Abstract
A family of alkoxybenzoate derivatives was synthesized and were found to selectivity congeal protic/aprotic polar solvents, gasoline, and oils over water; therefore, these organogelators could be used in water remediation as removal agents of fuels and oils. Due to their thermoreversibility, they can be easily separated from the mixtures and be reused; being good candidates for fuel recovery. The π-π stacking interactions were evaluated to establish a relationship between their chemical structure and the gelation process through UV–vis spectroscopy; the three-dimensional network was studied with polarized optical microscopy (POM) and scanning electron microscopy (SEM). It was found that the aromatic ring acts as a stacking unit due to the π-π interactions; the ester group provides a source of dipole–dipole interactions; and the alkyl chains in the ether group showed a significant influence in gelation with the increase of carbon atoms, which increases the effect of nonpolar dispersion interactions.
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References
Amabilino, D. B., Smith, D. K., & Steed, J. W. (2017). Supramolecular materials. Chemical Society Reviews, 46(9), 2404–2420. https://doi.org/10.1039/C7CS00163K
Ávila-Rovelo, N. R., & Ruiz-Carretero, A. (2020). Recent progress in hydrogen-bonded π-conjugated systems displaying J-type aggregates. Organic Materials, 02, 047–063. https://doi.org/10.1055/s-0040-1708502
Cai, X., & Zhao, Q. (2021). A mini review: Supramolecular gels based on calix[4]arene derivatives. Journal of Inclusion Phenomena and Macrocyclic Chemistry, 99(1–2), 13–22. https://doi.org/10.1007/s10847-020-01032-8
Chen J., Zhang L., Li Q., Wang M., Dong Y., and Yu X. (2020). Comparative study on the evolution of polar compound composition of four common vegetable oils during different oxidation processes, LWT-Food Science and Technology, 129. https://doi.org/10.1016/j.lwt.2020.109538.
Chivers, P. R., & Smith, D. K. (2019). Shaping and structuring supramolecular gels. Nature Reviews Materials, 4(7), 463–478. https://doi.org/10.1038/s41578-019-0111-6
Christ, E., Blanc, C., Ouahabi, A. A., Maurin, D., Le Parc, R., Bantignies, J. L., Guenet, J. L., Collin, D., & Mésini, P. J. (2016). Origin of invariant gel melting temperatures in the c-t phase diagram of an organogel. Langmuir, 32(19), 4975–4982. https://doi.org/10.1021/acs.langmuir.6b00995
Fameau, A. L., & Rogers, M. A. (2020). The curious case of 12-hydroxystearic acid - the Dr. Jekyll & Mr. Hyde of Molecular Gelators, Current Opinion in Colloid & Interface Science, 45, 68–82. https://doi.org/10.1016/j.cocis.2019.12.006
Fang, W., Zhang, Y., Wu, J., Liu, C., Zhu, H., & Tu, T. (2018). Recent advances in supramolecular gels and catalysis. Chemistry - an Asian Journal, 13(7), 712–729. https://doi.org/10.1002/asia.201800017
Ghosh, S., Praveen, V. K., & Ajayaghosh, A. (2016). The chemistry and applications of π -gels. The Annual Review of Materials Research, 46, 235–262. https://doi.org/10.1146/annurev-matsci-070115-031557
Jones, C. D., & Steed, J. W. (2016). Gels with sense: Supramolecular materials that respond to heat, light and sound. Chemical Society Reviews, 45(23), 6546–6596. https://doi.org/10.1039/C6CS00435K
Kizil, S., Karadag, K., Aydin, G. O., & Sonmez, H. B. (2015). Poly(Alkoxysilane) reusable organogels for removal of oil/organic solvents from water surface. Journal of Environmental Management, 149, 57–64. https://doi.org/10.1016/j.jenvman.2014.09.030
Kwon, S. Y., Massey, K., Watson, M. A., Hussain, T., Volpe, G., Buckley, C. D., Nicolaou, A., and Badenhorst, P. (2020). Oxidised metabolites of the omega-6 fatty acid linoleic acid activate dFOXO, Life Science Alliance, 3(2). DOI: https://doi.org/10.26508/lsa.201900356.
