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DOI: 10.1055/s-2004-836027
1-Methyl-3-butylimidazolium Decatungstate in Ionic Liquid: An Efficient Catalyst for the Oxidation of Alcohols
Publikationsverlauf
Publikationsdatum:
29. November 2004 (online)
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Abstract
An excellent system for the selective oxidation of benzylic and secondary alcohols with hydrogen peroxide catalyzed by 1-methyl-3-butylimidazolium decatungstate in [bmim][BF4] ionic liquid is described. The catalytic system is reusable and products are obtained in excellent yield under environmentally benign conditions.
Key words
ionic liquid - oxidation - sodium tungstate - 1-methyl-3-butylimidazolium decatungstate
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References
Synthesis of Catalyst [bmim] 4 [W 10 O 23 ]: The boiling solutions of Na2WO4·2H2O (16 g) in 100 mL H2O and 35 mL of 3 M HCl were mixed in a Erlenmeyer flask and further heated for 5 min to get yellow solution. To this was added 1-methyl-3-butylimidazolium bromide [bmim][Br] (4.4 g) in 50 mL H2O with stirring. A puff greenish white precipitate separates out instantly. Washed the solid with H2O thoroughly and then with MeOH (50 mL) and Et2O (50 mL). The solid was dried under air at r.t. to obtain puff white product.
16Representative Procedure for the Oxidation of Alcohols: Pre-saturated catalyst [bmim]4[W10O23] (100 mg) was dissolved in [bmim][BF4] ionic liquid (2 mL) by heating. Then added diphenyl carbinol (184 mg, 10 mmol) and heated the reaction mixture to 90 °C on oil bath, followed by drop-wise addition of hydrogen peroxide 30% solution (172 µL) with fast stirring. Then, 10 µL of reaction mixture were taken out at different time interval, extracted with Et2O and monitored by TLC and GC. The conversion percentage and purity of product was checked by gas chromatography (Table [2] ). On completion of reaction, the reaction mixture was cooled to r.t. and extracted with Et2O (3 × 3 mL). Finally, the solvent was evaporated under reduced pressure to obtain diphenyl ketone (175 mg, 96% yield).