Vegetable oils are a renewable and an environmentally friendly alternative to petroleum-based oils in lubrication and other important application areas. Vegetable oils fall into two broad chemical categories: triesters (or TG) and monoesters. Most vegetable oils are triesters of glycerol with FA, whose characteristics are dependent on the chemistry and composition of the FA residues. A small percentage of vegetable oils are monoesters of long-chain FA and fatty alcohols of varying chemistries. In this work, the free energy of adsorption (∆G ads ) of safflower (SA), high-oleic safflower (HOSA), and jojoba (JO), methyl oleate (MO), and methyl palmitate (MP) on steel were investigated. SA and HOSA are TG of vegetable oils with FA residues of radically different degrees of unsaturation. JO is a monoester vegetable oil. ∆G ads is one of the major factors affecting the boundary friction properties of lubricant ingredients. ∆G ads was found to increase in the order: HOSA ≤ SA < JO < MO ≤ MP. The results are consistent with the degree of functionality and other chemical properties of the oils studied.Paper no. J10390 in JAOCS 80, 697-704 (July 2003).KEY WORDS: Adsorption isotherm, boundary lubrication, coefficient of friction, free energy of adsorption, jojoba oil, methyl oleate, methyl palmitate, safflower oil, high-oleic safflower oil, vegetable oil.Vegetable oils are obtained from renewable agricultural sources (1,2). They are also nontoxic and have excellent environmental and safety characteristics. These properties make vegetable oils attractive alternatives to petroleum-based oils in lubrication and other applications (1-5). Vegetable oils can be grouped into two broad chemical categories (2). Most vegetable oils are triesters of glycerol with various types of FA and are commonly referred to as TG. A few vegetable oils are monoesters of long-chain FA and fatty alcohols of varying degrees of unsaturation.Most vegetable oils can be considered to be amphiphilic since they comprise distinctly separated regions of polar and nonpolar groups in the same molecule. The polar groups constitute at least one ester functional group. The nonpolar groups are hydrocarbons of varying chain lengths, degrees of unsaturation, and stereochemistry. Depending on the type of vegetable oil, functional groups such as epoxides and hydroxides may be present in the hydrocarbon portion of the molecule. The tribological and other properties of vegetable oils are highly dependent on the exact chemical composition of its polar and nonpolar groups. For example, a TG with a lower degree of unsaturation will have better oxidative stability than a TG with a higher degree of unsaturation (6-8).Most vegetable oils are considered functional fluids since they have at least one functional group (an ester) and are also liquid at room temperature. This property allows vegetable oils to be used in lubricant formulations as base oils and/or boundary additives. Most lubrication processes occur in one of three lubrication regimes: boundary, hydrodynamic, and mix...