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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 #311137
Title: Synthesis and physical properties of new coco-oleic dimer and trimer plus estolide branched esters

Author
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: 5/3/2015
Publication Date: 5/3/2015
Citation: Cermak, S.C., Bredsguard, J.W., Isbell, T., Murray, R.E. 2015. Synthesis and physical properties of new coco-oleic dimer and trimer plus estolide branched esters [abstract]. Annual Meeting and Expo of the American Oil Chemists' Society. IOP-P1, p. 15.

Interpretive Summary:

Technical Abstract: Estolides are a class of esters based on vegetable oils that 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 separate coco-oleic estolide into two components based on the extent of oligomerization: coco-oleic dimer estolide and coco-oleic trimer plus estolide and evaluate their physical properties as branched esters: viscosities, acid values (AV), Gardner colors, pour points (PP), and cloud points (CP). The coco-oleic dimer estolide esters had the lowest PP at 45 deg C with the 2-hexyldecanol and PP of -39 deg C with the 2-octyldodecanol. The best CP performer from the same series was 2-octyldodecanol with CP of -37 deg C. The coco-oleic trimer plus estolide esters had slightly higher PPs (-24 to -39 deg C) with the same alcohols. The viscosities and viscosity indexes were as expected in terms of trends. The coco-oleic dimer estolide esters ranged from 27.5-51.7 cSt @ 40 deg C and 3.0-9.5 cSt @ 100 deg C, whereas the coco-oleic trimer plus estolide esters ranged from 120.8-227.7 cSt @ 40 deg C and 17.9-29.4 cSt @ 100 deg C for the same series as the dimer esters. Outside the series tested, isostearyl trimer plus ester had the highest reported viscosity of 417.3 cSt @ 40 deg C and 38.9 cSt @ 100 deg C. These new oleic estolide esters showed great potential as commercial lubricants.