Esters from castor oil functionalized with aromatic amines as a potential lubricant. (9th October 2022)

• Record Type: Journal Article
• Authors: de Andrade Souza, Laura; Moreira, Denise Ramos; Ricardo, Nágila Maria Pontes Silva; Maier, Martin Edmund; Filho, Paulo Roberto Campos Flexa Ribeiro; Luna, Francisco Murilo Tavares; Petzhold, Cesar Liberato
• Is Part Of: Journal of the American Oil Chemists' Society. Volume 100:Number 2(2023)
• Page Start: 175
• Page End: 184
• Publication Date: 2022-10-09
• Subjects: aromatic amines -- bio‐based lubricant -- castor oil -- epoxide opening -- tribological properties; Oils and fats -- Periodicals; Soap -- Periodicals; Fats -- Periodicals; Food-Processing Industry -- Periodicals; Acides gras -- Périodiques; Aliments -- Industrie et commerce -- Périodiques; Huiles et graisses -- Périodiques; Savon -- Périodiques; Oliën; Chemie; Oils and fats; Soap; Periodicals; 547.77
• DOI: 10.1002/aocs.12648
• Languages: English
• ISSNs: 0003-021X

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.