Polymers 2012, 4(2), 1037-1055; doi:10.3390/polym4021037
Article

Modification of oligo-Ricinoleic Acid and Its Derivatives with 10-Undecenoic Acid via Lipase-Catalyzed Esterification

Received: 8 February 2012; in revised form: 24 March 2012 / Accepted: 5 April 2012 / Published: 17 April 2012
(This article belongs to the Special Issue Enzymes in Monomer and Polymer Synthesis)
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
Abstract: Lipases were employed under solvent-free conditions to conjugate oligo-ricinoleic acid derivatives with 10-undecenoic acid, to incorporate a reactive terminal double bond into the resultant product. First, undecenoic acid was covalently attached to oligo-ricinoleic acid using immobilized Candida antarctica lipase (CAL) at a 30% yield. Thirty percent conversion also occurred for CAL-catalyzed esterification between undecenoic acid and biocatalytically-prepared polyglycerol polyricinoleate (PGPR), with attachment of undecenoic acid occurring primarily at free hydroxyls of the polyglycerol moiety. The synthesis of oligo-ricinoleyl-, undecenoyl- structured triacylglycerols comprised two steps. The first step, the 1,3-selective lipase-catalyzed interesterification of castor oil with undecenoic acid, occurred successfully. The second step, the CAL-catalyzed reaction between ricinoleyl-, undecenoyl structured TAG and ricinoleic acid, yielded approximately 10% of the desired structured triacylglycerols (TAG); however, a significant portion of the ricinoleic acid underwent self-polymerization as a side-reaction. The employment of gel permeation chromatography, normal phase HPLC, NMR, and acid value measurements was effective for characterizing the reaction pathways and products that formed.
Keywords: biobased polyesters; castor oil; lipases; oligo-ricinoleic acid; polyglycerol polyricinoleate; ricinoleic acid; 10-undecenoic acid
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MDPI and ACS Style

Hayes, D.G.; Mannam, V.K.; Ye, R.; Zhao, H.; Ortega, S.; Montiel, M.C. Modification of oligo-Ricinoleic Acid and Its Derivatives with 10-Undecenoic Acid via Lipase-Catalyzed Esterification. Polymers 2012, 4, 1037-1055.

AMA Style

Hayes DG, Mannam VK, Ye R, Zhao H, Ortega S, Montiel MC. Modification of oligo-Ricinoleic Acid and Its Derivatives with 10-Undecenoic Acid via Lipase-Catalyzed Esterification. Polymers. 2012; 4(2):1037-1055.

Chicago/Turabian Style

Hayes, Douglas G.; Mannam, Vinay K.; Ye, Ran; Zhao, Haizhen; Ortega, Salvadora; Montiel, M. Claudia. 2012. "Modification of oligo-Ricinoleic Acid and Its Derivatives with 10-Undecenoic Acid via Lipase-Catalyzed Esterification." Polymers 4, no. 2: 1037-1055.

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