EMIES/p-TsOH型低共熔溶剂的合成及其氧化脱硫性能的研究
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摘要
通过1-乙基-3-甲基咪唑硫酸乙酯离子液体(EMIES)和对甲苯磺酸(p-TsOH)的混合物制备EMIES/p-TsOH型低共熔溶剂。其结构特征通过红外光谱、氢谱和热重技术进行了分析。并以EMIES/p-TsOH作为催化剂与萃取剂,H2O2作为氧化剂研究了其对模拟油中的硫化物的脱除性能。考察了反应温度、n(H2O2)/n(S)比、低共熔溶剂加入量及硫化物类型对脱硫效果的影响。在最佳的条件下,模拟油中二苯并噻吩(DBT)、4,6-二甲基二苯并噻吩(4,6-DMDBT)和苯并噻吩(BT)的脱除率分别为96.2%、92.2%和88.8%。经过五次循环使用后,DBT的脱除率仍达到93.6%。对该脱硫体系进行了动力学分析,其表观活化能为66.4 k J/mol。
The deep eutectic solvent(DESs)of EMIES/p-TsOH was synthesized by stirring a mixture of 1-ethyl-3-methylimidazolium ethyl sulfate(EM IES)and p-toluene sulfonic acid(p-TsOH),the structure of catalysts was characterized by infrared analysis(FT-IR),hydrogen spectrum analysis(~1H-NM R)and thermogravimetric analysis(TG),the desulfurization performance of model oil was investigated using EM IES/pTsOH as a catalyst and extraction agent and using H_2O_2as the oxidation,and the effects of the temperature,n(H_2O_2)/n(S)molar ratio,and the amount of DESs on the desulfurization activity were investigated in detail.Under the optimal conditions,the removal rate of dibenzothiophene(DBT),4,6-dimethyldibenzothiophene(4,6-DM DBT)and benzothiophene(BT)can reach up to 96.2%,92.2%and 88.8%,respectively.After five recycling runs,the removal rate of DBT can still reach 93.6%.The kinetic analysis of the desulfurization system indicates that the apparent activation energy is 66.4 k J/mol.
The deep eutectic solvent(DESs)of EMIES/p-TsOH was synthesized by stirring a mixture of 1-ethyl-3-methylimidazolium ethyl sulfate(EM IES)and p-toluene sulfonic acid(p-TsOH),the structure of catalysts was characterized by infrared analysis(FT-IR),hydrogen spectrum analysis(~1H-NM R)and thermogravimetric analysis(TG),the desulfurization performance of model oil was investigated using EM IES/pTsOH as a catalyst and extraction agent and using H_2O_2as the oxidation,and the effects of the temperature,n(H_2O_2)/n(S)molar ratio,and the amount of DESs on the desulfurization activity were investigated in detail.Under the optimal conditions,the removal rate of dibenzothiophene(DBT),4,6-dimethyldibenzothiophene(4,6-DM DBT)and benzothiophene(BT)can reach up to 96.2%,92.2%and 88.8%,respectively.After five recycling runs,the removal rate of DBT can still reach 93.6%.The kinetic analysis of the desulfurization system indicates that the apparent activation energy is 66.4 k J/mol.
引文
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[2]CAMPOS-MARTIN J M,CAPEL-SANCHEZ M C,PEREZ-PRESAS P,FIERRO J L G.Oxidative processes of desulfurization of liquid fuels[J].J Appl Chem Biotechnol,2010,85(7):879-890.
[3]LI H,ZHU W,LU J,JIANG X,GONG L,ZHU G,YAN Y.Deep oxidative desulfurization of fuels catalyzed by pristine simple tungstic acid[J].React Kinet Catal Lett,2009,96(1):165-173.
[4]CHEN J,CHEN C,ZHANG R,GUO L,HUA L,CHEN A,XIU Y,LIU X,HOU Z.Deep oxidative desulfurization catalyzed by an ionic liquid-type peroxotungsten catalyst[J].RSC Adv,2015,5(33):25904-25910.
[5]NIE Y,LI C,SUN A,MENG H,WANG Z.Extractive desulfurization of gasoline using imidazolium-based phosphoric ionic liquids[J].Energy Fuels,2006,20(5):2083-2087.
[6]EBER J,WASSERSCHEID P,JESS A.Deep desulfurization of oil refinery streams by extraction with ionic liquids[J].Green Chem,2004,6(7):316-322.
[7]LU H,REN W,WANG H,WANG Y,CHEN W,SUO Z.Deep desulfurization of diesel by ionic liquid extraction coupled with catalytic oxidation using an Anderson-type catalyst[(C4H9)4N]4NiM o6O24H6[J].Appl Catal,2013,453:376-382.
[8]HAGENSON L C,NAIK S D,DORAISWAMY L K.Rate enhancements in a solid-liquid reaction using PTC,microphase,ultrasound and combinations thereof[J].Chem Eng Sci,1994,49(24):4787-4800.
