A NEW CLASS OF IONIC SOLVENTS, ELECTROLYTES AND ENGINEERING FLUIDS BASED ON 1,3-ALKYLMETHYL-1,2,3-BENZOTRIAZOLIUM SALTS

https://doi.org/10.22146/ijc.21744

Ahmad Mudzakir(1*)

(1) Department of Chemistry Education, Indonesia University of Education (UPI), Jl. Dr. Setiabudhi 229 Bandung 40154
(*) Corresponding Author

Abstract


A new series of ionic liquids based on 1,3-alkylmethyl-1,2,3-benzotriazolium cation has been prepared. The spectroscopic, physical and electrochemical characteristics of this family of salts have been investigated with respect to potential usage as ionic solvents, electrolytes and engineering fluids. Incorporation of diverse anions including weak coordinating anion and pseudohalide with this benzotriazolium cation produces ionic liquids with advantageously low melting points and good thermal stability. Thermal analyses of these very stable salts included the determination of melting points (-65 to 164 oC) and decomposition temperatures (up to 291 oC). The electrochemical windows of representative benzotriazolium species has been investigated by cyclic voltammetry and determined to be ~ 3 V. The X-ray single crystal and spectroscopic studies revealed that weak hydrogen-bonding interactions between the benzotriazolium ring protons and the anions are present both in the solid state as well as in solution.


Keywords


ionic liquids; X-ray single crystal; thermal analysis; electrochemical analysis; benzotriazolium salt

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References

[1] Olivier, H. and Magna, L., 2002, J. Mol. Catal. A, 182–183, 419.

[2] Zhao, D., Wu, M., Kou, Y. and Min, E., 2002, Catal. Today, 74, 157.

[3] Sheldon, R., 2001, Chem. Commun., 2399.

[4] Gordon, C.M., 2001, Appl. Catal. A, 222, 101.

[5] Wasserscheid, P. and Keim, W., 2000, Angew. Chem., 112, 3926.

[6] Dupont, J., de Souza, R.F. and Suarez, P.A.Z., 2002, Chem. Rev., 102, 3667.

[7] Fuller, J., Carlin, R.T. and Osteryoung, R. A., 1997, J. Electrochem. Soc., 144, 3881.

[8] Karodia, N., Guise, S., Newlands, C. and Andersen, J., 1998, Chem. Commun., 2341.

[9] Adams, C.J., Earle, M.J. and Seddon, K.R., 1999, Chem. Commun., 1043.

[10] Freemantle, M., 2001, Chem. Eng. News, 79, 21.

[11] Wasserscheid, P., and Keim, W., 2000, Angew. Chem., 112, 3926.

[12] Welton, T., 1999, Chem. Rev., 99, 2071.

[13] Anthony, J.A., Maginn, E.J., and Brennecke, J.F., 2001, J. Phys. Chem. B., 105, 10942.

[14] Huddleston, J.G., Visser, A.E., Reichert, W.M., Willauer, H.D., Broker, G.A., and Rogers, R.D., 2001, Green Chem., 3, 156.

[15] Seddon, K.R., 1997, J. Chem. Tech. Biotechnol., 68, 351.

[16] Welton, T., 1999, Chem. Rev. 99, 2071.

[17] Hagiwara, R. and Ito, Y., 2000, J. Fluorine Chem. 105, 221.

[18] Bonhôte, P., Dias, A.P., Papageorgiou, N., Kalyanasundaram, K. and Grätzel, M. Inorg. Chem. 1996, 35, 1168.

[19] Perrin, D.D., Armarego, W.L.F. and Perrin, D.R., Purification of laboratory Chemicals, 3 rd Ed., Pergamon Press, New York, 1985.

[20] Krollpfeiffer, F., Rosenberg, A., and Mühlhausen, C., 1935, Justus Liebigs Ann. Chem., 515, 113.

[21] Abbott, P.J., Acheson, R.M., Foxton, M.W., Raulins, N.R., and Robinson, G.E., 1972, Perkin Trans., 1, 2182.

[22] Yamauchi, K., and Kinoshita, M., 1973, Perkin Trans., 1, 2506.

[23] Mathias, L.J., and Burkett, D., 1979, Tetrahedron Lett., 4709.

[24] Bergman, J., and Sand, P., 1984, Tetrahedron Lett., 25, 1957.

[25] Masahiro, H., Kiyoshi, Y. and Masayoschi, K., 1976, Bull. Chem. Soc. Japan, , 49(1), 283.

[26] Larsen, A.S., Holbrey, J.D., Tham, F.S., and Reed, C.A. 2000, J. Am. Chem. Soc., 122, 7264.

[27] Koel, M. 2000, Proc. Estonian Acad. Sci. Chem., 49, 145.

[28] Suarez, P.A.Z., Einloft, S., Dullius, J.E.L., de Souza, R F., and Dupont, J. 1998, J. Chim. Phys., 95, 1626.

[29] Avent, A.G., Chaloner, P.A., Day, M.P., Seddon, K.R. and Welton, T., Proceeding of the 8th International Symposium on Molten Salts, The Electrochemical Society, Pennington, NJ, 1992 : Proceeding Volume 92-16, p. 98-133.

[30] Hesse, M., Meier, H., and Zeeh, B., Spektros-kopische Methoden in der Organischen Chemie, 2nd ed., Thieme Verlag, Stuttgart, 1984.

[31] MacFarlane, D.R., Meakin, P., Sun, J., Amini, N and Forsyth, M., 1999, J. Phys. Chem. B, 103, 4164.



DOI: https://doi.org/10.22146/ijc.21744

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