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United States Department of Agriculture

Agricultural Research Service

Title: Synthesis of Estolide Esters from Cis-9-Octadecenoic Acid Estolides

Authors
item Harry-O`kuru, Rogers
item Isbell, Terry
item Weisleder, David

Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: November 20, 2000
Publication Date: N/A

Interpretive Summary: Seed oils are not as widely used in non-food industrial applications as they could be because the structure of most of these oils does not afford the stability and flexibility required in many industrial uses. New crop oils in particular need these added characteristics in order to economically entice farmers to invest in an alternate crop. In this work, therefore, we have used one of the components of seed oils to generate products with many desirable characteristics that make the oil amenable to several industrial uses and yet retains its natural biodegradability after it is spent.

Technical Abstract: Oleic acid (cis-9-octadecenoic acid) was converted in excellent yield to the estolide which was then esterified with 2,2-dimethypropan-1- ol (neopentyl alcohol), cis-9-octadecen-1-ol (oleyl alcohol) and 2-propanol to generate the corresponding capped estolide esters. Higher formula mass estolide esters were synthesized by reaction of the parent estolide with 1,3- propanediol, 2,2- dimethyl-1,3-propanediol and 1,5-pentanediol to give the corresponding diesters of oleic estolide, thus doubling the molecular size of the parent estolide. Physical characteristics of the products (pour points and viscosities) were determined in order to evaluate these products for possible industrial application.

Last Modified: 10/25/2014
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