LANGMUIR
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2025
·
IF 3.9
Li Li,Chao Song,Xiang Chen,Jingji Li,Lei Fan,Jie Han,Rong Guo
Lamellar liquid crystals (LLCs) exhibit significant potential in lubrication due to their unique layered structure. Introducing ionic liquids (ILs) to enhance the lubrication performance of the LLCs is a feasible approach. However, common ILs often demonstrate substantial corrosivity toward metals. In this study, LLCs were formed using oleic acid (OA) as the anion, alcoholamine solvents with corrosion-resistant properties (including monoethanolamine (MEA), diethanolamine (DEA), and triethanolamine (TEA)) as the cation, and glycerol (GL) as the solvent. The results reveal that the synergistic effect between the physical adsorption film and the tribochemical reaction film during friction significantly improves their lubricating performance. Notably, the OA/GL/MEA system outperforms OA/GL/DEA and OA/GL/TEA in lubrication properties, which can be attributed to its tighter intermolecular arrangement and smaller interlayer spacing, thereby providing enhanced mechanical strength. Furthermore, the ionic liquid-based LLCs exhibit negligible corrosiveness to steel, owing to the presence of carboxylic acid groups, unsaturated bonds, and hydroxyl groups in the molecular structure, which strengthen ILs adsorption on metal surfaces. Their combined lubrication efficacy and corrosion resistance render these LLCs highly promising for mechanical lubrication applications.
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FOOD CHEMISTRY
·
2022
·
IF 9.231
Rui Liu,Xiaoli Qin,Xiong Liu,Yonghua Wang,Jinfeng Zhong
The physicochemical properties and interactions of the complex of oleic acid (OA) and β-cyclodextrin (β-CD) were studied by experimental and computational methods. Differential scanning calorimetry and X-ray diffraction confirmed the successful preparation of OA/β-CD inclusion complex. The stability of the complex was improved, exhibiting a 61.2 °C higher degradation temperature and a lower peroxide value than OA. Raman and Fourier transform infrared spectroscopy studies revealed that the carboxyl group of OA entered into the β-CD cavity to form hydrogen bonds, which was confirmed by conformational search and weak interactions analysis. Dispersion energy from van der Waals (–290.79 kJ/mol) contributed 87.3% to total interaction energy (–253.88 kJ/mol). Topological analysis showed that four moderate hydrogen bonds were formed between OA and β-CD with the bond energy ranging from –76.05 to –30.25 kJ/mol. This work provided theoretical basis for the development of nutritional supplements containing unsaturated fatty acids encapsulated by β-CD.
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Catalysts
·
2021
·Vol. 11
·期 12
·1471
·
IF 4.146
Zhenzhen Li,Wei Liu,Guolong Yang
Synthesized oleic acid-based wax esters (e.g., cetyl oleate), which can replace spermaceti oil or jojoba oil, have been widely used in the cosmetic, pharmaceutical and other industries. In this work, 4-dodecylbenzenesulfonic acid (DBSA) has been successfully used as an efficient catalyst to synthesize oleic acid-based wax esters through esterification at 40 °C under solvent-free conditions. A 93.6% conversion rate of cetyl alcohol was obtained under optimal conditions: 10 mol% DBSA, a molar ratio of 1.3:1 oleic acid to alcohol, a reaction temperature 40 °C and a reaction time of 4 h. The effect of water content on esterification was investigated, and it was found that the inhibitory effect of water decreased significantly with increasing temperature. Moreover, DBSA-catalyzed esterification could be applied in the production of various oleic acid-based wax esters and excellent conversion (>90%) to esters was obtained under such mild conditions. DBSA-catalyzed low-temperature esterification is an efficient method for the production of liquid wax esters.Keywords:liquid wax esters;4-dodecylbenzenesulfonic acid;esterification;oleic acid;high-oleic sunflower seed oil
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Nutrition & Metabolism
·
2020
·Vol. 17
·期 1
·1-14
·
IF 3.211
Zeng Xin,Zhu Min,Liu Xiaohong,Chen Xuanmin,Yuan Yujia,Li Lan,Liu Jingping,Lu Yanrong,Cheng Jingqiu,Chen Younan
