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Oleic Acid
ACS Applied Energy Materials · 2023 · IF 6.4

Enhancing Charge Carrier Transport in the Carbon-Electrode-Based CsPbI2Br Perovskite Solar Cells via I/Br Homogenization Process Modulation and Oleic Acid Surface Passivation

Mingzhe Zhang,Wenhui Li,Wenning Zhao,Xiuxun Han

The carbon-electrode-based CsPbI2Br perovskite solar cells (C-PSCs) are promising photovoltaic technology because of their enhanced stability and low cost. However, the CsPbI2Br film suffers from uneven surface morphology with stripes and the defect-rich surface, which are detrimental to the charge carrier transport between perovskite and carbon. Here, we demonstrate that the formation of stripes is directly related to the I/Br homogenization process during annealing. By introducing a pre-annealing treatment before high temperature annealing, the I/Br homogenization process is modulated and the stripe is successfully wiped off. Besides, enhanced charge carrier transport in the C-PSCs is achieved. Oleic acid (OA) is then introduced to modify the stripe-free perovskite film surface. It is revealed that the carboxyl group in the OA molecule can passivate the undercoordinated Pb ions, leading to further improved charge carrier transport. Eventually, a power conversion efficiency (PCE) of 15.57% is achieved, which is among the highest PCE for the CsPbX3-based C-PSCs. This work demonstrates that combining surface planarization with surface passivation is an effective strategy for developing highly efficient C-PSCs.

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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2023 · IF 8.2

Immobilization of lipase on hydrophobic MOF synthesized simultaneously with oleic acid and application in hydrolysis of natural oils for improving unsaturated fatty acid production

Geling Kuang,Zichen Wang,Xiuyan Luo,Zixin Geng,Jiandong Cui,Muhammad Bilal,Ziyuan Wang,Shiru Jia

The hydrolysis of natural oils (vegetable oils and fats) by lipase has significant applications in food and medicine. However, free lipases are usually sensitive to temperature, pH and chemical reagents in aqueous solutions, which hinders their widespread industrial application. Excitingly, immobilized lipases have been widely reported to overcome these problems. Herein, inspired by lipase interface activation, a hydrophobic Zr-MOF (UiO-66-NH 2 -OA) with oleic acid was synthesized for the first time in an emulsion consisting of oleic acid and water, and the Aspergillus oryzae lipase (AOL) was immobilized onto the UiO-66-NH 2 -OA through hydrophobic interaction and electrostatic interaction to obtain immobilized lipase (AOL/UiO-66-NH 2 -OA). 1 H NMR and FT-IR data indicated that oleic acid was conjugated with the 2-amino-1,4-benzene dicarboxylate (BDC-NH 2 ) by amidation reaction. As a result, the V max and K cat values of AOL/UiO-66-NH 2 -OA were 179.61 μM﹒min −1 and 8.27 s −1 , which were 8.56 and 12.92 times higher than those of the free enzyme, respectively, due to the interfacial activation. After treated at 70 °C for 120 min, the immobilized lipase maintained 52 % of its original activity, but free AOL only retained 15 %. Significantly, the yield of fatty acids by the immobilized lipase reached 98.3 % and still exceeded 82 % after seven times of recycling.

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Journal of Environmental Chemical Engineering · 2023 · IF 7.7

Green diesel-like hydrocarbon production by H2-free catalytic deoxygenation of oleic acid via Ni/MgO-Al2O3 catalysts: Effect of the metal loading amount

Feng Shi,Hongyuan Wang,Yifei Chen,Yanling Lu,Defa Hou,Can Liu,Yi Lu,Xu Lin,Xiaoqin Yang,Zhifeng Zheng,Yunwu Zheng

