Physicochemical properties of amide-AlCl3 based ionic liquid analogues and their mixtures with copper salt

doi:10.1016/j.cjche.2018.06.018

摘要/Abstract

摘要： The physicochemical properties of three different amide-AlCl₃ based ionic liquid (IL) analogues and their mixtures with copper salt, such as conductivity, viscosity, density and isobutane solubility were determined over a wide range of temperatures. The effects of amide structure, amide/AlCl₃ molar ratio and CuCl modification on these physicochemical properties were investigated. Results showed that the conductivity of amide-AlCl₃ based IL analogues was much lower than that of traditional Et₃NHCl-AlCl₃ IL with same ligand/AlCl₃ molar ratio due to incomplete splitting of AlCl₃, whereas the density and viscosity of amide-AlCl₃ based IL analogues were slightly higher. The viscosity of amide-AlCl₃ based IL analogues was closely related to the amide structure, and followed the order of DMA-AlCl₃ > AA-AlCl₃ > NMA-AlCl₃ with same amide/AlCl₃ molar ratio. Meanwhile, the density of amide-AlCl₃ based IL analogues ranked in the following order:AA-AlCl₃ > NMA-AlCl₃ > DMA-AlCl₃. Increasing the amide/AlCl₃ molar ratio decreased the conductivity and density, while increased the viscosity. The solubility experiment indicated that the isobutane solubility in NMA-AlCl₃ was highest than that in two other IL analogues. Under the modification of CuCl, the conductivity, viscosity and density of these IL analogues increased, whereas the isobutane solubility decreased. These results provide the foundation for the development of a suitable IL analogue catalyst for isobutane alkylation.

关键词: Ionic liquid analogues, Conductivity, Density, Viscosity, Isobutane solubility

Abstract: The physicochemical properties of three different amide-AlCl₃ based ionic liquid (IL) analogues and their mixtures with copper salt, such as conductivity, viscosity, density and isobutane solubility were determined over a wide range of temperatures. The effects of amide structure, amide/AlCl₃ molar ratio and CuCl modification on these physicochemical properties were investigated. Results showed that the conductivity of amide-AlCl₃ based IL analogues was much lower than that of traditional Et₃NHCl-AlCl₃ IL with same ligand/AlCl₃ molar ratio due to incomplete splitting of AlCl₃, whereas the density and viscosity of amide-AlCl₃ based IL analogues were slightly higher. The viscosity of amide-AlCl₃ based IL analogues was closely related to the amide structure, and followed the order of DMA-AlCl₃ > AA-AlCl₃ > NMA-AlCl₃ with same amide/AlCl₃ molar ratio. Meanwhile, the density of amide-AlCl₃ based IL analogues ranked in the following order:AA-AlCl₃ > NMA-AlCl₃ > DMA-AlCl₃. Increasing the amide/AlCl₃ molar ratio decreased the conductivity and density, while increased the viscosity. The solubility experiment indicated that the isobutane solubility in NMA-AlCl₃ was highest than that in two other IL analogues. Under the modification of CuCl, the conductivity, viscosity and density of these IL analogues increased, whereas the isobutane solubility decreased. These results provide the foundation for the development of a suitable IL analogue catalyst for isobutane alkylation.

Key words: Ionic liquid analogues, Conductivity, Density, Viscosity, Isobutane solubility

Pengcheng Hu, Wei Jiang, Lijuan Zhong, Shufeng Zhou. Physicochemical properties of amide-AlCl₃ based ionic liquid analogues and their mixtures with copper salt[J]. Chinese Journal of Chemical Engineering, 2019, 27(1): 144-149.

Pengcheng Hu, Wei Jiang, Lijuan Zhong, Shufeng Zhou. Physicochemical properties of amide-AlCl₃ based ionic liquid analogues and their mixtures with copper salt[J]. Chin.J.Chem.Eng., 2019, 27(1): 144-149.

参考文献

[1] S.W. Liu, C.G. Chen, F.L. Yu, L. Li, Z.G. Liu, S.T. Yu, C. Xie, F.S. Liu, Alkylation of isobutane/isobutene using Bronsted-Lewis acidic ionic liquids as catalysts, Fuel 159(2015) 803-809.

[2] Z.C. Liu, X.H. Meng, R. Zhang, C.M. Xu, H. Dong, Y.F. Hu, Reaction performance of isobutane alkylation catalyzed by a composite ionic liquid at a short contact time, AICHE J. 60(2014) 2244-2253.

