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Synthesis of Novel Gemini Dicationic Acidic Ionic Liquids and Their Catalytic Performances in the Beckmann Rearrangement
Author(s) -
Liu Xiaofei,
Xiao Linfei,
Wu Hugjiltu,
Chen Jing,
Xia Chungu
Publication year - 2009
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200800382
Subject(s) - chemistry , beckmann rearrangement , catalysis , ionic liquid , yield (engineering) , chloride , zinc , inorganic chemistry , medicinal chemistry , organic chemistry , materials science , metallurgy
A series of novel gemini dicationic acidic ionic liquids (GDAILs), compounds 1 – 3 carrying two SO 3 H groups at the cation moieties and having anions of the type CF 3 SO $\rm{ _3^ - }$ , were synthesized in good yields ( Scheme 1 ). Some physicochemical properties of 1 – 3 were determined; due to their unique structures, these novel GDAILs showed noticeable hydrophilic properties and strong acidities ( Table 1 ). Beckmann rearrangements of oximes catalyzed by 1, 2 , or 3 /zinc chloride (GDAIL/ZnCl 2 ) were investigated ( Scheme 2 ); the corresponding amides were formed in up to 99% yield in the presence of 5 mol‐% of GDAIL/ZnCl 2 catalyst under optimized conditions ( Tables 2 and 3 ). The peculiar solubilities of 1 – 3 made the separation of the catalysts from the products very facile, and the catalytic system could be recycled and reused for three times.