低黏二氰胺类离子液体乙烯汽液相平衡研究
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摘要
从工业废气中回收分离乙烯(C_2H_4)具有重要意义,选用了三种低黏度二氰胺类离子液体,分别测定了293.15～333.15 K下其密度、黏度等物化性质,研究了其对乙烯(C_2H_4)吸收性能。采用非随机(局部)双液体模型(NRTL)关联了三种二元体系溶解度数据,实验值与计算值的平均相对偏差均小于3%。结果表明,低黏度二氰胺类离子液体对C_2H_4气体吸收性能良好,其中阳离子侧链长度增加和羟基功能团引入可增强对C_2H_4溶解度。同时,离子液体1-丁基-3-甲基咪唑二氰胺盐([Bmim][DCN])经过3次的吸收解吸循环,仍可以保持较好的C_2H_4吸收性能,表明该离子液体循环稳定性好,而1-丁基-3-甲基咪唑二氰胺盐([Bmim][DCN])对乙烯吸收量较高,具有作为C_2H_4吸收剂的潜力。
Three dicyandiamide-based ionic liquids with low viscosity were selected as absorbent for ethylene absorption. The physicochemical properties such as density and viscosity were measured at 293.15-333.15 K, and their properties were studied. The NRTL model was used to correlate the solubility data for the three binary systems.The average relative deviations(ARDs) between the experimental and calculated values of the three binary systems are 2.47%, 2.54% and 1.19%, respectively. The results show that the low viscous dicyandiamide-based ionic liquids presented good C_2H_4 absorption performance. The solubility of C_2H_4 in ionic liquids is improved by increasing the length of side-chain and introducing hydroxyl group in the imidazole cation. The C_2H_4 solubility would increase with decreasing temperature or increasing pressure. Furthermore, these ionic liquids such as[Bmim][DCN] exhibited outstanding reversibility after 3 times of absorption/desorption circulation. [Bmim][DCN]has the better C_2H_4 solubility than the other two, showing the potential to be C_2H_4 absorbent.
Three dicyandiamide-based ionic liquids with low viscosity were selected as absorbent for ethylene absorption. The physicochemical properties such as density and viscosity were measured at 293.15-333.15 K, and their properties were studied. The NRTL model was used to correlate the solubility data for the three binary systems.The average relative deviations(ARDs) between the experimental and calculated values of the three binary systems are 2.47%, 2.54% and 1.19%, respectively. The results show that the low viscous dicyandiamide-based ionic liquids presented good C_2H_4 absorption performance. The solubility of C_2H_4 in ionic liquids is improved by increasing the length of side-chain and introducing hydroxyl group in the imidazole cation. The C_2H_4 solubility would increase with decreasing temperature or increasing pressure. Furthermore, these ionic liquids such as[Bmim][DCN] exhibited outstanding reversibility after 3 times of absorption/desorption circulation. [Bmim][DCN]has the better C_2H_4 solubility than the other two, showing the potential to be C_2H_4 absorbent.
引文
[1]张勇.烯烃技术进展[M].北京:中国石化出版社,2008:251-252.Zhang Y.Technical Progress Olefins[M].Beijing:China Petrochemical Press,2008:251-252.
[2]李涛.以乙烯为原料的产业链延伸加工及其新进展[J].石油化工技术与经济,2014,30(2):11-15.Li T.Extending process of industrial chain with ethylene as material and its latest development[J].Technology&Economics in Petrochemicals,2014,30(2):11-15.
[3]张阳,王蕾,李明,等.世界及国内乙烯产能概况[J].当代化工,2018,47(1):113-115.Zhang Y,Wang L,Li M,et al.General situation of ethylene production capacity in the world and domestic[J].Contemporary Chemical Industry,2018,47(1):113-115.
[4]Eldridge R B.Olefin/paraffin separation technology:a review[J].Industrial&Engineering Chemistry Research,1993,32(10):2208-2212.
[5]谭雅文,丁雪.催化裂化干气乙烯回收利用技术研究进展[J].广东化工,2017,44(6):107.Tan Y W,Ding X.The development of recovery and utilization processes of ethylene in FCC dry gas[J].Guangdong Chemical Industry,2017,44(6):107.
[6]Zhang X P,Zhang X C,Dong H F,et al.Carbon capture with ionic liquids:overview and progress[J].Energy&Environmentalence,2012,5(5):6668-6681.
[7]Anthony J L,Anderson J L,Maginn E J.Anion effects on gas solubility in ionic liquids[J].Journal of Physical Chemistry B,2005,109(13):6266-6374.