[3] Q. Huang, G.Y. Zhao, S.J. Zhang, F.F. Yang, Improved catalytic lifetime of H₂SO₄ for isobutane alkylation with trace amount of ionic liquids buffer, Ind. Eng. Chem. Res. 54(2015) 1464-1469.

[4] T.L.T. Bui, W. Korth, S. Aschauer, A. Jess, Alkylation of isobutane with 2-butene using ionic liquids as catalyst, Green Chem. 11(2009) 1961-1967.

[5] K. Yoo, V.V. Namboodiri, R.S. Varma, P.G. Smirniotis, Ionic liquid-catalyzed alkylation of isobutane with 2-butene, J. Catal. 222(2004) 511-519.

[6] P.C. Hu, R. Zhang, X.H. Meng, H.Y. Liu, C.M. Xu, Z.C. Liu, Structural and spectroscopic characterizations of amide-AlCl₃-based ionic liquid analogues, Inorg. Chem. 55(2016) 2374-2380.

[7] P.C. Hu, Y.D. Wang, X.H. Meng, R. Zhang, H.Y. Liu, C.M. Xu, Z.C. Liu, Isobutane alkylation with 2-butene catalyzed by amide-AlCl₃-based ionic liquid analogues, Fuel 189(2017) 203-209.

[8] M.P. Atkins, K.R. Seddon, M. Swadzba-Kwasny, F. Coleman, Oligomerisation process, US Patent 0052838(2016) A1.

[9] F. Coleman, G. Srinivasan, M. Swadzba-Kwasny, Liquid coordination complexes formed by the heterolytic cleavage of metal halides, Angew. Chem. Int. Ed. 52(2013) 12582-12586.

[10] K. Matuszek, A. Chrobok, J. Hogg, F. Coleman, M. Swadzba-Kwasny, Friedel-crafts alkylation catalysed by GaCl₃-based liquid coordination complexes, Green Chem. 17(2015) 4255-4262.

[11] J.M. Hogg, F. Coleman, A. Ferrer-Ugalde, M.P. Atkins, M. Swadzba-Kwasny, Liquid coordination complexes:a new class of Lewis acids as safer alternatives to BF₃ in synthesis of polyalphaolefins, Green Chem. 17(2015) 1831-1841.

[12] L.J. Xue, E. Gurung, G. Tamas, Y.P. Koh, M. Shadeck, S.L. Simon, M. Maroncelli, E.L. Quitevis, Effect of alkyl chain branching on physicochemical properties of imidazolium-based ionic liquids, J. Chem. Eng. Data 61(2016) 1078-1091.

[13] A. Andresova, J. Storch, M. Traikia, Z. Wagner, M. Bendova, P. Husson, Branched and cyclic alkyl groups in imidazolium-based ionic liquids:molecular organization and physico-chemical properties, Fluid Phase Equilib. 371(2014) 41-49.

[14] Q.S. Liu, M. Yang, P.P. Li, S.S. Sun, U. Welz-Biermann, Z.C. Tan, Q.G. Zhang, Physicochemical properties of ionic liquids[C₃py] [NTf₂] and[C₆py] [NTf₂], J. Chem. Eng. Data 56(2011) 4094-4101.

[15] O.O. Okoturo, T.J. Vandernoot, Temperature dependence of viscosity for room temperature ionic liquids, J. Electroanal. Chem. 568(2004) 167-181.

[16] J.M. Hogg, L.C. Brown, K. Matuszek, P. Latos, A. Chrobok, M. Swadzba-Kwasny, Liquid coordination complexes of Lewis acidic metal chlorides:Lewis acidity and insights into speciation, Dalton Trans. 46(2017) 11561-11574.

[17] H.M.A. Abood, A.P. Abbott, A.D. Ballantyne, K.S. Ryder, Do all ionic liquids need organic cations? Characterisation of[AlCl₂·nAmide]⁺AlCl₄^- and comparison with imidazolium based systems, Chem. Commun. 47(2011) 3523-3525.

[18] A.P. Abbott, A.A. Al-Barzinjy, P.D. Abbott, G. Frisch, R.C. Harris, J. Hartley, K.S. Ryder, Speciation, physical and electrolytic properties of eutectic mixtures based on CrCl₃·6H₂O and urea, PCCP 16(2014) 9047-9055.

