Glycidyl esters of epoxidized fatty acids derived from soybean oil (EGS) and linseed oil (EGL) have been syn- thesized to have higher oxirane content, more reactivity and lower viscosity than epoxidized soybean oil (ESO) or epoxi- dized linseed oil (ELO). The EGS and ESO, for comparison, were used neat and in blends with diglycidyl ether of bisphenol A (DGEBA). Thermosetting resins were fabricated with the epoxy monomers and either BF3 catalyst or anhy- dride. The curing behaviors, glass transition temperatures, crosslink densities and mechanical properties were tested. The results indicated that polymer glass transition temperatures were mostly a function of oxirane content with additional influ- ence of glycidyl versus internal oxirane reactivity, pendant chain content, and chemical structure and presence of saturated components. EGS provided better compatibility with DGEBA, improved intermolecular crosslinking and glass transition temperature, and yielded mechanically stronger polymerized materials than materials obtained using ESO. Other benefits of the EGS resin blend systems were significantly reduced viscosities compared to either DGEBA or ESO-blended DGEBA counterparts. Therefore, EGS that is derived from renewable sources has improved potential for fabrication of structural and structurally complex epoxy composites, e.g., by vacuum-assisted resin transfer molding.

/pdf/vegetable-oil-derived-epoxy-monomers-and-polymer-blends-a-42wqapvzf7.pdf

Vegetable Oil-derived Epoxy Monomers and Polymer Blends: A Comparative Study with Review

Structured lipids (SLs) are lipids that have been chemically or enzymatically modified from their natural biosynthetic form. Because SLs are made to possess desired nutritional, physicochemical, or textural properties for various applications in the food industry, many research activities have been aimed at their commercialization. The production of SLs by enzymatic procedures has a great potential in the future market because of the specificity of lipases and phospholipases used as the biocatalysts. The aim of this review is to provide concise information on the recent research trends on the enzymatic synthesis of SLs of commercial interest, such as medium- and long-chain triacylglycerols, human milk fat substitutes, cocoa butter equivalents, trans-free or low-trans plastic fats (such as margarines and shortenings), low-calorie fats/oils, health-beneficial fatty acid-rich fats/oils, mono- or diacylglycerols, and structurally modified phospholipids. This limited review covers 108 research articles published between 2010 and 2014 which were searched in Web of Science.

Recent Research Trends on the Enzymatic Synthesis of Structured Lipids

EPA (eicosapentaenoic acid) and DHA (docosahexaenoic acid) products have been widely applied due to their medical and healthcare value. In this paper, the methods for extracting DHA and EPA from microalgae and related purification methods were summarized and analyzed. The yields of DHA and EPA from different species of microalgae were investigated. The optimal extraction and purification methods and microalgae species that are suitable for the extraction of EPA and DHA products were determined. Currently, organic solvents are extensively used to extract oil from microalgal biomasses. The supercritical fluid extraction technique is an ideal method for lipid extraction. Based on the findings presented in this paper, a combination of multiple methods is a better choice to extract and purify EPA and DHA from microalgae.

Extraction and purification of eicosapentaenoic acid and docosahexaenoic acid from microalgae: A critical review

Structured lipid (SL) enriched with arachidonic (ARA) and docosahexaenoic (DHA) acids was produced from tripalmitin using Lipozyme TL IM. The effects of acyl donors, that is, free fatty acids vs fatty acid ethyl esters, on the reactions were compared. The highest total incorporation of ARA and DHA was obtained when the reaction continued for 24 h, at a substrate mole ratio of 9, using free fatty acids as acyl donors (acidolysis). The SL prepared by a large-scale acidolysis reaction contained 17.69 ± 0.09% total ARA, 10.75 ± 0.15% total DHA, and 48.53 ± 1.40% sn-2 palmitic acid. SL thermograms exhibited multiple peaks indicating complexity of the triacylglycerol (TAG) distribution. RP-HPLC analysis of SL revealed nine of 26 TAG molecular species that were similar to those of human milk fat. Powdered infant formulas containing the SL were prepared by wet-mixing/spray-drying and dry-blending methods. Formula prepared with microencapsulated SL and the dry-blending method had better oxidative stability and col...

Synthesis of structured lipid enriched with omega fatty acids and sn-2 palmitic acid by enzymatic esterification and its incorporation in powdered infant formula.

