Synthesis of 1,4-Dioxaspiro[4.4] and 1,4-Dioxaspiro[4.5] Novel Compounds from Oleic Acid as Potential Biolubricant

Yehezkiel Steven Kurniawan(1), Yudha Ramanda(2), Kevin Thomas(3), Hendra Hendra(4), Tutik Dwi Wahyuningsih(5*)

(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada
(2) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada
(3) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada
(4) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada
(5) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada
(*) Corresponding Author


Two 1,4-dioxaspiro novel compounds which derivated from methyl 9,10-dihydroxyoctadecanoate (MDHO) with cyclopentanone and cyclohexanone had been synthesized by a sonochemical method in the presence of montmorillonite KSF catalyst. The MDHO compound had been prepared from 9,10-dihydroxyoctadecanoic acid (DHOA) and methanol. Meanwhile, DHOA was synthesized by hydroxylation of oleic acid with the solution of 1% KMnO4 under basic condition. The structures of the products were confirmed by FTIR, GC-MS, 1H-NMR, and 13C-NMR spectrometers. Hydroxylation reaction of oleic acid gave DHOA as a white solid powder in 46.52% yield (m.p. 131-132 °C). On the other side, esterification reaction via sonochemical method between DHOA and methanol gave MDHO as a white powder in 93.80% yield (m.p. 80-81 °C). The use of cyclopentanone in 45 min sonochemical method gave methyl 8-(3-octyl-1,4-dioxaspiro[4.4]nonan-2-yl)octanoate as a yellow viscous liquid in 50.51% yield. The other compound, methyl 8-(3-octyl-1,4-dioxaspiro[4.5]decan-2-yl)octanoate as yellow viscous liquid had been synthesized by similar method with cyclohexanone via the sonochemical method in 45.12% yield. From physicochemical properties, i.e. density, total acid number, total base number, and iodine value, gave the conclusion that these novel compounds are potential biolubricant candidates to be developed.


1,4-dioxaspiro; biolubricant; oleic acid; sonochemical method

Full Text:

Full Text PDF


[1] Zhu, Y., Romain, C., and Williams, C.K., 2016, Sustainable polymers from renewable resources, Nature, 540 (7633), 354–362.

[2] Salimon, J., Salih, N., and Yousif, E., 2010, Biolubricants: raw materials, chemical modifications and environmental benefits, Eur. J. Lipid Sci. Technol., 112 (5), 519–530.

[3] Carlsson, A.S., 2009, Plant oils as feedstock alternatives to petroleum – A short survey of potential oil crop platforms, Biochimie, 91 (6), 665–670.

[4] Gunstone, F.D., Harwood, J.L., and Dijkstra, A.J., 2007, The Lipid Handbook, 3rd Ed., Taylor & Francis Ltd, London, 38-69.

[5] Erhan, S.Z., Sharma, B.K, and Peres, J.M., 2006, Oxidation and low-temperature stability of vegetable oil-based lubricants, Ind. Crops Prod., 24 (3), 292–299.

[6] Talkit, K.M., Mahajan, D.T., and Massand, V.H., 2012, Physicochemical properties of soybean oil and their blends with vegetable oils for the evaluation of lubricant properties, J. Chem. Biol. Phys. Sci., 3 (1), 490–497.

[7] Edem, D.O., 2002, Palm Oil: biochemical, physiological, nutritional, hematological, and toxicological aspects: A review, Plant Foods Human. Nutr., 57, 319–341.

[8] Baur, F.J., and Brown, J.B., 1945, The fatty acids of corn oil, J. Am. Chem. Soc., 67 (11), 1899–1900.

[9] Mišurcová, L., Ambrožová, J., and Samek, D., 2011, Seaweed lipids as nutraceuticals, Adv. Food Nutr. Res., 64, 339–355.

[10] Orsavova, J., Misurcova, L., Ambrozova, J.V., Vicha, R., and Mlcek, J., 2015, Fatty acids composition of vegetable oils and its contribution to dietary energy intake and dependence of cardiovascular mortality on dietary intake of fatty acids, Int. J. Mol. Sci., 16 (6), 12871–12890.

[11] 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.

[12] 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.

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

[14] Anonymous, 2011, ASTM D1481: Standard test methods for density and relative density (specific gravity) of liquids by lipkin bicapillary pycnometer, ASTM, West Conshohochen, 1–5.

[15] Anonymous, 2011, ASTM D974: Standard test methods for acid number of petroleum products by color-indicator titration, ASTM, West Conshohochen, 1–7.

[16] Anonymous, 2011, ASTM D5984: Standard test methods for Total Base Number (TBN) in lubricant by color-indicator titration, ASTM, West Conshohochen, 1–3.

[17] Anonymous, 2011, ASTM D1959: Standard test methods for iodine value of oil and fat, ASTM, West Conshohochen, 1–3.

[18] Mang, T., and Dresel, W., 2007, Lubricants and Lubrication, Wiley, Weinheim, 308–310.


Article Metrics

Abstract views : 2182 | views : 2239

Copyright (c) 2017 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.

Analytics View The Statistics of Indones. J. Chem.