Science China-Chemistry
·
2017
·Vol. 60
·期 9
·1243-1249
·
IF 4.132
Zhang Honghua,Liu Ruixia,Zhang Ruirui,Huo Feng,Yang Zhiqiang,He Bin,Zhang Suojiang,Wang Yanji
Ionic liquid coupled with strong acid systems presents considerable promise in some catalytic fields. In the present work, the multiple complex systems composed by 98 wt% concentrated sulfuric acid and [Bmim][SbF 6 ] were investigated in the terms of stability, acidity and interaction properties. It was found that acidolysis of [Bmim][SbF 6 ] occurred in the 98 wt% concentrated sulfuric acid accompanied by HF releasing and SbF
− 6
degrading to [SbF 6− y
(HSO 4 )
y
] − . The species after acidolysis in the multiple complex systems were checked and confirmed by electrospray ionization mass spectrometry (ESI-MS), Fourier transform infrared spectroscopy (FT-IR), 1 H NMR and 19 F NMR. Acidity increased slightly with less than 1 wt% [Bmim][SbF 6 ] addition, while decreased with more proportion, which was determined based on the Hammett acidity functions H 0 , using 13 C NMR. The strong hydrogen bond S–O–H···F of interaction among the multiple complex systems was confirmed by molecular dynamic simulation.
研究领域:
化学
·
催化领域
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DOI
高影响因子
Food Bioscience
·
2024
·
IF 4.8
Xiaoqiang Zou,Mudassar Hussain,Imad Khan,Yanxi Wang,Bangzhi Jiang,Lei Zheng,Yuechao Pan,Jijie Hu,Azqa Ashraf
Medium- and long-chain structured lipids (MLSLs) rich in docosahexaenoic acid (DHA) and eicosapentaenoic acid (EPA) were synthesized by acidolysis of fish oil (Omax 1812, a mixture of sardine and anchovy oils) with caprylic acid (CA) using a lipase bio-imprinted with fatty acids as a catalyst. A bio-imprinted lipase for the acidolysis reaction was first prepared under optimal conditions, and its activity was 1.43 times higher than that of the non-bioimprinted. The bio-imprinted lipase was used as a catalyst to produce such MLSLs, and the reaction conditions were optimized. Under the optimal conditions, equilibrium was achieved in 8 h, and the total and the sn -1, 3 CA contents in the obtained product were 28.72% and 42.26%. Additionally, the total and the sn -2 DHA contents were 14.23% and 21.10%, respectively, and the total and the sn -2 EPA contents were 16.43% and 10.14%, respectively. These obtained MLSLs, rich in sn -1, 3 CA, and sn -2 DHA, EPA can deliver significant health benefits.
研究领域:
生物化学
·
食品科学
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DOI
高影响因子
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY
·
2013
·Vol. 91
·期 1
·55-62
·
IF 1.592
Qin Xiao-Li,Huang Hui-Hua,Lan Dong-Ming,Wang Yong-Hua,Yang Bo
Typoselectivity of crude CBD-T1 lipase ( Geobacillus sp. T1 lipase fused with a cellulose binding domain) was investigated. Multi-competitive reaction mixtures including a set of n -chain fatty acids (C8:0, C10:0, C12:0, C14:0, C18:1 n-9, C18:2 n-6 and C18:3 n-3) and tripalmitin-enriched triacylglycerols were studied in hexane. The crude CBD-T1 lipase discriminated strongly against C18:1 n-9 [competitive factor ( α ) = 0.23] and showed the highest preference for C8:0 ( α = 1). Utilizing the catalytic properties of crude CBD-T1 lipase, acidolysis of soybean oil with C8:0 was selected as a model reaction to investigate the ability of the lipase to produce MLM-type (medium-long-medium) structured lipids. Several reaction parameters (added water amount, reaction temperature, substrate molar ratio and reaction time) examined for incorporating C8:0 into soybean oil, the optimum conditions were: 1:3 (soybean oil/C8:0) of molar ratio, 3 mL of hexane, 50 °C of temperature, 48 h of reaction time, 20 % of crude CBD-T1 lipase (w/w total substrates), and 7.5 % of water (w/w enzyme). Under these conditions, the incorporation of C8:0 was 29.6 mol%. The results suggest that crude CBD-T1 lipase, which showed different fatty acid specificity profiles, is a potential biocatalyst for the modification of fats and oils.
