Oil Fatty Acid Ethyl Esters Research Articles

A SUCCESSFUL CASE OF LYMPHATIC EMBOLIZATION IN A PATIENT WITH PROLONGED LYMPHATIC LEAKAGE AFTER CYTOREDUCTIVE NEPHRECTOMY FOR METASTATIC RENAL CANCER

A 57-years-old woman was referred to our urological department due to a 7.2-cm tumor in the left kidney, detected on computed tomography (CT). Dynamic CT of the kidney confirmed the diagnosis of left renal cancer, with lung metastasis (cT2aN0M1). The patient had a poor prognosis (IMDC classification), given the following risk factors: Time from initial diagnosis to initiation of systemic therapy < 1year, hemoglobin of 8.4 g/dL, calcium of 10.7 mg/dL, and platelet of 74.2×104/mm3. Laparoscopic left radical nephrectomy was performed before systemic drug treatment because the solitary lung metastasis was relatively small (10 mm) and the patient had symptoms of hematuria and fever. The pathological diagnosis was a clear cell carcinoma with renal sinus invasion (pT3a). Four days postoperatively, the patient developed lymphatic leakage, and was unresponsive to diet and conservative treatment. Lymphatic embolization with iodized poppy oil fatty acid ethyl ester was performed 22 days postoperatively. Contrast material leakage from the left renal hilar lymph node was observed before embolization. Post-embolization CT confirmed no contrast leakage. The patient resumed oral feeding on the 28th postoperative day, and the drain was successfully removed the next day. She was discharged on the 35th postoperative day. On follow-up, increased lung metastases were observed on CT. She was treated with the combination of ipilimumab and nivolumab. After one course of treatment, a CT scan showed a further increased in lung metastases (RECIST: PD). Thus, she was initiated on cabozantinib monotherapy. Lymphatic embolization may be a safe and effective treatment for lymphatic leakage that does not improve with conservative treatment.

Epoxidation of unsaturated fatty acid ester promoted by imidazolium acidic ionic liquids: An unexpected selectivity phenomena

AbstractEpoxidation of linseed oil fatty acid ethyl esters promoted by a series of functionalized imidazolium ionic liquids was studied. In this reaction acidic imidazolium ILs behave not only as an acid catalysts but also play an additional role as a specific activator for the reaction of epoxidation of unsaturated fatty derivatives in H2O2/formic acid oxidation system. The obtained results indicate that the hydrogen‐bonding interaction of imidazolium cation with epoxide group influences the selectivity of the epoxidation reaction. In particular, the presence of unprotected weak “acid” C2‐H proton significantly lowers the selectivity to hydroxyl derivatives. The obtained results also point to another example of specific polyfunctionality of ILs, especially imidazolium one, used as surfactants and process activators.

Oxidation Stability: The Bottleneck for the Development of a Fully Renewable Biofuel from Wine Industry Waste.

Wine industry generates a large amount of biowaste, such as grape marc and wine lees, which is considered in the Directive (EU) 2018/2001 as an adequate feedstock to produce advanced biofuels. Grapeseed oil fatty acid ethyl esters (FAEEs) can be obtained from oil extracted from grape marc and bioethanol distilled from wine lees or wine surplus. Although FAEE still has no specific standard, grapeseed oil FAEE would fulfill all of the properties set by the standard EN 14214, except oxidation stability. This work analyzes the effect of natural antioxidants on the oxidation stability of grapeseed oil FAEE, using grapeseed oil fatty acid methyl esters (FAMEs) as a reference for comparison. On the one hand, the biofuel, produced with conventional transesterification, was mixed with FAME and FAEE produced via in situ transesterification. On the other hand, antioxidants extracted from grapeseed or defatted grapeseed flour were added to the biofuel. The results show that (1) FAEE has worse oxidation stability than FAME, (2) in situ transesterification improves the oxidation stability, and (3) addition of natural antioxidants is hindered by their low solubility in alkyl esters. Finally, the concentration of antioxidants, measured by UV–vis spectroscopy, showed a correlation between the absorbance at 285 nm (characteristic of phenolic compounds) and the induction time (IT) of the samples.