[8]Cheng X P,Mu T C,Wang X L,et al.Low pressure solubilities of vinyl chloride in ionic liquids[J].Journal of Chemical&Engineering Data,2008,53(12):2807-2809.
[9]Cheng X P,Yang G Y,Mu T C,et al.Absorption of vinyl chloride by room temperature ionic liquids[J].Clean-Soil Air Water,2010,37(3):245-248.
[10]Wasserscheid P,Welton T.Ionic Liquids in Synthesis[M].New York:Wiley-VCH,2003:25-26.
[11]Wasserscheid P,Welton T.Ionic Liquids in Synthesis[M].2nd ed.New York:Wiley-VCH,2008:57-60.
[12]张庆华,王瑞峰,李作鹏,等.离子液体在绿色催化和清洁合成中应用的进展[J].石油化工,2007,36(10):975-984.Zhang Q H,Wang R F,Li Z P,et al.Advances of ionic liquid application in green catalysis and clean synthesis[J].Petrochemical Technology,2007,36(10):975-984.
[13]刘维伟,胡松,陈文,等.功能型离子液体的合成表征及CO2吸收性能[J].化工学报,2012,63(1):139-145.Liu W W,Hu S,Chen W,et al.Synthesis and identification of functional ionic liquids and research on its performance of CO2absorption[J].CIESC Journal,2012,63(1):139-145.
[14]Anderson J L,Dixon J K,Brennecke J F.Solubility of CO2,CH4,C2H6,C2H4,O2,and N2in 1-hexyl-3-methylpyridinium bis(trifluoromethylsulfonyl)imide:comparison to other ionic liquids[J].Cheminform,2010,39(7):6266-6374.
[15]Chen J J,Li W W,Yu H Q,et al.Capture of H2S from binary gas mixture by imidazolium-based ionic liquids with nonfluorous anions:a theoretical study[J].AIChE Journal,2013,59(10):3824-3833.
[16]Mokrushin V,Assenbaum D,Paape N,et al.Ionic liquids for propene-propane separation[J].Chemical Engineering&Technology,2010,33(1):63-73.
[17]Manesh S M,Satyro M A,Marriott R A.Screening ionic liquids as candidates for separation of acid gases:solubility of hydrogen sulfide,methane,and ethane[J].AIChE Journal,2013,59(8):2993-3005.
[18]张慧,张红梅,沈锦优,等.氨基功能型离子液体吸收CO2的性能[J].化工学报,2016,67(12):5057-5065.Zhang H,Zhang H M,Shen J Y,et al.Absorption performance of CO2in amino-functionalized task-specific ionic liquids[J].CIESCJournal,2016,67(12):5057-5065.
[19]Zhao X,Xing H B,Yang Q W,et al.Differential solubility of ethylene and acetylene in room temperature ionic liquids:a theoretical study[J].Journal of Physical Chemistry B,2012,116(13):3944-3953.
[20]Chen K H,Lin W J,Yu X N,et al.Designing of anionfunctionalized ionic liquids for efficient capture of SO2from flue gas[J].AIChE Journal,2015,61(6):2028-2034.
[21]Cui G K,Zhang F T,Zhou X Y,et al.Tuning the basicity of cyano-containing ionic liquids to improve SO2capture through cyano-sulfur interactions[J].Chemistry:A European Journal,2015,21(14):5632-5639.
[22]Huang K,Zhang X M,Xu Y,et al.Protic ionic liquids for the selective absorption of H2S from CO2:thermodynamic analysis[J].AIChE Journal,2015,60(12):4232-4240.
[23]Camper D,Becker C,Koval C,et al.Low pressure hydrocarbon solubility in room temperature ionic liquids containing imidazolium rings interpreted using regular solution theory[J].Industrial&Engineering Chemistry Research,2005,44(6):1928-1933.
[24]Ferguson L,Scovazzo P.Solubility,diffusivity,and permeability of gases in phosphonium-based room temperature ionic liquids:data and correlations[J].Industrial&Engineering Chemistry Research,2007,46(4):1369-1374.
[25]Condemarin R,Scovazzo P.Gas permeabilities,solubilities,diffusivities,and diffusivity correlations for ammonium-based room temperature ionic liquids with comparison to imidazolium and phosphonium RTIL data[J].Chemical Engineering Journal,2009,147(1):51-57.
[26]Zhang J,Zhang Q H,Qiao B T,et al.Solubilities of the gaseous and liquid solutes and their thermodynamics of solubilization in the novel room-temperature ionic liquids at infinite dilution by gas chromatography[J].Journal of Chemical and Engineering Data,2007,52(6):2277-2283.
