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Oleic Acid
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2022 · IF 5.895

Unraveling the Thermal Oxidation Products and Peroxidation Mechanisms of Different Chemical Structures of Lipids: An Example of Molecules Containing Oleic Acid

Zheng Zhou,Yu-Lian Li,Feng Zhao,Ran Xin,Xu-Hui Huang,Yu-Ying Zhang,Dayong Zhou,Lei Qin

Lipid structures affect lipid oxidation, causing differences in types and contents of volatiles and nonvolatiles in various foods. In this study, the oxidation differences of monoacylglycerol (MAG), triacylglycerol (TAG), phosphatidylethanolamine (PE), and phosphatidylcholine (PC) with oleoyl residues and oleic acid (FA) during thermal treatment were investigated. Volatiles and nonvolatiles were monitored by gas chromatography–mass spectrometry and ultrahigh-performance liquid chromatography-Q-Exactive HF-X Orbitrap Mass Spectrometer, respectively. The results showed that the structures of MAG and TAG could delay the chain initiation reaction. The polar heads of PC and PE remarkably influenced the oxidation rate and the formation of the oxidation products probably due to the hydrogen bonds formed with free radicals. Among the volatile oxidation products, aldehydes, acids, and furans with eight or nine carbon atoms accounted for the majority in FA, MAG, TAG, and PC samples, but PE samples mainly generated ketones with nine or 10 carbon atoms. The formation of nonvolatile products in TAG samples possessed significant stage-specific changes. Fatty acid esters of hydroxy fatty acids were only produced in the free fatty acid oxidation model. The activity of chemical bonds participating in the truncation reaction decreased to both sides from the double bond position.

CAS / MDL: 140219-78-9
✓ 已验证 产品关联 DOI PubMed 高影响因子
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ACS Omega · 2022 · IF 4.132

Synthesis of Chainlike ZSM-5 with a Polyelectrolyte as a Second Template for Oleic Acid and Ethanol Cracking into Light Olefins

Wen He,Fuwei Li,Yufei Gu,Xiaofeng Wang,Hengshuo Gu,Hongbing Fu,Xiumei Liang,Zhixia Li

Chainlike ZSM-5 was synthesized in a tetrapropylammonium hydroxide (TPAOH) and poly(diallydimethylammonium chloride) (PDDA) dual-template system. The synthesis parameters and formation mechanism of chainlike zeolites were investigated. The optimized composition of the synthesis mixture was as follows: the PDDA/SiO2, TPAOH/SiO2, SiO2/Al2O3, and H2O/SiO2 molar ratios are, respectively, 0.16, 0.4, 50, and 40, with tetraethyl orthosilicate and aluminum nitrate as silicon/aluminum sources. The resultant ZSM-5 showed a cross-linked chainlike morphology, mesopore-dominated pore structure, and mild acidity. The formation of the chainlike zeolite was attributed to synergistic actions between PDDA and TPAOH. TPAOH acted as an alkali source and helped to induce nucleation and control the crystal size. PDDA acted as a soft template to promote crystal nucleation, and a hard template to form a three-dimensional mesoporous structure. Light olefin (C2–4=) selectivities from cracking of ethanol and oleic acid over the present chainlike ZSM-5 at 400 °C reached 90 and 75.7%, respectively, which were much higher than those from commercial ZSM-5 (75 and 52.3%, respectively), demonstrating the excellent hydrothermal stability and catalytic performance of the synthesized chainlike zeolite.