To develop an efficient and feasible catalyst for converting inedible vegetable oil to green biodiesel via a one-step decarboxylation process, a series of Ni-based MgO-Al 2 O 3 catalysts with different active Ni species were fabricated by adjusting the various Ni loading amounts (2.5–20%) and applied to the catalytic deoxygenation of OA to generate green biodiesel. Additionally, the structure-property relationship, deactivation mechanism and regeneration performance were also evaluated via various characterization technologies (XRD, BET, NH 3 -TPD, H 2 -TPR, XPS, SEM-EDX, HRTEM, TGA, Raman as well as GC/MS and UV-fluorescence spectra). The experimental results indicated that Ni introduction obviously enhanced the conversion ratio. Ni (10%)/MgO-Al 2 O 3 catalysts exhibited excellent catalytic performance with the highest HCs (95.12%), olefin content (57.37%) and green biodiesel content (75.90%) due to mild Brønsted-rich acidity sites, lower reduction temperature, higher active metallic Ni species content, suitable oxygen vacancy content and favorable texture properties via the decarbonylation reaction pathway. Furthermore, lower Ni loading was beneficial to gasoline and bioaviation fuel generation due to higher Brønsted-rich acidity sites and total acid amount, which boosted C-C scission by cracking reaction, and higher Ni content facilitated biodiesel formation. Additionally, Ni (10%)/MgO-Al 2 O 3 catalysts showed excellent reusability and regeneration due to Ni active species, but these advantages were slightly decreased (HCs: from 95.12% to 61.63%; biodiesel: from 75.90% to 57.52%) due to coke deposition and metal active species leaching and oxidation .

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FOOD RESEARCH INTERNATIONAL · 2020 · IF 4.972

Insights into the multi-scale structure and in vitro digestibility changes of rice starch-oleic acid/linoleic acid complex induced by heat-moisture treatment

Hai He,Bo Zheng,Hongwei Wang,Xiaoxi Li,Ling Chen

The study presents an innovative approach using heat-moisture treatment (HMT) to prepare rice starch-oleic acid (OA)/linoleic acid (LOA) complex. Relationship of the multi-scale structure- in vitro digestibility of rice starch-OA/LOA complex induced by HMT was established in this work. Herein, HMT induced the formation of single helices complex between OA/LOA and amylose or long side chains of amylopectin, which formed more V-type crystallite. HMT assisted complexation with OA/LOA resulted in higher ordered molecular chain aggregations in amorphous amylose background area, reduced the amorphous lamellae and made the double helices and A-type crystallite perfectly arranged. These structural alternations inhibited the molecular interactions (e.g., binding ability, catalyzed location) between rice starch and α-amylase, which eventually increased the resistant starch (RS) content and decreased the slow digestible starch (SDS) content. Moreover, HMT treated rice starch formed type II complex with OA and type I complex with LOA, and all the referred changes went more obvious with the increasing amount of OA than LOA. The results suggested that the OA/LOA was inserted inside the amylose spiral cavity and the amorphous lamellae of rice starch. The current study exhibited an in-depth research of the multi-scale structure within rice starch-OA/LOA complex and proposes a promising approach to ensure the starch products have designated digestibility.

CAS / MDL: 60-33-3 112-80-1
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FUEL · 2018 · IF 4.908

Efficient and stable Cu-Ni/ZrO2 catalysts for in situ hydrogenation and deoxygenation of oleic acid into heptadecane using methanol as a hydrogen donor

Zihao Zhang,Hao Chen,Changxue Wang,Kequan Chen,Xiuyang Lu,Pingkai Ouyang,Jie Fu

In this work, a series of ZrO 2 -supported Cu, Ni and bimetallic Cu-Ni catalysts were synthesized and evaluated for their activity and stability in the in situ hydrogenation and decarboxylation of oleic acid using methanol as a hydrogen donor. High-angle annular dark-field scanning transmission electron microscopy (HADDF-STEM), energy dispersive X-ray spectroscopy (EDS-mapping), X-ray diffraction (XRD) and temperature programmed reduction (TPR) characterizations revealed that the as-synthesized Cu-Ni/ZrO 2 was a Cu-Ni alloy that was highly dispersed on mixed m-ZrO 2 and t-ZrO 2 . The bimetallic Cu-Ni/ZrO 2 nanostructures not only exhibited better catalytic activity for the conversion of oleic acid compared to monometallic Cu/ZrO 2 and Ni/ZrO 2 catalysts but also demonstrated good reuse performance. The formation of the Cu-Ni alloy facilitated the decarboxylation reaction and inhibited the cracking reaction, leading to enhanced catalytic performance. The good stability of Cu-Ni/ZrO 2 was primarily due to the good hydrothermal stability of the ZrO 2 support.

