Traditionally, isoborneol was oxidized to produce camphor under toxic conditions, using chromium (VI) oxide and sulfuric acid (CrO3/H2SO4). Alternatively, the use of ethyl acetate and potassium peroxomonosulfate(C4H8O2/KSO4OH) produced camphor under less toxic conditions. The yields for this oxidation were found to be similar to that of the more toxic CrO3/H2SO4 system. This investigation also involved the synthesis of four ionic liquids containing the 1-hexyl-3-methylimidazolium ([hmim]+) or n-butylpyridine ([bpy]+) cations coupled with either trifluoroacetate anion ([CF3COO]-) or hexafluorophosphate anion ([PF6]-). These ionic liquids were substituted for the solvent ethyl acetate and KSO4OH was used as the oxidizing agent, which produced 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

253rd National Meeting (2017)

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