Soy oil conjugated linoleic acid production with solar light photoisomerization.

The objectives were (1) to produce soy oil conjugated linoleic acid (CLA) triacylglycerides in large quantities with solar light photoisomerization, utilizing iodine as a photosensitizer, (2) to study the temperature variation in the photoisomerized oil during various hours of the day, and (3) to study the variations in solar light intensity during various hours of the day. A 0.5% iodine containing soy oil in glass box with a glass lid was photoisomerized, under natural solar light for 0, 11, and 27 days, and CLA isomers were determined with gas chromatography with flame ionization detector. After 27 days of solar light photoisomerization, the cis-9, trans-11 CLA; other cis, trans CLA; trans-10, cis-12 CLA; trans, trans CLA, and total CLA were found to be 0.62 ± 0.05%, 1.04 ± 0.09%, 0.54 ± 0.11%, 6.16 ± 0.68%, and 8.37 ± 0.90%, respectively. The concentration of CLA isomers between 0 and 11 days was significantly different (p < .05), and the concentration of CLA isomers between 0 and 27 days was also significantly different (p < .05). There is no significant difference (p > .05) in CLA concentration between 11 and 27 days treatment. The CLA was not found in control soy oil samples. The CLA isomers were measured with GDFID in 45 min instead of 120min. The temperature of the edible oil in glass boxes ranged from 26 °C (8 a.m.) to 56 °C (1 p.m.). The light intensity ranged from 4,146 lux (7 p.m.) to 95,490 lux (12 p.m.). Glass lid on the glass box affected light transmission to a small but statistically significant extent (p < .05). The CLA isomers could be energy efficiently and inexpensively produced in soy oil by solar light photoisomerization, at low temperature and without needing expensive reactor vessels or catalysts. PRACTICAL APPLICATION: CLA was produced effectively with the iodine sensitized solar light photoisomerization. CLA is produced in large quantities, inexpensively, for possible food additive applications. Produced CLA is in the form of stable triacylglycerides.

Effects of gamma irradiation on aflatoxin B1 levels in soybean and on the properties of soybean and soybean oil.

Fungal infection is inevitable in the cultivation and storage process of soybean. Gamma irradiation is an effective method to control fungal growth and inactivate mycotoxins. The effects of gamma irradiation and fungal damage on the number of fungi, aflatoxin B1 content, proximate composition of soybeans, and quality of soybean oil (acid value, peroxide value, iodine value, fatty acid profile, tocopherols content, and oxidation stability) were investigated in this work. Growth of fungi caused some changes in proximate composition of soybean and qualities of soybean oil. However, the changes depended on the damage extent of soybeans. No significant change was found for the soybeans incubated for 30 days (moderately fungi-damaged). Gamma irradiation could completely eliminate the fungi and greatly reduce the content of aflatoxin B1 in soybeans at 10 kGy. For soybeans incubated for 30 days, there were no significant changes in the quality attributes, tocopherols content and oxidation stability of oil when the gamma irradiation dose was less than 20 kGy. Gamma irradiation is a promising method to improve the safety and economy of moderately fungi-damaged soybean used for feedstuff.

Sonocrystallization of Interesterified Soybean Oil: Effect of Saturation Level and Supercooling.

The aim of this study was to investigate the effects of supercooling and degree of saturation on lipid sonocrystallization under similar driving force of crystallization. Samples consisting of 100%, 50%, and 20% interesterified soybean oil (IESBO) diluted in high-oleic sunflower oil (HOSFO) were crystallized with and without high-intensity ultrasound (HIU). Two power levels were used by changing the amplitude of vibration of the tip (24 µm and 108 µm of tip amplitude). HIU operating at a frequency of 20 kHz was applied for 10 s. Sonication induced crystallization in the 100% IESBO sample and sonication power did not affect the results. A greater induction in crystallization was observed when higher power levels were used in the 50% IESBO sample, while no effect was observed in the crystallization kinetics of the 20% IESBO samples. Changes in the crystallization kinetics affected physical properties of the material, influencing elasticity. For example, sonication increased the elasticity of the 100% IESBO sample for both tip amplitudes from 435.9 ± 173.3 Pa to 72735.0 ± 9547.9 Pa for the nonsonicated and sonicated samples using 108 µm of amplitude, respectively. However, sonication only increased the elasticity in the 50% sample when used at the higher power level of 108 µm from 564.2 ± 175.2 Pa to 21774.0 ± 5694.9 Pa, and it did not affect the elasticity of the 20% IESBO samples. These results show that the level of saturation and the degree of supercooling affect sonication efficiency. PRACTICAL APPLICATIONS: High-intensity ultrasound (HIU) has been used as a novel method for changing the crystallization behavior of fats. HIU can be used to improve the physical properties of trans-free fats that are low in saturated fatty acids. Although recent studies have proven the effectiveness of this method to induce crystallization, the process must still be optimized to the industrial setting. All process parameters should be considered during the application of HIU, as they directly affect the final product. The aim of this paper was to investigate the effects of HIU and process conditions such as tip amplitude, degree of supercooling, and saturation level on the crystallization behavior of commercial interesterified soybean oil.

