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

https://doi.org/10.22146/ijc.24891

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

Abstract


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.

Keywords


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

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DOI: https://doi.org/10.22146/ijc.24891

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