Synthesis of Dioxo-Dioxane and Dioxo-Dioxepane Ethyl Oleate Derivatives as Bio-Lubricant Base Stocks

Tutik Dwi Wahyuningsih; Yehezkiel Steven Kurniawan

doi:10.22146/ijc.42317

Synthesis of Dioxo-Dioxane and Dioxo-Dioxepane Ethyl Oleate Derivatives as Bio-Lubricant Base Stocks

https://doi.org/10.22146/ijc.42317

Tutik Dwi Wahyuningsih^(1*), Yehezkiel Steven Kurniawan⁽²⁾

(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada, Sekip Utara, Yogyakarta 55281, Indonesia
(2) Ma Chung Research Center for Photosynthetic Pigments, Universitas Ma Chung, Malang 65151, Indonesia
(*) Corresponding Author

Abstract

In this study, two novel compounds, i.e., ethyl 8-(3-octyl-5,6-dioxo-1,4-dioxan-2-yl)octanoate and ethyl 8-(3-octyl-5,7-dioxo-1,4-dioxepan-2-yl)octanoate were prepared from oleic acid as the starting material. Both compounds were obtained from the esterification of the ethyl 9,10-dihydroxyoctadecanoate with dicarboxylic acids in the presence of p-toluenesulfonic acid as a catalyst. The chemical structures of the synthesized products were confirmed by FTIR, ¹H-NMR, and MS spectrometers. The bio-lubricant properties of the products, such as density, total acid number, total base number, and iodine value, were determined and the effect of the dioxane and dioxepane heterocyclic rings to their bio-lubricant properties was discussed. The esterification of ethyl 9,10-dihydroxyoctadecanoate with oxalic acid gave ethyl 8-(3-octyl-5,6-dioxo-1,4-dioxan-2-yl)octanoate compound in 93.9% yield, while the esterification of ethyl 9,10-dihydroxyoctadecanoate with malonic acid gave ethyl 8-(3-octyl-5,7-dioxo-1,4-dioxepan-2-yl)octanoate compound in 89.6% yield. The density and total base number of the products were close to the standard commercial lubricant values. Meanwhile, the total acid number and the iodine value of the ethyl 8-(3-octyl-5,6-dioxo-1,4-dioxan-2-yl)octanoate were smaller than the standard commercial lubricant, showing that this compound is a promising bio-lubricant in a real application.

Keywords

synthesis; dioxane; dioxepane; bio-lubricant; oleic acid

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References

[1] Zhu, Y., Romain, C., and Williams, C.K., 2016, Sustainable polymers from renewable resources, Nature, 540, 354–362.

[2] Imawan, A.C., Kurniawan, Y.S., Lukman, M.F., Jumina, Triyono, and Siswanta, D., 2018, Synthesis and kinetic study of the urea controlled release composite material: Sodium lignosulfonate from isolation of wood sawdust-sodium alginate-tapioca, Indones. J. Chem., 18 (1), 108–115.

[3] Wahyuningsih, T.D., Kurniawan, Y.S., Amalia, S., Wardhani, T.A.K., and Muriningsih, C.E.S., 2019, Diethanolamide derivatives as potential enhanced oil recovery from Indonesian castor oil and used frying oil: Isolation, synthesis and evaluation as nonionic biosurfactants, Rasayan J. Chem., 12 (2), 741–748.

[4] Zhou, Y., and Qu, J., 2017, Ionic liquids as lubricant additives: A review, ACS Appl. Mater. Interfaces, 9 (4), 3209–3222.

[5] Owuna, F.J., Dabai, M.U., Sokoto, M.A., Dangoggo, S.M., Bagudo, B.U., Birnin-Yauri, U.A., Hassan, L.G., Sada, I., Abubakar, A.L., and Jibrin, M.S., 2019, Chemical modification of vegetable oils for the production of biolubricants using trimethylolpropane: A review, Egypt. J. Pet., In Press, Corrected Proof.

[6] Chan, C.H., Tang, S.W., Mohd, N.K., Lim, W.H., Yeong, S.K., and Idris, Z., 2018, Tribological behavior of biolubricant base stocks and additives, Renewable Sustainable Energy Rev., 93, 145–157.

[7] 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.

[8] Sammaiah, A., Padmaja, K.V., and Prasad, R.B.N., 2014, Synthesis and evaluation of novel acyl derivates from Jatropha oil as potential lubricant base stocks, J. Agric. Food Chem., 62 (20), 4652–4660.

[9] Madankar, C.S., Dalai, A.K., and Naik, S.N., 2013, Green synthesis of biolubricant base stock from Canola oil, Ind. Crops Prod., 44, 139–144.

[10] Sonnenschein, M.F., Greaves, M.R., Bell, B.M., and Wendt, B.L., 2012, Design, polymerization, and properties of high-performance seed-oil-derived lubricants, Ind. Eng. Chem. Res., 51 (25), 8386–8393.

[11] Soni, S., and Agarwal, M., 2014, Lubricants from renewable energy sources – A review, Green Chem. Lett. Rev., 7 (4), 359–382.

[12] Panchal, T.M., Patel, A., Chauhan, D.D., Thomas, M., and Patel, J.V., 2017, A methodological review on bio-lubricants from vegetable oil based resources, Renewable Sustainable Energy Rev., 70, 65–70.

[13] Reeves, C.J., Siddaiah, A., and Menezes, P.L., 2017, A review on the science and technology of natural and synthetic biolubricants, J. Bio. Tribo. Corros., 3, 11.

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

[15] Hossain, M.A., Iqbal, M.A.M., Julkapli, N.M., Kong, P.S., Ching, J.J., and Lee, H.V., 2018, Development of catalyst complexes for upgrading biomass into ester-based biolubricants for automotive applications: A review, RSC Adv., 8, 5559–5577.

[16] Abdullah, B.M., Zubairi, S.I., Huri, H.Z., Hairunisa, N., Yousif, E., and Basu, R.C., 2016, Polyester based on linoleic acid for biolubricant basestocks: Low-temperature, tribological and rheological properties, PLoS ONE, 11 (3), e0151603.

[17] Salih, N., Salimon, J., and Yousif, E., 2011, The physicochemical and tribological properties of Oleic acid based triester biolubricants, Ind. Crops Prod., 34 (1), 1089–1096.

[18] Kurniawan, Y.S., Ramanda, Y., Thomas, K., Hendra, and Wahyuningsih, T.D., 2017, Synthesis of 1,4-dioxaspiro[4.4] and 1,4-dioxaspiro[4.5] novel compounds from oleic acid as potential biolubricant, Indones. J. Chem., 17 (2), 301–308.

[19] Kurniawan, Y.S., Anwar, M., and Wahyuningsih, T.D., 2017, New lubricant from used cooking oil: Cyclic ketal of ethyl 9,10-dihidroxyoctadecanoate, Mater. Sci. Forum, 901, 135–141.

[20] Wahyuningsih, T.D., and Kurniawan, Y.S., 2017, Green synthesis of some novel dioxolane compounds from Indonesian essential oils as potential biogreases, AIP Conf. Proc., 1823 (1), 020081.

DOI: https://doi.org/10.22146/ijc.42317