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AICHE JOURNAL · 2016 ·Vol. 63 ·期 6 ·2212-2220 · IF 2.98

Association extraction for vitamin E recovery from deodorizer distillate by in situ formation of deep eutectic solvent

Lei Qin,Jiangsheng Li,Hongye Cheng,Lifang Chen,Zhiwen Qi,Weikang Yuan

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 [N 4,4,4,4 ]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 [N 4,4,4,4 ]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 [N 4,4,4,4 ]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

研究领域: 化学工程 · 生物技术
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JOURNAL OF FOOD COMPOSITION AND ANALYSIS · 2024 · IF 4

Investigation into the effects of the refining steps before deodorization on the formation of trans fatty acids in linseed oils

Mengru Kong,Yanli Du,Xiaodie Chen,Ruixin Cai,Jianhua Xie,Mingyue Shen

Trans fatty acids (TFAs) are formed in refined linseed oil during the deodorization step. Effects of deodorization on TFA formation in vegetable oils have been intensively investigated. However, the role of refining process (degumming, neutralization, bleaching) before deodorization on TFA formation in the deodorization step remains unclear. In this study, TFA generation potential in linseed oils refined by different ways of degumming, neutralization, bleaching was evaluated, and changes in their quality indexes were also measured. Results showed that adequate refining could improve the quality of linseed oil, while inadequate neutralization or bleaching induced more TFA formation during the deodorization step, suggesting that pigments or free fatty acids in linseed oils might promote TFA formation. Meanwhile, spiked experiments, in which partly refined linseed oils were spiked with pigments or α-linolenic acid, confirmed that pigments or free fatty acids in linseed oils induced the isomerization of unsaturated fatty acids. This study demonstrated that TFA formation in refined linseed oils could be mitigated by optimizing refining processes before deodorization, and also provided theoretical basis for oil refining industry to control the oil quality.

研究领域: 食品科学 · 营养学
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JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE · 2020 ·Vol. 101 ·期 9 ·3605-3612 · IF 2.614

The inhibitory effects of sesamol and sesamolin on the glycidyl esters formation during deodorization of vegetables oils

Lipeng Han,Jiahui Li,Shujie Wang,Weiwei Cheng,Lukai Ma,Guoqin Liu,Dongxue Han,Li Niu

BACKGROUND Glycidyl esters (GEs) have attracted worldwide attention for their potential harm to human health. The GEs in edible oils mainly form during the deodorization of the oil refining processes. We used sesamol and sesamolin to inhibit the formation of GEs in model corn oil (MCO), model palm oil (MPO) and model rice bran oil (MRO) during a deodorization process. RESULTS The results showed that, in the three model oils, the total GE content was in the following order from highest to lowest: MRO (1437.98 μg kg −1 ) > MPO (388.64 μg kg −1 ) > MCO (314.81 μg kg −1 ). The inhibitory effect of the three antioxidants on the formation of GEs in the MCO was in the following order from strongest to weakest: tert-butylhydroquinone (TBHQ) > sesamol > sesamolin. CONCLUSION When the mass percentage of sesamol was 0.05%, its inhibition percentage on GEs was close to the inhibition percentage of 0.02% added TBHQ. The present study provides a foundation for understanding how to inhibit the formation of GEs in oils by adding sesamol during the deodorization process.

研究领域: 食品科学 · 健康与医学
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FOOD CHEMISTRY · 2024 · IF 8.5

Effect of deodorization conditions on fatty acid profile, oxidation products, and lipid-derived free radicals of soybean oil

Libin Sun,Zhe Huang,Junguo Wang,Dianyu Yu,Liqi Wang

Oxidative stability is a key quality characteristic of edible oils, and the oil’s antioxidant capacity decreases during the deodorization stage. This study explores the changes in radical formation, molecular structure, oxidative characteristics, fatty acids, and main bioactive compounds in soybean oil during deodorization. The lag phase decreased, whereas the total amount of spins of free radicals increased as the deodorization time increased from 90 to 150 min. The total amount of spins and percentage of alkyl radicals varied dramatically under different times and temperatures (220 ∼ 260 ℃). Results showed that identifying and quantifying the formed radicals can provide useful information for monitoring and controlling oil oxidation in vegetable oil refining systems. Therefore, to control early oxidation events, maximize refined oil product yield, and reduce energy consumption in the refining plant, the priority should be to minimize temperature during the oil refining process and then shorten the deodorization time.

