Synthesis, Characterization, and Evaluation of Castor Oil-Based Acylated Derivatives as Potential Lubricant Base Stocks

Synthesis, characterization, and evaluation of a series of novel acylated derivatives of castor oil as biolubricant base stocks are described. The acylated derivatives of castor oil, castor oil fatty acid methyl and 2-ethylhexyl esters were synthesized using different anhydrides (C₁–C₆) in about 90–95% yield. All the products were structurally characterized using NMR and IR spectral data. The acylated products were evaluated for their physicochemical and lubricant properties. Although these products belong to group V, based on viscosity index (130–156), acylated derivatives of castor fatty acid alkyl esters belong to group III, the category of base fluids as per API classification. The acylated products exhibited excellent pour point (−21 to −39 °C) and flash point (174–280 °C). The hexanoylated and butanoylated esters of castor oil exhibited excellent flash points of 280 and 272 °C, respectively. The air release value was found to be excellent in the range of 0.38–0.99 min, and NOACK volatilities in the range of 3.25–3.92%. The other lubrication properties such as load carrying capacity, and emulsion stability were found to be good. Therefore, these derivatives will have utility in hydraulic and metal working fluids and other industrial fluids with their wide range of properties

Synthesis and evaluation of anti-oxidant and cytotoxic activities of novel 10-undecenoic acid methyl ester based lipoconjugates of phenolic acids

The synthesis of five novel methyl 10-undecenoate-based lipoconjugates of phenolic acids from undecenoic acid was carried out. Undecenoic acid was methylated to methyl 10-undecenoate which was subjected to a thiol–ene reaction with cysteamine hydrochloride. Further amidation of the amine was carried out with different phenolic acids such as caffeic, ferulic, sinapic, coumaric and cinnamic acid. All synthesized compounds were fully characterized and their structures were confirmed by spectral data. The anti-oxidant activity of the synthesized lipoconjugates of phenolic acids was studied by the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging assay and also by the inhibition of linoleic acid oxidation in micellar medium by differential scanning calorimetry (DSC). The prepared compounds were also screened for their cytotoxic activity against five cell lines. It was observed that the lipoconjugates of caffeic acid, sinapic acid, ferulic acid, and coumaric acid displayed anticancer and anti-oxidant properties. The anticancer properties of these derivatives have been assessed by their IC50 inhibitory values in the proliferation of MDA-MB231, SKOV3, MCF7, DU 145 and HepG2 cancer cell lines

Preparation and Properties of Lubricant Base Stocks from Epoxidized Karanja Oil and Its Alkyl Esters

Lubricant base stocks of epoxidized oil and its alkyl esters namely epoxidized karanja fatty acid methyl, butyl, 2-methyl-1-propyl, and 2-ethylhexyl esters were synthesized from renewable nonedible source karanja oil (<i>Pongamia glabra</i>). The reaction was carried out using peroxy formic acid (HCOOH) generated <i>in situ,</i> 30 wt % aqueous hydrogen peroxide (H₂O₂) by monitoring oxirane oxygen value. The optimized conditions to obtain epoxidized products were oil/ester: HCOOH: H₂O₂ (1:2:8/1:1.5:3 mol/mol/mol). The epoxidized products were obtained in 90–97% conversion by GC analysis. All the products were characterized by GC, GC-MS, IR, ¹H NMR spectral studies. The synthesized products were evaluated for physicochemical and lubricant properties. Based on viscosity index all the products belong to group III, category of base fluids as per API classification. Expecting pour point values that are on higher side, other lubrication properties such as viscosity, VI, flash point, Cu corrosion value, and air release value were found to be good

Novel Acyl Derivatives from Karanja Oil: Alternative Renewable Lubricant Base Stocks

Lubricant base stocks of acylated oil and its derivatives, namely, propionylated, butanoylated, and hexanoylated karanja oil and fatty acid methyl esters, were synthesized from renewable nonedible source karanja oil (Pongamia glabra). The reaction was carried out by Prilezhaev dihydroxylation, an in situ peroxyformic acid generated using hydrogen peroxide and formic acid. The hydroxylated derivatives were acylated with three acid anhydrides (C₃, C₄, and C₆). All of the synthesized products were examined for their purity by GC and GC-MS and characterized by IR and ¹H NMR spectral studies. The acylated derivatives were evaluated for physicochemical and lubricant properties. Propionylated and butanoylated esters of KFAME were found suitable as IS: 3098 hydraulic fluids in ISO VG 46 and ISO VG 68 categories, respectively. In addition, propionylated esters of KFAME are also suitable as IS: 8406 gear oils (R&O type). Other lubrication properties such as viscosity, viscosity index of all products belonging to group III, category of base fluids as per API classification, Cu corrosion value, weld point, and air release value were found to be good. These base stocks may find applications in hydraulic fluids and metal-working fluids