深共融溶剂在燃油脱除有机硫化物中的应用
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摘要
深共融溶剂(deep eutectic solvents,DESs)萃取脱硫技术具有操作简易、条件温和、成本低、脱硫效果好等优点,为燃油中有机硫化物的绿色深度脱除开辟了一条新的途径。本文综述了近5年DESs在燃油脱除有机硫化物中的最新研究成果,主要从直接萃取脱硫和氧化/萃取脱硫两方面对DESs脱硫进行综述。首先对不同DESs的脱硫效果进行了归纳总结,如以四丁基溴化铵/聚乙二醇直接萃取脱硫,3次萃取后,二苯并噻吩的脱除率可达100%;以氯化胆碱/乙酸为萃取剂氧化萃取脱硫,对二苯并噻吩模拟油的氧化萃取脱硫率也可达100%,可满足超低硫要求。同时对影响DESs脱硫效果的因素,如DESs的结构、脱硫的温度、时间、剂油比、硫化物的种类及浓度、氧化剂等进行了分析。然后对DESs的回收方法进行了总结,指出了回收过程中面临的问题并讨论了不同DESs的萃取脱硫机理。最后指出DESs脱硫面临的问题并展望了DESs在燃油脱硫中未来的发展前景。
The extractive desulfurization of deep eutectic solvents(DESs) has provided a new green method for the deep desulfurization of fuel due to its simple operation, mild conditions, low cost and high desulfurization efficiency. This article summarizes the progress in the past five years on applying DESs in the removal of organic sulfur compounds from fuel, including direct extractive desulfurization and oxidative-extractive desulfurization. Firstly, the desulfurization results of different DESs are summarized.For example, the extraction efficiency of dibenzothiophene is 100% after three extraction stages by tetrabutyl ammonium bromide/polyethylene glycol; the removal efficiency of dibenzothiophene can reach100% for oxidative desulfurization with choline chloride/acetic acid as an extractant. The desulfurization of DESs can meet the requirement of ultra-low sulfur. The factors influencing the desulfurization efficiencies of DESs, such as the structures of DESs, the temperature and time of desulfurization, ratio of DESs to oil, types and concentrations of sulfides, and oxidants are also analyzed. Then, the recovery methods of DESs are summarized, and the problems in the recovery process are pointed out. The mechanisms of desulfurization are also discussed. Finally, the problems of DESs desulfurization are pointed out and the prospect of DESs in the desulfurization of fuels is reviewed.
The extractive desulfurization of deep eutectic solvents(DESs) has provided a new green method for the deep desulfurization of fuel due to its simple operation, mild conditions, low cost and high desulfurization efficiency. This article summarizes the progress in the past five years on applying DESs in the removal of organic sulfur compounds from fuel, including direct extractive desulfurization and oxidative-extractive desulfurization. Firstly, the desulfurization results of different DESs are summarized.For example, the extraction efficiency of dibenzothiophene is 100% after three extraction stages by tetrabutyl ammonium bromide/polyethylene glycol; the removal efficiency of dibenzothiophene can reach100% for oxidative desulfurization with choline chloride/acetic acid as an extractant. The desulfurization of DESs can meet the requirement of ultra-low sulfur. The factors influencing the desulfurization efficiencies of DESs, such as the structures of DESs, the temperature and time of desulfurization, ratio of DESs to oil, types and concentrations of sulfides, and oxidants are also analyzed. Then, the recovery methods of DESs are summarized, and the problems in the recovery process are pointed out. The mechanisms of desulfurization are also discussed. Finally, the problems of DESs desulfurization are pointed out and the prospect of DESs in the desulfurization of fuels is reviewed.
引文
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[35]MAO C F,ZHAO R X,LI X P.Phenylpropanoic acid-based DESs as efficient extractants and catalysts for the removal of sulfur compounds from oil[J].Fuel,2017,189:400-407
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[2]宋红艳,何静,李春喜.燃料油深度脱硫的技术策略及研究进展[J].石油化工,2015,44(3):279-286.SONG H Y,HE J,LI C X.Technical strategies and recent advances for deep desulfurization of duel oils[J].Petrochemical Technology,2015,44(3):279-286.
[3]王宏伟,贺振富,田辉平.FCC汽油非临氢脱硫技术进展[J].化工进展,2005,24(11):1216-1224.WANG H W,HE Z F,TIAN H P.Progress in desulfurization of FCCgasoline without hydrogenation[J].Chemical Industry and Engineering Progress,2005,24(11):1216-1224.
