脱芳复合萃取剂的研究进展
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摘要
复合萃取剂包括传统复合溶剂和新型复合溶剂。前者是有机溶剂与有机溶剂或无机盐的复配,后者则是不同种类的离子液体复配,它们不仅具有对芳烃的溶解性好、选择性高的优点,而且萃取后,萃余油的收率相对较高,已经成为继单一萃取剂用于油品(石脑油、重整汽油和模拟油等)脱芳烃研究之后又一新的研究热点。本文综述了国内外脱芳烃复合萃取剂的研究进展,重点介绍了两类复合萃取剂(萃取剂与醇类、胺类溶剂或无机盐复配和离子液体复配)在油品萃取脱芳烃中的应用;根据复合萃取剂中助萃取剂的种类不同,对用于萃取脱芳烃的复合萃取剂进行了分类总结;介绍了不同种类的萃取剂复配与不同种类的离子液体复配的研究进展;最后指出复合萃取剂在分离芳烃应用中具有选择性高、分配系数高、操作工艺简单有效且成本低廉等优点,是工业上萃取脱芳烃今后的发展趋势。
The composite extractants include the traditional and the novel composite solvents. The former is the combination of two different organic solvents, or organic solvents and inorganic salts; the latter is the combination of different kinds of ionic liquids, which not only have excellent solubility and selectivity to aromatics, but also have relatively high yield of residual oil after extraction. The ionic liquids have become a new research hotspot after the single extractant used for the dearomatization of oil products(naphtha, reformed gasoline and simulated oil). In this paper, the research progress of composite extractants for aromatics removal around the world was reviewed, and the application of two kinds of composite extractants(extractants mixed with alcohols, amines or inorganic salts and ionic liquids) in the extraction of aromatics from oils was mainly introduced. According to the different kinds of auxiliaries in composite extractants, the composite extractants used for extraction of aromatics were classified and summarized. The research development of different kinds of extractants and ionic liquids was also introduced. Finally, the application of composite extractants in the separation of aromatics which has the advantages of high selectivity, high distribution coefficient, simple and effective operation process and low cost, is the development trend of industrial extraction for aromatics removal in the future are pointed.
The composite extractants include the traditional and the novel composite solvents. The former is the combination of two different organic solvents, or organic solvents and inorganic salts; the latter is the combination of different kinds of ionic liquids, which not only have excellent solubility and selectivity to aromatics, but also have relatively high yield of residual oil after extraction. The ionic liquids have become a new research hotspot after the single extractant used for the dearomatization of oil products(naphtha, reformed gasoline and simulated oil). In this paper, the research progress of composite extractants for aromatics removal around the world was reviewed, and the application of two kinds of composite extractants(extractants mixed with alcohols, amines or inorganic salts and ionic liquids) in the extraction of aromatics from oils was mainly introduced. According to the different kinds of auxiliaries in composite extractants, the composite extractants used for extraction of aromatics were classified and summarized. The research development of different kinds of extractants and ionic liquids was also introduced. Finally, the application of composite extractants in the separation of aromatics which has the advantages of high selectivity, high distribution coefficient, simple and effective operation process and low cost, is the development trend of industrial extraction for aromatics removal in the future are pointed.
引文
[1]邱纯书.我国增产三苯的工艺路线评述[J].化工进展, 2008, 27(8):1215-1221.QIU Chunshu.Review of the measures for increasing BTX production in China[J]. Chemical Industry and Engineering Progress, 2008, 27(8):1215-1221.
[2]范秀英,张微.我国汽车尾气污染状况及其控制对策分析[J].环境科学, 1999(5):102-108.FAN Xiuying, ZHANG Wei. Vehicle pollution situation and its control in China[J]. Environmental Science, 1999(5):102-108.
[3]张红星.汽柴油品质量标准与清洁燃料生产技术手段[J].中国石油和化工标准与质量, 2007, 27(8):41-43.ZHANG Hongxing. Gasoline and diesel quality standards and clean fuel production technology[J]. China Petroleum and Chemical Standard and Quality, 2007, 27(8):41-43.
