From Fatty Acid Methyl Esters Research Articles

Preparation of 4,4-Dimethyloxazoline and Pyrrolidine Derivatives from Fatty Acid Methyl Esters Using Sodium Borohydride: Mild and Simple One-Pot Derivatization Procedures for a Gas Chromatographic–Mass Spectrometric Analysis of Fatty Acids

Procedures for preparing 4,4-dimethyloxazoline (DMOX) and pyrrolidine derivatives from fatty acid methyl esters (FAMEs) were modified to provide milder and simpler conditions for the derivatization reactions widely used in the mass spectrometric analysis of fatty acids. DMOX and pyrrolidine derivatives were obtained overnight at room temperature in the presence of sodium borohydride. The proposed method, involving a low-temperature condensation-cyclization of FAME to DMOX, allows for the direct preparation of DMOX derivatives from non-hydroxy, 2- and 3-hydroxy acid methyl esters. The described simple one-pot procedures are “mild” alternatives to existing methods, which require the use of elevated temperatures.

Experimental investigation and process simulation of biolubricant production from waste cooking oil

Waste cooking oil (WCO) or frying oil was used for synthesis of biolubricant via transesterification reaction. Biolubricant (dioleoyl ethylene glycol ester) was prepared from fatty acid methyl esters (FAMEs) of WCO with ethylene glycol (EG). The reaction was performed using calcium oxide (CaO) heterogeneous catalyst. Dioleoyl ethylene glycol ester is a potential biodegradable lubricant that could be used in industrial lubricant applications. The effect of changing operating conditions such as temperature, molar ratio of reactants, reaction time and catalyst loading was studied. The optimal conditions that achieved highest conversion were found to be 130 °C, 3.5: 1, 1.5 h and 1.2% (w/w) catalyst dosage. The produced biolubricant structure was tested using FTIR spectrum technique and its thermal stability was examined using TGA technique. The biolubricant properties were compared to two other biolubricants and also to specifications of four different ISO viscosity grade lubricants. It was found that produced biolubricant complies with ISO VG68 viscosity grade with better low temperature applicability. The process simulation was performed on Aspen HYSYS program version 9 using conversion reactor model and using Non-Random Two-Liquid (NRTL) activity coefficient model. Simulation results proved that the studied biolubricant production process is industrially applicable.

Synthesis of Trimethylolpropane Esters by Base‐Catalyzed Transesterification

AbstractTrimethylolpropane (TMP) esters are synthesized from fatty acid methyl esters (FAMEs) and TMP to produce a fluid with properties suitable for use as a lubricant base oil, exhibiting good stability, and low‐temperature performances. In this study, triacylglyceride (TAG) molecules are modified to produce FAME and then linked to TMP. Initially, vegetable oil is transesterified with excess methanol, and potassium hydroxide to produce crude FAME. The FAMEs are then refined and further transesterified with TMP and heating, under vacuum, using potassium carbonate catalyst. The conversion of TMP is successfully achieved by adding an excess of FAME to a reaction mixture of base and polyol in the second step. All reactions are monitored and confirmed using 1H‐NMR. The reactions proceed quickly as an efficient production of FAME and TMP to TMP triesters is successfully achieved by adding an excess of FAME slowly to a mixture of TMP and catalyst.Practical Applications: The major objective is to develop and optimize a reverse addition reaction method for TMP‐based biolubricant production. The highly enriched TMP biolubricant is prepared by reverse phase chromatography and these biolubricant products are characterized for oxidative stability index and low‐temperature performance. The optimum conditions are applied to different vegetable oils.

Production of Renewable Light Olefins from Fatty Acid Methyl Esters by Hydroprocessing and Sequential Steam Cracking

A route to produce renewable light olefins from fatty acid methyl esters (FAMEs), which are originally derived from waste cooking oils, has been demonstrated on a laboratory scale. Presaturation of...

Production of Hydrocarbon (C7-C20) from Hydrocracking of Fatty Acid Methyl Esters on Pd/Al-MCM-41 Catalyst

The production of hydrocarbon (C7-C20) and alcohol (C11-C19) from fatty acid methyl esters (FAMEs) compound are produced from the transesterification of the seed oil of the Nyamplung that has been conducted by the catalytic hydrocracking using Al-MCM-41 and Pd2+-impregnated-Al-MCM-41 catalysts. The performance of catalysts were compared by various analysis including the acidity that was determined by pyridine and FTIR, the crystal structure observed by XRD, the surface area and pore volume analyzed by BET/BJH, the surface morphology observed by TEM, the metal on the surface of catalyst observed by XPS and the product of the hydrocracking analyzed by GC-MS. Hexagonal structure of the MCM-41(100) was shown in the 2θ = 3o-5o of the diffractogram. The presence of impregnated Al and Pd observed at the 2θ = 20o and 34o, respectively. The Pd/Al-MCM-41 catalyst was more acidic than Al-MCM-41 catalyst. The surface area and pore volume of the catalyst decreased after the impregnation process. The tendency of catalytic hydrocracking of hydrocarbon produced was indicated that more amount of Palladium have more hydrocarbons aliphatic than alcohol.