Well over 1,000 different fatty acids are known which are natural components of fats, oils (triacylglycerols), and other related compounds (Gunstone & Norris, 1983). These fatty acids can have different alkyl chain lengths (typically ten or more carbon atoms), 0-6 carbon-carbon double bonds posessing

/pdf/distillation-of-natural-fatty-acids-and-their-chemical-49jfofhq9a.pdf

Distillation of Natural Fatty Acids and Their Chemical Derivatives

Enrichment of stearidonic acid in modified soybean oil by low temperature crystallisation

The concentration of stearidonic acid (SDA, 18:4 ω-3) in free fatty acid (FFA) and fatty acid ethyl ester (FAEE) forms by low temperature crystallization (winterization) was studied. For this purpose, modified soybean oil (initial SDA content, ~23%) was transformed into its corresponding FFA and FAEE by chemical hydrolysis and ethanolysis, respectively. In the first study, the FFA and FAEE were used as starting material for winterization and variables such as winterization time, type of solvent, and the oil:solvent ratio were evaluated until optimization of the process was achieved. In the second study, changes in the winterization procedure were introduced to obtain a remarkable improvement on the SDA purity of the final products. Since winterization of FAEE was not efficient due to its low melting points, the second study focused on FFA. The best relationship between SDA purity (59.8%) and SDA yield (82.3%) was attained by performing winterization of FFA with hexane at 10% oil:solvent ratio for 24 h. Scaled-up processes were also performed to obtain 59 g of FFA (purity 59.6%; yield 82.6%) enriched in SDA. The products obtained can be used as starting materials for the production of functional lipids and for clinical trials.

Concentration of Stearidonic Acid in Free Fatty Acid and Fatty Acid Ethyl Ester Forms from Modified Soybean Oil by Winterization

The main objective of the present work was to obtain fractions enriched in short (SCFAEE) and medium chain (MCFAEE) fatty acid ethyl esters (FAEE) from a blend of oils. For this purpose, coconut oil and dairy fat were blended and a transesterification of this blend was performed in order to transform the triacylglycerols into their corresponding FAEE. A detailed study of fractionation conditions for FAEE was carried out using short-path distillation. Different conditions were explored such as feed rates and temperatures; operating conditions, such as successive steps or a single step. The composition and yield of SCFAEE and MCFAEE were determined under different distillation conditions. Optimal fractionation of the desired compounds was achieved. High purity of SCFAEE and MCFAEE (94 wt%) was attained with a yield of ~50%. An increased yield of SCFAEE and MCFAEE was achieved (85%) with a purity of 83 wt%. A broad range of high value fractions was obtained depending on the conditions selected. The fractions we obtained can be used as starting materials for the production of functional lipids.

Fractionation of Short and Medium Chain Fatty Acid Ethyl Esters from a Blend of Oils via Ethanolysis and Short-Path Distillation

The concentration of stearidonic acid (SDA, 18:4 n-3) in free fatty acids (FFA) formed by selective esterification with dodecanol (lauryl alcohol) was studied. For this purpose, modified soybean oil (initial SDA content, ~23 %) was converted into its corresponding FFA by chemical hydrolysis. In a second step, the resulting FFA were esterified with dodecanol. Process variables such as the type of biocatalyst (lipase), substrate molar ratio and amount of lipase were evaluated. The best SDA concentration (58 %) and recovery (94 %) were attained by performing the esterification reaction for 4 h, with 1:1 molar ratio (dodecanol:FFA), and 5 % (w/w) Candida rugosa lipase as biocatalyst. It was observed that SDA was concentrated in the unesterified fraction.

Concentration of Stearidonic Acid in Free Fatty Acids Form from Modified Soybean Oil by Selective Esterification with Dodecanol

The objective of this study was to purify stearidonic acid (SDA, 18:4 ω-3) from modified soybean oil containing a mixture of over 20 fatty acids (23% SDA) Interest in obtaining purified fractions of SDA arises from reported health benefits associated with polyunsaturated fatty acids (PUFA), such as cardiovascular disease prevention In addition, SDA may also provide improved stability characteristics since its unsaturation index is less than longer PUFA, such as eicosapentaenoic acid (EPA, 20:5 ω-3) First, a chemical ethanolysis of modified soybean oil was performed to transform the triacylglycerols into fatty acid ethyl esters (FAEE) Then, the FAEE were fractionated and SDA-EE was purified by argentation silica gel (10% AgNO3) open column chromatography, which allows selectivity based on degree of unsaturation Different FAEE sample loads and mobile phases were explored until the best purification of SDA-EE was achieved The solvents used were hexane and hexane:acetone mixtures (99 and 95%) Under the optimal conditions, a fraction with high SDA-EE purity (96%) was obtained with 77% yield Besides, it was possible to obtain another fraction enriched in α-linolenic acid-EE (37% purity and 68% yield) and γ-linolenic acid-EE (22% purity and 61% yield) A scaled-up process resulted in 840 mg of final product composed of 97% SDA-EE with 71% yield

Purification of Stearidonic Acid from Modified Soybean Oil by Argentation Silica Gel Column Chromatography

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