Hydrogen bond promoted thermal stability enhancement of acetate based ionic liquid

doi:10.1016/j.cjche.2020.02.019

中国化学工程学报 ›› 2020, Vol. 28 ›› Issue (5): 1293-1301.DOI: 10.1016/j.cjche.2020.02.019

• Separation Science and Engineering • 上一篇下一篇

Hydrogen bond promoted thermal stability enhancement of acetate based ionic liquid

Ling Zhang¹, Ligang Wei¹, Shangru Zhai¹, Dingwei Zhao², Jian Sun², Qingda An¹

1 Faculty of Light Industry and Chemical Engineering, Dalian Polytechnic University, Dalian 116034, China;
2 Key Laboratory of Molecular Medicine and Biotherapy, School of Life Science, Beijing Institute of Technology, Beijing 100081, China

收稿日期:2019-12-03 修回日期:2020-01-23 出版日期:2020-05-28 发布日期:2020-07-29
通讯作者: Jian Sun, Qingda An
基金资助:
This work was financially supported by the National Natural Science Foundation of China (21776026), the Liaoning Revitalization Talents Program (XLYC1902037) and the start-up research funding of Beijing Institute of Technology (3160011181808).

Hydrogen bond promoted thermal stability enhancement of acetate based ionic liquid

Ling Zhang¹, Ligang Wei¹, Shangru Zhai¹, Dingwei Zhao², Jian Sun², Qingda An¹

1 Faculty of Light Industry and Chemical Engineering, Dalian Polytechnic University, Dalian 116034, China;
2 Key Laboratory of Molecular Medicine and Biotherapy, School of Life Science, Beijing Institute of Technology, Beijing 100081, China

Received:2019-12-03 Revised:2020-01-23 Online:2020-05-28 Published:2020-07-29
Contact: Jian Sun, Qingda An
Supported by:
This work was financially supported by the National Natural Science Foundation of China (21776026), the Liaoning Revitalization Talents Program (XLYC1902037) and the start-up research funding of Beijing Institute of Technology (3160011181808).

摘要/Abstract

摘要： Acetate-based imidazolium ionic liquids (ILs) are of great importance and widely applied in biomass processing and engineering but under stability issue due to the structure self-rearrangement induced by C₂-H deprotonation, by which the IL based biomass processing will be challenging. Herein, we demonstrated that the thermal stability of normal acetate-based imidazolim[C₈C₁Im] [OAc] could be significantly improved by changing its cation and anion environment with the presence of 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl) imide IL ([C₄C₁Im] [NTf₂]). When the molar fraction of[C₈C₁Im] [OAc] was 0.3, the thermal stability of[C₈C₁Im] [OAc] could be significantly improved (ΔT_5%dec=+43℃). Detailed information obtained from thermal gravimetric analysis (TGA) and nuclear magnetic resonance (NMR) revealed that the addition of[C₄C₁Im] [NTf₂] played a significant role in enhancing the thermal stability of[C₈C₁Im] [OAc]. It was proposed that the formation of an anion-π⁺ structure network between[C₈C₁Im] [OAc] and[C₄C₁Im] [NTf₂] via strong hydrogen bond interactions greatly affects the environment of hydrogen atom in the imidazolium ring of each IL.

关键词: Imidazolium salt, Binary ionic liquids, Thermal stability, Hydrogen bond interactions

Abstract: Acetate-based imidazolium ionic liquids (ILs) are of great importance and widely applied in biomass processing and engineering but under stability issue due to the structure self-rearrangement induced by C₂-H deprotonation, by which the IL based biomass processing will be challenging. Herein, we demonstrated that the thermal stability of normal acetate-based imidazolim[C₈C₁Im] [OAc] could be significantly improved by changing its cation and anion environment with the presence of 1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl) imide IL ([C₄C₁Im] [NTf₂]). When the molar fraction of[C₈C₁Im] [OAc] was 0.3, the thermal stability of[C₈C₁Im] [OAc] could be significantly improved (ΔT_5%dec=+43℃). Detailed information obtained from thermal gravimetric analysis (TGA) and nuclear magnetic resonance (NMR) revealed that the addition of[C₄C₁Im] [NTf₂] played a significant role in enhancing the thermal stability of[C₈C₁Im] [OAc]. It was proposed that the formation of an anion-π⁺ structure network between[C₈C₁Im] [OAc] and[C₄C₁Im] [NTf₂] via strong hydrogen bond interactions greatly affects the environment of hydrogen atom in the imidazolium ring of each IL.

