Traditionally, isoborneol was oxidized to produce camphor under toxic conditions, using chromium (VI) oxide and sulfuric acid (CrO3/H2SO4). Alternatively, the use of glacial acetic acid and sodium hypochlorite (NaOCl) produced camphor under less toxic conditions. However, the yields for the latter oxidation were significantly less than that of the more toxic CrO3/H2SO4 system. This investigation involved the synthesis of two ionic liquids containing the 1-hexyl-3-methylimidazolium cation ([hmim]+) coupled to either the trifluoroacetate anion ([CF3COO]-) or hexafluorophosphate anion ([PF6]-) . These ionic liquids were substituted for the solvent acetic acid and NaOCl was used as the oxidizing agent, producing a comparable yield to the CrO3/H2SO4 system through a greener process. Previous studies suggest ionic liquids can be recycled or reclaimed, stabilize intermediates better than traditional solvents and increase typical product yields.

Synthesis of camphor using ionic liquids

251st National Meeting (2016)

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