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Synthesis and physical properties of petroselinic based estolide esters

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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.
Cermak, Steven C. , Isbell, Terry A. , Evangelista, Roque L. , Johnson, Burton L.
Coriandrum sativum , esters , estolides , esterification , perchlorates , synthesis , processing technology , chemical structure , viscosity , kinetics , octanoic acid , thermal properties , melting point , biodegradable products , oxidative stability , oxidation , natural additives , biobased products , lubricants
p. 132-139.
Includes references
Industrial crops and products 2011 Jan., v. 33, no. 1
[Amsterdam; New York, NY]: Elsevier Science
Journal Articles, USDA Authors, Peer-Reviewed
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