Synthesis of hydroxyfatty esters by sequential epoxidation-hydrogenolysis: Solvent effects

The tandem/sequential combination of epoxidation and hydrogenolysis for unsaturated fatty esters is not straightforward, due to incompatibility problems with the impurities present or generated in the used solvents. The chlorinated impurities in alpha, alpha, alpha-trifluorotoluene leads to the form...

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Detalles Bibliográficos
Autores: Dorado, V., Herrerias, C. I., Fraile, J. M.
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2021
País:España
Institución:Universidad de Zaragoza
Repositorio:Zaguán. Repositorio Digital de la Universidad de Zaragoza
OAI Identifier:oai:zaguan.unizar.es:109634
Acceso en línea:http://zaguan.unizar.es/record/109634
Access Level:acceso abierto
Descripción
Sumario:The tandem/sequential combination of epoxidation and hydrogenolysis for unsaturated fatty esters is not straightforward, due to incompatibility problems with the impurities present or generated in the used solvents. The chlorinated impurities in alpha, alpha, alpha-trifluorotoluene leads to the formation of important amounts of chlorohydrins by HCl formation in the hydrogenolysis step. The use of trifluoroethanol (TFE) in the epoxidation step produces trifluoroacetic acid traces by oxidation, responsible for the opening of the epoxide with water and TFE. The solvent of choice was finally isobutyl acetate, which gathers the required physicochemical properties, with 85 % yield of hydroxystearates from methyl oleate in a sequential process.