[4]郑丽君,朱庆云,王春娇.国内外汽柴油质量标准分析及对我国的思考[J].中国石油和化工经济分析, 2015(9):5-9.ZHEN Lijun, ZHU Qingyun, WANG Chunjiao. Analysis of domestic and foreign quality standards for gasoline and diesel and thinking for China[J]. Economic Analysis of China Petroleum and Chemical Industry, 2015(9):5-9.
[5]史云鹤,李长明,周金波,等.石脑油萃取脱芳烃技术研究进展[J].化工进展, 2015, 34(2):360-369.SHI Yunhe, LI Changming, ZHOU Jingbo, et al. Research advances in extraction technology for dearomatization of naphtha[J]. Chemical Industry and Engineering Progress, 2015, 34(2):360-369.
[6] GAILE A A, ZALISHCHEVSKII G D, ERZHENKOV A S, et al.Extraction of aromatic hydrocarbons from reformates with mixtures of triethylene glycol and sulfolane[J]. Russian Journal of Applied Chemistry, 2007, 80(4):591-594.
[7] REICHARDT C, WELTON T. Solvents and solvent effects in organic chemistry[M]. Beijing:Chemical Industry Press, 1987.
[8] MAHMOUDI J, LOTFOLLAHI M N. Extraction of benzene from a narrow cut of naphtha via liquid-liquid extraction using puresulfolane and 2-propanol-sulfolane-mixed solvents[J]. Korean Journal of Chemical Engineering, 2010, 27(1):214-217.
[9]史云鹤,李长明,周金波,等.离心萃取法优选直馏石脑油脱芳烃萃取剂[J].应用化工, 2015(5):899-902.SHI Yunhe, LI Changming, ZHOU Jingbo, et al. Dearomatization effect study of composite extractant NMP-DMF to straight-run naphtha[J].Applied Chemical Industry, 2015(5):899-902.
[10] LABABIDI H, ALI S, FAHIM M. Optimization of aromatics extraction of naphtha reformate by propylene carbonate/diethylene glycol mixed solvent[J]. Industrial&Engineering Chemistry Research, 2006, 45(14):5086-5097.
[11] RADWAN G M, Al-MUHTASEB S A, FAHIM M A. Liquid-liquid equilibria for the extraction of aromatics from naphtha reformate by dimethylformamide/ethylene glycol mixed solvent[J]. Fluid Phase Equilibria,1997, 129(1/2):175-186.
[12]李晶晶,赵千舒,唐晓东,等.溶剂油萃取深度脱芳烃实验[J].化工进展, 2014, 33(8):1951-1956.LI Jingjing, ZHAO Qingshu, TANG Xiaodong, et al. Research on deep dearomatization of low aromatic solvent oils by extraction[J]. Chemical Industry and Engineering Progress, 2014, 33(8):1951-1956.
[13]张志刚,刘雷,李文秀,等.萃取精馏分离苯-环己烷三元混合溶剂的效应[J].化工学报, 2011, 62(9):2541-2545.ZHANG Zhigang, LIU Lei, LI Wenxiu, et al. Effect of ternary mixed solvent for separation of benzene-cyclohexane by extractive distillation[J]. CIESC Journal, 2011, 62(9):2541-2545.
[14]旷俊杰,杨基和,刘英杰,等.催化裂化回炼油溶剂精制新工艺的研究[J].精细石油化工, 2011, 28(6):52-54.KUANG Junjie, YANG Jihe, LIU Yingjie, et al. Study on new process of catalytic cracking refining solvent refining[J]. Speciality Petrochemicals, 2011, 28(6):52-54.
[15]薛凤凤,李冬,张琳娜,等.煤基石脑油萃取脱芳复合萃取剂[J].化工进展, 2017, 36(8):2897-2902.XUE Fengfeng, LI Dong, ZHANG Linna, et al. Composite extractant of liquid-liquid extraction aromatics for the coal-derived naphtha[J].Chemical Industry and Engineering Progress, 2017, 36(8):2897-2902.
[16] MAHMOUDI J, LOTFOLLAHI M N.(Liquid+liquid)equilibria of(sulfolane+benzene+n-hexane),(N-formylmorpholine+benzene+nhexane), and(sulfolane+N-formylmorpholine+benzene+n-hexane)at temperatures ranging from(298.15 to 318.15)K:experimental results and correlation[J]. Journal of Chemical Thermodynamics, 2010, 42(4):466-471.
