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Silver nanoparticles (AgNPs) were synthesized using a sustainable green approach utilizing deodorizer distillates of canola (CODD) and soybean oil (SODD) as both reducing and capping agents. This synthesis approach resulted in the formation of pale-yellow colored CODD-AgNPs and SODD-AgNPs, which was confirmed by distinctive absorption peaks at 420 nm and 408 nm, respectively via Ultraviolet-Visible (UV–Vis) spectroscopy. Fourier Transform Infrared (FTIR) analysis provided insights into the functional group interactions between CODD and SODD with their AgNPs. X-ray diffraction (XRD) confirmed the face-centered cubic lattice structure of both CODD-AgNPs and SODD-AgNPs. Further characterization via Atomic Force Microscopy (AFM), Transmission Electron Microscopy (TEM), and Scanning Electron Microscopy (SEM) revealed the sizes, shapes, and surface morphologies of CODD-AgNPs and SODD-AgNPs. Assessment of antioxidant activity using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) method demonstrated superior radical scavenging efficacy by CODD-AgNPs (IC50 value 1.07±0.04 µg/mL) and SODD-AgNPs (IC50 value 1.14±0.23 µg/mL) compared to CODD and SODD. Evaluation of antibacterial properties against Escherichia coli (E. coli) and Staphylococcus aureus (S. aureus) via disc diffusion method revealed potent antibacterial activities of CODD-AgNPs and SODD-AgNPs at 100 µg/mL concentration, surpassing the antibacterial efficacy of CODD and SODD. Furthermore, CODD-AgNPs and SODD-AgNPs exhibited significant anti-inflammatory potential at 500 µg/mL concentration, with IC50 values of 187.2 ± 1.28 µg/mL and 203.9 ± 2.08 µg/mL, respectively, highlighting their potential therapeutic applications. In conclusion, this study demonstrates the effective utilization of CODD and SODD in synthesizing AgNPs with enhanced biological functionalities, making them promising candidates for various biomedical applications.

旨在为植物油脱臭馏出物（DD 油）相关标准的制定以及产品的开发提供参考，收集了全球35个不同工厂来源大宗油料的DD油，对其理化指标、不皂化物和危害因子进行分析。结果表明：35个DD油样品的酸值（KOH）为68.1～191.3 mg/g，过氧化值为0.043～0.149 g/100 g，水分及挥发物含量为0.18%～1.98%，灰分含量均小于0.3 g/100 g，皂化值（KOH）为125.0～205.8 mg/g，不皂化物含量为2.80%～35.71%；DD油样品的植物甾醇含量为0.81%～18.23%，维生素E含量为0.13%～9.23%，角鲨烯含量为0.09%～2.56%；DD油样品中PAH4总含量为6.74～61.98 μg/kg，6种邻苯二甲酸酯（DEP、DMP、DIBP、DBP、BBP、DEHP）总含量为1.12～17.57 mg/kg。不同DD油理化指标、维生素E和植物甾醇含量存在较大差异，且样品中多环芳烃和塑化剂的污染水平较高，在DD油相关标准的制定及产品开发的过程中应给予必要的关注。In order to provide reference for the formulation of relevant standards and product development of vegetable oil deodorizer distillate (DD oil), DD oil from 35 different factories around the world was collected and its physicochemical properties, unsaponifiable matter and hazard factors were analyzed. The results showed that the acid value of DD oil samples was 68.1-191.3 mgKOH/g, the peroxide value was 0.043-0.149 g/100 g, the moisture and volatile matter content was 0.18%-1.98%, the ash content was less than 0.3 g/100 g, the saponification value was 125.0-205.8 mgKOH/g, and the unsaponifible matter content was 2.80%-35.71%. The contents of phytosterol and squalene, vitamin E and squalene were 0.81%-18.23%, 0.13%-9.23% and 0.09%-2.56%, respectively. In addition, the total content of PAH4 in DD oil samples was 6.74-61.98 μg/kg, and the total content of six phthalates (DEP, DMP, DIBP, DBP, BBP, DEHP) was 1.12-17.57 mg/kg. The physicochemical properties, vitamin E and phytosterol contents of different DD oil are quite different, and the pollution level of polycycilic aromatic hydrocarbons and plasticizers in the samples is high. Therefore, necessary attention should be paid to the formulation of DD oil related standards and product development.

