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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 #312665
Title: Mono-estolide synthesis from trans-8-hydroxy fatty acids by lipases in solvent-free media and their physical properties

Author
item MARTIN-ARJOL, IGNACIO - University Of Barcelona
item Isbell, Terry
item MANRESA, ANGELS - University Of Barcelona

Submitted to: Journal of the American Oil Chemists' Society
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 7/2/2015
Publication Date: 8/1/2015
Publication URL: https://handle.nal.usda.gov/10113/63246
Citation: Martin-Arjol, I., Isbell, T.A., Manresa, A. 2015. Mono-estolide synthesis from trans-8-hydroxy fatty acids by lipases in solvent-free media and their physical properties. Journal of the American Oil Chemists' Society. 92(8):1125-1141.

Interpretive Summary: This research produced novel oils (estolides) using lipases from starting fatty acids that had been made using a cell culture media from the most common vegetable oil fatty acid, oleic acid. The physical properties of these estolides were determined which will help define suitable industrial applications. In addition, structures for these estolides were well characterized by NMR and mass spectral instruments. This work will be useful to other researchers and industry to design complex molecules that have specific physical properties to meet the needs of industry and to use green chemistry processes which provides very specific functionalization of a molecule.

Technical Abstract: Pseudomonas aeruginosa 42A2 is known to produce two hydroxy-fatty acids, 10(S)-hydroxy-8(E)-octadecenoic and 7,10(S,S)-dihydroxy-8(E)-octadecenoic acids, when cultivated in a mineral medium using oleic acid as a single carbon source. These compounds were purified, 91 and 96 % respectively, to produce two new families of estolides: trans-8-estolides and saturated estolides from the monohydroxylated monomer. Trans-8-estolides were produced by three different lipases (Novozym 435, Lipozyme RM IM and Lipozyme TL IM) with reaction yields between 68.4 +/- 2.1 and 94.7 +/- 2.4 % in a solvent-free medium at 80 ºC in 168 h under vacuum. Novozym 435 was found to be the most efficient biocatalyst for both hydroxy-fatty acids with reaction yields of 71.7 +/- 2.3 and 94.7 +/- 2.4 %, respectively. Moreover, saturated estolides were also produced from a saturated 10(S)-hydroxy-8(E)-octadecenoic acid. These estolides were chemically and enzymatically synthesized with Novozym 435, under the previous described reaction conditions with yields of 60.7 +/- 2.1 and 71.2 +/- 2.3 % respectively. Finally, viscosity, glass transition temperature, decomposition temperatures, and enthalpies were determined to characterize both types of estolides. Thermal applications for both types of polyesters were improved since glass transition temperatures were lowered and decomposition temperatures were increased, with respect to their corresponding susbtrates.