Optimization of the production of biofuel form Jatropha oil using a recyclable anion-exchange resin

The study of an anion-exchange resin (Amberlyst A26 (OH)) catalyzed transesterification of Jatropha (Jatropha curcas L.) oil was conducted to determine the effects of three variables: reaction temperature, ethanol: oil molar ratio and catalyst amount, on Jatropha oil conversion (XJO) and fatty acid ethyl esters yield’s (YFAEEs). The modified central composite design that involved three independent factors (temperature, ethanol: oil molar ratio and the catalyst present) with two levels, but not included the non-linear stage, was employed to optimize the process. From the main factors and their interactions, the ethanol: oil molar ratio was found to highly affect the XJO and YFAEEs. In this study, the statistical analysis showed that curvature is not significant (p ≤ 0.05), and thus, from the model regression equations, linear model was found to be more suitable to optimize the responses. By using the regression analysis and the response surface plots, the optimum XJO and YFAEEs of 37.63% and 36.31%, respectively were predicted to be obtained at the optimum temperature of 55 °C, ethanol: oil molar ratio of 35:1 and catalyst amount of 15%. Employing higher amount of catalyst reduced the XJO and YFAEEs, particularly, when the variable interacted with the reaction temperature.

Sunflower oil-based MCC surface modification to achieve improved thermomechanical properties of a polypropylene composite

A biobased approach was taken to endow microcrystalline cellulose (MCC) with surface hydrophobicity using sunflower oil biodiesel (sunflower oil fatty acid ethyl esters, SFEEs) and thereby improve the compatibility with a hydrophobic polypropylene (PP) matrix. This environmentally friendly green chemistry approach introduces a monomolecular long-chain fatty acid layer on the MCC surface, making the surface hydrophobic. However, as per the X-ray Diffraction results, this surface modification process had no effect on the crystal structure of MCC. The inclusion of surface-modified MCC in the PP matrix significantly improves the thermomechanical properties of the composite. The tensile, impact and hardness properties of the surface-treated fiber reinforcements were improved by 11%, 71%, and 23%, respectively, compared to those of nonreinforced PP. The thermal stability also was improved considerably by the incorporation of modified MCC into PP.

Study on Morphology and Rheological Property of Organoclay Dispersions in Soybean Oil Fatty Acid Ethyl Ester over a Wide Temperature Range.

This work attempted to establish the relationship between the dispersion morphology and the viscous flow behavior of clay dispersions in soybean oil fatty acid ethyl ester (FAEE) at 2 and 65 °C. The clays used in this study include raw montmorillonite (Mt) and three kinds of organoclays prepared by ion exchange modification of Mt by cetyltrimethylammonium chloride (OC16), dihexadecyldimethylammonium chloride (ODC16), and trihexadecylmethylammonium chloride (OTC16), respectively. The X-ray diffraction and water contact angle results demonstrated that greater alkyl chain number of surfactants led to greater interlayer space and stronger hydrophobicity of organoclays. Due to the good affinity of the surfactant and FAEE, OC16 exhibited the most stable dispersion in FAEE between 2–65 °C, which resulted in the best flat rheological property. The molecular structures of multiple chain surfactants were quite different from that of FAEE, resulting in weak affinity between organoclays (ODC16 and OTC16) and FAEE. The sheets of ODC16 and OTC16 tended to aggregate at 2 °C, forming a gel structure, thus significantly increasing the low shear rate viscosity (LSRV) and yield stress. At 65 °C, with the expansion of FAEE and the stronger thermal motion of sheets, the dispersions of ODC16 and OTC16 were improved, destroying the original gel structure and resulting in significant decreases in LSRV and yield stress. This study confirmed that stable clay/FAEE dispersions tended to exhibit flat rheology, which could serve as a basis for the application of clay/biodiesel dispersion in deep-water drilling.

Lignin-Based Biopolymeric Active Packaging System for Oil Products.

