Synthesis, Characterization and Optimization of Oleyl Oleate Wax Ester Using Ionic Liquid Catalysts

https://doi.org/10.22146/ijc.59694

Naowara Al-Arafi(1), Nadia Salih(2*), Jumat Salimon(3)

(1) Department of Chemistry, Faculty of Science, Benghazi University, P.O. Box 1308, Benghazi, Libya
(2) Department of Chemical Sciences, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia
(3) Department of Chemical Sciences, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor, Malaysia
(*) Corresponding Author

Abstract


In this work, the synthesis of oleyl oleate wax ester using Brønsted acidic ionic liquid catalysts was carried out. Confirmation of oleyl oleate molecular structure has been performed using FTIR, NMR, and ESI-MS spectroscopies. The ability of ionic liquid catalysts for catalyzing the esterification reaction of oleic acid and oleyl alcohol to produce oleyl oleate was optimized. The ionic liquid catalyst ([NMP][CH3SO3]) was found to be the best catalyst for the esterification reaction of oleic acid and oleyl alcohol compared with the other acidic ionic liquids studied. The optimal reaction conditions were determined at a reaction time of 8 h; oleic acid to oleyl alcohol mole ratio of 1:1; ([NMP][CH3SO3]) with 9.9 wt.%; and reaction temperature of 90 °C. Under these conditions, the percentage yield of oleyl oleate wax ester was 86%.


Keywords


wax ester; Brønsted acidic ionic liquid catalyst; esterification reaction; oleic acid; oleyl alcohol

Full Text:

Full Text PDF


References

[1] da Silva, J.A.C., 2011, “Biodegradable lubricants and their production via chemical catalysis” in Tribology - Lubricants and Lubrication, Eds. Kuo, C.H., IntechOpen, Rijeka, Croatia, 185–200.

[2] Cheng, D., 2013, Wax ester biosynthetic pathway, Dissertations, Department of Biochemistry, Biophysics and Molecular Biology, Iowa State University, US.

[3] Samidin, S., Salih, N., and Salimon, J., 2021, Synthesis and characterization of trimethylolpropane based esters as green biolubricant basestock, Biointerface Res. Appl. Chem., 11 (5), 13638–13651.

[4] Liu, T., Peng, X., Chen, Y., Zhang, J., Jiao, C., and Wang, H., 2020, Solid-phase esterification between poly(vinyl alcohol) and malonic acid and its function in toughening hydrogels, Polym. Chem., 11 (29), 4787–4797.

[5] Weng, S.S., Chen, F.K., and Ke, C.S., 2013, Direct esterification of carboxylic acids with alcohols catalyzed by iron(III) acetylacetonate complex, Synth. Commun., 43 (19), 2615–2621.

[6] Naik, S., Kavala, V., Gopinath, R., and Patel, B.K., 2006, Tetrabutylammonium tribromide mediated condensation of carboxylic acids with alcohols, Arkivoc, 2006 (1), 119–127.

[7] Bartlewicz, O., Dąbek, I., Szymańska, A., and Maciejewski, H., 2020, Heterogeneous catalysis with the participation of ionic liquids, Catalysts, 10 (11), 1227.

[8] Liang, S.T., Wang, H.Z., and Liu, J., 2018, Progress, Mechanism and application of liquid metal catalysis system: A Review, Chem. Eur. J., 24 (67), 17616–17626.

[9] Gao, P., Zhang, L., Li, S., Zhou, Z., and Sun, Y., 2020, Novel heterogeneous catalysts for CO2 hydrogenation to liquid fuels, ACS Cent. Sci., 6 (10), 1657−1670.

[10] Soleimani, O., 2020, Properties and applications of ionic liquids, J. Chem. Rev., 2 (3), 169–181.

[11] Deng, Y., Shi, F., Beng, J., and Qiao, K., 2001, Ionic liquid as a green catalytic reaction medium for esterification, J. Mol. Catal. A: Chem., 165 (1-2), 33–36.

[12] Vafaeezadeh, M., and Alinezhad, H., 2016, Brønsted acidic ionic liquids: Green catalysts for essential organic reactions, J. Mol. Liq., 218, 95–105.

[13] Zhang, T. Li, X., Song, H., and Yao, S., 2019, Ionic liquid-assisted catalysis for glycosidation of two triterpenoid sapogenins, New J. Chem., 43 (43), 16881–16888.

[14] Al-Arafi, N., and Salimon, J., 2012, Production of oleic acid based wax ester using acidic homogeneous catalysts, J. Chem., 9, 181249.

[15] Sardar, S., Wilfred, C.D., and Leveque, J.M., 2017, One-pot Mannich base synthesis using task specific protic ionic liquids, Malays. J. Anal. Sci., 21 (5), 1203–1209.

[16] Salminen, E., Virtanen, P., and Mikkola, J.P., 2014, Alkaline ionic liquids applied in supported ionic liquid catalyst for selective hydrogenation of citral to citronellal, Front. Chem., 2, 3.

[17] Polesso, B.B., Bernard, F.L., Ferrari, H.Z., Duarte, E.A., Vecchia, F.D., and Einloft, S., 2019, Supported ionic liquids as highly efficient and low-cost material for CO2/CH4 separation process, Heliyon, 5 (7), e02183.

[18] Hu, Y.L., and Fang, D., 2016, Preparation of silica supported ionic liquids for highly selective hydroxylation of aromatics with hydrogen peroxide under solvent-free conditions, J. Mex. Chem. Soc., 60 (4), 207–217.

[19] Gu, Y., Zhang, J., Duan, Z., and Deng, Y., 2005, Pechmann reaction in non-chloroaluminate acidic ionic liquids under solvent-free conditions, Adv. Synth. Catal., 347 (4), 512–516.

[20] Trubiano, G., Borio, D., and Errazu, A., 2007, Influence of the operating conditions and the external mass transfer limitations on the synthesis of fatty acid esters using a Candida antarctica lipase, Enzyme Microb. Technol., 40 (4), 716–722.

[21] Ratti, R., 2014, Ionic Liquids: Synthesis and applications in catalysis, Adv. Chem., 2014, 729842.

[22] Salih, N., and Salimon, J., 2021, A Review on eco-friendly green biolubricants from renewable and sustainable plant oil sources, Biointerface Res. Appl. Chem., 11 (5), 13303–13327.

[23] Ishak, Z.I., Sairi, N.A., Alias, Y., Aroua, M.K.T., and Yusoff, R., 2017, A review of ionic liquids as catalysts for transesterification reactions of biodiesel and glycerol carbonate production, Catal. Rev. Sci. Eng., 59 (1), 44–93.

[24] Neto, B.A.D., and Spencer, J., 2012, The impressive chemistry, applications and features of ionic liquids: Properties, catalysis & catalysts and trends, J. Braz. Chem. Soc., 23 (6), 987-1007.

[25] Salimon, J., Salih, N., and Yousif, E., 2012, Industrial development and applications of plant oils and their biobased oleochemicals, Arabian J. Chem., 5 (2), 135–145.



DOI: https://doi.org/10.22146/ijc.59694

Article Metrics

Abstract views : 2380 | views : 1900


Copyright (c) 2021 Indonesian Journal of Chemistry

Creative Commons License
This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

 


Indonesian Journal of Chemistry (ISSN 1411-9420 /e-ISSN 2460-1578) - Chemistry Department, Universitas Gadjah Mada, Indonesia.

Web
Analytics View The Statistics of Indones. J. Chem.