Extractive desulfurization of diesel fuel by amide-based type IV deep eutectic solvents

Xu, Lixian; Luo, Yi; Liu, Hui; Yin, Jie; Li, Hongping; Jiang, Wei; Zhu, Wenshuai; Li, Huaming; Ji, Hongbing

doi:10.1016/j.molliq.2021.116620

Cited by 42 publications

(24 citation statements)

References 54 publications

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“…The Nernst partition coefficient ( K N ) is a key index to assess the extractive performance of extractants in liquid–liquid extraction. , To compare the EDS performance of TBAB/2CPL with the reported ILs or DESs, several representative DESs and ILs are listed in Table . It could be clearly seen that the K N value of TBAB/2CPL was greater than those of most DESs and ILs, as seen in Table , implying its higher extractive capacity.…”

Section: Results and Discussionmentioning

confidence: 99%

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Rational Design of Caprolactam-Based Deep Eutectic Solvents for Extractive Desulfurization of Diesel Fuel and Mechanism Study

Yin

Luo

et al. 2022

ACS Sustainable Chem. Eng.

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Deep eutectic solvents (DESs) are considered novel alternatives compared to organic solvents and ionic liquids. However, the low extractive efficiency of fuel oil has limited its wide application in desulfurization of diesel fuel. In this work, a series of caprolactam-based DESs were prepared using caprolactam as a hydrogen bond donor (HBD) and tetrabutylammonium halides as hydrogen bond acceptors (HBAs). By screening different halide anions and molar ratios of HBD and HBA, the DES tetrabutylammonium bromide/caprolactam (TBAB/CPL = 1:2) showed the highest desulfurization efficiency with the Nernst partition coefficient of 5.04, which was much higher than those of most metal-free DESs and ILs. The desulfurization efficiency could reach as high as 96.6% after a two-stage extraction. Finally, the extraction mechanism was investigated systematically using 1H nuclear magnetic resonance and Fourier transform infrared spectroscopies. Then, a density functional theory study suggested that hydrogen bonding and C–H···π interaction between DES and dibenzothiophene accounted for the higher desulfurization efficiency, enabling DES to effectively remove dibenzothiophene from the model fuels.

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Section: Results and Discussionmentioning

confidence: 99%

“…In this work, all of the calculations were supplemented at M06-2X-D3/6-311++G(d,p) in the Gaussian 16 program, which has been proved to have broad accuracy for noncovalent interactions . The interaction energy between DES and DBT can be expressed as where E is the energy of structural optimization.…”

Section: Experimental Sectionmentioning

confidence: 99%

Rational Design of Caprolactam-Based Deep Eutectic Solvents for Extractive Desulfurization of Diesel Fuel and Mechanism Study

Yin

Luo

et al. 2022

ACS Sustainable Chem. Eng.

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“…However, the HDS process has a poor effect on removing sulfur compounds with large steric hindrance (such as 4,6-DMDBT and 4-MDBT). , In order to achieve deep desulfurization, high temperature and high H 2 pressure are often required, which will cause huge economic cost. In order to make up for the deficiencies of HDS, some alternative methods such as extractive desulfurization (EDS), , oxidative desulfurization (ODS), − and photo-ODS − are now under consideration. Among them, the ODS process can remove almost all sulfur compounds in fossil fuels under mild conditions, so it has received widespread attention from society in recent years.…”

Section: Introductionmentioning

confidence: 99%

Deep Oxidative Desulfurization of Model Fuels Catalyzed by Subnanosized Ti Oxoclusters

et al. 2022

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Oxidative desulfurization is a highly effective approach to decrease the sulfur content in transportation fuel and has become an attractive research topic in recent years. Herewith, we have developed a new kind of carboxylic acid-functionalized imidazolium-based ionic liquid-stabilized Ti oxoclusters via a solvothermal method. The as-synthesized Ti oxoclusters were investigated by elemental analysis, Fourier transform infrared spectroscopy, diffuse reflectance UV–vis, X-ray diffraction, thermogravimetric analysis, high-resolution transmission electron microscopy (HRTEM), and high-angle annular dark field–scanning TEM. Characterization indicated that Ti oxoclusters existed in the form of subnanosized structure and uniformly dispersed with an average particle size of ca. 1 nm due to the protection role of the ionic liquids (ILs). Especially, Ti oxo–HSO4 afforded a superior catalytic activity in the extraction and catalytic oxidative desulfurization process with MeOH as an extractant and H2O2 as an oxidant. The full removal of dibenzothiophene in model fuels was achieved within 30 min at 60 °C. Besides, the Ti oxoclusters were robust and exhibited high stability in consecutive catalytic recycles. The parent Ti oxoclusters treated with H2O2 can afford Ti–OOH species, which was catalytically active species. The anion HSO4 – in IL played a crucial role in the activation of Ti–hydroperoxo species by forming hydrogen bonds. This may provide a new insight into the construction of metal oxoclusters for oxidative desulfurization.

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“…However, the harsh operating conditions led to high cost. 3,4 Therefore, a considerable number of more economical desulfurization methods have been explored during the last decade, including extractive, 5,6 adsorptive, 7,8 biological 9,10 and oxidative desulfurization (ODS). 11,12 Some of these methods have milder operating conditions and better removal efficiencies for the organic sulfur than HDS.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of modified amphiphilic quaternary ammonium silicotungstate and its application in heterogeneous catalytic oxidative desulfurization

Guo

Liu

2022

React. Chem. Eng.

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Extractive desulfurization of diesel fuel by amide-based type IV deep eutectic solvents

Cited by 42 publications

References 54 publications

Rational Design of Caprolactam-Based Deep Eutectic Solvents for Extractive Desulfurization of Diesel Fuel and Mechanism Study

Rational Design of Caprolactam-Based Deep Eutectic Solvents for Extractive Desulfurization of Diesel Fuel and Mechanism Study

Deep Oxidative Desulfurization of Model Fuels Catalyzed by Subnanosized Ti Oxoclusters

Synthesis of modified amphiphilic quaternary ammonium silicotungstate and its application in heterogeneous catalytic oxidative desulfurization

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