[27]Xing H B,Zhao X,Li R L,et al.Improved efficiency of ethylene/ethane separation using a symmetrical dual nitrile-functionalized ionic liquid[J].ACS Sustainable Chemistry&Engineering,2013,1(11):1357-1363.
[28]Yoshida Y,Baba O,Saito G.Ionic liquids based on dicyanamide anion:influence of structural variations in cationic structures on ionic conductivity[J].Journal of Physical Chemistry B,2007,111(18):4742-4749.
[29]Greaves T L,Drummond C J.Protic ionic liquids:properties and applications[J].Chemical Reviews,2008,108(1):206-237.
[30]Larriba M,Navarro P,Garcia 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.
[31]Gmehling J,Kolbe B,Kleiber M,et al.Chemical Thermodynamics for Process Simulation[M].New York:Wiley-VCH,2012:259-271.
[32]Liu X Y,Liu S Q,Bai L H,et al.Absorption and seperation of CO2/C3H8and C3H6/C3H8by ionic liquid:effect of molar volume[J].Journal of Natural Gas Science and Engineering,2018,58:266-277.
[33]Udagawa T,Ishimoto T,Tokiwa H,et al.Geometric isotope effect of various intermolecular and intramolecular C-H···O hydrogen bonds,using the multicomponent molecular orbital Method[J].The Journal of Physical Chemistry A,2006,110(22):7279-7285.
[34]Chen Y Y,Mutelet F,Jean-No?l J.Solubility of carbon dioxide,nitrous oxide and methane in ionic liquids at pressures close to atmospheric[J].Fluid Phase Equilibria,2014,372:26-33.
[2]李涛.以乙烯为原料的产业链延伸加工及其新进展[J].石油化工技术与经济,2014,30(2):11-15.Li T.Extending process of industrial chain with ethylene as material and its latest development[J].Technology&Economics in Petrochemicals,2014,30(2):11-15.
[3]张阳,王蕾,李明,等.世界及国内乙烯产能概况[J].当代化工,2018,47(1):113-115.Zhang Y,Wang L,Li M,et al.General situation of ethylene production capacity in the world and domestic[J].Contemporary Chemical Industry,2018,47(1):113-115.
[4]Eldridge R B.Olefin/paraffin separation technology:a review[J].Industrial&Engineering Chemistry Research,1993,32(10):2208-2212.
[5]谭雅文,丁雪.催化裂化干气乙烯回收利用技术研究进展[J].广东化工,2017,44(6):107.Tan Y W,Ding X.The development of recovery and utilization processes of ethylene in FCC dry gas[J].Guangdong Chemical Industry,2017,44(6):107.
[6]Zhang X P,Zhang X C,Dong H F,et al.Carbon capture with ionic liquids:overview and progress[J].Energy&Environmentalence,2012,5(5):6668-6681.
[7]Anthony J L,Anderson J L,Maginn E J.Anion effects on gas solubility in ionic liquids[J].Journal of Physical Chemistry B,2005,109(13):6266-6374.
[8]Cheng X P,Mu T C,Wang X L,et al.Low pressure solubilities of vinyl chloride in ionic liquids[J].Journal of Chemical&Engineering Data,2008,53(12):2807-2809.
[9]Cheng X P,Yang G Y,Mu T C,et al.Absorption of vinyl chloride by room temperature ionic liquids[J].Clean-Soil Air Water,2010,37(3):245-248.
[10]Wasserscheid P,Welton T.Ionic Liquids in Synthesis[M].New York:Wiley-VCH,2003:25-26.
[11]Wasserscheid P,Welton T.Ionic Liquids in Synthesis[M].2nd ed.New York:Wiley-VCH,2008:57-60.
[12]张庆华,王瑞峰,李作鹏,等.离子液体在绿色催化和清洁合成中应用的进展[J].石油化工,2007,36(10):975-984.Zhang Q H,Wang R F,Li Z P,et al.Advances of ionic liquid application in green catalysis and clean synthesis[J].Petrochemical Technology,2007,36(10):975-984.
[13]刘维伟,胡松,陈文,等.功能型离子液体的合成表征及CO2吸收性能[J].化工学报,2012,63(1):139-145.Liu W W,Hu S,Chen W,et al.Synthesis and identification of functional ionic liquids and research on its performance of CO2absorption[J].CIESC Journal,2012,63(1):139-145.
[14]Anderson J L,Dixon J K,Brennecke J F.Solubility of CO2,CH4,C2H6,C2H4,O2,and N2in 1-hexyl-3-methylpyridinium bis(trifluoromethylsulfonyl)imide:comparison to other ionic liquids[J].Cheminform,2010,39(7):6266-6374.
