Lactic-based Novel Amine Ionic Liquid: Synthesis and Characterization of [DEA][Lac]

Document Type : Research Paper


Department of Chemical Engineering, Faculty of Energy, Kermanshah University of Technology, Kermanshah, Iran


In this study, a novel amine ionic liquid “Diethanolamine Lactic” [DEA][Lac] was synthesized. The replacement of halogenated ion fluid was used as a modified methodology for the preparation of diethanolamine based on lactic acid. The ionic liquid was characterized using the Fourier transform infrared (FTIR) spectra and the nuclear magnetic resonance (NMR) spectroscopy. The changes in bands' wavelengths and the peaks of the participating elements and process materials have been confirmed before and after synthesis based on the results of FTIR analysis which demonstrate the successful synthesis of diethanolamine lactic. The NMR analysis also clearly confirms the synthesis of diethanolamine lactic acid. Analysis results were shown in the successful synthesis of the [diethanolamine] [lactic].   


[1]     Luo QX, An BW, Ji M, Zhang J. Hybridization of metal–organic frameworks and task-specific ionic liquids: fundamentals and challenges. Materials Chemistry Frontiers. 2018;2(2):219-34.
[2]     Wang LY, Xu YL, Li ZD, Wei YN, Wei JP. CO2/CH4 and H2S/CO2 selectivity by ionic liquids in natural gas sweetening. Energy & fuels. 2017 Dec 22;32(1):10-23.
[3]     Wei Z, Zhang ZH, Wang MM, Xu L, Liu B, Jiao H. Combination effect of ligands and ionic liquid components on the structure and properties of manganese metal–organic frameworks. CrystEngComm. 2017;19(36):5402-11.
[4]     Kinik FP, Uzun A, Keskin S. Ionic liquid/metal–organic framework composites: from synthesis to applications. ChemSusChem. 2017 Jul 21;10(14):2842-63.
[5]     Wang B, Qin L, Mu T, Xue Z, Gao G. Are ionic liquids chemically stable?. Chemical reviews. 2017 Feb 27;117(10):7113-31.
[6]     Cui G, Wang J, Zhang S. Active chemisorption sites in functionalized ionic liquids for carbon capture. Chemical Society Reviews. 2016;45(15):4307-39.
[7]     Basile A, Bhatt AI, O’Mullane AP. Stabilizing lithium metal using ionic liquids for long-lived batteries. Nature communications. 2016 Jun 13;7:ncomms11794.
[8]     Forsyth M, Girard GM, Basile A, Hilder M, MacFarlane DR, Chen F, Howlett PC. Inorganic-organic ionic liquid electrolytes enabling high energy-density metal electrodes for energy storage. Electrochimica Acta. 2016 Dec 1;220:609-17.
[9]     Ohno H, editor. Electrochemical aspects of ionic liquids. John Wiley & Sons; 2005 Aug 8.
[10]  O'regan B, Grätzel M. A low-cost, high-efficiency solar cell based on dye-sensitized colloidal TiO2 films. nature. 1991 Oct;353(6346):737.
[11]  Ye C, Liu W, Chen Y, Yu L. Room-temperature ionic liquids: a novel versatile lubricant. Chemical Communications. 2001(21):2244-5.
[12]  Wang Y, Yang H. Synthesis of CoPt nanorods in ionic liquids. Journal of the American Chemical Society. 2005 Apr 20;127(15):5316-7.
[13]  Ding K, Miao Z, Liu Z, Zhang Z, Han B, An G, Miao S, Xie Y. Facile synthesis of high quality TiO2 nanocrystals in ionic liquid via a microwave-assisted process. Journal of the American Chemical Society. 2007 May 23;129(20):6362-3.
[14]  Zhao D, Wu M, Kou Y, Min E. Ionic liquids: applications in catalysis. Catalysis today. 2002 May 15;74(1-2):157-89.
[15]  Geldbach TJ, Dyson PJ. A versatile ruthenium precursor for biphasic catalysis and its application in ionic liquid biphasic transfer hydrogenation: conventional vs task-specific catalysts. Journal of the American Chemical Society. 2004 Jul 7;126(26):8114-5.
[16]  Mora‐Pale M, Meli L, Doherty TV, Linhardt RJ, Dordick JS. Room temperature ionic liquids as emerging solvents for the pretreatment of lignocellulosic biomass. Biotechnology and bioengineering. 2011 Jun;108(6):1229-45.
[17]  Ouellet M, Datta S, Dibble DC, Tamrakar PR, Benke PI, Li C, Singh S, Sale KL, Adams PD, Keasling JD, Simmons BA. Impact of ionic liquid pretreated plant biomass on Saccharomyces cerevisiae growth and biofuel production. Green Chemistry. 2011;13(10):2743-9.
