Synthesis of fatty ketoesters by tandem epoxidation–rearrangement with heterogeneous catalysis

Unsaturated fatty esters can be easily transformed into ketoesters through a two-step process. The highly efficient epoxidation is carried out with tert-butyl hydroperoxide (TBHP) in α,α,α-trifluorotoluene (TFT) using a Ti–silica heterogeneous catalyst. The formed epoxide is easily rearranged by a h...

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Detalhes bibliográficos
Autores: Dorado, Vicente, Gil Llamas, Lena, Mayoral, José A., Herrerías, Clara I., Fraile, José M.
Formato: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2020
País:España
Recursos:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/220616
Acesso em linha:http://hdl.handle.net/10261/220616
Access Level:acceso abierto
Descrição
Resumo:Unsaturated fatty esters can be easily transformed into ketoesters through a two-step process. The highly efficient epoxidation is carried out with tert-butyl hydroperoxide (TBHP) in α,α,α-trifluorotoluene (TFT) using a Ti–silica heterogeneous catalyst. The formed epoxide is easily rearranged by a heterogeneous Brønsted acid, with Nafion–silica SAC13 as the most efficient one. Both reactions can be combined in a tandem process, with separation of the Ti–silica catalyst by filtration from the reaction medium and addition of the second acid catalyst to perform the second reaction. Each catalyst is separated individually and can be reused, with or without re-activation, under the same conditions to maximize the productivity.