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ACTA PHYSICO-CHIMICA SINICA · 2016 ·Vol. 32 ·期 11 ·2753-2760 · IF 0.844

Synthesis and Properties of a Novel Bio-Based Branched Heptadecylbenzene Sulfonate Derived from Oleic Acid

BIAN Peng-Cheng,ZHANG Da-Peng,GANG Hong-Ze,LIU Jin-Feng,MU Bo-Zhong,YANG Shi-Zhong

Bio-based surfactants have attracted increasing attention because they are made from renewable resources and have excellent surface/interfacial properties. In this study we prepared a novel bio-based branched alkylbenzene sulfonate surfactant by a four-step route using renewable oleic acids as starting materials. We evaluated the surface behavior, wettability, and biodegradability of our surfactant. The surfactant, 4-(1-heptadecyl) benzene sodium sulfonate (9ΦC17S), was synthesized using a facile four-step route involving alkylation, decarboxylation, sulfonation and neutralization, respectively. The chemical structure of 4-(1-heptadecyl) benzene sodium sulfonate was confirmed by infrared (IR) spectroscopy, electrospray ionization high resolution mass spectrometry (ESI HRMS) and 1H nuclear magnetic resonance (1H NMR) spectroscopy. The surfactant demonstrated an excellent surface tension of 32.54 mN·m-1 at the critical micelle concentration (CMC) of 317.5 mg·L-1 and outstanding interfacial tension of ~10-2 mN·m-1 at 8.36×104 mg·L-1 with 8.48×104 mg·L-1 Na2CO3. The surfactant also showed good biodegradability with an ultimate biodegradation score of 2.99. The surfactant had good wettability with an air/water/solid contact angle ( average) of 63.08° for a 0.500 g·L-1 9φC17S solution. This novel bio-based branched surfactant contributes to the structural diversity of biobased surfactants from renewable feedstock.

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TRANSITION METAL CHEMISTRY · 2019 ·Vol. 45 ·期 1 ·31-39 · IF 1.016

Polyethyleneimine-oleic acid micelle-stabilized gold nanoparticles for reduction of 4-nitrophenol with enhanced performance

Wang Longgang,Zhang Xuan,Cui Yanshuai,Guo Xiaolei,Chen Shengfu,Sun Haotian,Gao Dawei,Yang Qinghua,Kang Jianxin

Abstract Noble metal nanoparticles have been drawing great attention for the treatment of water pollutants. The catalytic activity of noble metal nanoparticles is usually reduced due to their aggregation. Amphiphilic molecule micelles have potential to stabilize the noble nanoparticles against aggregation. In this study, a novel facile method was reported for preparing polyethyleneimine-oleic acid (PEI-oleic acid) micelle-stabilized gold nanoparticles (PO-AuNPs n ), where the gold nanoparticles (AuNPs) were embedded in the shell area of micelles. When the molar ratio of [N] to [Au] was 50, 100, and 200, the mean diameter of AuNPs was 3.52 ± 0.42, 3.11 ± 0.28, and 2.85 ± 0.48 nm, respectively. The corresponding zeta potential of the PO-AuNPs n was determined to be 26.2, 28.9 and 35.7 mV, respectively. Furthermore, PO-AuNPs n remained stable in aqueous solution at room temperature for more than 1 month. More importantly, PO-AuNPs n had higher catalytic activity for 4-nitrophenol (4-NP) reduction in aqueous solution compared with previous reports, where PO-AuNPs 200 showed a K nor value of 9367 s −1  g −1 . It is believed that PO-AuNPs n showed high catalytic activity because of their small size, high stability, and the location of AuNPs in the shell area, which made it easier for AuNPs to contact with 4-NP. The method described in this report represents a new method to prepare small and stable noble metal nanoparticles for catalytic applications in the future.