Antioxidant activity of enzymatically modified soybean protein film with two different forms of added lignin (alkali lignin and lignosulfonate) was investigated using two stimulated food systems involving direct and indirect contact with soybean oil and fish fatty acid ethyl ester (FAEE). For the direct system, control and lignin-doped films were added to oil vials which were stored at dark under 40 °C whereas for indirect, films were used to cover oil-containing glass vials stored under standard commercial lighting conditions. Autoxidation of oil samples in the direct contact system was determined by peroxide value (PV), color, headspace oxygen, and volatile compounds, while for the indirect contact system photoxidation was determined by using PV and color. For the direct contact system with soybean oil, the PV was significantly lower during storage for both lignins used compared to the control (packaging system without lignin film). There was not a significant effect of lignin on the color of the oils (P > 0.05). Modified films tested in this study did not have a significant effect on headspace oxygen contents of oil samples; however, it resulted in reduced volatile compounds for both soybean oil and fish oil samples. Based on our observation, soybean protein films with lignin showed a greater impact on soybean oil than fish oil, possibly because of high initial oxidation levels in the fish oil. Enzymatic modified soy protein films with lignin are alternative active packaging materials for highly sensitive to oxidation by radical and UV light. PRACTICAL APPLICATION: Plastic packaging materials require the use of petroleum oil and are not biodegradable. Packaging materials made from renewable, biodegradable biopolymers are of great interest but often suffer from performance problems, such as weak mechanical properties compared to petroleum-based plastics. Applying modified biopolymeric film with lignin in the inner layer of food packaging system improved some aspects of their performance during storage, not only by preventing the migration of chemical compounds from the package to the food but also by radical scavenging activity and UV-blocking ability of the packaging system.

Rhizoclonium grande Bioethanol in Biofuel Production by Transesterification of Jatropha curcas Oil

There is a need for an alternative sustainable fuel based on renewable sources and efficient carbon dioxide scrubbers. Alkyl esters prepared by transesterification of vegetable oils from various plants have been evaluated. In this work the potential of sustainable macroalgae bioethanol in biofuel production by transesterification of Jatropha curcas oil was assessed. Rhizoclonium grande macroalgae was collected from Shimoni shores in Kwale, Shelly beach in Mombasa, Jamvi la Wageni in Mtongwe Likoni, English point near Kenya Marine and Fisheries Research Institute (KMFRI) Mombasa, dried and processed to obtain 5.36% ± 0.355% v/w bioethanol using Aspergilus niger for hydrolysis and Saccharomyces cerevisiae for fermentation. J. curcas seeds were collected from contracted farmers of Energy Africa in Shimba hills, Coast region. Oil from the seeds was machine cold pressed and solvent extracted using n-hexane giving 44% - 53%v/w yield. The physicochemical properties of the J. curcas oil were investigated. Transesterification of J. curcas oil was carried out using bioethanol from the algae with 63% - 70% FAEE yield. Characterisation of the bioethanol and ethyl esters was done using GC-MS. Physicochemical and fuel properties of the biofuel were investigated at Technical University of Mombasa (TUM), Jomo Kenyatta University of Agriculture and Technology (JKUAT), Government Chemist and Kenya Pipeline Laboratories in Mombasa. There was significant difference in physicochemical and fuel properties observed in density, calorific value, kinematic viscosity, pour point and cloud point between the Jatropha oil and Jatropha fatty acid ethyl esters (JAT FAEE) samples. No significant difference observed in the physicochemical and fuel properties between the JAT FAEE and standard biodiesel samples. This was according to statistical analysis of data done using STATA/SE 13.0 and Xlstat at 95% confidence level (P < 0.05) two-tailed. From the findings bioethanol from R. grande biomass used in transesterification has a potential to improve the sustainability, physicochemical and fuel properties of biofuel from J. curcas a non-food crop. The effect of the use of bioethanol and its byproduct on shelf life of the biofuel can further be investigated.

Use and limitations of a quartz crystal microbalance to measure viscosity of carbon dioxide-expanded fish oil fatty acid ethyl esters

The use of a quartz crystal microbalance (QCM) to determine the viscosity of CO2-expanded (CX) liquids was evaluated. This study presents a calibration method for QCM to be used for viscosity measurements at elevated hydrostatic pressures, taking into account the effects of hydrostatic pressure and surrounding fluid density on the resonant frequency of the QCM in an effort to isolate the effect of viscosity. The viscosity values obtained for CX fatty acid ethyl esters and CX ethanol with increasing pressure using the QCM were lower compared to literature data, indicating that the no-slip boundary condition between the QCM surface and the CX liquid was compromised. Thus, a QCM was found not to be suitable for measuring viscosity of CX liquids but could be used to determine the viscosities of gas-free liquids at ambient and elevated pressures.

