咪唑类离子液体高效吸收二氯甲烷

doi:10.12034/j.issn.1009-606X.218162

过程工程学报 ›› 2019, Vol. 19 ›› Issue (1): 173-180.DOI: 10.12034/j.issn.1009-606X.218162

咪唑类离子液体高效吸收二氯甲烷

吴文亮^1,2，李涛¹，高红帅^2*，尚大伟²，涂文辉²，王斌琦²，张香平^1,2*

1. 郑州大学化工与能源学院，河南郑州 450001 2. 中国科学院过程工程研究所离子液体清洁过程北京市重点实验室，多相复杂系统国家重点实验室，北京 100190

收稿日期:2018-03-29 修回日期:2018-07-11 出版日期:2019-02-22 发布日期:2019-02-12
通讯作者: 张香平 xpzhang@ipe.ac.cn
基金资助:
国家自然科学基金资助项目;山西省重点研发计划重点项目;科技北京百名领军人才培养工程

Efficient absorption of dichloromethane using imidazolium based ionic liquids

Wenliang WU^1,2, Tao LI¹, Hongshuai GAO^2*, Dawei SHANG², Wenhui TU², Binqi WANG², Xiangping ZHANG^1,2*

1. School of Chemical Engineering and Energy, Zhengzhou University, Zhengzhou, Henan 450001, China 2. Beijing Key Laboratory of Ionic Liquids Clean Process, State Key Laboratory of Multiphase Complex System, Institute of Process Engineering, Chinese Academy of Sciences, Beijing 100190, China

Received:2018-03-29 Revised:2018-07-11 Online:2019-02-22 Published:2019-02-12
Contact: xiangping zhang xpzhang@ipe.ac.cn

摘要/Abstract

摘要： 合成了一系列常规离子液体1-丁基-3-甲基咪唑四氟硼酸盐([Bmim][BF4])、1-丁基-3-甲基咪唑六氟磷酸盐([Bmim][PF6])、1-丁基-3-甲基咪唑双三氟甲磺酰亚胺盐([Bmim][NTf2])、1-丁基-3-甲基咪唑双氰胺盐([Bmim][DCA])、1-丁基-3-甲基咪唑硫氰酸盐([Bmim][SCN])、1-乙基-3-甲基咪唑硫氰酸盐([Emim][SCN])和N-丁基吡啶硫氰酸盐([BPy][SCN])，用智能重量分析仪(IGA)测定不同温度和分压下离子液体吸收二氯甲烷(DCM)的容量。结果表明，[Bmim][SCN]具有最高的二氯甲烷吸收容量(1.46 g/g, 303.15 K, 60 kPa)，5次循环后吸收能力无明显下降，[Bmim][SCN]基本可完全再生，能循环使用。量化计算结果表明[SCN]?可与二氯甲烷形成氢键，增强其对二氯甲烷的吸收能力。

关键词: 咪唑类离子液体, 二氯甲烷捕集, 吸收容量, 氢键

Abstract: In recent years, environment problems have been a hot issue of concern to the public. Chlorinated volatile organic compounds such as dichloromethane (DCM) have been a serious threat to the public health and environment as hazardous chemical substances. Solving these problems has become an urgent issue in nowadays society. Ionic liquids (ILs) are supposed to be potential solvents to absorb gases due to their unique structures and properties, which have exhibited excellent absorption capacity in NH3, SO2, CO2 and other gases. In this paper, a series of conventional ILs including [Bmim][BF4], [Bmim][PF6], [Bmim][DCA], [Bmim][SCN], [Bmim][NTf2], [Emim][SCN], [BPy][SCN] were synthesized and used as absorbents for dichloromethane (DCM) capture at different temperatures and partial pressures. The absorption capacities of DCM by ILs were measured by a highly sensible microbalance-intelligent gravimetric analyzer (IGA). It was found that [Bmim][SCN] has the highest absorption capacity to DCM (1.46 g/g, 303.15 K, 60 kPa) among these investigated ILs, and the absorption capacity of [Bmim][SCN] had no obvious decline after five absorption?desorption cycles. The densities and viscosities of [Bmim][SCN] with different mass fraction of DCM absorbed were measured in this work as well. And with the increase of the mass fraction of DCM absorbed, the density of DCM absorbed [Bmim][SCN] increased slightly, while the viscosity decreased dramatically. In addition, mechanism of DCM absorption by [Bmim][SCN] was investigated through FT-IR and 1H?NMR, implying the interaction between DCM and [Bmim][SCN] was physical interaction. Furthermore, the interactions between cations or anions of ILs and DCM were investigated by quantum chemical calculation, which demonstrated that the anions of ILs had a more significant influence on the absorption capacity than cations, on account of the strong hydrogen bond interaction between anion and DCM, which has a great agreement with the results of experiment. This work will provide a new sight for designing more competitive ILs for DCM capture.