Background Pyroptosis is a novel programmed cell death. It is identified as caspase-1 dependent and characterized by plasma-membrane rupture and release of proinflammatory intracellular contents inculuding IL-1 beta and IL-18. Pyroptosis is distinct from other forms of cell death, especially apoptosis that is characterized by nuclear and cytoplasmic condensation and is elicited via activation of a caspase cascade. In pyroptosis, gasdermin D (GSDMD) acts as a major executor, while NLRP3 related inflammasome is closely linked to caspase-1 activation. Given that pyroptosis has played a critical role in the progression of non-alcoholic steatohepatitis (NASH), here, we investigated whether the regulation of pyroptosis activation is responsible for the protective role of monounsaturated oleic acids in the context of hepatocellular lipotoxicity.Methods Human hepatoma cell line HepG2 cells were exposed to palmitic acid (PA) with or without oleic acids (OA) or/and endoplasmic reticulum (ER) stress inhibitor tauroursodeoxycholic acid (TUDCA) for 24 h. Besides, the cells were treated with the chemical ER stressor tunicamycin (TM) with or without OA for 24 h as well. The expressions of pyroptosis and ER stress related genes or proteins were determined by real-time PCR, Western blot or immunofluorescence. The morphology of pyroptosis was detected by acridine orange and ethidium bromide (AO/EB) staining. The release of IL-1 beta and tumor necrosis factor alpha (TNF-α) was determined by ELISA. Sprague–Dawley (SD) rats were fed with high fat diet (HFD) for 16 w, then, HFD was half replaced by olive oil to observe the protective effects of olive oil. The blood chemistry were analyzed, and the liver histology and the expressions of related genes and proteins were determined in the liver tissues.Results We demonstrated that PA impaired the cell viability and disturbed the lipid metabolism of HepG2 cells (P < 0.01), but OA robustly rescued cells from cell death (P < 0.001). More importantly, we found that instead of cell apoptosis, PA induced significant pyroptosis, evidenced by remarkably increased mRNA and protein expressions of inflammasome marker NLRP3, Caspase-1 and IL-1beta, as well as cell membrane perforation driving protein GSDMD (P < 0.05). Furthermore, we demonstrated that the PA stimulated ER stress was causally related to pyroptosis. The enhanced expressions of ER stress markers CHOP and BIP were found subcellular co-located to pyroptosis markers NLRP3 and ASC. Additionally,TM was able to induce pyroptosis like PA did, and ER stress inhibitor TUDCA was able to inhibit both PA and TM induced ER stress as well as pyroptosis. Furthermore, we demonstrated that OA substantially alleviated either PA or TM induced ER stress and pyroptosis in HepG2 cells (P < 0.01). In vivo, only olive oil supplementation did not cause significant toxicity, while HFD for 32 w obviously induced liver steatosis and inflammation in SD rats (P < 0.05). Half replacement of HFD with olive oil (a mixed diet) has remarkably ameliorated liver abnormalities, and particularly inhibited the protein expressions of either ER stress and pyroptosis markers (P < 0.05).Conclusion Palmitic acid induced predominant pyroptosis in HepG2 cells, and ER stress may be responsible for the induction of pyroptosis and subsequent cell death. Monounsaturated oleic acids were able to ameliorate hepatocellular lipotoxicity both in vitro and in vivo, and OA mediated inhibition of ER stress and pyroptosis may be the underlying mechanisms.
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ENERGY & FUELS
·
2020
·
IF 3.421
Yulong Yang,Tingting Cheng,Hairong Wu,Zhenjiang You,Dansen Shang,Jirui Hou
Oleic acid-modified titania (OA-TiO2) nanoparticles are synthesized for the application of enhanced oil recovery (EOR) in low-permeability reservoirs. The oleic acid is grafted onto the surface of titania by the esterification reaction under a specific condition. The well-dispersed OA-TiO2 is expected to exhibit an excellent interfacial activity and a strong wettability alteration capability, owing to its amphiphilic features. This work aims to explore the potential of employing OA-TiO2 in EOR and to unveil its mechanisms of displacing oil in porous media. The interfacial properties of OA-TiO2 are systematically investigated by determining its interfacial tension and contact angle. A microfluidic test on a 2.5-D microfluidic model and a series of core floods are carried out to study the oil-displacement efficiency of OA-TiO2 nanofluids. The experimental results demonstrate that oleic acid-modified titania nanoparticles show great potential in not only reducing the injection pressure but also enhancing hydrocarbon recovery in low-permeability reservoirs.
