辽宁石油化工大学化学化工与环境学部,辽宁 抚顺 113001
王鑫博(1993—),男,硕士研究生,724581317@qq.com
赵荣祥(1971—),男,博士,副教授,zylhzrx@126.com
收稿:2018-10-22,
修回:2018-12-28,
网络首发:2020-06-15,
纸质出版:2019-04-12
移动端阅览
王鑫博, 张延平, 李秀萍, 赵荣祥. EMIES/nC9H10O2基低共熔溶剂的制备及其氧化脱硫活性的研究[J]. 化工学报, 2019, 70(4): 1567-1574 DOI: 10.11949/j.issn.0438-1157.20181251.
WANG Xinbo, ZHANG Yanping, LI Xiuping, ZHAO Rongxiang. Preparation of EMIES/nC9H10O2-based deep eutectic solvents and its oxidative desulfurization activity[J]. CIESC Journal, 2019, 70(4): 1567-1574 DOI: 10.11949/j.issn.0438-1157.20181251.
王鑫博, 张延平, 李秀萍, 赵荣祥. EMIES/nC9H10O2基低共熔溶剂的制备及其氧化脱硫活性的研究[J]. 化工学报, 2019, 70(4): 1567-1574 DOI: 10.11949/j.issn.0438-1157.20181251. DOI:
WANG Xinbo, ZHANG Yanping, LI Xiuping, ZHAO Rongxiang. Preparation of EMIES/nC9H10O2-based deep eutectic solvents and its oxidative desulfurization activity[J]. CIESC Journal, 2019, 70(4): 1567-1574 DOI: 10.11949/j.issn.0438-1157.20181251. DOI:
通过简单加热1-乙基-3-甲基咪唑硫酸乙酯(EMIES)离子液体和3-苯丙酸(C
9
H
10
O
2
)的混合物,制备了一系列酸性低共熔溶剂EMIES/
n
C
9
H
10
O
2
(
n
=0.25
0.5
1
2
4)。通过FTIR,
1
H NMR和TGA的表征,确定EMIES/
n
C
9
H
10
O
2
的结构。以该低共熔溶剂为催化剂和萃取剂,H
2
O
2
为氧化剂,组成氧化-萃取脱硫体系,用于脱除模拟油中的硫化物。考察了原料配比、反应温度、氧硫比(O/S)、低共熔溶剂加入量和不同硫化物对脱硫性能的影响。结果表明,在EMIES和C
9
H
10
O
2
摩尔比为1∶1,反应温度为50℃,O/S比为8,低共熔溶剂加入量为1.5 g和模拟油5 ml的反应条件下,二苯并噻吩、4
6-二甲基二苯并噻吩和苯并噻吩的脱除率分别为94.8%、91.6%和46.4%。低共熔溶剂可循环使用6次,活性无明显下降。此外,对该氧化-萃取脱硫体系的脱硫机理进行了探讨。
A series of acidic deep eutectic solvents (DESs) EMIES/
n
C
9
H
10
O
2
(
n
=0.25
0.5
1
2
4) were synthesized by simply heating t
he mixture of 1-ethyl-3-methylimidazolium ethylsulfate (EMIES) and 3-phenylpropionic acid (C
9
H
10
O
2
). The structure of EMIES/
n
C
9
H
10
O
2
was determined by FTIR
1
H NMR and TGA characterization. The extraction-oxidation desulfurization system was developed to remove sulfides from model oil using EMIES/
n
C
9
H
10
O
2
as the extractant and catalyst
H
2
O
2
as the oxidation. The influences of raw material ratio
reaction temperature
O/S ratio
amount of DESs and different sulfide on the desulfurization performance were investigated. The experimental results demonstrated the optimal reaction conditions were molar ratio of EMIES to C
9
H
10
O
2
of 1∶1
temperature of 50℃
O/S ratio of 8
the amount of DESs of 1.5 g and 5 ml model oil. Removal rate of DBT
4
6-DMDBT and BT reached 94.8%
91.6% and 46.4%
respectively
under the optimal condition. The DESs can be reused for 6 times without significant decrease in activity. In addition
the desulfurization mechanism of the oxidation-extraction desulfurization system was discussed.
Lü H , Li P , Deng C , et al . Deep catalytic oxidative desulfurization (ODS) of dibenzothiophene (DBT) with oxalate-based deep eutectic solvents (DESs) [J ] . Chemical Communications , 2015 , 51 ( 53 ): 10703 - 10706 .
Stanislaus A , Marafi A , Rana M S . Recent advances in the science and technology of ultra low sulfur diesel (ULSD) production [J ] . Catalysis Today , 2010 , 153 ( 1/2 ): 1 - 68 .
Soleimani M , Bassi A , Margaritis A . Biodesulfurization of refractory organic sulfur compounds in fossil fuels [J ] . Biotechnology Advances , 2007 , 25 ( 6 ): 570 - 596 .