Effect of Furan Fatty Acids and 3-Methyl-2,4-nonanedione on Light-Induced Off-Odor in Soybean Oil.

Soybean oil is one of the most widely consumed vegetable oils. However, under photooxidative conditions, this oil develops a beany and green off-odor through a mechanism that has not yet been elucidated. Upon photooxidation, 3-methyl-2,4-nonanedione (3-MND) produces a strong aroma. In this study, the effect of furan fatty acids and 3-MND on odor reversion in soybean oil was investigated. Our findings suggest that the observed light-induced off-odor was likely attributable to the furan fatty acids present in the oil through the generation of 3-MND. While 3-MND may not be directly responsible for the development of light-induced off-odor, this compound appears to be involved because off-odor was detected in canola oil samples containing added 3-MND. In addition, in the present work, 3-hydroxy-3-methyl-2,4-nonanedione, which is derived from 3-MND, was identified for the first time in light-exposed soybean oil and shown to be one of the compounds responsible for odor reversion.

Ultrasound-assisted production of biodiesel from soybean oil using Brønsted acidic ionic liquid as catalyst.

Biodiesel production from soybean oil with methanol was performed in the presence of a Brønsted acidic ionic liquid-based catalyst under ultrasound irradiation. The influences of various parameters on the transesterification reaction, including the amount of catalyst, the molar ratio of methanol to oil, the temperature and the ultrasound power, were investigated. The optimal conditions were: methanol/oil molar ratio of 9:1, 1.0 wt.% catalyst in oil, ultrasound power of 200 W, and reaction temperature of 60°C. Under these conditions, the conversion of triglycerides to fatty acid methyl esters was about 93.2% within the reaction time of 60 min.

Effect of γ irradiation on the fatty acid composition of soybean and soybean oil.

Food irradiation is a form of food processing to extend the shelf life and reduce spoilage of food. We examined the effects of γ radiation on the fatty acid composition, lipid peroxidation level, and antioxidative activity of soybean and soybean oil which both contain a large amount of unsaturated fatty acids. Irradiation at 10 to 80 kGy under aerobic conditions did not markedly change the fatty acid composition of soybean. While 10-kGy irradiation did not markedly affect the fatty acid composition of soybean oil under either aerobic or anaerobic conditions, 40-kGy irradiation considerably altered the fatty acid composition of soybean oil under aerobic conditions, but not under anaerobic conditions. Moreover, 40-kGy irradiation produced a significant amount of trans fatty acids under aerobic conditions, but not under anaerobic conditions. Irradiating soybean oil induced lipid peroxidation and reduced the radical scavenging activity under aerobic conditions, but had no effect under anaerobic conditions. These results indicate that the fatty acid composition of soybean was not markedly affected by radiation at 10 kGy, and that anaerobic conditions reduced the degradation of soybean oil that occurred with high doses of γ radiation.

Ultrasound-assisted lipase-catalyzed transesterification of soybean oil in organic solvent system.

This work reports the transesterification of soybean oil with ethanol using two commercial immobilized lipases under the influence of ultrasound irradiation. The experiments were performed in an ultrasonic water bath, following a sequence of experimental designs to assess the effects of temperature, enzyme and water concentrations, oil to ethanol molar ratio and output irradiation power on the reaction yield. Results show that ultrasound-assisted lipase-catalyzed transesterification of soybean oil with ethanol might be a potential alternative route to conventional alkali-catalyzed method, as high reaction yields (~90 wt.%) were obtained at mild irradiation power supply (~100 W), and temperature (60 °C) in a relatively short reaction time, 4h, using Lipozyme RM IM as catalyst. The repeated use of the catalyst under the optimum experimental condition resulted in a decay in both enzyme activity and product conversion after two cycles. The use of Novozym 435 led to lower conversions (about 57%) but the enzyme activity was stable after eight cycles of use, showing, however, a reduction in product conversion after the forth cycle.