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JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY · 2026 · IF 6.7

NRF2-CD36 Axis-Mediated Oleic Acid-Induced Milk Fat Production in Dairy Cow Mammary Epithelial Cells

Caiyan Zhang,Fengxian Sui,Meiyan Liu,Yalin Xie,Jiadi Su,Jing Gao,Ye Lin,Yang Yang,Xiaoming Hou

Oleic acid (OA)-enriched diet significantly enhances CD36 expression and promotes milk fat production in the mammary gland. However, the mechanisms by which OA upregulates this process are unknown. Here, GC-MS analysis and molecular docking were used to assess OA-CD36 binding, while gene expression and ChIP assays clarified the OA-mediated regulation of CD36 and milk fat synthesis. The results showed that CD36 is highly expressed in the lactating mammary tissues of dairy cows and positively regulates milk fat production. OA enters dairy cow mammary epithelial cells via direct binding to CD36. OA stimulation elevates the CD36 expression and translocation. ChIP assays confirmed CD36 as a target gene of NRF2. OA also enhances NRF2 expression and nuclear translocation, which in turn upregulates CD36 expression and function. This study elucidates the NRF2–CD36 axis as a regulator of OA-driven milk fat synthesis in mammary tissue, offering practical value for dairy industry nutritional strategies.

CAS / MDL: 112926-00-8
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NEW JOURNAL OF CHEMISTRY · 2026 · IF 2.5

Unveiling the inhibition mechanism of oleic acid polyethylene glycol ester phosphate for Mg and Mg alloy

Chang Zhou,Guangliang Zhang,Xiumei Tai,He Jiang,Lianbing Cui

Compared to single-function inhibitors, the novel multifunctional corrosion inhibitor developed in this study—oleic acid polyethylene glycol ester phosphate (OPP400)—achieves synergistic corrosion inhibition through molecular engineering that integrates multiple active functional segments. Its corrosion inhibition behavior and mechanism on Mg and Mg alloy in 3.5 wt% NaCl solutions were systematically investigated. The corrosion inhibition performance of OPP400 was evaluated using a combination of EIS, PDP, SEM, AFM, and contact angle measurements. The results demonstrate that at the optimal concentration of 100 mg L−1, OPP400 achieves corrosion inhibition efficiencies of 89.07% for pure Mg and 79.55% for Mg alloy. The PDP curves reveal OPP400 to be a mixed-type corrosion inhibitor. EIS reveals a marked increase in charge transfer resistance and a marked decrease in double-layer capacitance, which indicates the formation of a dense adsorbed film on the metal surface. Mott–Schottky analysis further corroborates that OPP400 selectively blocks Cl− ions by reducing the carrier density in the oxide film and enhancing the energy barrier of the passivation film. Surface analysis reveals that OPP400 significantly reduces the surface roughness of the substrate and enhances its hydrophobicity, thereby increasing the water contact angle from 37° to more than 66°. The inhibition mechanism is attributed to the synergistic effects of chemical adsorption, hydrophobic layer formation, and ionic barrier action, which collectively block the penetration of corrosive species (e.g., Cl− and H3O+). This study offers critical theoretical basis and practical guidance for the molecular design of corrosion inhibitors targeting Mg and Mg alloy.

CAS / MDL: 1314-56-3
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Polymers · 2026 ·Vol. 18 ·期 18 ·2297 · IF 5.8

Toughening PLA via Diisocyanate-Induced Dynamic Vulcanization of Carboxylated Oleic Acid: Role of Crosslinked Network Topology

Diisocyanate-induced dynamic vulcanization of difunctional fatty acids has emerged as a universal strategy to efficiently improve the impact resistance of polylactic acid (PLA). However, how the crosslinked network topology of the in situ formed polyamide elastomer (COPA) affects its toughening efficacy on PLA remains unknown. Here, we synthesized two carboxylated fatty acids with distinct molecular architectures (TCOA and NCOA) from technical-grade and high-purity oleic acids via UV-initiated thiol-ene click chemistry. These two diacids, along with tetradecanedioic acid (TA) without a dangling chain, were dynamically vulcanized with hexamethylene diisocyanate (HDI) to toughen PLA. By varying NCO/COOH molar ratios between HDI and TCOA, their effects on gel content, crosslinking density, phase morphology, and mechanical properties of resulting blends were systematically investigated. With increasing the ratio, both gel content and interfacial adhesion with PLA in the blends were enhanced, accompanied by the transformation of phase structure from “sea-island” morphology to a partially or fully co-continuous one. At a molar ratio of 1.8:1, the notched impact strength value of the blend reached 86.5 kJ/m2. By substituting TCOA with high-purity NCOA or TA, comparable gel content and interfacial compatibilization level, and co-continuous morphologies were achieved. Notably, NCOA yielded a PLA blend with a remarkably higher impact toughness (131.0 kJ/m2). The linear chain structure of TA led to a higher crosslinking density of the formed TAPA domains, which unfavorably suppressed their cavitation during impact fracture and thus resulted in an inferior impact strength (7.0 kJ/m2). These findings provide valuable insights into the toughening mechanism of PLA via dynamic vulcanization of monomers.