Background: A wiped‐film molecular distillation (WFMD) pilot plant was used to evaluate process conditions for enriching phytonutrients (PN) from a novel vegetable oil deodorizer distillate (VODD) of the margarine and shortenings industry. This byproduct results from the incorporation of new blends of vegetable oils, such as soybean and palm oil, making it of interest due to its distinct chemical composition and matrix, which differ from those of deodorizer distillates studied previously. The significance of the present investigation is related to the properties of the oil blend, requiring the establishment of new process conditions for this specific VODD. Experimental design was used to evaluate the WFMD process variables, with the aim of removing free fatty acids and enabling eight PN to be concentrated in the reprocessing stages. Results: The product obtained after three WFMD stages presented a fivefold increase in the total PN concentration, compared to the raw material. Notably, the procedure provided enrichment ratios of 7.2‐fold for total tocopherols (including α‐, β‐, λ‐ and δ‐tocopherols), 4.5‐fold for total phytosterols (including campesterol, stigmasterol and β‐sitosterol) and 1.2‐fold for squalene, together with a deacidification efficiency of 78.93%. Conclusion: The proposed process provided significant concentration gains for all eight PN evaluated, resulting in a value‐added product. These excellent results were achieved using only three WFMD stages, without any need for additional processing steps. The data obtained at the pilot scale provide valuable insights for predicting the scalability of the process and facilitating potential industrial implementation. © 2023 Society of Chemical Industry. [ABSTRACT FROM AUTHOR]

The deodorizer distillate (DD) is a byproduct of vegetable oil processing industry and is rich in functional bioactive components. This study aimed to employ phosphorylation modification for DD to produce a new sustainable fatliquor. The bioactive ingredients in DD, namely fatty acids, sterols, and tocopherols, were determined by using HPLC and GLC. The results revealed that the DD sample contained a high percentage of unsaturated fatty acids (72.3%) and high levels of γ and δ-tocopherols (54.8% and 31.60%, respectively). Mechanical parameters (tensile strength, elongation at break, and tear strength) of leather were improved after being treated with the prepared fatliquor emulsion. Eventually, SEM showed that the texture of the fatliquored leather had been remarkably enhanced. Moreover, the fatliquored leather possessed effective antibacterial effect against the specified +ve, −ve bacteria, and Candida albicans microorganisms. The strength, fullness, soft handle, and elasticity of leather were all improved, and the grain of leather was protected from becoming loose after drying. [ABSTRACT FROM AUTHOR]

An economical way to reduce oil consumption and environmental problems in fuel production is the production of biodiesel from by-products and waste materials. By-products from the vegetable oil refining industry such as soap stock, acid oil, and fatty acid distillates are suitable for biodiesel production. In this study, biodiesel production was made using deodorizer distillate, which is the last step of the sunflower oil refining stage. Sunflower oil deodorizer distillate (SODD) obtained from oil facilities in Thrace region, and it was examined whether the fuel characteristics of the produced biodiesel comply with EN 14214 and ASTM D6751 standards. Biodiesel production from SODD was based on acidic catalysis method. H2SO4 was used as catalyst and methanol as alcohol. Catalyst amount, methanol to SODD ratio, reaction temperature and reaction time parameters were studied and optimum conditions were determined. As a result of the studies, the highest biodiesel yield was obtained in 1 wt% H2SO4, 12:1 methanol to SODD ratio, 65 °C reaction temperature, and 9-h reaction time. Biodiesel achieved 98.98% methyl ester concentration and 94.32% biodiesel yield. In addition, comparison of fuel properties of synthesized biodiesel with ASTM D6751 and EN 14214 showed well-matched values. Our study thus recommends SODD as a non-edible potential feedstock for biofuel production and industrial purposes. [ABSTRACT FROM AUTHOR]

Tocopherols and tocotrienols in the combined form are known as tocols. Changes of total and individual tocols and sterols concentration of canola oil and deodorizer distillate (DD) during different processing stages were evaluated with the application of gas chromatography (GC) and high-performance liquid chromatography (HPLC). For sterols analysis, GC coupled with flame ionization detector (FID) was used while tocols in canola oil samples and DD, normal phase (NP) HPLC was applied. The results of the present study indicated that levels of total and individual tocols and sterols content were decreased during processing (neutralization to deodorization). Deodorization was found to be the most effective process for the reduction of total sterols and tocols as 55.9% and 34.2%, respectively. A high amount of tocols and sterols was observed in DD. Among tocols and sterols; beta tocopherol (ß-T) and ß-sitosterol were found to be in greater concentration 53.97% and 31.82%, respectively. Therefore, DD could be used as a valuable byproduct in the cosmetics and food industries. [ABSTRACT FROM AUTHOR]

In the present study, high-performance liquid chromatography (HPLC) was used for the separation of tocopherols and triglycerides of processed soybean oil and deodorizer distillate (DD). The results of normal and reversed-phase modes of HPLC revealed that concentrations of tocopherols and triglycerides content were decreased during the neutralization, bleaching, and deodorization processes. The loss of individual tocopherols ranged between 55.16% and 63.25%. During processing, triglycerides containing stearicoleic- linoleic (SOL) moieties and palmitic-palmitic-linoleic (PPL) fragments showed greater reduction up to 38.14% and 37.69%, respectively. Among tocopherols and triglycerides; -tocopherol and oleic-oleic-oleic (OOO) were found to be in greater concentrations 5.53% and 19.78%, respectively in DD as compared to their counterparts. A maximum reduction of tocopherols was observed in the deodorization step. DD was found to be a rich source of bioactive components; therefore, it could be used for many industrial applications including pharmaceutical formulations, cosmetics, and food industries. [ABSTRACT FROM AUTHOR]