CAS / MDL: 26062-79-3
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ACS Omega · 2021 · IF 3.512

Detachment Force of Air Bubbles Detached from Low-Rank Coal Surface in the Presence of Adsorbed Oleic Acid–Dodecane Collector Mixture

Yinfei Liao,Hourui Ren,Maoyan An,Yijun Cao,Zhe Yang,Xiaodong Hao,Xingwei Song

It is well known that mixed collectors can effectively strengthen the flotation of low-rank coal. However, less concern has been paid to the detachment of low-rank coal flotation using mixed collectors. In this study, the force of air bubble detachment from low-rank coal surface treated by oleic acid (OA), dodecane (D), and oleic acid–dodecane (OA–D) collector mixture was investigated using microforce balance. The results showed that the process of bubble detachment from the low-rank coal surface was divided into three stages: relaxation stage, stretching stage, and sliding stage. The equilibrium contact angle and critical contact angle were the transition points between different stages. The order of detachment force required for bubble detachment from the surface of low-rank coal was OA–D > OA > D, indicating a synergistic effect between OA and D. Based on the three parameters of equilibrium contact angle, critical contact angle, and contact line length, a theoretical model was proposed to calculate the detachment force. The calculated results were in agreement with the measured results.

CAS / MDL: 112-40-3 112-80-1
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Processes · 2021 ·Vol. 9 ·期 3 ·404 · IF 2.847

Improving Low Rank Coal Flotation Using a Mixture of Oleic Acid and Dodecane as Collector: A New Perspective on Synergetic Effect

Maoyan An,Yinfei Liao,Yijun Cao,Xiaodong Hao,Longfei Ma

The mixed collector can improve low rank coal flotation efficiency, but its synergistic mechanism needs to be further explored. In this paper, oleic acid-dodecane (OA-D), oleic acid (OA), and dodecane (D) were employed to treat the low rank coal for revealing new synergistic mechanism of the mixed collector. First the surface free energy of the coal, the surface free energy of coal-water and coal-water-coal were calculated. Then wetting heat measurement, X-ray Photoelectron Spectroscopy (XPS) and FTIR were used to analyze synergistic mechanism of the mixed collector in depth. The results showed that OA-D obtained a higher combustible recovery than using OA and D, respectively. The essence of synergetic mechanism of OA-D was that they formed a relatively ordered “supramolecular structure” on the low rank coal surface, especially there were hydrophobic and van der Waals forces between the oleic acid chain and the dodecane chain that can promote the formation of a continuous collector film.Keywords:low rank coal;mixed collector;synergetic mechanism;supramolecular structure

CAS / MDL: 112-40-3 112-80-1
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JOURNAL OF MEMBRANE SCIENCE · 2020 · IF 7.183

Incorporation of oleic acid-modified Ag@ZnO core-shell nanoparticles into thin film composite membranes for enhanced antifouling and antibacterial properties

Xiujing Huang,Yingbo Chen,Xianshe Feng,Xiaoyu Hu,Yufeng Zhang,Lei Liu

In this study, Ag@ZnO-Oleic acid (OAc)/polyamide (PA) thin film nanocomposite (TFN) membranes were prepared by interfacial polymerization with dispersing hydrophobic Ag@ZnO-OAc core-shell nanoparticles in trimesoyl chloride (TMC) solutions. The Ag@ZnO-OAc nanoparticle structure and interactions between OAc and TMC were confirmed by TEM , XPS and FTIR. Surface morphology , roughness, chemical composition, hydrophilicity and charges of the synthesized membranes were characterized by SEM, FTIR, contact angle and zeta potential analyses. The results showed that incorporating the Ag@ZnO-OAc nanoparticles into the PA layer improved chemical and physical properties of the TFN membranes. Compared with the nanoparticle-free TFC membrane, the Ag@ZnO-OAc/PA TFN membrane showed a considerably higher salt rejection, and a lower flux decline rate when tested with filtration of BSA solution as a model foulant and a higher flux recovery with water flush. In addition, the Ag@ZnO-OAc/PA TFN membrane showed excellent antibacterial performance against E. coli and S. aureus .

