Preparation and characterization of bioactive oils nanoemulsions: Effect of oil unsaturation degree,emulsifier type and concentration

The effect of formulation parameters namely oil type, emulsifier type and concentration was assessed on various properties of the nanoemulsions. All nanoemulsions yielded droplets with a desirable size ranged from 38.5 to 127.9?nm. The findings showed that emulsifier type had significant effects on the physicochemical properties of emulsions. Emulsifier concentration had a negative correlation with droplet diameter, turbidity and positive correlation with polydispersity index, viscosity and creaming stability. Nanoemulsions prepared from pomegranate seed oil were different from that of two other oils in droplet size, viscosity, creaming and turbidity because of its higher intrinsic viscosity and degree of unsaturation.     

FT-NIR Spectroscopy of some long-chain fatty acids and alcohols

Fourier-transform (FT) near-infrared (NIR) spectroscopy has proved to be a powerful technique in investigating structure and thermodynamic properties of long-chain fatty acids and alcohols. In order to extract useful information from the NIR spectra, bands due to the second as well as first overtones of OH-stretching modes of the monomeric forms were employed. It has been also found that two-dimensional (2D) NIR correlation spectroscopy can accentuate useful information often obscured in the complicated NIR spectral data set.     

Elucidation of the double-bond position of long-chain unsaturated fatty acids by multiple-stage linear ion-trap mass spectrometry with electrospray ionization

Linear ion-trap (LIT) MS2 mass spectrometric approach toward locating the position of double bond(s) of unsaturated long-chain fatty acids and toward discerning among isomeric unsaturated fatty acids as dilithiated adduct ([M-H+2Li]+) ions are described in this report. Upon resonance excitation in a LIT instrument, charge-remote fragmentation that involves beta-cleavage with gamma-H shift (McLafferty rearrangement) is the predominant fragmentation pathway seen for the [M-H+2Li]+ ions of monoenoic long-chain fatty acids. The fragmentation process results in a dilithiated product ion of terminally unsaturated fatty acid, which undergoes consecutive McLafferty rearrangement to eliminate a propylene residue, and gives rise to another dilithiated adduct ion of terminally unsaturated fatty acid. In addition to the above-cited fragmentation process, the [M-H+2Li]+ ions of homoconjugated dienoic long-chain fatty acids also undergo alpha-cleavage(s) with shift of the allylic hydrogen situated between the homoconjugated double bonds to the unsaturated site. These fragmentation pathways lead to two types of CC bond cleavages that are allylic (alpha-cleavage) or vinylic, respectively, to the proximal CC double bond, resulting in two distinct sets of ion series, in which each ion series is separated by a CH2CHCH (40 Da) residue. These latter fragmentations are the predominant processes seen for the polyunsaturated long-chain fatty acids. The spectrum feature dependent on the position of unsaturated double bond(s) affords unambiguous assignment of the position of double bond(s) of long-chain unsaturated fatty acids.     

Effects of unsaturation on film structure and friction of fatty acids in a model base oil

The normal and friction forces between layers of three fatty acids (stearic, oleic, and linoleic acid) and a rosin acid (dehydroabietic acid) have been measured in n-hexadecane with a surface forces apparatus. Stearic, oleic, and dehydroabietic acid form loose-packed monolayers on mica surfaces when adsorbed from dry n-hexadecane. Linoleic acid forms an additional dimer layer between monolayer-covered surfaces, where it is stabilized by interactions between the double-bond-rich regions of the molecules. The monolayers formed by linoleic and dehydroabietic acid are thinner than the ones formed by stearic and oleic acid, but are not as easily removed from between the mica surfaces when the load or pressure is increased. The friction force increased linearly with load in all systems, and the friction coefficient increased with increasing unsaturation. Linoleic acid showed two regimes of linear friction with increasing load, corresponding to two different film thicknesses. Its friction was sensitive to sliding speed and adsorption time, and the thinner film observed at higher load had a lower friction coefficient. Such features were not observed for stearic and oleic acid, where the monolayers were removed and the friction coefficient changed to that of pure n-hexadecane at a pressure of 3.5 MPa.     

