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Frontiers of Chemical Science and Engineering

ISSN 2095-0179

ISSN 2095-0187(Online)

CN 11-5981/TQ

邮发代号 80-969

2019 Impact Factor: 3.552

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Frontiers of Chemical Science and Engineering  2022, Vol. 16 Issue (12): 1735-1742   https://doi.org/10.1007/s11705-022-2167-x
  本期目录
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
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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.

Key words： extractive desulfurization    nitrogen-containing heterocyclic ionic liquid    reduced density gradient analysis    desulfurization selectivity
收稿日期: 2021-12-05      出版日期: 2022-12-19
Corresponding Author(s): Zhiyong Zhou,Zhongqi Ren   
 引用本文:   
. [J]. Frontiers of Chemical Science and Engineering, 2022, 16(12): 1735-1742.
Guojia Yu, Dongyu Jin, Xinyu Li, Fan Zhang, Shichao Tian, Yixin Qu, Zhiyong Zhou, Zhongqi Ren. Extractive desulfurization of model fuels with a nitrogen-containing heterocyclic ionic liquid. Front. Chem. Sci. Eng., 2022, 16(12): 1735-1742.
 链接本文:  
https://academic.hep.com.cn/fcse/CN/10.1007/s11705-022-2167-x
https://academic.hep.com.cn/fcse/CN/Y2022/V16/I12/1735
Fig.1  
IL-[DBU][L-Pyro] BT DBT DMDBT
Extraction efficiency/% 64.25 69.05 30.94
Tab.1  
Fig.2  
Bond Source Calculation/cm?1 Experiment/cm?1
–C=N –C=N in DBU 1662.8 1593.8
–C=O –C=O in carbonyl group 1713.6 1648.1
–C=O –C=O in –COOH 1798.9 1680.7
–OH O–H in –COOH 3327.3 3392.2
–NH –NH in –NH···C=O 3041.4 3236.2
–CH2–CH2 Six-membered ring 2989.8 2934.1
–CH2–CH2 Seven-membered ring 3038.5 3102.2
–C–N –C–N in DBU 1342.7 1400.3
?C–N –C–N in L-Pyro 1227.1 1292.3
–CH –CH2– 766.9 693.1
Tab.2  
Fig.3  
Fig.4  
ILs Molar ratio S-removal efficiency/%
BT DBT DMDBT
[IL][PEG200] 1:2 65.55 67.82 31.55
1:1 67.32 70.83 36.16
2:1 67.15 70.31 35.22
Tab.3  
Fig.5  
Fig.6  
Fig.7  
Fig.8  
Fig.9  
Fig.10  
Extractants vext:voil T/°C S-contents/ppm Model oil Extraction cycle Sulfur removal/% Ref.
TEA:BA 1.5:1 30 500 n-Octane 1 70.61 (BT) [35]
TEA:2OHBA 1.5:1 30 500 n-Octane 1 81.0 (DBT) [35]
TBAB:HCOOH 1:0.5 30 500 n-Octane 1 80.47 (DBT) [11]
TBAC:2MA 1:1 30 1000 n-Octane 5 99.2 (BT) [36]
[C4mpip]FeCl4 1 g:5 mL 45 500 Tetradecane 5 96 [37]
ChCl·2CH3COOH 1:5 30 500 ? 1 7.8 (DBT) [38]
[C2(Mim)2](HSO4)2 1:1 (w:w) 30 ? FCC 1 56.9 [22]
TBAB/2EG 1.2:1 25 500 Isooctane 1 81.2 (DBT) [39]
[DBU][Im] 1:1 room temperature 500 n-Octane 1 79.2 (DBT) [25]
[Epy][NTf2] 1:1(w:w) 25 500 n-Octane 1 43.94 (BT) [40]
[Bpy][NTf2] 1:1(w:w) 25 500 n-Octane 1 58.50 (BT) [40]
[Hpy][NTf2] 1:1(w:w) 25 500 n-Octane 1 63.86 (BT) [40]
[TMG][Im] 1:1 room temperature 500 n-Octane 1 69.4 (DBT) [25]
TBAB:FA 1:1 30 500 1 60 (DBT) [41]
TDA:SA 1:1(w:w) 25 500 n-Dodecane 5 72.68 (TH) [23]
76.31 (BT) [23]
83.94 (DBT) [23]
[IL][PEG200] 1:1 20 500 Tetradecane 4 98.8 (BT/DBT) This work
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