Abstract
The desulfurization by adsorption of thiophene and 4,6-dimethyldibenzothiophene on unripe banana starch, dessert banana starch, corn starch, and porous corn starch was studied. The adsorbents were characterized by scanning electron microscopy, surface acidity measurement, and infrared spectroscopy with attenuated total reflection. The results showed low values of adsorption of both sulfur molecules on both banana starches, which is due to the absence of cavities or pores in their structure. In the case of corn starch, the presence of cavities or pores allows a greater adsorption capacity for thiophene and 4,6-dimethyldibenzothiophene. The mechanism of interaction between sulfured molecules and the starches can occur through free electron pair of sulfur or the π electron cloud of the aromatic ring with the Brönsted acid site of starches. The enzymatic modification applied to corn starch allowed obtaining a material with a greater number of cavities or pores, but that maintains their structure and physicochemical properties. The presence of pores of a larger size allows adsorbing a greater amount of sulfured molecules in comparison to the native starch.
Similar content being viewed by others
Data Availability
Not applicable.
Code Availability
Not applicable.
References
Ahmad, W., Ahmad, I., Ishaq, M., & Ihsan, K. (2017). Adsorptive desulfurization of kerosene and diesel oil by Zn impregnated montmorollonite clay. Arabian Journal of Chemistry, 10(2), S3263–S3269. https://doi.org/10.1016/j.arabjc.2013.12.025
Alcázar-Alay, S. C., & Almeida Meireles, M. A. (2015). Physicochemical properties, modifications and applications of starches from different botanical sources. Food Science and Technology, 35(2), 215–236. https://doi.org/10.1590/1678-457X.6749
Amaya, C. F., Osorio-Diaz, P., Agama-Acevedo, E., Yee-Madeira, H., & Bello-Pérez, L. A. (2011). Physicochemical and digestibility properties of double-modified banana (Musa paradisiaca L.) starches. Journal of Agricultural and Food Chemistry, 59(4), 1376–1382. https://doi.org/10.1021/jf1035004
Ashogbon, A. O., & Akintayo, E. T. (2014). Recent trend in the physical and chemical modification of starches from different botanical sources: A review. Starch/staerke, 66(1–2), 41–57. https://doi.org/10.1002/star.201300106
Baeza, P., Bassi, R., Villarroel, M., Ojeda, J., Araya, P., & Aguila, G. (2015). Adsorption of 4,6-dimethyldibenzothiophene over Cu/ZrO2. Journal of the Chilean Chemical Society, 60, 2817–2821. https://doi.org/10.4067/S0717-97072015000100009
Baeza, P., Aballay, P., Matus, Camú, E., Ramirez M., Eyzaguirre, J., Ojeda, J. (2019). Degradation of paracetamol adsorbed on inorganic supports under UV irradiation. Water Air Soil Pollut, 230-234. https://doi.org/10.1007/s11270-019-4095-z
Benhmid, A., Edbey, K., Bukhzam, A., Alhowari, H., Mekhemer, G. A. H., & Zaki, M. I. (2018). Surface acidity of the supported molybdenum oxide catalysts probed by potentiometric titration of n-butylamine. International Research Journal of Pure & Applied Chemistry, 16, 1–7. https://doi.org/10.9734/IRJPAC/2018/41667
Chen, Q., Zheng, X., Zhou, L., & Kang, M. (2019). Chemical modification of starch microcrystals and their application as an adsorbent for metals in aqueous solutions. BioResources, 14(1), 302–312.
Djoković, V., Krsmanović, R., Bozanić, D. K., McPherson, M., Van Tendeloo, G., Nair, P. S., Georges, M. K., & Radhakrishnan, T. (2009). Adsorption of sulfur onto a surface of silver nanoparticles stabilized with sago starch biopolymer. Colloids and Surfaces b: Biointerfaces, 73(1), 30–35. https://doi.org/10.1016/j.colsurfb.2009.04.022
Dura, A., Błaszczak, W., & Rosell, C. M. (2014). Functionality of porous starch obtained by amylase or amyloglucosidase treatments. Carbohydrate Polymers, 101, 837–845. https://doi.org/10.1016/j.carbpol.2013.10.013
Espinosa-Solis, V., Jane, J. L., & Bello-Perez, L. (2009). Physicochemical characteristics of starches from unripe fruits of mango and banana. Starch/staerke, 61, 291–299. https://doi.org/10.1002/star.200800103
Ghubayra, R., Nuttall, C., Hodgkiss, S., Craven, M., Kozhevnikova, E., & Kozhevnikov, I. (2019). Oxidative desulfurization of model diesel fuel catalyzed by carbon-supported heteropoly acids. Applied Catalysis b: Environmental, 253, 309–316. https://doi.org/10.1016/j.apcatb.2019.04.063