研究领域:
生物化学
·
食品科学
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DOI
高影响因子
JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE
·
2022
·Vol. 102
·期 11
·4714-4723
·
IF 4.125
Ke Cheng,Jianghua Zhang,Shasha Yang,Fawen Yin,Zixuan Li,Ting Wang,Dayong Zhou
BACKGROUND Efficient and sustainable production of structured phospholipids (SPLs) enriched in medium-chain fatty acids (MCFAs) in a heterogeneous manner is crucial for their potential applications in functional foods and drugs. Herein, for the first time, Zn- and Al-incorporated SBA-15 silicas were prepared by the coprecipitation method and further researched for catalytic synthesis of MCFA-enriched SPLs through acidolysis reaction of natural phospholipids with capric or caprylic acid. RESULTS The as-prepared Zn- and Al-incorporated SBA-15 samples exhibited superior catalytic activities under mild experimental conditions (50 °C, 6 h) to commercial homogeneous Lewis acids and benchmark enzymes. Correspondingly, the capric acid and caprylic acid incorporations were respectively achieved up to ~40.25 ± 0.40% (or 35.08 ± 0.09%) and 37.26 ± 0.38% (or 33.02 ± 0.13%) for Zn- (or Al-) incorporated SBA-15 catalyst. Moreover, various methods such as scanning electron microscopy with energy-dispersive X-ray spectrometry, ultraviolet–visible diffuse reflectance spectroscopy and pyridine–Fourier transform infrared spectroscopy were utilized to characterize the two catalysts in order to elucidate the possible structure–performance relationship. Accordingly, the above-mentioned satisfactory results are most probably due to the well-ordered mesostructures and large amounts of active Lewis acid sites existing in the investigated materials. Noticeably, the two catalysts featured good separation and excellent recyclability as well. CONCLUSION The Zn- and Al-incorporated SBA-15 catalysts studied in this work might shed light on novel, sustainable and economic alternatives for effective SPL production to diminish the applications of conventional homogeneous catalysts and biocatalysts in food industries. © 2022 Society of Chemical Industry.
研究领域:
食品科学
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生物化学
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PubMed
高影响因子
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY
·
2016
·Vol. 93
·期 10
·1347-1354
·
IF 1.505
Siyun Gu,Fengqin Feng,Yang Li,Wei Wei,Rongrong Lu
Dioleoyl; palmitoyl-rich triacylglycerols (OPO-rich TAG) were synthesized through Aspergillus oryzae lipase (AOL)-catalyzed acidolysis of palm stearin with commercial oleic acid by a one-step process in a stirred tank reactor and continuous packed bed reactor to evaluate the feasibility of using immobilized AOL. AOL was found to be valuable for the synthesis of OPO-rich TAG when compared with commercial lipase from Thermomyces lanuginose (Lipozyme ® TL IM; Novozymes A/S, Bagsvaerd, Denmark). The C52 (triglycerides with a carbon number of 52, stands for OPO, OPL, LPL and their isomers) content of AOL was higher (45.65 %), and the intensity of treatment (IOT: lipase amount × reaction time/TAG amount) of AOL was just 6.25 % of that of Lipozyme ® TL IM under similar reaction conditions in the stirred tank reactor. Response surface methodology were used to optimize the reaction conditions of the AOL-catalyzed acidolysis is reaction in the packed bed reactor. The optimal point for the set of experimental conditions generated were as follows: residence time 3.0 h; temperature 62.09 °C; substrate molar ratio 7.13 mol/mol. The highest C52 content obtained was 48.60 ± 2.36 %, with 57.46 ± 1.72 % total palmitic acid at the sn -2 position and 74.21 ± 2.45 % oleic acid at the sn -1,3 positions. The half-life of AOL was 24 h in the stirred tank reactor and 140 h in the packed bed reactor. The immobilized AOL achieved similar conversion and selectivity to commercial lipases for the catalyzed synthesis of OPO-rich TAG and may offer a cheaper alternative.
