|
|
Extractive desulfurization of model fuels with a nitrogen-containing heterocyclic ionic liquid |
Guojia Yu, Dongyu Jin, Xinyu Li, Fan Zhang, Shichao Tian, Yixin Qu, Zhiyong Zhou(), Zhongqi Ren() |
College of Chemical Engineering, Beijing University of Chemical Technology, Beijing 100029, China |
|
|
Abstract A nitrogen-containing ionic liquid was synthesized using an aromatic nitrogen-containing heterocyclic and an amino acid, and applied to the extractive desulfurization process to remove benzothiophene, dibenzothiophene, and 4,6-dimethyldibenzothiphene from a model fuel oil. Chemical characterizations and simulation using Gaussian 09 software confirmed the rationality of an ionic liquid structure. Classification of non-covalent interactions between the ionic liquid and the three sulfur-containing contaminants was studied by reduced density gradient analysis. The viscosity of the ionic liquid was adjusted by addition of polyethylene glycol. Under extraction conditions of the volume of ionic liquid to oil as 1:1 and temperature as room temperature, the desulfurization selectivity of ionic liquid followed the order of 4,6-dimethyldibenzothiphene (15 min) < benzothiophene (15 min) ≈ dibenzothiophene (10 min). Addition of p-xylene and cyclohexene to the fuel oil had little effect. The extractant remained stable and effective after multiple regeneration cycles.
|
Keywords
extractive desulfurization
nitrogen-containing heterocyclic ionic liquid
reduced density gradient analysis
desulfurization selectivity
|
Corresponding Author(s):
Zhiyong Zhou,Zhongqi Ren
|
Online First Date: 18 August 2022
Issue Date: 19 December 2022
|
|
1 |
M F Majid, H F M Zaid, C F Kait, K Jumbri, L C Yuan, S Rajasuriyan. Futuristic advance and perspective of deep eutectic solvent for extractive desulfurization of fuel oil: a review. Journal of Molecular Liquids, 2020, 306 : 112870
https://doi.org/10.1016/j.molliq.2020.112870
|
2 |
G J Yu, X J Wu, L Wei, Z Y Zhou, W Liu, F Zhang, Y X Qu, Z Q Ren. Desulfurization of diesel fuel by one-pot method with morpholinium-based Brønsted acidic ionic liquid. Fuel, 2021, 296 : 120551
https://doi.org/10.1016/j.fuel.2021.120551
|
3 |
W Jiang, L Dong, W Liu, T Guo, H P Li, S Yin, W S Zhu, H M Li. Biodegradable choline-like deep eutectic solvents for extractive desulfurization of fuel. Chemical Engineering and Processing, 2017, 115 : 34– 38
https://doi.org/10.1016/j.cep.2017.02.004
|
4 |
L W Hao, M R Wang, W J Shan, C L Deng, W Z Ren, Z Z Shi, H Y Lü. L-Proline-based deep eutectic solvents (DESs) for deep catalytic oxidative desulfurization (ODS) of diesel. Journal of Hazardous Materials, 2017, 339 : 216– 222
https://doi.org/10.1016/j.jhazmat.2017.06.050
|
5 |
Z G Zhu, H Y Lu, M Zhang, H Q Yang. Deep eutectic solvents as non-traditionally multifunctional media for the desulfurization process of fuel oil. Physical Chemistry Chemical Physics, 2021, 23( 2): 785– 805
https://doi.org/10.1039/D0CP05153E
|
6 |
J Liu, W Y Li, J Feng, X Gao. Effects of Fe species on promoting the dibenzothiophene hydrodesulfurization over the Pt/gamma-Al2O3 catalysts. Catalysis Today, 2021, 371 : 247– 257
https://doi.org/10.1016/j.cattod.2020.07.035
|
7 |
L G Chen, Y Xu, B H Wang, J Yun, F Dehghani, Y T Xie, X Liang. Mg-modified CoMo/Al2O3 with enhanced catalytic activity for the hydrodesulfurization of 4,6-dimethyldibenzothiophene. Catalysis Communications, 2021, 155 : 106316
https://doi.org/10.1016/j.catcom.2021.106316
|
8 |
M Rezaee, F Feyzi, M R Dehghani. Extractive desulfurization of dibenzothiophene from normal octane using deep eutectic solvents as extracting agent. Journal of Molecular Liquids, 2021, 333 : 115991
https://doi.org/10.1016/j.molliq.2021.115991
|
9 |
F Lima, J Gouvenaux, L C Branco, A J D Silvestre, I M Marrucho. Towards a sulfur clean fuel: deep extraction of thiophene and dibenzothiophene using polyethylene glycol-based deep eutectic solvents. Fuel, 2018, 234 : 414– 421
