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ARS Home » Midwest Area » Peoria, Illinois » National Center for Agricultural Utilization Research » Bio-oils Research » Research » Publications at this Location » Publication #299797

Title: Synthesis and physical properties of new estolide esters

item Cermak, Steven - Steve
item BREDSGUARD, JAKOB - Biosynthetic Technologies
item Isbell, Terry
item Murray, Rex

Submitted to: Annual Meeting and Expo of the American Oil Chemists' Society
Publication Type: Abstract Only
Publication Acceptance Date: 11/17/2013
Publication Date: 5/4/2014
Citation: Cermak, S.C., Bredsguard, J.W., Isbell, T., Murray, R.E. 2014. Synthesis and physical properties of new estolide esters. Annual Meeting and Expo of the American Oil Chemists' Society. p. 65.

Interpretive Summary:

Technical Abstract: Estolides are a class of esters based on vegetable oils that, in this case, are formed when the carboxylic acid functionality of one fatty acid reacts at the site of unsaturation of another fatty acid to form an ester linkage. The objective of this preliminary study was to synthesize new esters of estolides from either branch or linear chain alcohols and evaluate the physical properties: viscosity, acid value, Gardner color, pour points (PP), and cloud points (CP). The oleic free acid estolide that were esterified with branched alcohols had the best low temperature physical properties, PP and CP. The best PP performers from the branched series were 2-hexyldecanol, a 16 carbon chain branched material, and 2-octyldodecanol, a 20 carbon chain branched material, with a PP at -39 deg C. The best CP performers from the same series were 2-octyldodecanol, with a CP lower than -50 deg C, followed by the 2-hexyldecanol at -42 deg C. In general, the branched alcohols produced materials with better cold temperature properties than current commercially available materials. The viscosities and viscosity indices were as expected in terms of trends and ranges. The iso-stearyl alcohol had the most interesting viscosity at 40 deg C of 209.3 cSt which was higher than all other materials tested in this study. These new oleic estolide esters showed great potential as commercial lubricants.