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- Title
Tribology and oxidation studies of fatty acid sulfide derivatives synthesized via thiol-ene 'Click' additions.
- Authors
Sammaiah, Arukali; Padmaja, Korlipara V.; Prasad, Rachapudi B. N.
- Abstract
The synthesis of sulfide derivatives via thiol-ene addition reactions of methyl oleate and methyl 10- undecenoate as substrates is reported. The substrate fatty acids contained a terminal double bond in methyl 10-undecenoate and an internal double bond in methyl oleate. Thiol-ene addition of unsaturated fatty acid ester derivatives with hydroxy and amine functionality on the fatty acids was carried out under thermal conditions. The synthesized products were characterized by 1H, 13C NMR, FT-IR, and GC-MS analysis and evaluated for their antioxidant, extreme pressure (EP), and antiwear (AW) properties in base oil namely, epoxy jatropha fatty acid n-butyl esters (EJB). Synthesized products exhibited comparable antioxidant efficacy to butylated hydroxyl toluene (BHT). All four synthesized sulfide derivatives significantly enhanced the weld point of the base oil EJB and exhibited comparable performance to TCP (tricresyl phosphate) at 1 wt% level. Methyl 9(10)-(2-hydroxyethylthio) octadecanoate at 0.5% concentration exhibited considerable improvement in the wear scar of base oil from 0.834 to 0.422 mm. The synthesized sulfide derivatives have potential as multifunctional additives for biolubricant basestocks. Practical applications: Synthesis of multifunctional additives via thiol-ene addition under thermal conditions. The prepared sulfide derivatives were found to exhibit good antioxidant, antiwear, and extreme pressure additives. The synthesized additives exhibited comparable performance to commercial additives. The products are potential biobased alternatives for commercial additives. Sulfide derivatives as multifunctional additives.
- Subjects
SULFIDE synthesis; FATTY acid oxidation; TRIBOLOGY; THIOL derivatives; OLEATES; ADDITION reactions; FOURIER transform infrared spectroscopy; GAS chromatography/Mass spectrometry (GC-MS)
- Publication
European Journal of Lipid Science & Technology, 2016, Vol 118, Issue 3, p495
- ISSN
1438-7697
- Publication type
Article
- DOI
10.1002/ejlt.201500119