https://doi.org/10.1016/j.fuel.2018.07.043
|
10 |
K H Almashjary, M Khalid, S Dharaskar, P Jagadish, R Walvekar, T C S M Gupta. Optimisation of extractive desulfurization using choline chloride-based deep eutectic solvents. Fuel, 2018, 234 : 1388– 1400
https://doi.org/10.1016/j.fuel.2018.08.005
|
11 |
J J Li, H Xiao, X D Tang, M Zhou. Green carboxylic acid-based deep eutectic solvents as solvents for extractive desulfurization. Energy & Fuels, 2016, 30( 7): 5411– 5418
https://doi.org/10.1021/acs.energyfuels.6b00471
|
12 |
S H Ali, D M Hamad, B H Albusairi, M A Fahim. Removal of dibenzothiophenes from fuels by oxy-desulfurization. Energy & Fuels, 2009, 23( 12): 5986– 5994
https://doi.org/10.1021/ef900683d
|
13 |
T Welton. Ionic liquids in catalysis. Coordination Chemistry Reviews, 2004, 248( 21-24): 2459– 2477
https://doi.org/10.1016/j.ccr.2004.04.015
|
14 |
L C Player, B Chan, M Y Lui, A F Masters, T Maschmeyer. Toward an understanding of the forces behind extractive desulfurization of fuels with ionic liquids. ACS Sustainable Chemistry & Engineering, 2019, 7( 4): 4087– 4093
https://doi.org/10.1021/acssuschemeng.8b05585
|
15 |
D Camargo, R S Andrade, G A Ferreira, H Mazzer, L Cardozo, M Iglesias. Investigation of the rheological properties of protic ionic liquids. Journal of Physical Organic Chemistry, 2016, 29( 11): 604– 612
https://doi.org/10.1002/poc.3553
|
16 |
N E Paucar, P Kiggins, B Blad, K De Jesus, F Afrin, S Pashikanti, K Sharma. Ionic liquids for the removal of sulfur and nitrogen compounds in fuels: a review. Environmental Chemistry Letters, 2021, 19( 2): 1205– 1228
https://doi.org/10.1007/s10311-020-01135-1
|
17 |
R Abro, A A Abdeltawab, S S Al-Deyab, G R Yu, A B Qazi, S R Gao, X C Chen. A review of extractive desulfurization of fuel oils using ionic liquids. RSC Advances, 2014, 4( 67): 35302– 35317
https://doi.org/10.1039/C4RA03478C
|
18 |
J D Holbrey, I Lo’pez-Martin, G Rothenberg, K R Seddon, G Silvero, X Zheng. Desulfurisation of oils using ionic liquids: selection of cationic and anionic components to enhance extraction efficiency. Green Chemistry, 2008, 10( 1): 87– 92
https://doi.org/10.1039/B710651C
|
19 |
H S Butt, K C Lethesh, A Fiksdahl. Fuel oil desulfurization with dual functionalized imidazolium based ionic liquids. Separation and Purification Technology, 2020, 248 : 116959
https://doi.org/10.1016/j.seppur.2020.116959
|
20 |
J J Raj, S Magaret, M Pranesh, K C Lethesh, W C Devi, M A Mutalib. Dual functionalized imidazolium ionic liquids as a green solvent for extractive desulfurization of fuel oil: toxicology and mechanistic studies. Journal of Cleaner Production, 2019, 213 : 989– 998
https://doi.org/10.1016/j.jclepro.2018.12.207
|
21 |
M H Ibrahim, M Hayyan, M A Hashim, A Hayyan. The role of ionic liquids in desulfurization of fuels: a review. Renewable & Sustainable Energy Reviews, 2017, 76 : 1534– 1549
https://doi.org/10.1016/j.rser.2016.11.194
|
22 |
J J Li, X J Lei, X D Tang, X P Zhang, Z Y Wang, S Jiao. Acid dicationic ionic liquids as extractants for extractive desulfurization. Energy & Fuels, 2019, 33( 5): 4079– 4088
https://doi.org/10.1021/acs.energyfuels.9b00307
|
23 |
Q Wang, T Zhang, S L Zhang, Y C Fan, B Chen. Extractive desulfurization of fuels using trialkylamine-based protic ionic liquids. Separation and Purification Technology, 2020, 231 : 115923
https://doi.org/10.1016/j.seppur.2019.115923
|
24 |
H S Butt, K C Lethesh, A Fiksdahl. Fuel oil desulfurization with dual functionalized imidazolium based ionic liquids. Separation and Purification Technology, 2020, 248 : 116959
https://doi.org/10.1016/j.seppur.2020.116959
|
25 |
M X Li, Z Y Zhou, F Zhang, W S Chai, L L Zhang, Z Q Ren. Deep oxidative-extractive desulfurization of fuels using benzyl-based ionic liquid. AIChE Journal. American Institute of Chemical Engineers, 2016, 62( 11): 4023– 4034
https://doi.org/10.1002/aic.15326
|
26 |