✓ 已验证 产品关联 DOI 高影响因子
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NEW JOURNAL OF CHEMISTRY · 2021 ·Vol. 45 ·期 38 ·18070-18081 · IF 3.591

Synthesis of mesoporous Pt@SAPO-11 via in situ encapsulation for the decarboxylation of oleic acid to prepare C8–C17 alkanes

Xiaolong Liu,Jingye Ma,Hong Yuan

A series of mesoporous Pt@SAPO-11 catalysts with different Pt loadings were prepared using an in situ encapsulation process. These materials exhibited good topological structures and high Brunauer–Emmett–Teller (BET) surface areas (132–166 m2 g−1). Transmission electron microscopy images showed that the Pt nanoparticles in this material were in the 5–8 nm size range and were highly dispersed on the inner surfaces of the SAPO-11 support. N2-BET analyses demonstrated that the samples had mesoporous structures with average pore sizes of 7.3–8.5 nm. Characterization of the 1.0 wt% Pt@SAPO-11 catalyst by X-ray photoelectron spectroscopy and H2-temperature programmed reduction indicated strong interactions between the Pt nanoparticles and the carrier. This material was used to promote oleic acid decarboxylation under CO2 and gave a C8–C17 alkane yield of 80.8% after 4 h at 340 °C. After five repeated uses, the catalyst still gave a yield of 77.6%.

✓ 已验证 产品关联 DOI 高影响因子
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ACS Applied Materials & Interfaces · 2017 · IF 7.504

Self-Assembled Conjugated Polymer/Chitosan-graft-Oleic Acid Micelles for Fast Visible Detection of Aliphatic Biogenic Amines by “Turn-On” FRET

Haoquan Zhong,Chunchen Liu,Wenjiao Ge,Runcang Sun,Fei Huang,Xiaohui Wang

A fluorescent “turn-on” sensor for fast measurement of aliphatic biogenic amines (BAs) was developed based on fluorescent carboxylated polyfluorene (PFTBTCOOH)/chitosan-graft-oleic acid (CS-graft-OA) micelles. In this system, biobased CS-graft-OA micelles, prepared by graft modification of CS with OA, serve as the vector of the hydrophobic fluorescent probe. Bright turn-on fluorescence was achieved by the intermolecular fluorescence resonance energy transfer of the encapsulated PFTBTCOOH, driven by the formation of an electrostatic complex with aliphatic BAs, which facilitate visual identification. The peak intensity ratio of the PFTBTCOOH/CS-graft-OA micelles toward an increasing amount of aliphatic BAs was calibrated, giving a linear relationship. The fluorescence response of PFTBTCOOH/CS-graft-OA micelles to aliphatic BAs in milk and yogurt matrixes reaches a detection concentration as low as 10 μM, showing that the PFTBTCOOH/CS-graft-OA micelle solution is a potential chemosensor for fast and selective detection of trace aliphatic BAs, which is of great significance to public health and food safety.

✓ 已验证 DOI PubMed 高影响因子
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FOOD HYDROCOLLOIDS · 2024 · IF 11

Chitosan surface-modified bovine serum albumin-oleic acid self-assembled complexes: Improving the thermal stability, controlled release and bioaccessibility of fucoxanthin

Huiying Kuang,Liyuan Ma,Yuanjie Guo,Yixiang Liu

Fucoxanthin (FUCO) is a marine xanthophyll carotenoid with widespread potential physiological functions. However, poor water solubility and chemical instability limit FUCO's processing adaptability and bioavailability. In this study, chitosan surface-modified bovine serum albumin (BSA)-oleic acid (OA) self-assembled complexes were fabricated to improve the thermal stability as well as the controlled release and bioaccessibility of FUCO during gastrointestinal digestion. The results showed that glucose-grafted chitosan (GGC) could surface modify BSA-OA complexes by non-covalent affinity adhesion, resulting in a stable hydrophilic dispersion system with a polydispersity index <0.25 and a Zeta potential  > −20 mV. Fourier transform infrared spectroscopy and transmission electron microscope observations revealed that GGC covered the surface of BSA-OA particles through hydrogen bonding, hydrophobic and electrostatic interactions. The GGC-BSA-OA delivery system captured FUCO with >88.00% encapsulation efficiency. Additionally, embedding FUCO in the GGC-modified BSA-OA complex improved its thermal stability. In vitro, gastrointestinal digestion simulations showed that the GGC-modified protein shell had a controlled-release effect on FUCO, which prevented acidic pH from destroying FUCO due to premature release during gastric digestion and released it during intestinal digestion. As expected, GGC-BSA-OA, an encapsulated carrier, dramatically improved the FUCO's digestive stability (retention rate >74.00%), bioaccessibility (>54.42%), and micellization rate (>70.00%) in simulated gastrointestinal digestion. These findings suggested that GGC-BSA-OA as a delivery vehicle could effectively improve FUCO's thermal processing stability and absorbability.