[9]SHEN Y,LU X,MA X,HE J,ZHANG D,ZHAN H,XIA Q.Oxidative desulfurization of thiophene derivatives with H2O2in the presence of catalysts based on M oO3/Al2O3under mild conditions[J].Kinet Catal,2017,58(1):28-33.
[10]YANG Y,LV G,DENG L,LU B,LI J,ZHANG J,SHI J,DU S.Ultra-deep desulfurization of diesel fuel via selective adsorption over modified activated carbon assisted by pre-oxidation[J].J Cleaner Prod,2017,161:422-430.
[11]SAEEDIRAD R,GANJALI S T,BAZMI M,RASHIDI A.Effective mesoporous silica-ZIF-8 nano-adsorbents for adsorptive desulfurization of gas stream[J].J Taiwan Inst Chem Eng,2018,82:10-22.
[12]LI G,LI S,ZHANG M,WANG J,ZHU L,LIANG F,LIU R,MA T.Genetic rearrangement strategy for optimizing the dibenzothiophene biodesulfurization pathway in Rhodococcus erythropolis[J].Appl Environ M icrobiol,2008,74(4):971-976.
[13]LU Q,PENG W,XUN S,HE M,MA R,JIANG W,ZHU W,LI H.Controllable preparation of highly dispersed TiO2nanoparticles for enhanced catalytic oxidation of dibenzothiophene in fuels[J].Appl Organomet Chem,2018,32(6):e4351.
[14]CHAKMA S,DAS L,MOHOLKAR V S.Dye decolorization with hybrid advanced oxidation processes comprising sonolysis/Fenton-like/photo-ferrioxalate systems:A mechanistic investigation[J].Sep Purif Technol,2015,156:596-607.
[15]YAZU K,YAMAMOTO Y,FURUYA T,MIKI K,UKEGAWA K.Oxidation of dibenzothiophenes in an organic biphasic system and its application to oxidative desulfurization of light oil[J].Energy Fuels,2001,15(6):1535-1536.
[16]毛春峰,赵荣祥,李秀萍.CH3CONH2/ZnCl2低共熔溶剂脱除模拟油中的硫化物[J].辽宁石油化工大学学报,2017,37(5):1-7.(MAO Chun-feng,ZHAO Rong-xiang,LI Xiu-ping.Removal of sulfides from simulated oil by CH3CONH2/ZnCl2deep eutectic solvent[J].J Liaoning Shihua Univ,2017,37(5):1-7.)
[17]ALIZADEH A,FAKHARI M,KHODEAI M M,ABDI G,AMIRIAN J.Oxidative desulfurization of model oil in an organic biphasic system catalysed by Fe3O4@SiO2-ionic liquid[J].RSC Adv,2017,7(56):34972-34983.
[18]ZHANG S,ZHANG Q,ZHANG Z C.Extractive desulfurization and denitrogenation of fuels using ionic liquids[J].Ind Eng Chem Res,2004,43(2):614-622.
[19]BOSMANN A,DATSEVICH L,JESS A,LAUTER A,SCHMITZ C,WASSERSCHEID P.Deep desulfurization of diesel fuel by extraction with ionic liquids[J].Chem Commun,2001,(23):2494-2495.
[20]HUANG C,CHEN B,ZHANG J,LIU Z,LI Y.Desulfurization of gasoline by extraction with newionic liquids[J].Energy Fuels,2004,18(6):1862-1864.
[21]GANO Z S,MJALLI F S,AL-WAHAIBI T,AL-WAHAIBI Y,ALNASHEF I M.Extractive desulfurization of liquid fuel with Fe Cl3-based deep eutectic solvents:experimental design and optimization by central-composite design[J].Chem Eng Process,2015,93:10-20.
[22]LI C,LI D,ZOU S,LI Z,YIN J,WANG A,CUI Y,YAO Z,ZHAO Q.Extraction desulfurization process of fuels with ammonium-based deep eutectic solvents[J].Green Chem,2013,15(10):2793-2799.
[23]YIN J,WANG J,LI Z,LI D,YANG G,CUI Y,WANG A,LI C.Deep desulfurization of fuels based on an oxidation/extraction process with acidic deep eutectic solvents[J].Green Chem,2015,17(9):4552-4559.
[24]LIU W,JIANG W,ZHU W,ZHU W,LI H,GUO T,ZHU W,LI H.Oxidative desulfurization of fuels promoted by choline chloride-based deep eutectic solvents[J].J M ol Catal A:Chem,2016,424:261-268.
[25]CAO J,SHANG Y,QI B,SUN X,ZHANG L,LIU H,ZHANG H,ZHOU X.Synthesis of pillar[n]arenes(n=5 and 6)with deep eutectic solvent choline chloride 2FeCl3[J].RSC Adv,2015,5(13):9993-9996.