研究领域:
生物化学
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食品科学
·
酶工程
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高影响因子
JOURNAL OF CATALYSIS
·
2020
·
IF 7.888
Zifei Yan,Yunpeng Hu,Chencan Du,Jian Deng,Kai Wang,Guangsheng Luo
The acidolysis of epoxides is an important series reaction applied in the polymer industry including coating and rubber. Glycidyl neodecanoate, which is a green material of environmentally friendly coatings, is synthesized through the acidolysis reaction of epichlorohydrin (ECH) with neodecanoic acid. We developed a green catalyst named tetramethylammonium neodecanoate (TMAN) for this reaction. TMAN is totally recyclable and the reaction system can be homogeneous, thus combining the advantages of tertiary amines and quaternary ammonium salts, meanwhile eliminating their drawbacks. Comparing with tetramethylammonium chloride (TMAC) which is a traditional industrial catalyst, the amount of side product dichlorohydrin can be reduced by more than 50%, effective utilization of ECH and yield of the main product can be increased by 5% and 2% respectively, and the reaction time can be reduced by 20% or more. We suggested a main catalytic reaction network including the conversion of TMAN to TMAC at the late stage of the reaction, and TMAC can be easily recycled and reused to prepare TMAN. More importantly, after the replacement of material acid and the carboxylic anion of catalyst, this efficient catalytic system and the mechanism network can be applied to other acidolysis reactions of epoxides.
研究领域:
化学工程
·
绿色化学
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DOI
高影响因子
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
·
2020
·
IF 3.573
Zifei Yan,Jian Deng,Yuchao Chen,Guangsheng Luo
2,3-Epoxypropyl neodecanoate (EPDA) is an important synthon of eco-friendly coatings, and its preparation methods and the relevant reaction mechanisms remain to be further studied. In this work, the two-step preparation method of EPDA is investigated. Under the optimized process conditions in the acidolysis reaction, 99% conversion of neodecanoic acid and 91–93% effective utilization rate of epichlorohydrin could be realized. In the following ring-closure reaction, the two-step alkali treatment was applied, and it can significantly reduce the treatment time and improve the yield of EPDA by 3–5%. Besides, the mechanism of the acidolysis reaction catalyzed by tetramethylammonium chloride is proposed. The two chemical reaction pathways are put forward to explain the formation of side product dichloropropanol. Two effective ways to control the side reactions are suggested, including the control of temperature in the range of 70–90 °C and reducing the concentration of inorganic chlorine in the reaction system.
研究领域:
化学工程
·
有机合成
·
环境科学
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DOI
高影响因子
FOOD CHEMISTRY
·
2025
·
IF 9.8
Libin Sun,Jingwen Li,Danying Wu,Hong Wang,Dianyu Yu
The present study aimed to investigate the application of lysophospholipids from enzymatic degumming products and different acyl donors to form structured soybean phospholipids in the lipase-mediated acidolysis reaction. Sn -1 and sn -2 fatty acid compositions of structured phospholipids from soybean phosphatidylcholine (SP-SPC) were examined, indicating that the relative content of saturated fatty acid in SP-SPC sn -2 fatty acids increased. Liquid chromatography-mass spectrometry analysis suggested that there were seven SP-SPC molecules. Spectroscopy analysis and differential scanning calorimetry thermogram analysis indicated that the structure of SP-SPC was more stable than SPC due to its unique alkyl chain conformation and phase states. Polarized light microscopy observations suggested that SP-SPC had a strong birefringence phenomenon. The preparation of liposomes with SP-SPC showed a homogeneous double-layer with an almost constant C C strength. These results have important implications for the enzymatic preparation of structured soybean phosphatidylcholine and the information on its phase states.
研究领域:
食品科学
·
生物化学
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DOI
PubMed
高影响因子
CHEMICAL ENGINEERING JOURNAL
·
2023
·
IF 15.1
Fanglin Huo,Qing Liu,Zhendong Liu,Yangcheng Lu
Metal-incorporated zeolites as heterogeneous Lewis acid were applied in the ring-opening acidolysis of ethylene oxide with acrylic acid to prepare 2-hydroxyethyl acrylate (HEA). The catalysis characteristics, including Lewis acid strength and internal mass transfer resistance, were systematically investigated to facilitate the rational design of zeolite catalysts. Through modifying the Lewis acid strength of zeolites via different metals (Sn, Zr and Ti) incorporation and the internal mass transfer resistance of zeolites from the particle size, pore diameter or pore structure, it was found that the increased Lewis acidity can accelerate both the main and side reactions, resulting in the high activity but low selectivity of zeolite catalysts; the enhanced internal diffusion was the key to limiting subsequent cascade alcoholysis side reactions as well as the decline of catalytic performance. Based on these findings, Zr-containing zeolites featured with moderate Lewis acidity and uniform intracrystalline mesoporosity were designed and prepared, presenting excellent catalysis and recycling performance. These results demonstrated the great potential of the developed zeolite catalysts for the green synthesis of HEA as well as the similar ring-opening acidolysis of epoxides.
研究领域:
催化
·
化学工程
·
材料科学
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高影响因子
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