[19] Y. Fang, K. Yoshii, X. Jiang, X.G. Sun, T. Tsuda, N. Mehio, S. Dai, An AlCl₃ based ionic liquid with a neutral substituted pyridine ligand for electrochemical deposition of aluminum, Electrochim. Acta 160(2015) 82-88.

[20] S. Yous, J.H. Poupaert, I. Lesieur, P. Depreux, D. Lesieur, AlCl₃-DMF reagent in the Friedel-Crafts reaction. Application to the acylation reaction of 2(3H)-Benzothiazolones, J. Org. Chem. 59(1994) 1574-1576.

[21] A.G. Suarez, AlCl₃-DMA reagent in the regioselective solvent free Friedel-Crafts acylation reaction of benzodioxin derivatives, Tetrahedron Lett. 40(1999) 3523-3526.

[22] Y. Liu, R. Li, H.J. Sun, R.S. Hu, Effects of catalyst composition on the ionic liquid catalyzed isobutane/2-butene alkylation, J. Mol. Catal. A Chem. 398(2015) 133-139.

[23] Y. Liu, L.H. Wang, R. Li, R.S. Hu, Reaction mechanism of ionic liquid catalyzed alkylation:alkylation of 2-butene with deuterated isobutene, J. Mol. Catal. A Chem. 421(2016) 29-36.

[24] Z.C. Liu, C.M. Xu, C.P. Huang, Method for manufacturing alkylate oil with composite ionic liquid used as catalyst, US Patent 0133056(2004) A1.

[25] E.L. Smith, A.P. Abbott, K.S. Ryder, Deep eutectic solvents (DESs) and their applications, Chem. Rev. 114(2014) 11060-11082.

[26] Q.H. Zhang, K. De Oliveira Vigier, S. Royer, F. Jerome, Deep eutectic solvents:Syntheses, properties and applications, Chem. Soc. Rev. 41(2012) 7108-7146.

[27] Z.C. Liu, R. Zhang, C.M. Xu, R.G. Xia, Ionic liquid alkylation process produces highquality gasoline, Oil Gas J. 104(2006) 52-56.

[28] Y. Liu, R.S. Hu, C.M. Xu, H.Q. Su, Alkylation of isobutene with 2-butene using composite ionic liquid catalysts, Appl. Catal. A Gen. 346(2008) 189-193.

[29] M. Kermanioryani, M.I.A. Mutalib, Y. Dong, K.C. Lethesh, O.B.O. Ben Ghanem, K.A. Kurnia, N.F. Aminuddin, J.M. Leveque, Physicochemical properties of new imidazolium-based ionic liquids containing aromatic group, J. Chem. Eng. Data 61(2016) 2020-2026.

[30] R. Furth, On the theory of the liquid state 3. The holes theory of the viscous flow of liquids, Proc. Camb. Philos. Soc. 37(1941) 281-290.

[31] F.C. Auluck, D.S. Kothari, The hole theory of liquids, Nature 153(1944) 777.

[32] J. Shi, J.D. Wang, G.Z. Yu, M.H. Chen, Handbook of Chemical Engineering, Chemistry Industry Press, 1996126-187.

[33] A.P. Abbott, Application of hole theory to the viscosity of ionic and molecular liquids, ChemPhysChem 5(2004) 1242-1246.

[34] A.P. Abbott, Model for the conductivity of ionic liquids based on an infinite dilution of holes, ChemPhysChem 6(2005) 2502-2505.

[35] S.W. Tang, A.M. Scurto, B. Subramaniam, Improved 1-butene/isobutane alkylation with acidic ionic liquids and tunable acid/ionic liquid mixtures, J. Catal. 268(2009) 243-250.

[36] J. Zhang, C.P. Huang, B.H. Chen, P.J. Ren, M.Pu. Isobutane, 2-Butene alkylation catalyzed by chloroaluminate ionic liquids in the presence of aromatic additives, J. Catal. 249(2007) 261-268.

