Indonesian Journal of Chemistry
Vol 17, No 2 (2017)

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

Yehezkiel Steven Kurniawan (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada)
Yudha Ramanda (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada)
Kevin Thomas (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada)
Hendra Hendra (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada)
Tutik Dwi Wahyuningsih (Department of Chemistry, Faculty of Mathematics and Natural Sciences, Universitas Gadjah Mada)



Article Info

Publish Date
31 Jul 2017

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.

Copyrights © 2017






Journal Info

Abbrev

ijc

Publisher

Subject

Chemical Engineering, Chemistry & Bioengineering Chemistry

Description

Indonesian Journal of Chemistry is an International, peer-reviewed, open access journal that publishes original research articles, review articles, as well as short communication in all areas of chemistry including applied chemistry. The journal is accredited by The Ministry of Research, Technology ...