[4]郑凯元,曲凤娇,陈英杰.等.非加氢脱硫技术研究进展及其在原油预脱硫中的应用展望[J].化工进展,2013,32(12):2859-2866.ZHENG K Y,QU F J,CHEN Y J,et al.Progress of nonhydrodesulfurization technologies of producing clean fuels and predesulfurization of crude oil[J].Chemical Industry and Engineering Progress,2013,32(12):2859-2866.
[5]项小燕,林金清.离子液体萃取燃料油脱硫技术的研究进展[J].化工进展,2007,26(12):1681-1685.XIANG X Y,LIN J Q.Progress of extractive desulfurization technology with ionic liquids[J].Chemical Industry and Engineering Progress,2007,26(12):1681-1685.
[6]PAIVA A,CRAVEIRO R,AROSO I,et al.Natural deep eutectic solvents-solvents for the 21st century[J].ACS Sustainable Chemistry Engineering,2014,2:1063-1071.
[7]HOU Y C,YAO C F,WU W Z.Deep eutectic solvents:green solvents for separation applications[J].Acta Physico-Chimica Sinica,2018,34(8):873-885.
[8]LI C P,LI D,ZOU S S,et al.Extraction desulfurization process of fuels with ammonium-based deep eutectic solvents[J].Green Chemistry,2013,15:2793-2799.
[9]LI C P,ZHANG J J,LI Z,et al.Extraction desulfurization of fuels with‘metal ions’based deep eutectic solvents(MDESs)[J].Green Chemistry,2016,18:3789-3795.
[10]GANO Z S,MJALLI F S,AL-WAHAIBI T,et al.Extractive desulfurization of liquid fuel with FeCl3-based deep eutectic solvents:Experimental design and optimization by central-composite design[J].Chemical Engineering and Processing:Process Intensification,2015,93:10-20.
[11]GANO Z S,MJALLI F S,AL-WAHAIBI T,et al.The novel application of hydrated metal halide(SnCl2·2H2O)-based deep eutectic solvent for the extractive desulfurization of liquid fuels[J].International Journal of Chemical Engineering and Applications,2015,6(5):367-371.
[12]GANO Z S,MJALLI F S,AL-WAHAIBI T,et al.Desulfurization of liquid fuel via extraction with imidazole-containing deep eutectic solvent[J].Green Processing and Synthesis,2017,6(5):511-521.
[13]RAHMA W S A,MJALLI F S,AL-WAHAIBI T,et al.Polymericbased deep eutectic solvents for effective extractive desulfurization of liquid fuel at ambient conditions[J].Chemical Engineering Research and Design,2017,120:271-283.
[14]TANG X D,ZHANG Y F,LI J J,et al.Deep extractive desulfurization with arenium ion deep eutectic solvents[J].Industrial&Engineering Chemistry Research,2015,54:4625-4632.
[15]TANG X D,ZHANG Y F,LI J J,et al.Alkylation of thiophenic compounds catalyzed by deep eutectic solvents[J].Catalysis Communications,2015,70:40-43.
[16]LI J J,XIAO H,TANG X D,et al.Green carboxylic acid-based deep eutectic solvents as solvents for extractive desulfurization[J].Energy Fuels,2016,30(7):5411-5418.
[17]LI J J,ZHOU M,TANG X D,et al.Deep desulfurization of FCCgasoline by extraction with dicarboxylic acid-based deep eutectic solvents[J].Petroleum Science and Technology,2017,35(19):1903-1909.
[18]WANG X,JIANG W,ZHU W S,et al.A simple and cost-effective extractive desulfurization process with novel deep eutectic solvents[J].RSC Advances,2016,6:30345-30352.
[19]JIANG W,LI H P,WANG C,et al.Synthesis of ionic-liquid-based deep eutectic solvents for extractive desulfurization of fuel[J].Energy Fuels,2016,30:8164-8170.
[20]JIANG W,DONG L,LIU W,et al.Biodegradable choline-like deep eutectic solvents for extractive desulfurization of fuel[J].Chemical Engineering and Processing:Process Intensification,2017,115:34-38.
[21]SHU C H,SUNT H.Extractive desulfurisation of gasoline with tetrabutyl ammonium chloride-based deep eutectic solvents[J].Separation Science and Technology,2016,51:1336-1343.
[22]HADJ-KALI M K,MULYONO S,HIZADDIN H F,et al.Removal of thiophene from mixtures with n-heptane by selective extraction using deep eutectic solvents[J].Industrial&Engineering Chemistry Research,2016,55(30):8415-8523.
[23]CHENG H Y,LIU C Y,ZHANG J J,et al.Screening deep eutectic solvents for extractive desulfurization of fuel based on COSMO-RSmodel[J].Chemical Engineering&Processing:Process Intensification,2018,125:246-252.