Viscosity and rheological behavior of carbon dioxide-expanded fish oil fatty acid ethyl esters: Measurement using a rotational viscometer and modeling

The viscosity of fish oil fatty acid ethyl esters (FAEE) in equilibrium with CO2 was determined at 40, 55, and 70°C and pressures ranging from 0.1 to about 12MPa using a rotational rheometer equipped with a high pressure cell. Viscosity of CO2-expanded (CX) FAEE decreased due to the dissolution of CO2 with pressure, which was temperature dependent. The viscosity of CX FAEE was correlated using a new empirical model utilizing saturation pressure and temperature with temperature-dependent parameters, which allows interpolation of viscosity data for any pressure and temperature within the envelope of this study. As well, viscosity was modeled using available data for CO2 solubility in FAEE at specific temperatures of this study utilizing simpler models with only one parameter, such as the Grunberg and Nissan model. The rheological data suggest shear thickening behavior of CX FAEE at elevated pressures. The limitations of the rotational rheometer for measuring CX liquids at viscosities below 1mPas are discussed. Understanding of viscosity and rheological behavior of CX FAEE is essential for equipment and process design involving such lipids.

Optimization of reaction parameters for enzymatic glyceride synthesis from fish oil: Ethyl esters versus free fatty acids

Abstract Enzymatic conversion of fish oil free fatty acids (FFA) or fatty acid ethyl esters (FAE) into glycerides via esterification or transesterification was examined. The reactions catalyzed by Lipozyme™ 435, a Candida antarctica lipase, were optimized. Influence on conversion yields of fatty acid chain length, saturation degree, temperature, enzyme dosage, molar ratio glycerol:fatty acids, acyl source composition (w/w ratio FFA:FAE), and reaction time was evaluated collectively by multiple linear regression. All reaction variables influenced the conversion into glycerides. Transesterification of FAE produced the highest yields of 94–95% (w/w) conversion yield at 1:3 glycerol:FAE, 25 h, 66 °C, enzyme dosage 3.1%w/w.

Production of biodiesel from pentaclethra macrophylla seed oil

In the present work, the potentials of pentaclethra macrophylla (Africa oil bean) seed oil (PMSO) are evaluated for the first time as a feedstock for biodiesel. Methyl (PMFAME) and ethyl (PMFAEE) esters of PMSO were produced by standard transesterification procedure using potassium hydroxide (KOH) as catalyst and their qualities determined. Gas chromatography mass spectrometry (GCMS) runs of the biodiesels revealed that the linoleic acid (unsaturated fatty acid) of the methyl esters (55.68%) and ethyl esters (33.45%) of PMSO dominate the fatty acid profile. The viscosity, flash point, cloud point, pour point and acid number of PMFAME and PMFAEE were found to be 4.08 mm 2 /s and 4.16 mm 2 /s; 196°C and 198°C; –5°C and 2°C; 0°C and 1°C; 0.50 mgKOH/g and 0.20 mgKOH/g. The calculated cetane number of 36.72 and higher heating value of 40.47 KJ/g were obtained for both PMFAME and PMFAEE. These together with other fuel parameters were compared with those of soy oil fatty acid methyl esters (SFAME) and ethyl esters (SFAEE), diesel – fuel (D 2 ), ASTM and European (EN 14214) standards. The results obtained indicate that PMSO appears to be a potential feedstock for biodiesel production.