Highlights • GC–MS methods for analysing PAHs and PAEs in vegetable oil DDs were established. • Total PAHs amounts in the test DDs were ranging from 115.77 to 966.40 μg/kg. • Total PAEs concentrations in the test DDs ranged from 2.45 to 24.52 mg/kg. • PAHs/PAEs contents in the DDs were significantly higher than those in the edible oils. Abstract In this study, simple GC–MS methods for analysising sixteen PAHs and seven PAEs were individually established. The LOQs for PAHs and PAEs were ranging from 0.18 to 0.42 μg/kg and 0.19 to 1.50 μg/kg, respectively. The recoveries for DD samples were in the range of 84.8–115.5% and 84.2–109.3% for PAHs and PAEs, respectively. Furthermore, PAHs and PAEs concentrations in soybean, rapeseed, corn and rice bran oil distillates were evaluated. PAHs were found in all the DD samples and the concentrations of BaP, PAH4 and total PAHs were 0.89–55.58, 8.11–326.07 and 115.77–966.40 μg/kg, respectively. Correspondingly, total PAEs concentrations ranged from 2.45 to 24.52 mg/kg, and the mean value was 7.76 mg/kg. The results illustrated that the contents of PAHs and PAEs in the DDs were extremely higher than those in the edible oils, thus indicating that specific issues should be considered in the vegetable oil DDs and DD-based products. [ABSTRACT FROM AUTHOR]

Biodiesel, a diesel fuel alternative, is produced from vegetable oils and animal fats by the transesterification reaction of triacylglycerols and lower aliphatic alcohols. Beside number advantages related to fossil fuels, the main barrier to biodiesel wider commercial use is the high price of edible oils. Recently, the special attention was given to side-stream products of edible oil refining as low-cost triacylglycerol sources for biodiesel production because of their positive economic and ecological effects. In this paper, the different procedures for biodiesel production from side-stream refining products such as soapstock, spent bleaching earth and deodorizer distillate were analyzed. The main goal of this paper is to analyze the possibilities for reusing the by-products of edible oil refinement in the biodiesel production.

In cases when the separation achieved by one molecular distillation stage is not sharp enough, it is resorted to multiple stage schemes. This brings the issue of how to recycle the intermediate streams to optimize the process. The present paper proposes to use the source-sink assignment methodology to decide the recycle structure. The counter current scheme is also taken into account because it is usually regarded as the design of choice to recycle streams. The approach was applied to optimize the recycle structure of a two stages process for the separation of free fatty acids from soybean oil deodorizer distillate, to get a concentrate of tocopherols in the residual stream, within specification of acidity. The counter current scheme was also implemented. For this case study the optimal recycle structure gets 10% more product with a profit 0.6% larger than the counter current scheme, even if it has larger operative and investment costs. So, in this particular case, the reward for using a rigorous methodology was not that significant. However, the approach proposed here is systematic and necessarily leads to a structure with a performance greater than or equal to any other, because the superstructure explored includes all of them. [ABSTRACT FROM AUTHOR]

Fractions of rapeseed oil deodorizer distillate containing vinylsyringol and its dimer, which are degradation products of sinapic acid, and other phenolic compounds were investigated for their potential use as antioxidants in refined rapeseed oil. Vinylsysringol, vinylsyringol dimer (VSD), and sinapic acid could effectively inhibit the formation of hydroperoxides, propanal, and hexanal in rapeseed oil triglycerides during storage at 40°C in the dark and at 25°C under light. In the presence of tocopherol, the addition of VSD increased the oxidative stability considerably at low tocopherol concentrations (25 μM) and if the VSD concentration was 10-20 times as high as the tocopherol concentration. The addition of polyphenolic rich fractions of the deodorizer distillate to commercial rapeseed oil resulted in slightly accelerated lipid oxidation in the dark at 40°C but did not influence the formation of hydroperoxides under light at 25°C. Practical applications: This study does not give any implications to change the process conditions during refining in a way that VSD would be removed from the oil. On the other hand, the fractions could be added for their positive health effects or as flavouring in savory products without jeopardizing the storage stability of the oil. Fractions of rapeseed oil deodorizer distillate rich in phenolic compounds were investigated for their potential use as antioxidants in rapeseed oil. The isolated compounds effectively inhibited lipid oxidation in the dark and under light. In the presence of tocopherol, the addition of the dimer increased the oxidative stability considerably at low tocopherol and high vinly syringol dimer concentrations. The addition of polyphenolic rich fractions of the deodorizer distillate to commercial rapeseed oil resulted in slightly accelerated lipid oxidation in the dark at 40°C but did not influence the formation of hydroperoxides under light at 25°C. [ABSTRACT FROM AUTHOR]