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INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH
·
2018
·
IF 3.141
Zihao Zhang,Zhe Chen,Xin Gou,Hao Chen,Kequan Chen,Xiuyang Lu,Pingkai Ouyang,Jie Fu
Ni/AC (nickel on active carbon) catalysts with different Ni loadings were synthesized and studied for the decarboxylation and aromatization of oleic acid in the absence of H2 or hydrogen donors. Without the use of hydrogen source, the whole deoxygenation process became more economical. Moreover, oleic acid can be saturated using the H2 derived from the production of aromatics, which were also considered as the critical component in aviation biofuels. The structure and properties of the catalysts were investigated using X-ray diffraction, transmission electron microscopy, and temperature-programmed desorption of CH3COOH and CO. The experimental and characterization results revealed that 30% Ni/AC had a higher adsorption capacity of CH3COOH among the other Ni/AC catalysts and highly dispersed and small Ni particles, providing a heptadecane yield of 40.7%. It also contained 13.8% aromatics, which fulfills the requirement of aviation fuels. This Ni/AC catalyst showed good stability even after being reused thrice.
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LANGMUIR
·
2024
·
IF 3.7
Bin Wang,Kai Gao,Kai Wang,Yujie Wang,Qiuying Chang,He Yang
The tribological behavior of carboxylic acids, especially oleic acid, in boundary lubrication conditions is a subject of interest. This study presents the results of four-ball tribological tests conducted under varying contact pressures and sliding speeds. The findings reveal a critical turning speed within a confined zone, which causes a significant change in the frictional performances of oleic acid, leading to the formation of an ultralow wear tribofilm. This tribofilm, predominantly composed of oxyhydrogen compounds and hydrocarbons with more than five carbon atoms, is generated by the molecular action of oleic acid. Reactive nonequilibrium molecular dynamics simulations demonstrate that the shear speed-dependent decomposition modes of oleic acid and the transformation of the lubrication slip interface are the fundamental processes underlying the formation of this ultralow-wear boundary tribofilm.
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Sustainable Materials and Technologies
·
2024
·
IF 8.6
Rui Cai,Guangjin Hu,Yujie Chenyang,Zhixing Huang,Xiaohang Wang,Benyong Han
Five new amino-acid-functionalized methanesulfonate ionic liquids ([AAH][CH 3 SO 3 ]-ILs) were prepared using methanesulfonic acid and amino acids (AAs). The catalytic performances of the five synthesized [AAH][CH 3 SO 3 ]-ILs were evaluated for biodiesel synthesis via the esterification of oleic acid with methanol. Among them, IL [GluH][CH 3 SO 3 ] exhibited the optimal catalytic activity in the oleic acid esterification. An experimental design based on the RSM-BBD was used to optimize the reaction conditions. A conversion rate of 96.8 % was attained using the [GluH][CH 3 SO 3 ] catalyst for the oleic acid esterification at a catalyst load of 12 wt%, a molar ratio of 19.6:1, a reaction time of 3.5 h and a temperature of 103 °C. The [GluH][CH 3 SO 3 ]-catalyzed oleic acid esterification followed first-order kinetics with the activation energy and frequency factor of 9.86 kJ·moL −1 and 0.47 min −1 , respectively. The catalytic activity of the [GluH][CH 3 SO 3 ] catalyst did not considerably change during ten consecutive cycles of the esterification reaction. Operational simplicity, high conversion rate along with good reusability makes the IL [GluH][CH 3 SO 3 ] a promising catalyst for replacing traditional catalysts for the biodiesel preparation via the fatty acids esterification.
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JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY
·
2024
·
IF 2.8
Haoyu Liu,Jingye Ma,Hong Yuan,Xiang Shi
BACKGROUND A series of Pt@NZSM–5 and Pt/NZSM–5 nanosheets having different Si/Al ratios were prepared via an in situ synthesis and impregnation method, respectively, using C 22 H 45 –N + (CH 3 ) 2 –C 6 H 12 –N + (CH 3 ) 2 –C 6 H 13 (C 22–6–6 ) as the template agent. The oleic acid decarboxylation reaction was carried out using these materials under CO 2 atmosphere and the oleic acid cracking mechanism was inferred from the product distribution of the C8-C17 alkanes. RESULTS The Pt@NZSM–5 and Pt/NZSM–5 was found to comprise thinner nanosheets and exhibited strong metal–substrate interactions. Pt@NZSM–5 nanosheets with a Si/Al molar ratio of 100 had thicknesses of only 8–9 nm along with a mesopore/micropore capacity ratio of 2.7, an acid content of 11 cm 3 /g STP and a high Pt 0 /PtO x ratio. CONCLUSION The Pt@NZSM-5 and Pt/NZSM-5 nanosheets had an interconnected hierarchical system and a large number of metal active sites that facilitated the decarboxylation of oleic acid. The Pt@NZSM–5 nanosheets demonstrated excellent catalytic activity during the cracking of oleic acid under a CO 2 atmosphere, giving a yield of C8–C17 alkanes as high as 83.8% after 5 h at 320 °C. These Pt@NZSM–5 nanosheets also showed greater stability than the Pt/NZSM–5 specimens. © 2024 Society of Chemical Industry (SCI).
