Solubilization of Nitrogen Heterocyclic Compounds Using Different Surfactants
- 144 Downloads
In order to develop surfactant-enhanced remediation for nitrogen heterocyclic compounds (NHCs) (aniline, indole, and quinolone), the solubilization properties of micellar solutions of five surfactants, namely sodium dodecyl sulfate (SDS), rhamnolipid (RL), polysorbate (Tween 80), sorbitan monolaurate (Span 20), and iso-octyl phenoxy polyethoxy ethanol (TX-100) were investigated in this work. The solubilization capacities were quantified using critical micelle concentration (CMC) as well as thermodynamic and kinetic experiments. Besides, nuclear magnetic resonance (1H NMR) spectra were used to infer the locus of NHCs solubilized by SDS and TX-100. The results from the properties of five surfactants indicated that CMC was affected by temperature, while the micellization was spontaneous and could be both endothermic and exothermic based on the type of surfactant and temperature. Furthermore, the difference in compensation temperature was caused by different solubilization mechanism for various surfactants. The solubilization results showed that the solubilization of NHCs in the surfactant solutions followed a pseudo-first-order kinetic model. Meanwhile, the change in proton’s chemical shift depended on the structure of NHCs and the solubilization ability of surfactants. Finally, the orthogonal experiment (L16(43)) was elementarily designed to optimize the solubilization conditions of indole and the results showed that RL could be a better choice for solubilizing NHCs.
KeywordsSolubilization Nitrogen heterocyclic compounds Surfactants Micelle
The authors appreciate the financial support provided through the Science and Technology Project of Guangdong Province, China (Grant No.: 2014A020216038).
- Bhadani, A., Okano, T., Ogura, T., Misono, T., Sakai, K., Abe, M., et al. (2016). Structural features and surfactant properties of core–shell type micellar aggregates formed by gemini piperidinium surfactants. Colloids and Surfaces A: Physicochemical and Engineering Aspects, 494, 147–155.CrossRefGoogle Scholar
- Chatterjee, A. M. S. P., Sanyal, S. K., et al. (2001). Thermodynamics of micelle formation of ionic surfactants: A critical assessment for sodium dodecyl sulfate, cetyl pyridinium chloride and dioctyl sulfosuccinate (Na salt) by microcalorimetric, conductometric, and tensiometric measurements. The Journal of Physical Chemistry. B, 105, 12823–12831.CrossRefGoogle Scholar
- Chauhan, S., & Sharma, K. (2014). Effect of temperature and additives on the critical micelle concentration and thermodynamics of micelle formation of sodium dodecyl benzene sulfonate and dodecyltrimethylammonium bromide in aqueous solution: a conductometric study. The Journal of Chemical Thermodynamics, 71, 205–211.CrossRefGoogle Scholar
- Liang, X., Guo, C., Liao, C., Liu, S., Wick, L. Y., Peng, D., et al. (2017). Drivers and applications of integrated clean-up technologies for surfactant-enhanced remediation of environments contaminated with polycyclic aromatic hydrocarbons (PAHs). Environmental Pollution, 225, 129–140.CrossRefGoogle Scholar
- F. Lowe, D. L. Oubre & Ward, C. (1999). Surfactants and cosolvents for NAPL remediation: a technology practices manual. Boca Raton: CRC PressGoogle Scholar
- Yang, Z., Zhou, J., Xu, Y., Zhang, Y., Luo, H., Chang, K. L., & Wang, Y. (2017). Analysis of the metabolites of indole degraded by an isolated Acinetobacter pittii L1. BioMed Research International, 2017, 1–10.Google Scholar