离子液体在氨气分离回收中的应用及展望
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摘要
氨(NH_3)是典型有毒有害工业气态污染物,也是形成PM2.5中二次颗粒物的根本原因之一,大量含氨气体的排放严重威胁人类的生活环境和健康。采用传统的酸法或水法,通常存在腐蚀性强、污染重、能耗高等问题,且难以回收利用氨资源。离子液体因其极低的挥发性、较好的化学/热稳定性、酸碱可调及高的氨溶解度等特点,为高效低能耗NH_3分离提供了新途径。综述了近年来国内外离子液体在NH_3分离中的研究进展,重点总结了常规离子液体、功能离子液体及离子液体溶剂/材料对NH_3的吸收/吸附性能,阐明了阴阳离子、功能基团对NH_3吸收性能的影响规律及其吸收机理,并探讨了该方向的研究和发展趋势。
As one of the typical alkaline and poisonous pollutants, ammonia(NH_3) is widely considered as a primary factor for the formation of fog and haze, which has caused a wide range of environmental problems and serious harm to human health. The traditional technologies for NH_3 separation, like water scrubbing and acid scrubbing, have been applied in industries. However, some inherent drawbacks, such as severe corrosion, heavy pollution, high energy consumption, and hard to recover NH_3 resources come with yet. Ionic liquids(ILs) provide a novel way for efficient and energy-saving separation of NH_3 owing to their extremely low vapour pressure, good chemical/thermal stability and tuneable acidity and alkalinity. In this review, the recent advances on conventional ILs, functionalized ILs and IL-based solvents and materials for NH_3 absorption/adsorption have been overviewed. The NH_3 absorption capacities in different ILs were summarized and the effect of cations, anions and functional groups on NH_3 absorption and the mechanisms have been discussed, and the research and development trend of this direction are discussed.
As one of the typical alkaline and poisonous pollutants, ammonia(NH_3) is widely considered as a primary factor for the formation of fog and haze, which has caused a wide range of environmental problems and serious harm to human health. The traditional technologies for NH_3 separation, like water scrubbing and acid scrubbing, have been applied in industries. However, some inherent drawbacks, such as severe corrosion, heavy pollution, high energy consumption, and hard to recover NH_3 resources come with yet. Ionic liquids(ILs) provide a novel way for efficient and energy-saving separation of NH_3 owing to their extremely low vapour pressure, good chemical/thermal stability and tuneable acidity and alkalinity. In this review, the recent advances on conventional ILs, functionalized ILs and IL-based solvents and materials for NH_3 absorption/adsorption have been overviewed. The NH_3 absorption capacities in different ILs were summarized and the effect of cations, anions and functional groups on NH_3 absorption and the mechanisms have been discussed, and the research and development trend of this direction are discussed.
引文
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[13]Zeng S J,Gao H,Zhang X,et al.Efficient and reversible capture of SO2by pyridinium-based ionic liquids[J].Chem.Eng.J.,2014,251:248-256.
[14]Huang K,Cai D N,Chen Y,et al.Thermodynamic validation of 1-alkyl-3-methylimidazolium carboxylates as task-specific ionic liquids for H2S absorption[J].AIChE J.,2013,59(6):2227-2235.
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[22]Huang X,Margulis C J,Li Y,et al.Why is the partial molar volume of CO2so small when dissolved in a room temperature ionic liquid?Structure and dynamics of CO2dissolved in[Bmim[PF6][J].J.Am.Chem.Soc.,2005,127(50):17842-17851.
[23]Yunus N M,Mutalib M I A,Man Z,et al.Solubility of CO2in pyridinium based ionic liquids[J].Chem.Eng.J.,2012,18994-100.
[24]Kazarian S G,Briscoe B J,Welton T.Combining ionic liquids and supercritical fluids:in situ ATR-IR study of CO2dissolved in two ionic liquids at high pressures[J].Chem.Commun.,2000,202047-2048.
[25]Dong K,Zhang S J,Wang D X,et al.Hydrogen bonds in imidazolium ionic liquids[J].J.Phys.Chem.A,2006,110(31)9775-9782.
