Methyl Oleate

H-Transfer reactions of internal alkenes with tertiary amines as H-donors on carbon supported noble metals.[Pubmed:29376180]

Org Biomol Chem. 2018 Feb 14;16(7):1172-1177.

A hydride transfer reaction with tertiary amines was observed in the presence of noble metals on a carbon support. Hydride transfer had been documented previously in terms of activated allyl-type carbon-carbon double bonds containing carbonyl derivatives in the presence of triethyl amine (conjugate reduction). The proposed mechanism is a hydride transfer reaction in which the metal serves as the reaction partner of the hydrido-metal iminium adduct formation. The saturation of a non-activated internal double bond containing compound, such as Methyl Oleate and trans-5-decene as substrates, was observed for the first time in this work. The pre-reduced catalyst samples showed high activity; in the presence of Pd/C, Pt/C and Rh/C partial to complete conversion was detected at 140 degrees C in a p-xylene solvent without molecular hydrogen. Higher molecular weight byproducts of the amines were formed, while in the case of the substrates negligible amounts of unreacted but double bond migrated species were present. There is a possibility of usage of alkyl amines other than triethylamine; thus use of tributyl-, tripentyl-, trihexylamine and N,N-diisopropylethylamine, as well as cyclic 1-ethylpyrrolidine and 1-ethylpiperidine, was investigated. Cyclic amines and diisopropyl derivatives as H sources produced the highest conversion, while amines with longer alkyl chains showed minor activity. As a clear indication of H-donation, the formation of unsaturated amine species such as 1-ethyl-pyrrole and pyridine was observed.

Robust Organocatalysts for the Cleavage of Vegetable Oil Derivatives to Aldehydes through Retrobenzoin Condensation.[Pubmed:29578624]

Chemistry. 2018 Jun 7;24(32):8141-8150.

A series of thiazolium salts was prepared and tested for the cleavage of the alpha-hydroxyketone derived from Methyl Oleate. The robustness of these precatalysts was determined by dynamic thermogravimetric analyses (TGA). It has been shown that the stability of these species is mainly governed by the nature of the counter-anion and some of them were found to be stable until 350-400 degrees C. The alpha-hydroxyketone derived from Methyl Oleate was cleaved under reactive distillation conditions using optimized, thermally robust N-butylthiazolium triflate to give the cleavage product, namely, nonanal and methyl azelaaldehydate, with 85 and 70 % yields. A range of alpha-hydroxyketones derived from several fatty acids was cleaved to give the corresponding bio-based aldehydes with up to 98 % isolated yields. Finally, this protocol was successfully applied to a high-oleic sunflower oil derivative.

Heterogenization of Ketone Catalyst for Epoxidation by Low Pressure Plasma Fluorination of Silica Gel Supports.[Pubmed:29189761]

Molecules. 2017 Nov 30;22(12). pii: molecules22122099.

Low pressure plasma was used for preparing heterogeneous organocatalysts 2-(A)-(C) suitable for dioxirane-mediated epoxidations. Heterogenization was accomplished by adsorption of the methyl perfluoroheptyl ketone (2) on fluorinated supports (A)-(C) deriving from the treatment of commercial C(8)-silica gel in low pressure plasma fed with fluorocarbons. Catalyst 2-(C) proved to be the most efficient one, promoting epoxidation of an array of alkenes, including unsaturated fatty esters like Methyl Oleate (10) and the triglyceride soybean oil (11), with the cheap potassium peroxymonosulfate KHSO(5) (caroate) as a green oxidant. Notably, the perfluorinated matrix gives rise to the activation of caroate, generating singlet oxygen. Materials were characterized by infrared Attenuated Total Reflectance spectroscopy (ATR-FTIR), X-ray Photoelectron Spectroscopy (XPS ) and Emission Scanning Electron Microscope (FESEM).

Structural and functional insights into thermostable and organic solvent stable variant Pro247-Ser of Bacillus lipase.[Pubmed:29101046]

Int J Biol Macromol. 2018 Mar;108:845-852.