Ma X , Zhou A , Song C . A novel method for oxidative desulfurization of liquid hydrocarbon fuels based on catalytic oxidation using molecular oxygen coupled with selective adsorption [J ] . Catalysis Today , 2007 , 123 ( 1 / 2 / 3 / 4 ): 276 - 284 .
Ko N H , Lee J S , Huh E S , et al . Extractive desulfurization using Fe-containing ionic liquids [J ] . Energy & Fuels , 2008 , 22 ( 3 ): 1687 - 1690 .
Park J G , Ko C H , Yi K B , et al . Reactive adsorption of sulfur compounds in diesel on nickel supported on mesoporous silica [J ] . Applied Catalysis B: Environmental , 2008 , 81 ( 3/4 ): 244 - 250 .
Zhang S , Zhang Q , Zhang Z C . Extractive desulfurization and denitrogenation of fuels using ionic liquids [J ] . Industrial & Engineering Chemistry Research , 2004 , 43 ( 2 ): 614 - 622 .
Wu Z , Xue Y , Zhang Y , et al . SnS 2 nanosheet-based microstructures with high adsorption capabilities and visible light photocatalytic activities [J ] . RSC Advances , 2015 , 5 ( 31 ): 24640 - 24648 .
Abbott A P , Capper G , Davies D L , et al . Novel solvent properties of choline chloride/urea mixtures [J ] . Chemical Communications , 2003 , ( 1 ): 70 - 71 .
Li C , Li D , Zou S , et al . Extraction desulfurization process of fuels with ammonium-based deep eutectic solvents [J ] . Green Chemistry , 2013 , 15 ( 10 ): 2793 - 2799 .
Li J , Xiao H , Tang X , et al . Green carboxylic acid-based deep eutectic solvents as solvents for extractive desulfurization [J ] . Energy & Fuels , 2016 , 30 ( 7 ): 5411 - 5418 .
Gano Z S , Mjalli F S , Al-Wahaibi T , et al . Extractive desulfurization of liquid fuel with FeCl 3 -based deep eutectic solvents: experimental design and optimization by central-composite design [J ] . Chemical Engineering and Processing: Process Intensification , 2015 , 93 : 10 - 20 .
Li C , Zhang J , Li Z , et al . Extraction desulfurization of fuels with ‘metal ions based deep eutectic solvents (MDESs) [J ] . Green Chemistry , 2016 , 18 ( 13 ): 3789 - 3795 .
Ekezie F G C , Sun D W , Cheng J H . Acceleration of microwave-assisted extraction processes of food components by integrating technologies and applying emerging solvents: a review of latest developments [J ] . Trends in Food Science & Technology , 2017 , 67 : 160 - 172 .
Dai D , Wang L , Chen Q , et al . Selective oxidation of sulfides to sulfoxides catalysed by deep eutectic solvent with H 2 O 2 [J ] . Journal of Chemical Research , 2014 , 38 ( 3 ): 183 - 185 .
Yin J , Wang J , Li Z , et al . Deep desulfurization of fuels based on an oxidation-extraction process with acidic deep eutectic solvents [J ] . Green Chemistry , 2015 , 17 ( 9 ): 4552 - 4559 .
Kudtak B , Owczarek K , Namieśnik J . Selected issues related to the toxicity of ionic liquids and deep eutectic solvents—a review [J ] . Environmental Science and Pollution Research , 2015 , 22 ( 16 ): 11975 - 11992 .
Leclercq L , Suisse I , Nowogrocki G , et al . Halide-free highly-pure imidazolium triflate ionic liquids: preparation and use in palladium-catalysed allylic alkylation [J ] . Green Chemistry , 2007 , 9 ( 10 ): 1097 - 1103 .
Jiang X , Nie Y , Li C , et al . Imidazolium-based alkylphosphate ionic liquids—a potential solvent for extractive desulfurization of fuel [J ] . Fuel , 2008 , 87 ( 1 ): 79 - 84 .
邢鹏飞 , 赵荣祥 , 李秀萍 , 等 . Bi 2 WO 6 的制备及其在离子液体中的超深度氧化脱硫 [J ] . 中国炼油与石油化工 , 2017 , 19 ( 1 ): 99 - 105 .
Xing P F , Zhao R X , Li X P , et al . Preparation of Bi 2 WO 6 and its ultra-deep oxidative desulfurization performance in ionic liquids [J ] . China Petroleum Processing and Petrochemical Technology , 2017 , 19 ( 1 ): 99 - 105 .
Wheeler J L , Pugh M K , Atkins S J , et al . Thermal breakdown kinetics of 1-ethyl-3-methylimidazolium ethylsulfate measured using quantitative infrared spectroscopy [J ] . Applied Spectroscopy , 2017 , 71 ( 12 ): 2626 - 2631 .
Dubey S , Bharmoria P , Gehlot P S , et al . 1-Ethyl-3-methylimidazolium diethylphosphate based extraction of bioplastic “polyhydroxyalkanoates” from bacteria: green and sustainable approach [J ] . ACS Sustainable Chemistry & Engineering , 2017 , 6 ( 1 ): 766 - 773 .