[26]Crowhurst L,Mawdsley P R,Perez-Arlandis J M,et al.Solventsolute interactions in ionic liquids[J].Phys.Chem.Chem.Phys.2003,5(13):2790-2794.
[27]Cadena C,Anthony J L,Shah J K,et al.Why is CO2so soluble in imidazolium-based ionic liquids?[J].J.Am.Chem.Soc.,2004126(16):5300-5308.
[28]Anthony J L,Anderson J L,Maginn E J,et al.Anion effects on gas solubility in ionic liquids[J].J.Phys.Chem.B,2005,109(13)6366-6374.
[29]Bhargava B L,Balasubramanian S.Probing anion-carbon dioxide interactions in room temperature ionic liquids:gas phase cluster calculations[J].Chem.Phys.Lett.,2007,444(4/5/6):242-246.
[30]Seki T,Grunwaldt J D,Baiker A.In situ attenuated total reflection infrared spectroscopy of imidazolium-based room-temperature ionic liquids under"supercritical"CO2[J].J.Phys.Chem.B2009,113(1):114-122.
[31]Palomar J,Gonzalez-Miquel M,Bedia J,et al.Task-specific ionic liquids for efficient ammonia absorption[J].Sep.Purif.Technol.2011,82:43-52.
[32]Ruiz E,Ferro V R,de Riva J,et al.Evaluation of ionic liquids as absorbents for ammonia absorption refrigeration cycles using COSMO-based process simulations[J].Appl.Energ.,2014,123281-291.
[33]Bedia J,Palomar J,Gonzalez-Miquel M,et al.Screening ionic liquids as suitable ammonia absorbents on the basis of thermodynamic and kinetic analysis[J].Sep.Purif.Technol.2012,95:188-195.
[34]Zhang X,Dong H F,Huang Y,et al.Experimental study on gas holdup and bubble behavior in carbon capture systems with ionic liquid[J].Chem.Eng.J.,2012,209:607-615.
[35]Holbrey J D,Reichert W M,Swatloski R P,et al.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.
[36]Yokozeki A,Shiflett M B.Vapor-liquid equilibria of ammonia+ionic liquid mixtures[J].Appl.Energ.,2007,84(12):1258-1273.
[37]Iarikov D D,Hacarlioglu P,Oyama S T.Supported room temperature ionic liquid membranes for CO2/CH4separation[J].Chem.Eng.J.,2011,166(1):401-406.
[38]Li Z J,Zhang X P,Dong H F,et al.Efficient absorption of ammonia with hydroxyl-functionalized ionic liquids[J].RSC Adv.,2015,5(99):81362-81370.
[39]Shang D W,Bai L,Zeng S J,et al.Enhanced NH3capture by imidazolium-based protic ionic liquids with different anions and cation substituents[J].J.Chem.Technol.Biotechnol.,2018,93(5):1228-1236.
[40]Shang D W,Zhang X P,Zeng S J,et al.Protic ionic liquid BimNTf2with strong hydrogen bond donating ability for highly efficient ammonia absorption[J].Green Chem.,2017,19(4):937-945.
[41]Sherwood T K.Solubilities of sulfur dioxide and ammonia in water[J].Industrial and Engineering Chemistry,1925,17:745-747.
[42]Chen W,Liang S Q,Guo Y X,et al.Investigation on vapor-liquid equilibria for binary systems of metal ion-containing ionic liquid bmim Zn2Cl5/NH3by experiment and modified UNIFAC model[J].Fluid Phase Equilibr.,2013,360:1-6.
[43]Kohler F,Popp S,Klefer H,et al.Supported ionic liquid phase(SILP)materials for removal of hazardous gas compoundsefficient and irreversible NH3adsorption[J].Green Chem.,2014,16(7):3560-3568.
[44]Zeng S J,Liu L,Shang D W,et al.Efficient and reversible absorption of ammonia by cobalt ionic liquids through Lewis acidbase and cooperative hydrogen bond interactions[J].Green Chem.,2018,20(9):2075-2083.