A high yield method for the direct amidation of long-chain fatty acids

The amidation of long-chain fatty acids is the key step for preparing surfactants with excellent interfacial activity. Gas chromatography–mass spectrometry was employed to detect the reactants and products in the direct amidation reactions. The conversion and the concentration of the amides in the reaction process were also investigated to determine the best catalyst, the reaction rate constants, and activation energy. It was identified that the amidation reaction of the long-chain phenyl fatty acid was a zero-order reaction and 3,4,5-trifluorophenylboronic acid was the most effective catalyst by which the activation energy reduced to 55.79 kJ/mol from 95.44 kJ/mol. The method can be applied to other long-chain fatty acids, saturated or unsatureated. The turning-over-temperature was 156°C, over which high yields can be achieved without any catalyst. These provide a reference for the preparation of long-chain fatty acid amides.     

Thermal decomposition of long-chain fatty acids and its derivative in the presence of montmorillonite

In sedimentary environments or clay-rich rocks, clay minerals are usually combined with organic matter; however, little research has focused on the effects of combinations of organic matter and clay minerals on the thermal degradation of organics and on subsequent hydrocarbon generation. In this study, the long-chain fatty acid octadecanoic acid (OA) and its derivative octadecy trimethyl ammonium bromide (OTAB) were selected as model organics. The organics were prepared for clay–organic associations with Na-based montmorillonite (Mt(Na)). The thermal decomposition behaviors of these associations were studied via thermogravimetric (TG/DTG) analysis. In the presence of Mt(Na), OA decomposed at 275.2 °C, decomposing sooner than pure OA. The thermal decomposition behavior of OTAB is nearly consistent with that of pure OTAB, but for interlayer OTAB, the decomposition temperature increased to higher than 300 °C. The results indicate that Mt(Na) plays a dual role in the thermal decomposition of fatty acid. Mt(Na) may accelerate the thermal decomposition of OA, and inherent solid acidity levels may be the key factor. In addition, the interlayer structure of Mt(Na) can increase the thermal stability of OA and OTAB. The above results further demonstrate that the thermal decomposition behavior of a given organic material may also depend on its structure and composition. In the presence of Mt(Na), organics with amino and amine structures are more stable than those with carboxyl groups.

     

Analysis of long-chain fatty acids in grey wastewater with in-vial derivatisation

The presence and levels of long-chain fatty acids (C₆–C₂₀) in grey wastewater from bathrooms have been investigated. The acids were purified and concentrated by solid-phase extraction on strong anion exchange discs, in-vial derivatised to their corresponding methyl ester and subsequently analysed by GC-MS. The method was able to quantify the acids at concentration <1?µg/L with a recovery of 31–97%. The levels of fatty acids were found in the range of <0.5 to 27?100?µg/L and the highest levels were found for the saturated lauric (C₁₂), palmitic (C₁₆) and stearic (C₁₈) acids. The treatment efficiency of a local treatment plant was evaluated by comparing concentrations of fatty acids at the inlet and the outlet. It was found that the treatability decreases with increasing chain length for the saturated acids (19–100% degradation) whereas the corresponding mono unsaturated acids were more easily degraded.     

Polymerizable derivatives of long-chain fatty acids. IV. Vinyl esters

Contrary to some published reports, the vinyl esters of saturated fatty acids polymerize readily and rapidly. Vinyl oleate, when present in excess of 5%, and oxygen exert marked retarding effects. Techniques are described for the free-radical-initiated polymerization of the vinyl esters of caprylic, capric, lauric, myristic, palmitic, and stearic acids in bulk, dispersion, solution, and emulsion. Some data are given for polymerization in the presence of chain-transfer agents, such as carbon tetrachloride, dodecylmercaptan, and ethylbenzene. Conditions are reported for obtaining degrees of polymerization from about 2 (when chain-transfer agents are employed) to 10,000 (weight average). The weight average degree of polymerization increases markedly as the conversion increases, particularly above 80%. Even up to extremely high conversions, soluble polymers are obtained in most cases. Solubility characteristics, transition point data, molecular weights (osmometric and light-scattering), and isolation and purification techniques are also reported.     

