Interesterification Of Soybean Oil Research Articles

Interesterification of triglycerides with methyl acetate for the co-production biodiesel and triacetin using hydrotalcite as a heterogenous base catalyst

Biodiesel is a renewable fuel with several advantages over petro-based fuels and is conventionally produced by the transesterification of triglycerides with alcohols. Chemical interesterification of triglycerides is a good alternative as compared to transesterification, as it yields a value-added compound, triacetin, as a co-product instead of the already abundant commodity, glycerol. In this work, interesterification of soybean oil was carried out with methyl acetate to co-produce biodiesel and triacetin, using calcined hydrotalcite as a heterogeneous base catalyst. Several base catalysts were tested for this reaction. Calcined Mg-Al hydrotalcite (Mg:Al mole ratio – 3:1) was found as the best catalyst for achieving 95.9 % conversion of soybean oil triglycerides in 4 h and yielding 5.3 % selectivity of triacetin along with the value-added intermediates - monoacetindiglycerides and diacetinmonoglycerides, produced with a selectivity of 46 % and 48.7 %, respectively. The optimum reaction conditions were found at an oil to methyl acetate mole ratio of 1:50, catalyst loading of 0.04 g/cm3 and a temperature of 200 ºC. The catalysts were fully characterized before and after the reaction, and were found to possess high surface area with both basic and acidic sites. The effect of various reaction conditions on the rate of reaction, conversion of triglycerides and selectivity of triacetin were studied. The concentration profiles of the reactants, intermediates and products obtained at different temperatures were used to obtain the kinetic rate constants and the activation energy of each parallel step was evaluated. Reusability studies showed that the catalyst was stable and reusable up to three cycles.

Interesterification of Soybean Oil with Propylene Glycol in Supercritical Carbon Dioxide and Analysis by NMR Spectroscopy.

The time course study of high monoester mixtures from soybean oil (HMMS) synthesis, as healthier alternatives to trans food products, in a supercritical CO2 (SCCO2) medium with and without enzyme, was investigated. Phosphorous nuclear magnetic resonance (31P-NMR) was used to quantify the absolute amount of partially esterified acylglycerols (PEGs). Carbon NMR was utilized to determine the type and position of the fatty acids (FAs) of HMMS. Enzyme and time significantly influenced the synthesis of 1-monoglycerides (1-MGs), 2-MGs, and 1,2-diglycerides (1,2-DGs) in this alcoholysis of soybean oil with 1,2-propanediol, based on high catalytic activity and operational stability of Novozym 435 in SCCO2 during short reaction time. Results suggest that 4h is a suitable reaction time for this lipase-catalyzed interesterification (LIE) system for the synthesis of 2-MGs with a yield of 20%. The highest polyunsaturated fatty acid (PUFA) (65%) in the triglyceride (TG) of HMMS was produced after 4h of reaction. After 6h of reaction, a high level (20%) of saturated fatty acids (SFAs) was found in the TGs of HMMS, which were distributed between the sn-2 (5%) and sn-1, 3 (15%) positions.

Production of trans‐free margarine fat by enzymatic interesterification of soy bean oil, palm stearin and coconut stearin blend

AbstractTrans‐free structure lipids (SLs) were prepared from enzymatic interesterification (EI) of soybean oil (SBO), palm stearin (PS) and coconut stearin (CNS) blends in different ratios (0:70:30, 10:60:30, 20:50:30, 30:40:30 and 40:30:30% wt.) using Lipozyme RM IM at 65 °C for 8 h. After EI, the fatty acid composition of the SLs exhibited no change from the physical blends (PBs). Medium‐chain fatty acid was incorporated into the triacylglycerol of the SLs. The melting completion temperature decreased from 50–54 °C of PBs to 32–44 °C of SLs with a reduction in solid fat content. The small needle‐shaped crystals were observed in the SL samples. SL obtained from EI of 20:50:30 (SBO:PS:CNO) blend exhibited the highest potential to be used as a trans‐free margarine fat as it showed a similar SFC curve to the commercial margarine fat and crystallised into β′ polymorphic form.

Interesterification of Soybean Oil and Methyl Stearate Catalyzed by Guanidine‐Functionalized SBA‐15 Silica

AbstractThe main purpose of this study was to develop a heterogeneous interesterification catalyst for the modification of edible oils to enhance their physicochemical and functional performances. To achieve this, 1,3‐dicyclohexyl‐2‐octylguanidine was covalently immobilized on the SBA‐15 (Santa Barbara Amorphous 15) material and then used as solid catalysts for the interesterification between soybean oil and methyl stearate. The characterization of the guanidine‐functionalized SBA‐15 material included Fourier transform infrared spectra, scanning electron microscopy, elemental analysis, and nitrogen adsorption–desorption techniques. It was shown that the solid base catalyst could efficiently catalyze the interesterification reaction. After the interesterification, the fatty acid profiles and triacylglycerol compositions of interesterified products were substantially varied. The influence of interesterification parameters, such as the substrate ratio, reaction time, reaction temperature and catalyst loading, on the interesterification reaction was investigated regarding the percentage of stearic acid in interesterified triacylglycerols. The stearic acid percentage of 27.9 % was achieved at 100 °C within 4 h when the methyl stearate/soybean oil molar ratio of 6:1 was employed. The catalyst could be recovered easily by filtration and reused without significant loss of activity.

Sn-1,3-specific Interesterification of Soybean Oil with Medium-chain Triacylglycerol Catalyzed by Lipozyme TL IM

The structured lipids are produced through sn-1,3-specific interesterification of soybean oil with medium-chain triacylglycerol (MCT) in continuous reactions catalyzed by Thermomyces lanuginose lipase (Lipozyme TL IM). Cheap Lipozyme TL IM presents similar interesterification degree (ID), sn-1,3-specificity and residual activity as expensive Rhizomucor miehei in batch reactions. In packed-bed interesterification of soybean oil with MCT catalyzed by Lipozyme TL IM, the residence time has a significant effect on ID, while temperature has a small effect at 45–70°C. The sn-1,3-specificity of Lipozyme TL IM is not satisfactory when reaction temperature is higher than 60°C. The optimal residence time and temperature are 30–40min and 55°C, respectively. Among the solvents, including acetone, isopropanol, tert-butanol, and isobutanol, used to recover the activity of the used Lipozyme TL IM, acetone is the most suitable one than the other solvents.

Production tactic and physiochemical properties of low ω6/ω3 ratio structured lipid synthesised from perilla and soybean oil

Summary Structured lipid (SL) was synthesised by enzymatic interesterification of soybean oil and perilla oil. Response surface methodology (RSM) was used to determine the effects of three variables on the lipase-catalysed interesterification. Based on ridge analysis, combination of reaction time (X1; 18 h), reaction temperature (X2; 60 °C), and substrate mole ratio (X3; 1:1) were optimised for higher incorporation of ω3 (alpha (α) linolenic acid (ALA)) (Y). The predictive model was found to be adequate due to no significant lack of fit and satisfactory level of coefficient of determination (R2 = 0.97). Experiments were conducted under optimised conditions which were predicted by the model equations, obtained from RSM yielded SL with linoleic (44.01%) and ALA (35.82%) were detected at sn-2 position. The effects of antioxidants such as catechin, butylated hydroxytoluene (BHT) BHT and rosemary extracted on the oxidative stability in SL were investigated. Among all antioxidants, the highest stability was obtained from catechin.