An innovative intensified vitamin E (VE) recovery process from the methylated oil deodorizer distillates (MODDs) was proposed, where VE was in situ transferred into a deep eutectic solvent (DES) with an organic salt. To design the process, the chlorine based quaternary ammonium salts were primarily investigated, and [N4,4,4,4]Cl was selected as an association solvent which can efficiently form DES with α-tocopherol of the representative compound of VE. Based on the determined phase diagram of the DES freezing points, four phase regions were classified, and the effect of the [N4,4,4,4]Cl/tocopherol ratio and temperature on the extraction performance and phase transformation was figured out. Moreover, an intensified association extraction process via in situ forming DES of α-tocopherol with [N4,4,4,4]Cl was designed and validated by experiments. VE products were finally obtained from both model MODD (purity of 99.63%) and practical MODDs (purity of >79.18%), which verifies the excellent extraction efficiency for the proposed recovery method. © 2016 American Institute of Chemical Engineers AIChE J, 63: 2212-2220, 2017 [ABSTRACT FROM AUTHOR]

This article reported a new procedure for synthesizing ordered mesoporous sulfated zirconia (m-SZ), an effective oxophosphate process for strengthening thermal stability of the as-synthesized m-SZ catalyst forming mesoporous phosphated sulfated zirconia (m-PSZ). The study also afforded a new reaction routine for synthesizing the m-SZ through condensation method using Zr(SO) solution precursor in the incipient wetness impregnation method. The m-PSZ contained dense surface superacid sites being suitable for methanolysis of almost vegetable oils or animal fats producing methyl ester. The temperature of the condensation process was varied in the range of 70-100 °C, and the time periods were surveyed from 12 to 72 h for well self-assembling the mesoporous structure. The precipitation obtained from the condensations was calcined at 450 °C for 3 h after completely removing of the surface water overnight at 100 °C. The after calcination powder was the m-SZ catalyst. The HPO was used as precursor for oxophosphate process producing the m-PSZ catalyst. The m-PSZ catalyst was applied to the methyl ester synthesis using deodorizer distillate collected from vegetable oil refinery in Vietnam as feedstock. The methanolysis was established at 130 °C for 4 h to obtain the refined methyl esters after passing through a purification process. The refined biodiesel characteristics were determined for its using in diesel engine, and the results showed almost positive values. Some techniques were used in the research such as XRD, TEM, BET, TG-DTA, NH-TPD and GC-MS. [ABSTRACT FROM AUTHOR]

In this paper, cotton seed oil deodorizer distillate (CSODD), was recovered to obtain fatty acid sterol ester (FASE), which is one of the biological activated substances added as human therapeutic to lower cholesterol. Esterification reactions were carried out using Candida rugosa lipase as a catalyst, and the conversion of phytosterol was optimized using response surface methodology. The highest conversion (90.8 ± 0.4%) was reached at 0.84 wt% enzyme load, 1:25 solvent/CSODD mass ratio, and 44.2 °C after 12 H reaction. A kinetic model based on the reaction rate equation was developed to describe the reaction process. The activation energy of the reaction was calculated to be 56.9 kJ/mol and the derived kinetic parameters provided indispensable basics for further study. The optimization and kinetic research of synthesizing FASE from deodorizer distillate provided necessary information for the industrial applications in the near future. Experimental results showed that the proposed process is a promising alternative to recycle sterol esters from vegetable oil deodorizer distillates in a mild, efficient, and environmental friendly method. [ABSTRACT FROM AUTHOR]

Polylactide ( PLA) is the most used biodegradable and biobased food packaging polymer for rigid containers and films. However, its low ductility is a hurdle for increasing its applications in flexible food packaging. A solution is the use of additives. Palm oil deodorizer distillate ( PODC) is revealed to be an excellent additive promoting PLA ductility. PODC is a by-product of vegetable oil refining, which is available in stable quality and in sufficient amounts. Amorphous PLA/ PODC blends had an elongation at break of around 130% and that of semi-crystalline blends was still around 55% compared to the initial 5% of neat PLA. At the same time the PLA rigidity and high glass transition temperatures were kept. PODC was also a very efficient processing aid, allowing for film blow extrusion. The blends were stable in properties during six months without exudation. They complied with legal norms of Food Contact Materials ( EU 10/2011) and induced no sensorial alteration of packed food. Therefore PODC is a very interesting alternative to common plasticizers for the production of flexible PLA packaging films. © 2016 Society of Chemical Industry [ABSTRACT FROM AUTHOR]

