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United States Department of Agriculture

Agricultural Research Service


Location: Bio-oils Research

Title: Increased functionality of methyl oleate using alkene metathesis

item Doll, Kenneth - Ken

Submitted to: International Journal of Sustainable Engineering
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 9/23/2013
Publication Date: 11/10/2014
Publication URL:
Citation: Doll, K.M. 2014. Increased functionality of methyl oleate using alkene metathesis. International Journal of Sustainable Engineering. 7(4):322-329.

Interpretive Summary: Without modification, bio-oils have many shortcomings which can be difficult to overcome and limit their use in industrial areas. An approach to solve this problem is to use chemistry in order to improve the oil and make it into a truly valuable industrial material. Alkene metathesis is a chemical reaction which takes a mixture of two different chemicals and produces a different mixture which is a combination of the two. It has been used in synthesis of organic chemicals for many years but, only recently, has the technology been extended into the bio-oils area. Using this technology, a family of potentially useful compounds has been made, which incorporate some of the active parts of other molecules into an oil-based material. This new material has the properties which are imparted by the new groups, yet is still predominantly a bio-based product. For example, the addition of a 6 carbon ring to the material may improve its resistance to oxidation, and the addition of an ester group will help it become a potential component of polyester. This type of technology will lead to more widespread use of soybean oil, into areas where it currently does not have the properties to compete.

Technical Abstract: A series of alkene cross metathesis reactions were performed using a homogeneous ruthenium based catalyst. Using this technology, a variety of functional groups can be incorporated into the biobased starting material, methyl oleate. Trans-stilbene, styrene, methyl cinnamate and hexen-3-ol were all shown to give desirable products. Using this technology, aromatics, alcohols, or additional esters can all be incorporated into the products. For example, the cross metathesis reaction of methyl oleate with methyl cinnamate by the second generation Grubbs catalyst showed 70% conversion of the methyl oleate into products where half of the observed products contain an aromatic group and over 1/3 of the products contain an a-ß unsaturated methyl ester. This promising green route is versatile, and with appropriate selection of starting materials, is applicable to the synthesis of polymer precursors, industrial fluids, or any other application where the upgrade of natural oils is necessary.

Last Modified: 10/18/2017
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