CAS / MDL: 3317-61-1 3376-24-7
研究领域: 食品科学 · 化学
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ACS Sustainable Chemistry & Engineering · 2018 · IF 6.14

Enhanced Vitamin E Extraction Selectivity from Deodorizer Distillate by a Biphasic System: A COSMO-RS and Experimental Study

Hongye Cheng,Jiangsheng Li,Jingwen Wang,Lifang Chen,Zhiwen Qi

To enhance the extraction selectivity of vitamin E (VE) from the deodorizer distillate, a biphasic system with solvents of both organic chemical and the salt tetrabutylammonium chloride ([N4,4,4,4]Cl) was established. The organic solvent was tailored to extract the major component of deodorizer distillate (methyl linoleate), while the organic salt was designed to selectively extract VE by in situ forming a deep eutectic solvent. Three types of organic solvents, namely, ester, arene, and alkane, were analyzed by using the COSMO-RS model, and hexane, exhibiting stronger interaction with methyl linoleate and lower solubility of [N4,4,4,4]Cl, was screened and its suitability explained from the σ-profile and σ-potential points of view. The biphasic experiments demonstrated that the selectivity of VE by the one-pass extraction process was significantly enhanced by the biphasic system, and the important operation parameters of the dosage of solvent and initial concentration of VE were analyzed.

CAS / MDL: 616-38-6
研究领域: 食品科学 · 化学工程
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INTERNATIONAL JOURNAL OF FOOD PROPERTIES · 2021 · IF 2.727

Sesame oil inhibits the formation of glycidyl ester during deodorization

Lipeng Han,Jiahui Li,Shujie Wang,Weiwei Cheng,Lukai Ma,Guoqin Liu,Dongxue Han,Li Niu

Glycidyl ester (GE) has attracted worldwide attention due to its potential harm to human health. The GE in edible oil forms during the deodorization process of the oil refining, where antioxidants are used to inhibit its formation. To replace unsafe conventional synthetic antioxidants with natural antioxidants, sesame oil (SO) was used to inhibit the formation of GE in corn oil (CO), palm oil (PO), and rice bran oil (RO) during the deodorization process. The results showed that the content of GE in SO, CO, PO and RO followed the decreasing order of RO (1395.88 μg/kg) > PO (376.84 μg/kg) > CO (303.24 μg/kg) > SO (133.19 μg/kg). The concentration of diacylglycerol (DAG) in SO, CO, PO and RO followed the decreasing order of RO (11.64%) > PO (7.56%) > CO (4.11%) > SO (2.59%). The content of GE in oil could be affected by at least three factors: (i) unsaturated fatty acids could promote the formation of GE in oil; (ii) antioxidants in oil could inhibit the formation of GE by scavenging free radicals; and (iii) DAG, as a precursor, could lead to the formation of GE. This result suggested that SO could inhibit the formation of GE in CO, PO and RO. This indicated that when SO was added at 50%, its inhibitory effect was equivalent to that of tert-butylhydroquinone added at 0.02%.

