Synthesis of 2-Hydroxyethyl Esters from Castor Oil as Lubrication Bio-Additive Candidates for Low-Sulfur Fossil Diesel

https://doi.org/10.22146/ijc.73038

Arizal Firmansyah(1), Yulfi Zetra(2), Rafwan Year Perry Burhan(3*), Didik Prasetyoko(4), Novesar Jamarun(5)

(1) Department of Chemistry, Faculty of Science and Data Analytics, Institut Teknologi Sepuluh Nopember, Kampus ITS Keputih, Surabaya 60111, Indonesia; Department of Chemistry Education, Faculty of Science and Technology, Universitas Islam Negeri Walisongo Semarang, Kampus 3, Ngaliyan, Semarang 50185, Indonesia
(2) Department of Chemistry, Faculty of Science and Data Analytics, Institut Teknologi Sepuluh Nopember, Kampus ITS Keputih, Surabaya 60111, Indonesia
(3) Department of Chemistry, Faculty of Science and Data Analytics, Institut Teknologi Sepuluh Nopember, Kampus ITS Keputih, Surabaya 60111, Indonesia; Polytechnic of Energy and Mineral Akamigas, Jl. Gajah Mada No. 38, Cepu 58315, Indonesia
(4) Department of Chemistry, Faculty of Science and Data Analytics, Institut Teknologi Sepuluh Nopember, Kampus ITS Keputih, Surabaya 60111, Indonesia
(5) Department of Chemistry, University of Andalas, Limau Manis, Padang 25163, West Sumatera, Indonesia
(*) Corresponding Author

Abstract


The present work aims to study the synthesis of 2-hydroxyethyl esters from castor oil and its lubrication properties, promising as a lubrication bio-additive in low sulfur diesel fuel. This compound has been successfully synthesized from castor oil and ethylene glycol. The oil to ethylene glycol molar ratio was adjusted to 1:10, and the catalyst loading was used at 9% mole oil. Then, the mixture was refluxed for 5 h. The product components were characterized using GC-MS. The standard ASTM method was used to study the kinematic viscosity and lubrication. The product was dominated by 2-hydroxyethyl esters (94.16%), di-ester (1.12%), and cyclic ester (1.92%). The analysis of friction coefficient and wear scar diameter (WSD) using High-Frequency Reciprocating Rig (HFRR) shows the coefficient of friction and WSD of the product better than reference diesel fuel. From the results of this study, the 2-hydroxyethyl ester of castor oil, especially 2-hydroxyethyl ricinoleate, is the main responsible for the lubricating properties. Thus, 2-hydroxyethyl esters of castor oil can be proposed as an alternative bio-additive to improve the lubrication of low-sulfur fossil diesel fuels.

Keywords


2-hydroxyethyl ester; castor oil; lubrication; bio-additive; diesel

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References

[1] Sahin, Z., Kurt, M., and Durgun, O., 2018, Heat release analysis of gasoline fumigation in a diesel engine, Energy Procedia, 147, 322–328.

[2] Hoseinpour, M., Sadrnia, H., Tabasizadeh, M., and Ghobadian, B., 2017, Energy and exergy analyses of a diesel engine fueled with diesel, biodiesel-diesel blend and gasoline fumigation, Energy, 141, 2408–2420.

[3] Aklilu, A.Z., 2020, Gasoline and diesel demand in the EU: Implications for the 2030 emission goal, Renewable Sustainable Energy Rev., 118, 109530.

[4] Liddle, B., and Huntington, H., 2020, ‘On the Road Again’: A 118 country panel analysis of gasoline and diesel demand, Transp. Res. A: Policy Pract., 142, 151–167.

[5] Zhang, Y., Cao, Y., Tang, Y., Ying, Q., Hopke, P.K., Zeng, Y., Xu, X., Xia, Z., and Qiao, X., 2020, Wet deposition of sulfur and nitrogen at Mt. Emei in the West China Rain Zone, southwestern China: Status, inter-annual changes, and sources, Sci. Total Environ., 713, 136676.

