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

Polymers

Douglas G. Hayes²  Vinay K. Mannam²  Ran Ye²  Haizhen Zhao³  Salvadora Ortega¹ 

[1] Chemical Engineering Department, University of Murcia, Murcia 30071, Spain;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;

关键词: biobased polyesters;    castor oil;    lipases;    oligo-ricinoleic acid;    polyglycerol polyricinoleate;    ricinoleic acid;    10-undecenoic acid;   

DOI  :  10.3390/polym4021037

来源: mdpi

【 摘 要 】

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.

【 授权许可】

CC BY   
© 2012 by the authors; licensee MDPI, Basel, Switzerland.