Synthesis of A Novel Carrier Compound Thiazoethyl Methyl Eugenoxyacetate from Eugenol and Its Use in the Bulk Liquid Membrane Technique

Muhammad Cholid Djunaidi(1*), Pratama Jujur Wibawa(2), Ratna Hari Murti(3)

(1) Department of Chemistry, Faculty of Science and Mathematics, Universitas Diponegoro
(2) Department of Chemistry, Faculty of Science and Mathematics, Universitas Diponegoro
(3) Department of Chemistry, Faculty of Science and Mathematics, Universitas Diponegoro
(*) Corresponding Author


Research into the synthesis and use of a novel carrier compound, thiazoethyl methyl eugenoxyacetic acid (TMEAA) for selective transport of Cu(II), Cd(II) and Cr(III) metal ions in the bulk liquid membrane (BLM) technique was conducted. TMEAA was synthesized from eugenol. Eugenol was acidified into eugenoxyacetic acid and subsequently esterified using 4-methyl-5-thiazoethanol. Analysis of the result was performed using GC-MS and FTIR. The TMEAA obtained was liquid, viscous, blackish-brown and fragrant, with a yield of 88%. This compound was soluble in benzene and chloroform but insoluble in methanol. The GC-MS analysis result showed the presence of a single peak, with a retention time of 26.5 min and an area of 100%, while the disappearance of vibration mode at 1727 cm-1 was attributed to acid absorption and the FTIR spectrum indicated that formation of an ester group had occurred. TMEAA was used as a carrier compound in the BLM technique to transport Cu(II), Cd(II) and Cr(III), using chloroform as a solvent. The results showed that TMEAA was more selective for Cu(II) and Cd(II) than Cr(III). Moreover, the research proved that N and S groups of TMEAA were selective for Cu (II) and Cd (II).


Bulk Liquid Membrane (BLM); selective transport; thiazoethyl methyl eugenoxyacetic acid; eugenol

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[1] Misra, B.M., and Gill, J.S., 1996, Supported liquid membranes in metal separation, ACS Symp. Ser., 642, 361–368.

[2] Ramkumar, J., and Chandramouleeswaran, S., 2015, A Perceptive on Bulk Liquid Membrane: A Brief Review, Indian J. Adv. Chem. Sci., 3 (4), 293–298.

[3] Peterson, R.T., and Lamb, J.D., 1996, Design of macrocyclic carriers for liquid membrane, ACS Symp. Ser., 642, 130–141.

[4] Nezhadali, A., and Moeinpour, F., 2013, Comparative metal ion extraction of Ag(I), Cu(II), Ni(II), Zn(II), Mn(II), Cd(II) and Co(II) cations using dibenzo 18C6 as a carrier, Alexandria Eng. J., 52 (1), 123–127.

[5] Kazemi, S.V., and Shamsipur, M., 2005, Selective transport of lead(II) through a bulk liquid membrane using a cooperative carrier composed of benzylaza-12-crown-4 and oleic acid, Bull. Korean Chem. Soc., 26 (6), 930–934.

[6] Kazemi, S.V., and Hamidi, A.S., 2011, Competitive removal of lead(II), copper(II), and cadmium(II) ions through a bulk liquid membrane containing macrocyclic crown ethers and oleic acid as ion carriers, J. Chem. Eng. Data, 56 (2), 222–229.

[7] Eljaddi, T., Hor, M., Benjjar, A., Riri, M., Mouadli, H., Mountassir, Y., and Hlaibi, M., 2015, New supported liquid membrane for studying facilitated transport of U(VI) ions using Tributyl Phosphate (TBP) and Tri-n-Octylamine (TOA) as carriers from acid medium, BAOJ Chem., 1 (1), 1–9.

[8] Bartsch, R.A., and Way, J.D., 1996, Chemical separations with liquid membranes: An overview, ACS Symp. Ser., 642, 1–10.

[9] Djunaidi, M.C., Jumina, Siswanta, D., and Ulbricht, M., 2015, Synthesis of Fe ionic-imprinted polyeugenol using polyethylene glycol diglycidilether as cross-linking agent for sorption of Fe(III), Indones. J. Chem., 15 (3), 305–314.

[10] Djunaidi, M.C., Jumina, and Siswanta, D., 2016, Synthesis of ionic imprinted polymer particles for selective membrane transport of Fe(III) using polyeugenol as the functional polymer, Orient. J. Chem., 32 (1), 77–84.

[11] Djunaidi, M.C., Jumina, Siswanta, D., and Ulbricht, M., 2015, Selective transport of Fe(III) using polyeugenol as functional polymer with ionic imprinted polymer membrane method, Asian J. Chem., 27 (12), 4553–4562.

[12] Djunaidi, M.C., Jumina, Siswanta, D., and Ulbricht, M., 2016, Selective transport of Fe(III) using Ionic Imprinted Polymer (IIP) membrane particle, AIP Conf. Proc., 1699 (1), 060001.

[13] Cahyono, H., and Djunaidi, M.C., 2008, Synthesis of pyridine methyl eugenoxy acetate and selectivity study of Cu(II) in Bulk Liquid Membrane (BLM) transport, Proc. Nat. Conf. Chem. Educ., Sebelas Maret University, Surakarta, Indonesia.

[14] Djunaidi, M.C., Lusiana, R.A., Wibawa, P.J., Siswanta, D., and Jumina, 2007, Sintesis polyeugenol sebagai ekstraktan selektif logam krom(III), Alchemy, 6, 40–49.

[15] Lindoy, L.F., and Baldwin, D.S., 1989, Ligand design for selective metal-ion transport through liquid membranes, Pure Appl. Chem., 61 (5), 909–914.

[16] Cleij, M.C., Scrimin, P., Tecilla, P., and Tonellato, U., 1997, Efficient and highly selective copper(II) transport across a bulk liquid chloroform membrane mediated by lipophilic dipeptides, J. Org. Chem., 62 (16), 5592–5599.

[17] Brinchi, L., Germani, R., Mancini, M.V., Savelli, G., and Spreti, N., 2004, Carrier-mediated transport of toxic heavy metal ions in bulk liquid membranes, Eur. J. Org. Chem., 6, 1330–1335.

[18] Djunaidi, M.C., Lusiana, R.A., Wibawa, P.J., Siswanta, D., and Jumina, 2010, Sintesis turunan polieugenol sebagai carrier bagi recovery logam berat dengan teknik membran cair, Reaktor, 13 (1), 16–23.

[19] Djunaidi, M.C., Khabibi, and Trisna, D., 2010, Sintesis asam eugenoksi asetat (EOA) dari eugenol untuk ekstraktan logam berat dan recovery krom dari limbah elektroplating, Jurnal Kimia Sains dan Aplikasi, 13 (1), 12–17.

[20] Hancock, R.D., and Martell, A.E., 1989, Ligand design for selective complexation of metal ions in aqueous solution, Chem. Rev., 89 (8), 1875–1914.

[21] Djunaidi, M.C., Khabibi, and Ulumudin, I., 2017, Separation of Cu2+, Cd2+, and Cr3+ in a mixture solution using a novel carrier poly(methyl thiazoleethyl eugenoxy acetate) with BLM (Bulk Liquid Membrane) technique, IOP Conf. Ser. Mater. Sci. Eng., 172, 1757–1899.

[22] Ulewicz, M., Lesinska, U., Bochenska, M., and Walkowiak, W., 2007, Facilitated transport of Zn(II), Cd(II) and Pb(II) ions through polymer inclusion membranes with calix[4]-crown-6 derivatives, Sep. Purif. Technol., 54 (3), 299–305.


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