[6] Qiao, X., Shu, X., Tang, Y., Duan, L., Seyler, B.C., Guo, H., Xiao, Y., Ying, Q., and Zhang, H., 2021, Atmospheric deposition of sulfur and nitrogen in the West China rain zone: Fluxes, concentrations, ecological risks, and source apportionment, Atmos. Res., 256, 105569.

[7] Zhang, W., Li, X., Wang, H., Song, Y., Zhang, S., and Li, C., 2017, Deep desulfurization of model oil by photocatalytic air oxidation and adsorption using Ti(1−x)MxO2 (M=Zr, Ce), Korean J. Chem. Eng., 34 (12), 3132–3141.

[8] de León, J.N.D., Kumar, C.R., Antúnez-García, J., and Fuentes-Moyado, S., 2019, Recent insights in transition metal sulfide hydrodesulfurization catalysts for the production of ultra low sulfur diesel: A short review, Catalysts, 9 (1), 87.

[9] Matzke, M., Jess, A., and Litzow, U., 2015, Polar nitrogen-containing aromatic compounds as carriers of natural diesel lubricity, Fuel, 140, 770–777.

[10] Hsieh, P.Y., and Bruno, T.J., 2015, A perspective on the origin of lubricity in petroleum distillate motor fuels, Fuel Process. Technol., 129, 52–60.

[11] Hsieh, P.Y., Widegren, J.A., Slifka, A.J., Hagen, A.J., and Rorrer, R.A.L., 2015, Direct measurement of trace polycyclic aromatic hydrocarbons in diesel fuel with 1H and 13C NMR spectroscopy: Effect of PAH content on fuel lubricity, Energy Fuels, 29 (7), 4289–4297.

[12] Sukjit, E., and Dearn, K.D., 2011, Enhancing the lubricity of an environmentally friendly Swedish diesel fuel MK1, Wear, 271 (9-10), 1772–1777.

[13] Sun, L., Li, M., Ma, C., Li, P., and Li, J., 2016, Preparation and evaluation of lubricity additives for low sulfur diesel fuel, Energy Fuels, 30 (7), 5672–5676.

[14] Sun, L., Li, M., Ma, C., and Li, P., 2017, Preparation and evaluation of Jatropha curcas based catalyst and functionalized blend components for low sulfur diesel fuel, Fuel, 206, 27–33.

[15] Prasad, L., Das, L.M., and Naik, S.N., 2012, Effect of castor oil, methyl and ethyl esters as lubricity enhancer for low lubricity diesel fuel (LLDF), Energy Fuels, 26 (8), 5307–5315.

[16] Jiang, J., Zhang, Y., Zheng, Y., and Jiang, P., 2013, Transesterification of soybean oil with ethylene glycol, catalyzed by modified Li-Al layered double hydroxides, Chem. Eng. Technol., 36 (8), 1371–1377.

[17] Rezende, M.J.C., Perruso, C.R., Azevedo, D.A., and Pinto, A.C., 2005, Characterization of lubricity improver additive in diesel by gas chromatography-mass spectrometry, J. Chromatogr. A, 1063 (1-2), 211–215.

[18] Knothe, G., and Steidley, K.R., 2005, Lubricity of components of biodiesel and petrodiesel. The origin of biodiesel lubricity, Energy Fuels, 19 (3), 1192–1200.

[19] Hu, J., Du, Z., Li, C., and Min, E., 2005, Study on the lubrication properties of biodiesel as fuel lubricity enhancers, Fuel, 84 (12-13), 1601–1606.

[20] Yang, T., Rebsdorf, M., Engelrud, U., and Xu, X., 2005, Monoacylglycerol synthesis via enzymatic glycerolysis using a simple and efficient reaction system, J. Food Lipids, 12 (4), 299–312.

[21] Hobuss, C.B., da Silva, F.A., dos Santos, M.A.Z., de Pereira, C.M.P., Schulz, G.A.S., and Bianchini, D., 2020, Synthesis and characterization of monoacylglycerols through glycerolysis of ethyl esters derived from linseed oil by green processes, RSC Adv., 10 (4), 2327–2336.