CAS / MDL: 9001-62-1 9001-75-6
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SOLID STATE SCIENCES · 2025 · IF 3.3

Seed-assisted synthesis of ZSM-5 nanozeolites with high catalytic activities for cracking oleic acid to light olefins and light aromatics

Yanlin Wang,Hao Liu,Haoyu Liu,Hong Yuan

A series of nanosized ZSM-5 (SNZSM-5) zeolites has been synthesized by the seed-assisted method using silicalite-1 as seeds. Catalytic cracking of oleic acid to produce light olefins and light aromatics using SNZSM-5 as the catalyst was performed using a laboratory-scale fixed-bed reactor. The effects of the crystallization time and Si/Al molar ratio on the morphology and multilamellar structure of SNZSM-5 were studied to reveal how these properties affect the catalytic performance. Scanning electron microscopy, transmission electron microscopy, X-ray diffraction, temperature-programmed desorption of ammonia, and N 2 physisorption and desorption were performed to characterize the morphological features, acidities, and pore structures of the SNZSM-5 nanozeolites. Compared with conventional ZSM-5 zeolite, the SNZSM-5 nanozeolites possessed smaller particle diameters (90–450 nm), and they thus contained more intercrystalline voids. The Brunauer–Emmett–Teller surface areas (211–309 m 2  g −1 ) and mesopore volumes (0.08–0.27 cm 3  g −1 ) were both higher than those of ZSM-5 zeolite. Moreover, owing to the larger specific surface areas of the nanocrystals, more acidic sites can be exposed. Therefore, the SNZSM-5 nanozeolites showed higher catalytic activity and stability than conventional ZSM-5. The catalytic activity could be sustained for up to 35 h. Under the conditions of a reaction temperature of 500 °C, an oleic acid flow rate of 0.04 mL min −1 , and a nitrogen flow rate of 30 mL min −1 , the SNZSM-5 nanozeolite prepared with a Si/Al molar ratio of 16 showed the highest catalytic activity, producing up to 67 % yield of light olefins and showing 14.5 % selectivity for light aromatics.

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SEPARATION AND PURIFICATION TECHNOLOGY · 2024 · IF 8.1

Rough and porous silica-modified fiber membranes decorated with oleic acid for ultra-high flux and pH-responsive oil/water separation

Nuannuan Wang,Mengjiao Xu,Changyu Leng,Qingtao Ma,Jiale Wei,Luxiang Wang,Nannan Guo,Lili Ai,Shizhan Feng,Jiaojiao Dai,Xiaoting Xu,Lanlan Zhao