[17] LI J J, ZHAO Q S, TANG X D, et al. Liquid-liquid equilibria for the systems:heptane+benzene+solvent(propylene carbonate, DMF, or mixtures)at temperatures from(303.2 to 323.2)K[J]. Journal of Chemical&Engineering Data, 2014, 59(11):3307-3313.
[18]董红星,王晓宇,杨晓光.加盐萃取-精馏耦合分离苯-环己烷共沸物[J].化学工程, 2009, 37(4):1-3.DONG Hongxing, WANG Xiaoyu, YANG Xiaoguang. Separation of benzene-cyclohexane azeotrope by combined process of extraction with salt and distillation[J]. Chemical Engineering, 2009, 37(4):1-3.
[19]董红星,张进,刘文信,等. N,N-二甲基乙酰胺+硫氰酸钾复合溶剂萃取分离苯-环己烷的选择性[J].石油化工, 2010, 39(7):762-765.DONG Hongxing. ZHANG Jin, LIU Wenxin, et al. Selectivity of extraction separation of benzene-cyclohexane with dimethylacetamide+potassium thiocyanate composite solvent[J].Petrochemical Technology, 2010, 39(7):762-765.
[20]董红星,杨晓光,姚春艳,等.糠醛加盐复合萃取剂萃取精馏分离苯和正庚烷[J].石油化工, 2008, 37(4):356-358.DONG Hongxing, YANG Xiaoguang, YAO Chunyan, et al. Separation of benzene and n-heptane by extractive distillation with furfural and salt[J]. Petrochemical Technology, 2008, 37(4):356-358.
[21]杨玉敏,崔蕊,臧红霞,等.加盐萃取精馏法分离间二甲苯-对二甲苯的研究[J].广东化工, 2015, 42(19):38-39.YANG Yumin, CUI Rui, ZANG Hongxia, et al. Study on extractive distillation for separating of m-xylene and p-xylene[J]. Guangdong Chemical Industry, 2015, 42(19):38-39.
[22] YANG X, SONG Q, DONG H, et al. Liquid-liquid equilibria of benzene+n-heptane+DMF and benzene+n-heptane+DMF+ammonium thiocyanate[J]. Journal of Chemical&Engineering Data,2013, 59(1):22-27.
[23] HOLBREY J D, REICHERT W M, NIEUWENHUYZEN M, et al.Liquid clathrate formation in ionic liquid-aromatic mixtures[J].Chemical Communications, 2003, 4(4):476-477.
[24] GARCíA S, GARCíA J, LARRIBA M, et al. Liquid-liquid extraction of toluene from heptane by{[4bmpy][Tf2N]+[emim][CHF2CF2SO3]}ionic liquid mixed solvents[J]. Fluid Phase Equilibria, 2013, 337(2):47-52.
[25] GARCíA S, LARRIBA M, CASAS A, et al. Separation of toluene and heptane by liquid-liquid extraction using binary mixtures of the ionic liquids 1-butyl-4-methylpyridinium bis(trifluoromethylsulfonyl)imide and 1-ethyl-3-methylimidazolium ethylsulfate[J]. J. Chem. Eng. Data,2012, 57(9):2472-2478.
[26] NAVARRO P, LARRIBA M, GARCíA J, et al. Selective recovery of aliphatics from aromatics in the presence of the{[4empy][Tf2N]+[emim][DCA]}ionic liquid mixture[J]. Journal of Chemical Thermodynamics, 2016, 96:134-142.
[27] LARRIBA M, NAVARRO P, GARCíA J, et al. Liquid-liquid extraction of BTEX from reformer gasoline using binary mixtures of[4empy][Tf2N] and[emim][DCA] ionic liquids[J]. Energy&Fuels,2014, 28(10):6666-6676.
[28] LARRIBA M, NAVARRO P, GARCíA J, et al. Liquid-liquid extraction of toluene from heptane using[emim][DCA],[bmim][DCA],and[emim][TCM] ionic liquids[J]. Industrial&Engineering Chemistry Research, 2013, 52(7):2714-2720.