CAS / MDL: 14985-18-3
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BIOCHEMICAL ENGINEERING JOURNAL · 2024 · IF 3.7

Enzymatic synthesis of TMP esters based on pelargonic acid from the cleavage of oleic acid: Evaluation of synthetic process, physicochemical properties and lubrication performance

Qian Mao,Changliu He,Biqiang Chen,Xu Zhang

Biolubricants produced by chemically modifying vegetable oils are promising to replace mineral-based lubricants. However, the performances of biolubricants synthesized through traditional chemical modification routes, such as transesterification/esterification, epoxidation with further ring opening, and estolide formation, cannot satisfy the demands of extreme conditions. Meanwhile, complicated multi-step reactions cause expensive costs, which hinders their large-scale application. In this study, pelargonic acid (PA) derived from the cleavage of oleic acid was esterified with trimethylolpropane (TMP) to produce branched-chain esters (tri-TMP esters) catalyzed by the lipase ( Candida sp. 99–125 ), focusing on batch stability of the lipase, thermal-oxidation stability and lubrication performance of the product. The lipase maintained high activity for 4 continuous batches in 5 L enzyme reactor with the conversion of PA > 96% and the accumulation of tri-TMP esters > 84% in each batch. The obtained tri-TMP esters had a pour point of − 56 °C, a viscosity index of 137, and a flash point of 276 °C. Anti-oxidation stability test and thermogravimetric behaviors showed that the biolubricant had favorable thermal-oxidative stability. Friction tests verified that the product displayed excellent lubrication performance with a minimum coefficient of friction (COF) of 0.099 and an average wear spot diameter (WSD) of 221.5 µm. The green and high-selective synthetic pathway fills the defect of existing routes for the preparation of biolubricants from chemically modified vegetable oils.

CAS / MDL: 112-05-0 77-99-6
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GREEN CHEMISTRY · 2017 ·Vol. 19 ·期 17 ·4157-4168 · IF 9.125

Insight into forced hydrogen re-arrangement and altered reaction pathways in a protocol for CO2 catalytic processing of oleic acid into C8–C15 alkanes

Shiyou Xing,Pengmei Lv,Haoran Yuan,Lingmei Yang,Zhongming Wang,Zhenhong Yuan,Yong Chen

A new vision of using carbon dioxide (CO2) catalytic processing of oleic acid into C8–C15 alkanes over a nano-nickel/zeolite catalyst is reported in this paper. The inherent and essential reasons which make this achievable are clearly resolved by using totally new catalytic reaction pathways of oleic acid transformation in a CO2 atmosphere. The yield of C8–C15 ingredients reaches 73.10 mol% in a CO2 atmosphere, which is much higher than the 49.67 mol% yield obtained in a hydrogen (H2) atmosphere. In the absence of an external H2 source, products which are similar to aviation fuel are generated where aromatization of propene (C3H6) oxidative dehydrogenation (ODH) involving CO2 and propane (C3H8) and hydrogen transfer reactions are found to account for hydrogen liberation in oleic acid and achieve its re-arrangement in the final alkane products. The reaction pathway in the CO2 atmosphere is significantly different from that in the H2 atmosphere, as shown by the presence of 8-heptadecene, γ-stearolactone, and 3-heptadecene as reaction intermediates, as well as a CO formation pathway. Because of the highly dispersed Ni metal center on the zeolite support, H2 spillover is observed in the H2 atmosphere, which inhibits the production of short-chain alkanes and reveals the inherent disadvantage of using H2. The CO2 processing of oleic acid described in this paper will significantly contribute to future CO2 utilization chemistry and provide an economical and promising approach for the production of sustainable alkane products which are similar to aviation fuel.