[45]Wang J L,Zeng S J,Huo F,et al.Metal chloride anion-based ionic liquids for efficient separation of NH3[J].J.Clean Prod.,2019,206:661-669.
[46]Cao X Z,Song T Y,Wang X Q.Inorganic Chemistry[M].2nd ed.Beijing:Higher Education Press,1994:898-899.
[47]Akhmetshina A I,Petukhov A N,Mechergui A,et al.Evaluation of methanesulfonate-based deep eutectic solvent for ammonia sorption[J].J.Chem.Eng.Data,2018,63(6):1896-1904.
[48]Li Y H,Ali M C,Yang Q W,et al.Hybrid deep eutectic solvents with flexible hydrogen-bonded supramolecular networks for highly efficient uptake of NH3[J].ChemSusChem,2017,10(17):3368-3377.
[49]Lemus J,Bedia J,Moya C,et al.Ammonia capture from the gas phase by encapsulated ionic liquids(ENILs)[J].RSC Adv.,2016,6(66):61650-61660.
[50]Palomar J,Lemus J,Alonso-Morales N,et al.Encapsulated ionic liquids(ENILs):from continuous to discrete liquid phase[J].Chem.Comm.,2012,48(80):10046-10048.
[51]Ruckart K N,Zhang Y C,Reichert W M,et al.Sorption of ammonia in mesoporous-silica ionic liquid composites[J].Ind.Eng.Chem.Res.,2016,55(47):12191-12204.
[2]Erisman J W,Bleeker A,Galloway J,et al.Reduced nitrogen in ecology and the environment[J].Environ.Pollut.,2007,150(1):140-149.
[3]Sutton M A,Erisman J W,Dentener F,et al.Ammonia in the environment:from ancient times to the present[J].Environ.Pollut.,2008,156(3):583-604.
[4]Schafer D,Xia J Z,Vogt M,et al.Experimental investigation of the solubility of ammonia in methanol[J].J.Chem.Eng.Data,2007,52(5):1653-1659.
[5]Wang L,Huang X,Yu Y,et al.Eliminating ammonia emissions during rare earth separation through control of equilibrium acidity in a HEH(EHP)-Cl system[J].Green Chem.,2013,15(7):1889-1894.
[6]王芬,周敏.焦炉煤气中氨的回收[J].洁净煤技术,2009,(4):108-111.Wang F,Zhou M.Recovery of ammonia from coking product[J].Clean Coal Technol.,2009,(4):108-111.
[7]李强.氨回收系统存在问题及改进措施[J].大氮肥,2011,(6):418-419.Li Q.Problems in ammonia recovery system and improvement measures[J].Large Scale Nitrogenous Fertilizer Industry,2011,(6):418-419.
[8]林璐璐.氨回收工艺方案的选择[J].广东化工,2016,43(334):239-243.Lin L L.Process project selection for ammonia recovery[J].Guangdong Chemical Industry,2016,43(334):239-243.
[9]Lei Z G,Dai C N,Chen B H.Gas solubility in ionic liquids[J].Chem.Rev.,2014,114(2):1289-1326.
[10]Zeng S J,Zhang X P,Bai L,et al.Ionic liquid-based CO2capture systems:structure,interaction and process[J].Chem.Rev.,2017,117(14):9625-9673.
[11]Zhang X P,Zhang X C,Dong H F,et al.Carbon capture with ionic liquids:overview and progress[J].Energ.Environ.Sci.,2012,5(5):6668-6681.
[12]陈晏杰,姚月华,张香平,等.基于离子液体的合成氨驰放气中氨回收工艺模拟计算[J].过程工程学报,2011,11(4):644-651.Chen Y J,Yao Y H,Zhang X P,et al.Simulation and optimization of ammonia recovery with ionic liquid from purge gas in ammonia synthesis plant[J].Chin.J.Process Eng.,2011,11(4):644-651.
[13]Zeng S J,Gao H,Zhang X,et al.Efficient and reversible capture of SO2by pyridinium-based ionic liquids[J].Chem.Eng.J.,2014,251:248-256.
