Synthesis and physical properties of petroselinic based estolide esters

Abstract

A new series of petroselinic (Coriandrum sativum L.) based estolide 2-ethylhexyl (2-EH) esters were synthesized, as the capping material varied in length and in degrees of unsaturation, in a perchloric acid catalyzed one-pot process with the esterification process incorporated into an in situ second step to provide the coriander estolide 2-EH ester. The kinematic viscosities ranged from 53 to 75 cSt at 40°C and 9.1 to 14.6 cSt at 100°C with a viscosity index (VI) ranging from 151 to 165. The caprylic (C8) capped coriander estolide 2-EH ester had the lowest low-temperature properties (pour point=−33°C and cloud point=−33°C), while the coco-coriander estolide 2-EH ester produced an estolide with modest low-temperature properties (pour point=−24°C and cloud point=−25°C). The coco-coriander estolide 2-EH ester was explored for the ability to resist oxidative degradation with the use of an biodegradable additive package added in 1.5%, 3.5%, or 7.0% units based on weight. The oxidative stability increased as the amount of stability package increased (rotating pressurized vessel oxidation test (RPVOT) times 65–273min). Along with expected good biodegradability, these coriander estolide 2-EH esters had acceptable properties that should provide a specialty niche in the U.S. as a biobased lubricant.