL CONDENSATION;

EID: 33747800403     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.07.122     Document Type: Article

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13. Preparation of 1-methyl-3-(3-triethoxysilylpropylimidazolium chloride 1: (3-Chloropropyl)triethoxysilane (48.2 g, 0.2 mol) and N-methylimidazole (16.4 g, 0.2 mol) were placed in a 100 mL stainless steel autoclave, which was evacuated and sealed, then heated to 120 °C for 24 h. The sticky residue was washed with ethyl acetate/diethyl ether and dried at 60 °C in vacuum to afford 1 (58.1 g, 90% yield), a white solid under room temperature.
14. Preparation of imidazolium cation-based ionic liquid functionalized silica gels 2 and 3: Tetraethoxysilane (41.6 g, 0.2 mol) and 1 (32.2 g, 0.1 mol) were dissolved in 80 ml of ethanol, then 9.2 mL of 1% HCl aqueous was added. The resulting solution was stirred at 55 °C for 6 h and at room temperature for 24 h, and then the mixture was evaporated to dryness under reduced pressure. The residue was heated to 200 °C for 8 h to form 2 quantitatively (Scheme 1). Catalyst 2 (7.82 g) and zinc chloride (1.414 g) were suspended in methylene dichloride (50 mL), after stirring overnight at room temperature. Evaporation of the suspension afforded zinc chloride co-presented catalyst 3, which was used as catalyst for synthesis propylene carbonate from carbon dioxide and propylene oxide.
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