Publication: Modification of oligo-Ricinoleic Acid and its derivatives with 10-undecenoic acid via lipase-catalyzed esterification
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Date
2012-04-17
Authors
Hayes, Douglas G. ; Mannam, Vinay K. ; Ye, Ran ; Zhao, Haizhen ; Ortega Requena, Salvadora ; Montiel Morte, María Claudia
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Facultad de Química
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Publisher
MDPI
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DOI
https://doi.org/10.3390/polym4021037
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info:eu-repo/semantics/article
Description
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.
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Citation
Polymers 2012, 4(2), 1037-1055
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