[22] Pyo, Y.G., Hong, S.I., Kim, Y., Kim, B.H., and Kim, I.H., 2012, Synthesis of monoacylglycerol containing pinolenic acid via stepwise esterification using a cold active lipase, Biotechnol. Prog., 28 (5), 1218–1224.

[23] Luo, H., Zhai, Z., Fan, W., Cui, W., Nan, G., and Li, Z., 2015, Monoacylglycerol synthesis by glycerolysis of soybean oil using alkaline ionic liquid, Ind. Eng. Chem. Res., 54 (18), 4923–4928.

[24] Nosal, H., Moser, K., Warzała, M., Holzer, A., Stańczyk, D., and Sabura, E., 2020, Selected fatty acids esters as potential PHB-V bioplasticizers: Effect on mechanical properties of the polymer, J. Polym. Environ., 29 (1), 38–53.

[25] Rios, Í.C., Cordeiro, J.P., Arruda, T.B.M.G., Rodrigues, F.E.A., Uchoa, A.F.J., Luna, F.M.T., Cavalcante, C.L., and Ricardo, N.M.P.S., 2020, Chemical modification of castor oil fatty acids (Ricinus communis) for biolubricant applications: An alternative for Brazil’s green market, Ind. Crops Prod., 145, 112000.

[26] Changmai, B., Vanlalveni, C., Ingle, A.P., Bhagat, R., and Rokhum, L., 2020, Widely used catalysts in biodiesel production: A review, RSC Adv., 10 (68), 41625–41679.

[27] Wang, W., Shen, B., Li, Y., Ni, Q., Zhou, L., and Du, F., 2021, Friction reduction mechanism of glycerol monooleate-containing lubricants at elevated temperature - transition from physisorption to chemisorption, Sci. Prog., 104 (1), 1–15.

[28] Shen, W., Hirayama, T., Yamashita, N., Adachi, M., Oshio, T., Tsuneoka, H., Tagawa, K., Yagishita, K., and Yamada, N.L., 2022, Relationship between interfacial adsorption of additive molecules and reduction of friction coefficient in the organic friction modifiers-ZDDP combinations, Tribol. Int., 167, 107365.

[29] Yusoff, M.F.M., Xu, X., and Guo, Z., 2014, Comparison of fatty acid methyl and ethyl esters as biodiesel base stock: A review on processing and production requirements, J. Am. Oil Chem. Soc., 91 (4), 525–531.

[30] Rashid, U., Anwar, F., Moser, B.R., and Ashraf, S., 2008, Production of sunflower oil methyl esters by optimized alkali-catalyzed methanolysis, Biomass Bioenergy, 32 (12), 1202–1205.

[31] Sánchez, A., Maceiras, R., Cancela, A., and Rodríguez, M., 2012, Influence of n-hexane on in Situ transesterification of marine macroalgae, Energies, 5 (2), 243–257.

[32] Geller, D.P., and Goodrum, J.W., 2004, Effects of specific fatty acid methyl esters on diesel fuel lubricity, Fuel, 83 (17-18), 2351–2356.

[33] Sáez-Bastante, J., Pinzi, S., Jiménez-Romero, F.J., Luque de Castro, M.D., Priego-Capote, F., and Dorado, M.P., 2015, Synthesis of biodiesel from castor oil: Silent versus sonicated methylation and energy studies, Energy Convers. Manage., 96, 561–567.

[34] Dias, J.M., Araújo, J.M., Costa, J.F., Alvim-Ferraz, M.C.M., and Almeida, M.F., 2013, Biodiesel production from raw castor oil, Energy, 53, 58–66.

[35] Thakkar, K., Kachhwaha, S.S., and Kodgire, P., 2022, Multi-response optimization of transesterification reaction for biodiesel production from castor oil assisted by hydrodynamic cavitation, Fuel, 308, 121907.

