Design, Synthesis, and Tribological Behavior of an Eco-Friendly Methylbenzotriazole-Amide Derivative
Abstract
1. Introduction
2. Results
2.1. Synthesis
2.2. Stability Characterization
2.2.1. Thermal Stability
2.2.2. Storage Stability in Base Oil
2.3. Tribological Behavior
2.3.1. Different MeBz-2-C18 Additions
2.3.2. Comparison with the Commercial Additive
2.4. Lubrication Mechanism
2.4.1. Worn Surface Analysis
2.4.2. DFT Calculations
3. Materials and Methods
3.1. Materials
3.2. Synthesis of MeBz-2-Etn and MeBz-2-C18
3.2.1. Synthesis of MeBz-2-Etn
3.2.2. Synthesis of MeBz-2-C18
3.3. Characterizations
3.4. Preparation of Oil Samples
3.5. Tribological Testing
4. Conclusions
- (1)
- The covalently-bonded amide bond endows MeBz-2-C18 with superior thermal stability and better storage stability in synthetic base oil compared with T406. The residual mass of MeBz-2-C18 at 300 °C is 89.3%, while that of T406 is merely 11.0%.
- (2)
- The optimal addition of MeBz-2-C18 in the selected synthetic base oil is 0.5 wt.%, which reduces the ave. WSD and ave. COF by 21.6% and 3.2%, which is better than that of the commercial additive T406.
- (3)
- Worn surface analysis and DFT calculations suggest that MeBz-2-C18 has stronger adsorption on the metal surface than that of T406. The amide bond in MeBz-2-C18 breaks preferentially during friction, reducing the interfacial shear force and facilitating the film formation of iron oxides.
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
References
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Item | MeBz-2-Etn | MeBz-2-C18 | T406 | |
---|---|---|---|---|
Decomposition temperature (°C) | Initial | 19.7 | 185.5 | 76.8 |
Max. | 217.4 | 374.4 | 221.1 | |
Terminal | 236.0 | 434.7 | 420.3 | |
Residual mass (%) | @ Max. decomposition | 15.1 | 22.4 | 39.2 |
@200 °C | 44.8 | 99.9 | 71.9 | |
@300 °C | 1.8 | 89.3 | 11.0 | |
@400 °C | 1.0 | 1.3 | 1.3 |
Items | Base Oil | 0.5 wt.% MeBz-2-C18 | ||
Non-Wear | Wear | Non-Wear | Wear | |
SEM images (300X) | ||||
Element Distribution (carbon is represented in red, oxgen in green, iron in blue) | ||||
C (%) | 22.54 | 25.57 | 27.57 | 34.24 |
O (%) | 7.51 | 28.46 | 8.58 | 30.14 |
Fe (%) | 69.95 | 45.97 | 63.86 | 35.62 |
Binding Energy (eV) | Corresponding Bond | Content (%) | ||
---|---|---|---|---|
Base Oil_Wear | MeBz-2-C18_Wear | |||
C1s | 283.4 | Metal carbides | - | 3.3 |
284.8 | C–C/C=C | 86.9 | 80.6 | |
286.0 | C–O/C–N | 13.1 | 14.5 | |
288.5 | C=O | - | 1.6 | |
O1s | 529.6 | Fe–O | 13.1 | 30.0 |
531.9 | C=O | 86.9 | 63.3 | |
533.1 | C–O | - | 6.7 | |
Fe2p | 709.6 | Fe (2p3/2) | 51.8 | 48.1 |
711.0 | Fe3+ (2p3/2) | 34.3 | 32.2 | |
713.5 | Fe2+ (2p3/2) | - | 6.8 | |
723.5 | Fe2+ (2p1/2) | 13.9 | 12.9 | |
N1s | 399.4 | N–O | - | 86.9 |
401.7 | C–N | - | 13.1 |
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Yang, F.; Li, Z.; Yang, H.; Zhao, Y.; Sun, X.; Tang, Y. Design, Synthesis, and Tribological Behavior of an Eco-Friendly Methylbenzotriazole-Amide Derivative. Int. J. Mol. Sci. 2025, 26, 1112. https://doi.org/10.3390/ijms26031112
Yang F, Li Z, Yang H, Zhao Y, Sun X, Tang Y. Design, Synthesis, and Tribological Behavior of an Eco-Friendly Methylbenzotriazole-Amide Derivative. International Journal of Molecular Sciences. 2025; 26(3):1112. https://doi.org/10.3390/ijms26031112
Chicago/Turabian StyleYang, Fan, Zenghui Li, Hongmei Yang, Yanan Zhao, Xiuli Sun, and Yong Tang. 2025. "Design, Synthesis, and Tribological Behavior of an Eco-Friendly Methylbenzotriazole-Amide Derivative" International Journal of Molecular Sciences 26, no. 3: 1112. https://doi.org/10.3390/ijms26031112
APA StyleYang, F., Li, Z., Yang, H., Zhao, Y., Sun, X., & Tang, Y. (2025). Design, Synthesis, and Tribological Behavior of an Eco-Friendly Methylbenzotriazole-Amide Derivative. International Journal of Molecular Sciences, 26(3), 1112. https://doi.org/10.3390/ijms26031112