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Deoximation Reaction in Room Temperature Ionic Liquids under Mild Conditions
Author(s) -
Zhang Xiaoxia,
Lu Bin,
Wang Xiaoguang,
Zhao Jingxiang,
Cai Qinghai
Publication year - 2011
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201100041
Subject(s) - cyclohexanone oxime , chemistry , oxime , acetophenone , catalysis , ionic liquid , chloride , selectivity , hydrolysis , benzophenone , solvent , organic chemistry , medicinal chemistry
Deoximation in metal chloride ionic liquids based on 1‐alkyl‐3‐methylimidazolium and triethylene ammonium cations, such as AmimBr(Cl)‐MCl x (A=ethyl, butyl, benzyl; M=Al, Fe, Cu, Sn and Zn; x =2, 3) and Et 3 NHCl‐FeCl 3 were investigated under mild conditions. Ferrate chloride ionic liquid was proved to be an effective catalyst for deoximation of cyclohexanone oxime, exhibiting high conversion of oximes and selectivity to cyclohexanone. Good performance for the deoximation of other oximes such as salicylald oxime, acetone oxime, benzophenone oxime, 4‐nitrobenzald oxime, acetophenone oxime, 2‐chlorobenzaldehyde oxime, Acetald oxime, 2‐butanone oxime and (1 R )‐camphor oxime was also achieved with bmimBr‐FeCl 3 as catalyst and solvent. The deoximation was determined to carry out via acid‐catalytic hydrolysis and the reaction mechanism was proposed.