[29] GARCíA J, GARCíA S, TORRECLLA J S, et al. Solvent extraction of toluene from heptane with the ionic liquids N-ethylpyridinium bis(trifluoromethylsulfonyl)imide and z-methyl-N-ethylpyridinium bis(trifluoromethylsulfonyl)imide(z=2, 3, or 4)at T=313.2K[J]. J.Chem. Eng. Data, 2010, 55(11):4937-4942.
[30] GARCíA S, LARRIBA M, GARCíA J, et al. Alkylsulfate-based ionic liquids in the liquid-liquid extraction of aromatic hydrocarbons[J].Journal of Chemical Thermodynamics, 2012, 45(1):68-74.
[31] GARCíA S, GARCíA J, LARRIBA M, et al. Sulfonate-based ionic liquids in the liquid-liquid extraction of aromatic hydrocarbons[J]. J.Chem. Eng. Data, 2011, 56(7):3188–3193.
[32] GARCíA S, LARRIBA M, GARCíA J, et al. Liquid-liquid extraction of toluene from n-heptane using binary mixtures of N-butylpyridinium tetrafluoroborate and N-butylpyridinium bis(trifluoromethylsulfonyl)imide ionic liquids[J]. Chemical Engineering Journal, 2012, 180(4):210-215.
[33] LARRIBA M, GARCíA S, NAVARRO P, et al. Physical characterization of an aromatic extraction solvent formed by[bpy][BF4]and[4bmpy][Tf2N] mixed ionic liquids[J]. Journal of Chemical&Engineering Data, 2013, 58(6):1496-1504.
[34] LARRIBA M, NAVARRO P, GARCíA J, et al. Liquid-liquid extraction of toluene from n-heptane by{[emim][TCM]+[emim][DCA]}binary ionic liquid mixtures[J]. Fluid Phase Equilibria, 2014,364:48-54.
[2]范秀英,张微.我国汽车尾气污染状况及其控制对策分析[J].环境科学, 1999(5):102-108.FAN Xiuying, ZHANG Wei. Vehicle pollution situation and its control in China[J]. Environmental Science, 1999(5):102-108.
[3]张红星.汽柴油品质量标准与清洁燃料生产技术手段[J].中国石油和化工标准与质量, 2007, 27(8):41-43.ZHANG Hongxing. Gasoline and diesel quality standards and clean fuel production technology[J]. China Petroleum and Chemical Standard and Quality, 2007, 27(8):41-43.
[4]郑丽君,朱庆云,王春娇.国内外汽柴油质量标准分析及对我国的思考[J].中国石油和化工经济分析, 2015(9):5-9.ZHEN Lijun, ZHU Qingyun, WANG Chunjiao. Analysis of domestic and foreign quality standards for gasoline and diesel and thinking for China[J]. Economic Analysis of China Petroleum and Chemical Industry, 2015(9):5-9.
[5]史云鹤,李长明,周金波,等.石脑油萃取脱芳烃技术研究进展[J].化工进展, 2015, 34(2):360-369.SHI Yunhe, LI Changming, ZHOU Jingbo, et al. Research advances in extraction technology for dearomatization of naphtha[J]. Chemical Industry and Engineering Progress, 2015, 34(2):360-369.
[6] GAILE A A, ZALISHCHEVSKII G D, ERZHENKOV A S, et al.Extraction of aromatic hydrocarbons from reformates with mixtures of triethylene glycol and sulfolane[J]. Russian Journal of Applied Chemistry, 2007, 80(4):591-594.
[7] REICHARDT C, WELTON T. Solvents and solvent effects in organic chemistry[M]. Beijing:Chemical Industry Press, 1987.
[8] MAHMOUDI J, LOTFOLLAHI M N. Extraction of benzene from a narrow cut of naphtha via liquid-liquid extraction using puresulfolane and 2-propanol-sulfolane-mixed solvents[J]. Korean Journal of Chemical Engineering, 2010, 27(1):214-217.
[9]史云鹤,李长明,周金波,等.离心萃取法优选直馏石脑油脱芳烃萃取剂[J].应用化工, 2015(5):899-902.SHI Yunhe, LI Changming, ZHOU Jingbo, et al. Dearomatization effect study of composite extractant NMP-DMF to straight-run naphtha[J].Applied Chemical Industry, 2015(5):899-902.