Kyriacos, D. (2020). Vegetable Oils and Fats. In Wiley (Ed.), Biobased polyols for industrial polymers (pp. 51–131). DOI: https://doi.org/10.1002/9781119620358.ch3
Lai, Y. H., de Leon, A., Pangilinan, K., & Advincula, R. (2018). Superoleophilic and under-oil superhydrophobic organogel coatings for oil and water separation. Progress in Organic Coatings, 115, 122–129. https://doi.org/10.1016/j.porgcoat.2017.11.001
Lan, Y., Corradini, M. G., Weiss, R. G., Raghavan, S. R., & Rogers, M. A. (2015). To gel or not to gel: Correlating molecular gelation with solvent parameters. Chemical Society Reviews, 44, 6033–6058. https://doi.org/10.1039/C5CS00136F
Liu, J. W., Ma, J. T., & Chen, C. F. (2011). Structure-property relationship of a class of efficient organogelators and their multistimuli responsiveness. Tetrahedron, 67(1), 85–91. https://doi.org/10.1016/j.tet.2010.11.027
Lupi, F. R., Greco, V., Baldino, N., de Cindio, B., Fischer, P., & Gabriele, D. (2016). The effects of intermolecular interactions on the physical properties of organogels in edible oils. Journal of Colloid and Interface Science, 483, 154–164. https://doi.org/10.1016/j.jcis.2016.08.009
Maisonneuve, L., Chollet, G., Grau, E., and Cramail, H. (2016). Vegetable oils: A source of polyols for polyurethane materials, Oilseeds and fats crops and lipids, 23(5). DOI: https://doi.org/10.1051/ocl/2016031.
Matheson, A., Koustos, V., Dalkas, G., Euston, S., & Clegg, P. (2017). The microstructure of -sitosterol : -oryzanol edible organogels the microstructure of β - sitosterol : γ -oryzanol edible organogels. Langmuir, 33(18), 4537–4542. https://doi.org/10.1021/acs.langmuir.7b00040
Nunes, D. R., Reche-Tamayo, M., Ressouche, E., Raynal, M., Isare, B., Foury-Leylekian, P., Albouy, P. A., Brocorens, P., Lazzaroni, R., & Bouteiller, L. (2019). Organogel formation rationalized by hansen solubility parameters: shift of the gelation sphere with the gelator structure. Langmuir, 35(24), 7970–7977. https://doi.org/10.1021/acs.langmuir.9b00966
Santoro, N., Caprio, S., & Feldstein, A. E. (2013). Oxidized metabolites of linoleic acid as biomarkers of liver injury in nonalcoholic steatohepatitis. Clinical Lipidology, 8(4), 411–418. https://doi.org/10.2217/clp.13.39
Sarathy, S. M., Farooq, A., & Kalghatgi, G. T. (2018). Recent progress in gasoline surrogate fuels. Progress in Energy and Combustion Science, 65, 67–108. https://doi.org/10.1016/j.pecs.2017.09.004
Sato, H., Nogami, E., Yajima, T., & Yamagishi, A. (2014). Terminal effects on gelation by low molecular weight chiral gelators. Royal Society of Chemistry Advances, 4(4), 1659–1665. https://doi.org/10.1039/c3ra44070b
Sawalha, H., Venema, P., Bot, A., Flöter, E., Lan, Y., & van der Linden, E. (2020). Effects of oil type on sterol-based organogels and emulsions. Food Biophysics, 16, 109–118. https://doi.org/10.1007/s11483-020-09654-8
Schmidt, R., Adam, F. B., Michel, M., Schmutz, M., Decher, G., & Mésini, P. J. (2003). New bisamides gelators: relationship between chemical structure and fiber morphology. Tetrahedron Letters, 44(15), 3171–3174. https://doi.org/10.1016/S0040-4039(03)00456-8
Simon, F. X., Nguyen, T. T. T., Díaz, N., Schumtz, M., Demé, B., Jestin, J., Combet, J., & Mésini, P. (2013). Self-Assembling properties of a series of homologous ester-diamides-from ribbons to nanotubes. Soft Matter, 9(35), 8483–8493. https://doi.org/10.1039/c3sm51369f
Suzuki, M., Maruyama, Y., & Hanabusa, K. (2016). Gel-solution phase transition of organogels with photoreversibility: L-amino acid organogelators with azobenzene. Tetrahedron Letters, 57(31), 3540–3543. https://doi.org/10.1016/j.tetlet.2016.06.111
Suzuki, M., Yumoto, M., Shirai, H., & Hanabusa, K. (2008). A family of low-molecular-weight organogelators based on nα, nε-diacyl-l-lysine: Effect of alkyl chains on their organogelation behaviour. Tetrahedron, 64(45), 10395–10400. https://doi.org/10.1016/j.tet.2008.08.061
Wang, X., Cui, W., Li, B., Zhang, X., Zhang, Y., & Huang, Y. (2020). Supramolecular self-assembly of two-component systems comprising aromatic amides/schiff base and tartaric acid. Frontiers of Chemical Science and Engineering, 14(6), 1112–1121. https://doi.org/10.1007/s11705-019-1865-5
Wang, Z. (2010). Williamson Ether Synthesis. In Comprehensive organic name reactions and reagents, John Wiley and Sons, pp. 3026–3030. DOI: https://doi.org/10.1002/9780470638859.conrr673.