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Advanced Optical Materials · 2023 ·Vol. 11 ·期 13 ·2300064 · IF 9

Tailoring Molecular Dimensions of Cesium Lead Bromide Perovskites with Varying Compositions of Oleic Acid and Oleylamine

Guoqing Xu,Shuoshuo Zang,Hewen Liu

The evidence on deciphering nucleation and growth of cesium lead halide perovskite crystals, and establishing the phase diagram of cesium lead halide perovskites of different dimensions is still lacking. In this work, a facile method for the synthesis of cesium lead bromide crystals of different molecular level dimensions at room temperature is presented by varying the OA/OAm ratios without changing the proportions of Cs and Pb precursors. Bromide ions are gradually released in the systems through the gamma-ray radiation chemistry of bromobenzene. As the volume ratios of OA/OAm increase, different products such as CsBr, Cs 4 PbBr 6 (0D), white δ -CsPbBr 3 (1D), γ -CsPbBr 3 (3D) associated with PbBr 2 sheets, and γ -CsPbBr 3 are obtained in order. 1D δ -CsPbBr 3 can be transformed into 2D CsPb 2 Br 5 through CsBr stripping in water. The phase diagram established in this work is helpful for understanding the nucleation and growth mechanism of Cs–Pb–Br perovskite crystals of different dimensions. The nucleation of Cs–Pb–Br perovskite crystals is driven by the supersaturation of either CsBr or PbBr 2 caused by varying OA/OAm ratios, i.e., 0D Cs 4 PbBr 6 at the supersaturation of CsBr, while 3D γ -CsPbBr 3 at the supersaturation of PbBr 2 . 1D perovskite is the intermediate state between 0D and 3D perovskites.

✓ 已验证 产品关联 DOI 高影响因子
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JOURNAL OF GEOPHYSICAL RESEARCH-ATMOSPHERES · 2023 ·Vol. 128 ·期 12 ·e2023JD038675 · IF 4.4

Existence of Crystalline Ammonium Sulfate Nuclei Affects Chemical Reactivity of Oleic Acid Particles Through Heterogeneous Nucleation

Wenli Liu,Keren Liao,Qi Chen,Longkun He,Yingjun Liu,Mikinori Kuwata

Organic aerosol particles are oxidized by atmospheric oxidants. These particles are occasionally internally mixed with solid materials such as soot and inorganic crystals. However, potential impacts of the particles' mixing states on chemical reactivity have rarely been investigated. This study investigated the influence of the existence of crystalline ammonium sulfate on chemical reactivity of oleic acid particles with ozone for the temperature range of −20°C to +35°C using an aerosol flow tube reactor. The chemical compositions of the resulting particles were monitored using online instruments for deriving the reactive uptake coefficients ( γ ) of ozone by oleic acid. The values of γ were not significantly influenced by the existence of ammonium sulfate when the temperature of the reactor was higher than the melting point of oleic acid (∼13°C). The values of γ were unmeasurably small for the lower temperature range when oleic acid particles were internally mixed with crystalline ammonium sulfate. No significant change in γ was observed for the temperature range down to −13°C when the inorganic salt was absent, likely due to the formation of supercooled liquid. The difference in chemical reactivity can be explained by the occurrence of heterogeneous nucleation induced by inorganic seed. Key Points Reactive uptake coefficients of ozone for non-seeded and seeded oleic acid particles were obtained under a wide temperature range Seed particle suppressed chemical reactivity of oleic acid at low temperature, while supercooled liquid formed when it was absent Mixing state could influence viscosity and phase state of particles as well as temperature Plain Language Summary Mixing states of particles in the atmosphere are complex and change with time. Part of fresh particles could consist of organic matter only after emission, while some particles are internally mixed with other materials, such as soot, mineral dust, and inorganic salts. Particles experience complicated atmospheric processes during transport, like oxidation, coagulation, and condensation. These processes could modify particle physical and chemical properties, including mixing state. However, the impact of mixing state of particles on oxidation process has rarely been investigated. We conducted a series of ozonolysis experiments of non-seeded and seeded oleic acid particles under a wide temperature range. This study demonstrated that internally mixed inorganic crystals suppressed chemical reactivity of oleic acid by promoting heterogeneous nucleation under lower temperature. Colder condition was needed for homogeneous nucleation of non-seeded particles, as they could form supercooling liquid. Our results indicate mixing state is also an important factor to regulate particle viscosity and phase state.