[10] LABABIDI H, ALI S, FAHIM M. Optimization of aromatics extraction of naphtha reformate by propylene carbonate/diethylene glycol mixed solvent[J]. Industrial&Engineering Chemistry Research, 2006, 45(14):5086-5097.
[11] RADWAN G M, Al-MUHTASEB S A, FAHIM M A. Liquid-liquid equilibria for the extraction of aromatics from naphtha reformate by dimethylformamide/ethylene glycol mixed solvent[J]. Fluid Phase Equilibria,1997, 129(1/2):175-186.
[12]李晶晶,赵千舒,唐晓东,等.溶剂油萃取深度脱芳烃实验[J].化工进展, 2014, 33(8):1951-1956.LI Jingjing, ZHAO Qingshu, TANG Xiaodong, et al. Research on deep dearomatization of low aromatic solvent oils by extraction[J]. Chemical Industry and Engineering Progress, 2014, 33(8):1951-1956.
[13]张志刚,刘雷,李文秀,等.萃取精馏分离苯-环己烷三元混合溶剂的效应[J].化工学报, 2011, 62(9):2541-2545.ZHANG Zhigang, LIU Lei, LI Wenxiu, et al. Effect of ternary mixed solvent for separation of benzene-cyclohexane by extractive distillation[J]. CIESC Journal, 2011, 62(9):2541-2545.
[14]旷俊杰,杨基和,刘英杰,等.催化裂化回炼油溶剂精制新工艺的研究[J].精细石油化工, 2011, 28(6):52-54.KUANG Junjie, YANG Jihe, LIU Yingjie, et al. Study on new process of catalytic cracking refining solvent refining[J]. Speciality Petrochemicals, 2011, 28(6):52-54.
[15]薛凤凤,李冬,张琳娜,等.煤基石脑油萃取脱芳复合萃取剂[J].化工进展, 2017, 36(8):2897-2902.XUE Fengfeng, LI Dong, ZHANG Linna, et al. Composite extractant of liquid-liquid extraction aromatics for the coal-derived naphtha[J].Chemical Industry and Engineering Progress, 2017, 36(8):2897-2902.
[16] MAHMOUDI J, LOTFOLLAHI M N.(Liquid+liquid)equilibria of(sulfolane+benzene+n-hexane),(N-formylmorpholine+benzene+nhexane), and(sulfolane+N-formylmorpholine+benzene+n-hexane)at temperatures ranging from(298.15 to 318.15)K:experimental results and correlation[J]. Journal of Chemical Thermodynamics, 2010, 42(4):466-471.
[17] LI J J, ZHAO Q S, TANG X D, et al. Liquid-liquid equilibria for the systems:heptane+benzene+solvent(propylene carbonate, DMF, or mixtures)at temperatures from(303.2 to 323.2)K[J]. Journal of Chemical&Engineering Data, 2014, 59(11):3307-3313.
[18]董红星,王晓宇,杨晓光.加盐萃取-精馏耦合分离苯-环己烷共沸物[J].化学工程, 2009, 37(4):1-3.DONG Hongxing, WANG Xiaoyu, YANG Xiaoguang. Separation of benzene-cyclohexane azeotrope by combined process of extraction with salt and distillation[J]. Chemical Engineering, 2009, 37(4):1-3.
[19]董红星,张进,刘文信,等. N,N-二甲基乙酰胺+硫氰酸钾复合溶剂萃取分离苯-环己烷的选择性[J].石油化工, 2010, 39(7):762-765.DONG Hongxing. ZHANG Jin, LIU Wenxin, et al. Selectivity of extraction separation of benzene-cyclohexane with dimethylacetamide+potassium thiocyanate composite solvent[J].Petrochemical Technology, 2010, 39(7):762-765.
[20]董红星,杨晓光,姚春艳,等.糠醛加盐复合萃取剂萃取精馏分离苯和正庚烷[J].石油化工, 2008, 37(4):356-358.DONG Hongxing, YANG Xiaoguang, YAO Chunyan, et al. Separation of benzene and n-heptane by extractive distillation with furfural and salt[J]. Petrochemical Technology, 2008, 37(4):356-358.
