Citation: Koon-Kee Kow, Kamaliah Sirat. Novel manganese(II)-based deep eutectic solvents: Synthesis and physical properties analysis[J]. Chinese Chemical Letters, ;2015, 26(10): 1311-1314. doi: 10.1016/j.cclet.2015.05.049 shu

Novel manganese(II)-based deep eutectic solvents: Synthesis and physical properties analysis

Koon-Kee Kow ^, ,
Kamaliah Sirat

1.
Department of Chemistry, Faculty of Science, Universiti Putra Malaysia, Serdang 43400, Malaysia

Corresponding author: Koon-Kee Kow,
Received Date: 26 February 2015
Available Online: 19 May 2015

Type IV deep eutectic solvent (DES) involves the formation of metal-based eutectics from metal salts or metal salt hydrate incombination with various hydrogen-bonddonors(HBDs) suchas urea, ethylene glycol or acetamide. In current study, twodistinguished approaches were used to synthesize potential DESs, given as the direct heating and the evaporatingmethods. Successful synthesized DESswere subjected forphysical properties characterization by Fourier TransformInfrared (FTIR) Spectroscopy, thermal stability, viscosity, and conductivity analyses. Five novelmanganese (II)-basedDESswere successfully synthesized as reported in this study. Data obtained indicated that the MnCl₂·4H₂O·acetamide DES exhibits the lowest freezing point (27.5℃), highest thermal stability (193℃ point of dehydration), lowest viscosity (η=112.8 cP) and the highest conductivity (0.12723 mS/cm). The findings obtained reveal the characteristics, nature or features of synthesized DESs as potential industrial solvents.
- Ionic liquid,
- Deep eutectic solvents,
- Manganese,
- Solvent synthesis,
- Physical properties
1. [1]
  [1] P. Wasserschield, T. Welton, Ionic Liquids in Synthesis, Wiley-VCH, Weinheim, 2003.
2. [2]
  [2] M.A. Kareem, F.S. Mjalli, M.A. Hashim, I.M. Alnashef, Phosphonium-based ionic liquids analogues and their physical properties, J. Chem. Eng. Data 55(2010) 4632-4637.
3. [3]
  [3] J. Sun, M. Forsyth, D.R. MacFarlene, Room-temperature molten salts based on the quaternary ammonium ion, J. Phys. Chem. B 102(1998) 8858-8864.
4. [4]
  [4] S.J. Zhang, Y.H. Chen, R.X.F. Ren, et al., Solubility of CO₂ in sulfonate ionic liquids at high pressure, J. Chem. Eng. Data 50(2005) 230-233.
5. [5]
  [5] A. Paiva, R. Craveiro, I. Aroso, et al., Natural deep eutectic solvents-solvents for the 21st century, ACS Sust. Chem. Eng. 2(2014) 1063-1071.
6. [6]
  [6] C.M. Wang, X.Y. Luo, X. Zhu, et al., The strategies for improving carbon dioxide chemisorption by functionalized ionic liquids, RSC Adv. 3(2013) 15518-15527.
7. [7]
  [7] M.A. Navarra, J. Manzi, L. Lombardo, S. Panero, B. Scrosati, Ionic liquid-based membranes as electrolytes for advanced lithium polymer batteries, Chem-SusChem 4(2011) 125-130.
8. [8]
  [8] X. Ge, C.D. Gu, Y. Lu, X.L. Wang, J.P. Tu, A Versatile protocol for the ionothermal synthesis of nanostructured nickel compounds as energy storage materials from a choline chloride-based ionic liquid, J. Mater. Chem. A 1(2013) 13454-13461.
9. [9]
  [9] M. Hayyan, F.S. Mjalli, M.A. Hashim, I.M. Alnashef, X.M. Tan, Electrochemical reduction of dioxygen in bis (trifluoromethylsulfonyl) imide based Ionic liquids, J. Electroanal. Chem. 657(2011) 150-157.
10. [10]
  [10] P.D. de María, Z. Maugeri, Ionic liquids in biotransformations:from proof-ofconcept to emerging deep-eutectic-solvents, Curr. Opin. Chem. Biol. 15(2011) 220-225.
11. [11]
  [11] N.V. Plechkova, K.R. Seddon, Applications of ionic liquids in the chemical industry, Chem. Soc. Rev. 37(2008) 123-150.
12. [12]
  [12] C. Ruß, B. König, Low melting mixtures in organic synthesis-an alternative to ionic liquids? Green Chem. 14(2012) 2969-2982.
13. [13]
  [13] X. Ge, C.D. Gu, X.L. Wang, J.P. Tu, Endowing manganese oxide with fast adsorption ability through controlling the manganese carbonate precursor assembled in ionic liquid, J. Colloid Interface Sci. 438(2015) 149-158.
14. [14]
  [14] D.V. Wagle, H. Zhao, G.A. Bakar, Deep eutectic solvents:sustainable media for nanoscale and functional materials, Acc. Chem. Res. 47(2014) 2299-2308.
15. [15]
