Readily scalable methodology for the synthesis of nonsymmetric glyceryl diethers by a tandem acid-/base-catalyzed process

Leal-Duaso, Alejandro (Universidad de Zaragoza) ; Gracia-Barberán, Sara ; Mayoral, José A. (Universidad de Zaragoza) ; García, José I. ; Pires, Elisabet (Universidad de Zaragoza)

Resumen: A useful optimized synthetic methodology has been designed for the synthesis of nonsymmetric glyceryl diethers from epichlorohydrin. A tandem process combining a cheap, heterogeneous, and fully recoverable acid catalyst and alkaline hydroxide is used for the synthesis of a variety of glycerol-derived ethers bearing different alkyl substituents in 1 and 3 positions. Different heterogeneous acid catalysts have been tested for the reaction of epichlorohydrin with several alcohols, the best results being obtained with readily available recoverable and inexpensive montmorillonite-K10 and Nafion NR50. For the second reaction step, potassium hydroxide is used. In all the cases, good yields of the desired glyceryl diethers are obtained in smooth reaction conditions, always with total conversion of epichlorohydrin and without the need of intermediate purification. Scale-up of the tandem process has been carried out with good results.

Idioma: Inglés

DOI: 10.1021/acs.oprd.9b00411

Año: 2020

Publicado en: ORGANIC PROCESS RESEARCH & DEVELOPMENT 24, 2 (2020), 154-162
ISSN: 1083-6160

Factor impacto JCR: 3.317 (2020)

Categ. JCR: CHEMISTRY, ORGANIC rank: 20 / 57 = 0.351 (2020) - Q2 - T2
Categ. JCR: CHEMISTRY, APPLIED rank: 26 / 74 = 0.351 (2020) - Q2 - T2

Factor impacto SCIMAGO: 0.904 - Physical and Theoretical Chemistry (Q1) - Organic Chemistry (Q1)

Financiación: info:eu-repo/grantAgreement/ES/DGA/E37-17R
Financiación: info:eu-repo/grantAgreement/ES/MCIU/RTI2018-093431-B-I00

Tipo y forma: Article (PostPrint)

Área (Departamento): Área Química Orgánica (Dpto. Química Orgánica)