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ENERGY & FUELS
·
2025
·
IF 5.3
Haoyu Liu,Yanlin Wang,Hong Yuan
The introduction of mesopores to zeolite crystals via small organic templates has attracted widespread attention. In this study, we used cetylpyridinium bromide (CET–PyBr) to direct the synthesis of hierarchical meso-microporous ZSM-5 zeolite (HMM). By varying the CET–PyBr and sodium sulfate contents in the initial gel, the pore structure and acidity of the HMM were systematically modified. X-ray diffraction (XRD), Fourier-transform infrared (FTIR) spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), and N2 adsorption/desorption were utilized to investigate HMM’s mesoporous network. In HMM, mesopore formation was attributed to the assembly of nanocrystal clusters. By optimizing the organic templates, the HMM formation mechanism was elucidated. The acidities of the HMM catalysts were further characterized using temperature-programmed ammonia desorption, magic angle spinning nuclear magnetic resonance, and Py-IR spectroscopy. At 500 °C, the catalytic cracking of oleic acid over HMM yielded up to 54.0% light olefins, and HMM maintained its activity for up to 40 h. HMM’s homogeneous mesopores and moderate acidity contributed to its extended lifespan and enhanced its gaseous product yield.
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JOURNAL OF APPLIED POLYMER SCIENCE
·
2024
·Vol. 141
·期 33
·e55847
·
IF 2.7
Chao Zhang,Erlei Yu,Heyun Wang,Dong Huang,Guojun Ding,Zhonghua Zhao,Zhong Wei
In response to the health and environmental concerns associated with the plasticizer dioctyl phthalate (DOP), this research explores the utilization of methyl oleate (MO) derived from plant oil, 1,2,4-Benzeneticarboxylic anhydride (TMA) and isobutyric anhydride (IA) as a precursor for synthesizing a hyperbranched polyester named IA-MO-TMA. This polyester serves as an alternative plasticizer for Polyvinyl chloride (PVC). The chemical structure of IA-MO-TMA was thoroughly characterized using Fourier Transform Infrared Spectrometer (FTIR) and nuclear magnetic resonance hydrogen spectra, and its molecular weight was assessed. The PVC film, plasticized with IA-MO-TMA, underwent comprehensive testing using techniques such as differential scanning calorimetry, scanning electron microscopy, and thermogravimetric analysis. Notably, the glass transition temperature ( T g ) of the plasticized PVC film exhibited a significant reduction from 75°C to −6.7°C. The plasticized film demonstrated an elongation at break of 318.1%, a tensile strength of 19.2 MPa, and a plasticizing efficiency of 109.9%. Moreover, the use of IA-MO-TMA as a plasticizer increased the initial decomposition temperature of PVC film from 235.6 to 264.1°C. Additionally, the extraction rate of IA-MO-TMA in petroleum ether was found to be 35.6% lower than that of DOP.
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FOOD CHEMISTRY
·
2024
·
IF 8.5
Mianzhang Zhang,Zixin Huang,Pallavi Jayavanth,Ziming Luo,Hua Zhou,Caihuan Huang,Shiyi Ou,Fu Liu,Jie Zheng
Esterification of anthocyanins with saturated fatty acids have been widely investigated, while that with unsaturated fatty acids is little understood. In this study, crude extract (purity ∼ 35 %) of cyanidin-3- O -glucoside (C3G) from black bean seed coat was utilized as reaction substrate, and enzymatically acylated with unsaturated fatty acid (oleic acid). Optimization of various reaction parameters finally resulted in the highest acylation rate of 54.3 %. HPLC-MS/MS and NMR analyses elucidated the structure of cyanidin-3- O -glucoside-oleic acid ester (C3G-OA) to be cyanidin-3- O -(6″-octadecene)-glucoside. Introduction of oleic acid into C3G improved the lipophilicity, antioxidant ability, and antibacterial activity. Further, the color and substance stability analyses showed that the susceptibility of C3G and C3G-OA to different thermal, peroxidative, and illuminant treatments were highly pH dependent, which suggested individual application guidelines. Moreover, C3G-OA showed lower toxicity to normal cell (QSG-7701) and better inhibitory effect on the proliferation of HepG2 cells than C3G, which indicated its potential anti-tumor bioactivity.
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