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Modification of oligo-Ricinoleic Acid and Its Derivatives with 10-Undecenoic Acid via Lipase-Catalyzed Esterification
Department of Biosystems Engineering and Soil Science, University of Tennessee, 2506 E.J. Chapman Drive, Knoxville, TN 37996-4531, USA
College of Food Science and Technology, Nanjing Agricultural University, Nanjing 210095, Jiangsu, China
Chemical Engineering Department, University of Murcia, Murcia 30071, Spain
* Author to whom correspondence should be addressed.
Received: 8 February 2012; in revised form: 24 March 2012 / Accepted: 5 April 2012 / Published: 17 April 2012
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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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.
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.
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.