Key words: Imidazolium based ionic liquids, Dichloromethane capture, Absorption capacity, Hydrogen bond

吴文亮李涛高红帅尚大伟涂文辉王斌琦张香平. 咪唑类离子液体高效吸收二氯甲烷[J]. 过程工程学报, 2019, 19(1): 173-180.

Wenliang WU Tao LI Hongshuai GAO Dawei SHANG Wenhui TU Binqi WANG. Efficient absorption of dichloromethane using imidazolium based ionic liquids[J]. Chin. J. Process Eng., 2019, 19(1): 173-180.

参考文献

[1]. Yu J, Cai W, Chen J, et al. Conversion Characteristics and Mechanism Analysis of Gaseous Dichloromethane Degraded by a VUV Light in Different Reaction Media [J]. J. Environ. Sci., 2012, 24(10): 1777-1784.
[2]. Yun JH, Choi DK. Adsorption Equilibria of Chlorinated Organic Solvents onto Activated Carbon[J]. Ind. Eng. Chem. Res., 1998, 37: 1422-1427.
[3]. Schlosser PM, Bale AS, Gibbons CF, et al. Human Health Effects of Dichloromethane: Key Findings and Scientific Issues [J]. Environ. Health Perspect, 2015, 123(2):114-119.
[4]. Ozturk B, Yilmaz D. Absorptive Removal of Volatile Organic [J]. Process Saf. Environ., 2006, 84(B5): 391-398.
[5]. Shestakova M, Sillanpaa M. Removal of Dichloromethane from Ground and Wastewater: A Review [J]. Chemosphere, 2013, 93(7): 1258-1267.
[6]. Borkar C, Tomar D, Gumma S. Adsorption of Dichloromethane on Activated Carbon [J]. J. Chem. Eng. Data, 2010, 55: 1640-1644.
[7]. Lemus J, Martin-Martinez M, Palomar J. Removal of Chlorinated Organic Volatile Compounds by Gas Phase Adsorption with Activated Carbon [J]. Chem. Eng. J., 2012, 211-212: 246-254.
[8]. Zhou L, Zhang X, Chen Y. Facile Synthesis of Al-fumarate metal–organic Framework Nano-flakes and Their Highly Selective Adsorption of Volatile Organic Compounds [J]. Mater. Lett., 2017, 197: 224-227.
[9]. Zhou L, Zhang X, Chen Y. Modulated Synthesis of Zirconium Metal–organic Framework UiO-66 with Enhanced Dichloromethane Adsorption Capacity [J]. Mater. Lett., 2017, 197:167-170.
[10]. Leng Y, Wang J, Zhu D, et al. Heteropolyanion-based Ionic Liquids: Reaction-induced Self-separation Catalysts for Esterification [J]. Angew. Chem. Int. Ed., 2009, 48(1): 168-71.
[11]. Dong K, Liu X, Dong H, et al. Multiscale Studies on Ionic Liquids [J]. Chem. Rev., 2017, 117(10): 6636-6695.
[12]. Shang D, Zhang X, Zeng S, et al. Protic Ionic Liquid [Bim][NTf2] with Strong Hydrogen Bond Donating Ability for Highly Efficient Ammonia Absorption [J]. Green Chem., 2017, 19(4): 937-945.
[13]. Zeng S, Wang J, Bai L, et al. Highly Selective Capture of CO2 by Ether-functionalized Pyridinium Ionic Liquids with Low Viscosity [J]. Energy Fuels, 2015, 29(9): 6039-6048
[14]. Che S, Dao R, Zhang W, et al. Designing an Anion-functionalized Fluorescent Ionic Liquid as an Efficient and Reversible Turn-off Sensor for Detecting SO2 [J]. Chem. Commun., 2017, 53(27): 3862-3865.
[15]. Yang D, Han Y, Qi H, et al. Efficient Absorption of SO2 by EmimCl-EG Deep Eutectic Solvents [J]. ACS Sustain. Chem. Eng., 2017, 5(8): 6382-6386.
[16]. Zeng S, Zhang X, Gao H, et al. SO2-induced Variations in the Viscosity of Ionic Liquids Investigated by in Situ Fourier Transform Infrared Spectroscopy and Simulation Calculations [J]. Ind. Eng. Chem. Res., 2015, 54(43): 10854-10862.