Crude vegetable oils and fats after oil extraction may contain contaminants introduced in the supply chain. Many of these contaminants are largely removed from the oil by the refining process. However, these contaminants will concentrate in the refinery by-products; acid oil from soapsplitting and filter blowing, spent bleaching earth, and deodorizer distillate. The contaminant levels in these by-products are calculated by determining the lipids balance of the refinery and the fate of the contaminants in the refining process. Calculations of some example oils with characteristic contaminant levels show that deodorizer distillate from chemical refining has a high-contamination risk, deodorizer distillate from physical refining and spent bleaching earth has a medium risk, whereas acid oil from soapsplitting and filter blowing have a low-contamination risk. Extracted oils and fats contain impurities like free fatty acids, phospholipids, etc., and may contain contaminants like polycyclic aromatic hydrocarbons and pesticides. The impurities and some entrained oil form the refinery by-products; acid oil, spent earth, and deodorizer distillate. The contaminants will concentrate in these by-products. For application in animal feed, acid oil is relatively safe (green), oil from spent bleaching earth requires contaminant analysis (orange), whereas contaminant levels in deodorizer distillate are often too high for use in feed (red). [ABSTRACT FROM AUTHOR]

In this research work, it was optimized the reaction conditions for the chemistry esterification of unsaponifiable matter in soybean oil deodorizer distillate. The process involves (i) alkaline hydrolysis of saponifiable matter; (ii) acidulation of soaps and (iii) acid catalyzed esterification of resulting total fatty acid. To determine the best process conditions to get the higher conversion rates of total fatty acids to ethylic esters, preserving the tocopherols, it was used, to analyze the results, the response surface methodology in a 2nd order factorial planning. In the step (i) saponification of soybean oil deodorizer distillate saponifiable matter using NaOH:total fatty acids molar ratio = 2:1, temperature = 80º C and reaction time of 40 min. In the step (ii) the resulting soaps were rapidly and stoichiometrically converted in free fatty acids with sulfuric acid (23 %), using an acid molar excess of 50 %, at 80º C, for 40 min and under atmospheric pressure. In the step (iii) the optima conditions for the esterification reaction of soybean oil deodorizer distillate were: ethanol:total fatty acids molar ratio from 6.4 to 11.2:1, SO2H4 concentration from 0.9 to 1.5 % and reaction time from 1.3 to 2.6 h, with ethyl esters conversion rates up to 98 %. The mathematical model obtained is predictive and statistically significant (p

In this research work, the reaction conditions for the direct acid esterification of free fatty acid from soybean oil deodorizer distillate was optimized, using anhydrous ethyl alcohol and concentrated sulfuric acid as catalyst to determine the best process conditions to get the best conversion rates of free fatty acids to ethylic esters, preserving the tocopherols. The conversion extent of free fatty acids to ethyl esters was optimized using a Response Surface Methodology obtained through a second order factorial experimental design. The optima conditions for the direct acid esterification of soybean oil deodorizer distillate were: ethanol:free fatty acids from 6.4 to 11.2:1, H2SO4 concentration from 0.9 to 1.5 % and reaction time from 1.3 to 2.6 h, with conversions extent above 94 %. No significant tocopherol losses were observed during the process. Results showed a good fit between mathematical model and data obtained at different processing conditions, making this model predictive and statistically significant (p< 0,05).

Deodorizer distillates are valuable by-products of edible oil refining and can have a wide range of characteristics. The value and uses clearly depend on their composition. A knowledge of their composition would allow refining processes, to be compared and the influence of deodorization conditions to be determined. In this paper, TLC/FID is applied to determine deodorizer composition in a rapid, single step analysis, separating hydrocarbons, free fatty acids, triglycerides and sterols. This analysis had similar reproducibility to other chromatographic techniques.

Abstract: The recovery of squalene from deodorizer distillate derived from the physical refining of olive oil was evaluated by combining pressurized acidic esterification in a closed system with vacuum distillation. Esterification was carried out at 341, 359, 366, 391 and 395 K. The reaction at 395 K was found to be satisfactory as it decreased the acid value by 99.21% and generated a FAME concentration of 67.53% within 1 h. In order to demonstrate that the generation of FAME from deodorizer distillate was mainly due to the transformation of FFA, the reaction extent, which characterizes the reaction and simplifies calculations, was evaluated for FFA removal and the generation of FAME. Subsequent vacuum distillation allowed the separation of one fraction rich in FAME (94%), which can be used as a biofuel and accounted for 85% of the initial mass, and another fraction that was rich in squalene (78%) and may be used for manufacturing pharmaceutical products. The global squalene yield was 117 g kg−1 initial deodorizer distillate. [Copyright &y& Elsevier]

Phytosterols have been recovered from the deodorizer distillate produced in the final deodorization step of vegetable oil refining by various processes. The deodorizer distillate contains mainly free fatty acids (FFAs), phytosterols, and tocopherols. The presence of FFAs hinders recovery of phytosterols. In this study, fermentation of soybean oil deodorizer distillate (SODD) with Candida tropicalis 1253 was carried out. FFAs were utilized as carbon source and converted into cellular components as the yeast cells grew. Phytosterols concentration in SODD increased from 15.2 to 28.43 % after fermentation. No significant loss of phytosterols was observed during the process. Microbial fermentation of SODD is a potential approach to concentrate phytosterols before the recovery of phytosterols from SODD. During SODD fermentation, sterols-rich yeast cells were produced and the content of total sterols was as high as 6.96 %, but its major sterol was not ergosterol, which is the major sterol encountered in Saccharomyces cerevisiae. Except ergosterol, other sterols synthesized in the cells need to be identified. [ABSTRACT FROM AUTHOR]

