With the increasingly demanding engine conditions and the implementation of “double carbon” policies, the demand for high-quality lubricants that are cost-effective and environmentally friendly is increasing. Additives, especially high-performance friction modifiers, play an important role in boosting lubricant efficiency and fuel economy, so their developments are at the forefront of lubrication technologies. In this study, 1,3-dioleoamide-2-propyloleate (DOAPO), which incorporates polar amide, ester, and nonpolar alkyl chains, was synthesized from 1,3-diamino-2-propanol to give an eco-friendly organic friction modifier. Nuclear magnetic resonance (NMR), high-resolution mass spectrometry (HR-MS), Fourier-transform infrared spectroscopy (FT-IR), and thermogravimetric analysis (TGA) were used to characterize the structure and thermal stability of DOAPO. Meanwhile, the storage stability and tribological behaviors of DOAPO in synthetic base oil were studied and compared with a commercial oleamide. The results show that DOAPO has better thermal stability and better storage stability in synthetic base oil. Additionally, 0.5 wt.% of DOAPO could shorten the running-in period and reduce the average friction coefficient (ave. COF) and wear scar diameter (ave. WSD) by 8.2% and 16.2%, respectively. The worn surface analysis and theoretical calculation results show that the ester bond in DOAPO breaks preferentially during friction, which can reduce the interfacial shear force and easily react with metal surfaces to form iron oxide films, thus demonstrating a better friction-reducing and anti-wear performance.

Harsh modern industrial working conditions require high-performance lubricants, but traditional additives are limited by single functionality and poor compatibility, driving the development of multifunctional alternatives. Two novel hindered phenolic amide–esters (MADE, DAME) were synthesized and characterized. Their thermal/storage stability, antioxidant and tribological properties in synthetic oil were evaluated, with commercial 1010 and T203 as references. DFT calculations and worn surface analysis were also employed to clarify the lubrication mechanism. The results indicate that MADE exhibits better thermal/storage stability, comprehensive antioxidation and lubricating performance than DAME, with residual mass of 85.3% and 73.2% at 300 °C, respectively. A total of 1 wt.% MADE shortens the running-in period to 200 s (vs. 300 s for base oil), reduces the average. WSD by 12.1% and wear volume by 60.2%. Mechanistically, MADE adsorbs strongly on metal surfaces and forms a protective tribofilm via tribochemical reaction, exhibiting synergistic antioxidant and anti-wear effects. This work establishes a novel and sustainable paradigm for developing next-generation, multifunctional lubricant additives with high performance.