CAS / MDL: 1948-33-0 96-24-2
研究领域: 食品科学 · 健康与医学
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3 Biotech · 2020 ·Vol. 10 ·期 2 ·1-10 · IF 1.798

Immobilization of Lipozyme TL 100L for methyl esterification of soybean oil deodorizer distillate

Zheng Jianyong,Wei Wei,Wang Shengfan,Li Xiaojun,Zhang Yinjun,Wang Zhao

An immobilization method for binding cross-linked enzyme aggregates of Lipozyme TL 100L on macroporous resin NKA (CLEA-TLL@NKA) was developed in this study. The esterification activity of CLEA-TLL@NKA reached 6.4 U/mg. The surface structure of immobilized lipase was characterized by scanning electron microscopy. Methyl esterification reaction of soybean oil deodorizer distillate (SODD) was catalyzed by CLEA-TLL@NKA, which the conversion rate reached 98% and its activity retained over 90% after 20 batches of reaction. Compared with the commercial enzyme Lipozyme TLIM, half-life ( t 1/2 ) of CLEA-TLL@NKA increased by 25 times and the catalytic activity increased by approximate 10 times. Thus, CLEA-TLL@NKA had high catalytic activity, good operational stability, and potential industrial application in the field of oil processing.

研究领域: 生物化学 · 食品科学
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SEPARATION AND PURIFICATION TECHNOLOGY · 2017 · IF 3.359

Integrated process for extracting vitamin E with high purity from the methylated oil deodorizer distillate

Lei Qin,Qian Zeng,Jingjing Zhang,Hongye Cheng,Lifang Chen,Zhiwen Qi

An enhanced process integrating an extraction with ionic liquid (IL) as solvent and a two-step reextraction is proposed to recover high purity vitamin E from the methylated oil deodorizer distillate (MODD). Conditions for the extraction with solvent [C 6 MIm]Ac were optimized and its reusability was investigated. A crude concentrated vitamin E phase (extract phase) was acquired with some co-extracted fatty acid methyl ester (FAME). In order to remove the co-extracted FAME and obtain the high purity vitamin E, a two-step reextraction process was designed, where n -hexane was proved to be the most promising solvent with the selectivity of 728.01 and partition coefficient of 18.92 to methyllinoleate. Based on the proposed process, high purity vitamin E could be finally obtained from both the model MODD (purity of 99.26%) and two different practical MODDs (purity   >   79.08%) with [C 6 MIm]Ac as extractant and a small amount of n -hexane and water as reextractants. It means that the integrated extraction process with high performance is a promising method for recovery of vitamin E from MODDs.

研究领域: 食品科学 · 化学工程
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FOOD CHEMISTRY · 2024 · IF 8.5

Deodorization mechanism of the main aroma compounds on the fishy odor in boiled fish during heating

Mi Tang,Xinping Liu,Yong Yu,Hankun Zhu,Liang Ma,Kangting Sun,Xin Feng,Yuhao Zhang

A boiled fish simulation system was constructed to explore the deodorization effect of main aroma compounds (MAC) on myofibrillar protein (MP) with main fishy compounds (MFC) during heating. The results showed that the MFC content of boiled fish was reduced by 63.10–78.10 % when boiled by heat-stable emulsions loading MAC. Specifically, adding linalool, anethole, and myrcene significantly elevated the free percentage of hexanal, heptanal, and 1-octen-3-ol after heating, while the free percentage of octanal and nonanal markedly increased by adding anethole and limonene. Molecular docking exhibited that MAC and MFC possessed co-binding sites with myosin. Linalool and anethole were competitively bound to MP through hydrophobic and hydrogen bonding sites, while myrcene and limonene were via hydrophobic interaction sites. Moreover, MAC-MP formed a relatively stable structure, exhibiting increased α-helix content and decreased surface hydrophobicity, which reduced the available sites for MFC binding, ultimately desorbed MFC (65.46 %–95.89 %).

研究领域: 食品科学 · 生物化学
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ACS Omega · 2021 · IF 3.512

Integrated Utilization Strategy for Soybean Oil Deodorizer Distillate: Synergically Synthesizing Biodiesel and Recovering Bioactive Compounds by a Combined Enzymatic Process and Molecular Distillation

