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Mono-Estolide Synthesis from trans-8-Hydroxy-Fatty Acids by Lipases in Solvent-Free Media and Their Physical Properties

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Journal of the American Oil Chemists' Society

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 °C 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. 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 substrates.

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Acknowledgments

This work was supported by the Ministerio de Economía y Competitividad (CTQ2014-59632-R), Spain, and by the IV Pla de Recerca de Catalunya (Generalitat de Catalunya) grant 2014SGR534. I. Martin-Arjol was a grateful recipient of an APIF-fellowship from the University of Barcelona. We also thank Novozymes for kindly providing the lipase samples, Karl E. Vermillion who performed the NMR experiments in the National Center for Agricultural Utilization Research, USDA, in Peoria, Il, USA; Dr. I. Fernández Vidal and Dr. M. C. Puigjaner Vallet from the Centres Científics i Tecnològics (CCiT) of the University of Barcelona who performed the spectrometric and calorimetric analyses of the samples, respectively; and Dr. Joan Llorens Llacuna from Chemical Engineering Department of University of Barcelona who facilitated the rheometer utilization.

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Authors and Affiliations

  1. Departament de Microbiologia i Parasitologia Sanitàries, Facultat de Farmàcia, Universitat de Barcelona, Av. Joan XXIII s/n., 08028, Barcelona, Spain

    Ignacio Martin-Arjol & Angels Manresa

  2. Bio-Oils Research, National Center for Agricultural Utilization Research, USDA, Agricultural Research Service, 1815 North University Street, Peoria, IL, USA

    Terry A. Isbell

Authors
  1. Ignacio Martin-Arjol
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  2. Terry A. Isbell
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  3. Angels Manresa
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Correspondence to Ignacio Martin-Arjol or Angels Manresa.

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Martin-Arjol, I., Isbell, T.A. & Manresa, A. Mono-Estolide Synthesis from trans-8-Hydroxy-Fatty Acids by Lipases in Solvent-Free Media and Their Physical Properties. J Am Oil Chem Soc 92, 1125–1141 (2015). https://doi.org/10.1007/s11746-015-2687-3

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  • DOI: https://doi.org/10.1007/s11746-015-2687-3

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