Lubricants and lubricant additives: II. Performance characteristics of some substituted fatty acid esters

Abstract

Sixty-one compounds, principally substituted fatty esters of mono- and polyhydric alcohols, but including some amides and two imidazolidines, were prepared and evaluated as lubricants and lubricant additives for paraffin and diester base oils. The effects of chloro, phosphato, phosphorodithio, thio, epithio, mercapto, and sulfuryl substituents, alone and in certain combinations, on the performances of the compounds as antiwear and extreme pressure lubricants were investigated. The epithio (thiirane) group was the most effective and consistent in enhancing extreme pressure and antiwear performances of the compounds as additives. Sulfurized and chloro-sulfone derivatives also were effective, but perhaps somewhat less predictably so, than the epithio derivatives. The phosphato and phosphorodithio derivatives were good, consistent, antiwear additives, but only the latter seemed potentially useful for improving extreme pressure lubrication. Structure-performance correlations favor use of the esters over the amides.