Proline derivatives incorporating hydrophobic long-chain derived from natural and synthetic fatty acids

The α-hydrophobic long chain-α-amino esters are prepared by α-hydroxylation of a series of fatty acid esters [derived from oleic acid (OA), linoleic acid (LA), arachidonic acid (ARA) and docosahexaenoic acid (DHA)] followed by Mitsunobu reaction and hydrazinolysis of the phthalimide. These amino esters are mixed with aldehydes and electrophilic alkenes to give very good chemical yields and diastereoselectivities of prolinate derivatives incorporating a hydrophobic long chain at the α-position. This multicomponent 1,3-dipolar cycloaddition (1,3-DC) takes place at room temperature. The synthesis of the homologue hydrophobic chain of OA is performed by its oxidation to aldehyde/racemic N-tert-butylsulfinyl imine/Neff reaction. Final 1,3-DC with benzaldehyde and N-methylmaleimide affords homologue prolinate derivative in good yield.     

Wettability of calcite and mica modified by different long-chain fatty acids (C18 acids)

The effect of long-chain fatty acid adsorption on the wetting states of calcite and mica powders is investigated. The selected long-chain fatty acids are saturated or unsaturated aliphatic acids (stearic acid and oleic acid, respectively) and naphthenic acids with saturated or unsaturated aromatic rings (18-cyclohexyloctadecanoic acid and 18-phenoloctadecanoic acid, respectively). The amount of irreversibly adsorbed acid is determined by thermogravimetric analysis. The affinity of water and n-decane for these samples before and after modification is deduced from their adsorption isotherm and microcalorimetry. Thermodynamic analysis of surface pressure and spreading tension are performed based on adsorption isotherms. The enthalpy versus coverage curve for water adsorption and its comparison to liquefaction enthalpy is shown to be a meaningful method for characterizing the wettability of a surface. The naphthenic acid with unsaturated aromatic ring deeply modifies the calcite to an oil-wet state. The mica powder was not as strongly modified as calcite by these acid molecules.     

Thermal behaviors of vinyl esters of long-chain fatty acids and their comblike polymers

Phase transition behaviors of vinyl esters of long-chain fatty acids (C₁₂–C₁₈) and their comblike polymers have been investigated by the thermal analysis combining with X-ray diffraction and infrared spectroscopy. Effect of the length of hydrocarbon chain on the thermal behaviors of both monomers and polymers have been elucidated. Vinyl stearate exhibits three crystalline modifications, α (hexagonal), β₁ (monoclinic, M_∥) and β₂ (monoclinic, O⊥) forms. With shortening of the alkyl chain the polymorphic behaviors become simpler. The thermal behaviors of the resultant polymers are influenced by the packing mode of monomer molecules and the polymerization temperature.     

Determination of the position distribution of fatty acids in natural phosphatidylcholines

Summary It has been shown that the snake venom ofVipera lebetina obtusa/ul can be used as a source of phospholipase A.A method is given for the accelerated enzymatic hydrolysis of natural phosphatidylcholines in order to determine the position distribution of the fatty acids by bringing the pH of the medium to 10.15.A technique for calculating the composition of the diglycerides of the phosphatidylcholines is given.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Uzbek SSR. Translated from Khimiya Prirodnykh Soedinenii, No. 2, pp. 137–141, March, 1971.     

The effect of water on the ion trap analysis of trimethylsilyl derivatives of long-chain fatty acids and alcohols

Gas chromatography/mass spectrometry (GC/MS), with an ion trap mass analyzer, was used to examine the very-long-chain cuticular acid and certain non-acid wax constituents on the leaf sheath surface of Sorghum bicolor before and during 36 hours of light exposure. The mass spectra of the trimethylsilylated acids and alcohols did not match any of those published in searchable mass spectral libraries. The observed differences can be related to the interaction between water and the trimethylsilylated acids and alcohols. Understanding the observed mass spectra of the very-long-chain plant waxes is critical for studies that employ GC/MS with the ion trap mass analyzer to elucidate cuticular wax compositions on plants.