[21]杨玉敏,崔蕊,臧红霞,等.加盐萃取精馏法分离间二甲苯-对二甲苯的研究[J].广东化工, 2015, 42(19):38-39.YANG Yumin, CUI Rui, ZANG Hongxia, et al. Study on extractive distillation for separating of m-xylene and p-xylene[J]. Guangdong Chemical Industry, 2015, 42(19):38-39.
[22] YANG X, SONG Q, DONG H, et al. Liquid-liquid equilibria of benzene+n-heptane+DMF and benzene+n-heptane+DMF+ammonium thiocyanate[J]. Journal of Chemical&Engineering Data,2013, 59(1):22-27.
[23] HOLBREY J D, REICHERT W M, NIEUWENHUYZEN M, et al.Liquid clathrate formation in ionic liquid-aromatic mixtures[J].Chemical Communications, 2003, 4(4):476-477.
[24] GARCíA S, GARCíA J, LARRIBA M, et al. Liquid-liquid extraction of toluene from heptane by{[4bmpy][Tf2N]+[emim][CHF2CF2SO3]}ionic liquid mixed solvents[J]. Fluid Phase Equilibria, 2013, 337(2):47-52.
[25] GARCíA S, LARRIBA M, CASAS A, et al. Separation of toluene and heptane by liquid-liquid extraction using binary mixtures of the ionic liquids 1-butyl-4-methylpyridinium bis(trifluoromethylsulfonyl)imide and 1-ethyl-3-methylimidazolium ethylsulfate[J]. J. Chem. Eng. Data,2012, 57(9):2472-2478.
[26] NAVARRO P, LARRIBA M, GARCíA J, et al. Selective recovery of aliphatics from aromatics in the presence of the{[4empy][Tf2N]+[emim][DCA]}ionic liquid mixture[J]. Journal of Chemical Thermodynamics, 2016, 96:134-142.
[27] LARRIBA M, NAVARRO P, GARCíA J, et al. Liquid-liquid extraction of BTEX from reformer gasoline using binary mixtures of[4empy][Tf2N] and[emim][DCA] ionic liquids[J]. Energy&Fuels,2014, 28(10):6666-6676.
[28] LARRIBA M, NAVARRO P, GARCíA J, et al. Liquid-liquid extraction of toluene from heptane using[emim][DCA],[bmim][DCA],and[emim][TCM] ionic liquids[J]. Industrial&Engineering Chemistry Research, 2013, 52(7):2714-2720.
[29] GARCíA J, GARCíA S, TORRECLLA J S, et al. Solvent extraction of toluene from heptane with the ionic liquids N-ethylpyridinium bis(trifluoromethylsulfonyl)imide and z-methyl-N-ethylpyridinium bis(trifluoromethylsulfonyl)imide(z=2, 3, or 4)at T=313.2K[J]. J.Chem. Eng. Data, 2010, 55(11):4937-4942.
[30] GARCíA S, LARRIBA M, GARCíA J, et al. Alkylsulfate-based ionic liquids in the liquid-liquid extraction of aromatic hydrocarbons[J].Journal of Chemical Thermodynamics, 2012, 45(1):68-74.
[31] GARCíA S, GARCíA J, LARRIBA M, et al. Sulfonate-based ionic liquids in the liquid-liquid extraction of aromatic hydrocarbons[J]. J.Chem. Eng. Data, 2011, 56(7):3188–3193.
[32] GARCíA S, LARRIBA M, GARCíA J, et al. Liquid-liquid extraction of toluene from n-heptane using binary mixtures of N-butylpyridinium tetrafluoroborate and N-butylpyridinium bis(trifluoromethylsulfonyl)imide ionic liquids[J]. Chemical Engineering Journal, 2012, 180(4):210-215.
[33] LARRIBA M, GARCíA S, NAVARRO P, et al. Physical characterization of an aromatic extraction solvent formed by[bpy][BF4]and[4bmpy][Tf2N] mixed ionic liquids[J]. Journal of Chemical&Engineering Data, 2013, 58(6):1496-1504.
[34] LARRIBA M, NAVARRO P, GARCíA J, et al. Liquid-liquid extraction of toluene from n-heptane by{[emim][TCM]+[emim][DCA]}binary ionic liquid mixtures[J]. Fluid Phase Equilibria, 2014,364:48-54.