[36] Guo, S., Li, C., Zhang, Y., Yang, M., Jia, D., Zhang, X., Liu, G., Li, R., Bing, Z., and Ji, H., 2018, Analysis of volume ratio of castor/soybean oil mixture on minimum quantity lubrication grinding performance and microstructure evaluation by fractal dimension, Ind. Crops Prod., 111, 494–505.

[37] Bekele, B.A., Ourgessa, A.W., Terefe, A.A., and Hailu, S.S., 2018, Studies on Ethiopian castor seed (Ricinus communis L.): Extraction and characterization of seed oil, J. Nat. Prod. Resour., 4 (2), 188–190.

[38] Pečar, D., and Goršek, A., 2015, Kinetic modeling of ethylene glycol monoesterification, Int. J. Chem. Kinet., 47 (10), 658–663.

[39] Hiware, S.B., and Gaikar, V.G., 2020, Solvent-free esterification of stearic acid and ethylene glycol with heterogeneous catalysis in a stirred batch microwave reactor, SN Appl. Sci., 2 (4), 712.

[40] Clayden, J., Greeves, N., Warren, S., and Wothers, P., 2001, Organic Chemistry, Oxford University Press, Oxford, UK.

[41] Long, Y., Galipaud, J., Weihnacht, V., Makowski, S., Martin, J.M., and De Barros Bouchet, M.I., 2022, Achieving superlubricity using selected tribo-pairs lubricated by castor oil and unsaturated fatty acids, Tribol. Int., 169, 107462.

[42] Heikal, E.K., Elmelawy, M.S., Khalil, S.A., and Elbasuny, N.M., 2017, Manufacturing of environment friendly biolubricants from vegetable oils, Egypt. J. Pet., 26 (1), 53–59.

[43] McNutt, J., and He, Q.S., 2016, Development of biolubricants from vegetable oils via chemical modification, J. Ind. Eng. Chem., 36, 1–12.

[44] Encinar, J.M., Nogales-Delgado, S., Sánchez, N., and González, J.F., 2020, Biolubricants from rapeseed and castor oil transesterification by using titanium isopropoxide as a catalyst: Production and characterization, Catalysts, 10 (4), 366.

[45] Sukjit, E., Poapongsakorn, P., Dearn, K.D., Lapuerta, M., and Sánchez-Valdepeñas, J., 2017, Investigation of the lubrication properties and tribological mechanisms of oxygenated compounds, Wear, 376-377, 836–842.

[46] Canoira, L., García Galeán, J., Alcántara, R., Lapuerta, M., and García-Contreras, R., 2010, Fatty acid methyl esters (FAMEs) from castor oil: Production process assessment and synergistic effects in its properties, Renewable Energy, 35 (1), 208–217.

[47] Bouaid, A., Vázquez, R., Martinez, M., and Aracil, J., 2016, Effect of free fatty acids contents on biodiesel quality. Pilot plant studies, Fuel, 174, 54–62.

[48] Anantapinitwatna, A., Ngaosuwan, K., Kiatkittipong, W., Wongsawaeng, D., Anantpinijwatna, A., Quitain, A.T., and Assabumrungrat, S., 2021, Water influence on the kinetics of transesterification using CaO catalyst to produce biodiesel, Fuel, 296, 120653.

[49] Sundus, F., Masjuki, H.H., and Fazal, M.A., 2017, Analysis of tribological properties of palm biodiesel and oxidized biodiesel blends, Tribol. Trans., 60 (3), 530–536.

[50] Loehlé, S., Matta, C., Minfray, C., Mogne, T.L., Iovine, R., Obara, Y., Miyamoto, A., and Martin, J.M., 2015, Mixed lubrication of steel by C18 fatty acids revisited. Part I: Toward the formation of carboxylate, Tribol. Int., 82, 218–227.

[51] Loehlé, S., Matta, C., Minfray, C., Mogne, T.L., Iovine, R., Obara, Y., Miyamoto, A., and Martin, J.M., 2016, Mixed lubrication of steel by C18 fatty acids revisited. Part II: Influence of some key parameters, Tribol. Int., 94, 207–216.



DOI: https://doi.org/10.22146/ijc.73038

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