Extractive performance of an acidic phosphonium-based deep eutectic solvent for simultaneous desulfurization and denitrogenation of real gasoline

Authors

    Leila Zarin Department of Applied Chemistry, Faculty of Chemistry and Petroleum Sciences, Bu–Ali Sina University, Hamedan, Iran
    Javad Saien * Department of Applied Chemistry, Faculty of Chemistry and Petroleum Sciences, Bu–Ali Sina University, Hamedan, Iran saien@basu.ac.ir

Keywords:

Liquid–liquid extraction, gasoline purification, total sulfur and nitrogen, Solvent regeneration, Extraction mechanism

Abstract

Hydrodesulfurization and hydrodenitrification in petroleum refinery are often associated with certain limitations of a huge energy consumption and restricted efficacy in removing total sulfur and nitrogen content. This study elucidates employing a selective liquid–liquid extraction process for desulfurization and denitrogenation of real gasoline using an efficient deep eutectic solvent (DES), obtained from methyltriphenylphosphonium bromide and para-toluensulfonic acid in a 3:7 molar ratio. The results show remarkable extraction efficiencies of 50.5% for the total sulfur compounds and 93.5% for the total nitrogen compounds in a single extraction step. After five extraction steps, these efficiencies were improved to 89.3% and 99.3%, respectively, using DES:gasoline volume ratio of 1:1 at 45 ºC. In solvent regeneration via vacuum evaporation, 86.5% of its performance was retained after three stages in extracting sulfur and 91.0% in extracting nitrogen compounds. From NMR analysis, detailed information was obtained regarding the dominant interactions and the extraction mechanism involving acid-base interaction and π– π bonding, dominant for pyridine, and C–H⋯O hydrogen bonding for thiophene, examined by using the DES with a synthetic gasoline. The results totally demonstrate the benefits of utilizing such ecofriendly solvents for purifying fuels.

Downloads

Download data is not yet available.

References

J. Chow, R. J. Kopp and P. R. Portney, Energy resources and global developme, 2003, 302, 1528–1531.

B. Pawelec, R. M. Navarro, J. M. Compos-Martin and J. L. G. Fierro, Catal. Sci. Technol. 2010, 1, 23–42.

A. M. Liaquat, M. A. Kalam, H. H. Masjuki and M. J. Hussan, Atmos. Environ. 2010, 44, 3869–3877.

A. Stanislaus, A. Marafi and M. S. Rana, Catal. Today, 2010, 153, 1–68.

M. Zulhaziman, H. F. Hizaddin, M. K. Hadj-Kali and M. A. Hashim, Sep. Purif. Technol. 2017, 196, 61–70.

I. Mochida and K. H. Choi, J. Jpn. Pet. Inst. 2004, 47, 145–163.

Y. Horii, H. Onuki, S. Doi, T. Mori, H. Sato, T. Ookuro and T. Sugawara, U.S. Patent, 1996, 5,494-572.

S. S. Cheng and T. F. Yen, Energy Fuels, 2008, 22, 1400–1401.

J. H. Kim, X. Ma, A. Zhou and C. Song, Catal. Today, 2006, 111, 74–83.

P. Xu, B. Yu, F. L. Li, X. F. Cai and C. Q. Ma, Trends Microbiol, 2006, 14, 398–405.

L. Zarin,; J. Saien,; F. Jafari and F. Ahmadi, J. Mol. Liq, 2024, 415, 126276.

A. P. Abbott, G. Capper, D. L. Davies, R. K. Rasheed and V. Tambyrajah, Chem. Commun, 2003, 1, 70–71.

F. Lima, M. Dave, A. J. Silvestre, L. C. Branco and I. M. Marrucho, ACS Sustainable Chem. Eng, 2019, 7, 11341-11349.

M. Rogošić and K. Z. Kučan, J. Ind. Eng. Chem, 2019, 72, 87–99.

Z. Li, D. Liu, Z. Men, L. Song, Y. Lv, P. P. Wu, Y. Zhang and Q. Chen, Green Chem. 2018, 20, 31123–120.

C. Ercan and Y. Wang, KBR Technology Center: Houston, TX, 2009.

M. A. Quddus, S. Ahmed and S. N. Sarwar, Pet. Sci. Technol, 2007, 25, 829–840.

S. E. E. Warrag, I. A. Adeyemi, N. R. Rodriguez, I. M. Nashef, M. Van Sint Annaland, M. C. Kroon and C. J. Peters, J. Chem. Eng. Data, 2018, 63, 1088–1100.

