Esters from castor oil functionalized with aromatic amines as a potential lubricant
Laura de Andrade Souza, Denise Ramos Moreira, Nágila Maria Pontes Silva Ricardo, Martin E. Maier, Paulo Roberto Campos Flexa Ribeiro Filho, F. Murilo T. Luna, César Liberato Petzhold
Abstract
Abstract Vegetable oils are very promising alternatives to fossil lubricants due to their abundance, low cost, excellent performance, and environmental friendliness. Due to its multifunctional structure, castor oil is an excellent precursor in the synthesis of new biolubricants. However, it showed poor thermal‐oxidative stability and a higher pour point. This study used castor oil fatty acids prepared by transesterification (EHRO), epoxidation (TEPO), and oxirane ring opening with the aromatic amines aniline (ANIL) and p ‐anisidine (ANIS). The chemical structure of these oils was verified by 1 H and 13 C NMR analysis, and mass spectrometry. Measurements show that the presence of an aromatic amine increases the viscosity resulting in 172 (ANIL) and 199 (ANIS) cSt at 40°C, but reduces viscosity index to 16 and 1, respectively. In addition, the amine groups can scavenge radicals increasing their thermal and oxidative stability. These products do not oxidize copper, and tribological analysis reveals that ANIS has the lowest torque with wear equivalent to commercial mineral lubricant NH‐140.