Deodorizer distillate is an important by-product obtained during deodorization in the edible oil industries. It is a complex mixture of many health beneficial constituents like phytosterols, tocopherols and squalene. In the present study a simple gas chromatographic method with mass spectrometry was used for the separation, detection and quantification of different components present in the deodorizer distillate in a very short analysis time of 18 min. A simple saponification procedure without derivatization was used for their analysis followed by GC-MS analysis. Phytosterols concentration (21.27-25.53%) was the most abundant in canola and palm distillate samples whereas, squalene and tocopherol were present in concentration ranges of 2.89-13.21% and 1.29-5.81%, respectively. The present study revealed that the unsaponifiable fraction of deodorizer distillate could be used in cosmetic preparations due to its appreciable amount of bioactive constituents. [ABSTRACT FROM AUTHOR]

Abstract: A new method for isolating sterols from sunflower oil deodorizer distillate (DOD) was developed. The most salient feature of which is that, unlike most alternatives, it requires no distillation. Briefly, the method uses methanol in the presence of p-toluenesulphonic acid as catalyst to convert free fatty acids and acyl glycerides in DOD into fatty acid methyl esters (FAMEs). The resulting glycerin and excess reagents are removed by washing with water and, finally, the product is cooled in the absence of solvents to obtain sterols in 92±2% purity. [ABSTRACT FROM AUTHOR]

Abstract: Soapstock and deodorizer distillates are the major by-products from vegetable oil refining. They have little commercial value and are sold at a fraction of the oil cost. However, their characterization reveals the presence of numerous types of compounds, which could be extremely valuable if extracted at low cost. The literature in this area is discontinuous and warrants the effort to produce a comprehensive review. The aim of this review is to combine and condense the body of research performed on these materials, as well as to suggest the best routes for characterization and extraction. Utilization of the components is also discussed. [Copyright &y& Elsevier]

Abstract: Thirty-five samples of vitamin E supplement softgels, obtained from store shelves, were analyzed for 17 dioxin and furan congeners. Of these samples, 14 were identified as natural vitamin E, containing D-α-tocopherol, as well as lesser amounts of β-, α-, and δ-tocopherols, and the remaining 21 were labeled as synthetic vitamin E, containing a mixture of D- and L-α-tocopherol. The supplements were collected during the years of 2002 and 2004. The seven natural vitamin E supplements collected in 2002 were found to contain significant quantities of dioxins and furans, with an average total toxic equivalence (TEQ) of 0.79pg/g, compared to 0.10g/g for the 2004 natural vitamin E supplements. The 21 synthetic vitamin E supplements collected during the same time period showed little or no contamination, with an average TEQ of 0.057pg/g. Eight samples of deodorizer distillate, from which natural vitamin E is derived, were also collected and analyzed. The distillates exhibit an overall congener pattern similar to that found in the natural vitamin E, but at a much higher average TEQ of 3.4pg/g. This suggests the possibility of carryover of contamination to the vitamin E samples from the deodorizer distillate during the extraction process. The natural vitamin E supplements collected in 2004 have much lower levels of contamination, suggesting that improved extraction processes may be in use, effectively reducing contamination. [Copyright &y& Elsevier]

Abstract: Soybean oil deodorizer distillate (SODD) was enzymatically modified to obtain a product mixture comprised mainly of sterol esters, tocopherols, and fatty acid ethyl esters. Firstly, the original SODD was mixed with oleic acid to reduce its melting point from 65–70 to 30–35°C and also to produce a reaction mixture with a ratio of free fatty acids (FFA) to sterols close to 2 to improve the progress of sterols esterification. Two enzymatic steps were used in order to separate sterols esterification and ethyl esterification in time and space. The first enzymatic step (in the presence of Candida rugosa lipase) allowed to efficiently transform more than 90% of the original sterols in a short period of time (5h). The second enzymatic step (in the presence of Novozym 435) converted more than 95% of the FFA in less than 3h. In addition, the stability of both biocatalysts has been evaluated and both bioprocesses have been scaled-up reutilizing the same batch of lipase up to 8 and 3 times for the first and the second enzymatic step, respectively. The final product obtained is intended to be used as starting material for the purification of sterol esters, tocopherols, and fatty acid ethyl esters via supercritical fluid extraction. [Copyright &y& Elsevier]

Abstract: Ethanolysis of a raffinate product-obtained after distillation of olive oil-catalyzed by three commercial lipases (from Candida antarctica, Rhizomucor miehei and Thermomyces lanuginosa) was studied. Uni-response model derived from a generalized Michaelis–Menten mechanism was utilized to describe the rates of formation of ethyl esters from the fatty acids present in the precursor oil. The rate constants for the ethanolysis of triacylglycerols and steryl esters under the reaction conditions were compared. Moreover, inactivation of three lipases was evaluated. Because the half-life of the enzyme is comparable to or even shorter than the half-life of the reaction, the intrinsic reaction rate and enzyme deactivation must both be considered in modeling the kinetics. [Copyright &y& Elsevier]