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TISSUE & CELL · 2025 · IF 2.5

Oleic acid inhibits the proliferation, invasion and migration of tongue squamous cell carcinoma cells under high glucose conditions through S100A9-HK2/PKM2-SOD2 signaling pathway

Yujie Ma,Runqiang Liu,Juan Zhan,Yihan Lai,Sicheng Li,Wei Wang,Yisen Shao,Lin Jiang

The incidence of tongue squamous cell carcinoma (TSCC) has been increasing annually. Type 2 diabetes mellitus (T2DM) is one of the risk factors for TSCC, with hyperglycemia being a hallmark of T2DM that promotes the development of oral cancer and results in poorer prognoses for TSCC patients who also have T2DM. Oleic acid (OA), a component of Brucea javanica oil emulsion, exhibits both anti-cancer and anti-diabetic properties. However, the precise regulatory mechanisms of OA on tongue squamous cell carcinoma (TSCC) under high glucose conditions have yet to be fully elucidated. Our findings demonstrated that high glucose significantly enhanced the migratory, invasive, and proliferative capabilities of TSCC cells. Notably, OA treatment effectively reversed these high glucose-induced enhancements in TSCC cellular activities. Furthermore, our research revealed that OA exerted its anti-tumor effects by stabilizing its binding with S100A9, which modulated the glycolytic pathway. Ultimately, we confirmed that the anti-tumor mechanism of OA in TSCC patients with T2DM was associated with the inactivation of the S100A9-HK2/PKM2-SOD2 pathway. In summary, OA inhibited the proliferation, migration, and invasion of TSCC cells under high glucose conditions through the regulation of the S100A9-HK2/PKM2-SOD2 pathway.

CAS / MDL: 1310-73-2
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MOLECULES · 2026 ·Vol. 31 ·期 4 ·594 · IF 5.1

Mechanism of Water-Enhanced Volatile Aldehyde Release in Oil Fumes from Thermal Oxidation of Oleic Acid: Insights from Synchrotron Radiation Photoionization and Gas Chromatography–Mass Spectrometry

Bing Qian,Xuan Zhu,Chulian Su,Hongxing Li,Qiong Wu,Chengyuan Liu,Yang Pan,Bingjun Han

Thermal oxidation of edible oils during high-temperature cooking produces complex fumes containing harmful volatile compounds. However, the role of water, a common co-reactant in practical cooking, remains insufficiently understood. In this study, oleic acid was used as a model compound to investigate thermal oxidation. Online monitoring using synchrotron radiation photoionization mass spectrometry (SR-PIMS) revealed that water significantly increased the emission of volatile acetaldehyde and acrolein, with maximum increases of 164% and 123% at 10% water addition. Complementary offline GC-MS analysis showed enhanced formation of (E)-2-decenal, (E,E)-2,4-decadienal, and (E)-2-undecenal, suggesting these unsaturated aldehydes may be key intermediates. Mechanistically, oleic acid underwent free radical-mediated peroxidation to form (E)-2-decenal, (E)-2-undecenal, and (E,E)-2,4-decadienal. These intermediates subsequently decomposed into acetaldehyde and acrolein via hydration, retro-aldol condensation, and hydroperoxide scission, with water accelerating both processes. Overall, these findings highlight water’s critical role in promoting the generation of harmful volatile aldehydes in oil fumes.

CAS / MDL: 112-80-1
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FOOD RESEARCH INTERNATIONAL · 2026 · IF 8.8

Ice recrystallization inhibition by amylose-oleic acid complex: Enhancing the freezing tolerance and shape fidelity of starch-based 3D printing ink in long-term frozen storage

Zhongyu Zuo,Ming Zhang,Xinxia Zhang,Ting Li,Anbang Hui,Mengdi Chen,Shunqian Xu,Li Wang

The ink with starch-lipid complex exhibits a high stability in frozen storage. • Starch-lipid complex enhances the shape fidelity of printed model. • Complex may suppress ice growth consistent with the Gibbs-Thomson effect. • Conformation of lipid molecule affects complex adsorption on ice surface. Developing starch-based 3D printing inks with stable texture and high shape fidelity is essential for producing higher value-added food products. However, inhibiting ice recrystallization and maintaining structural stability during cold-chain transport and frozen storage remain significant challenges. To address these questions, this study validates the hypothesis that starch-lipid complex intervenes the ice crystal growth in starch-based 3D printing ink, and investigates the effects of molecular conformation on the ice surface behavior of starch–lipid complexes. The amylose-oleic acid (OA) complex greatly suppresses ice recrystallization by stably adsorbing on the freezing interface, which induces a disordered arrangement of ice crystals. MD simulation supported a proposed mechanism for ice recrystallization inhibition that is consistent with the Gibbs–Thomson effect. The resulting edible ink of starch-OA complex exhibited a lower growth rate of ice crystal size (from 33.33 ± 2.44 μm 2 to 96.51 ± 22.68 μm 2 after 80 d at −24 °C) when compared with a control group (from 65.88 ± 5.43 μm 2 to 187.78 ± 21.98 μm 2 ). Moreover, the starch-OA complex still retains the ability to resist ice crystal growth after high-temperature treatment (e.g., 95 °C), enabling adapting to a variety of food processing conditions. This work offers potential applications for the starch-lipid complex in cold storage-enabling material and food preservation. Download: Download high-res image (216KB) Download: Download full-size image