Interfacial tension of marine lipids in contact with high pressure carbon dioxide

Abstract Interfacial tension (IFT) of fish oil triglycerides (TG) and fatty acid ethyl esters (FAEE) in contact with carbon dioxide (CO2) was measured according to the pendant drop method at 40, 55 and 70 °C and pressures up to 25 MPa. The IFT of both TG and FAEE decreased substantially with CO2 pressure. The IFT of FAEE vanished at elevated pressures, whereas that of TG decreased to a fairly constant level of about 2 mN/m. The IFT was correlated using a model taking into account the density, pressure and temperature of CO2, thereby facilitating the calculation of the ideal pendant drop volume as well as the surface excess concentration of CO2. In the pressure range studied, the pendant drop volume for FAEE decreased with pressure, whereas for TG it increased at elevated presssures due to the predominant effect of buoyancy. Furthermore, the change in IFT over time was determined at 55 °C for TG in contact with CO2 at pressures up to 11.4 MPa showing a decrease of IFT over time at low pressures, whereas at higher pressures it remained nearly constant. IFT influences drop formation as well as the disintegration of falling films thereby affecting the performance of separation processes.

Density of marine lipids in equilibrium with carbon dioxide

The density of marine lipids in equilibrium with carbon dioxide (CO 2) was determined using a view cell equipped with a novel spring balance based on Archimedes’ principle. The densities of fish oil triglycerides (TG) and fish oil fatty acid ethyl esters (FAEE) were measured at pressures ranging from 0.1 to about 25 MPa and temperatures of 40, 55 and 70 °C. In the pressure and temperature ranges investigated, the density increased with pressure and decreased with temperature. The density increase from atmospheric pressure to about 25 MPa at temperatures of 40, 55 and 70 °C was 4.1, 3.2, 2.7% and 5.3, 4.0, 3.6% for TG and FAEE, respectively. Volumetric expansion of fish oil TG and FAEE saturated with CO 2 was determined at 40 °C and pressures ranging from 0.1 to 22 MPa. With increasing pressure a relative volume change of up to 38 and 67% was observed for TG and FAEE, respectively. The density and volumetric expansion of lipids in equilibrium with CO 2 are important for optimal design of high pressure processes involving mass and momentum transfer.

Marine phospholipids—a promising new dietary approach to tumor-associated weight loss

Advanced tumor disease very often evokes excessive loss of body weight. Among others, fish oil or marine fatty acid ethyl esters were investigated for treatment of cancer cachexia with controversial results. In this study, a new formulation of marine fatty acids was investigated, the marine phospholipids, with more than 50% of phospholipid-bound fatty acids being eicosapentaenoic and docosahexaenoic acid. Thirty-one tumor patients with various tumor entities suffering from weight loss were asked to take marine phospholipids (1.5 g/day) as softgel capsules for a period of 6 weeks. Compliance, body weight, appetite, and quality of life as well as the fatty acid profile in plasma and blood cells were monitored; 17 patients could be analyzed. Marine phospholipids were very well accepted; low-dose supplementation resulted in a significant increase of eicosapentaenoic and docosahexaenoic acid in plasma phospholipids; therefore, significantly reducing the n-6 to n-3 fatty acid ratio. A stabilization of body weight was achieved (median weight change of +0.6% after 6 weeks), while appetite and quality of life improved. These promising first results encourage further investigation of marine phospholipids in cancer care.

Food additives obtained by supercritical extraction from natural sources

This work addresses thermodynamic modeling, simulation and optimization of supercritical extraction of fish oil fatty acid ethyl esters (FAEE) with ethane as alternative solvent to carbon dioxide. The objective is the production of pharmaceutical grade concentrates of eicosapentaenoic acid (EPA) and docohexaenoic acid (DHA) esters, which are the most valuable omega-3 polyunsaturated fatty acid esters. The pharmaceutical grade concentrates can be obtained at relatively low cost to be incorporated as food additives. The Group Contribution Equation of State (GC-EoS) has been extended to include ethane–ester interaction parameters. Process optimizations have been performed for a simple column-separator scheme, for both carbon dioxide and ethane. Numerical results have shown higher solubility of FAEE in ethane, as well as a slightly better selectivity to EPA and DHA.

