Extraction Behavior of Indole from Simulated Wash Oil Using Halogen-Free Ionic Liquids

Indole is an important raw material in the chemical industry, and more than 1 wt % indole is contained in wash oil. Therefore, the extraction of indole from wash oil is of much importance. The conventional separation methods generally cost much money, pollute the environment, and corrode the metallic devices due to the use of large amounts of inorganic acid and alkali solutions, and therefore, new methods should be proposed. In this work, a solvent extraction process for separating indole from simulated wash oil by five halogen-free ionic liquids (HFILs) has been designed, and the extraction behavior of indole has been evaluated. All the studied HFILs presented excellent extraction behavior for indole, and the whole separation process took no more than 5 min. For the same HFIL, the minimum residual indole contents remained the same, even if the initial indole contents changed. Among the HFILs, 1-butyl-3-methylimidazolium dimethyl phosphate ([Bmim][DMP]) has attracted more attention than other HFILs. The results showed that [Bmim][DMP] could extract over 96.9 wt % indole from the simulated wash oil, and the minimum residual indole content was as low as 2.1 g/dm³. For indole, [Bmim][DMP] presented a maximum distribution coefficient of 201, which was much improved compared to other methods. The HFILs could be regenerated by using diethyl ether with ease. The regenerated HFILs could be reused, and the extraction behavior remained the same as the original HFILs. Based on FT-IR results, a mechanism of hydrogen bonds forming between HFILs and indole was proposed. In addition, the superiorities of HFILs over other separation agents in reusability, amounts needed, distribution coefficient for indole, and chemical structure were proved by comparison.