CAS / MDL: 122-32-7
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Materials · 2024 ·Vol. 17 ·期 11 ·2620 · IF 3.1

Epoxidized Soybean Oleic Acid/Oligomeric Poly(lactic acid)-Grafted Nano-Hydroxyapatite and Its Role as a Filler in Poly(L-lactide) for Potential Bone Fixation Application

Chen Huang,Xin-Yu Luo,Zi-Sheng Chao,Yue-Fei Zhang,Kun Liu,Wen-Jun Yi,Li-Jun Li,Zeyan Zhou

One of the most effective strategies for modifying the surface properties of nano-fillers and enhancing their composite characteristics is through polymer grafting. In this study, a coprecipitation method was employed to modify hydroxyapatite (HAP) with epoxidized soybean oleic acid (ESOA), resulting in ESOA-HAP. Subsequently, oligomeric poly(lactic acid) (OPLA) was grafted onto the surface of ESOA-HAP, yielding OPLA-ESOA-HAP. HAP, ESOA-HAP, and OPLA-ESOA-HAP were comprehensively characterized. The results demonstrate the progressive grafting of ESOA and OPLA onto the surface of HAP, resulting in enhanced hydrophobicity and improved dispersity in organic solvent for OPLA-ESOA-HAP compared to HAP. The vitality and adhesion of Wistar rat mesenchymal stem cells (MSCs) were assessed using HAP and modified HAP materials. Following culture with MSCs for 72 h, the OPLA-ESOA-HAP showed an inhibition rate lower than 23.0% at a relatively high concentration (1.0 mg/mL), which is three times lower compared to HAP under similar condition. The cell number for OPLA-ESOA-HAP was 4.5 times higher compared to HAP, indicating its superior biocompatibility. Furthermore, the mechanical properties of the OPLA-ESOA-HAP/PLLA composite almost remained unaltered ever after undergoing two stages of thermal processing involving melt extrusion and inject molding. The increase in the biocompatibility and relatively high mechanical properties render OPLA-ESOA-HAP/PLLA a potential material for the biodegradable fixation system.

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AICHE JOURNAL · 2025 · IF 4

Hierarchical catalysts with controllable C?C and C?O bond activation ability for selective hydrogenation of oleic acid

Jinlin Mei,Zhentao Liu,Zhengkai Cao,Aocheng Wang,Xiaoyang Kong,Aijun Duan,Chunya Wang,Chunming Xu,Xilong Wang

Hierarchical Y/SBA-15 meso-microporous composites (YS- x ) and corresponding highly dispersed catalysts (Ni/YS- x ) were prepared and applied to the production of jet fuel range hydrocarbons by the selective hydrogenation of oleic acid. Small particle size and electron-deficient Ni δ+ are detrimental to the C  C bond activation of the η 1 (C)-acyl conformation and inhibit the decarbonylation/decarboxylation pathway. Besides, the activation ability of the C  C bond is regulated to avoid excessive cleavage by the acidity and diffusion properties of the hierarchical Ni/YS- x catalysts, thus affecting their hydroisomerization and hydrocracking properties. The abundant acid sites are beneficial to the selective activation of the C  O bond of the η 2 (C, O)-aldehyde conformation and the promotion of the reductive deoxygenation pathway. The optimal Ni/YS-1 shows the highest iso / n -alkane ratio ( i / n = 6.26) and superior jet fuel range hydrocarbons yield (48.8%, 340°C), which is a benefit from its outstanding acid–metal balance and worthy diffusion property.

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