Z Q Ren, L Wei, Z Y Zhou, F Zhang, W Liu. Extractive desulfurization of model oil with protic ionic liquids. Energy & Fuels, 2018, 32( 9): 9172– 9181
https://doi.org/10.1021/acs.energyfuels.8b01936
|
27 |
O U Ahmed, F S Mjalli, A W Talal, Y Al-Wahaibi, I M Nashef. Extractive desulfurization of liquid fuel using modified pyrollidinium and phosphonium based ionic liquid solvents. Journal of Solution Chemistry, 2018, 47( 3): 468– 483
https://doi.org/10.1007/s10953-018-0732-1
|
28 |
J L Wang, R J Zhao, B X Han, N Tang, K X Li. Extractive and oxidative desulfurization of model oil in polyethylene glycol. RSC Advances, 2016, 6( 41): 35071– 35075
https://doi.org/10.1039/C6RA00996D
|
29 |
W Jiang, K Zhu, H P Li, L H Zhu, M Q Hua, J Xiao, C Wang, Z Z Yang, G Y Chen, W S Zhu, H Li, S Dai. Synergistic effect of dual Brønsted acidic deep eutectic solvents for oxidative desulfurization of diesel fuel. Chemical Engineering Journal, 2020, 394 : 124831
https://doi.org/10.1016/j.cej.2020.124831
|
30 |
I M Alecu, J J Zheng, Y Zhao, D G Truhlar. Computational thermochemistry: scale factor databases and scale factors for vibrational frequencies obtained from electronic model chemistries. Journal of Chemical Theory and Computation, 2010, 6( 9): 2872– 2887
https://doi.org/10.1021/ct100326h
|
31 |
X Wang, W Jiang, W S Zhu, H P Li, S Yin, Y H Chang, H M Li. A simple and cost-effective extractive desulfurization process with novel deep eutectic solvents. RSC Advances, 2016, 6( 36): 30345– 30352
https://doi.org/10.1039/C5RA27266A
|
32 |
T Lu, F W Chen. Multiwfn: a multifunctional wavefunction analyzer. Journal of Computational Chemistry, 2012, 33( 5): 580– 592
https://doi.org/10.1002/jcc.22885
|
33 |
D V Wagle, C A Deakyne, G A Baker. Quantum chemical insight into the interactions and thermodynamics present incholine chloride based deep eutectic solvents. Journal of Physical Chemistry B, 2016, 120( 27): 6739– 6746
https://doi.org/10.1021/acs.jpcb.6b04750
|
34 |
W Jiang, H Li, C Wang, W Liu, T Guo, H Liu, W S Zhu, H M Li. Synthesis of ionic liquid-based deep eutectic solvents for extractive desulfurization of fuel. Energy & Fuels, 2016, 30( 10): 8164– 8170
https://doi.org/10.1021/acs.energyfuels.6b01976
|
35 |
X Zhao, G Zhu, L Jiao, F Yu, C Xie. Formation and extractive desulfurization mechanisms of aromatic acid based deep eutectic solvents: an experimental and theoretical study. Chemistry, 2018, 24( 43): 11021– 11032
https://doi.org/10.1002/chem.201801631
|
36 |
C Shu, T Sun. Extractive desulfurisation of gasoline with tetrabutyl ammonium chloride-based deep eutectic solvents. Separation and Purification Technology, 2016, 51( 8): 1336– 1343
|
37 |
W Jiang, W Zhu, H Li, W Xin, Y Sheng, Y Chang, H M Li. Temperature-responsive ionic liquid extraction and separation of the aromatic sulfur compounds. Fuel, 2015, 140 : 590– 596
https://doi.org/10.1016/j.fuel.2014.09.083
|
38 |
W Zhu, C Wang, H Li, P Wu, S Xun, W Jiang, Z G Chen, Z Zhao, H M Li. One-pot extraction combined with metal-free photochemical aerobic oxidative desulfurization in deep eutectic solvent. Green Chemistry, 2015, 17( 4): 2464– 2472
https://doi.org/10.1039/C4GC02425G
|
39 |
N Khan, V C Srivastava. Quaternary ammonium salts-based deep eutectic solvents: utilization in extractive desulfurization. Energy & Fuels, 2021, 35( 15): 12734– 12745
https://doi.org/10.1021/acs.energyfuels.1c01220
|
40 |
J M Wu, X M Wu, P P Zhao, Z H Wang, L Z Zhang, D M Xu, J Gao. Extraction desulphurization of fuels using ZIF-8-based porous liquid. Fuel, 2021, 300 : 121013
https://doi.org/10.1016/j.fuel.2021.121013
|
41 |
P Makos, G Boczkaj. Deep eutectic solvents based highly efficient extractive desulfurization of fuels-eco-friendly approach. Journal of Molecular Liquids, 2019, 296 : 111916
https://doi.org/10.1016/j.molliq.2019.111916
|
|
Viewed |
|
|
|
Full text
|
|
|
|
|
Abstract
|
|
|
|
|
Cited |
|
|
|
|
|
Shared |
|
|
|
|
|
Discussed |
|
|
|
|