Liquid–Liquid Equilibrium for Systems of (Fatty Acid Ethyl Esters + Ethanol + Soybean Oil and Fatty Acid Ethyl Esters + Ethanol + Glycerol)

Fatty acid ethyl esters (FAEEs) have great potential for biodiesel fuel production because the raw materials are renewable. Soybean oil (SBO), ethanol, fatty acid ethyl esters, and glycerol are partially miscible in the reaction process. The mutual solubility data of the reaction components are essential for the production design and process operation. In this work, fatty acid ethyl esters were produced by transesterification of soybean oil with ethanol using NaOH as a catalyst. The phase diagrams and tie lines of the fatty acid ethyl esters + ethanol + soybean oil system and fatty acid ethyl esters + ethanol + glycerol system were drawn in the range from (300.15 to 343.15) K. The results indicate that the transesterification reaction is carried out in the ethanol phase. When the temperature increases to 343.15 K, the soybean oil + ethanol mixture becomes a homogeneous phase. The distribution coefficient of fatty acid ethyl esters between the soybean oil phase and the ethanol phase decreases with the incr...

Biodegradability of biodiesel fuel of animal and vegetable origin

AbstractOne of the positive features of biofuel concerning environmental protection is its high biodegradability. Fuel is considered to be biodegradable if not less than 90% of it degrades within 21 days. The aim of this work was to determine the biodegradability of various kinds of fatty acid methyl esters and their mixtures with fossil diesel fuel in natural environments. It was determined that fatty acid methyl esters meet the requirements for biodegradability set by the EU. Of rapeseed oil fatty acid methyl esters (RME), 91.2% degraded within 21 days, compared to 94.2% of rapeseed oil fatty acid ethyl esters, 98.3% of linseed oil fatty acid methyl esters (LSME), 90% of tallow fatty acid methyl esters, and 92.5% of pork lard fatty acid methyl esters (LME), while the amount of degraded fossil diesel fuel reached only 57.3%. The biodegradability of multi‐component biofuels containing RME, LSME and LME is similar; the best is of a mixture of 70% RME, 6% LSME and 24% LME. It was determined that more than 90% of multi‐component biofuel and fossil diesel fuel mixtures degrade within 21 days when they contain 35% and more of multi‐component biofuel.

Supercritical carbon dioxide fractionation of fish oil fatty acid ethyl esters

Fractionation of fish oil fatty acid ethyl esters was investigated with the aim of obtaining a lipid fraction enriched in ω-3 fatty acids and with a suitable EPA/DHA ratio. The results obtained highlight the possibility of modifying the original fatty acid ethyl esters concentration by optimizing the extraction conditions in terms of pressure, temperature, and supercritical carbon dioxide flow rate. Supercritical fluid fractionation (SFF) appears to be a useful processing technique for changing the composition of lipids in order to obtain high value functional products. The use of proper fractionation temperatures and pressures along the column influenced the solvent-to-feed ratio to obtain fractions with suitable composition for market requirements.

Oxidative stability of biodiesel from soybean oil fatty acid ethyl esters

Biodiesel consists of long-chain fatty acid esters, derived from renewable sources such as vegetable oils, and its utilization is associated to the substitution of the diesel oil in engines. Depending on the raw material, biodiesel can contain more or less unsaturated fatty acids in its composition, which are susceptible to oxidation reactions accelerated by exposition to oxygen and high temperatures, being able to change into polymerized compounds. The objective of this work was to determine the oxidative stability of biodiesel produced by ethanolysis of neutralized, refined, soybean frying oil waste, and partially hydrogenated soybean frying oil waste. The evaluation was conducted by means of the Rancimat® equipment, at temperatures of 100 and 105ºC, with an air flow of 20 L h-1. The fatty acid composition was determined by GC and the iodine value was calculated. It was observed that even though the neutralized, refined and waste frying soybean oils presented close comparable iodine values, biodiesel presented different oxidative stabilities. The biodiesel from neutralized soybean oil presented greater stability, followed by the refined and the frying waste. Due to the natural antioxidants in its composition, the neutralized soybean oil promoted a larger oxidative stability of the produced biodiesel. During the deodorization process, the vegetable oils lose part of these antioxidants, therefore the biodiesel from refined soybean oil presented a reduced stability. The thermal process degrades the antioxidants, thus the biodiesel from frying waste oil resulted in lower stability, the same occuring with the biodiesel from partially hydrogenated waste oil, even though having lower iodine values than the other.