Oxidative removal of dibenzothiophene from model oil by C6H11NO/nCF3SO3H deep eutectic solvents

doi:10.16085/j.issn.1000-6613.2019-1027

Abstract

Abstract:

Deep eutectic solvents C₆H₁₁NO/nCF₃SO₃H(n=0.25,0.5,1) were synthesized by simply heating and stirring the mixture of caprolactam(C₆H₁₁NO) and trifluoromethanesulfonic acid(CF₃SO₃H). The structural characteristics of C₆H₁₁NO/nCF₃SO₃H were determined by infrared spectroscopy(FTIR) and hydrogen spectroscopy(¹HNMR). An extraction-oxidation desulfurization system was composed of C₆H₁₁NO/0.5CF₃SO₃H deep eutectic solvent and H₂O₂, and it was applied to remove dibenzothiophene(DBT) in model oil. The effects of n(CF₃SO₃H)∶n(C₆H₁₁NO), reaction temperature, O/S, dosage of C₆H₁₁NO/0.5CF₃SO₃H and different types of sulfides on desulfurization rate were studied. The experimental results indicated that under the optimum conditions of V(oil) 5mL, n(CF₃SO₃H)∶n(C₆H₁₁NO)=0.5, reaction temperature 60℃, O/S=6 and V(DESs) 1.0mL, the desulfurization rates of DBT, 4,6-DMDBT, BT and real oil were 99.4%, 98.6%, 83.6% and 61.6%, respectively. The stability of deep eutectic solvent was studied by infrared spectroscopy of recovered C₆H₁₁NO/0.5CF₃SO₃H. The interaction between DBT and DESs was analyzed by infrared spectroscopy of DBT, DESs and DBT-DESs. This interaction promoted the process of oxidative desulfurization. After five recycling runs, its desulfurization rate was still as high as 91.9%, indicating that C₆H₁₁NO/0.5CF₃SO₃H had high catalytic desulfurization activity and stability.

Key words: C₆H₁₁NO/0.5CF₃SO₃H, deep eutectic solvents, oxidation, extraction, dibenzothiophene

摘要：

通过简单加热并搅拌己内酰胺（C₆H₁₁NO）和三氟甲磺酸（CF₃SO₃H）的混合物合成了C₆H₁₁NO/nCF₃SO₃H（n=0.25，0.5，1）型酸性低共熔溶剂。利用红外光谱（FTIR）和氢谱（¹HNMR）确定了C₆H₁₁NO/nCF₃SO₃H的结构特征。以C₆H₁₁NO/0.5CF₃SO₃H低共熔溶剂和H₂O₂组成萃取-氧化脱硫系统，并将其应用于脱除模拟油中的二苯并噻吩（DBT）。研究n(CF₃SO₃H)∶n(C₆H₁₁NO)、反应温度、O/S、C₆H₁₁NO/0.5CF₃SO₃H的加入量和不同类型的硫化物对脱硫效果的影响。实验结果表明，在模拟油体积为5mL、n(CF₃SO₃H)∶n(C₆H₁₁NO)=0.5、反应温度为60℃、 O/S=6、C₆H₁₁NO/0.5CF₃SO₃H的加入量为1.0mL的最佳反应条件下，C₆H₁₁NO/0.5CF₃SO₃H对DBT、4,6-DMDBT、BT和真实油的脱硫率分别达99.4%、98.6%、83.6%和61.6%。红外表征分析了DBT与DESs之间存在相互作用，这种作用促进了氧化脱硫的进程。催化剂5次循环反应以后，其脱硫率仍高达91.9%，表明C₆H₁₁NO/0.5CF₃SO₃H低共熔溶剂具有较高的脱硫性能和稳定性。

关键词: C₆H₁₁NO/0.5CF₃SO₃H, 低共熔溶剂, 氧化, 萃取, 二苯并噻吩

CLC Number:

TE624

Haoran LIU, Yunqi WANG, Xiuping LI, Rongxiang ZHAO. Oxidative removal of dibenzothiophene from model oil by C₆H₁₁NO/nCF₃SO₃H deep eutectic solvents[J]. Chemical Industry and Engineering Progress, 2020, 39(5): 1632-1640.

刘昊然, 王韵淇, 李秀萍, 赵荣祥. C₆H₁₁NO/nCF₃SO₃H型低共熔溶剂氧化脱除模拟油中的二苯并噻吩[J]. 化工进展, 2020, 39(5): 1632-1640.

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Oxidative removal of dibenzothiophene from model oil by C₆H₁₁NO/nCF₃SO₃H deep eutectic solvents

C₆H₁₁NO/nCF₃SO₃H型低共熔溶剂氧化脱除模拟油中的二苯并噻吩

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