[14]Huang K,Cai D N,Chen Y,et al.Thermodynamic validation of 1-alkyl-3-methylimidazolium carboxylates as task-specific ionic liquids for H2S absorption[J].AIChE J.,2013,59(6):2227-2235.
[15]Luo X Y,Guo Y,Ding F,et al.Significant improvements in CO2capture by pyridine-containing anion-functionalized ionic liquids through multiple-site cooperative interactions[J].Angew Chem.Int.Edit.,2014,53(27):7053-7057.
[16]Shi W,Maginn E J.Molecular simulation of ammonia absorption in the ionic liquid 1-ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide(EmimTf2N)[J].AIChE J.,2009,55(9):2414-2421.
[17]Li G H,Zhou Q,Zhang X P,et al.Solubilities of ammonia in basic imidazolium ionic liquids[J].Fluid Phase Equilibr.,2010,297(1):34-39.
[18]Huang W J,Sun G M,Zheng D X,et al.Vapor-liquid equilibrium measurements of NH3+H2O+ionic liquid(DmimCl,DmimBF4and DmimDMP)systems[J].J.Chem.Eng.Data,2013,58(5)1354-1360.
[19]Yokozeki A,Shiflett M B.Ammonia solubilities in roomtemperature ionic liquids[J].Ind.Eng.Chem.Res.,2007,46(5)1605-1610.
[20]Yokozeki A,Shiflett M B.Vapor-liquid equilibria of ammonia plus ionic liquid mixtures[J].Appl.Energ.,2007,84(12):1258-1273.
[21]Aki S,Mellein B R,Saurer E M,et al.High-pressure phase behavior of carbon dioxide with imidazolium-based ionic liquids[J].J.Phys.Chem.B,2004,108(52):20355-20365.
[22]Huang X,Margulis C J,Li Y,et al.Why is the partial molar volume of CO2so small when dissolved in a room temperature ionic liquid?Structure and dynamics of CO2dissolved in[Bmim[PF6][J].J.Am.Chem.Soc.,2005,127(50):17842-17851.
[23]Yunus N M,Mutalib M I A,Man Z,et al.Solubility of CO2in pyridinium based ionic liquids[J].Chem.Eng.J.,2012,18994-100.
[24]Kazarian S G,Briscoe B J,Welton T.Combining ionic liquids and supercritical fluids:in situ ATR-IR study of CO2dissolved in two ionic liquids at high pressures[J].Chem.Commun.,2000,202047-2048.
[25]Dong K,Zhang S J,Wang D X,et al.Hydrogen bonds in imidazolium ionic liquids[J].J.Phys.Chem.A,2006,110(31)9775-9782.
[26]Crowhurst L,Mawdsley P R,Perez-Arlandis J M,et al.Solventsolute interactions in ionic liquids[J].Phys.Chem.Chem.Phys.2003,5(13):2790-2794.
[27]Cadena C,Anthony J L,Shah J K,et al.Why is CO2so soluble in imidazolium-based ionic liquids?[J].J.Am.Chem.Soc.,2004126(16):5300-5308.
[28]Anthony J L,Anderson J L,Maginn E J,et al.Anion effects on gas solubility in ionic liquids[J].J.Phys.Chem.B,2005,109(13)6366-6374.
[29]Bhargava B L,Balasubramanian S.Probing anion-carbon dioxide interactions in room temperature ionic liquids:gas phase cluster calculations[J].Chem.Phys.Lett.,2007,444(4/5/6):242-246.
[30]Seki T,Grunwaldt J D,Baiker A.In situ attenuated total reflection infrared spectroscopy of imidazolium-based room-temperature ionic liquids under"supercritical"CO2[J].J.Phys.Chem.B2009,113(1):114-122.
[31]Palomar J,Gonzalez-Miquel M,Bedia J,et al.Task-specific ionic liquids for efficient ammonia absorption[J].Sep.Purif.Technol.2011,82:43-52.
[32]Ruiz E,Ferro V R,de Riva J,et al.Evaluation of ionic liquids as absorbents for ammonia absorption refrigeration cycles using COSMO-based process simulations[J].Appl.Energ.,2014,123281-291.