[26]DAI D,WANG L,CHEN Q,HE M.Selective oxidation of sulfides to sulfoxides catalysed by deep eutectic solvent with H2O2[J].J Chem Res,2014,38(3):183-185.
[27]LU H,LI P,DENG C,REN W,WANG S,LIU P.Deep catalytic oxidative desulfurization(ODS)of dibenzothiophene(DBT)with oxalate-based deep eutectic solvents(DESs)[J].Chem Commun,2015,51(53):10703-10706.
[28]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.
[29]HOLBREY J D,REICHERT W M,SWATLOSKI R P,GRANT A.Efficient,halide free synthesis of new,low cost ionic liquids:1,3-dialkylimidazolium salts containing methyl-and ethyl-sulfate anions[J].Green Chem,2002,4(5):407-413.
[30]LI C,LI D,ZOU S,LI Z,YIN J,WANG A,CUI Y,YAO Z.Extraction desulfurization process of fuels with ammonium-based deep eutectic solvents[J].Green Chem,2013,15(10):2793-2799.
[31]WHEELER J L,PUGH M K,ATKINS S J,PORTER J M.Thermal breakdown kinetics of 1-ethyl-3-methylimidazolium ethylsulfate measured using quantitative infrared spectroscopy[J].Appl Spectrosc,2017,71(12):2626-2631.
[32]HAO L,WANG M,SHAN W,DENG C,REN W,SHI Z,LV H.L-proline-based deep eutectic solvents(DESs)for deep catalytic oxidative desulfurization(ODS)of diesel[J].J Hazard M ater,2017,339:216-222.
[33]GOMEZ E,GONZLEZ B,CALVAR N,TOJO E,DOMINGUEZ A.Physical properties of pure 1-ethyl-3-methylimidazolium ethylsulfate and its binary mixtures with ethanol and water at several temperatures[J].J Chem Eng Data,2006,51(6):2096-2102.
[34]DONG Y,NIE Y,ZHOU Q.Highly efficient oxidative desulfurization of fuels by Lewis acidic ionic liquids based on iron chloride[J].Chem Eng Technol,2013,36(3):435-442.
[35]YUAN B,LI Y,YU F,LI X,XIE C,YU S.Benzylation with benzyl alcohol catalyzed by[ChCl][TfOH]2,a brnsted acidic des with reaction control self-separation performance[J].Catal Lett,2018,148(7):2133-2138.
[36]CHEN W J,XUE Z M,WANG J F,JIANG J Y,ZHAO X H,MU T C.Investigation on the thermal stability of deep eutectic solvents[J].Acta Phy Chim Sin,2017,34(8):904-911.
[37]SHU C,SUN T,ZHANG H,JIA J,LOU Z.A novel process for gasoline desulfurization based on extraction with ionic liquids and reduction by sodium borohydride[J].Fuel,2014,121:72-78.
[38]JIANG W,ZHU W,LI H,WANG X,YIN S,CHANG Y,LI H.Temperature-responsive ionic liquid extraction and separation of the aromatic sulfur compounds[J].Fuel,2015,140:590-596.
[38]SHU C,SUN T,ZHANG H,JIA J,LOU Z.A novel process for gasoline desulfurization based on extraction with ionic liquids and reduction by sodium borohydride[J].Fuel,2014,121:72-78.
[40]CHEN J,CHEN C,ZHANG R,LI G,LI H,CHEN A,XIU Y,LIU X,HOU Z.Deep oxidative desulfurization catalyzed by an ionic liquidtype peroxotungsten catalyst[J].RSC Adv,2015,5(33):25904-25910.
[41]ZHANG C,PAN X,WANG F,LIU X.Extraction-oxidation desulfurization by pyridinium-based task-specific ionic liquids[J].Fuel,2012,102:580-584.
[42]GAO H,GUO C,XING J,LIU H.Deep desulfurization of diesel oil with extraction using pyridinium-based ionic liquids[J].Sep Sci Technol,2012,47(2):325-330.
[43]ZHU W S,LI H,GU Q Q,WU P,ZHU G,YAN Y S,CHEN G Y.Kinetics and mechanism for oxidative desulfurization of fuels catalyzed by peroxo-molybdenum amino acid complexes in water-immiscible ionic liquids[J].J M ol Catal A:Chem,2011,336(1):16-22.
[44]WANG D,QIAN E W,AMANO H,OKATA K,ISHIHARA A,KABE T.Oxidative desulfurization of fuel oil:Part I.Oxidation of dibenzothiophenes using tert-butyl hydroperoxide[J].Appl Catal A:Gen,2003,253(1):91-99.
[45]WEI L,ZHOU Z Y,CHEN S P,XU C D,SU D,SCHUSTER M E,SUN S G.Electrochemically shape-controlled synthesis in deep eutectic solvents:Triambic icosahedral platinum nanocrystals with high-index facets and their enhanced catalytic activity[J].Chem Commun,2013,49(95):11152-11154.
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