Abstract
Disruption of the three-dimensional network of suberin in cork by cholinium hexanoate leads to its efficient and selective isolation. The reaction mechanism, which likely involves selective cleavage of some inter-monomeric bonds in suberin, was still unanswered. To address this question, the role of the ionic liq. during suberin depolymn. and during cleavage of std. compds. carrying key chem. ...
Abstract
Disruption of the three-dimensional network of suberin in cork by cholinium hexanoate leads to its efficient and selective isolation. The reaction mechanism, which likely involves selective cleavage of some inter-monomeric bonds in suberin, was still unanswered. To address this question, the role of the ionic liq. during suberin depolymn. and during cleavage of std. compds. carrying key chem. functionalities was herein investigated. A clear demonstration that the ionic liq. catalyzes the hydrolysis of acylglycerol ester bonds was attained herein, both exptl. and computationally (DFT calcns.). This behavior is related to cholinium hexanoate capacity to activate the nucleophilic attack of water. The data showed also that the most favorable reaction is the hydrolysis of acylglycerol ester bonds, with the C2 position reporting the faster kinetics, while most of the linear aliph. esters remained intact. The study emphasizes that the ionic liq. plays the dual role of solvent and catalyst and leads to suberin efficient extn. through a mild depolymn. It is also one of the few reports of ionic liqs. as efficient catalysts in the hydrolysis of esters. [on SciFinder(R)]
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