[17]. Wang J, Petit C, Zhang X, et al. Simultaneous Measurement of CO2 Sorption and Swelling of Phosphate-based Ionic Liquid [J]. Green Energy Environ., 2016, 1(3): 258-265.
[18]. Meng X, Wang J, Jiang H, et al. Guanidinium-based Dicarboxylic Acid Ionic Liquids for SO2 Capture [J]. J. Chem. Technol. Biot., 2017, 92(4): 767-774.
[19]. Liu X, Huang Y, Zhao Y, et al. Ionic Liquid Design and Process Simulation for Decarbonization of Shale Gas [J]. Ind. Eng. Chem. Res., 2016, 55(20): 5931-5944.
[20]. Zeng S, Gao H, Zhang X, et al. Efficient and Reversible Capture of SO2 by Pyridinium-based Ionic Liquids [J]. Chem. Eng. J., 2014, 251: 248-256.
[21]. Li Z, Zhang X, Dong H, et al. Efficient Absorption of Ammonia with Hydroxyl-functionalized Ionic Liquids [J]. RSC Adv., 2015, 5(99): 81362-81370.
[22]. Shang D, Bai L, Zeng S, et al. Enhanced NH3 Capture by Imidazolium-based Protic Ionic Liquids with Different Anions and Cation Substituents [J]. J. Chem. Technol. Biot., 2017, DOI 10.1002/jctb.5467.
[23]. Lei Z, Han J, Zhang B, et al. Solubility of CO2 in Binary Mixtures of Room-temperature Ionic Liquids at High Pressures [J]. J. Chem. Eng. Data, 2012, 57(8): 2153-2159.
[24]. Lei Z, Dai C, Chen B. Gas Solubility in Ionic Liquids [J]. Chem. Rev., 2014, 114(2): 1289-1326.
[25]. Ando RA, Siqueira LJA, Bazito FC, et al. The Sulfur Dioxide-1-butyl-3-methylimidazolium Bromide Interaction_drastic Changes in Structural and Physical Properties [J]. J. Phys. Chem. B, 2007, 111: 8717-8719.
[26]. Ren SH, Hou YC, Wu WZ, et al. Properties of Ionic Liquids Absorbing SO2 and the Mechanism of the Absorption [J]. J. Phys. Chem. B, 2010, 114: 2175-2179.
[27]. Brown P, Gurkan BE, Hatton TA. Enhanced Gravimetric CO2 Capacity and Viscosity for Ionic Liquids with Cyanopyrrolide Anion [J]. AIChE J., 2015, 61(7): 2280-2285.
[28]. Feldheim DL, Hendrickson SM, Krejcik M, et al. Kinetics of Dichloromethane Absorption into the Conductive Polymers [J]. J. Phys. Chem., 1995, 99: 3288-3293.
[29]. Borisch J, Pilkenton S, Miller LM, et al. TiO2 Photocatalytic Degradation of Dichloromethane: An FTIR and Solid-state NMR Study [J]. J. Phys. Chem. B, 2004, 108: 5640-5646.
[30]. Ding F, He X, Luo X, et al. Highly Efficient CO2 Capture by Carbonyl-containing Ionic Liquids Through Lewis Acid-base and Cooperative C-HO Hydrogen Bonding Interaction Strengthened by the Anion [J]. Chem. Commun., 2014, 50(95): 15041-15044.
[31]. Noack K, Schulz PS, Paape N, et al. The Role of the C2 Position in Interionic Interactions of Imidazolium Based Ionic Liquids: A Vibrational and NMR Spectroscopic Study [J]. Phys. Chem. Chem. Phys., 2010, 12(42): 14153-14161.
[32]. Meng Z, Dolle A, Carper WR. Gas Phase Model of An Ionic Liquids: Semi-empirical and Ab Initio Bonding and Molecular Structure [J]. J. Mol. Strut., 2002, 585: 119-128.

咪唑类离子液体高效吸收二氯甲烷

Efficient absorption of dichloromethane using imidazolium based ionic liquids

PDF

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 2

编辑推荐

Metrics

[1]	许海洋孟祥展夏大厦惠岚峰王慧. 功能化离子液体萃取分离甘氨酸[J]. 过程工程学报, 2019, 19(3): 544-552.
[2]	孟建陈璐璐李延斌高保娇. 非水介质中表面引发接枝聚合法制备接枝微粒PMAA/SiO2及其对阿魏酸的氢键吸附性能[J]. 过程工程学报, 2015, 15(4): 646-652.