Back-propagation artificial neural network and response surface methodology were used to build a predictive model of the combined effects of molecular distillation's independent variables including evaporating temperature, feed flow rate and wiper rolling speed for the recovery of tocopherol from rapeseed oil deodorizer distillate. The optimum operating conditions obtained from the quadratic form of the response surface methodology and artificial neural network models were evaporating temperature 473 K, wiper rolling speed 150 r min−1, feed flow rate 90 ml h−1 when feed temperature 353 K and vacuum 0.02 torr. The results demonstrated a high predictive accuracy of artificial neural network compared to response surface methodology. The interior relationships between parameters are shown well by response surface methodology. [ABSTRACT FROM AUTHOR]

Abstract: In this study, a simple method for the determination of free fatty acids, phytosterols, tocopherols, mono and diglycerides present in canola oil deodorizer distillate (DD) and soapstock samples was developed. Analytes were derivatized “in situ” using a mixture of hexamethyldisilazane (HMDS), pyridine and trifluoroacetic acid; separated by gas chromatography (GC) with mass spectrometry (MS) for final detection. Two drying procedures were evaluated for drying deodorizer distillate samples before derivatization: freeze drying and drying at 100°C for 24h. The use of high temperatures caused the degradation of tocopherols and phytosterols, while lyophilization did not affect the substances negatively. The chromatographic conditions used in this work allow for the separation and quantification of oleic, linoleic and linolenic acids, monoolein and monolinolein in both samples, and brassicasterol and α-tocopherol in deodorizer distillate samples. MS provided an accurate identification for the compounds which were at very low concentrations (>0.09%). Oleic acid was the most abundant compound in both samples. Deodorizer distillate was an important source of tocopherols which were not detected in the soapstock samples. [Copyright &y& Elsevier]

Abstract: Nowadays, vitamins and sterols are produced synthetically, so the interest in the extraction of these compounds from natural sources is increasing. The aim of this work is to develop a supercritical fluid process to concentrate the vitamin E (tocopherol) presents in the by-product of the refining process of different vegetable oils, like corn, sunflower, canola and soybean, known as the deodorizer distillate (DD). This by-product is rich in high aggregated value compounds like sterols, tocopherols, squalene and fatty acids. The simulation of the vitamin E concentration from the deodorizer distillate using supercritical carbon dioxide was done in a semi-batch mode using operational conditions varying from 40 to 80°C for temperature and from 90 to 350bar for pressure, using the Rachford-Rice procedure. Tocopherol, squalene, linoleic acid and stigmasterol were chosen the key-components to represent the raw material. Different operational conditions were necessary to separate the main components present in the deodorizer distillate, and it indicates the necessity of a process with extractors in series to raise the separation in steps. The temperature, 40°C, is the better one to promote the effective separation between all the components involved, but different conditions of pressure is necessary to separate the linoleic acid (90bar), stigmasterol (250bar) and squalene (350bar) from tocopherol. The separation between stigmasterol and squalene is the more difficult among the others. [Copyright &y& Elsevier]

Soybean oil is the most consumed oil in the world, representing 54% of the consumption in the worldwide market. The high production of soybean oil produces high quantities of a by-product known as deodorizer distillate or soybean sludge. This by-product is produced during the refining steps that consist of deodorization, bleaching, and refining. The soybean sludge is composed of high aggregated compounds, such as tocopherols (vitamin E), sterols (campesterol, β-sitosterol), squalene, and fatty acids. The tocopherols are concentrated in the deodorizer distillate from 11 to 13%. They are used as antioxidants and as additives in the food industry. The sterols, present in the deodorizer distillate in lower concentration, are a very important raw material in the production of hormones and in the preparation of vitamins. The squalene is a hydrocarbon mostly used in cosmetic preparations and in the biosynthesis of cholesterol. The fatty acids, making up 70% of the soybean sludge, have low quality because of the processing steps and have limited uses that do not involve food in spite of high costs. Therefore, the motivation of this work is to concentrate the vitamin E, adding value to the raw material, and concentrating other compounds of industrial interest. To concentrate vitamin E, the soybean sludge, kindly supplied by CEVAL S.A., is applied to the extractor and submitted to the operational conditions of 40, 60 and 80 °C at 90 and 170 bar. The sampling, during the extraction, is done with a micrometric valve, where the raffinate is separated from the solvent and recovered. The tocopherols are concentrated in the extractor and the fatty acids are extracted during the extraction process. The tocopherols are concentrated to at least 40% from a natural source. A better efficiency of the process was obtained at lower conditions of temperature and pressure. From the experimental data, an economic evaluation of an industrial process to concentrate tocopherol was studied and it was concluded that this process is technically and economically viable. [Copyright &y& Elsevier]