Key words: Imidazolium salt, Binary ionic liquids, Thermal stability, Hydrogen bond interactions

Ling Zhang, Ligang Wei, Shangru Zhai, Dingwei Zhao, Jian Sun, Qingda An. Hydrogen bond promoted thermal stability enhancement of acetate based ionic liquid[J]. 中国化学工程学报, 2020, 28(5): 1293-1301.

Ling Zhang, Ligang Wei, Shangru Zhai, Dingwei Zhao, Jian Sun, Qingda An. Hydrogen bond promoted thermal stability enhancement of acetate based ionic liquid[J]. Chinese Journal of Chemical Engineering, 2020, 28(5): 1293-1301.

参考文献

[1] S.J. Zeng, X. Zhang, L.P. Bai, X.C. Zhang, H. Wang, J.J. Wang, D. Bao, M.D. Li, X.Y. Liu, S.J. Zhang, Ionic-liquid-based CO₂ capture systems:structure, interaction and process, Chem. Rev. 117(2017) 9625-9673.
[2] G.K. Cui, J.J. Wang, S.J. Zhang, Active chemisorption sites in functionalized ionic liquids for carbon capture, Chem. Soc. Rev. 45(2016) 4307-4339.
[3] S.B. Wang, X.C. Wang, Imidazolium ionic liquids, imidazolylidene heterocyclic carbenes, and zeolitic imidazolate frameworks for CO₂ capture and photochemical reduction, Angew Chem Int Edit. 55(2016) 2308-2320.
[4] S.J. Zhang, J. Sun, X.C. Zhang, J.Y. Xin, Q.Q. Miao, J.J. Wang, Ionic liquid-based green processes for energy production, Chem. Soc. Rev. 43(2014) 7838-7869.
[5] L.S. Guo, J. Sun, Q.J. Ge, N. Tsubaki, Recent advances in direct catalytic hydrogenation of carbon dioxide to valuable C²⁺ hydrocarbons, J. Mater. Chem. A 6(2018) 23244-23262.
[6] J. Sun, J.Q. Wang, W.G. Cheng, J.X. Zhang, X.H. Li, S.J. Zhang, Y.B. She, Chitosan functionalized ionic liquid as a recyclable biopolymer-supported catalyst for cycloaddition of CO₂, Green Chem. 14(2012) 654-660.
[7] C.J. Clarke, W.C. Tu, O. Levers, A. Brohl, J.P. Hallett, Green and sustainable solvents in chemical processes, Chem. Rev. 118(2018) 747-800.
[8] S.P.M. Ventura, F.A.E. Silva, M.V. Quental, D. Mondal, M.G. Freire, J.A.P. Coutinho, Ionic-liquid-mediated extraction and separation processes for bioactive compounds:past, present, and future trends, Chem. Rev. 117(2017) 6984-7052.
[9] L.C. Tome, I.M. Marrucho, Ionic liquid-based materials:a platform to design engineered CO₂ separation membranes, Chem. Soc. Rev. 45(2016) 2785-2824.
[10] S.F. Wang, X.Q. Li, H. Wu, Z.Z. Tian, Q.P. Xin, G.W. He, D.D. Peng, S.L. Chen, Y. Yin, Z.Y. Jiang, M.D. Guiver, Advances in high permeability polymer-based membrane materials for CO₂ separations, Energy Environ. Sci. 9(2016) 1863-1890.
[11] W.J. Qian, J. Texter, F. Yan, Frontiers in poly(ionic liquid)s:syntheses and applications, Chem. Soc. Rev. 46(2017) 1124-1159.
[12] C.N. Dai, J. Zhang, C.P. Huang, Z.G. Lei, Ionic liquids in selective oxidation:catalysts and solvents, Chem. Rev. 117(2017) 6929-6983.
[13] J.M. Zheng, J.A. Lochala, A. Kwok, Z.Q.D. Deng, J. Xiao, Research progress towards understanding the unique interfaces between concentrated electrolytes and electrodes for energy storage applications, Adv Sci 4(2017) 1700032.
[14] H.Y. Che, S.L. Chen, Y.Y. Xie, H. Wang, K. Amine, X.Z. Liao, Z.F. Ma, Electrolyte design strategies and research progress for room-temperature sodium-ion batteries, Energy Environ. Sci. 10(2017) 1075-1101.
[15] L. Shuai, M.T. Amiri, Y.M. Questell-Santiago, F. Heroguel, Y.D. Li, H. Kim, R. Meilan, C. Chapple, J. Ralph, J.S. Luterbacher, Formaldehyde stabilization facilitates lignin monomer production during biomass depolymerization, Science 354(2016) 329-333.
[16] Z.R. Zhang, J.L. Song, B.X. Han, Catalytic transformation of lignocellulose into chemicals and fuel products in ionic liquids, Chem. Rev. 117(2017) 6834-6880.
