Location: Bio-oils Research Unit
Title: Synthesis and physical properties of pennycress estolide 2-ethylhexyl esters Authors
Submitted to: Association for the Advancement of Industrial Crops Conference
Publication Type: Abstract Only
Publication Acceptance Date: September 11, 2011
Publication Date: September 11, 2011
Citation: Cermak, S.C., Isbell, T., Evangelista, R.L. 2011. Synthesis and physical properties of pennycress estolide 2-ethylhexyl esters [abstract]. Association for the Advancement of Industrial Crops Conference. p. 1. Technical Abstract: Pennycress (Thlaspi arvense L.) is a new crop that is currently being developed as an off-season rotation crop between annual corn and soybean production in Central Illinois by USDA-NCAUR. This rotation scheme may offer distinct advantages to farmers by providing additional farm income from an otherwise fallow season with little impact on the subsequent soybean production. The seed contains up to 36% oil with the major fatty acid as erucic (38.1%). The fatty acid composition of pennycress has been shown to have physical properties suitable for biofuels like hydro-treated renewable jet fuel (HRJ). Like many developing new crops, many aspects of pennycress growth, development, potential products, and economic success have yet to be fully characterized. The development of a new crop often depends on the synthesis of novel “green” compounds. Estolides are one such derivative of new crop oils which show promise in industrial applications. Estolides are formed when the carboxylic acid functionality of one fatty acid links to the site of unsaturation of another fatty acid to form esters. Estolides were derived from coriander fatty acids and various other fatty acids in the presence of an acid catalyst at 60 deg C for 24 hours. The free acid estolides were then esterified to the 2-ethylhexyl esters under standard conditions. These new estolide esters were converted to their corresponding hydroxy fatty acid and the degrees of polymerization were determined by GC analysis. Physical properties (pour points, cloud points and viscosities) of the coriander estolide esters were compared to previously synthesized homo-estolides and coco-estolides, which have current industrial applications. These new estolides show promise as a cheap alternative bio-based material.