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Tribology and oxidation studies of fatty acid sulfide derivatives synthesized via thiol‐ene “Click” additions
Author(s) -
Sammaiah Arukali,
Padmaja Korlipara V.,
Prasad Rachapudi B. N.
Publication year - 2016
Publication title -
european journal of lipid science and technology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.614
H-Index - 94
eISSN - 1438-9312
pISSN - 1438-7697
DOI - 10.1002/ejlt.201500119
Subject(s) - chemistry , organic chemistry , base oil , antioxidant , fatty acid , sulfide , ene reaction , double bond , thiol , materials science , scanning electron microscope , composite material
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 1 H, 13 C 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.