Tailoring Synthetic Pelargonic Acid Esters for Bio-Based Lubricant Applications: Exploring the Relationship between Structure and Properties

Michele Emanuele Fortunato, Francesco Taddeo, Rosa Vitiello, Rosa Turco, Riccardo Tesser, Vincenzo Russo, and Martino Di Serio

ACS Sustainable Chem. Eng. 2023, Publication Date:August 10, 2023



Pelargonic acid (PA) is commercially obtained by oxidative cleavage of fatty acid double bonds. Its esters are interesting compounds used to create bio-based products. An industrially relevant application of these compounds is in the field of solvent manufacturing and formulation of green lubricating oils. The physical–chemical and rheological properties of these esters are influenced by the structural features of the alcohol used as starting materials, such as chain length, number of unsaturation, and degree of branching. This work provides an in-depth study of the existing structure–properties relations for fatty acid alkyl esters obtained from PA and different alcohols [i.e., 2-ethylhexanol (EtHex), ethylene glycol, 1,3-propanediol, 1,4-butanediol, trimethylolpropane, and pentaerythritol]. The aim is to evaluate the use of the synthesized product for the formulation of bio-based lubricants. The chosen alcohols are frequently employed in the preparation of bio-based lubricants. In addition, most of them, such as EtHex and diols, can be derived from biomass sources, contributing to the sustainability of the obtained products. For comparison purposes, some of these alcohols were also used for the synthesis of the corresponding oleic acid esters, which were chosen as a benchmark due to their common use in the synthesis of bio-based lubricants. The influence of the structural factors on the viscosity, pour point (PP), and oxidation stability of the synthesized esters was highlighted by comparing the obtained results. Pelargonates showed lower viscosities and higher PPs than that of the oleates, but they present high stabilities to the oxidation due to the absence of unsaturation.