Wu, D., Zhang, F., Lou, W., Li, D., & Chen, J. (2017). Chemical characterization and toxicity assessment of fine particulate matters emitted from the combustion of petrol and diesel fuels. Science of the Total Environment, 605–606, 172–179. https://doi.org/10.1016/j.scitotenv.2017.06.058
Zapién-Castillo, S., Díaz-Zavala, N.P., Melo-Banda, J.A., Schwaller, D., Lamps, J.P., Schumtz, M., Combet, J., and Mésini, J.P. (2020). Structure of nanotubes self-assembled from a monoamide organogelator, International Journal of Molecular Sciences, 21(14), 4960, 1–13. DOI: https://doi.org/10.3390/ijms21144960.
Zapién-Castillo, S., Montes-Patiño, J.J., Pérez-Sanchez, J.F., Lozano-Navarro, J.I., Melo-Banda, J.A., Mésini, J.P., and Díaz-Zavala, N.P. (2021). Recovery of fuels using the supramolecular gelation ability of a hydroxybenzoic acid bisamide derivative, Water, Air, & Soil Pollution 232(39). DOI: https://doi.org/10.1007/s11270-021-04991-x.
Zeng, C., Wan, Z., Xia, H., Zhao, H., & Guo, S. (2020). Structure and properties of organogels developed by diosgenin in canola oil. Food Biophysics, 15, 452–462. https://doi.org/10.1007/s11483-020-09643-x
Zhang, B., Chen, S., Luo, H., Zhang, B., Wang, F., and Song, J. (2019). Porous amorphous powder form phase-selective organogelator for rapid recovery of leaked aromatics and spilled oils, Journal of Hazardous Materials, 384. https://doi.org/10.1016/j.jhazmat.2019.121460.
Zhang, X., Dai, R., Sun, H., Zhang, Y., Liu, D., Wang, M., Sun, M., & Yu, H. (2020). Mandelic acid-derived organogelators: applications of their solid form in rapid and efficient remediation of marine oil spills. Materials Chemistry Frontiers, 4(1), 222–230. https://doi.org/10.1039/C9QM00603F
Zhao, X., Zhao, L., Xiao, Q., & Xiong, H. (2020). Intermolecular hydrogen-bond interaction to promote thermoreversible 2’-deoxyuridine-based aie-organogels. Chinese Chemical Letters, 4, 222–230. https://doi.org/10.1016/j.cclet.2020.10.008
Acknowledgements
Authors would like to acknowledge the Tecnológico Nacional de México-Instituto Tecnológico de Ciudad Madero (TecNM-ITCM) for the reagents and materials provided through the Proyecto de Investigación Científica, the Consejo Nacional de Ciencia y Tecnología (CONACyT) for the project 295494 for the Tbmx-GC-MS, and the project 282278 (JFPS, JILN), and for Ph.D. candidate scholarship (JESS).
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Jaime E. Sosa-Sevilla and Nancy P. Díaz-Zavala conceived and designed the experiments and wrote the paper, Nancy P. Díaz-Zavala, Silvia B. Brachetti-Sibaja and Jessica I. Lozano-Navarro analyzed the data and revised the manuscript; Jaime E. Sosa-Sevilla and Josué F. Pérez-Sánchez performed the experiments, and analyzed the data. All authors have read and agreed to the published version of the manuscript.
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Sosa-Sevilla, J.E., Brachetti-Sibaja, S.B., Pérez-Sánchez, J.F. et al. Alkoxybenzoate Derivatives: Design and Gelation Effect on Organic Solvents, Fuels, and Oils. Water Air Soil Pollut 232, 239 (2021). https://doi.org/10.1007/s11270-021-05194-0
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DOI: https://doi.org/10.1007/s11270-021-05194-0