Fatty acid profile and fuel-derived physico-chemical properties of biodiesel obtained from an indigenous green microalga, Desmodesmus sp. (I-AU1), as potential source of renewable lipid and high quality biodiesel

Organic sources of biodiesel such as microalgae are considered as potential renewable energy resources. These organisms are considered as sunlight-driven cellular factories that convert carbon dioxide to high amounts of lipids that can be used for biofuel production. This paper describes the possibility of using Desmodesmus sp. (I-AU1) for biodiesel production by evaluating its fatty acid profile distribution pattern and estimating the fuel-derived physical and chemical properties from fatty acid methyl esters (FAMEs) obtained from the trans-esterified microalgal oil. Growth rate, oil content, biomass, and lipid productivity of the algal strain have been investigated under nitrogen-starved (0.375 g L−1 NaNO3 in BG 11 medium) autotrophic condition for 22 days. Maximum average biomass yield of Desmodesmus sp. (I-AU1) is 0.745 g L−1 having 36.14% lipid content per dry weight of biomass, with a specific growth rate of 0.20 day−1. Fatty acid profiling of the biodiesel obtained from Desmodesmus sp. (I-AU1) contained total saturated fatty acid (SAFA) methyl esters of 31.02%, while the total monounsaturated fatty acid (MUFA) (C18:1) is 25.64%. Percentage composition of SAFA and MUFA for the microalga was 56.66%, which is high compared to that of most of related studies. Fuel properties were determined by empirical equations and were found to be within the limits of biodiesel standards ASTM D6751 (American) and EN 14214 (European). The quality properties of the biodiesel were low density (0.88 g cm−3), low kinematic viscosity (2.81 mm2 s−1), cetane number (43.47), oxidation stability (5.96 h), and cold filter plugging point (−7.41 °C). Hence, Desmodesmus sp. (I-AU1) has potential as a feedstock for the production of quality biodiesel.

Photofermentaion and lipid accumulation by Rhodobacter sp. KKU-PS1 using malic acid as a substrate

Photofermentation and lipid accumulation by the purple non-sulfur photosynthetic bacterium, Rhodobacter sp. KKU-PS1, from malic acid was investigated in batch fermentation. Media compositions including malic acid concentration, glutamate concentration, amount of vitamin addition and Fe concentration were optimized by response surface methodology with central composite design in order to achieve a maximum hydrogen production rate (Rm). The predicted Rm of 11.7 mL H2/L. h was obtained under optimal media compositions of 2.36 g/L malic acid, 224 mg/L glutamate, and 13.5 mL/L of vitamin solution addition along with 64 mg/L of Fe. The cellular lipid content in Rhodobacter sp. KKU-PS1 was checked at the end of photo-fermentative process. A nitrogen limited condition was suitable for lipid accumulation by Rhodobacter sp. KKU-PS1. A maximum lipid production of approximately 592 mg/L was obtained with 4.7 g/L malic acid, 159 mg/L glutamate, 21.7 mL/L of vitamin solution along with 330 mg/L Fe (equivalent to C/N ratio of 132). Triacylglycerol (TAG) was the major component of the lipid in which the predominant fatty acid was octadecanoic acid (C18:1) in the form of oleic acid (C18:1n-9). The physicochemical properties of biodiesel predicted from fatty acid methyl esters (FAMEs) compositions of lipid produced by Rhodobacter sp. KKU-PS1 under the suitable conditions indicated that the lipid produced by the strain KKU-PS1 has a fairly good potential for use as biodiesel.

An enhanced procedure for measuring organic acids and methyl esters in PM<sub>2.5</sub>