[17] K.H. Kim, T. Dutta, J. Sun, B. Simmons, S. Singh, Biomass pretreatment using deep eutectic solvents from lignin derived phenols, Green Chem. 20(2018) 809-815.
[18] F. Xu, J. Sun, M. Wehrs, K.H. Kim, S.S. Rau, A.M. Chan, B.A. Simmons, A. Mukhopadhyay, S. Singh, Biocompatible choline-based deep eutectic solvents enable one-pot production of cellulosic ethanol, ACS Sustain. Chem. Eng. 6(2018) 8914-8919.
[19] F. Xu, J. Sun, N.V.S.N.M. Konda, J. Shi, T. Dutta, C.D. Scown, B.A. Simmons, S. Singh, Transforming biomass conversion with ionic liquids:Process intensification and the development of a high-gravity, one-pot process for the production of cellulosic ethanol, Energ. Environ. Sci. 9(2016) 1042-1049.
[20] J.K. Xu, Y.C. Sun, R.C. Sun, Ionic liquid pretreatment of woody biomass to facilitate biorefinery:structural elucidation of alkali-soluble hemicelluloses, ACS Sustain. Chem. Eng. 2(2014) 1035-1042.
[21] J. Shi, J.M. Gladden, N. Sathitsuksanoh, P. Kambam, L. Sandoval, D. Mitra, S. Zhang, A. George, S.W. Singer, B.A. Simmons, S. Singh, One-pot ionic liquid pretreatment and saccharification of switchgrass, Gree Chem. 15(2013) 2579-2589.
[22] E. Husson, T. Auxenfans, M. Herbaut, M. Baralle, V. Lambertyn, H. Rakotoarivonina, C. Remond, C. Sarazin, Sequential and simultaneous strategies for biorefining of wheat straw using room temperature ionic liquids, xylanases and cellulases, Bioresour. Technol. 251(2018) 280-287.
[23] T. Dutta, N.G. Isern, J. Sun, E. Wang, S. Hull, J.R. Cort, B.A. Simmons, S. Singh, Survey of lignin-structure changes and depolymerization during ionic liquid pretreatment, ACS Sustain. Chem. Eng. 5(2017) 10116-10127.
[24] Y.Y. Yang, H.L. Fan, J.L. Song, Q.L. Meng, H.C. Zhou, L.Q. Wu, G.Y. Yang, B.X. Han, Free radical reaction promoted by ionic liquid:a route for metal-free oxidation depolymerization of lignin model compound and lignin, Chem. Commun. 51(2015) 4028-4031.
[25] M.A.R. Martins, U. Domanska, B. Schroder, J.A.P. Coutinho, S.P. Pinho, Selection of ionic liquids to be used as separation agents for terpenes and terpenoids, ACS Sustain. Chem. Eng. 4(2016) 548-556.
[26] P. Moyer, M.D. Smith, N. Abdoulmoumine, S.C. Chmely, J.C. Smith, L. Petridis, N. Labbe, Relationship between lignocellulosic biomass dissolution and physicochemical properties of ionic liquids composed of 3-methylimidazolium cations and carboxylate anions, Phys. Chem. Chem. Phys. 20(2018) 2508-2516.
[27] J. Sun, J. Shi, N.V.S.N.M. Konda, C. Dan, Efficient dehydration and recovery of ionic liquid after lignocellulosic processing using pervaporation, Biotechnol. Biofuels 10(2017) 154.
[28] Z.Y. Meng, J. Sun, J.Q. Wang, J.X. Zhang, Z.Z. Fu, W.G. Cheng, X.P. Zhang, An efficient and stable ionic liquid system for synthesis of ethylene glycol via hydrolysis of ethylene carbonate, Chinese J Chem Eng. 18(2010) 962-966.
[29] A.M.d.C. Lopes, R.M. Łukasik, Separation and recovery of a hemicellulose-derived sugar produced from the hydrolysis of biomass by an acidic ionic liquid, ChemSusChem 11(2018) 1099-1107.
[30] P.A. Hunt, C.R. Ashworth, R.P. Matthews, Hydrogen bonding in ionic liquids, Chem. Soc. Rev. 44(2015) 1257-1288.
[31] S.M. Chen, S.J. Zhang, X.M. Liu, J.Q. Wang, J.J. Wang, K. Dong, J. Sun, B.H. Xu, Ionic liquid clusters:structure, formation mechanism, and effect on the behavior of ionic liquids, Phys. Chem. Chem. Phys. 16(2014) 5893-5906.
[32] Y. Chen, Y.Y. Cao, Y.W. Zhang, T.C. Mu, Hydrogen bonding between acetate-based ionic liquids and water:three types of IR absorption peaks and NMR chemical shifts change upon dilution, J. Mol. Struct. 1058(2014) 244-251.