Gutierrez-Alejandre, A., Larrubia, M., Ramirez, J., & Busca, G. (2006). FT-IR evidence of the interaction of benzothiophene with the hydroxyl groups of H-MFI and H-MOR zeolites. Vibrational Spectroscopy, 41, 42–47. https://doi.org/10.1016/j.vibspec.2005.12.008
Haroon, M., Wang, L., Yu, H., Abbasi, N. M., Zain-ul-Abdin, Saleem, M., & Wu, J. (2016). Chemical modification of starch and its application as an adsorbent material. RSC Advances, 6(82), 78264–78285. https://doi.org/10.1039/C6RA16795K
Hasan, Z., & Jhung, S. H. (2015). A facile method to disperse non-porous metal organic frameworks: Composite formation with a porous metal organic framework and application in adsorptive desulfurization. ACS Applied Materials & Interfaces, 7(19), 10429–10435. https://doi.org/10.1021/acsami.5b01642
Ishaq, M., Sultan, S., Ahmad, I., Ullah, H., Yaseen, M., & Amir, A. (2017). Adsorptive desulfurization of model oil using untreated, acid activated and magnetite nanoparticle loaded bentonite as adsorbent. Journal of Saudi Chemical Society, 21(2), 143–151. https://doi.org/10.1016/j.jscs.2015.02.003
Jha, D., Haider, M. B., Kumar, R., Byamba-Ochir, N., Shim, W. G., Sivagnanam, M. B., & Moon, H. (2019). Enhanced adsorptive desulfurization using Mongolian anthracite-based activated carbon. ACS Omega, 4(24), 20844–20853. https://doi.org/10.1021/acsomega.9b03432J
Jung, Y. S., Lee, B. H., & Yoo, S. H. (2017). Physical structure and absorption properties of tailor-made porous starch granules produced by selected amylolytic enzymes. PLoS ONE, 12(7), e0181372. https://doi.org/10.1371/journal.pone.0181372
Liu, Q., Li, F., Lu, H., & Li, M. (2017). Enhanced dispersion stability and heavy metal ion adsorption capability of oxidized starch nanoparticles. Food Chemistry, 242, 256–263. https://doi.org/10.1016/j.foodchem.2017.09.071
López, O. V., Zaritzky, N. E., & García, M. A. (2010). Physicochemical characterization of chemically modified corn starches related to rheological behavior, retrogradation and film forming capacity. Journal of Food Engineering, 100(1), 160–168. https://doi.org/10.1016/j.jfoodeng.2010.03.041
Luo, Z., Fu, X., He, X., Luo, F., Gao, Q., & Yu, S. (2008). Effect of ultrasonic treatment on the physicochemical properties of maize starches differing in amylose content. Starch/staerke, 60, 646–653. https://doi.org/10.1002/star.200800014
Nazal, M. K., Khaled, M., Atieh, M. A., Aljundi, I. H., Oweimreen, G. A., & Abulkibash, A. M. (2019). The nature and kinetics of the adsorption of dibenzothiophene in model diesel fuel on carbonaceous materials loaded with aluminum oxide particles. Arabian Journal of Chemistry, 12(8), 3678–3691. https://doi.org/10.1016/j.arabjc.2015.12.003
Oliveira L. S. and Franca A. S. (2012). Low-cost adsorbents from agrifood wastes. In Encyclopedia of food science research, C. L. Turner and J. A. Randovski (Eds.), (vol. 1, pp. 171–210). Nova Publishers, New York, NY, USA.
Peralta, C., Camú, E., Bassi, P., Villarroel, M., Ojeda, J., & Baeza, P. (2016). Denitrogenation by adsorption of pyridine on Ni/support adsorbents. Journal of the Chilean Chemical Society, 2016(4), 3211–3213. https://doi.org/10.4067/S0717-97072016000400012
Rivera, V., Suarez-Méndez, A., Pascual-Mathey, L., Gutierrez, A., Vera, M., & Fuentes, G. (2019). On the interaction of thiophene and zeolite-Y in the thiophene-based oligomers formation. Revista Mexicana de Ingeniería Química, 19(1), 471–479. https://doi.org/10.24275/rmiq/Mat617
Sadare, O. O., & Daramola, M. O. (2019). Adsorptive desulfurization of dibenzothiophene (DBT) in model petroleum distillate using functionalized carbon nanotubes. Environmental Science and Pollution Research, 26(32), 32746–32758. https://doi.org/10.1007/s11356-019-05953-x
Sainz-Díaz, C. I., Francisco-Márquez, M., & Vivier-Bunge, A. (2010). Molecular structure and spectroscopic properties of polyaromatic heterocycles by first principle calculations: Spectroscopic shifts with the adsorption of thiophene on phyllosilicate surface. Theoretical Chemistry Accounts, 125, 83. https://doi.org/10.1007/s00214-009-0666-1
Saleh, T. A., Siddiqui, M. N., & Al-Arfaj, A. A. (2014). Synthesis of multiwalled carbon nanotubes-titania nanomaterial for desulfurization of model fuel. Journal of Nanomaterial, 940639, 1–66. https://doi.org/10.1155/2014/940639