S. E. E. Warrag, R. D. Alli and M. C. Kroon, J. Chem. Eng. Data, 2019, 64, 4882–4892.

L. Zarin, J. Saien, D. Dastan and F. Jafari, J. Ind. Eng. Chem, 2025, in press.

M. Rogošić and K. Z. Kučan, J. Chemists Chem. Eng, 2018, 67, 385–394.

M. H. Al-Abdullah, G. T. Kalghatgi and H. Babiker, Fuel, 2015, 153, 67–69.

A. Oseev, M. Zubtsov and R. Lucklum, Procedia Eng, 2012, 47, 1382–1385.

L. Zarin, J. Saien, D. Dastan and F .Jafari, J. Mol. Liq, 2025, 425, 127197.

Y. Liu, J. B. Friesen, J. B. McAlpine, D. C. Lankin, S. N. Chen and G. F. Pauli, J. Nat. Prod, 2018, 81, 679–690.

J. Liu and W. S. Li, Pet. Sci. Technol, 2019, 37, 21–27.

S. Tahir, U. Y. Qazi, Z. Naseem, N. Tahir, M. Zahid, R. Javaid and I. Shahid, Fuel, 2021, 305, 121502.

S. E. E. Warrag, A. S. Darwish, F. O. Abuhatab, I. A. Adeyemi, M. C. Kroon and I. M. AlNashef, Ind. Eng. Chem. Res, 2020, 59(27), 11723–11733.

R. D. Alli and M. C. Kroon, Fluid Phase Equilib, 2018, 477, 1–11.

A. Amonov and S. Scheiner, ChemPhysChem, 2023, 24, e202300326.

National Institute of Standards and Technology, NIST Standard Reference Database 69: NIST Chemistry WebBook, National Institute of Standards and Technology, Gaithersburg, MD, 2025. https://webbook.nist.gov

M. Larriba, M. Ayuso, P. Navarro, N. Delgado-Mellado, M. Gonzalez-Miquel, J. García and F. Rodríguez, ACS Sustainable Chem. Eng, 2018, 6, 1039–1047.

D. Julia, A. C. Gomes, M. Pillinger, A. D. Lopes, R. Valença, J. C. Ribeiro, I. Gonçalves and S. S. Balula, J. Mol. Liq, 2020, 309, 113093.

C. Shu and T. Sun, Sep. Sci. Technol, 2016, 51, 1336–1343.

Li, J.; Xiao, H.; Tang, X.; Zhou, M. Green carboxylic acid-based deep eutectic solvents as solvents for the extraction desulfurization. Energy Fuels 2016, 30, 5411–5418.

Z. S. Gano, F. S. Mjalli, T. Al-Wahaibi and Y. M. Al-Wahaibi, Synth, 2017, 6, 511–521.

F. Rafiei Moghadam, S. Azizian, M. Bayat, M. Yarie, E. Kianpour and M. A. Zolfigol, Fuel, 2017, 208, 14–22.

D. L. Pavia, G. M. Lampman, G. S. Kriz and J. R. Vyvyan, 5th ed.; Cengage Learning: Stamford, CT, 2015.

A. F. Kamarudine, H. F. Hizaddin, A. El-Balidi, E. M. Ali, M. A. Hashim and M. K. Hadj-Kali, Molecules, 2020, 25, 5093.

C. A. Hunter, Angew. Chem. Int. Ed, 1993, 32, 1584–1586.

M. K. Hadj-Kali, S. Mulyono, H. F. Hizaddin, I. Wazeer, L. El-Bildi, E. Ali, M. A. Hashim and I. M. Alnashef, Ind. Eng. Chem. Res, 2016, 55, 8415–8423.

C. Li, D. Li, S. Zou, J. Yin, A. Wang, Y. Cui, Z. Yao and Q. Zhao, Green Chem. 2013, 15, 2793–2799.

F. Abohatab, A. S. Darwish, T. Lemaoui, S. E. E. Warrag, Y. Benguerba, M. C. Kroon and I. M. Alnashef, J. Chem. Eng. Data, 2020, 65, 5443–5457.

Y. Wang, L. Yu, Y. Chen and J. Li, Green Process. Synth, 2025, 14, 0069s.

S. Yamada, Springer: Singapore, 2022, 7–41

Graphical Abstract

Downloads

Published

2025-04-01

Issue

Section

Articles

How to Cite

Leila Zarin, & Javad Saien. (2025). Extractive performance of an acidic phosphonium-based deep eutectic solvent for simultaneous desulfurization and denitrogenation of real gasoline. Jeecpjournal, 2(2), 44-48. https://jeecpjournal.com/index.php/jeecp/article/view/14