[33] J.M.M. Araujo, A.B. Pereiro, J.N.C. Lopes, L.P.N. Rebelo, I.M. Marrucho, Hydrogenbonding and the dissolution mechanism of uracil in an acetate ionic liquid:new insights from NMR spectroscopy and quantum chemical calculations, J. Phys. Chem. B 117(2013) 4109-4120.
[34] Y.-L. Wang, A. Laaksonen, M.D. Fayer, Hydrogen bonding versus π-π stacking interactions in imidazolium-oxalatoborate ionic liquid, J. Phys. Chem. B 121(2017) 7173-7179.
[35] Y.Y. Cao, T.C. Mu, Comprehensive investigation on the thermal stability of 66 ionic liquids by thermogravimetric analysis, Ind. Eng. Chem. Res. 53(2014) 8651-8664.
[36] M.T. Clough, K. Geyer, P.A. Hunt, J. Mertes, T. Welton, Thermal decomposition of carboxylate ionic liquids:trends and mechanisms, Phys. Chem. Chem. Phys. 15(2013) 20480-20495.
[37] H. Tokuda, K. Hayamizu, K. Ishii, M. Susan, M. Watanabe, Physicochemical properties and structures of room temperature ionic liquids. 2. Variation of alkyl chain length in imidazolium cation, J. Phys. Chem. B 109(2005) 6103-6110.
[38] Y. Cao, Y. Chen, X. Sun, Z. Zhang, T. Mu, Water sorption in ionic liquids:kinetics, mechanisms and hydrophilicity, Phys. Chem. Chem. Phys. 14(2012) 12252-12262.
[39] Y. Cao, Y. Chen, L. Lu, Z. Xue, T. Mu, Water sorption in functionalized ionic liquids:kinetics and intermolecular interactions, Ind. Eng. Chem. Res. 52(2013) 2073-2083.
[40] M.C. Kroon, W. Buijs, C.J. Peters, G.J. Witkamp, Quantum chemical aided prediction of the thermal decomposition mechanisms and temperatures of ionic liquids, Thermochim. Acta 465(2007) 40-47.
[41] C. Maton, N. De Vos, C.V. Stevens, Ionic liquid thermal stabilities:decomposition mechanisms and analysis tools, Chem. Soc. Rev. 42(2013) 5963-5977.
[42] P. Navarro, M. Larriba, J. Garcia, F. Rodriguez, Thermal stability, specific heats, and surface tensions of (emim DCA +4empy Tf₂N) ionic liquid mixtures, J. Chem. Thermodyn. 76(2014) 152-160.
[43] R. Hayes, G.G. Warr, R. Atkin, Structure and nanostructure in ionic liquids, Chem. Rev. 115(2015) 6357-6426.
[44] R.P. Matthews, I.J. Villar-Garcia, C.C. Weber, J. Griffith, F. Cameron, J.P. Hallett, P.A. Hunt, T. Welton, A structural investigation of ionic liquid mixtures, Phys. Chem. Chem. Phys. 18(2016) 8608-8624.
[45] R.P. Matthews, T. Welton, P.A. Hunt, Competitive pi interactions and hydrogen bonding within imidazolium ionic liquids, Phys. Chem. Chem. Phys. 16(2014) 3238-3253.
[46] Y. Fukaya, K. Hayashi, M. Wada, H. Ohno, Cellulose dissolution with polar ionic liquids under mild conditions:required factors for anions, Green Chem. 10(2008) 44-46.
[47] Y. Fukaya, A. Sugimoto, H. Ohno, Superior solubility of polysaccharides in low viscosity, polar, and halogen-free 1,3-dialkylimidazolium formates, Biomacromolecules 7(2006) 3295-3297.
[48] T. Cremer, C. Kolbeck, K.R.J. Lovelock, N. Paape, R. Wolfel, P.S. Schulz, P. Wasserscheid, H. Weber, J. Thar, B. Kirchner, F. Maier, H.P. Steinruck, Towards a molecular understanding of cation-anion interactions-probing the electronic structure of imidazolium ionic liquids by NMR spectroscopy, X-ray photoelectron spectroscopy and theoretical calculations, Chem-Eur. J. 16(2010) 9018-9033.
[49] E. Liu, M. Li, L. Das, Y. Pu, J. Shi, Understanding lignin fractionation and characterization from engineered switchgrass treated by an aqueous ionic liquid, ACS Sustain. Chem. Eng. 6(2018) 6612-6623.
[50] K.H. Kim, T. Dutta, J. Sun, B. Simmons, S. Singh, Biomass pretreatment using deep eutectic solvent from lignin derived phenols, Green Chem. 20(2018) 809-815.

