Screening and selection of lipases for the enzymatic production of polyglycerol polyricinoleate

Bódalo, A.; Bastida, Jaume; Máximo, M.F.; Montiel, M.C.; Gómez, M.; Ortega, S.

doi:10.1016/j.bej.2009.05.004

Cited by 24 publications

(23 citation statements)

References 21 publications

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“…A similar objective was achieved previously by us; moreover, lauric acid was successfully attached onto the -OH termini of ricinoleic acid oligomers using immobilized Candida antarctica lipase, CAL [17]. For the second synthesis, undecenoic was reacted with PGPR prepared via CAL-catalyzed esterification (Scheme II) [5][6][7].…”

Section: Introductionmentioning

confidence: 84%

“…PDI values remained low throughout the time course of reaction, residing between 1.1 and 1.2. Further research is needed to determine if the percent incorporation of undecenoic acid can be increased without increasing the final FFA concentration, perhaps by adding undecenoic acid into the reaction mixture in small batchwise increments throughout the time course of reaction, and/or by applying a more effective means of water removal than free evaporation, such as high vacuum pressure [7,8]. (It is known that the small amount of non-hydroxy fatty acid present in technical grade ricinoleic acid is readily incorporated as end groups for oligo-ricinoleic acid [9], suggesting the former approach may be successful.)…”

Section: Cal-catalyzed Esterification Of Oligo-ricinoleic Acid and 10mentioning

confidence: 99%

“…In addition, polyglycerol polyricinoleate, PGPR, consisting of oligo-ricinoleic acid chains grafted onto polyglycerol via ester bond formation, is a well-known biobased and biocompatible emulsifier for foods and pharmaceuticals [5][6][7]. oligo-Ricinoleic acid and its derivatives (including PGPR [8]) are readily formed using lipases under nonaqueous media and moderate operating conditions; e.g., 50-80 °C and near-ambient pressure [9].…”

Section: Introductionmentioning

confidence: 99%

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

Hayes

Mannam

et al. 2012

Polymers

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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. OPEN ACCESSPolymers 2012, 4 1038

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Section: Introductionmentioning

confidence: 84%

Section: Cal-catalyzed Esterification Of Oligo-ricinoleic Acid and 10mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

Hayes

Mannam

et al. 2012

Polymers

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“…El poliricinoleato es un estólido oligomérico, obtenido principalmente por autocondensación del ácido ricinoléico, para la obtención de poliglicerol-poliricinoleato, un surfactante (W/O), muy empleado en la industria alimenticia [8] , también se obtiene mediante biosíntesis enzimática [9] . El ácido ricinoléico ha sido empleado en la formación de copolímeros con otros ácidos como el sebásico los cuales son biodegradables [10] .…”

Section: Introductionunclassified

“…Son materiales de morfología segmentada en dos fases: segmentos suaves o flexibles correspondientes con el macropoliol y segmentos duros o rígidos provenientes del isocianato y del extensor de cadena de bajo peso molecular. Los segmentos duros actúan como un relleno de alto modulo y los suaves proveen extensibilidad [7] .El poliricinoleato es un estólido oligomérico, obtenido principalmente por autocondensación del ácido ricinoléico, para la obtención de poliglicerol-poliricinoleato, un surfactante (W/O), muy empleado en la industria alimenticia [8] , también se obtiene mediante biosíntesis enzimática [9] . El ácido ricinoléico ha sido empleado en la formación de copolímeros con otros ácidos como el sebásico los cuales son biodegradables [10] .…”

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Síntesis de poli ácido láctico y poli ricinoleato empleando calentamiento por microondas y su utilización en la producción de termoplasticos de poliuretano

2011

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Resumen: En este trabajo se realiza la síntesis de poliuretano termoplástico (TPU) utilizando oligómeros sintetizados a partir de ácido DL Láctico y ácido ricinoléico. Estos polioles fueron obtenidos desde fuentes renovables, mediante la policondensación de los monómeros sin catalizador. Se evalúo el efecto de las microondas en las reacciones, donde se encuentraron efectos no térmicos que disminuyen la energía de activación y aumentan la constante de velocidad, en una cinética de tercer orden; el seguimiento y la caracterización de los productos intermedios se realiza mediante la cuantificación de valor ácido por titulación (ASTM D4662 -03) y número de hidroxilos (ASTM D4274 -05). Los termoplásticos obtenidos se caracterizan mediante las siguientes pruebas: resistencia tensil y % elongación (ASTM D882-97), análisis de calorimetría diferencial de barrido (DSC), espectroscopía infrarroja (IR) y microscopía de fuerza atómica (AFM). Los TPU se obtuvieron con un porcentaje de segmentos suaves del 50%, todos presentan morfología segmentada y segregación de fases. Las formulaciones con poli(DL ácido Láctico) y Difenilmetanodiisocianato (MDI) presentan la mayor rigidez y temperatura de transición vítrea (Tg). Palabras-claves: Poliuretano termoplástico, poli(DL ácido Láctico), poliricinoleato. Synthesis of Poly Lactic Acid and Poly Ricinoleate Using Microwave Heating and Their Use in the Production of Polyurethane ThermoplasticAbstract: In this paper we report on the synthesis of thermoplastic polyurethane (TPU) using oligomers synthesized from DL Lactic acid and ricinoleic acid. These polyols were obtained from renewable sources by polycondensation of monomers without catalysts. The effect of microwaves on the reactions was evaluated, where non-thermal effects were found to lower the activation energy and increase the rate constant in a third-order kinetics. The monitoring and characterization of intermediate products was done by quantification of acid value by titration (ASTM D4662 -03) and hydroxyl number (ASTM D4274 -05). Thermoplastics obtained are characterized by the following tests: tensile strength and elongation percentage (ASTM D882-97), analysis of differential scanning calorimetry (DSC), infrared spectroscopy (IR) and atomic force microscopy (AFM). TPU was obtained with a percentage of 50% soft segments, all have segmented morphology and segregation of phases. The formulations with poly(DL lactic acid) and Methylene diphenyl diisocyanate (MDI) have the highest stiffness and glass transition temperature (Tg). Keywords: Thermoplastic polyurethane, poly(DL lactic acid), polyricinoleate. IntroducciónLa utilización de productos naturales como aceites vegetales y grasas ha atraído la atención de científicos y de la industria en los últimos años, debido a consideraciones ambientales. Estas materias primas son sostenibles, renovables, y lo más importante, biodegradables. En los aceites vegetales se han realizado modificaciones químicas en los grupos éster y dobles enlaces, para obtener una amplia gama de biopolímero...

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PGPR, Polyglycerolpolyricinoleate, E476

Christiansen

2014

Emulsifiers in Food Technology

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Screening and selection of lipases for the enzymatic production of polyglycerol polyricinoleate

Cited by 24 publications

References 21 publications

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

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

Síntesis de poli ácido láctico y poli ricinoleato empleando calentamiento por microondas y su utilización en la producción de termoplasticos de poliuretano

PGPR, Polyglycerolpolyricinoleate, E476

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