Abstract. A solid-phase extraction (SPE) pretreatment procedure allowing organic acids to be separated from methyl esters in fine aerosol has been developed. The procedure first separates the organic acids from fatty acid methyl esters (FAMEs) and other nonacid organic compounds by aminopropyl-based SPE cartridge and then quantifies them by gas chromatography/mass spectrometry. The procedure prevents the fatty acids and dimethyl phthalate from being overestimated, and so allows us to accurately quantify the C4–C11 dicarboxylic acids (DCAs) and the C8–C30 monocarboxylic acids (MCAs). Results for the extraction of DCAs, MCAs, and AMAs in eluate and FAMEs in effluate by SAX and NH2 SPE cartridges exhibited that the NH2 SPE cartridge gave higher extraction efficiency than the SAX cartridge. The recoveries of analytes ranged from 67.5 to 111.3 %, and the RSD ranged from 0.7 to 10.9 %. The resulting correlations between the aliphatic acids and FAMEs suggest that the FAMEs had sources similar to those of the carboxylic acids, or were formed by esterifying carboxylic acids, or that aliphatic acids were formed by hydrolyzing FAMEs. Through extraction and cleanup using this procedure, 17 aromatic acids in eluate were identified and quantified by gas chromatography/tandem mass spectrometry, including five polycyclic aromatic hydrocarbon (PAH): acids 2-naphthoic, biphenyl-4-carboxylic, 9-oxo-9H-fluorene-1-carboxylic, biphenyl-4,4´-dicarboxylic, and phenanthrene-1-carboxylic acid, plus 1,8-naphthalic anhydride. Correlations between the PAH acids and the dicarboxylic and aromatic acids suggested that the first three acids and 1,8-naphthalic anhydride were secondary atmospheric photochemistry products and the last two mainly primary.

Synthesis and application of fatty acid derived templates for the preparation of mesostructured silica material

Bio-Organic-Salts (BOSs) synthesized from fatty acid methyl esters (FAMESs) have been developed for use as a bio-derived template for mesostructured material.

Effects of household detergent on anaerobic fermentation of kitchen wastewater from food waste disposer

This study examines the effects of household detergent on anaerobic methane fermentation of wastewater from food waste disposers (FWDs). Anaerobic toxicity assay (ATA) demonstrated that methane production substantially decreased at a higher detergent concentration. The Gompertz three-parameter model fitted well with the ATA results, and both the extent of methane production (M) and methane production rate (Rm) obtained from the model were strongly affected by the concentration of the detergent. The 50% inhibitory concentration (IC50) of the detergent was 603mg/L based on Rm. Results from fatty acid methyl esters (FAMEs) analysis of microbial culture revealed that deterioration of methane fermentation was attributed to impaired structure of anaerobic microbial membrane due to detergent. This study suggests that wastewater from FWD could be used for methane production, but it is necessary to reduce the concentration of detergent prior to anaerobic fermentation.

Regiospecific synthesis of new fatty N-acyl trihalomethylated pyrazoline derivatives from fatty acid methyl esters (FAMEs)

A series of new fatty N-acyl trihalomethylated pyrazoline derivatives from fatty acid methyl esters was synthesized by the cyclocondensation of respective fatty hydrazides with 4-alkoxy-1,1,1-trialomethyl-3-alquen-2-ones. Efficient and regiospecific cyclizations catalyzed by BF3·MeOH gave the desired products in good to excellent yields and at high purity.

Síntese de novas amidas graxas a partir da aminólise de ésteres metílicos

Recent biochemical and pharmacological studies have led to the characterization of different fatty acid amides as a new family of biologically active lipids. Here, we describe the synthesis of new amides from C16:0, 18:0, 18:1 and 18:1, OH fatty acids (FFA) families with cyclic and acyclic amines and demonstrate for the first time that these compounds produce citotoxic effects. Application of this method to the synthesis of fatty acid amides was performed using the esters aminolysis as a key step and various carboxylic amides were prepared in good yield from fatty acid methyl esters (FAMEs).

Melting Characteristics and Hardness of Milkfat Blend Sucrose Polyesters

ABSTRACTSucrose polyesters (SPE) are noncaloric fat substitutes prepared from fatty acid methyl esters (FAME) and sucrose. Our objectives were to determine and compare the effects of supplementing FAME from hydrolyzed milkfat with 25% FAME derived from beef tallow, coconut oil, or myristic acid on melting characteristics, hardness, and fatty acid profiles of SPE. DSC thermograms revealed different melting profiles among the SPE and anhydrous milkfat. Milkfat:tallow, milkfat:coconut, and milkfat SPE differed (p<0.05) in hardness from milkfat at 12.5, 22, and 27.5°C. Fatty acid compositions of the SPE were also different. Adjustments of melting characteristics, hardness, and fatty acid substituents of SPE are essential when substituting milkfat SPE for selected natural fats in foods.

Location of double bonds in polyunsaturated fatty acids by gas chromatography-mass spectrometry after 4,4-dimethyloxazoline derivatization

The location of double bonds in polyunsaturated fatty acids is determined by gas chromatography-mass spectrometry after 4,4-dimethyloxazoline (DMOX) derivatization. A procedure for DMOX preparation, starting from fatty acid methyl esters (FAMEs) is proposed. The most interesting properties of these derivatives are presented especially for the analysis of long-chain polyenoic fatty acids. The use of DMOX derivatives in combination with FAMEs can be very useful for the identification of fatty acids in unknown samples.