CAS / MDL: 57-10-3 57-11-4
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INDUSTRIAL CROPS AND PRODUCTS · 2022 · IF 6.449

Tuning the hydrophobicity of bio-based waterborne polyurethane by leveraging a diol derived from oleic acid

Li Wang,Qiang Gao,Jing Li,Le Jiang,Songhang Wang,Haojun Fan,Yi Chen,Jun Yan,Jun Xiang

Vegetable oils containing long aliphatic chains are widely used to obtain polyols and further produce eco-friendly bio-based waterborne polyurethanes (BWPU). However, the effect of the long aliphatic chains on the properties of BWPU, especially hydrophobicity, has been awfully neglected in previous works. Here, we have successfully prepared a series of linear anionic BWPU by incorporating an oleic-based primary glycol (OPG) with long aliphatic chains into polytetrahydrofuran ether glycol (PTMG) in different proportions. Firstly, the optimized reaction conditions for efficient synthesis of OPG via the thiol-ene photo-click reaction are: 2 wt% photoinitiator 1173, molar ratio of -SH to -C C- of 2:1, and reaction time of 1 h. Then, the effect of incorporating OPG on BWPU’s properties, especially the intrinsic hydrophobicity, was extensively investigated. Specifically, due to the long hydrophobic aliphatic chain, the particle size of the BWPU dispersions increased with the increase of OPG content, and correspondingly the absolute value of zeta potential decreased. Additionally, the water contact angle of the BWPU films increased from 60.8° to 90.3°, and their water absorption decreased from 7.88% to 3.21%, exhibiting enhanced hydrophobicity and water resistance. This work demonstrates the designed and synthesized vegetable oil-based diol with a long aliphatic chain plays a positive role in tailoring the hydrophobicity of bio-based WPU, which holds great promises for applications in waterproof and self-cleaning coatings.

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INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH · 2019 · IF 3.375

Selective Hydroconversion of Oleic Acid into Aviation-Fuel-Range Alkanes over Ultrathin Ni/ZSM-5 Nanosheets

Fuxiang Feng,Li Wang,Xiangwen Zhang,Qingfa Wang

Ultrathin Ni/ZSM-5 nanosheet catalysts with different acid concentrations, B/L (Brønsted/Lewis acid sites) ratios, and nanosheet thicknesses are designed for the hydroconversion of oleic acid into aviation-fuel-range alkanes (AFRAs). The role of acid concentration/distribution and nanosheet thickness was investigated. High acid concentration enhances the hydrodeoxygenation (HDO) reaction and intrinsic deoxygenation activity because of the synergistic effect between acid sites and metal sites. The selective cracking reaction can be enhanced by tailoring nanosheet thickness and acid distribution. The thin nanosheet favors isomerization, the selective cracking reaction, as well as the generation of central branched isomers. External acid sites dominate the primary cracking and central C–C cracking of the deoxygenated products, but internal acid sites promote the deeper cracking and terminal C–C cracking. Formation of aromatics is thoroughly suppressed at low reaction temperature (≤533 K). A high AFRA yield of 41.4% is achieved over the 3 nm nanosheet catalyst with Si/Al = 300 and B/L = 0.18.

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LIFE SCIENCES · 2018 · IF 3.234

Oleic acid protects saturated fatty acid mediated lipotoxicity in hepatocytes and rat of non-alcoholic steatohepatitis

Xuanming Chen,Linzhao Li,Xiaohong Liu,Ruixi Luo,Guangneng Liao,Lan Li,Jingping Liu,Jingqiu Cheng,Yanrong Lu,Younan Chen