Thermostability of enzymes is an important issue in protein engineering and has been studied in detail. Still there is no hard and fast rule to define the conditions which will provide thermal stability. Understanding the various factors and mechanism responsible for thermal stability will add on new insights into our present knowledge in this area. Pro247-Ser variant was constructed based on homology modelling and rational design. It exhibited 60 fold increase in thermal stability at 60 degrees C and+0.7M shift in C1/2 value for urea denaturation as compared to WT. Variant displayed noticeable tolerance to organic solvents. With decrease in Km, catalytic efficiency of Pro247-Ser variant was increased by 12 fold. The activity and stability assay including circular dichroism and fluorescence spectroscopy favoured increased thermal performance of variant. Hydrolytic activity of variant was found to be high in comparison to control for all p-nitrophenol esters investigated. The immobilized variant enzyme demonstrated nearly two fold enhanced conversion of Methyl Oleate than WT enzyme. The additional molecular interactions of variant residue might contribute to increased thermostability of lipase. The homology modeling predicted formation of additional hydrogen bonds between Ser247/O-Thr251/OG1 as well as Ser247/O-Glu250/N.

Statistical optimization for lipase production from solid waste of vegetable oil industry.[Pubmed:29424632]

Prep Biochem Biotechnol. 2018 Apr 21;48(4):321-326.

The production of biofuel using thermostable bacterial lipase from hot spring bacteria out of low-cost agricultural residue olive oil cake is reported in the present paper. Using a lipase enzyme from Bacillus licheniformis, a 66.5% yield of methyl esters was obtained. Optimum parameters were determined, with maximum production of lipase at a pH of 8.2, temperature 50.8 degrees C, moisture content of 55.7%, and biosurfactant content of 1.693 mg. The contour plots and 3D surface responses depict the significant interaction of pH and moisture content with biosurfactant during lipase production. Chromatographic analysis of the lipase transesterification product was methyl esters, from kitchen waste oil under optimized conditions, generated methyl palmitate, methyl stearate, Methyl Oleate, and methyl linoleate.

Effect of Protective Agents on Silver Nanoparticle Preparation by Vacuum Evaporation on Running Hydrocarbon Solution.[Pubmed:29442925]

J Nanosci Nanotechnol. 2018 Apr 1;18(4):2547-2554.

In order to simply compare the performance of protective agents in the preparation of metal nanoparticles, a systematic investigation based on the same synthetic conditions is necessary. We successfully achieved this objective using improved vacuum evaporation on running oil substrate (VEROS) method. The efficient synthesis of nanoparticles with the improved VEROS method enabled us to characterize them by various analytical methods. In this study, five types of protective agents with different functional groups were employed to clarify their effect on the preparation of silver nanoparticles. They are sorbitan monooleate, oleylamine, oleic acid, oleyl alcohol, and Methyl Oleate. Particles synthesized by the improved VEROS method were evaluated by transmission electron microscope (TEM) and UV-vis spectrophotometer. These results indicate that sorbitan monooleate and oleic acid effectively protect the aggregation between particles. It is also evident from the evaluation of powdered nanoparticles isolated from the trap solution by thermogravimetric analysis (TGA) that these protective agents adsorb on the surface of the particles. On the other hand, the aggregates of silver nanoparticles were formed in the cases using oleic alcohol and Methyl Oleate. Silver nanoparticles were obtained in the case of oleylamine but the material efficiency of silver was extremely low. As a result, our systematic investigation using the improved VEROS method disclosed suitable protective agents in the preparation of silver nanoparticles with the physical method.

Experimental and numerical investigations on spray characteristics of fatty acid methyl esters.[Pubmed:29515835]

R Soc Open Sci. 2018 Feb 21;5(2):171121.

A comparative experimental and numerical study is conducted to establish the significance of the use of single-component over multi-component representatives of biodiesel, diesel and their blend for predicting spray tip penetration. Methyl Oleate and methyl laurate are used as single-component representative fuels for biodiesel. The pure components n-heptane, n-dodecane and n-tetradecane are used as single-component representative fuels for diesel. Methyl laurate is found to represent biodiesel of coconut, whereas Methyl Oleate is found to represent biodiesel having high percentage of long-chain fatty acid esters. The spray tip penetration of Methyl Oleate is found to be in good agreement with the measured spray tip penetration of karanja biodiesel. The spray tip penetration prediction of n-heptane fuel is closely following diesel spray tip penetration along with that of n-tetradecane and n-dodecane. The study suggests that the knowledge of the single-component representatives of biodiesel, diesel and their blend is sufficient to predict the spray tip penetration of the corresponding biodiesel, diesel and their blend under non-evaporating environment.

Methyl oleate is a fatty acid methyl ester (FAME). Methyl oleate substantially improves the antioxidation ability but markedly impaired the antiwear capacity of zinc dialkyldithiophosphate (ZDDP).

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