[33]Bedia J,Palomar J,Gonzalez-Miquel M,et al.Screening ionic liquids as suitable ammonia absorbents on the basis of thermodynamic and kinetic analysis[J].Sep.Purif.Technol.2012,95:188-195.
[34]Zhang X,Dong H F,Huang Y,et al.Experimental study on gas holdup and bubble behavior in carbon capture systems with ionic liquid[J].Chem.Eng.J.,2012,209:607-615.
[35]Holbrey J D,Reichert W M,Swatloski R P,et al.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.
[36]Yokozeki A,Shiflett M B.Vapor-liquid equilibria of ammonia+ionic liquid mixtures[J].Appl.Energ.,2007,84(12):1258-1273.
[37]Iarikov D D,Hacarlioglu P,Oyama S T.Supported room temperature ionic liquid membranes for CO2/CH4separation[J].Chem.Eng.J.,2011,166(1):401-406.
[38]Li Z J,Zhang X P,Dong H F,et al.Efficient absorption of ammonia with hydroxyl-functionalized ionic liquids[J].RSC Adv.,2015,5(99):81362-81370.
[39]Shang D W,Bai L,Zeng S J,et al.Enhanced NH3capture by imidazolium-based protic ionic liquids with different anions and cation substituents[J].J.Chem.Technol.Biotechnol.,2018,93(5):1228-1236.
[40]Shang D W,Zhang X P,Zeng S J,et al.Protic ionic liquid BimNTf2with strong hydrogen bond donating ability for highly efficient ammonia absorption[J].Green Chem.,2017,19(4):937-945.
[41]Sherwood T K.Solubilities of sulfur dioxide and ammonia in water[J].Industrial and Engineering Chemistry,1925,17:745-747.
[42]Chen W,Liang S Q,Guo Y X,et al.Investigation on vapor-liquid equilibria for binary systems of metal ion-containing ionic liquid bmim Zn2Cl5/NH3by experiment and modified UNIFAC model[J].Fluid Phase Equilibr.,2013,360:1-6.
[43]Kohler F,Popp S,Klefer H,et al.Supported ionic liquid phase(SILP)materials for removal of hazardous gas compoundsefficient and irreversible NH3adsorption[J].Green Chem.,2014,16(7):3560-3568.
[44]Zeng S J,Liu L,Shang D W,et al.Efficient and reversible absorption of ammonia by cobalt ionic liquids through Lewis acidbase and cooperative hydrogen bond interactions[J].Green Chem.,2018,20(9):2075-2083.
[45]Wang J L,Zeng S J,Huo F,et al.Metal chloride anion-based ionic liquids for efficient separation of NH3[J].J.Clean Prod.,2019,206:661-669.
[46]Cao X Z,Song T Y,Wang X Q.Inorganic Chemistry[M].2nd ed.Beijing:Higher Education Press,1994:898-899.
[47]Akhmetshina A I,Petukhov A N,Mechergui A,et al.Evaluation of methanesulfonate-based deep eutectic solvent for ammonia sorption[J].J.Chem.Eng.Data,2018,63(6):1896-1904.
[48]Li Y H,Ali M C,Yang Q W,et al.Hybrid deep eutectic solvents with flexible hydrogen-bonded supramolecular networks for highly efficient uptake of NH3[J].ChemSusChem,2017,10(17):3368-3377.
[49]Lemus J,Bedia J,Moya C,et al.Ammonia capture from the gas phase by encapsulated ionic liquids(ENILs)[J].RSC Adv.,2016,6(66):61650-61660.
[50]Palomar J,Lemus J,Alonso-Morales N,et al.Encapsulated ionic liquids(ENILs):from continuous to discrete liquid phase[J].Chem.Comm.,2012,48(80):10046-10048.
[51]Ruckart K N,Zhang Y C,Reichert W M,et al.Sorption of ammonia in mesoporous-silica ionic liquid composites[J].Ind.Eng.Chem.Res.,2016,55(47):12191-12204.