We have shown recently that plant steryl and stanyl esters, used as plasma cholesterol-lowering food supplements, can be efficiently prepared from the sterols and stanols via lipase-catalysed esterification with fatty acids and transesterification with fatty acid methyl esters or triacylglycerols [Weber, N., Weitkamp, P., & Mukherjee, K. D. (2001). Journal of Agricultural and Food Chemistry, 49, 67–71]. In continuation of this work, sterols contained in three different steam distillates obtained from rapeseed oil by conventional deodorization or from rapeseed oil or a mixture of soybean and rapeseed oils by physical refining have been converted to a high degree in situ to the corresponding long-chain acyl esters via esterification and/or transesterification with fatty acids and/or triacylglycerols using lipase from Candida rugosa as biocatalyst in vacuo (20–40 mbar) at 40 °C. The steryl esters formed were purified to &ges;90% by deacidification, flash chromatography on silica gel and solvent fractionation using acetone-water (9:1,v/v). [Copyright &y& Elsevier]

The isolation of tocopherols and sterols together as a concentrate from sunflower oil deodorizer distillate was investigated. The sunflower oil deodorizer distillate was composed of 24.9% unsaponifiable matter with 4.8% tocopherols and 9.7% sterols, 28.8% free fatty acid (FFA) and 46.3% neutral glycerides. The isolation technology included process steps such as biohydrolysis, bioesterification and fractional distillation. The neutral glycerides of the deodorizer distillates were hydrolyzed by Candida cylindracea lipase. The total fatty acids (initial FFA plus FFA from neutral glycerides) were converted into butyl esters with Mucor miehei lipase. The esterified product was then fractionally distilled in a Claisen-vigreux flask. The first fraction, which was collected at 180-230°C at 1.00 mm of Hg for 45 min, contained mainly butyl esters, hydrocarbons, oxidized products and some amount of free fatty acids. The fraction collected at 230-260°C at 1.00 mm Hg for 15 min was rich in tocopherols (about 30%) and sterols (about 36%). The overall recovery of tocopherols and sterols after hydrolysis, esterification and distillation were around 70% and 42%, respectively, of the original content in sunflower oil deodorizer distillate. [ABSTRACT FROM AUTHOR]

Separation of sterols and tocopherols from fatty acids in deodorizer distillate was facilitated through lipase-catalyzed modification of fatty acids in canola, mixed and soya deodorizer distillates. The fatty acid esterification with methanol catalyzed by SP-382 (an immobilized nonspecific lipase) proceeded rapidly, with conversion of fatty acid to methyl ester in 5 h being 96.5, 83.5 and 89.4%, respectively. A model mixture of pure oleic acid and dl-α-tocopherol was used to study any potential side reactions that may lower the tocopherol content during the esterification reaction. Under the conditions employed, the loss of tocopherol was less than 5%. Simple vacuum distillation (1-2 mm Hg) was employed to remove the volatile fraction (methyl esters of fatty acids, some fatty acids and other volatiles) of the esterified deodorizer distillate, leaving behind sterols, sterol esters and tocopherols. Sterols and tocopherols were almost completely retained in the residue fraction with recoveries in the range of 95%. Overall recoveries of sterols and tocopherols after esterification and distillation were over 90% for all the deodorizer distillate samples. [ABSTRACT FROM AUTHOR]

The use of liquid water at elevated temperatures and pressures as an extractive solvent for separating mixtures of compounds which occur in natural oils has been studied. A southern pine tall oil and a distillate from the deodorization of soybean oil were extracted with liquid water at temperatures from 298 to 312°C and pressures between 103 and 121 bar. Results indicate that water can be used to extract fatty and resin acids from crude tall oil to obtain a product with a high acid content that produces less pitch during distillation. The process can also be used to extract fatty acids from vegetable oil deodorizer distillate. [ABSTRACT FROM AUTHOR]

Tocopherols and tocotrienols in the combined form are known as tocols. Changes of total and individual tocols and sterols concentration of canola oil and deodorizer distillate (DD) during different processing stages were evaluated with the application of gas chromatography (GC) and high-performance liquid chromatography (HPLC). For sterols analysis, GC coupled with flame ionization detector (FID) was used while tocols in canola oil samples and DD, normal phase (NP) HPLC was applied. The results of the present study indicated that levels of total and individual tocols and sterols content were decreased during processing (neutralization to deodorization). Deodorization was found to be the most effective process for the reduction of total sterols and tocols as 55.9% and 34.2%, respectively. A high amount of tocols and sterols was observed in DD. Among tocols and sterols; beta tocopherol (β-T) and β-sitosterol were found to be in greater concentration 53.97% and 31.82%, respectively. Therefore, DD could be used as a valuable by-product in the cosmetics and food industries., Competing Interests: Conflict of interest The authors have declared no conflicts of interest., (© TÜBİTAK.)