Seredych, M., Hulicova-Jurcakova, D., & Bandosz, T. J. (2010). Effect of the incorporation of nitrogen to a carbon matrix on the selectivity and capacity for adsorption of dibenzothiophenes from model diesel fuel. Langmuir, 26(1), 227–233. https://doi.org/10.1021/la902059y
Soleimani, M., Bassi, A., & Margaritis, A. (2007). Biodesulfurization of refractory organic sulfur compounds in fossil fuels. Biotechnology Advances, 25, 570–596. https://doi.org/10.1016/j.biotechadv.2007.07.003
Srivastav, A., & Srivastava, V. C. (2009). Adsorptive desulfurization by activated alumina. Journal of Hazardous Materials, 170, 1133–1140. https://doi.org/10.1016/j.jhazmat.2009.05.088
Sun, H., Zhao, P., Ge, X., Xia, Y., Hao, Z., Liu, J., & Peng, M. (2010). Recent advances in microbial raw starch degrading enzymes. Applied Biochemistry and Biotechnology, 160(4), 988–1003. https://doi.org/10.1007/s12010-009-8579-y
Uzunova, S., Uzunov, I., Atanasova, G., Angelova, D., & Ivanov, I. (2019). Selective adsorption of thiophene and its polyaromatic derivatives from fuels on pyrolyzed rice husks: a thermodynamic study. Journal of Chemical Technology & Metallurgy, 54(5), 962–977. https://dl.uctm.edu/journal/node/j2019-5/12_18-191_962-977.pdf
Xiao, J., Li, Z., Liu, B., Xia, Q., & Yu, M. (2008). Adsorption of benzothiophene and dibenzothiophene on ion-impregnated activated carbons and ion-exchanged Y zeolites. Energy & Fuels, 22, 3858–3863. https://doi.org/10.1021/ef800437e
Xie, G., Shang, X., Liu, R., Hu, J., & Liao, S. (2011). Synthesis and characterization of a novel amino modified starch and its adsorption properties for Cd(II) ions from aqueous solution. Carbohydrate Polymers, 84(1), 430–438. https://doi.org/10.1016/j.carbpol.2010.12.003
Xue, L., Zhang, D., Xu, Y., & Liu, X. (2017). Adsorption of Thiophene compounds on MoO3/γ-Al2O3 catalysts with different mesopore sizes. Microporous and Mesoporous Materials, 238, 46–55. https://doi.org/10.1016/j.micromeso.2016.03.004
Yadav, B. S., Guleria, P., & Yadav, R. B. (2013). Hydrothermal modification of Indian water chestnut starch: Influence of heat-moisture treatment and annealing on the physicochemical, gelatinization and pasting characteristics. LWT-Food Science and Technology, 53(1), 211–217. https://doi.org/10.1016/j.lwt.2013.02.007
Yoosuk, B., Silajan, A., & Prasassarakich, P. (2020). Deep adsorptive desulfurization over ion-exchanged zeolites: Individual and simultaneous effect of aromatic and nitrogen compounds. Journal of Cleaner Production, 248, 119291. https://doi.org/10.1016/j.jclepro.2019.119291
Zdravkov, B., Čermák, J., Šefara, M., & Janků, J. (2007). Pore classification in the characterization of porous materials: A perspective. Central European Journal of Chemistry, 5(2), 385–395. https://doi.org/10.2478/s11532-007-0017-9
Zhang, B., Cui, D., Liu, M., Gong, H., Huang, Y., & Han, F. (2012). Corn porous starch: Preparation, characterization and adsorption property. International Journal of Biological Macromolecules, 50(1), 250–256. https://doi.org/10.1016/j.ijbiomac.2011.11.002
Zhou, A., Ma, X., & Song, C. (2009). Effects of oxidative modification of carbon surface on the adsorption of sulfur compounds in diesel fuel. Applied Catalysis B Environmental, 87, 190–199. https://doi.org/10.1016/j.apcatb.2008.09.024
Zhou, W., Zhou, Y., Wei, Q., Ding, S., Jiang, S., Zhang, Q., & Liu, M. (2017). Continuous synthesis of mesoporous Y zeolites from normal inorganic aluminosilicates and their high adsorption capacity for dibenzothiophene (DBT) and 4,6-dimethyldibenzothiophene (4,6-DMDBT). Chemical Engineering Journal, 330, 605–615. https://doi.org/10.1016/j.cej.2017.08.005
Funding
The authors are grateful to Pontifical Catholic University of Valparaíso for financial support through DI-PUCV 039.443/2020.
Author information
Authors and Affiliations
Contributions
Not applicable.
Corresponding author
Ethics declarations
Ethics Approval
Not applicable.
Consent to Participate
Not applicable.
Consent for Publication
Not applicable.
Conflict of Interest
The authors declare no competing interests.
Additional information
Publisher's Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Baeza, P., Pasten, B., Concha, J. et al. Removal of Thiophene and 4,6-Dimethyldibenzothiophene by Adsorption on Different Kinds of Starches. Water Air Soil Pollut 232, 395 (2021). https://doi.org/10.1007/s11270-021-05353-3
Received:
Accepted:
Published:
DOI: https://doi.org/10.1007/s11270-021-05353-3