Hydrogen bond promoted thermal stability enhancement of acetate based ionic liquid

Hydrogen bond promoted thermal stability enhancement of acetate based ionic liquid

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 6

编辑推荐

Metrics

本文评价

[1]	Bingxiao Feng, Lining Hao, Chaoting Deng, Jiaqiang Wang, Hongbing Song, Meng Xiao, Tingting Huang, Quanhong Zhu, Hengjun Gai. A highly hydrothermal stable copper-based catalyst for catalytic wet air oxidation of m-cresol in coal chemical wastewater[J]. 中国化学工程学报, 2023, 57(5): 338-348.
[2]	Ziqing Yuan, Ziyu Chen, Jianxin Mao, Renxian Zhou. The size effect and high activity of nanosized platinum supported catalysts for low temperature oxidation of volatile organic compounds[J]. 中国化学工程学报, 2021, 39(11): 135-143.
[3]	Li Li, Hong Qi. Gas separation using sol-gel derived microporous zirconia membranes with high hydrothermal stability[J]. Chinese Journal of Chemical Engineering, 2015, 23(8): 1300-1306.
[4]	梁蕊, 杨美荣, 轩小鹏. Thermal Stability and Thermal Decomposition Kinetics of 1-Butyl-3-methylimidazolium Dicyanamide[J]. , 2010, 18(5): 736-741.
[5]	LIU Wei (刘伟), ZHANG Baoquan (张宝泉), LIU Xiufeng (刘秀凤) and XU Liming (徐黎明). Thermal Stability of Silica-Zirconia Membranes[J]. , 2006, 14(1): 31-36.
[6]	柯明, 汪燮卿, 张凤美. 磷改性ZSM-5分子筛物化性质和裂解制乙烯性能的研究[J]. , 2003, 11(6): 671-676.