[15]Chen J J,Li W W,Yu H Q,et al.Capture of H2S from binary gas mixture by imidazolium-based ionic liquids with nonfluorous anions:a theoretical study[J].AIChE Journal,2013,59(10):3824-3833.
[16]Mokrushin V,Assenbaum D,Paape N,et al.Ionic liquids for propene-propane separation[J].Chemical Engineering&Technology,2010,33(1):63-73.
[17]Manesh S M,Satyro M A,Marriott R A.Screening ionic liquids as candidates for separation of acid gases:solubility of hydrogen sulfide,methane,and ethane[J].AIChE Journal,2013,59(8):2993-3005.
[18]张慧,张红梅,沈锦优,等.氨基功能型离子液体吸收CO2的性能[J].化工学报,2016,67(12):5057-5065.Zhang H,Zhang H M,Shen J Y,et al.Absorption performance of CO2in amino-functionalized task-specific ionic liquids[J].CIESCJournal,2016,67(12):5057-5065.
[19]Zhao X,Xing H B,Yang Q W,et al.Differential solubility of ethylene and acetylene in room temperature ionic liquids:a theoretical study[J].Journal of Physical Chemistry B,2012,116(13):3944-3953.
[20]Chen K H,Lin W J,Yu X N,et al.Designing of anionfunctionalized ionic liquids for efficient capture of SO2from flue gas[J].AIChE Journal,2015,61(6):2028-2034.
[21]Cui G K,Zhang F T,Zhou X Y,et al.Tuning the basicity of cyano-containing ionic liquids to improve SO2capture through cyano-sulfur interactions[J].Chemistry:A European Journal,2015,21(14):5632-5639.
[22]Huang K,Zhang X M,Xu Y,et al.Protic ionic liquids for the selective absorption of H2S from CO2:thermodynamic analysis[J].AIChE Journal,2015,60(12):4232-4240.
[23]Camper D,Becker C,Koval C,et al.Low pressure hydrocarbon solubility in room temperature ionic liquids containing imidazolium rings interpreted using regular solution theory[J].Industrial&Engineering Chemistry Research,2005,44(6):1928-1933.
[24]Ferguson L,Scovazzo P.Solubility,diffusivity,and permeability of gases in phosphonium-based room temperature ionic liquids:data and correlations[J].Industrial&Engineering Chemistry Research,2007,46(4):1369-1374.
[25]Condemarin R,Scovazzo P.Gas permeabilities,solubilities,diffusivities,and diffusivity correlations for ammonium-based room temperature ionic liquids with comparison to imidazolium and phosphonium RTIL data[J].Chemical Engineering Journal,2009,147(1):51-57.
[26]Zhang J,Zhang Q H,Qiao B T,et al.Solubilities of the gaseous and liquid solutes and their thermodynamics of solubilization in the novel room-temperature ionic liquids at infinite dilution by gas chromatography[J].Journal of Chemical and Engineering Data,2007,52(6):2277-2283.
[27]Xing H B,Zhao X,Li R L,et al.Improved efficiency of ethylene/ethane separation using a symmetrical dual nitrile-functionalized ionic liquid[J].ACS Sustainable Chemistry&Engineering,2013,1(11):1357-1363.
[28]Yoshida Y,Baba O,Saito G.Ionic liquids based on dicyanamide anion:influence of structural variations in cationic structures on ionic conductivity[J].Journal of Physical Chemistry B,2007,111(18):4742-4749.
[29]Greaves T L,Drummond C J.Protic ionic liquids:properties and applications[J].Chemical Reviews,2008,108(1):206-237.
[30]Larriba M,Navarro P,Garcia 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.
[31]Gmehling J,Kolbe B,Kleiber M,et al.Chemical Thermodynamics for Process Simulation[M].New York:Wiley-VCH,2012:259-271.
[32]Liu X Y,Liu S Q,Bai L H,et al.Absorption and seperation of CO2/C3H8and C3H6/C3H8by ionic liquid:effect of molar volume[J].Journal of Natural Gas Science and Engineering,2018,58:266-277.
[33]Udagawa T,Ishimoto T,Tokiwa H,et al.Geometric isotope effect of various intermolecular and intramolecular C-H···O hydrogen bonds,using the multicomponent molecular orbital Method[J].The Journal of Physical Chemistry A,2006,110(22):7279-7285.
[34]Chen Y Y,Mutelet F,Jean-No?l J.Solubility of carbon dioxide,nitrous oxide and methane in ionic liquids at pressures close to atmospheric[J].Fluid Phase Equilibria,2014,372:26-33.