[24]WARRAG S E E,RODRIGUEZ N R,NASHEF I M,et al.Separation of thiophene from aliphatic hydrocarbons using tetrahexylammoniumbased deep eutectic solvents as extracting agents[J].Journal of Chemical&Engineering Data,2017,62(9):2911-2919.
[25]WARRAG S E E,ADEYEMI I,RODRIGUEZ N R,et al.Effect of the type of ammonium salt on the extractive desulfurization of fuels using deep eutectic solvents[J].Journal of Chemical&Engineering Data,2018,63(4):1088-1095.
[26]YIN J M,WANG J P,LI Z,et al.Deep desulfurization of fuels based on oxidation/extraction process with acidic deep eutectic solvents[J].Green Chemistry,2015,17:4552-4559.
[27]LüH Y,LI C P,DENG C L,et al.Deep catalytic oxidative desulfurization(ODS)of dibenzothiophene(DBT)with oxalate-based deep eutectic solvents(DESs)[J].Chemical Communications,2015,51:10703-10706.
[28]HAO L W,WANG M R,SHAN W J,et al.L-proline-based deep eutectic solvents(DESs)for deep catalytic oxidative desulfurization(ODS)of diesel[J].Journal of Hazardous Materials,2017,339:216-222.
[29]ZHU W S,WANG C,LI H P,et al.One-pot extraction combined with metal-free photochemical aerobic oxidative desulfurization in deep eutectic solvent[J].Green Chemistry,2015,17:2464-2472.
[30]侯良培,赵荣祥,李秀萍,等.甲基咪唑盐酸盐/草酸型低共熔溶剂的制备及其在模拟油中氧化脱硫中的应[J].化工学报,2016,67(9):3972-3980.HOU L P,ZHAO R X,LI X P,et al.Preparation of methylimidazole hydrochloride/oxalic acid type deep eutectic solvent and its application in oxidative desulfurization of model oil[J].CIESC Journal,2016,67(9):3972-3980.
[31]毛春峰,赵荣祥,李秀萍.氯化胆碱/草酸低共熔溶剂高效脱除模拟油中硫[J].化学工程,2017,45(5):6-10.MAO C F,ZHAO R X,LI X P.High removal rate of sulfur in model oil by ChCl/H2C2O4deep eutectic solvents[J].Chemical Engineering(China),2017,45(5):6-10.
[32]毛春峰,赵荣祥,李秀萍,等.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 C F,ZHAO R X,LI X P,et al.Removal of sulfides from simulated oil by CH3CONH2/ZnCl2deep eutectic solvent[J].Journal of Liaoning Shihua University,2017,37(5):1-7.
[33]侯良培,赵荣祥,李秀萍,酸性低共熔溶剂四乙基氯化铵/三氟乙酸高效催化氧化脱除模拟油中的硫化物[J].化工学报,2017,68(4):1614-1620.HOU L P,ZHAO R X,LI X P,Highly efficient catalytic oxidation desulfurization from model oil based on acid deep eutectic solvents tetraethylammonium chloride/trifluoroacetic acid[J].CIESC Journal,2017,68(4):1614-1620.
[34]侯良培,赵荣祥,李秀萍.[C4Pyr]Cl/n TsOH型低共熔溶剂的制备及其氧化脱除模拟油中的二苯并噻吩[J].石油化工,2017,46(7):888-895.HOU L P,ZHAO R X,LI X P.Preparation of C4Pyr]Cl/n TsOH deep eutectic solvents and its application in oxidative removal of dibenzothiophene from model oil[J].Petrochemical Technology,2017,46(7):888-895.
[35]MAO C F,ZHAO R X,LI X P.Phenylpropanoic acid-based DESs as efficient extractants and catalysts for the removal of sulfur compounds from oil[J].Fuel,2017,189:400-407
[36]MAO C F,ZHAO R X,LI X P.Propionic acid-based deep eutectic solvents:synthesis and ultra-deep oxidative desulfurization activity[J].RSC Advances,2017,7:42590-42596.
[37]LIU W,JIANG W,ZHU W Q,et al.Oxidative desulfurization of fuels promoted by choline chloride-baseddeep eutectic solvents[J].Journal of Molecular Catalysis A:Chemical,2016,424:261-268.
[38]JIANG W,DONG L,LIU W,et al.Designing multifunctional SO3H-based polyoxometalate catalysts for oxidative desulfurization in acid deep eutectic solvent[J].RSC Advances,2017,7:55318-55325.
[39]ZAID H F M,KAIT C F,MUTALI M I A.Extractive deep desulfurization of diesel using choline chloride-glycerol eutecticbased ionic liquid as a green solvent[J].Fuel,2017,192:10-17.
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