Aim This study aims to demonstrate the protective effects of monounsaturated oleic acid (OA) against saturated palmitic acid (PA) induced cellular lipotoxicity in hepatocytes and rats with non-alcoholic steatohepatitis (NASH). Main methods Human hepatoma cell line HepG2 cells and neonatal rat primary hepatocytes were treated with PA or/and OA for 24 h. SD rats were fed with high fat diet (HFD) to induce NASH. From the 16th w, the HFD was full or half replaced by olive oil to observe the protective effects. Key findings In vitro, OA substantially alleviated PA induced cellular apoptosis, oxidative stress, ER stress, mitochondrial dysfunction, as well as inflammation in hepatocytes. In vivo, only olive oil supplementation had no detrimental effects, while HFD developed NASH in normal rats. Full replacement of HFD with olive oil had profoundly reversed NASH. Noteworthily, half replacement of HFD with olive oil (a mixed diet) has ameliorated NASH injury as well. It strikingly changed the hepatic histology from macrovesicular-steatosis into entire microvesicular-steatosis, and significantly reduced inflammation, ballooning and fibrosis. Significance Our study has demonstrated in both hepatocytes and NASH rats that oleic acids had great potential to combat the saturated fatty acids induced hepatic lipotoxicity. Only half replacement of HFD by monounsaturated fatty acids rich diet still had significant therapeutic outcome in NASH rats. Redirecting the toxic saturated fatty acids into triglyceride storage and reduction of cholesterol accumulation might be the possible explanation of OA driven protection in this scenario.

CAS / MDL: 112-80-1 7664-38-2
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EUROPEAN JOURNAL OF INORGANIC CHEMISTRY · 2013 ·Vol. 2013 ·期 31 ·5428-5435 · IF 3.12

Magnetic and Stable H3PW12O40-Based Core@shell Nanomaterial towards the Esterification of Oleic Acid with Methanol

Shi Li,Shang-Ru Zhai,Jian-Ming Zhang,Zuo-Yi Xiao,Qing-Da An,Ming-Hui Li,Xiao-Wei Song

Graphical A novel, magnetically recoverable, and stable catalyst, Fe 3 O 4 @SiO 2 –NH 2 /HPW@CS/HPW, has been prepared and a high methyl oleate yield of 93.2 % was achieved in the esterification of methanol and oleic acid. A magnetically retrievable and stable composite, Fe 3 O 4 @SiO 2 –NH 2 /HPW@CS/HPW, in which H 3 PW 12 O 40 (abbreviated as HPW hereafter) was successfully anchored onto the surface of a cross-linked chitosan coating on magnetic Fe 3 O 4 cores, has been prepared by means of chemical bonding between the amino and HPW components. The resultant composites were characterized by different physicochemical techniques, such as TEM, SEM, FTIR, and vibrating sample magnetometry (VSM). An improved synthesis of methyl oleate from oleic acid and methanol was observed with the as-prepared material as catalyst with easy recovery by simply using an external magnet. A yield of 93.2 % of methyl oleate was achieved under the optimal reaction conditions, that is, a 20:1 molar ratio of methanol to oleic acid and 0.4 g catalyst at 60 °C for 4 h. It was demonstrated that improved catalytic performance and facilitated separation were simultaneously achieved in the esterification reactions as a result of the core@shell structures in which stabilized HPW and magnetic cores are integrated into one body.

CAS / MDL: 13822-56-5 111-30-8
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ACS Applied Materials & Interfaces · 2015 · IF 6.723

Monodispersed Hollow SO3H-Functionalized Carbon/Silica as Efficient Solid Acid Catalyst for Esterification of Oleic Acid

Yang Wang,Ding Wang,Minghui Tan,Bo Jiang,Jingtang Zheng,Noritatsu Tsubaki,Mingbo Wu

SO3H-functionalized monodispersed hollow carbon/silica spheres (HS/C-SO3H) with primary mesopores were prepared with polystyrene as a template and p-toluenesulfonic acid (TsOH) as a carbon precursor and −SO3H source simultaneously. The physical and chemical properties of HS/C-SO3H were characterized by N2 adsorption, TEM, SEM, XPS, XRD, Raman spectrum, NH3-TPD, element analysis and acid–base titration techniques. As a solid acid catalyst, HS/C-SO3H shows excellent performance in the esterification of oleic acid with methanol, which is a crucial reaction in biodiesel production. The well-defined hollow architecture and enhanced active sites accessibility of HS/C-SO3H guarantee the highest catalytic performance compared with the catalysts prepared by activation of TsOH deposited on the ordered mesoporous silicas SBA-15 and MCM-41. At the optimized conditions, high conversion (96.9%) was achieved and no distinct activity drop was observed after 5 recycles. This synthesis strategy will provide a highly effective solid acid catalyst for green chemical processes.

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