  [15] M. Hayyan, F.S. Mjalli, M.A. Hashim, I.M. Alnashef, An investigation of the reaction between 1-butyl-3-methylimidazolium trifluoromethanesulfonate and superoxide ion, J. Mol. Liq. 181(2013) 44-50.
16. [16]
  [16] Y.S. Hu, Z.X. Wang, X.J. Huang, L.Q. Chen, Physical and electrochemical properties of new binary room-temperature molten salt electrolyte based on LiBETI and acetamide, Solid State Ionics 175(2004) 277-280.
17. [17]
  [17] E.R. Cooper, C.D. Andrews, P.S. Wheatly, et al., Ionic liquids and eutectic mixtures as solvent and template in synthesis of zeolite analogues, Nature 430(2004) 1012-1016.
18. [18]
  [18] M. Francisco, A. van den Bruinhorst, M.C. Kroon, Low-Temperature-Temperature Mixtures (LTTMs):a new generation of designer solvents, Angew. Chem. Int. Ed. 52(2013) 3074-3085.
19. [19]
  [19] A.P. Abbott, M. Azam, K.S. Ryder, S. Saleem, In situ electrochemical digital holographic microscopy; a study of metal electrodeposition in deep eutectic solvents, Anal. Chem. 85(2013) 6653-6660.
20. [20]
  [20] A.P. Abbott, K. El Ttaib, G. Frisch, K.J. McKenzie, K.S. Ryder, Electrodeposition of copper composites from deep eutectic solvents based on choline chloride, Phys. Chem. Chem. Phys. 11(2009) 4269-4277.
21. [21]
  [21] C.D. Gu, J.L. Zhang, W.Q. Bai, et al., Electro-brush plating from deep eutectic solvent:a case of nanocrystalline Ni coatings with superior mechanical property and corrosion resistance, J. Electrochem. Soc. 162(2015) D159-D165.
22. [22]
  [22] G.F. Cai, J.P. Tu, C.D. Gu, et al., One-step fabrication of nanostructured NiO films from deep eutectic solvent with enhanced electrochromic performance, J. Mater. Chem. A 1(2013) 4286-4292.
23. [23]
  [23] C.D. Gu, J.P. Tu, One-step fabrication of nanostructured Ni film with lotus effect from deep eutectic solvent, Langmuir 27(2011) 10132-10140.
24. [24]
  [24] Y.T. Dai, J. van Spronsen, G.J. Witkamp, R. Verpoorte, Y.H. Choi, Natural deep eutectic solvents as new potential media for green technology, Anal. Chim. Acta 766(2013) 61-68.
25. [25]
  [25] J.C. Barron, The Electrochemistry of Zn in Deep Eutectic Solvents,Ph.D thesis, University of Leicester, 2009.
26. [26]
  [26] A.P. Abbott, G. Capper, D.L. Davies, R.K. Rasheed, V. Tambyrajah, Ionic liquids and their use as solvent, US Patent, 7183433 B2,2007.
27. [27]
  [27] W.J. Guo, Y.C. Hou, S.H. Ren, S.D. Tian, W.Z. Wu, Formation of deep eutectic solvents by phenols and choline chloride and their physical properties, J. Chem. Eng. Data 58(2013) 866-872.
28. [28]
  [28] M. Avalos, R. Babiano, P. Cintas, J.L. Jiménez, J.C. Palacios, Greener media in chemical synthesis and processing, Angew. Chem. Int. Ed. 45(2006) 3904-3908.
29. [29]
  [29] Q.H. Zhang, K. De Oliveira Vigier, S. Royer, F. Jérôme, Deep eutectic solvents:syntheses, properties and applications, Chem. Soc. Rev. 41(2012) 7108-7146.
30. [30]
  [30] H.Y. Wang, Y. Jing, X.H. Wang, Y. Yao, Y.Z. Jia, Structure and physico-chemical properties of three analogous ionic liquids containing magnesium chloride, J. Mol. Liq. 170(2012) 20-24.
31. [31]
  [31] W.Y. Guo, X.M. Zhang, Metal-ion interactions with sugars. The crystal structure and FTIR study of an SrCl₂-fructose complex, Carbohydr. Res. 339(2004) 1421-1426.
32. [32]
  [32] K. Dill, S. Bromberg, Molecular Driving Forces:Statistical Thermodynamics in Biology, Chemistry, Physics, and Nanoscience, Garland Science, San Diego, 2010, pp. 616-617.
33. [33]
  [33] G. Aullón, D. Bellamy, A.G. Orpen, L. Brammer, E.A. Bruton, Metal-bound chlorine often accepts hydrogen bonds, Chem. Commun. 6(1998) 653-654.
34. [34]
  [34] H. Zhao, G.A. Baker, S. Holmes, New eutectic ionic liquids for lipase activation and enzymatic preparation of biodiesel, Org. Biomol. Chem. 9(2011) 1908-1916.
35. [35]
  [35] R. Mrozek, Z. Rzaçzyńska, M. Sikorska-Iwan, Thermal analysis of manganese (II) complexes with glycine, J. Therm. Anal. Calorim. 63(2001) 839-846.
36. [36]
  [36] A.A. Shamsuri, D.K. Abdullah, Ionic liquids:preparations and limitations, Makara Sains 14(2010) 101-106.
37. [37]
  [37] J.I. García, H. García-Martín, E. Pires, Glycerol based solvents:synthesis, properties and applications, Green Chem. 16(2014) 1007-1033.
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