Evaluation of physical and chemical properties of imidazolium based ionic liquid:1-butyl 3-methylimidazoium methyl sulfate.
Subject Areas :seyed mohammadreza shoja 1 , majid abdouss 2 , ali akbar miran beigi 3
1 - PhD student in Applied Chemistry, Department of Chemistry, Amirkabir University of Technology, Tehran, Iran
2 - Prof. of Organic Chemistry, Department of Chemistry, Amirkabir University Of Technology, Tehran, Iran
3 - Associate Prof. of Analytical Chemistry, Oil Refining Department, Research Institute of Petroleum Industry, Tehran, Iran
Keywords: Ionic liquid, Physical and Chemical Properties, Synthesis and identification, Electrochemical window,
Abstract :
In this work, the imidazolium based ionic liquid, i.e. 1-butyl 3-methylimidazolium methyl sulfate [BMIM][MeSO4], was synthesized and identified using NMR, FT-IR, and elemental analysis (CHNOS). Physical and chemical properties of this ionic liquid including density, viscosity, surface tension, refractive index, pH, and speed of sound were initially investigated in the temperature range of 10°C-90°C as well as its electrochemical window at ambient temperature. The results showed that, this ionic liquid had a wide electrochemical window (6V) and all the mentioned physical and chemical parameters except pH were completely temperature-dependent and decreased by increasing temperature. The pH of the ionic liquid was almost constant in the desired temperature range. The results of this research can be utilized as a database on the mentioned temperature range for this ionic liquid.
[1] Campose Toimil, M.; Orallo, F.; Santana, L.; Uriarte, E.; Broorg. Med. Chem Left. 12, 783-789, 2012.
[2] Balan, D.; Adolffen, H.; Tetrahedron 44, 2521–2524, 2003.
[3] De Clereq, E.A.; Curr. Opin. Antivitral Res. 67, 57-75, 2005.
[4] Debenedetti, S.L.; Nadinic, E.L.; Coussio, J.D.; De Kimpe, N.; Phylochemistry 48, 807-811, 1998
[5] Biot, C.; Glorian, G.; Maciejewski, L.A.; Brocard, J.S.J Med Chem. 40, 3715-3718, 1997.
[6] Hafez, E.A.A.; Elnagdi, M.H.; Elagamey, A.G.A.; ELTaweel, F.M.A.A.; Heterocycles 26, 903-907, 1987.
[7] Beagley, P.; Blackie, M.A.; Chibale, K.; Clarkson, C.; Meijboom, R.; Moss, J.R.; Dalton Transactions. 15, 3046-3051, 2003.
[8] Morgan, L.R.; Jursic, B.S.; Hooper, C.L.; Neumann, D.M.; Thangaraj, K.; LeBlanc, B.; Bioorg Med Chem Lett. 12, 3407-3411, 2002.
[9] Heravi, M.M.; Sadjadi, S.; Haj, N.M.; Oskooie, H.A.; Bamoharram, F.F.; Catalysis Communications 10, 1643-1646, 2009.
[10] Abdolmohammadi, S.; Balalaie, S.; Tetrahedron Letters 48, 3299-3303, 2007.
[11] Paul, S.; Bhattacharyya, P.; Das, A.R. Tetrahedron Letters 52, 4636-4641, 2011.
[12] Mehrabi, H.; Abusaidi, H.; Journal of the Iranian Chemical Society 7, 890-894, 2010.
[13] Heravi, M. M.; Zakeri, M.; Mohammadi, N.; Chinese Journal of Chemistry 29, 1163-1166, 2011.
[14] Khurana, J.M.; Nand, B.; Saluja, P.; Tetrahedron 66, 5637-5641, 2010.
[15] Shaker, R.M.; Dei Pharmazie 51, 148-151, 1996.
[16] Jiang, W.; Xiang, Z.; Xu, B.; Li, X.; Liu, F.; Fan, G.; New Journal of Chemistry 40, 372-376, 2016.
[17] Seifi, M.; Sheibani, H.; Catalysis Letters 126, 275-279, 2008.
[18] Mohammadi Ziarani, G.; Badiei, A.; Azizi, M.; Zarabadi, P.;Iranian Journal of Chemistry and Chemical Engineering (IJCCE) 30, 59-65, 2011.
[19] Montazeri, N.; Noghani, T.; Ghorchibeigy, M.; Zoghi, R.; Journal of Chemistry 14, 5-14, 2014.
[20] Patel, D.S.; Avalani, J.R.; Raval DK.; Journal of Saudi Chemical Society 20, 401-405, 2016.
[21] Karimi, A.R.; Sedaghatpour, F.; Synthesis 20, 1731-1735, 2010.
[22] Khurana, J.M.; Kumar, S.; Tetrahedron Letters 50, 4125-4127, 2009.
[23] Montaghami, A.; Montazeri, N.; Oriental Journal of Chemistry 30, 1361-1364, 2014.
[24] Tanuraghaj, H.M.; Farahi, M.; Tetrahedron Letter, 60, 557-559, 2019.
[25] Farahi, M.; Karami, B.; Tanuraghaj, H.M.; Bazrafshan, Z.; Journal of Heterocyclic Chemistry 55, 125-131, 2018.
[26] Tabatabaeian, K.; Heidari, H.; Mamaghani, M.; Mahmoodi, N.O.; Applied Organometallic Chemistry 26, 56-61, 2012.
[27] Saha, M.; Pal, A.K.; Tetrahedron letters 20, 125-128, 2012.
[28] Fotouhi, L.; Heravi, M.M.; Fatehi, A.; Bakhtiari, K.; Tetrahedron Letters 48, 5379-5381, 2007.
[29] Mosaddegh, E.; Poshtiban, F.; Hassankhani, A.; Alizadeh, M.; Ghazanfari, D., Journal of the Iranian Chemical Society 11, 639-643. 2014.
[30] Karami, B.; Khodabakhshi, S.; Eskandari, K.; Tetrahedron Letters 53, 1445-1446, 2012.
[31] Shaterian, H.R. and Aghakhanizadeh, M.; Chinese Journal of Catalysis 34, 1690-1696, 2013.
[32] Poorabbas, B.; Mardaneh, J.; Rezaei, Z.; Kalani, M.; Pouladfar, G.; Alami, M.H.; Soltani, J.; Shamsi-Zadeh, A.; Abdoli-Oskooi, S.; Saffar, M, J.; Alborzi, A. Iranian journal of microbiology 7, 127-135, 2015.
[33] Mahdiyoun, S.M.; Ahanjan, M.; Goudarzi, M.; Rezaee, R.; J Mazandaran Univ Med Sci. 25, 97-107, 2015.
[34] Aghamahdi, F.; Hashemian, H.; Shafiei, M.; Akbarian, Z.; Rostam Nejad, M.; Fallah Karkan, M.; Iranian Journal of Neonatology IJN 4, 21-5, 2013.
[35] Madani, S.H.; Khazaee, S.; Kanani, M.; Shahi, M.; J Kermanshah Univ Med Sci. 12, 25-32, 2008.