Physicochemical properties of amide-AlCl₃ based ionic liquid analogues and their mixtures with copper salt

Physicochemical properties of amide-AlCl₃ based ionic liquid analogues and their mixtures with copper salt

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 15

编辑推荐

Metrics

本文评价

[1]	Abdelgadir Bashir Banaga, Yan-Bin Li, Zhi-Hao Li, Bao-Chang Sun, Guang-Wen Chu. Experimental investigation of the mixing efficiency via intensity of segregation along axial direction of a rotating bar reactor[J]. 中国化学工程学报, 2023, 59(7): 153-159.
[2]	Hae-Kyun Park, Dong-Hyuk Park, Bum-Jin Chung. Influence of the electrolyte conductivity on the critical current density and the breakdown voltage[J]. 中国化学工程学报, 2023, 59(7): 169-175.
[3]	Tinghao Jia, Yunbo Yu, Qing Liu, Yao Yang, Ji-Jun Zou, Xiangwen Zhang, Lun Pan. Theoretical and experimental study on the inhibition of jet fuel oxidation by diarylamine[J]. 中国化学工程学报, 2023, 56(4): 225-232.
[4]	Songsong Wang, Hong Li, Changyuan Tao, Renlong Liu, Yundong Wang, Zuohua Liu. Study on cavern evolution and performance of three mixers in agitation of yield-pseudoplastic fluids[J]. 中国化学工程学报, 2023, 55(3): 111-122.
[5]	Jianhui Zhou, Guohao Du, Jianfeng Hu, Xin Lai, Shan Liu, Zhengguo Zhang. The establishment of Boron nitride@sodium alginate foam/polyethyleneglycol composite phase change materials with high thermal conductivity, shape stability, and reusability[J]. 中国化学工程学报, 2023, 54(2): 11-21.
[6]	Xianglin Liu, Minjie Xu, Chenxi Cao, Zixu Yang, Jing Xu. Effects of zinc on χ-Fe₅C₂ for carbon dioxide hydrogenation to olefins: Insights from experimental and density function theory calculations[J]. 中国化学工程学报, 2023, 54(2): 206-214.
[7]	Yifeng Chen, Hang Yu, Jingjing Chen, Xiaohua Lu, Xiaoyan Ji. Viscous behavior of 1-hexyl-methylimidazolium bis(trifluoromethylsulfonyl)imide/titanium dioxide/polyethylene glycol[J]. 中国化学工程学报, 2023, 54(2): 280-287.
[8]	Baodong Zhao, Yinglei Wang, Fulei Gao, Yajing Liu, Weixiao Liu, Feng Ding. Understanding the alkyl effect of geminal dinitropropyl ester energetic plasticizers on hydroxyl terminated polybutadiene (HTPB): Simultaneous tuning on low temperature behavior and processability[J]. 中国化学工程学报, 2023, 54(2): 364-371.
[9]	Yufei Wang, Zihao Chen, Rui Chen, Jie Wei. A self-healing and conductive ionic hydrogel based on polysaccharides for flexible sensors[J]. 中国化学工程学报, 2023, 53(1): 73-82.
[10]	Yang Liu, Qiu Han, Guiliang Li, Haibo Lin, Fu Liu, Gang Deng, Dingfeng Lv, Weijie Sun. Purifying chylous plasma by precluding triglyceride via carboxylated polyethersulfone microfiltration membrane[J]. 中国化学工程学报, 2022, 49(9): 130-139.
[11]	Fenfen You, Qing-Hong Shi. In situ investigation of lysozyme adsorption into polyelectrolyte brushes by quartz crystal microbalance with dissipation[J]. 中国化学工程学报, 2022, 48(8): 106-115.
[12]	Yaqi Ren, Shuqian Xia. Synthesis and mechanism analysis of a new oil soluble viscosity reducer for flow improvement of Chenping heavy oil[J]. 中国化学工程学报, 2022, 45(5): 58-67.
[13]	Anil Kumar Nain. Study of intermolecular interactions in binary mixtures of methyl acrylate with benzene and methyl substituted benzenes at different temperatures: An experimental and theoretical approach[J]. 中国化学工程学报, 2022, 44(4): 212-238.
[14]	Mingxia Tian, Aili Wang, Hengbo Yin. Evolution of copper nanowires through coalescing of copper nanoparticles induced by aliphatic amines and their electrical conductivities in polyester films[J]. 中国化学工程学报, 2022, 44(4): 284-291.
[15]	Shiqi Yang, Zhentao Wang, Qian Kong, Bin Li, Junfeng Wang. Visualization on electrified micro-jet instability from Taylor cone in electrohydrodynamic atomization[J]. 中国化学工程学报, 2022, 44(4): 456-465.