Stack R J , Cotta M A . Effect of 3-phenylpropanoic acid on growth of and cellulose utilization by cellulolytic ruminal bacteria [J ] . Applied and Environmental Microbiology , 1986 , 52 ( 1 ): 209 - 210 .
Wilkes J S , Zaworotko M J . Air and water stable 1-ethyl-3-methylimidazolium based ionic liquids [J ] . Journal of the Chemical Society , Chemical Communications , 1992 , ( 13 ): 965 - 967
Yuan B , Li Y , Yu F , et al . Benzylation with benzyl alcohol catalyzed by [ChCl ] [TfOH ] 2 , a Brønsted acidic DES with reaction control self-separation performance [J ] . Catalysis Letters , 2018 , 148 ( 7 ): 2133 - 2138 .
Jiang Y , Zhu W , Li H , et al . Oxidative desulfurization of fuels catalyzed by Fenton‐like ionic liquids at room temperature [J ] . ChemSusChem , 2011 , 4 ( 3 ): 399 - 403 .
Mokhtar W N A W , Bakar W A W A , Ali R , et al . Deep desulfurization of model diesel by extraction with N , N -dimethylformamide: optimization by Box–Behnken design [J ] . Journal of the Taiwan Institute of Chemical Engineers , 2014 , 45 ( 4 ): 1542 - 1548 .
Li F , Liu R , Wen J , et al . Desulfurization of dibenzothiophene by chemical oxidation and solvent extraction with Me 3 NCH 2 C 6 H 5 Cl·2ZnCl 2 ionic liquid [J ] . Green Chemistry , 2009 , 11 ( 6 ): 883 - 888 .
Qiu L , Cheng Y , Yang C , et al . Oxidative desulfurization of dibenzothiophene using a catalyst of molybdenum supported on modified medicinal stone [J ] . RSC Advances , 2016 , 6 ( 21 ): 17036 - 17045 .
Ede S R , Kundu S . Microwave synthesis of SnWO 4 nanoassemblies on DNA scaffold: a novel material for high performance supercapacitor and as catalyst for butanol oxidation [J ] . ACS Sustainable Chemistry & Engineering , 2015 , 3 ( 9 ): 2321 - 2336 .
Dong Y , Nie Y , Zhou Q . Highly efficient oxidative desulfurization of fuels by Lewis acidic ionic liquids based on iron chloride [J ] . Chemical Engineering & Technology , 2013 , 36 ( 3 ): 435 - 442 .
Chen J , Chen C , Zhang R , et al . Deep oxidative desulfurization catalyzed by an ionic liquid-type peroxotungsten catalyst [J ] . RSC Advances , 2015 , 5 ( 33 ): 25904 - 25910 .
Chen X , Song D , Asumana C , et al . Deep oxidative desulfurization of diesel fuels by Lewis acidic ionic liquids based on 1- n -butyl-3-methylimidazolium metal chloride [J ] . Journal of Molecular Catalysis A: Chemical , 2012 , 359 : 8 - 13 .
Zhu W S , Li H , Gu Q Q , et al . Kinetics and mechanism for oxidative desulfurization of fuels catalyzed by peroxo-molybdenum amino acid complexes in water-immiscible ionic liquids [J ] . Journal of Molecular Catalysis A: Chemical , 2011 , 336 ( 1/2 ): 16 - 22 .
Komintarachat C , Trakarnpruk W . Oxidative desulfurization using polyoxometalates [J ] . Industrial & Engineering Chemistry Research , 2006 , 45 ( 6 ): 1853 - 1856 .
Wei L , Zhou Z Y , Chen S P , et al . Electrochemically shape-controlled synthesis in deep eutectic solvents: triambic icosahedral platinum nanocrystals with high-index facets and their enhanced catalytic activity [J ] . Chemical Communications , 2013 , 49 ( 95 ): 11152 - 11154 .
Gao H , Guo C , Xing J , et al . Deep desulfurization of diesel oil with extraction using pyridinium-based ionic liquids [J ] . Separation Science and Technology , 2012 , 47 ( 2 ): 325 - 330 .
Mao C , Zhao R , Li X . Phenylpropanoic acid-based DESs as efficient extractants and catalysts for the removal of sulfur compounds from oil [J ] . Fuel , 2017 , 189 : 400 - 407 .
Zaid H F M , Chong F K , Mutalib M I A . Extractive deep desulfurization of diesel using choline chloride-glycerol eutectic-based ionic liquid as a green solvent [J ] . Fuel , 2017 , 192 : 10 - 17 .
Maggi R , Piscopo C G , Sartori G , et al . Supported sulfonic acids: metal-free catalysts for the oxidation of hydroquinones to benzoquinones with hydrogen peroxide [J ] . Applied Catalysis A: General , 2012 , 411 : 146 - 152 .
0
浏览量
1
下载量
2
CSCD
关联资源
相关文章
相关作者
相关机构
京公网安备11010102001995号