Wen Lv,Chunjian Wu,Sen Lin,Xuping Wang,Yonghua Wang

Soybean oil deodorizer distillate (SODD) is well recognized as a good source of both biodiesel and high-value bioactive compounds of tocopherols, squalene, and phytosterols. To achieve a one-step synthesis of biodiesel and recovery of bioactive compounds from SODD, four commercial immobilized enzymes (Novozym 435, Lipozyme TLIM, Lipozyme RMIM, and Lipozyme RM) and one self-prepared immobilized lipase MAS1-H108A were compared. The results showed that immobilized lipase MAS1-H108A due to the better methanol tolerance and higher catalytic activity gave the highest biodiesel yield of 97.08% under the optimized conditions: molar ratio of 1:2 (oil/methanol), temperature of 35 °C, and enzyme loading of 35 U/g SODD, even after 10 persistent cycles without significant decrease of activity. Simultaneously, there was no loss of tocopherols and squalene in SODD during the enzymatic reaction. Pure biodiesel (characterized by fourier transform infrared (FT-IR) and nuclear magnetic resonance (NMR)) and a high concentration of bioactive compounds could be successfully separated by molecular distillation at 100 °C. In a word, this work provides an interesting idea to achieve environmentally friendly treatment of SODD by combining an enzymatic process and molecular distillation, and it is suitable for industrial production.

研究领域: 生物化学 · 可再生资源与环境工程
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FOOD CHEMISTRY · 2025 · IF 9.8

Mechanisms of deodorizing rapeseed oil with ethanol steam at a low temperature: A focus on free fatty acids, tocopherols, and phytosterols

Yu Gao,Yiyang Dong,Fangrong Liu,Aifeng Niu,Shilin Liu,Wenlin Li,Chengming Wang

Previous studies have demonstrated that deodorization of oil with ethanol steam at a low-temperature (L-ESD) can achieve the same effect in removing harmful substances and preserving micronutrients while better inhibiting the formation of new harmful substances compared to deodorization with water steam at a high-temperature. To elucidate the mechanism of ESD, the kinetics and thermodynamics of ethanol steam deodorized distillate were studied in comparison with those of water steam deodorized distillate. Results revealed their deodorization kinetics and thermodynamic models, and further indicated that the additional effects of ethanol steam on free fatty acids (FFAs), tocopherols and phytosterols were related to their intermolecular forces besides the higher vapor pressure of ethanol compared to water steam, and the difference of intermolecular force of ethanol on the various FFAs, tocopherols or phytosterols depended on the number of double bonds, the number, lengths of the substituents and hydrophobicity through comparing the difference of structure between substances.

CAS / MDL: 102-71-6
研究领域: 食品科学 · 化学工程
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MICROCHEMICAL JOURNAL · 2025 · IF 5.1

Effective extraction of tocopherols from soybean oil deodorizer distillate methyl esters using phenolic deep eutectic solvents

Jingnan Chen,Xianli Fu,Guolong Yang,Wei Liu

Nature tocopherols are mainly produced from vegetable oil deodorized distillates. And development of simple and green extraction method is highly desirable for nature tocopherols separation. In this work, a green, rapid and mild (room temperature) solvent extraction method based on phenolic deep eutectic solvents (DES) has been developed to simultaneously extract three isomers of tocopherols (α-, γ-, δ-tocopherol) from soybean oil deodorizer distillate methyl esters (SODD-ME) for the first time. Tetrabutyl ammonium chloride-based DESs (TBAC-DESs) were used as extraction solvents. The effect of factors on the extraction efficiency of three individuals and total tocopherols was investigated. The optimal extraction conditions were determined as follows: DES composed of TBAC and 4-methylphenol (molar ratio of 1:1), DES/SODD-ME 6:1 (w/w), hexane/SODD-ME 1:1 (w/w) and vortex-assisted extraction of 1 min at room temperature. Under these conditions, the maximum extraction efficiency of total tocopherols was (97.5 ± 0.5)%. And the molecular structure of the phenolic DESs had significant effect on the extraction selectivity on α-, γ- and δ- tocopherol from SODD-ME. The underlying extraction mechanism was that the TBAC-phenol DESs combined the three tocopherols by both hydrogen bonding and π-π interaction.

研究领域: 食品科学与工程 · 绿色化学
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