The effect of ultrasound on lipase-catalyzed hydrolysis of soy oil in solvent-free system.

Comparative studies of lipase-catalyzed hydrolysis of soy oil in solvent-free system were carried out in shaking bath and in ultrasonic bath. A suitable ultrasonic power of 1.64 W cm(-2) was determined to guarantee satisfactory hydrolysis extent and lipase activity. The influence of temperature, pH, enzyme concentration and water/oil ratio was investigated subsequently. Compared with that in shaking bath, optimum temperature and inactivation temperature of lipase in ultrasonic bath were about 5-10 degrees C higher, while pH effect in ultrasonic bath was similar; ultrasound also led to a smooth increase of reaction rate at relatively higher enzyme loading and less use of water to saturate hydrolysis substrate. In optimum conditions, the overall hydrolysis reaction rate in the ultrasonic bath process was above 2-fold than that in the shaking bath process.

Kinetics of photoirradiation-induced synthesis of soy oil-conjugated linoleic acid isomers.

Photoirradiation of soy oil with UV/visible light has been shown to produce significant amounts of trans,trans conjugated linoleic acid (CLA) isomers through conversion of various synthesized intermediate cis,trans isomers. The objective of this study was to determine the kinetics of CLA isomers synthesis to better understand the production of various isomers. Soy oil was irradiated with UV/visible light for 144 h in the presence of an iodine catalyst and CLA isomers analyzed by gas chromatography (GC). Arrhenius plots were developed for the conversion of soy oil linoleic acid (A) to form cis-, trans/trans-, cis-CLA (B), conversion of cis-, trans/trans-, cis-CLA to form trans,trans-CLA (C) with respect to B, and formation of trans,trans-CLA isomers with respect to C. The kinetics of consumption of linoleic acid (LA) to form cis-, trans/trans-, cis-CLA was found to be of second-order with a rate constant of 9.01 x 10-7 L/mol s. The rate of formation of cis-, trans/trans-, cis-CLA isomers depends on the rate of formation from LA and its rate of consumption to form trans,trans-CLA isomers. The conversion of cis-, trans/trans-, cis-CLA isomers to trans,trans-CLA isomers was found to be of first-order with a rate constant of 2.75 x 10-6 s-1. However, the formation of thermodynamically stable trans,trans-CLA isomers (C) with respect to C was found to be a zero-order reaction with a rate constant of 10.66 x 10-7 mol/L s. The consumption of LA was found to be the rate-determining step in the CLA isomers formation reaction mechanism. The findings provide a better understanding of the mechanism of CLA isomers synthesis by photoirradiation and the factors controlling the ratio of various isomers.

Photochemical production of conjugated linoleic acid from soybean oil.

Conjugated linoleic acid (CLA), an anticarcinogenic compound with numerous other health benefits, is present mainly in dairy and beef lipids. The main CLA isomer present in dairy and beef lipids is cis 9, trans 11 CLA at a 0.5% concentration. The typical minimum human dietary intake of CLA is 10 times less than the 3 g/d suggested requirement that has been extrapolated from animal and cell-line studies. The objectives of this study were to produce CLA isomers from soybean oil by photoisomerization of soybean oil linoleic acid and to study the oxidation status of the oil. Refined, bleached, and deodorized soybean oil with added iodine concentrations of 0, 0.1, 0.25, and 0.5% was exposed to a 100-W mercury lamp for 0 to 120 h. An SP-2560 fused-silica capillary GC column with FID was used to analyze the esterified CLA isomers in the photoisomerized oil. The CLA content of the individual isomers was optimized by response surface methodology. Attenuated total reflectance (ATR)-FTIR spectra in the 3400 to 3600 cm(-1) range and 1H NMR spectra in the 8 to 12 ppm range of the photoisomerized soybean oil were obtained to follow hydroperoxide formation. The largest amount of cis 9, trans 11 CLA isomer in soybean oil was 0.6%, obtained with 0.25% iodine and 84 h of photoisomerization. Lipid hydroperoxide peaks in the ATR-FTIR spectra and aldehyde peaks in the 1H NMR spectra were not observed in the photoisomerized soybean oil, and the spectra were similar to that of fresh soybean oil. This study shows that CLA isomers can be produced simply and inexpensively from soybean oil by photoisomerization.