The design of fiber membranes with both ultra-high flux and pH-responsive oil/water separation is challenging but of great significance to environmental protection and human health. In this work, the pH-responsive fiber membranes were prepared by immersing the silica-modified polyacrylonitrile fiber substrates into oleic acid solution. The obtained membranes exhibited highly rough surface structures (Ra = 14.26 µm), large pore sizes (5.35 µm), high porosities (86.04%), and pH-responsive functional groups, respectively. The pH-responsive fiber membranes also had superhydrophobic surfaces and excellent selective separation for oil/water mixtures, for example, a trichloromethane permeation flux of 87,829 L m -2 h - 1 for immiscible oil/water separation, and a water permeation flux of 69,802 L m -2 h - 1 after turning the pH of water from 7 to 13. The above data were much higher than those of stimulus-responsive fiber membranes used for oil/water separation. In addition, the pH-responsive fiber membranes were also used for separating water-in-oil emulsions and oil-in-water emulsions, and achieved the highest separation flux of 15,120 L m -2 h - 1 . This work provides a simple strategy for the preparation of a stimulus responsiveness and high-performance material that can be used in the direction of treating practical oily wastewater.

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FOOD CHEMISTRY · 2024 · IF 8.5

Fabrication and characterization of oleic acid/sesame protein isolate/ poly (vinyl) alcohol core-shell nanofibers: Mitigating lipid oxidation by emulsion electrospinning

Meiyu Chen,Qinbo Jiang,Jiawen Li,Junjie Weng,Tianyi Yan,Yaqin Hu,Xiangyu Wang,Hui Zhang

Formulated oil-in-water (O/W) emulsions of oleic acid (OA) using sesame protein isolate (SPI) were processed via emulsion electrospinning with poly (vinyl) alcohol (PVA) to fabricate core-shell nanofibers for lipid oxidation prevention. The emulsion droplet size and viscosity increased as the oil volume fraction rose from 5 % to 30 %. The morphology tests and Fourier transform infrared spectroscopy (FTIR) confirmed the uniformity of nanofibers and OA encapsulation with hydrogen bonding. The thermal stability, mechanical properties, and water contact angle (WCA) of the nanofiber films improved with increased OA content. Encapsulation efficiency was 94.76 % and storage stability was maintained for 7 days in 5 % oil fraction nanofibers. The nanofibers showed lower oxidation and superior oxidative resistance to free OA, with the lowest peroxide value (POV, 2.14 mmol/L) and thiobarbituric acid-reactive substances (TBARS, 36.75 μmol/L). In conclusion, the OA/SPI/PVA (PE) core-shell nanofibers via emulsion electrospinning are efficient for fatty acid encapsulation in functional foods.

✓ 已验证 DOI PubMed 高影响因子
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Processes · 2021 ·Vol. 9 ·期 2 ·391 · IF 2.847

In Situ Modification of Activated Carbons by Oleic Acid under Microwave Heating to Improve Adsorptive Removal of Naphthalene in Aqueous Solutions

Zhansheng Wu,Pengyun Liu,Zhilin Wu,Giancarlo Cravotto

This study aimed to improve the adsorption capacity of activated carbon (AC) towards naphthalene (NAP) in aqueous solutions. Starch-based AC (SAC) and pulverized coal-based AC (PCAC) were prepared in a one-pot procedure by activation with oleic acid and KOH under microwave heating. Brunauer–Emmett–Teller (BET) specific surface areas reached 725.0 and 912.9 m2/g for in situ modified SAC (O-SAC1) and PCAC (O-PCAC1), respectively. π–π bond, H-bond, and hydrophobic effects were directly involved in the NAP adsorption process. Batch adsorption data were well fitted by pseudo-second order kinetics and the Freundlich isotherm model. As compared to ACs prepared with only KOH activation, NAP adsorption capacities of PCAC and SAC prepared by the one-pot method increased by 16.9% and 13.7%, respectively. Influences of varying factors were investigated in column adsorption of NAP using O-SAC1 and O-PCAC1. Based on breakthrough curves analysis, the larger column height (H), lower flow rate (Q0), and lower initial concentration (C0) resulted in the longer breakthrough and exhaustion times in both cases. Specifically, we concluded that O-PCAC1 exhibits better adsorption capacity than O-SAC1 in the given conditions. The optimized operating parameters were 1 cm (H), 1 mL/min (Q0) and 30 mg/L (C0). Finally, column adsorption data could be well fitted by the Thomas model.

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