Estolides Synthesis Catalyzed by Immobilized Lipases

Erika C G Aguieiras,Danielle O Rosas,Marta A P Langone,Mônica A P Da Silva,Juliana V Bevilaqua,Cláudia O Veloso

doi:10.4061/2011/432746

Erika C G Aguieiras, Danielle O Rosas + Show 4 more

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https://doi.org/10.4061/2011/432746

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Abstract

Estolides are vegetable-oil-based lubricants obtained from oleic acid or any source of hydroxy fatty acids. In this work, the estolides synthesis from oleic acid and methyl ricinoleate (biodiesel from castor oil), using immobilized commercial lipases (Novozym 435, Lipozyme RM-IM, and Lipozyme TL-IM) in a solvent-free medium was investigated. Acid value was used to monitor the reaction progress by determining the consumption of acid present in the medium. Novozym 435 showed the best performance. Water removal improved the conversion. Novozym 435 was more active at atmospheric pressure. Novozym 435 was reused four times with conversion reaching 15% after the fourth reaction at 80°C. Estolides produced under the reaction conditions used in this work presented good properties, such as, low temperature properties as pour point (−24°C), viscosity (23.9 cSt at 40°C and 5.2 cSt at 100°C), and viscosity index (153).

Highlights

Estolides are a class of polyesters based on vegetable oils that are formed when the carboxylic acid functionality of one fatty acid reacts at the site of unsaturation of another fatty acid [1] or by covalent ester bonds between hydroxyl moiety of one hydroxyl acid and the carboxyl moiety of another hydroxyl acid molecule [2]
The enzymatic synthesis of ricinoleic acid estolides using lipases have been investigated as an alternative to overcome the common problems that occur in a conventional route
Under the experimental conditions used in this work, the main reaction is the esterification between oleic acid and methyl ricinoleate producing estolide and water

Summary

Introduction

Estolides are a class of polyesters based on vegetable oils that are formed when the carboxylic acid functionality of one fatty acid reacts at the site of unsaturation of another fatty acid [1] or by covalent ester bonds between hydroxyl moiety of one hydroxyl acid and the carboxyl moiety of another hydroxyl acid molecule [2]. These compounds have a variety of potential applications as greases, plastics, inks, cosmetics, viscosity controller for chocolate, emulsifier in margarine, and lubricants [3,4,5]. Immobilized enzymes can be separated from the reaction media for reuse [2]

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