[18]  Azizi D, Larachi F. Immiscible dual ionic liquid-ionic liquid mineral separation of rare-earth minerals. Separation and Purification Technology. 2018 Jan 31;191:340-53.
[19]  Karpińska M, Wlazło M, Domańska U. Investigation on the ethylbenzene/styrene separation efficiency with ionic liquids in liquid–liquid extraction. Chemical Engineering Research and Design. 2017 Dec 1;128:214-20.
[20]  Mashuga M, Olasunkanmi L, Adekunle A, Yesudass S, Kabanda M, Ebenso E. Adsorption, thermodynamic and quantum chemical studies of 1-hexyl-3-methylimidazolium based ionic liquids as corrosion inhibitors for mild steel in HCl. Materials. 2015 Jun 17;8(6):3607-32.
[21]  Hanza AP, Naderi R, Kowsari E, Sayebani M. Corrosion behavior of mild steel in H2SO4 solution with 1, 4-di [1′-methylene-3′-methyl imidazolium bromide]-benzene as an ionic liquid. Corrosion Science. 2016 Jun 1;107:96-106.
[22]  Likhanova NV, Domínguez-Aguilar MA, Olivares-Xometl O, Nava-Entzana N, Arce E, Dorantes H. The effect of ionic liquids with imidazolium and pyridinium cations on the corrosion inhibition of mild steel in acidic environment. Corrosion Science. 2010 Jun 1;52(6):2088-97.
[23]  Kodama K, Tsuda R, Niitsuma K, Tamura T, Ueki T, Kokubo H, Watanabe M. Structural effects of polyethers and ionic liquids in their binary mixtures on lower critical solution temperature liquid-liquid phase separation. Polymer journal. 2011 Mar;43(3):242.
[24]  Sun J, Macfarlane DR, Forsyth M. A new family of ionic liquids based on the 1-alkyl-2-methyl pyrrolinium cation. Electrochimica acta. 2003 May 30;48(12):1707-11.
[25]  Golding J, Hamid N, Macfarlane DR, Forsyth M, Forsyth C, Collins C, Huang J. N-methyl-N-alkylpyrrolidinium hexafluorophosphate salts: novel molten salts and plastic crystal phases. Chemistry of materials. 2001 Feb 19;13(2):558-64.
[26]  Zhang C, Xin B, Xi Z, Zhang B, Li Z, Zhang H, Li Z, Hao J. Phosphonium-based ionic liquid: a new phosphorus source toward microwave-driven synthesis of nickel phosphide for efficient hydrogen evolution reaction. ACS Sustainable Chemistry & Engineering. 2017 Dec 20;6(1):1468-77.
[27]  Yu L, Garcia D, Ren R, Zeng X. Ionic liquid high temperature gas sensors. Chemical Communications. 2005(17):2277-9.
[28]  Zhou ZB, Matsumoto H, Tatsumi K. Low‐melting, low‐viscous, hydrophobic ionic liquids: aliphatic quaternary ammonium salts with perfluoroalkyltrifluoroborates. Chemistry–A European Journal. 2005 Jan 7;11(2):752-66.
[29]  Pernak J, Syguda A, Mirska I, Pernak A, Nawrot J, Pra̧dzyńska A, Griffin ST, Rogers RD. Choline‐derivative‐based ionic liquids. Chemistry–A European Journal. 2007 Aug 17;13(24):6817-27.
[30]  Zhang Z, Zhang Q, Zhang Q, Zhang T, Li W. Isobaric vapor–liquid equilibrium of tert-butyl alcohol + water + triethanolamine-based ionic liquid ternary systems at 101.3 kPa. Journal of Chemical & Engineering Data. 2015 Jun 9;60(7):2018-27.
[31]  Heintz A. Recent developments in thermodynamics and thermophysics of non-aqueous mixtures containing ionic liquids. A review. The Journal of Chemical Thermodynamics. 2005 Jun 1;37(6):525-35.
[32]  Speight JG. Chemical Transformations in the Environment. Environmental Organic Chemistry for Engineers; Butterworth-Heinemann: Oxford, UK. 2017:305-53.
[33]  Giernoth R. In situ ir spectroscopy. In: Rogers RD, Seddon KR, editors. ionic liquids: Toward the detection of reactive intermediates in transition metal catalysis. American Chemical Society; 2005.
[34]  Lin-Vien D, Colthup NB, Fateley WG, Grasselli JG. The handbook of infrared and Raman characteristic frequencies of organic molecules. Elsevier; 1991 Dec 2.
[35]  Lv B, Xia Y, Shi Y, Liu N, Li W, Li S. A novel hydrophilic amino acid ionic liquid [C2OHmim][Gly] as aqueous sorbent for CO2 capture. International Journal of Greenhouse Gas Control. 2016 Mar 1;46:1-6.
[36] de Castro CA, Langa E, Morais AL, Lopes ML, Lourenço MJ, Santos FJ, Santos MS, Lopes JN, Veiga HI, Macatrão M, Esperança JM. Studies on the density, heat capacity, surface tension and infinite dilution diffusion with the ionic liquids [C4mim][NTf2],[C4mim][dca],[C2mim][EtOSO3] and [Aliquat][dca]. Fluid Phase Equilibria. 2010 Jul 15;294(1-2):157-79.